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Eicosanoid

(total 329)
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No Structure COMMON NAME NAME DATA No INFORMANT SYMBOL FORMULA MOL.WT(ave) Download BIOOGICAL ACTIVITY PHYSICAL AND CHEMICAL PROPERTIES SPECTRAL DATA CHROMATOGRAM DATA SOURCE CHEMICAL SYNTHESIS METABOLISM GENETIC INFORMATION NOTE REFERENCES
MELTING POINT BOILING POINT DENSITY REFRACTIVE INDEX OPTICAL ROTATION SOLUBILITY UV SPECTRA IR SPECTRA NMR SPECTRA MASS SPECTRA OTHER SPECTRA
1
PROSTAGLANDIN A1
7-[2(R)-(3(S)-Hydroxy-1(E)-octenyl)-5-oxo-3-cyclopenten-1(R)-yl]heptanoic acid / (8R,12S,13E,15S)-15-Hydroxy-9-oxo-10,13-prostadienoic acid
XPR1000
Shouzo Yamamoto
PGA1
C20H32O4 336.466 Download ChemDraw structure file
Prostaglandin A1 relaxes uterine muscle and shows hypotensive effects on rat and dog (Ref. 0002).
42-44degC (Ref. 1005)
ORD (H2O, C=0.0040g/ml) : 256(+35.000deg), 220(-43.000deg) (Ref. 1101)
ETHANOL, CHLOROFORM (Ref. 1005), METHANOL (Ref. 1101)
l EtOHmax = 217nm(e 11,650) (Ref. 1005)
NUJOL : n 3420, 2740, 2700, 2660, 2600, 1715, 1700, 1585, 1275, 1200,1180, 1020, 720cm-1 (Ref. 1005)
1H-NMR(CDCl3, TMS) : d, 7.52(dd, 1H), 6.17(dd, 1H), 5.6(m, 2H), 4.1(m, 1H, 15-CH), 3.25(12H) (Ref. 1005)
m/e, 336(M+), 318(M-18), 300(M-36), 265(M-71), 247, 219, 190 (Ref. 1005)
ORD(H2O, C=0.0040g/100ml), 256(+35, 000deg), 220(-43,000deg) (Ref. 1101)

Prostaglandin A1 is found in human seminal plasma (Ref. 0001).



2
PROSTAGLANDIN A2
7-[2(R)-(3(S)-Hydroxy-1(E)-octenyl)-5-oxo-3-cyclopenten-1(R)-yl]-5(Z)-heptenoic acid
XPR1001
Shouzo Yamamoto
PGA2
C20H30O4 334.450 Download ChemDraw structure file
Antitumor activity of prostaglandin A2 is known (Ref. 0038), and prostaglandin A2 rduces blood pressure (Ref. 0002).
[a]d-20=+140deg(C=1.15, CHLOROFORM) (Ref. 1042)
ETHANOL, CHLOROFORM, METHANOL, DIETHYLETHER (Ref. 1005)
EtOH: 217 nm (e 9900) (Ref. 1005)
NUJOL : n 3400, 1705, 1580, 1255, 1115, 1070, 1015 cm-1 (Ref. 1005)
1H-NMR(CDCl3) : d 7.57(dd, 1H, 10-CH), 6.2(dd, 1H, 11-CH), 5.6(m, 2H, 13,14-CH), 5.4 (m, 2H, 5,6-CH), 4.12(1H, m, 12-CH), 3.23(m, 1H), 0.89(t, 3H, 0-CH3) (Ref. 1043). METHYL ESTER : 13C-NMR(CDCl3) 210.3, 174.0, 165.0, 135.2, 133.3, 131.0, 130.2, 126.7, 72.4, 52.1, 51.5, 49.6, 37.3, 33.5, 31.8, 27.4, 26.7, 25.1, 24.8, 22.6, 14.0 (Ref. 1044)
m/e 334(M+), 316, 190 (Ref. 1005)


Prostaglandin A2 was found in human semen in an amount of about 50 micrograms per ml as measured in combination with prostaglandins A1, B1 and B2 (Ref. 0001).
Prostaglandin A2 is produced by non-enzymatic degradation of prostaglandin E2 (Ref. 0039), and human serum has an enzymatic activity to convert prostaglandin E2 to A2 (Ref. 0040).


3
19-HYDROXY-PROSTAGLANDIN A2
7-[2(R)-(3(S),7-Dihydroxy-1(E)-octenyl)-5-oxo-3-cyclopenten-1(R)-yl]-5(Z)-heptenoic acid / 15(S),19-Dihydroxy-9-oxo-8(12),13-trans-prostadienoic acid
XPR1031
Shouzo Yamamoto
19-HYDROXY-PGA2
C20H30O5 350.449 Download ChemDraw structure file
19-Hydroxy-prostaglandin A2 relaxes uterine myometriuim (Ref. 0082).
DIETHYL ETHER, CHLOROFORM, ETHANOL (Ref. 1104)
l EtOHmax = 217 nm(e sim10,000) (Ref. 1104)
5.87, 6.30, 10.3mm (Ref. 1104)
1H-NMR : d 5.75-5.50(m, 2H,13, 14-CH), 5.50-5.25(m, 2H, 5,6-CH), 1.15(d, 3H, 20-CH) (Ref. 1104)
METHYL ESTER ; m/e 364(M+), 246, 328, 315 (Ref. 1104)


The compound is contained in human seminal plasma in a considerable amount (Ref. 0001), but it is attributed presumably to a degradation product of 19-hydroxy-prostagaldnin E2 (Ref. 0094).




4
PROSTAGLANDIN B1
7-[2-(3(S)-Hydroxy-1(E)-octenyl)-5-oxo-1-cyclopenten-1-yl]heptanoic acid / (E,S)-15-Hydroxy-9-oxo-8(12),13-prostadienoic acid
XPR1100
Shouzo Yamamoto
PGB1
C20H32O4 336.466 Download ChemDraw structure file

70-71degC (Ref. 1102)
l max = 278nm(e 28,650) (Ref. 1103)
5.91, 6.10, 6.27, 10.3mm (Ref. 1104)
1H-NMR :d 6.87(d, J=16Hz, 1H, 13-CH), 6.25(d,d, J=16.6Hz, 1H, 14-CH), 4.38(1H, 15-CH) (Ref. 1105)
METHYL ESTER ; m/e 350(M+), 332, 319, 301, 251, 219 (Ref. 1106)


Prostaglandin B1 is found in human seminal plasma (Ref. 0001).



5
PROSTAGLANDIN B2
7-[2-(3(S)-Hydroxy-1(E)-octenyl)-5-oxo-1-cyclopenten-1-yl]-5(Z)-heptenoic acid
XPR1101
Shouzo Yamamoto
PGB2
C20H30O4 334.450 Download ChemDraw structure file

MeOH: 278 nm (e 26000) (Ref. 1045)
METHYL ESTER ; 1H-NMR : d 6.9(d, J=16Hz, 1H, 13-CH), 6.3(dd, J=5.5, 16Hz, 1H,14-CH), 5.7-5.1(m, 2H), 4.5-4.1(m, 1H, 15-CH), 3.65(S, 3H, OCH3), 3.15-2.85(m, 2H, 7-CH) (Ref. 1046)
METHYL ESTER; m/e 348(M+), 317, 249, 247, 245, 217, 215, 133, 119, 109 (Ref. 1046)


Prostaglandin B2 was found in human seminal plasma in an amout of 50 micrograms per ml as measured in combination with prostaglandins A1,A2 and B1 (Ref. 0001).

Prostaglandin E2 is converted to prostaglandin B2 non-enzymatically at alkaline condition (Ref. 0039). Huma serum contains a dehydrase converting prostaglandin E2 to A2, an isomerase converting prostaglandin A2 to C2, and another isomerase converting prostaglandin C2 to B2 (Ref. 0040).


6
19-HYDROXY-PROSTAGLANDIN B2
7-[2-(3(S),7-Dihydroxy-1(E)-octenyl)-5-oxo-1-cyclopenten-1-yl]-5(Z)-heptenoic acid / 15(S),19-Dihydroxy-9-oxo-5-cis-8(12),13-trans-prostatrienoic acid
XPR1131
Shouzo Yamamoto
19-HYDROXY-PGB2
C20H30O5 350.449 Download ChemDraw structure file
19-Hydroxy-prostaglandin B2 relaxes uterine myometriuim (Ref. 0082).
ETHANOL (Ref. 1104)
l EtOHmax = 278 nm(e sim20,000) (Ref. 1104)
5.92, 6.09, 6.26, 10.3mm (Ref. 1104)




The compound is contained in human seminal plasma in a considerable amount (Ref. 0001), but it is attributed presumably to a degradation product of 19-hydroxy-prostagaldnin E2 (Ref. 0094).




7
PROSTAGLANDIN C2
7-[2-(3(S)-Hydroxy-1(E)-octenyl)-5-oxo-2-cyclopenten-1(R)-yl]-5(Z)-heptenoic acid
XPR1201
Shouzo Yamamoto
PGC2
C20H30O4 334.450 Download ChemDraw structure file

METHANOL, CHLOROFORM (Ref. 1047)
l MeOHmax = 234 nm (e 17000) (Ref. 1047)
CHLOROFORM solution, n 1750,1715 cm-1 (Ref. 1047)
METHYL ESTER ; d 6.3(d, J=16Hz, 1H, 13-CH), 6.1-5.95(m, 2H, 11-CH), 5,7(dd, J=6,16Hz, 1H, 14-CH), 5.7-5.1(m, 2H, 5,6-CH), 4.4-4.0(m, 1H, 15-CH), 3.69(S, 3H, OCH3), 3.3-3.0(m, 1H,8-CH), 3.0-2.8(m, 2H, 10-CH) (Ref. 1046)
METHYL ESTER; m/e 348(M+), 330, 249, 245, 217, 215, 190, 133, 119, 109 (Ref. 1046)



Prostaglandin A isomerase converts prostaglandin A2 to C2, and the enzyme is found in human serum (Ref. 0040) and in the plasma of rabbit, cat, pig, dog and rat (Ref. 0041).


8
PROSTAGLANDIN D2
7-[5(S)-Hydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)-3-oxocyclopentan-1(R)-yl]-5(Z)-heptenoic acid
XPR1301
Shouzo Yamamoto
PGD2
C20H32O5 352.465 Download ChemDraw structure file
Biological significance of prostaglandin D2 was unknown except anti-aggregatory and bronchoconstrictive activities (Ref. 0009). Recently prostaglandin D2 has been noted as antineoplastic agent (actually attributed to D12-prostaglandin J2) (Ref. 0010/0011) and as a sleep-inducing compound (Ref. 0012). Prostaglandin D2 binds to a receptor with 7 transmembrane domains (DP) coupled to a Gs protein (Ref. 0003).
68degC (Ref. 1010)
[a]d-20=9deg (C=2.11,THF) (Ref. 1012)
ETHYL ACETATE,THF,CHLOROFORM (Ref. 1012)
KBr : 3400-2500, 1740, 1700, 975cm-1 (Ref. 1010)
1H-NMR(270MHz, CDCl3) : d 5.63(dd,J=7 & 16Hz,1H,14-CH), 5.43(dd,J=16 & 8.5Hz,1H,13-CH), 4.47(m, 1H, 9-CH), 4.09(bq, J=7Hz, 1H, 15-CH), 2.87(dd, J=12 & 8.5Hz, 1H, 12-CH), 2.45(m, 2H, 10-CH2), 1.95(bm, 1H, 8-CH) (Ref. 1011)
m/e 334, 316, 246, 245, 191, 190, 161, 55 (Ref. 1012)


In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin D2. Prostaglandin D2 is produced in barin, lung, spleen, mast cells and other tissues (Ref. 0005).
Prostaglandin D2 is produced by isomerization of 9,11-endoperoxide of prostaglandin H2. There are two isozymes of prostaglandin D synthase (hematopoietic type and lipocalin type) distinguished by glutathione reequirement and effect of inhibitor (Ref. 0005). Prostaglandin D2 is either reduced to 9a,11b-prostaglandin F or oxidized to 15-keto-prostaglandin D2 by a specific dehydrogenase (Ref. 0009). Non-enzymatic transformation of prostaglandin D2 produces anti-neoplastic D12-prostaglandin J2 (Ref. 0011).
cDNA and genomic DNA of prostaglandin D synthase were cloned (Ref. 0005). cDNA for DP was isolated (Ref. 0011).

9
PROSTAGLANDIN E1
7-[3(R)-Hydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)-5-oxocyclopentan-1(R)-yl]-heptanoic acid / (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid
XPR1400
Shouzo Yamamoto
PGE1
C20H34O5 354.481 Download ChemDraw structure file
Prostaglandin E1 is generally considered as active as E2, and the biological activities of both compounds are compared in references (Ref. 0002/0088). However, platelet aggregation is inhibited by prostaglandin E1 whereas prostaglandin E2 is much less active (Ref. 0002).
115-117degC (Ref. 1107)
[a]578=-61.6deg(C=0.56, TETRAHYDROFURAN) (Ref. 1108)
DIETHYL ETHER, ETHYL ACETATE (Ref. 1107), METHANOL (Ref. 1106), TETRAHYDROFURAN (Ref. 1108)
METHYL ESTER ; n 1726, 1717sh, 1699, 980 cm-1 (Ref. 1109)
1H-NMR(CDCl3+DMSO-d6,TMS) : d 5.70-5.51(m, 2H), 4.14-3.86(m, 2H), 2.72(d,d, 1H)(Ref. 1109). 13C-NMR(CHCl3-CH3OH, TMS) : d 215.2(C-9), 176.7(C-1), 136.6(C-14), 131.9(C-13), 72.9(C-15), 71.6(C-11), 54.6(C-8), 54.2(C-12), 45.9(C-10), 36.9(C-16), 33.8(C-2), 31.5(C-18), 29.0(C-4), 28.6(C-5), 27.4(C-7), 26.3(C-6), 25.0(C-17), 24.5(C-3), 22.5(C-19), 13.8(C-20) (Ref. 1008)
METHYL ESTER ; m/e 350, 332, 319, 301, 279 (Ref. 1104)


Prostaglandin E1 is contained in human seminal plasma in an amount of 25 microgram/ml (Ref. 0001), and has been found in ovine seminal plasma and seminal vesicle, human menstrual and amniotic flluid, human uterine endometrium, umbilical cord, placental vessels and decidua, frog spinal cord, rat adrenal, human and bovine thymus, frog intestine, rat fat tissue, and human phrenic nerve (Ref. 0082/0083/0084/0085/0086/0087).
Prostagalndin E1 is produced from H1 at almost the same rate of E2 synthesis from H2 by an enzyme of bovine seminal vesicle (Ref. 0089).


10
Prostaglandin E2
7-[3(R)-Hydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl-5-oxocyclopentan-1(R)-yl]-5(Z)-heptenoic acid
XPR1401
Shouzo Yamamoto
PGE2
C20H32O5 352.465 Download ChemDraw structure file
Prostaglandin E2 exhibits various biological activities such as vasodilatation, uterine contraction, gastrointestinal contraction, bronchodilatation, diuresis, pyrexia, inhibition of gastric secretion, bone resorption and immunosuppression (Ref. 0002). Prostaglandin E2 is a ligand to receptors present in the cell membrane, and there are at least 4 subtypes of its receptor. Different tissue distributions and signal transductions of these receptor subtypes explain a variety of biological activities of prostaglandin E2 (Ref. 0003).
65-66degC (Ref. 1001)
[a]d-26=-61.0deg(C=1.0, TETRAHYDROFURAN) (Ref. 1001)
ETHYL ACETATE,THF,CHLOROFORM(Ref. 1002/1006). STABILITIES: to be stable under neutral condition. to decompose to PGA2 under acidic and to PGB2 under basic conditions (Ref. 1004/1005)
d,l-mixture ; 3400, 1710, 970cm-1 (Ref. 1003)
13C-NMR(CDCl3) : 214.71(C9),178.39(C1), 136.62(C14), 131.52(C13), 130.91(C5), 126.69(C6), 73.19(C15), 72.13(C11), 54.55(C12), 53.51(C8), 46.23(C10), 37.00 (C16), 33.56(C2), 31.73(C18), 26.47(C4), 25.20(C7,17), 24.60(C3), 22.64(C19), 14.04. (Ref. 1002). 1H-NMR(CDCl3) : d5.67(dd, J=6.6Hz, 15.4, 1H, 14-CH), 5.57(dd, J=8.1, 15.4Hz, 1H, 13-CH), 5.40(m, 2H, 5.6-CH), 4.12(q, J=6.5, 6.7, 6.8Hz, 1H, 15-CH), 4.06(q, J=8.1, 8.2, 8.3Hz, 1H, 11-CH), 2.72(dd, J= (Ref. 1002)
d,l-mixture ; 334(M+-18), 316, 298, 190 (Ref. 1003)


Prostaglandin E2 was found to be accummulating in human semen in an amount of about 13 microgram per ml (Ref. 0001). In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin E2.
Prostaglandin E2 is produced from arachidonic acid via prostaglandins G2 and H2 by the catalyses of prostaglandin endoperoxide synthase (cyclooxygenase) (Ref. 0004) and prostaglandin E synthase (Ref. 0005). Two isoforms of the cyclooxygnease enzyme responsible for prostaglandin H2 synthesis are present. Cyclooxygenase-1 is constitutively found in most mammalian tissues, while cyclooxygnease-2 is induced rapidly and transiently in physiological and pathological events, especially in inflammation (Ref. 0004). The biological activities of prostaglandin E2 are lost by oxidation of its 15-hydroxyl group catalyzed by 15-hydroxyprostaglandin dehydrogenase (Ref. 0006).
cDNAs of the two cyclooxygenase isozymes responsible for prostaglandin H2 synthesis have been cloned, and the primary structures of these enzymes were deduced from the nucleotide seuences (Ref. 0007/0008). Their genomic DNA were also cloned, and the genomic structure were eludicated (Ref. 0007). cDNAs of four subtypes of prostaglandin E2 receptors (EP1-4) were cloned, and the 7-transmembrane domain structures of the receptors coupled with certain G proteins were reported (Ref. 0003).

11
PROSTAGLANDIN E3
7-[3(R)-Hydroxy-2(R)-(3(S)-hydroxyocta-1(E),5(Z)-dienyl)-5-oxocyclopentan-1(R)-yl]-5(Z)-heptenoic acid / (5Z,8R,11R,12R,13E,15S,17Z)-11,15-Dihydroxy-9-oxo-5,13,17-prostatrienoic acid
XPR1402
Shouzo Yamamoto
PGE3
C20H30O5 350.449 Download ChemDraw structure file
As presented in Table 1 of reference (Ref. 0002), prostaglandin E3 is 1/10-1/2 as active as prostaglandin E2.
84.5-85.5degC (Ref. 1113)
[a]d-24=-48.9deg(C=1.2, TETRAHYDROFURAN) (Ref. 1114)
TETRAHYDROFURAN (Ref. 1114)
METHYL ESTER ; 1H-NMR(CDCl3) : d 5.8-5.5(m, 2H,13, 14-CH), 5.5-5.2(m, 4H, 5,6,17,18-CH), 4.4-3.8(m, 2H, 11,15-CH), 0.95(t, 3H, 20-CH) (Ref. 1115)
METHYL ESTER ; m/e 346(M-18), 328(M-18x2), 315, 297, 277, 259, 188 (Ref. 1116)


Prostaglandin E3 is contained in human seminal plasma in an amount of 5.5 micrograms/ml (Ref. 0001), and also found in ovine seminal vesicle and plasma (Ref. 0083).



12
15-KETOPROSTAGLANDIN E2
7-[3(R)-Hydroxy-2(R)-(3-oxo-1(E)-octenyl)-5-oxocyclopentan-1(R)-yl]-5(Z)-heptenoic acid
XPR1411
Shouzo Yamamoto
15-KETO-PGE2
C20H30O5 350.449 Download ChemDraw structure file
It is well known that the biological activities of various prostaglandins are reduced upon their dehydrogenation at carbon-15 by the catalysis of 15-hydroxyprostaglandin dehydrogenase (Ref. 0044).
METHYL ESTER ; l MeOHmax = 227nm (e sim 9000) (Ref. 1055)

DIMETHOXIME TMS ETHER METHYL ESTER ; m/z 494(M+), 479, 463, 404, 373, 321, 180 (Ref. 1055)


15-Keto-prostaglandin E2 is the oxidized product of prostaglandin E2 by 15-hydroxyprostaglandin dehydrogenase, which is present in lung, kidney, placenta and other tissues and catalyzes the NAD- or NADP-dependent dehydrogenation of 15-hydroxyl group (Ref. 0006).

15-Keto-prostaglandin E2 is further metabolized by its D13-reduction, b-oxidation and w oxidation. The ultimate metabolite is (7a-hydroxy-5,11-diketotetranorprosta-1,16-dioic acid) and excreted in urine (Ref. 0045).
cDNA for placental 15-hydroxyprostaglandin dehydrogenase was cloned (Ref. 0046).

13
PROSTAGLANDIN E-MAJOR URINARY METABOLITE
8-[2(R)-(2-Carboxyethyl)-5(R)-hydroxy-3-oxocyclopentan-1(R)-yl]-6-oxooctanoic acid
XPR1421
Shouzo Yamamoto
PGE-MUM
C16H24O7 328.358 Download ChemDraw structure file

ETHYL ACETATE (Ref. 1061)

DIMETHYL ESTER DI-O-METHYLOXIME TMS ETHER DERIVATIVE ; m/e 486, 455, 369, 365, 355, 286, 279, 268, 265, 196, 115 (Ref. 1061)


When prostaglandin E2 or E1 was administered intravenously to man, 7a-hydroxy-5,11-diketo-tetranor-prosta-1,16-dioic acid was found as a major urinary metabolite (PGE-MUM) (Ref. 0045).




14
6-KETO-PROSTAGLANDIN E1
7-[3(R)-Hydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)-5-oxocyclopentan-1(R)-yl]-6-oxoheptanoic acid
XPR1430
Shouzo Yamamoto
6-KETO-PGE1
C20H32O6 368.464 Download ChemDraw structure file
6-Keto-prostaglandin E1 is a stable metabolite. The compound inhibits platelet aggregation with activity comparable or greater than prostaglandin D2 although less potent than prostaglandin I2. Its vasodilatory and hypotensive activities, bronchodilatory property, and inhibition of gastric acid secretion were reported (Ref. 0054).
65degC (Ref. 1053)
[a]d-20=-50deg(C=1.55, METHANOL) (Ref. 1053)
METHANOL, CHLOROFORM (Ref. 1053)
KBr: n 3400, 1740, 1720, 1710, 1245, 1160, 1075, 970 cm-1 (Ref. 1053)
1H-NMR(CDCl3) : d 5.58(m, 2H, 13,14-CH), 4.09(m, 1H, 11-CH), 4.02(m, 1H, 15-CH), 2.7(2H, 7-CH), 2.69(IH, 10b-CH), 2.45-2.47(m, 3H, 5,8,12-CH), 2.29(1H, 10a-CH), 2.28(2H, 2-CH), 1.58 - 1.32(12H), 0.91(t, 3H, 20-CH3) (Ref. 1069). METHYL ESTER ; 13C-NMR(CDCl3) : 216.6, 208.4, 173.8, 138.0, 126.5, 72.3, 51.5, 44.6, 45.7, 42.4, 37.6, 33.8, 31.8, 25.2, 24.5, 23.4, 22.6, 14.0 (Ref. 1053)
DIRECT EXPOSURE AMMONIA CI, POSITIVE : 386(M++18), 368(M+), 351, 350, 244, 136. NEGATIVE : 368(M+) ,350, 338, 332 (Ref. 1054)


There were reports of prolonged biological activity of chemically unstable prostaglandin I2, which suggested a possible transformation of prostaglandin I2 to a more stable metabolite with potent bioactivity (Ref. 0053). Futher investigations led to the discovery of 6-keto-prostaglandin E1.
A potential role of 9-hydroxyprostaglandin dehydrogenase was demonstrated in the transformation of prostaglandin I2 to 6-keto-prostaglandin E1 (Ref. 0053).


15
PROSTAGLANDIN F1a
7-[3(R),5(S)-Dihydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)cyclopentan-1(R)-yl]-heptanoic acid / (8R,9S,11R,13E,15S)-9,11,15-Trihydroxyprost-13-enoic acid
XPR1500
Shouzo Yamamoto
PGF1a
C20H36O5 356.497 Download ChemDraw structure file
In terms of contraction of gastrointestinal smooth muscles, prostaglandin F1a was repoprted to be about 10 times less active than prostaglandin F2a (Ref. 0082). Reference (Ref. 0002) contains a table for comparison of biological activities of various prostaglandins including F1a.
102-103degC (Ref. 1110)
[a]d-25=+30deg(ETHANOL) (Ref. 1005)
DIETHYL ETHER, ETHYL ACETATE, METHANOL (Ref. 1110), ETHANOL (Ref. 1005)
d,l-PGF1a ; KBr : n 3330, 1716, 967 cm-1 (Ref. 1111)
1H-NMR(ACETONE-d6, TMS) : d 5.50(2H, 13-,14-CH), 3.75-4.3(m, 3H), 0.88(t, 3H) (Ref. 1102)1H-NMR(CD3OD, TMS, 300MHz):d4.10(1H, 9-CH), 3.81(1H, 11-CH), 2.36(1H, 10b-CH), 1.57(1H, 10a-CH)(Ref. 1112)
m/e 356(M+), 338, 320 (Ref. 1102)


Prostaglandin F1a is contained in human seminal plasma in an amount of 3.6 microgram/ml (Ref. 0001), and is detected in ovine seminal plasma and seminal vesicle, human amniotic fluid, umbilical cord, placental vessels and decidua, frog spinal cord and intestine, and rat adrenal (Ref. 0084).



16
PROSTAGLANDIN F2a
7-[3(R),5(S)-Dihydroxy-2(R)-(3(S)-hydroxy-1(E)-octenylcyclopentan-1(R)-yl]-5(Z)-heptenoic acid
XPR1501
Shouzo Yamamoto
PGF2a
C20H34O5 354.481 Download ChemDraw structure file
Prostaglandin F2a exhibits various biological activities such as uterine contraction, gastrointestinal contraction, bronchoconstriction, luteolysis and vasoconstriction (Ref. 0002). Prostaglandin F2a is a ligand to a receptor (FP) present in the cell membrane (Ref. 0003).
25-35degC (Ref. 1007)
[a]d-25=23.8 deg(C=1,THF) (Ref. 1001)
ETHYL ACETATE, ACETONE, DIETHYLETHER (Ref. 1005). STABILITIES: to be stable under neutral and basic conditions (Ref. 1004)
NEAT : 3320, 2640, 1710, 1295, 1260, 1245, 1120, 1080, 1055, 1025, 975cm-1 (Ref. 1005)
1H-NMR(d6-ACETONE) : d 5.48(m, 4H), 4.05(m, 3H), 0.9(t, 3H, 20-CH3) (Ref. 1005). 13C-NMR : 176.6(C1), 135.0(C14), 132.8(C5), 129.1(C13 or C6), 128.9(C6 or C13), 77.2(C11), 72.9(C15), 71.8(C9), 55.0(C12), 49.9(C8), 42,6(C10), 36.8(C16), 33.2(C2), 31,5(C18), 26.3(C4), 25.1(C7), 25.1(C17), 24.5 (Ref. 1008)
354(M+), 336, 318, 292, 274, 264(100), 247, 229, 191, 177, 165, 137, 99, 81, 67 (Ref. 1009)


Prostaglandin F2a was found to be accummulating in human semen in an amount of about 2 microgram per ml (Ref. 0001). In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin F2a.
Prostaglandin F synthase reduces 9,11-endoperoxide of prostaglandin H2 requiring NADPH, and produces prostaglandin F2a. The same enzyme also reduces 9-keto group of prostaglandin D2 producing 11b-prostaglandin F2 (Ref. 0005).
cDNA for prostaglandin F synthase was cloned from bovine lung (Ref. 0005). cDNA for prostaglandin F2a receptor (FP) was cloned, and its 7ptransmembrane structure was reported (Ref. 0003).

17
PROSTAGLANDIN F3a
7-[3(R),5(S)-Dihydroxy-2(R)-(3(S)-hydroxyocta-1(E),5(Z)-dienyl)cyclopentan-1(R)-yl]-5(Z)-heptenoic acid / (5Z,8R,9S,11R,12R,13E,15S,17Z)-9,11,15-Trihydroxyprosta-5,13,17-trienoic acid
XPR1502
Shouzo Yamamoto
PGF3a
C20H32O5 352.465 Download ChemDraw structure file

[a]d-26=+29.6deg(C=0.54, TETRAHYDROFURAN) (Ref. 1114)
TETRAHYDROFURAN (Ref. 1114)

TRI-TMS ETHER, METHYL ESTER ; AMMONIA CI : m/e, 600(M+18), 585, 583(M+1), 510, 493, 420, 403 (Ref. 1117)


Prostaglandin F3a is found in bovine lung (Ref. 0083).



18
15-KETOPROSTAGLANDIN F2a
7-[3(R),5(S)-Dihydroxy-2(R)-(3-oxo-1(E)-octenyl)cyclopentan-1(R)-yl]-5(Z)-heptenoic acid
XPR1511
Shouzo Yamamoto
15-KETO-PGF2a
C20H32O5 352.465 Download ChemDraw structure file
It is well known that the biological activities of various prostaglandins are reduced upon their dehydrogenation at carbon-15 by the catalysis of 15-hydroxyprostaglandin dehydrogenase (Ref. 0044).




15-Keto-prostaglandin F2a is the oxidized product of prostaglandin F2a by 15-hydroxyprostaglandin dehydrogenase, which is present in lung, kidney, placenta and other tissues and catalyzes the NAD- or NADP-dependent dehydrogenation of 15-dydroxyl group (Ref. 0006).

15-Keto-prostaglandin F2a is further metabolized by its D13-reduction, b-oxidation and w oxidation. The ultimate metabolite is 5a,7a-dihydroxy-11-keto-tetranorprosta-1,16-dioic acid, and excreted in urine (Ref. 0047).
cDNA for placental 15-hydroxyprostaglandin dehydrogenase was cloned (Ref. 0046).

19
PROSTAGLANDIN Fa-MAJOR URINARY METABOLITE
8-[2(R)-(2-Carboxyethyl)-3(S),5(R)-dihydroxycyclopentan-1(R)-yl]-6-oxooctanoic acid
XPR1521
Shouzo Yamamoto
PGFa-MUM
C16H26O7 330.373 Download ChemDraw structure file


DIMETHYL ESTER DI-TMS ETHER ; m/e 502(M+), 487, 412, 397, 325, 322, 291, 254, 241, 228, 217, 191, 179, 143 (Ref. 1062)


When prostaglandin F2a was administered intravenously to female subjects, 5a,7a-dihydroxy-11-keto-tetranor-prosta-1,16-dioic acid was found as a major urinary metabolite (PGFa-MUM) (Ref. 0047).




20
PROSTAGLANDIN G2
7-[2(R)-(3(S)-Hydroperoxy-1(E)-octenyl)-1(R),4(S)-5,6-dioxabicyclo[2.2.1]-heptan-3(R)-yl]-5(Z)-heptenoic acid
XPR1601
Shouzo Yamamoto
PGG2
C20H32O6 368.464 Download ChemDraw structure file
Prostaglandin G2 is a metabolic intermediate, but the compound as such has biological activities of bronchoconstriction and vasoconstriction (Ref. 0013/0020).
13C-NMR : d 84.6(C15) (Ref. 1016)



Prostaglandin G2 is produced by bis-dioxygenation and cyclization of arachidonic acid as an intermediate for the biosyntheses of various prostaglandins and thromboxanes. The responsible enzyme is prostaglandin endoperoxide synthase usually referred to as fatty acid cyclooxygenase, and distributed in various animal tissues (Ref. 0015/0019).
Prostaglandin endoperoxide synthase is a bifunctional enzyme with an oxygenase activity (fatty acid cyclooxygenase) producing prostaglandin G2 from arachidonic acid and a peroxidase activity (prostagladnin hydroperoxidase) converting prostaglandin G2 to prostaglandin H2 (Ref. 0019). The enzyme is usually referred to briefly as cyclooxygenase. There are two isozymes of the enzyme. Cyclooxygenase-1 is a constitutive enzyme expressed in most mammalian cells, while cyclooxygenase-2 is a product of immediate early gene and is induced rapidly and transiently in certain types of cell by various bioactive compounds (Ref. 0004/0008).
cDNA and genomic DNA each for cyclooxygenas-1 and 2 were cloned (Ref. 0007).
Stability:unstable in water around neutrality with a half life of about 5 min at 37degC and decomposes to PGE2, PGD2, PGF2 and 12L-hydroxy-5,8,10-heptadecatrienoic acid(Ref. 0068).
21
PROSTAGALANDIN H2
7-[2(R)-(3(S)-Hydroxy-1(E)-octenyl)-1(R),4(S)-5,6-dioxabicyclo[2.2.1]heptan-3(R)-yl]-5(Z)-heptenoic acid
XPR1701
Shouzo Yamamoto
PGH2
C20H32O5 352.465 Download ChemDraw structure file
Prostaglandin H2 is a metabolic intermediate, but the compound as such is bioactive to aggregate platelets and to contract artery (Ref. 0013/0020).
CHLOROFORM, METHYLENE CHLORIDE, ETHYL ACETATE (Ref. 1018/1019)
METHYL ESTER:to be cited the Chart(Ref. 1018)
1H-NMR :to be cited the Chart(Ref. 1018). 13C-NMR(CD2Cl2) : 178.5(C1), 133.5, 130.4, 130,0, 128.4, 82.1, 79.6(C9 & C11), 72.7(C15), 50.4, 48.2, 42.4, 37.0, 33.1, 31.7, 26.9, 26.3, 25.1, 24.5, 22.7, 14.0 (Ref. 1019)
15-TRIMETHYLSILYL ETHER METHYL ETHER :to be cited the Chart(Ref. 1020)


Prostaglandin H2 is produced by 15-hydroperoxide reduction of prostaglandin G2 as an intermediate for the biosyntheses of various prostaglandins and thromboxanes. The responsible enzyme is prostaglandin endoperoxide synthase usually referred to as fatty acid cyclooxygenase, and distributed in various animal tissues (Ref. 0015/0019).
Prostaglandin endoperoxide synthase is a bifunctional enzyme with an oxygenase activity (fatty acid cyclooxygenase) producing prostaglandin G2 from arachidonic acid and a peroxidase activity (prostagladnin hydroperoxidase) converting prostaglandin G2 to prostaglandin H2 (Ref. 0019). The enzyme is usually referred to briefly as cyclooxygenase. There are two isozymes of the enzyme. Cyclooxygenase-1 is a constitutive enzyme expressed in most mammalian cells, while cyclooxygenase-2 is a product of immediate early gene and is induced rapidly and transiently in certain types of cell by various bioactive compounds (Ref. 0004/0008).
cDNA and genomic DNA each for cyclooxygenase-1 and 2 were cloned (Ref. 0007).
Stability:unstable in water around neutrality with a half life of about 5 min at 37degC and decomposes to PGE2, PGD2, PGF2 and 12L-hydroxy-5,8,10-heptadecatrienoic acid(Ref. 0068).
22
Prostaglandin A3
9-oxo-15S-hydroxy-prosta-5Z,10,13E,17Z-tetraen-1-oic acid
XPR1702
Takehiko Yokomizo
C20H28O4 332.434 Download ChemDraw structure file





PGA3 is non-enzymatic dehydration product of PGE3.




