 |
|
| 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 | |
Prostaglandin A1 relaxes uterine muscle and shows hypotensive effects on rat and dog (Ref. 0002). |
42-44  C (Ref. 1005) |
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) |
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 | |
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). |
|||||||||||||
| 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 | |
19-Hydroxy-prostaglandin A2 relaxes uterine myometriuim (Ref. 0082). |
DIETHYL ETHER, CHLOROFORM, ETHANOL (Ref. 1104) |
l EtOHmax = 217 nm(e  10,000) (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) |
|||||||||||||
| 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 | |
70-71 C (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 | |
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). |
|||||||||||||||
| 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 | |
19-Hydroxy-prostaglandin B2 relaxes uterine myometriuim (Ref. 0082). |
ETHANOL (Ref. 1104) |
l EtOHmax = 278 nm(e 20,000) (Ref. 1104) |
5.92, 6.09, 6.26, 10.3mm (Ref. 1104) |
|||||||||||||||
| 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 | |
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) |
||||||||||||||
| 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 | |
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). |
68 C (Ref. 1010) |
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). |
|||||||||||
| 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 | |
115-117 C (Ref. 1107) |
[a]578=-61.6 (C=0.56, 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 | |
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). |
65-66 C (Ref. 1001) |
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 | |
As presented in Table 1 of reference (Ref. 0002), prostaglandin E3 is 1/10-1/2 as active as prostaglandin E2. |
84.5-85.5 C (Ref. 1113) |
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) |
||||||||||||||
| 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 | |
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 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 | |
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 | |
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). |
65 C (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 | |
102-103 C (Ref. 1110) |
d,l-PGF1a ; KBr : n 3330, 1716, 967 cm-1 (Ref. 1111) |
m/e 356(M+), 338, 320 (Ref. 1102) |
||||||||||||||||
| 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 | |
25-35 C (Ref. 1007) |
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). |
|||||||||||||
| 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 | |
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 | |
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 | |
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 | |
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 37 C 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 | |
METHYL ESTER:to be cited the Chart(Ref. 1018) |
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 37 C 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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
13,14-dihydro-15keto PGE1 is a week inhibitor of ADP-induced platelet aggregation in human PRP. |
|||||||||||||||||||
| 29 |  |
15-keto Prostaglandin E1 |
9,15-dioxo-11a-hydroxy-prost-13E-en-1-oic acid |
XPR1709 | Takehiko Yokomizo |
C20H32O5 | 352.465 | |
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 | |
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 | |
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 | |
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 | |
||||||||||||||||||||
| 34 |  |
20-hydroxy Prostaglandin E2 |
9-oxo-11a,15S,20-trihydroxy-prosta-5Z,13E-dien-1-oic acid |
XPR1714 | Takehiko Yokomizo |
C20H32O6 | 368.464 | |
||||||||||||||||||||
| 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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
||||||||||||||||||||
| 49 |  |
Prostaglandin D1 |
9a,15S-dihydroxy-11-oxo-prost-13E-en-1-oic acid |
XPR1731 | Takehiko Yokomizo |
C20H34O5 | 354.481 | |
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 | |
||||||||||||||||||||
| 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 | |
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 | |
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 | |
||||||||||||||||||||
| 54 |  |
11-deoxy Prostaglandin E1 |
9-oxo-15S-hydroxy-prosto-13E-en-1-oic acid |
XPR1736 | Takehiko Yokomizo |
C20H34O4 | 338.482 | |
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 | |
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 | |
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 | |
||||||||||||||||||||
| 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 | |
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 | |
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 | |
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 | |
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 | |
||||||||||||||||||||
| 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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
||||||||||||||||||||
| 69 |  |
Prostaglandin F1b |
9b,11a,15S-trihydroxy-prost-13E-en-1-oic acid |
XPR1751 | Takehiko Yokomizo |
C20H36O5 | 356.497 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
||||||||||||||||||||
| 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 | |
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 | |
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 |
|
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 | |
||||||||||||||||||||
| 89 |  |
15(R)-Prostaglandin D2 |
9a,15R-dihydroxy-11-oxo-prosta-5E,13E-dien-1-oic acid |
XPR1772 | Takehiko Yokomizo |
C20H32O5 | 352.465 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
||||||||||||||||||||
| 98 |  |
Prostaglandin F1b |
9b,11a,15S-trihydroxy-prost-13E-en-1-oic acid |
XPR1781 | Takehiko Yokomizo |
C20H36O5 | 356.497 | |
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 |
|
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 | |
||||||||||||||||||||
| 101 |  |
Prostaglandin F2a dimethyl amine |
1-dimethylamino-9a,11a,15S-trihydroxy-prosta-5Z,13E-diene |
XPR1784 | Takehiko Yokomizo |
C22H4NO3 | 330.272 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
||||||||||||||||||||
| 113 |  |
8-iso Prostaglandin F3a |
9a,11a,15S-trihydroxy-(8b)-prosta-5Z,13E,17Z-trien-1-oic acid |
XPR1797 | Takehiko Yokomizo |
C20H32O5 | 352.465 | |
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 | |
||||||||||||||||||||
| 115 |  |
6a-Prostaglandin I1 |
6R,9a-epoxy-11a,15S-dihydroxy-prost-13E-en-1-oic acid |
XPR1799 | Takehiko Yokomizo |
C20H34O5 | 354.481 | |
||||||||||||||||||||
| 116 |  |
6b-Prostaglandin I1 |
6S,9a-epoxy-11a,15S-dihydroxy-prost-13E-en-1-oic acid |
XPR1800 | Takehiko Yokomizo |
C20H34O5 | 354.481 | |
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 | |
[a]D=78 (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). |
Stability:unstable in water around neutrality with a half life of about 5 min at 37 C 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 | |
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). |
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) |
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 | |
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 | |
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). |
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 | |
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). |
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 | |
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). |
Stability:unstable in water around neutrality with a half life of about 40 sec at 37 C 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 | |
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 | |
Thromboxane B2 as s stable degradation product of thromboxane A2 shows diminishd biological activity (Ref. 0014). |
95-96 C (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 | |
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 | |
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) |
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 | |
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) |
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 | |
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). |
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 37 C 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 | |
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) |
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). |
|||||||||||||
| 130 |  |
12-oxo-Leukotriene B4 |
5S-hydroxy-12-keto-[6Z, 8E, 10E, 14Z]-eicosatetraenoic acid |
XPR3111 | Takao Shimizu |
12-oxo-LTB4 |
C20H30O4 | 334.450 | |
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. |
||||||||||||||
| 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 | |
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 | |
||||||||||||||||||||
| 133 |  |
Leukotriene B4 Ethanolamide |
N-(2-hydroxyethyl)-5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraenamide |
XPR3114 | Takehiko Yokomizo |
C22H37NO4 | 379.534 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
||||||||||||||||||||
| 140 |  |
20-trifluoro Leukotriene B4 |
5S,12R-dihydroxy-20,20,20-trifluoro-6Z,8E,10E,14Z-eicosatetraenoic acid |
XPR3121 | Takehiko Yokomizo |
C20H29F3O4 | 390.437 | |
||||||||||||||||||||
| 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 | |
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) |
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). |
||||||||||||||
| 142 |  |
11-trans Leukotriene C4 |
5S-hydroxy-6R-(S-glutathionyl)-7E,9E,11E14Z-eicosatetraenoic acid |
XPR3202 | Takehiko Yokomizo |
C30H47N3O9 | 593.709 | |
||||||||||||||||||||
| 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 | |
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) |
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 | |
||||||||||||||||||||
| 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 | |
Leukotriene E4 stimulates airway smooth muscles from different animal species, and is less potent than C4 in contracting isolated guinea pig ileum (Ref. 0022). |
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) |
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 | |
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 | |
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 | |
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 | |
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) |
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) |
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 | |
Lipoxin B4 is either vasoconstrictive or vasodilatory, and blocks the cytotoxic action of NK cell (Ref. 0035). |
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) |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
METHYL ESTER;l EtOHmax = 237nm (e 31,000) (Ref. 1081) |
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 | |
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). |
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 | |
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 | |
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 | |
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). |
DIETHYL ETHER , ACETONE , BENZENE (Ref. 1083) |
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 | |
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 | |
l max = 237nm (Ref. 1089) |
METHYL ESTER TMS ETHER ; m/e 406(M+), 391, 375, 316, 295 (Ref. 1089) |
||||||||||||||||||
| 164 |  |
(R),(Z,E,Z,Z)-8-Hydroxy-5,9,11,14-eicosatetraenoic acid |
XPR6114 | Shouzo Yamamoto |
8(R)-HETE |
C20H32O3 | 320.466 | |
The compound is involved in the maturation of starfish oocyte (Ref. 0074). |
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) |
||||||||||||||||
| 165 |  |
(R),(Z,Z,Z)-12-Hydroxy-5,8,14-eicosatetraenoic acid |
XPR6122 | Shouzo Yamamoto |
C20H34O3 | 322.482 | |
The compound has vasodilatory activity, and may be involved in the wound-healing of corneal injury (Ref. 0075). |
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 | |
The compound stimulates chemotactic and chemokinetic activities of human polymorphonuclear leukocytes (Ref. 0066). |
DIETHYL ETHER (Ref. 1081) |
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) |
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 | |
The compound is active in stimulated secretion of somatostatin, insulin and glucagon, vasodilataion and regulation of intracellular calcium (Ref. 0078). |
||||||||||||||||||
| 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 | |
The compound relaxes intestinal artery (Ref. 0078). |
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) |
|||||||||||||||
| 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 | |
The compound relaxes intestinal artery, inhibits vasopressin-dependent water flow in urinary bladder, and regulates intracellular calcium level (Ref. 0078). |
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) |
||||||||||||||||
| 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 | |
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]  =-2,75(C=0.70, CHLOROFORM) 14(S),15(R)-EET METHYL ESTER ; [a]=+2.78(C=0.82, CHLOROFORM) (Ref. 1099) |
|||||||||||||||||
| 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 | |
