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| 1 |  |
Allocholesterol / Coprostenol / 4:5-Coprosten-3-ol |
Cholest-4-en-3b-ol |
SST0001 | Hideaki Nishino |
C27H46O1 | 386.654 | |
132  (ether-methanol) (Ref. 0002) |
[a]23/D=+43.7 (c=1 in benzene) (Ref. 0002) |
Freely sol in benzene, acetone, ether, chloroform, dioxane, pyridine; less sol in methanol, alcohol (Ref. 0002) |
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| 2 |  |
Androsterone / Cis-androsterone / 3a-Hydroxy-17-androstanone / Androstan-3(a)-ol-17-one / 3(a)-Hydroxyetioallocholan-17-one / 3-Epihydroxyetioallocholan-17-one |
3a-Hydroxy-5a-androstan-17-one |
SST0002 | Hideaki Nishino |
C19H30O2 | 290.440 | |
185-185.5 C (Ref. 0006) |
Sol in most organic solvents. Barely sol in water. (Ref. 0007) |
Not precipitated by digitonin. (Ref. 0007) |
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| 3 |  |
Bufotalin |
16-(Acetyloxy)-3,14-dihydroxybufa-20,22-dienolide / 3b,14,16b-Trihydroxy-5b-bufa-20,22-dienolide 16-acetate |
SST0003 | Hideaki Nishino |
C26H36O6 | 444.560 | |
[a]20/D=+5.4 (c=0.5 in CHCl3) (Ref. 0013) |
Sol in alcohol, chloroform (Ref. 0017) |
max. 300 nm (Ref. 0015) |
1H n.m.r. (100 MHz), employing spin-decoupling experiments, lead to the following assignments: the pyrone ring protons, d 6.17 (Ha, Doublet, Jab 9Hz, Jac 1Hz), 8.04 (Hb, Quartet, Jab 9Hz, Jbc 2.7Hz), 7.24 (Hc), while in ring D the 17a-proton Hd appeared as a doublet at d 2.72, J 9Hz. Because Jed and Jef were both 9Hz, He corresponded to a sextet at d 5.54 with Jeg 2 Hz. The methylene protons Hf and Hg gave signals at d 2.66 and 1.9, respectively. (Ref. 0016) |
m/e: 444 (M, 5%) (M for C26H36O6=444); 384 (M-60, 100%); 336 (M-60-18, 61%); 351 (M-60-18-15, 9%); 348 (M-60-36, 10%); 341 (M-60-43, 80%); 323 (M-60-43-18, 68%). Metastable ion peaks at m/e 332.0 (440 to 384), 349.0 (384 to 366), and 303.0 (384 to 341) were observed. (Ref. 0016) |
A couple of methods for partial synthesis. Prepare the 16-ketone of cinobufagin, reduce 14,15b-epoxide group with chromous acetate to yield b-hydroxy ketone and a,b-unsaturated ketone. Selectively reduce the b-hydroxy ketone with Urushibara nickel A to produce alcohol, which is acetylated to provide diacetate. Treat the diacetate with HCl in methanol to give bufotalin. Alternatively reduce first the a,b-unsaturated ketone with Urushibara nickel A to allylic alcohol. After acetylation subject the olefin to hypoiodous acid or hypobromous acid, then treat the resulting halohydrin with Urushibara nickel A. Hydrogenolyze the product to bufotalin 3b-acetate. (Ref. 0018) |
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| 4 |  |
Chlorogenin |
5a-Spirostan-3b,6a-diol |
SST0004 | Hideaki Nishino |
C27H44O4 | 432.636 | |
Saponin useful as fish poisons. (Ref. 0025) |
[a]24/546 = -52 (chloroform or isopropanol) (Ref. 0023) |
Sol in methanol, isopropanol. (Ref. 0023) |
d (pyridine) 0.83 (19-Me), 0.86 (18-Me), 1.12d(21-Me, J=7Hz), 1.05d (27-Me, J=7Hz), 3.30d (26-H2, J=11Hz), 3.39dd (26-H2, J=11, 3Hz), 4.45ddd (16-H, J=7, 7, 7Hz), 3.70m (3H and 6H). (Ref. 0024) |
m/e 432 (Ref. 0024) |
Root of amole (California soap plant, lily family, Chlorogalum pomeridianum Kunth) (Ref. 0025) |
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| 5 |  |
Cholestanol / b-Cholestanol |
Dihydroxycholesterol / 3b-Hydroxycholestan / 5a-Cholestan-3b-ol |
SST0005 | Hideaki Nishino |
C27H48O1 | 388.669 | |
Accumulation within the nervous system in cerebrotendinous xanthomatosis patients. (Ref. 0031) |
141.5-142 C (Ref. 0026) |
[a] 22/D=+28.8 (Ref. 0026) |
Freely sol in heated alcohol, ethylether, chloroform. Approximately 1 g/100 ml alcohol or 200 ml methanol. (Ref. 0028) |
9.20(19-H), 9.36(18-H) (Ref. 0029) |
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| 6 |  |
Coprostenol / 3b-Cholestanol / Stercorin |
5b-Cholestan-3b-ol |
SST0006 | Hideaki Nishino |
C27H48O1 | 388.669 | |
101 C (methanol) (Ref. 0035) |
[a]18/D=+28 (c=1.8 in chloroform) (Ref. 0036) |
Sol in ethylether, chloroform, benzene. Slightly sol in methanol (1g/145 ml). Sol in water. (Ref. 0036) |
Separation from cholesterol using TLC. (Ref. 0034) |
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| 7 |  |
7-Dehydrocholesterol / Provitamin D3 |
Cholesta-5,7-dien-3b-ol |
SST0007 | Hideaki Nishino |
7-DHC |
C27H44O1 | 384.638 | |
149-150 C (Ref. 0043) |
Sol in ether, chloroform. Slightly sol in methanol. Insol in water (Ref. 0045) |
nm(e): min. 230 (150), max. 262.5 (740), max. 271 (1,040), min. 276 (883), max. 281.5 (1,075), min. 288 (553), max. 293 (615), max. 321 (36). (Ref. 0008) |
E1%/1cm (l, nm): 39.1 (2,300), 193 (2,625), 271 (2,710), 230 (2,760), 280 (2,815), 144 (2,880), 160 (2,930), 0.9 (3,210). (Ref. 0046) |
Possibly excess accumulation relates to holoprosencephalic disorder. (Ref. 0055) |
Precipitable by digitonin. (Ref. 0042) |
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| 8 |  |
Desmosterol / 24-Dehydrocholesterol / Desmesterol |
Cholesta-5,24-dien-3b-ol |
SST0008 | Hideaki Nishino |
C27H44O1 | 384.638 | |
[a]/D=-37.9 , [a]27/D=-40.2 (c=1 in chloroform) (Ref. 0057) |
Sol in ether, benzene, chloroform, ethanol. (Ref. 0061) |
max. 320nm (E1%/1cm, 240), 433nm (E1%/1cm, 154), min. 256nm (E1%/1cm, 93), 393nm (E1%/1cm, 109), (7  10-7 M in 97% sulfate) (Ref. 0057) |
m/e: 91(31%), 93(48%), 95(52%), 105(37%), 107(41%), 109(33%), 117(12%), 119(44%), 121(34%), 123(15%), 129(100%), 130(17%), 131(20%), 133(26%), 135(17%), 143(20%), 145(32%), 147(22%), 149(13%), 159(25%), 161(18%), 173(12%), 213(13%), 245(12%) (Ref. 0058) |
Synthesis from 3b-hydroxybisnorcholenic acid and 3b-hydroxynorcholenic acid by lithium-ethylamine-induced hydrogenolysis of the methyl ether derivatives of allyl alcohol. (Ref. 0060) Synthesis from 3b-acetoxy-23,24-dinorchol-5-en-22-ol by coupling reaction between dimethylallyllithium and a bromide. (Ref. 0062) Synthesis from 16a, 17a-epoxypregnenolone by employing the potassium-assisted oxy-Cope rearrangement as a key stereodirecting process at C-20. (Ref. 0063) |
Possibly excess accumulation relates to lethal multiple malformations. (Ref. 0064) |
Conversion to cholesterol in vivo. (Ref. 0056) |
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| 9 |  |
a-Ecdysone |
2,3,14,22,25-Pentahydroxycholest-7-en-6-one |
SST0009 | Hideaki Nishino |
C27H44O6 | 464.635 | |
[a]20/578 = +62 (Ref. 0067) |
Sol in ethanol. (Ref. 0065) |
KBr (/cm): 1658, 1652 (Ref. 0069) |
n max. 73(18-H), 107(19-H), 124 and 131(21-H), 138(26-H and 27-H) cps (Ref. 0070) |
m/e (t-190 ): 446(3%), 428(29), 418(2), 413(2), 410(3), 372(3), 359(4), 348(8), 330(15), 315(18), 300(23), 279(17), 267(5), 255(8),250(13), 249(10), 99(100), 81(61) (Ref. 0071) |
Synthesis from stigma-22-ene-3,6-dione by dividing three partial structure, A-ring, B, C-ring, and side chain. (Ref. 0068) Synthesis from 3b-hydroxy-23,24-bisnorchol-5-en-22-oic acid, readily available starting material. (Ref. 0070) Synthesis from (20S)-2b,3b-diacetoxy-20-formyl-5b-pregn-7-en-6-one by Grinard reaction with 2-methyl-3-butyn-2-oltetrahydropyran-2-yl ether, followed by hydrogenation of the triple bond, removal of the protecting groups, and hydroxylation in 14a-position. (Ref. 0071) Synthesis from methyl 14a-hydroxy-2b,3b-isopropylidenedioxy-6-oxo-22,23-bisnor-5b-chol-7-enoate. (Ref. 0074) |
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| 10 |  |
b-Ecdysone / 20-Hydroxyecdysone / Ecdysterone / Crustecdysone / Isoinokosterone |
2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one |
SST0010 | Hideaki Nishino |
C27H44O7 | 480.634 | |
Molting and metamorphosis hormone for Insecta and Crustacea. Much potent than a-ecdysone. (Ref. 0077) |
240-242 C (methanol-ethylacetate) (Ref. 0079) |
[a]28/D = +63 (c=1.0, methanol) (Ref. 0080) |
Sol in methanol, ethanol. (Ref. 0080) |
n KBr/max. 1656, 1615, 1387, 1229, 1053, 917, 878 /cm (Ref. 0079) |
Pyridine-d5: 1.07(19-H), 1.20(18-H), 1.36(26- and 27-H), 1.56(21-H), 6.17(7-H) (Ref. 0079) |
m/e: 480 (ecdysone+0), 462 (M-H2O), 444 (M-2H2O), 426 (M-3H2O), 408 (M-4H2O) (Ref. 0077) |
Synthesis from hydroxylated aldehyde precursor, (20S)-2b,3b-diacetoxy-5a-hydroxy-20-methoxycarbonylpregn-7-en-6-one. (Ref. 0079) Synthesis from 20b-hydroxy-5a-pregnane-3,6-dione via 2b,3b-diacetoxy-5a-pregn-7-ene-6,20-dione. (Ref. 0083) Stereospecific synthesis from 20bbenzoyloxy-5-pregnen-3b-ol. (Ref. 0084) Stereocontrolled total synthesis from 2b,3b,20b,-triacetoxy-5a-pregnan 6-one via acetylene-cationcyclization. (Ref. 0085) |
The complete structure of natural b-ecdysone determined by a three-dimensional X-ray analysis using convolution molecule method. (Ref. 0076) |
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| 11 |  |
Equilin |
3-Hydroxyestra-1,2,5(10),7-tetraen-17-one / 1,3,5,7-Estratetraen-3-ol-17-one |
SST0011 | Hideaki Nishino |
C18H20O2 | 268.350 | |
loge=3.36 (282nm) (Ref. 0089) |
Synthesis from 19-nortestosterone acetate via four intermediates. (Ref. 0089) Relatively simple synthesis from dienone compound. (Ref. 0092) Synthesis from estratetraene via several novel steroid intermediates and reactions. (Ref. 0093) Total synthesis from estra-1,3,5(10),8-tetraenes by oxidation with m-chloroperbenzoic acid, rearrangement of the resulting epoxide with acid, catalytic hydrogenation, and dehydration. (Ref. 0094) Synthesis by conversion of equilenine. (Ref. 0095/0096) |
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| 12 |  |
Ergosterol / Ergosterin / Provitamin D2 |
Ergosta-5,7,22-trien-3b-ol |
SST0012 | Hideaki Nishino |
C28H44O1 | 396.648 | |
Antirachitic activity as 1,25-dihydroxyergocalciferol. (Ref. 0102) |
168 C (alcohol) (Ref. 0098) |
bp0.01 = 250 C (Ref. 0098) |
Sol in heated chloroform, benzene. Slightly sol in methanol, ethanol, ether, petroleum ether. Insol in water. (Ref. 0050) |
max. nm (e); 262 (6,940); 271 (10,000); 282 (10,600); 293 (6,060). min. nm (e); 230 (1,430); 263 (6,850); 275.5 (8,580); 289 (5,450); 317.5 (35) (Ref. 0008) |
E 1%/1cm: nm(e); 36.1 (2,300); 175 (2,620); 173 (2,630); 253 (2,710); 217 (2,755); 268 (2,820); 138 (2,890); 158 (2,930); 0.8 (3,175) (Ref. 0046) |
Precipitable by digitonin. Positive in Rosenheim reaction. (Ref. 0097) |
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| 13 |  |
b-Estradiol / Cis-estradiol / Estradiol / 3,17-Epidihydroxyestratriene / Dihydrofollicular hormone / Dihydrofolliculin / Dihydroxyestrin / Dihydrotheelin / Compudose 365 / Dihydromenformon / Dimenformon / Diogyn / Estrovite / Femestral / Gynergon / Gynoestryl / Lamdiol / Macrodiol / Oestergon / Ovahormon / Ovasterol / Ovocyclin / Ovocylin / Perlatanol / Primofol / Profoliol / Progynon-dh |
Estra-1,3,5(10)-triene-3b,17b-diol |
SST0013 | Hideaki Nishino |
C18H24O2 | 272.382 | |
Most potent estrogenic activity. (Ref. 0103) |
173-179 C (Ref. 0104) |
[a]25/D= from +76 to +83 (dioxane) (Ref. 0104) |
Hardly sol in water. Sol in organic solvents like alcohol, acetone, dioxane. Slightly sol in vegetable oil. (Ref. 0104) |
max. 225, 280nm (Ref. 0104) |
e=2,120 (281nm), E1%/1cm=78 (Ref. 0105) |
Ovary, placenta, testis, adrenal cortex of animals. (Ref. 0104) |
Very weak estrogenic activity in 17a-form. (Ref. 0103) |
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| 14 |  |
estriol / 16a-Hydroxyestradiol / Follicular hormone hydrate / Oestriol / Trihydroxyestrin / Aacifemine / Colpogyn / Destriol / Gynasan / Hormomed / Klimax E / Klimoral / Oekolp / Ortho-gynest / Ovesterin / Ovestin / Ovo-vinces / Theelol / Tridestrin / Triovex |
Estra-1,3,5(10)-triene-3,16,17-triol / 3,16a,17b-Trihydroxy-D1,3,5-estratriene |
SST0014 | Hideaki Nishino |
C18H24O3 | 288.381 | |
Insol in water. Sol in alcohol, dioxane, chloroform, ether, vegetable oils. Freely sol in pyridine. (Ref. 0112) |
max. 280nm (Ref. 0113) |
E1%/1cm=75, e=2,150 (280nm) (Ref. 0113) |
Partial synthesis from estrone by transforming a-keto to a-glycol with sodium amalgam in dilute ethanolic acetic acid (Ref. 0111) , Synthesis from zinc-acetic acid reduction of 16-oximino-17-ketosteroids and 16,17-diketosteroids. (Ref. 0119) Synthesis from 3b-hydroxyandrostane-17-one by formation of an enol acetate of a 17-ketosteroid followed by epoxidation with perbenzoic acid. (Ref. 0120) |
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| 15 |  |
Estrone / Oestrone / Theelin / Folliculin / Follicular hormone / Tokokin / Thelykinin / Ketohydroxyestrin / Hiestrone / Menformon / Glandubolin / Cristallovar / Destrone / Endofolliculina / Estrol / Femidyn / Folikrin / Ovex / Kolpon / Crinovaryl / Folisan / Disynformon / Hormovarine / Oestroperos / Wynestron / Thelestrin / Kestrone / Estrusol / Estrugenone / Femestrone INJ. / Folipex / Follestrine / Follidrin / Follicunodis / Hormofollin / Oestrin / Oestroform / Ovifollin / Perlatan / Ketodestrin / Unden |
3-Hydroxyestra-1,3,5(10)-trien-17-one / 1,3,5-Estratrien-3-ol-17-one |
SST0015 | Hideaki Nishino |
C18H22O2 | 270.366 | |
[a]22/D=+152 (Ref. 0123) |
3g sol in 100 ml water (25 C), 1g sol in 96% alcohol (15C) 250ml, boiling alcohol 50ml, acetone 50ml (15C), chloroform 110 ml (15C), boiling benzene 145ml. Sol in diozane, pyridine, fixed alkali hydroxides. Slightly sol in ether, vegetable oils. (Ref. 0125) |
max. 282, 296nm(p-dioxane, e=2300, 2130); 300, 450nm (conc.sulfate); 239, 293nm (0.1M NaOH) (Ref. 0125) |
nmax (CHCl3): 1,693/cm (methyl ether) (Ref. 0126) |
(chloroform)d: 1.08 (3H,s,-CH3), 3.69 (3H,s,OCH3), 6.39-6.72 (2H,m,C2H), 7.08 (1H,d,J=9Hz,C,H) (methyl ether) (Ref. 0126) |
m/e 298 (M+) (methyl ether) (Ref. 0126) |
E1%/1cm=77 (280nm, e = 2,080) (Ref. 0105) |
Stereospecific synthesis from b-m-anisylethylmalonic ester by condensation if the sodio derivative with the acid chloride of ethyl hydrogen glutarate. (Ref. 0128) Total synthesis from tricyclic ketoester compounds. (Ref. 0123/0129/0130/0131/0132) New synthesis methods by intramolecular cycloaddition reaction of olefinic o-quinodimethane. (Ref. 0126/0133/0134/0135) |
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| 16 |  |
a1-Sitosterol / Citrostadienol |
4-Methylstigmasta-7,24(28)-dien-3-ol |
SST0016 | Hideaki Nishino |
C30H50O1 | 426.717 | |
Sol in alcohol, benzene, pyridine (Ref. 0139) |
m/e more than 200%: M(3), M-15(3), M-(15+18)(-), M-98(57), M=(98+15)(8), M-(98+18)(3), M-127(3), M-(98+15+18)(4), M-141(100), M-(139+18)(8), M-(141+18)(7), M-165(10), M-181(6), M-(165+18)(3), M-184(2), M-185(3), M-(181+18)(9) (Ref. 0140) |
Synthesis from D7-cholesten-3-one by methylation and reduction. (Ref. 0138) |
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| 17 |  |
b-Sitosterol / 22:23-Dihydrostigmasterol |
Stigmast-5-en-3b-ol |
SST0017 | Hideaki Nishino |
C29H50O1 | 414.707 | |
TMS-derivatives (MW = 486): 129(100%), 357(98%), 396(66%), 121(58%), 145(45%), 215(42%) (Ref. 0148) |
Stereospecific synthesis 24-ethylcholesta-5,22,25-trien-3b-ol by hydrogenation and ring opening. (Ref. 0157) |
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| 18 |  |
g-Sitosterol / Clionasterol |
Stigmast-5-en-3b-ol |
SST0018 | Hideaki Nishino |
C29H50O1 | 414.707 | |
Stereospecific synthesis 24-ethylcholesta-5,22,25-trien-3b-ol by hydrogenation and ring opening. (Ref. 0157) |
Different stereoconfiguration in C-24 from b-sitosterol. (Ref. 0165) |
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| 19 |  |
Stigmasterol, Anti-stiffness factor / 3b-Hydroxy-24-ethyl-D5,22-cholestadiene |
Stigmasta-5,22-dien-3b-ol |
SST0019 | Hideaki Nishino |
C29H48O1 | 412.691 | |
Antistiffness factor. (Ref. 0177) |
Insol in water. Sol in organic solvents (Ref. 0172) |
TMS : 484(22%), 394(35%), 255(63%), 145(32%), 133(38%), 129(100%) (Ref. 0148) |
Simple purification as acetic ester bromide because of the insolubility in ethylether. (Ref. 0178) |
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| 20 |  |
Testosterone / Trans-testosterone / Geno-cristaux gremy / Malestrone (AMPS) / Orquisteron / Percutacrine androgenique / Primotest / Primoteston / Sustanon / Mertestate / Testobase / Virosterone / Virormone / Testryl / Testrone / Homosterone / Oreton-f / Teslen |
17b-Hydroxyandrost-4-en-3-one / D4-Androsten-17b-ol-3-one |
SST0020 | Hideaki Nishino |
C19H28O2 | 288.424 | |
154-154.5 C (Ref. 0179) |
[a]24/D = +109 (c = 4 in alcohol) (Ref. 0179) |
Insol in water. Sol in alcohol, ether, other organic solvents. (Ref. 0184) |
E1%/1cm=582 (240nm, e = 16,800) (Ref. 0186) |
Synthesis from cholesterol via dehydroandrosterone. (Ref. 0184) |
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| 21 |  |
21-Acetoxypregnenolone / Acetoxanon |
3b,21-Dihydroxy-5-pregnen-20-one-21-acetate / 5-Pregnene-3b,21-diol-20-one-21-acetate / Pregnenolone-21-acetate |
SST0021 | Hideaki Nishino |
A.O.P. |
C23H34O4 | 374.514 | |
Synthesis as an intermediate in desoxycorticosterone acetate synthesis (Ref. 0188) |
184-185 (Ref. 0188) |
Slightly sol in ether, pentane. Sol in chloroform, toluene (Ref. 0189) |
Anti-inflammatory (Ref. 0188) |
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| 22 |  |
Allopregnane |
5a-Pregnane |
SST0022 | Hideaki Nishino |
C21H36 | 288.511 | |
84-85 (acetone+methanol) (Ref. 0189) |
[a]/D = +18.0 (c = 1.388 in chloroform) (Ref. 0191) |
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| 23 |  |
Allotetrahydrocortisone / Reichstein's Substance Dehydro-C / 11-Dehydro C |
5a-Pregnane-3a,17a,21-triol-11,20-dione |
SST0023 | Hideaki Nishino |
C21H32O5 | 364.476 | |
Synthesis as 3a,21-diacetate form (Ref. 0196) |
212-214 (Ref. 0195) |
Bovine adrenal (Ref. 0195) |
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| 24 |  |
Androstane / 5 -Androstane / Etioallocholane |
5a-Androstane |
SST0024 | Hideaki Nishino |
C19H32 | 260.457 | |
50-50.5 (acetone-methanol) (Ref. 0199) |
Sol in acetone, alcohol, methanol, ether, petroleum ether (Ref. 0199) |
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| 25 |  |
11b-Hydroxyisoandrosterone / 11b-Hydroxyepiandrosterone |
5a-Androstane-3b,11b-diol-17-one / 3b,11b-Dihydroxy-5a-androstan-17-one |
SST0025 | Hideaki Nishino |
C19H30O3 | 306.440 | |
235-238 (acetone+ether) (Ref. 0200) |
m/e = 450(M+), 435(M-15), 394(M-56), 360(M-90), 345(M-(90+15)), 270(M-2 90), 255(M-[(290)+15]), 214(M-[(290)+56]), 199(M-[(290)+56+15]), 156 (Ref. 0203) |
Induction of d-aminolevulinate synthase and porphyrins (Ref. 0202) |
Precipitable by digitonin (Ref. 0200) |
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| 26 |  |
Androstenediol |
5-Androstene-3b,17b-diol / 3b,17b-Dihydroxy-5-androstene |
SST0026 | Hideaki Nishino |
C19H30O2 | 290.440 | |
Sol in isopropanol, insol in water (Ref. 0205) |
No crest growth in capon (Ref. 0205) |
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| 27 |  |
3b,16a-Dihydroxy-5-androstene |
SST0027 | Hideaki Nishino |
C19H30O2 | 290.440 | |
Synthesis from 5-androsten-3b-ol-16-one by the sodium borohydride reduction or by reduction of 3b-acetoxy-5-androsten-16-one to 3b-acetoxy-5-androsten-16b-ol, which is in turn tosylated and epimerized at C16 (Ref. 0206) |
216-217 (aqueous methanol) (Ref. 0206) |
Sol in ethanol, dioxane (Ref. 0206) |
Tranquilizer (Ref. 0206) |
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| 28 |  |
Androstenedione / Androtex |
4-Androstene-3,17-dione |
SST0028 | Hideaki Nishino |
C19H26O2 | 286.409 | |
[a]17/D = +2.26 (Ref. 0210) |
Sol in chloroform (Ref. 0210) |
max. 235 nm (chloroform) (Ref. 0208) |
Adrenal cortex (Ref. 0207) |
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| 29 |  |
5a-Androst-16-en-3a-ol / 3a-Hydroxy-5a-androst-16-ene / 16-[5a]Androsten-3a-ol |
SST0029 | Hideaki Nishino |
C19H30O | 274.441 | |
142.5-143 (Ref. 0213) |
Sol in chloroform (Ref. 0213) |
m/e 346(M), 331(M-15), 256(M-90), 241(M-(90+15)) (Ref. 0214) |
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| 30 |  |
Antheridiol |
3b,22,23-Trihydroxy-7-oxostigmasta-5,24(28)-dien-29-oic acid g-lactone |
SST0030 | Hideaki Nishino |
C29H42O5 | 470.641 | |
Synthesis of 22,23 isomers from 3-tetrahydropyran-2'-yloxy22,23-bisnorchol-5-en-24-al by aldol condensation (Ref. 0227) A new synthetic route by condensation of the 2-lithio derivative of 3-isopropylfuran with 3-tetrahydropyran-2'-yloxy22,23-bisnorchol-5-en-24-al (Ref. 0230) Synthesis from C22 aldehyde by aldol condensation (Ref. 0231) |
250-255 (Ref. 0224) |
Sol in hot methanol, slightly sol in chloroform, very slightly sol in water (Ref. 0224) |
nKBr max. 3390, 1742, 1672/cm (Ref. 0224) |
Olefin protons (5.69,5.77 ppm) methyl-groups at C-18 and C-19 (0.70,1.20 ppm) (Ref. 0225) |
|||||||||||||||
| 31 |  |
Azacosterol / Diazasterol |
17b-[[3-(Dimethylamino)propyl]-methylamino]androst-5-en-3b-ol / N-Methyl-N-[3(dimethylamino)propyl]-17b-aminoandrost-5-en-3b-ol / 20,25-Diazacholesterol |
SST0031 | Hideaki Nishino |
C25H44ON2 | 388.630 | |
Synthesis from 3b-hydroxyandrost-5-en-17-one (Ref. 0234) |
146-148 C (acetone+methanol) (Ref. 0234) |
[a]25/D=-54.5 (Ref. 0234) |
Sol in ether anhydride, isopropylalcohol. (Ref. 0234) |
Effective application to therapy for hypercholesterolemia. Oral ingestioin, 15% decrease (0.5mg/kg body weight), 35% decrease (3mg/kg body weight). (Ref. 0234) |
Preparation of dihydrochloride salt. (Ref. 0234) |
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| 32 |  |
Budesonide / S-1320 / Preferid / Pulmicort / Rhinocort / Sprirocort |
16,17-Butylidenebis(oxy)-11,21-dihydroxypregna-1,4-diene-3,20-dione / (R,S)-11b,16a,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with butylaldehyde |
SST0032 | Hideaki Nishino |
C25H34O6 | 430.534 | |
Synthesis. (Ref. 0235) |
221-232 C (Ref. 0235) |
[a]25/D=+98.9 (c=0.28 in methylene chloride) (Ref. 0235) |
Quantification of the epimer and impurities in HPLC. (Ref. 0237) |
Pharmacodynamics. (Ref. 0236) |
|||||||||||||||
| 33 |  |
Bufalin |
3,14-Dihydroxybufa-20,22-dienolide |
SST0033 | Hideaki Nishino |
C24H34O4 | 386.524 | |
[a]/D=-20 (Ref. 0239) |
Sol in alcohol, chloroform. (Ref. 0239) |
nmax 3080, 2945, 1725, 1640, 1545 /cm (Ref. 0241) |
pmr (100MHz) 0.71 and 0.96(18 and 19 methyls), 4.14 (3a proton), 6.25(doublet, Ha,J=10Hz), 7.28(partially masked doublet, Hc,J=2Hz), 8.85(quartet, Hb,J=10 and 2Hz) (Ref. 0241) |
M+ 386, 368, 350, 325, 250, 232, 214, 207, 203, 147 (Ref. 0241) |
|||||||||||||||
| 34 |  |
Bufogenin B / Desacetylbufotalin |
3,14,16-Trihydroxybufa-20,22-dienolide |
SST0034 | Hideaki Nishino |
C24H34O5 | 402.524 | |
Synthesis from bufotalin. (Ref. 0247) |
210-223 C (Ref. 0247) |
[a]19/D=+30 (c=1.039 in dioxane) (Ref. 0247) |
Sol in dioxane. Very sparingly sol in chloroform, methanol, acetone. (Ref. 0247) |
Chinese medicine (Ch'an Su, Bufo asiaticus = isolated from Bufo gargarizans Canter, a Chinese toad), or also yielded from bufotalin. (Ref. 0247) |
Cardiotonic steroid. (Ref. 0247) |
||||||||||||||
| 35 |  |
Calusterone / U-22550 / Methosarb |
17-Hydroxy-7,17-dimethylandrost-4-en-3-one / 7b,17a-Dimethyltestosterone |
SST0035 | Hideaki Nishino |
C21H32O2 | 316.478 | |
Synthesis (Ref. 0248) |
127-129 C (acetone) (Ref. 0248) |
[a]/D=+57 (chloroform) (Ref. 0248) |
UV max (alcohol): 243nm (Ref. 0248) |
Carcinostatic agent (Ref. 0248) |
|||||||||||||||
| 36 |  |
Campesterol |
(24R)-Ergost-5-en-3b-ol |
SST0036 | Hideaki Nishino |
C28H48O | 400.680 | |
157-158 C (acetone) (Ref. 0249) |
[a]23/D=-33 (22.5mg in 5ml chloroform) (Ref. 0249) |
Small amounts in oils prepared from rapeseed, soybean, malt (wheat germ). (Ref. 0249) |
|||||||||||||||||
| 37 |  |
Chondrillasterol |
Stigmasta-7,22-dien-3-ol |
SST0037 | Hideaki Nishino |
C29H48O | 412.691 | |
168-169 C (chloroform-methanol) (Ref. 0251) |
[a]24/D=-2 (chloroform) (Ref. 0251) |
Sol in chloroform, methanol. (Ref. 0251) |
Isolation from green algae (Scenedesmus obliquus (Turpin) Kuetz, Scenedesmaceae) (Ref. 0251) |
Stereoisomer of a-spinasterol. (Ref. 0251) |
|||||||||||||||
| 38 |  |
Chonemorphine |
N20,N20-Dimethyl-5a-pregnane-3b,20-diamine / 3b-Amino-20a-dimethylamino-5a-pregnane |
SST0038 | Hideaki Nishino |
C23H42ON2 | 362.592 | |
Synthesis from Acetoxy-3a-bisnorallo cholanique. (Ref. 0255) |
149 C (Ref. 0255) |
[a]/D=+25 (chloroform, c=1) (Ref. 0255) |
Sol in chloroform, ether. (Ref. 0255) |
Stereochemistry. (Ref. 0256) |
|||||||||||||||
| 39 |  |
Cinobufotalin |
16-(Acetyloxy)-14,15-epoxy-3,5-dihydroxybufa-20,22-dienolide / 14,15b-Epoxy-3b,5,16b-trihydroxy-5b-bufa-20,22-dienolide 16-acetate |
SST0039 | Hideaki Nishino |
C26H34O7 | 458.544 | |
259-262 C (acetone) (Ref. 0257) |
[a]20/D=+11 (Ref. 0257) |
UV max: 295nm (loge=3.72) (Ref. 0257) |
Isolation from Chinese drug, Ch'an Su, prepared from Chinese toad (Bufo asiaticus=Bufo gargarizans Cantor) (Ref. 0247) |
||||||||||||||||
| 40 |  |
Convallamarogenin |
D25-5b,20b,22a-Spirostendiol-(1b,3b) |
SST0040 | Hideaki Nishino |
C27H42O4 | 430.620 | |
259-261 C (chloroform+methanol) (Ref. 0259) |
[a]27/D=-79.1 (c=1.02 in chloroform) (Ref. 0258) |
Sol in methanol, chloroform, ethanol. (Ref. 0258) |
nnujol/max: 3095, 1655, 877/cm (vinyl-form double bond) 3350, 3295/cm (Ref. 0259) |
Root of a lily of the valley (Convallaria majalis L.) (Ref. 0259) |
|||||||||||||||
| 41 |  |
Convallatoxin |
3b-[(6-Deoxy-a-L-mannopyranosyl)oxy]-5,14-dihydroxy-19-oxo-5b-card-20(22)-enolide |
SST0041 | Hideaki Nishino |
C29H42O10 | 550.638 | |
Synthesis from strophanthidin and acetobromrhamnose. (Ref. 0266) |
Cardiotonic drug. (Ref. 0263) |
||||||||||||||||||
| 42 |  |
Cortisone |
17a,21-Dihydroxy-4-pregnene-3,11,20-trione / 17-Hydroxy-11-dehydrocorticosterone / 11-Dehydro-17-hydroxycorticosterone / D4-Pregnene-17a,21-diol-3,11,20-trione |
SST0042 | Hideaki Nishino |
C21H28O5 | 360.444 | |
UVmax: 237nm (e=14,000) (Ref. 0270) |
Action as a glucocorticoid. (Ref. 0270) |
||||||||||||||||||
| 43 |  |
Cortisone phosphate |
17a-Hydroxy-4-pregnene-3,11,20-trione-21-dihydrogen phosphate |
SST0043 | Hideaki Nishino |
C21H29O8P | 440.424 | |
UV max (methanol): 238nm (e=15,200), (water): 244nm (e=15,900) (Ref. 0286) |
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| 44 |  |
Cynanchogenin |
12-[(3,4-Dimethyl-1-oxo-2-pentenyl)oxy]-3,8,14-trihydroxypregn-5-en-20-one |
SST0044 | Hideaki Nishino |
C28H42O6 | 474.629 | |
165-167 C (ether+petr. ether) (Ref. 0289) |
[a]22/D=-39.5 (c=1.24 in 90% ethanol) (Ref. 0289) |
Sol in petroleum ether, ethanol. (Ref. 0289) |
UVmax (ethanol): 218 nm (loge=4) (Ref. 0288) |
lKBr/max/cm: n/OH: 3480, n/C=O: 1700, n/C=C: 1638 (Ref. 0288) |
Isolation from the root of Cynanchum caudatum Max., Asclepiadaceae (Ref. 0288) |
||||||||||||||
| 45 |  |
cyproterone |
6-Chloro-1,2-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione / 6-Chloro-6-dehydro-17a-hydroxy-1,2a-methyl-eneprogesterone / 6-Chloro-1,2a-methylene-4,6-pregnadien-17a-ol-3,20-dione |
SST0045 | Hideaki Nishino |
C22H27O3Cl | 374.901 | |
Preparation as a free alcohol form. (Ref. 0294) |
237.5-240 C (ethyl acetate) (Ref. 0294) |
UVmax (methanol): 281nm (e=17,280) (acetate) (Ref. 0294) |
Metabolism in human body (Ref. 0294) |
Anti-androgenic activity as an acetate. (Ref. 0294) |
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| 46 |  |
11-Dehydrocorticosterone / Substance A |
21-Hydroxypregn-4-ene-3,11,20-trione / D4-Pregnen-21-ol-3,11,20-trione / 17-(1-Keto-2-hydroxyethyl)-D4-androsten-3,11-dione |
SST0046 | Hideaki Nishino |
C21H28O4 | 344.445 | |
178-180 C (aq.acetone) (Ref. 0295) |
Relatively sol in benzene. (Ref. 0295) |
l max = 237.5nm (acetate), E1%=386 (Ref. 0296) |
Found in adrenal cortex. Isolation of 333 mg from 1000 lbs beef glands. (Ref. 0295) |
||||||||||||||||
| 47 |  |
Dehydroergosterol |
Ergosta-5,7,9(11),22-tetraen-3b-ol |
SST0047 | Hideaki Nishino |
C28H42O | 394.632 | |
146 C (Ref. 0300) |
bp0.5=230 C (Ref. 0300) |
[a]15/D=+149.2 (c=1.9 in chloroform) (Ref. 0300) |
Sol in methanol (1g/800ml), ether, chloroform, benzene. (Ref. 0300) |
l max: 342.0, 325.5, 311.0, 296 nm (Ref. 0301) |
|||||||||||||||
| 48 |  |
7-Dehydrositosterol |
Stigmasta-5,7-dien-3b-ol |
SST0048 | Hideaki Nishino |
C29H48O | 412.691 | |
144-145 C (Ref. 0302) |
[a]21/D=-116 (c=2 in chloroform) (Ref. 0302) |
Sparingly sol in methanol, alcohol. Sol in other organic solvent. Insol in water.(Ref. 0302) |
Almost same absorption spectrum as ergosterol. (Ref. 0302) |
Separation from b-sitosterol in soybean oil. (Ref. 0302) |
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| 49 |  |
Delmadinone acetate |
17-(Acetyloxy)-6-chloropregna-1,4,6-triene-3,20-dione / 6-chloro-17-hydroxypregna-1,4,6-triene-3,20-dione acetate / 1,6-Bisdehydro-6-chloro-17a-acetoxyprogesterone |
SST0049 | Hideaki Nishino |
DMA |
C23H27O4Cl | 402.911 | |
Preparation method. (Ref. 0303) |
168-170 C. (Ref. 0303) |
[a]/D=-83 (chloroform) (Ref. 0303) |
UVmax (ethanol): 229, 258, 297nm (loge=4.00, 4.00, 4.03). (Ref. 0303) |
Application for regulation of generation in cats and dogs. (Ref. 0306) |
||||||||||||||
| 50 |  |
Diflorason |
6,9-Difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione / 6a,9a-difluoro-16b-methyl-D1,4-pregnadiene-11b,17a,21-triol-3,20-dione / 6a,9a-Difluoro-16b-methylprednisolone |
SST0050 | Hideaki Nishino |
C22H28O5F2 | 410.452 | |
Preparation of free alcohol form and 21-acetate. Decrease of arachidonic acid and hydroxyeicosatetraenoic acid in psoriasis. (Ref. 0309) |
|||||||||||||||||||
| 51 |  |
Difluprednate |
21-(Acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)pregna-1,4-diene-3,20-dione / 6a,9-Difluoro-11b,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate 17-butyrate / 6a,9a-Difluoroprednisolone-21-acetate-17-butyrate |
SST0051 | Hideaki Nishino |
C27H34O7F2 | 508.551 | |
191-194 (methylene chloride/ether/petr. ether) (Ref. 0312) |
[a]22/D=+31.7 (c=0.5 in dioxane).(Ref. 0312) |
UVmax (ethanol): 237-238nm (E1%/1cm 320). (Ref. 0312) |
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| 52 |  |
Digalogenin |
(25R)-5a-Spirostan-3b,15b-diol |
SST0052 | Hideaki Nishino |
C27H44O4 | 432.636 | |
218.5-220.5 C (methanol) (Ref. 0315) |
[a]21/D=-75 (chloroform) (Ref. 0315) |
Sol in chloroform, methanol (Ref. 0315) |
No carbonyl bond. 25a-Sapogenin possessing two hydroxyl groups. (Ref. 0315) |
Isolated from seeds of Digitalis purpurea. (Ref. 0315) |
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| 53 |  |
Diginatigenin |
3b,12b,14,16b-Tetrahydroxy-5b-card-20(22)-enolide / 12-Hydroxygitoxigenin |
SST0053 | Hideaki Nishino |
C23H34O6 | 406.512 | |
[a]20/D=+34 (methanol) (Ref. 0319) |
UVmax (ethanol): 218nm (loge=4.18) (98%w/w sulfate): 230, 310, 390, 490nm (E1%/1cm 160, 130, 210, 85) (Ref. 0319) |
[M]/D=+138 (Ref. 0321) |
Cardiotonic agent (Ref. 0316) |
Strong fluorescence in phosphate, which is a specific reaction to cardiotonic glycosides possessing hydroxyl group at C-16 (Ref. 0316) |
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| 54 |  |
Digitogenin |
(25R)-5a-Spirostan-2a,3b,15b-triol |
SST0054 | Hideaki Nishino |
C27H44O5 | 448.635 | |
280-283 C (Ref. 0327) |
[a]19/D=-81 (c=1.4 in chloroform) (Ref. 0327) |
Insol in water. Sol in 30% chloroform, 35% boiling alcohol, 100% alcohol (20 C). (Ref. 0327) |
lchloroform/max: 2.81, 2.90 (hydroxyl) 10.22, 10.90, 11.14, 11.53m (spiroketal) (Ref. 0327) |
Aglycon of digitonin. (Ref. 0322) |
Exhibits no color reaction even by treatment with conc. sulfate. (Ref. 0327) |
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| 55 |  |
Digitoxigenin |
3,14-Dihydroxycard-20(22)-enolide / D20,22-3,14,21-Trihydroxynorcholenic acid lactone |
SST0055 | Hideaki Nishino |
C23H34O4 | 374.514 | |
Sol in alcohol, chloroform, acetone. Slightly sol in ethylacetate. Very sparingly sol in ether, water. (Ref. 0331) |
Isolation from seeds of Apocinacae. (Ref. 0337) |
Cardiotonic agent. (Ref. 0336) |
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| 56 |  |
Digoxigenin |
3,12,14-Trihydroxycard-20(22)-enolide / D20,22-3b,12b,14,21-Tetrahydroxynorcholenic acid lactone |
SST0056 | Hideaki Nishino |
C23H34O5 | 390.513 | |
Synthesis from deoxycholic acid (Ref. 0346) |
222 C (Ref. 0342) |
[a]20/546=+27.0 (c=1.77 in methanol) (Ref. 0342) |
Aglycon (non-sugar moiety) of digoxin, a cardiac glycoside, from leaves of Digitalis lanata, prepared from hydrolyzate of digixin. (Ref. 0342) |
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| 57 |  |
Dihydroequilin |
Estra-1,3,5(10),7-tetraene-3,17-diol |
SST0057 | Hideaki Nishino |
C18H22O2 | 270.366 | |
Both of 17a- and 17b-forms can be prepared by reduction of equilin, which is found in urine of pregnant mares. (Ref. 0347) |
281 nm (e=1,955) (Ref. 0347) |
In 8-15m, a finger print region, different from a-dihydroequilin. (Ref. 0347) |
Isolation of 17a- and 17b-forms from urine of pregnant mares. (Ref. 0349) |
1/50 activity of estrone. (Ref. 0347) |
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| 58 |  |
Dihydrotachysterol |
9,10-Secoergosta-5,7,22-trien-3b-ol |
SST0058 | Hideaki Nishino |
C28H46O | 398.664 | |
Preparation form reduction of tachysterol (Ref. 0350) |
125-127 C (90% methanol) (Ref. 0350) |
[a]22/D=+97.5 (chloroform) (Ref. 0350) |
Insol in water. Sol in organic solvents. (Ref. 0350) |
UV max: 242, 251, 261nm (E1%/1cm 870, 1010, 650) (Ref. 0350) |
Increase of calcium ion concentration in blood. (Ref. 0350) |
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| 59 |  |
Dinosterol |
4,23-Dimethylergost-22-en-3-ol / 4a-Methyl-5a(H)-D22-23,24-dimethylcholestan-3b-ol |
SST0059 | Hideaki Nishino |
C30H52O | 428.733 | |
Stereospecific synthesis. (Ref. 0354) |
220-222 C (methanol-chloroform) (Ref. 0351) |
100MHz, seven alkyl linked methyl signals (d0.70(3H,s)), 0.80 (3H,d,J=7Hz), 0.84 (3H,s), 0.85 (3H,d,J=7Hz), 0.94 (6H,d,J=6.5Hz, isopropyl), 0.95 (3H,d,J=6Hz), olefinic proton signal (d4.87(1H,q,J=1.2,10Hz)), proton signal due to a secondary alcohol (d3.10(1H,m) |
Determination of structure by X-ray crystallography. (Ref. 0352) |
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| 60 |  |
Diosgenin |
(25R)-Spirost-5-en-3b-ol |
SST0060 | Hideaki Nishino |
C27H42O3 | 414.621 | |
Preparation from yamogenin. Simple stereospecific synthesis. (Ref. 0363) |
[a]25/D=-129 (c=1.4 in chloroform) (Ref. 0358) |
Sol in organic solvents, acetic acid. (Ref. 0355) |
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| 61 |  |
Epicholestenol |
Cholest-5-en-3a-ol |
SST0061 | Hideaki Nishino |
C27H48O | 388.669 | |
141.5 C (alcohol). (Ref. 0364) |
[a]30/D=-35 (c=1 in alcohol). (Ref. 0364) |
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| 62 |  |
16-Epiestriol |
Estra-1,3.5(10)-triene-3,16b,17b-triol / D1,3,5-Estratriene-3,16b,17b-triol |
SST0062 | Hideaki Nishino |
C18H24O3 | 288.381 | |
289-291 C (methanol+benzene). (Ref. 0369) |
[a]15/D=+76 (c=0.297 in ethanol). (Ref. 0369) |
Estrogenic activity. (Ref. 0367) |
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| 63 |  |
Equilenin |
3-Hydroxyestra-1,3,5,7,9-pentaen-17-one / 11,12,13,14,15,16-Hexahydro-3-hydroxy-13-methyl-17H-cyclopenta[a]phenanthren-17-one / 1,3,5:10,6,8-Estra-pentaen-3-ol-17-one |
SST0063 | Hideaki Nishino |
C18H18O2 | 266.334 | |
Total synthesis from 7-methoxy-1-keto-1,2,3,4-tetrahydrophenanthren prepared from 1-naphthylamine-6-sulfonic acid (Cleve's acid). (Ref. 0371/0372/0373) Synthesis from 1-keto-1,2,3,4-tetrahydrophenanthrene. (Ref. 0374) Synthesis from 1-keto-2-methyl-7-methoxy-1,2,3,4-tetrahydrophenanthrene. (Ref. 0375) Synthesis as methyl ether. (Ref. 0376) Synthesis from 1,4,8(9)-trien-11b-olunder acidic condition at room temperature. (Ref. 0095) Synthesis from estra-1,3-5(10),8-tetraenes. (Ref. 0094) Synthesis by coupling of m-methoxystyrene and diazoketone. (Ref. 0377) |
258-259 C (dil. alc.). (Ref. 0371) |
[a]16/D=+87 (12.8mg/1.8ml in dioxane). (Ref. 0371) |
0.63g/100ml alcohol (18 C), 2.5g/100ml alcohol (boiling). (Ref. 0371) |
UVmax (ethanol): 231, 270, 282, 292, 325, 340nm (logEmolar=3.85, 3.87, 3.74, 3.58, 3.68, each) (Ref. 0372) |
Isolationfrom urine of pregnant mares. (Ref. 0371) |
Strong estrogenic acitvity. (Ref. 0371) |
|||||||||||||
| 64 |  |
b-Estradiol / (+)-Estradiol |
Estra-1,3,5-(10)-triene-3,17-diol |
SST0064 | Hideaki Nishino |
C18H24O2 | 272.382 | |
Enantioselective synthesis from 1,3-dihydrobenzo[c] thiophene-2,2-dioxide (Ref. 0107) |
UVmax: 225, 280 nm (Ref. 0379) |
The strongest estrogen in mammals. (Ref. 0103) |
Properties, synthesis, and analysis as valerate. (Ref. 0380) |
||||||||||||||||
| 65 |  |
Estradiol benzoate |
b-Estradiol-3-benzoate |
SST0065 | Hideaki Nishino |
C25H28O3 | 376.488 | |
191-196 C (alcohol). (Ref. 0381) |
[a]25/D=+58 to +63 (c=2 in dioxane). (Ref. 0381) |
Ppt with digitonin. (Ref. 0381) |
|||||||||||||||||
| 66 |  |
Estramustine |
Estra-1,3,5(10)-triene-3,17-diol 3-[bis(2-chloroethyl)carbamate] / Estradiol 3-bis(2-chloroethyl)carbamate / Estra-1,3,5(10)triene-3,17b-diol 3-[N,N-Bis(2-chloroethyl)carbamate] |
SST0066 | Hideaki Nishino |
C23H31O3NCl2 | 440.403 | |
Preparation. (Ref. 0383) |
104-105 C (benzene-petr. ether) (Ref. 0383) |
[a]20/D=+50 (in dioxane) (Ref. 0383) |
UVmax (alcohol): 270.7, 276.5nm (Ref. 0383) |
Anti-tumor drug. (Ref. 0383) |
|||||||||||||||
| 67 |  |
Estrone |
3-Hydroxyestra-1,3,5(10)-trien-17-one / 1,3,5-Estratrien-3-ol-17-one |
SST0067 | Hideaki Nishino |
C18H22O2 | 270.366 | |
[a]22/D=+152 (c=0.995 in chloroform) (Ref. 0123) |
Sol in water (25 ): 0.003g/100ml. Sol in 96% alcohol 250ml, acetone 50ml, chloroform 110ml (1g estrone, 15C). Sol in alcohol 50ml, benzene 145ml (1g estrone, boiling). Sol in dioxane, pyridine, fixed alkali hydroxide. Slightly sol in ether, vegetable oils. (Ref. 0123) |
UVmax: 283-285nm (Ref. 0384) |
Infrared spectra of estrone methyl esters. (Ref. 0385) |
Ppt with digitonin. (Ref. 0123) |
|||||||||||||||
| 68 |  |
Ethinyl estradiol |
19-Nor-17a-pregna-1,3,5(10)-trien-20-yne-3,17-diol / 17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol |
SST0068 | Hideaki Nishino |
C20H24O2 | 296.403 | |
Preparation from estrone. (Ref. 0391) |
145-146 C (Ref. 0391) |
[a]/D=+1 (in dioxan) (Ref. 0391) |
Insol in water. Sol in the proportion of 1: 6 ethanol, 4 ehter, 5 acetone, 4 dioxane, 20 chloroform. Sol in vegetable oils, fixed alkalihydroxides solution. (Ref. 0391) |
UVmax (ethanol): 281nm (e=2040  60) (Ref. 0392) |
NMR spectra. (Ref. 0392) |
Estrogenic activity (application to hormonotherapy for human and animals). (Ref. 0391) |
Properties (Ref. 0392) |
||||||||||||
| 69 |  |
Ethisterone |
17a-Hydroxypregn-4-en-20-yn-3-one / 17a-Ethynyltestosterone / 17a-Ethynyl-17b-hydroxy-4-androsten-3-one / 17a-Ethinyltestosterone / 17a-Ethynyl-4-androsten-17b-ol-3-one |
SST0069 | Hideaki Nishino |
C21H28O2 | 312.446 | |
Preparation by addition of acetylene to dehydroepiandrosterone, followed by Oppenauer oxidation. (Ref. 0391) |
269-275 C (Ref. 0391) |
Insol in water. Slightly sol in alcohol, acetone, ether, chloroform, vegetable oils. (Ref. 0391) |
UVmax (methanol): 241nm (E1%/1cm 513) (Ref. 0391) |
||||||||||||||||
| 70 |  |
Ethynodiol |
19-Nor-pregn-4-en-20-yne-3,17-diol / 17a-Ethynyl-19-norandrost-4-ene-3b,17b-diol / 17a-Ethynyl-4-estrene-3b,17b-diol |
SST0070 | Hideaki Nishino |
ED |
C20H28O2 | 300.435 | |
147-149 C (Ref. 0393) |
[a]/D=-39 (EtOH) (Ref. 0393) |
Sol in alcohol.(Ref. 0393) |
Particularly no strong absorbance. (Ref. 0393) |
nKBr/max 3300/cm (Ref. 0393) |
Progesterone activity. (Ref. 0393) |
|||||||||||||
| 71 |  |
Fucosterol |
Stigmasta-5,24(28)-dien-3-ol |
SST0071 | Hideaki Nishino |
C29H48O | 412.691 | |
Synthesis from 3b-hydroxy-20-iso-D5-cholenic acid (Ref. 0397) |
124 C (methanol). (Ref. 0394) |
220-230 C/0.2mm.(Ref. 0394) |
[a]20/D=-38.42 (c=5 in chloroform). (Ref. 0394) |
Sol in almost all organic solvents. (Ref. 0394) |
GLC. (Ref. 0140) |
||||||||||||||
| 72 |  |
Funtumine |
3-Amino-5-pregnan-20-one / 3a-Amino-20-oxo-5a-pregnane |
SST0072 | Hideaki Nishino |
C21H35ON | 317.509 | |
126 C (ethyl acetate). (Ref. 0401) |
[a]/D=+95 (c=1.7, chloroform). (Ref. 0401) |
Effective on liver cancer. (Ref. 0401) |
|||||||||||||||||
| 73 |  |
Gamabufotalin |
3b,11a,14-Trihydroxy-5b-bufa-20,22-dienolide |
SST0073 | Hideaki Nishino |
C24H34O5 | 402.524 | |
254 C (alcohol+ether). (Ref. 0404) |
[a]18/D=+1.26 (c=0.793 in methanol). (Ref. 0404) |
Very sparingly sol in chloroform, acetone, water. Somewhat more sol in methanol. (Ref. 0404) |
UVmax about 300nm. (Ref. 0404) |
Digitalis-like activity. (Ref. 0406) |
|||||||||||||||
| 74 |  |
Gentrogenin / Botogenin |
(25R)-3b-Hydroxyspirost-5-en-12-one / 20a,22A,25D-Spirost-5-en-3b-ol-12-one |
SST0074 | Hideaki Nishino |
C27H40O4 | 428.604 | |
Precursor for synthesis of pharmaceutically-active steroid. (Ref. 0407) |
215-216 C (methanol) (Ref. 0407) |
[a]28/D=-56 (c=1.02 in chloroform). (Ref. 0407) |
|||||||||||||||||
| 75 |  |
Gitogenin / Digin |
(25R)-5a-Spirostan-2a,3b-diol |
SST0075 | Hideaki Nishino |
C27H44O4 | 432.636 | |
266-268 C (Ref. 0411) |
[a]20/D=-75 (c=1.02in chloroform) (Ref. 0414) |
Sol in chloroform, hot alcohol. Sparingly sol in cold ethylacetate, ether. Insol in water. (Ref. 0414) |
General absorption at aroud 230-320nm (Ref. 0414) |
Cardiotonic agent. (Ref. 0410) |
|||||||||||||||
| 76 |  |
Gitoxigenin |
3b,14,16b-Trihydroxy-5b-card-20(22)-enolide / D20.22-3,14,16,21-Tetrahydroxynorcholenic acid lactone. |
SST0076 | Hideaki Nishino |
C23H34O5 | 390.513 | |
234 C (Ref. 0416) |
[a]20/545=+38.5 (c=0.68 in methanol). (Ref. 0415) |
max (96% sulfate): 310, 485, 520nm (Ref. 0416) |
Cardiotonic action. (Ref. 0417) |
||||||||||||||||
| 77 |  |
Gratiogenin |
20,24-Epoxy-3,25-dihydroxy-9-methyl-19-nor-9b-lanost-5-en-11-one |
SST0077 | Hideaki Nishino |
C30H48O4 | 472.700 | |
UVmax: 290mm (loge=2.0) (EtOH). (Ref. 0418) |
3620, 3588, 1691/cm (Ref. 0419) |
m/e = 105, 109, 119, 127, 135, 143, 172, 173, 175, 192, 309, 327, 371, 413, 439, 454, 472. (Ref. 0419) |
CD(c=0.69 g/l): l(De)=340(O), 317(+3.65, inflexion), 305(+5.60, plateau), 298(+5.80), 240mm(O). (Ref. 0419) |
||||||||||||||||
| 78 |  |
Hecogenin |
(25R)-3b-Hydroxy-5a-spirostan-12-one |
SST0078 | Hideaki Nishino |
C27H42O4 | 430.620 | |
Conversion of isoandrosterone to mixture consisting of tigogenin and neotigogenin via 18 steps, further conversion to steroidal sapogenin such as hecogenin (Ref. 0358) |
264-266 C (Ref. 0358) |
[a]/D=+8 (chloroform) (Ref. 0358) |
Sol in ether, ethylacetate, benzene, acetone. (Ref. 0358) |
||||||||||||||||
| 79 |  |
Hexahydroequilenin |
Estra-5,7,9-triene-3b,17b-diol |
SST0079 | Hideaki Nishino |
C18H24O2 | 272.382 | |
168-168.5 C (Ref. 0420) |
High estrogenic activity (rat). (Ref. 0420) |
||||||||||||||||||
| 80 |  |
24-Hydroxycholesterol |
Cholest-5-ene-3b,24-diol |
SST0080 | Hideaki Nishino |
C27H46O2 | 402.653 | |
||||||||||||||||||||
| 81 |  |
25-Hydroxycholesterol |
Cholest-5-ene-3,25-diol / D5-Cholestene-3b,25-diol |
SST0081 | Hideaki Nishino |
C27H46O2 | 402.653 | |