23
Prostaglandin B3
9-oxo-15S-hydroxy-prosta-5Z,8(12),13E,17Z-tetraen-1-oic acid
XPR1703
Takehiko Yokomizo
C20H28O4 332.434 Download ChemDraw structure file





PGB3 is a non-enzymatic dehydration product resulting from the treatment of PGE3 with strong base.




24
13,14-dihydro-15keto Prostaglandin D2
9a-hydroxy-11,15-dioxo-prost-5Z-en-1-oic acid
XPR1704
Takehiko Yokomizo
C20H32O5 352.465 Download ChemDraw structure file





13,14-dihydro-15keto PGD2 is a metabolite of PGD2 which is formed through the PG 15-dehydrogenase pathway.(Ref. 2003)




25
Prostaglandin D3
9a,15S-dihydroxy-11-oxo-prosta-5Z,13E,17Z-trien-1-oic acid
XPR1705
Takehiko Yokomizo
C20H30O5 350.449 Download ChemDraw structure file
PGD3 has almost same ability to decrease systemic blood pressure in rats and to decrease intraocular pressure in rabbits.(Ref. 2005/2006/2007) However, it is 3 to 5 times more potent than PGD2 in the inhibition of ADP-induced human platelet aggregation.<<




PGD3 is produced by the metabolism of EPA via the cyclooxygenase pathway.(Ref. 2004)




26
D17-Prostaglandin E1
9-oxo-11a,15S-dihydroxy-prosta-13E,17Z-dien-1-oic acid
XPR1706
Takehiko Yokomizo
C20H32O5 352.465 Download ChemDraw structure file
D17-PGE1 is about half as potent as PGE1 as an inhibitor of ADP-induced aggregation of rabbbit PRP.(Ref. 2008) In humanPRP, D17-PGE1 is a more potent antiplatelet agonist than PGE1.




D17-PGE1 is produced by the cyclooxigenase metabolism of w-3 arachidonic acid.




27
13,14-dihydro Prostaglandin E1
9-oxo-11a,15S-dihydroxy-prostan-1-oic acid
XPR1707
Takehiko Yokomizo
C20H36O5 356.497 Download ChemDraw structure file
13,14-dihydro PGE1 is an inhibitor of ADP-induced platelet aggregation in human PRP.









28
13,14-dihydro-15keto Prostaglandin E1
9,15-dioxo-11a-hydroxy-prostan-1-oic acid
XPR1708
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file
13,14-dihydro-15keto PGE1 is a week inhibitor of ADP-induced platelet aggregation in human PRP.




13,14-dihydro-15keto PGE1 is a metabolite of PGE1.(Ref. 2010/2011)




29
15-keto Prostaglandin E1
9,15-dioxo-11a-hydroxy-prost-13E-en-1-oic acid
XPR1709
Takehiko Yokomizo
C20H32O5 352.465 Download ChemDraw structure file
15-keto PGE1 has very slight biological activity compared to PGE1.(Ref. 2013)




15-keto PGE1 is the inactive metabolite of PGE1 via PG15-dehydrogenase




30
19(R)-hydroxy Prostaglandin E1
9-oxo-11a,15S,19R-trihydroxy-prost-13E-en-1-oic acid
XPR1710
Takehiko Yokomizo
C20H34O6 370.480 Download ChemDraw structure file
19(R)-hydroxy PGE1 has contractile activity on smooth muscle preparations.(Ref. 2014/2015)




19(R)-hydroxy PGE1 is the major prostaglandin found in the semen of primates.




31
5-trans Prostaglandin E2
9-oxo-11a,15S-dihydroxy-prosta-5E,13E-dien-1-oic acid
XPR1711
Takehiko Yokomizo
C20H32O5 352.465 Download ChemDraw structure file
5-trans PGE2 has 18 times potency in activating adenylate cyclase compared to PGE2.(Ref. 2017) 5-trans PGE2 accelerates fibrinolysis by enhancing plasminogen activation mediated dby tissue-type plasminogen activator.(Ref. 2018) And it also inhibits platelet




5-trans PGE2 is naturally produced by some gorgonian corals and is also a common impurity in commercial lots of PGE1.




32
13,14-dihydro-15keto Prostaglandin E2
9,15-dioxo-11a-hydroxy-prost-5Z-en-1-oic acid
XPR1712
Takehiko Yokomizo
C20H32O5 352.465 Download ChemDraw structure file





13,14-dihydro-15keto PGE2 is the primary metabolite of PGE2 in plasma via PG 15-dehydrogenase.(Ref. 2010)




33
19(R)-hydroxy Prostaglandin E2
9-oxo-11a,15S,19R-trihydroxy-prosta-5Z,13E-dien-1-oic acid
XPR1713
Takehiko Yokomizo
C20H32O6 368.464 Download ChemDraw structure file
19(R)-hydroxy PGE2 is a potent smooth muscle relaxant and a selective agonist for the EP2 receptor.(Ref. 2014/2015)









34
20-hydroxy Prostaglandin E2
9-oxo-11a,15S,20-trihydroxy-prosta-5Z,13E-dien-1-oic acid
XPR1714
Takehiko Yokomizo
C20H32O6 368.464 Download ChemDraw structure file





20-hydroxy PGE2 is a product of cytochrome P450 metabolism of PGE2.(Ref. 2019/2020)




35
6,15-diketo-13,14-dihydro Prostaglandin F1a
6,15-dioxo-9a,11a-dihydroxy-prostan-1-oic acid
XPR1715
Takehiko Yokomizo
C20H34O6 370.480 Download ChemDraw structure file
6,15-diketo-13,14-dihydro PGF1a is hown to enhance the intracellular cAMP and cholesterol catabolism in bovine arterial smooth muscle cells.(Ref. 2021)









36
D17-6-keto Prostaglandin F1a
6-oxo-9a,11a,15S-trihydroxy-prosta-13E,17Z-dien-1-oic acid
XPR1716
Takehiko Yokomizo
C20H32O6 368.464 Download ChemDraw structure file





D17-6-keto PGF1a is no enzymatic hydrolysis product of PGI3.




37
15-keto Prostaglandin F1a
9a,11a-dihydroxy-15-oxo-prost-13E-en-1-oic acid
XPR1717
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file
In fish, the 15-keto compounds (including 15-keto PGF1a) serve as post-ovulatory pheromones and are more active tha the parent prostaglandins.(Ref. 2022)




15-keto PGF1a is the initial metabolite of PGF1a via PG 15-dehydrogenase.




38
19(R)-hydroxy Prostaglandin F1a
9a,11a,15S,19R-tetrahydroxy-prost-13E-en-1-oic acid
XPR1718
Takehiko Yokomizo
C20H36O6 372.496 Download ChemDraw structure file





19(R)-hydroxy PGF1a is and w-1 hydroxylase metabolite of 19(R)-hydroxy PGF1a.(Ref. 2023)




39
11b-Prostaglandin F2a
9a,11b,15S-trihydroxy-prosta-5Z,13E-dien-1-oic acid
XPR1719
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file





11b-PGF2a is the primary plasma metabolite of PGD2 in vivo.(Ref. 2025)




40
13,14-dihydro-15-keto Prostaglandin F2a
9a,11a-dihydroxy-15-oxo-prost-5Z-en-1-oic acid
XPR1720
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file





13,14-dihydro-15-keto PGF2a is the first prominent plasma metabolite of PGF2a via PG 15-dehydrogenase pathway.(Ref. 2026)




41
15(R)-Prostaglandin F2a
9a,11a,15R-trihydroxy-prosta-5Z,13E-dien-1-oic acid
XPR1721
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file
15(R)-PGF2a has only quarter of the ability of PGF2a in hamster antifertility studies(Ref. 2027) due to reduced affinity for FP receptors.




15(R)-PGF2a is the C-15 epimer of the naturally occurring PGF2a.




42
19(R)-hydroxy Prostaglandin F2a
9a.11a,15S,19R-tetrahydroxy-prosta-5Z,13E-dien-1-oic acid
XPR1722
Takehiko Yokomizo
C20H34O6 370.480 Download ChemDraw structure file





19(R)-hydroxy PGF2a is an w-1 hydroxylase metabolite of PGF2a found in human semen.




43
20-hydroxy Prostaglandin F2a
9a,11a,15S,20-tetrahydroxy-prosta-5Z,13E-dien-1-oic acid
XPR1723
Takehiko Yokomizo
C20H34O6 370.480 Download ChemDraw structure file





20-hydroxy PGF2a is the w-oxidation product of PGF2a via P450 w-oxidation in cultured type-II alveolar cells from pregnant rabbits.(Ref. 2028)




44
Prostaglandin H1
9a,11a-epidioxy-15S-hydroxy-prost-13E-en-1-oic acid
XPR1724
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file
PGH1 is known as suicide substrate and inhibits platelet thromboxane synthase with a Ki of 28 mM.(Ref. 2029)




PGH1 is a cylooxygenase metabolige of DGLA.




45
Prostaglandin I3
6,9a-epoxy-11a,15S-dihydroxy-prosta-5Z,13E,17Z-trien-1-oic acid
XPR1725
Takehiko Yokomizo
C20H29O5 349.441 Download ChemDraw structure file
PGI3 has equal ability to PGI2 in inhibitting human platelet aggregation.(Ref. 2031)




PGI3 is synthesized from EPA by cyclooxygenase and PGI synthase.




46
D12-Prostaglandin J2
11-oxo-15S-hydroxy-prosta-5Z,9,12E-trien-1-oic acid
XPR1726
Takehiko Yokomizo
C20H30O4 334.450 Download ChemDraw structure file
D12-PGJ2 has antitumor and antibiral activity, inhibiting growth of cultured L1210 cells with an IC50 of 0.7 mg/ml.(Ref. 2033)




D12-PGJ2 is a decomposition product of PGD2 in the presence of albumin.(Ref. 2032)




47
15-epi Prostaglandin A1
9-oxo-15R-hydroxy-prostsa-10,13E-dien-1-oic acid
XPR1728
Takehiko Yokomizo
C20H32O4 336.466 Download ChemDraw structure file





15-epi PGA1 is produced by gorgonia soft corals.(Ref. 2000)




48
13,14-dihydro-15-keto Prostaglandin A2
9-oxo-15R-hydroxy-prostsa-10,13E-dien-1-oic acid
XPR1729
Takehiko Yokomizo
C20H30O4 334.450 Download ChemDraw structure file





13,14-dihydro-15-keto PGA2 is produced via non-enzymatic dehydration of 13,14-dihydro-15-keto PGE2, whose process is a ccelerated by the presence of albumin.(Ref. 2001/2002)




49
Prostaglandin D1
9a,15S-dihydroxy-11-oxo-prost-13E-en-1-oic acid
XPR1731
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file
Prostaglandin D1 inhibits ADP-induced human platelet aggregation effect (IC50 value of 320 ng/ml). (Ref. 2040)Prostaglandin D1 inhibits the increase in vascular permeability in rat skin produced by prostaglandin E1, E2 and D2.(Ref. 2073) PGD1 is equal in activity to PGF1 alpha in causing constriction of central and peripheral airways of the dog.(Ref. 2083)









50
15(S)-15-methyl Prostaglandin D2
9a,15S-dihydroxy-11-oxo-15-methyl-prosta-5Z,13E-dien-1-oic acid
XPR1732
Takehiko Yokomizo
C21H34O5 366.492 Download ChemDraw structure file
15(S)-15-methyl Prostaglandin D2 is reported to inhibit ADP-induce human platelet aggregation (IC50 value of 320 ng/ml) and increase systemic blood pressure in rat. (Ref. 2040)15(S)-15-methyl Prostaglandin D2 shows strong anti-fertility effect in hamster (100% at 50 mg/hamster).(Ref. 2040)









51
15-deoxy-D12.14-Prostaglandin D2
9a-hydroxy-11-oxo-prosta-5Z,12E,14E-trien-1-oic acid
XPR1733
Takehiko Yokomizo
C20H30O4 334.450 Download ChemDraw structure file
15-deoxy-D12.14-Prostaglandin D2 shows cytotoxity on murine leukemia cell line (IC50 value of 0.3 mg/ml).(Ref. 1047) 15-deoxy-D12.14-Prostaglandin D2 is a potent activator of eosinophils, inducing calcium mobilization, actin polymerization, and CD11b expression.(Ref. 2074)
lmax=296nm e296=18300



PGD2 and other metabolites are separated with HPLC. Please reffer following paper.(Ref. 2084)


15-deoxy-D12.14-Prostaglandin D2 is formed from Prostaglandin D2 via D12-Prostaglandin D2. This reaction is proceeded under co-culture with Prostaglandin D2 and serum.(Ref. 2084)


52
16,16-dimethyl Prostaglandin D2
9a,15R-dihydroxy-11-oxo-16,16-dimethyl-prosta-5Z,13E-dien-1-oic acid
XPR1734
Takehiko Yokomizo
C22H36O5 380.518 Download ChemDraw structure file
16,16-dimethyl Prostaglandin D2 enhances ADP-induce human platelet aggregation and increase increase systemic blood pressure in rat. (Ref. 2040)









53
Prostaglandin E1 Alcohol
1,11a,15S-trihydroxy-prost-13E-en-9-one
XPR1735
Takehiko Yokomizo
C20H36O4 340.497 Download ChemDraw structure file
Prostaglandin E1 Alcohol shows bronchodialational effect on human respiratory tract muscle.(Ref. 2042)Prostaglandin E1 Alcohol shows agnoist effects selectively for EP2 and EP4.(Ref. 2085)Prostaglandin E1 Alcohol inhibits M-CSF synthesis by bone marrow stromal cells.(Ref. 2086)









54
11-deoxy Prostaglandin E1
9-oxo-15S-hydroxy-prosto-13E-en-1-oic acid
XPR1736
Takehiko Yokomizo
C20H34O4 338.482 Download ChemDraw structure file
11-deoxy Prostaglandin E1 shows spieces and subtype dependent EP agonistic effect. In guinea pig, 11-deoxy Prostaglandin E1 induce bronchodilation and vasodepression. (Ref. 2043) 11-deoxy Prostaglandin E1 is reported to increase cAMP release via EP receptors in Jurkat cells. (Ref. 2079) The Ki value of each murine EPs is 600 nM (EP1), 45 nM (EP2), 1.1 nM (EP3), 23 nM (EP4) .(Ref. 2036) 11-deoxy Prostaglandin E1, a selective EP2/EP3/EP4 agonist, inhibites IL-1beta-induced IL-6 production in human gingival fibroblast.(Ref. 2089) 11-deoxy Prostaglandin E1 stimulates K secretion through EP2 receptors at EC50 values of 8.3 nM in guinea pig distal colonic mucosa .(Ref. 2090)









55
15(R)-Prostaglandin E1
9-oxo-11a,15R-dihydroxy-prost-13E-en-1-oic acid
XPR1737
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file
15(R)-Prostaglandin E1 dosen't have biological significance but inhibit 15-hydroxy PGDH (IC50 value of 189 mM).(Ref. 2044)









56
15(S)-15-methyl Prostaglandin E1
9-oxo-11a,15S-dihydroxy-15-methyl-prost-13E-en-1-oic acid
XPR1738
Takehiko Yokomizo
C21H36O5 368.508 Download ChemDraw structure file
15(S)-15-methyl Prostaglandin E1 shows weak constriction effect on human respiratory tract smooth muscle.(Ref. 2045)15(S)-15-methyl Prostaglandin E1 at 300 ng/kg administered systemically (subcutaneously), selectively suppresses PMN-dependent edema formation.(Ref. 2078) In hamsters, 15(S)-15-methyl Prostaglandin E1 of 150 micrograms reduced the number of PMNLs adherent to blood vessels and infiltrating the ICT (infiltrated connective tissue) and other inflammation.(Ref. 2091)









57
16,16-dimethyl Prostaglandin E1
9-oxo-11a,15R-dihydroxy-16,16-dimethyl-prost-13E-en-1-oic acid
XPR1739
Takehiko Yokomizo
C22H38O5 382.534 Download ChemDraw structure file
16,16-dimethyl Prostaglandin E1 shows vascular constriction in human.(Ref. 2045) 16,16-dimethyl Prostaglandin E1 inhibited electrically evoked [3H]norepinephrine (NE) overflow from the isolated, superfused rabbit iris-ciliary body without affecting basal tritium efflux.(Ref. 2092)









58
9-deoxy-9-methylene Prostaglandin E2
9-methylene-11a,15S-dihydroxy-prosta-5Z,13E-dien-1-oic acid
XPR1740
Takehiko Yokomizo
C21H34O4 350.492 Download ChemDraw structure file
9-deoxy-9-methylene Prostaglandin E2 decreases blood pressure in rat and (Ref. 2047)









59
9-deoxy-9-methylene-16,16-dimethyl Prostaglandin E2
9-methylene-11a,15R-dihydroxy-16,16-dimethyl-prosta-5Z,13E-dien-1-oic acid
XPR1741
Takehiko Yokomizo
C23H38O4 378.545 Download ChemDraw structure file
9-deoxy-9-methylene-16,16-dimethyl Prostaglandin E2 shows term dependent termination of pregnant in conbination with other PGs.(Ref. 2048)









60
11b-Prostaglandin E2
9-oxo-11b,15S-dihydroxy-prosta-5Z,13E-dien-1-oic acid
XPR1742
Takehiko Yokomizo
C20H32O5 352.465 Download ChemDraw structure file
11b-Prostaglandin E2 induces bone resorption at 10-8 ~ 10-6 M in rats.(Ref. 2049)









61
11-deoxy Prostaglandin E2
9-oxo-15S-hydroxy-prosta-5Z,13E-dien-1-oic acid
XPR1743
Takehiko Yokomizo
C20H32O4 336.466 Download ChemDraw structure file
11-deoxy Prostaglandin E2 shows strong bronchoconstriction of human smooth muscle .(Ref. 2045)









62
11-deoxy-16,16-dimethyl Prostaglandin E2
9-oxo-15R-hydroxy-16,16-dimethyl-prosta-5Z,13E-dien-1-oic acid
XPR1744
Takehiko Yokomizo
C22H36O4 364.519 Download ChemDraw structure file
In rat, 11-deoxy-16,16-dimethyl Prostaglandin E2 inhibits secretion of gastric acid secretion so that suppresses ulcer formation.(Ref. 2050) 11-deoxy-16,16-dimethyl Prostaglandin E2 contracts human resporatory tract smooth muscle.(Ref. 2045)









63
15(R)-15-methyl Prostaglandin E2
9-oxo-11a,15R-dihydroxy-15-methyl-prosta-5Z,13E-dien-1-oic acid
XPR1745
Takehiko Yokomizo
C21H34O5 366.492 Download ChemDraw structure file
15(R)-15-methyl Prostaglandin E2 shows increase of bicarbonate secretion in duodenum and inhibition of gastric acid secretion.(Ref. 2051)









64
15(S)-15-methyl Prostaglandin E2
9-oxo-11a,15S-dihydroxy-15-methyl-prosta-5Z,13E-dien-1-oic acid
XPR1746
Takehiko Yokomizo
C21H34O5 366.492 Download ChemDraw structure file
15(S)-15-methyl Prostaglandin E2 inhibits gastric acid secretion and consequent ulcer formation.(Ref. 2052)









65
16,16-dimethyl Prostaglandin E2
9-oxo-11a,15R-dihydroxy-16,16-dimethyl-prosta-5Z,13E-dien-1-oic acid
XPR1747
Takehiko Yokomizo
C22H36O5 380.518 Download ChemDraw structure file
16,16-dimethyl Prostaglandin E2 shows cervical ripening and uterine constriction and consequent inhibition of ulcer formation.(Ref. 2041/2046) 16,16-dimethyl Prostaglandin E2 increases eNOS mRNA expression of adult microvessels to values in the newborn pig.(Ref. 2076) 16,16-dimethyl Prostaglandin E2 prevents indomethacin-induced gastric lesions.(Ref. 2080)









66
16-phenyl tetranor Prostaglandin E2
9-oxo-11a,15S-dihydroxy-16-phenyl-17,18,19,20-tetranor-prosta-5Z13E-dien-1-oic acid
XPR1748
Takehiko Yokomizo
C22H28O5 372.455 Download ChemDraw structure file
16-phenyl tetranor Prostaglandin E2 induces hypotation in dogs and inhibit bronchoconstriction induced by histamine.(Ref. 2053)









67
17-phenyl trinor Prostaglandin E2
9-oxo-11a,15S-dihydroxy-17-phenyl-18,19,20-trinor-prosta-5Z13E-dien-1-oic acid
XPR1749
Takehiko Yokomizo
C23H30O5 386.481 Download ChemDraw structure file
17-phenyl trinor Prostaglandin E2 shows constriction of the guinea pig ileum and strong anti-fertility effect in hamster.(Ref. 2054)









68
11-deoxy Prostaglandin F1a
9a,15S-dihydroxy-prost-13E-en-1-oic acid
XPR1750
Takehiko Yokomizo
C20H36O4 340.497 Download ChemDraw structure file
11-deoxy Prostaglandin F1a shows inhibits gastric acid secretion and induces uterine constriction. (Ref. 2055/2056) 11-deoxy Prostaglandin F1a shows vasopression and bronchoconstriction effect in guinea pig.(Ref. 2043)









69
Prostaglandin F1b
9b,11a,15S-trihydroxy-prost-13E-en-1-oic acid
XPR1751
Takehiko Yokomizo
C20H36O5 356.497 Download ChemDraw structure file
Prostaglandin F1b increase respiratory rate after application intravenously.(Ref. 2057)









70
11-deoxy Prostaglandin F1b
9b,15S-dihydroxy-prost-13E-en-1-oic acid
XPR1752
Takehiko Yokomizo
C20H36O4 340.497 Download ChemDraw structure file
11-deoxy Prostaglandin F1b shows vasodepression and bronchodilationeffect in guinea pig.(Ref. 2043)









71
Prostaglandin F2a 1,11-lactone
9a,11a,15S-trihydroxy-prosta-5Z,13E-dien-1-oic acid, 1,11-lactone
XPR1753
Takehiko Yokomizo
C20H32O4 336.466 Download ChemDraw structure file
Prostaglandin F2a 1,11-lactone shows reduction of vasoacitivity and anti-fertility effect.(Ref. 2058)









72
Prostaglandin F2a 1,15-lactone
9a,11a,15S-trihydroxy-prosta-5Z,13E-dien-1-oic acid, 1,15-lactone
XPR1754
Takehiko Yokomizo
C20H32O4 336.466 Download ChemDraw structure file
Prostaglandin F2a 1,15-lactone terminates pregnancy at early stage.(Ref. 2059)









73
Prostaglandin F2a Alcohol methyl ether
1-methyl-9a,11a,15S-trihydroxy-prosta-5Z,13E-diene
XPR1755
Takehiko Yokomizo
C21H38O4 354.524 Download ChemDraw structure file
Prostaglandin F2a Alcohol methyl ether shows hypotensive effect in ocular.(Ref. 2060)









74
Prostaglandin F2a dimethyl amide
N,N-dimethyl-9a,11a,15S-trihydroxy-prosta-5Z,13E-dien-1-amide
XPR1756
Takehiko Yokomizo
C22H39O4 367.543 Download ChemDraw structure file
Prostaglandin F2a dimethyl amide shows inhibition of PGF2a -induced contraction in gerbil colon.









75
Prostaglandin F2a Ethanolamide
N-(2-hydroxyethyl)-9a,11a,15S-trihydroxy-prosta-5Z,13E-dien-1-amide
XPR1757
Takehiko Yokomizo
C22H39NO5 397.549 Download ChemDraw structure file
Prostaglandin F2a Ethanolamide shows dialation effect in cat iris sphincter.(Ref. 2062)









76
Prostaglandin F2a isopropyl ester
9a,11a,15S-trihydroxy-prosta-5Z,13E-dien-1-oic acid, isopropyl ester
XPR1758
Takehiko Yokomizo
C23H40O5 396.561 Download ChemDraw structure file
Prostaglandin F2a isopropyl ester is easily hydrolyzed into PGF2a and reduces intraocular pressure after admiration into eyes.(Ref. 2063)









77
5-trans Prostaglandin F2a
9a,11a,15S-trihydroxy-prosta-5E,13E-dien-1-oic acid
XPR1759
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file
5-trans Prostaglandin F2a shows incease of respiratory rate in rabbit.(Ref. 2057)









78
11-deoxy Prostaglandin F2a
9a,15S-dihydroxy-prosta-5Z,13E-dien-1-oic acid
XPR1760
Takehiko Yokomizo
C20H34O4 338.482 Download ChemDraw structure file
11-deoxy Prostaglandin F2a shows smooth muscle contraction effect in rabbit aorta, dog saphenous vein, guinea pig trachea.(Ref. 2064)









79
13,14-dihydro Prostaglandin F2a
9a,11a,15S-trihydroxy-prost-5Z-en-1-oic acid
XPR1761
Takehiko Yokomizo
C20H36O5 356.497 Download ChemDraw structure file
13,14-dihydro Prostaglandin F2ainduce leuteolysis in hamster.(Ref. 2034)









80
15(S)-15-methyl Prostaglandin F2a
9a,11a,15S-trihydroxy-15-methyl-prosta-5Z,13E-dien-1-oic acid
XPR1762
Takehiko Yokomizo
C21H36O5 368.508 Download ChemDraw structure file
Intramuscularly injection of 15(S)-15-methyl Prostaglandin F2a induce abortion.(Ref. 2067) 15(S)-15-methyl Prostaglandin F2a causes sustained contractions in human vascular smooth muscle tissues (fetal aorta and arterial smooth muscle from chorionic vessels).(Ref. 2077)15(S)-15-methyl Prostaglandin F2a shows reduction of serum progesterone and induction of luteolysis in non-pregnant animal.(Ref. 2065)









81
17-phenyl trinor Prostaglandin F2a
9a,11a,15S-trihydroxy-17-phenyl-18,19,20-trinor-prosta-5Z,13E-dien-1-oic acid
XPR1763
Takehiko Yokomizo
C23H32O5 388.497 Download ChemDraw structure file
17-phenyl trinor Prostaglandin F2a reduces the intraocular pressure in the cat eye.(Ref. 2038)









82
Prostaglandin F2b
9b,11a,15S-trihydroxy-prosta-5Z,13E-dien-1-oic acid
XPR1764
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file
Prostaglandin F2b shows bronchodialation effect in guinea pig and cat.(Ref. 2069)









83
16,16-dimethyl Prostaglandin F2b
9b,11a,15R-trihydroxy-16,16-dimethyl-prosta-5Z,13E-dien-1-oic acid
XPR1765
Takehiko Yokomizo
C22H38O5 382.534 Download ChemDraw structure file
16,16-dimethyl Prostaglandin F2b reduce asthmatic bronchospasm.(Ref. 2070)









84
15-deoxy-D12.14-Prostaglandin J2
11-oxo-prosta-5Z,9,12E,14Z-tetraen-1-oic acid
XPR1766
Takehiko Yokomizo
C20H28O3 316.435 Download ChemDraw structure file
15-deoxy-D12.14-Prostaglandin J2 induces lipogenesis and adipocyte differentiation in cultured cell line.(Ref. 2035) 15-deoxy-D12.14-Prostaglandin J2 shows powerful proapoptotic effects by inhibiting I kappa B alpha degradation.(Ref. 2075)









85
16,16-dimethyl Prostaglandin A1
9-oxo-15R-hydroxy-16,16-dimethyl-prosta-10,13E-dien-1-oic acid
XPR1767
Takehiko Yokomizo
C22H36O4 364.519 Download ChemDraw structure file
16,16-dimethyl Prostaglandin A1 shows inhibition against infection of HSV and HIV-1 at the ID50 of 3.8-7.3 and 2.5 mg/ml respectively. (Ref. 2039) 16,16-dimethyl Prostaglandin A1 shows dose-dependent inhibition in growth of human oral squamous carcinoma cells.(Ref. 2071) 16,16-dimethyl Prostaglandin A1 shows cell cycle arrest at the G1/S phase due to nhibiting DNA synthesis. (Ref. 2081)
16,16-dimethyl Prostaglandin A1 is soluble in organic solvents (i.e. methyl acetate, DMSO, ethanol) at least 50 mg/ml and also in aqueous buffers or isotonic saline at least 2 mg/ml. But in basic solutions (pH >7.4) 16,16-dimethyl Prostaglandin A1 will be converted into 16,16-dimethyl Prostaglandin PGB1.
lmax=216nm e216=13000




16,16-dimethyl Prostaglandin A1 is a metabolism resistant analogue of PGA1.

16,16-dimethyl Prostaglandin A1 is a metabolism resistant analogue of PGA1.