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 | |
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.  5.7(Ref. 7001) |
oil(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] |
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) |
|||||||||||||
| 173 |  |
Anandamide (20:2, n-6) |
N-cis-11,14-eicosadienoyl ethanolamine |
XPR7002 | Keizo Waku |
C22H27NO2 | 337.455 | |
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 | |
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 | |
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) |
|||||||||||||||
| 176 |  |
Anandamide (20:3, n-3) |
N-cis-11, 14,17-eicosatrienoylethanolamine |
XPR7005 | Keizo Waku |
C22H39NO2 | 349.551 | |
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 | |
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 | |
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) |
||||||||||||||||
| 179 |  |
Anandamide (20:5, n-3) |
N-cis-5,8, 11,14,17-eicosapentaenoylethanolamine |
XPR7008 | Keizo Waku |
C22H35N02 | 327.527 | |
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 | |
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 | |
Binding of this compound to the brain cannabinoid receptor (CB1), Ki (nM)>1000(Ref. 7001) |
67 - 68 C (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 | |
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 | |
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 | |
Binding of this compound to the brain cannabinoid receptor (CB1)was not found. (Ref. 7001) |
100-101 C (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 | |
Binding of this compound to the brain cannabinoid receptor (CBl)was not found. (Ref. 7001) |
74-75 C(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 | |
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 | |
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 | |
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 | |
Binding of this compoud to the brain cannabinoid receptor (CBl), Ki(nM)>10000 (Ref. 7001) |
colorless oil (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 | |
Binding of this compound to the brain cannabinoid receptor(CB1),Ki(nM)>10000 (Ref. 7001) |
colorless oil (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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
colorless oil (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 | |
colorless oil (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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 |  |
( )-N-(1-methyl-2-hydroxy-2-phenylethyl)arachidonoyl amide |
XPR7044 | Keizo Waku |
C29H43NO2 | 437.657 | |
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 ( )phenylpropanolamine.Yield 67 %. (Ref. 7001) |
|||||||||||||||||
| 216 |  |
a-methyl anandamide |
XPR7045 | Keizo Waku |
C23H39NO | 345.562 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
colorless liquid (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 | |
colorless oil (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 | |
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 (50 C 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 | |
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 50 C 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 | |
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 50 C. Yield 65%. (Ref. 7009) |
|||||||||||||||||||
| 230 |  |
(16,16-dimethyldocosa-cis-5,8,11,14-tetraenoyl)-2'-methoxyethylamine |
XPR7059 | Keizo Waku |
C27H47NO2 | 417.668 | |
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 50 C.Yield 4l %. (Ref. 7009) |
|||||||||||||||||||
| 231 |  |
(16,16-dimethyldocosa-cis-5,8,11,14-tetraenoyl)propylamine |
XPR7060 | Keizo Waku |
C27H47NO | 401.668 | |
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 50 C.Yield 44%. (Ref. 7009) |
|||||||||||||||||||
| 232 |  |
N-((R)-(-)-2-hydroxypropyl)a,a-dimethylarachidonoylamide |
XPR7061 | Keizo Waku |
C25H43NO2 | 389.614 | |
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 | |
This compound was synthesized from eicosanoylchloride and ethanolamine. (Ref. 7010) |
||||||||||||||||||||
| 234 |  |
N-eicosanoyl-(2'-fluoroethyl)amine |
XPR7063 | Keizo Waku |
C22H44NOF | 357.589 | |
This compound was synthesized from eicosanoylchloride and 2-fluoroethylamine. (Ref. 7010) |
||||||||||||||||||||
| 235 |  |
arachidonoyl-N-(4-benzenesulfonamide)amide |
XPR7064 | Keizo Waku |
C26H37N202S | 3210.999 | |
This compound was synthesized from arachidonoylchloride and 4-aminobenzenesulfonamide. (Ref. 7010) |
||||||||||||||||||||
| 236 |  |
arachidonoyl-(4'-bromobenzenesulfon)amide |
XPR7065 | Keizo Waku |
C26H35O3SBr | 507.524 | |
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 | |
This compound was synthesized from arachidonoylchloride and morpholine. (Ref. 7010) |
||||||||||||||||||||
| 238 |  |
arachidonoyl-(2'-(4-bezenesulfonamide)ethyl)amide |
XPR7067 | Keizo Waku |
C29H42NSO3 | 484.715 | |
This compound was synthesized from arachidonoylchloride and 2-(4'-benzenesulfonamide)ethylamine. (Ref. 7010) |
||||||||||||||||||||
| 239 |  |
arachidonoyl-(2'-phenoxyethyl)amide |
XPR7068 | Keizo Waku |
C29H41NO2 | 435.641 | |
This compound was synthesized from arachidonoylchloride and phenoxyethylamine. (Ref. 7010) |
||||||||||||||||||||
| 240 |  |
arachidonoyl-(2'-fluoroethyl)amide |
XPR7069 | Keizo Waku |
C23H36NOF | 361.536 | |
This compound was synthesized from arachidonoylchloride and 2-fluoroethylamine. (Ref. 7010) |
||||||||||||||||||||
| 241 |  |
2-methylarachidonoyl-(2'-fluoroethyl)amide |
XPR7070 | Keizo Waku |
C23H38NOF | 363.552 | |
This compound was synthesized from 2-methylarachidonoylchloride and 2-fluoroethylamine. (Ref. 7010) |
||||||||||||||||||||
| 242 |  |
2-isopropylarachidonoyl-(2'-hydroxyethyl)amide |
XPR7071 | Keizo Waku |
C26H43NO2 | 401.625 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 |  |
( )-2,16,16-trimethyl-5,8,11,14-all-cis-docosatetraenoyl-2'-fluoroethyamine |
XPR7080 | Keizo Waku |
C27H47FNO | 420.667 | |
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 |  |
( )-2,16,16-trimethyl-5,8,11,14-all-cis-tricosatetraenoyl-2'-fluoroethylamine |
XPR7081 | Keizo Waku |
C28H48NOF | 433.685 | |
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 |  |
( )-2,16,-dimethyl-5,8,11,14-all-cis-docosatetraenoyl-2'-fluoroethylamine |
XPR7082 | Keizo Waku |
C26H45FNO | 406.640 | |
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 |  |
( )-2,17,17,-trimethyl-5,8,11,14-all-cis-docosatetraenoyl-2'-fluoroethylamine |
XPR7083 | Keizo Waku |
C27H47FNO | 420.667 | |
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 |  |
( )-2,17,-dimethyl-5,8,11,14-all-cis-docosatetraenoyl-2'-fluoroethylamine |
XPR7084 | Keizo Waku |
C26H44FNO | 405.632 | |
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 |  |
( )-2-methyl-5,8,11,14-all-cis-tricosatetraenoyl-2'-fluoroethylamine |
XPR7085 | Keizo Waku |
C26H45FNO | 406.640 | |
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 | |
Effect of 2-arachidonoylglycerol on the specific binding of CP55940 to rat synaptosomal membrane. Ki= 3.1 M (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) |
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 85 C 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 | |
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 85 C 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 | |
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 85 C 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 | |
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 | |
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 | |
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 | |
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 | |
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 | |
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 C under vacuum for 3 min. (Ref. 7014) |
|||||||||||||||||
| 266 |  |
2-oleoylglycerol |
2-Mono(9'-octadecenoyl)glycerol |
XPR7095 | Keizo Waku |
C21H40O4 | 356.540 | |
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 85 C under vacuum for 3 min. (Ref. 7014) |
|||||||||||||||||
| 267 |  |
2-linoleoylglycerol |
2-Mono((all Z)-9',12'-octadecadienoyl)glycerol |
XPR7096 | Keizo Waku |
C2lH38O4 | |
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 85 C 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 | |
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 85 C 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 | |
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 85 C 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 | |
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 85 C 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 | |
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 85 C 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 | |
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 85 C 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 | |
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 C 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 | |
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 C 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 | |
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) |
||||||||||||||||
| 276 |  |
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 | |
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 -28.9 (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) |
||||||||||||||
| 277 |  |
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 | |
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 +10.9 (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) |
||||||||||||||
| 278 |  |
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 | |
[a]D +45.5 (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) |
|||||||||||||||
| 279 |  |
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 | |
[a]D -80.0 (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) |
|||||||||||||||
| 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 | |
20-Acetoxyclavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8022) |
[a]D -31.1 (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) |
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 | |
20-Acetoxyclavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8022) |
[a]D +3.7 (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) |
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 | |
20-Acetoxyclavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8022) |
[a]D +26.4 (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) |
20-Acetoxyclavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8024) |
|||||||||||||
| 283 |  |
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 | |
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 -1.2 (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) |
Photoisomerization of chlorovulone I (fluoresent lamp, benzene, 40 hr) gave a mixture of chlorovulones I, II and III.(Ref. 8025) |
|||||||||||||
| 284 |  |
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 | |
(-)-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 +22.7 (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) |
|||||||||||||||
| 285 |  |
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 | |
[a]D +27.3 (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) |
Photoisomerization of chlorovulone I (fluoresent lamp, benzene, 40 hr) gave a mixture of chlorovulones I, II and III.(Ref. 8025) |
|||||||||||||||
| 286 |  |
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 | |
12-O-acetylchlorovulone IV[a]D -12 (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) |
||||||||||||||||||
| 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 | |
[a]D -24.1 (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 | |
[a]D +6.0 (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 | |
[a]D +15.2 (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 | |
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) |
||||||||||||||||||
| 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 | |
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) |
|||||||||||||||||||
| 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 | |
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) |
||||||||||||||||||
| 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 | |
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) |
|||||||||||||||||||
| 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 | |
Punaglandin 3 inhibits L 1210 leukemia cell proliferation with ac IC50 value of 0.02 mg/ml.(Ref. 8029) |
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) |
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 | |
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) |
|||||||||||||||||||
| 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 | |
Punaglandin 4 inhibits L 1210 leukemia cell proliferation with ac IC50 value of 0.07 mg/ml.(Ref. 8034) |
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) |
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 | |
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) |
|||||||||||||||||||
| 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 | |
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) |
||||||||||||||||||
| 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 | |
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) |