Preparation by treatment of 3b-acetoxy-5-cholestene-25-one with methylmagnesium. (Ref. 0425/0426) Not product of biogenesis, but oxidation of cholesterol in the air. (Ref. 0422) Efficient and simple synthesis. Regioselective protocol without forming 24-hydroxyisomer. (Ref. 0433) Synthesis of 25-hydroxycholesteryl 3b-acetate by UV-irradiation of 3b-acetoxycholestane. (Ref. 0434) Generally available synthesis method from pregnenolone and the acetate (Ref. 0428) Synthesis from 2-lithiodithian (Ref. 0428)Synthesis from stigmasterol (Ref. 0432) Synthesis from 5b-cholestan-3a,25-diol derived from lithocholic acid. (Ref. 0435) Synthesis by using (h3-allyl)palladium. (Ref. 0429) |
(CDCl3) d 5.33(m, H-6); 3.48(m, -CH-O); 1.19(s,H3C-C(26) and H3C-C(27)); 1.00(s,H3C-C(19)); 0.92(d,J=7Hz,CH3); 0.67(s,H3C-C(18)). |
Contamination as a trace component in cholesterol preparation. (Ref. 0422) |
|||||||||||||||||
| 82 |  |
Isoestradiol / 8a-Estradiol / 8-Epiestradiol / 8-Isoestradiol-17b |
8a-Estra-1,3,5(10)-triene-3,17b-diol / D1.3.5-8a-Epiestratriene-3,17b-diol |
SST0082 | Hideaki Nishino |
C18H24O2 | 272.382 | |
Sol in methanol, chloroform.(Ref. 0086) |
|||||||||||||||||||
| 83 |  |
9b-Ergosterol / Isopyrocalciferol |
9b-Ergosta-5,7,22-trien-3b-ol |
SST0083 | Hideaki Nishino |
C28H44O | 396.648 | |
112-115 C (ether-methanol) (Ref. 0437) |
Sol in chloroform (Ref. 0437) |
UV max: 262, 280nm. (Ref. 0437) |
One of ergosterol stereoisomers. Ppt with digitonin. (Ref. 0437) |
||||||||||||||||
| 84 |  |
Isorubijervine / 18-Hydroxysolanidine |
Solanid-5-ene-3b,18-diol |
SST0084 | Hideaki Nishino |
C27H43O2N | 413.636 | |
[a]25/D=+6.5 (c=0.97 in abs. ethanol). (Ref. 0438) |
|||||||||||||||||||
| 85 |  |
Methandriol |
17a-Methyl-5-androstene-3b,17b-diol |
SST0085 | Hideaki Nishino |
MAD |
C20H32O2 | 304.467 | |
max. mm (E1%/1cm): 235(141), 309(155), 355(136), 390(168)[I], 438(373), 497(209). min. mm(E1%/1cm): 226(136), 258(105), 335(123), 372(123), 478(145). (Ref. 0446) |
1.08(C18), 1.08(C19), 2.55(M,C4), 5.39(M,C6), 1.38(C20). (Ref. 0447) |
Function as an anabolic steroid.(Ref. 0444) |
||||||||||||||||
| 86 |  |
Methandrostenolone |
17b-Hydroxy-17-methylandrosta-1,4-dien-3-one / 17a-Methyl-17b-hydroxyandrosta-1,4-dien-3-one / 1-Dehydro-17a-methyltestosterone |
SST0086 | Hideaki Nishino |
C20H28O2 | 300.435 | |
163-164 C (acetone+ether). (Ref. 0448) |
[a]26/D=0 (c=1.150 in chloroform). (Ref. 0448) |
Sol in chloroform. (Ref. 0448) |
UVmax: 245nm (e=15,600). (Ref. 0448) |
In methylenechloride: 2.74m, 5.98m, 6.14m, 6.21m, 7.29m, 7.52m, 8.86m, 9.23m, 10.68m, 10.83m, 11.28m, 12.23m. (Ref. 0448) |
M/D+356 (dioxan). (Ref. 0448) |
Anabolic action (androgen activity). (Ref. 0448) |
|||||||||||||
| 87 |  |
Moxestrol |
11b-Methoxy-19-nor-17a-pregna-1,3,5(10)-trien-20-yne-3,17-diol / 3,17-Dihydroxy-11b-methoxy-19-nor-17a-pregna-1,3,5-trien-20-yne / 17a-Ethynyl-11b-methoxyestra-1,3,5(10)-triene-3,17b-diol / 11b-Methoxy-17a-ethynyl-D1,3,5(10)-estratriene-3,17b-diol / 11b-methoxy-17a-ethynylestradiol |
SST0087 | Hideaki Nishino |
C21H26O3 | 326.429 | |
Preparation. (Ref. 0450) |
280 C. (Ref. 0450) |
[a]20/D=+29 (c=0.6 in EtOH). (Ref. 0450) |
UVmax (ethanol): 280nm (e1%/1cm=58.4) (Ref. 0450) |
Estrogenic acitivity. (Ref. 0450) |
|||||||||||||||
| 88 |  |
Neoergosterol |
19-Norergosta-5,7,9,22-tetraen-3b-ol |
SST0088 | Hideaki Nishino |
C27H40O1 | 380.606 | |
[a]17/D=-11 (c=2 in chloroform). (Ref. 0451) |
Absorption maximum at around 265-270nm (ether). (Ref. 0451) |
nCS2max: 3600/cm (hydroxy), 970/cm (side chain double bond), 809/cm (aromatic ring). (Ref. 0453) |
|||||||||||||||||
| 89 |  |
Ouabagenin / G-Strophanthidin |
1b,3b,5,11a,14,19-Hexahydroxy-5b-card-20(22)-enolide |
SST0089 | Hideaki Nishino |
C23H34O8 | 438.511 | |
Preparation by HCl-treatment of ouabain in acetone. (Ref. 0262) |
+0.288 (Ref. 0262) |
[a]17/D=+11.32 (c=1.27). (Ref. 0262) |
Sol in boiling water (1g/10ml, less than 1% solubility at room temperature). Also sol in dil. alcohol. Insol in alcohol anhydride. (Ref. 0262) |
Isolation from ouabain, a glycoside from Strophanthus gratus. (Ref. 0262) |
LD50 (cat), mean systolic dose in frog. (Ref. 0455) |
Evidence for steroid structure of ouabagenin. (Ref. 0456) |
|||||||||||||
| 90 |  |
Periplogenin / 19-Desoxostrophanthidine |
3b,5,14-Trihydroxy-5b-card-20(22)-enolide |
SST0090 | Hideaki Nishino |
C23H34O5 | 390.513 | |
Found in the bark and wood of Periploca graece. (Ref. 0457) Found in Strophanthus eminii Asch et Pax. Apocynaceae. (Ref. 0458) In several species of Strophanthus genus. (Ref. 0461) Isolation accompanied in preparation of strophanthidine from Strophanthus eminii Asch. Et Pax., Apocynaceae. (Ref. 0457) Yielding of periplobiose (C13H24O9) and periplogenin (C23H34O5) in hydrolysis of periplocin. (Ref. 0457) |
|||||||||||||||||||
| 91 |  |
Prednisolone / Meticortelone |
11,17,21-Trihydroxypregna-1,4-diene-3,20-dione / 1,4-Pregnadiene-3,20-dione-11b,17a,21-triol / 1,4-Pregnadien-11b,17a,21-triol-3,20-dione / 3,20-Dioxo-11b,17a,21-trihydroxy-1,4-pregnadiene |
SST0091 | Hideaki Nishino |
C21H28O5 | 360.444 | |
Sparingly sol in water. Sol 1g in 30ml alcohol, 180ml chloroform, 50ml acetone, methanol, dioxane. (Ref. 0465) |
Biosynthesis from cortisol by Corynebacterium simplex. (Ref. 0465) |
More effective than natural corticosteroid as inflammatory drug. (Ref. 0465) Glucocorticoid stronger 3-4 times than natural cortisone, hydrocortisone in eosinopenic response and liver glycogen storage in adrenalectomized mice, thymus degeneration in untreated mice. |
|||||||||||||||||
| 92 |  |
Prednisone / Meticorten |
17,21-Dihydroxypregna-1,4-diene-3,11,20-trione / 1,4-Pregnadiene-17a,21-diol-3,11,20-trione |
SST0092 | Hideaki Nishino |
C21H26O5 | 358.428 | |
Synthesis from cortisone with Corynebacterium simplex. (Ref. 0465) |
Very sparingly sol in water. Sol 1g in 150ml alcohol, 200ml chloroform. Slightly sol in methanol, dioxane. (Ref. 0465) |
Anti-inflammatory action. (Ref. 0465) More efficient rather than natural corticosteroid. 3-4 Times stronger glucocorticoid than natural cortisone, hydrocortisone in eosinopenic response and liver glycogen storage in adrenalectomized mice, thymus degeneration in untreated mice. |
|||||||||||||||||
| 93 |  |
Prednival |
11,21-Dihydroxy-17-[(1-oxopentyl)-oxy]pregna-1,4-diene-3,20-dione / 11b,17,21-Trihydroxypregna-1,4-diene-3,20-dione 17-valerate / Prednisolone 17-valerate |
SST0093 | Hideaki Nishino |
C26H36O6 | 444.560 | |
Preparation from 17a,21-cyclic orthoesters. (Ref. 0466) |
210-213 C (methanol). (Ref. 0466) |
[a]/D=+3.5 (dioxane). (Ref. 0466) |
Glucocorticoid. (Ref. 0466) |
||||||||||||||||
| 94 |  |
Lumisterol |
9b,10a-Ergosta-5,7,22-trien-3b-ol |
SST0094 | Hideaki Nishino |
C28H44O | 396.648 | |
Preparation by UV-irradiation of ergosterol suspended in benzene-alcohol solution. (Ref. 0437) |
118 C (Ref. 0437) |
Insol in water. Sol in organic solvents. (Ref. 0437) |
|||||||||||||||||
| 95 |  |
Pregnane |
5b-Pregnane / 17b-Ethyletiocholane |
SST0095 | Hideaki Nishino |
C21H36 | 288.511 | |
83.5 C (methanol). (Ref. 0470) |
Sol in chloroform, methanol. (Ref. 0470) |
Isolation from urine of pregnant women. (Ref. 0470) |
Androgenic activity. (Ref. 0470) |
||||||||||||||||
| 96 |  |
Pregnanediol |
(3a,5b,20S)-Pregnane-3,20-diol |
SST0096 | Hideaki Nishino |
C21H36O2 | 320.509 | |
239 C (acetone or ethanol). (Ref. 0472) |
[a]20/D=+27.4 (c=0.7 in alcohol). (Ref. 0472) |
Sparingly sol in organic solvents. (Ref. 0472) |
|||||||||||||||||
| 97 |  |
3,20-Pregnanedione |
SST0097 | Hideaki Nishino |
C21H32O2 | 316.478 | |
Preparation from 4,11-pregnadien-3,20-dione. (Ref. 0476) |
123 C (Ref. 0474) |
Insol in water. Sol in organic solvents. (Ref. 0474) |
||||||||||||||||||
| 98 |  |
3a-Hydroxy-5b-pregnan-20-one / Pregnan-3a-ol-20-one |
SST0098 | Hideaki Nishino |
C21H34O2 | 318.493 | |
Preparation by hydrolysis of sodium pregnanediol glucuronidate. (Ref. 0478) |
In urine of pregnant women, pregnant hogs. (Ref. 0477) |
Not ppt with digitonin. (Ref. 0477) |
||||||||||||||||||
| 99 |  |
Pregnan-3b-ol-20-one |
3b-Hydroxy-5b-pregnan-20-one |
SST0099 | Hideaki Nishino |
C21H34O2 | 318.493 | |
149 C (dil.alcohol). (Ref. 0479) |
Sol in ether. (Ref. 0479) |
||||||||||||||||||
| 100 |  |
Pregnan-20a-ol-3-one |
20a-Hydroxy-5b-pregnan-3-one |
SST0100 | Hideaki Nishino |
C21H34O2 | 318.493 | |
Preparation from pregnanolon-acetate. (Ref. 0480) |
152 C (acetone) (Ref. 0480) |
Androgenic acitvity. (Ref. 0481) |
|||||||||||||||||
| 101 |  |
20b-Hydroxy-5b-pregnan-3-one / Pregnan-20b-ol-3-one |
SST0101 | Hideaki Nishino |
C21H34O2 | 318.493 | |
Yielded by acetylation, partial saponification, oxidation, and hydrolysis of pregnandiol-3(b),20(b), which is synthesized from pregnandiol-3(a),20(a). (Ref. 0481) |
172 C (dil. acetone) (Ref. 0481) |
Sol in methanol. (Ref. 0481) |
Found in urine of pregnant women. (Ref. 0481) |
High androgenic activity. (Ref. 0481) |
||||||||||||||||
| 102 |  |
Substanz T |
20,21-Dihydroxypregn-4-ene-3,11-dione / 4-Pregnene-20,21-diol-3,11-dione |
SST0102 | Hideaki Nishino |
C21H30O4 | 346.460 | |
About 210 C. (Ref. 0482) |
[a]20/D=+176 (acetone). (Ref. 0482) |
240 mm (loge=about 4.2), because of keto-group. (Ref. 0482) |
Found in adrenal glands. (Ref. 0482) |
||||||||||||||||
| 103 |  |
11b,17,20b,21-Tetrahydroxypregn-4-en-3-one / 17-(1,2-Dihydroxyethyl)androsten-3-one-11,17-diol / 4-Pregnene-11b,17a,20b,21-tetrol-3-one /4-Pregnane-11b,17a,20b,21-tetrol-3-one |
SST0103 | Hideaki Nishino |
C21H32O5 | 364.476 | |
UVmax: 240nm (Ref. 0483) |
||||||||||||||||||||
| 104 |  |
17,20,21-Trihydroxypregn-4-ene-3,11-dione / 4-Pregnene-17a,20b,21-triol-3,11-dione |
SST0104 | Hideaki Nishino |
C21H30O5 | 362.460 | |
208-209 C (acetone+ether) (Ref. 0485) |
In adrenal glands. (Ref. 0485) |
|||||||||||||||||||
| 105 |  |
17a-Pregnenetriolone |
17a,20b,21-trihydroxypregn-4-en-3-one / 17-(1,2-Dihydroxyethyl)-D4-androsten-3-on-17a-ol / 4-Pregnen-17a,20b,21-triol-3-one |
SST0105 | Hideaki Nishino |
C21H32O4 | 348.476 | |
Synthesis from 17-ethynyltestosterone. (Ref. 0486) |
190 C (methanol) (Ref. 0486) |
[a]/D=+63 (c=1 in dioxane) (Ref. 0486) |
Sol in dioxane, chloroform, methanol. (Ref. 0486) |
UVmax: 240nm (loge=4.1) (Ref. 0486) |
|||||||||||||||
| 106 |  |
Pregnenolone methyl ether |
3b-Methoxypregn-5-en-20-one. |
SST0106 | Hideaki Nishino |
C22H34O2 | 330.504 | |
+0.19(5) (Ref. 0487) |
[a]18/D=+18 (c=1.085 in chloroform) (Ref. 0487) |
Sol in methanol, chloroform. (Ref. 0487) |
Anti-inflammatory action. (Ref. 0488) |
||||||||||||||||
| 107 |  |
Pseudohecogenin / 4-Hecogenin |
3b,26-Dihydroxy-5a-furost-20(22)-en-12-one |
SST0107 | Hideaki Nishino |
C27H42O4 | 430.620 | |
Preparation by hydrolysis of hecogenin. (Ref. 0357) |
190-191 C (Ref. 0490) |
UVmax (ethanol): 213nm (e=6,400) (Ref. 0490) |
nNIJOL/max: 3320 (hydroxy), 1706 (ketone), 1688/cm (vinyl ether). (Ref. 0490) |
||||||||||||||||
| 108 |  |
Pyrocalciferol / 9a-Lumisterol |
10a-Ergosta-5,7,22-trien-3b-ol / 9a-Lumista-5,7,22-trien-3b-ol |
SST0108 | Hideaki Nishino |
C28H44O | 396.648 | |
93-95 C (Ref. 0491) |
Sol in alcohol. (Ref. 0491) |
274, 294mm (Ref. 0491) |
Distribution (Ref. 0437) |
Different configuration at C-9 and C-10 from ergosterol. (Ref. 0437) |
|||||||||||||||
| 109 |  |
Rubijervine / Rubigervine |
D5-3b-12a-Dihydroxysolanidene / Solanid-5-ene-3b,12a-diol |
SST0109 | Hideaki Nishino |
C27H43O2N | 413.636 | |
240-246 C (Ref. 0493) |
[a]25/D=+19.0 (c=1 ethanol) (Ref. 0493) |
Sparingly sol in water. Sol in ethanol, methanol, benzene, chloroform. Slightly sol in ether, petroleum ether. (Ref. 0493) |
1048, 1028, 1016, 1003/cm, strongest at 1048. (Ref. 0495) |
X-ray analysis of structure. (Ref. 0442) |
Isolation from various species from Veratrum, Liliaceae. (Ref. 0493) |
||||||||||||||
| 110 |  |
Ruscogenin / Ruscorectal |
(25R)-Spirost-5-ene-1b,3b-diol |
SST0110 | Hideaki Nishino |
C27H42O4 | 430.620 | |
n max: 898, 922/cm (same strength). (Ref. 0497) |
Application for therapy of hemorroids. (Ref. 0497) |
||||||||||||||||||
| 111 |  |
Sarmentogenin |
3b,11a,14-Trihydroxy-5b-card-20(22)-enolide |
SST0111 | Hideaki Nishino |
C23H34O5 | 390.513 | |
||||||||||||||||||||
| 112 |  |
Sarsasapogenin / Parigenin |
(25S)-Spirostan-3b-ol |
SST0112 | Hideaki Nishino |
C27H44O3 | 416.636 | |
199-199.5 (Ref. 0502) |
Sol in alcohol, acetone, benzene, chloroform. (Ref. 0502) |
(Asym.-CH2-), 2910, 2873 (Sym.-CH3), 2864 (Sym.-CH3), 2935. (as acetate) (Ref. 0509) |
326 c.p.s (C-19 methyl-group), 338 c.p.s (C-18 methyl-group), 321-326 c.p.s. (C-21,C-27 methyl-group) (Ref. 0508) |
||||||||||||||||
| 113 |  |
Sarverogenin |
7b,8-Epoxy-3b,11a,14-trihydroxy-12-oxo-5b-card-20(22)-enolide |
SST0113 | Hideaki Nishino |
C23H30O7 | 418.480 | |
Sol in water, methanol, chloroform. (Ref. 0510) |
UVmax: 218, 277.5nm (loge=4.2, 1.83) (Ref. 0511) |
886-777/cm (7.8-epoxy 14b-hydroxyl) (Ref. 0513) |
d5.03(C-3),d5.63(11b-proton),d3.93,d3.43,d3.20,d2.83,d2.6,d1.31, d1.13,d1.08,d1.06. (Ref. 0514) |
M=418; 400[M-18]; 382[400-18]; 372[400-28(CO)]; 364[382-18]; 354[372-18, or 382-28(CO)]; 339[354-15(CH3)] (Ref. 0513) |
|||||||||||||||
| 114 |  |
Scillarenin |
3b,14-Dihydroxybufa-4,20,22-trienolide |
SST0114 | Hideaki Nishino |
C24H32O4 | 384.508 | |
Presentation of IR spectra as the acetate. (Ref. 0519) |
|||||||||||||||||||
| 115 |  |
Scilliroside |
6b-(Acetyloxy)-3b-(b-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide |
SST0115 | Hideaki Nishino |
C32H44O12 | 620.685 | |
168-170 (hemihydrate) (Ref. 0521) |
[a]20/D=-59 to 60 (methanol, c=1) (Ref. 0521) |
Sol in lower alcohol, ethylene glycol, dioxane, glacial acetic acid. Slightly sol in water, acetone, chloroform, ethyl acetate. Insol in ether, petroleum ether. (Ref. 0521) |
lmax: 300nm (loge=3.73, 96% ethanol), 295, 505nm (E1%/1cm 260, 315, 98% sulfate) (Ref. 0521) |
Found in Urginea maritima (L.) Baker, Liliaceae, originated from the shore areas of the Mediterranean Sea (the bulbs had ever been utilized as cardiotonic drugs or diuretic agents). (Ref. 0521) |
Revised structure. (Ref. 0522) |
||||||||||||||
| 116 |  |
a1-Sitosterol / Citrostadienol / 24-Ethylidene-lophenol |
4-Methylstigmasta-7,24(28)-dien-3-ol |
SST0116 | Hideaki Nishino |
C30H50O | 426.717 | |
209mm (e=5,500) (Ref. 0137) |
Ppt with digitonin. (Ref. 0139) |
||||||||||||||||||
| 117 |  |
Solanidine / Solatubine |
Solanid-5-en-3b-ol |
SST0117 | Hideaki Nishino |
C27H43ON | 397.636 | |
Presence as an aglycon of solanine derived from Solanum tuberosum (potato), S. nigrum (woody-night-shade), S. lycopersicum (tomato). (Ref. 0525) |
Function as an aglycon of solanine, a species of alkaloids.(Ref. 0525) |
||||||||||||||||||
| 118 |  |
Solanocapsine / Solanocapsin |
3-Amino-16,23-epoxy-16,28-seco-solanidan-23-ol / 3b-Amino-22,26-imino-16b,23-oxido-5a,22a,23b,25a-cholestan-23-ol / 3b-Amino-22,26-imino-16b,23-oxido-5a,22R,23S,25R-cholestan-23-ol |
SST0118 | Hideaki Nishino |
C27H46O2N2 | 430.666 | |
213-215 (monohydrate) (Ref. 0531) |
(chloroform) 3587, 3355 (NH-atomic rotation-vibration), 3305, 1280, 1245, 1218, 1205, 1160, 1140, 1113, 1096, 1078, 1057, 1040, 1018, 1008, 965, 950, 926, 908, 880, 870, 800, 767, 698/cm (Ref. 0531) |
Function as an alkaloid. (Ref. 0530) |
|||||||||||||||||
| 119 |  |
Solasodine / Solancarpidine / Solanidine-s / Purapuridine |
Spirosol-5-en-3b-ol / Solasod-5-en-3b-ol / D5-20bF,22aF,27-Azaspirosten-3b-ol / 3b-Hydroxy-22(27)-imino-25a-5-furostene |
SST0119 | Hideaki Nishino |
C27H43O2N | 413.636 | |
10.3, 10.4, 11.2, 11.5m (azaoxaspirane bands) (Ref. 0536) |
Function as an alkaloid. (Ref. 0535) |
Strating material for synthesis of steroidal agents. (Ref. 0536) |
|||||||||||||||||
| 120 |  |
a-Spinasterol / a-Spinasterin / Bessisterol / Hitodesterol |
Stigmasta-7,22-dien-3-ol |
SST0120 | Hideaki Nishino |
C29H48O | 412.691 | |
Synthesis from 7-dehydrostigmasteryl benzoate. (Ref. 0541) |
Needed for growth of fruit-fly, Drosophila. (Ref. 0542) |
Ppt with digitonin. (Ref. 0539) |
|||||||||||||||||
| 121 |  |
Spironolactone |
7-(Acetylthio)-17-hydroxy-3-oxo-pregn-4-ene-21-carboxylic acid g-lactone / 17-Hydroxy-7-mercapto-3-oxo-17a-pregn-4-ene-21-carboxylic acid g-lactone,7-acetate / 3-(3-Oxo-7a-acetylthio-17b-hydroxy-4-androsten-17a-yl) propionic acid g-lactone |
SST0121 | Hideaki Nishino |
C24H32O4S | 416.574 | |
Preparation. (Ref. 0543) |
134-135 (methanol) (Ref. 0543) |
[a]20/D=-33.5 (chloroform) (Ref. 0543) |
Insol in water. Sol in organic solvents. (Ref. 0543) |
UVmax: 238nm (e=20,200) (Ref. 0543) |
8.78 p.p.m (C10-CH3) (Ref. 0544) |
Rotatory dispertion curve: [f]=-2540, l=345mm. (Ref. 0544) |
|||||||||||||
| 122 |  |
Squalene / Spinacene / Supraene |
2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene |
SST0122 | Hideaki Nishino |
C30H50 | 410.718 | |
Synthesis using geraniol. (Ref. 0553) Stereoisomer-specific synthesis. (all-trans-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene). (Ref. 0554/0556) Synthesis from 2-farnesylthiothiazoline. (Ref. 0557) Application of general synthetic method of 1,5-diene. (Ref. 0558) Synthesis of trans-cis-trans-trans isomer, and preparation of tritium-labeled squalene. (Ref. 0559) |
about -75 (Ref. 0547) |
n20/D=1.4965 (Ref. 0547) |
Insol in water. Sol in ether, petroleum ether, carbon tetrachloride, acetone. Sparingly sol in glacial acetic acid, alcohol. (Ref. 0547) |
Comparison between natural and synthetic compounds. Identification of characteristic peaks at around 9-11m,12m (Ref. 0553) |
Molar refraction 139.6, 139.8, 139.9 (Ref. 0547) |
Intermediate in cholesterol biosynthesis. (Ref. 0554) |
Sterilizer. (Ref. 0547) |
Somewhat stinks in oily state. (Ref. 0547) 12cps.viscosity at 25 C. (Ref. 0547) The flashing point, about 200C. (Ref. 0547) Intermediate for synthesis of drugs. (Ref. 0547) Intermediate for organic pigments, synthetic rubber, aroma, surfactants. (Ref. 0551/0552) Iodine value 377.6 (Ref. 0547) Occupied 50-80% of liver oil. (Ref. 0547) Crystal structure (Ref. 0555) |
|||||||||||
| 123 |  |
Stigmastanol / b-Sitostanol / Fucostanol |
Dihydro-b-sitosterol |
SST0123 | Hideaki Nishino |
C29H52O | 416.723 | |
[a]20/D=+25 (c=1.1 in chloroform) (Ref. 0147) |
Sol in methanol, chloroform. (Ref. 0147) |
||||||||||||||||||
| 124 |  |
Stigmasterol |
Stigmasta-5,22-dien-3b-ol / 3b-Hydroxy-24-ethyl-D5,22-cholestadiene |
SST0124 | Hideaki Nishino |
C29H48O | 412.691 | |
170 (Ref. 0176) |
[a]22/D=-51 (c=2 in chloroform) (Ref. 0176) |
Insol in water. Sol in organic solvents. (Ref. 0176) |
Isolation from phytosterols mixture extracted from soy or calabar beans. (Ref. 0176) |
Anti-rigidity factor. (Ref. 0176) |
|||||||||||||||
| 125 |  |
Tanghinigenin |
7b,8-Epoxy-3b,14-dihydroxy-5b-card-20(22)-enolide |
SST0125 | Hideaki Nishino |
C23H32O5 | 388.497 | |
187-188 C (aceton+petroleum ether) (Ref. 0561) |
[a]25/D=+14.1 (c=1.138 in chloroform) (Ref. 0561) |
UVmax: 217nm (loge=4.22, chloroform) (Ref. 0561) |
11.29-11.39m and 12.81-12.87m KBr two bands-derived structure (Ref. 0562) |
NMR spectra of 3-O-acetyl-tanghinigenin. (Ref. 0562) |
|||||||||||||||
| 126 |  |
Tetrahydrocortisone |
3a,17a,21-Trihydroxy-5b-pregnane-11,20-dione / 3a,17a,21-Pregnanetriol-11,20-dione / 11,20-Pregnanedione-3a,17a,21-triol |
SST0126 | Hideaki Nishino |
THE |
C21H32O5 | 364.476 | |
190 C (anhyd. ethanol) (Ref. 0564) |
[a]25/D=+85.0 (c=1.0 in 100% ethanol) (Ref. 0564) |
Sol in alcohol, ethylacetate. (Ref. 0564) |
Characteristic band at 1041/cm. (Ref. 0564) |
|||||||||||||||
| 127 |  |
Adonitoxin / Adovern |
3b-[(6-Deoxy-a-L-mannopyranosyl)-oxy]-14,16b-dihydroxy-19-oxo-5b-card-20(22)-enoride |
SST0127 | Hideaki Nishino |
C29H42O10 | 550.638 | |
238-240 C (Ref. 0566) |
1640, 1756, 1726/cm (Ref. 0566) |
||||||||||||||||||
| 128 |  |
Adrenosterone / Reichstein's Substance G |
Androst-4-ene-3,11,17-trione |
SST0128 | Hideaki Nishino |
C19H24O3 | 300.392 | |
220-224bC (alcohol) (Ref. 0483) |
UVmax: 235nm (Ref. 0483) |
Crystallographic analysis. (Ref. 0569) |
Metabolism of adrenosterone-1,2-3H in control and hypothyroid patients. (Ref. 0570) |
||||||||||||||||
| 129 |  |
Aldosterone / Elektrocortin / Electrocortin / Aldocortin |
11b,21-Dihydroxy-3,20-dioxopregn-4-en-18-ol; 3,20-Diketo-11b,18-oxido-4-pregnene-18,21-diol |
SST0129 | Hideaki Nishino |
C21H28O5 | 360.444 | |
UVmax: 240nm (loge=4.20 for the monohydrate; e mol 15,000 for the anhydr.) (Ref. 0574) |
Hydroxyl band at 2.92m, D4-3-keto band at 6.05 and 6.18m, saturated carbonyl at 5.87m. (Ref. 0574) |
Adrenocortical steroid regulates matabolism of electrolyte and water. Synthesized in zona glomerulosa, transported by albumin. Secreted 400mg/day in human male adult. The secretion is influenced by ACTH, GH, plasma sodium/potassium ions, and renin-angiotensin system, which induces resorbing of sodium, chloride, bicarbonate ions and potassium ion from uresis. Activity can be detected at the dose of 0.05-0.01mg in rat urinary sodium retention assay. 16mg Desoxycorticosterone acetate must be needed to retain the same activity. (Ref. 0579) |
|||||||||||||||||
| 130 |  |
Alfadolone acetate / Alphadolone acetate / GR 2/1574 |
3a,21-Dihydroxy-5a-pregnane-11,20-dione 21-acetate / 21-Acetoxy-3a-hydroxy-5a-pregnane-11,20-dione |
SST0130 | Hideaki Nishino |
C23H34O5 | 390.513 | |
Preparation from 5a-androstane-3,17-dione. (Ref. 0580) |
175-177 (acetone-hexane) (Ref. 0580) |
[a]26/D=+97 (c=1.02 in chloroform) (Ref. 0580) |
nmax(Nujol) 3500, 1755, 1718, 1200/cm. (Ref. 0580) |
Constituent of anesthetic. (Ref. 0580) |
Strong positive in blue-tetrazolium reaction. (Ref. 0580) |
||||||||||||||
| 131 |  |
Alfaxalone / Alphaxalone / GR 2/234 |
3a-Hydroxy-5a-pregnane-11,20-dione |
SST0131 | Hideaki Nishino |
C21H32O3 | 332.477 | |
Preparation from hecogenin. (Ref. 0196) |
IR spectra. (Ref. 0196) |
||||||||||||||||||
| 132 |  |
Algestone / Alphasone |
16a, 17-Dihydroxypregn-4-ene-3,20-dione / 16a,17-Dihydroxyprogesterone / 4-Pregnene-16a,17a-diol-3,2-dione |
SST0132 | Hideaki Nishino |
C21H30O4 | 346.460 | |
Preparation from 16-dehydroprogesterone. (Ref. 0585) |
225 (ethanol+dichloromethane) (Ref. 0585) |
nNuiol/max 3390, 1711, 1612, 1081/cm. (Ref. 0586) |
[M]/D+336. (Ref. 0586> |
Anti-inflammatory action as an acetonide in topical tissues. (Ref. 0588) |
|||||||||||||||
| 133 |  |
Algestone acetophenide / Alphasone acetophenide / P-DHP / Bovitrol / Deladroxone / Droxone |
16a,17-Dihydroxypregn-4-ene-3,20-dione cyclic acetal with acetophenone / 16a,17a-Dihydroxyprogesterone acetophenide |
SST0133 | Hideaki Nishino |
C29H36O4 | 448.594 | |
Preparation from 16a,17a-dihydroxyprogesterone. (Ref. 0588) |
150-151 (95% ethanol) (Ref. 0588) |
[a]23/D=+51 (chloroform) (Ref. 0588) |
Unlike inactive 16a,17a-dihydroxyprogesterone as a progestagen, the acetonide exhibits three-times higher activity than progesterone. No androgenic activity, No anti-androgenic activity, estrogenic activity, anti-DCA activity, corticoid activity in a used dose. (Ref. 0588) |
Stable in boiling inorganic acid. (Ref. 0588) |
|||||||||||||||
| 134 |  |
Allylestrenol / Gestanin / Gestanol / Orageston / Gestanyn / Gestanon / Turinal |
17-(2-Propenyl)estr-4-en-17b-ol / 17a-Allylestr-4-en-17b-ol / 17a-allyl-17-hydroxy-19-nor-4-androstene / 17-Hydroxy-17a-allyl-4-estrene |
SST0134 | Hideaki Nishino |
C21H32O | 300.478 | |
Easily oxidized. (Ref. 0589) |
|||||||||||||||||||
| 135 |  |
a-Amyrin / a-Amyrenol / Viminalol |
Urs-12-en-3b-ol |
SST0135 | Hideaki Nishino |
C30H50O | 426.717 | |
bp0.7 243 C (Ref. 0597) |
Sol in 22 parts of 98% alc. Sol in ether, benzene, chloroform, glacial acetic acid. Slightly sol in petroleum ether. (Ref. 0597) |
Strong terminal methylene absorption at 887/cm (Ref. 0599) |
Plants. Ficus variegata Blume, Moraceae; Balanophora elongata Blume, Balanophoraceae; Erythroxylum coca Lam; var. novogranatense Morris, var spruceanum Burck, Erythroxylaceae. Mainly the acetate, latex from Erythroxylaceae, latex from rubber tree. (Ref. 0591) |
||||||||||||||||
| 136 |  |
b-Amyrin / b-Amyrenol |
Olean-12-en-3b-ol / 3b-Hydroxyolean-12-ene |
SST0136 | Hideaki Nishino |
C30H50O | 426.717 | |
197-197.5 C (petr. ether or alc.) (Ref. 0605) |
bp0.8 260 C (Ref. 0605) |
[a]19/D=+99.8 (c=1.3 in benzene) (Ref. 0605) |
Less solubility than a-form. Sol in 37 parts of 98% alcohol. (Ref. 0605) |
||||||||||||||||
| 137 |  |
Anagestone |
17-Hydroxy-6a-methylpregn-4-en-20-one / 6a-Methyl-4-pregnen-17a-ol-20-one |
SST0137 | Hideaki Nishino |
C22H34O2 | 330.504 | |
190-193 C (methanol+dichloromethane) (Ref. 0613) |
[a]20/D=+51 (in chloroform) (Ref. 0613) |
Progestin action as an acetate (oral ingestion to rabbits, influence to the uterus). (Ref. 0612) Formation of knot in the mammary glands when used as a contraceptive steroid for a long time (Beagle dogs). (Ref. 0611) Malignant tumor formation in the mammary glands when used as a contraceptive steroid for a long time (Beagle dogs). Estradiol, ethynylestradiol are faster removed from blood (used together with mestranol in Rhesus monkey). (Ref. 0610) Influence on the morphological structure of rhesus monkey mammary glands. (Ref. 0610) |
|||||||||||||||||
| 138 |  |
Androisoxazole / Neo-penden |
17-Methyl-5a-androstano[3,2-C]-isoxazol-17b-ol / 2,3,3a,3b,4,5,5a,6,10,10a,10b,11,12,12a-Tetradecahydro-1,10a,12a-trimethyl-1H-cyclopenta[7,8]phenanthro[2,3-C]isoxazol-1-ol /17b-Hydroxy-17a-methylandrostano[3,2-C]isoxazole |
SST0138 | Hideaki Nishino |
C21H31O2N1 | 329.476 | |
169-170 C (Ref. 0614) |
[a]/D=+19 (Ref. 0614) |
UVmax (ethanol): 226nm (loge=3.71) (Ref. 0614) |
High anabolic agent. low androgenic activity (Ref. 0614) |
||||||||||||||||
| 139 |  |
3b,11b-Dihydroxy-5a-androstan-17-one / Androstane-3b,11b-diol-17-one |
SST0139 | Hideaki Nishino |
C19H30O3 | 306.440 | |
235-238 C (acetone+ether) (Ref. 0200) |
Ppt with digitonin. (Ref. 0200) |
|||||||||||||||||||
| 140 |  |
Cetadiol |
D5-Androstene-3b-16a-diol / 5-Androstene-3b,11a-diol |
SST0140 | Hideaki Nishino |
C19H30O2 | 290.440 | |
Preparation from 5-androstene-3b,16b-diol via the formation of 3.16-di-p-toluenesulfonate, hydrolysis at C3, and epimerization at C16 by exchange reaction with p-toluenesulfonate acetate. Alternatively, from 5-androsten-3b-ol-16-one (hemihydrate) as a starting material, synthesis via 3b-acetoxy-5-androsten-16b-ol, tosylation at C16, and epimerization. (Ref. 0206) |
216-217 C (methanol aq.) (Ref. 0206) |
Tranquilizer. No androgenic activity, no anabolic activity. (Ref. 0206) |
|||||||||||||||||
| 141 |  |
a-Antiarin |
3-[(6-Deoxy-b-D-glucopyranosyl)oxy]-5,12,14-trihydroxy-19-oxocard-20(22)-enolide |
SST0141 | Hideaki Nishino |
C29H42O11 | 566.637 | |
220-235 C (Ref. 0617) |
Sol in water, alcohol. Slightly sol in ether. (Ref. 0617) |
||||||||||||||||||
| 142 |  |
Asiaticoside / Madecassol |
2a,3b,23-Trihydroxyurs-12-en-28-oic acid O-6-deoxy-a-L-mannopyranosyl-O-b-D-glucopyranosyl-O-b-D-glucopyranosyl ester |
SST0142 | Hideaki Nishino |
C48H78O19 | 959.122 | |
235-238 C (Ref. 0622) |
[a]20/D=-14 (alc.) (Ref. 0622) |
Plants. Active component of Centella asiatica (L.) Urban, Umbelliferae. Trisaccharide moiety linked to the aglycone: asiatic acid(Ref. 0622) |
Metabolism in rat. Hydrolysis in Caecal microflora. (Ref. 0623) |
Application to therapy for wound. (Ref. 0622) |
|||||||||||||||
| 143 |  |
Batrachotoxin |
Batrachotoxinin A 20-(2,4-Dimethyl-1H-pyrrole-3-carboxylate) / 3a,9a-Epoxy-14b,18b-(epoxyethano-N-methylimino)-5b-pregna-7,16-diene-3b,11a,20a-triol,20a-ester with 2,4-dimethylpyrrole-3-carboxylic acid |
SST0143 | Hideaki Nishino |
C31H42O6N2 | 538.675 | |
Partial synthesis from batrachotoxinin A. (Ref. 0626) |
UVmax (methanolic HCl): 262, 234 nm (loge=3.70,3.99), end absorption (Ref. 0626) |
0.85, 1.48 (doublet), 2.25, 2.2 ; 2.25 ; 2.45, 2.35, 3.40 (2H), 5.6-6.3 (about 3H), 8.74 broad (  0.4H) (Ref. 0625) |
Mass 399,2413 (C24H33NO4, 9 rings or double bonds), CH17/17(carbon skeleton C17 (potentially) highly unsaturated OH-groups in ring system), no intense C4H7NO (not ring A of samandarine), no intense C6H12NO (not ring F, no tomatidine) C4H10NO, C7H6-8NO, C7H8NO2 (NO within 4C, NO2 within 7C) (Ref. 0625/0626) |
Separation from the related compound in two-dimensional TLC. (Ref. 0626) |
Plants. Extraction from skin of Columbian arrow poison frog (Kokoi frog), genus Phyllobates bicolor. (Ref. 0624) |
||||||||||||||
| 144 |  |
Batrachotoxinin A |
1,2,3,4,7a,10,11,11a,12,13-Decahydro-14-(1-hydroxyethyl)-2,11a-dimethyl-7H-9,11b-epoxy-13a,5a-propenophenanthro[2,1-F][1,4]oxazepine-9,12(8H)-diol / 3a,9a-Epoxy-14b,18b-(epoxyethano-N-methylimino)-5b-pregna-7,16-diene-3b,11a,20a-triol |
SST0144 | Hideaki Nishino |
C24H35O5N | 417.538 | |
End absorption (Ref. 0625) |
1645/cm (Ref. 0625) |
0.85,1.42,2.30,2.66,3.42(-2H),5.5-6.3(-4H) (Reference TMS d=0.0, solvent CDCl3); 0.85(19-CH3), 1.90(d)(6.5)(21-CH3), 2.48(s)(N-CH3), 2.89(s)(18-CH2), 3.22(d)(18)(H-11), 4.57(q)(6.5)(H-20), 5.72(t)(2)(H-7), 6.24(dd)(2.5,5)(H-16)(TMS, d=0.0, CDCl3) (Ref. 0626) |
m/e ion 399 C24_H33NO4, 370 C23H32NO3, (342)(C22H32NO3), 312 C20H24_O3, 294 C20H22O2, 286 C18H22O3, 279 C19H19O2, 276 C20H20O, 261 C19H17O, 224 C16H16O, 219 C17H15, (206), 184 C13H12O, (166) C10H16NO, 88 C4H10NO, 71 C4H9N (Ref. 0626) |
Crystal structure of O-p-bromobenzoate derivative. (Ref. 0631) |
Separation from batrachotoxin and batrachotoxinin B, C in preparative TLC. Rf=0.54. (Ref. 0625) |
Color reactions; (1) iodoplatinate. +; (2) Ehrlich reaction, none (3) dimethylaminocinnamaldehyde, none. (Ref. 0625) |
|||||||||||||
| 145 |  |
Betamethasone / Betadexamethasone / Flubenisolone / b-Methasone / Beta-corlan / Becort / Betafluorene / Betasolon / Betnelan / Betnesol / Tablets / Celestan / Celrstene / Celestone / Visubeta |
9-Fluoro-11b,17,21-trihydroxy-16b-methylpregna-1,4-diene-3,20-dione / 9a-Fluoro-16b-methylprednisolone / 16b-Methyl-9a-fluoro-D1-hydrocortisone / 16b-Methyl-9a-fluoroprednisolone |
SST0145 | Hideaki Nishino |
C22H29O5F | 392.461 | |
231-234 C (ethyl acetate) (Ref. 0635) |
[a]/D=+108 (acetone) (Ref. 0635) |
UVmax (methanol) 238nm (e=15,200) (Ref. 0635) lNujol/max 2.90, 2.95, 5.88, 6.10, 6.15, 6.20, 11.25m |
Synthesis as a 21-acetate. (Ref. 0634) |
||||||||||||||||
| 146 |  |
Betulin / Trochol / Betulinol |
Lup-20(29)-ene-3b,28-diol / Lup-20(30)-ene-3b,28-diol |
SST0146 | Hideaki Nishino |
C30H50O2 | 442.717 | |
248-251 C (methanol-chloroform) (Ref. 0637) |
Sparingly sol in cold water, petroleum ether, carbon disulfide. Sol in 149 parts alcohol, 251 parts ether, 113 parts chloroform, 417 parts benzene. Sol in acetic acid. (Ref. 0637) |
||||||||||||||||||
| 147 |  |
Bolasterone / Myagen / U-19763 |
17b-Hydroxy-7a,17-dimethylandrost-4-en-3-one / 7a,17-Dimethyltestosterone |
SST0147 | Hideaki Nishino |
C21H32O2 | 316.478 | |
Synthesis by reaction of D5-7-keto steroid with methylmagnesium halide or methyl lithium to obtain 7-methyl carbinol, followed by successive several reactions. (Ref. 0643) |
163-165 C (Ref. 0643) |
In oral ingestion to rat, myotropic activity, androgenic activity; 1, 1 in 17-methyltestosterone; 13.4, 3.0 in bolasterone (because of 7a-methyl-group). Anabolic assay in monkey, higher activity than halotestin. Accordingly, since a smaller dose of bolasterone will be enough, in clinical application, toxicity to liver shall be relatively lowered. (Ref. 0643/0644) |
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| 148 |  |
Boldenone / Dehydrotestosterone |
17b-Hydroxyandrosta-1,4-dien-3-one / 1,4-Androstadien-17b-ol-3-one / 3-Oxo-17b-hydroxy-1,4-androstadien |
SST0148 | Hideaki Nishino |
C19H26O2 | 286.409 | |
Synthesis from testosterone. Also can be synthesized from D5-17b-hydroxy-androsten-3-on. (Ref. 0449) |
164-166 C (Ref. 0449) |
[a]25/D=+25 (chloroform) (Ref. 0449) |
UVmax: 243-244mm (Ref. 0645) |
Carbon tetrachloride, 3675, 3500 (free and associate hydroxy), 1670 (3-ketone), 1632 (D4-double bond), 1607/cm (D1-double bond) (Ref. 0645) |
In anabolic action in muscle, 17-cyclopentenyl ether (Quinbolone) exerts lower toxicity to liver in oral ingestion.(Ref. 0645) |
Weakly positive in Zimmermann reaction, orange-colored by spray with ethanol-sulfate.(Ref. 0645) |
|||||||||||||
| 149 |  |
Bufogenin B / Desacetylbufotalin |
3b,14,16b-Trihydroxy-5b-bufa-20,22-dienolide |
SST0149 | Hideaki Nishino |
C24H34O5 | 402.524 | |
Prepared by removal of acetyl-group from Bufotalin. (Ref. 0247) |
210-223 C (Ref. 0247) |
Very sparingly sol in chloroform, methanol, acetone. (Ref. 0247) |
Animals. Separation from Chinese drug prepared from Chinese toads (Bufo asiaticus = Bufo gargarizans Cantor). (Ref. 0247) |
Toxin secreted from skin glands of toads. (Ref. 0247) |
|||||||||||||||
| 150 |  |
Bufotoxin / Vulgarobufotoxin |
Bufotalin 3-suberoylarginine ester |
SST0150 | Hideaki Nishino |
C40H60O10N4 | 756.925 | |
Partial synthesis.(Ref. 0650) |
198-202 C (Ref. 0647) |
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| 151 |  |
Calotropin |
[2a(2S,3S,4S,6R),3b,5a]-14-Hydroxy-19-oxo-3,2-[(tetrahydro-3,4-dihydroxy-6-methyl-2H-pyran-2,3-diyl)bis(oxy)]card-20(22)-enolide |
SST0151 | Hideaki Nishino |
C29H40O9 | 532.623 | |
UVmax: 217, 310nm (EtOH, loge=4.21, 1.49). (Ref. 0657) |
Almost same structure as apocannoside, cymarin. Isolation of both forms from extract of Apocynum cannabinum L.(Apocynaceae), possessing cytotoxic activity to tumors. (Ref. 0655) |
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| 152 |  |
Canrenone / Phanurane |
17-Hydroxy-3-oxo-17a-pregna-4,6-diene-21-carboxylic acid g-lactone / 17a-(2-Carboxyethyl)-17b-hydroxyandrosta-4,6-dien-3-one lactone /17a-(2-Carboxyethyl)-17b-hydroxy-3-oxo androsta-4,6-diene lactone / 6-Dehydrotestosterone-17a-propionic acid g-lactone / 3-(3-oxo-17b-hydroxy-4,6-androstadien-17a-yl) propionic acid g-lactone |
SST0152 | Hideaki Nishino |
C22H28O3 | 340.456 | |
Preparation by dehydrogenation of 17-hydroxy-3-oxo-17a-pregn-4-ene-21-carboxylic acid g-lactone. (Ref. 0543) |
[a]/D=+24.5 (chloroform). (Ref. 0543) |
UVmax: 283nm (e=26,700). (Ref. 0543) |
Competitive agent to the action of aldosterone. Diuretic. 50% Bolck of effect of desoxycorticosterone on the ratio of sodium-potassium in urine of adrenalectomized rats by oral ingestion of 12mg. (Ref. 0543) |
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| 153 |  |
Cephalosporin P1 |
6a,16b-Bis(acetyloxy)-3a,7b-dihydroxy-29-nordammara-17(20),24-dien-21-oic acid |
SST0153 | Hideaki Nishino |
C33H50O8 | 574.745 | |
147 C (Ref. 0662) |
[a]20/D=+28 (c=2.7 in chloroform) (Ref. 0662) |
Immediately sol in most organic solvents. Slightly sol in chloroform, ethanol. (Ref. 0662) |
UVmax: 211nm (e=9,140). (Ref. 0662) |
Antibiotics. Inhibition of proliferation of most Gram-positive bacteria. All five species of cephalosporins share the common properties to helvolic acid (antibiotic produced by Aspergillus fumigatus). Most active cephalosporin, P1, exhibits the same activity as aureomycin and terramycin. The activity of P1 is twice higher than helvolic acid (in cylinder plate method, effect to S. aureus). (Ref. 0662) |
Cephalosporin P consists at least of five components, P1, P2, P3, P4, and P5. P1 is the most active one. P1 is stable in organic solvent and as sodium salt in solution (pH7.0) at room temperature. At pH8.0, slowly become inactive, and at pH9.6, rapidly inactivated. (Ref. 0662) Cephalosporin P1 is not C32H48O8, but, maybe possess one more methyl-group at C8, perhaps C33H50O8. (Ref. 0664) Revision to C33H50O8 by NMR and mass. (Ref. 0655/0666) |
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| 154 |  |
Cerberin / Veneniferin / Monoacetylneriifolin |
SST0154 | Hideaki Nishino |
C32H48O9 | 576.718 | |
Sol in alcohol, chloroform, acetic acid, pyridine. Slightly sol in ethyl acetate, acetone, water. Very sparingly sol in ether, benzene. (Ref. 0671) |
Positive by Tollens' reagent. Positive by sodium nitroprusside. By treatment with conc. sulfate, the color chages from lemon-yellow to wine-red, which shows green-fluorescence. Reacted with m-dinitrobenzene, the violet color changes to indigo blue (characteristic to cardiac glycoside). Reacted with Liebermann-Burchard reagent, sows emerald green-color. Negative by Keller-Killiani reagent. In sealed tube, by treatment with dil. sulfate, cerberin reduces Benedict's solution. (Ref. 0671) |
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| 155 |  |
Cerberoside / Thevetin B / Thevanil |
3b-[(O-b-D-Glucopyranosyl-(1 to 6)-O-b-D-glucopyranosyl-(1 to 2)-6-deoxy-3-O-methyl-a-L-glucopyranosyl)oxy]-14-hydroxy-5b-card-20(22)-enolide |
SST0155 | Hideaki Nishino |
C42H66O18 | 858.963 | |
197-201 C (water) (Ref. 0672) |
Sol in water, alcohol, acetic acid, pyridine. Slightly sol in ethyl acetate, acetone. Sparingly sol in ether, benzene, chloroform. (Ref. 0671) |
Plants. Found in a species of Cerbera odollam Gaertn., Apocynaceae, Thevetia neriifolia Juss., (a species of Apocynaceae). (Ref. 0671) |
Weaker cardiotonic drug than cerberin. E.M.D.50 (mg/kg pigeon)=150.2 11.6, LD50 (mg/kg cat)=813.778. (Ref. 0671) |
||||||||||||||||
| 156 |  |
Cevadine / Veratrine |
(Z)-4a,9-epoxycevane-3b,4,12,14,16b,17,20-Heptol 3-(2-methyl-2-butenoate) |
SST0156 | Hideaki Nishino |
C32H49O9N | 591.733 | |
Synthesis by hydrogenation of veracevine 3-(3'-bromoangelate). (Ref. 0675) |
[a]20/D=+12.8 (c=3.2 in alc.) (Ref. 0673) |
Sol in alcohol, ether (1g/about 15ml). Sparingly sol in water. (Ref. 0673) |
Very strong absorbance in short wavelength region, but the peak cannot be detected. (Ref. 0673) |
Absorbance as evidence for the presence of ether-linked carbonyl-group. Absorbance as evidence for the presence of many hydroxyl-groups. (Ref. 0674) |
A species of Sabadilla alkaloid utilized for an insecticide. Stimulative to mucous membrane. Strong toxicity by ingestion. Strong side effect. (Ref. 0674) |
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| 157 |  |
Cevine |
4,9-Epoxycevane-3a,4b,12,14,16b,17,20-heptol. |
SST0157 | Hideaki Nishino |
C27H43O8N | 509.632 | |
Hydrochloride, 247 C. (Ref. 0679) |
[a]17/D=-17.5 (aq. alc.). (Ref. 0679) |
Sol in water, alcohol. Slightly sol in ether. (Ref. 0679) |
Plants. Alkamine (aminoalcohol) yielded by hydrolysis of cevadine. (Ref. 0677) |
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| 158 |  |
Chlormadinone acetate / Gestafortin / Lormin / Luteran / Verton / Lutestral / Lutoral[Syntex] / Normenon / Menstridyl / Cero |
6-Choloro-17-hydroxy-pregna-4,6-diene-3,20-dione acetate; 6-Chloro-6-dehydro-17a-hydroxyprogesterone acetate / 6-Chloro-6-dehydro-17a-acetoxyprogesterone / 17a-Acetoxy-6-chloro-6,7-dehydroprogesterone |
SST0158 | Hideaki Nishino |
C23H29O4Cl | 404.927 | |
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| 159 |  |
16a-Chloroestrone 3-methyl ether / Atheran |
16a-Chloro-3-methoxyestra-1,3,5(10)-trien-17-one |
SST0159 | Hideaki Nishino |
C19H23O2Cl | 318.837 | |
Preparation from estrone methyl ether enol acetate by reaction with chlorine and potassium carbonate in carbon tetrachloride. (Ref. 0683) |
177-179 C (chloroform). (Ref. 0683) |
[a]/D=+161 (chloroform). (Ref. 0683) |
Anticholesteremic agent. Applicable because of weak estrogenic activity (1/100 estron). (Ref. 0683) |
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| 160 |  |
6a-Chloro-17,21-dihydroxy-pregna-1,4-diene-3,11,20-trione / 6a-Chloro-1,4-pregnadiene-17a,21-diol-3,11,20-trione |
SST0160 | Hideaki Nishino |
C21H25O5Cl | 392.873 | |
Preparation as the 21-acetate by selenium dioxide dehydrogenation of 6a-chlorocortisone 21-acetate. (Ref. 0684) |
The 21-acetate, C23H27ClO6, 217-219 C (acetone+hexane). (Ref. 0684) |
The 21-acetate [a]/D=+144 (chloroform). (Ref. 0684) |
The 21-acetate; UVmax (ethanol): 237nm (loge=4.19). (Ref. 0684) |
Use as a glucocorticoid to topical tissues. Thymolytic activity, 4; anti-inflammatory activity, 4 when the values for hydrocortisone acetate are 1, respectively, in oral ingestion to adrenalectomized rats. (Ref. 0684) |
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| 161 |  |
Cimigenol / Cimicifugol |
16,23:16,24-Diepoxy-9,19-cyclo-9b-lanostane-3b,15a,25-triol |
SST0161 | Hideaki Nishino |
C30H48O5 | 488.699 | |
216-217 C (Ref. 0688) |
[a]/D=+38.2 (c=1.99 in chloroform). (Ref. 0688) |
No characteristic absorbance. (Ref. 0688) |
lKBr/max 3280/cm(OH). (Ref. 0688) |
One split signal (3H, J=5-6c/sec.), belonging to secondary methyl group. (Ref. 0685) |
468 (osmometer) (Ref. 0688) |
No change in heating reflux in 5% NaOH (MeOH) for 1 h. Resistant to NaIO4 (MeOH). Not absorb H2. Production of several species in mixture by heating reflux in 5% HCl (MeOH) for 1 h. No change in heating reflux in 5% AcOH for 5 h. (Ref. 0688) |
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| 162 |  |
4-Chlorotestosterone / Clostebol |
4-Chloro-17b-hydroxyandrost-4-en-3-one |
SST0162 | Hideaki Nishino |
C19H27O2Cl | 322.869 | |
Yielded by treatment of 4a,5-oxidoandrostane-17b-ol-3-one acetate with HCl in acetic acid, convertion to 4b-chloroandrostane-5a,17b-diol-3-one-17-acetate, and heating to remove water. (Ref. 0689) Preparation by treatment of 4x,5x-oxidoandrosta-17b-ol-3-one with 1 part of 37% HCl in acetone. (Ref. 0690) |
188-190 C (acetone+hexane). (Ref. 0690) |
[a]20/D=+148 (chloroform). (Ref. 0690) |
UVmax (95% ethanol): 256nm (loge=4.13). (Ref. 0690) |
Anabolic action. Anabolic-androgenic ratio is 0.88 as the acetate when testosterone propionate is 0.28. (Ref. 0689) |
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| 163 |  |
Colocynthin |
25-(Acetyloxy)-2-(b-D-glucopyranosyloxy)-16,20-dihydroxy-9-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione / 2-O-b-D-Glucopyranosylcucurbitacin E |
SST0163 | Hideaki Nishino |
C38H54O13 | 718.828 | |
[a]/D=+50 (c=0.4 in ethanol). (Ref. 0691) |
Sol in ethanol, acetone, chloroform. Sparingly sol in ether, water. (Ref. 0691) |
UVmax: 234-236nm (loge=4.11). (Ref. 0691) |
Like a-elaterin, exhibits 3570, 3450(OH), 1725(Ac), 1685(C:C-CO), 1660, 1625, 1415 (diosphenol)/cm. Others, 1425, 1390, 1370, 1250, 1220, 1120, 1070/cm (Ref. 0692) |
Plants. Fruits of Citrullus colocynthis Schred., Cucurbitaceae. (Ref. 0691) |
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| 164 |  |
Colpormon / Colpogynon |
3,16a-Bis(acetyloxy)estra-1,3,5(10)-trien-17-one / 3,16a-Dihydroxyestrone diacetate / 3,16a-Diacetoxy-D1,3,5-estratrien-17-one |
SST0164 | Hideaki Nishino |
C22H26O5 | 370.439 | |
Synthesis from b-hydroxyandrostane-17-one (isoandrosterone). Estriol is yielded by lithium aluminum hydride-treatment. (Ref. 0120) |
179-180 C. (Ref. 0120) |
[a]28/D=+122 (chloroform). (Ref. 0120) |
[M]/D=+451. (Ref. 0120) |
Estrogenic acitivty. (Ref. 0120) |
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| 165 |  |
Conessine / Neriine / Roquessine / Wrightine |
3b-(Dimethylamino)con-5-enine |
SST0165 | Hideaki Nishino |
C24H40N2 | 356.588 | |
[a]20/D=+25.3 (c=0.7 in anhydrous alcohol) (Ref. 0693) |
Slightly sol in water. (Ref. 0693) |
798, 826, 1665/cm (Ref. 0695) |
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| 166 |  |
Coproergostane / Pseudoergostane |
5b-Ergostane |
SST0166 | Hideaki Nishino |
C28H50 | 386.697 | |
Synthesis from cholanic acid via norcholyl-methyl-ketone. (Ref. 0701) |