86
16,16-dimethyl Prostaglandin A2
9-oxo-15R-hydroxy-16,16-dimethyl-prosta-5Z,10,13E-trien-1-oi acid
XPR1768
Takehiko Yokomizo
C22H34O4 362.503 Download ChemDraw structure file
16,16-dimethyl Prostaglandin A2 shows inhibitory effect on the proliferation of Sendai virus in monkey cells.(Ref. 1053) 16,16-dimethyl Prostaglandin A2 significantly increases mouse survival against nfection with influenza A by an average of 40% and decreases virus titers in the lungs without alteration of the host immune response.(Ref. 2082)
16,16-dimethyl Prostaglandin A2 is soluble in organic solvents (i.e. methyl acetate, DMSO, ethanol) at least 50 mg/ml and also in aqueous buffers or isotonic saline at least 2.4 mg/ml. But in basic solutions (pH >7.4) 16,16-dimethyl Prostaglandin A2 will be converted into 16,16-dimethyl Prostaglandin PGB2.
lmax=215nm e216=12200









87
16,16-dimethyl Prostaglandin A2 methyl ester
9-oxo-15R-hydroxy-16,16-dimethyl-prosta-5Z,10,13E-trien-1-oi acid, methyl ester
XPR1769
Takehiko Yokomizo
Download ChemDraw structure file
16,16-dimethyl Prostaglandin A2 methyl ester shows increase of survival from influenza A virus in infected mice (10 mg/day). Daily treatment of mice with 16,16-dimethyl Prostaglandin A2 methyl ester delayed tumour appearance, inhibited tumour growth and increased the survival time by 15-35%.(Ref. 2072)









88
d12-Prostaglandin D2
9a,15S-dihydroxy-11-oxo-prosta-5Z,12E-dien-1-oic acid
XPR1771
Takehiko Yokomizo
C20H32O5 352.465 Download ChemDraw structure file
d12-PGD2 is catalyzed to d12-PGJ2, which has antimitotic and carcinogenic activities.(Ref. 2142)(Ref. 2143)









89
15(R)-Prostaglandin D2
9a,15R-dihydroxy-11-oxo-prosta-5E,13E-dien-1-oic acid
XPR1772
Takehiko Yokomizo
C20H32O5 352.465 Download ChemDraw structure file
15(R)-PGD2 is reported to have potent agonistic effect to the DP2 receptor 5 time higher than PGD2.(Ref. 2144)









90
11-deoxy-11-methylene Prostaglandin D2
9a,15S-dihydroxy-11-methylene-prosta-5Z,13E-dien-1-oic acid
XPR1773
Takehiko Yokomizo
C21H34O4 350.492 Download ChemDraw structure file
11-deoxy-11-methylene PGD2 has been reported to be essentially without agonist activity on human platelets, a DP receptor assay.(Ref. 2145)









91
11-deoxy-11-methylene-15-keto Prostaglandin D2
9a-hydroxy-11-methylene-15-oxo-prosta-5Z,13E-dien-1-oic acid
XPR1774
Takehiko Yokomizo
C21H32O4 348.476 Download ChemDraw structure file
PGD2 has been reported to have two receptors, DP1 and CRTH2. The latter was recently identified on human eosinophils, and 11-deoxy-11methylene-15-keto PGD2 ischemically stable ligand for this receptor.(Ref. 2146)









92
15(R)-15-methyl Prostaglandin D2
9a,15R-dihydroxy-11-oxo-15methyl-prosta-5Z.13E-dien-1-oic acid
XPR1775
Takehiko Yokomizo
C21H34O5 366.492 Download ChemDraw structure file
15(R)-15-methyl PGD2 is reported as a potent selective agonist for the DP2 and CRTH2 and induce CD11b expression, actin polymerization, and chemotaxis in eosinophyils.(Ref. 2147)









93
11b-Prostaglandin E1
9-oxo-11b,15S-dihydroxy-prost-13E-en-1-oic acid
XPR1776
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file
11b-PGE1 is reported to contract the rat uterus and guinea pig ileum with less potent activity.(Ref. 2148)









94
8-iso Prostaglandin E1
9-oxo-11a,15S-dihydroxy-(8b)-prost-13E-en-1-oic acid
XPR1777
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file
8-iso PGE1 is reported as a pulmonary vasoconstrictor in anesthetized dogs at similar concentration to PGF2a.(Ref. 2150)




8-iso PGE1 is an isoprostane which is found in human semen at the concentration of 7 mg/ml.(Ref. 2149)




95
1a,1b-dihomo Prostaglandin E1
9-oxo-11a,15S-dihydroxy-1a,1b-dihomo-prost-13E-en-1-oic acid
XPR1778
Takehiko Yokomizo
C22H38O5 382.534 Download ChemDraw structure file
1a,1b-dihomo PGE1 is produced during incubation of whole sheep seminal vessels but not in human. 1a,1b-dihomo PGE1 has been reported the activity in ex vivo preparations of rat aorta and rat PRP.(Ref. 2151)









96
15(R)-Prostaglandin E2
9-oxo-11a,15R-dihydroxy-prosta-5Z,13E-dien-1-oic acid
XPR1779
Takehiko Yokomizo
C20H32O5 352.465 Download ChemDraw structure file
15(R)-PGE2 is shown to inhibito fertility at a dose of 1.0 mg in hamsters.(Ref. 2152)









97
8-iso Prostaglandin E2
9-oxo-11a,15S-dihydroxy-(8b)-prosta-5Z,13E-dien-1-oic acid
XPR1780
Takehiko Yokomizo
C20H32O5 352.465 Download ChemDraw structure file
8-iso PGE2 inhibits U-46619 or I-BOP-induced platelet aggregation with IC50 values of 0.5 and 5 mM.(Ref. 2153) 8-iso PGE2 is also reported to decrease 80% of the GFR and renal plasma flow without affecting blood pressure in infusing into the renal artery of rats.(Ref. 2154)









98
Prostaglandin F1b
9b,11a,15S-trihydroxy-prost-13E-en-1-oic acid
XPR1781
Takehiko Yokomizo
C20H36O5 356.497 Download ChemDraw structure file
PGF1b has been reported to show enhance respiratory rate in experimental animals after intravenous application.(Ref. 2155)









99
11-deoxy Prostaglandin F1b
9b,15S-dihydroxy-prost-13E-en-1-oic acid
XPR1782
Takehiko Yokomizo
Download ChemDraw structure file
11-deoxy PGF1b shows vasodepressor and bronchodilator activities in guinea pigs at a dose of 500 mg/kg.(Ref. 2156)









100
Prostaglandin F2a Alcohol
1,9a,11a,15S-tetrahydroxyprosta-5Z,13E-dien
XPR1783
Takehiko Yokomizo
C20H36O4 340.497 Download ChemDraw structure file
PGF2a Alcohol is reported to retain ocular hypotensive properties (Ref. 2157), but the target receptor is not cleared yet.(Ref. 2158)









101
Prostaglandin F2a dimethyl amine
1-dimethylamino-9a,11a,15S-trihydroxy-prosta-5Z,13E-diene
XPR1784
Takehiko Yokomizo
C22H4NO3 330.272 Download ChemDraw structure file
PGF2a is shown to inhibit the contractile effects of PGF2a by60% at 6 ng/ml.(Ref. 2159)









102
Prostaglandin F2a methyl ester
9a,11a,15S-trihydroxy-prosta-5Z,13E-dien-1-oic acid, methyl ester
XPR1785
Takehiko Yokomizo
C21H36O5 368.508 Download ChemDraw structure file
PGF2a methyl ester is reported to have higher ocular hypotensive activity than PGF2a with application to eyes of cats at 2.5 mg of dose.(Ref. 2093)









103
15(R)-Prostaglandin F2a
9a,11a,15R-trihydroxy-prosta-5Z,13E-dien-1-oic acid
XPR1787
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file
In hamster antifertility study, 15(R)-PGF2a is reported quarter potency of PGF2a, which is due to reduced affinity to FP receptors.(Ref. 2152)









104
8-iso Prostaglandin F2a
9a,11a,15S-trihydroxy-(8b)-prosta-5Z,13E-dien-1-oic acid
XPR1788
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file
8-iso PGF2a is reported to inhibit platelet aggregation induced by U-46619 (1 mM) and I-BOP (0.3 mM) with IC50 of 1.6 mM and 1.8 mM, respectively.(Ref. 2094)




In normal human urine, 8-iso PGF2a level are about 180-200 pg/mg of creatinine.(Ref. 2095)




105
8-iso-13,14-dihydro-15-keto Prostaglandin F2a
9a,11a-dihydroxy-15-oxo-(8b)-prost-5Z-en-1-oic acid
XPR1789
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file
8-iso-13,14-dihydro-15-keto PGF2a weakly has been reported to inhibit the U-46619 or collagen-induced platelet aggregation.(Ref. 2096)









106
8-iso-15-keto Prostaglandin F2a
9a,11a-dihydroxy-15-oxo-(8b)-prosta-5Z,13E-dien-1-oic acid
XPR1790
Takehiko Yokomizo
C20H32O5 352.465 Download ChemDraw structure file
In vasoconstriction studies, 8-iso-15-keto PGF2a has been reported as a membern of vasoconstrictor on the rato isolated thoraacic aorta through TP receptor.(Ref. 2097)









107
20-ethyl Prostaglandin F2a
9a,11a-15S-trihydroxy-20a,20b-dihomoprosta-5Z,13E-dien-1-oic acid
XPR1791
Takehiko Yokomizo
C22H38O5 382.534 Download ChemDraw structure file
20-ethyl PGF2a is considered as an intraocular hypotensive agent compared to unoprostone, due to the natural15(S) allylic hydroxyl in the lower side chain.









108
15(R)-15-methyl Prostaglandin F2a
9a,11a,15R-methyl-prosta-5Z,13E-dien-1-oic acid
XPR1792
Takehiko Yokomizo
C21H36O5 368.508 Download ChemDraw structure file
15(R)-15-methyl PGF2a is converted into the active 15(S)-isomer, which induce luteolysis after injection in rhesus monkeys at a dose of 12 mg/animal.(Ref. 2098)









109
15(S)-15-methyl Prostaglandin F2a methyl ester
9a,11a,15S-trihydroxy-15-methyl-prosta-5Z,13E-dien-1-oic acid, methyl ester
XPR1793
Takehiko Yokomizo
C22H38O5 382.534 Download ChemDraw structure file
15(S)-15methyl PGF2a methylester is hydrolysed in vivo to 15(S)-15-methyl PGF2a shown as a potent uterine stimulant and abortifacient.<<>><<>><<>>









110
17-phenyl trinor Prostaglandin F2a amide
9a,11a,15S-trihydroxy-17-phenyl-18,19,20-trinor-5Z,13E-dien-1-amide
XPR1794
Takehiko Yokomizo
C23H33NO4 387.512 Download ChemDraw structure file
17-phenyl trinor PGF2a amide is expected to show the typical intraocular effects of latanoprost. In vivo study revlealed that 17-phenyl trinor PGF2a amide was converted the amides of various PGs to the free acids.(Ref. 2102)









111
17-phenyl trinor Prostaglandin F2a isopropyl ester
9a,11a,15S-trihydroxy-17-phenyl-18,19,20-trinor-prosta-5Z,13E-dien-1-oic acid, isopropyl ester
XPR1795
Takehiko Yokomizo
C26H38O5 430.577 Download ChemDraw structure file
In the monky, 17-phenyl trinor PGF2a isopropyl ester shows the most potent activity in reducing IOP, lowering the IOP 1.3 mmHg below the level achieved by latanoprost at the dose of 3 mg/eye.<<>>









112
8-iso Prostaglandin F2b
9b,11a,15S-trihydroxy-(8b)-prosta-5Z,13E-dien-1-oic acid
XPR1796
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file
8-iso PGF2b has been reported to show very weak contraction of human umbilical vein artery and does not promote aggregation of human whole blood.(Ref. 2104)(Ref. 2096)









113
8-iso Prostaglandin F3a
9a,11a,15S-trihydroxy-(8b)-prosta-5Z,13E,17Z-trien-1-oic acid
XPR1797
Takehiko Yokomizo
C20H32O5 352.465 Download ChemDraw structure file
There is only one report on 8-iso PGF3a showing inactive in a TP receptor mediated assay of human platelet shape change, where 8-iso PGF2a has an ED50 value of 1 mM.(Ref. 2105)









114
Prostaglandin H2
9a,11a-epidioxy-15S-hydroxy-prosta-5Z,13E-dien-1-oic acid
XPR1798
Takehiko Yokomizo
C20H32O5 352.465 Download ChemDraw structure file
PGH2 was firstly reported as a potent vasoconstrictor.(Ref. 2106) And PGH2 has been reported as a TP receptor agonist which irreversibly aggregates huma platelets at 50-100 ng/ml and also as a suicide substrate for platelet TX synthase prosessing a Ki value of 18 mM .(Ref. 2107)









115
6a-Prostaglandin I1
6R,9a-epoxy-11a,15S-dihydroxy-prost-13E-en-1-oic acid
XPR1799
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file
6a-PGI1 is reported to promote cAMP accumulation in human thyroied slices and cells in a concentration dependent manner.(Ref. 2108) And also exhibits 6a-PGI1 inhibition of ADP-induced platelet aggregation at the IC50 value of 350 ng/ml.(Ref. 2109)









116
6b-Prostaglandin I1
6S,9a-epoxy-11a,15S-dihydroxy-prost-13E-en-1-oic acid
XPR1800
Takehiko Yokomizo
C20H34O5 354.481 Download ChemDraw structure file
6b-PGI1 has a Kact for adenylate cyclase in NCB-20 cells of 4.2 mM compared with 18 nM for PGI2.(Ref. 2110)









117
PROSTAGLANDIN I2
5(Z)-[7(R)-Hydroxy-6(R)-(3(S)-hydroxyocten-1(E)-yl)-1(S),5(R)-2-oxabicyclo[3.3.0]oct-3-ylidenpentanoic acid
XPR1801
Shouzo Yamamoto
PGI2
C20H32O5 352.465 Download ChemDraw structure file
Prostaglandin I2 is a potent anti-aggregatory agent for platelets, relaxes blood vessels, and enhances vascular permeability (Ref. 0014). It binds to a receptor with 7 transmembrne domains (IP) coupled to a Gs protein (Ref. 0003).
[a]D=78deg(C=0.8820, CHCl3) (Ref. 1014)
METHYL ESTER ; LIQUID MELT n 3370, 1740, 1695cm-1 (Ref. 1014)
1-H-NMR(D2O, GLYCINE BUFFER, pH10.4) : d 5.60(m, 2H, 13,14-CH), 4.66(m, 1H, 9-CH), 4.39(t, 1H, 5-CH), 4.15(q, 1H, 15-CH), 3.97(q, 1H, 11-CH), 2.20(t, 2H, 2-CH2) (Ref. 1013)
11,15-BIS(TRIMETHYLSILYL) ETHER METHYL ESTER ; 495(M+-CH3), 479, 439, 423, 349, 327, 323, 315, 313, 199, 173 (Ref. 1014)


In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin I2. Prostaglandin I2 is produced in blood vessels, lung and other tissues (Ref. 0013).
Prostaaglandin I2 is produced by isomerization of 9,11-endoperoxide of prostaglandin H2 by the catalysis of prostaglandin I synthaase (Ref. 0015/0016). Prostaglandin I2 is unstable and decomposes readily to 6-keto-prostaglandin F2a. Its 2,3-dinor derivative is a major urinary metabolite (Ref. 0017).
cDNA (Ref. 0016) and genomic DNA (Ref. 0018) for prostaglandin I synthase were cloned. cDNA for IP was isolated (Ref. 0003).
Stability:unstable in water around neutrality with a half life of about 5 min at 37degC and decomposes to 6-keto-PGF1a(Ref. 0011).
118
6-KETOPROSTAGLANDIN F1a
7-[3(R),5(S)-Dihydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)cyclopentan-1(R)-yl]-6-oxoheptanoic acid
XPR1811
Shouzo Yamamoto
6-KETO-PGF1a
C20H36O6 372.496 Download ChemDraw structure file
Degradation of prostaglandin I2 to 6-keto-prostaglandin F1a brings about the loss of biological activities. For example, the hypotensive effect of prostaglandin I2 is at least 100 times mor active than 6-keto-prostaglandin F1a (Ref. 0013).
[a]d-21= -9.6deg (C=1.04 METHANOL) (Ref. 1053)
DIETHYL ETHER(Ref. 1052)METHANOL, ACETONE, ETHYL ACETATE (Ref. 1053)
NEAT: n 3400, 1715, 1245, 1045, 975, 915, 875, 845, 800, 730 cm-1 (Ref. 1053)
1H-NMR(ACETONE-D6) : d 6.1-5.4(bs, 4H), 5.5-5.2(m, 2H), 4.7-3.5(m, 3H), 2.5-1.1 (m, 22H), 0.86(t, 3H) (Ref. 1053)
METHYL ESTER ; 366(M+-18), 348, 335, 330, 323, 319, 279, 265, 223, 196, 195, 164, 143, 121, 111, 99, 95, 71 (Ref. 1053). DIRECT EXPOSURE AMMONIA CI POSITIVE : 370, 353, 244, 163, 153, 136. NEGATIVE : 368, 351, 334, 316, 225, 219, 166, 135, 127 (Ref. 1054)


When prostaglandin I2 is produced in animal tissues, it is unstable in aqueous solution, especially at acidic pH, and readily decomposed to 6-keto-prostaglandin F1a (Ref. 0013). Therefore, 6-keto-prostaglandin F1a is detected where prostaglandin I2 is produced.
6-Keto-prostaglandin F1a is subjected to b-oxidation, and converted to 2,3-dinor-6-keto-prostaglandin F1a which appears in urine as a major metabolite (Ref. 0017).


119
2,3-DINOR-6-KETOPROSTAGLANDIN F1a
5-[3(R),5(S)-Dihydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)cyclopentan-1(R)-yl]-4-oxopentanoic acid
XPR1821
Shouzo Yamamoto
2,3-DINOR-6-KETO-PGF1a
C18H32O6 344.443 Download ChemDraw structure file

[a]20.2D= +16.9deg (C=1.76 CHLOROFORM, measured after 24 hours at 20degC) (Ref. 1060)
METHANOL (Ref. 1059)

METHOXIME TRI-TMS ETHER METHYL ESTER ; m/e 601(M+), 586, 570, 530, 511, 496, 480, 440, 421, 390, 350, 300, 294, 263, 217, 205, 191, 73 (Ref. 1059)


When prostaglandin I2 or its non-enzymatic degradation product (6-keto-prostaglandin F1a) was infused into man, a major urinary metbolite was 2,3-dinor-6-keto-prostaglandin F1a, a b-oxidation product (Ref. 0017).



120
PROSTAGLANDIN J2
7-[2(R)-(3(S)-Hydroxy-1(E)-octenyl)-3-oxo-4-cyclopenten-1(R)-yl]-5(Z)-heptenoic acid
XPR1901
Shouzo Yamamoto
PGJ2
C20H30O4 334.450 Download ChemDraw structure file
The anti-tumor and anti-viral activities of prostaglandin J2 are attributed to D12-prostaglandin J2 which is a degradation product of prostagladnin J2 and is characteristic of its alkylidene cyclopentenone structure (Ref. 0010).
ACETONITRILE(Ref. 1048)CHLOROFORM, ETHANOL (Ref. 1049)
l MeOHmax = 305(e 1200), 216(e 9900)nm (Ref. 1049)
n 3400, 3200, 2660, 1710, 1085, 970 cm-1 (Ref. 1049)
1H-NMR(CDCl3) : d 7.75-7.55(m, 1H, 9-CH), 6.30-6.10(m, 1H, 10-CH), 5.90(brs, 2H, OH), 5.75-5.35(m, 4H), 4.30-3.95(m, 1H, 15-CH) (Ref. 1049)
TMS ETHER ; M+ 478.2934 (Ref. 1049)



In aqueous solution prostaglandin D2 undergoes non-enzymatic dehydration and is converted to prostaglandin J2 (Ref. 0010).


121
7-[2(E)-(3(S)-Hydroxyoctylidene)-3-oxo-4-cyclopenten-1(R)-yl]-5(Z)-heptenoic acid
XPR1911
Shouzo Yamamoto
D12-PGJ2
C20H30O4 334.450 Download ChemDraw structure file
D12-Prostaglandin J2 is considered to be an ultimate metabolite of prostaglandin D2 with anti-tumor and anti-viral activities (Ref. 0042). The compound has no cell surface recptor, but is transported into cells and then inot nuclei. The biological activities of D12-prostaglandin J2 are due to the syntheses of various proteins including heat shock proteins, g-glutamylcysteine synthetase, collagen and heme oxygenase (Ref. 0043).
METHANOL(Ref. 1050)ETHANOL, CHLOROFORM, ETHYL ACETATE (Ref. 1051)
l EtOHmax = 244(e 6100)nm (Ref. 1051)
n : 2930, 1700, 1640, 1580, 1232, 028 cm-1 (Ref. 1051)
1H-NMR(CDCl3) : d 7.5(dd, 1H, 9-CH), 6.56(t, 1H, 13-CH), 6.35(dd,1 H, 10-CH), 5.48(m, 2H, 5,6-CH), 3.88(m, 1H, 15-CH), 3.44(m, 1H, 8-CH) (Ref. 1051)
m/e 334(M+), 316, 245, 236 (Ref. 1051)



In human plasma prostaglandin D2 is dehydrated and converted to 9-deoxy-D9,12-13,14-dihydro-prostaglandin D2 (D12-prostaglandin J2) catalyzedby serum albumin (Ref. 0042).


122
THROMBOXANE A2
7-[3-(3(S)-Hydroxy-1(E)-octenyl)-1(S),5(S),4,6-dioxabicyclo[3.1.1]hept-2-yl]-5(Z)-heptenoic acid
XPR2001
Shouzo Yamamoto
TXA2
C20H32O5 352.465 Download ChemDraw structure file
Thromboxane A2 aggregates platelets and constricts blood vessels and bronchi (Ref. 0014). Thromboxane A2 binds to a specific recptor (TP) coupled to Gq protein (Ref. 0033).




Thromboxane A2 is produced in platelets, polymorphonuclear leukocytes, macrophages, lung, kidney and spleen of various animals upon various biological stimulations (Ref. 0013).

Prostaglandin H2 produced by the catalysis of cyclooxygenase is further metabolized to thrombaxne A2 by thromboxane synthaase. Thromboxane A2 is unstable (half life 30 sec) and its oxetane ring is hydrolyzed to hemiacetal thromboxane B2 (Ref. 0017). The major urinary metabolite of tromboxane B2 is 2,3-dinor-thromboxane B2 (Ref. 0031), and 11-dehydro-thromboxane B2 is known as a suitble parameter for monitoring thromboxane production in human (Ref. 0032).
cDNA and genomic DNA for thromboxane A synthase (Ref. 0016) and those fro thromboxane A2 receptor (Ref. 0033) were cloned.
Stability:unstable in water around neutrality with a half life of about 40 sec at 37degC and decomposes to TXB2 and 12-hydroxy-5,8,10-heptadecatrienoic acid(Ref. 0013).
123
THROMBOXANE A3
7-[3-(3(S)-Hydroxy-1(E),5(Z)-octadienyl)-1(S),5(S),4,6-dioxabicyclo[3.1.1]hept-2-yl ]-5(Z)-heptenoic acid
XPR2002
Shouzo Yamamoto
TXA3
C20H30O5 350.449 Download ChemDraw structure file
Thromboxane A3 did not cause platelet aggregation unlike thromboxane A2, and inhibited platelet aggregation by other agonists (Ref. 0090).






Prostaglandin H3 is produced from 5,8,11,14,17-eicosapentaenoic acid, which is one-eighth as efficient a substrate as arachidonic acid, by the catalysis of fatty acid cyclooxygenase, and then transformed to unstable thromboxane A3 (Ref. 0090), which is converted non-enzymatically to stable thromboxane B3.


124
THROMBOXANE B2
7-[Tetrahydro-4(S),6-dihydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)-2H-pyran-3(S)-yl]-5(Z)-heptenoic acid
XPR2101
Shouzo Yamamoto
TXB2
C20H34O6 370.480 Download ChemDraw structure file
Thromboxane B2 as s stable degradation product of thromboxane A2 shows diminishd biological activity (Ref. 0014).
95-96degC (Ref. 1033)
[a]d-25=57.4deg(C=0.26 ETHYL ACETATE) (Ref. 1033)
ETHYL ACETATE (Ref. 1035)
FILM: n 3380, 1705cm-1 (Ref. 1033)
1H-NMR(CDCl3) : d 5.86(m, 1H, 14-CH), 5.72(m, 1H, 13-CH), 5.46(m, 2H, 5,6-CH), 5.35 and 5.23(m, 1H, 11-CH), 4.41(m, 1H, 12-CH), 4.22(m, 1H, 15-CH), 4.11(m, 1H, 9-CH), 2.35(t, 2H, 2-CH2), 0.89(m, 3H, 20-CH3) (Ref. 1034)
m/e 335, 317 (Ref. 1033)


Thromboxane B2 as a stable degradation product of bioactive but unstable thromboxane A2 is detected in the tissue where thromboxane A2 is produced (Ref. 0013).
The major urinary metabolite of tromboxane B2 is 2,3-dinor-thromboxane B2 (Ref. 0031), and 11-dehydro-thromboxane B2 is known as a suitble parameter for monitoring thromboxane production in human (Ref. 0032). 11-Hydroxythromboxane B2 dehydrogenase responsible for the 11-dehydro-thromboxane B2 production was identified as cytosolic aldehyde dehydrogenase (Ref. 0034).


125
THROMBOXANE B3
7-[Tetrahydro-4(S),6-dihydroxy-2(R)-(3(S)-hydroxy-1(E),5(Z)-octadienyl)-2H-pyran-3(S)-yl]-5(Z)-heptenoic acid
XPR2102
Shouzo Yamamoto
TXB3
C20H32O6 368.464 Download ChemDraw structure file

DIETHYL ETHER (Ref. 1118), ETHYL ACETATE, CHLOROFORM (Ref. 1119)
FILM : n 3392, 3010, 2932, 1713, 1407, 1363, 1231, 1154, 1104, 1024, 973, 895 cm-1 (Ref. 1119)
1H-NMR(CDCl3, TMS) : d 5.85(dd, J=17.5, 6.3Hz,1H, 14-CH), 5.71(dd, J=17.5, 7.5Hz, 1H, 13-CH), 5.55(td, J=20.0, 12.5Hz, 1H, 18-CH), 5.48-5.31(m, 4H, 5,6,11,17-CH), 4.41(dd, J=12.5, 7.5Hz, 1H, 12-CH), 4.23(dt, J=12.5, 6.3Hz, 1H, 15-CH), 4.08(m, 1H, 9-CH), 2.40-2.24(m, 4H, 4,16-CH), 2.18-1.96(m, 7H, 2,7,10,19-CH), 1.81(m, 2H, 3-CH), 1.74-1.63(m, 2H, 3-CH), 1.45(tdd, J=8.8, 5.0, 5.0Hz, 1H, 8-CH), 0.96(t, J=7.5Hz, 3H, 20-CH) (Ref. 1119) 13C-NMR(CDCl3) : 177.25, 136.52, 135.22, 130.75, 129.22, 127.49, 123.66, 123.59, 92.56, 71.58, 69.20, 64.95, 44.99, 36.01, 34.72, 32.89, 26.31, 24.80, 24.58, 24.58, 20.76, 14.21(Ref. 1119)
FAB : m/e 351(M+1-H2O), 333, 315, 307 (Ref. 1119)



Prostaglandin H3 is produced from 5,8,11,14,17-eicosapentaenoic acid by the catalysis of fatty acid cyclooxygenase, and then transformed to unstable thromboxane A3 (Ref. 0090), which is converted non-enzymatically to stable thromboxane B3.


126
2,3-DINORTHROMBOXANE B2
5-[Tetrahydro-4(S),6-dihydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)-2H-pyran-3(S)-yl]-3(Z)-pentenoic acid
XPR2111
Shouzo Yamamoto
2,3-DINOR-TXB2
C18H30O6 342.427 Download ChemDraw structure file

ETHYL ACETATE, DIETHYL ETHER, DICHLOROMETHANE (Ref. 1057)
METHYL ESTER ; 1H-NMR(CDCl3) : d 5.77-5.0(m, 6H), 4.50-3.96(m, 5H), 3.71(s, 3H, OCH3), 3.20-3.00(m, 2H) (Ref. 1057)
METHYL ESTER TRIS-TMS ETHER ; m/e 557, 482, 467, 411, 338, 301, 295, 267, 228, 225, 217 (Ref. 1056)


When thromboxane B2 is infused, 2,3-dinor-thromboxane B2 is found in urine of monkey (Ref. 0031) and man (Ref. 0048) as a major metabolite.

2,3-Dinor-thromboxane B2 is a b-oxidation product of thromboxane B2.


127
11-DEHYDROTHROMBOXANE B2
7-[Tetrahydro-4(S)-hydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)-6-oxo-2H-pyran-3(S)-yl]-5(Z)-heptenoic acid
XPR2121
Shouzo Yamamoto
11-DEHYDRO-TXB2
C20H32O6 368.464 Download ChemDraw structure file

METHANOL, ETHYL ACETATE (Ref. 1058)
METHYL ESTER ; CHLOROFORM solution, n 1730 cm-1 (Ref. 1057)
METHYL ESTER ; 1H-NMR(CDCl3) : d 5.86-5.78(m, 2H), 5.56-5.32(m, 2H), 5.13-4.72(m, 1H), 5.23-4.05(m, 2H), 3.67(S, 3H, OCH3)(Ref. 1057)
METHYL ESTER BIS-TMS ETHER ; m/e 526(M+), 511, 455, 370, 295 (Ref. 1057)


When thromboxane B2 is infused, 11-dehydro-thromboxane B2 is found as a major metabolite in the blood of rabbit (Ref. 0049) and man (Ref. 0032). The compound appears in urine as one of the mejor metabolites (Ref. 0032/0049).

11-Hydroxythromboxane B2 dehydrogenase is considered to be the enzyme responsible for 11-dehydro-thromboxane B2 production (Ref. 0034).


128
LEUKOTRIENE A4
5(S),6(S)-Epoxyeicosa-7(E),9(E),11(Z),14(Z)-tetraenoic acid
XPR3001
Shouzo Yamamoto
LTA4
C20H30O3 318.450 Download ChemDraw structure file
Leukotriene A4 as such is biologically less active than its active metabolites, leukotrienes B4 and C4. For example, leukotriene A4 is at least two orders of magnitude less potent than leukotrienes C4, D4 and E4 in contraction of guinea pig lung strips (Ref. 0022).
[a]d-25=-21.9deg(C=0.32,CYCLOHEXANE) (Ref. 1024)
SOL. IN CYCLOHEXANE,METHANOL(Ref. 1024). STABILITIES : to decompose to 5,12-DIHYDROXY-6,8,10,14-EICOSATETRAENOIC ACID and 5,6-DIHYDROXY-7,9,11,14-EICOSATETRAENOIC ACID under neutral aqueous solution at 37degC with one minite of half-life(Ref. 1030).
METHYL ESTER ; l MeOHmax = 269(e 30,500), 278(e 40,000), 287(e 34,400) nm (Ref. 1031)

METHYL ESTER ; 332(M+), 316, 300, 221, 189, 181, 129, 101 (Ref. 1029)


Leukotriene A4 is produced as an intermediate for the biosyntheses of leukotrienes B4 and C4 in polymorphonuclear leukocytes, mast cells and macrophages of various animal species (Ref. 0022).
Arachidonate 5-lipoxygenase is a bifunctional enzyme with a 5-oxygenase activity converting arachidonic acid to 5-hydroperoxy-6,8,11,14-eicosatetraenoic acid and a leukotriene A synthase activity converting the 5-hydroperoxy acid to leukotriene A4. The same enzyme produces leukotriene A4 from arachidonic acid via 5-hydroperoxy acid (Ref. 0025). The produced leukotriene A4 ia converted either to leukotriene B4 or to leukotriene C4 (Ref. 0022).
cDNA and genomic DNA for 5-lipoxygenase were cloned (Ref. 0007).
Stability:unstable in water around neutrality with a half life of about 1 min at 37degC and decomposes to 5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid and 5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid(Ref. 0021)
129
LEUKOTRIENE B4
5(S),12(R)-Dihydroxyeicosa-6(Z),8(E),10(E),14(Z)-tetraenoic acid
XPR3101
Shouzo Yamamoto
LTB4
C20H32O4 336.466 Download ChemDraw structure file
Leukotriene B4 causes adhesion of leukocytes to endothelial cells, stimulates chemotaxis and chemokinesis of leukocytes(Ref. 0022), and enhances superoxide anion production by human polymorphonuclear leukocytes (Ref. 0023). Leukotriene B4 binds to a specific receptor with 7 transmembrane domains coupled to Gi/Go or Gq protein (Ref. 0024).
METHANOL (Ref. 1021)
METHANOL : 260(e 38,000), 270.5(e 50,000), 281(e 39,000)nm (Ref. 1021)
1H-NMR(250MHz, D2O) : d 6.45(m, 1H, 8-CH), 6.15(m, 2H, 9,10-CH), 6.0(m, 1H, 7-CH), 5.65(m, 1H, 11-CH), 5.40(m, 1H, 15-CH), 5.25(m, 2H, 6,14-CH), 4.60(5-CH), 4.05(m, 1H, 12-CH), 2.15(m, 2H, 13-CH), 2.00(m, 1H, 2-CH), 1.85(m, 2H, 16-CH), 1.35-1.60(m, 4H, 3,4-CH), 1.00-1.25(m, 6H, 17,18,19-CH), 0.70(m, 3H, 20-CH) (Ref. 1022)
m/e 336, 319, 301 (Ref. 1023)


Leukotriene B4 is produced by polymorphonuclear leukocytes and macrophages of various animal species upon various stimulations on the cells (Ref. 0021/0022).
Arachidonic acid is metabolized to leukotrienen A4 with 5,6-epoxide by 5-lipoxygenases, and the product is further transformed to leukotrienee B4 by leukotriene A hydrolase (Ref. 0025). Leukotriene B4 is metabolized to lose its bioactivities either by w-oxidation (Ref. 0022) or by leukotriene B4 12-hydroxydehydrogenase (Ref. 0026).
cDNA and genomic DNA of 5-lipoxygenase (Ref. 0007) and cDNA for Leukotriene A hydrolase (Ref. 0007) were cloned. cDNA for leukotriene B 12-hydroxydehydrogenase was cloned (Ref. 0027).

130
12-oxo-Leukotriene B4
5S-hydroxy-12-keto-[6Z, 8E, 10E, 14Z]-eicosatetraenoic acid
XPR3111
Takao Shimizu
12-oxo-LTB4
C20H30O4 334.450 Download ChemDraw structure file
Increase in intracellular calcium in human leukocytes probably through BLT (LTB4 receptor). The IC 50 value is 100 times higher than that of LTB4.
Soluble in ethanol, methanol, ethyl acetate, acetonitril
UV maxima 316 nm, Absorbance at 320 nm is 41000/M



12-oxo-LTB4 is eluted at 7.8 min on RP-HPLC system as follows: Solvent:acetonitril/water/acetic acid, 50:50:0.01 (v/v/v), 0.01 % (w/v) Na2EDTA, pH 5.6 with ammonia Flow: 1 ml/min, isocratic Column: Cosmosil 5C18-AR (4.6 x 150 mm, Nacalai tesque, Tokyo) (Ref. 3111)
This metabolite is derived from LTB4 by LTB4 12-hydroxydehydrogenase. LTB4 12-hydroxydehydrogenase is expressed most abunduntly in liver and kidney.