|||||||||||||||||||
| 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 | |
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) |
|||||||||||||||||
| 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 | |
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) |
|||||||||||||||||||
| 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 | |
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) |
|||||||||||||||||||
| 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 | |
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) |
|||||||||||||||||||
| 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 | |
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) |
||||||||||||||||||
| 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 | |
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) |
|||||||||||||||||||
| 306 |  |
punaglandin 6 |
methyl (5S,6R)-7-[(1R,2S)-4-chloro-2-hydroxy-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenyl]-5,6-diacetoxyheptanoate |
XPR8031 | Yasuji Yamada |
PUG 6 |
C25H37ClO8 | 501.009 | |
1H-NMR(300MHz, CDCl3)dppm 0.85(3H, t, J=6.2Hz), 1.3(6H, m), 1.6(4H, m), 1.73(1H, ddd, J=1.2, 8.4, 15.4Hz), 2.03(2H, dt, J=6.2, 6.4Hz), 2.10(3H, s), 2.10(1H, dd, J=1.4, 13.5Hz), 2.11(3H, s), 2.12(1H, ddd, J=4.5, 15.4Hz), 2.3(2H, t), 2.54(1H, s), 2.66(1H, dd, J=4.5, 8.4Hz), 2.77(1H, dd, J=1.4, 13.5Hz), 3.65(3H, s), 5.11(1H, br d, J=3.4Hz), 5.28(1H, ddd, J=1.2, 3.4, 8Hz), 5.65(1H, dt, J=6.4, 11.1Hz), 7.29(1H, s). (Ref. 8036/8037)13C-NMR(75MHz, CDCl3)dppm 14.0, 20.6, 20.8, 21.1, 22.5, 25.5, 27.5, 29.0, 30.0, 31.5, 33.4, 35.8, 51.6, 55.1, 72.1, 72.2, 78.9, 121.3, 134.4, 136.2, 157.6, 170.6, 170.6, 173.5, 196.7. (Ref. 8036/8037) |
||||||||||||||||||
| 307 |  |
punaglandin 7 |
methyl (5Z,7S)-7-[(1R,2S)-4-chloro-2-hydroxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenyl]-5-heptenoate |
XPR8032 | Yasuji Yamada |
PUG 7 |
C23H31ClO6 | 438.941 | |
|||||||||||||||||||
| 308 |  |
punaglandin 8 |
methyl (5Z,7S)-7-[(1R,2S)-4-chloro-2-hydroxy-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenyl]-5-heptenoate |
XPR8033 | Yasuji Yamada |
PUG 8 |
C23H33ClO6 | 440.957 | |
1H-NMR(300MHz, CDCl3)dppm 0.86(3H, t, J=6.7Hz), 1.3(6H, m), 1.7(2H, m), 1.98(3H, s), 2.00(2H, dt, J=6.7, 7.0Hz), 2.19(2H, dt, J=6.7, 7.0Hz), 2.3(2H, t), 2.38(1H, dd, J=7.1, 14.7Hz), 2.53(1H, dd, J=8.1, 14.7Hz), 3.18(1H, s), 3.65(3H, s), 5.32(1H, ddd, J=7.1, 8.1, 11.2Hz), 5.57(1H, dd, J=6.7, 7Hz), 5.64(1H, dt, J=6.7, 7.0Hz), 5.83(1H, dd, J=9.6, 10.7Hz), 5.94(1H, dd, J=3.3, 9.6Hz), 7.26(1H, s). (Ref. 8036/8037) |
||||||||||||||||||
| 309 |  |
clavulolactone I (Ref. 8038) |
(R)-4-{(1Z,3E)-3-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-1-propenyl}-4-butanolide |
XPR8034 | Yasuji Yamada |
C22H28O5 | 372.455 | |
[a]D -7.8 (C 0.26, CHCl3)(Ref. 8038) |
lEtOHmax 231 nm(log e4.14),292 nm(log e4.20)(Ref. 8038) |
nfilmmax1770,1732, 1704, 1643, and 1230cm-1(Ref. 8038) |
1H-NMR(500MHz,CDCl3)dppm0.88(3H,t,J=6.9Hz),1.20-1.35(6H,m),1.94(2H,m),1.97-2.04(1H,m),2.04(3H,s),2.48-2.58(1H,m),2.60(1H,d,J=9.5Hz),2.62(1H,dd,J=2.5,9.5Hz),2.70(1H,dd,J=8.3,14.6Hz),2.93(1H,dd,J=6.9,14.6Hz),5.18(1H,ddd,J=6.9,8.3,10.8Hz),5.53(1H,q,J=7.3Hz),5.53-5.59(1H,m),6.01(1H,ddd,J=0.6,8.7,10.9Hz),6.45(1H,d,J=6.1Hz),6.67(1H,ddd,J=1.2,10.9,12.8Hz),7.01(1H,d,J=12.8Hz),7.48(1H,d,J=6.1Hz).(Ref. 8038) 13C-NMR(125MHz,CDCl3)dppm14.0,21.3,22.5,27.4,29.7,29.0,29.3,31.5,36.0,75.5,85.1,120.7,123.3,125.0,135.1,135.4,138.2,138.4,158.2,169.2,176.3,193.3.(Ref. 8038) |
EIMS m/z 372 (M+). HREIMS m/z 372.1916 for C22H28O5, calcd 372.1937.(Ref. 8038) |
Clavulolactone I was converted from clavulone I.(Ref. 8038) |
||||||||||||||
| 310 |  |
clavulolactone II (Ref. 8039) |
(R)-4-{(1E,3E)-3-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-1-propenyl}-4-butanolide |
XPR8035 | Yasuji Yamada |
C22H28O5 | 372.455 | |
[a]D -25.6 (C 0.26, CHCl3)(Ref. 8039) |
lEtOHmax 292 nm(e16500),231 nm(e12500)(Ref. 8039) |
nfilmmax1778,1745, 1704, 1644, and 1231cm-1(Ref. 8039) |
1H-NMR(400MHz,CDCl3)dppm0.87(3H,t,J=7.2Hz),1.20-1.34(6H,m),1.94(2H,brq,J=6.3Hz),2.02(3H,s),2.04(1H,m),2.52(1H,m),2.55(2H,m),2.71(1H,brdd,J=8.1,14.2Hz),2.91(1H,brdd,J=7.1,14.2Hz),5.15(1H,m),5.15(1H,m),5.52(1H,m),6.17(1H,dd,J=4.9,14.7Hz),6.42(1H,d,J=6.1Hz),6.82(1H,ddd,J=1.5,12.0,14.7Hz),6.91(1H,brd,J=12.0Hz),7.50(1H,brd,J=6.1Hz).(Ref. 8039) 13C-NMR(100MHz,CDCl3)dppm14.0,21.2,22.5,27.4,27.7,28.2,29.0,31.5,35.8,78.6,85.2,121.0,124.9,128.9,135.06,135.14,137.2,140.8,158.0,169.3,176.2,193.3.(Ref. 8039) |
EIMS m/z 372 (M+). HREIMS m/z 372.1920 for C22H28O5, calcd 372.1937.(Ref. 8039) |
Clavulolactone II was converted from clavulone II.(Ref. 8039) |
||||||||||||||
| 311 |  |
clavulolactone III (Ref. 8038) |
(R)-4-{(1E,3Z)-3-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-1-propenyl}-4-butanolide |
XPR8036 | Yasuji Yamada |
C22H28O5 | 372.455 | |
[a]D -7.3 (C 0.21, CHCl3)(Ref. 8039) |
lEtOHmax 293 nm(e15500),229 nm(e17900)(Ref. 8039) |
nfilmmax1778,1742, 1698, 1643, and 1232cm-1(Ref. 8039) |
1H-NMR(400MHz,CDCl3)dppm0.88(3H,t,J=7.1Hz),1.22-1.33(6H,m),1.97(2H,brq,J=7.2Hz),2.03(3H,s),2.05(1H,m),2.47(1H,m),2.58(2H,dd,J=6.9,9.3Hz),2.65(1H,brdd,J=7.6,14.3Hz),2.84(1H,brdd,J=7.3,14.3Hz),5.10(1H,brdd,J=7.3,7.9Hz),5.22(1H,m),5.54(1H,m),6.08(1H,dd,J=7.3,15.6Hz),6.38(1H,d,J=6.1Hz),6.53(1H,d,J=11.3Hz),7.49(1H,d,J=6.1Hz),7.82(1H,brdd,J=11.3,15.6Hz).(Ref. 8039) 13C-NMR(100MHz,CDCl3)dppm14.0,21.6,22.5,27.4,28.6,28.6,29.0,31.4,35.7,80.0,85.0,121.1,127.6,132.4,135.0,136.6,139.8,139.8,156.3,169.6,176.5,194.0.(Ref. 8039) |
EIMS m/z 372 (M+). HREIMS m/z 372.1961 for C22H28O5, calcd 372.1937.(Ref. 8039) |
Clavulolactone III was converted from clavulone III.(Ref. 8039) |
||||||||||||||
| 312 |  |
17,18-dehydroclavulone I (Ref. 8038) |
methyl (4R,5Z,7E)-4-acetoxy-7-[(S)-2-acetoxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate |
XPR8037 | Yasuji Yamada |
C25H32O7 | 444.517 | |
[a]D -27.1 (C 0.31, CHCl3)(Ref. 8038) |
lEtOHmax 228 nm(loge3.98),293nm(loge4.01)(Ref. 8038) |
nfilmmax1770,1732,1704,1643, and 1230cm-1(Ref. 8038) |
1H-NMR(500MHz,CDCl3)dppm0.96(3H,t,J=7.5Hz),1.90-2.02(2H,m),2.00-2.10(2H,m),2.03(3H,s),2.04(3H,s),2.38(2H,q,J=7.3Hz),2.67-2.76(2H,m),2.69(1H,dd,J=8.0,14.2Hz),2.98(1H,dd,J=7.4,14.2Hz),3.69(3H,s),5.21(1H,dt,J=7.6,10.8Hz),5.23(1H,ddd,J=7.4,8.0,10.9Hz),5.39(1H,dt,J=7.4,10.8Hz),5.50(1H,dt,J=7.5,10.9Hz),5.78(1H,dt,J=5.4,8.1Hz),5.86(1H,ddd,J=1.1,8.1,11.1Hz),6.43(1H,d,J=6.1Hz),6.59(1H,dd,J=11.1,12.7Hz),7.27(1H,d,J=12.7Hz),7.48(1H,d,J=6.1Hz).(Ref. 8038) 13C-NMR(125MHz,CDCl3)dppm14.2,20.6,21.0,21.2,25.7,29.8,29.8,35.8,51.8,69.4,85.1,121.4,124.2,124.6,126.2,132.5,133.1,135.2,135.7,138.9,157.8,169.1,169.9,172.9,193.1.(Ref. 8038) |
EIMS m/z 444 (M+). HREIMS m/z 384.1925 for C23H28O5 (M-CH3-CO2H)+, calcd 384.1937.(Ref. 8038) |
17,18-Dehydroclavulone I was isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8038) |
||||||||||||||
| 313 |  |
sodium (4R,5E,7E)-7-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-4-hydroxy-5-heptenoate |
XPR8038 | Yasuji Yamada |
C20H27O5Na | 370.415 | |
[a]D -92.3 (C 0.16, MeOH)(Ref. 8040) |
lMeOH&max 301 nm(log e4.01),233 nm(log e4.03)(Ref. 8040) |
nfilmmax3382,1694,1633,1567, and 1556cm-1(Ref. 8040) |
1H-NMR(400MHz,CD3OD)dppm0.93(3H,t,J=6.9Hz),1.25-1.40(6H,m),1.85-1.95(2H,brm),2.00(2H,m),2.37(2H,brm),2.72(1H,dd,J=7.4,14.0Hz),2.84(1H,dd,J=8.2,14.0Hz),4.34(1H,brm),5.16(1H,ddd,J=7.4,8.2,11.0Hz),5.45(1H,td,J=7.3,11.0Hz),6.30(1H,dd,J=5.5,15.0Hz),6.32(1H,d,J=6.0Hz),6.92(1H,d,J=11.9Hz),7.09(1H,dd,J=11.9,15.0Hz),7.40(1H,dd,J=0.8,6.0Hz).(Ref. 8040) 13C-NMR(100MHz,CD3OD)dppm15.2,24.4,29.2,31.2,33.5,35.1,38.5,73.6,81.1,124.7,126.3,133.2,135.4,135.7,140.7,150.3,165.2,198.9.(Ref. 8040) |
ESIMS m/z 371 (M+H)+. HREIMS m/z 330.1834 for C20H26O4 (M-NaOH)+, calcd 330.1831.(Ref. 8040) |
CDlEtOH&ext(De)nm 257(+5.4),230(-15.3).(Ref. 8040) |
This marine prostanoidesodium solts was isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8040) |
||||||||||||||
| 314 |  |
sodium (4R,5E,7Z)-7-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-4-hydroxy-5-heptenoate |
XPR8039 | Yasuji Yamada |
C20H27O5Na | 370.415 | |
[a]D -83.2 (C 0.095, MeOH)(Ref. 8040) |
lMeOH&max 305 nm(log e4.11),233 nm(log e4.14)(Ref. 8040) |
nfilmmax3382,1694,1574, and 1550cm-1(Ref. 8040) |
1H-NMR(400MHz,CD3OD)dppm0.93(3H,t,J=6.9Hz),1.25-1.40(6H,m),1.88(2H,brm),2.02(2H,m),2.36(2H,brm),2.62(2H,m),4.29(1H,brm),5.26(1H,ttd,J=1.6,7.6,11.0Hz),5.48(1H,td,J=7.3,11.0Hz),6.21(1H,dd,J=5.5,15.3Hz),6.28(1H,d,J=6.0Hz),6.70(1H,d,J=11.4Hz),7.34(1H,d,J=6.0Hz),7.73(1H,dd,J=11.4,15.3Hz).(Ref. 8040) 13C-NMR(100MHz,CD3OD)dppm15.2,24.4,29.1,31.1,33.4,35.2,39.0,73.6,80.6,124.9,126.7,135.2,136.7,137.2,140.1,149.4,163.0,198.7(Ref. 8040) |
ESIMS m/z 371 (M+H)+. HREIMS m/z 330.1832 for C20H26O4 (M-NaOH)+, calcd 330.1831.(Ref. 8040) |
CDlEtOH&ext(De)nm 257(+4.0),228(-12.3).(Ref. 8040) |
This marine prostanoidesodium solts was isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8040) |
||||||||||||||
| 315 |  |
preclavulone lactone I (Ref. 8041) |
(R)-4-{(Z)-3-[(1R,2S)-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenyl]-1-propenyl}-4-butanolide |
XPR8040 | Yasuji Yamada |
C20H28O3 | 316.435 | |
[a]D -168.0 (Ref. 8041) |
lCH3CN&max 215 nm(e5740)(Ref. 8041) |
n 1775 and 1706cm-1(Ref. 8041) |
1H-NMR(500MHz,CDCl3)dppm0.89(3H,t,J=7.5Hz),1.2-1.4(6H,m),1.92(1H,dtd,8.4,9.7,12.9Hz),2.01(2H,brq,J=7.3Hz),2.11(1H,dt,J=2.3,5.9),2.27(1H,brtd,J=7.0,14.5Hz),2.32(1H,brtd,J=7.1,14.5Hz),2.41(1H,qd,J=6.6,12.9Hz),2.52(2H,m),2.57(2H,dd,J=6.6,9.7Hz),2.72(1H,qt,J=2.3,7.0Hz),5.27(1H,dt,J=6.6,8.4Hz),5.36(1H,brtd,J=7.1,10.8Hz),5.53(1H,dd,J=8.4,11.1Hz),5.54(1H,m),5.56(1H,td,J=7.2,11.1Hz),6.16(1H,dd,J=2.3,5.1Hz),7.60(1H,dd,J=2.3,5.8Hz).(Ref. 8041) 13C-NMR(125MHz,CDCl3)dppm14.0,22.5,27.3,27.5,28.9,29.1,29.2,31.3,31.5,46.3,50.3,76.0,125.2,129.9,130.9,133.1,133.4,167.2,177.0,210.6(Ref. 8041) |
HRFABMS m/z 316.2028 for C20H28O3 (M+), calcd 316.2038.(Ref. 8041) |
Preclavulone lactones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8041) |
Preclavulone lactone I was synthesized from (S)-(-)-malic acid.(Ref. 8041) |
Preclavulone lactone may possibly be biosynthesized from preclavulon A. Clavulones may be biosynthesized from preclavulone lactones via clavulolactones by oxygenation at C-12, dehydration between C-7 and C-8, and esterification at C-1 and C-4. (Ref. 8041) |
||||||||||||
| 316 |  |
preclavulone lactone II (Ref. 8041) |
(R)-4-{(E)-3-[(1R,2S)-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenyl]-1-propenyl}-4-butanolide |
XPR8041 | Yasuji Yamada |
C20H28O3 | 316.435 | |
[a]D -110 (Ref. 8041) |
1H-NMR(500MHz,CDCl3)dppm0.89(3H,t,J=7.2Hz),1.2-1.4(6H,m),1.96(1H,m),2.00(2H,brq,J=7.3Hz),2.11(1H,m),2.27(1H,m),2.32(1H,m),2.37(1H,m),2.50(2H,m),2.52(2H,m),2.67(1H,qt,J=2.4,7.0Hz),4.89(1H,q,J=6.7Hz),5.33(1H,brtd,J=7.8,10.9Hz),5.52(1H,brtd,J=7.3,10.9Hz),5.58(1H,brdd,J=6.7,15.2Hz),5.76(1H,brtd,J=7.7,15.2Hz),6.15(1H,dd,J=2.4,5.8Hz),7.58(1H,dd,J=2.4,5.8Hz).(Ref. 8041) 13C-NMR(125MHz,CDCl3)dppm14.0,22.5,27.3,28.5,28.7,29.2,31.3,31.5,33.1,46.9,50.2,80.4,125.2,130.1,131.5,133.0,133.1,166.9,176.8,210.6(Ref. 8041) |
Preclavulone lactones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8041) |
Preclavulone lactone may possibly be biosynthesized from preclavulon A. Clavulones may be biosynthesized from preclavulone lactones via clavulolactones by oxygenation at C-12, dehydration between C-7 and C-8, and esterification at C-1 and C-4. (Ref. 8041) |
||||||||||||||||
| 317 |  |
4-epiclavulone II (Ref. 8042) |
methyl (4R,5E,7E)-4-acetoxy-7-[(R)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate |
XPR8042 | Yasuji Yamada |
C25H34O7 | 446.533 | |
[a]D -18.7 (C 0.30, CHCl3)(Ref. 8042) |
lEtOHmax 228 nm(log e4.28),291 nm(log e4.27)(Ref. 8042) |
nfilmmax1738,1732,1704,1644,and 1232cm-1(Ref. 8042) |
1H-NMR(500MHz,CDCl3)dppm0.88(3H,t,J=7.2Hz),1.20-1.34(6H,m),1.94(2H,q,J=6.8Hz),1.98-2.06(2H,m),2.03(3H,s),2.09(3H,s),2.37(2H,t,J=7.4Hz),2.71(1H,dd,J=8.4,14.1Hz),2.98(1H,dd,J=7.0,14.1Hz),3.67(3H,s),5.18(1H,ddd,J=7.0,8.4,10.9Hz),5.43(1H,dt,J=6.4,7.0Hz),5.50(1H,dt,J=7.4,10.9Hz),6.07(1H,dd,J=6.4,11.9Hz),6.41(1H,d,J=6.1Hz),6.70(1H,ddd,J=1.0,11.9,15.1Hz),6.88(1H,d,J=15.1Hz),7.48(1H,d,J=6.1Hz).(Ref. 8042) 13C-NMR(125MHz,CDCl3)dppm14.0,20.9,21.2,22.5,27.4,29.1,29.2,29.6,31.5,35.9,51.8,72.7,85.3,121.1,126.0,129.4,135.1,135.1,136.7,141.5,157.9,169.2,169.9,172.9,193.4.(Ref. 8042) |
EIMS m/z 446 (M+). HREIMS m/z 446.2315 for C25H34O7 (M+), calcd 446.2305.(Ref. 8042) |
4-Epiclavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8042) |
4-Epiclavulone II was synthesized from clavulone II.(Ref. 8042) |
|||||||||||||
| 318 |  |
4-epiclavulone III (Ref. 8042) |
methyl (4R,5E,7Z)-4-acetoxy-7-[(R)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate |
XPR8043 | Yasuji Yamada |
C25H34O7 | 446.533 | |
[a]D -10.0 (C 0.06, CHCl3)(Ref. 8042) |
lEtOHmax 229 nm(log e4.23),295 nm(log e4.14)(Ref. 8042) |
nfilmmax1738,1698 and 1229cm-1(Ref. 8042) |
1H-NMR(500MHz,CDCl3)dppm0.88(3H,t,J=7.1Hz),1.21-1.34(6H,m),1.94(2H,q,J=7.3Hz),1.99-2.07(2H,m),2.03(3H,s),2.09(3H,s),2.40(2H,t,J=7.4Hz),2.63(1H,dd,J=7.3,14.2Hz),2.87(1H,dd,J=8.1,14.2Hz),3.68(3H,s),5.21(1H,ddd,J=7.3,8.1,10.9Hz),5.45(1H,dd,J=5.4,5.8Hz),5.53(1H,dt,J=7.3,10.9Hz),6.01(1H,dd,J=5.4,15.6Hz),6.35(1H,d,J=6.1Hz),6.51(1H,d,J=11.3Hz),7.51(1H,d,J=6.1Hz),7.73(1H,ddd,J=1.3,11.3,15.6Hz).(Ref. 8042) 13C-NMR(125MHz,CDCl3)dppm14.0,21.0,21.7,22.5,27.4,29.0,29.2,29.7,31.5,35.6,51.7,72.4,85.2,121.3,126.3,133.4,134.7,135.6,136.7,141.0,156.1,169.7,170.2,173.2,194.1.(Ref. 8042) |