64 C (acetone). (Ref. 0701) |
[a]19/D=+25.3 (c=2 in chloroform) (Ref. 0701) |
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| 167 |  |
Coprostane / Pseudocholestane |
5b-cholestane |
SST0167 | Hideaki Nishino |
C27H48 | 372.670 | |
72 C (alcohol) (Ref. 0702) |
[a]11/D=+25.1 (c=2 in chloroform) (Ref. 0040) |
Characteristic bands at 900 and 1070/cm. (Ref. 0040) |
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| 168 |  |
Corticosterone / Compd B / Reichstein's Substance H / Kendall's Compd B |
11b,21-Dihydroxypregn-4-ene-3,20-dione / 4-Pregnene-11b,21-diol-3,20-dione |
SST0168 | Hideaki Nishino |
C21H30O4 | 346.460 | |
180-182 C (acetone). (Ref. 0615) |
[a]15/D=+223 (c=1.1 in alc.). (Ref. 0615) |
Insol in water. Sol in general organic solvents. (Ref. 0269) |
UVmax: 240nm (loge=Ca.4) (Ref. 0615) |
Animals. Main biosynthesis site is the zona fasciculata of adrenal cortex. (Ref. 0269) |
A glucocorticoid as adrenocortical steroid, same as cortisol and cortisone. However, weaker both in glycogen storage action and anti-inflammatory effect than the other two species. Utilized as a precursor to aldosterone, which is biosynthesized as a strong mineralcorticoid in adrenocortical zona glomerulosa by active 18-hydroxylase. (Ref. 0615) |
By conc. sulfate, turned to be orange-yellow colored solution, which emits strong fluorescence. (Ref. 0615) |
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| 169 |  |
Cortivazol / MK-650 / H3625 / Altim / Diaster / Dilaster / Idaltim |
11b,17,21-Trihydroxy-6,16a-dimethyl-2'-phenyl-2'H-pregna-2,4,6-trieno[3,2-C]pyrazol-20-one 21-acetate / 1,2,3,3A,3B,7,10,10A,10B,11,12,12A-Dodecahydro-1,11-dihydroxy-2,5,10A,12A-tetramethyl-7-phenylcyclopenta[7,8]phenanthro[2,3-C]pyrazol-1-ylhydroxymethylketoneacetate / 6,16a-dimethyl-11b,17a, 21-trihydroxy-2'-phenyl[3,2-C]pyrazolo-4,6-pregnadien-20-one 21-acetate |
SST0169 | Hideaki Nishino |
C32H38O5N2 | 530.655 | |
Obtained by hydrolysis of 2-hydroxymethylene-17a,20,20,21-bismethylenedioxy-6,16a-dimethyl-4,6-pregnadiene-11b-ol-3-one. (Ref. 0706) |
[a]23/D=+14 (chloroform). (Ref. 0706) |
UVmax (methanol): 283, 315nm (e=15,700, 19,000). (Ref. 0706) |
Glucocorticoid action. Anti-inflammatory effect. In systemic granuloma, cortivazol, 551 (oral ingestion to male Holtzman rats (Ca.125g) every day for a week) when 9a-fluoro-16a-methyl-1,4,6-pregnatriene-11b,17a,21-triol-3,20-dione21-acetate (D6-dexamethasone), 150. 75-Times higher activity to human rheumatoid arthritis pain than hydrocortisone. No reports on sodium retention activity. (Ref. 0706) |
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| 170 |  |
Cortolone |
3a,17a,20a,21-tetrahydroxypregnan-11-one / 3a,17a,20a,21-pregnanetetrol-11-one |
SST0170 | Hideaki Nishino |
C21H34O5 | 366.492 | |
Synthesis from pregnane-3a,17a-diol-11,20-dione as a starting material. (Ref. 0708) Synthesis by treatment of D20-allopregnene-3b,20-diol diacetate with perbenzoic acid, and |
208-209 C (acetone). (Ref. 0707) |
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| 171 |  |
Cucurbitacin A |
25-(Acetyloxy)-2,16,20-trihydroxy-9-(hydroxymethyl)-19-norlanosta-5,23-diene-3,11,22-trione |
SST0171 | Hideaki Nishino |
C32H46O9 | 574.702 | |
207-208 C (ethyl acetate) (Ref. 0710) |
[a]27/D=+97.3 (c=1.04 in ethanol) (Ref. 0710) |
UVmax (ethanol): 229, 290nm (loge=4.03, loge=2.26), inflexion: 330-350nm (loge=1.81-1.64). (Ref. 0710) |
Plants. Fruits of Cucurbitaceae cucumis Myriocarpus, C. Leptodermis. (Ref. 0710) |
Bitter taste component of Cucurbitaceae. Minimum lethal dose (M.L.D), 0.7mg/kg rabbit (i.v.). (Ref. 0710) |
Neutral, included one acetyl group. (Ref. 0710) |
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| 172 |  |
Cucurbitacin C |
25-(Acetyloxy)-3,16,20-trihydroxy-9-(hydroxymethyl)-19-norlanosta-5,23-diene-11,22-dione |
SST0172 | Hideaki Nishino |
C32H48O8 | 560.719 | |
207-207.5 C (ethyl acetate) (Ref. 0710) |
[a]27/D=+95.2 (c=1.03 in ethanol). (Ref. 0710) |
UVmax (ethanol): 231, 298nm (e=11,100, 11,131). (Ref. 0712) |
nmax 1731, 1256 (OAc), 1689, 1631 (CO-C:C)/cm. (Ref. 0712) |
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| 173 |  |
Cucurbitacin B |
25-(Acetyloxy)-2,16,20-trihydroxy-9-methyl-19-norlanosta-5,23-diene-3,11,22-trione / 1,2-Dihydro-a-elaterin |
SST0173 | Hideaki Nishino |
C32H46O8 | 558.703 | |
Strong absorption maxima at 2.92, 5.82, 5.92, 6.17m (Ref. 0715) |
Toxic. (M.L.D.(eel), 0.5mg/kg). (Ref. 0710) Bitter taste component of Cucurbitaceae. (Ref. 0714) Make a decoction of the roots to utilize for fishing, suicide, or killing old, weak, or sick people by California Indians. When using as a drug, extract from seeds or roots was supplied for rheumatoid arthritis or venereal disease. Strong diarrheal activity in the roots. Utilization of the roots for making Stoughton's Bitters in California. (Ref. 0715) |
X-ray crystallography. Reduction of Tollens reagent. Positive in Molish reaction. Positive in acetic acid test. Red-colored when solving in acetic acid containing sulfate. In Liebermann- and Liebermann-Burchard tests, burgundy-colored by reacted with hydrogen bromide in acetic acid, purple-colored by reacted with antimony pentachloride in chloroform. Negative in ferric chloride and legal test. Zerevitionv determinations: 0.824 and 0.824%H. (Ref. 0715) Interrelationships in Cucurbitacins B, D (Elatericin A), E (a-elaterin), I (Elatericin B). (Ref. 0717) Stereochemistry of cucurbitacins. (Ref. 0719) |
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| 174 |  |
Cucurbitacin D / Elatericin A |
2b,16b,20,25-Tetrahydroxy-9-methyl-19-nor-9b,10a-lanosta-5,23-diene-3,11,22-trione |
SST0174 | Hideaki Nishino |
C30H46O7 | 518.682 | |
nmax: 3425, 1689, 1626, 1377, 1088, 1058, 983/cm (Ref. 0716) |
Bitter taste component. Anti-tumor activity. (Ref. 0716) |
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| 175 |  |
Cucurbitacin F |
2,3,16,20,25-Pentahydroxy-9-methyl-19-norlanosta-5,23-diene-11,22-dione |
SST0175 | Hideaki Nishino |
C30H44O7 | 516.666 | |
244-245 C (chloroform) (Ref. 0714) |
[a]/D=+38 (c=1.2 in ethanol) (Ref. 0714) |
lmax, mm (E1%/1cm): 232(228), 300(2.7) in neutral solution, unchanged in alkaline solution (Ref. 0714) |
nmax (in KBr): 1690, 1629/cm ab-unsaturated ketone group), 1700/cm (isolated ketone group) (Ref. 0718) |
Bitter taste component. (Ref. 0718) |
Revision as C30H46O7. No color reaction by tetrazolium blue. Direct relationship between Cucurbitacin D and F because reduction of Dihydrocucurbitacin D by sodium borohydride results in Dihydrocucurbitacin F. (Ref. 0718) |
||||||||||||||
| 176 |  |
Cucurbitacin I / Elatericin B |
2,16,20,25-Tetrahydroxy-9-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione / 1,2-Dehydroelatericin A. |
SST0176 | Hideaki Nishino |
C30H42O7 | 514.650 | |
[a]/D=-52 (c=1.56 in chloroform) (Ref. 0716) |
Sol in dil. alkali, ethylacetate, chloroform, benzene. (Ref. 0716) |
nmax: 3410, 1685, 1660, 1629, 1606, 1413, 1090, 1005/cm (Ref. 0716) |
Complete separation from Cucurbitacin D in developing solvent of ethylacetate:benzene (1:1) or chloroform:benzene (1:1) in paper chromatography. Not clearly separated in a developing solvent consisted of only chloroform. Strong color-reaction by treatment with ferric chloride in ethanol. (Ref. 0714) |
Diarrheal agent. Anti-tumor activity. (Ref. 0716) |
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| 177 |  |
Cucurbitacin E / a-Elaterin |
25-(Acetyloxy)-2,16,20-trihydroxy-9-methyl-19-nor-9b,10a-lanosta-1,5,23-triene-3,11,22-trione |
SST0177 | Hideaki Nishino |
C32H44O8 | 556.687 | |
Slightly sol in alcohol. Insol in water. Sol in petroleum ether, chloroform. |
Strong peak at 234mm (e=11,700), shoulder at 267mm (e=8,350) (Ref. 0720) |
mmax: 3450, 1723, 1683, 1660, 1627, 1412, 1370, 1130, 1090, 990/cm (Ref. 0720) |
Plants. Fruits of Ecballium elaterium (L.) A. Rich., Cucurbitaceae (squirting cucumber). (Ref. 0720) |
The fruit juice, called Elaterium, had been used as a strong diarrheal agent from ancient times. Recorded in The British Pharmacopeia. Very strong anti-tumor activity to mouse sarcoma-37 transplanted in the muscle by intraperitoneal injection together with b-elaterin. No significant anti-tumor activity by the dermenchysis of Cucurbitacin E only. (Ref. 0720) |
Upon addition of NaOH, disappear shoulder (267mm) in ultraviolet region, new peak appeared at 318mm (e= 5,000). This bathochromic shift is reversed by addition of acid. Strong color-reaction by treatment with ferric chloride in ethanol. (Ref. 0720) Five methyl groups bound to quaternary atoms of tetracyclic nucleus. (Ref. 0713) Stereochemistry. (Ref. 0719) |
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| 178 |  |
Cucurbitacin G |
2,16,20,24,25-Pentahydroxy-9-methyl-19-norlanost-5-ene-3,11,22-trione |
SST0178 | Hideaki Nishino |
C30H46O8 | 534.681 | |
149-150 C (Ref. 0714) |
[a]/D=+84 (c=1.5 in chloroform). (Ref. 0714) |
Sol in chloroform, benzene. (Ref. 0714) |
lmax., mm (E1%/1cm): 282(4.2) in neutral solution, 314(99) in alkaline solution.(Ref. 0714) |
Have ever been found along with Dihydrocucurbitacin D because of the same m.p. and very similar IR spectra. However, completely separated each other in paper chromatography. (Ref. 0714) |
Plants. Roots of Cucumis hirsutus Sond., Cucurbitaceae.(Ref. 0714) |
Bitter taste component. (Ref. 0714) |
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| 179 |  |
Cucurbitacin H |
2,16,20,24,25-Pentahydroxy-9-methyl-19-norlanost-5-ene-3,11,22-trione |
SST0179 | Hideaki Nishino |
C30H46O8 | 534.681 | |
[a]/D=+57 (c=1.5 in chloroform). (Ref. 0714) |
Amorphous. Unable to crystallize by rechromatography using acid-washed alumina or formamide-impregnated paper. (Ref. 0714) |
Plants. Bitter taste component in roots of Cucumis hirsutus. (Ref. 0714) |
Bitter taste component. (Ref. 0714) |
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| 180 |  |
Cucurbitacin J |
2,16,20,24,25-Pentahydroxy-9-methyl-19-norlanosta-1,5-diene-3,11,22-trione |
SST0180 | Hideaki Nishino |
C30H44O8 | 532.666 | |
[a]/D=-36 (c=1.0 in chloroform). (Ref. 0721) |
nmax: 1695, 1664/cm (Ref. 0721) |
Separated from Cucurbitacin D in paper chromatography using chloroform:benzene (1:1) as a developing solvent. Not separated using ethylacetate:benzene. (Ref. 0714) |
Bitter taste component .(Ref. 0714) |
Different only atomic orientation of hydroxyl group at C24 between Cucurbitacin J and K, each other. (Ref. 0721) |
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| 181 |  |
Cucurbitacin K |
2,16,20,24,25-Pentahydroxy-9-methyl-19-norlanosta-1,5-diene-3,11,22-trione |
SST0181 | Hideaki Nishino |
C30H44O8 | 532.666 | |
[a]/D=-74 (c=1.0 in chloroform) (Ref. 0721) |
nmax: 1695, 1664/cm. (Ref. 0721) |
Bitter taste component. (Ref. 0714) |
Different only atomic orientation of hydroxyl group at C24 between Cucurbitacin J and K, each other. (Ref. 0721) |
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| 182 |  |
Cucurbitacin L |
2,16,20,25-Tetrahydroxy-9-methyl-19-norlanosta-1,5-diene-3,11,22-trione / 23,24-Dihydrocucurbitacin L |
SST0182 | Hideaki Nishino |
C30H44O7 | 516.666 | |
Plants. Roots of Citrullus ecirrhosus Sond.(Colocynthis ecirrhosus Chakrav.), Cucurbitaceae (Ref. 0721) |
Bitter taste component. (Ref. 0714) |
Identical with 23,24-dihydrocucurbitacin I. (Ref. 0721) |
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| 183 |  |
Cyclobuxine / Alkaloid A. |
14a-Methyl-3b,20a-bis(methylamino)-4-methylene-9,19-cyclo-5a,9b-pregnan-16a-ol |
SST0183 | Hideaki Nishino |
C25H42ON2 | 386.614 | |
[a]23/D=+98 (chloroform). (Ref. 0724) |
lmax: 6.09, 11.20m (terminal methylene). (Ref. 0724) |
5.20, 5.43 (2H, doublets, J 1C.1S.; terminal methylene), 5.92 (1H, octuplet, J'S3,7,9.5C./S.; CH2CHOH-CH), 7.53 and 7.57 (6H, two NCH3), 8.87 and 9.03 (6H, two tertiary CH3), 8.92 (3H, doublet, J6 C./S.; one sec. CH3) and 9.72 and 9.95J (2H, doublets, J4C./S.; cyclopropyl methylene). (Ref. 0724) |
Application as a drug for therapy of various diseases, such as malaria, venerealdisease from ancient times. Also effective as an anti-tuberculosis. (Ref. 0724) |
Determination of stereochemistry. (Ref. 0725) |
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| 184 |  |
Danazol / Win 17.757 / Danol |
17a-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol / 17a-Pregn-4-en-20-yno[2,3-d]isoxazol-17-ol / 1-Ethynyl-2,3,3A,3B,4,5,10,10A,10B,11,12,12A-dodecahydro-10A,12A-dimethyl-1H-cyclopenta[7,8]phenanthro-[3,2-D]-isoxazol-1-ol / 17a-Etynyl-17b-hydroxy-4-androsteno[2,3-D]isoxazole |
SST0184 | Hideaki Nishino |
C22H27O2N | 337.455 | |
Preparation by reaction of 2-hydroxymethylene-3-ketosteroid and hydroxylamine. (Ref. 0726) |
224.4-226.8 C (Ref. 0726) |
UVmax (ethanol): 286nm (e=11,300) (Ref. 0726) |
Suppressor to prehypphysis function (gonadal inhibitor) (inhibition of gonadotropin-release in normal human). Inhibition of synthesis of androgen in Leydig cell. (Ref. 0727) Similar effect also in albino rats, rats, mice, rabbits to human. (Ref. 0419) Espacially effective in therapy of precocious pubery, endometriosis, virginal breast hypertrophy, chronic cystic mastitis. (Ref. 0728) |
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| 185 |  |
Dehydroepiandrosterone / Dehydroisoandrosterone / Trans-Dehydroandrosterone / 17-Hormoforin / Diandron / Psicosterone / 17-Chetouis |
3b-Hydroxyandrost-5-en-17-one / D5-Androsten-3b-ol-17-one |
SST0185 | Hideaki Nishino |
C19H28O2 | 288.424 | |
[a]18/D=+10.9 (c=0.4 in alc.). (Ref. 0734) |
Sol in benzene, alcohol ether. Slightly sol in chloroform, petroleum ether. (Ref. 0209) |
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| 186 |  |
Deoxyxorticosterone / 21-Hydroxyprogesterone / Desoxycorticosterone / 11-Deoxycorticosterone / Cortexone / Desoxycortone / Kendall's Desoxy Compound B / Reichstein's Substance Q |
21-Hydroxypregn-4-ene-3,20-dione / 4-Pregnen-21-ol-3,20-dione |
SST0186 | Hideaki Nishino |
C21H30O3 | 330.461 | |
[a]22/D=+178 (c=1.5 in alcohol). (Ref. 0188) |
Sol in alcohol, acetone. (Ref. 0188) |
UVmax 240nm (loge=Ca, 4). (Ref. 0615) |
Action as an adrenocortical steroid (Salt-regulating). (Ref. 0615) |
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| 187 |  |
Desatrine |
4a,9-Epoxycevane-3b,4,6a,7a,14,15a,16b,20-octol 6,7-Diacetate 15-(2-methylbutanoate) / Protoverine 6,7-diacetate 15-(2-methylbutyrate) / Protoverine 6,7-diacetate 15(L)-2'-methylbutyrate |
SST0187 | Hideaki Nishino |
C36H55O12N | 693.821 | |
232-233 C (Ref. 0737) |
[a]26/D=-46 (c=0.95 in pyridine) (Ref. 0737) |
Plants. Synthesis. Preparation from treatment of protoveratrine B with periodate, followed by alkalization with ammonium hydroxide. protoveratrine is an alkaloid isolated from Veratrum album. Later identified as a mixture of A- and B-forms. (Ref. 0737) |
Insecticide. Also applicable to the therapy for hypertension. (Ref. 0737) |
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| 188 |  |
Protoveratrine A / Pro-Amid / Protalba |
4a,9-Epoxycevane-3b,4,6a,7a,14,15a,16b,20-octol-6,7-diacetate 3(S)-(2-hydroxy-2-methylbutanoate) / 15(R)-(2-Methylbutanoate)-protoverine 3-(d)-2'-Hydroxy-2'-methylbutyrate 6,7-diacetate 15-(L)-2'-methylbutyrate |
SST0188 | Hideaki Nishino |
C41H63O14N | 793.937 | |
Sol in chloroform, pyridine, hot alcohol. Insol in water, petroleum ether. (Ref. 0742) |
Application as an antihypertensive. Somewhat bitter, induces a sneezing. (Ref. 0737) |
Structure determination of protoveratrine A and B. (Ref. 0737) Protoveratrine is a mixture of two alkaloids, which share very similar structure. However, hydrolysis yields one different product. (Ref. 0742/0743) In hydrolysis by p-touenesulfonic acid, yields 1.88 mol acetic acid, 0.92 mol 2-methylbutyric acid, 0.93 mol 2-hydroxy-2-methylbutyric acid. (Ref. 0742) |
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| 189 |  |
Protoveratriene B / Veratetrine / Neoprotoveratrine |
4a,9-Epoxycevane-3b,4,6a,7a,14,15a,16b,20-octol-6,7-diacetate 3(S)-(2,3-dihydroxy-2-methylbutanoate)15(R)-(2-methylbutanoate) / Protoverine3-(d)-thred-2',3'-dihydroxy-2'-methylbutyrate 6,7-diacetate 15-(L)-2'-methylbutyrate |
SST0189 | Hideaki Nishino |
C41H63O15N | 809.937 | |
Sol in chloroform, pyridine, hot alcohol. Insol in water, petroleum ether. (Ref. 0742) |
Application as an antihypertensive. Somewhat bitter, induces a sneezing. (Ref. 0737) |
Structure determination of protoveratrine A and B. (Ref. 0737) Protoveratrine is a mixture of two alkaloids, which share very similar structure. However, hydrolysis yields one different product. (Ref. 0742) Proportion to protoveratrine A, diverse in each root and rhizome, from 0.36 to 0.58. (Ref. 0742) Hydrolysis yields 2 mol acetic acid, 1 mol (-)a-methyl-butylic acid, and 1 mol (+)a-methyl-a,b-dioxy-butylic acid. (Ref. 0743) |
|||||||||||||||||
| 190 |  |
Descinolone / 21-Deoxytriamcinolone |
9-Fluoro-11b,16a,17-trihydroxypregna-1,4-diene-3,20-dione / 9a-Fluoro-1,4-pregnadiene-11b,16a,17a-triol-3,20-dione |
SST0190 | Hideaki Nishino |
C21H27O5F | 378.434 | |
Sol in methanol, ethyl acetate. (Ref. 0744) |
Preparation by microbiological dehydrogenation: 1 % innoculation of Nocardia corallina (ATCC 999) cultured for 8 h in beef extract, yeast extract, peptone, and cerelose medium. Add 9a-fluoro-11b,16a,17a-trihydroxy-4-pregnene-3,20-dione solubilized in methanol and further culture at 28 C for 17 h. Extract the content into ethyl acetate for purification. (Ref. 0744) |
In glucocorticoid activity (rat liver glycogen analysis), 4-times higher than hydrocortisone. No sodium retention activity. (Ref. 0744) |
Preparation of the acetate, 16a-acetoxy 9a-fluoro-11b,17a-dihydroxy-1,4-pregnadiene-3,20-dione by overnight treatment in acetic anhydride-pyridine. m.p. 242-244 , [a]25/D=+27.3 (c=0.768, methanol), lmax 239mm (e=16,200): nmax 3509, 3413, 1736, 1695, 1672, 1629, 1250/cm. The isopropylidene derivative, 9aFluoro-11b-hydroxy-16a,17a-isopropylidenedioxy-1,4-pregnadiene-3,20-dione: m.p. 307, [a]25/D=+102 (c=0.975), lmax 238mm (e=15,500), nmax 3333, 1712, 1667, 1626, 1176, 1059/cm. (Ref. 0744) |
||||||||||||||||
| 191 |  |
Deslanoside / Deacetyllanatoslde C / Desacetyllanatoside C / Desacetyldigilanide C / Purpureaglycoside C / Cedilanid-D / Desace / Desaci / Lanimerck (ampuls) |
(3b,5b,12b)-3-[(O-b-D-glucopyranosyl-(1 to 4)-O-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1 to 4)-O-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1 to 4)-2,6-dideoxy-b-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxycard-20(22)-enolide |
SST0191 | Hideaki Nishino |
C47H74O19 | 943.079 | |
||||||||||||||||||||
| 192 |  |
Desonide / Prednacinolone / D-2083 / Steroderm / Tridesilon |
11,21-Dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione / 11b,16a,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone / 16a-Hydroxyprednisolone-16a,17-acetonide; 11b,21-Dihydroxy-16a,17-isopropylidenedioxy-1,4-pregna-diene-3,20-dione / 16a-Hydroxy-D1-hydrocortisone-16a,17a-acetonide / 16a,17a-Isopropylidenedioxyprednisolone |
SST0192 | Hideaki Nishino |
C24H32O6 | 416.507 | |
nmax: 3401,1709, 1661, 1616, 1603, (inflection), 1087, 1053/cm. (Ref. 0748) |
The acetonide form exerts stronger glucocorticoid activity than parent free steroids. Can make the synthetic non-halogenated corticoids much stronger: in thymus involution and liver glycogen, the acetonide shows 17-times, 13-times stronger activities, respectively (in adrenalectomized immature male rat). One of most synthetic corticoids, one of most active compounds. LD50, 2.4-times higher than prednisolone. Anti-inflammatory action. (Ref. 0748/0749/0750) |
||||||||||||||||||
| 193 |  |
Desoximetasone / A41-304 / R-2113 / HOE304 / Esperson / Topicorte / Topiderm / Topisolon |
9-Fluoro-11b,21-dihydroxy-16a-methylpregna-1,4-diene-3,20-diene-3,20-dione / 9a-Fluoro-16a-methyl-17-desoxyprednisolone / 9a-Fluoro-16a-methyl-D1-corticosterone |
SST0193 | Hideaki Nishino |
C22H29O4F4 | 433.457 | |
Preparation from 3a-hydroxy-11,20-dioxo-16a-methyl-pregnane or 3a-acetoxy-20-oxo-16a-methyl-5b,D9(11)-pregnene. (Ref. 0753) |
217 C (ethyl acetate) (Ref. 0753) |
[a]/D=+109 (chloroform) (Ref. 0753) |
Sol in alcohol, acetone, chloroform, ethylacetate (hot). Slightly sol in ether, benzene. Insol in water, dil. acid, alkaline solution. (Ref. 0753) |
UVmax: 238nm (e=15,750). (Ref. 0753) |
39.8(C-1), 63.5(C-2), 7.2(C-3), 68.2(C-4), 25.6(C-5), 162.1(C-6), 165.3(C-7), 159.0(C-8), 91.3(C-9), 14.45(C-10), 122.0(C-11), 149.5(C-12), 147.8(C-13), 144,3(C-14), 159.6(C-15), 162.1(C-16), 125.3(C-17), 176.4(C-18), 169.7(C-19), -17.4(C20), 123.3(C-21), 170.7(C-16Me) (Ref. 0753) |
Corticoid exerting anti-inflammatory action in application to peripheral skin. Analysis by modified cotton pellet granuloma method. (Ref. 0753) Can make the anti-inflammatory action and thymolytic activity much stronger by 9a-fluoro substitution than 16a-methyl-D1-corticosterone. Potassium diuresis, sodium diuresis. much lower inhibitiory effect to growth than prednisolone and dexamethasone when compared with a dose of same anti-inflammatory action. (Ref. 0754/0755) |
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| 194 |  |
Cortexolone / 17-Hydroxydesoxycorticosterone / Reichstein's Substance S / 11-Desoxycortisone |
17,21-Dihydroxypregn-4-ene-3,20-dione / 4-Pregnene-17a,21-diol-3,20-dione / 17-(1-Keto-2-hydroxyethyl)-4-androsten-17a-ol-3-one / 11-Desoxy-17-hydroxycorticosterone |
SST0194 | Hideaki Nishino |
C21H30O4 | 346.460 | |
207-209 C (Ref. 0757) |
Very sparingly sol in water, ether. Sol in acetone, methanol, alcohol. (Ref. 0757) |
UVmax: 240nm (loge=4.23). (Ref. 0757) |
The acetate, C23H32O5, m.p. 237.2-240.2 , [a]24/D=+116 (acetone), UVmax 242nm (E1%/1cm 448) (Ref. 0758) The monoacetate (pregnene-4-diol-17(b),21-dione-3,20-monoacetate-21), C23H32O5, m.p. 235-238 (formation of sinter at 232), [a]/D=+1184 (c=0.7), lmax=242mm (e=14,700). Strongly and rapidly reduces silver nitrate-ammoniacal solution. Characteristic scarlet-color reaction in conc. sulfate. (Ref. 0272) |
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| 195 |  |
Dexamethasone / Hexadecadrol / Calonat / Decasone / Decacortin / Deronil / Decadron / Fluormone / Dekacort / Dexa-cortisyl / Millicorten / Fortecortin / Anaflogistico / Spoloven / Luxazone / Dectancyl / Dexameth / Dexasone / Dexinoral / Gammacorten / Dextelan / Policort / Dexacortal / Deseronil / Corson / Dergramin / Hexadrol / Deltafluorene / Oradexon / Dexa-cortidelt / Aeroseb-D / Dexinolon / Decaderm / Dexafarma / Cortisumman / Dexasine / Loverine / Maxidex / Dexa-Scheroson |
9-Fuloro-11b,17,21-trihydroxy-16a-methylpregna-1,4-diene-3,20-dione / 9a-Fluoro-16a-methylprednisolone / 16a-Methyl-9a-fluoro-1,4-pregnadiene-11b,17a,21-triol-3,20-dione / 16a-Methyl-9a-fluoro-prednisolone / 1-Dehydro-16a-methyl-9a-fluorohydrocortisone / 16a-methyl-9a-fluoro-D1-hydrocortisone |
SST0195 | Hideaki Nishino |
C22H29O5F | 392.461 | |
Sol in water (10 mg/100 ml at 25 ). Sol in acetone, ethanol, chloroform. (Ref. 0762) |
As the 21-acetate, lmax: 239mm (e=14,900); as the 21-acetate, lmax: 239mm (e=14,500). (Ref. 0762) |
Most active steroid in glucocorticoid activity (Liver glycogen activity in rat), systemic granuloma activity (in intact Holzman rat), and anti-inflammatory action (in human). Negative in sodium retention (rats), less than 1 (human). (Ref. 0762) The eosinopenic activity is 4 to 6-times higher than prednisone and prednisolone in mouse, dog, and human. In granuloma pouch test, 6.5-times higher than prednisolone acetate. In thymus involution (rats) and nitrogen excretion (dogs), 25-times higher than prednisolone acetate and prednison. (Ref. 0762/0763) |
|||||||||||||||||
| 196 |  |
Dichlorisone / Diloderm / Disoderm |
9,11b-Dichloro-17,21-dihydroxy-pregna-1,4-diene-3,20-dione / 9a,11b-Dichloro-1,4-pregnadi-ene-17a,20-diol-3,21-dione / 9a,11b-Dichloroanalog of prednisolone |
SST0196 | Hideaki Nishino |
C21H26O4Cl2 | 413.334 | |
Preparation by halogenation of 1,4,9(11)-pregnatriene-17a,21-diol-3,20-dione-21-acetate. (Ref. 0764) |
238-241 C (Ref. 0764) |
[a]20/D=+134 (pyridine) (Ref. 0764) |
UVmax (methanol): 237nm (e=15,400) (Ref. 0764) |
lNujol/max: 3.0, 5.86, 6.04, 6.22, 6.25m (Ref. 0764) |
[M]/D=+737 (dioxane) (Ref. 0764) |
Antipruritic in peripheral tissues. In granuloma pouch test, strong anti-inflammatory agent. (Ref. 0764) |
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| 197 |  |
Diginin |
3b-(Diginosyloxy)-12a,20a-epoxy-14b,17a-pregn-5-ene-11,15-dione |
SST0197 | Hideaki Nishino |
C28H40O7 | 488.613 | |
155-183 C (unclear melting range). (Ref. 0766) |
UVmax (ethanol): 309nm (loge=1.94), 310nm(loge=2.00) (Ref. 0768) |
(chloroform) 3585(OH), 1735(C=O), 1712(C=O), 1655(C=C), 1095, 1060, 1032(C-O-C), 891, 872, 853(CO-C-O-C) (Ref. 0768) |
Optical rotatory dispersion: in methanol, [M]-13,650 (335 mm, through), +11, 100 (292.5 mm, peak) (Ref. 0768) |
Isolation from the leaves of Digitalis purpurea L., Scrophulariaceae. (Ref. 0765) |
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| 198 |  |
Digitalin / Digitalinum Verum / Digitalinum True / Schmiedeberg's Diginorgin |
SST0198 | Hideaki Nishino |
C36H56O14 | 712.821 | |
Paper chromatography: Rf 0.00 (Ref. 0775) |
In Keller-Kiliani reaction, pink color in sulfate layer, no color in acetic acid layer. (Ref. 0775) |
|||||||||||||||||||
| 199 |  |
Digitonin / Digitin |
SST0199 | Hideaki Nishino |
C56H92O29 | 1229.312 | |
[a]20/D=-40 (pyridine, c=2.6) (Ref. 0778) |
Isolation from seeds of Digitalis purpurea L., Scrophulariaceae. (Ref. 0777) |
Application to quantification of cholesterol in plasma, bile acid, and tissues. (Ref. 0778) |
||||||||||||||||||
| 200 |  |
Dimethisterone / Secrosteron |
17b-Hydroxy-6a-methyl-17-(1-propynyl)androst-4-en-3-one / 6a-Methyl-17-(1-propynyl)testosterone / 6a,21-Dimethyl-17b-hydroxy-17a-pregn-4-en-20-yn-3-one / 6a,21-Dimethylethisterone / 17a-Ethynyl-6a,21-dimethyltestosterone / 17a-Ethynyl-17-hydroxy-6a,21-dimethylandrost-4-en-3-one |
SST0200 | Hideaki Nishino |
C23H32O2 | 340.499 | |
Synthesis from 17a-ethynyl-17b-hydroxy-derivatives of androstane. (Ref. 0779) |
99-102 C (Ref. 0779) |
[a]24/D=+12 (c=1.0) (Ref. 0779) |
Insol in water. Sol in ethanol. Slightly sol in acetone, chloroform. (Ref. 0779) |
UVmax: 241nm (loge=4.16) (Ref. 0779) |
Progestin activity. (Ref. 0779) |
||||||||||||||
| 201 |  |
Dromostanolone Propionate / Drostanolone propionate / Drolban / Emdisterone / Masterid / Masteril / Masterone / Permastril |
2a-Methyl-17b-(1-oxopropoxy)-5a-androstan-3-one / 17b-Hydroxy-2a-methyl-androstan-3-one propionate / 2a-Methylandrostan-17b-ol-3-one propionate / 2a-Methyldihydrotestosterone propionate |
SST0201 | Hideaki Nishino |
C23H36O3 | 360.530 | |
Synthesis by hydrogenation of 2-hydroxymethylene-3-ketoandrostanes. (Ref. 0780) |
126-130 C (Ref. 0780) |
[a]/D=+24 (Ref. 0780) |
Anti-tumor drug. (Ref. 0780) |
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| 202 |  |
Dydrogesterone / Duphaston / Gestatron / Prodel / Retrone |
9b,10a-Pregna-4,6-diene-3,20-dione / 10a-Pregna-4,6-diene-3,20-dione / 6-Dehydro-retro-progesterone / 10a-Isopregnenone |
SST0202 | Hideaki Nishino |
C21H28O2 | 312.446 | |
169-170 C (acetone+hexane). (Ref. 0781) |
[a]25/D=-484.5 (chloroform). (Ref. 0782) |
UVmax: 286nm (e=26,400). (Ref. 0781) |
nmax, 888, 1574, 1617, 1656, 1695/cm. (Ref. 0781) |
High progestin activity to a same degree as 9b,10a-pregn-4-ene-3,20-dione (oral ingestion). Strong elevation of progestin activity in 6-dehydro-progesterone (pregna-4,6-diene-3,20-dione) by introduction of double bond to C6-C7 of progesterone (pregn-4-ene-3,20-dione). (Ref. 0781) |
|||||||||||||||
| 203 |  |
Echujin / Echugin |
SST0203 | Hideaki Nishino |
C42H66O17 | 842.963 | |
165-172 (acetate) (Ref. 0785) |
Toxic glycoside. LD50 i.v. in cats: 0.3mg/kg (Ref. 0520) |
|||||||||||||||||||
| 204 |  |
Enoxolone / Uralenic acid / Biosone |
3b-Hydroxy-11-oxo-20b-olean-12-en-29-oic acid / 3b-Hydroxy-11-oxoolean-12-en-30-oic acid / 18b-Glycyrrhetinic acid |
SST0204 | Hideaki Nishino |
C30H46O4 | 470.684 | |
Plants. Roots of licorice. (Ref. 0789) |
Metabolism. (Ref. 0790) |
Stereochemistry. (Ref. 0788) |
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| 205 |  |
Epiandrosterone / Isoandrosterone |
3b-Hydroxy-5a-androstan-17-one / 3b-Hydroxy-17-androstanone / 3b-Androstanol-17-one / 3b-Hydroxyetioallocholan-17-one |
SST0205 | Hideaki Nishino |
C19H30O2 | 290.440 | |
Animals. The trace amount is present in healthy human urine.(Ref. 0793) |
Androgen activity, weaker than androsterone. (Ref. 0793) |
d-Form: ppt with digitonin. (Ref. 0791) |
|||||||||||||||||
| 206 |  |
Epicholestanol |
5a-Cholestan-3a-ol; 3a-Hydroxycholestane; e-Cholestanol |
SST0206 | Hideaki Nishino |
C27H48O | 388.669 | |
[a]20/D=+32.2 (c=2.0 in chloroform). (Ref. 0366) |
Lower solubility than cholestanol. (Ref. 0794) |
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| 207 |  |
3-Epihexahydroequilenin |
Estra-5,7,9-triene-3a,17a-diol / 5(10),6,8-Estratriene-3a,17a-diol / 5,7,9-Estratriene-3a,17a-diol |
SST0207 | Hideaki Nishino |
C18H24O2 | 272.382 | |
Preparation by reduction of equilenin. (Ref. 0795) |
[a]20/D=+68 (c=0.9 in alcohol) (Ref. 0795) |
Very sol in pyridine. (Ref. 0795) |
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| 208 |  |
Equilin glycol / 7,8-Dihydroxyestrone |
3,7,8-Trihydroxyestra-1,3,5(10)-triene-17-one / 1,3,5-Estratrien-17-one-3,7,8-triol |
SST0208 | Hideaki Nishino |
C18H22O4 | 302.365 | |
Preparation from equilin extracted from pregnant mares. (Ref. 0087) |
II, Sol in water. Slightly sol in organic solvents. (Ref. 0087) |
Estrogen activity. (Ref. 0087) |
Two preparations with high melting point and low melting point. However they are proved to be identical compound by acetylation: shift of m.p. to 211-212 C, [a]26/D= +90 and +92 (in alcohol), respectively. Dehydrogenation of equilin glycol yields 7-ketoestrone, which turns to be 7-hydroxy-estrone by reduction. (Ref. 0087) |
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| 209 |  |
Ergostane |
SST0209 | Hideaki Nishino |
C28H50 | 386.697 | |
Synthesis from allocholanic acid. (Ref. 0796) |
85 C (ether+methanol). (Ref. 0796) |
[a]20/D=+17 (c=2 in chloroform). (Ref. 0796) |
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| 210 |  |
Ergostanol |
SST0210 | Hideaki Nishino |
C28H50O | 402.696 | |
Preparation by hydrogenation of ergosta-14,22-dien-7-one. (Ref. 0797) |
144-145 C (Ref. 0797) |
[a]20/D=+15.9 (c=1.8 in chloroform). (Ref. 0797) |
Ppt with digitonin. (Ref. 0797) |
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| 211 |  |
a-Ergostenol |
Ergost-8(14)-en-3b-ol |
SST0211 | Hideaki Nishino |
C28H48O | 400.680 | |
||||||||||||||||||||
| 212 |  |
b-Ergostenol |
Ergost-14-en-3b-ol |
SST0212 | Hideaki Nishino |
C28H48O | 400.680 | |
a-Preparation by treatment of ergostenol with HCl-gas in chloroform. (Ref. 0800) |
141 C (alcohol). (Ref. 0800) |
[a]20/D=+21.2 (c=0.9 in chloroform) (Ref. 0800) |
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| 213 |  |
g-Ergostenol |
Ergost-7-en-3b-ol / 3b-Hydroxergost-7-ene |
SST0213 | Hideaki Nishino |
C28H48O | 400.680 | |
146 C (isopropanol) (Ref. 0802) |
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| 214 |  |
Escigenin / Aescigenin |
16a,21a-Epoxyolean-12-ene-3b,22a,23,28-tetrol |
SST0214 | Hideaki Nishino |
C30H48O5 | 488.699 | |
UVmax (anhydrous alcohol): 275nm (loge=1.58) (Ref. 0804) |
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| 215 |  |
Escin / Aescin / Aescusan / Reparil |
SST0215 | Hideaki Nishino |
|
Plants. Saponin produced in seeds of Aesculus hippocastanum L., Hippocastanaceae horse chestnut tree.(Ref. 0810) |
a-Escin, LD50 in mice, rats, guinea pigs: 320, 720, 475 mg/kg orally; 3.2, 5.4, 15.2 mg/kg i.v. hemolytic index; 1:20,000. b-Escin, hemolytic index; 1:40,000. LD50 in mice, rats, guinea pigs: 134, 400, 188mg/kg orally; 1.4, 2.0, 7.2mg/kg i.v., respectively. (Ref. 0816) |
Ppt with cholesterol. Escin can be separated into two isomers, a-escin and b-escin, because of different properties in melting point, optical rotation, hemolytic index, solubility in water. (Ref. 0805) Escin had ever been regarded as an glycoside from aescigenin (C30H48O5). Isolation and purification by chromatography. (Ref. 0811/0812/0813) Escin is a mixture of two major Glycosides. The aglycon is protoescigenin, which is acylated at C-22 with acetic acid. The sugar parts are composed of Glucuronic acid and two D-Glucose molecules. The difference in two main glycosides is based on acylated compound at C-21, angelic acid or tiglic acid. Hydroxyl group at C-3 is linled to D-glucuronic acid, which is connected to 2 molecules of D-glucose at 2, 4-positions. One of D-glucose molecules is often substituted with D-xylose or D-galactose. (Ref. 0814/0815) |
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| 216 |  |
Estranediol B / 3,17-Dihydroxyestrane / Octahydrofollicular Hormone / Octahydroestrone / Hexahydrodesoxyestriol / Hexahydroestradiol |
Estrane-3a,17a-diol |
SST0216 | Hideaki Nishino |
C18H30O2 | 278.430 | |
Preparation along with stereoisomer by hydrogenation of estrone. The diacetate, C22H34O4, crystallization from methanol. M.p.160 (Ref. 0818) |
Animals. Presence in urine of non-pregnant women. Formed by non-enzymic reduction of estrone. (Ref. 0818) |
Estrogenic hormone (Ref. 0818) |
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| 217 |  |
5,6,8-Estratrien-3b-ol-17-one / 5,7,9-Estratrien-3b-ol-17-one |
SST0217 | Hideaki Nishino |
C18H22O2 | 270.366 | |
138-139.5 C (Ref. 0420) |
Insol in water. Sol in alcohol, ether, other organic solvents. (Ref. 0420) |
UVmax: 269.5, 278mm (e=345,240), shoulder at 278mm. UVmin: 249, 276mm (e=95,233) (Ref. 0420) |
Animals. Urine of pregnant mares. Pure praparation weighing about 160mg was obtained from 10,000 gallon of urine. (Ref. 0420) |
Ring B is benzenoid, not ring A, so bond isomer of estrone. Not ppt with digitonin. The oxime, C18H23NO2, m.p. 195-197 (dec.). The acetate, C18H21O(OCOCH3), m.p.158. The benzoate, C25H26O3, m.p.196-198. Strong positive in the Liebermann-Burchard reaction and Salkowski reaction. The latter reaction is reversible like ergosterol. Negative in Rosenhelm test. Deep yellow color reaction by tetranitromethane. (Ref. 0420) |
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| 218 |  |
Ethylestrenol / Orabolin / Durabolin-O / Orgaboral / Maxibolin / Orgabolin (Obsolete) |
19-Nor-17a-pregn-4-en-17-ol / 17a-Ethylestr-4-en-17b-ol / 17a-Ethyl-17b-hydroxy-4-estrene / 17b-Hydroxy-17a-ethyl-19-nor-4-androstene |
SST0218 | Hideaki Nishino |
C20H32O | 288.467 | |
Synthesis from 19-nortestosterone as a starting material. (Ref. 0819) |
76-78 C (Ref. 0819) |
[a]/D=+31 (chloroform) (Ref. 0819) |
Anabolic action. Strong progestational agent, at least same activity as already known D4-3-ketones. (Ref. 0819) |
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| 219 |  |
Fludrocortisone / 9a-Fluorohydrocortisone / 9a-Fluorocortisol / Fluodrocortisone / Fluohydrisone / Fluohydrocortisone / Alflorone / Astonin-H / F-Cortef / Florinef / Fludrocortone |
9-Fluoro-11b,17,21-trihydroxypregn-4-ene-3,20-dione / 9a-Fluoro-17-hydroxycorticosterone |
SST0219 | Hideaki Nishino |
C21H29O5F | 380.450 | |
Preparation from 4-pregnen-9b,11b-oxido-17a,21-diol-3,20-dione 21-acetate. Preparation from 9a-fluorohydrocortisone acetate by deacetylation with sodium methylate. (Ref. 0820) |
260-262 C (dec.). (Ref. 0820) |
[a]23/D=+139 (c=0.55 in 95% ethanol). (Ref. 0820) |
Sol in water. (Ref. 0820) |
UVmax (ethanol): 239nm (e=17,600). (Ref. 0820) |
lNujol/max 3.0m(OH), 5.84m(20-carbonyl), 6.07m, 6.20m(D4-3-ketone) (Ref. 0820) |
Anti-inflammatory effect. Application to domestic animals as as adrenocortical steroid. (Ref. 0820) |
Several times increase in glucocorticoid activity by halogenation. (Ref. 0820) |
||||||||||||
| 220 |  |
Flumedroxone acetate / WG537 / Demigran |
17-(Acetyloxy)-6a-(trifluoromethyl)pregn-4-ene-3,20-dione / 17-Hydroxy-6a-(trifluoromethyl)pregn-4-ene-3,20-dione acetate / 17-Acetoxy-6a-(trifluoromethyl)progesterone / 17-Hydroxy-6a-(trifluoromethyl)progesterone acetate / 6a-(Trifluoromethyl)-17-hydroxyprogesterone acetate |
SST0220 | Hideaki Nishino |
C24H31O4F3 | 440.496 | |
Preparation by UV-irradiation of 17a-acetoxyprogesterone-3-ethyl enol ether in trifluoroiodomethane-pyridine, followed by hydrolysis of the product, 6-trifluoromethyl-17a-acetoxypregesterone-3-ethyl enol ether. (Ref. 0821) |
206-207 C (Ref. 0821) |
[a]20/D=+30 (Ref. 0821) |
UVmax (ethanol): 234nm(e=15,600) (Ref. 0821) |
Oral progestational activity (Clauberg assay, modified by McPhail) is 1 to 2 when relative activity of 6a-methyl-17a-acetoxyprogesterone is 1. (Ref. 0821) |
Remarkable increase in oral progestational activity by introduction of a-fluorine, chlorine, or bromine to C-6 of 17a-acetoxyprogesterone. (Ref. 0821) |
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| 221 |  |
Flumethasone / 6a-Fluorodexamethasone / Aniprime / Cortexilar / Flucort / Methagon |
6a,9-Difluoro-11b,17a,21-trihydroxy-16a-methylpregna-1,4-diene-3,20-dione / 6a,9a-Difluoro-16a-methylprednisolone |
SST0221 | Hideaki Nishino |
C22H28O5F2 | 410.452 | |
Preparation by dehydration of 6a-fluoro-16a-methyl Substance S in mesyl chloride and pyridine-dimethylformamide. (Ref. 0822) |
Glucocorticoid, anti-inflammatory action, application to domestic animals as an adrenocortical steroid. Promotion of sodium ion excretion. (Ref. 0822) The strongest anti-inflammatory effect among 6a-fluoro-16a-methylcorticoids: hydrocortisone, 1; 6a-fluoro-16a-methylprednisolone acetate, 60; 6a,9a-difluoro-16a-methylhydrocortisone acetate, 65; 6a,9a-difluoro-16a-methylprednisolone acetate, 300. High effect on patients suffering from rheumatoid arthritis according to clinical test in Mexico and USA. (Ref. 0823) |
Four substitutions, D1-double bond, 6a-fluorine, 9a-fluorine, and 16a-methylgroup increase anti-inflammatory effect, respectively. (Ref. 0822) |
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| 222 |  |
Fluocinolone acetonide / Dermalar / Jellin / Localyn / Fluovitef / Fluocinil / Synamol / Synsac / Synandone / Synalar |
6a,9-Difluoro-11b,21-dihydroxy-16a,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione / 6a,9a-Difluoro-11b,16a,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone / 6a,9a-Difluoro-16a-hydroxyprednisolone 16,17-acetonide / 6a,9a-Difluoro-16a,17a-isopropylidenedioxy-1,4-pregnadiene-3,20-dione |
SST0222 | Hideaki Nishino |
C24H30O6F2 | 452.488 | |
Praparation by acetate-treatment of 6a,9a-difluoro-16a-hydroxyprednisolone, which is synthesized from available 16a,17a-oxido-D5-pregnene-3b,21-diol-20-one 21-acetate. (Ref. 0824) |
265-266 C (acetone+hexane). (Ref. 0824) |
[a]/D=+95 (chloroform). (Ref. 0824) |
UVmax: 238nm (loge=4.21). (Ref. 0824) |
Observation of IR spectra. (Ref. 0825) |
Glucocorticoid activity. High anti-inflammatory action (no sodium retention). Application to domestic animals as an adrenocortical steroid in peripheral tissues. Anti-inflammatory action; 100-times higher than hydrocortisone. High suppressor effect on allergy reactions like rheumatoid arthritis and asthma in clinical trial. (Ref. 0824) |
||||||||||||||
| 223 |  |
Fluocortolone / Ultralan Oral |
6a-Fluoro-11b,21-dihydroxy-16a-methylpregna-1,4-diene-3,20-dione / 6a-Fluoro-16a-methyl-1-dehydrocorticosterone / 6a-Fluoro-16a-methyl-D1,4-pregnadiene-11b,21-diol-3,20-dione |
SST0223 | Hideaki Nishino |
C22H29O4F | 376.462 | |
Synthesis by substrate-structure-directed specific 11b-hydroxylation in Curvularia lunata. (Ref. 0827) |
188-190.5 C. (Ref. 0826) |
[a]20/D=+100 (dioxane). (Ref. 0826) |
Metabolism after i.v. injection, oral ingestion. Isolation as fluocortolone-21-carbonic acid in soluble form from urine. (Ref. 0830) No influence on nitrogen balance. Inhibitory effect on removal of 17-ketosteroids, 17-hydroxy-corticosteroids into urine by 50%, 55-65%, respectively (human, 20 to 60mg/day). (Ref. 0831) |
Glucocorticoid activity: 3 to 10 times higher than hydrocortisone acetate (ED50, 0.003 to 0.01 (mg/animal/day) in mouse gluconeogenesis). In granuloma pouch, ED50: 0.0005 (0.0002 to 0.001) (topical), 0.02 (0.01 to 0.04) (subcutaneous), 0.02 (0.01-0.03) (oral) (mg/animal/day). Thymolytic activity, 17 times higher than hydrocortisone acetate (ED50, 0.006 (0.003 to 0.013) mg/animal/day), Promotion of sodium-potassium excretion. (Ref. 0826/0828) Less suppressor effect to Cortisol secretion by 10mg Fluocortolone than by 45mg STC407 (6-dehydro-16-methylene-hydrocortisone). (Ref. 0829) |
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| 224 |  |
Fluoxymesterone / Androsterolo / Androfluorene / Androfluorone / Fluotestin / Halotestin / Oratestin / Oratestryl / Testoral / Ultandren. |
9-Fluoro-11b,17b-dihydroxy-17-methylandrost-4-en-3-one / 11b,17b-Dihydroxy-9a-fluoro-17a-methyl-4-androsten-3-one / 9a-Fluoro-11b-hydroxy-17a-methyltestosterone |
SST0224 | Hideaki Nishino |
C20H29O3F | 336.441 | |
Synthesis by utilization of reaction with Grignard reagent from 11b-hydroxy-4-androstene-3,17-dione. (Ref. 0832) |
270 C (dec.) (Ref. 0832) |
[a]/D=+109 (ethanol) (Ref. 0832) |
UVmax (methanol): 240nm(e=16,700) (Ref. 0832) |
Strong androgen activity. Anabolic activity, androgenic activity; ;20.0, 9.5 in fluoxymesterone; 1, 1 in 17-methyltestosterone (oral ingestion). (Ref. 0832) |
Reaction of fluoxymesterone with chromium trioxide in acetic acid yields 17b-hydroxy-9a-fluoro-17-methyl-4-androstene-3,11-dione (m.p. 213-220 (dec.), [a]/d=+144 (chloroform), C20H27O3F, anabolic activity, androgenic activity; 22, 8.5; 1, 1 in 17-methyltestosterone, respectively. Stronger anabolic activity than fluoxymesterone. (Ref. 0832) |
||||||||||||||
| 225 |  |
Fluperolone acetate / P-1742 / ALAcortril / Methral |
17(S9-[2-(Acetyloxy)-1-oxo-propyl]-9-fluoro-11b,17a-dihydroxyandrosta-1,4-dien-3-one / 9-Fluoro-11b,17a-dihydroxy-17(S)-lactoylandrosta-1,4-diene-3-one 17b-acetate / 9a-Fluoro-11b,17a,21-trihydroxy-21-methylpregna-1,4-diene-3,20-dione 21-acetate / 17b-[2-Acetoxypropionyl]-9a-fluoro-11b,17-dihydroxyandrosta-1,4-dien-3-one / 21-Methyl-9a-fluoroprednisolone acetate / 9a-Fluoro-21-methyl-1,4-pregnadiene-11b,17a,21B-triol-3,20-dione 21-acetate |
SST0225 | Hideaki Nishino |
C24H31O6F | 434.498 | |
215-253 C (Ref. 0833) |
[a]/D=+87 (Ref. 0833) |
UVmax: 239nm (e=15,350) (Ref. 0833) |
No electrolyte-regulating activity, raises only slight natriuresis in adrenalectomized rats. In granuloma pouch test, one sixth anti-inflammatory effect of 9a-fluoroprednisolone acetate. Through 21-methyl substitution, can remove completely the strong sodium retention activity from 9a-fluoroprednisolone molecules and leaves anti-inflammatory effect. (Ref. 0833) |