LTB4 12-hydroxydehydrogenase cDNA is cloned from various animals. The accession numbers in DDBJ/EMBL/Genbank are shown in ( ). Pig (D49386) (Ref. 3112) (Ref. 3113) Human (D49387) (Ref. 3112) Rat (U66322) (Ref. 3114)

131
10,11,14,15-tetrahydro-12-keto-Leukotriene B4
5S-hydroxy-12R-keto-[6Z, 8E]-eicosatedienoic acid
XPR3112
Takao Shimizu
10,11,14,15-tetrahydro-12-keto-LTB4
C20H34O4 338.482 Download ChemDraw structure file
unknown
Soluble in ethanol, methanol, ethyl acetate, acetonitril
UV maxima 235 nm, Absorbance at 320 nm is 30500/M



10, 11, 14, 15-tetrahydro-12-oxo-LTB4 is eluted at 12.6min on RP-HPLC system as follows: Solvent:acetonitril/water/acetic acid, 50:50:0.01 (v/v/v), 0.01 % (w/v) Na2EDTA, pH 5.6 with ammonia Flow: 1 ml/min, isocratic Column: Cosmosil 5C18-AR (4.6 x 150 mm, Nacalai tesque, Tokyo) (Ref. 3111)





132
LeukotrieneB4 dimethyl amide
N,N-dimethy-5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraenamide
XPR3113
Takehiko Yokomizo
C22H37NO3 363.534 Download ChemDraw structure file
Leukotriene B4 dimethylamide inhibits LTB4 induced degranulation of human neutrophils at the concentration of 130 nM (Ki) and release of lysozyme of PMNL.(Ref. 2120/2121/2122) The effect may be due to the antagonistic effect against LTB4 receptor.(Ref. 2120)









133
Leukotriene B4 Ethanolamide
N-(2-hydroxyethyl)-5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraenamide
XPR3114
Takehiko Yokomizo
C22H37NO4 379.534 Download ChemDraw structure file
LTB4-EA is reported as a potent antagonist about 3 fold higher affinity for the human LTB4 receptor that LTB4. And LTB4-EA antagonizes the LTB4-induced contractions of guinea pig lung parenchyma with 10 nM as an EC50.(Ref. 2123)









134
6-trans Leukotriene B4
5S,12R-dihydroxy-6E,8E,10E,14Z-eicosatetraenoic acid
XPR3115
Takehiko Yokomizo
C20H32O4 336.466 Download ChemDraw structure file
6-trans LTB4 is reported as a chemoattractant to neutrophils but the properties is relatively weal compared with LTB4.(Ref. 2124)









135
6-trans-12-epi Leukotriene B4
5S,12S-dihydroxy-6E,8E,10E,14Z-eicsatetraenoic acid
XPR3116
Takehiko Yokomizo
C20H32O4 336.466 Download ChemDraw structure file
6-trans-12-epi LTB4 is reported as a weak chemotactic factors for PMNL with 20 times less potency thant LTB4 .(Ref. 2127)









136
12-epi Leukotriene B4
5S,12S-dihydroxy-6Z,8E,10E,14Z-eicsatetraenoic acid
XPR3117
Takehiko Yokomizo
C20H32O4 336.466 Download ChemDraw structure file
12-epi LTB4 has a week agonistic character at both recombinant human BLT1 and BLT2 approximately 10 _M for complete activation.(Ref. 2128)









137
20-carboxy Leukotriene B4
5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraene-1,20-dioic acid
XPR3118
Takehiko Yokomizo
C20H30O6 366.449 Download ChemDraw structure file
The biological activity of 20-carboxy LTB4 is only about 2.6% compared to that of LTB4 in causing PMNL degradation.(Ref. 2130)




20-carboxy LTB4 is a metabolite of LTB4 in human neutrophils




138
14,15-dehydro Leukotriene B4
5S,12R-dihydroxy-6Z,8E,10E-eicosatriene-14-ynoic acid
XPR3119
Takehiko Yokomizo
C20H30O4 334.450 Download ChemDraw structure file
14,15-dehydro LTB4 is reported as a selective ligand for the BLT1 and act as a selective antagonist of LTB4 in vivo.(Ref. 2131)









139
20-hydroxy Leukotriene B4
5S,12R,20-trihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid
XPR3120
Takehiko Yokomizo
C20H32O5 352.465 Download ChemDraw structure file
20-hydroxy LTB4 is commonly accepted as a inactive metabolite of LTB4 but reported to contract parenchymal strips from guinea pig lung (Ref. 2129) and as a good ligand form BLT2 receptor.(Ref. 2128)









140
20-trifluoro Leukotriene B4
5S,12R-dihydroxy-20,20,20-trifluoro-6Z,8E,10E,14Z-eicosatetraenoic acid
XPR3121
Takehiko Yokomizo
C20H29F3O4 390.437 Download ChemDraw structure file
20-trifluoro LTB4 has equal chemotactic activity to LTB4 with an EC50 of 3 nM (Ref. 2133/2134) but not degranulation activity of neutrophils.(Ref. 2132/2133/2134)









141
LEUKOTRIENE C4
5(S)-Hydoxy-6(R)-S-g-glutamylcysteinylglycinyleicosa-7(E),9(E),11(Z),14(Z)-tetraenoic acid
XPR3201
Shouzo Yamamoto
LTC4
C30H47O9N3S1 625.775 Download ChemDraw structure file
Leukotriene C4 is a potent stimulator of airway smooth muscles and causes bronchoconstriction as demonstrated in vitro and in vivo experiments, and gastrointestinal smooth muscles are also contracted. Vascular permeability is enhanced by leukotriene C4 at concentrations lower by 3-4 orders of magnitude than histamine (Ref. 0022). Gasstrointestinal smooth muscles are contracted (Ref. 0021/0022). Leukotriene C4 binds to a receptor with 7 transmembrane domains coupled to Gia/o protein (CysLT1) with an affinity lower by two orders of magnitude than that of leukotriene D4 (Ref. 0030).
METHANOL (Ref. 1024)
l MeOHmax = 270(e 32,000), 280(e 40,000), 290(e 31,000)nm (Ref. 1024)

the Chart(Ref. 1025)


Leukotriene C4 is produced by polymorphonuclear leukocytes, mast cells and macrophages of various animal species upon various stimulations on the cells (Ref. 0021/0022).
Arachidonic acid is metabolized to leukotrienen A4 with 5,6-epoxide by 5-lipoxygenases, and the product is further transformed to leukotrienee C4 incorporating glutathione by the catalysis of leukotriene C synthase (Ref. 0021).
cDNA and genomic DNA of 5-lipoxygenase (Ref. 0007) and those for leukotriene C synthase (Ref. 0028/0029) were cloned. cDNA for CysLT1 was cloned (Ref. 0030).

142
11-trans Leukotriene C4
5S-hydroxy-6R-(S-glutathionyl)-7E,9E,11E14Z-eicosatetraenoic acid
XPR3202
Takehiko Yokomizo
C30H47N3O9 593.709 Download ChemDraw structure file
The contraction effect on guinea pig parenchymal and ileum is almost equal to LTC4.(Ref. 2137/2138)









143
LEUKOTRIENE D4
5(S)-Hydroxy-6(R)-S-cysteinylglycinyleicosa-7(E),9(E),11(Z),14(Z)-tetraenoic acid
XPR3301
Shouzo Yamamoto
LTD4
C25H40O6N2S1 496.661 Download ChemDraw structure file
Leukotriene D4 stimulates airway smooth muscles and causes bronchoconstriction. Vascular permeability is enhanced. Gasstrointestinal smooth muscles are contracted (Ref. 0021/0022). Leukotriene D4 binds to a receptor with 7 transmembrane domains coupled to Gia/o protein (CysLT1) with an affinity higher by two orders of magnitude than that of leukotriene C4 (Ref. 0030).
METHANOL (Ref. 1026)
l MeOHmax = 270(e 32,000), 280(e 40,000), 290(e 31,000)nm (Ref. 1027)

N-ACETYL, 5-TRIMETHYLSILYL ETHER DIMETHYL ESTER derivative ; 638(M+), 623, 607, 548, 508, 405, 404, 315, 314, 274, 273 (Ref. 1026)


Leukotriene D4 is produced by basophils, eosinophils and macrophages of various animal species upon various stimulations on the cells (Ref. 0021/0022).
g-Glutamyl transpeptidase hydrolyzes the glutathione moiety of leukotriene C4 and produces leukotriene D4 liberating glutamic acid (Ref. 0022),
cDNA for CysLT1 was cloned (Ref. 0030).

144
11-trans Leukotriene D4
5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E14Z-eicosatetraenoic acid
XPR3302
Takehiko Yokomizo
C25H40N2O6 464.595 Download ChemDraw structure file
The potency for contraction of guinea pig ileum, trachea, and parenchyma of 11-trans LTD4 is 10-25% compared to LTD4.(Ref. 2139/2140)









145
LEUKOTRIENE E4
5(S)-Hydroxy-6(R)-S-cysteinyleicosa-7(E),9(E),11(Z),14(Z)-tetraenoic acid
XPR3401
Shouzo Yamamoto
LTE4
C23H37O5N1S1 439.610 Download ChemDraw structure file
Leukotriene E4 stimulates airway smooth muscles from different animal species, and is less potent than C4 in contracting isolated guinea pig ileum (Ref. 0022).
DIMETHYL ESTER ; [a]d-20=+35.2deg (Ref. 1063)
METHANOL (Ref. 1063/1028)
MONO-POTASSIUM SALT;l = 270(e 40000), 280(e 49400), 291nm( e 40000) (Ref. 1028)
DIMETHYL ESTER ; 1H-NMR(CDCl3) : d 6.33(dd, J=14.5Hz, 10Hz, 1H, 10CH), 6.0(t, J=10Hz, 1H, 11-CH), 5.62(dd, J=14.4, 9.6Hz, 1H, 7-CH), 5.3(m, J=10,9Hz, 1H, 14-CH), 3.71 and 3.62(2S, 6H, OCH3), 3.65(m, 1H, 5-CH), 3.4(m, 1H, 6-CH), 2.95(t, J=9Hz, 2H, 13-CH), 2.02(m, 2H, 16-CH), 0.86(t, J=6Hz, 3H, 20-CH) (Ref. 1063)



When leukotriene C4 was injected into male subjects, leukotriene E4 was found as a major urinary metabolite (Ref. 0050). Incubation of leukotriene D4 with human polymorphonuclear leukocytes produced leukotriene E4 (Ref. 0051).
Leukotriene D4 is converted to E4 by extracellular action of a dipeptidase released from granules of human polymorphonuclear leukocytes (Ref. 0051). Leukotriene E4 is transformed to leukotriene F4 by g-glultamyltransferase in the presence of glutathione, and to N-acetyl leukotriene E4 by incubation with rat liver microsomes (Ref. 0052).


146
11-trans Leukotriene E4
5S-hydroxy-6R-(S-cysteinyl)-7E,9E,11E14Z-eicosatetraenoic acid
XPR3402
Takehiko Yokomizo
C23H37NO5 407.544 Download ChemDraw structure file
11-trans LTE4 has equal potency to LTE4 in contracting guinea pig ileum.(Ref. 2141)









147
N-ACETYL-LEUKOTRIENE E4
5(S)-Hydroxy-6(R)-S-(N-acetylcysteinyl)eicosa-7(E),9(E),11(Z),14(Z)-tetraenoic acid
XPR3411
Shouzo Yamamoto
N-ACETYL-LTE4
C25H39O6N1S1 481.646 Download ChemDraw structure file

l = 280 nm (270sh, 290sh) (Ref. 1067)





Upon subcutaneous injection of leukotriene C4 in rats N-acetyl leukotriene E4 and N-acetyl 11-trans-leukotriene E4 are found in feces. Leukotriene E4 is transformed to N-acetyl leukotriene E4 by incubation with rat liver microsomes (Ref. 0052).


148
LEUKOTRIENE F4
5(S)-Hydroxy-6(R)-S-glutamylcysteinyleicosa-7(E),9(E),11(Z),14(Z)-tetraenoic acid
XPR3501
Shouzo Yamamoto
LTF4
C28H44O8N2S1 568.724 Download ChemDraw structure file

l = 270sh, 280(e 40000), 290sh nm (Ref. 1064)
N-TRIFLUOROACETYL METHYL ESTER ; n 3300, 1720, 1650, 1200, 985cm-1 (Ref. 1065)
N-TRIFLUOROACETYL METHYL ESTER ; 1H-NMR(CDCl3) : d 6.9-5.2(m, 8H), 5.0-4.5(m, 2H), 3.8-3.6(m, 1H, 5-CH), 3.79(s, 3H, OCH3), 3.76(s, 3H, OCH3), 3.67(s, 3H, OCH3), 3.6-3.3(m, 1H, 6-CH), 3.1-2.7(m, 4H), 0.9(t, J=7Hz, 3H, 20-CH3) (Ref. 1065)
N-TRIFLUOROACETYL METHYL ESTER ; 701(M+), 688, 675, 674, 662, 657, 649, 648, 578, 550, 465 (Ref. 1065)



Leukotriene E4 is transformed to leukotriene F4 by g-glultamyltransferase in the presence of glutathione (Ref. 0052).


149
LIPOXIN A4
5(S),6(R),15(S)-Trihydroxyeicosa-7(E),9(E),11(Z),13(E)-tetraenoic acid
XPR4001
Shouzo Yamamoto
LXA4
C20H32O5 352.465 Download ChemDraw structure file
Lipoxin A4 is either vasoconstrictive or vasodilatory, and has immunoregulatory activities blocking the cytotoxic action of NK cell, inhibiting adherence and chemotaxis of leukocytes induced by FMLP, PAF or leukotriene B4 (Ref. 0035).
DIETHYL ETHER, METHANOL (Ref. 1037)
l MeOHmax = 287, 301(e 50,000), 316nm (Ref. 1037/1038)
1H-NMR(250MHz, 5% CD3OD/D2O ) : d 0.8-0.9(brt, 3H), 1.2-1.8(m, 14H), 2.1-2.3(m, 2H), 3.4-3.6(m, 1H), 3.95-4.05(t, J=6.8Hz, 1H), 4.1-4.2(q, J=7.1Hz, 1H), 5.6-5.85(seven lines, 2H), 5.9-6.1(m, 2H), 6.2-6.45(m, 2H), 6.6-6.8(m, 2H) (Ref. 1037)
TMS-derivs. ; 582(M+), 492, 482, 379, 289, 203, 173, 171 (Ref. 1036)


Lipoxin A4 is produced by activated leukocytes (Ref. 0035/0036).
Dual lipoxygenation pathways are considered for lipoxin A4 synthesis from arachidonic acid; either 15-lipoxygenase and 5-lipoxygenase in leukocytes or 5-lipoxygenase in leukocytes and 12-lipoxygenase in platelets (Ref. 0035).
cDNA for a receptor specific for lipoxin A4 was cloned out of orphan cDNAs (Ref. 0037).

150
LIPOXIN B4
5(S),14(R),15(S)-Trihydroxyeicosa-6(E),8(Z),10(E),12(E)-tetraenoic acid
XPR4101
Shouzo Yamamoto
LXB4
C20H32O5 352.465 Download ChemDraw structure file
Lipoxin B4 is either vasoconstrictive or vasodilatory, and blocks the cytotoxic action of NK cell (Ref. 0035).
METHYL ESTER ; [a]d-20=19.2deg(C=1.16, CHLOROFORM) (Ref. 1041)
METHANOL (Ref. 1039)
l MeOHmax = 288, 300(e 50,000), 315nm (Ref. 1040)
METHYL ESTER ; CHCl3 solution, n 3610, 3470, 3030, 3015, 2960, 2935, 2860, 1735, 1605, 1440, 1230, 1000, 980cm-1 (Ref. 1041)
1H-NMR(250MHz, CDCl3) : d 6.68(m, 2H), 6.36(dd, J=14.8 and 10.5Hz, 1H), 6.23(dd, J=14.1 and 10.7Hz, 1H), 6.0(m, 2H), 5.75(m, 2H), 4.17(m, 2H), 3.70(m, 1H), 3.65(s, 3H), 2.34(t, J=7.1Hz, 2H), 1.78-1.21(m, 12H), 0.86(t, J=6.4Hz, 3H) (Ref. 1041)
TRIMETHYLSILYL ETHER METHYL ESTER ; 582(M+), 492, 482, 409, 402, 379, 329, 319, 307, 289, 203, 173 (Ref. 1040)


Lipoxin B4 is produced by activated leukocytes (Ref. 0035/0036).
Dual lipoxygenation pathways are considered for lipoxin B4 synthesis from arachidonic acid; either 15-lipoxygenase and 5-lipoxygenase in leukocytes or 5-lipoxygenase in leukocytes and 12-lipoxygenase in platelets (Ref. 0035).


151
LEUKOTRIENE B5
5(S),12(R)-Dihydroxy-6(Z),8(E),10(E),14(Z),17(Z)-eicosapentaenoic acid
XPR4102
Shouzo Yamamoto
LTB5
C20H30O4 334.450 Download ChemDraw structure file
Leukotriene B5 is about 1/30 as active as leukotriene B4 in stimulating aggregation of rat neutrophils, migration and lysosomal enzyme release of human polymorphonuclear leukocytes, and bradykinin-induced vascular permeability (Ref. 0092). Leukotriene B5 is much less active than B4 to increase intracellular calciuim level in human neutrophils (Ref. 0093).
METHANOL (Ref. 1120)
l max = 260sh, 270, 290sh nm (Ref. 1121)
METHYL ESTER DIACETATE ; 1H-NMR(BENZEN-d6, 270MHz) : 6.79(dd, J=11.53, 14.83Hz, 1H, 8-CH), 6.34(dd, J=10.55, 14.83Hz, 1H, 10-CH), 6.09(dd, J=10.87, 14.83Hz, 1H, H-9), 6.03(t, J=11.53Hz, 7-CH), 5.90(dt, J =Ca.9.5, 11Hz, 5-CH), 5.63(dd, J=6.92, 14.82Hz, 11-CH), 5.60-5.38(m, 5H, 12,14,15,17,18-CH), 5.33(t, J=10.22Hz, 6-CH), 3.35(s, 3H), 2.83(m, 2H, 16-CH), 2.47(m, 1H, 13-CH), 2.38(m, 1H, 13-CH), 1.74(s, 3H), 1.68(s, 3H), 0.95(t, J=7.5Hz, 3H, 20-CH) (Ref. 1120)
METHYL ESTER TRIMETHYLSILYL ETHER M/E, 492(M+), 477, 461, 402, 391, 383,293, 267, 229, 217, 203 (Ref. 1121)


Leukotriene B5 is hardly detectable in human neutrophils, but is produced in the subjects fed with 5,8,11,14,17-eicosapentaenoic acid (Ref. 0091).
Leukotriene B5 is produced via leukotriene A5 from 5,8,11,14,17-eicosapentaenoic acid, which is almost as active as arachidonic acid as substrate (Ref. 0065).


152
HEPOXILIN A3
8-Hydroxy-11,12(S,S)-epoxyeicosa-5,14(Z,Z),9(E)-trienoic acid
XPR5001
Shouzo Yamamoto
HxA3
C20H32O4 336.466 Download ChemDraw structure file
As the biological activities of hepoxilin A3, insulin secretion from pancreas is stimulated, the enhanced vascular permeability by bradykinin is potentiated, hyperpolarization in hippocampal CA1 neurons is caused, and platelet aggregation is inhibited. At the molecular level hepoxilin A3 releases intracellular calcium, and opens potassium channel. Hepoxilin-specific binding proteins are present in human neutrophils (Ref. 0055).
DIETHYL ETHER (Ref. 1071)

METHYL ESTER TRIS-TMS ETHER ; m/e 422(M+), 407, 391, 332, 311, 282, 269(base peak) (Ref. 1070)


Hepoxilin A3 together with hepoxilin B3 is produced from arachidonic acid or more directly from 12(S)-hydroperoxy-5,8,10,14-eicosatetraenoic acid in various animal tissues including brain, pineal gland, pancreas and skin (Ref. 0055).
The presence of hepoxilin synthase was suggested by a finding that intact cells (skin) and tissue slices (brain hippocampus and pineal gland) transformed 12(S)-hydroperoxy-5,8,10,14-eicosatetraenoic acid to hepoxilins A3 and B3, but tissue boiling inhibited the hepoxilin production (Ref. 0056).


153
TRIOXILIN A3
8,11(R),12(S)-Trihydroxyeicosa-5(Z,9(E,14(Z)-trienoic acid
XPR5011
Shouzo Yamamoto
TrXA3
C20H34O5 354.481 Download ChemDraw structure file


METHYL ESTER TRIS-TMS ETHER ; m/e 444, 384, 371, 353, 281, 243, 213(base peak) (Ref. 1074)




Trioxilin A3 is produced from hepoxilin A3 by the catalysis of hepoxilin epoxide hydrase of rat liver cytosol (Ref. 0058).


154
HEPOXILIN B3
10-Hydroxy-11(R),12(S)-epoxyeicosa-5,8,14(Z,Z,Z)-trienoic acid
XPR5101
Shouzo Yamamoto
HxB3
C20H32O4 336.466 Download ChemDraw structure file
Little has been described about the biological actvity of hepoxilin B3 except for its poteniation of glucose-dependent insulin secretion (Ref. 0055) and of bradykinin-induced increase of vascular permeability (Ref. 0057).
ACETATE, METHYL ESTER ; [a]d-23=-10.9deg(C=0.11, CHLOROFORM) (Ref. 1073)
DIETHYL ETHER (Ref. 1071)
ACETATE METHYL ESTER ; n(CHLOROFORM) 2956, 1743, 1550, 1372, 1234, 1033, 999cm-1 (Ref. 1073)
ACETATE METHYL ESTER ; 1H-NMR(C6D6) : d 5.67(dd, J=9.2, 6.4Hz, 1H, 10-CH), 5.52, 5.46, 5.42, 5.35, 5.32, 3.36(s, 3H, OCH3), 2.95(m, 2H, 7-CH), 2.92(m, 1H, 11-CH), 2.86(ddd, J=7.4, 7.4, 2.1Hz, 1H, 12-CH), 2.30(ddd, J=14.8, 7.4, 7.4Hz, 1H, 13-CH), 2.18(ddd, J=14.8, 7.4, 7.4Hz, 1H, 13-CH), 2.12(t, J=7.4Hz, 2H, 2-CH), 1.98(dt, J=7.4, 7.4Hz, 2H, 4-CH), 1.92(dt, J=8.8, 8.8Hz, 2H, 16-CH), 1.65(s, 3H, COCH3), 1.60(tt, J=7.4, 7.4Hz, 2H, 3-CH), 1.25(m, 6H), 0.88(t, J=7.0Hz, 3H, 20-CH). (Ref. 1073) 13NMR(C6D6) : 134.22, 133.35, 130.17, 127.74, 124.31, 123.37, 70.86, 58.30, 55.71, 50.94, 33.30, 31.71, 29.66, 29.52, 27.59, 26.73, 25.00, 22.88, 20.53, 14.23 (Ref. 1073)
METHYL ESTER TMS ETHER ; m/e 311, 282, 269(base peak) (Ref. 1073)


Hepoxilin B3 together with hepoxilin A3 is produced from arachidonic acid or more directly from 12(S)-hydroperoxy-5,8,10,14-eicosatetraenoic acid in various animal tissues including brain, pineal gland, pancreas and skin (Ref. 0055).
The presence of hepoxilin synthase was suggested by a finding that intact cells (skin) and tissue slices (brain hippocampus and pineal gland) transformed 12(S)-hydroperoxy-5,8,10,14-eicosatetraenoic acid to hepoxilins A3 and B3, but tissue boiling inhibited the hepoxilin production (Ref. 0056).


155
TRIOXILIN B3
10,11(S),12(R)-Trihydroxyeicosa-5,8,14(Z,Z,Z)-trienoic acid
XPR5111
Shouzo Yamamoto
TrXB3
C20H34O5 354.481 Download ChemDraw structure file


METHYL ESTER TRIS-TMS ETHER ; m/e 342, 315, 269, 225, 213, 129(base peak) (Ref. 1074)




Trioxilin B3 is produced by hydrolysis of hepoxilin B3 with ammonium sulfate fraction of rat lung cytosol (Ref. 0056).


156
5(S)-Hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid
XPR6001
Shouzo Yamamoto
5(S)-HPETE
C20H32O4 336.466 Download ChemDraw structure file

DIETHYL ETHER (Ref. 1077). ETHYL ACETATE (Ref. 1078)
l MeOHmax = 230nm (Ref. 1076)






Arachidonic acid is oxygenated at the position 5 by the 5-oxygenase activity of arachidonate 5-lipoxygenase, and transformed to 5(S)-hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid, which is further converted to leukotriene A4 by the same enzyme. Thus, the 5-hydroperoxy acid is an intermediate for leukotriene A4 synthesis (Ref. 0025).
cDNA and genomic DNA of 5-lipoxygenase were cloned (Ref. 0007).

157
12(S)-Hydroperoxy-5,8,10,14-(Z,Z,E,Z)-eicosatetraenoic acid
XPR6002
Shouzo Yamamoto
12(S)-HPETE
C20H32O4 336.466 Download ChemDraw structure file
There are reports for various biological activities of 12(S)-hydroperoxy acid such as neurotransmission, melatonin secretion, inhibition of platelet function and constriction of basilar artery, but a general theory has not been established (Ref. 0059/0060).
DIETHYL ETHER (Ref. 1077), ETHYL ACETATE (Ref. 1078)
METHYL ESTER;l EtOHmax = 237nm (e 31,000) (Ref. 1081)






When arachidonic acid is allowed to react with 12-lipoxygenase, the predominant product is 12(S)-hydroperoxy-5,8,10,14-(Z,Z,E,Z)-eicosatetraenoic acid (Ref. 0059). The produced 12(S)-hydroperoxy acid is a precursor of hepoxilin (Ref. 0055).
cDNA and genomic DNA for 12-lipoxygenases were cloned (Ref. 0060).

158
15(S)-Hydroperoxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid
XPR6003
Shouzo Yamamoto
15(S)-HPETE
C20H32O4 336.466 Download ChemDraw structure file
15-Lipoxygenase present in rabbit reticulocytes is presumed to be involved in the breakdown of mitochondrial membrane and the maturation of red cells (Ref. 0062). The enzyme is active with esterified polyunsaturated fatty acids contained in the membrane of subcelluar orgnelles or serum lipoprotein, and its peroxy products may be involved in the pathogenesis of arteriosclerosis (Ref. 0063).
DIETHYL ETHER (Ref. 1077), ETHYL ACETATE(Ref. 1078), ETHANOL(Ref. 1086), METHANOL(Ref. 1087)
lmax = 236nm(e 27000) (Ref. 1086) lmax(ISO-OCTANE) = 236nm(e 30000) (Ref. 1085)
METHYL ESTER ; 1H-NMR(360MHz) : d 6.61(dd, J=11, 15.5Hz, 1H, 13-CH), 6.03(dd, J=10.5, 11Hz, 1H, 12-CH), 5.61(J=7.5Hz, 1H, 14-CH), 5.46(dd, J=7.5, 10.5Hz, 1H,11-CH), 5.39(m, 4H, 5,6,8,9-CH), 4.39(m, 1H, 15-CH), 3.67(s, 3H, OCH3), 2.98(2H, 10-CH), 2.81(2H, 7-CH), 2.33(2H, 2-CH), 2.11(2H, 4-CH), 1.72(2H, 3-CH), 1.64(2H, 16-CH), 1.30(6H), 0.88(3H, 20-CH) (Ref. 1087)




When arachidonic acid is allowed to react with 15-lipoxygenase, the predominant product is 15(S)-hydroperoxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid (Ref. 0061). The 15-hydroperoxy acid is further transformed to dihydroperoxy acids or 14,15-epoxy acid with a conjugated triene by the catalyses of 12- and 15-lipoxygenases (Ref. 0065), and is a precursor for lipoxin biosynthesis (Ref. 0035).
cDNA and genomic DNA of 15-lipoxygenases were cloned (Ref. 0064).

159
(R),(Z,E,Z,Z)-8-Hydroperoxy-5,9,11,14-eicosatetraenoic acid
XPR6014
Shouzo Yamamoto
8(R)-HPETE
C20H32O4 336.466 Download ChemDraw structure file

ETHYL ACETATE , METHANOL (Ref. 1092)
l max = 235.8nm (e 28,000) (Ref. 1092)




The compound is produced by the catalysis of 8(R)-lipoxygenase as an intermediate of coral prostanoid biosynthesis (Ref. 0073).




160
5(S)-Hydroxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid
XPR6101
Shouzo Yamamoto
5(S)-HETE
C20H32O2 304.467 Download ChemDraw structure file

METHYL ESTER ; [a]d-23=+14.0deg(C=2.0, BENZENE) (Ref. 1079)
DIETHYL ETHER (Ref. 1080)
METHYL ESTER ; l MeOHmax = 235nm (e 30,500) (Ref. 1080)

METHYL ESTER ETHER ; m/e 406(M+), 391, 375, 316, 305, 255, 216, 215, 203, 190, 155, 150, 143, 136, 105, 80, 79 (Ref. 1080)



When arachidonic acid is oxygenated by 5-lipoxygenase, 5(S)-hydroperoxy-6,,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid is produced (Ref. 0025). The latter compound is reduced to a corresponding 5(S)-hydroxy acid with whole cells or crude enzyme preparations.


161
12(S)-Hydoxy-5,8,10,14-(Z,E,Z,Z)-eicosatetraenoic acid
XPR6102
Shouzo Yamamoto
12(S)-HETE
C20H32O3 320.466 Download ChemDraw structure file
There are reports for various biological activities of 12(S)-hydroxy acid such as rat hypothalamic secretion of LH-RH, stimulated chemotactic activity of human eosinophils and neutrophils, stimulated migration of epidermal tumor cells and rat aortic smooth muscle cells, involvement in angiotension II-mediated aldosterone biosynthesis in human adrenal glomerulosa, and expression or activation of GpIIb/IIIa in tumor cells, but a general theory has not been established (Ref. 0059/0060).
METHYL ESTER ; [a]d-25=+1.50deg(C=0.2, CHLOROFORM) (Ref. 1082), [a]d-22=+13deg(C=1.5, ACETONE) (Ref. 1083)
DIETHYL ETHER , ACETONE , BENZENE (Ref. 1083)
METHYL ESTER ; l MeOHmax = 234nm (Ref. 1084)METHYL ESTER ; l EtOHmax = 237nm(e 30500) (Ref. 1081)
NEAT : n 3480b, 1710, 1460, 1400cm-1 (Ref. 1083)
1H-NMR(250MHz, ACETONE-D6) ; d 6.58(dd, J=15.3, 11.0Hz, 1H, 10-CH), 5.97(t, J=11.0Hz, 1H, 9-CH), 5.72(dd, J=15.3, 6.2 Hz, 1H, 11-CH), 5.29(m, 5H, 5,6,8,14,15-CH), 4.16(q, J=6.3Hz, 1H, 12-CH), 2.94(t, J=6.1Hz, 2H, 7-CH), 2.27(t,J= 7.4Hz, 2H,2-CH), 2.22(m, 2H, 13-CH), 1.66 and 2.14(m, 2H, 4-and 16-CH), 0.87(t, J=6.3Hz, 3H, 20-CH) (Ref. 1083). 13NMR(C6D6) : 174.3, 137.77, 132.02, 129.98, 129.62, 128.88, 128.69, 125.96, 124.44 (Ref. 1083)
METHYL ESTER ; m/e 316, 303, 223, 191, 141, 107(base peak) (Ref. 1084)



When arachidonic acid is oxygenated by 12-lipoxygenase, 12(S)-hydroperoxy-5,8,10,14-(Z,Z,E,Z)-eicosatetraenoic acid is produced (Ref. 0059). The latter compound is reduced to a corresponding 12(S)-hydroxy acid with whole cells or crude enzyme preparations.


162
15(S)-Hydroxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid
XPR6103
Shouzo Yamamoto
15(S)-HETE
C20H32O3 320.466 Download ChemDraw structure file
In connection with biological activities of 15-hydroxyeicosatetraenoic acid, there are reports for pain response of skin, mucus secretion in airway, histamine hypersensitivity, prolactin secretion, and regulation of protein phosporylation and cell signalling (Ref. 0064).
DIETHYL ETHER (Ref. 1086)
METHYL ESTER ; l (ISOOCTANE) = 236nm(e 27200) (Ref. 1086)
METHYL ESTER ; 1H-NMR(90MHz) : d 6.56(dd, J=11, 14.5Hz, 1H, 13-CH), 6.02(dd, J=11,11Hz, 1H, 12-CH), 5.7(dd, J=6.8, 14.5Hz, 1H,14-CH), 5.51(dd, J=6,11Hz, 1H, 11-CH), 4.16(dd, J=6.8, 6.8Hz, 1H, 15-CH), 3.69(s, 3H, OCH3), 2.98(2H, 10-CH), 2.84(2H, 7-CH), 2.35(2H, 2-CH), 2.08(2H, 4-CH), 1.47(2H, 16-CH), 2.3-0.9(11H) (Ref. 1086)
METHYL ESTER TMS ETHER ; m/e 406(M+), 391, 335, 316, 305, 225, 173 (Ref. 1086)



When arachidonic acid is oxygenated by 15-lipoxygenase, 15(S)-hydroperoxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid is produced (Ref. 0061). The latter compound is reduced to a corresponding 15(S)-hydroxy acid with whole cells or crude enzyme preparations.


163
(R),(Z,Z,E,Z)-12-Hydroxy-5,8,10,14-eicosatetraenoic acid
XPR6112
Shouzo Yamamoto
12(R)-HETE
C20H32O3 320.466 Download ChemDraw structure file

METHANOL (Ref. 1089), ETHYL ACETATE , 1-CHLOROBUTANE (Ref. 1090)
l max = 237nm (Ref. 1089)

METHYL ESTER TMS ETHER ; m/e 406(M+), 391, 375, 316, 295 (Ref. 1089)


The compound is detected in the pathological skin of psoriasis patient (Ref. 0069), and it is a P-450 product from arachidonic acid as demonstrated with microsomal preparations of bovine cornea (Ref. 0070) and rat liver (Ref. 0071). The compound is also found in sea urchin eggs (Ref. 0072).



164
(R),(Z,E,Z,Z)-8-Hydroxy-5,9,11,14-eicosatetraenoic acid
XPR6114
Shouzo Yamamoto
8(R)-HETE
C20H32O3 320.466 Download ChemDraw structure file
The compound is involved in the maturation of starfish oocyte (Ref. 0074).
8(S)-ISOMER METHYL ESTER ; [a]d-22=-4.75deg(C=0.4, CHLOROFORM) (Ref. 1091)
ETHYL ACETATE (Ref. 1092)
METHYL ESTER ; l max = 235.8nm (e 28,000)(Ref. 1092)
8(S)-ISOMER METHYL ESTER ; 1H-NMR(CDCl3) : d 6.56(dd, J=14.5, 11.1Hz, 1H, 10-CH), 6.00(brt, J=11.1, 9.7Hz, 1H, 11-CH), 5.72(dd, J=7.3, 14.5Hz, 1H, 9-CH), 5.59-5.16(m, 5H), 4.23(q, 1H,8-CH), 3.71(s, 3H,OCH3), 2.95(t, 2H,13-CH), 2.35(t, 4H, 4,7-CH), 2.11(sextet, 4H), 1.73(pentet, 2H, 3-CH), 1.56(brs, S, 1H, OH), 1.32(m, 6H), 0.91(t, 3H, 20-CH) (Ref. 1091)
METHYL ESTER, TMS ETHER ; m/e 265 (Ref. 1092). 8(S)-ISOMER METHYL ESTER TMS ETHER ; m/e 406, 391, 316, 265, 243 (Ref. 1091)






165
(R),(Z,Z,Z)-12-Hydroxy-5,8,14-eicosatetraenoic acid
XPR6122
Shouzo Yamamoto
C20H34O3 322.482 Download ChemDraw structure file
The compound has vasodilatory activity, and may be involved in the wound-healing of corneal injury (Ref. 0075).
METHYL ESTER ; [a]d-23=-3.0deg(C=0.8, ACETONE) (Ref. 1093)
ETHYL ACETATE (Ref. 1094)
METHYL ESTER ; 1H-NMR(CDCL3) : d 5.63-5.51(m, 1H), 5.47-5.28(m, 5H), 3.67(S, 3H), 3.67-3.57(m, 1H), 2.79(t, J=5.5Hz, 2H), 2.32(t, J=7.4Hz, 3H), 2.30-1.99(m, 6H), 1.76-1.39(m, 6H), 1.40-1.23(m, 6H), 0.88(t, J=6.8Hz, 3H) (Ref. 1093)
METHYL ESTER TMS ETHER ; m/e 393, 319, 297 (Ref. 1094)


The compound is produced from arachidonic acid which is incubated with bovine corneal microsomes in the presenc of NADPH (Ref. 0075).