EIMS m/z 446 (M+). HREIMS m/z 446.2328 for C25H34O7 (M+), calcd 446.2305.(Ref. 8042) |
4-Epiclavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8042) |
4-Epiclavulone III was synthesized from clavulone III.(Ref. 8042) |
|||||||||||||
| 319 |  |
clavirin I (Ref. 8043) |
(Z)-2-[(R)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]acetaldehyde |
XPR8044 | Yasuji Yamada |
C17H22O4 | 290.354 | |
Clavirins showed growth-inhibitory activity toward Hela S3 at 1 mg/ml.(Ref. 8043) |
[a]D -17.1 (C 0.48, CHCl3)(Ref. 8043) |
nfilmmax1735,1714,1682, and 1227cm-1(Ref. 8043) |
1H-NMR(500MHz,CDCl3)dppm0.88(3H,t,J=7.1Hz),1.20-1.36(6H,m),1.96(2H,brq,J=7.1Hz),2.05(3H,s),2.68(1H,dd,J=7.7,14.6Hz),2.77(1H,dd,J=7.4,14.6Hz),5.23(1H,dt,J=7.1,10.9Hz),5.59(1H,ddd,J=7.4,7.7,10.9Hz),6.21(1H,d,J=7.6Hz),6.49(1H,d,J=6.2Hz),7.56(1H,d,J=6.2Hz),10.79(1H,d,J=7.6Hz).(Ref. 8043) 13C-NMR(125MHz,CDCl3)dppm14.0,21.3,22.5,27.4,29.0,31.4,36.0,83.5,120.1,129.9,136.0,136.1,150.2,169.5,11.7,192.9.(Ref. 8043) |
HREIMS m/z 230.1298 for C15H18O2 (M+-CH3CO2H), calcd 230.1307.(Ref. 8043) |
Clavirins were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8043) |
Clavirin I and II were synthesized from 4-alkoxy-2-cyclopentenone.(Ref. 8043) |
Clavirins may possibly be biosynthesized from clavulone.(Ref. 8043) |
||||||||||||
| 320 |  |
clavirin II (Ref. 8043) |
(E)-2-[(R)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]acetaldehyde |
XPR8045 | Yasuji Yamada |
C17H22O4 | 290.354 | |
Clavirins showed growth-inhibitory activity toward Hela S3 at 1 mg/ml.(Ref. 8043) |
[a]D -33.7 (C 0.43, CHCl3)(Ref. 8043) |
1H-NMR(500MHz,CDCl3)dppm0.88(3H,t,J=7.1Hz),1.20-1.40(6H,m),1.95(2H,brq,J=7.2Hz),2.09(3H,s),2.88(1H,dd,J=7.1,14.5Hz),2.91(1H,dd,J=7.5,14.5Hz),5.23(1H,ddd,J=1.6,7.2,10.9Hz),5.62(1H,ddd,J=7.1,7.5,10.9Hz),6.53(1H,d,J=8.0Hz),6.54(1H,d,J=6.2Hz),7.65(1H,d,J=6.2Hz),10.33(1H,d,J=8.0Hz).(Ref. 8043) 13C-NMR(125MHz,CDCl3)dppm14.0,21.3,22.5,27.5,28.9,31.4,37.3,84.4,120.1,125.6,134.8,136.5,149.4,159.3,169.2,190.6,192.5.(Ref. 8043) |
Clavirins were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8043) |
Clavirin I and II were synthesized from 4-alkoxy-2-cyclopentenone.(Ref. 8043) |
Clavirins may possibly be biosynthesized from clavulone.(Ref. 8043) |
||||||||||||||
| 321 |  |
15-epi-prostaglandin A2(Ref. 8044) |
(5Z, 13E)-(8R,12S,15R)-15-hydroxy-9-oxoprost-5,10,13-trienoic acid |
XPR8046 | Yasuji Yamada |
(15R)-PGA2 |
C20H34O4 | 338.482 | |
nfilmmax1350 and 970cm-1(Ref. 8044) |
1H-NMRdppm5.41, 5.58.(Ref. 8044) |
15-Epi-prostaglandin A 2 and its acetate methyl ester were isolated from Caribbean Gorgonian, Plexaura homomalla.(Ref. 8044) |
||||||||||||||||
| 322 |  |
15-epi-prostaglandin A2 acetate, methyl ester(Ref. 8044) |
methyl (5Z, 13E)-(8R,12S,15R)-15-hydroxy-9-oxoprost-5,10,13-trienoate |
XPR8047 | Yasuji Yamada |
C23H34O5 | 390.513 | |
nfilmmax1735 and 1710cm-1(Ref. 8044) |
1H-NMRdppm0.89(3H,t),1.98(3H,s),3.22(1H),3.61(3H,s),5.15(1H),5.2-5.7(4H),6.12(1H,dd,J=6.12,7.44Hz),7.44(1H,dd,J=6.12,7.44Hz).(Ref. 8044) |
15-Epi-prostaglandin A 2 and its acetate methyl ester were isolated from Caribbean Gorgonian, Plexaura homomalla.(Ref. 8044) |
|||||||||||||||||
| 323 |  |
15-epi-prostaglandin E2 acetate, methyl ester(Ref. 8045) |
(5Z, 13E)-(8R,11R,12R,15R)-11,15-dihydroxy-9-oxoprost-5,13-dienoic acid |
XPR8048 | Yasuji Yamada |
(15R)-PGE2 |
C20H32O5 | 352.465 | |
15-Epi-prostaglandin E2 and its methyl ester were isolated from Gorgonian, Plexaura homomalla.(Ref. 8045) |
||||||||||||||||||
| 324 |  |
15-epi-prostaglandin E2 methyl ester(Ref. 8045) |
methyl (5Z, 13E)-(8R,11R,12R,15R)-11,15-dihydroxy-9-oxoprost-5,13-dienoate |
XPR8049 | Yasuji Yamada |
C21H34O5 | 366.492 | |
15-Epi-prostaglandin E2 and its methyl ester were isolated from Gorgonian, Plexaura homomalla.(Ref. 8045) |
|||||||||||||||||||
| 325 |  |
prostaglandin F2a -11-acetate(Ref. 8046) |
(5Z,13E)-(8R,9S,11R,12R,15S)-11-acetoxy-9,15-dihydroxyprost-5,13-dienoic acid |
XPR8050 | Yasuji Yamada |
C22H36O6 | 396.518 | |
Prostaglandin F2a -11-acetate was isolated from soft coral, Lobophyton depressum.(Ref. 8046) |
|||||||||||||||||||
| 326 |  |
prostaglandin F2a -11-acetate methyl ester(Ref. 8046) |
methyl (5Z,13E)-(8R,9S,11R,12R,15S)-11-acetoxy-9,15-dihydroxyprost-5,13-dienoate |
XPR8051 | Yasuji Yamada |
C23H38O6 | 410.544 | |
55 (hexane)(Ref. 8046) |
nKBr&max3700, 3610, 3510, 1740, 1730, and 970 cm-1(Ref. 8046) |
1H-NMR(270MHz,CDCl3)dppm0.88(3H,t,J=6.0Hz),1.26(6H,brs),2.04(3H,s),2.32(2H,t,J=7.2Hz),2.39(1H,ddd,J=15.2,9.0,5.4Hz),2.55(1H,ddd,J=11.8,8.4,7.0Hz),3.67(3H,s),4.08(1H,q,J=6.1Hz),4.17(1H,dd,J=5.4,3.5Hz),4.90(1H,ddd,J=9.0,7.0,3.8Hz),5.41(2H,m),5.53(1H,m),5.55(1H,m).(Ref. 8046) |
CIMS m/z 411 ([M++1], 1), 392(7), 350(6), 332(98),314(100),288(2),282(15). (Ref. 8046) |
Prostaglandin F2a -11-acetate methyl ester was isolated from soft coral, Lobophyton depressum.(Ref. 8046) |
|||||||||||||||
| 327 |  |
18-acetoxyprostaglandin F2a -11-acetate(Ref. 8046) |
(5Z,13E)-(8R,9S,11R,12R,15S)-11,18-diacetoxy-9,15-dihydroxyprost-5,13-dienoic acid |
XPR8052 | Yasuji Yamada |
C24H38O8 | 454.554 | |
18-Acetoxyprostaglandin F2a -11-acetate was isolated from soft coral, Lobophyton depressum.(Ref. 8046) |
|||||||||||||||||||
| 328 |  |
18-acetoxyprostaglandin F2a -11-acetate methyl ester(Ref. 8046) |
methyl (5Z,13E)-(8R,9S,11R,12R,15S)-11,18-diacetoxy-9,15-dihydroxyprost-5,13-dienoate |
XPR8053 | Yasuji Yamada |
C25H40O8 | 468.580 | |
nneat&max3470,1740,1730,1715,1465,1435,1375,1260,1030, and 970cm-1(Ref. 8046) |
1H-NMR(270MHz,CDCl3)dppm0.90(3H,t,J=7.2Hz),2.04(3H,s),2.31(2H,t,J=7.0Hz),2.38(1H,ddd,J=15.3,9.0,5.5Hz),2.55(1H,ddd,J=10.8,8.4,6.8Hz),3.67(3H,s),4.08(1H,dt,J=5.6,4.0Hz),4.17(1H,dd,J=5.5,3.5Hz),4.82(1H,q,J=5.3Hz),4.90(1H,ddd,J=9.0,6.8,4.0Hz),5.40(2H,m),5.54(2H,m.(Ref. 8046) |
CIMS m/z 450 ([M-H2O]+, 5), 408(5), 390(12), 372(16), 348(20), 330(100), 312(66), 298(18), 280(20). (Ref. 8046) |
18-Acetoxyprostaglandin F2a -11-acetate methyl ester was isolated from soft coral, Lobophyton depressum.(Ref. 8046) |
||||||||||||||||
| 329 |  |
5-trans-prostaglandin A2(Ref. 8047) |
(5E, 13E)-(8R,12S,15S)-15-hydroxy-9-oxoprost-5,10,13-trienoic acid |
XPR8054 | Yasuji Yamada |
5-trans-PGA2 |
C20H30O4 | 334.450 | |
[a]D +128 (CHCl3)(Ref. 8047) |
lmax 217 nm(e9050))(Ref. 8047) |
HREIMS m/z 478.2998 for TMS derivative C26H46O4 Si2, calcd 478.2932.(Ref. 8047) |
5-trans-Prostaglandin A2 was isolated from Gorgonian, Plexaura homomalla.(Ref. 8047) |
|||||||||||||||
| AUTHOR | : | Bergstrom, S. |
| TITLE | : | Prostaglandins: members of a new hormonal system. These physiologically very potent compounds of ubiquitous occurrence are formed from essential fatty acids PubMed ID:4291104 |
| JOURNAL | : | Science. |
| VOL | : | 157 PAGE : 382-391 (1967) |
| AUTHOR | : | Bergstrom, S., Carlson, L. A., and Weeks, J. R. |
| TITLE | : | The prostaglandins: a family of biologically active lipids PubMed ID:4873508 |
| JOURNAL | : | Pharmacol Rev. |
| VOL | : | 20 PAGE : 1-48 (1968) |
| AUTHOR | : | Negishi, M., Sugimoto, Y., and Ichikawa, A. |
| TITLE | : | Molecular mechanisms of diverse actions of prostanoid receptors PubMed ID:7492609 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 1259 PAGE : 109-119 (1995) |
| AUTHOR | : | Smith, W. L., Garavito, R. M., and DeWitt, D. L. |
| TITLE | : | Prostaglandin endoperoxide H synthases (cyclooxygenases)-1 and -2 PubMed ID:8969167 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 271 PAGE : 33157-33160 (1996) |
| AUTHOR | : | Urade, Y., Watanabe, K., and Hayaishi, O. |
| TITLE | : | Prostaglandin D, E, and F synthases PubMed ID:8777570 |
| JOURNAL | : | J Lipid Mediat Cell Signal. |
| VOL | : | 12 PAGE : 257-273 (1995) |
| AUTHOR | : | Hansen, H. S. |
| TITLE | : | 15-hydroxyprostaglandin dehydrogenase. A review PubMed ID:184496 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 12 PAGE : 647-679 (1976) |
| AUTHOR | : | Funk, C.D. |
| TITLE | : | Molecular biology in the eicosanoid field . PubMed ID:8341804 |
| JOURNAL | : | Progr. Nucleic Acid Res. |
| VOL | : | 45 PAGE : 67-98 (1993) |
| AUTHOR | : | Herschman, H.R. |
| TITLE | : | Prostaglandin synthase 2. PubMed ID:8341804 |
| JOURNAL | : | Biochim. Biophys. Acta |
| VOL | : | 1299 PAGE : 125-140 (1996) |
| AUTHOR | : | Giles, H., and Leff, P. |
| TITLE | : | The biology and pharmacology of PGD2 PubMed ID:3283848 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 35 PAGE : 277-300 (1988) |
| AUTHOR | : | Fukushima, M. |
| TITLE | : | Biological activities and mechanisms of action of PGJ2 and related compounds: an update PubMed ID:1438462 |
| JOURNAL | : | Prostaglandins Leukot Essent Fatty Acids. |
| VOL | : | 47 PAGE : 1-12 (1992) |
| AUTHOR | : | Negishi,M., Koizumi,T., and Ichikawa,A. |
| TITLE | : | Biological actions of D12-prostaglandin J2. PubMed ID:8777585 |
| JOURNAL | : | J. Lipid Mediators Cell Signaling |
| VOL | : | 12 PAGE : 443-448 (1995) |
| AUTHOR | : | Hayaishi, O. |
| TITLE | : | Sleep-wake regulation by prostaglandins D2 and E2 PubMed ID:3049580 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 263 PAGE : 14593-14596 (1988) |
| AUTHOR | : | Moncada, S., and Vane, J. R. |
| TITLE | : | Pharmacology and endogenous roles of prostaglandin endoperoxides, thromboxane A2, and prostacyclin PubMed ID:116251 |
| JOURNAL | : | Pharmacol Rev. |
| VOL | : | 30 PAGE : 293-331 (1978) |
| AUTHOR | : | Whittle, B. J., and Moncada, S. |
| TITLE | : | Pharmacological interactions between prostacyclin and thromboxanes PubMed ID:6313114 |
| JOURNAL | : | Br Med Bull. |
| VOL | : | 39 PAGE : 232-238 (1983) |
| AUTHOR | : | Pace-Asciak,C.R., and Smith,W.L. |
| TITLE | : | Enzymes in the biosynthesis and catabolism of the eicosanoids: prostaglandins, thromboxanes, leukotrienes and hydroxy fatty acids. |
| JOURNAL | : | The Enzymes |
| VOL | : | 16 PAGE : 543-603 (1983) |
| AUTHOR | : | Tanabe, T., and Ullrich, V. |
| TITLE | : | Prostacyclin and thromboxane synthases PubMed ID:8777569 |
| JOURNAL | : | J Lipid Mediat Cell Signal. |
| VOL | : | 12 PAGE : 243-255 (1995) |
| AUTHOR | : | Needleman, P., Turk, J., Jakschik, B. A., Morrison, A. R., and Lefkowith, J. B. |
| TITLE | : | Arachidonic acid metabolism PubMed ID:3017195 |
| JOURNAL | : | Annu Rev Biochem. |
| VOL | : | 55 PAGE : 69-102 (1986) |
| AUTHOR | : | Yokoyama, C., Yabuki, T., Inoue, H., Tone, Y., Hara, S., Hatae, T., Nagata, M., Takahashi, E. I., and Tanabe, T. |
| TITLE | : | Human gene encoding prostacyclin synthase (PTGIS): genomic organization, chromosomal localization, and promoter activity PubMed ID:8812456 |
| JOURNAL | : | Genomics. |
| VOL | : | 36 PAGE : 296-304 (1996) |
| AUTHOR | : | Yamamoto,S. (1983) Enzymes in the arachidonic acid cascade. in Prostaglandins and related substances (Pace-Asciak,C.R. and Granstroem,E., eds), pp171-202, Elsevier, Amsterdam |
| TITLE | : | |
| JOURNAL | : | |
| VOL | : | PAGE : - () |
| AUTHOR | : | Chijimatsu, Y., Nguyen, T. V., and Said, S. I. |
| TITLE | : | Effects of prostaglandin endoperoxide analogs on contractile elements in lung and gastrointestinal tract PubMed ID:866698 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 13 PAGE : 909-916 (1977) |
| AUTHOR | : | Samuelsson, B., and Hammarstrom, S. |
| TITLE | : | Leukotrienes: a novel group of biologically active compounds PubMed ID:6293196 |
| JOURNAL | : | Vitam Horm. |
| VOL | : | 39 PAGE : 1-30 (1982) |
| AUTHOR | : | Hammarstrom, S. |
| TITLE | : | Leukotrienes PubMed ID:6311078 |
| JOURNAL | : | Annu Rev Biochem. |
| VOL | : | 52 PAGE : 355-377 (1983) |
| AUTHOR | : | Sumimoto, H., Takeshige, K., and Minakami, S. |
| TITLE | : | Superoxide production of human polymorphonuclear leukocytes stimulated by leukotriene B4 PubMed ID:6322859 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 803 PAGE : 271-277 (1984) |
| AUTHOR | : | Yokomizo, T., Izumi, T., Chang, K., Takuwa, Y., and Shimizu, T. |
| TITLE | : | A G-protein-coupled receptor for leukotriene B4 that mediates chemotaxis PubMed ID:9177352 |
| JOURNAL | : | Nature. |
| VOL | : | 387 PAGE : 620-624 (1997) |
| AUTHOR | : | Ford-Hutchinson, A. W., Gresser, M., and Young, R. N. |
| TITLE | : | 5-Lipoxygenase PubMed ID:7979243 |
| JOURNAL | : | Annu Rev Biochem. |
| VOL | : | 63 PAGE : 383-417 (1994) |
| AUTHOR | : | Yokomizo,T., Izumi,T., Takahashi,T., Kazama,T., Kobayashi,Y., Sato,F., Taketani,Y., and Shimizu,T. |
| TITLE | : | Enzymatic inactivation of leukotrieneB4 by a novel enzyme found in the porcine kidney. Purification and properties of leukotriene B4 12-hydroxydehydrogenase. PubMed ID:8394361 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 268 PAGE : 18128-18135 (1993) |
| AUTHOR | : | Yokomizo,T., Ogawa,Y., Uozumi,N., Kume,K., Izumi,T., Shimizu,T. |
| TITLE | : | cDNA cloning, expression, and mutagenesis study of leukotriene B4 12-hydroxydehydrogenase. PubMed ID:8576264 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 271 PAGE : 2844-2850 (1996) |
| AUTHOR | : | Lam, B. K., Penrose, J. F., Freeman, G. J., and Austen, K. F. |
| TITLE | : | Expression cloning of a cDNA for human leukotriene C4 synthase, an integral membrane protein conjugating reduced glutathione to leukotriene A4 PubMed ID:8052639 |
| JOURNAL | : | Proc Natl Acad Sci U S A. |
| VOL | : | 91 PAGE : 7663-7667 (1994) |