Synthesized several C21 epimers. (Ref. 0833) Among six species of topical steroids as medicine, in vasoconstrictor test, 10 (3 to 35) when with fluocinolone acetnide is 100, in rank third, in subcutaneous thymolytic test, 21(11 to 27) in mice (rank second) and 16 in rats (rank third) when with betamethasone alcohol is 100. (Ref. 0835) |
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| 226 |  |
Fluprednidene acetate / Fluprednylidene 21-acetate / StL 1106 / Etacortin / Decoderm sine Gentamycin |
21-(Acetyloxy)-9-fluoro-11b,17-dihydroxy-16-methylenepregna-1,4-diene-3,20-dione / 9a-Fluoro-11b,17,21-trihydroxy-16-methylenepregna-1,4-diene-3,20-dione 21-acetate / 9a-Fluoro-16-methylene-D1,4-pregnadiene-11b,17,21-triol-3,20-dione 21-acetate / 16-Methylene-9a-fluoroprednisolone 21-acetate / 9a-Fluoro-16-methyleneprednisolone 21-acetate |
SST0226 | Hideaki Nishino |
C24H29O6F | 432.482 | |
t4.74, 4.94 (C-16=CH2). |
Anti-inflammatory medicine (topical). (Ref. 0838) |
||||||||||||||||||
| 227 |  |
Flurogestone acetate / Flugestone acetate / Chronogest / SC-9880 / Cronolone / Synchronate |
17-(Acetyloxy)-9-fluoro-11b-hydroxypregn-4-ene-3,20-dione / 9-Fluoro-11b,17-dihydroxypregn-4-ene-3,20-dione-17-acetate / 17a-Acetoxy-9a-fluoro-11b-hydroxyprogesterone / 9-Fluoro-11b,17-dihydroxyprogesterone 17-acetate |
SST0227 | Hideaki Nishino |
C23H31O5F | 406.488 | |
Synthesis by reaction of 16,17a-epoxy-4,9(11)-pregnadiene-3,20-dione with hydriodic acid in acetic acid. (Ref. 0839) |
266-269 C (benzen+petr. ether or ethyl acetate+petr. ether) (Ref. 0839) |
[a]20/D=+77.6 (in chloroform) (Ref. 0839) |
UVmax (methanol): 238nm(e=17,500) (Ref. 0839) |
Progestin activity. Application to regulation of the estrus (mating time) in domestic animals as a progestational agent. In Clauberg assay, oral ingestion, 25-times higher activity than subcutaneous progesterone. Compared with oral progesterone, 2500-times higher activity, 25-times higher than norlutin, 5-times higher than 6a-methyl-17a-acetoxy-progesterone. (Ref. 0839) |
|||||||||||||||
| 228 |  |
Formocortal / FI 6341 / fluoroforymlon / Cortocin-F / Cutisterol / Deflamene / Fluderma |
21-(Acetyloxy)-3-(2-chloroethoxy)-9-fluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-20-oxopregna-3,5-diene-6-carboxaldehyde / 3-(2-Chloroethoxy)-9-fluoro-11b,16a,17,21-tetrahydroxy-20-oxopregna-3,5-diene-6-carboxaldehyde,cyclic 16,17-acetal with acetone,21-acetate / 3-(2-Chloroethoxy)-6-formyl-9a-fluoropregna-3,5-diene-11b,16a,17,21-tetrol-20-one 21-acetate 16a,17a-acetonide / 3-(2-Chloroethoxy)-9a-fluoro-6-formyl-11b,21-dihydroxy-16a,17a-isopropylidenedioxypregna-3,5-dien-20-one |
SST0228 | Hideaki Nishino |
C29H38O8FCl | 569.058 | |
Synthesis from 9a-fluoro-cortisone-21-acetate 3-cycloethyleneketal as the starting material. (Ref. 0840) |
180-182 C (ether-petroleum ether). (Ref. 0840) |
[a]20/D=+26 (chloroform). (Ref. 0840) |
UVmax (ethanol): 216, 324nm (e=12,100, 17,100). (Ref. 0840) |
Glucocorticoid action. In granuloma pouch assay, ED50; topical, 0.001mg; oral, 0.105mg. Relative potency (F-acetate, 1); in granuloma pouch assay, 680 in topical, 36 in oral, s.c., 23; cotton pellets, 6.5 in topiocal; hepatic glycogen, 130; inhibition of total plasmatic corticosterone (FOH=1), 29. (Ref. 0840) |
|||||||||||||||
| 229 |  |
Formyldienolone / Esiclene |
11a,17b-Dihydroxy-17-methyl-3-oxoandrosta-1,4-diene-2-carboxaldehyde / 2-Formyl-17a-methylandrosta-1,4-diene-11a,17b-diol-3-one / 2-Formyl-11a-hydroxy-D1-methyltestosterone |
SST0229 | Hideaki Nishino |
C21H28O4 | 344.445 | |
209-212 C (ethyl acetate) (Ref. 0842) |
[a]25/D=-105 (chloroform) (Ref. 0842) |
Sol in water. (Ref. 0842) |
Method for synthesis of tritium-labeled formyldienolone and the metabolism. In oral ingestion, the blood concentration reached the maximum at 2 h and slowly decreased for the course of 22 h. Highest radioactivity in liver. Detected as little as 4% in urine. Recovered 42% in feces. (Ref. 0842) |
Anabolic steroid action. (Ref. 0841) |
|||||||||||||||
| 230 |  |
Friedelin |
D:A-Friedooleanan-3-one / friedelan-3-one |
SST0230 | Hideaki Nishino |
C30H50O | 426.717 | |
261-265 C (Ref. 0844) |
Sol in chloroform (1 g/8.6 ml), 99% alcohol (1 g/264 ml). (Ref. 0844) |
||||||||||||||||||
| 231 |  |
Fungisterol |
Ergosta-6,8,22-trien-3b-ol / D6:7,8:9,:22:23-Ergostatriene-3-ol |
SST0231 | Hideaki Nishino |
C28H44O | 396.648 | |
147.5 C (alcohol+ether+ethyl acetate) (Ref. 0848) |
[a]15/D=-21.9 (chloroform) (Ref. 0848) |
e 283mm = 9980 (Ref. 0848) |
Bacteria, molds. Purification from sterol crystal of Penicillium chrysogenum. (Ref. 0848) |
Investigation on the biosynthetic pathway of fungisterol. (Ref. 0851) |
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| 232 |  |
Funtessine |
3b-Amino-5a-conanin-12b-ol |
SST0232 | Hideaki Nishino |
C22H38ON2 | 346.550 | |
194-195 C (methanol) (Ref. 0852) |
[a]/D=+49 (c=1 in chloroform) (Ref. 0852) |
Plants. Barks of Funtumia latifolia Stapf., Apocynaceae. (Ref. 0852) |
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| 233 |  |
Gestonorone caproate / Gestronol caproate / SH 582 / Depostat |
17-Hydroxy-17-norpregn-4-ene-3,20-dione hexanoate / 17a-Hydroxy-19-norprogesterone caproate / 17-Hydroxyestr-4-ene-3-one hexanoate |
SST0233 | Hideaki Nishino |
C26H38O4 | 414.578 | |
Synthesis from pregnadienolone or pregnadienolone-3-acetate as the starting material. Can obtain biologically active compounds from the product through successive several reactions. Can remove 19-methyl group by aromatization of D1,4-3-Keto-compound or intramolecular odidation. (Ref. 0853) |
123-124 C (Ref. 0853) |
[a]/D=+13 (chloroform) (Ref. 0853) |
UVmax: 239nm (e=17,540) (Ref. 0853) |
Effect on excretion of estrogen, 17-ketosteroids, 17-hydroxycorticosteroids, pregnanetriol into urine by intramuscular injection. (Ref. 0853) |
Application to therapy for prostate hypertrophy. (Ref. 0854) |
||||||||||||||
| 234 |  |
F-gitonin / Gitogenin b-Lycotetraoside |
O-b-D-Glucopyranosyl-(1-2glc1)-O-b-D-xylopyranosyl-(1-3glc1)-O-b-D-glucopyranosyl-(1-4)-O-b-D-galactopyranosyl 25D,5a-spirostane-2a,3b-diol (gitogenin b-lycotetraoside) |
SST0234 | Hideaki Nishino |
C50H82O23 | 1051.172 | |
nmax: 862, 898, 924, and 982/cm (intensity 898  924) (Ref. 0856) |
Plants. Saponin extracted from leaves of Digitalis purpurea L., Scrophulariaceae. (Ref. 0855) |
Application as a cardiotonic medicine. (Ref. 0855) |
|||||||||||||||||
| 235 |  |
Gitoxin / Anhydrogitalin / Bigitalin / Pseudodigitoxin |
3b-[(O-2,6-Dideoxy-b-D-ribo-hexopyranosyl-(1-4)-O-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-b-D-ribo-hexopyranosyl)oxy]-14,16b-dihydroxy-5b-card-20(22)-enolide |
SST0235 | Hideaki Nishino |
C41H64O14 | 780.938 | |
Insol in chloroform, ethylacetate, acetone. Sol in mixture of chloroform with alcohol or pyridine, dil. alcohol. (Ref. 0859) |
lmax = 219mm (E1%/1cm=191) (Ref. 0860) |
Application as a cardiotonic medicine. In cats, average lethal dose is 0.443 0.014mg. (digitoxin, 0.3750.015 mg, so gitoxin possesses 83% toxicity of digitoxin) (Ref. 0860) |
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| 236 |  |
Gypsogenin / Githagenin / Albasapogenin / Gypsophilasapogenin |
3b-Hydroxy-23-oxooleann-12-en-28-oic acid |
SST0236 | Hideaki Nishino |
C30H46O4 | 470.684 | |
sol in hot water, ether. (Ref. 0865) |
Gypsogenin is identical to githagenin. The acetate, sintering 173 , m.p. 188-189, [a]/D=+79 (c=6.70 in chloroform). The methyl ester of the acetate, m.p. 191, [a]/D=+80 (c=1.318 in chloroform) (Ref. 0865) |
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| 237 |  |
Halcinonide / SQ-18,566 / Halciderm / Halog |
21-Chloro-9-fluoro11b-hydroxy-16a,17-[(1-methylethylidene)bis(oxy)]pregn-4-ene-3,20-dione / 21-Chloro-9-fluoro-11b,16a,17-trihydroxypregn-4-ene-3,20-dione cyclic 16,17-acetal with acetone / 21-Chloro-9a-fluoro-11b-hydroxy-16a,17a-isopropylidenedioxy-4-pregn-ene-3,20-dione / 9a-Fluoro-21-chloro-11b,16a,17a-trihydroxypregn-4-ene-3,20-dione 16,17-acetonide. |
SST0237 | Hideaki Nishino |
C24H32O5FCl | 454.959 | |
Synthesis from 21-chloro-9a-fluoro-11b,16a,17a-trihydroxy-4-pregnene-3,20-dione as a starting material. (Ref. 0866) |
264-265 C (acetone-petr. ether) (Ref. 0866) |
[a]25/D=+155 (chloroform) (Ref. 0866) |
Sol in acetone, ethylacetate, petroleum ether. (Ref. 0866) |
UVmax (methanol): 238 nm (e=16,400) (Ref. 0866) |
nmax: 3425, 1725, 1660, 1620, 860/cm (Ref. 0866) |
Application as a topical anti-inflammatory medicine. In thymus involution assay, it has been resolved that the introduction of chloride to C21 make the activity increased, and D4-form exerts higher effect than D1,4-form. No introduction of sodium retention activity in Salt-loaded adrenalectomized rats. (Ref. 0866) Rank as topical anti-inflammatory agent in vasocontrictor assay and stripped-skin assay: equivalent to those of betamethasone valerate (9a-fluoro-11b,17a-21-trihydroxy-16bmethylpregna-1,4-diene-3,20-dione 17-valerate) and SQ15,361 (9a-fluoro-21-chloro-11b,16a,17a-trihydroxypregna-1,4-diene 3,20-dione,16,17-acetonide), and higher activities than SQ20,589 (21-chloro-11b,16a,17a-trihydroxypregna-1,4-diene 3,20-dione,16,17-acetonide) and SQ20,811 (21-chloro-11b,16a,17a-trihydroxypregn-4-ene-3,20-dione,16,17-acetonide). (Ref. 0867) |
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| 238 |  |
Haloprogesterone / Prohalone |
17-Bromo-6a-fluoropregn-4-ene-3,20-dione / 17a-Bromo-6a-fluoroprogesterone / 6a-Fluoro-17a-bromoprogesterone |
SST0238 | Hideaki Nishino |
C21H28O2FBr | 411.348 | |
Sol in acetone, glacial acetic acid. (Ref. 0868) |
nKBr/max: 1621, 1680, (D4-3-ketone doublet), 1704 (20-ketone)/cm (Ref. 0869) |
First derivative of 6.17-dihalogenated progesterone. (Ref. 0869) |
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| 239 |  |
Hederagenin / Caulosapogenin / Melanthigenin |
3b-23-Dihydroxyolean-12-en-28-oic acid |
SST0239 | Hideaki Nishino |
C30H48O4 | 472.700 | |
332-334 C (alc.) (Ref. 0875) |
[a]20/D=+81 (c=0.7 in pyridine). (Ref. 0875) |
Sol in pyridine. Also sol in a mixture of chloroform and alcohol. Slowly sol in alcohol. Insol in water. Sol in dil. alcoholic NaOH. Insol in alkali solution. (Ref. 0872) |
emax: 2860 at 210 mm. (Ref. 0874) |
Plants. Glycoside isolated from petals of Polyscias nodosa or Hedera helix. (Ref. 0870) Glycoside extracted from aril of fruit seed of Ackee (Blighia sapida Koenig). (Ref. 0872) Isolation as acid Sapogenin, Melanthigenin, yielded by hydrolysis of alcohol extract of delipidated seed of Nigella sativa L. (Ranunculaceae). (Ref. 0873) Isolation as Caulosapogenin by hydrolysis of aqueous-ethanolic solution of a saponin, Caulosaponin, from bloom stalks of Clematis vitalba Linn, (Ranunculaceae), Caulophyllum thalictroides, Linn, Michaux (Berberidaceae). (Ref. 0874) |
Aglycon of saponin inducing hemolysis of rabbit blood. (Ref. 0872) |
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| 240 |  |
a-Hederin / Helixin (the saponin) |
SST0240 | Hideaki Nishino |
C41H66O12 | 750.956 | |
[a]20/D=+14.5 (c=0.92 in methanol) (Ref. 0879) |
Hemolytic index, 1:150000; LD50 (rat), 4.5mg/kg; Preventive activity to edema. 1.1mg/kg. (Ref. 0879) |
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| 241 |  |
Hellebrin / Hellebrigenin / Glucorhamnoside |
3b-[(6-Deoxy-4-O-b-D-glucopyranosyl-a-L-mannopyranosyl)oxy]-5b,14-dihydroxy-19-oxobufa-20,22-dienolide |
SST0241 | Hideaki Nishino |
C36H52O15 | 724.789 | |
283-284 C (hot methanol) (Ref. 0880) |
Sol in dil. alcohol. Slightly sol in water. Insol in ether. (Ref. 0880) |
lmax = 300 mm (logE1%/1cm=1.96) (Ref. 0880) |
Plants. Glycoside extracted from rhizome of Helleborus niger L., Ranunculaceae. (Ref. 0880) 0.30-1.5% Hellebrin included in the rhizome of Helleborus viridis, H. odorus, H. multifidus, H. dumetorum subsp. atrorubens, H. purpurascens, H. cyclophyllus, and H. bocconei subsp. siculus. Trace amount of Hellebrin in the rhizome of H. orientalis. No hellebrin in H. foetidus, H. lividus subsp. corsicus, H. niger (several samples investigated), H. vesicarius. (Ref. 0881) |
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| 242 |  |
Holarrhenine |
3b-(Dimethylamino)con-5-enin-12b-ol / 12b-Hydroxyconessine |
SST0242 | Hideaki Nishino |
C24H40ON2 | 372.587 | |
Insol in water. Sol in alcohol, chloroform. Slightly sol in ether, acetone, ethylacetate. (Ref. 0882) |
Plants. Extraction from leaves and barks of Holarrhena congolensis Stapf, Apocynaceae. (Ref. 0882) |
The hydrobromide, C24H38N2O, 2HBr, Molecular mass 532.3. [a]/D=+11 or +12.1 (anhydrous salt) (Ref. 0882) Evidence for identification to 12b-hydroxy-5a-pregnane prepared from hydrolysis of hecogonin as a hydroxy 5a-pregnane through Hofmann reaction and Emde reaction. Confirmation of holarrhenin structure as 12b-hydroxyconessin. (Ref. 0884) |
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| 243 |  |
Hydrallostane / Allodihydrohydrocortisone / Allodihydro F |
11b,17a,21-Trihydroxy-5a-pregnane-3,20-dione / 11b,17a,21-Trihydroxyallopregnane-3,20-dione / Allopregnane-11b,17a,21-triol-3,20-dione; 4,5a-Dihydrocortisol / 5a-Dihydrohydrocortisone |
SST0243 | Hideaki Nishino |
C21H32O5 | 364.476 | |
[a]25/D=+83 (acetone) (Ref. 0887) |
Insol in water. Sol in methanol, acetone, chloroform. (Ref. 0887) |
nKBr/max: 3640, 2400, 1705 (broad)/cm (Ref. 0887) |
Animals. Extraction from adrenal glands of bovine and swine. (Ref. 0885) |
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| 244 |  |
Hydrocortisone / Cortisol / Ala-Cort / Cremesone / Cobadex / Cort-dome / Cortef / Cortifoam / Cortril / Dome cort / Efcorbin / Efcorlin / EF-cortelan / Efcortelin / Reichstein's Substance M / Scheroson F / Sigmacort / Texacort / Demacort / Proctocort / Epicort / Ficortril / Genacort (Lotion) / Hidro-colisona / HVB / Hydro-adreson / Hydrocortisyl / Hydrocortone / Lubricort / Meusicort |
11b,17,21-Trihydroxypregn-4-ene-3,20-dione-4-pregnene-11b,17a,21-triol-3,20-dione / 17-Hydroxycorticosterone |
SST0244 | Hideaki Nishino |
C21H30O5 | 362.460 | |
Sol in water (0.28 mg/ml, 25 ), ethanol (15.0 mg/ml), methanol (6.2 mg/ml), acetone (9.3 mg/ml), chloroform (1.6 mg/ml), propyleneglycol (12.7 mg/ml), ether (about 0.35 mg/ml). (Ref. 0295) |
UVmax: 242nm (E1%/1cm=445) (Ref. 0889) |
Complete identification in IR spectra. (Ref. 0892) |
Animals. Isolation from adrenal glands. (Ref. 0295/0888) Found in urine of Cushing's syndrome accompanied with severe diabetes. (Ref. 0889) Extraction from blood in adrenal glands of dogs dosed with ACTH. (Ref. 0890) Conversion from cholesterol in adrenal glands. (Ref. 0893) Synthesis from 11-oxygenation of 11-desoxy-17-hydroxycorticosterone in Streptomyces fradiae. (Ref. 0894) |
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| 245 |  |
Hydroxydione sodium / Hydroxydione succinate / Presuren / Viadril |
21-(3-Carboxy-1-oxopropoxy)-5b-pregnane-3,20-dione sodium salt / 21-Hydroxypregnane-3,20-dione sodium hemisuccinate |
SST0245 | Hideaki Nishino |
C25H35O6Na | 454.532 | |
Synthesis as a sodium salt by Palladium-reduction and acetic anhydride-treatment of deoxycorticosterone. (Ref. 0895) |
195-197 C (free acid) (Ref. 0895) |
[a]20/D=+95 (in chloroform, free acid) (Ref. 0895) |
Sol in water. Also sol in mild alkaline buffer, acetone, chloroform. (Ref. 0895) |
UVmax: 280nm (e=93.2) (Ref. 0895) |
Soluble steroid applied to human, mouse, rat, cat, dog, and monkey as an anesthetic. AD50 21.5mg/kg, LD50 250mg/kg, TI(LD50/AD50) 11.5. More excellent than thiopental sodium (TI, 4) (i.v. injection). (Ref. 0895) |
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| 246 |  |
17-Hydroxy-16-methylene-D6-progesterone / 17-Hydroxy-16-methylenepregna-4,6-diene-3,20-dione / 6-Dehydro-17a-hydroxy-16-methyleneprogesterone |
SST0246 | Hideaki Nishino |
C22H28O3 | 340.456 | |
Synthesis from 3b-acetoxy-16b-methyl-16a,17b-oxido-D5-pregnen-20-one as a starting material. (Ref. 0896) |
196.5-197 C (methanol) (Ref. 0896) |
Sol in benzene, caproic acid anhydride. (Ref. 0896) |
UVmax: 283nm (loge=4.51) (Ref. 0896) |
881, 1597, 1630, 1658, 1672 (D4,6-3-ketone), 1705 (H-bridge), 1724(20-CO), 3480(assoc,OH), 3610(free OH)/cm (Ref. 0896) |
Application as an oral progestogen. (Ref. 0896) |
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| 247 |  |
17a-Hydroxyprogesterone 3-cyclopentyl enol ether / 3-(Cyclopentyloxy)-17-hydroxypregna-3,5-dien-20-one |
SST0247 | Hideaki Nishino |
C26H38O3 | 398.578 | |
Synthesis as 17a-acetate. (Ref. 0897) |
184.5-186.5 C (Ref. 0897) |
[a]/D=-115 (dioxane) (Ref. 0897) |
Application as progestin. (Ref. 0897) |
17a-Acetoxyprogesterone 3-cyclopentylenol ether, Gestovis, solid, m.p. 137-138 , [a]/D=-147 (dioxane) (Ref. 0897) |
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| 248 |  |
8-Isoestrone / 8a-Estrone / 8-Epiestrone |
3-Hydroxy-8a-estra-1,3,5(10)-trien-17-one / D1.3.5-8-Epiestratrien-3-ol-17-one |
SST0248 | Hideaki Nishino |
C18H22O2 | 270.366 | |
[a]20/D=+94 (dioxane) (Ref. 0086) |
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| 249 |  |
Jervine |
(3b,23b)-17,23-Epoxy-3-hydroxyveratramen-11-one |
SST0249 | Hideaki Nishino |
C27H39O3N | 425.603 | |
Synthesis from 3b-acetoxy-5a-etiojirv-12(13)-en-17-one as a starting material. (Ref. 0910) |
NMR spectra of degradated products. (Ref. 0909) |
Moved to sneeze. (Ref. 0899) |
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| 250 |  |
11-Ketoprogesterone / 11-Oxoprogesterone / U-1258 / Ketogestin |
Pregn-4-ene-3,11,20-trione |
SST0250 | Hideaki Nishino |
C21H28O3 | 328.445 | |
Synthesis by reaction of corticosteron (11b,21-dihydroxypregn-4-ene-3,20-dione) with CH3C6H4SO2Cl in pyridine. (Ref. 0911) |
172-174 C (Ref. 0911) |
Insol in water. Sol in acetone, chloroform. (Ref. 0911) |
Utilization to ketosis. (Ref. 0911) |
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| 251 |  |
Kurchessine |
N,N,N',N'-Tetramethylpregn-5-ene-3b,20a-diamine / 3b,20a-Bis(dimethylamino)-5-pregnene |
SST0251 | Hideaki Nishino |
C25H44N2 | 372.630 | |
140-141 C (acetone) (Ref. 0913) |
Perhaps identical compound to sarcodinine extracted from Saracococa pruniformis Lindl., Euphorbiaceae. (Ref. 0913) |
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| 252 |  |
Kurcholessine |
3b-(Dimethylamino)-4a-methyl-5a-conanine-5,7b-diol |
SST0252 | Hideaki Nishino |
C25H44O2N2 | 404.629 | |
218.5-221.5 C (acetone) (Ref. 0912) |
Very sol in chloroform, methanol, ethanol, pyridine. Sparingly sol in hot acetone. Insol in ethylacetate, benzene, petroleum ether, water. (Ref. 0912) |
Me2Na+C-3:J=7.71; MeNa+C-18/C-20:J=7.80 (Ref. 0915) |
m+/e 71(79%), 84(100%), 156(19%), 324(24%), 389(22%; m+/e-CH3), 404(16%) (Ref. 0915) |
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| 253 |  |
Lupeol / Monogynol B / b-Viscol / Fagarasterol |
Lup-20(29)-en-3b-ol |
SST0253 | Hideaki Nishino |
C30H50O | 426.717 | |
215 C (alcohol or acetone) (Ref. 0916) |
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| 254 |  |
Lynestrenol / 3-Desoxynorlutin / Ethinylestrenol / Exlutona / Exlutena / Orgametril / Orgametil |
19-Nor-17a-pregn-4-en-20-yn-17-ol / 17a-Ethinyl-17b-hydroxyestr-4-ene / 17a-Ethynylestr-4-en-17b-ol / 17a-Ethynyl-19-nor-androst-4-en-17b-ol |
SST0254 | Hideaki Nishino |
C20H28O | 284.436 | |
Preparation method. (Ref. 0819) |
158-160 C (Ref. 0819) |
[a]/D=-13 (chloroform) (Ref. 0819) |
Metabolism in human. Excreted 16% in the day of dose, additional 24% excreted in 4 days, which is somewhat delayed than norethisterone. Found 3% in plasma as a conjugated form after 24 h. The half-life is 30 min. in plasma as a free form. Lynestrenol cannot be detected in urine. (Ref. 0923) Excreted 31.2 to 57.6% in 5 days after administration to human irrespective of oral or i.v. Biological half-life was 26.5 h. About 10% of metabolite in urine was excreted as a sulfate-conjugated form. Rapidly disappeared from plasma than norethisterone. (Ref. 0924) |
Progestin. Oral contraceptive when taken along with mestranol. (Ref. 0819) |
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| 255 |  |
Medrogestone / AY62022 / Colpro / Colprone / Prothil |
6,17-Dimethylpregna-4,6-diene-3,20-dione / 6,17a-Dimethyl-6-dehydroprogesterone |
SST0255 | Hideaki Nishino |
C23H32O2 | 340.499 | |
144-146 C (ether). (Ref. 0926) |
[a]23/D=+79 (c=1 in chloroform) (Ref. 0926) |
UVmax: 288mm (e=25,000), 289mm (e=24,900) (Ref. 0926) |
Progestin activity. Same activity as 6a-methyl-17-acetoxyprogesterone in oral administration. No androgen activity. Clauberg test (relative potency): subcutaneous, 5 (progesterone=1); oral, 10 (norethindrone=1). (Ref. 0925) Progesterone exerts no effect in oral administartion, but the 6,17-substituents do. (Ref. 0926) |
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| 256 |  |
Medroxyprogesterone |
17-Hydroxy-6a-methylpregn-4-ene-3,20-dione / 17a-Hydroxy-6a-methylprogesterone / 6a-Methyl-17a-hydroxyprogesterone / 6a-Methyl-4-pregnen-17a-ol-3,20-dione |
SST0256 | Hideaki Nishino |
C22H32O3 | 344.488 | |
Synthesis from 17a-hydroxyprogesterone bisethylene acetal as a starting material. (Ref. 0928) |
220-223.5 C (chloroform) (Ref. 0928) |
[a]25/D=+75 (chloroform) (Ref. 0928) |
UVmax (ethanol): 241nm (e=16,150) (Ref. 0928) |
6a-Methyl-17a-hydroxyprogesterone and the acetate are the strongest progestational agents of the known compound. Application for regulation of the estruation (mating season) in domestic animals. (Ref. 0928) |
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| 257 |  |
Medrysone / Hydroxymesterone / U-8471 / HMS / Spectramedryn |
11b-Hydroxy-6a-methylpregn-4-ene-3,20-dione / 11b-Hydroxy-6a-methylprogesterone / 6a-Methyl-11b-hydroxyprogesterone |
SST0257 | Hideaki Nishino |
C22H32O3 | 344.488 | |
Synthesis. (Ref. 0930) |
155-158 C (Ref. 0930) |
[a]/D=+189 (in chloroform) (Ref. 0930) |
Application to therapy for the inflammatory in eyes as a glucocorticoid. Never increases intraocular pressure. Never brings about the reactivation of herpetic keratitis. (Ref. 0929) |
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| 258 |  |
Megestrol acetate / Megace / Niagestin / Ovaban |
17a-Hydroxy-6-methylpregna-4,6-diene-3,20-dione acetate / 17a-Acetoxy-6-methylpregna-4,6-diene-3,20-dione / 6-Dehydro-6-methyl-17a-acetoxy-progesterone / 6-Methyl-D4,6-pregnadien-17a-ol-3,20-dione acetate |
SST0258 | Hideaki Nishino |
C24H32O4 | 384.508 | |
Synthesis from D5-pregnene-3b-17a-diol-20-one acetate as a starting material. (Ref. 0931) |
218-220 C (Ref. 0931) |
[a]/D=+11 (Ref. 0931) |
lmax 289mm (e=24,000) (Ref. 0931) |
lKBr/max 1580, 1625, 1660, 1710, 1730/cm (Ref. 0931) |
Utilize as a mixture for anti-tumor medicine or oral contraceptive. Application to the progestational action, the regulation of estruation (mating season) in domestic animals. Compared with 19-nor-17a-ethynyl testosterone (norlutin) as the standard, more than 2 to 3-times higher than progestational potency (Clauberg assay, oral route) in animal experiments. (Ref. 0931) Dimethylpolysiloxane implant is the most effective application. Same activity in 1/6 to 1/25 dose as other medicine. (Ref. 0932) |
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| 259 |  |
Meprednisone / Betapred / Betapar / Deltacortene beta / Betalone / Deltisona B |
17,21-Dihydroxy-16b-methylpregna-1,4-diene-3,11,20-trione / 16b-Methylprednisone |
SST0259 | Hideaki Nishino |
C22H28O5 | 372.455 | |
Preparation by hydrolysis of 16b-methylprednisone acetate (m.p. 230-233 , [a]CHF/D=+216, lMeOH/max= 238mm (15,100)) in potassium-bicarbonate-aqueous methanol. (Ref. 0633) Preparation by hydrolysis of 16b-methylprednisone 21-acetate in potassium bicarbonate. (Ref. 0935/0635) Synthesis from 5a-pregn-16-en-3b-ol-11,20-dione acetate. (Ref. 0936) |
lCHF/max 2.90, 1625, 5.82, 6.00, 6.14, 6.19, 11.21m (Ref. 0635) |
Glucocorticoid. High anti-inflammatory action. No salt retention in animal experiments and clinical application. (Ref. 0633/0935) In rats, 16b-methyl cortical steroids (hydrocortisone=1) compound, liver glycogen, systematic granulo A ; cortisone, 0.4, 2; hydrocortisone, 0.6, 4; prednisone, 1, 26; prednisolone, 1.5, 23; 9a-fluorohydrocortisone, 8.5, 23; 9a-fluoroprednisolone, 11, 70. They all exert no sodium retention activity in adrenalectomized rats. Except 16b-methyl forms of cortisone, hydrocortisone, and 9a-fluorohydrocortisone, show equivalent metabolic activity and anti-inflammatory action in human. (Ref. 0635) The 21-acetate possesses the same activity. (Ref. 0936) |
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| 260 |  |
Mestanolone / Androstalone (Roussel) |
17b-Hydroxy-17-methyl-5a-androstan-3-one / 17b-Hydroxy-17a-methyl-3-androstanone / 17a-Methyl-androstan-17b-ol-3-one / 17a-Methylandrostan-3-on-17b-ol |
SST0260 | Hideaki Nishino |
C20H32O2 | 304.467 | |
Yielded by oxidation of 17-methyl-3,17-androstanediol. (Ref. 0444) |
192-193 (ethyl acetate) (Ref. 0444) |
Insol in water. Sol in acetone, alcohol, ether, ethylacetate. (Ref. 0444) |
Androgenic activity. (Ref. 0444) |
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| 261 |  |
Mestranol / Norquen / Ovastol |
3-Methoxy-19-nor-17a-pregna-1,3,5(10)-trien-20-yn-17-ol / 17a-Ethynyl-3-methoxy-1,3,5(10)-estratrien-17b-ol / 17a-Ethynylestradiol 3-methylether |
SST0261 | Hideaki Nishino |
C21H26O2 | 310.430 | |
150-151 C (methanol or acetone) (Ref. 0937) |
Estrogenic activity, administered as an oral contraceptive in a combination. (Ref. 0937) |
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| 262 |  |
Methenolone / Metenolone |
17b-Hydroxy-1b-methyl-5a-androst-1-en-3-one / 1-Methyl-D1-androsten-17b-ol-3-one |
SST0262 | Hideaki Nishino |
C20H30O2 | 302.451 | |
Synthesis from D2'-pyrazolino-4',3':1,2-androstanol-(17b)-on-(3) (Ref. 0938) |
149.5-152 C (isopropyl ether) (Ref. 0938) |
[a]/D=+58.9 . (Ref. 0938) |
Anabolic action. (Ref. 0938) |
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| 263 |  |
6a-Methylprednisolone / Artisone-Wyeth / Medrate / Medrol / Medrone / Metastab / Metrisone / Promacortin / Suprametil / Urbason |
11b,17a,21-Trihydroxy-6a-methyl-1,4-pregnadiene-3,20-dione / 1-Dehydro-6a-methylhydrocortisone / D1-6a-Methylhydrocortisone / 6a-Methyl-11b,17a,21-triol-1,4-pregnadiene-3,20-dione |
SST0263 | Hideaki Nishino |
C22H30O5 | 374.471 | |
lNujol/max: 5.83, 6.01, 6.19, SH.6.21m. (Ref. 0940) |
Glucocorticoid action. Stronger than hydrocortisone. (Ref. 0939) |
||||||||||||||||||
| 264 |  |
17-Methyltestosterone / Anertan (Tabl) / Glosso-Sterandryl / Homandren (Tebl) / Malestrone (Tebl) / Metandren / Neo-Hombreol M / Nu-Man / Orchisterone-M / Oreton-M / Perandren (Lozenges) / Synadrotabs / Testhormona / Testosid (Tabl) / Testovviron (Tabl) |
17b-Hydroxy-17-methylandrost-4-en-3-one / 17a-Methyl-D4-androsten-17b-ol-3-one |
SST0264 | Hideaki Nishino |
C20H30O2 | 302.451 | |
Synthesis from 17-methyl-D5,6-androstendiol-(3,17). (Ref. 0941) |
161.5-164.5 C (Ref. 0941) |
[a]/D=+76.4 (alcohol) (Ref. 0941) |
Sol in alcohol, methanol, ether, other organic solvents. Slightly sol in vegetable oils. Insol in water. (Ref. 0941) |
Androgen activity. (Ref. 0941) |
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| 265 |  |
RP12,222 / Pandrocine / Penmestrol |
17a-Methyltestosterone 3-cyclopentyl enol ether / 3-(Cyclopentyloxy)-17-methylandrosta-3,5-dien-17b-ol |
SST0265 | Hideaki Nishino |
C25H38O2 | 370.568 | |
Preparation by enol esterification of 17-methyltestosterone. (Ref. 0897) |
148-152 C (Ref. 0897) |
[a]/D=-150 (in dioxane) (Ref. 0897) |
Myotropic, androgen action. Weaker in non-oral administration, reversely stronger in oral-administration (stronger 5-times more than 17a-methyltestosterone). Anti-breast cancer action (effective even by subcutaneous ingection). (Ref. 0897) |
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| 266 |  |
Methyltrienolone / R1881 |
17b-Hydroxy-17-methylestra-4,9,11-trien-3-one / 17b-Hydroxy-17-methyl-19-norandrosta-4,9,11-trien-3-one / 17a-Methyl-4,9,11-estratrien-17b-ol-3-one |
SST0266 | Hideaki Nishino |
C19H24O2 | 284.393 | |
Synthesis from 3-chloro-4,5-seco 5-oxo 17-benzoxy 19-nor-androsta 2,9-diene as a starting material. (Ref. 0942) |
170 C (diisopropyl ether) (Ref. 0942) |
[a]20/D=-58.7 (c=0.5 in ethanol) (Ref. 0942) |
Anabolic action. (Ref. 0942) |
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| 267 |  |
19-Nortestosterone |
17b-Hydroxyestr-4-en-3-one / 17b-Hydroxy-4-estren-3-one / 4-Estren-17b-ol-3-one / 17b-Hydroxy-19-nor-4-androsten-3-one |
SST0267 | Hideaki Nishino |
C18H26O2 | 274.398 | |
Sol in alcohol, ether, chloroform. (Ref. 0944) |
UVmax (ethanol): 240.5mm (e=17,000), 307-310mm (Ref. 0944) |
lCS2/max 2.77m(OH), 6.02m (conj, C'=0) (Ref. 0944) |
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| 268 |  |
Nandrolone p-hexyloxyphenylpropionate / Nortestosterone-hexoxyphenylpropionate / Anador / Anadur |
17b-[3-[4-(Hexyloxy)phenyl]-1-oxopropoxy]estr-4-en-3-one / 17b-Hydroxyestr-4-en-3-one p-(hexyloxy)hydrocinnamate / 17b-Hydroxyestr-4-en-3-one p-hexyloxyphenylpropionate / 17b-Hydroxy-19-norandrost-4-en-3-one p-hexyloxyphenyl propionate / 19-Nortestosterone-3-(p-hexyloxyphenyl)propionate |
SST0268 | Hideaki Nishino |
C33H46O4 | 506.716 | |
Synthesis started by solubilization of testosterone and p-hexoxyhydrocinnamoyl anhydride in pyridine. (Ref. 0945) |
53-55 C (Ref. 0945) |
[a]/D=+45 (c=1.0 in dioxane) (Ref. 0945) |
Anabolic action. Improvement in the strength and duration by esterification. The improvement is dependent on the length of p-alkoxy group. (Ref. 0945) |
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| 269 |  |
Neriantin |
SST0269 | Hideaki Nishino |
C29H42O9 | 534.638 | |
206-208 C (methanol+ethyl acetate) (Ref. 0947) |
Sol in water, alcohol. (Ref. 0947) |
lmax 217, 274mm (Ref. 0947) |
Plants. Obtained by purification from extract of leaves of Nerium oleander L., Apocynaceae. (Ref. 0946) |
Cardiotonic glycoside. (Ref. 0947) |
Neriantin is a steroidal glycoside consisting of Neriantogenin and glucose. (Ref. 0947) |
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| 270 |  |
Norbolethone / WY-3475 / Genabol |
DL-13-Ethyl-17-hydroxy-18,19-di-nor-17a-pregn-4-en-3-one / DL-13b,17a-Diethyl-17b-hydroxygon-4-en-3-one |
SST0270 | Hideaki Nishino |
C21H32O2 | 316.478 | |
144-145 C (alcohol) (Ref. 0948) |
UVmax: 241nm (e=16,500) (Ref. 0948) |
Estrogen-antagonistic, androgen-myotropic, progestational activities are present in d-enantiomer, not in l-enantiomer. No interaction between enantiomers. Among the steroid and the related compound, the activity is detected in natural stereochemical structure, little or no pharmaceutical activity in l-enantiomer. (Ref. 0949) |
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| 271 |  |
Norethandrolone / Nilevar / Solevar |
17-Hydroxy-19-norpregn-4-en-3-one / 17a-Ethyl-19-Nortestosterone / 17a-Ethyl-17-hydroxy-19-norandrost-4-en-3-one / 17a-Ethyl-17-hydroxy-4-norandrosten-3-one |
SST0271 | Hideaki Nishino |
C20H30O2 | 302.451 | |
Synthesis by hydrogen-reduction of 17-ethynyl-19-nortestosterone in the presence of palladium-on-charcoal catalyst, or by formation of estrone methyl ether through ethynylation. The former yield is 73%. (Ref. 0937) |
137-138 C (methanol) (Ref. 0937) |
[a]/D=+25 (methanol) (Ref. 0937) |
Insol in water. Sol in alcohol, benzene, ether, ethylacetate. (Ref. 0937) |
UVmax: 240nm (logE=4.22) (Ref. 0937) |
(KBr disk), 2.84, 6.06, 6.23, 6.90, 7.38, 7.95, 9.09, 10.06, 11.2m (Ref. 0937) |
In the lavator ani test by Eisenberg and Gorgan for anabolic activity as well as weight increase in seminal vesicle and ventral prostate for androgenic activity, along with testosterone propionate as the standard, among 17-alkyl-19-nortesto-sterone compounds tested, 17-ethyl-19-nortestosterone shows high anabolic activity and relatively low androgenic activity (1/16 of testosterone propionate), so that possible most applicable to medication. In oral ingestion to rats, this compound is at least 5-times higher anabolic activity than 17-methyltestosterone and 19-nortestosterone. 17-Ethyltestosterone, not 19-noranalog, is very weak anabolic agent. (Ref. 0937) |
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| 272 |  |
Norethindrone / Norpregneninolone / 19-Norethisterone / Anhydrohydroxynorprogesterone / Mini-Pill / Conludag / Micronor / Micronovum / Nor-QD / Norluten / Primolut N / Norluton / Norlutin / Noralutin |
17-Hydroxy-19-nor-17a-pregn-4-en-20-yn-3-one / 19-Nor-17a-ethynyltestosterone / 17a-Ethynyl-19-nortestosterone / 19-Nor-17a-ethynyl-17b-hydroxy-4-androsten-3-one / 19-Nor-17a-ethynylandrosten-17b-ol-3-one; 17a-Ethynyl-19-nortestosterone. |
SST0272 | Hideaki Nishino |
C20H26O2 | 298.419 | |
Synthesis: starting from 19-nortestosterone, which is easily prepared from estron, by utilizing D4-androstene-3,17-dione, an intermediate of 19-nor-17a-ethynyltestosterone synthesis. Nitrogen substitution of 3-ethoxy-19-nor-D3,5-androstadien-17-one in toluene solution by the addition to t-amyl alcohol dissolved with potassium. Stir for 14 h with gassing with acetylene at room temperature. Dilute with water, adjust the pH to 1 with 50% HCl, bubble with acetylene gas until running out of volatile materials. Cool down the residues, collect the solid, recrystallize several times with ethyl acetate. (Ref. 0950) |
203-204 C (ethyl acetate) (Ref. 0950) |
UVmax (ethanol): 240nm (loge=4.24) (Ref. 0950) |
nchloroform/max 1668/cm=1 (means free hydroxyl group) (Ref. 0950) |
As progestin, in oral ingestion to animals, several times higher effect when compared with 17-ethynyltestosterone. Evidence of the same effect in human female by clinical application. (Ref. 0950) |
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| 273 |  |
Norethynodrel / Enidrel |
17-Hydroxy-19-nor-17 a-pregn-5(10)-en-20-yn-3-one / 17a-Ethynyl-17-hydroxy-5(10)-estren-3-one / 13-Methyl-17-ethynyl-17-hydroxy-1,2,3,4,6,7,8,9,11,12,13,14,16,17-tetradecahydro-15H-cyclopenta[a]-phenanthren-3-one |
SST0273 | Hideaki Nishino |
C20H26O2 | 298.419 | |
Synthetic progestin. (Ref. 0951) |
169-170 C (methanol) (Ref. 0951) |
[a]/D=+108 (1% chloroform) (Ref. 0951) |
Progestin action. Administration for maintenance of pregnancy.(Ref. 0951) |
Norethynodrel passes by placenta in a high concetration. In addition to the metabolites, can be extracted from fetus. (Ref. 0951) |
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| 274 |  |
Norgesterone / Norvinodrel / Vinylestrenolone |
17-Hydroxy-19-nor-17a-pregna-5(10),20-dien-3-one / 17b-Hydroxy-17a-vinylestr-5(10)-en-3-one / 17a-Vinyl-5(10)-estren-17b-ol-3-one |
SST0274 | Hideaki Nishino |
C20H28O2 | 300.435 | |
Preparation by synthesis of 17a-ethynyl-3-methoxyestra-1,3,5(10),8-tetraen-17b-ol. (Ref. 0952) |
138-139 C (light petroleum) (Ref. 0952) |
[a]/D=+161 (chloroform) (Ref. 0952) |
nmax(Nujl) 3400, 1704, 992, 931/cm. (Ref. 0952) |
No androgenic activity, little estrogenic activity. Progestational activity, maybe apply as a claudogenic agent.(Ref. 0953) |
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| 275 |  |
Norgestrel / Ovrette |
13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-20-yn-3-one /13b-Ethyl-17a-ethynyl-17b-hydroxygon-4-en-3-one / 17a-Ethynyl-18-homo-19-nortestosterone |
SST0275 | Hideaki Nishino |
C21H28O2 | 312.446 | |
Synthesis from 13b-ethyl-17a-ethynyl-3-methoxygona-2,5(10)-dien-17b-ol or 13b-ethyl-17a-ethynyl-17a-hydroxygon-5(10)-en-3-one. (-)-Form can be synthesized from (-)-13b-ethyl-3-hydroxygona-1,3,5(10)-trien-17-one. (+)-Form can be synthesized from (+)-13b-ethyl-3-methoxygona-1,3,5(10)-trien-17b-ol. (Ref. 0948) |
UVmax (ethanol): 241nm (e=16,700) (Ref. 0948) |
In nature, (+)-form is active, so that synthesized ( ) or (+)-forms possess progestin activity. (Ref. 0954) |
(-)-Form, optical rotatory dispersion (dioxane, c 0.0482, 280); [a]/400=-237 , [a]/362=-707, [a]/357=-685, [a]/349=-815, [a]/335=-262, [a]/325=+403, [a]/300=+1195, [a]/280=+1105, [a]/265=+1170. (Ref. 0948) |
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| 276 |  |
Norgestrienone |
17-Hydroxy-19-nor-17a-pregna-4,9,11-trien-20-yn-3-one / 17a-Ethynyl-4,9,11-estratrien-17b-ol-3-one / 17a-Ethynyl-17b-hydroxy-3-oxo-4,9,11-estratriene / 17a-Ethynyl-13b-methyl-D4,9,11-gonatriene-17b-ol-3-one |
SST0276 | Hideaki Nishino |
C20H22O2 | 294.387 | |
Synthesis from mono oxim. (Ref. 0955) |
169 C (diisopropyl ether) (Ref. 0955) |
[a]20/D=+63 (c=0.5 in alc.) (Ref. 0955) |
Sol in alcohol, ether, acetone, benzene, chloroform. Insol in water, dil. acid solutions, alkali. (Ref. 0955) |
UVmax: 342, 238nm (e= 29,100, 5,920) (Ref. 0955) |
Progestin activity. (Ref. 0955) |
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| 277 |  |
Normethandrone / Methylnortestosterone / Orgasteron / Metalutin / Methalutin |
17b-Hydroxy-17-methylestr-4-en-3-one / 17a-Methyl-19-nortestosterone |
SST0277 | Hideaki Nishino |
C19H28O2 | 288.424 | |
Preparation from 3-ethoxy-19-nor-D3,5-androstadien-17-one, via reaction with methylmagnesium bromid and acid hydrolysis. Preparation by birch reduction of 17-methylest diol methyl ether. The latter protocol is better for large scale preparation. (Ref. 0950) |
156-158 C (Kofler) (Ref. 0950) |
[a]/D=+33 (preparation by birch reduction method). [a]/D=+31 (prepared from 3-ethoxy-19-nor-D3,5-androstadien-17-one). (Ref. 0950) |
UVmax (ethanol): 240nm (loge=4.23) (Ref. 0950) |
nCS2/max 1680/cm and band exhibiting free hydroxyl group. (Ref. 0950) |
Evidence for the same androgenic activity as 17a-methyltestosterone in chick comb test by preliminary experiment using animals. However, somewhat weaker in increase of rat seminal vesicle weight. (Ref. 0950) |
||||||||||||||
| 278 |  |
Oxandrolone / Anavar / Provitar / Vasorome |
17b-Hydroxy-17-methyl-2-oxa-5a-androstan-3-one / Dodecahydro-3-hydroxy-6-(hydroxymethyl)-3,3a,6-trimethyl-1H-benz[e]indene-7-acetic acid d-lactone |
SST0278 | Hideaki Nishino |
C19H30O3 | 306.440 | |
Synthesis from 1-androstene-3,17-dione. (Ref. 0956) |
235-238 C (Ref. 0956) |
[a]25/D=-23 (Ref. 0956) |
lmax 2.87, 5.79m (Ref. 0956) |
Stronger anabolic action than 17b-hydroxy-17a-methylandrostan-3-one (oral administration, nitrogen retention activity). Essentially not androgenic. Anabolic agent available via oral ingestion. (Ref. 0956) |
|||||||||||||||
| 279 |  |
Oxymetholone / Anasterone / Adroyd / Anapolon / Anadrol / Plenastril / Protanabol / Nastenon / Synasteron |
17b-Hydroxy-2-(hydroxymethylene)-17-methyl-5a-androstan-3-one / 2-Hydroxymethylene-17a-methyldihydrotestosterone / 4,5a-Dihydro-2-hydroxymethylene-17a-methyltestosterone / 2-Hydroxymethylene-17a-methyl-17b-hydroxy-5a-androstan-3-one / 2-Hydroxymethylene-17a-methylandrostan-17b-ol-3-one |
SST0279 | Hideaki Nishino |
C21H32O3 | 332.477 | |
Synthesis from 2a-methyltestosterone. The recovery is 65%. (Ref. 0780) |
178-180 C (ethyl acetate) (Ref. 0780) |
[a]/D=+38 (Ref. 0780) |
UVmax: 285nm (loge=3.99) (Ref. 0780) |
Anabolic action and anti-tumor activity, espacially via oral ingestion, strong anabolic agent with very weak androgenic action. (Ref. 0780) |
The enol acetate, m.p. 144-148 , [a]/D=+27 (ethanol), lmax 255mm (loge=4.09), C23H34O4. The enol propionate, m.p. 135, [a]/D=+26 (ethanol), lmax 257mm (loge=4.11), C24H36O4. The enol benzoate, m.p. 188-190, [a]/D=0, lmax 230mm (loge=4.19), C28H36O4. (Ref. 0780) |
||||||||||||||
| 280 |  |
Paramethasone / Flumethone / Haldrate / Paramezone / Dilar / Dillar / Cortiden / Alondra / Metilar |
6a-Fluoro-11b,17,21-trihydroxy-16a-methylpregna-1,4-diene-3,20-dione / 6a-Fluoro-16a-methylprednisolone / 16a-Methyl-6a-fluoroprednisolone |
SST0280 | Hideaki Nishino |
C22H29O5F | 392.461 | |
Synthesis from 16a-methylpregnenolone acetate. (Ref. 0823) |
The 21-acetate: [a]/D=+85 (Ref. 0823) |
The 21-acetate: sol in ethanol, acetone; slightly sol in water. (Ref. 0823) |
The 21-acetate, UVmax (ethanol): 243nm (loge=4.16) (Ref. 0823) |
The 21-acetate, lmax (KBr) 5.80-5.85, 6.03, 6.16, 6.22m (Ref. 0823) |
Anti-inflammatory activity. Sixty-times higher activity than hydrocortisone and no sodium retention. Highly effective therapy for rheumatoid arthritis patients in clinical application. (Ref. 0823) |
||||||||||||||
| 281 |  |
Peruvoside / Cannogenin a-L-thevetoside / Encordin |
(3b,5b)-3-[(6-Deoxy-3-O-methyl-a-L-glucopyranosyl)oxy]-14-hydroxy-19-oxocard-20(22)-enolide |
SST0281 | Hideaki Nishino |
C30H44O9 | 548.665 | |
Preparation of thevetose by Kiliani's hydrolysis. (Ref. 0957) |
Sol in water (1 g/about 2500 ml). Very sol in chloroform, acetone. Sparingly sol in methanol, ethanol. |
Plants. Yellow oleander or seeds of tropical garden plant, Thevetia peruviana (Pers.) K. Schum. (Th. neriifolia Juss.), Apocynaceae (trumpet flower in Florida). (Ref. 0957) |
Application to heart failure. Inotropic effect. Equivalent activity with ouabain. In animal experiments, very different dose amount between inotropic effect and arrhythmia when compared with ouabain and proscillaridine. (Ref. 0958) |
Cannogenine-thevetoside structure. (Ref. 0958) |
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| 282 |  |
Prednylidene / Dacortilen / Decortilen / Sterocort |
11b,17,21-Trihydroxy-16-methylenepregna-1,4-diene-3,20-dione / D1,4-pregnadiene-16-methylene-11b,17a,21-triol-3,20-dione / 16-Methylene-11b,17a,21-trihydroxypregna-1,4-diene-3,20-dione / 16-Methyleneprednisolone |
SST0282 | Hideaki Nishino |
C22H28O5 | 372.455 | |
Synthesis from 16-methyl-5,16-pregnadien-3b-ol-20-one-acetate. (Ref. 0959) |
233-235 C (Ref. 0959) |
[a]23/D=+31 (dioxane) (Ref. 0959) |
UVmax: 243nm(e=15,900) (Ref. 0959) |
Glucocorticoid action. (Ref. 0959) |
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| 283 |  |
Pregnenolone / Arthenolone / Enelone / Natolone / Prenolon / Regnosone / Skinostelon |
3b-Hydroxypregn-5-en-20-one / D5-Pregnen-3b-ol-20-one / 17b-(1-Ketoethyl)-D5-androsten-3b-ol |
SST0283 | Hideaki Nishino |
C21H32O2 | 316.478 | |
Very sparingly sol in water. The other solubility (g/100ml); carbon tetrachloride, 0.5; petroleum ether, 0.1; ethylacetate, 1.1; acetone, 0.6; chloroform, 7.0; ethanol, 1.9; benzene, 0.9; isopropanol, 1.5; propylene glycol, 0.1; dioxane, 3.1; benzyl alcohol, 8.1. |
|||||||||||||||||||
| 284 |  |
Proscillaridin / Proscillaridin A / Desglucotransvaaline / Scillarenin 3b-Rhamnoside / Caradrin / Cardion / Carmazon / Herzo / Proscillan / Prostosin / Proszin / Protasin / Purosin-TC / Sandoscill / Scillacrist / Scilla Didier / Simeon / Solestril / Stellarid / Talucard / Talusin / Urgilan |
3b-[(6-Deoxy-a-L-mannopyranosyl)oxy]-14-hydroxybufa-4,20,22-trienolide / 14-Hydroxy-3b-(rhamnosyloxy)bufa-4,20,22-trienolide / 3b-Rhamnosido-14b-hydroxy-D4,20,22-bufatrienolide |
SST0284 | Hideaki Nishino |
C30H42O8 | 530.650 | |
298-300mm (loge=3.58-3.65) (Ref. 0518) |
Cardiotonic action. LD50 (cats)=0.157mg/kg.(Ref. 0518) |
||||||||||||||||||
| 285 |  |
17b-Hydroxy-2-(1-pyrrolidinylmethyl)androst-4-en-3-one / 2-(1-Pyrrolidyl)methyltestosterone |
SST0285 | Hideaki Nishino |
C24H37O2N | 371.556 | |