166
(S),(Z,E,E)-12-Hydroxy-5,8,10-heptadecatrienoic acid
XPR6201
Shouzo Yamamoto
HHT
C18H30O3 294.429 Download ChemDraw structure file
The compound stimulates chemotactic and chemokinetic activities of human polymorphonuclear leukocytes (Ref. 0066).
METHYL ESTER ; [a]d-25 =+7.5deg(C=0.2, CHLOROFORM) (Ref. 1088)
DIETHYL ETHER (Ref. 1081)
METHYL ESTER ; ETHANOL : 232nm(e 33,400)(Ref. 1081). METHANOL : 240nm (Ref. 1088)
METHYL ESTER ; 1H-NMR(CDCl3) : d 6.17(dd, J=15.11, 10.36Hz, 1H, 10-CH), 6.04(dd, J=15,05, 10.52Hz, 1H, 9-CH), 5.66(dt, J=15.16, 6.48Hz, 1H), 5.60(dd, J=17.17, 7.04Hz, 1H, 11-CH), 5.42(m, 2H, 5-CH, 6-CH), 4.1(m, 1H, 12-CH), 3.66(s, 3H, COOCH3), 2.81(m, 2H, 7-CH), 2.36(t, J=7.51Hz, 2H, 2-CH), 2.1-0.85(m, 16H, CH2 and CH3) (Ref. 1088)
METHYL ESTER TMS ETHER ; m/e 366(M+), 335, 295, 276, 225, 173, (128)(Ref. 1017) METHYL ESTER ; 298(M+), 224 (Ref. 1088)



When prostaglandin H2 reacts with thromboxane A synthase and the endoperoxide moiety is cleaved, the production of thromboxane A2 is accompanied by the formation of 12(S)-hydroxy-5,8,10-heptadecatrienoic acid in an almost equimolar amount liberating malondialdehyde (Ref. 0067). This compound is also a product of non-enxymatic degradation of prostaglandin H2 (Ref. 0068).


167
5(6)OXIDO-8,11,14-EICOSATRIENOIC ACID
(Z,Z,Z)-5,6-Epoxy-8,11,14-eicosatrienoic acid
XPR6300
Shouzo Yamamoto
5,6-EET
C20H32O3 318.450 Download ChemDraw structure file
The compound is active in stimulated secretion of somatostatin, insulin and glucagon, vasodilataion and regulation of intracellular calcium (Ref. 0078).

METHYL ESTER ; m/e 334(M+), 316, 303, 283, 267, 233, 190, 176, 163,143(base peak) (Ref. 1095). METHYL ESTER ; m/e 334(M+), 316, 303, 285, 245 (Ref. 1096)


The compound is produced when arachidonic acid in the presence of NADPH is incubated with the liver microsomes of rat (Ref. 0076) or rabbit (Ref. 0077).



168
8(9)OXIDO-5,11,14-EICOSATRIENOIC ACID
(Z,Z,Z)-8,9-Epoxy-5,11,14-eicosatrienoic acid
XPR6301
Shouzo Yamamoto
8,9-EET
C20H32O3 318.450 Download ChemDraw structure file
The compound relaxes intestinal artery (Ref. 0078).
8(S)9(R)-EET METHYL ESTER ; [a]d-23=+2.33deg(C=1, ACETONE) (Ref. 1098)
CHLOROFORM (Ref. 1099)
1H-NMR(CDCl3) : d 5.70-5.08(m, 6H), 3.06-2.65(m, 4H), 2.62-1.04(complex m, 18H), 0.88(t, 3H) (Ref. 1099)
METHYL ESTER ; m/e 334(M+), 316, 303, 290, 245, 193, 183, 175, 165 (Ref. 1096)


The compound is produced when arachidonic acid in the presence of NADPH is incubated with the liver microsome of rat (Ref. 0076) or rabbit (Ref. 0077). It is also found in rabbit kidney (Ref. 0079) and human urine (Ref. 0080).



169
11(12)OXIDO-5,8,14-EICOSATRIENOIC ACID
(Z,Z,Z)-11,12-Epoxy-5,8,14-eicosatrienoic acid
XPR6302
Shouzo Yamamoto
11,12-EET
C20H32O3 318.450 Download ChemDraw structure file
The compound relaxes intestinal artery, inhibits vasopressin-dependent water flow in urinary bladder, and regulates intracellular calcium level (Ref. 0078).
11(R),12(S)-EET METHYL ESTER ; [a]d-23=+4.94deg(C=1.64 ,ACETONE) (Ref. 1098) 11(S),12(R)-EET METHYL ESTER ; [a]d-24=-2.34deg(C=0.66, CHLOROFORM) (Ref. 1099)
1H-NMR(CDCl3) : d 5.54-5.20(m, 6H), 3.61(s, 3H), 3.00-2.68(m, 4H), 2.37-2.00(m, 10H), 1.81-1.54(m, 2H), 1.46-1.13(m, 6H), 0.88(t, J=7Hz, 3H) (Ref. 1098)
METHYL ESTER ; m/e 340(M+), 322, 309, 227, 155 (Ref. 1096)


The compound is produced when arachidonic acid in the presence of NADPH is incubated with the liver microsome of rat (Ref. 0076) or rabbit (Ref. 0077).



170
14(15)OXIDO-5,8,11-EICOSATRIENOIC ACID
14,15-Epoxy-(Z,Z,Z)-5,8,11-eicosatrienoic acid
XPR6303
Shouzo Yamamoto
14,15-EET
C20H32O3 318.450 Download ChemDraw structure file
The compound stimulates glulcagon release, inhibits vasopressin-dependent water flow in urinary bladder, regulates intracellular calcium level, and inhibits platelet aggregation (Ref. 0078).
14(R),15(S)-EET METHYL ESTER ; [a]d-24=-2,75deg(C=0.70, CHLOROFORM) 14(S),15(R)-EET METHYL ESTER ; [a]d-24=+2.78deg(C=0.82, CHLOROFORM) (Ref. 1099)

METHYL ESTER ; m/e 334(M+), 316, 281, 263, 220, 161, 147, 119, 91(base peak) (Ref. 1095). METHYL ESTER ; m/e 334(M+), 316, 303, 263, 245, 235, 234, 220, 119, 91 (Ref. 1096)


The compound is produced when arachidonic acid in the presence of NADPH is incubated with the liver microsome of rat (Ref. 0076) or rabbit (Ref. 0077). It is also found in rabbit kidney (Ref. 0079) and human urine (Ref. 0080).



171
17(R)(18S)OXIDO-5,8,11,14-EICOSATETRATENOIC ACID
17,18-(R,S)-Epoxy-5,8,11,14-(Z,Z,Z,Z)-eicosatetraenoic acid
XPR6304
Shouzo Yamamoto
17(18)EpETE
C20H28O3 316.435 Download ChemDraw structure file


d,l-mixture, METHYL ESTER ; m/e 303, 301, 285, 275, 273, 271, 260, 257, 253, 245, 243, 231, 217, 213, 206, 199, 187, 180, 173, 159, 145, 131, 119, 117, 105, 93, 91(100%), 81, 79, 71, 67, 59, 57, 55 (Ref. 1100)


The compound is produced when the microsomes of monkey seminal vesicle is incubated with 5,8,11,14,17-eicosapentaenoic acid (Ref. 0081).



172
Anandamide(20:4, n-6)
N-Arachidonoylethanolamine
XPR7001
Keizo Waku
C22H37NO2 347.535 Download ChemDraw structure file
Anandamide inhibited the specific binding of cannabinoid probe to synaptosomal membrane and produced a concentration-dependent inhibition of the electrically evoked twitch response of the mouse vas deferens, a characteristic effect of psychotropic cannabinoids. Anandamidefunctions as a natural ligand for the cannabinoid receptor (CBl). Binding to rat brain CB1, Ki(nM) = 39.pm5.7(Ref. 7001)
soluble in organic solvent(Ref. 7001)
1H NMR spectra.The peaks attributed to double bond protons(d5.30 to 5.45, multiplet)were coupled with those of protons that have the chemical shifts of doubly allylic protons(d2.75 to 2.90, multiplet). (Ref. 7001)
CID measurement of m/z 348 MH+ion gave rise to the following significant fragments:m/z 287, 245 ,203, 62 (highest abundance), and 44. m/z 62 fragment ion is HOCH2CH2NH2+. (Ref. 7001)

1-Anthroyl derivatives of various types of N-acylethanolamine were separated by reverse phase HPLC (Ref. 7005)
[Chromatogram 7001]
Originally found in porcine brain (Ref. 7006). It was also found in rat brain (Ref. 7005)and testis(Ref. 7008)
N-Arachidonoylethanolamine was synthesized from arachidonyl chloride and ethanolamine. The product was purified by silica gel column chromatography. It was 97 % pure as judged by GC-MS. (Ref. 7001)
It was biosynthesized from N-acylphosphatidylethanolamine by phospholipase D like reaction in rat brain microsomes (Ref. 7005).It was hydrolyzed by the anandamide amidohydrolase in rat brain microsomes to ethanolamine and arachidonic acid (Ref. 7007).
1. CB1(Ref. 7002) 2. CB2(Ref. 7003) 3. CB1A(Ref. 7004)

173
Anandamide (20:2, n-6)
N-cis-11,14-eicosadienoyl ethanolamine
XPR7002
Keizo Waku
C22H27NO2 337.455 Download ChemDraw structure file
Binding of 20:2 anandamide to the Brain cannabinoid receptor (CB1)Ki (nM)= 1500(Ref. 7001)
oil (Ref. 7001)
soluble in organic solvent (Ref. 7001)
1H NMR (CDCl3) d5.90 (br s, 1H), 5.30-5.38 (m, 4H), 3.70 (t, J=4.4Hz, 2H), 3.40-3.45 (m, 2H), 2.78 (t, J=5.4Hz,2H), 2.18 (t, J=7.1 Hz, 2H), 2.00-2.12 (m, 2H), 1.50-1.70 (m, 8H), 1.30 (br s, 8H), 0.89 (t, J=7.5 Hz, 3H). (Ref. 7001)




Anandamide (20:2, n-6) was prepared from cis-11, 14-eicosadienoyl chloride and ethanolamine in 81 % yield as a colorless oil. (Ref. 7001)
Chemically synthesized. (Ref. 7001)


174
Anandamide (18:3, n-6)
N-cis-6,9,12-octadecatrienoylethanolamine
XPR7003
Keizo Waku
C20H35NO2 321.497 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CB1) Ki (nM)= 4600pm300 (Ref. 7001)
oil (Ref. 7001)
soluble in organic solvent (Ref. 7001)
1H NMR (CDCl3) d6.13 (br s 1H), 5.29-5.41 (m, 6H), 3.71 (t, J=5.1 Hz, 2H), 3.41 (q, J=5.1 Hz, 2H), 2.80 (t, J=5.7 Hz, 4H), 2.20 (t, J=8.1 Hz, 2H), 2.00-2.12 (m, 4H), 1.60-1.70 (m, 4H), 1.31 (brs 6H), 0.88 (t, J=7.5Hz, 3H). (Ref. 7001)




This compound was synthesized from cis-octadecatrienoyl chloride and ethanolamine in 79 % yield as a colorless oil. (Ref. 7001)



175
Anandamide (18:2, n-6)
N-cis-9-cis-12-Octadecadienoylethanolamine
XPR7004
Keizo Waku
C20H37NO2 323.513 Download ChemDraw structure file
The binding of this compound to the brain cannabinoid receptor (CBl) was scarecely found Ki(nM)>2500(Ref. 7001)
oil (Ref. 7001)
soluble in organic solvents (Ref. 7001)
1H NMR (CDCl3) d5.90 (br s 1H), 5.30-5.39 (m, 4H), 3.72 (t, J=5.1 Hz, 2H), 3,42 (q, J=5.4 Hz, 2H), 2.76 (t, J=5.7 Hz, 2H), 2.20 (t, J=8.1 Hz, 2H), 2.01-2.06 (m, 4H), 1.60-1.70 (m, 2H), 1.30 (br s 14H), 0.88 (t, J=7.2Hz, 3H). (Ref. 0001)




Anandamide (l8:2, n-6) was prepared from cis-9,cis-12-octadecadienoylchloride and ethanolamine in 84 % yield as a colorless oil. (Ref. 7001)
This compound was found in rat brain and testis. (Ref. 7002/7003)


176
Anandamide (20:3, n-3)
N-cis-11, 14,17-eicosatrienoylethanolamine
XPR7005
Keizo Waku
C22H39NO2 349.551 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CB1)is scarecely found Ki (nM)> 10000(Ref. 7001)
oil (Ref. 7001)
soluble in organic solvent (Ref. 7001)
1H NMR (CDCl3) d5.90 (br s 1H), 5.30-5.39 (m, 4H), 3.72 (t, J=5.1 Hz, 2H), 3.42 (q, J=5.4 Hz, 2H), 2.80 (t, J=5.7 Hz, 4H), 2.20 (t, J=8.l Hz, 2H), 2.01-2.12 (m, 4H), 1.56-1.67 (m, 4H), 1.26 (br s 10H), 0.97 (t, J=7.5 Hz, 3H). (Ref. 7001)




This compound was prepared from cis-11,14,17-eicosatrienoyl chloride and ethanolamine in 50 % yield as a colorless oil. (Ref. 7001)



177
Anandamide (18:4, n-3)
N-cis-6,9,12,15-Octadecatetraenoylethanolamine
XPR7006
Keizo Waku
C20H33NO2 319.482 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CB1) Ki (nM)>1000 (Ref. 7001)
oil (Ref. 7001)
soluble in organic solvent (Ref. 7001)
1H NMR (CDCl3) d5.92 (br s 1H), 5.33-5.40 (m, 8H), 3.72 (t, J=5.1 Hz, 2H), 3.42 (q, J=5.2 Hz, 2H), 2.79-2.84 (m, 6H), 2.22 (t, J=7.8Hz, 2H), 2.02-2.12 (m, 4H), 1.60- 1.72 (m, 2H), 1.38-1.48 (m, 2H), 0.98 (t, J= 7.5 Hz, 3H). (Ref. 7001)




cis-6,9,12,15-Octadecatetraenoyl chloride and ethanolamine in 76 % yield as a colorless oil.(Ref. 7001)



178
Anandamide (18:3, n-3)
N-cis-9,12,15-Octadecatrienoylethanolamine
XPR7007
Keizo Waku
C20H35N02 303.505 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CB1) Ki (nM) = 4600pm300(Ref. 7001)
oil (Ref. 7001)
soluble in organic solvent (Ref. 7001)
1H NMR (CDCl3) d6.13 (br s, 1H), 5.29-5.42 (m, 6H), 3.71 (t, J=5.1 Hz, 2H), 3.41 (q, J=5.1 Hz, 2H), 2.80 (t, J=5.7 Hz, 4H), 2.20 (t, J=8.1 Hz, 2H), 2.04-2.12 (m, 4H), 1.63 (t, J=6.9 Hz, 2H), 1.31 (br s 10H), 0.97 (t, J=7.5 Hz, 3H). (Ref. 7001)




This compound was prepared from cis-9,12,15-octadecatrienoyl chloride and ethanolaminein 74 .5% yield as a colorless oil. (Ref. 7001)
This compound was not found in rat brain and testis. (Ref. 0002/0003)


179
Anandamide (20:5, n-3)
N-cis-5,8, 11,14,17-eicosapentaenoylethanolamine
XPR7008
Keizo Waku
C22H35N02 327.527 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CB1) Ki (nM) = 162.3pm13.6 (Ref. 7001)
oil (Ref. 7001)
soluble in organic solvent (Ref. 7001)
1H NMR (CDCl3) d5.90 (br s 1H), 5.22-5.42 (m, 10H), 3.71 (t, J= 5.1 Hz, 2H), 3.41 (q, J=4.9 Hz, 2H), 2.79-2.86 (m, 8H), 2.05-2.22 (m, 6H), 1.60-1.72 (m, 2H), 0.97 (t, J=7.9 Hz, 3H) (Ref. 7001)




This compound was synthesized from cis-5,8,11,14,17-eicosapentaenoyl chloride and ethanolamine in 72% yield as a colorless oil. (Ref. 7001)



180
Anandamide (22:6, n-3)
N-cis-4,7,10,13,16,19-docosahexanoylethanolamine
XPR7009
Keizo Waku
C24H37N02 353.564 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CB1) Ki (nM) = 324.1pm9.2 (Ref. 7001)
oil (Ref. 7001)
soluble in organic solvent (Ref. 7001)
1H NMR (CDCl3) d5.90 (br s 1H), 5.28-5.42 (m, 12H), 3.72 (t, J=5.1 Hz, 2H), 3.41 (q, J=4.9 Hz, 2H), 2.77-2.88 (m, 10H), 2.42 (t, J=8.1 Hz, 2H), 2.22-2.30 (m, 2H), 2.02-2.14 (m, 2H), 0.97 (t,J=7.8 Hz, 3H) (Ref. 7001)




This compound was synthesized from docosahexanoyl chloride and ethanolamine in 65 % yield as a colorless oil. (Ref. 7001)



181
Anandamide (20:l, n-9)
N-cis-11 -eicosaenoylethanolamine
XPR7010
Keizo Waku
C22H43N02 335.590 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CB1), Ki (nM)>1000(Ref. 7001)
67 - 68degC (Ref. 7001)
soluble in organic solvent (Ref. 7001)
1H NMR (CDCl3) d5.90 (br s 1H), 5.32-5.36 (m, 2H), 3.70 (t, J=5.1 Hz, 2H), 3.40-3.42 (m, 2H), 2.18 8t, J=7.8 Hz, 2H), 1.96-2.02 (m, 4H), 1.54-1.63 (m, 6H), 0.86 (t, J=6.1 Hz, 3H). (Ref. 7001)




This compound was synthesized from cis-11-eicosaenoylchloride and ethanolamine in 70 % yield. (Ref. 7001)



182
Anandamide (20:3, n-6)
dihomo-g-linolenoylethanol amide
XPR7011
Keizo Waku
C22H39NO2 349.551 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CB1), Ki(nM)=53.4 pm5.5 (Ref. 7001)
colorless oil, soluble in organic solvent (Ref. 7001)





This compound was synthesized from di-homo-g-linoleoylchloride and ethanolamine. (Ref. 7001)



183
Anandamide (22:4, n-6)
docosatetraenoylethanolamide
XPR7012
Keizo Waku
C24H41NO2 375.588 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor CB1,Ki= 34.4pm3.2 (Ref. 7001)
colorless oil (Ref. 7001)
soluble in organic solvent (Ref. 7001)





This compound was synthesized from docosatetraenoylchloride and ethanolamine. (Ref. 7001)



184
Anandamide (16:0)
palmitoylethanolamide
XPR7013
Keizo Waku
C18H37NO2 299.492 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CB1)was not found. (Ref. 7001)
100-101degC (Ref. 7001)
1H NMR (CDCl3) d6.00 (br s 1H), 3.72 (t, J=5.1 Hz, 2H),




This compound was synthesized from palmitoylchloride and ethanolamine in 79 % yield. (Ref. 7001)



185
oleoylamide
XPR7014
Keizo Waku
C20H38NO2 324.521 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CBl)was not found. (Ref. 7001)
74-75degC(Ref. 7001)
1H NMR (CDCl3) d5.42 (br s, 2H), 5.32-5.36 (m, 2H), 2.22 (t, J=7.8 Hz 2H), 1.98-2.02 (m,6H), 1.62-1.66 (m, 4H), 1.27-1.31 (m, 16H), 0.88 (t, J=6.9Hz, 3H). (Ref. 7001)




This compound was synthesized from oleic acid and ammonium hydroxide in 60 % yield.(Ref. 7001)



186
cis-5,8,11,14-eicosatetrayoyl ethanolamide
XPR7015
Keizo Waku
C22H29NO2 339.471 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CBl)was not found. (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d6.15 (br s 1H), 3.73 (t, J=




This compound was prepared from cis-5,8,11,14-eicosatetrayoic acid and ethanolamine in 64% yield.(Ref. 7001)



187
anandamide 0-phosphate
XPR7016
Keizo Waku
C22H38NO5P 427.515 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CBl),Ki(nM)= 190.8pm11.1(Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.34-5.42 (m, 8H), 3.98 (br s 2H), 3.46 (br s 2H), 2.77-2.81 (m, 6H), 2.26 (t, J=6.8Hz, 2H), 2.00-2.06 (m, 4H), 1.60-1.69 (m, 2H), 1.29-1.42 (m, 6H), 0.88 (t, J=6.9Hz,3H) (Ref. 7001)




This compound was synthesized from N-hydroxysuccinimide ester of arachidonic acid and O-phosphoethanolamine in 60% yield. (Ref. 7001)



188
N-arachidonoylglycine
XPR7017
Keizo Waku
C22H35NO3 361.518 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CBl),Ki(nM)>10000(Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d6.25 (br s 1H), 5.30-5.37 (m, 8H), 4.05 (d, J=5.1Hz, 2H), 2.76-2.82 (m, 6H), 2.22 (t, J=7.8Hz, 2H), 2.04-2.18 (m, 2H), 1.70-1.82 (m, 4H), 1.25-1.35 (m, 6H), 0.89 (t, J=7.1Hz, 3H) (Ref. 7001)




This compound was synthesized from arachidonoylchloride and glycine in potassium hydroxide solution. Yield is 34%. (Ref. 7001)



189
N-arachidonoyl-D-serine
XPR7018
Keizo Waku
C23H37NO4 391.544 Download ChemDraw structure file
Binding of this compoud to the brain cannabinoid receptor (CBl), Ki(nM)>10000 (Ref. 7001)
colorless oil (Ref. 7001)
d4-25= -8.9deg(C=1,CHCl3)(Ref. 7001)
1H NMR (CD3OD) d5.30-5.43 (m, 8H), 4.49 (t, J=4.8Hz, 1H), 3.80-3.88 (m, 2H), 2.80-2.86 (m, 6H), 2.30 (t, J=6.6Hz, 2H), 2.04-2.18 (m, 4H), 1.66-1.72 (m, 2H), 1.29-1.39 (m, 6H), 0.90 (t, J=6.9Hz, 3H) (Ref. 7001)




This compound was synthesized from D-serine and N-hydroxysuccinimide ester of arachidonic acid. The yield was 60 %. (Ref. 7001)



190
N-arachidonoyl-L-serine
XPR7019
Keizo Waku
C23H37NO4 391.544 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor(CB1),Ki(nM)>10000 (Ref. 7001)
colorless oil (Ref. 7001)
d4-25= +8.9deg (Ref. 7001)
1H NMR (CD3OD) d5.33-5.40 (m, 8H), 4.50 (t, J=4.8 Hz, 1H), 3.78-3.90 (m, 2H), 2.80-2.86 (m, 6H), 2.29 (t, J=6.6Hz, 2H), 2.04-2.18 (m, 4H), 1.64-1.72 (m, 2H), 1.29-1.39 (m, 6H), 0.90 (t, J=7.2Hz, 3H) (Ref. 7001)




this compound was synthesized from D-serine and N-hydroxysuccinimide ester of arachidonicacid. yield is 55%. (Ref. 7001)



191
N-ethyl arachidonoyl amide
XPR7020
Keizo Waku
C22H37NO 331.535 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CB1), Ki (nM)= 34.0pm2.7 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.31-5.41 (m, 8H), 3.22-3.34 (m, 2H), 2.78-2.84 (m, 6H), 1.68-1.78 (m, 4H), 1.22-1.40 (m, 6H), 1.13 (t, J=7.3, 3H), 0.88 (t, J=7.1H, 3H) (Ref. 7001)




This compound was synthesized from arachidonoyl chloride and ethylamine, yield is 73 %. (Ref. 7001)



192
N-methyl arachidonoyl amide
XPR7021
Keizo Waku
C22H37NO 331.535 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CB1),Ki(nM)= 60.0pm7.4 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.80 (br s, lH), 5.30-5.40 (m, 8H), 2.78-2.85 (m, 9H), 2.03-2.19 (m, 6H), 1.66-1.76 (m, 2H), 1.25-1.34 (m, 6H), 0.88 (t, J=9Hz, 3H) (Ref. 7001)




This compound was synthesized from arachidonoylchloride and methylamine.Yield is 67 %.(Ref. 7001)



193
arachidonoyl amide
XPR7022
Keizo Waku
C22H33NO 327.504 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CBl),Ki (nM)>1000 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.82 (br s, lH), 5.31-5.42 (m, 8H), 2.79-2.85 (m, 6H), 2.23 (t, J=8.1Hz, 2H), 2.04-2.15 (m, 4H), 1.70-1.77 (m, 2H), 1.25-1.38 (m, 6H), 0.89 (t, J=6.8Hz,3H). (Ref. 7001)




This compound was synthesized from arachidonyl chloride and ammonium hydroxide. Yield is 80 %. (Ref. 7001)



194
N-propylarachidonoyl amide
XPR7023
Keizo Waku
C23H39NO 345.562 Download ChemDraw structure file
Binding of this compound to the rat brain cannabinoid receptor (CBl), Ki= 11.7pm2.1 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.62 (br s, 1H), 5.26-5.38 (m, 8H), 3.13 (q, J=6Hz, 2H), 2.62-2.80 (m, 6H), 2.10 (t, J=7.3Hz, 2H), 1.96-2.06 (m, 4H), 1.56-1.66 (m, 2H), 1,38-1.48 (m, 2H), 1.20-1.32 (m, 6H), 0.79-0.86 (m, 6H) (Ref. 7001)




This compound was synthesized from arachidonoylchloride and n-propylamine.Yield 71%. (Ref. 7001)



195
N-isopropyl arachidonoyl amide
XPR7024
Keizo Waku
C23H39NO 345.562 Download ChemDraw structure file
Binding of this compound to the rat brain cannabinoid receptor (CBl), Ki (nM)= 13.6pm1.1(Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.30-5.44 (m, 8H), 4.02-4.12 (m, 1H), 2.76-2.86 (m, 6H), 2.02-2.16 (m, 6H), 1.66-1.76 (m, 2H), 1.26-1.38 (m, 6H), 1.14 (d, J=6.6Hz, 6H), 0.89 (t, J=6.9Hz, 3H) (Ref. 7001)




This compound was synthesized from arachidonoylchloride and isopropylamine.Yield 46%.(Ref. 7001)



196
N-butylarachidonoyl amide
XPR7025
Keizo Waku
C24H41NO 359.588 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CB1),Ki (nM)= 235.7pml4.2 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.26-5.44 (m, 8H), 3.24 (q, J=6Hz, 2H), 2.76-2.86 (m, 6H), 2.02-2.22(m, 6H), 1.64-1.78 (m, 2H), 1.22-1.56 (m, 10H), 0.86-0.98 (m, 6H). (Ref. 7001)




This compound was synthesized from arachidonoylchloride and n-butylamine. Yield is 56%. (Ref. 7001)



197
N-tert-butyl arachidonoyl amide
XPR7026
Keizo Waku
C24H41NO 359.588 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CBl),Ki(nM)>1000 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CCCl3) d5.30-5.40 (m,




This compound was synthesized from arachidonoyl chloride and tert-butylamine. Yield 72 % (Ref. 7001)



198
N-amyl arachidohoyl amide
XPR7027
Keizo Waku
C25H43NO 373.615 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CBl),Ki(nM)>l000 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.70 (br s lH), 5.23-5.33 (m, 8H), 3.15 (q, J=3Hz, 2H), 2.71-2.77(m, 6H), 1.97-2.16 (m, 6H), 1.58-1.68 (m, 2H), 1.18-1.42 (m, l2H), 0.79-0.85 (m, 6H). (Ref. 7001)




This compound was synthesized from arachidonoylchloride and amylamine.Yield 70 % (Ref. 7001)



199
N-(3-methylbutyl)arachidonoyl amide
XPR7028
Keizo Waku
C25H43NO 373.615 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CBl),Ki(nM)= 575.1pm35.3 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.30-5.42 (m, 8H), 3.26 (q, J=3Hz, 2H), 2.76-2.86 (m, 6H), 2.02-2.20 (m, 6H), 1.68-1.78 (m, 2H), 1.54-1.64 (m, lH), 1.26-1.40 (m, 8H), 0.82-0.96 (m, 9H) (Ref. 7001)




This compound was synthesized from arachidonoylchloride and isoamylamine.Yield 7l % (Ref. 7001)



200
N-(1,1-dimethylpropyl)arachidonoyl amide
XPR7029
Keizo Waku
C25H43NO 373.615 Download ChemDraw structure file
Binding of this compound to the brain cannabinoid receptor (CBl),Ki(nM)= 446.7pm40.3 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.28-5.38 (m, 8H), 5.10 (br s, lH), 2.67-2.82 (m, 6H), 2.04-2.12 (m, 6H), 1.66-1.76 (m, 4H), 1.24-1.32 (m, l2 H), 0.81-0.90 (m, 6H). (Ref. 7001)




This compound was synthesized from arachidonoyl chloride and 1,1-dimethylpropylamine.Yield 58 % (Ref. 7001)



201
N-((R-(-)-1-methylpropyl)arachidonoyl amide
XPR7030
Keizo Waku
C24H41NO 359.588 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl),Ki(nM)= 239.9pm63.8 (Ref. 7001)
colorless oil (Ref. 7001)
d4-25= -7.08deg(c=l,EtOH)(Ref. 7001)
1H NMR (CDCl3) d5.30-5.42 (m, 8H), 5.20 (br s, lH), 3.86-4.00 (m, lH), 2.75-2.86 (m, 6H), 2.00-2.20 (m, 6H), 1.65-1.80 (m, 2H), 1.22-1.50 (m, 8H), 1.10 (d, J=7.5Hz, 3H),0.82-0.92 (m, 6H). (Ref. 7001)




This compound was synthesized from arachidonoyl chloride and (R)-(-)-sec-butylamine.Yield 63 % (Ref. 7001)



202
N-((S)-(+)-1-methylpropyl)arachidonoyl amide
XPR7031
Keizo Waku
C24H41NO 359.588 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 377.2pm55.4 (Ref. 7001)
colorless oil (Ref. 0001)
d4-25= +7.08deg (C=1, EtOH) (Ref. 0001)
1H NMR (CDCl3) d5.30-5.42 (m, 8H), 5.22 (br s, lH), 3.88-3.98 (m, lH), 2.75-2.90 (m, 6H), 2.00-2.20 (m, 6H), 1.65-1.76 (m, 2H), 1.22-1.50 (m, 8H), 1.12 (d, J=7.5Hz, 3H), 0.82-0.96 (m, 6H). (Ref. 7001)




This compound was synthesized from arachidonoylchloride and (S)-(+)-sec-butylamine. Yield 55%. (Ref. 7001)



203
N-(3-hydroxypropyl)arachidonoylamide
XPR7032
Keizo Waku
C23H39NO2 361.561 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl),Ki(nM)= 29.9pm0.4(Ref. 7001)
colorless oil (Ref. 0001)
1H NMR (CDCl3) d6.42 (br s lH), 5.22-5.38 (m, 8H), 3.90 (br s, lH), 3.54 (t, J=5.5 Hz, 2H), 3.32 (q, J=6Hz, 2H), 2.62-2.80 (m, 6H), 1.92-2.18 (m, 6H), 1.50-1.70 (m, 4H), 1.20-1.3 (m, 6H), 0.90 (t, J=7Hz, 3H). (Ref. 7001)




This compound was synthesized from arachidonoyl chloride and 3-amino-l-propanol. Yield 68%. (Ref. 7001)



204
N-(1,1-dimethyl-2-hydroxyethyl)arachidonoyl amide
XPR7033
Keizo Waku
C24H41NO2 375.588 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 161.8pm34.1 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.50 (br s, 1H), 5.28-5.40 (m,8H), 3.57 (s, 2H), 2.78-2.90 (m, 6H), 2.02-2.20 (m, 6H), 1.62-1.74 (m, 2H), 1.20-1.40 (m, 12H), 0.89 (t, J=7.1Hz, 3H). (Ref. 7001)




This compound was synthesized from arachidonoyl chloride and 2-amino-2-methyl-l-propanol.Yield 48 %. (Ref. 7001)



205
N-(5-hydroxypentyl)arachidonoyl amide
XPR7034
Keizo Waku
C25H43NO2 389.614 Download ChemDraw structure file
Binding to the rat brain cannabinoid receptor (CBl), Ki(nM)= 497.4pm27.1 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.60 (br s lH), 5.22-5.42 (m, 8H), 3.64 (t, J=5.5Hz, 2H), 3.20-3.32 (m, 2H), 2.76-2.89 (m, 6H), 2.00-2.22 (m, 6H), 1.90 (br s lH), 1.20-1.80 (series of m, l4H), 0.89 (t, J=7.1Hz, 3H). (Ref. 7001)




This compound was synthesized from arachidonoylchloride and 5-amino-l-pentanol. Yield 6l %. (Ref. 7001)



206
N-(2-methoxyethyl)arachidonoyl amide
XPR7035
Keizo Waku
C23H39NO 345.562 Download ChemDraw structure file
Binding to the rat brain cannabinoid receptor (CBl), Ki(nM)= 85.2pm3.8 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.80 (br s lH), 5.30-5.42 (m, 8H), 3.45 (d, J=2.1Hz, 4H), 3.35 (s, 3H), 2.75-2.85 (m, 6H), 2.00-2.20 (m, 6H), 1.62-1.80 (m, 2H), 1.20-1.40 (m, 6H), 0.89 (t, J=6.8Hz, 3H) (Ref. 7001)




This compound was synthesized from arachidonoylchloride and methoxyethylamine. Yield 4l%. (Ref. 7001)



207
N'-arachidonoyl-N''-diethylethylenediamine
XPR7036
Keizo Waku
C26H46N2O 402.656 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki(nM)>1000 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d6.10 (br s lH), 5.26-5.42 (m, 8H), 3.22-3.30 (m, 2H), 2.76-2.90 (m, 6H), 2.50-2.62 (m, 6H), 1.66-1.80 (m, 2H), 1.20-1.40 (m, 6H), 1.02 (t, J=7.1Hz, 6H), 0.89 (t, J=6.5Hz, 3H). (Ref. 7001)




This compound was synthesized from arachidonoylchloride and N,N-diethylenediamine. Yield 70 %. (Ref. 7001)



208
N,N-dimethyl arachidonoyl amide
XPR7037
Keizo Waku
C22H37NO 331.535 Download ChemDraw structure file
Binding to the rat brain cannabinoid receptor (CBl), Ki(nM)>1000 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.24-5.44 (m, 8H), 2.99 (s, 3H), 2.94 (s, 3H), 2.76-2.86 (m, 6H), 2.31 (t, J=7Hz, 2H), 2.00-2.18 (m, 4H), 1.66-1.78 (m, 2H), 1.20-1.38 (m, 6H), 0.89 (t, J=7.lHz, 3H)(Ref. 7001)




This compound was synthesized from arachidonoyl chloride and dimethylamine. Yield 59 %. (Ref. 7001)