| AUTHOR | : | Penrose, J. F., Spector, J., Baldasaro, M., Xu, K., Boyce, J., Arm, J. P., Austen, K. F., and Lam, B. K. |
| TITLE | : | Molecular cloning of the gene for human leukotriene C4 synthase. Organization, nucleotide sequence, and chromosomal localization to 5q35 PubMed ID:8626689 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 271 PAGE : 11356-11361 (1996) |
| AUTHOR | : | Lynch, K. R., O'Neill, G. P., Liu, Q., Im, D. S., Sawyer, N., Metters, K. M., Coulombe, N., Abramovitz, M., Figueroa, D. J., Zeng, Z., et al. |
| TITLE | : | Characterization of the human cysteinyl leukotriene CysLT1 receptor PubMed ID:10391245 |
| JOURNAL | : | Nature. |
| VOL | : | 399 PAGE : 789-793 (1999) |
| AUTHOR | : | Kindahl,H. |
| TITLE | : | Metabolism of thromboxane B2 in the cynomolgus monkey. PubMed ID:404670 |
| JOURNAL | : | Prostaglandins |
| VOL | : | 13 PAGE : 619-629 (1997) |
| AUTHOR | : | Westlund, P., Granstrom, E., Kumlin, M., and Nordenstrom, A. |
| TITLE | : | Identification of 11-dehydro-TXB2 as a suitable parameter for monitoring thromboxane production in the human PubMed ID:3755250 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 31 PAGE : 929-960 (1986) |
| AUTHOR | : | Ushikubi, F., Hirata, M., and Narumiya, S. |
| TITLE | : | Molecular biology of prostanoid receptors; an overview PubMed ID:8777578 |
| JOURNAL | : | J Lipid Mediat Cell Signal. |
| VOL | : | 12 PAGE : 343-359 (1995) |
| AUTHOR | : | Westlund, P., Fylling, A. C., Cederlund, E., and Jornvall, H. |
| TITLE | : | 11-Hydroxythromboxane B2 dehydrogenase is identical to cytosolic aldehyde dehydrogenase PubMed ID:8200461 |
| JOURNAL | : | FEBS Lett. |
| VOL | : | 345 PAGE : 99-103 (1994) |
| AUTHOR | : | Serhan, C. N. |
| TITLE | : | Lipoxin biosynthesis and its impact in inflammatory and vascular events PubMed ID:8155718 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 1212 PAGE : 1-25 (1994) |
| AUTHOR | : | Brady,H.R., and Serhan,C.N. |
| TITLE | : | Lipoxins: putative braking signals in host defense, inflammation and hypersensitivity. PubMed ID:8834158 |
| JOURNAL | : | Curr. Opinion Hephrol.Hypertension |
| VOL | : | 5 PAGE : 20-27 (1996) |
| AUTHOR | : | Fiore,S., Maddox,J.F., Perez,H.D., and Serhan,C.N. |
| TITLE | : | Identification of a human cDNA encoding a functional high affinity lipoxin A4 receptor. PubMed ID:8834158 |
| JOURNAL | : | J. Exp. Med. |
| VOL | : | 180 PAGE : 253-260 (1994) |
| AUTHOR | : | Fukushima,M. |
| TITLE | : | Prostaglandin J2-anti-tumor and anti-viral activities and the mechanisms involved. PubMed ID:2073399 |
| JOURNAL | : | Eicosanoids |
| VOL | : | 3 PAGE : 189-199 (1990) |
| AUTHOR | : | Pike,J.E., Lincoln,F.H., and Schneider,W.P. |
| TITLE | : | Prostanoic acid chemistry. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 34 PAGE : 3552-3557 (1969) |
| AUTHOR | : | Polet, H., and Levine, L. |
| TITLE | : | Metabolism of prostaglandins E, A, and C in serum PubMed ID:234423 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 250 PAGE : 351-357 (1975) |
| AUTHOR | : | Jones, R. L., Cammock, S., and Horton, E. W. |
| TITLE | : | Partial purification and properties of cat plasma prostaglandin A isomerase PubMed ID:4648784 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 280 PAGE : 588-601 (1972) |
| AUTHOR | : | Narumiya, S., and Fukushima, M. |
| TITLE | : | delta 12-Prostaglandin J2, an ultimate metabolite of prostaglandin D2 exerting cell growth inhibition PubMed ID:3857041 |
| JOURNAL | : | Biochem Biophys Res Commun. |
| VOL | : | 127 PAGE : 739-745 (1985) |
| AUTHOR | : | Negishi,M., Koizumi,T., and Ichikawa,A. |
| TITLE | : | Biological actions of D12-prostaglandin J2 . PubMed ID:8777585 |
| JOURNAL | : | J. Lipid Mediators Cell Signalling |
| VOL | : | 12 PAGE : 443-448 (1995) |
| AUTHOR | : | Anggard, E. |
| TITLE | : | The biological activities of three metabolites of prostaglandin E 1 PubMed ID:5951401 |
| JOURNAL | : | Acta Physiol Scand. |
| VOL | : | 66 PAGE : 509-510 (1966) |
| AUTHOR | : | Hamberg,M., and Samuelsson,B. |
| TITLE | : | On the metabolism of prostaglandin E1 and E2 in man. PubMed ID:5126221 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 246 PAGE : 6713-6721 (1971) |
| AUTHOR | : | Ensor, C. M., and Tai, H. H. |
| TITLE | : | 15-Hydroxyprostaglandin dehydrogenase PubMed ID:8777575 |
| JOURNAL | : | J Lipid Mediat Cell Signal. |
| VOL | : | 12 PAGE : 313-319 (1995) |
| AUTHOR | : | Granstrom, E., and Samuelsson, B. |
| TITLE | : | On the metabolism of prostaglandin F-2-alpha in female subjects PubMed ID:5125749 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 246 PAGE : 5254-5263 (1971) |
| AUTHOR | : | Roberts, L. J., 2nd, Sweetman, B. J., Payne, N. A., and Oates, J. A. |
| TITLE | : | Metabolism of thromboxane B2 in man. Identification of the major urinary metabolite PubMed ID:914816 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 252 PAGE : 7415-7417 (1977) |
| AUTHOR | : | Westlund, P., Kumlin, M., Nordenstrom, A., and Granstrom, E. |
| TITLE | : | Circulating and urinary thromboxane B2 metabolites in the rabbit: 11-dehydro-thromboxane B2 as parameter of thromboxane production PubMed ID:3520685 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 31 PAGE : 413-443 (1986) |
| AUTHOR | : | Orning, L., Kaijser, L., and Hammarstrom, S. |
| TITLE | : | In vivo metabolism of leukotriene C4 in man: urinary excretion of leukotriene E4 PubMed ID:2992461 |
| JOURNAL | : | Biochem Biophys Res Commun. |
| VOL | : | 130 PAGE : 214-220 (1985) |
| AUTHOR | : | Lee, C. W., Lewis, R. A., Corey, E. J., and Austen, K. F. |
| TITLE | : | Conversion of leukotriene D4 to leukotriene E4 by a dipeptidase released from the specific granule of human polymorphonuclear leucocytes PubMed ID:6293969 |
| JOURNAL | : | Immunology. |
| VOL | : | 48 PAGE : 27-35 (1983) |
| AUTHOR | : | Hammarstrom,S., Oerning,L., and Bernstroem,K. |
| TITLE | : | Metabolism of leukotrienes. PubMed ID:3001504 |
| JOURNAL | : | Molecular and Cellular Biochemistry |
| VOL | : | 69 PAGE : 7-16 (1985) |
| AUTHOR | : | Wong, P. Y., Lee, W. H., Chao, P. H., Reiss, R. F., and McGiff, J. C. |
| TITLE | : | Metabolism of prostacyclin by 9-hydroxyprostaglandin dehydrogenase in human platelets. Formation of a potent inhibitor of platelet aggregation and enzyme purification PubMed ID:6997309 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 255 PAGE : 9021-9024 (1980) |
| AUTHOR | : | Moore, P. K., and Griffiths, R. J. |
| TITLE | : | Review: 6 keto-prostaglandin-E1 PubMed ID:6361908 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 26 PAGE : 509-517 (1983) |
| AUTHOR | : | Pace-Asciak, C. R. |
| TITLE | : | Hepoxilins: a review on their cellular actions PubMed ID:7947989 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 1215 PAGE : 1-8 (1994) |
| AUTHOR | : | Pace-Asciak, C. R., Reynaud, D., and Demin, P. M. |
| TITLE | : | Hepoxilins: a review on their enzymatic formation, metabolism and chemical synthesis PubMed ID:7769965 |
| JOURNAL | : | Lipids. |
| VOL | : | 30 PAGE : 107-114 (1995) |
| AUTHOR | : | Wang,M.-M., Demin,P.M., and Pace-Asciak,C.R. (1996) Epimer-specific actions of hepoxilins A3 and B3 on PAF- and bradykinin-evoked vascular permeability in the rat skin in vivo. in Platelet-activating factor and related lipid mediators (Nigam,S. et al., eds.), pp239-241, Plenum Press, New York |
| TITLE | : | |
| JOURNAL | : | |
| VOL | : | PAGE : - () |
| AUTHOR | : | Pace-Asciak, C. R., and Lee, W. S. |
| TITLE | : | Purification of hepoxilin epoxide hydrolase from rat liver PubMed ID:2722835 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 264 PAGE : 9310-9313 (1989) |
| AUTHOR | : | Yamamoto, S., Suzuki, H., and Ueda, N. |
| TITLE | : | Arachidonate 12-lipoxygenases PubMed ID:9373619 |
| JOURNAL | : | Prog Lipid Res. |
| VOL | : | 36 PAGE : 23-41 (1997) |
| AUTHOR | : | Yoshimoto, T., and Yamamoto, S. |
| TITLE | : | Arachidonate 12-lipoxygenase PubMed ID:8777566 |
| JOURNAL | : | J Lipid Mediat Cell Signal. |
| VOL | : | 12 PAGE : 195-212 (1995) |
| AUTHOR | : | Bryant, R. W., Bailey, J. M., Schewe, T., and Rapoport, S. M. |
| TITLE | : | Positional specificity of a reticulocyte lipoxygenase. Conversion of arachidonic acid to 15-S-hydroperoxy-eicosatetraenoic acid PubMed ID:6804460 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 257 PAGE : 6050-6055 (1982) |
| AUTHOR | : | Schewe, T., Rapoport, S. M., and Kuhn, H. |
| TITLE | : | Enzymology and physiology of reticulocyte lipoxygenase: comparison with other lipoxygenases PubMed ID:3087141 |
| JOURNAL | : | Adv Enzymol Relat Areas Mol Biol. |
| VOL | : | 58 PAGE : 191-272 (1986) |
| AUTHOR | : | Harats,D., Mulkins,M.A., and Sigal,E. |
| TITLE | : | A possible role for 15-lipoxygenase in atherogenesis. |
| JOURNAL | : | TCM |
| VOL | : | 5 PAGE : 29-36 (1995) |
| AUTHOR | : | Kuehn,H., and Thiele,B.-J. |
| TITLE | : | Arachidonate 15-lipoxygenase. |
| JOURNAL | : | J. Lipid Mediators Cell Signalling |
| VOL | : | 12 PAGE : 157-170 (1995) |
| AUTHOR | : | Yamamoto, S. |
| TITLE | : | Mammalian lipoxygenases: molecular structures and functions PubMed ID:1420284 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 1128 PAGE : 117-131 (1992) |
| AUTHOR | : | Goetzl, E. J., and Gorman, R. R. |
| TITLE | : | Chemotactic and chemokinetic stimulation of human eosinophil and neutrophil polymorphonuclear leukocytes by 12-L-hydroxy-5,8,10-heptadecatrienoic acid (HHT) PubMed ID:621391 |
| JOURNAL | : | J Immunol. |
| VOL | : | 120 PAGE : 526-531 (1978) |
| AUTHOR | : | Hamberg,M., and Samauaelsson,B. |
| TITLE | : | Prostaglandin endoperoxides, novel transformation of arachidonic acid in human platelets. PubMed ID:4215079 |
| JOURNAL | : | Proc. Natl. Acad. Sci. USA |
| VOL | : | 71 PAGE : 3400-3404 (1974) |
| AUTHOR | : | Nugteren, D. H., and Hazelhof, E. |
| TITLE | : | Isolation and properties of intermediates in prostaglandin biosynthesis PubMed ID:4776443 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 326 PAGE : 448-461 (1973) |
| AUTHOR | : | Woollard,P.M. |
| TITLE | : | Stereochemical differencce between 12-hydroxy-5,8,10,14-eicosatetraenoic acid in platelets and psoriatic lesions. PubMed ID:3707572 |
| JOURNAL | : | Biochem. Biophys. Res. Commun. |
| VOL | : | 136 PAGE : 169-175 (1986) |
| AUTHOR | : | Schwartzman, M. L., Balazy, M., Masferrer, J., Abraham, N. G., McGiff, J. C., and Murphy, R. C. |
| TITLE | : | 12(R)-hydroxyicosatetraenoic acid: a cytochrome-P450-dependent arachidonate metabolite that inhibits Na+,K+-ATPase in the cornea PubMed ID:2825178 |
| JOURNAL | : | Proc Natl Acad Sci U S A. |
| VOL | : | 84 PAGE : 8125-8129 (1987) |
| AUTHOR | : | Capdevila,J., Yadagiri,P., Manna,S., and Falck,J.R. |
| TITLE | : | Absolute configuration of the hydroxyeicosatetraenoic acids (HETEs) formed during catalytic oxygenation of arachidonic acid by microsomal cytochrome P-450. PubMed ID:3101677 |
| JOURNAL | : | Biochem. Biophpys. Res. Commun. |
| VOL | : | 141 PAGE : 1007-1011 (1986) |
| AUTHOR | : | Hawkins,D.J., and Brash,A.R. |
| TITLE | : | Eggs of the sea urchin, Strongylocentrotus purpuratus, contain a prominent (11R) and (12R) lipoxygenase activity. PubMed ID:3108255 |
| JOURNAL | : | J. Bio. Chem. |
| VOL | : | 262 PAGE : 7629-7634 (1987) |
| AUTHOR | : | Brash,A.R., Baertschi,S.W., Ingram,C.D., and Harris,T.M. |
| TITLE | : | On non-cyclooxygenase prostaglandin synthesis in the sea whip coral, Plexaura homomalla: an 8(R)-lipoxygenase pathway leads to formation of an a-ketol and a racemic prostanoid. PubMed ID:2824470 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 262 PAGE : 15829-15839 (1987) |
| AUTHOR | : | Meijer,L., Brash,A.R., Bryant,R.W., Ng,K., Maclouf,J., and Sprecher,H. |
| TITLE | : | Stereospecific induction of starfish oocyte maturation by (8R)-hydroxyeicosatetraenoic acid. PubMed ID:3097019 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 261 PAGE : 17040-17047 (1986) |
| AUTHOR | : | Murphy,R.C., Falck,J.R., Lumin,S., Yadagiri,P., Zirrolli,J.A., Balazy,M.., Masferrer,J.L., Abraham,N.G., and Schwartzman,M.L. |
| TITLE | : | 12(R)-Hydroxyeicosatrienoic acid: a vasodilator cytochrome P-450-dependent arachidonate metabolite form the bovine corneal epithelium. PubMed ID:3141417 |
| JOURNAL | : | J. Bio. Chem. |
| VOL | : | 263 PAGE : 17197-17202 (1988) |
| AUTHOR | : | Chacos,N., Falck,J.R., Wixtrom,C., and Capdevilla,J. |
| TITLE | : | Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid. PubMed ID:6803794 |
| JOURNAL | : | Biochem. Biophpys. Res. Commun. |
| VOL | : | 104 PAGE : 916-922 (1982) |
| AUTHOR | : | Oliw,E.H., Guengerich,F.P., and Oates,J.A. |
| TITLE | : | Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates. PubMed ID:6803794 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 257 PAGE : 3771-3779 (1982) |
| AUTHOR | : | Fitzpatrick, F. A., and Murphy, R. C. |
| TITLE | : | Cytochrome P-450 metabolism of arachidonic acid: formation and biological actions of "epoxygenase"-derived eicosanoids PubMed ID:3072574 |
| JOURNAL | : | Pharmacol Rev. |
| VOL | : | 40 PAGE : 229-241 (1988) |
| AUTHOR | : | Falck, J. R., Schueler, V. J., Jacobson, H. R., Siddhanta, A. K., Pramanik, B., and Capdevila, J. |
| TITLE | : | Arachidonate epoxygenase: identification of epoxyeicosatrienoic acids in rabbit kidney PubMed ID:3625040 |
| JOURNAL | : | J Lipid Res. |
| VOL | : | 28 PAGE : 840-846 (1987) |