Synthesis from 2-Hydroxymethylene-testosterone. (Ref. 0971) |
193-195 C (benzene). (Ref. 0971) |
[a]20/D=+40 (c=1.294 in chloroform) (Ref. 0971) |
||||||||||||||||||
| 286 |  |
Quinbolone / Anabolicum vister |
17b-(1-Cyclopenten-1-yloxy)androsta-1,4-dien-3-one / 1-Dehydrotestosterone 17-cyclopent-1'-enyl ether |
SST0286 | Hideaki Nishino |
C24H32O2 | 352.510 | |
Synthesis from 5a-androstan-17b-ol-3-one 17-(1'-ethoxy)-cyclopentyl ether. (Ref. 0972) |
133-135 C (ethanol) (Ref. 0972) |
[a]20/D=+61 (dioxane) (Ref. 0972) |
Insol in water. Sol in most organic solvents. Very sparingly sol in ethanol, hexane. Also sol in sesami oil: 40-45mg/ml. (Ref. 0972) |
UVmax: 244-245nm (E1%/1cm 430-450) (Ref. 0972) |
Anabolic action. Ratio of anabolic to androgenic is 3, three times stronger than methyltestosterone (oral administration) (Ref. 0972) |
||||||||||||||
| 287 |  |
Quinestrol / Estrovis |
3-(Cyclopentyloxy)-19-nor-17a-pregna-1,3,5(10)-trien-20-yn-17-ol / 17a-Ethinylestradiol 3-cyclopentyl ether |
SST0287 | Hideaki Nishino |
C25H32O2 | 364.520 | |
Synthesis by treatment of estron by potassium acetylide. (Ref. 0973) |
107-108 C (Ref. 0973) |
[a]25/D=+5 (c=0.5 in dioxane) (Ref. 0973) |
Estrogen action. Relative oral uterotrophic potency (estrone, 1); 45. (Ref. 0973) |
||||||||||||||||
| 288 |  |
Resibufogenin / Respigon |
14,15b-Epoxy-3b-hydroxy-5b-bufa-20,22-dienolide / 3b-Hydroxy-14b,15b-epoxy-5bbufa-20,22-dienolide / 3b-Hydroxy-14b,15b-oxido-bufadien-(20;22)-olide |
SST0288 | Hideaki Nishino |
C24H32O4 | 384.508 | |
[a]22/D=-7.1 (c=1.259 in chloroform) (Ref. 0975) |
Differed from digitalis, stimulating activity to respiration. Also cardiotonic medicine (tested in hypotensive (50-70mmHg) dogs). Although believed that cardiotonic glycosides usually exert the function because of having C-14OH group, Resibufogenin possesses no C-14OHgroup. Possibly, configuration of C-D ring is essential rather than C-14OH group for cardiotonic action. (Ref. 0981) |
The 3-acetate, m.p. 218-203 , [a]/D=-1, lmax=297.5mn (loge=3.73) (Ref. 0974/0975) The hydrochloride, m.p. 230, [a]/D=+15, lmax=298mm (loge=3.74) (Ref. 0974) Resibufogenin is secondary-tertiary epoxide. (Ref. 0976) Efficient recovery of resibufogenin by conversion of 14-dehydrobufalin to halohydrin, followed by treatment with basic alumina or hot pyridine. (Ref. 0979) Synthesis from 14-anhydrobufalone. The 3-acetate, m.p. 217-220, IR, 3010, 1745-1710, 1635, 1535, 1250, 1240, 1230/cm, lmax=300nm (e=5650), Mass, m/e=426(M+). (Ref. 0980) |
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| 289 |  |
Artebufogenin A, 14a-Artebufogenin |
3b-Hydroxy-14b-15-keto-bufadien-(20,22)-olide |
SST0289 | Hideaki Nishino |
C24H32O4 | 384.508 | |
Cardiotonic medicine (Ref. 0982) |
|||||||||||||||||||
| 290 |  |
Marinobufagin |
3b,5b-Dihydroxy-14b,15b-oxido-bufadien-olide |
SST0290 | Hideaki Nishino |
C24H32O5 | 400.508 | |
212-213 C (Ref. 0975) |
[a]/D=+11 (Ref. 0975) |
Animals. Isolation from South American toads, Bufo marinus. (Ref. 0982) |
Cardiotonic agent. (Ref. 0982) |
||||||||||||||||
| 291 |  |
Artebufogenin B / 14b-Artebufogenin |
3b-Hydroxy-14a-14-keto-bufadien-(20,22)-olide |
SST0291 | Hideaki Nishino |
C24H32O4 | 384.508 | |
The 3-acetate, m.p. 235 , [a]/D=-63, Preparation by the following treatments: preparation of 14a-artebufogenin (artebufogenin A) by perchloric acid-treatment of resibufogenin and processing of the product by alminium oxide. (Ref. 0978) |
235 C (as 3-acetate) (Ref. 0977) |
[a]/D=-63 (Ref. 0977) |
Cardiotonic action. (Ref. 0982) |
||||||||||||||||
| 292 |  |
Samandarine |
1a,4a-Epoxy-3-aza-A-homoandrostan-16b-ol |
SST0292 | Hideaki Nishino |
C19H31O2N | 305.455 | |
187-188 C (abs. methanol or 50% acetone) (Ref. 0984) |
[a]17/D=+43.3 (acetone) (Ref. 0984) |
Animals. Isolation from secretory glands of skin from European fire salamander (Salamandra maculosa) and Salamandridae, e.g., Alpine salamander (Salamandra atra). (Ref. 0983) |
Stereochemistry. (Ref. 0984) |
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| 293 |  |
Scillaren A / Glucoproscillaridin A / Transvaalin |
3-b-O-[4-O-D-Glucopyranosyl-(a-L-rhamnopyranosido)]-14b-bufa-4,20,22-trienolide |
SST0293 | Hideaki Nishino |
C36H52O13 | 692.790 | |
Sol in alcohol, methanol. Insol in chloroform, ether. Sparingly sol in water. (Ref. 0988) |
lmax 300mm (loge=3.74), lmax 299mm (loge=3.74) (Ref. 0994) |
1720/cm (5.81m)(C=O), 1639/cm (6.10m), 1603/cm (6.24m)(C=C) (Ref. 0994) |
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| 294 |  |
Scillaridin A |
14-Hydroxy-14b-bufa-3,5,20,22-tetraenolide |
SST0294 | Hideaki Nishino |
C25H32O3 | 380.520 | |
245-250 C (Ref. 0986) |
[a]20/D=-62.7 (chloroform) (Ref. 0986) |
Cardiotonic agent. (Ref. 0965) |
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| 295 |  |
a-Solanine / a-Solatunine |
SST0295 | Hideaki Nishino |
C45H73O15N | 868.059 | |
286 C (Ref. 0995) |
[a]20/D=-59 (pyridine) (Ref. 0995) |
Plants. Isolation from several species of Solanum (eggplants, potatoes), especially S. tuberosum L. (potato), S. nigrum L. (woody nightshade), Lycopersicon esculentum Mill., Solanaceae (tomato). (Ref. 0524) |
Solanine acts as a very strong toxin in chicken embryo ( injection into egg yalk), mouse, rats, rabbits (non-oral administration). However, not toxic by oral ingestion to mouse, even by a dose of 1g/kg body wt. The aglycon, solanidine, is by far less toxic than solanine. Death by solanine poisoning is caused by hypoergasia of central nervous system. (Ref. 0997) |
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| 296 |  |
Solasonine / Solanine-S / Purapurine |
(22R,25R)-Spiro-5-en-3b-yl-O-6-deoxy-a-L-mannopyranosyl-b-D-glucopyranosyl-b-D-galactopyranoside |
SST0296 | Hideaki Nishino |
C45H73O16N | 884.058 | |
Sol in hot alcohol, hot dioxane. Sparingly sol in hot water, dil. acetic acid. Insol in chloroform, ether. (Ref. 0998) |
Paperchromatography: solasonine, 0.55 Rf; solamargin, 0.73 Rf; solasodin, 0.90-0.95 Rf. (Ref. 1003) |
Plants. Extracted from seeds and fruits of Poro-poro, called in Maoriname, such as Solanum aviculare Forst F. and S. Sodomeum L., S. xanthocarpum (Schrad and Wendl.), Solanaceae. (Ref. 0998/0999/1000) Extraction from fruits of S. laciniatum Ait., S. nodiflorum Jacq., S. miniatum Bernh., S. nigrum L., S. gracile Otto, S. douglasii Dum., and S. aviculare Forst. (Ref. 1001/1002) |
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| 297 |  |
Stanolone / Anaboleen / Anabolex / Anaprotin / Androlone / Cristerona MB / Neodrol / Proteina / Stanaprol |
17b-Hydroxy-5a-androstan-3-one / 17b-Hydroxy-3-androstanone / 3-Oxo-17b-hydroxyandrostane / Androstan-17b-ol-3-one / 4-Dihydrotestosterone |
SST0297 | Hideaki Nishino |
C19H30O2 | 290.440 | |
[a]20/D=+32.4 (alcohol) (Ref. 1005) |
Sol in acetone, ether, alcohol, ethylacetate. Insol in water. (Ref. 1005) |
Band much close to 9.5m. (Ref. 1008) |
Androgen activity. (Ref. 1007) |
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| 298 |  |
Stanozolol / Androstanazole / Stanazol / Winstrol / Stromba / Stanozol / Tevabolin |
17-Methyl-2H-5a-androst-2-eno[3,2-c]pyrazol-17b-ol / 1,2,3,3a,3b,4,5,5a,6,8,10,10a,10b,11,12,12a-Hexadecahydro-1,10a,12a-trimethylcyclopenta[7,8]-phenanthro[2,3-c]pyrazol-1-ol / 17b-Hydroxy-17a-methylandrostano[3,2-C]pyrazole |
SST0298 | Hideaki Nishino |
C21H32ON2 | 328.492 | |
Preparation: first, treatment of 17a-methylandrostan-17b-ol-3-one with ethyl formate and sodium methoxide, second, condensation of the product, 2-hydroxy-methylene derivative, with hydrazine. (Ref. 1009) |
229.8-242.0 C (alc.) (Ref. 1009) |
UVmax 223nm (e=4740) (Ref. 1009) |
Estrogenic activity (vaginal cornification), androgenic activity (ventral prostate growth), myotrophic activity (levator ani growth), anabolic activity (nitrogen retention). In oral adminostration, as an anabolic agent, 35-times higher than methyltestosterone. as an androgenic agent, 1/4 activity of methyltestosterone. No progestin activity even if increased dose amount in rats and rabbits. (Ref. 1009) |
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| 299 |  |
Stenbolone / Stenbolone (Rescinded Usan) |
17b-Hydroxy-2-methyl-5a-androst-1-en-3-one / 2-Methyl-5a-androst-1-en-17b-ol-3-one / 2-Methyl-17b-hydroxy-5a-androst-1-en-3-one / D1-2-Methylandrosten-17b-ol-3-one |
SST0299 | Hideaki Nishino |
C20H30O2 | 302.451 | |
155-158 C (acetone+hexane) (Ref. 1011) |
Sol in hexane, benzene. (Ref. 1011) |
Uvmax (95% ethanol): 241nm (loge=3.99) (Ref. 1011) |
lmax (KBr) 5.99m (Ref. 1011) |
Androgenic and myotrophic potency: 50, 50 when those of testosterone propionate are 100 and 100, respectively. (Ref. 1012) |
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| 300 |  |
Strophanthidin / Apocynamarin / Convallatoxigenin / Corchorin / Cymarigenin / Cynotoxin / Corchorgenin / Corchsularin |
3b,5,14-Trihydroxy-19-oxo-5b-card-20(22)-enolide |
SST0300 | Hideaki Nishino |
C23H32O6 | 404.497 | |
171-175 C (Ref. 1013) |
[a]25/D=+43.1 (c=2.8 in methanol) (Ref. 1013) |
Sol in alcohol, acetone, chloroform, benzene, glacial acetic acid. Insol in water, ether, petroleum ether. (Ref. 1013) |
lmax 303mm (loge=1.5, carbonyl group) (Ref. 1021) |
Cardiotonic agent. (Ref. 1014) |
Identical to Cymarigenin isolated from Apocynum cannabinum. The Benzoate, [a]26/D=+47.8 (c=1.067 in acetone), C30H36O7. The p-bromobenzoate, [a]20/D=+42.0 (c=1.094 in acetone), m.p. 222-224, C30H35O7Br. The oxime, [a]23/D=+74.3 (c=1.009 in pyridine), m.p. 270-275, C23H33O6N. The phenylhydrazone, [a]20/D=-5.0 (c=1.000 in chloroform), m.p. 230-232, C29H38O5N2. The p-bromophenylhydrazone, [a]25.5/D=+105.5 (c=1.004 in chloroform), m.p. 180-185 (Ref. 1013) Identical compound to Corchorin, Corchorgenin, Corchsularin. (Ref. 1017) Reviews.(Ref. 1018/1019)Aglycone yielded by hydrolysis of k-strophanthoside with hydrochloride. (Ref. 1020/1021) |
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| 301 |  |
Tanghinin |
3b-[(2-O-Acetyl-6-deoxy-3-O-methyl-a-l-glucopyranosyl)oxy]-7b,8-epoxy-14-hydroxy-5b-card-20(22)-enolide |
SST0301 | Hideaki Nishino |
C32H46O10 | 590.702 | |
123-131 C (methanol+ether) (Ref. 0561) |
Cardiotonic glycosides. LD50 (cats)=0.3524 0.0389mg/kg. Tanghinigenin as an aglycone, 1.0160.0876 mg/kg (Ref. 0561) |
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| 302 |  |
Testolactone / Fludestrin / Teslac / NSC-23759 / SQ 9538 |
D-Homo-17a-oxaandrosta-1,4-diene-3,17-dione / 13-Hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oic acid d-lactone / 1,2,3,4,4a,4b,7,9,10,10a-Decahydro-2-hydroxy-2,4b-dimethyl-7-oxo-1-phenanthrenepropionic acid d-lactone / Delta-1-testololactone / 1-Dehydrotestololactone / 17a-oxo-D-homo-1,4-androstadiene-3,17-dione / D1-Testolactone |
SST0302 | Hideaki Nishino |
C19H24O3 | 300.392 | |
218-219 C (acetone) (Ref. 1025) |
[a]23/D=-45.6 (c=1.242 in chloroform) (Ref. 1025) |
UVmax (ethanol) 242nm (e=15,800) (Ref. 1025) |
lmax (Nujol) 5.83m (lactone carbonyl), 6.01, 6.15, 6.22m (D1.4-3-ketone) (Ref. 1025) |
Useful as an experimental antineoplastic. (Ref. 1025) |
The semicarbazone, m.p. 250-260 (dec.), C20H27N3O3, lmax (alc.) 244mm (e=12,200), 297mm (e=22,600, characteristic of D1.4-3-semicarbazones. (Ref. 1025) |
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| 303 |  |
Testosterone 17-chloral hemiacetal / Testosterone 17-hemiacetal with chloral |
17b-(2,2,2-Trichloro-1-hydroxyethoxy) androst-4-en-3-one / 17b-(1-Hydroxy-2,2,2-trichloroethoxy) androst-4-en-3-one |
SST0303 | Hideaki Nishino |
C21H29O3Cl3 | 435.811 | |
Add testosterone dissolved in benzene anhydride into chloral solution and incubate for a few minutes by shaking until being clear solution. Further incubation results in formation of solid precipitates. Filter, wash the ppt with benzene, and dry at room temperature until yielding hemiacetal. M.p.194-196 C. Hemiacetal can be formed as crystal in ethylacetate (m.p. 200-201C). (Ref. 1027) |
200-201 C (ethyl acetate). (Ref. 1027) |
UVmax(ethanol) 241nm (e=16,300) (Ref. 1027) |
Remarkable increase in androgenic activity through conversion of 17-hydroxy group of testosterone to methoxy. Testosterone 17-Chloral Hemiacetal possesses 4-5 times stronger androgenic potency than testosterone propionate in rat. However, the acetate exhibits only half a titer of testosterone propionate (Ref. 1027) |
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| 304 |  |
Testosterone 17b-Cypionate / Depo-testosterone / Testosterone cyclopentylpropionate / Depovirin / Pertestis / Testergon / Testodrin / Prolongatum |
17b-(3-Cyclopentyl-1-oxopropoxy)androst-4-en-3-one |
SST0304 | Hideaki Nishino |
C27H40O3 | 412.605 | |
Synthesis by conversion of b-cyclopentylpropionate into the acid chloride and reaction with testosterone. (Ref. 1028) |
101-102 C (Ref. 1028) |
[a]25/D = +87 (chloroform). (Ref. 1028) |
Sol in oils. (Ref. 1028) |
Strong androgen agent. Stronger and more persisting effect than testosterone propionate and testosterone in castrated rats. According to increase in seminal vesicle weight, it reached to 200 mg at the maximum after 10 days by testosterone or testosterone propionate and thereafter decreased slowly. On the other hand, by testosterone 17b-cypionate, the weight reached to 500-600 mg at the maximum after 12 days and persisted without notable decrease even after 30 days. Molecular mass 412.59. (Ref. 1028) |
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| 305 |  |
Testosterone 17-phenylacetate / Perandren phenylacetate |
17b-[(Phenylacetyl)oxy]androst-4-en-3-one |
SST0305 | Hideaki Nishino |
C27H34O3 | 406.557 | |
Synthesis by reaction of testosterone with phenylacetyl chloride in pyridine. (Ref. 1030) |
[a]25/D = +80.0 (dioxane) (Ref. 1031) |
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| 306 |  |
Testosterone propionate / Neo-Hombreol / Perandren / Sterandryl (amps.) / Androsan (amps.) / Androtest P / Bio-Testiculina / Orchisterone-P / Orquisteron-P / Testrex; Testodrin / Testosid / Testoxyl / Uniteston / Homandren (amps.) / Hormoteston / Nasdol / Propiokan / Testaform / Recthormone Testosterone / Testogen / Testonique / Testormol / Tostrin / Enarmon / Anertan |
D4-androstene-17b-propionate-3-one |
SST0306 | Hideaki Nishino |
C22H32O3 | 344.488 | |
Synthesis from D4-androsten-17-ol propionate using CrO3. Bacterial synthesis from androstenediol propionate. (Ref. 1032) |
Insol in water. Sol in alcohol, ether, pyridine, the other organic solvents, vegetable oils. (Ref. 1032) |
Androgenic agent (Ref. 1032) |
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| 307 |  |
Thevetin A |
SST0307 | Hideaki Nishino |
C42H64O19 | 872.946 | |
208-210 C (water) (Ref. 0672) |
Plants. Isolation from seeds of Thevetia neriifolia Juss. (Apocynaceae), Cerbera Odollam. (Ref. 0672) |
Cardiotonic glycoside. (Ref. 0672) |
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| 308 |  |
Tomatidine |
5a-Tomatidan-3b-ol / 5a,20bF,22aF,25bF,27-Azaspirostan-3b-ol |
SST0308 | Hideaki Nishino |
C27H45O2N | 415.652 | |
202-206 C (ethyl acetate) (Ref. 1040) |
[a]25/D=+8 (chloroform) (Ref. 1040) |
10.0, 10.25, 10.4, 11.1, 11.5m (azaoxaspiranebands) (Ref. 1040) |
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| 309 |  |
Tomatillidine |
3b-Hydroxy-16,28-secosolanida-5,22(28)-dien-24-one |
SST0309 | Hideaki Nishino |
C27H41O2N | 411.620 | |
[a]/D=-18.1 (chloroform) (Ref. 1042) |
lmax(KBr) 5.98m(C=N and CO) (Ref. 1042) |
t-CH3, 0.64ppm; t-and sec-CH3, 0.96ppm; sec-CH3, 1.08ppm; one olefinic proton, 5.35ppm; teo sec-CH3, 0.90(J=5cps) and 1.12ppm (J=6cps); and one olefinic proton, 5.35ppm (Ref. 1042) |
m/e=140 (Ref. 1042) |
O.R.D. in MeOH (c 0.12)[a]/290 = +366 , [a]/240 = -666; in dioxane (c 0.19), [a]/405 = -48, [a]/392 = -15, [a]/378 = -48[a]/360 = -3, [a]/369 = -18, [a]/352 = +42, [a]/348 = +33, [a]/298 = +446 (Ref. 1042) |
Plants. Extraction from Solanum tomatillo Phil., Solanaceae (Ref. 1041) |
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| 310 |  |
Tomatine / Lycopersicin |
SST0310 | Hideaki Nishino |
C50H83O21N | 1034.188 | |
263-268 C (methanol) (Ref. 1045) |
[a]20/D = -18 (c=0.55 in pyridine) (Ref. 1045) |
Sol in ethanol, methanol, dioxane, propylene glycol. Insol in water, ether, petroleum ether. The hydrochloride salts are sol in water. (Ref. 1043) |
Antibiotics. Effective on pathogenic microorganism to plants and animals, not effective on E. coli (1 mg/ml), little effective on S. aureus. (Ref. 1043) |
Stable in strong alkaline solution. Boiling in 1N HCl easily leads to production of insoluble crystal, tomatidine hydrochloride and clear supernatant including reducing sugars by hydrolysis. (Ref. 1043). Two moles of glucose, one mole of galactose, one mole of xylose are obtained from hydrolyzates of tomatine. (Ref. 1033). There are a,b1,b2,g,d type-tomatines. Only the a-type contains complete sugar-chains, those of others are incomplete, for examole, one sugar deletion or substitution. (Ref. 1046). a-Tomatine contains 4 moles of sugar bound to 1 mole of tomatidine: 2moles of D-glucose, 1mole of D-xylose, and 1 mole of D-galactose. (Ref. 1047/1048). Substitute for digitonin as steroid precipitant (Ref. 1049) |
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| 311 |  |
Trenbolone / Trienbolone / Trienolone |
17b-Hydroxyestra-4,9,11-trien-3-one; 4,9,11-Estratrien-17b-ol-3-one / 17b-Hydroxy-19-norandrosta-4,9,11-trien-3-one /19-Norandrosta-4,9,11-trien-17b-ol-3-one |
SST0311 | Hideaki Nishino |
C18H22O2 | 270.366 | |
Preparation from 3-chloro-4,5-seco-5-oxo-17-benzoxy-19-nor-androsta-2,9-dien (Ref. 1050). 17b-Hydroxyestra-5(10),9(11)-dien-3-one was reacted with 2,3-dichloro-5,6-dicyano-p-benzo-quinone in dioxane, left atroom temperature, filter and wash the precipitate with dioxane, and evaporated. Solubilize the black ppt in methylene chloride and ether, filter with magnesol. the yellowish eluate is sol in methylene chloride, and adsorbed to the same quantity of magnesol. methylene chloride eluate is colorless. crystal solids are formed by evaporation, and crystalized in aceton-water (Ref. 1051) |
[a]20/D = -19 (c=0.45 in ethanol) (Ref. 1050) |
lmax 238mm(e = 6,070), 341.5mm(e = 27,900) (Ref. 1051) |
Effectiveness of trienbolon acetate on cows. (Ref. 1053) |
Higher activity as anabolic steroid by nitrogen retention effect. 17-ketosteroids and 17-hydroxycorticosteroids are not decreased. Blood clotting factors are not increased, especially V, VII, X factors and prothrombin. (Ref. 1052) |
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| 312 |  |
Triamcinolone / CL 19823 / Adcortyl / Aristocort / Celeste / Delphicort / Kenacort / Ledercort / Omcilon / Orion / Tricortale / Volon |
9-Fluoro-11b,16a,17,21-tetrahydroxypregna-1,4-diene-3,20-dione / D1-9a-Fluoro-16a-hydroxyhydrocortisone / 9a-Fluoro-16a-hydroxy-prednisolone / D1-16a-Hydroxy-9a-fluorohydrocortisone / 16a-Hydroxy-9a-fluoroprednisolone |
SST0312 | Hideaki Nishino |
C21H27O6F | 394.434 | |
Reaction of 21-Acetoxy-4,9(11),16-pregnatriene-3,20-dione(I) with osmiun tetroxide in benzene plus pyridine results in formation of 9a-fluoro-11b,16a,17a,21-tetrahydroxy-4-pegnene-3,20-dione, which is subjected to hydrogenation by microorganism (Cornyebacterium Simplex) to produce 16a,21-Diacetoxy-9a-fluoro-11b,17a-dihydroxy-1,4-pregnadiene-3,20-dione. Its saponification leads to the final product. (Ref. 1054) Alternatively, microorganic dehydrogenation of 16a,21-diacetoxy-9a-fluoro-11b,17a-dihydroxy-4-pregnene-3,20-dione by C. simplex or Nocardia corallina. The acetylation produces 16a,21-Diacetoxy-9a-fluoro-11b,17a-dihydroxy-1,4-pregnadiene-3,20-dione. Its saponification leads to the final objective compound. (Ref. 1055) Preparation through 16a-hydroxylation in Streptomyces roseochromogenus. (Ref. 1056) |
Strong glucocorticoid activity, also diacetate form, no retention activity of sodium ions. With rat liver glycogen assay (subcutaneous methods), free form is 13-times stronger than hydrocortisone, and the diacetate is 15-36-times stronger than hydrocortisone (Ref. 1054) Anti-inflammatory action. No retention activity of sodium ions because of 16a-hydroxyl group (Ref. 1057) |
||||||||||||||||||
| 313 |  |
Triamcinolone acetonide / Adcortyl-A / Aristoderm / Cutinolone Simple / Ftorocort / Kenacort-A / Kenalog / Kenaquart / Ledercort D / Omcilon-A / Rineton / Solodelf / Tramacin / Tricinolon / Vetalog / Volon A / Volonimat |
9-Fluoro-11b,21-dihydroxy-16a,17-[1-methylethyliden-ebis(oxy)]pregna-1,4-diene-3,20-dione / 9a-Fluoro-11b,16a,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone / 9a-Fluoro-16a-hydroxyprednisolone acetonide / Triamcinolone 16a,17-acetonide / 9a-Fluoro-11b,21-dihydroxy-16a,17a-isopropylidenedioxy-1,4-pregnadiene-3,20-dione / 9a-fluoreo-16a,17-isopropylidenedioxyprednisolone. |
SST0313 | Hideaki Nishino |
C24H31O6F | 434.498 | |
292-294 C (Ref. 1058) |
Sparingly sol in methanol, acetone, ethylacetate. (Ref. 1058) |
UVmax (anhydrous alcohol): 238-239nm (e=14,600) (Ref. 1055) |
nmax 3470, 1724, 1677, 1630, 1623 (inflection) /cm (Ref. 1055) |
Glucocorticoid to human. Cortisteroid to domestic animals. Anti-inflammatory effect. These effects are much greater than triamcinolone. Compund (liver glycogen, anti-inflammatory action); 9a-Fluoro-16a-hydroxyprednisolone (14(9-22), 4); 9a-Fluoro-16a-hydroxycortisol (11(7-19), 1); Triamcinolone acetonide (92(48-176), 40); Cortisol acetate (1, 1) (Ref. 1058) |
|||||||||||||||
| 314 |  |
Triamcinolone hexacetonide / Triamcunolone acetonidetert-butyl acetate / Tatba / CL-34433 / Aristospan / Lederspan |
9-Fluoro-11b,16a,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone / 21-(3,3-Dimethylbutyrate), 21-tert-butyl-acetate-9a-fluoro-11b-hydroxy-16a,17a-(isopropylidenedioxy) pregna-1,4-diene-3,20-dione / 21-(3,3-Dimethylbutyryloxy)-9a-fluoro-11b-hydroxy-16a,17a-(isopropylidenedioxy) pregna-1,4-diene-3,20-dione |
SST0314 | Hideaki Nishino |
C30H41O7F | 532.641 | |
Synthesis through reaction of triamcinolone with perchloric acid in keton or aldehyde (Ref. 1057) |
295-296 C (Ref. 1057) |
Sol in chloroform, dimethylacetoamide (75 g/100 ml), ethylacetate (0.77g/100ml), methanol (0.59g/100ml), diethylcarbonate (0.50g/100ml), glycerin (0.42g/100ml), propylene glycol (0.13g/100ml), absolute alcohol (0.03g/100ml). Sparingly sol in water (0.0004g/100ml) (25 ). (Ref. 1057) |
Anti-inflammatory action, glucocorticoid effect. Stronger activity in topical tissues than triamcinolone. (Ref. 1057) More toxic than triamcinolon. (Ref. 1059) LD50(mg/kg body weight)(d: days); Mouse; about 800(7d),141(114-174)(14d),132(107-162)(21d). Rat; 94(60-305)(7d),35(25-50)(14d),32(24-43)(21d). (Ref. 1059) |
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| 315 |  |
Uscharidin |
2,14-Dihydroxy-19-oxo-3-[(tetrahydro-6-methyl-2,3-dioxo-2h-pyran-2-yl)oxy]card-20(22)-enolide |
SST0315 | Hideaki Nishino |
C29H38O9 | 530.607 | |
Isolation form Calotropis procera R.Br., Asclepiadaceae (Ref. 0653) |
Cardiac glycoside. Arrow poison in Africa. Lethal dose 0.15mg/kg cat. (Ref. 0653) |
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| 316 |  |
Uzarin |
3b-[(6-O-b-D-glucopyranosyl-b-D-glucopyranosyl)oxy]-14-hydroxy-5a-card-20(22)-enolide |
SST0316 | Hideaki Nishino |
C35H54O14 | 698.795 | |
UVmax: 217nm (loge=4.23) (Ref. 1065) |
Plants. Contained in African medicine, uzara, which is extracted from dried roots of a Gomphocarpus sp, Asclepiadaceae. (Ref. 1063) Also isolated from uzara of a Xysmalobium undulatum R. BR. (Ref. 1064). Also isolated from roots and seed of a Pachycarpus schinzianus (Schltr.) N. E. BR. (Ref. 1065) Preparation from glycoside of Nerium odorum Sol. (Ref. 1067) |
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| 317 |  |
Uzarigenin / Odorigenin |
3b,14-Dihydroxy-5a-card-20(22)-enolide |
SST0317 | Hideaki Nishino |
C23H34O4 | 374.514 | |
246-248 C (methanol/chloroform/ether) (Ref. 1070) |
lmax=217mm (e=16,400) (Ref. 1070) |
t=9.2,9.1(6H of C-19,C-18), 7.3(1H of 17a-H), 6.0,5.6(1H of 3-,14-OH), 5.1(2H of 21-CH2), 4.1ppm (1H of 22CH-group) (dimethylsulfoxide) (Ref. 1070) |
374(M+), (372), 356, 341, 338, 323, 204, 203 (Ref. 1070) |
Plants. Isolated from African medicine, uzara, which is extracted from deied roots of Gomphocarpus sp, Asclepiadaceae. (Ref. 1063) Also isolated from uzara of Xysmalobium undulatum R. BR. (Ref. 1064). Also isolated from roots and seeds of Pachycarpus schinzianus (Schltr.) N. E. BR. (Ref. 1065). Preparation from glycosides of Nerium odorum Sol. (Ref. 1067) |
Antidiarrheal action. (Ref. 1067) |
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| 318 |  |
Veralkamine / Veralcamine |
17-Methyl-18-nor-16,28-secosolanida-5,12-diene-3b,16b-diol /17-Methyl-20a-((2S,5S)-5-methyl-2-piperidyl)-18-nor-17a-pregna-5,12-diene-3b,16b-diol / (22S:25S)-12,26-epimino-17b-methyl-18-norcholesta-5,12-diene-3b-diol / (17S:12S:25S)-22,26-epimino-18-(13-17)-abeo-cholesta-5,12-diene-3b,16b-diol |
SST0318 | Hideaki Nishino |
C27H43O2N | 413.636 | |
(carbon tetrachloride), 3230 (broad) and 3635/cm (hydroxyl absorption) (Ref. 1073) |
singlet at d=0.96(18-H3,19-H3), two dublets at 0.97(27-H3) and 0.81(21-H3), three multiplets at 3.41(3-H), 4.0(16-H), 5.25ppm (6-H and 12-H) (Ref. 1073) |
m/e 412(M-1), 315(M-98), 413(M+), 98(M+-315) (Ref. 1073) |
Plants. Alkaloid from Veratrum album sp. lobelianium (Bernh.) Suessenguth, Liliaceae (Ref. 1072) |
Complete determination of structure. First natural steroid possessing 18-nor-17b-methyl skeleton. Ppt by digitonin (evidence for 3b-hydroxyl group). No C-nor-D-homo steroid skeleton, which is often found in Veratrum bases. (Ref. 1073/1074) X-ray analysis of structure. Confirmation of stereochemical structure determined before. (Ref. 1075) |
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| 319 |  |
Vernadigin |
Strophadogenin-3b-D-diginoside |
SST0319 | Hideaki Nishino |
C30H44O10 | 564.664 | |
228.5-230 C (Ref. 0567) |
UVmax: 218 nm(log e=4.2), which shows butenolide ring. (Ref. 0567) |
1640, 1750 (a,b-unsaturated five-membered lactone); 1780 (carbonyl); 3450, 3510/cm (hydroxyl) (Ref. 0567) |
Plants. Extracted from Adonis vernalis L., Ranunculaceae. One of two cardenolides found positive in Kedde test, different from five cardenolides; cymarin, adonitoxin, strophanthidin, strophadogenin (16-hydroxystrophanthidin), and acetyladnitoxin (Ref. 0567) |
Cardiac glycoside (Ref. 0567) |
Yields aglycon and sugar portion by hydrolysis through boiling in 0.05 N HCl-50% aqueous methanol for 20 min (analyzed in silicagel chromatogrephy). The aglycon is estimated as strophadogenin because of 240-242 C m.p. |
||||||||||||||
| 320 |  |
Withaferin A |
(20S,22R)-5,6b-Epoxy-4b,22,27-trihydroxy-1-oxo-5b-ergosta-2,24-dien-26-oic acid d-lactone / 4b,27-Dihydroxy-1-oxo-5b,6b-epoxywitha-2,24-dienolide |
SST0320 | Hideaki Nishino |
C28H38O6 | 470.598 | |
[a]28/D=+125 (c=1.30 in chloroform) (Ref. 1078) |
Uvmax (ethanol): 214, 335nm (e=17,300,165) (Ref. 1078) |
lmax 2.81, 2.94 (hydroxyl), 3.33, 5.92m (a,b-unsaturated d-lactone,a,b-unsaturated cyclohexanone). (Ref. 1078) |
6.18(d,J=10Hz,C-2H), 6.97(dd,J=10 and 6Hz,C-3H), 3.75(d,J=6Hz,C-4H), 3.20(W1/2 to 4Hz,C-5H), 4.40(dt,J=12 and 3.5Hz,C-22H), 1.38(s,C-10CH3), 0.68(s,C13-CH3), 0.97(d,J=6Hz,C-20CH3), 2.03(s,C-24CH3), 4.35(s,C-25CH2OH). (Ref. 1077) |
ORD(C 0.0944)[f]/600 = +522 , [f]/589 = +522, [f]/500 = +820, [f]/400 = +2609, [f]/367 = +4510, [f]/343 = +1603, l0 333.5mm, [f]/319 = -895, l0 309mm, [f]/273 = +7679, [f]/262.5 = +5628, [f]/252 = +3504, [f]/247 = +5591. (Ref. 1078) |
Antifungal and antitumor activities. Significant effect on mouse sarcoma-180 by dose of 30mg/kg. (Ref. 1078) |
||||||||||||||
| 321 |  |
Withanolide D |
4b,20a,(R)-Dihydroxy-1-oxo-5b,6b-epoxywitha-2,24-dienolide |
SST0321 | Hideaki Nishino |
C28H38O6 | 470.598 | |
6.21(d,J=10Hz,C-2H), 6.97(dd,J=10 and 6Hz,C-3H), 3.77(d,J=6Hz,C-4H), 3.25(W1/2 to 4Hz,C-6H), 4.25(dd,J=12 and 5Hz,C-22H), 1.41(s,C-10CH3), 0.85(s,C-13CH3), 1.27(s,C-20CH3), 1.91(two methyl signal). (Ref. 1077) |
Plants. One of predominant steroids extracted from the leaves of Withania somnifera Dun., Solanaceae. 0.05% dry weight of leaves. (Ref. 1077) |
Antibacterial action. (Ref. 1076) |
Ever called chemotype II of W. Somnifera (chemotype I is Withaferin A). (Ref. 1077) |
||||||||||||||||
| 322 |  |
Wortmannin |
1,6bb,7,8,9a,10,11,11b-Octahydro-11-hydroxy-1-(methoxymethyl)-9ab,11bb-dimethyl-3H-furo[4,3,2-de]indeno[4,5-h][2]benzopyran-3,6,9-trione acetate |
SST0322 | Hideaki Nishino |
C23H24O8 | 428.432 | |
238-239 C (Ref. 1081) |
[a]26/D=+89 (c=1.1 in chloroform) (Ref. 1081) |
Unstable in pH3-8 fluids. (Ref. 1081) |
lmax 257, 292nm (e=11,770, 7,700) (Ref. 1081) |
Crystal. Data: M=428, orthorhombic, a=2567(7), b=702(1), c=1177(2)pm, P=2119.4 106pm3, Dm=1.34, Z=4, Dc=1.34, space group P2,2,2, (D4/2,No.19). (Ref. 1082) |
Extracted from Penicillium wortmannii Klocker. (Ref. 1080) |
Antibacterial antibiotics. Cause spiral waving characteristic in Botrytis allii Hypae. (Ref. 1080) |
|||||||||||||
| 323 |  |
Tetrahymanol |
Gammacerane 3b-ol |
SST0323 | Hideaki Nishino |
C30H52O | 428.733 | |
60-MC. proton NMR. 4 sharp peaks characteristic of triterpenoid methyl groups at t 9.03 with area corresponding to eight methyls (46,49,51, and 58 c.p.s with relative areas 1:3:1:3). (Ref. 1107). |
Isolated from a protozoan, Tetrahymena pyriformis. First pentacyclic triterpenoid alcohol in animal kingdom (ever found only in plant kingdom). (Ref. 1107) |
In vitro biosynthesis of tetrahymanol: lyophilize T. pyriformis, suspend in Ringer phosphate medium and break in Potter-Elvehjem homogenizer, and added[14C]-squalene and [3H]-squalene 2,3-oxide.In the homogenate, squalene can be directly converted to tetrahymanol. Squalene-2,3-oxide is not the intermediate. The enzyme system holds the biosynthetic activity after lyophilization. There seems to be no interconversion between squalene and squalene-2,3-oxide. The oxygen molecules of tetrahymanol might not be derived from atmosphere. (Ref. 1105) The enzyme system involving in biosynthesis was soluble and isolated in cell- and lipid free-system. Downstream reaction from squalene, the system requires no oxygens, hydrohen at C-3 and oxygen at C-21 are from medium. (Ref. 1104) Tetrahymanol from T. pyriformis can be substituted with ergosterol. This is because ergosterol blocks the synthesis of tetrahymanol. (Ref. 1103) Inhibition of tetrahymanol biosynthesis by cholesterol. Treatments influencing on activity of membrane-bound enzyme, membrane structure and function inhibits the late pathway of biosynthesis. (Ref. 1101) Changes of fatty acid composition by ergosterol substitution. (Ref. 1099/1100) 3b-(b-Dimethylaminoethoxy)-androst-5-en-17-one inhibits the biosynthesis of Tetrahymanol. (Ref. 1097/1098) Contribution to maintenance of structure and function of membrane required for cell proliferating phase and interphase. (Ref. 1092/1093/1095/1099/1100/1101) Crystal structure of tetrahymanol hemihydrate. (Ref. 1096) Inhibition to proliferation by 20a-hydroxycholesterol and 7-ketocholesterol. (Ref. 1095) Inhibition of biosynthesis of Tetrahymena pyriformis squalene synthetase by cholesterol. (Ref. 1093) Relation of swimming rate and membrane fluidity. (Ref. 1092) Purification of squalene-tetrahymanol cyclase (Ref. 1085) |
X-ray analysis of tetrahymanol p-bromobenzoate ester. M.p. 297-298.5 (anal.calcd. for C37H55BrO2). The crystal shows orthorhombic system holding space group C222. Four molecules per unit cell, exhibiting a=13.06, b=6.33, c=38.06A dimensions. B-dimension is relatively shorter so that tetrahymanol skeleton should be flat. This estimation coinsides well with the non-chair forms of D- and E-rings. (Ref. 1107) Revised structure. (Ref. 1106) |
||||||||||||||||
| 324 |  |
3-Acetylstrophadogenin |
SST0324 | Hideaki Nishino |
C25H34O8 | 462.533 | |
m.p. 238-240 C (Ref. 0567) |
Sol in pyridine. (Ref. 0567) |
220mm(loge=4.18) (butenolide ring) (Ref. 0567) |
1625, 1700, 1798 (a,b-unsaturated five-membered lactone), 1740 (ester group), 1720 (carbonyl group)/cm. (Ref. 0567) |
Paper chromatography.(Ref. 0567) |
Plants. Found in green parts of Adonis vernalis L. in addition to five cardenolides: cymarin, adonitoxin, strophanthidin, strophadogenin (16-hydroxy-strophanthidin), and acetyladonitoxin in paper chromatography.(Ref. 0567) |
Cardiotonic glycoside. (Ref. 0567) |
Positive color reaction with Kedde reagent. Strophadogenin can be yielded by mild alkali hydrolysis. Hydrolysis in 3% KOH produces volatile acid, which turned out to be acetic acid. (Ref. 0567) |
|||||||||||||
| 325 |  |
Cafestol / Cafesterol |
3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-7-hydroxy-10b-methyl-5a,8-methano-5aH-cyclohepta[5,6]naphthol[2,1-b]-furan-7-methanol |
SST0325 | Hideaki Nishino |
C20H28O3 | 316.435 | |
lmax (EtOH) 223, 290 mm (loge=3.66,3.63) (Ref. 1109) |
Circular dichroism and X-ray crystal analysis (Ref. 1115) |
||||||||||||||||||
| 326 |  |
Withacnistin |
4b-Hydroxy-18-acetoxy-1-oxo-5b,6b-epoxywitha-2,24-dienolide |
SST0326 | Hideaki Nishino |
C30H40O7 | 512.634 | |
130-135 C (Ref. 1078) |
[a]27/D=+123 (c=1.21) (Ref. 1078) |
Sol in ethanol, methanol, methanol-water(9:1), petroleum ether, chloroform, formamide. |
lmax 215mm (e=16,100) (Ref. 1078) |
lmax 2.81, 2.93, 3.31, 5.78, 5.92, 8.05, 9.63m. (Ref. 1078) |
3.82d(10.0,C-2), 3.04dd(10.0,6.0,C-3), 6.24d, 5.78d(C-18), 8.60[-0.08](C-19), 8.90d(6.5)[0.04](C-21), 8.08[0.07](C-27), 8.08[0.25](C-28), 7.93(-COCH3),Dt=t[CDCl3-benzene(1:1)]-t(CDCl3). (Ref. 1078) |
m/e 125(C7H9O2),181(C11H17O2), M+ 512(C30H40O7),167(C9H11O3), 154(C8H10O3), 141(C7H9O3), 124(C7H8O2), 389(C23H33O5). (Ref. 1078) |
ORD(c=0.033)[f]/600=+461 , [f]/589=+461, [f]/500=+778, [f]/400=+2305, [f]/368=+4148, [f]/343=+1440, l/0=334mm, [f]/317.5=-1095, l/0=307mm, [f]/272=+7202, [f]/261=+5992, [f]/250=+4206,[f]/243=+6741 (Ref. 1078) |
Plants. Leaves of Acnistus arborescens (L.). (Ref. 1078) |
The acetate, m.p. 131-132 , [a]25/D=+180 (c=1.90); UVlmax 217mm (e=15,500); IRlmax 3.31, 5.76, 5.90, 8.06, 9.62; C32H42O8. (Ref. 1078) |
||||||||||
| 327 |  |
3-Ethoxy-2,3-dihydrowithacnistin |
SST0327 | Hideaki Nishino |
C32H46O8 | 558.703 | |
[a]24/D=+29 (c=0.46) (Ref. 1078) |
Sol in ethanol, methanol-water (9:1), petroleum ether, chloroform, formamide. (Ref. 1078) |
lmax 227mm(e=8,600) (Ref. 1078) |
lmax 2.78, 2.90, 3.31, 5.78, 5.88, 8.95, 9.62m (Ref. 1078) |
Plants. Leaves from Acnistus arborescens (L.). (Ref. 1078) |
The acetate, m.p. 216-217 (dec.sintered at 2130); [a]23/D=+16 (c=1.16); UVlmax 227mm (e=8,900); IRlmax 3.30, 5.75, 5.88, 8.06, 9.65m; C34H48O9 (Ref. 1078) |
|||||||||||||||
| 328 |  |
squalamine |
3b-N-1{N-[3-(4-aminobutyl)]-1,3-diaminopropane}-7a,24z-dihydroxy-5a-cholestane 24-sulfate |
SST0328 | Hideaki Nishino |
C34H66O5N3S | 628.971 | |
Synthesis of analogues as 6b-hydroxy-3-aminosterols from hyodeoxycholic acid. (Ref. 1119) |
Two-dimensional NMR spectroscopy(Ref. 1118). |
Purification by the following steps: acetonitrile extraction, lyophilization, Bio-Gel P-3 gel filtration, C18 reversed-phase HPLC, cation-exchange HPLC, C4 reversed-phase HPLC. (Ref. 1117) |
Tissues of dog fish shark, Squalus acanthias. (Ref. 1117) |
Permializes large unilamellar phospholipid vesicles. (Ref. 1121) |
Position of spermidine and sulphate groups (Ref. 1118). |
||||||||||||||
| 329 |  |
cholesterol glucuronide |
SST9001 | Etsuko Yasugi |
C33H54O7 | 562.778 | |
2800-3000 cm-1 (methylene) 1600 cm-1 (carboxy salt) 1000-1100 cm-1 (hydroxy group) |
||||||||||||||||||||
| 330 |  |
5b-cholestane-3a,7a,26-triol |
SST9002 | Etsuko Yasugi |
C27H48O3 | 420.668 | |
2 46 |
25Rform [a]  +15.9, 25Sform [a] +8.8" |
|||||||||||||||||||
| 331 |  |
5b-cholestane-3a,7a,25-triol |
SST9003 | Etsuko Yasugi |
C27H48O3 | 420.668 | |
181-183 C (Ref. 9003) |
cm-1 3480,2925,2860,1465,1378,1160,1150,1070 and 980 (Ref. 9003) |
621,546,531,456,441,366,351,255,253,131(base peak) (TMS deriv.) (Ref. 9003) |
human bile (Ref. 9002) |
|||||||||||||||||
| 332 |  |
5b-cholestane-3a,7a,24-triol |
SST9004 | Etsuko Yasugi |
C27H48O3 | 420.668 | |
1H-NMR 18-CH3 19-CH3 21-CH3 26,27-CH3 24R form 66.0 91.0 91.0 91.5 24Sform 65.0 90.0 88.5 92.5 (in H2) |
546,531,503,456,441,413,366,351,323,255,145(base peak),73 (TMS deriv.) (Ref. 9001) |
human bile (Ref. 9002) |
||||||||||||||||||
| 333 |  |
5b-cholestane-3a,7a,24,26-tetrol |
SST9005 | Etsuko Yasugi |
C27H48O4 | 436.668 | |
noncrystalline material (Ref. 9004) |
cm-1 (CHCl3) 3350 (Ref. 9004) |
1H-NMR 18-CH3=0.70, 19-CH3=0.96, 21-CH3=1.00, 27-CH3=1.23 (Ref. 9004) |
681,632,591,542,501,452,411,343,321(base peak),294,281,253,233,213 (TMS deriv.) (Ref. 9004) |
human bile (Ref. 9004) |
||||||||||||||||
| 334 |  |
5b-cholestane-3a,7a,25,26-tetrol |
SST9006 | Etsuko Yasugi |
C27H48O4 | 436.668 | |
200-202 C (Ref. 9005) |
||||||||||||||||||||
| 335 |  |
5b-cholestane-3a,7a,26,27-tetrol |
SST9007 | Etsuko Yasugi |
C27H48O4 | 436.668 | |
136.5-138 C (Ref. 9004) |
cm-1 3300 (Ref. 9004) |
1H-NMR 18-CH3=0.70, 19-CH3=0.95, 21-CH3=0.933b-H=3.75, 7b-H=3.97, 26- AND 27-CH2=4.02 (Ref. 9004) |
544,529,454,364,343,281,255(base peak),253 (TMS deriv.) (Ref. 9004) |
human bile (Ref. 9004) |
||||||||||||||||
| 336 |  |
w-trichechol |
5b-cholestane-3a,6a,7b,25,26-pentol |
SST9008 | Etsuko Yasugi |
C27H48O5 | 452.667 | |
709,632,619,542,529,452,439,363,285,253,219,195(base peak) (TMS deriv.) (Ref. 9006) |
manatee (Trichechus manatus latirostris) bile (Ref. 9006) |
||||||||||||||||||
| 337 |  |
5b-cholestane-3a,6b,7a,26-tetrol |
SST9009 | Etsuko Yasugi |
C27H48O4 | 436.668 | |
634,544,529,489,454,441,285,253,195(base peak) (TMS deriv.) (Ref. 9006) |
manatee (Trichechus manatus latirostris) bile (Ref. 9006) |
|||||||||||||||||||
| 338 |  |
3a,12a,25-trihydroxy-5b-cholestan-7-one |
SST9010 | Etsuko Yasugi |
C27H46O4 | 434.652 | |
188-189 C (Ref. 9007) |
cm-1(KBr) 3350,1695 (Ref. 9007) |
1H-NMR(pyridine-d5) 18-CH3=0.77, 19-CH3=1.02, 21-CH3=1.20, 26,27-CH3=1.39, 3b-H=3.75, 12b-H=4.24 (Ref. 9007) |
560,470,380,359,341,269,251,131(base peak) (TMS deriv.) (Ref. 9007) |
cerebrotendinous xanthomatosis patient bile and feces (Ref. 9007) |
||||||||||||||||
| 339 |  |
5b-cholestane-3a,7a,12a,24,25,26-hexol |
SST9011 | Etsuko Yasugi |
C27H48O6 | 468.666 | |
1H-NMR 18-CH3 19-CH3 21-CH3 27-CH3 3b,7b,12b,24-H 26-H2 24R form 0.80 0.98 1.23 1.53 3.40-4.50 4.00 24Sform 0.77 0.95 1.20 1.45 3.40-4.50 3.92 (Ref. 9008) |
797,681,617,591,527,501,437,411,347,343,321,253,219(base peak)(TMS deriv.) (Ref. 9008) |
|||||||||||||||||||
| 340 |  |
5a-cholestane-3a,7a,12a,25-tetrol |
SST9012 | Etsuko Yasugi |
C27H48O4 | 436.668 | |
noncrystalline material (Ref. 9007) |
1H-NMR(pyridine-d5) 18-CH3=0.81, 19-CH3=0.89, 21-CH3=1.23, 26,27-CH3=1.36, 7b-H=4.05, 3b,12b-H=4.16 (Ref. 9007) |
343,253 (TMS deriv.) (Ref. 9007) |
cerebrotendinous xanthomatosis patient urine and feces (Ref. 9008) |
|||||||||||||||||
| 341 |  |
5b-cholestane-3a,7a,12a,22,25-pentol |
SST9013 | Etsuko Yasugi |
C27H48O5 | 452.667 | |
1H-NMR 18-CH3 19-CH3 21-CH3 26,27-CH3 22Rform 0.84 1.00 1.40 1.44 22Sform 0.86 1.00 1.39 1.40 (Ref. 9021) |
653,563,473,453,433,383,363,343,293,261,253,171(base peak),131,81,73 (TMS deriv.) (Ref. 9012) |
cerebrotendinous xanthomatosis patient bile and urine (22R form only) (Ref. 9011) |
||||||||||||||||||
| 342 |  |
27-nor-5b-cholest-25-ene-3a,7a,12a,24-tetrol |
SST9014 | Etsuko Yasugi |
C26H44O4 | 420.625 | |
195-197 C (Ref. 9002) |
cm-1 (KBr) 3450(OH) 1636,883(-CH=CH2) (Ref. 9002) |
1H-NMR(pyridine-d5) 18-H3=0.83, 19-H3=1.00, 21-H3=1.24, 3b-H=3.78, 7b-H=4.09, 12b-H=4.26, 24-H=4.35, 25-H=6.15, 26-H2=5.35, 5.55 (Ref. 9002) |
708,618,528,481,438,349,343,294,281,253(base peak),157,129 (TMS deriv.) (Ref. 9002) |
human bile (Ref. 9002) |
||||||||||||||||
| 343 |  |
5b-cholane-3a,7a,23,24-tetrol |
SST9015 | Etsuko Yasugi |
C24H42O4 | 394.588 | |
224.5-226.5 C (Ref. 9002) |
cm-1 (KBr) 3350(OH) (Ref. 9002) |
1H-NMR(pyridine-d5) 18-H3=0.74, 19-H3=0.96, 21-H3=1.11, 3b,7b,23b-H =3.4-4.5, 24-H2=3.90 (Ref. 9002) |
579,489,399,309(base peak),283,267,255,199(TMS deriv.) (Ref. 9002) |
human bile (Ref. 9002) |
||||||||||||||||
| 344 |  |
5b-cholestane-3a,7a,12a,23-tetrol |
SST9016 | Etsuko Yasugi |
C27H48O4 | 436.668 | |
cm-1 (KBr) 23Sform 3400(OH),1080,1040,980,950,920 23Rform 3340(OH),1080,1030,980,950,918 (Ref. 9012) |
1H-NMR(pyridine-d5) 18-H3 26,27-H 19-H3 21-H3 3b-H 7b,23-H 12b-H 23Rform 0.89 1.00,1.03 1.01 1.39 3.70 4.10 4.32 23Sform 0.88 0.95,0.98 1.00 1.38 3.70 4.10 4.32 (Ref. 9012) |
|||||||||||||||||||
| 345 |  |
5b-cholestane-3a,7a,12a,24-tetrol |
SST9017 | Etsuko Yasugi |
C27H48O4 | 436.668 | |
cm-1 3500 (Ref. 9016) |
m/e= 681,634,591,544,501,454,411,364,343,321,253,145(base peak),55 (TMS deriv.) (Ref. 9017) |
|||||||||||||||||||
| 346 |  |
26-deoxy-5b-ranol |
27-nor-5b-cholestane-3a,7a,12a,24-tetrol |
SST9018 | Etsuko Yasugi |
C26H46O4 | 422.641 | |
1HNMR (pyridine-d5) 18-H3 19-H3 26-H3 21-H3 3b,7b,12b,24-H 24R form 0.79 0.99 1.15 1.27 3.5-4.4 24Sform 0.84 1.01 1.17 1.28 3.5-4.4 (Ref. 9019) |
m/e= 530,515,501,440,433,425,411,351,343,335,321,281,253,131(base peak) (TMS deriv.) (Ref. 9019) |
||||||||||||||||||
| 347 |  |
26-deoxy-5a-ranol |
27-nor-5a-cholestane-3a,7a,12a,24-tetrol |
SST9019 | Etsuko Yasugi |
C26H46O4 | 422.641 | |
||||||||||||||||||||
| 348 |  |
5b-cholestane-3a,7a,12a-triol |
SST9020 | Etsuko Yasugi |
C27H48O3 | 420.668 | |
186-187.5 C (Ref. 9022) |
+30.4 (Ref. 9024) |
m/e= 546,456,366(base peak),253 (TMS deriv.) (Ref. 9023) |
||||||||||||||||||
| 349 |  |
5b-cholest-25-ene-3a,7a,12a-triol |
SST9021 | Etsuko Yasugi |
C27H46O3 | 418.652 | |
164 C (Ref. 9025) |
cm-1 (NUJOL) 3660(OH),1650,883(CH2=C. ) (Ref. 9025) |
cerebrotendinous xanthomatosis patient bile (Ref. 9023) |
||||||||||||||||||
| 350 |  |
27-nor-5b-cholestane-3a,7a,12a,24,25,26-hexol |
SST9022 | Etsuko Yasugi |
C26H46O6 | 454.640 | |
174-175 C (Ref. 9002) |
cm-1 (KBr) 3350(OH) (Ref. 9002> |
1H-NMR 18-H3=0.80, 19-H3=0.99, 21-H3=1.32, 3b,7b,12b,24,25,26-H=3.50-4.40 (Ref. 9002) |
||||||||||||||||||
| 351 |  |
5b-cholestane-3a,7a,12a,25-tetrol |
SST9023 | Etsuko Yasugi |
C27H48O4 | 436.668 | |
+36.8 (Ref. 9024) |
m/e= 724,709,634,619,544,529,454,439,364,349,131(base peak)(TMS DERIV.)(Ref. 9028) |
|||||||||||||||||||
| 352 |  |
5b-cholestane-3a,7a,12a,23,25-pentol |
SST9024 | Etsuko Yasugi |
C27H48O5 | 452.667 | |
23Rform:non-crystalline material, 23Sform209-210 C(Ref. 9031) |
||||||||||||||||||||
| 353 |  |
5b-cholestane-3a,7a,12a,24,25-pentol |
SST9025 | Etsuko Yasugi |
C27H48O5 | 452.667 | |
cm-1(KBr) 3420(OH) (Ref. 9024) |
1H-NMR(CD3OD) 18-H3=72.4 H2, 19-H3=92.2, 21-H3=103.6, 26,27-H3=114.4,116.8, (Ref. 9024) |
|||||||||||||||||||
| 354 |  |
scymnol |
5b-cholestane-3a,7a,12a,24,26,27-hexol |
SST9026 | Etsuko Yasugi |
C27H48O6 | 468.666 | |
120-123 C (Ref. 9033) |
+34 (Ref. 9033) |
cm-1(KBr) 3400(OH) (Ref. 9033) |
|||||||||||||||||
| 355 |  |
27-nor-5b-cholestane-3a,7a,12a,24,25-pentol |