209
N,N-diethyl arachidonoyl amide
XPR7038
Keizo Waku
C24H41NO 359.588 Download ChemDraw structure file
Binding to the rat brain cannabinoid receptor (CBl), Ki(nM)>1000 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.30-5.42 (m, 8H), 3.20-3.42 (m, 4H), 2.76-2.86 (m, 6H), 2.29 (t, J=7.l Hz, 2H), 2.00-2.20 (m, 4H), 1.60-1.80 (m, 2H), 1.22-1.40 (m, 6H), 1.04-1.20 (m, 6H), 0.90 (t, J=6.1Hz, 3H). (Ref. 7001)




This compound was synthesized from arachidonoyl chloride and diethylamine. Yield 66%.(Ref. 7001)



210
N-methyl -N-(2-hydroxyethyl)arachidonoyl amide
XPR7039
Keizo Waku
C23H39NO2 361.561 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki(nM)>10000 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.30-5.42 (m, 8H), 3.77 (t, J=5Hz, 2H), 3.55 (t, J=7.8Hz,2H), 2.04-2.15 (m, 4H), 1.64-1.75 (m, 2H), 1.25-1.38 (m, 6H), 0.89 (t, J=6.8Hz, 3H). (Ref. 7001)




This compound was synthesized from arachidonoyl chloride and 2-(methylamino)ethanol. Yield 75 %.(Ref. 7001)



211
N-ethyl -N-(2-hydroxyethyl)arachidonoyl amide
XPR7040
Keizo Waku
C24H41NO2 375.588 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki(nM)>10000 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.31-5.42 (m, 8H), 3.75 (t, J=4.6 Hz, 2H), 3.51 (t, J=4.6Hz, 2H), 3.34(q, J=7.l Hz, 2H), 3.34 (q, J=7.l Hz, 2H), 2.79-2.86 (m, 6H), 2.35 (t, J=7.8Hz, 2H), 2.04-2.15(m, 4H), 1.64-1.77 (m, 2H), 1.25-1.40 (m, 6H), 1.19 (t, J=7.l Hz, 3H), 0.89 (t, J=7.lHz, 3H).(Ref. 7001)




This compound was synthesized from arachidonoyl chloried and 2-(ethylamino)ethanol. Yield 83 %. (Ref. 7001)



212
N-propyl -N-(2-hydroxyethyl)arachidonoyl amide
XPR7041
Keizo Waku
C25H43NO2 389.614 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki(nM)>10000 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.30-5.42 (m, 8H), 3.76 (t, J=4.9 Hz, 2H), 3.52 (t, J=4.4 Hz, 2H), 3.24 (t, J=8.l Hz, 2H), 2.79-2.86 (m, 6H), 2.35 (t, J=8.l Hz, 2H), 2.02-2.20 (m, 4H), 1.54-1.76 (m, 4H), 1.25-1.38 (m, 6H), 0.86-0.89 (m, 6H). (Ref. 7001)




This compound was synthesized from arachidonoyl chloride and 2-(propylamino)ethanol. Yield 6l %. (Ref. 7001)



213
N,N-(di-2-hydroxyethyl)arachidonoylamide
XPR7042
Keizo Waku
C24H41NO3 391.587 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki>10000 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.60-5.42 (m, 8H), 3.83 (t, J=4.9Hz, 2H), 3.77 (t, J=5.lHz, 2H), 3.54(t, J=5.1Hz, 2H), 3.49 (t, J=4.9Hz, 2H), 2.77-2.86 (m, 6H), 2.40 (t, J=7.3Hz, 2H), 2.02-2.16 (m, 4H), 1.69-1.76 (m, 2H), 1.25-1.38 (m, 6H), 0.88 (t, J=6.6Hz, 3H). (Ref. 7001)




This compound was synthesized from arachidonoyl chloride and diethanolamine. Yield 45 %. (Ref. 7001)



214
N-hydroxy -N-arachidonoyl amide
XPR7043
Keizo Waku
C20H33NO 303.482 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki (nM)>1000 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.30-5.43 (m, 8H), 2.78-2.86 (m, 6H), 2.02-2.17 (m, 6H), l.70-1.78(m, 2H), 1.22-1.38 (m, 6H), 0.89 (t, J=6.9 Hz, 3H). (Ref. 7001)




This compound was synthesized from arachidonoyl chloride and hydroxylamine hydrochloride.Yield 49%. (Ref. 7001)



215
(pm)-N-(1-methyl-2-hydroxy-2-phenylethyl)arachidonoyl amide
XPR7044
Keizo Waku
C29H43NO2 437.657 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki(nM)>1000 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d7.27-7.35 (m, 5H), 5.54 (br s , lH), 5.63-5.41 (m, 8H), 4.84 (br s, lH),4.31-4.36 (m, lH), 3.60 (br s, lH), 2.78-2.85 (m, 6H), 2.01-2.22 (m, 6H), 1.67-1.77 (m, 2H),1.25-1.37 (m, 6H), 1.01 (d, J=7.l Hz, 3H), 0.89 (t, J=7.l Hz, 3H). (Ref. 7001)




This compound was synthesized from arachidonoylchloride and (pm)phenylpropanolamine.Yield 67 %. (Ref. 7001)



216
a-methyl anandamide
XPR7045
Keizo Waku
C23H39NO 345.562 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 32.5pm5.1 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d6.10 (br s lH), 5.22-5.40 (m, 8H), 3.75 (t, J=5.1Hz, 2H), 3.42 (q, J=4.9 Hz, 2H), 2.74-2.86 (m, 6H), 2.20-2.30 (m, lH), 2.00-2.12 (m, 4H), 1.68-1.80 (m, lH), 1.20-1.50 (m, 6H), 1.16 (d, J=6.6Hz, 3H), 0.89 (t, J=6.9Hz, 3H). (Ref. 7001)




This compound was synthesized from arachidonic acid and ethanolamine. Yield 82 %. (Ref. 7001)



217
a,a-dimethyl anandamide
XPR7046
Keizo Waku
C24H41NO 359.588 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 25.5pm2.8 (Ref. 7001)
colorless oil(Ref. 7001)
1H NMR (CDCl3) d6.10 (br s, lH), 5.30-5.42 (m, 8H), 3.75 (t, J=5.l Hz, 2H), 3.42 (q, J=4.9Hz, 2H), 2.78-2.86 (m, 6H), 2.00-2.10 (m, 4H), 1.50-1.62 (m, 4H), 1.24-1.40 (m, 4H), 1.22 (s, 6H), 0.90 (t, J=6.9 Hz, 3H). (Ref. 7001)




This compound was synthesized from arachidonic acid and ethanolamine. Yield 47 %.(Ref. 7001)



218
N-propyl a-methyl arachidonoyl amide
XPR7047
Keizo Waku
C24H41NO 359.588 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 7.4pm0.2 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.20-5.45 (m,




This compound was synthesized from arachidonic acid and propylamine. Yield 84 %. (Ref. 7001)



219
N-propyl a,a-dimethylarachidonoyl amide
XPR7048
Keizo Waku
C25H43NO 373.615 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 6.9pm0.7 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.60 (br s, lH), 5.30-5.40 (m, 8H), 3.20-3.23 (m, 2H), 2.79-2.84 (m, 6H), 2.00-2.10 (m, 4H), 1.20-1.60 (series of m, 10H), 1.15 (s, 6H), 0.86-0.94 (m, 6H). (Ref. 7001)




This compound was synthesized from arachidonic acid and propylamine. Yield 70 %. (Ref. 7001)



220
N-isopropyl a-methyl arachidonoyl amide
XPR7049
Keizo Waku
C24H41NO 359.588 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 8.4pm1.1 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.30-5.42 (m, 8H), 4.02-4.14 (m, lH), 2.76-2.90 (m, 6H), 1.92-2.12 (m, 5H), 1.10-1.60 (series of m, 17H), 0.89 (t, J=6.9Hz, 3H). (Ref. 7001)




This compound was synthesized from arachidonic acid and isopropylamine. Yield 85 %. (Ref. 7001)



221
N-isopropyl a,a-dimethylarachidonoyl amide
XPR7050
Keizo Waku
C25H43NO 373.615 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 7.2pm0.1 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.20-5.50 (m, 9H), 4.04-4.14 (m, lH), 2.76-2.90 (m, 6H), 1.90-2.15 (m, 4H), 1.10-1.60 (series of m, 20H), 0.90 (t, J=6.9Hz, 3H). (Ref. 7001)




This compound was synthesized from arachidonic acid and isopropylamine. Yield 78 %. (Ref. 7001)



222
N-((S)-(+)-2-hydroxypropyl) a ,a-dimethylarachidonoyl amide
XPR7051
Keizo Waku
C25H43NO2 389.614 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 46.6pm2.2 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d5.95 (br s, lH), 5.30-5.42 (m, 8H), 3.92-3.96 (m, lH), 3.40-3.50 (m, lH), 3.02-3.23 (m, lH), 2.70-2.95 (m, 7H), 2.20-2.28 (m, lH), 2.00-2.15 (m, 4H), 1.70-1.75 (m, 2H) 1.20-1.52 (series of m, 14H), 0.89 (t, J=6.7Hz, 3H). (Ref. 7001)




This compound was synthesized from arachidonic acid and (S)-(+)-l-amino-2-propanol. Yield is 57 %. (Ref. 7001)



223
N-((R)-(-)-1-methyl-2-hydroxyethyl)a,a-dimethylarachidonoyl amide
XPR7052
Keizo Waku
C25H43NO2 389.614 Download ChemDraw structure file
Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 3l.lpm1.0 (Ref. 7001)
colorless oil(Ref. 7001)
1H NMR (CDCl3) d5.80 (br s, lH), 5.30-5.42 (m, 8H), 4.01-4.12 (m, lH), 3.60-3.68 (m, lH), 3.50-3.55 (m, lH), 2.98-3.01 (m, lH), 2.76-2.84 (m, 6H), 1.90-2.10 (m, 4H), 1.15-1.62 (series of m, l7H), 0.90 (t, J=7.1Hz, 3H). (Ref. 7001)




This compound was synthesized from arachidonic acid and (R)-(-)-2-amino-l-propanol. Yield is 45 %. (Ref. 7001)



224
N-((S)-(+)-1-methyl-2-hydroxyethyl)a,a-dimethylarachidonoyl amide
XPR7053
Keizo Waku
C25H43NO2 389.614 Download ChemDraw structure file
binding to the brain cannabinoid receptor (CBl), Ki(nM)= 191.4pm24.5 (Ref. 7001)
colorless oil(Ref. 7001)
1H NMR (CDCl3) d5.80 (br s, lH), 5.30-5.42 (m, 8H), 4.01-4.12 (m, lH), 3.60-3.68 (m, lH),3.50-3.55 (m, lH), 2.98-3.01 (m, lH), 2.76-2.84 (m, 6H), 1.90-2.10 (m, 4H), 1.15-1.62 (series of m, l7H), 0.90 (t, J=7.l Hz, 3H). (Ref. 7001)




This compound was synthesized from arachidonic acid and (S)-(+)-2-amino-l-propanol. Yield is 44 %. (Ref. 7001)



225
N-(1-methyl-2-hydroxyethyl)arachidonoylamide (R)
XPR7054
Keizo Waku
C23H39NO2 361.561 Download ChemDraw structure file
colorless liquid (Ref. 7012>.
d4-25= +10.9deg (Ref. 7012)
1H NMR (200 MHz, CDCl3) d(TMS)5.57 (m, 1H), 5.47-5.30 (m, 8H), 4.14-4.02 (m, 1H), 3.71-3.48 (m, 2H), 2.84-2.81 (m, 6H), 2.24-2.01 (m, 6H), 1.77-1.65 (m, 2H), 1.39-1.26 (m, 6H), 1.17 (d, J=3.46Hz, 3H), 0.89 (t, J=6.12Hz, 3H) (Ref. 7012)


Rf 0.3(5% MeOH/CHCl3) (Ref. 0012)

This compound was synthesized from arachidonic acid and (R)-(-)-2-amino-l-propanol in 69% yield. (Ref. 7012)



226
N-(2-methyl-2-hydroxyethyl)arachidonoylamide (S)
XPR7055
Keizo Waku
C23H39NO2 361.561 Download ChemDraw structure file
colorless oil (Ref. 7012)
d4-25= +9.44deg (Ref. 7012)
1H NMR (200 MHz, CDCl3) d(TMS)6.42 (m, 1H), 5.46-5.30 (m, 8H), 3.93-3.85 (m, 1H), 3.47-3.36 (m, 1H), 3.16-3.03 (m, 1H), 2.83-2.80 (m, 6H), 2.26-2.01 (m, 6H), 1.78-1.64 (m, 2H), 1.39-1.25 (m, 6H), 1.18 (d, J=3.18Hz, 3H), 0.89 (t, J=6.43 Hz, 3H) (Ref. 7012)


Rf 0.3(5% MeOH/CHCl3)

This compound was synthesized from arachidonic acid and (S)-(+)-l-amino-2-propanol in 63% yield. (Ref. 7012)



227
(16,16-dimethyldocosa-cis-5,8,11,14-tetraenoyl)ethanolamine
XPR7056
Keizo Waku
C26H45NO2 403.641 Download ChemDraw structure file
1H NMR (CDCl3) d5.79 (br s, lH, NH), 5.38 (m, 6H, 5,6,8,9,11,12-vinyl-H), 5.21 (m, 2H, 14,15-vinyl-H), 3.44, 3.43 (s&d overlapped, 4H, OCH2-CH2-N), 3.36 (s, 3H, OCH3), 2.92 (t, 2H, J=6.0Hz, 13-CH2), 2.80 (m, 4H, 7,10-CH2), 2.18 (t, 2H, J=7.7Hz, 2-CH2), 2.12 (m, 2H, 4-CH2), 1.71(p, 2H, J=7.7Hz, 3-CH2), 1.25 (m, 10H, 17-21CH2), 1.08 (s, 6H, gem-Me2), 0.86 (m, 3H, 22-CH2) (Ref. 7009)




This compound was synthesized from 16,16-dimethyldocosa-cis-5,8,11,14-tetraenoic methyl ester, NaCN and ethanolamine by heating (50degC in methanol)in a sealed tube. Yield 82 %. (Ref. 7009)



228
(R)-(16,16-dimethyldocosa-cis-5,8,11,14-tetraenoyl)-1'-hydroxy-2'-propylamine
XPR7057
Keizo Waku
C27H47NO2 417.668 Download ChemDraw structure file
1H NMR (CDCl3) d5.73 (br d, 1H, J=6.5Hz, NH), 5.36 (m, 6H, 5,6,8,9,11,12-vinyl-H), 5.21 (m, 2H, 14,15-vinyl-H), 4.04 (m, lH, N-CH), 3.64 (br m, 1H, OCH3), 3.52 (br m, 1H, OCH'), 3.18 (br s, 1H, OH), 2.91 (t, 2H, J=5.9Hz, 13-CH2), 2.79 (m, 4H, 7,10-CH2), 2.18 (t, 2H, J=7.6Hz,2-CH2), 2.08 (m, 2H, 4-CH2), 1.71 (p, 2H, J=7.4 Hz, 3-CH2), 1.27 (m, 10H, 17-21-CH2), 1.15 (d, 3H, J=6.8Hz, N-C-CH3), 1.08 (s, 6H, gem-Me2), 0.86 (m, 3H, 22-CH3) (Ref. 7009)




(R)-(16,16-Dimethyldocosa-cis-5,8,11,14-tetraenoic methyl ester (methyl alcohol solution), NaCN and (R)-(-)-2-amino-1-propanol are heated at 50degC overnight in a sealed tube. Yield 77%. (Ref. 7009)



229
(S)-(16,16-dimethyldocosa-cis-5,8,11,14-tetraenoyl)-2'-hydroxy-1'-propylamine
XPR7058
Keizo Waku
C27H47NO2 417.668 Download ChemDraw structure file
1H NMR (CDCl3) d5.99 (br s, 1H, NH), 5.36 (m, 6H, 5,6,8,9,11,12-vinyl-H), 5.18 (m, 2H,14,15-vinyl-H), 3.89 (m, 1H, O-CH), 3.42 (m, 1H, NCH), 3.10 (m, 1H, NCH'), 2.92 (t,2H, J=6.1Hz, 13-CH2), 2.81 (m, 4H, 7,10-CH2), 2.21 (t, 2H, J=7.6Hz, 2-CH2), 2.09 (m, 2H, 4-CH2), 1.71 (p, 2H, J=7.5Hz, 3-CH2), 1.25 (br, m, 10H, 17-21-CH2), 1.18 (d, 3H, J=6.3Hz, O-C-CH3), 1.08 (s, 6H, gem-Me2), 0.87 (m, 3H, 22-CH39) (Ref. 7009)




A methanol solution of the corresponding ester , NaCN and (S)-(+)-1-amino-2-propanol are heated 2-days in a hot block at 50degC. Yield 65%. (Ref. 7009)



230
(16,16-dimethyldocosa-cis-5,8,11,14-tetraenoyl)-2'-methoxyethylamine
XPR7059
Keizo Waku
C27H47NO2 417.668 Download ChemDraw structure file
1H NMR (CDCl3) d5.79 (br s, 1H, NH), 5.38 (m, 6H, 5,6,8,9,11,12-vinyl-H), 5.21 (m, 2H, 14,15-vinyl-H), 3.44,3.43 (s & d overlapped, 4H, O-CH2-CH2-N), 3.36 (s, 3H, OCH3), 2.92 (t, 2H, J=6.0Hz, 13-CH2), 2.80 (m, 4H, 7,10-CH2), 2.18 (t, 2H, J=7.7Hz, 2-CH2), 2.12(m, 2H, 4-CH2), 1.71 (p, 2H, J=7.7Hz, 3-CH2), 1.25 (m, 10H, 17-21-CH2), 1.08 (s, 6H, gem-Me2), 0.86 (m, 3H, 22-CH2) (Ref. 7009)




A methanol solution of the corresponding ester, NaCN and 2-methoxyethylamine heated 2-days in a hot block at 50degC.Yield 4l %. (Ref. 7009)



231
(16,16-dimethyldocosa-cis-5,8,11,14-tetraenoyl)propylamine
XPR7060
Keizo Waku
C27H47NO 401.668 Download ChemDraw structure file
1H NMR (CDCl3) d5.36 (overlap m, 7H, NH, 5,6,8,9,11,12-vinyl-H), 5.21 (m, 2H, 14,15-vinyl-H), 3.21 (q, 2H, J=6.7Hz, N-CH2), 2.92 (t, 2H, J=5.9Hz, 13-CH2), 2.80 (m, 4H, 7,10-CH2), 2.16,2.12 (t, m, 4H, J=7.6Hz, 2&4-CH2), 1.71 (p, 2H, J=7.4Hz, 3-CH2), 1.52 (hx, 2H, J=7.3Hz, 2'-CH2), 1.25 (m, 10H, 17-21-CH2), 1.08 (s, 6H, gem-Me2), 0.91,0.87 (t,m, 6H, 3'-CH3, 22-CH3) (Ref. 7009)




Heating a methanolic solution of the corresponding ester, NaCN and n-propylamine for 2days in a hot block at 50degC.Yield 44%. (Ref. 7009)



232
N-((R)-(-)-2-hydroxypropyl)a,a-dimethylarachidonoylamide
XPR7061
Keizo Waku
C25H43NO2 389.614 Download ChemDraw structure file
Binding to the brain cannabinoid receptor(CBl), Ki(nM)= 153.9pm30.0 (Ref. 7001)
colorless oil (Ref. 7001)
1H NMR (CDCl3) d 5.95 (br s, l H), 5.30-5.42 (m, 8H), 3.92-3.96 (m, 1H), 3.40-3.50 (m, 1H), 3.02-3.23 (m, 1H), 2.70-2.95 (m, 7H), 2.20-2.28(m, 1H), 2.00-2.15 (m, 4H), 1.70-1.75 (m, 2H), 1.20-1.52 (series of m, 14H), 0.89 (t, J=6.7 Hz, 3H), (Ref. 7001)




This compound was synthesized from arachidonic acid and (R)-(-)-l-amino-2-propanolyield 63%. (Ref. 7001)



233
N-eicosanoylethanolamine
XPR7062
Keizo Waku
C22H45NO2 355.598 Download ChemDraw structure file





This compound was synthesized from eicosanoylchloride and ethanolamine. (Ref. 7010)



234
N-eicosanoyl-(2'-fluoroethyl)amine
XPR7063
Keizo Waku
C22H44NOF 357.589 Download ChemDraw structure file





This compound was synthesized from eicosanoylchloride and 2-fluoroethylamine. (Ref. 7010)



235
arachidonoyl-N-(4-benzenesulfonamide)amide
XPR7064
Keizo Waku
C26H37N202S 3210.999 Download ChemDraw structure file





This compound was synthesized from arachidonoylchloride and 4-aminobenzenesulfonamide. (Ref. 7010)



236
arachidonoyl-(4'-bromobenzenesulfon)amide
XPR7065
Keizo Waku
C26H35O3SBr 507.524 Download ChemDraw structure file





This compound was synthesized from the reaction of arachidonic acid and p-bromobenzene sulfonamide in the presence of l-ethyl-3-[3-(dimethylamino)propyl]carbodiimide and 4-dimethylaminopyridene in methylene chloride at room temperature. (Ref. 7010)



237
arachidonoylmorpholine
XPR7066
Keizo Waku
C24H35NO 353.541 Download ChemDraw structure file





This compound was synthesized from arachidonoylchloride and morpholine. (Ref. 7010)



238
arachidonoyl-(2'-(4-bezenesulfonamide)ethyl)amide
XPR7067
Keizo Waku
C29H42NSO3 484.715 Download ChemDraw structure file





This compound was synthesized from arachidonoylchloride and 2-(4'-benzenesulfonamide)ethylamine. (Ref. 7010)



239
arachidonoyl-(2'-phenoxyethyl)amide
XPR7068
Keizo Waku
C29H41NO2 435.641 Download ChemDraw structure file





This compound was synthesized from arachidonoylchloride and phenoxyethylamine. (Ref. 7010)



240
arachidonoyl-(2'-fluoroethyl)amide
XPR7069
Keizo Waku
C23H36NOF 361.536 Download ChemDraw structure file





This compound was synthesized from arachidonoylchloride and 2-fluoroethylamine. (Ref. 7010)



241
2-methylarachidonoyl-(2'-fluoroethyl)amide
XPR7070
Keizo Waku
C23H38NOF 363.552 Download ChemDraw structure file





This compound was synthesized from 2-methylarachidonoylchloride and 2-fluoroethylamine. (Ref. 7010)



242
2-isopropylarachidonoyl-(2'-hydroxyethyl)amide
XPR7071
Keizo Waku
C26H43NO2 401.625 Download ChemDraw structure file





This compound was synthesized from 2-isopropylarachidonoylchloride and ethanolamine. (Ref. 7010)



243
5,8,11,14-all-cis-heneicosatetraenoylethanolamine
XPR7072
Keizo Waku
C23H40NO2 362.569 Download ChemDraw structure file
oil (Ref. 7011)
d0.88 (t, J=7.5Hz, 3H), 1.3 (br s 8H), 1.60-2.30 (m, 8H), 2.82 (br s, 7H), 3.30-3.50 (m, 2H), 3.65-3.80 (m, 2H), 5.20-5.55 (m, 8H), 6.05 (br s, 1H) (Ref. 7011)




This compound was synthesized from 5,8,11,14-all-cis-Heneicosatetraenoylchloride and ethanolamine. Yield 76 %. (Ref. 7011)



244
5,8,11,14-all-cis-docosatetraenoylethanolamine
XPR7073
Keizo Waku
C24H42NO2 376.596 Download ChemDraw structure file
oil (Ref. 7011)
d 0.88 (t, J=7.5Hz, 3H), 1.29 (br s, 10H), 1.60-1.90 (m, 2H), 2.0-2.30 (m, 6H), 2.65-2.95 (m, 7H), 3.30-3.55 (m, 2H), 3.65-3.80 (m, 2H), 5.20-5.55 (m, 8H), 5.9 (br s, 1H) (Ref. 7011)




This compound was synthesized from 5,8,11,14-all-cis-docosatetraenoylchloride and ethanolamine. Yield 35 %. (Ref. 7011)



245
5,8,11,14-all-cis-tricosatetraenoylethanolamine
XPR7074
Keizo Waku
C25H44NO2 390.622 Download ChemDraw structure file
oil (Ref. 7011)
d0.89 (t, J=7.5Hz, 3H), 1.29 (br s, 12H), 1.60-1.90 (m, 2H), 2.05-3.50 (m, 6H), 2.65-2.95 (m, 7H), 3.30-3.50 (m, 2H), 3.60-3.85 (m, 2H), 5.20-5.55 (m, 8H), 5.95 (br s, 1H) (Ref. 7011)




This compound was synthesized from 5,8,11,14-tricosatetraenoyl chloride and ethanolamine. Yield 57%. (Ref. 7011>



246
5,8,11,14-all-cis-tetracosanoylethanolamide
XPR7075
Keizo Waku
C26H46NO2 404.649 Download ChemDraw structure file
oil (Ref. 7011)
d0.88 (J=7.5Hz, 3H), 1.28 (br s, 14H), 1.60-1.90 (m, 2H), 2.05-2.30 (m, 6H), 2.75-2.95 (m, 7H), 3.35-3.55 (m, 2H), 3.65-3.80 (m, 2H), 5.20-5.55 (m, 8H), 5.85 (br s, 1H). (Ref. 7011)




This compound was synthesized from 5,8,11,14-tetracosanoylchloride and ethanolamine. Yield 66%. (Ref. 7011)



247
16,16-dimethyl-5,8,11,14-all-cis-docosatetraenoylethanolamine
XPR7076
Keizo Waku
C26H45NO2 403.641 Download ChemDraw structure file
yellow oil (Ref. 7011)
d0.88 (t, J=5.4Hz, 3H), 1.09 (s, 6H), 1.27 (br s, 10H), 1.62-1.86 (m, 2H), 2.03-2.30 (m, 4H), 2.68-2.98 (m, 6H), 3.40 (dt, J=4.0, 6.3Hz, 2H), 3.71 (t, J=5.0Hz, 2H), 5.13-5.41 (m, 8H), 6.19 (br s, 1H) (Ref. 7011)




This compound was synthesized from 16,16-dimethyl-5,8,11,14-docosatetraenoylchloride and ethanolamine. Yield 93%. (Ref. 7011)



248
17,17-dimethyl-5,8,11,14-all-cis-docosatetraenoylethanolamide
XPR7077
Keizo Waku
C26H46NO2 404.649 Download ChemDraw structure file
oil (Ref. 7011)
d0.88 (s, 6H), 0.90 (t, J=7.5Hz, 3H), 1.20 (br s, 8H), 1.60-2.30 (m, 8H), 2.70-2.95 (m, 7H), 3.35-3.55 (m, 2H), 3.65-3.80 (m, 2H), 5.20-5.60 (m, 8H), 6.05 (br s, 1H) (Ref. 7011)




This compound was synthesized from 17,17-dimethyl-docosatetraenoylchloride and ethanolamine. Yield 61%. (Ref. 7011)



249
17,17-dimethyl-5,8,11,14-all-cis-heneicosanoylethanolamine
XPR7078
Keizo Waku
C25H44NO2 390.622 Download ChemDraw structure file
oil (Ref. 7011)
d0.85 (s, 6H), 0.90 (t, J=7.5Hz, 3H), 1.25 (br s, 6H), 1.65-2.30 (m, 8H), 2.65-2.95 (m, 7H), 3.30-3.50 (m, 2H), 3.65-3.80 (m, 2H), 5.20-5.50 (m, 8H), 6.05 (br s, 1H) (Ref. 7011)




This compound was synthesized from 17,17-dimethyl-5,8,11,14-heneicosanoyl chloride and ethanolamine. Yield 40%. (Ref. 7011)



250
17-methyl-5,8,11,14-all-cis-docosatetraenoylethanolamine
XPR7079
Keizo Waku
C25H44NO2 390.622 Download ChemDraw structure file
oil (Ref. 7011)
d0.90 (m, 6H), 1.28 (br s, 9H), 1.60-2.35 (m, 8H), 2.65-2.95 (m, 7H), 3.30-3.50 (m, 2H), 3.65-3.85 (m, 2H), 5.20-5.60 (m, 8H), 5.95 (br s, 1H) (Ref. 7011)




This compound was synthesized from 17-methyl-5,8,11,14-docosatetraenoylchloride and ethanolamine. Yield 64%. (Ref. 7011)



251
(pm)-2,16,16-trimethyl-5,8,11,14-all-cis-docosatetraenoyl-2'-fluoroethyamine
XPR7080
Keizo Waku
C27H47FNO 420.667 Download ChemDraw structure file
yellow oil (Ref. 7011)
d0.88 (t, J=4.0Hz, 3H), 1.09 (s, 6H), 1.16 (d, J=6.9Hz, 3H), 1.26 (br s, 10H), 1.39-2.34 (m, 5H), 2.72-2.98 (m, 6H), 3.58 (ddt, J=29.0, 5.0, 4.5Hz, 2H), 4.49 (dt, J=47.5, 4.6Hz, 2H), 5.13-5.53 (m, 8H), 5.82 (br s, 1H) (Ref. 7011)




This compound was synthesized from 2,16,16-trimethyl-5,8,11,14-all-cis-docosatetraenoylchloride and2-fluoroethanolamine.Yield 65%. (Ref. 7011)



252
(pm)-2,16,16-trimethyl-5,8,11,14-all-cis-tricosatetraenoyl-2'-fluoroethylamine
XPR7081
Keizo Waku
C28H48NOF 433.685 Download ChemDraw structure file
oil (Ref. 7011)
d0.88 (t, 6.0Hz, 3H), 1.09 (s, 6H), 1.16 (d, J=6.8Hz, 3H), 1.25 (br s, 10H), 1.39-2.40 (m, 5H), 2.81-2.97 (m, 6H), 3.57 (ddt, J=28.5, 5.2, 4.5Hz, 2H), 4.49 (dt, J=47.4, 4.6Hz, 2H), 5.13-5.52 (m, 8H), 5.86 (br s, 1H) (Ref. 7011)




This compound was synthesized from 2,16,16-trimethyl-5,8,11,14-tricosatetraenoylchloride and 2-fluoroethylamine. Yield 57%. (Ref. 7011)



253
(pm)-2,16,-dimethyl-5,8,11,14-all-cis-docosatetraenoyl-2'-fluoroethylamine
XPR7082
Keizo Waku
C26H45FNO 406.640 Download ChemDraw structure file
oil (Ref. 7011)
d0.88 (t, J=6.0Hz, 3H), 0.94 (d, J=6.2Hz, 2H), 1.16 (d, J=6.8Hz, 3H), 1.25 (br s, 10H), 1.36-2.60 (m, 6H), 2.70-2.90 (m, 6H), 3.60 (ddt, J=28.5, 5.1, 4.6Hz, 2H), 4.49 (dt, J=47.4, 4.8Hz, 2H), 5.15-5.60 (m, 8H), 5.81 (br s, 1H) (Ref. 7011)




This compound was synthesized from 2,16,dimethyl-5,8,11,14-docosatetraenoylchloride and 2-fluoroethylamine. Yield 37%. (Ref. 7011)



254
(pm)-2,17,17,-trimethyl-5,8,11,14-all-cis-docosatetraenoyl-2'-fluoroethylamine
XPR7083
Keizo Waku
C27H47FNO 420.667 Download ChemDraw structure file
oil (Ref. 7011)
d0.85 (s, 6H), 0.90 (t, J=6.0Hz, 3H), 1.15 (d, J=7.0Hz, 3H), 1.25 (br s, 8H), 1.40-2.40 (m, 7H), 2.70-2.95 (m, 6H), 3.58 (ddt, J=28.5, 5.2, 4.5Hz, 2H), 4.50 (dt, J=47.4, 4.6 Hz, 2H), 5.20-5.55 (m, 8H), 5.85 (br s, 1H) (Ref. 7011)




This compound was synthesized from 2,17,17,-trimethyl-5,8,11,14-docosatetraenoylchloride and 2-fluoroethylamine. Yield 72%. (Ref. 7011)



255
(pm)-2,17,-dimethyl-5,8,11,14-all-cis-docosatetraenoyl-2'-fluoroethylamine
XPR7084
Keizo Waku
C26H44FNO 405.632 Download ChemDraw structure file
oil (Ref. 7011)
d0.80-0.98 (m, 6H), 1.15 (d, J=6.5Hz, 3H), 1.25 (br s, 8H), 1.38-2.40 (m, 8H), 2.65-3.0 (m, 6H), 3.60 (ddt, J=28.5, 5.2, 4.6Hz, 2H), 4.50 (dt, J=47.5, 4.8Hz, 2H), 5.20-5.55 (m, 8H), 5.80 (br s, 1H) (Ref. 7011)




This compound was synthesized from 2,17,-dimethyl-5,8,11,14-docosatetraenoylchloride and 2-fluoroethylamine. Yield 69%. (Ref. 7011)



256
(pm)-2-methyl-5,8,11,14-all-cis-tricosatetraenoyl-2'-fluoroethylamine
XPR7085
Keizo Waku
C26H45FNO 406.640 Download ChemDraw structure file
oil (Ref. 7011)
d0.88 (t, J=6.0 Hz, 3H), 1.13 (d, J=7.5Hz, 3H), 1.25 (br s, 12H), 1.38-2.40 (m, 7H), 2.70-2.95 (m, 6H), 3.60 (ddt, J=28.5, 5.2, 4.5Hz, 2H), 4.50 (dt, J=47.5, 4.5Hz, 2H), 5.20-5.60 (m, 8H), 5.80 (br s, 1H) (Ref. 7011)




This compound was synthesized from 2-methyl-5,8,11,14-tricosatetraenoylchloride and 2-fluoroethylamine. Yield 72%. (Ref. 7011)



257
2-Arachidonoylglycerol
2-Mono((all Z)-5', 8', 11', 14'-eicosatetraenoyl)glycerol
XPR7086
Keizo Waku
2-AG
C23H38O4 378.545 Download ChemDraw structure file
Effect of 2-arachidonoylglycerol on the specific binding of CP55940 to rat synaptosomal membrane. Ki= 3.1pmM (Ref. 7014)The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by 2-arachidonoylglycerol is demonstrated as follows. (Ref. 7014)
[Table 7086]
soluble in the organic solvent(Ref. 0014)