| AUTHOR | : | Toto, R., Siddhanta, A., Manna, S., Pramanik, B., Falck, J. R., and Capdevila, J. |
| TITLE | : | Arachidonic acid epoxygenase: detection of epoxyeicosatrienoic acids in human urine PubMed ID:3580381 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 919 PAGE : 132-139 (1987) |
| AUTHOR | : | Oliw, E. H. |
| TITLE | : | Biosynthesis of 18(RD)-hydroxyeicosatetraenoic acid from arachidonic acid by microsomes of monkey seminal vesicles. Some properties of a novel fatty acid omega 3-hydroxylase and omega 3-epoxygenase PubMed ID:2509448 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 264 PAGE : 17845-17853 (1989) |
| AUTHOR | : | Horton, E. W. |
| TITLE | : | Hypotheses on physiological roles of prostaglandins PubMed ID:4302663 |
| JOURNAL | : | Physiol Rev. |
| VOL | : | 49 PAGE : 122-161 (1969) |
| AUTHOR | : | Speroff, L., and Ramwell, P. W. |
| TITLE | : | Prostaglandins in reproductive physiology PubMed ID:4914185 |
| JOURNAL | : | Am J Obstet Gynecol. |
| VOL | : | 107 PAGE : 1111-1130 (1970) |
| AUTHOR | : | Horton, E. W. |
| TITLE | : | Biological activities of pure prostaglandins PubMed ID:5318739 |
| JOURNAL | : | Experientia. |
| VOL | : | 21 PAGE : 113-118 (1965) |
| AUTHOR | : | Karim, S. M., Hillier, K., and Devlin, J. |
| TITLE | : | Distribution of prostaglandins E1,E2, F1-alpha and F2-alpha in some animal tissues PubMed ID:4386742 |
| JOURNAL | : | J Pharm Pharmacol. |
| VOL | : | 20 PAGE : 749-753 (1968) |
| AUTHOR | : | Karim, S. M., Sandler, M., and Williams, E. D. |
| TITLE | : | Distribution of prostaglandins in human tissues PubMed ID:12262295 |
| JOURNAL | : | Bri Pharm Chemother. |
| VOL | : | 31 PAGE : 340-344 (1967) |
| AUTHOR | : | Kirtland, S. J. |
| TITLE | : | Prostaglandin E1: a review PubMed ID:2901111 |
| JOURNAL | : | Prostaglandins Leukot Essent Fatty Acids. |
| VOL | : | 32 PAGE : 165-174 (1988) |
| AUTHOR | : | Horton,E.W., and Main,I.H.M. |
| TITLE | : | The relationship between the chemical structure of prostagladnins and their biological activities. |
| JOURNAL | : | Mem. Soc. Endocr. |
| VOL | : | 14 PAGE : 29-36 (1966) |
| AUTHOR | : | Ogino, N., Miyamoto, T., Yamamoto, S., and Hayaishi, O. |
| TITLE | : | Prostaglandin endoperoxide E isomerase from bovine vesicular gland microsomes, a glutathione-requiring enzyme PubMed ID:838703 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 252 PAGE : 890-895 (1977) |
| AUTHOR | : | Needleman, P., Raz, A., Minkes, M. S., Ferrendelli, J. A., and Sprecher, H. |
| TITLE | : | Triene prostaglandins: prostacyclin and thromboxane biosynthesis and unique biological properties PubMed ID:218223 |
| JOURNAL | : | Proc Natl Acad Sci U S A. |
| VOL | : | 76 PAGE : 944-948 (1979) |
| AUTHOR | : | Prescott, S. M., Zimmerman, G. A., and Morrison, A. R. |
| TITLE | : | The effects of a diet rich in fish oil on human neutrophils: identification of leukotriene B5 as a metabolite PubMed ID:2996057 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 30 PAGE : 209-227 (1985) |
| AUTHOR | : | Terano, T., Salmon, J. A., and Moncada, S. |
| TITLE | : | Biosynthesis and biological activity of leukotriene B5 PubMed ID:6326200 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 27 PAGE : 217-232 (1984) |
| AUTHOR | : | Seya, A., Terano, T., Tamura, Y., and Yoshida, S. |
| TITLE | : | Comparative effect of leukotriene B4 and leukotriene B5 on calcium mobilization in human neutrophils PubMed ID:2852812 |
| JOURNAL | : | Prostaglandins Leukot Essent Fatty Acids. |
| VOL | : | 34 PAGE : 47-50 (1988) |
| AUTHOR | : | Taylor, P. L., and Kelly, R. W. |
| TITLE | : | 19-Hydroxylated E prostaglandins as the major prostaglandins of human semen PubMed ID:4855446 |
| JOURNAL | : | Nature. |
| VOL | : | 250 PAGE : 665-667 (1974) |
| AUTHOR | : | Corey, E. J., Schaaf, T. K., Huber, W., Koelliker, U., and Weinshenker, N. M. |
| TITLE | : | Total synthesis of prostaglandins F2-alpha and E2 as the naturally occurring forms PubMed ID:5411057 |
| JOURNAL | : | J Am Chem Soc. |
| VOL | : | 92 PAGE : 397-398 (1970) |
| AUTHOR | : | Donaldson,R.E., Saddler,J.C., Byrn,S., McKenzie, A.T., and Fuchs, P.L. |
| TITLE | : | A Triply Convergent Total Synthesis of L-(-)-Prostaglandin E2. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 48 PAGE : 2167-2188 (1983) |
| AUTHOR | : | Chen, S.-M.L., Schaub, R.E., and Grudzinskas,C.V. |
| TITLE | : | Prostaglandins and Congeners.19. Vinylstannanes:Useful Organometallic Reagents for the Synthesis of Prostaglandins and Prostaglandin Intermediates. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 43 PAGE : 3450-3454 (1978) |
| AUTHOR | : | Karim, S. M., Devlin, J., and Hillier, K. |
| TITLE | : | The stability of dilute solutions of prostaglandins E1, E2, F1-alpha and F2-alpha PubMed ID:5724918 |
| JOURNAL | : | Eur J Pharmacol. |
| VOL | : | 4 PAGE : 416-420 (1968) |
| AUTHOR | : | Pike, J.E., Lincoln,F.H., and Schneider,W.P. |
| TITLE | : | Prostanoic Acid Chemistry. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 34 PAGE : 3552-3557 (1969) |
| AUTHOR | : | Sih, C. J., Heather, J. B., Sood, R., Price, P., Peruzzotti, G., Lee, L. F., and Lee, S. S. |
| TITLE | : | Asymmetric total synthesis of (minus)-prostaglandin E1 and (minus)-prostaglandin E2 PubMed ID:1133372 |
| JOURNAL | : | J Am Chem Soc. |
| VOL | : | 97 PAGE : 865-874 (1975) |
| AUTHOR | : | Bundy, G. L., Schneider, W. P., Lincoln, F. H., and Pike, J. E. |
| TITLE | : | The synthesis of prostaglandins E 2 and F 2a from (15R)- and (15S)-PGA 2 PubMed ID:5016033 |
| JOURNAL | : | J Am Chem Soc. |
| VOL | : | 94 PAGE : 2123-2124 (1972) |
| AUTHOR | : | Lukacs,G., Piriou,F., and Gero,S.D. |
| TITLE | : | Carbon-13 Nuclear Magnetic Resonance Spectroscopy of Naturally Occurring Substances. Prostaglandins. |
| JOURNAL | : | Tetrah. Lett. |
| VOL | : | PAGE : 515-518 (1973) |
| AUTHOR | : | Horvath, G. |
| TITLE | : | Mass spectral studies on prostaglandins. IV--Prostaglandin F2alpha PubMed ID:990421 |
| JOURNAL | : | Biomed Mass Spectrom. |
| VOL | : | 3 PAGE : 127-136 (1976) |
| AUTHOR | : | Hayashi,M., and Tanouchi,T. |
| TITLE | : | Syntheses of 11-Dehydro-13,14-dihydro-PGE1 and PGD2. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 38 PAGE : 2115-2116 (1973) |
| AUTHOR | : | Jenny,E.F., and Schä$ublin,P. |
| TITLE | : | Total Synthesis of Prostaglandin D2. |
| JOURNAL | : | Tetrah. Lett. |
| VOL | : | PAGE : 2235-2238 (1974) |
| AUTHOR | : | Ogawa,Y., Nunomoto,M., and Shibasaki,M. |
| TITLE | : | A Novel Synthsis of Prostaglandin D2. |
| JOURNAL | : | J. Org. Chm. |
| VOL | : | 51 PAGE : 1625-1627 (1986) |
| AUTHOR | : | Kotovych,G., Aarts,G.H.M., Takashima,T.T., and Bigam,G. |
| TITLE | : | The Solution Conformation of Prostacyclin as Determined by High Field Proton Magnetic Resonance Techniques. |
| JOURNAL | : | Can. J. Chem. |
| VOL | : | 58 PAGE : 974-983 (1980) |
| AUTHOR | : | Johnson,R.A., Lincoln,F.H., Nidy,E.G., Schneider,W.P., Thompson,J.L., and Axen,U. |
| TITLE | : | Synthesis and Characterization of Prostacyclin, 6-Ketoprostaglandin F1a, Prostaglandin I1, and Prostaglandin I3. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 100 PAGE : 7690-7705 (1978) |
| AUTHOR | : | Moncada, S., Ferreira, S. H., and Vane, J. R. |
| TITLE | : | Bioassay of prostaglandins and biologically active substances derived from arachidonic acid PubMed ID:727046 |
| JOURNAL | : | Adv Prostaglandin Thromboxane Res. |
| VOL | : | 5 PAGE : 211-236 (1978) |
| AUTHOR | : | Porter,N.A., Byers,J.D., Ali,A.E., and Eling,T.E. |
| TITLE | : | Prostaglandin G2. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 102 PAGE : 1183-1184 (1980) |
| AUTHOR | : | Hamberg,M., Svensson,J., Wakabayashi,T., and Samuelsson,B. |
| TITLE | : | Isolation and Structure of Two Prostaglandin Endoperoxides That Cause Platelet Aggregation. PubMed ID:4521806 |
| JOURNAL | : | Proc. Nat. Acad. Sci. USA |
| VOL | : | 71 PAGE : 345-349 (1974) |
| AUTHOR | : | Gorman, R. R., Sun, F. F., Miller, O. V., and Johnson, R. A. |
| TITLE | : | Prostaglandins H1 and H2. Convenient biochemical synthesis and isolation. Further biological and spectroscopic characterization PubMed ID:887795 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 13 PAGE : 1043-1053 (1977) |
| AUTHOR | : | Porter,N.A., Byers,J.D., Holden,K.M. and Menzel,D.B. |
| TITLE | : | Synthesis of Prostaglandin H2. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 101 PAGE : 4319-4322 (1979) |
| AUTHOR | : | Johnson, R. A., Nidy, E. G., Baczynskyj, L., and Gorman, R. R. |
| TITLE | : | Synthesis of prostaglandin H2 methyl ester PubMed ID:915166 |
| JOURNAL | : | J Am Chem Soc. |
| VOL | : | 99 PAGE : 7738-7740 (1977) |
| AUTHOR | : | Corey,E.J., Marfat,A., Goto,G., and Brion F. |
| TITLE | : | Leukotriene B. Total Synthesis and Assignment of Stereochemistry. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 102 PAGE : 7984-7985 (1980) |
| AUTHOR | : | Merrer,Y.L., Gravier-Pelletier,C., Micas-Languin,D., Mestre,F., Durö$ault,A., and Depezay,J.-C. |
| TITLE | : | Total Synthesis of Leukotriene B4 [(+)-LTB4] and Homo-LTB4 from D-Mannitol. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 54 PAGE : 2409-2416 (1989) |
| AUTHOR | : | Yergey, J. A., Kim, H. Y., and Salem, N., Jr. |
| TITLE | : | High-performance liquid chromatography/thermospray mass spectrometry of eicosanoids and novel oxygenated metabolites of docosahexaenoic acid PubMed ID:2942056 |
| JOURNAL | : | Anal Chem. |
| VOL | : | 58 PAGE : 1344-1348 (1986) |
| AUTHOR | : | Corey,E.J., Clark,D.A., Goto,G., Marfat,A., Mioskowski,C., Samuelsson,B., and Hammarströ$m,S. |
| TITLE | : | Stereospecific Total Synthesis of a 'Slow Reacting Substance' of Anaphylaxis, Leucotriene C-1. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 102 PAGE : 1436-1439 (1980) |
| AUTHOR | : | Pace-Asciak, C. R. |
| TITLE | : | Mass spectra of prostaglandins and related products PubMed ID:2521759 |
| JOURNAL | : | Adv Prostaglandin Thromboxane Leukot Res. |
| VOL | : | 18 PAGE : 1-565 (1989) |
| AUTHOR | : | Morris, H. R., Taylor, G. W., Rokach, J., Girard, Y., Piper, P. J., Tippins, J. R., and Samhoun, M. N. |
| TITLE | : | Slow reacting substance of anaphylaxis, SRS-A; assignment of the stereochemistry PubMed ID:7422903 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 20 PAGE : 601-607 (1980) |
| AUTHOR | : | Lewis, R. A., Austen, K. F., Drazen, J. M., Clark, D. A., Marfat, A., and Corey, E. J. |
| TITLE | : | Slow reacting substances of anaphylaxis: identification of leukotrienes C-1 and D from human and rat sources PubMed ID:6106193 |
| JOURNAL | : | Proc Natl Acad Sci U S A. |
| VOL | : | 77 PAGE : 3710-3714 (1980) |
| AUTHOR | : | Cohen,N., Banner,B.L., Lopresti,R.J., Wong,F., Rosenberger,M., Liu,Y.-Y., Thom,E., and Liebman,A.A. |
| TITLE | : | Enantiospecific Syntheses of Leukotrienes C4, D4, and E4 and [14,153H2]Leukotriene E4 Dimethyl Ester. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 105 PAGE : 3661-3672 (1983) |
| AUTHOR | : | Mckay,S.W., Maller,O.N.B., Shrubasall,P.R., Smith,J.M., Baker,S.R., Jamieson,W.B., and Ross,W.J. |
| TITLE | : | Semi Preparative High Performance Liquid Chromatography and Spectroscopic Characterization of 8 Genometric Isomers of Leukotriene A Methyl Ester. |
| JOURNAL | : | J. Chromatogr. |
| VOL | : | 214 PAGE : 249-256 (1981) |
| AUTHOR | : | Borgeat,P., and Samuelsson,B. |
| TITLE | : | Arachidonic Acid Metabolism in Polymorphonuclear Leukocytes: Unstable Intermediate in Formation of Dihydroxy Acids. PubMed ID:290996 |
| JOURNAL | : | Proc. Nat. Acad. Sci. USA |
| VOL | : | 76 PAGE : 3213-3217 (1979) |
| AUTHOR | : | Cory,E.J., Arai,Y., and Mioskowski,C. |
| TITLE | : | Total Synthesis of ()-5,6-Oxido-7,9-trans,11,14-cis-eicosapentaenoic Acid, a Possible Precursor of SRSA. |
| JOURNAL | : | J. Am. Che. Soc. |
| VOL | : | 101 PAGE : 6748-6749 (1979) |
| AUTHOR | : | Svensson, J., Hamberg, M., and Samuelsson, B. |
| TITLE | : | On the formation and effects of thromboxane A2 in human platelets PubMed ID:998278 |
| JOURNAL | : | Acta Physiol Scand. |
| VOL | : | 98 PAGE : 285-294 (1976) |
| AUTHOR | : | Hanessian,S., and Lavallee,P. |
| TITLE | : | A Stereospecific, Total Synthesis of Thromboxane B2. |
| JOURNAL | : | Can. J. Chem. |
| VOL | : | 55 PAGE : 562-565 (1977) |
| AUTHOR | : | Kotovych,G., and Aarts,G.H.M. |
| TITLE | : | A High Field Proton Magnetic Resonance Study of the Solution Conformation of Thromboxane B2. |
| JOURNAL | : | Can. J. Chem. |
| VOL | : | 58 PAGE : 1111-1117 (1980) |
| AUTHOR | : | Kelly,R.C., Schletter,I., and Stein,S.J. |
| TITLE | : | Synthesis of Thromboxane B2. |
| JOURNAL | : | Tetrah. Lett. |
| VOL | : | PAGE : 3279-3282 (1976) |
| AUTHOR | : | Serhan, C. N., Hamberg, M., and Samuelsson, B. |
| TITLE | : | Trihydroxytetraenes: a novel series of compounds formed from arachidonic acid in human leukocytes PubMed ID:6422933 |
| JOURNAL | : | Biochem Biophys Res Commun. |
| VOL | : | 118 PAGE : 943-949 (1984) |
| AUTHOR | : | Adams,J., Fitzsimmons,B.J., Girard,Y., Leblanc,Y, Evans,J.F., and Rokach,J. |
| TITLE | : | Enantiospecific and Stereospecific Synthesis of Lipoxin A. Stereochemical Assignment of the Natural Lipoxin A and Its Possible Biosynthesis. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 107 PAGE : 464-469 (1985) |