SST9027 | Etsuko Yasugi |
C26H46O5 | 438.640 | |
1H-NMR(pyridine-d5) 18-H3=0.82, 19-H3=1.00, 21-H3=1.26, 26-H3=1.52, 3b,7b,12b,24,25-H=3.55-4.40 (Ref. 9032) |
human urine (Ref. 9032/9037/9008/9038),human serum (Ref. 9010),cerebrotendinous xanthomatosis patient urine (Ref. 9007),human bile (Ref. 9002),liver disease patient serum (Ref. 9041),liver disease patient urine (Ref. 9009), urine and feces of patient with sitosterolemia and xanthomatosis (Ref. 9036), urine from patient with bile retention (Ref. 9039), patient urine with complete extrahepatic bile retention (Ref. 9040) |
|||||||||||||||||||
| 356 |  |
24-nor-5b-cholestane-3a,7a,12a,25-tetrol |
SST9028 | Etsuko Yasugi |
C26H46O4 | 422.641 | |
124-126 C (Ref. 9043) |
cm-1(KBr) 3400(OH) (Ref. 9043) |
1H-NMR(CDCl3) 18-H3=0.65, 19-H3=0.85, 21-H3=0.95, 26,27-H3=1.16 (Ref. 9043) |
||||||||||||||||||
| 357 |  |
5b-cyprinol |
5-b-cholestane-3a,7a,12a,26,27-pentol |
SST9029 | Etsuko Yasugi |
C27H48O5 | 452.667 | |
+35.5 (Ref. 9046) |
cm-1(NUJOL) 3400 (Ref. 9045) |
1H-NMR(d7-DMF) 18-H3=41.0 cps, 19-H3=52.5 (Ref. 9047) |
|||||||||||||||||
| 358 |  |
26-deoxy-26-nor-5-ranol |
26,27-dinor-5b-cholestane-3a,7a,12a,24-tetrol |
SST9030 | Etsuko Yasugi |
C25H44O4 | 408.614 | |
cm-1(KBr) 3340(OH), 1080,1030,980,950,918 (Ref. 9052) |
1H-NMR(pyridine-d5) 18-H3=0.83, 19-H3=1.02, 21-H3=1.25, 25-H3=1.35, 3b,7b,12b,24H=3.70-4.35 (Ref. 9052) |
m/z= 696,606,516,426,343,337,253 (TMS deriv.) (Ref. 9052) |
Arthroleptis poecilonotus?, Aubria subsigillata, Dicroglossus occipitalis, Rana pipiens bile (Ref. 9020) |
||||||||||||||||
| 359 |  |
cholesterol a-epoxide |
5,6a-epoxy-5a-cholesta-3b-ol |
SST9031 | Etsuko Yasugi |
C27H46O2 | 402.653 | |
||||||||||||||||||||
| 360 |  |
5-cholestene-3b,7a-diol (7a-hydroxycholesterol) |
SST9032 | Etsuko Yasugi |
C27H46O2 | 402.653 | |
GC-EI-MS(TMS) M/E=546[M], 456[M-HOTMS] (Ref. 9061) |
||||||||||||||||||||
| 361 |  |
5-cholestene-3b,7b-diol (7b-hydroxycholesterol) |
SST9033 | Etsuko Yasugi |
C27H46O2 | 402.653 | |
167 - 171 C (Ref. 9086) |
spectrum (Ref. 9060) |
GC-EI-MS(TMS) M/E=546[M], 456[M-HOTMS] (Ref. 9061) |
porcine liver lipid (Ref. 9087) , pregnant horse serum (Ref. 9086), auto-oxidation of cholesterol (Ref. 9062/9064/9065/9066/9067) , photo-oxidation of egg yolk lipid (Ref. 9060), reaction product of rat liver microsomes and cholesterol (Ref. 9061/9069), butter and cheese fat (Ref. 9070), dried egg powder (Ref. 9071/9072) |
|||||||||||||||||
| 362 |  |
7-keto-5-cholesten-3b-ol (7-ketocholesterol) |
SST9034 | Etsuko Yasugi |
C27H44O2 | 400.637 | |
GC-EI-MS(TMS) (Ref. 9061) |
||||||||||||||||||||
| 363 |  |
5a,6a-epoxycholestan-3b-ol (5a,6a-epoxycholesterol) |
SST9035 | Etsuko Yasugi |
C27H46O2 | 402.653 | |
auto-oxidation of cholesterol (Ref. 9065/9066/9067), in human serum (Ref. 9089), reaction product of rat liver microsomes and cholesterol (Ref. 9061/9069), in reaction mixture of rat sub-hepatic cells and cholesterol (Ref. 9088), reaction product of bovine liver microsomes and cholesterol (Ref. 9090), butter and cheese fat |
||||||||||||||||||||
| 364 |  |
5b,6b-epoxycholestan-3b-ol (5b,6b-epoxycholesterol) |
SST9036 | Etsuko Yasugi |
C27H46O2 | 402.653 | |
auto-oxidation of cholesterol (Ref. 9065/9066/9067/9092), photo-oxidation of egg yolk lipid (Ref. 9060), human serum (Ref. 9089), reaction product of rat liver microsomes and cholesterol (Ref. 9069), In reaction mixture of rat sub-hepatic cells and cholesterol (Ref. 9090), reaction product of bovine liver microsomes and cholesterol |
||||||||||||||||||||
| 365 |  |
cholestane-3b,5a,6b-triol (3b,5a,6b-trihydroxycholestanol) |
SST9037 | Etsuko Yasugi |
C27H48O3 | 420.668 | |
228 - 235 C (Ref. 9088) |
GC-EI-MS(TMS) M/E=636[M], 546[M-HOTMS], 456, 403, 367, 321, 217(Ref. 9090) |
product of X-ray irradiation to cholesterol (Ref. 9088), auto-oxidation of cholesterol (Ref. 9065/9066/9067), photo-oxidation of egg yolk lipid (Ref. 9060), human serum (Ref. 9089), in reaction mixture of rat sub-hepatic cells and cholesterol (Ref. 9090), reaction product of bovine liver microsomes and cholesterol |
||||||||||||||||||
| 366 |  |
5-cholestene-3b,7a,12a-triol (3b,7a,12a-trihydroxycholestanol) |
SST9038 | Etsuko Yasugi |
C27H46O3 | 418.652 | |
194 - 195 C (Ref. 9093) |
EI-MS M/E=382[M-2xH2O], 364[M-3xH2O], 251(Ref. 9093) |
|||||||||||||||||||
| 367 |  |
5-cholestene-3b,22-diol (22-hydroxycholesterol) |
SST9039 | Etsuko Yasugi |
C27H46O2 | 402.653 | |
GC-EI-MS(TMS) M/E=546[M], 531[M-CH3], 475[M-(CH2)2CH(CH3)2],173 (Ref. 9095) |
infant feces (Ref. 9095) |
|||||||||||||||||||
| 368 |  |
5-cholestene-3b,24-diol (24-hydroxy-cholesterol) |
SST9040 | Etsuko Yasugi |
C27H46O2 | 402.653 | |
GC-EI-MS(TMS) M/E=546[M], 503[M-CH(CH3)2], 456[M-HOTMS], 413[503-HOTMS], 159, 145 (Ref. 9095) |
infant feces (Ref. 9095) |
|||||||||||||||||||
| 369 |  |
5-cholestene-3b,25-diol (25-hydroxycholesterol) |
SST9041 | Etsuko Yasugi |
C27H46O2 | 402.653 | |
GC-EI-MS(TMS) (Ref. 9069) |
||||||||||||||||||||
| 370 |  |
5-cholestene-3b,26-diol (26-hydroxy-cholesterol) |
SST9042 | Etsuko Yasugi |
C27H46O2 | 402.653 | |
|||||||||||||||||||||
| 371 |  |
3,5-cholestadien-7-one |
SST9043 | Etsuko Yasugi |
C27H42O1 | 382.622 | |
109 - 111 C (Ref. 9062) |
lmax = 280nm, e=23000(in EtOH) (Ref. 9062) |
|||||||||||||||||||
| 372 |  |
4,6-cholestadien-3-one |
SST9044 | Etsuko Yasugi |
C27H42O1 | 382.622 | |
lmax = 287nm (Ref. 9089) |
GC-EI-MS (Ref. 9089) |
|||||||||||||||||||
| 373 |  |
4-cholesten-3-one |
SST9045 | Etsuko Yasugi |
C27H44O1 | 384.638 | |
lmax = 241nm (Ref. 9089) |
GC-EI-MS (Ref. 9089) |
|||||||||||||||||||
| 374 |  |
5-stigmastene-3b,7a-diol (7a-hydroxy-b-sitosterol) |
SST9046 | Etsuko Yasugi |
C29H50O2 | 430.706 | |
|||||||||||||||||||||
| 375 |  |
5-stigmastene-3b,7b-diol (7b-hydroxy-b-sitosterol) |
SST9047 | Etsuko Yasugi |
C29H50O2 | 430.706 | |
|||||||||||||||||||||
| 376 |  |
7-keto-5-stigmastene-3b-ol (7-keto-b-sitosterol) |
SST9048 | Etsuko Yasugi |
C29H48O2 | 428.690 | |
GC-EI-MS(TMS) (Ref. 9061) |
||||||||||||||||||||
| 377 |  |
5,6-epoxystigmastan-3b-ol (5,6-epoxy-b-sitosterol) |
SST9049 | Etsuko Yasugi |
C29H50O2 | 430.706 | |
|||||||||||||||||||||
| 378 |  |
5-stigmastene-3b,5a,6b-triol |
SST9050 | Etsuko Yasugi |
C29H52O3 | 448.721 | |
GC-EI-MS(TMS) M/E=664[M], 574[M-HOTMS], 484[M-2xHOTMS], 431, 395, 349, 217 (Ref. 9090) |
In reaction mixture of rat liver sub-cellular fraction and b-sitosterol (Ref. 9090) |
|||||||||||||||||||
| 379 |  |
4-stigmasten-3-one |
SST9051 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
EI-MS M/E=397[M-CH3], 271[M-C10H21], 229 (Ref. 9099) |
b-sitosterol auto-oxidation (Ref. 9099) |
|||||||||||||||||||
| 380 |  |
5-stigmasten-3-one |
SST9052 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
EI-MS M/E=412[M], 397[M-CH3], 229 (Ref. 9099) |
b-sitosterol auto-oxidation (Ref. 9099) |
|||||||||||||||||||
| 381 |  |
4-stigmastene-3,6-dione |
SST9053 | Etsuko Yasugi |
C29H46O2 | 426.674 | |
EI-MS M/E=411[M-CH3], 275[M-C10H21], 243 (Ref. 9099) |
b-sitosterol auto-oxidation (Ref. 9099) |
|||||||||||||||||||
| 382 |  |
4-stigmastene-3b,26-diol (26-hydroxy-b-sitosterol) |
SST9054 | Etsuko Yasugi |
C29H50O2 | 430.706 | |
GC-EI-MS(TMS) M/E=574[M], 559[M-CH3], 484[M-HOTMS], 445, 255, 129 (Ref. 9069) |
reaction product of rat liver microsomes and b-sitosterol (Ref. 9069) |
|||||||||||||||||||
| 383 |  |
24[R]-5-ergostene-3b,7a-diol (7a-hydroxy-campesterol) |
SST9055 | Etsuko Yasugi |
C28H48O2 | 416.680 | |
GC-EI-MS(TMS)(Ref. 9069) |
reaction product of rat liver microsomes and campesterol (Ref. 9069) |
|||||||||||||||||||
| 384 |  |
24[R]-5-ergostene-3b,7b-diol (7b-hydroxy-campesterol) |
SST9056 | Etsuko Yasugi |
C28H48O2 | 416.680 | |
GC-EI-MS(TMS)(Ref. 9069) |
reaction product of rat liver microsomes and campesterol (Ref. 9069) |
|||||||||||||||||||
| 385 |  |
7-keto-24[R]-5-ergosten-3b-ol (7-keto-campesterol) |
SST9057 | Etsuko Yasugi |
C28H46O2 | 414.664 | |
GC-EI-MS(TMS)(Ref. 9069) |
reaction product of rat liver microsomes and campesterol (Ref. 9069) |
|||||||||||||||||||
| 386 |  |
24[R]-5-ergosten-3b,26-diol (26-hydroxy-campesterol) |
SST9058 | Etsuko Yasugi |
C28H48O2 | 416.680 | |
GC-EI-MS(TMS) M/E=560, 545, 470, 431, 255, 129 (Ref. 9069) |
reaction product of rat liver microsomes and campesterol (Ref. 9069) |
|||||||||||||||||||
| 387 |  |
cholestanol |
5a-cholestan-3b-ol |
SST9059 | Etsuko Yasugi |
C27H48O1 | 388.669 | |
acetate 430(25)M+,415(9),370(58),355(23),317(6),275(30),257(37),215(100) (Ref. 9101) |
|||||||||||||||||||
| 388 |  |
coprostanol |
5b-cholestan-3b-ol |
SST9060 | Etsuko Yasugi |
C27H48O1 | 388.669 | |
[a]D +28 (Ref. 9103) |
1H-NMR(CDCl3) (Ref. 9100) |
388(76)M+,373(94),370(24),355(53),331(24),316(6),288(15),262(12),257(9),233(97),215(100) (Ref. 9106) |
human and carnivore feces (Ref. 9103) |
||||||||||||||||
| 389 |  |
cholesterol |
cholest-5-en-3b-ol |
SST9061 | Etsuko Yasugi |
C27H46O1 | 386.654 | |
388(98)M+,371(46),368(64),353(52),301(56),275(100),273(36),260(12),255(50),247(40),246(12),231(42),229(36),213(68) acetate 368(100)M+-HOAc,353(28),275(4),260(13),255(22)247(26),229(3),216(18) (Ref. 9108) |
|||||||||||||||||||
| 390 |  |
campesterol |
(24R)-24-methylcholest-5-en-3b-ol |
SST9062 | Etsuko Yasugi |
C28H48O1 | 400.680 | |
158 C (Ref. 9103) |
[a]D +33 (Ref. 9103) |
400(100)M+,385(50),382(62),367(50),315(60),289(65),274(14),273(50),261(20), 255(82),246(10),231(44),229(25),213(74) (Ref. 9108) |
|||||||||||||||||
| 391 |  |
22,23-dihydrobrassicasterol |
(24S)-24-methylcholest-5-en-3b-ol |
SST9063 | Etsuko Yasugi |
C28H48O1 | 400.680 | |
acetate m.p. 151-152 C (Ref. 9106) |
|||||||||||||||||||
| 392 |  |
crinosterol |
(24E,24S)-24-methylcholesta-5,22-dien-3b-ol |
SST9064 | Etsuko Yasugi |
C28H46O1 | 398.664 | |
398(100)M+,383(13),380(18),365(18),355(9),337(22),300(49),271(56),255(96), 213(37) (Ref. 9109) |
|||||||||||||||||||
| 393 |  |
brassicasterol |
(22E,24R)-24-methylcholesta-5,22-dien-3b-ol |
SST9065 | Etsuko Yasugi |
C28H46O1 | 398.664 | |
398(100)M+,383(16),380(19),365(18),355(11),337(28),300(56),271(65),255(94),213(34) (Ref. 9109) |
|||||||||||||||||||
| 394 |  |
24-methylenecholesterol(chalinasterol) |
24-methyl-5,24(28)-dien-3b-ol |
SST9066 | Etsuko Yasugi |
C28H46O1 | 398.664 | |
398(100)M+-HOAC,365(15),396(46),281(17),272(5),259(9),255(11),253(30),228 (10),213(23),211(9),201(6) (Ref. 9106) |
|||||||||||||||||||
| 395 |  |
sitosterol |
(24R)-24ethylcholest-5-en-3b-ol |
SST9067 | Etsuko Yasugi |
C29H50O1 | 414.707 | |
[a]D -37 (Ref. 9103) |
414(100)M+,399(45),396(54),381(42),329(50),303(70),275(18),273(54),255(60),246(12),231(58),229(25),213(78) (Ref. 9108) |
||||||||||||||||||
| 396 |  |
stigmasterol |
(22E,24S)-24ethylcholesta-5,22-dien-3b-ol |
SST9068 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
[a]D -49 (Ref. 9103) |
412(78)M+,397(8),394(6),379(7),369(24),351(31),327(4),314(3),301(2),299(54),273(26),271(73),255(100),253(22),246(4),231(18),229(20),211(12) (Ref. 9108) |
||||||||||||||||||
| 397 |  |
fucosterol |
(24(28)E)-24ethylcholesta-5,24(28)-dien-3b-ol |
SST9069 | Etsuko Yasugi |
C29H48O | 412.691 | |
[a]D -40 (Ref. 9103) |
acetate 394(80)M+-HOAc,379(8),296(100),281(23),273(3),255(6),253(11),229(3),228(11),227(4),213(11) (Ref. 9113) |
||||||||||||||||||
| 398 |  |
isofucosterol |
[24(28)Z]-24ethylcholesta-5,24(28)-dien-3b-ol |
SST9070 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
acetate 394(40)M+-HOAc,379(5),296(100),281(13),273(2),255(13),253(6),229(3),228(7),227(3),213(9) (Ref. 9113) |
|||||||||||||||||||
| 399 |  |
clerosterol |
(24S)-24ethylcholesta-5,25-dien-3b-ol |
SST9071 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
412(100)M+,397(26),394(59),379(37),328(17),314(37),310(12),299(37),273(26),271(21),255(37),231(26),229(33),213(63) (Ref. 9115) |
|||||||||||||||||||
| 400 |  |
22,23-dihydrospinasterol(schottenol) |
(24R)-24ethyl-5a-cholest-7-en-3b-ol |
SST9072 | Etsuko Yasugi |
C29H50O1 | 414.707 | |
[a]D +11 (Ref. 9103) |
414(88)M+,399(32),396(3),381(8),273(29),255(100),246(17),229(41) (Ref. 9118) |
||||||||||||||||||
| 401 |  |
spinasterol |
(22E,24S)-24ethyl-5a-cholesta-7,22-dien-3b-ol |
SST9073 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
[a]D -4 (Ref. 9103) |
412(21)M+,397(13),379(3),369(17),351(9),271(100),255(63),246(27),229(28) (Ref. 9118) |
||||||||||||||||||
| 402 |  |
avenasterol |
[24(28)z]-24ethyl-5a-cholesta-7,24(28)-dien-3b-ol |
SST9074 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
acetate 1H-NMR(CDCl3) (Ref. 9107) |
acetate 454(3)M+,439(5),379(6),356(38),341(7),327(4),313(100),296(21),288 (9),281(11),273(6),255(19),253(41),228(11),213(27),201(8) (Ref. 9119) |
||||||||||||||||||
| 403 |  |
ergosterol |
(22E,24R)-24-methylcholesta-5,7,22-trien-3b-ol |
SST9075 | Etsuko Yasugi |
C28H44O1 | 396.648 | |
[a]D -132 (Ref. 9103) |
lmax 282nm (loge=4.08) (Ref. 9138) |
acetate 438(7)M+,378(68),363(74),351(11),337(10),253(68),251(38),237(18), 235(15),213(14),157(100) (Ref. 9106) |
|||||||||||||||||
| 404 |  |
lophenol |
4a-methyl-5a-cholest-7-en-3b-ol |
SST9076 | Etsuko Yasugi |
C28H48O1 | 400.680 | |
acetate 442(100)M+,427(25),382(11),367(12),329(11),287(8),269(64),243(19), 227(34) (Ref. 9124) |
|||||||||||||||||||
| 405 |  |
gramisterol(24-methylenelophenol) |
4a,24-dimethyl-5a-cholesta-7,24(28)-dien-3b-ol |
SST9077 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
412(24)M+,397(17),394(4),379(6),328(26),314(9),310(6),285(100),269(20),267 (15),260(9),245(8),241(11) (Ref. 9126) |
|||||||||||||||||||
| 406 |  |
citrostadienol |
[24(28)Z]-4a-methyl-24ethyl-5a-cholesta-7,24(28)-dien-3b-ol |
SST9078 | Etsuko Yasugi |
C30H50O1 | 426.717 | |
acetate 468(4)M+,453(4),393(6),379(48),355(6),327(100),310(20),302(7),295 (10),287(4),269(15),267(34),243(6),242(10),241(10),227(20) (Ref. 9127) |
|||||||||||||||||||
| 407 |  |
obtusifoliol |
4a,14a,24-trimethyl-5a-cholesta-8,24(28)-dien-3b-ol |
SST9079 | Etsuko Yasugi |
C30H50O1 | 426.717 | |
acetate 468(60)M+,453(100),408(4),393(24),369(9),341(2),324(3),301(9),287 (22),227(20) (Ref. 9128) |
|||||||||||||||||||
| 408 |  |
cycloeucalenol |
4a,14a,24-trimethyl-9b,19-cyclo-5a-cholest-24(28)-en-3b-ol |
SST9080 | Etsuko Yasugi |
C30H50O1 | 426.717 | |
acetate 468(7)M+,453(8),408(100),393(51),384(5),365(7),343(5),300(10),285 (3),283(13) (Ref. 9128) |
|||||||||||||||||||
| 409 |  |
lanosterol |
5a-lanosta-8,24-dien-3b-ol |
SST9081 | Etsuko Yasugi |
C30H50O1 | 426.717 | |
[a]D +58 (Ref. 9136) |
acetate 468(79)M+,453(100),408(10),393(62),315(5),301(13),297(5),255(11),241(14),229(10) (Ref. 9135) |
||||||||||||||||||
| 410 |  |
agnosterol |
5a-lanosta-7.9(11),24-trien-3b-ol |
SST9082 | Etsuko Yasugi |
C30H48O1 | 424.702 | |
[a]D +69 (Ref. 9136) |
lmax=237,244,251nm (Ref. 9138) |
wool fat (Ref. 9138) |
|||||||||||||||||
| 411 |  |
cycloartenol |
9b,19-cyclo-5a-lanost-24en-3b-ol |
SST9083 | Etsuko Yasugi |
C30H50O1 | 426.717 | |
426(55)M+,411(53),408(72),393(60),365(24),339(25),315(9),286(57),175(44), 97(100) (Ref. 9140) |
higher plants (Ref. 9105) |
||||||||||||||||||
| 412 |  |
27-methylenecycloartenol |
24-methyl-9b,19-cyclo-5a-lanost-24(28)-en-3b-ol |
SST9084 | Etsuko Yasugi |
C31H52O1 | 440.744 | |
[a]D +43 (Ref. 9136) |
440(49)M+,425(40),422(50),407(46),379(14),353(13),315(10),300(58),175(49), 107(100) (Ref. 9140) |
higher plants (Ref. 9105) |
|||||||||||||||||
| 413 |  |
campestanol |
(24R)-24-methyl-5a-cholestan-3b-ol |
SST9085 | Etsuko Yasugi |
C28H50O1 | 402.696 | |
+31 (Ref. 9103) |
acetate 1H-NMR(CDCl3) 3-CH=4.684(TT),3-OAc=2.019(S),18-CH3=0.646(S),19-CH3=0.816(S),21-CH3=0.893(D),26-CH3=0.848(D),27-CH3=0.799(D),28-CH3=0.768(D) (Ref. 9117) |
acetate:444[M+](17%),429(2%),384(31%),369(16%),330(2%),317(1%),315(1%),276 (33%),275(21%),257(6%),230(14%),215(100%),201(19%),147(34%),81(53%) (Ref. 9144) |
|||||||||||||||||
| 414 |  |
ergostanol |
(24S)-24-methyl-5a-cholestan-3b-ol |
SST9086 | Etsuko Yasugi |
C28H50O1 | 402.696 | |
+16 (Ref. 9103) |
acetate 1H-NMR(CDCl3) 3-CH=4.684(TT),3-OAc=2.019(S),18-CH3=0.646(S),19-CH3=0.816(S),21-CH3=0.902(D),26-CH3=0.852(D),27-CH3=0.781(D),28-CH3=0.772(D) (Ref. 9106) |
acetate : 444[M+](48%), 429(12%), 384(47%), 369(34%), 276(35%), 275(43%), 230(27%), 217(26%), 216(51%), 215(100%), 201(20%) (Ref. 9148) |
|||||||||||||||||
| 415 |  |
stigmastanol |
(24R)-24ethyl-5a-cholestan-3b-ol |
SST9087 | Etsuko Yasugi |
C29H52O1 | 416.723 | |
+25 (Ref. 9103) |
acetate 1H-NMR(CDCl3) 3-CH=4.683(TT),3-OAc=2.018(S),18-CH3=0.648(S),19-CH3=0.817(S),21-CH3=0.904(D),26-CH3=0.833(D),27-CH3=0.814(D),29-CH3=0.843(T) (Ref. 9106) |
free:416[M+](10%), 401(3%), 290(6%), 257(3%), 248(7%), 233(98%), 215(100%), 201(11%) acetate:458[M+](57%), 443(4%), 398(47%), 383(21%), 344(3%), 317(2%), 290 (13%), 276(37%), 275(30%), 257(8%), 230(30%), 215(100%), 201(19%) (Ref. 9106) |
|||||||||||||||||
| 416 |  |
poriferastanol |
(24S)-24ethyl-5a-cholestan-3b-ol |
SST9088 | Etsuko Yasugi |
C29H52O1 | 416.723 | |
+25 (Ref. 9103) |
acetate 1H-NMR(CDCl3) 3-CH=4.684(TT),3-OAc=2.017(S),18-CH3=0.647(S),19-CH3=0.817(S),21-CH3=0.908(D),26-CH3=0.827(D),27-CH3=0.809(D),29-CH3=0.851(T) (Ref. 9152) |
acetate:458[M+](18%), 443(2%), 398(32%), 383(13%), 344(3%), 276(23%), 275 (21%), 257(6%), 230(15%), 215(100%), 201(17%) (Ref. 9144) |
|||||||||||||||||
| 417 |  |
22-dehydrocholesterol |
(22E)-cholesta-5,22-dien-3b-ol |
SST9089 | Etsuko Yasugi |
C27H44O1 | 384.638 | |
acetate 145-149 C (Ref. 9155) |
acetate 1H-NMR(CDCl3) 3-CH=4.602(M),3-OAc=2.030(S),6-CH=5.370(BRD),18-CH3= 0.692(S),19-CH3=1.020(S),21-CH3=1.010(D),22-CH=5.207(DD),23-CH=5.208(DD), 26-CH3 AND 27-CH3=0.858(D) AND 0.862(D) (Ref. 9106) |
free:384[M+](30%),369(9%),366(49%),351(16%),300(48%),285(12%),282(11%),273 (25%),271(26%),255(100%),213(25%) acetate:366[M+-HOAc](100%), 351(11%), 282(7%), 255(55%), 245(6%), 228(7%) 213(12%) (Ref. 9115) |
|||||||||||||||||
| 418 |  |
desmosterol |
cholesta-5,24-dien-3b-ol |
SST9090 | Etsuko Yasugi |
C27H44O1 | 384.638 | |
-41 (Ref. 9103) |
acetate 1H-NMR(CDCl3) 3-CH=4.603(M),3-OAc=2.030(S),6-CH=5.374(BRD),18-CH3= 0.678(S),19-CH3=1.018(S),21-CH3=0.936(D),24-CH=5.090(T),26-CH3=1.681(S), 27-CH3=1.601(S) (Ref. 9106) |
acetate:366[M+-HOAc](51%), 351(11%), 253(23%), 213(10%), 145(24%), 69(100%) (Ref. 9144) |
|||||||||||||||||
| 419 |  |
clionasterol |
(24S)-24ethylcholest-5-en-3b-ol |
SST9091 | Etsuko Yasugi |
C29H50O1 | 414.707 | |
-42 (Ref. 9103) |
acetate 1H-NMR(CDCl3) 3-CH=4.604(M),3-OAc=2.031(S),6-CH=5.375(BRD),18-CH3= 0.678(S),19-CH3=1.020(S),21-CH3=0.926(D),26-CH3=0.831(D),27-CH3=0.812(D), 29-CH3=0.855(T) (Ref. 9157) |
acetate:396[M+-HOAc](100%),381(22%),288(15%),275(15%),255(18%),213(18%) (Ref. 9106) |
|||||||||||||||||
| 420 |  |
poriferasterol |
(22E,24R)-24ethylcholesta-5,22-dien-3b-ol |
SST9092 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
156 C (Ref. 9103) |
-49 (Ref. 9103) |
acetate 1H-NMR(CDCl3) 3-CH=4.604(M),3-OAc=2.031(S),6-CH=5.373(BRD),18-CH3= 0.695(S),19-CH3=1.021(S),21-CH3=1.025(D), 22-CH=5.164(DD),23-CH=5.022(D), 26-CH3=0.844(D), 27-CH3=0.792(D) ,29-CH3=0.812(T) (Ref. 9155) |
free : 412[M+](100%),397(13%),394(14%),379(17%),369(25%),351(39%),327(5%), 314(16%), 300(36%), 283(13%), 271(56%), 255(59%), 253(14%), 241(9%), 239(8%), 231(8%), 229(6%) (Ref. 9106) |
||||||||||||||||
| 421 |  |
24-ethyldesmosterol |
24ethylcholesta-5,24-dien-3b-ol |
SST9093 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
acetate 139-141 C (Ref. 9157) |
acetate 1H-NMR(CDCl3) 3-CH=4.604(M),3-OAc=2.028(S),6-CH=5.374(BRD),18-CH3=0.682(S),19-CH3=1.020(S),21-CH3=0.970(D),26-CH3 AND 27-CH3=1.627(S) AND 1.632(S),29-CH3=0.932(T) (Ref. 9157) |
acetate : 394[M+-HOAc](32%),379(6%),296(100%),281(23%),253(18%),228(8%), 213(9%),55(81%) (Ref. 9144) |
|||||||||||||||||
| 422 |  |
22-dehydroclerosterol |
(22E,24S)-24ethylcholesta-5,22,25-trien-3b-ol |
SST9094 | Etsuko Yasugi |
C29H46O1 | 410.675 | |
acetate 146-150 C (Ref. 9162) |
acetate 1H-NMR(CDCl3) 3-CH=4.601(M),3-OAc=2.030(S),6-CH=5.370(BRD),18-CH3= 0.691(S),19-CH3=1.012(S),21-CH3=1.011(D),22-CH=5.243(DD),23-CH=5.171(DD), 24-CH=2.420(Q),26-CH3=1.646(D), 27-CH3=4.694(M), 29-CH3=0.833(T) (Ref. 9157) |
acetate:452[M+](0.3%),409(0.2%),392(100%),377(3%),363(3%),282(5%),255(32%), 253(12%), 228(3%), 213(7%) (Ref. 9162) |
|||||||||||||||||
| 423 |  |
24-methylene-25-methylcholesterol |
24,25-dimethylcholesta-5,24(28)-dien-3b-ol |
SST9095 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
acetate 1H-NMR(CDCl3) 3-CH=4.603(M),3-OAc=2.030(S),6-CH=5.372(BRS),18-CH3= 0.688(S),19-CH3=1.021(S),21-CH3=0.963(D),26-CH3=1.057(S),27-CH3=1.057(S), 28-CH2=4.659(S) AND 4.832(S),29-CH3=1.057(S) (Ref. 9155) |
|||||||||||||||||||
| 424 |  |
lathosterol |
5a-cholest-7-en-3b-ol |
SST9096 | Etsuko Yasugi |
C27H46O1 | 386.654 | |
free : 1H-NMR(CDCl3) 3-CH=3.60(M), 7-CH=5.158(M), 18-CH3=0.531(S), 19-CH3= 0.793(S), 21-CH3=0.917(D), 26-CH3 AND 27-CH3=0.861(D) AND 0.866(D) (Ref. 9102) |
|||||||||||||||||||
| 425 |  |
24-epifungisterol |
(24R)-24-methyl-5a-cholest-7-en-3b-ol |
SST9097 | Etsuko Yasugi |
C28H48O1 | 400.680 | |
free : 1H-NMR(CDCl3) 3-CH=3.60(M),7-CH=5.15(M),18-CH3=0.536(S),19-CH3= 0.800(S),21-CH3=0.916(D),26-CH3=0.852(D),27-CH3=0.804(D),28-CH3=0.775(D) (Ref. 9166) |
|||||||||||||||||||
| 426 |  |
fungisterol |
(24S)-24-methyl-5a-cholest-7-en-3b-ol |
SST9098 | Etsuko Yasugi |
C28H48O1 | 400.680 | |
acetate 1H-NMR(CDCl3) 3-CH=4.695(TT),3-OAc=2.026(S),7-CH=5.144(M),18-CH3= 0.531(S),19-CH3=0.810(S),21-CH3=0.924(D),26-CH3=0.856(D),27-CH3=0.785(D), 28-CH3=0.778(D) (Ref. 9117) |
free: 400[M+](100%),385(31%),382(6%),367(7%),273(25%),255(71%),253(2%)(Ref. 9167) |
||||||||||||||||||
| 427 |  |
episterol |
24-methyl-5a-cholesta-7.24(28)-dien-3b-ol |
SST9099 | Etsuko Yasugi |
C28H46O1 | 398.664 | |
131 C (Ref. 9103) |
+6 (Ref. 9103) |
acetate 1H-NMR(CDCl3) 3-CH=4.695(TT),3-OAc=2.025(S),7-CH=5.148(DD),18-CH3= 0.537(S),19-CH3=0.811(S),21-CH3=0.954(D),25-CH=2.231(SEPTET),26-CH3 AND 27-CH3=1.024(D) AND 1.028(D),28-CH2=4.652(S) AND 4.715(D) (Ref. 9152) |
acetate : 440[M+](1%),425(3%),365(2%),356(22%),315(2%),313(100%),255(14%), 253(9%),227(12%),213(26%) (Ref. 9144) |
||||||||||||||||
| 428 |  |
22-dihydrochondrillasterol |
(24S)-24ethyl-5a-cholest-7-en-3b-ol |
SST9100 | Etsuko Yasugi |
C29H50O1 | 414.707 | |
acetate 165-167 C (Ref. 9106) |
acetate 1H-NMR(CDCl3) 3-CH=4.694(TT),3-OAc=2.026(S),7-CH=5.146(DD),18-CH3= 0.533(S),19-CH3=0.809(S),21-CH3=0.931(D),26-CH3=0.832(D),27-CH3=0.812(D), 29-CH3=0.855(T) (Ref. 9157) |
acetate : 456[M+](100%),441(22%),396(18%),381(16%),315(10%),288(10%),273 (14%),255(79%),229(30%),213(38%) (Ref. 9106) |
|||||||||||||||||
| 429 |  |
chondrillasterol |
(22E,24R)-24ethyl-5a-cholesta-7.22-dien-3b-ol |
SST9101 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
169 C (Ref. 9103) |
-1 (Ref. 9103) |
acetate 1H-NMR(CDCl3) 3-CH=4.69(M), 3-OAc=2.03(S), 7-CH=5.146(M), 18-CH3= 0.548(S),19-CH3=0.815(S),21-CH3=1.031(D),22-CH=5.169(DD),23-CH=5.032(DD), 26-CH3=0.846(D), 27-CH3=0.794(D), 29-CH3=0.818(T) (Ref. 9169) |
acetate : 454[M+](33%),439(14%),411(15%),394(3%),379(5%),351(14%),342(21%), 315(21%),313(100%),300(4%),288(16%),273(10%),255(47%),241(7%),229(22%), 213(20%) (Ref. 9106) |
||||||||||||||||
| 430 |  |
zymostenol |
5a-cholest-8-en-3b-ol |
SST9102 | Etsuko Yasugi |
C27H46O1 | 386.654 | |
129 C (Ref. 9103) |
+50 (Ref. 9103) |
acetate 1H-NMR(CDCl3) 3-CH=4.700(TT),3-OAc=2.023(S),18-CH3=0.606(S),19-CH3=0.963(S),21-CH3=0.923(D),26-CH3 AND 27-CH3=0.863(D) AND 0.867(D)(Ref. 9106) |
acetate : 428[M+](89%),413(18%),368(5%),353(16%),315(9%),255(23%),229(37%), 213(46%),55(100%) (Ref. 9144) |
||||||||||||||||
| 431 |  |
zymosterol |
5a-cholesta-8.24-dien-3b-ol |
SST9103 | Etsuko Yasugi |
C27H44O1 | 384.638 | |
+49 (Ref. 9103) |
acetate 1H-NMR(CDCl3) 3-CH=4.70(M),3-OAc=2.03(S),18-CH3=0.61(S),19-CH3= 0.98(S),21-CH3=0.95(D),24-CH=5.08(T),26-CH3=1.68(S),27-CH3=1.61(S)(Ref. 9106) |
acetate : 426[M+](23%),411(10%),351(8%),315(1%),313(3%),255(3%),229(11%), 213(32%),69(100%),55(51%) (Ref. 9144) |
|||||||||||||||||
| 432 |  |
(24R)-24ethyl-5a-cholest-8-en-3b-ol |
SST9104 | Etsuko Yasugi |
C29H50O1 | 414.707 | |
acetate 131-134 C (Ref. 9106) |
free : 1H-NMR(CDCl3) 3-CH=3.62(M),18-CH3=0.605(S),19-CH3=0.947(S),21-CH3= 0.924(D),26-CH3=0.827(D),27-CH3=0.807(D),29-CH3=0.841(T)(Ref. 9149) |
free : 414[M+](100%),399(21%),396(2%),273(10%),255(6%),246(8%),231(6%), 229(9%),213(6%)(Ref. 9149) |
||||||||||||||||||
| 433 |  |
5a-cholest-8(14)-en-3b-ol |
SST9105 | Etsuko Yasugi |
C27H46O1 | 386.654 | |
+20 (Ref. 9103) |
acetate 1H-NMR(CDCl3) 3-CH=4.716(TT),3-OAc=2.022(S),18-CH3=0.838(S), 19-CH3=0.704(S),21-CH3=0.929(D),26-CH3 AND 27-CH3=0.863(D) AND 0.866(D) (Ref. 9147) |
acetate : 428[M+](100%),413(18%),368(6%),353(13%),315(16%),288(7%),273(6%), 255(21%),229(42%),213(42%),81%(80%),55(83%)(Ref. 9144) |
||||||||||||||||||
| 434 |  |
(24R)-24ethyl-5a-cholest-8(14)-en-3b-ol |
SST9106 | Etsuko Yasugi |
C29H50O1 | 414.707 | |
acetate 1H-NMR(CDCl3) 3-CH=4.703(M),3-OAc=2.022(S),18-CH3=0.841(S),19-CH3= 0.705(S),21-CH3=0.936(D),26-CH3=0.837(D),27-CH3=0.815(D),29-CH3=0.847(T) (Ref. 9147) |
acetate : 456[M+](100%),441(9%),396(4%),381(5%),315(12%),288(7%),276(13%), 255(15%),229(27%),213(22%) (Ref. 9147) |
Dioscoreaceae(yam) leaf propagule(Ref. 9147) |
||||||||||||||||||
| 435 |  |
9(11)-dehydroergosterol |
(22E,24R)-24ergosta-5,7,9(11),22-tetraen-3b-ol |
SST9107 | Etsuko Yasugi |
C28H42O1 | 394.632 | |
145-147 C (Ref. 9171) |
+147 (Ref. 9171) |
free : 311, 324, 339nm (Ref. 9171) |
free 1H-NMR(CDCl3) 3-CH=3.600(M),6-CH,7-CH AND 11-CH=5.385(M),5.496(M) AND 5.655(M),18-CH3=0.562(S),19-CH3=1.227(S),21-CH3=1.001(D),22-CH AND 23-CH= 5.182(M), 26-CH3 AND 27-CH3=0.805(D) AND 0.822(D),2-CH3=0.899(D) (Ref. 9171) |
free: 394[M+](44%),379(4%),376(51%),361(6%),333(3%),269(13%),267(4%),251 (100%),249(15%),227(10%),225(10%),224(6%),223(8%),209(20%),207(6%) (Ref. 9171) |
|||||||||||||||
| 436 |  |
isocitrostadienol |
[24(28)e]-4a-methyl-24ethyl-5a-cholesta-7,24(28)-dien-3b-ol |
SST9108 | Etsuko Yasugi |
C30H50O1 | 426.717 | |
acetate 142-145 C (Ref. 9113) |
acetate 1H-NMR(CDCl3) 3-CH=4.406(DT),3-OAc=2.054(S),7-CH=5.177(M),18-CH3= 0.542(S),19-CH3=0.843(S),21-CH3=0.995(D),25-CH=2.201(SEPTET),26-CH3 AND 27-CH3=0.980(D) AND 0.983(D),28-CH=5.185(Q),29-CH3=1.574(D),30-CH3=0.853(D) (Ref. 9130) |
acetate : 468[M+,12%),453(10%),393(9%),370(66%),355(5%),327(100%),310(8%), 302(5%),295(5%),287(4%),269(19%),267(9%),243(9%),242(5%),241(9%),227(22%) 215(8%) (Ref. 9130) |
|||||||||||||||||
| 437 |  |
4a,14a,24-trimethyl-5a-cholesta-9(11),24(28)-dien-3b-ol |
SST9109 | Etsuko Yasugi |
C30H50O1 | 426.717 | |
acetate 105-107 C (Ref. 9130) |
acetate 1H-NMR(CDCl3) 3-CH=4.368(DT),3-OAc=2.052(S),11-CH=5.300(DT),18-CH3= 0.660(S),19-CH3=1.003(S),21-CH3=0.912(D),25-CH=2.236(SEPTET),26-CH3 AND 27-CH3=1.026(D) AND 1.031(D),28-CH2=4.665(S) AND 4.717(S),30-CH3=0.842(D)32-CH3=0.750(S) (Ref. 9130) |
acetate : 468[M+](16%),453(57%),425(27%),408(18%),393(89%),341(100%),301 (20%),281(50%),241(34%),227(30%),215(27%),201(29%) (Ref. 9174) |
||||||||||||||||||
| 438 |  |
4a,14a,24-trimethyl-5a-cholesta-7,9(11),24(28)-trien-3b-ol |
SST9110 | Etsuko Yasugi |
C30H48O1 | 424.702 | |
acetate 123-124 C (Ref. 9175) |
acetate : 237,243,251nm (Ref. 9028) |
acetate 1H-NMR(CDCl3) 3-CH=4.397(DT),3-OAc=2.059(S),7-CH=5.411(D),11-CH= 5.390(D),18-CH3=0.581(S),19-CH3=0.952(S),21-CH3=0.922(D),25-CH=2.238(SEPTET),26-CH3 AND 27-CH3=1.029(D) AND 1.033(D),28-CH2=4.668(S) AND 4.722 ,30-CH3=0.866(D),32-CH3=0.8 |
acetate: 466[M+,97%),451(19%),406(8%),391(24%),367(14%),339(100%),300(22%), 299(32%),298(22%),281(11%),274(14%),239(65%),227(22%),226(35%),225(30%), 213(22%),211(22) (Ref. 9175) |
|||||||||||||||||
| 439 |  |
cycloartanol |
9b,19-cyclo-5a-lanostan-3b-ol |
SST9111 | Etsuko Yasugi |
C30H52O1 | 428.733 | |
+45 (Ref. 9136) |
acetate 1H-NMR(CDCl3) 3-CH=4.567(DD),3-OAc=2.051(S),18-CH3=0.959(S),19-CH2= 0.338(D) AND 0.576(D),21-CH3=0.861(D),26-CH3 AND 27-CH3=0.865(D) AND 0.871(D),30-CH3=0.846(S) 31-CH3 AND 32-CH3=0.889(S) AND 0.896(S)(Ref. 9176) |
acetate : 470[M+](1%),455(2%),410(8%),395(9%),367(3%),357(1%),355(1%), 341(3%),297(6%),288(10%),273(3%),55(100%) (Ref. 9144) |
|||||||||||||||||
| 440 |  |
cyclosadol |
(23E)-24-methyl-9b,19-cyclo-5a-lanost-23En-3b-ol |
SST9112 | Etsuko Yasugi |
C31H52O1 | 440.744 | |
acetate 1H-NMR(CDCl3) 3-CH=4.54(m),3-OAc=2.05(S),18-CH3=0.96(S),19-CH2= 0.34(D) AND 0.58(D),21-CH3=0.84(D),23-CH=5.03(M),25-CH=2.80(M),26-CH3= 0.84(D),27-CH3=0.84(D),28-CH3=1.61(S),30-CH3=0.85(S),31-CH3=0.90(S), 32-CH3=0.90(S) (Ref. 9139) |
acetate: 482[M+](13%),467(9%),422(68%),407(60%),385(9%),379(25%),353(20%), 325(53%),300(26%),297(18%),295(11%),255(10%),241(10%),229(25%),203(74%), 107(100%) (Ref. 9179) |
||||||||||||||||||
| 441 |  |
cyclobranol |
24-methyl-9b,19-cyclo-5a-lanost-24en-3b-ol |
SST9113 | Etsuko Yasugi |
C31H52O1 | 440.744 | |
+38.4 (Ref. 9180) |
acetate 1H-NMR(CDCl3) 3-CH=4.54(M),3-OAc=2.05(S),18-CH3=0.96(S),19-CH2= 0.34(D) AND 0.58(D),21-CH3=0.91(D),26-CH3=1.63(S),27-CH3=1.63(S),28-CH3=1.63(S),30-CH3=0.85(S),31-CH3=0.89(S),32-CH3=0.89(S) (Ref. 9106) |
acetate : 482[M+](,21%),467(11%),422(100%),407(76%),379(33%),353(26%), 339(24%),338(7%),323(7%),300(27%),297(41%),285(14%) (Ref. 9106) |
|||||||||||||||||
| 442 |  |
24-dihydrolanosterol |
5a-lanost-8-en-3b-ol |
SST9114 | Etsuko Yasugi |
C30H52O1 | 428.733 | |
+62 (Ref. 9103) |
acetate 1H-NMR(CDCl3) 3-CH=4.52(DD),3-OAc=2.05(S),18-CH3=0.686(S),19-CH3=1.003(S),21-CH3=0.888(D),26-CH3=0.863(D),27-CH3=0.869(D),30-CH3=0.880(S) 31-CH3=0.882(S),32-CH3=0.874(S) (Ref. 9134) |
acetate : 470[M+](40%),455(100%),410(1%),395(60%),357(1%),315(4%),301(3%), 297(9%),296(12%) (Ref. 9135) |
|||||||||||||||||
| 443 |  |
parkeol |
5a-lanosta-9(11),24-dien-3b-ol |
SST9115 | Etsuko Yasugi |
C30H50O1 | 426.717 | |
+77 (Ref. 9136) |
acetate 1H-NMR(CDCl3) 3-CH=4.46(M),3-OAc=2.05(S),11-CH=5.20(M),18-CH3=0.65(S),19-CH3=1.07(S),21-CH3=0.89(D),24-CH=5.10(M),26-CH3=1.69(S),27-CH3=1.59(D),30-CH3=0.87(S),31-CH3=0.89(S),32-CH3=0.74(S) (Ref. 9106) |
acetate: 468[M+](43%),453(100%),408(6%),393(99%),384(8%),383(11%),355(80%),341(6%),323(7%),316(13%),315(10%),301(19%),295(20%),271(14%),257(16%),255(17%),241(23%) (Ref. 9106) |
|||||||||||||||||
| 444 |  |
epicholestanol |
5a-cholestan-3a-ol |
SST9116 | Etsuko Yasugi |
C27H48O1 | 388.669 | |
free : 1H-NMR(CDCl3) 3-CH=4.03(M), 18-CH3=0.65(S), 19-CH3=0.77(S), 21-CH3=0.92(D), 26-CH3=0.87(D), 27-CH3=0.87(D) (Ref. 9049) acetate : 1H-NMR(CDCl3) 3-CH=5.01(BR.S), 3-OAc=2.05(S),18-CH3=0.65(S), 19-CH3=0.79(S), 21-CH3=0.90(D), 26-CH3=0.87(D), |
free : 388[M+](78%),373(67%),370(7%),355(52%),331(3%),262(26%),248(12%),234(65%),233(100%),230(9%),219(17%),217(34%),215(98%),201(15%) (Ref. 9106) |
Porifera(esperiopsis edwardii) (Ref. 9187) |
|||||||||||||||||
| 445 |  |
(22E)-5a-cholest-22En-3b-ol |
SST9117 | Etsuko Yasugi |
C27H46O1 | 386.654 | |
acetate:1H-NMR(CDCl3):3-CH=4.68(M), 18-CH3=0.66(S), 19-CH3=0.82(S), 21-CH3=0.99(D), 22-CH=5.2-5.32(M), 23-CH=5.2-5.32(M), 26-CH3=0.86(D), 27-CH3=0.85(D) (Ref. 9189) |
||||||||||||||||||||
| 446 |  |
24-methyl-5a-cholest-24(28)-en-3b-ol |
SST9118 | Etsuko Yasugi |
C28H48O1 | 400.680 | |
free : 1H-NMR(CDCl3): 18-CH3=0.65(S), 19-CH3=0.82(S), 21-CH3=0.94(D), 26-CH3=1.02(D), 27-CH3=1.02(D), 28-CH2=4.68 (Ref. 9191) |
free : 400[M+](4%),385(5%),367(0.8%),316(100%),301(36%),273(63%),259(5%),255(10%),246(6%),233(21%),215(32%),203(10%),201(8%) (Ref. 9149) acetate: 442[M+](1%),427(1%),358(46%),343(11%),315(21%),298(2%),283(4%),255(11%),215(23%), 55(100%) |
Nematodea(Meloidogyne incognite, Meloidogyne arenariai, Pratylenchus agilis) (Ref. 9144/9192), maize (Ref. 9144), Porifera(Axinella cannabina) (Ref. 9149), Porifera (Hymeniacidon perleve) (Ref. 9188), scallop (Ref. 9195), Holoturoidea(Stichopus japonicus) (Ref. 9191), marine unicellular algae (Ref. 9194) |
||||||||||||||||||
| 447 |  |
5-dihydrostigmasterol |
(22E,24S)-24ethyl-5a-cholestan-3b-ol |
SST9119 | Etsuko Yasugi |
C30H50O1 | 426.717 | |
acetate:1H-NMR(CDCl3) : 3-CH=4.68(TT), 3-OAc=2.02(S), 18-CH3=0.67(S), 19-CH3=0.82(S), 21-CH3=1.01(D), 22-CH=5.15(DD), 23-CH=5.01(DD), 26-CH3=0.84(D), 27-CH3=0.79(D), 29-CH3=0.80(T) (Ref. 9112) |
acetate : 456[M+](42%),441(4%),413(4%),396(21%),381(3%),358(7%),353(31%),344(32%),329(8%),316(27%),315(37%),302(10%),257(58%),255(18%),241(10%),229(10%), 43(100%) (Ref. 9112) |
tomato seed (Ref. 9110), Cleodendron plants (Ref. 9117), Cucurbitaceae plants (Ref. 9151), Leguminosae plants seed (Ref. 9196), Caryophyllales plants(spatial arrangement at C-24 unknown) (Ref. 9197), Myxomycetes(Dictyostelium discoideum) (Ref. 9195), maize(spatial arrangement at C-24 unknown) (Ref. 9198), Nematodea (spatial arrangement at C-24 unknown) |
|||||||||||||||||
| 448 |  |
5-dihydroclerosterol |
(24S)-24ethyl-5a-cholest-25-en-3b-ol |
SST9120 | Etsuko Yasugi |
C29H50O1 | 414.707 | |
acetate 123-125 C (Ref. 9157) |
acetate:1H-NMR(CDCl3): 3-CH=4.68(TT), 18-CH3=0.64(S), 19-CH3=0.81(S), 21-CH3=0.89(D), 26-CH3=1.56(D), 27-CH=4.64(D),27-CH=4.72(DT), 29-CH3=0.80(T),3-OAc=2.02(S) (Ref. 9152) |
acetate : 456[M+](100%),441(15%),396(7%),381(15%),358(33%),343(37%), 315(98%),302(22%),283(15%),257(48%),255(59%),229(22%),215(85%) (Ref. 9152) |
|||||||||||||||||
| 449 |  |
(23E)-24-methylcholesta-5,23-dien-3b-ol |
SST9121 | Etsuko Yasugi |
C28H46O1 | 398.664 | |
free:1H-NMR(CDCl3): 3-CH=3.53(M), 6-CH=5.36(DT), 18-CH3=0.69(S), 19-CH3=1.01(S), 21-CH3=0.89(D), 23-CH=5.14(T),26-CH3=0.99(D), 27-CH3=0.99(D), 28-CH3=1.55(S) (Ref. 9106) |
free : 398[M+](11%),383(9%),380(1%),314(17%),301(26%),300(17%),283(67%),271(100%),255(6%),253(7%),241(11%),227(11%),215(32%),213(17%)(Ref. 9102)acetate: 380[M+-HOAc](97%),365(11%),296(8%),283(100%),259(6%),255(11%), 253(42%),227(8%),215(12%),213(13%),159(3 |
|||||||||||||||||||
| 450 |  |
24-methyldesmosterol |
24-methylcholesta-5,24-dien-3b-ol |
SST9122 | Etsuko Yasugi |
C28H46O1 | 398.664 | |
-46.7 (Ref. 9199) |
free:1H-NMR(CDCl3): 3-CH=3.53(M), 6-CH=5.35(BR.D), 18-CH3=0.68(S),19-CH3=1.01(S), 21-CH3=0.96(D), 26-CH3,27-CH3 AND 28-CH3=1.62(S) AND 1.63(S)(Ref. 9200) |
||||||||||||||||||
| 451 |  |
codisterol |
(24S)-24-methylcholesta-5,25-dien-3b-ol |
SST9123 | Etsuko Yasugi |
C28H46O1 | 398.664 | |
acetate 134-136 C (Ref. 9203) |
acetate : 890, 1645, 1750cm-1(Ref. 9202) |
free:1H-NMR(CDCl3): 18-CH3=0.67(S), 19-CH3=1.01(S), 21-CH3=0.91(D), 26-CH3=1.64(S), 27-CH2=4.66(BR.S), 28-CH3=0.99(D)(Ref. 9199) |
|||||||||||||||||
| 452 |  |
(23E)-24ethylcholesta-5,23-dien-3b-ol |
SST9124 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
free:1H-NMR(CDCl3): 3-CH=3.52(M), 6-CH=5.35(M), 18-CH3=0.69(S), 19-CH3=1.01(S), 21-CH3=0.89(D), 23-CH=5.08(DD), 25-CH=2.23(M), 26-CH3=1.00(D), 27-CH3=1.00(D), 29-CH3=0.95(T)(Ref. 9207) |
1 29 |
|||||||||||||||||||
| 453 |  |
24,24-dimethylcholesta-5,25-dien-3b-ol |
SST9125 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
acetate 146-148 C (Ref. 9203) |
free:1H-NMR(CDCl3):18-CH3=0.67(S), 19-CH3=1.01(S), 21-CH3=0.91(D), 26-CH3=1.68(S), 27-CH2=4.66(S), 28-CH=1.01(S), 29-CH3=1.01(S)(Ref. 9158) |
acetate : 454[M+](1%),394(100%),379(8%),310(10%),281(4%),273(4%),255(11%),253(10%),228(10%),213(13%) (Ref. 9203) |
||||||||||||||||||
| 454 |  |
29-methylisofucosterol |
[24(28)z]-24-propylcholesta-5,24(28)-dien-3b-ol |
SST9126 | Etsuko Yasugi |
C30H50O1 | 426.717 | |
free:1H-NMR(CDCl3):3-CH=3.54, 6-CH=5.35(M), 18-CH3=0.68(S), 19-CH3=1.01(S), 21-CH3=0.95(D), 25-CH=2.80(M), 26-CH3=0.97(D), 27-CH3=0.97(D), 28-CH=5.01(DD), 30-CH3=0.94(T)(Ref. 9209) |
|||||||||||||||||||
| 455 |  |
stellasterol |
(22E,24S)-24-methyl-5a-cholesta-7,22-dien-3b-ol |
SST9127 | Etsuko Yasugi |
C28H46O1 | 398.664 | |
free:1H-NMR(CDCl3): 3-CH=3.60(M), 7-CH=5.16(M), 18-CH3=0.54(S), 19-CH3=0.80(S), 21-CH3=1.01(D), 22-CH AND 23-CH=5.16(M), 26-CH3=0.84(D), 27-CH3=0.82(D), 28-CH3=0.91(D) (Ref. 9149) |
free : 398[M+](22%),383(8%),365(1%),355(3%),300(13%),299(10%),271(100%),255(34%),246(25%),231(13%),229(20%),213(17%) (Ref. 9149) acetate : 440[M+](47%),425(16%),397(9%),380(6%),365(11%),342(21%),337(7%),313(100%),288(25%),273(7%),255(64%),253(1 |
||||||||||||||||||
| 456 |  |
5,6-dihydroergosterol |
(22E,24R)-24-methyl-5a-cholesta-7,22-dien-3b-ol |
SST9128 | Etsuko Yasugi |
C28H46O1 | 398.664 | |
free : 968, 1660, 3020, 3040, 3610cm-1 (Ref. 9217) |
free:1H-NMR(CDCl3): 3-CH=3.60(M), 7-CH=5.15(M), 18-CH3=0.54(S), 19-CH3=0.80(S), 21-CH3=1.02(D), 22-CH AND 23-CH=5.18(M), 26-CH3=0.84(D), 27-CH3=0.82(D), 28-CH3=0.91(D) (Ref. 9149) |
free : 397[M+](16%),383(6%),355(12%),300(10%),299(7%),271(100%),255(26%),246(20%),231(10%),229(16%),213(12%) (Ref. 9123) acetate: 440[M+](53%),425(14%),397(10%),380(10%),365(10%),342(23%), 315(34%),313(100%),299(10%),288(30%),273(10%),25 |
|||||||||||||||||
| 457 |  |
peposterol |
24ethyl-5a-cholesta-7,24-dien-3b-ol |
SST9129 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
+5.0 (Ref. 9186) |
acetate : 800, 930cm-1 (Ref. 9222) |
acetate:1H-NMR(CDCl3):3-CH=4.70(TT), 3-OAc=2.03(S), 7-CH=5.15(DT), 18-CH3=0.52(S), 19-CH3=0.81(S), 21-CH3=0.97(D), 26-CH3=1.63(BR.S),27-CH3=1.63(BR.S), 29-CH3=0.93(T) (Ref. 9106) |
acetate : 454[M+](3%),439(6%),379(5%),356(28%),313(100%),296(8%),255(15%),253(22%),227(8%),213(21%) (Ref. 9151) |
||||||||||||||||
| 458 |  |
isoavenasterol |
[24(28)e]-24ethyl-5a-cholesta-7,24(28)-dien-3b-ol |
SST9130 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
acetate 155 C (Ref. 9106) |
acetate : 800, 820, 830, 900cm-1 (Ref. 9223) |
acetate:1H-NMR(CDCl3) : 3-CH=4.70(TT), 3-OAc=2.03(S), 7-CH=5.15(M), 18-CH3=0.54(S), 19-CH3=0.81(S), 21-CH3=1.00(D),25-CH=2.20(SEPT.), 26-CH3=0.98(D), 27-CH3=0.98(D), 28-CH=5.18(Q), 29-CH3=1.57(D)(Ref. 9161) |
acetate : 454[M+](2%),439(4%),379(3%),356(37%),313(100%),296(7%),255(14%),253(15%),227(10%),213(21%) (Ref. 9151) |
||||||||||||||||
| 459 |  |
(24S)-24ethyl-5a-cholesta-7,25-dien-3b-ol |
SST9131 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
acetate : 202nm (e= 8000) (Ref. 9224) |
free : 890, 1645, 3080cm-1 acetate : 890, 1645, 1736, 3080cm-1 (Ref. 9224) |
free:1H-NMR(CDCl3): 3-CH=3.60(M), 7-CH=5.16(BR.S), 18-CH3=0.53(S), 19-CH3=0.80(S), 21-CH3=0.91(D), 26-CH3=1.57(S), 27-CH2=4.69(BR.S), 29-CH3=0.80(T)(Ref. 9205) |
free : 412[M+](21%),397(10%),394(4%),379(5%),369(15%),300(20%),299(11%),273(25%),272(19%),271(100%),255(50%),253(9%),246(21%),231(22%)(106)acetate:454[M+](30%),439(25%),394(9%),379(11%),341(9%),313(100%),299(7%) 288(11%),273(8%),255(30%),229(11%),228( |
|||||||||||||||||
| 460 |  |
25-dehydrochondrillasterol |
(22E,24S)-24ethyl-5a-cholesta-7,22,25-trien-3b-ol |
SST9132 | Etsuko Yasugi |
C29H46O1 | 410.675 | |
acetate : 204nm (e= 14,200) (Ref. 9224) |
free : 890, 976, 1645, 3080cm-1 acetate : 890, 976, 1645, 1734, 3080cm-1 (Ref. 9224) |
free:1H-NMR(CDCl3): 3-CH=3.60(M), 7-CH=5.16(BR.S), 18-CH3=0.55(S), 19-CH3=0.80(S), 21-CH3=1.02(D), 22-CH=5.22(M), 23-CH=5.22(M), 26-CH3=1.65(S), 27-CH2=4.71(S), 29-CH3=0.83(T) (Ref. 9205) |
free : 410[M+](31%),395(8%),392(4%),381(5%),300(14%),273(30%),272(30%),271(100%),255(14%),246(10%),231(10%),229(10%)213(14%) (Ref. 9146) acetate : 452[M+](20%),437(7%),423(9%),392(7%),363(8%),342(20%),313(100%),299(8%),288(6%),255(48%),229(17 |
||||||||||||||||
| 461 |  |
24,25-dimethyl-5a-cholesta-7,24(28)-dien-3b-ol |
SST9133 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
acetate : 795, 822, 890, 1245, 1735cm-1 (Ref. 9228) |
free:1H-NMR(CDCl3) : 3-CH=3.60(M), 7-CH=5.16(M), 18-CH3=0.55(S), 19-CH3=0.80(S), 21-CH3=0.97(D), 26-CH3=1.06(S), 27-CH3=1.06(S), 28-CH2=4.66(BR.S) AND 4.84(BR.S), 29-CH3=1.06(S) (Ref. 9228) |
free : 412[M+](9%),397(14%),314(41%),299(9%),285(5%),271(100%),255(13%), 246(11%),231(13%),227(10%) acetate : 454[M+](9%),439(12%),379(4%),356(43%),342(9%),313(100%),296(4%),288(6%),281(4%),273(6%),255(14%),253(6%),227(14%),213(20%) (Ref. 9228) |
bur cucmber (Ref. 9228) |
|||||||||||||||||
| 462 |  |
fecosterol |
24-methyl-5a-cholesta-8,24(28)-dien-3b-ol |
SST9134 | Etsuko Yasugi |
C28H46O1 | 398.664 | |
free : 1270, 2960, 3350cm-1 (Ref. 9229) |
free:1H-NMR(CDCl3) : 3-CH=3.61(M), 18-CH3=0.62(S), 19-CH3=0.95(S), 21-CH3=1.01(D), 26-CH3=1.04(D), 27-CH3=1.04(D), 28-CH2=4.66(BR.S) AND 4.71(BR.S) (Ref. 9229) |
||||||||||||||||||
| 463 |  |
(22E,24S)-24ethyl-5a-cholesta-8,22-dien-3b-ol |
SST9135 | Etsuko Yasugi |
C29H48O1 | 412.691 | |
acetate 151-153 C (Ref. 9042) |
free:1H-NMR(CDCl3): 3-CH=3.62(M), 18-CH3=0.62(S), 19-CH3=0.95(S), 21-CH3=1.03(D), 22-CH=5.14(DD), 23-CH=5.02(DD), 26-CH3=0.85(D), 27-CH3=0.80(D), 29-CH3=0.81(T) (Ref. 9149) |
free : 412[M+](100%),397(25%),394(4%),379(5%),369(7%),314(5%),299(5%),273(46%),271(31%),257(14%),255(19%),246(35%),229(36%),213(11%)(Ref. 9123)acetate:454[M+](100%),439(24%),411(11%),394(4%),379(13%),341(3%),315(42%),313(53%),299(11%),288(53%) |
||||||||||||||||||
| 464 |  |
(24R)-24-methyl-5a-cholest-8(14)-en-3b-ol |
SST9136 | Etsuko Yasugi |
C28H48O1 | 400.680 | |
acetate:1H-NMR(CDCl3): 3-CH=4.72(TT), 3-OAc=2.02(S),18-CH3=0.84(S),19-CH3=0.70(S), 21-CH3=0.93(D), 26-CH3=0.85(D),27-CH3=0.80(D), 28-CH3=0.78(D) (Ref. 9147) |
||||||||||||||||||||
| 465 |  |
(24S)-24-methyl-5a-cholest-8(14)-en-3b-ol |
SST9137 | Etsuko Yasugi |
C28H48O1 | 400.680 | |
+11 (Ref. 9217) |
free : 3610cm-1 (Ref. 9217) |
acetate:1H-NMR(CDCl3) : 3-CH=4.72(TT), 3-OAc=2.03(S),18-CH3=0.84(S),19-CH3=0.71(S), 21-CH3=0.94(D), 26-CH3=0.86(D), 27-CH3=0.79(D), 28-CH3=0.79(D) (Ref. 9122) |
acetate : 442[M+](100%),427(16%),382(3%),367(7%),315(11%),308(7%),288(3%),225(16%),229(25%),213(20%) (Ref. 9147) |
|||||||||||||||||
| 466 |  |
24-dehydropollinastanol |
14a-methyl-9b,19-cyclo-5a-cholest-24en-3b-ol |
SST9138 | Etsuko Yasugi |
C28H46O1 | 398.664 | |
free : 3040, 3610cm-1 acetate : 1733, 3040cm-1 (Ref. 9235) |
free:1H-NMR(CDCl3): 18-CH3=0.96(S), 19-CH2=0.07(D) AND 0.43(D), 21-CH3=0.89(D), 26-CH3=1.69(BR.S), 27-CH3=1.60(BR.S),32-CH3=0.89(S) (Ref. 9236) |
free : 398[M+](36%),383(52%),380(43%),365(43%),286(30%),270(13%),268(12%),231(17%),217(17%),205(28%),69(100%) (Ref. 9176) acetate : 440[M+](5%),425(2%),380(28%),311(3%),297(2%),286(2%),269(6%), 267(5%),231(3%),227(3%),213(3%),205(6%),201(5%),43(100%) (13 |
|||||||||||||||||
| 467 |  |
24-methylenepollinastanol |
14a,24-dimethyl-9b,19-cyclo-5a-cholest-24(28)-en-3b-ol |
SST9139 | Etsuko Yasugi |
C29H48O2 | 428.690 | |
free : 885, 1658, 3040, 3080, 3610cm-1 acetate : 885, 1635, 1735, 3040cm-1 (Ref. 9235) |
acetate:1H-NMR(CDCl3): 3-CH=4.80(M), 3-OAc=2.03(S), 18-CH3=0.96(S), 19-CH2=0.08(D) AND 0.44(D), 21-CH3=0.90(D), 26-CH3=1.03(D), 27-CH3=1.03(D), 28-CH2=4.66(D) AND 4.71(S), 32-CH3=0.90(S) (Ref. 9131) |
free : 412[M+](79%),397(84%),394(100%),379(68%),300(57%),287(34%), 269(28%) (Ref. 9180) acetate : 454[M+](12%),439(7%),411(4%),394(95%),379(45%),351(6%),329(5%), 300(6%),269(28%),267(14%),213(8%),55(100%) ( |
|||||||||||||||||
| 468 |  |
(24R)-14a-methyl-24ethyl-5a-cholest-9(11)-en-3b-ol |
SST9140 | Etsuko Yasugi |
C30H52O1 | 428.733 | |
acetate 97-98 C (Ref. 9240) |