2-arachidonoylglycerol was purified by TLC using petroleum ether:diethylether:acetic acid(20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)
This compound was distributed in rat brain (Ref. 7014) and canine gut (Ref. 7017).
2-Arachidonoyl-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and arachidonic anhydride. 2-arachidonoylglycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85degC under vacuum for 3 min. (Ref. 7014)
2-arachidonoylglycerol was easily hydrolyzed in the rat brain to arachidonic acid and glycerol.(Ref. 7013)


258
1-Arachidonoylglycerol
1-Mono((all Z)-5', 8', 11', 14'-eicosatetraenoyl)glycerol
XPR7087
Keizo Waku
1-AG
C23H38O4 378.545 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by 1-arachidonoylglycerol is demonstrated as follows. (Ref. 7014)
[Table 7087]



1-arachidonoylglycerol was purified by TLC using petroleum ether:diethylether:acetic acid(20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)

1-Arachidonoyl-sn-glycerol was synthesized from 2,3-O-isopropyridene-sn-glycerol and arachidonic acid anhydride using dimethylaminopyridine as a catalyst. The purified l-arachidonoyl-2,3-isopropyrideneglycerol was treated with boric acid and boric acid trimethylester, at 85degC under vacuum for 3 min, to yield 1-arachidonoylglycerol. (Ref. 7014)



259
3-Arachidonoylglycerol
3-Mono((all Z)-5', 8', 11', 14'-eicosatetraenoyl)glycerol
XPR7088
Keizo Waku
3-AG
C23H38O4 378.545 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by 3-arachidonoylglycerol is demonstrated as follows. (Ref. 7014)
[Table 7088]



3-arachidonoylglycerol was purified by TLC using petroleum ether:diethylether:acetic acid(20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)

3-Arachidonoyl-sn-glycerol was synthesized from 1,2-O-isopropyridene-sn-glycerol and arachidonic acid anhydride using dimethylaminopyridine as a catalyst. The purified l,2-isopropyrideneglycerol-3-arachidonoylglycerol was treated with boric acid and boric acid trimethylester, at 85degC under vacuum for 3 min, to yield 3-arachidonoylglycerol. (Ref. 7014)



260
Ether-linked analogue of 2-arachidonoylglycerol
2-O-((all Z)-5',8',11',14'-Eicosatetraenyl)glycerol
XPR7089
Keizo Waku
Ether type 2-AG
C23H40O3 364.562 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by 2-eicosatetraenylglycerol is demonstrated as follows. (Ref. 7014)
[Table 7089]



2-Eicosatetraenylglycerol was purified by TLC (ethyl acetate as solvent, Rf, 0.48). (Ref. 7014)

2-Eicosatetraenyl-1,3-benzylideneglycerol was obtained by condensating eicosatetraenyl iodide and 1,3-benzylideneglycerol using dimethylformamide as the solvent and Ag2O and tetra-n-butylammonium iodide as catalysts. 2-Eicosatetraenylglycerol was prepared from 2-eicosatetraenyl-1,3-benzylideneglycerol by treatment of boric acid and boric acid trimethylester. (Ref. 7014)



261
Ether-linked analogue of 1-arachidonoylglycerol
1-O-((all Z)-5',8',11',14'-Eicosatetraenyl)glycerol
XPR7090
Keizo Waku
Ether type 1-AG
C23H40O3 364.562 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by 1(3)-eicosatetraenylglycerol is demonstrated as follows. (Ref. 0014)
[Table 7090]



1(3)-Eicosatetraenylglycerol was purified by TLC (ethyl acetate as solvent, Rf, 0.48). (Ref. 7014)

1(3)-Eicosatetraenyl-1,2-O-isopropylideneglycerol was obtained by condensating eicosatetraenyl iodide and 1,2-O-isopropylideneglycerol using dimethylformamide as the solvent and Ag2O and tetra-n-butylammonium iodide as catalysts. 1(3)-Eicosatetraenylglycerol was prepared from 1(3)-eicosatetraenyl-1,2-O-isopropylideneglycerol by treatment of boric acid and boric acid trimethylester. (Ref. 7014)



262
Methylene-linked analogue of 2-arachidonoylglycerol
2-Hydroxymethyl (all Z)-7,10,13,16-docosatetraen-1-ol
XPR7091
Keizo Waku
Methylene linked 2-AG
C23H40O2 348.563 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014)
[Table 7091]



The Rf value for the methylene-linked analogue of 2-arachidonoylglycerol in the TLC system using hexane:ethyl acetate (6:4) as the developing solvent was 0.15. (Ref. 7017)

The eicosatetraenol iodide and diethyl malonate were mixed and refluxed for 4 hr in a mixture of tetrahydrofuran and dimethylformamide. The diethylmalonate derivative was reduced in dry diethylether with LiAlH4. (Ref. 7014)



263
2-Hydroxypropyl arachidonate
XPR7092
Keizo Waku
C23H38O3 362.546 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014)
[Table 7092]



This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (65:35:19) as the solvent system (Rf, 0.20) (Ref. 7014)

2-Oxopropylarachidonate was prepared from hydroxyacetone and arachidonic anhydride. The resultant 2-oxopropyl arachidonate was treated with NaBH4 to yield 2-hydroxypropylarachidonate. (Ref. 7014)



264
3-Hydroxypropyl arachidonate
XPR7093
Keizo Waku
C23H38O3 362.546 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014)
[Table 7093]



This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.58). (Ref. 7014)

This compound was prepared from 1,3-propanediol and arachidonic anhydride using dimethylaminopyridine as a catalyst and purified by TLC. (Ref. 7014)



265
2-eicosatetraynoyl(n-6)glycerol
2-Mono(5',8',11',14'-eicosatetraynoyl)glycerol
XPR7094
Keizo Waku
C23H30O4 370.482 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014)
[Table 7094]



This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)

2-Eicosatetraynoyl-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and eicosatetraynoyl anhydride. 2-Eicosatetraynoylglycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85 degC under vacuum for 3 min. (Ref. 7014)



266
2-oleoylglycerol
2-Mono(9'-octadecenoyl)glycerol
XPR7095
Keizo Waku
C21H40O4 356.540 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014)
[Table 7095]



This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)

2-Oleoyl-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and oleoyl anhydride. 2-Oleoylglycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85degC under vacuum for 3 min. (Ref. 7014)



267
2-linoleoylglycerol
2-Mono((all Z)-9',12'-octadecadienoyl)glycerol
XPR7096
Keizo Waku
C2lH38O4 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014)
[Table 7096]



This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)

2-Linoleoyl-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and linoleoyl anhydride. 2-Linoleoylglycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85degC under vacuum for 3 min. (Ref. 7014)



268
2-g-linolenoylglycerol
2-Mono((all Z)-6',9',12'-octadecatrienoyl)glycerol
XPR7097
Keizo Waku
C21H36O4 352.508 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014)
[Table 7097]



This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)

2-gLinolenoyl-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and glinolenoyl anhydride. 2-gLinolenoylglycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85degC under vacuum for 3 min. (Ref. 7014)



269
2-eicosatrienoyl(n-3)glycerol
2-Mono((all Z)-11',14',17'-eicosatrienoyl)glycerol
XPR7098
Keizo Waku
C23H40O4 380.561 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014)
[Table 7098]



This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)

2-Eicosatrienoyl(n-3)-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and eicosatrienoyl(n-3) anhydride. 2-Eicosatrienoyl(n-3)glycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85degC under vacuum for 3 min. (Ref. 7014)



270
2-eicosatrienoyl(n-6)glycerol
2-Mono((all Z)-8',11',14',-eicosatrienoyl)glycerol
XPR7099
Keizo Waku
C23H40O4 380.561 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014)
[Table 7099]



This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)

2-Eicosatrienoyl(n-6)-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and eicosatrienoyl(n-6) anhydride. 2-Eicosatrienoyl(n-6)glycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85degC under vacuum for 3 min. (Ref. 7014)



271
2-eicosatrienoyl(n-9)glycerol
2-Mono((all Z)-5',8',11',-eicosatrienoyl)glycerol
XPR7100
Keizo Waku
C23H40O4 380.561 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014)
[Table 7100]



This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)

2-Eicosatrienoyl(n-9)-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and eicosatrienoyl(n-9) anhydride. 2-Eicosatrienoyl(n-9)glycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85degC under vacuum for 3 min. (Ref. 7014)



272
2-eicosapentaenoyl(n-3)glycerol
2-Mono((all Z)-5',8',11',14',17'-eicosapentaenoyl)glycerol
XPR7101
Keizo Waku
C23H36O4 376.530 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014)
[Table 7101]



This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)

2-Eicosapentaenoyl(n-3)-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and eicosapentaenoyl(n-3) anhydride. 2-Eicosapentaenoyl(n-3)glycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85degC under vacuum for 3 min. (Ref. 7014)



273
2-docosatetraenoyl(n-6)glycerol
2-Mono((all Z)-7',10',13',16'-docosatetraenoyl)glycerol
XPR7102
Keizo Waku
C25H42O4 406.599 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014)
[Table 7102]



This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)

2-Docosatetraenoyl(n-6)-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and docosatetraenoyl(n-6) anhydride. 2-Docosatetraenoyl(n-6)glycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85 degC under vacuum for 3 min. (Ref. 7014)



274
2-docosahexaenoyl(n-3)glycerol
2-Mono((all Z)-4',7',10',13',16',19'-docosahexaenoyl)glycerol
XPR7103
Keizo Waku
C25H38O4 402.567 Download ChemDraw structure file
The increase of [Ca2+]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014)
[Table 7103]



This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)

2-Docosahexaenoyl(n-3)-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and docosahexaenoyl(n-3) anhydride. 2-Docosahexaenoyl(n-3)glycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85 degC under vacuum for 3 min. (Ref. 7014)



275
N-oleoylethanolamine/N-oleoylethanolamide
N-(cis-9-octadecenoyl) ethanolamine/N-(hydroxyethyl) oleamide
XPR7501
Takehiko Yokomizo
OEA
C20H39NO2 325.529 Download ChemDraw structure file
Causes a potent and persistent decrease in food intake and gain in body mass(Ref. 7503).
Soluble in ethanol and DMSO

HPLC/MS (Ref. 7504)




Synthesized from N-oleoyl-phosphatidylethanolamine by phosphodiesterase or from free oleic acid and ethanolamine by acyltransferase(Ref. 7501).
Degraded by amidohydrolase(Ref. 7502).


276
clavulone I(Ref. 8001/8003)/claviridenone-d(Ref. 8002/8006)
methyl (4R,5Z,7E)-4-acetoxy-7-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate
XPR8001
Yasuji Yamada
C25H34O7 446.533 Download ChemDraw structure file
Clavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8001)Clavulone I showed strong antiproliferative activity in the human myeloid leukemia (HL-60) cells (IC50 0.2 mg/ml). Clavulone arrests the cells in the G1-phase and inhibits the cell growth of HL-60 cells by inhibiting S-phase DNA synthesis.(Ref. 8009)Clavulone showed positive chronotropic action on the cultured myocardial cells.(Ref. 8014)
[a]D -28.9deg(C 0.36, CHCl3)(Ref. 8001)
Clavulones are soluble in MeOH, EtOH, CHCl3 or hexane.
lmax(EtOH) 230 nm(e13600),292 nm(e17300)(Ref. 8001)
nmax(film)1730,1700,1635,and 1230cm-1(Ref. 8001)
1H-NMR(270MHz,CDCl3)dppm0.88(3H,t,J=6.7Hz),2.03(3H,s),2.05(3H,s),2.38(2H,t,J=7.7Hz),2.66(1H,dd,J=7,14.5Hz),2.97(1H,dd,J=7,14.5Hz),3.70(3H,s),5.22(1H,dt,J=10.9,7Hz),5.45(1H,dt,J=10.9,8Hz),5.78(1H,m),5.86(1H,t,J=10Hz),6.42(1H,d,J=6.3Hz),6.59(1H,dd,J=10,12.5Hz),7.25(1H,d,J=12.5Hz),7.47(1H,d,J=6.3Hz).(Ref. 8001)13C-NMR(67.8MHz,CDCl3)dppm14.0(q),20.9(q),21.2(q),22.5(t),27.4(t),29.0(t),29.8(t),29.8(t),31.4(t),35.9(t),51.7(q),69.4(d),85.2(s),121.0(d),124.3(d),124.4(d),134.9(d),137.5(s),138.7(d),157.8(d),169.0(s),169.7(s),172.7(s),193.0(s).(Ref. 8001)

CDlext(EtOH)(De)nm 248(+3.8),291(-5.0).(Ref. 8022)

Clavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8001/8002/8003/8006)
Clavulone I was synthesized from cyclopentadiene and methyl 3-chloroformylpropionate as a racemic form.(Ref. 8007)Clavulones were synthesized from L-(+)-diethyl tartarate and D-mannitol as a natural form.(Ref. 8008)Other synthesis of clavulone.(Ref. 8015/8016/8017)
The biosynthesis of clavulone is suggested to proceed from arachidonic acid via 8(R)-HEPETE and pre-clavulone A.(Ref. 8004/8005/8012/8013)


277
clavulone II(Ref. 8001/8003)/claviridenone-c(Ref. 8002/8006)
methyl (4R,5E,7E)-4-acetoxy-7-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate
XPR8002
Yasuji Yamada
C25H34O7 446.533 Download ChemDraw structure file
Clavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8001)Clavulone showed positive chronotropic action on the cultured myocardial cells.(Ref. 8014)Clavulone II showed strong antiproliferative activity in the human myeloid leukemia (HL-60) cells (IC50 0.2 mg/ml).(Ref. 8019)Clavulone II was entrapped into lipid microspheres of 0.2 mm diameter to lipo-drug. Daily treatment with lipo-clavulone II (12.5 mg/kg/day, i.p.) on days 1 through 5 markedly prolonged the survival time (73% ILS) of mice inoculated with sarcoma 180 as compared with that of corresponding dose of respective free clavulone II.(Ref. 8021)
[a]D +10.9deg(C 0.35, CHCl3)(Ref. 8001)
Clavulones are soluble in MeOH, EtOH, CHCl3, or hexane.
lmax(EtOH) 230 nm(e14500),292 nm(e19300) (Ref. 8001)
nmax(film)1730,1700,1640,and 1230cm-1(Ref. 8001)
1H-NMR(270MHz,CDCl3)dppm0.88(3H,t,J=6.9Hz),2.07(3H,s),2.08(3H,s),2.38(2H,t,J=7.5Hz),2.69(1H,dd,J=8,14.5Hz),2.88(1H,dd,J=7,14.5Hz),3.68(3H,s),5.22(1H,m),5.52(1H,dt,J=10.9,8Hz),5.42(1H,q,J=7Hz),6.02(1H,dd,J=7,14.5Hz),6.41(1H,d,J=6.3Hz),6.75(1H,dd,J=11.6,14.5Hz),6.87(1H,d,J=11.6Hz),7.47(1H,d,J=6.3Hz).(Ref. 8001)13C-NMR(67.8MHz,CDCl3)dppm14.0(q),21.0(q),21.2(q),22.5(t),27.4(t),29.1(t),29.1(t),29.6(t),31.5(t),36.0(t),51.8(q),72.8(d),85.1(s),121.1(d),126.9(d),129.3(d),135.0(d),137.0(s),141.3(d),158.1(d),169.5(s),169.9(s),172.9(s),193.4(s).(Ref. 8001)

CDlext(EtOH)(De)nm 250(+4.2),293(-3.4).(Ref. 8022)

Clavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8001/8002/8003/8006)
Clavulone II was synthesized from cyclopentadiene and methyl 3-chloroformylpropionate as a racemic form.(Ref. 8007)Clavulones were synthesized from L-(+)-diethyl tartarate and D-mannitol as a natural form.(Ref. 8008)Other synthesis of clavulone.(Ref. 8010/8011/8015/8016/8017/8018)
The biosynthesis of clavulones is suggested to proceed from arachidonic acid via 8(R)-HEPETE and pre-clavulone A.(Ref. 8004/8005/8012/8013)


278
clavulone III(Ref. 8001/8003)/claviridenone-b(Ref. 8002/8006)
methyl (4R,5E,7Z)-4-acetoxy-7-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate
XPR8003
Yasuji Yamada
C25H34O7 446.533 Download ChemDraw structure file
Clavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8001)Clavulone showed positive chronotropic action on the cultured myocardial cells.(Ref. 8014)
[a]D +45.5deg(C 0.22, CHCl3)(Ref. 8001)
Clavulones are soluble in MeOH, EtOH, CHCl3, or hexane.
lmax(EtOH) 230 nm(e17200),295 nm(e17600)(Ref. 8022)
nmax(film)1735,1690,1640,and 1230cm-1(Ref. 8022)
1H-NMR(270MHz,CDCl3)dppm0.88(3H,t,J=6.9Hz),2.04(3H,s),2.10(3H,s),2.39(2H,t,J=7.5Hz),2.66(1H,dd,J=7,14.5Hz),2.86(1H,dd,J=7,14.5Hz),3.67(3H,s),5.21(1H,dt,J=11,7Hz),5.52(1H,dt,J=11,8Hz),5.44(1H,q,J=6Hz),6.02(1H,dd,J=6,15.5Hz),6.36(1H,d,J=6.3Hz),6.52(1H,d,J=11.2Hz),7.50(1H,d,J=6.3Hz),7.74(1H,dd,J=11.2,15.5Hz).(Ref. 8001)13C-NMR(67.8MHz,CDCl3)dppm14.0(q),21.0(q),21.7(q),22.5(t),27.4(t),29.1(t),29.2(t),29.8(t),31.5(t),35.6(t),51.7(q),72.5(d),85.3(s),121.4(d),126.5(d),133.4(d),134.8(d),135.7(s),141.0(d),156.1(d),169.7(s),170.1(s),173.1(s),194.1(s).(Ref. 8001)

CDlext(EtOH)(De)nm 245(+3.4),297(-0.6).(Ref. 8022)

Clavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8001/8002/8003/8006)
Clavulones were synthesized from L-(+)-diethyl tartarate and D-mannitol as a natural form.(Ref. 8008)Other synthesis of clavulone.(Ref. 8010/8015/8016/8017/8018)
The biosynthesis of clavulones is suggested to proceed from arachidonic acid via 8(R)-HEPETE and pre-clavulone A.(Ref. 8004/8005/8012/8013)


279
clavulone IV(Ref. 8022)/claviridenone-a(Ref. 8002/8006)
methyl (4R,5Z,7Z)-4-acetoxy-7-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate
XPR8004
Yasuji Yamada
C25H34O7 446.533 Download ChemDraw structure file
Clavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8001)Clavulone showed positive chronotropic action on the cultured myocardial cells.(Ref. 8014)
[a]D -80.0deg(CHCl3)(Ref. 8022)
Clavulones are soluble in MeOH, EtOH, CHCl3, or hexane.
lmax(EtOH) 230 nm(e10600),295 nm(e9900)(Ref. 8022)
nmax(film)1730,1695,1640,and 1240cm-1(Ref. 8022)
1H-NMR(270MHz,CDCl3)dppm0.88(3H,t,J=6.9Hz),2.03(3H,s),2.07(3H,s),2.36(2H,t,J=7.5Hz),2.65(1H,dd,J=7.3,14.2Hz),2.83(1H,dd,J=8,14.2Hz),3.68(3H,s),5.27(1H,m),5.52(1H,m),5.73(1H,t,J=10.6Hz),5.83(1H,m),6.39(1H,d,J=5.9Hz),7.02(1H,d,J=12.5Hz),7.49(1H,d,J=5.9Hz),7.61(1H,t,J=11.5Hz).(Yamada Yasuji)13C-NMR(67.8MHz,CDCl3)dppm14.0(q),21.1(q),21.6(q),22.5(t),27.4(t),29.1(t),29.6(t),29.8(t),31.5(t),36.1(t),51.7(q),68.1(d),85.0(s),121.5(d),126.0(d),127.9(d),134.8(d),136.5(d),136.6(d),137.0(s),156.7(d),169.9(s),170.1(s),172.9(s),194.2(s).(Yasuji Yamada)

CDlext(EtOH)(De)nm 245(+1.2),290(-1.4).(Ref. 8022)

Clavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8003/8006/8022)
Clavulones were synthesized from L-(+)-diethyl tartarate and D-mannitol as a natural form.(Ref. 8008)Other synthesis of clavulone.(Ref. 8015/8016/8017)
The biosynthesis of clavulones is suggested to proceed from arachidonic acid via 8(R)-HEPETE and pre-clavulone A.(Ref. 8004/8005/8012/8013)


280
20-acetoxyclavulone I (Ref. 8024)
methyl (4R,5Z,7E)-4-acetoxy-7-[(S)-2-acetoxy-2-[(Z)-7-acetoxy-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate
XPR8005
Yasuji Yamada
C27H36O9 504.569 Download ChemDraw structure file
20-Acetoxyclavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8022)
[a]D -31.1deg(C 0.09, CHCl3)(Ref. 8024)
20-Acetoxyclavulones are soluble in MeOH, EtOH, CHCl3, or hexane.
lmax(EtOH) 230 nm(e10900),288 nm(e13700)(Ref. 8024)
nmax(film)1735,1705,1640,and 1235cm-1(Ref. 8024)
1H-NMR(270MHz,CDCl3)dppm2.03(3H,s),2.05(6H,s),2.38(2H,t,J=7.5Hz),2.66(1H,dd,J=8,14.5Hz),3.00(1H,dd,J=7,14.5Hz),3.70(3H,s),4.04(2H,t,J=6.6Hz),5.22(1H,m),5.47(1H,m),5.79(1H,m),5.79(1H,m),5.84(1H,t,J=10.2Hz),6.42(1H,d,J=6.3Hz),6.58(1H,dd,J=10.2,12.5Hz),7.27(1H,d,J=12.5Hz), 7.47(1H,d,J=6.3Hz).(Ref. 8024)13C-NMR(67.8MHz,CDCl3)dppm21.0(q,2C),21.3(q),25.6(t),27.3(t),28.5(t),29.0(t),29.8(t,2C),35.8(t),51.8(q),64.5(t),69.4(d),85.1(s),121.5(d),124.2(d),124.6(d),134.5(d),135.2(d),137.4(s),138.9(d),157.8(d),169.1(s),169.9(s),171.2(s),172.9(s),193.1(s).(Ref. 8024)

CDlext(EtOH)(De)nm 247(+2.6),290(-3.6).(Ref. 8022/8024)

20-Acetoxyclavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8024)




281
20-acetoxyclavulone II (Ref. 8024)
methyl (4R,5E,7E)-4-acetoxy-7-[(S)-2-acetoxy-2-[(Z)-7-acetoxy-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate
XPR8006
Yasuji Yamada
C27H36O9 504.569 Download ChemDraw structure file
20-Acetoxyclavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8022)
[a]D +3.7deg(C 0.54, CHCl3)(Ref. 8024)
20-Acetoxyclavulones are soluble in MeOH, EtOH, CHCl3, or hexane.
lmax(EtOH) 230 nm(e14200),292 nm(e18700)(Ref. 8024)
nmax(film)1730,1700,1640,and 1235cm-1(Ref. 8024)
1H-NMR(270MHz,CDCl3)dppm2.05(3H,s),2.07(3H,s),2.08(3H,s),2.38(2H,t,J=7.3Hz),2.69(1H,dd,J=7.6,16Hz),2.87(1H,dd,J=7.3,16Hz),3.68(3H,s),4.04(2H,t,J=6.9Hz),5.20(1H,m),5.41(1H,q,J=7Hz),5.51(1H,dt,J=11,7.3Hz),6.03(1H,dd,J=7,14.8Hz),6.41(1H,d,J=6.9Hz),6.74(1H,dd,J=12.2,14.8Hz),6.86(1H,d,J=12.2Hz),7.47(1H,d,J=5.9Hz).(Ref. 8024)13C-NMR(67.8MHz,CDCl3)dppm21.0(q,2C),21.2(q),25.6(t),27.3(t),28.5(t),29.2(t,2C),29.5(t),36.0(t),51.8(q),64.4(t),72.8(d),85.0(s),121.5(d),126.8(d),129.3(d),134.5(d),135.0(d),136.8(s),141.3(d),158.1(d),169.5(s),169.9(s),171.2(s),172.9(s),193.3(s).(Ref. 8024)

CDlext(EtOH)(De)nm 247(+2.6),295(-1.0).(Ref. 8022/8024)

20-Acetoxyclavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8024)




282
20-acetoxyclavulone III (Ref. 8024)
methyl (4R,5E,7Z)-4-acetoxy-7-[(S)-2-acetoxy-2-[(Z)-7-acetoxy-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate
XPR8007
Yasuji Yamada
C27H36O9 504.569 Download ChemDraw structure file
20-Acetoxyclavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8022)
[a]D +26.4deg(C 0.86, CHCl3)(Ref. 8024)
20-Acetoxyclavulones are soluble in MeOH, EtOH, CHCl3, or hexane.
lmax(EtOH) 230 nm(e12400),295 nm(e12100)(Ref. 8024)
nmax(film)1730,1695,1640,and 1235cm-1(Ref. 8024)
1H-NMR(270MHz,CDCl3)dppm2.02(3H,s),2.05(3H,s),2.10(3H,s),2.39(2H,t,J=7.6Hz),2.62(1H,dd,J=7.6,14.2Hz),2.87(1H,dd,J=7.3,14.2Hz),3.68(3H,s),4.04(2H,t,J=6.9Hz),5.21(1H,m),5.44(1H,q,J=5.9Hz),5.51(1H,m),6.03(1H,dd,J=5.9,15.5Hz),6.36(1H,d,J=6.3Hz),6.52(1H,d,J=11.2Hz),7.50(1H,d,J=6.3Hz),7.47(1H,dd,J=11.2,15.5Hz).(Ref. 8024)13C-NMR(67.8MHz,CDCl3)dppm21.0(q,2C),21.7(q),25.6(t),27.3(t),28.5(t),29.0(t),29.2(t),29.8(t),35.6(t),51.7(q),64.4(t),72.5(d),85.2(s),121.8(d),126.4(d),133.5(d),134.2(d),135.6(s),136.9(d),141.1(d),156.0(d),169.9(s),170.1(s),171.2(s),173.1(s),194.0(s).(Ref. 8024)

CDlext(EtOH)(De)nm 243(+2.5),291(-0.6).(Ref. 8022/8024)

20-Acetoxyclavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8024)




283
chlorovulone I (Ref. 8025/8026)
methyl (5Z,7E)-7-[(R)-4-chloro-2-hydroxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate
XPR8008
Yasuji Yamada
C21H29O4Cl 380.905 Download ChemDraw structure file
Chlorovulone I showed the strong antiproliferative and cytotoxic activities in himan promyelocytic leukemia (HL-60) ((IC50 0.01 mg/ml, cytotoxic effect >0.1 mg/ml).(Ref. 8019/8023/8025)Chlorovulone I was entrapped into lipid microspheres of 0.2 mm diameter to lipo-drug. Daily treatment with lipo-chlorovulone I (1.6 mg/kg/day, i.p.) on days 1 through 5 markedly prolonged the survival time (135% ILS) of mice inoculated with sarcoma 180 as compared with that of corresponding dose of respective free chlorovulone I.(Ref. 8021)
[a]D -1.2deg(C 0.17, CHCl3)(Ref. 8025)
Chlorovulones are soluble in MeOH, EtOH, CHCl3, or hexane.
lmax(EtOH) 243 nm(e14600),315 nm(e15100)(Ref. 8025)
nmax(CHCl3)1705cm-1(Ref. 8025)
1H-NMR(400MHz,CDCl3)dppm0.88(3H,t,J=7.2Hz),1.30(6H,m),1.80(2H,quint.,J=7.4Hz),1.97(2H,brq,J=7.0Hz),2.35(2H,t,J=7.4Hz),2.42(2H,m),2.67(1H,ddd,J=0.5,7.8,14.2Hz),2.82(1H,ddd,J=0.5,7.5,14.2Hz),3.68(3H,s),5.22(1H,ttd,J=1.5,7.7,10.9Hz),5.54(1H,ttd,J=1.4,8.7,10.9Hz),6.11(1H,tdd,J=7.9,0.9,10.9Hz),6.77(1H,tdd,J=1.5,10.9,12.6Hz),7.21(1H,d,J=0.6Hz),7.33(1H,brd,J=12.6Hz).(Ref. 8025)13C-NMR(100MHz,CDCl3)dppm13.9(q),22.4(t),24.3(t),27.1(t),27.3(t),29.0(t),31.4(t),33.2(t),33.6(t),51.6(q),77.7(s),121.7(d),123.8(d),127.9(d),134.8(d),136.4(s),137.9(s),143.6(d),154.0(d),173.6(s),187.7(s).(Ref. 8025)

CDlext(EtOH)(De)nm 232(+7.6),265(-6.1),360(+3.1).(Ref. 8028)

Chlorovulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8025/8026)
Photoisomerization of chlorovulone I (fluoresent lamp, benzene, 40 hr) gave a mixture of chlorovulones I, II and III.(Ref. 8025)



284
chlorovulone II (Ref. 8025/8026)
methyl (5E,7E)-7-[(R)-4-chloro-2-hydroxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate
XPR8009
Yasuji Yamada
C21H29O4Cl 380.905 Download ChemDraw structure file
(-)-Chlorovulone II showed the strong antiproliferative and cytotoxic activities in himan promyelocytic leukemia (HL-60) ((IC50 0.01 mg/ml, cytotoxic effect >0.1 mg/ml).(Ref. 8023)
[a]D +22.7deg(C 0.075, CHCl3)(Ref. 8025)
Chlorovulones are soluble in MeOH, EtOH, CHCl3, or hexane.
lmax(EtOH) 237 nm(e10000),312 nm(e10100)(Ref. 8025)
nmax(CHCl3)3560,3300,1730,1705, and 1635cm-1(Yamada Yasuji)
1H-NMR(400MHz,CDCl3)dppm0.88(3H,t,J=7.1Hz),1.30(6H,m),1.82(2H,quint.,J=7.4Hz),1.96(2H,brq,J=7.5Hz),2.30(2H,t,J=7.5Hz),2.35(2H,t,J=7.4Hz),2.68(1H,brdd,J=7.9,14.3Hz),2.81(1H,brdd,J=7.5,14.3Hz),3.67(3H,s),5.23(1H,ttd,J=1.4,7.7,10.9Hz),5.55(1H,brtd,J=7.5,10.9Hz),6.28(1H,td,J=7.4,15.1Hz),6.77(1H,tdd,J=1.3,11.9,15.1Hz),7.03(1H,d,J=11.9Hz),7.20(1H,s).(Ref. 8025)



Chlorovulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8025/8026)
Photoisomerization of chlorovulone I (fluoresent lamp, benzene, 40 hr) gave a mixture of chlorovulones I, II and III.(Ref. 8025)(-)-Cholovulone II was synthesized from D-(-)-diethyl tartarate.(Ref. 8026)



285
chlorovulone III (Ref. 8025/8026)
methyl (5E,7Z)-7-[(R)-4-chloro-2-hydroxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate
XPR8010
Yasuji Yamada
C21H29O4Cl 380.905 Download ChemDraw structure file

[a]D +27.3deg(C 0.033, CHCl3)(Ref. 8025)
Chlorovulones are soluble in MeOH, EtOH, CHCl3, or hexane.
lmax(EtOH) 238 nm(e13200),315 nm(e11900)(Ref. 8025)
nmax(CHCl3)1725,1700, and 1630cm-1(Yamada Yasuji)
1H-NMR(400MHz,CDCl3)dppm0.88(3H,t,J=7.1Hz),1.30(6H,m),1.81(2H,quint.,J=7.5Hz),2.00(2H,brq,J=6.9Hz),2.30(2H,brq,J=7.5Hz),2.35(2H,t,J=7.5Hz),2.55(1H,brdd,J=7.6,14.4Hz),2.67(1H,brdd,J=8.3,14.4Hz),3.68(3H,s),5.29(1H,ttd,J=1.7,7.6,10.9Hz),5.38(1H,brtd,J=7.4,10.9Hz),6.19(1H,td,J=7.1,15.7Hz),6.68(1H,d,J=11.4Hz),7.15(1H,s),7.56(1H,tdd,J=1.4,11.4,15.7Hz).(Ref. 8025)



Chlorovulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8025/8026)
Photoisomerization of chlorovulone I (fluoresent lamp, benzene, 40 hr) gave a mixture of chlorovulones I, II and III.(Ref. 8025)



286
chlorovulone IV (Ref. 8025/8026)
methyl (5Z,7Z)-7-[(R)-4-chloro-2-hydroxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate
XPR8011
Yasuji Yamada
C21H29O4Cl 380.905 Download ChemDraw structure file

12-O-acetylchlorovulone IV[a]D -12deg(C 0.025, CHCl3)(Ref. 8025)
Chlorovulones are soluble in MeOH, EtOH, CHCl3, or hexane.
12-O-acetylchlorovulone IV1H-NMR(400MHz,CDCl3)dppm0.88(3H,t,J=7.2Hz),1.79(2H,quint.,J=7.4Hz),1.81(2H,quint.,J=7.5Hz),1.97(2H,brq,J=7.4Hz),2.04(3H,s),2.35(2H,t,J=7.4Hz),2.70(1H,brdd,J=7.1,14.3Hz),2.94(1H,brdd,J=7.4,14.3Hz),3.67(3H,s),5.21(1H,brq,J=10.8Hz),5.54(1H,brtd,J=7.4,10.8Hz),6.02(1H,brtd,J=8.8,10.8Hz),6.98(1H,d,J=12.0Hz),7.44(1H,s),7.55(1H,brt,J=12.0Hz).(Ref. 8025)



Chlorovulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8025/8026)




287
10,11-epoxychlorovulone I (Ref. 8027)
methyl (5Z,7E)-7-[(2S,3S,4R)-4-chloro-3,4-epoxy-2-hydroxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentanylidene]-5-heptenoate
XPR8012
Yasuji Yamada
C21H29O5Cl 396.905 Download ChemDraw structure file
10,11-Epoxychlorovulone I showed the strong antiproliferative and cytotoxic activities in himan promyelocytic leukemia (HL-60) ((IC50 0.04 mg/ml, cytotoxic effect >0.3 mg/ml).(Ref. 8019/8027)
[a]D -24.1deg(C 0.44, CHCl3)(Ref. 8025)
10,11-Epoxychlorovulone I is soluble in MeOH, EtOH, CHCl3, or hexane.
lmax(EtOH) 300 nm(e4300)(Ref. 8027)
nmax(CHCl3)3580,1740, and 1625cm-1(Ref. 8027)
1H-NMR(400MHz,CDCl3)dppm0.88(3H,t,J=7.2Hz),1.80(2H,quint.,J=7.4Hz),1.99(2H,brq,J=7.7Hz),2.33(2H,t,J=7.3Hz),2.39(2H,m),2.72(1H,brd,J=7.3Hz),3.68(3H,s),3.96(1H,s),5.23(1H,m),5.60(1H,m),6.13(1H,tdd,J=7.9,10.9,1.0Hz),6.82(1H,tdd,J=1.6,10.9,12.5Hz),7.54(1H,d,J=12.5Hz).(Ref. 8027)
HRCIMS m/z 397.1815 (M+1, calcd for C21H3035ClO5, 397.1780)(Ref. 8027)