| AUTHOR | : | Serhan, C. N., Nicolaou, K. C., Webber, S. E., Veale, C. A., Dahlen, S. E., Puustinen, T. J., and Samuelsson, B. |
| TITLE | : | Lipoxin A. Stereochemistry and biosynthesis PubMed ID:3097008 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 261 PAGE : 16340-16345 (1986) |
| AUTHOR | : | Serhan,C.N., Hamberg,M., and Samuelsson,B. |
| TITLE | : | Lipoxins: Novel Series of Biologically Active Compounds Formed from Arachidonic Acid in Human Leukocytes. PubMed ID:6089195 |
| JOURNAL | : | Proc. Nat. Acad. Sci. USA |
| VOL | : | 81 PAGE : 5335-5339 (1984) |
| AUTHOR | : | Serhan, C. N., Hamberg, M., Samuelsson, B., Morris, J., and Wishka, D. G. |
| TITLE | : | On the stereochemistry and biosynthesis of lipoxin B PubMed ID:3083410 |
| JOURNAL | : | Proc Natl Acad Sci U S A. |
| VOL | : | 83 PAGE : 1983-1987 (1986) |
| AUTHOR | : | Nicolaou,K.C., and Webber,S.E. |
| TITLE | : | Stereocontrolled Total Synthesis of Lipoxin B. |
| JOURNAL | : | Synthesis |
| VOL | : | PAGE : 453-461 (1986) |
| AUTHOR | : | Corey, E. J., and Moinet, G. |
| TITLE | : | Direct, stereocontrolled synthesis of a prostaglandins using the bicyclo[2.2.1]heptene approach PubMed ID:4746271 |
| JOURNAL | : | J Am Chem Soc. |
| VOL | : | 95 PAGE : 6331-6332 (1973) |
| AUTHOR | : | Schneider, W. P., Bundy, G. L., Lincoln, F. H., Daniels, E. G., and Pike, J. E. |
| TITLE | : | Isolation and chemical conversions of prostaglandins from Plexaura homomalla: Preparation of prostaglandin E2, prostaglandin F2alpha, and their 5,6-trans isomers PubMed ID:13095 |
| JOURNAL | : | J Am Chem Soc. |
| VOL | : | 99 PAGE : 1222-1232 (1977) |
| AUTHOR | : | Cooper, G. F., and Fried, J. |
| TITLE | : | Carbon-13 nuclear magnetic resonance spectra of prostaglandins and some prostaglandin analogs PubMed ID:4514326 |
| JOURNAL | : | Proc Natl Acad Sci U S A. |
| VOL | : | 70 PAGE : 1579-1584 (1973) |
| AUTHOR | : | Floyd,M.B., Schaub,R.E., Siuta,G.J., Skotnicki,J.S., Grudzinskas,C.V., Weiss,M.J., Dessy,F., and VanHumbeeck,L. |
| TITLE | : | Prostaglandins and Congeners. 22. Synthesis of 11-Substituted Derivatives of 11-Deoxyprostaglandins E1 and E2. Potential Bronchodilators. PubMed ID:7401116 |
| JOURNAL | : | J. Med. Chem. |
| VOL | : | 23 PAGE : 903-913 (1980) |
| AUTHOR | : | Kelly,R.C., Schletter,I, Jones,R.L. |
| TITLE | : | Total Synthesis of PGC2 Methyl Ester. Comparison with Enzymatically Produced Material. PubMed ID:7401116 |
| JOURNAL | : | Prostaglandins |
| VOL | : | 4 PAGE : 653-660 (1973) |
| AUTHOR | : | Corey,E.J., and Cyr, C.R. |
| TITLE | : | Transformation of Prostaglandin A2 into Prostaglandin C2. |
| JOURNAL | : | Tetrah. Lett. |
| VOL | : | PAGE : 1761-1763 (1974) |
| AUTHOR | : | Mubarik Ali,S., Chapeleo,C.B., Finch,M.A.W., Roberts,S.M., Woolley,G.T., Cave,R.J., and Newton,R.F. |
| TITLE | : | Preparation and Some Reactions of 2-Oxatricyclo[3.3.0.04.6]oct-7-en-3-one: Synthesis of 9-Deoxa-9,10-dehydroprostaglandin D2. |
| JOURNAL | : | J. Chem. Soc. Perkin I |
| VOL | : | PAGE : 2093-2097 (1980) |
| AUTHOR | : | Bundy,G.L., Morton,D.R., Peterson,D.C., Nishizawa,E.E., and Miller,W.L. |
| TITLE | : | Synthesis and Platetet Aggregation Inhibiting Activity of Prostaglanin D Analogues. PubMed ID:6854581 |
| JOURNAL | : | J. Med. Chem. |
| VOL | : | 26 PAGE : 790-799 (1983) |
| AUTHOR | : | Fitzpatrick,F.A., and Wynalda,M.A. |
| TITLE | : | Albumin-catalyzed Metabolism of Prostaglandin D2. Identification of Products Formed in vitro. PubMed ID:6578214 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 258 PAGE : 11713-11718 (1983) |
| AUTHOR | : | Kikawa, Y., Narumiya, S., Fukushima, M., Wakatsuka, H., and Hayaishi, O. |
| TITLE | : | 9-Deoxy-delta 9, delta 12-13,14-dihydroprostaglandin D2, a metabolite of prostaglandin D2 formed in human plasma PubMed ID:6584883 |
| JOURNAL | : | Proc Natl Acad Sci U S A. |
| VOL | : | 81 PAGE : 1317-1321 (1984) |
| AUTHOR | : | Pace-Asciak,C. |
| TITLE | : | Isolation, Structure, and Biosynthesis of 6-Ketoprostaglandin F1a in the Rat Stomach. PubMed ID:1254872 |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 98 PAGE : 2348-2349 (1976) |
| AUTHOR | : | Tanaka,T., Hazato,A., Bannai,K., Okamura,N., Sugiura,S., Manabe,K., Toru,T., Kurozumi,S., Suzuki,M., Kawagishi,T., et al |
| TITLE | : | Nitro-Olefin Trapping Reaction of Enolates In Situ Generated by Conjugate Addition Reaction: Short Synthesis of PGE1, 6-Oxo-PGE1, 6-Oxo-PGF1a, and PGI2. |
| JOURNAL | : | Tetrahedron |
| VOL | : | 43 PAGE : 813-824 (1987) |
| AUTHOR | : | Cepa, S. R., Hall, E. R., and Venton, D. L. |
| TITLE | : | Positive-negative, chemical-ionization, direct exposure mass spectrometry of underivatized prostaglandins PubMed ID:6547237 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 27 PAGE : 645-652 (1984) |
| AUTHOR | : | Morrison, A. R., McLaughlin, L., Bloch, M., and Needleman, P. |
| TITLE | : | A novel cyclooxygenase metabolite of arachidonic acid PubMed ID:6436248 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 259 PAGE : 13579-13583 (1984) |
| AUTHOR | : | Kindahl,H. |
| TITLE | : | Metabolism of Thromboxane B2 in the Cynomolgus Monkey. PubMed ID:404670 |
| JOURNAL | : | Prostaglandins |
| VOL | : | 13 PAGE : 619-629 (1977) |
| AUTHOR | : | Nelson, N. A., Jackson, R. W., and Sebek, O. K. |
| TITLE | : | Synthesis of thromboxane B2 metabolites PubMed ID:704927 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 16 PAGE : 85-92 (1978) |
| AUTHOR | : | Roberts, L. J., 2nd, Sweetman, B. J., and Oates, J. A. |
| TITLE | : | Metabolism of thromboxane B2 in the monkey PubMed ID:97291 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 253 PAGE : 5305-5318 (1978) |
| AUTHOR | : | Pace-Asciak, C. R., Carrara, M. C., and Domazet, Z. |
| TITLE | : | Identification of the major urinary metabolites of 6-ketoprostaglandin F1alpha (6K-PGF1alpha) in the rat PubMed ID:907663 |
| JOURNAL | : | Biochem Biophys Res Commun. |
| VOL | : | 78 PAGE : 115-121 (1977) |
| AUTHOR | : | Meese,C.O. |
| TITLE | : | A Novel Synthesis of 2,3-Dinor-6-oxo-prostaglandin F1a. |
| JOURNAL | : | Tetrah. Lett |
| VOL | : | 25 PAGE : 2199-2200 (1984) |
| AUTHOR | : | Hamberg, M., and Samuelsson, B. |
| TITLE | : | The structure of the major urinary metabolite of prostaglandin E2 in man PubMed ID:5784182 |
| JOURNAL | : | J Am Chem Soc. |
| VOL | : | 91 PAGE : 2177-2178 (1969) |
| AUTHOR | : | Granstrom, E., and Samuelsson, B. |
| TITLE | : | The structure of a urinary metabolite of prostaglandin F2a in man PubMed ID:5791928 |
| JOURNAL | : | J Am Chem Soc. |
| VOL | : | 91 PAGE : 3398-3400 (1969) |
| AUTHOR | : | Rosenberger,M., Newkom,C., and Aig,E.R. |
| TITLE | : | Total Synthesis of Leukotriene E4, a Member of the SRS-A Family. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 105 PAGE : 3656-3661 (1983) |
| AUTHOR | : | Denis, D., Charleson, S., Rackham, A., Jones, T. R., Ford-Hutchinson, A. W., Lord, A., Cirino, M., Girard, Y., Larue, M., and Rokach, J. |
| TITLE | : | Synthesis and biological activities of leukotriene F4 and leukotriene F4 sulfone PubMed ID:6300970 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 24 PAGE : 801-814 (1982) |
| AUTHOR | : | Okuyama, S., Miyamoto, S., Shimoji, K., Konishi, Y., Fukushima, D., Niwa, H., Arai, Y., Toda, M., and Hayashi, M. |
| TITLE | : | Structural analogs of leukotrienes C and D avd their contractile activities PubMed ID:7139817 |
| JOURNAL | : | Chem Pharm Bull (Tokyo). |
| VOL | : | 30 PAGE : 2453-2462 (1982) |
| AUTHOR | : | Ellis,F., Mills,L.S., and North,P.C. |
| TITLE | : | A Total Synthesis of Leukotriene F4 (LTF4). |
| JOURNAL | : | Tetrah. Lett. |
| VOL | : | 23 PAGE : 3735-3736 (1982) |
| AUTHOR | : | Hagmann, W., Denzlinger, C., and Keppler, D. |
| TITLE | : | Production of peptide leukotrienes in endotoxin shock PubMed ID:3967766 |
| JOURNAL | : | FEBS Lett. |
| VOL | : | 180 PAGE : 309-313 (1985) |
| AUTHOR | : | Foster, A., Fitzsimmons, B., and Letts, L. G. |
| TITLE | : | The synthesis of N-acetyl-leukotriene E4 and its effects on cardiovascular and respiratory function of the anesthetized pig PubMed ID:3763939 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 31 PAGE : 1077-1086 (1986) |
| AUTHOR | : | Kotovych,G. and Aarts,G.H.M. |
| TITLE | : | Homonuclear One- and Two-Dimentional Nuclear Overhauser Effect Experiments and Spin-Echo Correlated Spectroscopy. Application to Prostaglandin E1 and 6-Keto-Prostaglandin E1. |
| JOURNAL | : | Can. J. Chem. |
| VOL | : | 60 PAGE : 2617-2624 (1982) |
| AUTHOR | : | Walker, I. C., Jones, R. L., and Wilson, N. H. |
| TITLE | : | The identification of an epoxy-hydroxy acid as a product from the incubation of arachidonic acid with washed blood platelets PubMed ID:523677 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 18 PAGE : 173-178 (1979) |
| AUTHOR | : | Pace-Asciak, C. R., Mizuno, K., and Yamamoto, S. |
| TITLE | : | Resolution by DEAE-cellulose chromatography of the enzymatic steps in the transformation of arachidonic acid into 8, 11, 12- and 10, 11, 12-trihydroxy-eicosatrienoic acid by the rat lung PubMed ID:6405454 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 25 PAGE : 79-84 (1983) |
| AUTHOR | : | Corey,E.J. and Su,W. |
| TITLE | : | Total Synthesis of Biologically Active Metabolites of Arachidonic Acid. The Two 8-Hydroxy-11,12(S,S)-epoxyeicosa-5,14(Z),9(E)-trienoic Acids. |
| JOURNAL | : | Tetrah. Lett. |
| VOL | : | 25 PAGE : 5119-5122 (1984) |
| AUTHOR | : | Moghaddam, M. F., Gerwick, W. H., and Ballantine, D. L. |
| TITLE | : | Discovery of the mammalian insulin release modulator, hepoxilin B3, from the tropical red algae Platysiphonia miniata and Cottoniella filamentosa PubMed ID:2180942 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 265 PAGE : 6126-6130 (1990) |
| AUTHOR | : | Pace-Asciak, C. R., Granstrom, E., and Samuelsson, B. |
| TITLE | : | Arachidonic acid epoxides. Isolation and structure of two hydroxy epoxide intermediates in the formation of 8,11,12- and 10,11,12-trihydroxyeicosatrienoic acids PubMed ID:6406490 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 258 PAGE : 6835-6840 (1983) |
| AUTHOR | : | Corey,E.J., Kang,J., Laguzza,B.C. and Jones, R.L. |
| TITLE | : | Total Synthesis of 12-(S)-10-Hydroxy-trans-11,12-epoxyeicosa-5,9,14-(Z)-Trienoic Acids, Metabolites of Arachidonic Acid in Mammalian Blood Platelets. |
| JOURNAL | : | Tetrah. Lett. |
| VOL | : | 24 PAGE : 4913-4916 (1983) |
| AUTHOR | : | Corey,E.J., Wright,S.W. and Matsuda,S.P.T. |
| TITLE | : | Stereochemistry and Mechanism of the Biosynthesis of Leukotriene A4 from 5(S)-Hydroxy-6(E),8,11,14(Z)-eicosatetraenoic Acid. Evidence for an Organoiron Intermediates. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 111 PAGE : 1452-1455 (1989) |
| AUTHOR | : | Porter,N.A., Logan,J. and Kontoyiannidou,V. |
| TITLE | : | Preparation and Purification of Arachidonic Acid Hydroperoxides of Biological Importance. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 44 PAGE : 3177-3181 (1979) |
| AUTHOR | : | Boeynaems, J. M., Brash, A. R., Oates, J. A., and Hubbard, W. C. |
| TITLE | : | Preparation and assay of monohydroxy-eicosatetraenoic acids PubMed ID:7004263 |
| JOURNAL | : | Anal Biochem. |
| VOL | : | 104 PAGE : 259-267 (1980) |
| AUTHOR | : | Corey,E.J. and Hashimoto,S. |
| TITLE | : | A Practical Process for Large-Scale Synthesis of (S)-5-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoic Acid (5-HETE). |
| JOURNAL | : | Tetrah. Lett. |
| VOL | : | 22 PAGE : 299-302 (1981) |
| AUTHOR | : | Borgeat,P., Hamberg,M. and Samuelsson,B. |
| TITLE | : | Transformation of Arachidonic Acid and Homo-g-linolenic Acid by Rabbit Polymorphonuclear Leukocytes. Monohydroxy Acids from Novel Lipoxygenases. PubMed ID:826538 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 251 PAGE : 7816-7820 (1976) |
| AUTHOR | : | Hamberg,M. and Samuelsson,B. |
| TITLE | : | Prostaglandin Endoperoxides. Novel Transformation of Arachidonic Acid in Human Platelets. PubMed ID:4215079 |
| JOURNAL | : | Proc. Nat. Acad. Sci. USA |
| VOL | : | 71 PAGE : 3400-3404 (1974) |
| AUTHOR | : | Corey,E.J., Niwa,H. and Knolle,J. |
| TITLE | : | Total Synthesis of (S)-12-Hydroxy-5,8,14-cis-10-trans-eicosatetraenoic Acid (Samuelsson's HETE). |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 100 PAGE : 1942-1943 (1978) |
| AUTHOR | : | Leblanc,Y., Fitzsimmons,B.J., Adams,J., Perez,F. and Rokach,J. |
| TITLE | : | The Total Synthesis of 12-HETE and 12,20-DiHETE. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 51 PAGE : 789-793 (1986) |
| AUTHOR | : | Just,G. and Wang,Z.Y. |
| TITLE | : | Total Synthesis of 8(S)-, 9(S)-, 11(S)-, and 12(S)-HETE Methyl Esters. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 51 PAGE : 4796-4802 (1986) |
| AUTHOR | : | Hamberg,M. and Samuelsson,B. |
| TITLE | : | On the Specificity of the Oxygenation of Unsaturated Fatty Acids Catalyzed by Soybean Lipoxidase. PubMed ID:6070850 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 242 PAGE : 5329-5335 (1967) |
| AUTHOR | : | Baldwin,J.E., Davies,D.I., Hughes,L. and Gutterridge,N.J.A. |
| TITLE | : | Synthesis from Arachidonic Acid of Potential Prostaglandin Precursors. |
| JOURNAL | : | J. Chem. Soc. Perkin I |
| VOL | : | PAGE : 115-121 (1979) |
| AUTHOR | : | Van Os, C. P., Rijke-Schilder, G. P., Van Halbeek, H., Verhagen, J., and Vliegenthart, J. F. |