acetate:1H-NMR(CDCl3) : 3-CH=4.68(M), 3-OAc=2.02(S), 11-CH=5.29(DT),18-CH3=0.66(S), 19-CH3=0.98(S), 21-CH3=0.88(D), 26-CH3=0.84(D), 27-CH3=0.82(D), 29-CH3=0.85(T) (Ref. 9106) |
acetate : 470[M+](31%),455(100%),410(3%),395(24%),329(3%),287(5%),273(6%), 269(7%),261(8%),227(8%),213(7%) (Ref. 9240) |
||||||||||||||||||
| 469 |  |
a-amyrin, a-amyrenol |
12-uresen-3b-ol |
SST9141 | Etsuko Yasugi |
C30H50O1 | 426.717 | |
dissolves slightly in ether, benzene, chloroform, glacial acetic acid, petroleum ether (Ref. 9241) |
component of various seeds containing Asterales: Artemesia Vulgaris and Lactuca denticulate <<>> |
||||||||||||||||||
| 470 |  |
12-uresen-3b-acetoxide |
SST9142 | Etsuko Yasugi |
C32H52O2 | 468.754 | |
1H-NMR: 2.033(Ac), 4.500(CH-O), 5.117(olefinic H) (Ref. 9246) |
component of various seeds containing Asterales: Artemesia vulgaris<<>> |
|||||||||||||||||||
| 471 |  |
12-uresen-3b-methoxide |
SST9143 | Etsuko Yasugi |
C31H52O1 | 440.744 | |
M/Z: 440, 218, 203 (Ref. 9248) |
component of Cortaderia toetoe <<>> |
|||||||||||||||||||
| 472 |  |
a-amyrose, a-amyrenone |
12-uresen-3-one |
SST9144 | Etsuko Yasugi |
C30H48O1 | 424.702 | |
||||||||||||||||||||
| 473 |  |
b-amyrin, b-amyrenol |
12-oleanen-3b-ol |
SST9145 | Etsuko Yasugi |
C30H50O1 | 426.717 | |
260 (0.8mmHg) <<>> |
|||||||||||||||||||
| 474 |  |
12-oleanen-3b-acetoxide |
SST9146 | Etsuko Yasugi |
C32H52O2 | 468.754 | |
1H-NMR : 2.041(Ac), 4.500(CH-O), 5.183(olefinic H) (Ref. 9246) |
||||||||||||||||||||
| 475 |  |
12-oleanen-3b-methoxide |
SST9147 | Etsuko Yasugi |
C31H52O1 | 440.744 | |
M/Z: 440, 218, 203 (Ref. 9248) |
||||||||||||||||||||
| 476 |  |
balanophorin |
12-oleanen-3b-palmitoxide |
SST9148 | Etsuko Yasugi |
C46H80O2 | 665.126 | |
||||||||||||||||||||
| 477 |  |
b-amyrone |
12-oleanen-3-one |
SST9149 | Etsuko Yasugi |
C30H48O1 | 424.702 | |
177-179 C (Ref. 9243) |
[a] D=+107.2 (CHCl3) (Ref. 9243) |
||||||||||||||||||
| 478 |  |
d-amyrin |
13-oleanen-3b-ol |
SST9150 | Etsuko Yasugi |
C30H50O1 | 426.717 | |
212-213.5 C (Ref. 9243) |
|||||||||||||||||||
| 479 |  |
d-amyrone |
13-oleanen-3-one |
SST9151 | Etsuko Yasugi |
C30H48O1 | 424.702 | |
198-201 C (Ref. 9243) |
|||||||||||||||||||
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| TITLE | : | Isolation of bufalin-3-sulfate from the skin of Bufo vulgaris Formosus Boulenger. |
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| JOURNAL | : | Jpn J Pharmacol. |
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| TITLE | : | Studies on the synthesis of cardiotonic steroids. III. New and effective route to bufadienolides. |
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| TITLE | : | Isolierung und Aufteilung der Chloroformloslichen Bestandteile der Chinesischen Krotengiftdroge Ch'an Su. |
| JOURNAL | : | Helv. Chim. Acta |
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| TITLE | : | Calusterone in the therapy for advanced breast cancer PubMed ID:5066641 |
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| TITLE | : | Isolation of a new phytosterol: Campesterol. |
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| TITLE | : | On the constitution of campesterol. |
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| JOURNAL | : | Phytochemistry |
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| TITLE | : | Mittheilungen aus dem chemischpharmakologischen Laboratorium des Botanischen Gartens zu Buitenzorg (Java). |
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| TITLE | : | Chemistry of chonemorphine: A steroidal alkaloid of Chonemorpha macrophylla G.Don and Chonemorpha penangensis. |
| JOURNAL | : | Chem.Ind.(London) |
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| AUTHOR | : | Chatterjee,A.,and Das,B. |
| TITLE | : | Chemistry of chonemorphine, The steroidal alkaloid of Chonemorpha macrophylla G.Don and Chonemorpha penangensis |
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| VOL | : | 1960 PAGE : 290-290 (1960) |
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| TITLE | : | Alcaloides steroides IX. Derives amino-20 et diamino-3,20 du pregnane-5a-: alcaloides du Funtumia africana (benth.) Stapf et du Malouetia bequaertiana woods. |
| JOURNAL | : | Bull. Soc. Chim. France |
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| TITLE | : | Synthesis of chonemorphine stereoisomers. |
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| TITLE | : | Konstitution des Cinobufotalins. Über Krötengifte, 28. Mitteilung. |
| JOURNAL | : | Helv. Chim. Acta |
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| TITLE | : | Über Saponine der Spirostanolreihe, VI. Die Konstitution des Convallamarogenins. |
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| TITLE | : | Studies on the steroidal components of domestic plants-XLI. Constituents of Reineckia carnea Kunth (6) structure of reineckiagenin, isoreineckiagenin and isocarneagenin. |
| JOURNAL | : | Tetrahedron |
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| TITLE | : | Über pflanzliche Herzgifte, VIII. Mitteil.: Über das Convallatoxin. |
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| TITLE | : | Convallatoxin. |
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| TITLE | : | Über g-Strophanthin (Ouabain) und g-Strophanthidin. |
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| TITLE | : | Darstellung eines krystallisierten herzwirksamen Glykosides aus Convallaria majalis, L. |
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| TITLE | : | Die Glykoside des Milchsaftes von Antiaris toxicaria Lesch aus Bogor (Java) . Glykoside und Aglykone, 243. Mitteilung. |
| JOURNAL | : | Helv. Chim. Acta |
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| TITLE | : | Die Glykoside der Zwiebeln von Ornithogalum umbellatum L. sowie Prüfung der Zwiebeln von Ornithogalum prasinum (Lindl.). Glykoside und Aglykone, 198. Mitteilung. |
| JOURNAL | : | Helv. Chim. Acta |
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| TITLE | : | Chemical studies on the adrenal cortex. I. Fractionation studies on hormone concentrates. |
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| TITLE | : | The chemistry of crystalline substances isolated from the suprarenal gland. |
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| TITLE | : | Über Bestandteile der Nebennieren-Rinde VI. Trennungsmethoden, sowie Isolierung der Substanzen F. a. H und J. |
| JOURNAL | : | Helv. Chim. Acta |
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| TITLE | : | Chemical studies of the suprarenal cortex. II. The identification of a substance which possesses the qualitative action of cortin; Its conversion into a diketone closely related to androstenedione. |
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| AUTHOR | : | Sarett,L.H. |
| TITLE | : | Partial synthesis of pregnene-4-triol-17(b),20(b),21-dione-3,11 and pregnene-4-diol-17(b),21-trione-3,11,20 monoacetate. |
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| TITLE | : | Seitenkettenabbau von Gallensäuren direkt zu Ketolen vom Typus der Nebennierenrinden-Hormone. |
| JOURNAL | : | Experientia |
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| TITLE | : | Über Steroide (65. Mitteilung). Ein einfacher Abbau der Gallensaure-Seitenkette VIII. Überführung der Desoxy-cholsäure in 3,12-Disubstituierte Ketole vom Typus der Nebennierenrinden-Hormone. |
| JOURNAL | : | Helv. Chim. Acta |
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| TITLE | : | Über Steroide. Ein einfacher Abbau der Gallensauren-Seitenkette IX. Überführung der D5-3b-Oxy-cholensäure in 11-Desoxy-corticosteronester und -äther. |
| JOURNAL | : | Helv. Chim. Acta |
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| TITLE | : | Über Gallensäuren und verwandte Stoffe. 22. Mitteilung. 11a-Keto-und 11a-Oxy-cholansäure. |
| JOURNAL | : | Helv. Chim. Acta |
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| TITLE | : | Über Gallensäuren und verwandte Stoffe. Derivate der ätio-cholansäure mit Sauerstoff in 3- und 11-Stellung. |
| JOURNAL | : | Helv. Chim. Acta |
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| AUTHOR | : | Hegner,P.,and Reichstein,T. |
| TITLE | : | Über Bestandteile der Nebennierenrinde und verwandte Stoffe. 61. Mitteilung. 11-Keto-progesteron. |
| JOURNAL | : | Helv. Chim. Acta |
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| TITLE | : | Steroids derived from bile acids. V. Introduction of oxygen at C11. |
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| TITLE | : | Microbiological oxygenation of steroids at carbon 11. |
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| TITLE | : | Microbiological hydroxylation of progesterone. |
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| TITLE | : | A new method for the preparation of 17(a)-hydroxy-20-ketopregnanes. |
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| AUTHOR | : | Sarett,L.H. |
| TITLE | : | Preparation of pregnane-17a,21-diol-3,11,20-trione acetate. |
| JOURNAL | : | J. Am. Chem. Soc. |
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| TITLE | : | The preparation of 3-keto-D4-steroids. |
| JOURNAL | : | J. Am. Chem. Soc. |
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| AUTHOR | : | Sarett,L.H.,Arth,G.E.,Lukes,R.M.,Beyler,R.E.,Poos,G.I.,Johns,W.F.,and Constantin,J.M. |
| TITLE | : | Stereospecific total synthesis of cortisone. |
| JOURNAL | : | J. Am. Chem. Soc. |
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| AUTHOR | : | Poos,G.I.,Hirschmann,R.,Bailey,G.A.,Cutler,F.A.,Jr,Sarett,L.H.,and Chemerda,J.M. |
| TITLE | : | Water-soluble steroid phosphates. |
| JOURNAL | : | Chem. Ind.(London) |
| VOL | : | 1958 PAGE : 1260-1261 (1958) |
| AUTHOR | : | Cutler,F.A.,Jr.,Conbere,J.P.,Lukes,R.M.,Fisher,J.F.,Mertel,H.E.,Hirschmann,R.,Chemerda,J.M.,Sarett,L.H.,and Pfister,K.,3rd. |
| TITLE | : | Synthesis of cortisone-21 phosphate. |
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| AUTHOR | : | Mitsuhashi,H.,and Shimizu,Y. |
| TITLE | : | Studies of the constituents of Asclepiadaceae plants. I. On the components of Cynanchum Caudatum Max. |
| JOURNAL | : | Chem. Pharm. Bull. |
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| TITLE | : | Studies on the constituents of Asclepiadaceae plants.II. On the structure of cynanchogenin from Cynanchum caudatum Max. |
| JOURNAL | : | Chem. Pharm. Bull. |
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| TITLE | : | Structure of cynanchogenin and sarcostin. |
| JOURNAL | : | Steroids |
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| TITLE | : | Studies on the components of Asclepiadaceae plants-XXII. Structures of cynanchogenin and sarcostin. |
| JOURNAL | : | Tetrahedron |
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| TITLE | : | Carbon-13 nuclear magnetic resonance spectroscopy of C/D-cis polyoxypregnanes. I. |
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| TITLE | : | [Biodynamics of 1,2 alpha-methyl-6-chloro-pregna-4,6-diene-17 alpha-acetoxy-3,20-dione (cyproterone acetate) after oral administration in man. On alkyl-substituted steroids. IX] PubMed ID:4361164 |
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| TITLE | : | Über Bestandteile der Nebennierenrinde (X). Zur Kenntnis des Cortico-sterons. |
| JOURNAL | : | Helv. Chim. Acta |
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| TITLE | : | The partial synthesis of dehydrocorticosterone acetate. |
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| TITLE | : | Über Bestandteile der Nebennierenrinde und verwandte Stoffe. 62. Mitteilung. Teilsynthese des 11-Dehydro-corticosterons. |
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| TITLE | : | Über Steroide. (68. Mitteilung). Ein einfacher Abbau der Gallensauren-Seitenkette X. Neue Partialsynthesen von 11-Dehydro-corticosteron sowie 11-Keto-progesteron. |
| JOURNAL | : | Helv. Chim. Acta |
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| TITLE | : | Über die Ultraviolett-Bestrahlung des Dehydro-ergosterins. |
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| TITLE | : | Die Konstitution des Lumisterins und der Erhitzungsprodukte des Vitamins D2 (Calciferols). |
| JOURNAL | : | Ber. |
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| TITLE | : | Chromophoric groups. Part II. Absorption spectra of naphthalene, hydronaphthalenes, and related compounds. |
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| TITLE | : | Über das 7-Dehydro-sitosterin. |
| JOURNAL | : | Hoppe-Seyler's Z. Physiol. Chem. |
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| TITLE | : | Steroids. CXXVII. 6-Halo progestational agents. |
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| TITLE | : | Steroid anti-estrogens. |
| JOURNAL | : | Steroids |
| VOL | : | 1 PAGE : 185-209 (1963) |
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| TITLE | : | Control of reproduction and of undesirable social and sexual behaviour in dogs and cats PubMed ID:4738952 |
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| TITLE | : | Percutaneous absorption and excretion of tritium-labeled diflorasone diacetate, a new topical corticosteroid in the rat, monkey and man PubMed ID:102707 |
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| TITLE | : | Glucocorticoid in inflammatory proliferative skin disease reduces arachidonic and hydroxyeicosatetraenoic acids PubMed ID:887938 |
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| TITLE | : | Comparative anti-inflammatory properties of systemically administered betamethasone 17-benzoate and 6 alpha, 9 alpha difluoroprednisolone 21-acetate 17-butyrate PubMed ID:5500915 |
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| TITLE | : | The local anti-inflammatory properties of betamethasone 17-benzoate and 6 alpha, 9 alpha difluoroprednisolone 21-acetate 17-butyrate PubMed ID:5500916 |
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| TITLE | : | Über Saponine der Spirostanolreihe, VII. Über Digalogenin, ein neues Sapogenin aus den Samen von Digitalis purpurea L. |
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| TITLE | : | Mitteilung Über Herzglykoside. Lanatosid D. Ein neues genuines Glykosid aus Digitalis lanata Ehrh. |
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| TITLE | : | Umwandlung von Cardenoliden durch Mikroorganismen: II. Diginatigenin aus Gitoxigenin. 3. Mitteilung Über Reaktionen mit Mikroorganismen. |
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| TITLE | : | Bioconversion of cardiac aglycones by Gibberella sauinettii (Mont.) Sacc. |
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| TITLE | : | The hydrogenation of equilenin to an isoestradiol. |
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| JOURNAL | : | Tetrahedron. |
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| TITLE | : | Sexualhormone X. Herstellung des 17-Methyl-testosterons und anderer Androsten- und Androstanderivate. Zusammenhänge zwischen chemischer Konstitution und männlicher Hormonwirkung. |
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| TITLE | : | Über Steroide (22. Mitteilung). 17-Epimere Methyl-androstendiole und Methyl-testosterone. |
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| TITLE | : | Die Kernresonanzspektren von Steroiden in Polaren Lösungsmitteln-II. |
| JOURNAL | : | Tetrahedron |
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| TITLE | : | Herstellung weiterer 1-Dehydro-steroide auf mikrobiologischem Wege. Mikrobiologische Reaktionen, 7. Mitteilung. |
| JOURNAL | : | Helv. Chim. Acta |
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| TITLE | : | Gewinnung von 1;4-Bisdehydro-3-oxo-steroiden. Über Steroide, 139. Mitteilung. |
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| TITLE | : | Comparative study of estrogen action PubMed ID:4725783 |
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| TITLE | : | Über das Neo-ergosterin. |
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| TITLE | : | Über einige Derivate des Neo-ergosterins. |
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| TITLE | : | Steroids with an aromatic B-ring. |
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| TITLE | : | Beweis des Steringerüstes von Ouabagenin. Glykoside und Aglykone, 180. Mitteilung. |
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| TITLE | : | Über Periplocin, das genuine herzwirksame Glykosid der Periploca graeca. (15. Mitteilung Über Herzglykoside). |
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| TITLE | : | Die Glykoside der Samen von Strophanthus Eminii Asch. et Pax. Glykoside und Aglykone, 56. Mitteilung. |
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| TITLE | : | Konfiguration des Periplogenins und des allo-Periplogenins. Glykoside und Aglykone, 28. Mitteilung. |
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| TITLE | : | Konfiguration des Periplogenins und Alloperiplogenins. II. Glykoside und Aglykone, 31. Mitteilung. |
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| TITLE | : | Synthetic periplogenin. |
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| TITLE | : | Steroids and related natural products. 88. Synthesis of periplogenin PubMed ID:4854409 |
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| TITLE | : | Microbiological transformation of steroids-X. 1-Dehydro analogs of cortical steroids. |
| JOURNAL | : | Tetrahedron |
| VOL | : | 18 PAGE : 581-589 (1962) |
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| TITLE | : | New antiarthritic steroids. |
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| TITLE | : | Corticosteroid 17a-monoesters from 17a,21-cyclic orthoesters. |
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| TITLE | : | Crystalline Vitamin D. |
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| TITLE | : | Studies in the sterol group. Part XXXI. The structure of lumisterol. |
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| VOL | : | 1937 PAGE : 411-414 (1937) |
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| TITLE | : | Über das Lumisterin |
| JOURNAL | : | Justus Liebigs Ann Chem. |
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| AUTHOR | : | Butenandt,A. |
| TITLE | : | Über das Pregnandiol, einen neuen Sterin-Abkömmling aus Schwangeren-Harn (2. Mitteil.). |
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| TITLE | : | Sterols. XXX. The structure of pregnanetriol-B. |
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| TITLE | : | Über das Pregnandiol, einen neuen Sterin-Abkömmling aus Schwangeren-Harn. |
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| AUTHOR | : | Fish,W.R.,Dorfman,R.I.,and Young,W.C. |
| TITLE | : | Metabolism of the steroid hormones. III. The isolation of pregnandiol-3(a),20(a) from the urine of pregnant chimpanzees. |
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| TITLE | : | Notiz Über die katalytische Hydrierung des Progesterons. |
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| TITLE | : | Sterols. XVIII. Preparation of epi-allo-pregnanolone from allo-pregnandiol. |
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| TITLE | : | Über Bestandteile der Nebennierenrinde und verwandte Stoffe. 44. Mitteilung. 11-Dehydro-progesteron |
| JOURNAL | : | Helv. Chim. Acta |
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| TITLE | : | Sterols. XVII. Isolation of pregnanolone from human pregnancy urine. |
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| AUTHOR | : | Marrian,G.F.,and Gough,N. |
| TITLE | : | The isolation of pregnane-3(a)-ol-20-one from the hydrolysis products of sodium pregnanediol glucuronidate. |
| JOURNAL | : | Biochem. J. |
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| TITLE | : | Sterols. XX. The pregnanolones. |
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| TITLE | : | Über Pregnanol-(20)-on-(3). |
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| TITLE | : | Sterols. XXII. The pregnandiols and pregnanolones. |
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| TITLE | : | Über Bestandteile der Nebennierenrinde und verwandte Stoffe. (30. Mitteilung). Substanz T. |
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| TITLE | : | Über Cortin, das Hormon der Nebennieren-rinde. I. Mitteilung. |
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| TITLE | : | Über Bestandteile der Nebennierenrinde und verwandte Stoffe. 54. Mitteilung. Trennungsmethoden, Isolierung, von Substanz U und ihre Teilsynthese aus Substanz E. |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 24 PAGE : 247-264 (1941) |
| AUTHOR | : | Logemann,W. |
| TITLE | : | Zur Darstellung von Inhaltsstoffen der Nebennierenrinde und verwandter Verbindungen. Das b-D4-Pregnentriol (17,20,21) On(3). |
| JOURNAL | : | Naturwiss. |
| VOL | : | 27 PAGE : 196-197 (1939) |
| AUTHOR | : | Ruzicka,L.,and Müller,P. |
| TITLE | : | Über Steroide und Sexualhormone. (54. Mitteilung) Die Anlagerung von Sauerstoff an D4.$1$7-21-Acetoxy-Pregnadienon-(3). |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 22 PAGE : 755-757 (1939) |
| AUTHOR | : | Butenandt,A.,and Grosse,W. |
| TITLE | : | Über den Ersatz der 3-sändigen Hydroxylgruppe im Pregnenolon und Androstendiol durch Chlor. |
| JOURNAL | : | Ber. |
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| TITLE | : | The preparation of a series of 3b-methoxy-D5-steroids. |
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| TITLE | : | The degradation of 6-methoxy-bisnor-i-cholenic acid. |
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| TITLE | : | Studies in the synthesis of cortisone. Part XII. Improvements in the conversion of sapogenins into pregnan-20-ones. |
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| TITLE | : | Solanum-alkaloide. XIX. Mitt.: Isolierung von Solanocapsin aus Solanum pseudocapsicum L., Solanum capsicastrum Link und Solanum hendersonii hort. |
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| JOURNAL | : | Tetrahedron |
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| TITLE | : | Spinasterol and some of its esters. |
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| VOL | : | 60 PAGE : 1901-1903 (1938) |
| AUTHOR | : | de Winter,M.S.,Siegmann,C.M.,and Szpilfogel,S.A. |
| TITLE | : | 17-Alkylated 3-deoxo-19-nortestosterones. |
| JOURNAL | : | Chem. Ind. (London) |
| VOL | : | 1959 PAGE : 905-905 (1959) |
| AUTHOR | : | Fried,J.,and Sabo,E.F. |
| TITLE | : | 9a-Fluoro derivatives of cortisone and hydrocortisone. |
| JOURNAL | : | J. Am. Chem. Soc. |
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| AUTHOR | : | Godtfredsen,W.O.,and Vangedal,S. |
| TITLE | : | 6a-Trifluoromethyl-17a-acetoxy-progesterone and some unsaturated analogs. |
| JOURNAL | : | Acta Chem. Scand. |
| VOL | : | 15 PAGE : 1786-1786 (1961) |
| AUTHOR | : | Edwards,J.A.,Ringold,H.J.,and Djerassi,C. |
| TITLE | : | Steroids. CXXII. 6a-Fluoro-16a-methylcorticoids-synthesis and biological activity. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 81 PAGE : 3156-3157 (1959) |
| AUTHOR | : | Edwards,J.A.,Ringold,H.J.,and Djerassi,C. |
| TITLE | : | Steroids. CXXXVI. Synthesis of a new class of potent cortical hormones. 6a-Fluoro-and 6a,9a-difluoro-16a-methylprednisolone and related steroids. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 82 PAGE : 2318-2322 (1960) |
| AUTHOR | : | Mills,J.S.,Bowers,A.,Djerassi,C.,and Ringo,H.J. |
| TITLE | : | Steroids. CXXXVII. Synthesis of a new class of potent cortical hormones. 6a,9a-Difluoro-16a-hydroxyprednisolone and its acetonide. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 82 PAGE : 3399-3404 (1960) |
| AUTHOR | : | Sammul,O.R.,Brannon,W.L.,and Hayden,A.L. |
| TITLE | : | Infrared spectra of some compounds of pharmaceutical interest. |
| JOURNAL | : | J. Assoc. Offic. Agr. Chem. |
| VOL | : | 47 PAGE : 918-991 (1964) |
| AUTHOR | : | Domenico,A.,Gibian,H.,Kerb,U.,Kieslich,K.,Kramer,M.,Neumann,F.,and Raspe,G. |
| TITLE | : | Chemie und Pharmakologie eines neuen entzündungshemmenden Corticosterons, des 6a-Fluor-16a-Methyl-1,4-Pregnadien-11 b,21-Diol-3,20-Dion (Fluocortolon) und seines Capronates. |
| JOURNAL | : | Arzneimittelforschung. |
| VOL | : | 15 PAGE : 46-50 (1965) |
| AUTHOR | : | Kieslich, K., Petzoldt, K., Kosmol, H., and Koch, W. |
| TITLE | : | [Preparation of 6-alpha-fluoro-11-beta, 21-dihydroxy-16-alpha-methyl-1,4-pregnadiene-3, 20-dione (fluocortolone) via substrate-structure-directed specific 11-beta-hydroxylation by Curvularia lunata] PubMed ID:5816548 |
| JOURNAL | : | Justus Liebigs Ann Chem. |
| VOL | : | 726 PAGE : 168-176 (1969) |
| AUTHOR | : | Gillich, K. H., Kruskemper, H. L., Kodding, R., and Delbruck, A. |
| TITLE | : | [Metabolic balance studies during oral administration of Fluocortolone] PubMed ID:4301840 |
| JOURNAL | : | Int Z Klin Pharmakol Ther Toxikol. |
| VOL | : | 1 PAGE : 197-202 (1968) |
| AUTHOR | : | von Schoning, G., Balbach, P., and Drews, J. |
| TITLE | : | [Effect of 6-dehydro-16-methylne hydrocortisone dexamethasone and fluocoolone on cortisol sretion and gluse tolerance in man] PubMed ID:5504385 |
| JOURNAL | : | Klin Wochenschr. |
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| AUTHOR | : | Gerhards, E., Nieuweboer, B., Schulz, G., and Gibian, H. |
| TITLE | : | [Metabolism of 6 -fluor-16 -methylpregna-1,4-dien-ll,21-diol-3,20-dion (fluocortolone) in man. Isolation of 6 -hydroxylated metabolites (alkyl-substituted steroids VII)] PubMed ID:5109849 |
| JOURNAL | : | Acta Endocrinol (Copenh). |
| VOL | : | 68 PAGE : 98-126 (1971) |
| AUTHOR | : | Breuer,H.,Burgmann,W.,and Luchmann,A. |
| TITLE | : | Klinisch-experimentelle Untersuchungen mit 16a-Methylcorticosteron-Derivaten. |
| JOURNAL | : | Arzneimittelforschung. |
| VOL | : | 15 PAGE : 50-53 (1965) |
| AUTHOR | : | Herr,M.E.,Hogg,J.A.,and Levin,R.H. |
| TITLE | : | Synthesis of potent oral anabolic-androgenic steroids. |
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| AUTHOR | : | Agnello, E. J., Pinson, R., Jr., Figdor, S. K., Hughes, G. M., Ordway, H. W., Bloom, B. M., and Laubach, G. D. |
| TITLE | : | The synthesis of corticosteroids methylated at C-21 PubMed ID:13681623 |
| JOURNAL | : | Experientia. |
| VOL | : | 16 PAGE : 357-358 (1960) |
| AUTHOR | : | Agnello,E.J.,Figdor,S.K.,Hughes,G.M.K.,Ordway,H.W.,Pinson,R.,Jr., Bloom,B.M.,and Laubach,G.D. |
| TITLE | : | A stereospecific synthesis of C-21-methylated corticosteroids. |
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| TITLE | : | Vasoconstrictor and systemic activities of topical steroids PubMed ID:4966856 |
| JOURNAL | : | Arch Dermatol. |
| VOL | : | 97 PAGE : 407-410 (1968) |
| AUTHOR | : | Taub,D.,Hoffsommer,R.D.,and Wendler,N.L. |
| TITLE | : | 16-Methylene and D15-16-methyl cortical steroids. |
| JOURNAL | : | J. Org. Chem. |
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| AUTHOR | : | Taub,D.,Hoffsommer,R.D.,and Wendler,N.L. |
| TITLE | : | Synthesis and chemistry of 16-methylene and D15-16-methyl cortical steroids. |
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| AUTHOR | : | von Werder,F.,Mannhardt,H.J.,Bork,K.H.,Metz,H.,Brückner,K.,and Irmscher,K. |
| TITLE | : | Synthesen des lokal entzündungshemmenden Fluprednyliden-21-acetate |
| JOURNAL | : | Arzneimittelforschung. |
| VOL | : | 18 PAGE : 7-10 (1968) |
| AUTHOR | : | Bergstrom,C.G.,Nicholson,R.T.,Elton,R.L.,and Dodson,R.M. |
| TITLE | : | 17a-Acetoxy-9-halo-11-oxygenated progesterones. A new class of orally active progestins. |
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| TITLE | : | Synthesis of 3-(2'-chloroethoxy)-6-formyl-delta-3,5-pregnadienes. A new class of highly active anti-inflammatory corticosteroids PubMed ID:5964110 |
| JOURNAL | : | Experientia. |
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| TITLE | : | 1,11-Ossidosteroidi.-Nota I. 1a,11a-ossidoandrostani. |
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| TITLE | : | Absorption, distribution and excretion of 2-formyl-17 alpha-methylandrosta-1,4,diene-11 alpha, 17 beta-dihydroxy-3-one PubMed ID:4801664 |
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| TITLE | : | Sur la cerine et la friedeline. |
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| TITLE | : | Friedelin and epifriedelinol from Ceratopetalum apetalum D. Don. |
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| TITLE | : | Friedelin and cerin. |
| JOURNAL | : | Chem. Ind. (London) |
| VOL | : | 1955 PAGE : 1156-1158 (1955) |
| AUTHOR | : | Kane,V.V.,and Stevenson,R. |
| TITLE | : | Friedelin and related compounds-V. The action of N-bromosuccinimide on friedelin and derivatives. |
| JOURNAL | : | Tetrahedron |
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| TITLE | : | Friedelin and related compounds. VI. Azahomofriedelanes. |
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| TITLE | : | Studies on the chemical composition of mold. (VII). On the chemical structure of fungisterol (1). |
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| TITLE | : | Studies on the chemical composition of mold (IX). On the chemical structure of fungisterol (3). |
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| TITLE | : | Studies on the chemical composition of mold (supplement to part IX). |
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| TITLE | : | Studies on the chemical composition of mold (X). |
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| AUTHOR | : | Khuong-Huu,Q.,Yassi,J.,Monneret,C.,and Goutrel,R. |
| TITLE | : | Alcaloïdes sté roïdiques. XXXVII.-Structure de la funtessine, nouvel alcaloïde des é corces du Funtumia latifolia Stapf., Apocynacé es |
| JOURNAL | : | Bull. Soc. Chim. France |
| VOL | : | 1965 PAGE : 1831-1834 (1965) |
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| AUTHOR | : | Kawasaki, T., and Nishioka, I. |
| TITLE | : | Digitalis saponins. II. Leaf saponins of Digitalis purpurea L PubMed ID:5888638 |
| JOURNAL | : | Chem Pharm Bull (Tokyo). |
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| TITLE | : | Digitalis saponins-IV. Structure of F-gitonin. |
| JOURNAL | : | Tetrahedron |
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| TITLE | : | Die Glykoside der Blätter der Digitalis purpurea. |
| JOURNAL | : | Arch. Pharm. |
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| TITLE | : | Die Darstellung und chemische Zusammensetzung der aktiven Substanzen aus den Digitalisblättern, ihre pharmakologischen und therapeutischen Eigenschaften. |
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| TITLE | : | Digitalis Glucosides. Part III. Glucosides of Digitalis lanata. |
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| TITLE | : | Contribution to the chemistry and pharmacology of the Digitalis purpurea glycosides. |
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| TITLE | : | Über ein in Chloroform unlösliches Glykosid aus Digitalis-Blättern, das Gitoxin. |
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| TITLE | : | Studies on digitalis glycosides. XXXI. Stepwise degradation of polydigitoxosides of Cardenolides. |
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| TITLE | : | Polyterpene und Polyterpenoide. CX. Überführung des Gypsogenins in Hederagenin. |
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| TITLE | : | Sapogenins. Part VIII. The sapogenin of Fuller's herb. |
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| TITLE | : | 16-Hydroxylated steroids. XXIII. 21-Chloro-16a-hydroxycorticoids and their 16a,17a-acetonides. |
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| TITLE | : | Evaluation of corticosteroids intended for use as topical anti-inflammatory drugs PubMed ID:4210465 |
| JOURNAL | : | Curr Ther Res Clin Exp. |
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| TITLE | : | Steroids. CXLIV. Synthesis of some 6a,17a-dihaloprogesterones. |
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| TITLE | : | Steroids and related products. XII. The synthesis of 6a-fluoro-17a-bromoprogesterone. |
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| TITLE | : | Phytochemische Untersuchungen in der Familie der Araliaceae. I. Saponinartige Glykoside aus den Blättern von Polyscias nodosa und Hedera helix. |
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| JOURNAL | : | Helv. Chim. Acta |
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| TITLE | : | The isolation and identification of hederagenin from Ackee, Blighia sapida Koenig (Sapindaceae). |
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| TITLE | : | Saponins. I. The sapogenin obtained from soapnuts. |
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| TITLE | : | Untersuchungen in der Familie der Araliaceae, Speziell Über die Glykoside und Oxydasen aus den Blättern von Polyscias nodosa Forst und Hedera helix L. |
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| AUTHOR | : | van der Haar,A.W. |
| TITLE | : | Beiträge zur Chemie der Saponine. (Polyscias-Saponine, Krystallin. a-Hederin, Guajac- und Saponaria-Saponine, Senegin, Digitonin und Aralia-Saponine). |
| JOURNAL | : | Biochem. Z. |
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| AUTHOR | : | van der Haar,A.W. |
| TITLE | : | Untersuchungen Über die Saponine. (V. Mitteilung). Weitere Studien am a-Hederin und an seinem Hederagenin. |
| JOURNAL | : | Ber. |
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| TITLE | : | Über Triterpene, XIX. Reindarstellung und Strukturermittlung der Saponine des Efeus (Hedera helix L.). |
| JOURNAL | : | Z. Naturforsch. |
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| AUTHOR | : | Karrer,W. |
| TITLE | : | Über Hellebrin, ein krystallisiertes Glykosid aus Radix Hellebori nigri. |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 26 PAGE : 1353-1367 (1943) |
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| TITLE | : | The alkaloids of Holarrhena congolensis Stapf. |
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| TITLE | : | Holarrhenin aus Holarrhena congolensis Stapf. |
| JOURNAL | : | Helv. Chim. Acta |
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| AUTHOR | : | van Hove,L. |
| TITLE | : | Contribution a l'etude des alcaloides de l'Holarrhena congolensis Stapf. Structure de l'holarrhenine. |
| JOURNAL | : | Tetrahedron |
| VOL | : | 7 PAGE : 104-117 (1959) |
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| TITLE | : | Isolierung und Konstitutionsermittlung weiterer Pregnanverbindungen aus Nebennieren. |
| JOURNAL | : | Helv. Chim. Acta |
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| TITLE | : | Steroids. XXX. Partial synthesis of allopregnane-3 beta, 11 beta, 17 alpha, 21-tetrol-20-one PubMed ID:14946186 |
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| TITLE | : | Synthesis of Reichstein's Substance C and related compounds. |
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| TITLE | : | Chemical studies of the suprarenal cortex. IV. Structures of compounds C, D, E, F, and G. |
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| TITLE | : | Isolation of 17-Hydroxycorticosterone from the urine in a case of Cushing's syndrome associated with severe diabetes mellitus. |
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| TITLE | : | Isolation of 17-hydroxycorticosterone from blood obtained from adrenal veins of dogs PubMed ID:14794726 |
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| TITLE | : | Über Bestandteile der Nebennierenrinde und verwandte Stoffe. (74. Mitteilung). Konfiguration der Cortico-Steroide. |
| JOURNAL | : | Helv. Chim. Acta |
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| AUTHOR | : | Wendler,N.L.,Graber,R.P.,Jones,R.E.,and Tishler,M. |
| TITLE | : | Synthesis of 11-hydroxylated cortical steroids. 17(a)-Hydroxycorticosterone. |
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| TITLE | : | Adrenal conversion of C14 labeled cholesterol and acetate to adrenal cortical hormones. |
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| TITLE | : | A partial microbiological synthesis of hydrocortisone PubMed ID:13084650 |
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| TITLE | : | Steroid anesthetic agent. |
| JOURNAL | : | Science |
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| TITLE | : | Steroid derivatives. XXXI. A novel synthesis of 16-methylene-17a-acyloxy-20-ketopregnane derivatives. |
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| TITLE | : | D4-3-Keto steroidal enol ethers. Paradoxical dependency of their effectiveness on the administration route. |
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| TITLE | : | New syntheses of estrone, d,l-8-iso-oestrone and d,l-19-nortestosterone. |
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| TITLE | : | On the alkaloids of white Hellebore. I. Isolation of constituent alkaloids. |
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| TITLE | : | 2-(1-Pyrrolidinyl)-methyl-testosteron. |
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| TITLE | : | Herstellung von ungesättigten Lactonen der Steroidreihe, VIII. Synthese von Bufadienoliden, II; Resibufogenin und Derivate. |
| JOURNAL | : | Justus Liebigs Ann Chem. |
| VOL | : | 1973 PAGE : 5-10 (1973) |
| AUTHOR | : | Leigh, J. M., and Caldwell, A. D. |
| TITLE | : | Some effects of resibufogenin: an aglycone of animal origin PubMed ID:4390620 |
| JOURNAL | : | J Pharm Pharmacol. |
| VOL | : | 21 PAGE : 708-709 (1969) |
| AUTHOR | : | Fieser,L.F.,and Fieser,M. (1959), 20.40 Marinobufagin and Resibufogenin, in Steroids, (Fieser,L.F.,and Fieser,M., eds) pp794-797, Reinhold Publishing Corporation, New York |
| TITLE | : | |
| JOURNAL | : | |
| VOL | : | PAGE : - () |
| AUTHOR | : | Schöpf,C.,and Braun,W. |
| TITLE | : | über Samandarin, das Hauptalkaloid im Gift des Feuer- und Alpensalamanders. |
| JOURNAL | : | Justus Liebigs Ann Chem. |
| VOL | : | 514 PAGE : 69-90 (1934) |
| AUTHOR | : | Wölfel,E.,Schöpf,C.,Weitz,G.,and Habermehl,G. |
| TITLE | : | Die Konstitution und Konfiguration des Samandarins. |
| JOURNAL | : | Ber. |
| VOL | : | 94 PAGE : 2361-2373 (1961) |
| AUTHOR | : | Stoll,A.,Kreis,W.,and Hofmann,A. |
| TITLE | : | Über Scillarenase. (3. Mitteilung Über Herzglucoside). |
| JOURNAL | : | Z. Physiol. Chem. |
| VOL | : | 222 PAGE : 24-38 (1933) |
| AUTHOR | : | Stoll,A.,Hofmann,A.,and Helfenstein,A. |
| TITLE | : | Die Natur der Sauerstoffatome im Scillaridin A (6. Mitteilung Über Herzglucoside). |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 17 PAGE : 641-664 (1934) |
| AUTHOR | : | Stoll,A.,Hofmann,A.,and Kreis,W. |
| TITLE | : | Die Doppelbindungen des Scillaridins A. (7. Mitteilung Über Herzglucoside) |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 17 PAGE : 1334-1354 (1934) |
| AUTHOR | : | Stoll,A.,and Hofmann,A. |
| TITLE | : | Umsetzungsprodukte von Scillaren A (8. Mitteilung Über Herzglucoside). |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 18 PAGE : 82-95 (1935) |
| AUTHOR | : | Stoll,A.,and Kreis,W. |
| TITLE | : | Genuine Glucoside der Digitalis purpurea, die Purpureaglucoside A und B. (9. Mitteilung Über Herzglucoside) |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 18 PAGE : 120-141 (1935) |
| AUTHOR | : | Stoll,A.,and Hofmann,A. |
| TITLE | : | Die Hydrierung des Scillarens A und die physiologische Prüfung einiger Scillarenderivate (10. Mitteilung Über Herzglucoside). |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 18 PAGE : 401-419 (1935) |
| AUTHOR | : | Stoll,A.,Hofmann,A.,And Helfenstein,A. |
| TITLE | : | Die identität der a-Scillansäure mit Allocholansäure. 11. Mitteilung Über Herzglucoside. |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 18 PAGE : 644-659 (1935) |
| AUTHOR | : | Stoll,A.,Hofmann,A.,and Peyer,J. |
| TITLE | : | Die Bruttoformeln des Scillaridins A und seiner Derivate (13. Mitteilung Über Herzglucoside). |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 18 PAGE : 1247-1251 (1935) |
| AUTHOR | : | Stoll,A.,and Renz,J. |
| TITLE | : | Die Überführung von Scillaren A in Epi-allo-lithocholsäure (3b-Oxy-allo-Cholansäure). (17. Mitteilung Über Herzglykoside). |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 24 PAGE : 1380-1388 (1941) |
| AUTHOR | : | Fieser,L.F.,and Fieser,M. (1959) Plant Bufadienolides, Scillaren A, in Steroids, (Fieser,L.F.,and Fieser,M., eds) pp782-784, Reinhold Publishing Corporation, New Tork |
| TITLE | : | |
| JOURNAL | : | |
| VOL | : | PAGE : - () |
| AUTHOR | : | Kuhn,R.,and Löw,I. |
| TITLE | : | Die Konstitution des Solanins. |
| JOURNAL | : | Angew. Chem. |
| VOL | : | 66 PAGE : 639-640 (1954) |
| AUTHOR | : | Kuhn,R.,Löw,I.,and Trischmann,H. |
| TITLE | : | Die Konstitution des Solanins. |
| JOURNAL | : | Ber. |
| VOL | : | 88 PAGE : 1492-1507 (1955) |
| AUTHOR | : | Nishie, K., Gumbmann, M. R., and Keyl, A. C. |
| TITLE | : | Pharmacology of solanine PubMed ID:4105761 |
| JOURNAL | : | Toxicol Appl Pharmacol. |
| VOL | : | 19 PAGE : 81-92 (1971) |
| AUTHOR | : | Bell,R.C.,and Briggs,L.H. |
| TITLE | : | Solanum Alkaloids. Part I. The Alkaloid from the Fruit of Solanum aviculare. |
| JOURNAL | : | J. Chem. Soc. |
| VOL | : | 1942 PAGE : 1-2 (1942) |
| AUTHOR | : | Briggs,L.H.,Newbold,R.P.,and Stace,N.E. |
| TITLE | : | Solanum alkaloids. Part II. Solasonine. |
| JOURNAL | : | J. Chem. Soc. |
| VOL | : | 1942 PAGE : 3-12 (1942) |
| AUTHOR | : | Kuhn,R.,and Löw,I. |
| TITLE | : | Die Alkaloidglykoside der Blätter von Solanum aviculare. |
| JOURNAL | : | Ber. |
| VOL | : | 88 PAGE : 289-294 (1955) |
| AUTHOR | : | Dayal,B., Batta,A.K., Shefer,S., Tint,G.S., Salen,G., and Mosbach,E.H. |
| TITLE | : | Preparation of 24(R)-and 24(S)-5b-Cholestane-3a,7a,24-Triols and 25(R)- and 25(S)-5b-Cholestane-3a,7a,26-Triols by A Hydroboration Procedure. PubMed ID:632683 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 19 PAGE : 191-196 (1978) |
| AUTHOR | : | Kuroki,S., Shimazu,K., Kuwabara,M., Une,M., Kihira,K., Kuramoto,T., and Hoshita, T. |
| TITLE | : | Identification of Bile Alcohols in Human Bile. PubMed ID:3989382 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 26 PAGE : 230-240 (1985) |
| AUTHOR | : | Cohen,B.I., Tint,G.S., Kuramoto,T., and Mosbach,E.H. |
| TITLE | : | New Bile Alcohols---Synthesis of 5b-Cholestane-3a,7a,25-Triol and 5b- Cholestane-3a,7a,25-24(14C)-Triol. PubMed ID:1145673 |
| JOURNAL | : | Steroids |
| VOL | : | 25 PAGE : 365-378 (1975) |
| AUTHOR | : | Une,M., Shinonaga,N., Matoba,N., Kuroki,S., Kihira,K., and Hoshita,T. |
| TITLE | : | Identificaiion New Bile Alcohols,5b-Cholestane-3a,7a,24,26-Tetrol, 5b-Cholestane-3a,7a,25,26-Tetrol, 5b-Cholestane-3a,7a,26,27-Tetrol in Human Gallbladder Bile. PubMed ID:3559394 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 27 PAGE : 1318-1323 (1986) |