10,11-Epoxychlorovulone I was isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8027)
Epoxidation of chlorovulone I with excess 5% aqueous sodium hypochlorite solution in DMF gave 10,11-epoxychlorovulone I.(Ref. 8027)



288
bromovulone I (Ref. 8028)
methyl (5Z,7E)-7-[(R)-4-bromo-2-hydroxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate
XPR8013
Yasuji Yamada
C21H29O5Br 441.356 Download ChemDraw structure file
Bromovulone I showed the strong antiproliferative and cytotoxic activities in himan promyelocytic leukemia (HL-60) ((IC50 0.025 mg/ml, cytotoxic effect >0.4 mg/ml).(Ref. 8019/8023/8028)
[a]D +6.0deg(C 0.05, MeOH)(Yamada Yasuji)
Bromovulone I is soluble in MeOH, EtOH, CHCl3, or hexane.
lEtOHmax 247 nm(e12000),312 nm(e12000)(Ref. 8028)
nmax(CHCl3)3300,1730, 1700, and 1630cm-1(Ref. 8028)
1H-NMR(400MHz,CDCl3)dppm0.89(3H,t,J=7.2Hz),1.30(6H,m),1.80(2H,quint.,J=7.4Hz),1.98(2H,brq,J=7.0Hz),2.36(2H,t,J=7.4Hz),2.42(2H,m),2.66(1H,brdd,J=7.8,14.9Hz),2.81(1H,brdd,J=7.6,14.9Hz),3.69(3H,s),5.22(1H,brtd,J=7.8,11.0Hz),5.55(1H,brtd,J=7.0,11.0Hz),6.11(1H,brtd,J=7.3,10.9Hz),6.77(1H,brdd,J=10.9,12.6Hz),7.35(1H,d,J=12.6Hz),7.43(1H,d,J=0.5Hz).(Ref. 8028)
EIMS m/z 424 and 426 (1:1)(Ref. 8028)
CDlext(EtOH)(De)nm 235(+5.6),260(-3.0),360(+1.2).(Ref. 8028)

Bromovulone I was isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8028)




289
iodovulone I (Ref. 8028)
methyl (5Z,7E)-7-[(R)-4-iodoo-2-hydroxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate
XPR8014
Yasuji Yamada
C21H29O5I 488.356 Download ChemDraw structure file
Iodovulone I showed the strong antiproliferative and cytotoxic activities in himan promyelocytic leukemia (HL-60) ((IC50 0.06 mg/ml, cytotoxic effect >0.4 mg/ml).(Ref. 8019/8023/8028)
[a]D +15.2deg(C 0.07, MeOH)(Yamada Yasuji)
Iodovulone I is soluble in MeOH, EtOH, CHCl3, or hexane.
lmax(EtOH) 240 nm(e22000),313 nm(e19500)(Ref. 8028)
nmax(CHCl3)3300,1720, 1690, and 1620cm-1(Ref. 8028)
1H-NMR(400MHz,CDCl3)dppm0.89(3H,t,J=7.2Hz),1.30(6H,m),1.80(2H,quint.,J=7.4Hz),1.97(2H,brq,J=7.7Hz),2.36(2H,t,J=7.4Hz),2.42(2H,m),2.65(1H,brdd,J=7.7,14.3Hz),2.78(1H,brdd,J=7.4,14.3Hz),3.69(3H,s),5.21(1H,brtd,J=7.7,11.0Hz),5.55(1H,brtd,J=7.4,11.0Hz),6.10(1H,tdd,J=7.9,0.9,10.9Hz),6.77(1H,brdd,J=10.9,12.6Hz),7.34(1H,d,J=12.6Hz),7.69(1H,d,J=0.5Hz).(Ref. 8028)
CIMS m/z 473 (M+1)(Ref. 8028)
CDlext(EtOH)(De)nm 235(+11.4),260(-5.3),365(+2.7).(Ref. 8028)

Iodovulone I was isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8028)




290
punaglandin 1
methyl (5S,6R,7R)-7-[(1R,2S)-4-chloro-2-hydroxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenyl]-5,6,7-triacetoxyheptanoate
XPR8015
Yasuji Yamada
PUG 1
C27H37ClO10 557.029 Download ChemDraw structure file

[a]D+10.6deg(c 2.4, MeOH)(Ref. 8029/8036/8037)
lmax (MeOH)228 nm(e7900) (Ref. 8029/8036/8037)
nmax(CHCl3)3500, 3430, 2930, 2860, 1740, 1610, 1375, 1235, 1025cm-1 (Ref. 8029/8036/8037)
1H-NMR(500MHz, CDCl3)dppm 1.00(3H, t, J=7.5Hz), 1.6(4H, m), 2.00(3H, s), 2.05(2H, m), 2.08(3H, s), 2.11(3H, s), 2.2(2H, m), 2.45(1H, dd, J=8.1, 14.7Hz), 2.53(1H, dd, J=7.0, 14.7Hz), 2.75(1H, d, J=4.2Hz), 2.78(2H, m), 3.57(1H, s), 3.65(3H, s), 5.18(1H, ddd, J=5.3, 5.3, 7.5Hz), 5.24(1H, dt, J=1.7.10.6Hz), 5.30(1H, ddd, J=7, 8.1, 10.8Hz), 5.34(1H, dd, J=4.2, 5.3Hz), 5.41(1H, dt, J=7, 10.6Hz), 5.61(1H, dt, J=7,10.8Hz), 5.61(1H, dd, J=5.3, 5.3Hz), 7.26(1H, s). (Ref. 8029/8036/8037)13C-NMR(125MHz, CDCl3)dppm1 4.3(q), 20.2(t), 20.7(t), 20.9(q), 21.0(q), 21.1(q), 25.8(t), 30.1(t), 33.5(t), 39.4(t), 51.8(q), 53.4(d), 70.0(d), 71.6(d), 72.9(d), 77.2(s), 121.5(d), 126.0(d), 132.9(d), 134.6(d), 136.1(s), 158.1(d), 170.4(s), 170.5(s), 171.3(s), 173.8(s), 196.0(s). (Ref. 8029/8036/8037)
EIMS(30 eV)m/z 496(3), 478(5), 447(17), 418(25), 387(100), 358(22), 327(37), 267(58).DCIMS m/z 574(100). (Ref. 8029/8036/8037)


Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)




291
punaglandin 1 acetate
methyl (5S,6R,7R)-7-[(1R,2S)-2-acetoxy-4-chloro-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenyl]-5,6,7-triacetoxyheptanoate
XPR8016
Yasuji Yamada
C29H39ClO11 599.066 Download ChemDraw structure file

1H-NMR(300MHz, CDCl3)dppm 0.9(3H, t), 1.6(4H, m), 1.6(2H, m), 1.9(3H, s), 2.0(3H, s), 2.1(3H, s), 2.1(2H, m), 2.2(3H, s), 2.3(2H, s), 2.8(1H, t), 2.9(1H, dd), 3.1(1H, d), 3.5(1H, dd), 3.6(3H, s), 5.3(1H, m), 5.3(1H, m), 5.3(1H, m), 5.3(1H, m), 5.3(1H, m), 5.6(1H, dt), 5.7(1H, dt), 7.8(1H, s). (Ref. 8036/8037)



Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)




292
punaglandin 2
methyl (5S,6R,7R)-7-[(1R,2S)-4-chloro-2-hydroxy-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenyl]-5,6,7-triacetoxyheptanoate
XPR8017
Yasuji Yamada
PUG 2
C27H39ClO10 559.045 Download ChemDraw structure file

[a]D+8.8deg(c 1.9, MeOH)(Ref. 8029/8036/8037)
lmax (MeOH)227 nm(e7500) (Ref. 8029/8036/8037)
nmax(CH2CI2) 3420(br), 2920, 1730(br), 1375, 1230, 1045cm-1 (Ref. 8029/8036/8037)
1H-NMR(500MHz, CDCl3)dppm 0.85(3H, t, J=6.7Hz), 1.26(6H, m), 1.6(4H, m), 1.95(2H, m), 1.98(3H, s), 2.06(3H, s), 2.09(3H, s), 2.3(2H, m), 2.40(1H, dd, J=7.9, 14.4Hz), 2.48(1H, dd, J=7.3, 14.4Hz), 2.74(1H, d, J=4.2Hz), 3.48(1H, s), 3.65(3H, s), 5.18(1H, ddd, J=5.3, 5.3, 7.5Hz), 5.25(1H, dt, J=7.3, 7.9, 10.9Hz), 5.31(1H, dd, J=4.2, 5.3Hz), 5.61(1H, dd, J=5.3, 5.3Hz), 5.63(1H, dt, J=7, 10.9Hz), 7.26(1H, s).(Ref. 8029/8036/8037)13C-NMR(125MHz, CDCl3)dppm 14.2(q), 20.2(t), 20.9(q), 21.0(q), 21.1(q), 22.7(t), 27.6(t), 29.3(t), 30.2(t), 31.7(t), 33.5(t), 39.5(t), 51.9(q), 53.5(d), 70.0(d), 71.7(d), 72.9(d), 77.2(s), 121.1(d), 136.0(d), 136.8(s), 158.2(d), 170.4(s), 170.6(s), 171.9(s), 173.8(s), 196.0(s). (Ref. 8029/8036/8037)
EIMS(70 eV)m/z 498(1), 480(1), 467(4), 447(5), 387(100), 327(100), 285(28).CIMS m/z 541(7), 499(58), 481(30), 439(13), 421(100), 361(59).HRCIMS m/z 499.21350 for C25H3635Cl, calcd 499.20988.DCIMS m/z 576 (M++NH4).(Ref. 8029/8036/8037)


Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)




293
punaglandin 2 acetate
methyl (5S,6R,7R)-7-[(1R,2S)-2-acetoxy-4-chloro-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenyl]-5,6,7-triacetoxyheptanoate
XPR8018
Yasuji Yamada
C29H41ClO11 601.082 Download ChemDraw structure file

[a]D+10deg(c 0.6, MeOH) (Ref. 8036/8037)
lmax(CHCl3) 242 nm(e5600) (Ref. 8036/8037)
nmax(CHCl3) 2960, 2920, 2870, 1740(br), 1440, 1370, 1225, 1030cm-1 (Ref. 8036/8037)
1H-NMR(300MHz, CDCl3)dppm 0.86(3H, t, J=6.0Hz), 1.26(6H, m), 1.6(4H, m), 1.90(3H, s), 1.99(3H, s), 2.05(3H, s), 2.09(2H, m), 2.14(3H, s), 2.3(2H, t), 2.77(1H, dd, J=8.3, 10.2Hz), 2.87(1H, dd, J=8.3, 10.2Hz), 3.01(1H, d, J=1.7Hz), 3.65(3H, s), 5.10(1H, dt, J=2.4, 7.8Hz), 5.27(1H, br dt, J=1.1Hz), 5.33(1H, dd, J=1.1, 7.8Hz), 5.50(1H, dt, J=1.7, 7.8Hz), 5.58(1H, dt, J=2.4, 7.8Hz), 7.82(1H, s). (Ref. 8036/8037)13C-NMR(75MHz, CDCl3)dppm 14.0, 20.4, 20.6, 20.8, 21.0, 21.6, 22.5, 27.5, 29.0, 30.3, 31.4, 33.4, 51.6, 52.9, 69.5, 71.1, 72.7, 83.8, 120.0, 136.4, 137.7, 155.1, 169.3, 169.9, 169.9, 170.7, 173.3, 195.0. (Ref. 8036/8037)
EIMS(70 eV)m/z 387(2.6), 378(1.0),327(3.8), 308(1.2), 279(42.5), 167(66.6), 149(99.5), 46(100). (Ref. 8036/8037)


Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)




294
punaglandin 3
methyl (5S,6R,7E)-7-[(2S)-4-chloro-2-hydroxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate
XPR8019
Yasuji Yamada
PUG 3
C25H33ClO8 496.977 Download ChemDraw structure file
Punaglandin 3 inhibits L 1210 leukemia cell proliferation with ac IC50 value of 0.02 mg/ml.(Ref. 8029)
[a]D+66.8deg(c 0.54, MeOH) (Ref. 8029/8036/8037)
lmax (MeOH)238 nm(e8600) (Ref. 8029/8036/8037)
nmax(CHCl3) 3100-3600(br), 2960, 2940, 1725, 1680(sh), 1378, 1235, 1110-990(br) cm-1 (Ref. 8029/8036/8037)
1H-NMR(300MHz, CDCl3)dppm 0.94(3H, t, J=7.5Hz), 1.6(4H, m), 2.05(2H, m), 2.05(3H, s), 2.09(3H, s), 2.3(2H, m), 2.68(1H, dd, J=7.0, 14.3Hz), 2.74(2H, br dd, J=7.1, 7.1Hz), 3.01(1H, dd, J=8.1, 14.3Hz), 3.50(1H, s), 3.65(3H, s), 5.2(1H, m), 5.2(1H, m), 5.25(1H, m), 5.41(1H, m), 5.53(1H, m), 6.02(1H, dd, J=4.3, 9.1Hz), 6.35(1H, d, J=9.1Hz), 7.27(1H, s). (Ref. 8029/8036/8037)13C-NMR(75MHz, CDCl3)dppm 14.2(q), 20.2(t), 20.5(t), 20.8(q), 20.8(q), 25.6(t), 29.6(t), 33.2(t), 35.6(t), 51.7(q), 69.8(d), 73.7(d), 77.2(s), 122.0(d), 126.1(d), 130.5(d), 132.5(d), 133.1(d), 137.2(s), 140.5(s), 155.7(d), 169.9(s), 171.1(s), 173.8(s), 186.6(s). (Ref. 8029/8036/8037)
EIMS(25 eV)m/z 478(1), 418(14), 387(50), 376(14), 358(26), 327(100), 275(30), 267(38), 253(30), 235(35). (Ref. 8029/8036/8037)


Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)
Punaglandin 3 was synthesized from D-(-)-diethyl tartrate and 2-deoxy-D-ribose.(Ref. 8030)



295
punaglandin 3 acetate
methyl (5S,6R,7E)-7-[(2S)-2-acetoxy-4-chloro-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate
XPR8020
Yasuji Yamada
C27H35ClO9 539.014 Download ChemDraw structure file

[a]D+31deg(c 2.7, CHCl3) (Ref. 8036/8037)
lmax(CHCl3) 251 nm(e8000) (Ref. 8036/8037)
nmax(CHCl3) 3020, 2960, 2940, 2929, 2870, 1744(br), 1370, 1220(br), 1020(br) cm-1 (Ref. 8036/8037)
1H-NMR(300MHz, CDCl3)dppm 0.94(3H, t, J=7.5Hz), 1.6(4H, m), 1.9(2H, m), 2.05(3H, s), 2.08(3H, s), 2.10(3H, s), 2.3(2H, t), 2.70(2H, t, J=7.0Hz), 2.8(1H, dd, J=6.6, 14.0Hz), 3.33(1H, dd, J=8.7, 14.0Hz), 3.63(3H, s), 5.2(1H, m), 5.2(1H, m), 5.2(1H, m), 5.38(1H, ddd, J=2, 7, 10.2Hz), 5.46(1H, dt, J=7.0, 10.6Hz), 5.86(1H, dd, J=4.1, 9.4Hz), 6.47(1H, d, J=9.4Hz), 7.59(1H, s). (Ref. 8036/8037)13C-NMR(75MHz, CDCl3)dppm 14.2, 20.2, 20.6, 20.7, 20.8, 21.6, 25.7, 30.0, 33.3, 33.9, 51.6, 69.6, 73.3, 83.3, 120.9, 121.5, 125.9, 130.4, 132.7, 133.8, 135.4, 151.5, 169.3, 169.9, 170.1, 173.6, 185.4. (Ref. 8036/8037)
EIMS(70 eV)m/z 538(0.1), 496(0.1), 478(0.3), 436(0.3), 387(7.0), 376(8.4), 358(10.9), 345(5.3), 327(25.9), 285(12.5), 253(26.2), 235(25.4), 207(21.5), 43(100). (Ref. 8036/8037)


Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)




296
punaglandin 4
methyl (5S,6R,7E)-7-[(2S)-4-chloro-2-hydroxy-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate
XPR8021
Yasuji Yamada
PUG 4
C25H35ClO8 498.993 Download ChemDraw structure file
Punaglandin 4 inhibits L 1210 leukemia cell proliferation with ac IC50 value of 0.07 mg/ml.(Ref. 8034)
[a]D+46.3deg(c 1.6, MeOH) (Ref. 8029/8036/8037)
lmax (MeOH)240 nm(e6900) (Ref. 8029/8036/8037)
nmax(CHCl3) 3150-3600(br), 2930, 2860(sh), 1725, 1675(sh), 1375, 1150-1300(br), 1000-1100(br) cm-1 (Ref. 8029/8036/8037)
1H-NMR(300MHz, CDCl3)dppm 0.86(3H, t, J=7.1Hz), 1.3(6H, m), 1.6(4H, m), 2.0(2H, m), 2.05(3H, s), 2.10(3H, s), 2.3(2H, m), 2.62(1H, dd, J=7.2, 13.5Hz), 2.95(1H, dd, J=8.5, 13.5Hz), 3.63(3H, s), 3.63(1H, s), 5.25(1H, m), 5.25(1H, m), 5.41(1H, m), 5.52(1H, dt, J=6.7, 10.9Hz), 6.01(1H, dd, J=4.3, 9.1Hz), 6.33(1H, d, J=9.1Hz), 7.25(1H, s). (Ref. 8029/8036/8037)13C-NMR(75MHz, CDCl3)dppm 14.2(q), 20.2(t), 20.5(t), 20.8(q), 20.8(q), 25.6(t), 29.6(t), 33.2(t), 35.6(t), 51.7(q), 69.8(d), 73.7(d), 77.2(s), 122.0(d), 126.1(d), 130.5(d), 132.5(d), 133.1(d), 137.2(s), 140.5(s), 155.7(d), 169.9(s), 171.1(s), 173.8(s), 186.6(s). (Ref. 8029/8036/8037)
EIMS(70 eV)m/z 420(2), 387(23), 378(8), 360(6), 347(19), 327(100), 285(44), 267(84), 253(74), 235(82). (Ref. 8029/8036/8037)


Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)
Punaglandin 4 was synthesized from D-(-)-diethyl tartrate and 2-deoxy-D-ribose.(Ref. 8030)Punaglandin 4 was synthesized from (4S)-3-chloro-4-(dimethyl-t-butylsilyloxy)cyclopent-2-enone which is available in five steps from phenol.(Ref. 8031/8034)Other synthesis of punaglandin 4.(Ref. 8032/8033/8035)



297
punaglandin 4 acetate
methyl (5S,6R,7E)-7-[(2S)-2-acetoxy-4-chloro-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate
XPR8022
Yasuji Yamada
C27H35ClO9 539.014 Download ChemDraw structure file

[a]D+9.4deg(c 3.6, CHCl3) (Ref. 8036/8037)
lmax(CHCl3) 249 nm(e6700) (Ref. 8036/8037)
nmax(film) 3020, 2960, 2920, 2860, 1740(br), 1680(sh), 1440, 1370, 1220(br), 1020 cm-1 (Ref. 8036/8037)
1H-NMR(300MHz, CDCl3)dppm 0.86(3H, t, J=6.3Hz), 1.3(6H, m), 1.6(4H, m), 1.94(2H, t, J=6.7Hz), 2.06(3H, s), 2.09(3H, s), 2.11(3H, s), 2.3(2H, m), 2.77(1H, dd, J=6.6, 14.3Hz), 3.31(1H, dd, J=6.6, 14.3Hz), 3.64(3H, s), 5.07(1H, m), 5.1(1H, dt, J=6.6, 10.7Hz), 5.49(1H, dt, J=6.7, 10.7Hz), 5.86(1H, dd, J=4.1, 9.2Hz), 6.47(1H, d, J=9.2Hz), 7.6(1H, s). (Ref. 8036/8037)13C-NMR(75MHz, CDCl3)dppm 14.5, 21.1, 21.2, 21.2, 22.1, 23.0, 27.9, 29.4, 30.5, 32.0, 33.8, 34.4, 52.1, 70.0, 73.7, 83.8, 120.9, 130.8, 136.3, 137.6, 139.0, 152.1, 169.8, 170.3, 170.6, 173.6, 185.9. (Ref. 8036/8037)
EIMS(70 eV)m/z 540(3.2), 498(0.8), 480(0.5), 462(1.6), 438(2.2), 420(3.8), 387(25.1), 378(23.5), 327(50.6), 308(29.3), 266(41.4), 253(44.2), 237(37.5), 222(43.4), 207(37.3), 43(100). (Ref. 8036/8037)


Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)




298
Z-punaglandin 3
methyl (5S,6R,7Z)-7-[(2S)-4-chloro-2-hydroxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate
XPR8023
Yasuji Yamada
(7Z)-PUG 3
C25H33ClO8 496.977 Download ChemDraw structure file

1H-NMR(300MHz, CDCl3)dppm 0.95(3H,t,J=7.5Hz), 1.6(4H,m), 2.0(2H,m), 2.03(3H,s), 2.10(3H,s), 2.3(2H,m), 2.47(1H,dd,J=7.3,14.5Hz), 2.59(1H,dd,J=7.7,14.5Hz), 2.74(2H,dd,J=6.4,7.2Hz), 3.5(1H,s), 3.64(3H,s), 5.1(1H,m), 5.1(1H,m), 5.1(1H,m), 5.2(1H,m), 5.36(1H,dt,J=7.2,10.9Hz), 6.08(1H,d), 6.32(1H,dd,J=3.5,7.7Hz), 7.20(1H,s). (Ref. 8029/8036/8037)
EIMS(70 eV)m/z 436(1.2), 418(0.9), 387(5.2), 376(4.1), 345(7.5), 327(41.7), 285(28.2), 43(100). (Ref. 8029/8036/8037)


Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)




299
Z-punaglandin 3 acetate
methyl (5S,6R,7Z)-7-[(2S)-2-acetoxy-4-chloro-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate
XPR8024
Yasuji Yamada
C27H35ClO9 539.014 Download ChemDraw structure file

[a]D+19deg(c 1.8, CHCl3) (Ref. 8036/8037)
lmax(CHCl3) 255 nm(e9000), 242 nm(e7900) (Ref. 8036/8037)
1H-NMR(300MHz, CDCl3)dppm 0.95(3H, t, J=7.5Hz), 1.6(4H, m), 2.00(3H, s), 2.02(3H, s), 2.07(2H, m), 2.10(3H, s), 2.3(2H, m), 2.63(1H, dd, J=6.7, 14.5Hz), 2.73(2H, t, J=4.8Hz), 2.88(1H, dd, J=6.7, 14.5Hz), 3.64(3H, s), 5.15(1H, ddd, J=6.7, 7.5, 10.6Hz), 5.18(1H, dt, J=3.4Hz), 5.20(1H, dt, J=4.8, 10.5Hz), 5.40(1H, dt, J=7.0, 10.5Hz), 5.53(1H, dt, J=7.3, 10.6Hz), 6.1(1H, d), 6.46(1H, dd, J=3.4, 7.7Hz), 7.53(1H, s). (Ref. 8036/8037)13C-NMR(75MHz, CDCl3)dppm 14.2, 20.6, 20.6, 20.8, 20.8, 21.6, 25.7, 30.0, 33.4, 35.3, 51.6, 69.9, 74.0, 82.1, 120.9, 125.8, 132.7, 133.7, 136.0, 136.5, 139.6, 150.1, 169.5, 169.6, 170.0, 173.7, 193.8. (Ref. 8036/8037)
EIMS(70 eV)m/z 538(3.5), 478(2.4), 436(2.8), 418(12.5), 387(16.3), 376(20.8), 366(11.2), 358(23.0), 345(13.4), 327(28.6), 43(100). (Ref. 8036/8037)


Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)




300
Z-punaglandin 4
methyl (5S,6R,7Z)-7-[(2S)-4-chloro-2-hydroxy-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate
XPR8025
Yasuji Yamada
(7Z)-PUG 4
C25H35ClO8 498.993 Download ChemDraw structure file
Z-Punaglandin 4 inhibits L 1210 leukemia cell proliferation with ac IC50 value of 0.06 mg/ml.(Ref. 8034)
1H-NMR(300MHz, CDCl3)dppm 0.87(3H, t, J=6Hz), 1.3(6H, m), 1.6(4H, m), 1.97(2H, m), 2.03(3H, s), 2.10(3H, s), 2.3(2H, m), 2.44(1H, dd, J=8, 14Hz), 2.56(1H, dd, J=8, 14Hz), 2.79(1H, s), 3.64(3H, s), 5.2(1H, m), 5.2(1H, m, J=3.4Hz), 5.57(1H, dt, J=7.6, 10.9Hz), 6.07(1H, d), 6.32(1H, dd, J=3.6, 7.8Hz), 7.20(1H, s). (Ref. 8029/8036/8037)



Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)
Z-Punaglandin 4 was synthesized from (4S)-3-chloro-4-(dimethyl-t-butylsilyloxy)cyclopent-2-enone which is available in five steps from phenol.(Ref. 8031/8034)Other synthesis of Z-punaglandin 4.(Ref. 8032/8033/8035)



301
Z-punaglandin 4 acetate
methyl (5S,6R,7Z)-7-[(2S)-2-acetoxy-4-chloro-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate
XPR8026
Yasuji Yamada
C27H35ClO9 539.014 Download ChemDraw structure file

[a]D+11deg(c 1.8, CHCl3) (Ref. 8036/8037)
lmax (MeOH)254 nm(e6700), 241 nm(e5100) (Ref. 8036/8037)
1H-NMR(300MHz, CDCl3)dppm 0.87(3H, t, J=6.1Hz), 1.3(6H, m), 1.6(4H, m), 1.9(2H, m), 2.00(3H, s), 2.02(3H, s), 2.10(3H, s), 2.3(2H, m), 2.58(1H, dd), 2.86(1H, dd), 3.64(3H, s), 5.2(1H, m), 5.2(1H, m), 5.54(1H, dt, J=8.8, 10.7Hz), 6.09(1H, d), 6.46(1H, dd, J=3.9, 7.8Hz), 7.53(1H, s). (Ref. 8036/8037)13C-NMR(75MHz, CDCl3)dppm 14.0, 20.6, 20.8, 21.6, 22.6, 23.1, 27.5, 29.0, 30.0, 31.5, 33.5, 35.4, 51.6, 69.8, 74.0, 82.3, 120.6, 135.7, 135.8, 136.5, 142.5, 149.0, 173.1, 173.4, 173.7, 176.3, 190.8. (Ref. 8036/8037)
EIMS(70 eV)m/z 540(3.2), 480(0.9), 438(2.7), 429(2.6), 420(3.5), 387(18.6), 378(17.2), 360(14.1), 327(27.9), 308(20.4), 285(14.9), 43(100). (Ref. 8036/8037)


Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)




302
punaglandin 3 epoxide
methyl (5S,6R,7E)-7-[(2S,3R,4S)-4-chloro-3,4-epoxy-2-hydroxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentanylidene]-5,6-diacetoxyheptanoate
XPR8027
Yasuji Yamada
C25H33ClO9 512.977 Download ChemDraw structure file

[a]D+16deg(c 3.0, MeOH) (Ref. 8036/8037)
lmax(CHCl3) 245 nm(e7400) (Ref. 8036/8037)
nmax(film) 3483(br), 3010, 2960, 2875, 1736(br), 1375, 1223(br), 1024 cm-1 (Ref. 8036/8037)
1H-NMR(300MHz, CDCl3)dppm 0.94(3H, t, J=7.5Hz), 1.6(4H, m), 2.0(2H, m), 2.03(3H, s), 2.08(3H, s), 2.3(2H, m), 2.7(2H, m), 2.8(1H, m), 2.8(1H, m), 3.65(3H, s), 3.67(1H, s), 3.96(1H, s), 5.2(1H, m), 5.2(1H, m), 5.2(1H, m), 5.4(1H, m), 5.58(1H, m), 5.98(1H, dd, J=4.2, 9.0Hz), 6.54(1H, d, J=9.0Hz). (Ref. 8036/8037)13C-NMR(75MHz, CDCl3)dppm 14(q), 20.2(t), 20.6(t), 20.7(q), 20.8(q), 25.7(t), 29.6(t), 29.7(t), 33.2(t), 34.2(t), 51.8(q), 66.7(d), 69.5(d), 73.6(d), 93.1(s), 120.9(d), 125.9(d), 132.8(d), 133.9(d), 138.6(s), 139.9(d), 169.9(s), 170.7(s), 173.6(s), 187.3(s). (Ref. 8036/8037)
EIMS(70 eV)m/z 512(0.1), 494(0.8), 403(3.4), 343(24.3), 283(18.9), 43(100). (Ref. 8036/8037)


Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)




303
punaglandin 4 epoxide
methyl (5S,6R,7E)-7-[(2S,3R,4S)-4-chloro-3,4-epoxy-2-hydroxy-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentanylidene]-5,6-diacetoxyheptanoate
XPR8028
Yasuji Yamada
C25H35ClO9 514.993 Download ChemDraw structure file

[a]D+22.5deg(c 0.8, MeOH) (Ref. 8036/8037)
1H-NMR(300MHz, CDCl3)dppm 0.86(3H, t, J=6.0Hz), 1.2(6H, m), 1.5(6H, m), 2.0(2H, m), 2.03(3H, s), 2.09(3H, s), 2.3(2H, m), 2.76(1H, dd, J=8, 4Hz), 2.85(1H, dd, J=8, 4Hz), 3.55(1H, s), 3.66(3H, s), 3.95(1H, s), 5.2(1H, m), 5.2(1H, m), 5.59(1H, m), 5.97(1H, dd, J=4.4, 8.9Hz), 6.55(1H, d, J=8.9Hz). (Ref. 8036/8037)
EIMS(70 eV)m/z 514(0.2), 496(4), 436(1), 423(5), 403(7), 343(39), 283(22), 269(22), 43(100). (Ref. 8036/8037)


Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)




304
punaglandin 5
methyl (5S,6R)-7-[(1R,2S)-4-chloro-2-hydroxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenyl]-5,6-diacetoxyheptanoate
XPR8029
Yasuji Yamada
PUG 5
C25H35ClO8 498.993 Download ChemDraw structure file

[a]D+10.2deg(c 4.7, CHCl3) (Ref. 8036/8037)
lmax(CHCl3) 244 nm(e5000) (Ref. 8036/8037)
nmax(CHCl3) 3450(br), 3010, 2960, 2930, 2870, 1748, 1600, 1440, 1380, 1230, 1170, 1040 cm-1 (Ref. 8036/8037)
1H-NMR(300MHz, CDCl3)dppm 0.94(3H, t, J=7.3Hz), 1.6(4H, m), 1.73(1H, dd, J=7.8, 15.2Hz), 2.0(2H, t), 2.08(3H, s), 2.09(3H, s), 2.16(1H, dd, J=8.1, 14.3Hz), 2.3(2H, t), 2.58(1H, s), 2.65(1H, dd, J=4.6, 8.5Hz), 2.67(1H, dd, J=7.7, 7.8Hz), 2.77(2H, t), 2.80(1H, dd, J=8.0, 8.5Hz), 3.64(3H, s), 5.1(1H, m), 5.1(1H, m), 5.1(1H, m), 5.11(1H, br d, J=3.4Hz), 7.30(1H, s). (Ref. 8036/8037)13C-NMR(75MHz, CDCl3)dppm 14.2, 20.2, 20.6, 20.9, 25.7, 29.9, 30.0, 33.4, 35.9, 38.7, 51.6, 55.1, 72.2, 73.7, 77, 121.6, 125.9, 132.9, 134.3, 134.6, 157.5, 170.6, 170.7, 171.1, 196.6. (Ref. 8036/8037)
EIMS(70 eV)m/z 480(0.4), 419(5.9), 389(9.4), 387(8.1), 329(31.4), 285(10.8), 43(100). (Ref. 8036/8037)


Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)




305
punaglandin 5 acetate
methyl (5S,6R)-7-[(1R,2S)-4-chloro-2-hydroxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenyl]-5,6-diacetoxyheptanoate
XPR8030
Yasuji Yamada
C27H37ClO9 541.030 Download ChemDraw structure file

[a]D+8deg(c 1.2, MeOH) (Ref. 8036/8037)
lmax(CHCl3) 240 nm(e4500) (Ref. 8036/8037)
1H-NMR(300MHz, CDCl3)dppm 0.95(3H, t, J=7Hz), 1.6(4H, m), 1.9(2H, m), 2.0(2H, m), 2.1(3H, s), 2.2(3H, s), 2.2(3H, s), 2.3(2H, m), 2.3(2H, m), 2.6(2H, t), 3.0(1H,dd), 3.2(1H, t), 3.6(3H, s), 5.0(1H, m), 5.2(1H, dt, J=10.5Hz), 5.2(1H, dd, J=8, 10Hz), 5.3(1H, m), 5.4(1H, m), 5.5(1H, ddd, J=1, 7, 10.8Hz), 7.5(1H, s). (Ref. 8036/8037)13C-NMR(75MHz, CDCl3)dppm 14.2, 20.6, 20.9, 21.0, 21.5, 25.7, 26.4, 30.0, 33.4, 35, 36, 52, 52.2, 72.3, 72.8, 85.5, 121.0, 123.0, 125.7, 132.8, 133.4, 155.6, 169.9, 170.3, 170.5, 173.0, 197. (Ref. 8036/8037)
EIMS(70 eV)m/z 480(4.9), 420(27.4), 407(13.6), 378(12.4), 360(25.6), 329(33.4), 269(29.2), 43(100). (Ref. 8036/8037)


Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)




306
punaglandin 6