| AUTHOR | : | Kuramoto,T., Cohen,B.I., Rothschild,M.A., Donor,D.A., and Mosbach,E.H. |
| TITLE | : | Chemical Synthesis 5b-Cholestane-3a,7a,24,25-Tetrol and Its Metabolism in the Perfused Rabbit Liver. PubMed ID:659442 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 253 PAGE : 4688-4692 (1978) |
| AUTHOR | : | Kuroki,S., Schteingart,C.D., Hagey,L.R., Cohen,B.I., Mosbach,E.H., Hofmann,A.F., Matoba,N., Une,M., Hoshita,T., and Odell,D.K. |
| TITLE | : | Bile Salts of the West Indian Manatee, Trichechus Manatus Latirostris: Novel Bile Alcohol Sulfates and Absence of Bile Acids. PubMed ID:3392467 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 29 PAGE : 509-522 (1988) |
| AUTHOR | : | Shimazu,K., Kuwabara,M., Yoshii,M., Kihira,K., Takeuchi,H., Nakano,I., Ozawa,S., Onuki,M., Hatta,Y., and Hoshita,T. |
| TITLE | : | Bile Alcohol Profiles in Bile, Urine, and Feces of a Patients with Cerebrotendinous Xanthomatosis. PubMed ID:3700361 |
| JOURNAL | : | J. Biochem. |
| VOL | : | 99 PAGE : 477-483 (1986) |
| AUTHOR | : | Hiraoka,T., Kihira,K., Kajiyama,G., Kuramoto,T., and Hoshita,T. |
| TITLE | : | Identification of 5b-Cholestane-3a,7a,12a,24,25,26-Hexol in Human Urine. PubMed ID:3668388 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 28 PAGE : 895-899 (1987) |
| AUTHOR | : | Hiraoka,T., Kihira,K., Kohda,T., Kosaka,D., Kajiyama,G., and Hoshita,T. |
| TITLE | : | Urinary Bile Alcohols in Liver Dysfunction. PubMed ID:3677435 |
| JOURNAL | : | Clin. Chim. Acta |
| VOL | : | 169 PAGE : 127-132 (1987) |
| AUTHOR | : | Hiraoka,T., Kihira,K., Kosaka,D., Kohda,T., Hoshita,T., and Kajiyama,G. |
| TITLE | : | Identification of Bile Alcohols in Serum from Healthy Humans. PubMed ID:3242175 |
| JOURNAL | : | Steroids |
| VOL | : | 51 PAGE : 543-550 (1988) |
| AUTHOR | : | Kihira,K., Kuramoto,T., and Hoshita,T. |
| TITLE | : | New Bile Alcohols---Synthesis of (22R)-and (22S)-5b-Cholestane-3a,7a, 12a,22,25-Pentols. PubMed ID:1265799 |
| JOURNAL | : | Steroids |
| VOL | : | 27 PAGE : 383-393 (1976) |
| AUTHOR | : | Kuramoto,T., Matsumoto,N., and Hoshita,T. |
| TITLE | : | Syntheses of 22- and 23-Hydroxylated Bile Alcohols. |
| JOURNAL | : | Chem. Pharm. Bull. |
| VOL | : | 26 PAGE : 2788-2792 (1978) |
| AUTHOR | : | Yasuhara,M., Kuramoto,T., and Hoshita,T. |
| TITLE | : | Identification of 5b-Cholestane-3a,7a,12a,23b-Tetrol, 5b-Cholestane- 3a,7a,12a,24a-Tetrol,and 5b-Cholestane-3a,7a,12a,24 |
| JOURNAL | : | Steroids |
| VOL | : | 31 PAGE : 333-345 (1978) |
| AUTHOR | : | Hoshita,T., Yasuhara,M., Une,M., Kibe,A., Itoga,E., Kito,S., and Kuramoto,T. |
| TITLE | : | Occurrence of Bile Alcohol Glucuronides in Bile of Patients with Cerebrotendinous Xanthomatosis. PubMed ID:7462799 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 21 PAGE : 1015-1021 (1980) |
| AUTHOR | : | Shimizu,K., Noda,F., and Yamasaki,K. |
| TITLE | : | Preparation of 3a,7a,12a-Trihydroxy-24a-Oxocoprostane and 3a,7a,12a,24x-Tetrahydroxycoprostane |
| JOURNAL | : | J. Biochem. |
| VOL | : | 45 PAGE : 625-627 (1958) |
| AUTHOR | : | Masui,T., and Staple,E. |
| TITLE | : | The Separation of the Stereoisomers of Bile Steroids,5b-Cholestane-3a, 7a,12a,24a-Tetrol and 5b-Cholestane-3a,7a,12a,24b-Tetrol, by Thin Layer Chromatography. PubMed ID:6041713 |
| JOURNAL | : | Steroids |
| VOL | : | 9 PAGE : 443-450 (1967) |
| AUTHOR | : | Murata,M., Kuramoto,T., and Hoshita,T. |
| TITLE | : | Identification of Bile Alcohols in Normal Rabbit Bile. PubMed ID:663971 |
| JOURNAL | : | Steroids |
| VOL | : | 31 PAGE : 319-332 (1978) |
| AUTHOR | : | Noma,Y., Noma,Y., Kihira,K., Yasuhara,M., Kuramoto,T., and Hoshita,T. |
| TITLE | : | Isolation of New C26 Bile Alcohols from Bullfrog Bile. PubMed ID:1087897 |
| JOURNAL | : | Chem. Pharm. Bull. |
| VOL | : | 24 PAGE : 2686-2691 (1976) |
| AUTHOR | : | Kihira,K., Noma,Y., Tsuda,K., Watanabe,T., Yamamoto,Y., Une,M., and Hoshita,T. |
| TITLE | : | Absolute Configuration at C-24 of 5b-Ranol, a Principal Bile Alcohol of the Bullfrog. PubMed ID:3487609 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 27 PAGE : 393-397 (1986) |
| AUTHOR | : | Anderson,I.G., Haslewood,G.A.D., Oldham,R.S., Amos,B., and Tokes,L. |
| TITLE | : | A More Detailed Study of Bile Salt Evolution, Including Techniques for Small-Scale Identification and Their Application to Amphibian Biles. PubMed ID:4218097 |
| JOURNAL | : | Biochem. J. |
| VOL | : | 141 PAGE : 485-494 (1974) |
| AUTHOR | : | Une,M., Matsumoto,N., Kihira,K., Yasuhara,M., Kuramoto,T., and Hoshita,T. |
| TITLE | : | Bile Salts of Frogs: A New Higher Bile Acid, 3a,7a,12a,26-Tetrahydroxy- 5b-Cholestanoic Acid from the Bile of Rana Plancyi. PubMed ID:7381321 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 21 PAGE : 269-276 (1980) |
| AUTHOR | : | Kazuno,T., and Mori,A. |
| TITLE | : | The Synthesis of Trihydroxycoprostane |
| JOURNAL | : | Proc. Japan Acad. |
| VOL | : | 30 PAGE : 486-488 (1954) |
| AUTHOR | : | Oftebro,H., Bjorkhem,I., Skrede,S., Schreiner,A., and Pedersen,J.I. |
| TITLE | : | Cerebrotendinous Xanthomatosis a Defect in Mitochondrial 26-Hydroxylation Required For Normal Biosynthesis of Cholic Acid. PubMed ID:7410549 |
| JOURNAL | : | J. Clin. Invest. |
| VOL | : | 65 PAGE : 1418-1430 (1980) |
| AUTHOR | : | Shefer,S., Dayal,B., Tint,G.S., Salen,G., and Mosbach,E.H. |
| TITLE | : | Identification of Pentahydroxy Bile Alcohols in Cerebrotendinous Xanthomatosis: Characterization of 5b-Cholestane-3a,7a,12a,24,25-Pentol and 5b-Cholestane-3a,7a,12a,23,25-Pentol. PubMed ID:1141769 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 16 PAGE : 280-286 (1975) |
| AUTHOR | : | Hoshita,T. |
| TITLE | : | Synthesis of 3a,7a,12a,25,26-and 3a,7a,12a,24,25-Pentahydroxycoprostanes |
| JOURNAL | : | J. Biochem. |
| VOL | : | 52 PAGE : 176-179 (1962) |
| AUTHOR | : | Karlaganis,G., Karlaganis,V., and Sjovall,J. |
| TITLE | : | Identification of 27-Nor-5b-Cholestane-3a,7a,12a,24,25,26-Hexol and Partial Characterization of the Bile Alcohol Profile in Urine. PubMed ID:6548247 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 25 PAGE : 693-702 (1984) |
| AUTHOR | : | Pearlman,W.H. |
| TITLE | : | The Preparation of C-27 Steroids from Bile Acids I. Coprostanetetrol-3(a),7(a),12(a),25 |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 69 PAGE : 1475-1476 (1947) |
| AUTHOR | : | Setoguchi,T., Salen,G., Tint,G.S., and Mosbach,E.H. |
| TITLE | : | A Biochemical Abnormality in Cerebrotendinous Xanthomatosis Impairment of Bile Acid Biosynthesis Associated with Incomplete Degradation of the Cholesterol Side Chain. PubMed ID:4825231 |
| JOURNAL | : | J. Clin. Invest. |
| VOL | : | 53 PAGE : 1393-1401 (1974) |
| AUTHOR | : | Tint,G.S., Dayal,B., Batta,A.K., Shefer,S., Joanen,T., Mcnease,L., and Salen,G. |
| TITLE | : | Biliary Bile Acids, Bile Alcohols, and Sterols of Alligator Mississippiensis. PubMed ID:7354247 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 21 PAGE : 110-117 (1980) |
| AUTHOR | : | Wolthers,B.G., Volmer,M., Van Der Molen,J., Koopman,B.J., Jager,A.E.J., and Waterreus,R.J. |
| TITLE | : | Diagnosis of Cerebrotendinous Xanthomatosis (CTX) and Effect of Chenodeoxycholic Acid Therapy by Analysis of Urine Using Capillary Gas Chromatography. PubMed ID:6883710 |
| JOURNAL | : | Clin. Chim. Acta |
| VOL | : | 131 PAGE : 53-65 (1983) |
| AUTHOR | : | Hoshita,T., Yasuhara,M., Kihira,K., and Kuramoto,T. |
| TITLE | : | Identification of (23S)-5b-Cholestane-3a,7a,12a,23,25-Pentol in Cerebrotendinous Xanthomatosis. PubMed ID:941184 |
| JOURNAL | : | Steroids |
| VOL | : | 27 PAGE : 657-664 (1976) |
| AUTHOR | : | Kuwabara,M., Ushiroguchi,T., Kihira,K., Kuramoto,T., and Hoshita,T. |
| TITLE | : | Identification of Bile Alcohols in Urine from Healthy Humans. PubMed ID:6726087 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 25 PAGE : 361-368 (1984) |
| AUTHOR | : | Bridgwater,R.J., Briggs,T., and Haslewood,G.A.D. |
| TITLE | : | Isolation from Shark Bile and Partial Synthesis of Scymnol |
| JOURNAL | : | Biochem. J. |
| VOL | : | 82 PAGE : 285-290 (1962) |
| AUTHOR | : | Kouchi,M. |
| TITLE | : | Studies on the Bile of Shark, Mustelus Manazo |
| JOURNAL | : | Hiroshima J. Med. Sci. |
| VOL | : | 13 PAGE : 341-350 (1964) |
| AUTHOR | : | Okuda,K., Enomoto,S., Morimoto,K., and Kazuno,T. |
| TITLE | : | The Isolation of a New Bile Sterol, 3a,7a,12a-Trihydroxy-24,27- Epoxycoprostane, from Stingray Bile |
| JOURNAL | : | J. Biochem. |
| VOL | : | 51 PAGE : 441-442 (1962) |
| AUTHOR | : | Dayal,B., Tint,G.S., Toome,V., Batta,A.K., Shefer,S., and Salen,G. |
| TITLE | : | Synthesis and Structure of 26(or 27)-Nor-5b-Cholestane-3a,7a,12a,24s,25-Pentol Isolated from the Urine and Feces of a Patient with Sitosterolemia and Xanthomatosis. PubMed ID:2985722 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 26 PAGE : 298-305 (1985) |
| AUTHOR | : | Ludwig-Kohn,H., Henning,H.V., Szedat,A., Matthaei,D., Spiteller,G., Reiner,J., and Egger,H-J. |
| TITLE | : | The Identification of Urinary Bile Alcohols by Gas Chromatography-Mass Spectrometry in Patients with Liver Disease and in Healthy Individuals. PubMed ID:6409629 |
| JOURNAL | : | Eur. J. Clin. Invest. |
| VOL | : | 13 PAGE : 91-98 (1983) |
| AUTHOR | : | Karlaganis,G., Alme,B., Karlaganis,V., and Sjovall,J. |
| TITLE | : | Bile Alcohol Glucuronides in Urine. Identification of 27-Nor-5b-Cholestane-3a,7a,12a,24,25-Pentol in Man. PubMed ID:7230796 |
| JOURNAL | : | J. Steroid Biochem. |
| VOL | : | 14 PAGE : 341-345 (1981) |
| AUTHOR | : | Ichimiya,H., Yanagisawa,J., and Nakayama,F. |
| TITLE | : | Significance of Bile Alcohol in Urine of a Patient with Cholestasis: Identification of 5b-Cholestane-3a,7a,12a,26,27-Pentol (5b-Cyprinol) and 5b-Cholestane-3a,7a,12a,26-Tetrol (27-Deoxy-5b-Cyprinol). PubMed ID:6499098 |
| JOURNAL | : | Chem. Pharm. Bull. |
| VOL | : | 32 PAGE : 2874-2877 (1984) |
| AUTHOR | : | Ichimiya,H., Yanagisawa,J., and Nakayama,F. |
| TITLE | : | Altered Metabolism of Bile Alcohol and Bile Acid in Complete Extrahapatic Cholestasis: Qualitative and Quantitative Aspects. PubMed ID:3655557 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 28 PAGE : 1028-1037 (1987) |
| AUTHOR | : | Hiraoka,T., Kosaka,D., Kajiyama,G., Kohda,T., Funakura,T., Yamauchi,T., Kihira,K., and Hoshita,T. |
| TITLE | : | Measurement of Serum Bile Alcohol Levels in Liver Dysfunction, Using Isotope Dilution-Mass Spectrometry. PubMed ID:3067328 |
| JOURNAL | : | Scand. J. Gastroenterol. |
| VOL | : | 23 PAGE : 821-826 (1988) |
| AUTHOR | : | Hiraoka,T., Kohda,T., Kosaka,D., Yamauchi,T., Kihira,K., Kuramoto,T., Hoshita,T., and Kajiyama,G. |
| TITLE | : | Identification of Bile Alcohols in Rat Bile. PubMed ID:2621416 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 30 PAGE : 1889-1893 (1989) |
| AUTHOR | : | Dayal,B., Shefer,S., Tint,G.S., Salen,G., and Mosbach,E.H. |
| TITLE | : | C26-Analogs of Naturally Occurring C27 Bile Alcohols. PubMed ID:965840 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 17 PAGE : 478-484 (1976) |
| AUTHOR | : | Kibe,A., Nakai,S., Kuramoto,T., and Hoshita,T. |
| TITLE | : | Occurrence of Bile Alcohols in the Bile of a Patient with Cholestasis. PubMed ID:7400689 |
| JOURNAL | : | J. Lipid Res. |
| VOL | : | 21 PAGE : 594-599 (1980) |
| AUTHOR | : | Hoshita,T., Kouchi,M., and Kazuno,T. |
| TITLE | : | Synthesis of 3a,7a,12a,26,27-Pentahydroxycoprostane |
| JOURNAL | : | J. Biochem. |
| VOL | : | 53 PAGE : 291-294 (1963) |
| AUTHOR | : | Haslewood,G.A.D., and Tammar,A.R. |
| TITLE | : | Bile Salts of Sturgeons (acipenseridae) and of the Paddlefish Polyodon Spathula: A New Partial Synthesis of 5b-Cyprinol. PubMed ID:5665889 |
| JOURNAL | : | Biochem. J. |
| VOL | : | 108 PAGE : 263-268 (1968) |
| AUTHOR | : | Cross,A.D., Landis,P.W., and Murphy,J.W. |
| TITLE | : | Steroids CCLXXVII. Spectra and Stereochemistry XIX. A Comparative Study of the NMR Spectra of Some Steroids in Five Solvents. The Structure of 'Acipenserol-A'. |
| JOURNAL | : | Steroids |
| VOL | : | 5 PAGE : 655-662 (1965) |
| AUTHOR | : | Anderson,I.G., Banister,K.E., Haslewood,G.A.D., Cho,D., and Tokes,L. |
| TITLE | : | Bile Salts of Fishes Collected on the Zaire River Expedition (1974-5): Their Chemical Nature and Its Possible Significance. |
| JOURNAL | : | Zool. J. Linn. Soc. |
| VOL | : | 68 PAGE : 41-51 (1980) |
| AUTHOR | : | Kuramoto,T., Kikuchi,H., Sanemori,H., and Hoshita,T. |
| TITLE | : | Bile Salts of Anura. PubMed ID:4727363 |
| JOURNAL | : | Chem. Pharm. Bull. |
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| AUTHOR | : | Hoshita,T., Yukawa,M., and Kazuno,T. |
| TITLE | : | The Isolation of a New Bile Alcohol, 5b-Cholestane-3a,7a,12a,26,27- Pentol from the Bile of Conger Myriaster |
| JOURNAL | : | Steroids |
| VOL | : | 4 PAGE : 569-574 (1964) |
| AUTHOR | : | Kazuno,T., Betsuki,S., Tanaka,Y., and Hoshita,T. |
| TITLE | : | Stero-bile acids and bile alcohols. LXXV. Studies on Bile of Rana Nigromaculata. PubMed ID:5861329 |
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| TITLE | : | NMR Spectra of Sterols(in Japanese language) |
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| TITLE | : | Isolation of 22-Dehydrocampesterol from the Seeds of Brassica Juncea. |
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| TITLE | : | Stereoselective Synthesis of the C-24 and C-25 Stereoisomeric Pairs of 24- Ethyl-26-Hydroxy- and 24-Ethyl-[26-2H]Sterols and Their D22-Derivatives; Reassignment of 13C N.M.R. Signals of the Pro-R and Pro-S Methyl Groups at. |
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| TITLE | : | 24b-Methylcholesta-5,22e,25-Tri-en-3b-ol and 24a-Ethyl-5a-Cholest-22e -en-3b-ol from Clerodendrum Fragrans. |
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| JOURNAL | : | Lipids |
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| JOURNAL | : | Fette, Seifen, Anstrichm. |
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| TITLE | : | Constituents of Clerodenron Infortunatum (Bhat)-Ii Structure of Clerosterol,Clerodol,Clerodolone and Clerodone. |
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| TITLE | : | Sterols of some Clerodendrum species (Verbenaceae): occurrence of the 24 alpha- and 24 beta-epimers of 24-ethylsterols lacking a delta 25-bond PubMed ID:2799860 |
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| TITLE | : | Co-occurrence of C-24 Epimeric 24-Ethyl-D7-Sterols in the Roots of Trichosanthes Japonica. |
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| TITLE | : | The Unsaponifiables of Vernonia Anthelmintica Seed Oil. |
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| TITLE | : | Triterpene Alcohols and Sterols in the Seeds of Brassica Napus. |
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| TITLE | : | The Neutral Constituents of the Cactus Lophocereus Schottii. The Structure of Lophenol---4a-Methyl-D7-Cholesten-3b-ol---A Link in Sterol Biogenesis |
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| AUTHOR | : | Itoh,T., Tamura,T., and Matsumoto,T. |
| TITLE | : | Triterpene Alcohols in the Seeds of Solanaceae. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 17 PAGE : 1723-1726 (1977) |
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| AUTHOR | : | Itoh, T., Tamura, T., and Matsumoto, T. |
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| JOURNAL | : | Lipids. |
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| AUTHOR | : | Akihisa,T., Shimizu,N., Kawaguchi,R., Tamura,T., and Matsumoto,T. |
| TITLE | : | 1H NMR Spectra of Some Tetracyclic and Pentacyclic 3b-Monoacetoxytriterpenes with Eu(Dpm)3. |
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| TITLE | : | Application of Mass Spectrometry To the Structural Investigation of 9,19- Cycloterols and Triterpenes. |
| JOURNAL | : | J. Chem. Soc.(B) |
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| TITLE | : | Studies of 13C NMR Spectra of 13C-Enriched Cycloartenol Biosynthesized from[1-13C]-,[2-13C]- and [1,2-13C2]-Acetate. Revised 13C NMR Spectral Assignments of Cycloartenol and Cycloartanol and 13C NMR Spectral Support for the. |
| JOURNAL | : | Magn. Reson. Chem. |
| VOL | : | 25 PAGE : 683-687 (1987) |
| AUTHOR | : | Bentley,H.R., Henry,J.A., Irivine,D.S., and Spring,F.S. |
| TITLE | : | Triterpene Resinols and Related Acids. Part XXVIII. The Nonsaponifiable Fraction from Strychnos Nux-Vomica Seed Fat: The Structure of Cycloartenol |
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| VOL | : | PAGE : 3673-3678 (1953) |
| AUTHOR | : | Akihisa,T., Yano,K., Kawaguchi,R., Yokota,T., Tamura,T., and Matsumoto,T. |
| TITLE | : | (24E)-and (24Z)-24-Ethylidenecycloartanols from Neolitsea Sericea. |
| JOURNAL | : | J. Jpn. Oil Chem. Soc.(Yukagaku) |
| VOL | : | 37 PAGE : 126-129 (1988) |
| AUTHOR | : | Chitwood, D. J., and Lusby, W. R. |
| TITLE | : | Metabolism of plant sterols by nematodes PubMed ID:1779708 |
| JOURNAL | : | Lipids. |
| VOL | : | 26 PAGE : 619-627 (1991) |
| AUTHOR | : | Kircher, H. W., and Rosenstein, F. U. |
| TITLE | : | Purification of campesterol and preparation of 7-dehydrocampesterol, 7-campestenol and campestanol PubMed ID:4857275 |
| JOURNAL | : | Lipids. |
| VOL | : | 9 PAGE : 333-337 (1974) |
| AUTHOR | : | Akihisa,T., Shimizu,N., Ghosh,P., Thakur,S., Rosenstein,F.U., Tamura,T., and Matsumoto,T. |
| TITLE | : | Sterols of the Cucurbitaceae. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 26 PAGE : 1693-1700 (1987) |
| AUTHOR | : | Akihisa,T., Tanaka,N., Yokota,T., Tanno,N., and Tamura,T. |
| TITLE | : | 5a-Cholest-8(14)-en-3b-ol and Three 24-Alkyl-D8(14)-Sterols from the Bulbils of Dioscorea Batatas. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 30 PAGE : 2369-2372 (1991) |
| AUTHOR | : | Itoh,T., Sica,D., and Djerassi,C. |
| TITLE | : | Minor and Trace Sterols in Marine Invertebrates. Part 35. Isolation and Structure Elucidation of Seventy-Four Sterols from the Sponge Axinella Cannabina. |
| JOURNAL | : | J. Chem. Soc., Perkin Trans. I |
| VOL | : | PAGE : 147-153 (1983) |
| AUTHOR | : | Misso,N.L.A., and Goad,L.J. |
| TITLE | : | Investigation on the D23-,D24(28)-and D25-Sterols of Zea Mays. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 23 PAGE : 73-82 (1984) |
| AUTHOR | : | Akihisa,T., Thakur,S., Rosenstein,F.U., and Matsumoto,T. |
| TITLE | : | Sterols of Cucurbitaceae: the Configuration at C-24 of 24-Alkyl-D5-,D7- and D8-Sterols. |
| JOURNAL | : | Lipids |
| VOL | : | 21 PAGE : 39-47 (1986) |
| AUTHOR | : | Akihisa,T., Tamura,T., Matsumoto,T., Kokke,W.C.M.C.,Ghosh,P., and Thakur,S. |
| TITLE | : | (22Z,24S)-Stigmasta-5, 22, 25-Trien-3b-ol and Other Novel Sterols from Clerodendrum Scandens: First Report of the Isolation of a Cis-D22-Unsaturated Sterols from a Higher Plant. |
| JOURNAL | : | J. Chem. Soc., Perkin Trans. I |
| VOL | : | PAGE : 2213-2218 (1990) |
| AUTHOR | : | Kalidindi,R.S., Rao,Ch.B., Akihisa,T., and Matsumoto,T. |
| TITLE | : | Sterols of Spirastrella Inconstans(Dendy) and Axinella Sp. from the Indian Ocean. |
| JOURNAL | : | Indian J.Chem. |
| VOL | : | 27 PAGE : 160-162 (1988) |
| AUTHOR | : | Nes, W. D., Norton, R. A., Crumley, F. G., Madigan, S. J., and Katz, E. R. |
| TITLE | : | Sterol phylogenesis and algal evolution PubMed ID:11607106 |
| JOURNAL | : | Proc Natl Acad Sci U S A. |
| VOL | : | 87 PAGE : 7565-7569 (1990) |
| AUTHOR | : | Akihisa,T., Kojima,S., Yokota,T., and Tamura,T. |
| TITLE | : | 24-Methylene-25-Methylcholesterol and Both C-24 Epimers of 24-Ethyl-22-Dehydrocholesterol in a Freshwater Green Alga Hydrodictyon Reticulatum. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 30 PAGE : 3621-3624 (1991) |
| AUTHOR | : | Lusby,W.R., Oliver,J.E., Mckibben,G.H., and Thompson,M.J. |
| TITLE | : | Free and Esterified Sterols of Cotton Buds and Anthers. |
| JOURNAL | : | Lipids |
| VOL | : | 22 PAGE : 80-83 (1987) |
| AUTHOR | : | Akihisa,T., Kokke,W.C.M.C., Tamura,T., and Matsumoto,T. |
| TITLE | : | Sterols of Kalanchoe Pinnata : First Report of the Isolation of Both C-24 Epimers of 24-Alkyl-D25-Sterols from a Higher Plant. |
| JOURNAL | : | Lipids |
| VOL | : | 26 PAGE : 660-665 (1991) |
| AUTHOR | : | Kalinowska,M., Nes,W.R., Crumley,F.G., and Nes,W.D. |
| TITLE | : | Stereochemical Differences in the Anatomical Distribution of C-24 Alkylated Sterols in Kalanchoe Daigremontiana. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 29 PAGE : 3427-3434 (1990) |
| AUTHOR | : | Gladu,P.K., Patterson,G.W., Wikfors,G.H., and Lusby,W.R. |
| TITLE | : | Free and Combined Sterols of Pavlova Gyrans. |
| JOURNAL | : | Lipids |
| VOL | : | 26 PAGE : 656-659 (1991) |
| AUTHOR | : | Lokley,W.J.S., Roberts,D.P., Rees,H.H., and Goodwin,T.W. |
| TITLE | : | 24-Methylcholesta-5,24(25)-Dien-3b-ol : A New Sterols from Withania Somnifera. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | PAGE : 3773-3776 (1974) |
| AUTHOR | : | Akihisa,T., Nishimura,Y., Roy,K., Ghosh,P., Thakur,S., and Tamura,T. |
| TITLE | : | Sterols of Three Leguminosae Seeds : Occurrence of 24a-Ethyl-5a-Cholest-9(11)-en-3b-ol and Both C-24 Epimers of 24-Ethylcholesta-5,25-Dien-3b-ol. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 30 PAGE : 4029-4032 (1991) |
| AUTHOR | : | Thakur,S., Ghosh,P., Akihisa,T., Shimizu,N., Tamura,T., and Matsumoto,T. |
| TITLE | : | Configurations at C-24 of 24-Alkylsterols from Clerodendrum Infortunatum Linn. |
| JOURNAL | : | Indian J.Chem. |
| VOL | : | 27 PAGE : 17-20 (1988) |
| AUTHOR | : | Matsumoto,T., Asano,S., and Itoh,T. |
| TITLE | : | 24-Methylene-25-Methylcholesterol, a Sterol from the Seeds of Brassica Juncea. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 22 PAGE : 2619-2622 (1983) |
| AUTHOR | : | Itoh,T., Tamura,T., Mitsuhashi,T., and Matsumoto,T. |
| TITLE | : | Sterols of Liliaceae. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 16 PAGE : 140-141 (1977) |
| AUTHOR | : | Salt,T.A., Xu,S., Patterson,G.W., and Adler,J.H. |
| TITLE | : | Diversity of Sterol Biosynthetic Capacity in the Caryophyllidae. |
| JOURNAL | : | Lipids |
| VOL | : | 26 PAGE : 604-613 (1991) |
| AUTHOR | : | Matsumoto,T., Nakagawa,M., and Itoh,T. |
| TITLE | : | 24a-Methyl-5a-Cholest-7-en-3b-ol from Seed Oil of Helianthus Annuus. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 23 PAGE : 921-923 (1984) |
| AUTHOR | : | Norton,R.A., and Nes,W.D. |
| TITLE | : | Indentification of Ergosta-6(7),8(14),25(27)-Trien-3b-ol and Ergosta-5(6),7(8),25(27)-Trien-3b-ol,Two New Steroidal Trienes Synthesized by Prototheca Wickerharmii. |
| JOURNAL | : | Lipids |
| VOL | : | 26 PAGE : 247-249 (1991) |
| AUTHOR | : | Palmer,M.A., and Bowden,B.N. |
| TITLE | : | The Sterols and Triterpenes of Sorghum Vulgare Grains. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 14 PAGE : 2049-2053 (1975) |
| AUTHOR | : | Akihisa,T., Tamura,T., Matsumoto,T., Kokke,W.C.M.C., and Yokota,T. |
| TITLE | : | Isolation of Acetylenic Sterols from a Higher Plant. Further Evidence That Marine Sterols are Not Unique. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 54 PAGE : 606-610 (1989) |
| AUTHOR | : | Schmitt,P., and Benveniste,P. |
| TITLE | : | Effect of AY-9944 on Sterol Biosynthesis in Suspension Cultures of Bramble Cells. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 18 PAGE : 445-450 (1979) |
| AUTHOR | : | Delsesh,C., Kashman,Y., and Djerassi,C. |
| TITLE | : | Ergosta-5,7,9(11),22-Tetraen-3b-ol and Its 24-Ethyl Homolog,Two New Marine Sterols from the Red Sea Sponge Biemna Fortis. |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 62 PAGE : 2037-2045 (1979) |
| AUTHOR | : | Nes, W. D., Xu, S. H., and Haddon, W. F. |
| TITLE | : | Evidence for similarities and differences in the biosynthesis of fungal sterols PubMed ID:2678609 |
| JOURNAL | : | Steroids. |
| VOL | : | 53 PAGE : 533-558 (1989) |
| AUTHOR | : | Itoh,T., Yoshida,K., Yatsu,T., Tamura,T., Matsumoto,T., and Spencer,G.F. |
| TITLE | : | Triterpene Alcohols and Sterols of Spanish Olive Oil. |
| JOURNAL | : | J. Am. Oil Chem. Soc. |
| VOL | : | 58 PAGE : 545-550 (1981) |
| AUTHOR | : | Raederstorff,D., and Rohmer,M. |
| TITLE | : | The Action of the Systemic Fungicides Tridemorph and Fenpropimorph on Sterol Biosynthesis by the Soil Amoeba Acanthamoeba Polyphaga. PubMed ID:3569273 |
| JOURNAL | : | Eur. J. Biochem. |
| VOL | : | 164 PAGE : 421-426 (1987) |
| AUTHOR | : | Akihisa,T., Kokke,W.C.M.C., Yokota,T., Tamura,T., and Matsumoto,T. |
| TITLE | : | 4a,14a-Dimethyl-5a-Ergesta-7,9(11),24(28)-Trien-3b-ol from Phaseolus Vulgaris and Gynostemma Pentaphyllum. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 29 PAGE : 1647-1651 (1990) |
| AUTHOR | : | Akihisa,T., Inada,Y., Ghosh,P., Thakur,S., Rosenstein,F.U., Tamura,T., and Matsumoto,T. |
| TITLE | : | Compositions of Triterpene Alcohols of Seeds and Mature Plants of Family Cucurbitaceae. |
| JOURNAL | : | J. Am. Oil Chem. Soc. |
| VOL | : | 65 PAGE : 607-610 (1988) |
| AUTHOR | : | Berti,G., Bottari,F., Marsili,A., Morelli,I., and Polvani,N. |
| TITLE | : | 31-Norcycloartanol and Cycloartanol from Polypodium Vulgare. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | PAGE : 125-130 (1967) |
| AUTHOR | : | Pinhas,H. |
| TITLE | : | Structure of a Cyclo-Triterpene : The Cyclosadol. |
| JOURNAL | : | Bull. Soc. Chim. Fr. |
| VOL | : | PAGE : 2037-2039 (1969) |
| AUTHOR | : | Itoh,T., Shimizu,N., Tamura,T., and Matsumoto,T. |
| TITLE | : | 24-Methyl-E-23-Dehydrolophenol,a New Sterol and Two Other 24-Methyl-E-D23-Sterols in Zea Mays Germ Oil. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 20 PAGE : 1353-1356 (1981) |
| AUTHOR | : | Endo T, Misu O, Inaba Y |
| TITLE | : | Studies on the Ferulates Contained in Rice Bran Oil. The Structure of (in Japanese language). |
| JOURNAL | : | J. Jpn. Oil Chem. Soc. (Yukagaku) |
| VOL | : | 7 PAGE : 89-98 (1968) |
| AUTHOR | : | Ito, T., Tamura, T., and Matsumoto, T. |
| TITLE | : | Methylsterol compositions of 19 vegetable oils PubMed ID:4785177 |
| JOURNAL | : | J Am Oil Chem Soc. |
| VOL | : | 50 PAGE : 300-303 (1973) |
| AUTHOR | : | Ponsinet,G., and Ourisson,G. |
| TITLE | : | Chemotaxonomic Study on the Family Euphorbiaceae. Distribution of Triterpenes in the Latex of Euphorbiaceae. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 7 PAGE : 89-98 (1968) |
| AUTHOR | : | Stankovic,S.K., Bastic,M.B., and Jovanovic,J.A. |
| TITLE | : | Composition of the Triterpene Alcohol Fraction of Horse Chestnut Seed. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 24 PAGE : 119-121 (1985) |
| AUTHOR | : | Khalid,S.A., Varga,E., Szendrei,K., and Duddeck,H. |
| TITLE | : | Isolation of Lanosta-9(11),24-Dien-3b-Yl Acetate from Leuzea Carthamoides. |
| JOURNAL | : | J. Nat. Prod. |
| VOL | : | 52 PAGE : 1136-1138 (1989) |
| AUTHOR | : | Akihisa,T., Sakamaki,H., Ichinohe,Y., Tamura,T., and Matsumoto,T. |
| TITLE | : | Platinum-Catalyzed Oxidation of D4- and D5- Unsaturated and Saturated Steroidal Alcohols. |
| JOURNAL | : | J. Jpn. Oil Chem. Soc. |
| VOL | : | 35 PAGE : 382-385 (1986) |
| AUTHOR | : | Hill,R.A., Kirk,D.N., Makin,H.L.J., and Murphy,G.M. (1991) in Dictionary of Steroids - Chemical Data, Structures and Bibliographies, Chapman and Hall, London |
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| VOL | : | PAGE : - (1991) |
| AUTHOR | : | Seldes,A.M., Gros,E.G., Suarez,A., Rovirosa,J., and San-Martin,A. |
| TITLE | : | Novel Sterols from the Sponge Esperiopsis Edwardil. |
| JOURNAL | : | Tetrahedron |
| VOL | : | 44 PAGE : 1359-1362 (1988) |
| AUTHOR | : | Erdman,T.R., and Thomson.R.H. |
| TITLE | : | Sterols from the Sponges Cliona Celata Grant and Hymeniacidon Perleve Montagu.. |
| JOURNAL | : | Tetrahedron |
| VOL | : | 28 PAGE : 5163-5173 (1972) |
| AUTHOR | : | Kalinovskaya,N.I., Kuznetsova,T.A., Popov,A.M., Antoniv,S.A., and Elyakov,G.B. |
| TITLE | : | Steroid Metabolites of the Far Eastern Holothurian Stichopus Japonicus Selenka.. |
| JOURNAL | : | Comp. Biochem. Physiol. |
| VOL | : | 76 PAGE : 167-171 (1983) |
| AUTHOR | : | Kobayashi, M., and Mitsuhashi, H. |
| TITLE | : | Marine sterols. VI(1). Sterols of the scallop, Patinopecten yessoensis PubMed ID:1209689 |
| JOURNAL | : | Steroids. |
| VOL | : | 26 PAGE : 605-624 (1975) |
| AUTHOR | : | Kalinovskaya,N.I., Kuznetsova,T.A., and Elyakov,G.B. |
| TITLE | : | Sterol Composition of Pacific Holothurian Stichopus Japonicus Selenka. |
| JOURNAL | : | Comp. Biochem. Physiol. |
| VOL | : | 74 PAGE : 597-601 (1983) |
| AUTHOR | : | Chitwood,D.J., Mcclure,M.A., Feldlaufer,M.F., Lusby,W.R., and Oliver,J.E. |
| TITLE | : | Sterol Composition and Ecdysteroid Content of Eggs of the Root-Knot Nematodes Meloidogyne Incognita and M.Arenaria. |
| JOURNAL | : | J. Nematol. |
| VOL | : | 19 PAGE : 352-360 (1987) |
| AUTHOR | : | Teshima,S., Patterson,G.W., and Dutky,S.R. |
| TITLE | : | Sterols of the Oyster, Crassostrea Virginica. |
| JOURNAL | : | Lipids |
| VOL | : | 15 PAGE : 1004-1011 (1980) |
| AUTHOR | : | Nichols,P.D., Volkman,J.K., and Johns,R.B. |
| TITLE | : | Sterols and Fatty Acids of the Marine Unicellular Alga, Fcrg 51. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 22 PAGE : 1447-1452 (1983) |
| AUTHOR | : | Heftmann, E., Wright, B. E., and Liddel, G. U. |
| TITLE | : | The isolation of Delta22-stigmasten-3beta-ol from Dictyostelium discoideum PubMed ID:13712749 |
| JOURNAL | : | Arch Biochem Biophys. |
| VOL | : | 91 PAGE : 266-270 (1960) |
| AUTHOR | : | Akihisa,T., Nishimura,Y., Nakamura,N., Roy,K., Ghosh,P., Thakur,S., and Tamura,T. |
| TITLE | : | Sterols of Cajanus Cajan and Three Other Leguminosae Seeds. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 31 PAGE : 1765-1768 (1992) |
| AUTHOR | : | Salt,T.A., Xu,S., Patterson,G.W., and Adler,J.H. |
| TITLE | : | Diversity of Sterol Biosynthetic Capacity in the Caryophyllidae. |
| JOURNAL | : | Lipids |
| VOL | : | 26 PAGE : 604-613 (1991) |
| AUTHOR | : | Chitwood,D.J., Hutzell,P.A., and Lusby,W.R. |
| TITLE | : | Sterol Composition of the Corn Cyst Nematode, Heterodera Zeae, and Corn Roots. |
| JOURNAL | : | J. Nematol. |
| VOL | : | 17 PAGE : 64-68 (1985) |
| AUTHOR | : | Li,H.T., and Djerassi,C. |
| TITLE | : | Structural and Stereochemical Aspects of Base-Catalyzed Double Bond Isomerization of Sterols with Unsaturated Side Chains. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 47 PAGE : 4298-4303 (1982) |
| AUTHOR | : | Scheid,F., and Benveniste,P. |
| TITLE | : | Ergosta-5,23-Dien-3b-ol and Ergosta-7,23-Dien-3b-ol, Two New Sterols from Zea Mays Etiolated Coleoptiles. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 18 PAGE : 1207-1209 (1979) |
| AUTHOR | : | Salt, T. A., Lozano, R., Lusby, W. R., Chitwood, D. J., and Thompson, M. J. |
| TITLE | : | 24-Methyl-23-dehydrocholesterol: a new sterol intermediate in C-24 demethylation from the nematodes Panagrellus redivivus and Caenorhabditis elegans? PubMed ID:3445294 |
| JOURNAL | : | Steroids. |
| VOL | : | 48 PAGE : 451-460 (1986) |
| AUTHOR | : | Rubinstein,I., and Goad,L.J. |
| TITLE | : | Sterols of the Siphonous Marine Alga Codium Fragile. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 13 PAGE : 481-484 (1974) |
| AUTHOR | : | Akihisa,T., Gebreyesus,T., Hayashi,H., and Tamura,T. |
| TITLE | : | Co-occurrence of C-24 Epimeric 24-Ethylsterols Possessing and Lacking a D25-Bond in Kalanchoe Petitiana. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 31 PAGE : 163-166 (1992) |
| AUTHOR | : | Garg,V.K., and Nes,W.R. |
| TITLE | : | Changes in D5-and D7-Sterols During Germination and Seedling Development of Cucurbita Maxima. |
| JOURNAL | : | Lipids |
| VOL | : | 20 PAGE : 876-883 (1985) |
| AUTHOR | : | Garg,V.K., and Nes,W.R. |
| TITLE | : | Occurrence of D5-Sterols in Plants Producing Predominantly D7-Sterols : Studies on the Sterol Compositions of Six Cucurbitaceae Seeds. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 25 PAGE : 2591-2597 (1986) |
| AUTHOR | : | Kokke,W.C.M.C., Pak,C.S., Fenical,W., and Djerassi,C. |
| TITLE | : | Minor and Trace Sterols in Marine Invertebrates. XII. Occurrence of 24(R+S)-Isopropenylcholesterol, 24(R+S)-Methylcholesta-5,25-Dien-3b-ol,and 24(R+S)-Methylcholesta-7,25-Dien-3b-ol in the Caribbean Sponge, Verongia Cauliformis. |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 62 PAGE : 1310-1318 (1979) |
| AUTHOR | : | Itoh,T., Sica,D., and Djerassi,C. |
| TITLE | : | (24S)-24H-Isocalysterol : A New Steroidal Cyclopropene from the Marine Sponge Calyx Niceaensis. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 48 PAGE : 890-892 (1983) |
| AUTHOR | : | Ayanoglu,E., Chan,A., and Djerassi,C. |
| TITLE | : | Use of N-Lithioethylenediamine in the Double Bond Isomerization and Degradation of Sterol Side Chains. |
| JOURNAL | : | Tetrahedron |
| VOL | : | 35 PAGE : 1591-1594 (1979) |
| AUTHOR | : | Kokke,W.C.M.C., Shoolery,J.N., Fenical,W., and Djerassi,C. |
| TITLE | : | Biosynthetic Studies of Marine Lipids. 4. Mechanism of Side Chain Alkylation in (E)-24-Propylidenecholesterol by a Chrysophyte Alga. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 49 PAGE : 3742-3752 (1984) |
| AUTHOR | : | Idler, D. R., Safe, L. M., and MacDonald, E. F. |
| TITLE | : | A new C-30 sterol (Z)-24-propylidenecholest-5-en-3 -ol (29-methylisofucosterol) PubMed ID:5149572 |
| JOURNAL | : | Steroids. |
| VOL | : | 18 PAGE : 545-553 (1971) |
| AUTHOR | : | Yasuda,S. |
| TITLE | : | Occurrence of 29-Methylisofucosterol in Ascidians. |
| JOURNAL | : | Bull. Jpn. Soc. Sci. Fish. |
| VOL | : | 42 PAGE : 1307-1307 (1976) |
| AUTHOR | : | Sheikh,Y.M., and Djerassi,C. |
| TITLE | : | Sterolds from Sponges. |
| JOURNAL | : | Tetrahedron |
| VOL | : | 30 PAGE : 4095-4103 (1974) |
| AUTHOR | : | Kobayashi,M., Tsuru,R., Todo,K., and Mitsuhashi,H. |
| TITLE | : | Marine Sterols-II. Asterosterol, a New C26 Sterol from Asterias Amurensis Lutken. |
| JOURNAL | : | Tetrahedron |
| VOL | : | 29 PAGE : 1193-1196 (1973) |
| AUTHOR | : | Anastasia,M., and Fiecchi,A. |
| TITLE | : | Stereospecific Synthesis of the Marine Sterol Stellasterol,(22e,24s)-5a-Ergosta-7,22-Dien-3b-ol. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 46 PAGE : 1726-1728 (1981) |
| AUTHOR | : | Matsumoto,T., Shigemoto,T., and Itoh,T. |
| TITLE | : | (22E,24S)-5a-Ergosta-7,22-Dien-3b-ol from the Seeds of Cucumis Sativus. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 22 PAGE : 1300-1301 (1983) |
| AUTHOR | : | Smith, A. G., Rubinstein, I., and Goad, L. J. |
| TITLE | : | The sterols of the echinoderm Asterias rubens PubMed ID:4772271 |
| JOURNAL | : | Biochem J. |
| VOL | : | 135 PAGE : 443-455 (1973) |
| AUTHOR | : | Dickson,L.G., Patterson,G.W., Cohen,C.F., and Dutky,S.R. |
| TITLE | : | Two Novel Sterols from Inhibited Chlorella Ellipsoidea. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 11 PAGE : 3473-3477 (1972) |
| AUTHOR | : | Raederstorff,D., and Rohmer,M. |
| TITLE | : | The Action of the Systemic Fungicides Tridemorph and Fenpropimorph on Sterol Biosynshesis by the Soil Amoeba Acanthamoeba Polyphaga. PubMed ID:3569273 |
| JOURNAL | : | Eur. J. Biochem. |
| VOL | : | 164 PAGE : 421-426 (1987) |
| AUTHOR | : | Akihisa,T., Hori,T., Suzuki,H., Sakoh,T., Yokota,T., and Tamura,T. |
| TITLE | : | 24b-Methyl-5a-Cholest-9(11)-en-3b-ol,Two 24b-Alkyl-D5,7,9(11)-Sterols and Other 24b-Alkylsterols from Chlorella Vulgaris. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 31 PAGE : 1769-1772 (1992) |
| AUTHOR | : | Zielinski, J., Milkova, T., Popov, S., Marekov, N., and Djerassi, C. |
| TITLE | : | Minor and trace sterols in marine invertebrates. Isolation and structure elucidation of 24-methyl-5 alpha-cholesta-7,9(11), 24(28)-trien-3 beta-ol, the first naturally occurring delta 7,9(11) unsaturated marine sterol PubMed ID:7157438 |
| JOURNAL | : | Steroids. |
| VOL | : | 39 PAGE : 675-680 (1982) |
| AUTHOR | : | Takaishi,Y., Murakami,Y., Ohashi,T., Nakano,K., Murakami,K., and Tomimatsu,T. |
| TITLE | : | Three Triterpenes from Astraeus Hygrometricus. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 26 PAGE : 2341-2344 (1987) |
| AUTHOR | : | Nes,W.R., Krevits,K., Joseph,J., Nes,W.D., Harris,B., Gibbons,G.F., and Patterson,G.W. |
| TITLE | : | The Phylogenetic Distribution of Sterols in Tracheophytes. |
| JOURNAL | : | Lipids |
| VOL | : | 12 PAGE : 511-527 (1977) |
| AUTHOR | : | Cattel,L., Balliano,G., and Caputo,O. |
| TITLE | : | Stigmasta-7,E-24(28)-Dien-3b-ol from Bryonia Dioica Roots. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 18 PAGE : 861-862 (1979) |
| AUTHOR | : | Sucrow,W. |
| TITLE | : | Zwei Neue D7-Sterine Aus Momordica Charantia. |
| JOURNAL | : | Chem. Ber. |
| VOL | : | 99 PAGE : 3559-3567 (1966) |
| AUTHOR | : | Itoh,T., Kikuchi,Y., Tamura,T., and Matsumoto,T. |
| TITLE | : | Co-occurrence of Chondrillasterol and Spinasterol in Two Cucurbitaceae Seeds as Shown by 13C NMR. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 20 PAGE : 761-764 (1981) |
| AUTHOR | : | Seo,S., Uomori,A., Yoshimura,Y., Takeda,K., Seto,H., Ebizuka,Y., Noguchi,H., and Sankawa,U. |
| TITLE | : | Biosynthesis of 24b-Ethylsterols in Cultured Cells of Trichosanthes Kirilowii(Cucurbitaceae) Fed with [1,2-13C2]-and [2-13C2H3]-Acetate: Reinvestigation of the Stereochemistry at C-25. |
| JOURNAL | : | J. Chem. Soc. Perkin Trans. I |
| VOL | : | PAGE : 1969-1974 (1989) |
| AUTHOR | : | Akihisa,T., Takahashi,S., Sahashi,N., Kokke,W.C.M.C., and Tamura,T. |
| TITLE | : | 24S-Chirality of 24-Alkylsterols Possessing a D25-Double Bond from Polypodium Formosanum. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 31 PAGE : 1353-1357 (1992) |
| AUTHOR | : | Akihisa,T., Tamura,T., and Matsumoto,T. |
| TITLE | : | 24-Methylene-25-Methyllathosterol : A Sterol from Sicyos Angulatus. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 26 PAGE : 575-577 (1987) |
| AUTHOR | : | Dolle,R.E., Schmidt,S.J., Erhard,K.F., and Kruse,L.I. |
| TITLE | : | Synthesis of Zymosterol, Fecosterol, and Related Biosynthetic Sterol Intermediates. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 111 PAGE : 278-284 (1989) |
| AUTHOR | : | Kato,T., Shoami,M., and Kawase,Y. |
| TITLE | : | Comparison of Tridemorph with Buthiobate in Antifungal Mode of Action. |
| JOURNAL | : | J. Pesticide Sci. |
| VOL | : | 5 PAGE : 69-79 (1980) |
| AUTHOR | : | Barton,D.H.R., Corrie,J.E.T., Widdowson,D.A., Bard,M., and Woods,R.A. |
| TITLE | : | Biosynthesis of Terpenes and Sterols. Part IX. The Sterols of Some Mutant Yeasts and Their Relationship to the Biosynthesis of Ergosterol. |
| JOURNAL | : | J. Chem. Soc. Perkin Trans. I |
| VOL | : | PAGE : 1326-1333 (1974) |
| AUTHOR | : | Herber,R., Villoutreix,J., Granger,P., and Chapelle,S. |
| TITLE | : | Influence De L'Anaerobiose Sur La Composition en Sterols De Mucor Hiemalis. PubMed ID:6883220 |
| JOURNAL | : | Can. J. Microbiol. |
| VOL | : | 29 PAGE : 606-611 (1983) |
| AUTHOR | : | Harvey,H.R., Bradshaw,S.A., O'hara,S.C.M., Eglinton,G., and Corner,E.D.S. |
| TITLE | : | Lipid Composition of the Marine Dinoflagellate Scripsiella Trochoidea. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 27 PAGE : 1723-1729 (1988) |
| AUTHOR | : | Kircher, H. W., and Rosenstein, F. U. |
| TITLE | : | Reaction of ergosteryl acetate with maleic anhydride and preparation of 5,7-ergostadien-3beta-ol1,2 PubMed ID:1177664 |
| JOURNAL | : | Lipids. |
| VOL | : | 10 PAGE : 517-523 (1975) |
| AUTHOR | : | Thompson,M.J., Dutky,S.R., Lehner,Y., Standifier,L.N., and Herbert,E.W. |
| TITLE | : | 24-Methylenepollinastanol and 24-Dehydropollinastanol-Two Sterols of Pollen. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 17 PAGE : 1053-1056 (1978) |
| AUTHOR | : | Nes,W.D., Benson,M., Lundin,R.E., and Le,P.H. |
| TITLE | : | Conformational Analysis of 9b,19-Cyclopropyl Sterols : Detection of the Pseudoplanar Conformer by Nuclear Overhauser Effects and Its Functional Implications. |
| JOURNAL | : | Proc. Natl. Acad. Sci. U.S.A. |
| VOL | : | 85 PAGE : 5759-5763 (1988) |
| AUTHOR | : | Akihisa,T., Ahmad,I., Singh,S., Tamura,T., and Matsumoto,T. |
| TITLE | : | 14a-Methylzymosterol and Other Sterols from Wrightia Tinctoria Seeds. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 27 PAGE : 3231-3234 (1988) |
| AUTHOR | : | Nes,W.D., and Schmidt,J.O. |
| TITLE | : | Isolation of 25(27)-Dehydrolanost-8-enol from Cereus Giganteus and Its Biosynthetic Implications. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 27 PAGE : 1705-1708 (1988) |
| AUTHOR | : | Knapp,F.F., Phillips,D.O., Goad,L.J., and Goodwin,T.W. |
| TITLE | : | Isolation of 14a-Methyl-9b,19-Cyclo-5a-Ergost-24(28)-en-3b-ol from Musa Sapientum. |
| JOURNAL | : | Phytochemistry |
| VOL | : | 11 PAGE : 3497-3500 (1972) |
| AUTHOR | : | Akihisa,T., Shimizs,N., Tamura,T., and Matsumoto,T. |
| TITLE | : | (24R)-14a-Methyl-24-Ethyl-5a-Cholest-9(11)-en-3b-ol : A New 14a-Methylsterol from Cucumis Sativus. |
| JOURNAL | : | Lipids |
| VOL | : | 21 PAGE : 491-493 (1986) |
| AUTHOR | : | Lue-Cam,C.A. |
| TITLE | : | Triterpenoids of Isertia Hypoleuca Leaves. |
| JOURNAL | : | Phytochem. |
| VOL | : | 12 PAGE : 475-476 (1973) |
| AUTHOR | : | V.Tamelen,E.E., Seiler,M.P. and Wierenga,W. |
| TITLE | : | Biogenetic-Type Total Synthesis.G-Amyrin,b-Amyrin,and Germnnicol. |
| JOURNAL | : | J.Am.Chem.Soc. |
| VOL | : | 94 PAGE : 8229-8231 (1972) |
| AUTHOR | : | Wahlberg,I., Karlsson,K. and Enzell,C.R. |
| TITLE | : | Non-Volatile Constituents of Deertongue Leaf. |
| JOURNAL | : | Acta Chem.Scand. |
| VOL | : | 26 PAGE : 1383-1388 (1972) |
| AUTHOR | : | Shinga,T., Yokoi,T.Niwa,M. and Kikuch,T. |
| TITLE | : | Application of Tris(Dipivaloylmethanate)Europium to the Assignments of Methyl Resonances of Triterpene Acetate Related to b-Amyrin. |
| JOURNAL | : | Chem.Pharm.Bull. |
| VOL | : | 21 PAGE : 2252-2256 (1973) |
| AUTHOR | : | Bryce,T.A., Eglinton,G. and Hamilton,J. |
| TITLE | : | Triterpenoids from New Zealand Plants. The Tritertene Methyl Ethers of Cortaperia Toetoe Zotov. |
| JOURNAL | : | Phytochem. |
| VOL | : | 6 PAGE : 727-733 (1967) |
| AUTHOR | : | Corey,E.J., Ortiz De Montellano,P.R. |
| TITLE | : | Emzymic Synthesis of b-Amyrin from 2,3-Oxidosqualen. |
| JOURNAL | : | J.Am.Chem.Soc. |
| VOL | : | 89 PAGE : 3362-3363 (1967) |
| AUTHOR | : | Lawrie,W., Mclean,J. and Olubajo,O.O.O. |
| TITLE | : | Triterpenes from Balata Resin. |
| JOURNAL | : | Pytochem. |
| VOL | : | 9 PAGE : 1669-1670 (1970) |
| AUTHOR | : | Boar,R.B. and Allen,J. |
| TITLE | : | b-Amyrin Triterpenoids. |
| JOURNAL | : | Pytochem. |
| VOL | : | 12 PAGE : 2571-2578 (1973) |
| AUTHOR | : | Barton,D.H.R. et.al. |
| TITLE | : | |
| JOURNAL | : | J.Chem.Soc., Chem.C2/3/7/12/26/27 |
| VOL | : | 2 PAGE : 2- () |
| AUTHOR | : | Atallah,A.M., Aexei,R.T., Ramsey,R.B. and Nicholas,H.J. |
| TITLE | : | Biosynthesis in Pelargonium Hortorom. |
| JOURNAL | : | Phytochem. |
| VOL | : | 14 PAGE : 1529-1533 (1975) |
+24
= +94.3
= +95
= -91.2
= -104
=+83.5
=+77
=+88.4
=+54.5