| TITLE | : | Double dioxygenation of arachidonic acid by soybean lipoxygenase-1. Kinetics and regio-stereo specificities of the reaction steps PubMed ID:6783108 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 663 PAGE : 177-193 (1981) |
| AUTHOR | : | Nicolaou,K.C., Stylianides,N.A. and Ramphal,J.Y. |
| TITLE | : | Stereocontrolled Total Synthesis of Methyl 12(S)-Hydroxy-5Z,8E,10E-heptadecatrienoate. |
| JOURNAL | : | J. Chem. Soc. Perkin Trans. I |
| VOL | : | PAGE : 2131-2132 (1989) |
| AUTHOR | : | Hawkins, D.J. and Brash,A.R. |
| TITLE | : | Eggs of the Sea Urchin, Strongylocentrotus purpuratus, Contain a Prominent (11R) and (12R) Lipoxygenase Activity. PubMed ID:3108255 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 262 PAGE : 7629-7634 (1987) |
| AUTHOR | : | Woollard,P.M. |
| TITLE | : | Stereochemical Difference Between 12-Hydroxy-5,8,10,14-eicosatetraenoic Acid in Platelets and Psoriatic Lesions. PubMed ID:3707572 |
| JOURNAL | : | Biochem. Biophys. Res. Commun. |
| VOL | : | 136 PAGE : 169-176 (1986) |
| AUTHOR | : | Yadagiri,P., Lumin,S., Mosset,P., Capdevila,J. and Falck,J.R. |
| TITLE | : | Enantiospecific Total Synthesis of 8- and 12-Hydroxyeicosatetraenoic Acid. |
| JOURNAL | : | Tetrah. Lett. |
| VOL | : | 27 PAGE : 6039-6040 (1986) |
| AUTHOR | : | Bundy, G. L., Nidy, E. G., Epps, D. E., Mizsak, S. A., and Wnuk, R. J. |
| TITLE | : | Discovery of an arachidonic acid C-8 lipoxygenase in the gorgonian coral Pseudoplexaura porosa PubMed ID:2867091 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 261 PAGE : 747-751 (1986) |
| AUTHOR | : | Shin,D.-S., Yadagiri,P., Falck,J.R., Masferrer,J.L. and Schwartzman,M.L. |
| TITLE | : | Synthesis and Structure Confirmation of Compound D, a Proinflammatory Arachidonate Metabolite. |
| JOURNAL | : | Tetrah. Lett. |
| VOL | : | 30 PAGE : 3923-3926 (1989) |
| AUTHOR | : | Murphy,R.C., Falck,J.R., Lumin,S., Yadagiri,P., Zirrolli,J.A., Balazy,M., Masferrer,J.L., Abraham,N.G. and Schwartzman,M.L. |
| TITLE | : | 12(R)-Hydroxyeicosatrienoic Acid: A Vasodilator Cytochrome P-450-dependent Arachidonate Metabolite from the Bovine Corneal Epithelium. PubMed ID:3141417 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 263 PAGE : 17197-17202 (1988) |
| AUTHOR | : | Chacos,N., Falck,J.R., Wixtrom,C. and Capdevila,J. |
| TITLE | : | Novel Epoxides Formed during the Liver Cytochrome P-450 Oxidation of Arachidonic Acid. PubMed ID:6803794 |
| JOURNAL | : | Biochem. Biophys. Res. Commun. |
| VOL | : | 104 PAGE : 916-822 (1982) |
| AUTHOR | : | Oliw,E.H., Guengerich,F.P. and Oates,J.A. |
| TITLE | : | Oxygenation of Arachidonic Acid by Hepatic Monooxygenases. Isolation and Metabolism of Four Epoxide Intermediates. PubMed ID:6801052 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 257 PAGE : 3771-3781 (1982) |
| AUTHOR | : | Moustakis,C.A., Viala,J., Capdevila,J. and Falck,J.R. |
| TITLE | : | Total Synthesis of the Cytochrome p-450 Epoxygenase Metabolites 5(R),6(S)-, 5(S),6(R)-, and 14(R),15(S)-Epoxyeicosatrienoic Acid (EET) and Hydration Products 5(R),6(R)- and 14(R),15(R)-Dihydroxyeicosatrienoic Acid (DHET). |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 107 PAGE : 5283-5285 (1985) |
| AUTHOR | : | Mosset,P., Yadagiri,P., Lumin,S., Capdevila,J. and Falck,J.R. |
| TITLE | : | Arachidonic Epoxygenase: Total Synthesis of Both Enantiomers of 8,9- and 11,12-epoxyeicosatrienoic Acid. |
| JOURNAL | : | Tetrah. Lett. |
| VOL | : | 27 PAGE : 6035-6038 (1986) |
| AUTHOR | : | Falck,J.R., Manna,S. and Capdevila,J. |
| TITLE | : | Enantiospecific Synthesis of Methyl 11,12- and 14,15-Epoxyeicosatrienoate. |
| JOURNAL | : | Tetrah. Lett. |
| VOL | : | 25 PAGE : 2443-2446 (1984) |
| AUTHOR | : | VanRollins, M. |
| TITLE | : | Synthesis and characterization of cytochrome P-450 epoxygenase metabolites of eicosapentaenoic acid PubMed ID:2215089 |
| JOURNAL | : | Lipids. |
| VOL | : | 25 PAGE : 481-490 (1990) |
| AUTHOR | : | Andersen, N. H. |
| TITLE | : | Dehydration of prostaglandins: study by spectroscopic method PubMed ID:5785003 |
| JOURNAL | : | J Lipid Res. |
| VOL | : | 10 PAGE : 320-325 (1969) |
| AUTHOR | : | Ramwell,P.W., Shaw,J.E., Clarke,G.B., Grostic,M.F., Kaiser,D.G. and Pike, J.E. |
| TITLE | : | Prostaglandins (Review). |
| JOURNAL | : | Progr. Chem. Fats Other Lipids |
| VOL | : | 9 PAGE : 233-273 (1968) |
| AUTHOR | : | Jones, R. L. |
| TITLE | : | 15-hydroxy-9-oxoprosta-11, 13-dienoic acid as the product of a prostaglandin isomerase PubMed ID:5064903 |
| JOURNAL | : | J Lipid Res. |
| VOL | : | 13 PAGE : 511-518 (1972) |
| AUTHOR | : | Hamberg, M., and Samuelsson, B. |
| TITLE | : | Prostaglandins in human seminal plasma. Prostaglandins and related factors 46 PubMed ID:5903721 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 241 PAGE : 257-263 (1966) |
| AUTHOR | : | Collins, P., Jung, C. J., and Pappo, R. |
| TITLE | : | Prostaglandin studies: the total synthesis of DL-prostaglandin B1 PubMed ID:12310168 |
| JOURNAL | : | Isr J Chem. |
| VOL | : | 6 PAGE : 839-841 (1968) |
| AUTHOR | : | Struijk,M.C.B., Beerthuis,R.K., Pabon,H.J.J. and Van Dorp,D.A. |
| TITLE | : | Specificity in the Enzymic Conversion of Polyunsaturated Fatty Acids into Prostaglandins. |
| JOURNAL | : | Recueil |
| VOL | : | 85 PAGE : 1233-1250 (1966) |
| AUTHOR | : | Bergströ$m,S. and Sjö$vall |
| TITLE | : | The Isolation of Prostaglandin E from Sheep Prostate Glands. |
| JOURNAL | : | Acta Chem. Scand. |
| VOL | : | 14 PAGE : 1701-1705 (1960) |
| AUTHOR | : | Corey, E. J., Vlattas, I., and Harding, K. |
| TITLE | : | Total synthesis of natural (levo) and enantiomeric (dextro) forms of prostaglandin El PubMed ID:5782511 |
| JOURNAL | : | J Am Chem Soc. |
| VOL | : | 91 PAGE : 535-536 (1969) |
| AUTHOR | : | Hayashi,M. and Miyamoto,T. |
| TITLE | : | Chemistry of Prostaglandins. |
| JOURNAL | : | Metabolism and Disease (Taisha) |
| VOL | : | 12 PAGE : 1461-1476 (1975) |
| AUTHOR | : | Bergströ$m,S. and Sjö$vall |
| TITLE | : | The Isolation of Prostaglandin F from Sheep Prostate Glands. PubMed ID:12336881 |
| JOURNAL | : | Acta Chem. Scand. |
| VOL | : | 14 PAGE : 1693-1700 (1960) |
| AUTHOR | : | Miyano, M., Dorn, C. R., and Mueller, R. A. |
| TITLE | : | Prostaglandins. IV. A synthesis of F-type prostaglandins. A total synthesis of prostaglandin F 1 PubMed ID:5037449 |
| JOURNAL | : | J Org Chem. |
| VOL | : | 37 PAGE : 1810-1818 (1972) |
| AUTHOR | : | De Clercq, P., Samson, M., Tavernier, D., Van Haver, D., and Vandewalle, M. |
| TITLE | : | Conformational analysis of prostaglandins F1 based on proton nuclear magnetic resonance spectral data PubMed ID:894396 |
| JOURNAL | : | J Org Chem. |
| VOL | : | 42 PAGE : 3140-3144 (1977) |
| AUTHOR | : | Okamoto,S., Kobayashi,Y. and Sato,F. |
| TITLE | : | A Highly Efficient Synthesis of Natural PGE3 and 5,6-Dihydro PGE3 via Two-component Coupling Process. |
| JOURNAL | : | Tetrah. Lett. |
| VOL | : | 30 PAGE : 4379-4382 (1989) |
| AUTHOR | : | Corey, E. J., Shirahama, H., Yamamoto, H., Terashima, S., Venkateswarlu, A., and Schaaf, T. K. |
| TITLE | : | Stereospecific total synthesis of prostaglandins E3 and F3 alpha PubMed ID:5548346 |
| JOURNAL | : | J Am Chem Soc. |
| VOL | : | 93 PAGE : 1490-1491 (1971) |
| AUTHOR | : | Samuelsson,B. |
| TITLE | : | Prostaglandins and Related Factors. 17. The Structure of Prostaglandin E3. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 85 PAGE : 1878-1879 (1963) |
| AUTHOR | : | Bergströ$m,S., Dressler,F., Ryhage,R., Samuelsson,B. and Sjö$vall |
| TITLE | : | The Isolation of Two Further Prostaglandins from Sheep Prostate Glands. Prostaglndin and Related Factors 8. |
| JOURNAL | : | Ark. Kemi. |
| VOL | : | 19 PAGE : 563-567 (1962) |
| AUTHOR | : | Smith, D. R., Weatherly, B. C., Salmon, J. A., Ubatuba, F. B., Gryglewski, R. J., and Moncada, S. |
| TITLE | : | Preparation and biochemical properties of PGH3 PubMed ID:531219 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 18 PAGE : 423-438 (1979) |
| AUTHOR | : | Hamberg, M. |
| TITLE | : | Transformations of 5,8,11,14,17-eicosapentaenoic acid in human platelets PubMed ID:6249377 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 618 PAGE : 389-398 (1980) |
| AUTHOR | : | Nakamura,N., Nagai,H., Yoneda,M., Suga,H., Kawamura,M. and Iguchi,S. |
| TITLE | : | Synthesis of Thromboxane B3 and Its Direct Separation from Thromboxane B2 by Reversed-Phase High Performance Liquid Chromatography. |
| JOURNAL | : | Chem. Pham. Bull. |
| VOL | : | 41 PAGE : 1769-1773 (1993) |
| AUTHOR | : | Corey,E.J., Pyne,S.G. and Su,W. |
| TITLE | : | Total Synthesis of Leukotriene B5. |
| JOURNAL | : | Tetrah. Lett. |
| VOL | : | 24 PAGE : 4883-4886 (1983) |
| AUTHOR | : | Murphy, R. C., Pickett, W. C., Culp, B. R., and Lands, W. E. |
| TITLE | : | Tetraene and pentaene leukotrienes: selective production from murine mastocytoma cells after dietary manipulation PubMed ID:6119740 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 22 PAGE : 613-622 (1981) |
| AUTHOR | : | Krakoff, L. R., Vlachakis, N., Mendlowitz, M., and Stricker, J. |
| TITLE | : | Differential effect of prostaglandin A1 in hypertensive patients with low, normal and high renin PubMed ID:1077785 |
| JOURNAL | : | Clin Sci Mol Med Suppl. |
| VOL | : | 2 PAGE : 311s-313s (1975) |
| AUTHOR | : | Granstrom, E., Hamberg, M., Hansson, G., and Kindahl, H. |
| TITLE | : | Chemical instability of 15-keto-13,14-dihydro-PGE2: the reason for low assay reliability PubMed ID:7384561 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 19 PAGE : 933-957 (1980) |
| AUTHOR | : | Fitzpatrick, F. A., Aguirre, R., Pike, J. E., and Lincoln, F. H. |
| TITLE | : | The stability of 13,14-dihydro-15 keto-PGE2 PubMed ID:7384560 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 19 PAGE : 917-931 (1980) |
| AUTHOR | : | Hirata, Y., Hayashi, H., Ito, S., Kikawa, Y., Ishibashi, M., Sudo, M., Miyazaki, H., Fukushima, M., Narumiya, S., and Hayaishi, O. |
| TITLE | : | Occurrence of 9-deoxy-delta 9,delta 12-13,14-dihydroprostaglandin D2 in human urine PubMed ID:3053696 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 263 PAGE : 16619-16625 (1988) |
| AUTHOR | : | Kulkarni,P.S.,Kaufman,P.L.,Srinivasan,B.D. |
| TITLE | : | Eicosapentaenoic acid metabolism in cynomolgus and rhesus conjunctiva and eyelid. PubMed ID:2846724 |
| JOURNAL | : | J.Ocul.Pharmacol. |
| VOL | : | 3 PAGE : 349-356 (1987) |
| AUTHOR | : | Bundy,G.L.,Morton,D.R.,Peterson,D.C. |
| TITLE | : | Synthesis and platelet aggregation inhibiting activity of prostaglandin D analogues. PubMed ID:6854581 |
| JOURNAL | : | J.Med.Chem. |
| VOL | : | 26 PAGE : 790-799 (1983) |
| AUTHOR | : | Goh, Y., Nakajima, M., Azuma, I., and Hayaishi, O. |
| TITLE | : | Effects of prostaglandin D2 and its analogues on intraocular pressure in rabbits PubMed ID:3236567 |
| JOURNAL | : | Jpn J Ophthalmol. |
| VOL | : | 32 PAGE : 471-480 (1988) |
| AUTHOR | : | Kulkarni, P. S., and Srinivasan, B. D. |
| TITLE | : | Prostaglandins E3 and D3 lower intraocular pressure PubMed ID:4019112 |
| JOURNAL | : | Invest Ophthalmol Vis Sci. |
| VOL | : | 26 PAGE : 1178-1182 (1985) |
| AUTHOR | : | Kobzar, G., Mardla, V., Jarving, I., Lohmus, M., Vahemets, A., Samel, N., and Lille, U. |
| TITLE | : | Comparison of the inhibitory effect of E-prostaglandins in human and rabbit platelet-rich plasma and washed platelets PubMed ID:7904921 |
| JOURNAL | : | Comp Biochem Physiol C. |
| VOL | : | 106 PAGE : 489-494 (1993) |
| AUTHOR | : | Hamberg,M. and Samuelsson,B. |
| TITLE | : | On the metabolism of prostaglandins E1 and E2 in man. PubMed ID:5126221 |
| JOURNAL | : | J.Biol.Chem. |
| VOL | : | 246 PAGE : 6713-6721 (1971) |
| AUTHOR | : | Leonhardt, A., Krauss, M., Gieler, U., Schweer, H., Happle, R., and Seyberth, H. W. |
| TITLE | : | In vivo formation of prostaglandin E1 and prostaglandin E2 in atopic dermatitis PubMed ID:9115911 |
| JOURNAL | : | Br J Dermatol. |
| VOL | : | 136 PAGE : 337-340 (1997) |
| AUTHOR | : | Westwick, J. |
| TITLE | : | The effect of pulmonary metabolites of prostaglandins E1, E2 and F2alpha on ADP-induced aggregation of human and rabbit platelets [proceedings] PubMed ID:974413 |
| JOURNAL | : | Br J Pharmacol. |
| VOL | : | 58 PAGE : 297P-298P (1976) |
| AUTHOR | : | Kelly, R. W., Taylor, P. L., Hearn, J. P., Short, R. V., Martin, D. E., and Marston, J. H. |
| TITLE | : | 19-Hydroxyprostaglandin E1 as a major component of the semen of primates PubMed ID:817207 |
| JOURNAL | : | Nature. |
| VOL | : | 260 PAGE : 544-545 (1976) |
| AUTHOR | : | Woodward, D. F., Protzman, C. E., Krauss, A. H., and Williams, L. S. |
| TITLE | : | Identification of 19 (R)-OH prostaglandin E2 as a selective prostanoid EP2-receptor agonist PubMed ID:8248550 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 46 PAGE : 371-383 (1993) |
| AUTHOR | : | Hensby, C. N., and MacDermot, J. |
| TITLE | : | Structure-activity relationships of prostanoids that activate adenylate cyclase of neuronal hybrid cells [proceedings] PubMed ID:535664 |
| JOURNAL | : | Biochem Soc Trans. |
| VOL | : | 7 PAGE : 1302-1304 (1979) |
| AUTHOR | : | Shimokawa, M., Urano, T., and Kinoshita, T. |
| TITLE | : | trans-5-prostaglandin E2 stimulates plasminogen activation by tissue-type plasminogen activator PubMed ID:1445933 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 1137 PAGE : 317-320 (1992) |
| AUTHOR | : | Oliw, E. H. |
| TITLE | : | Observations on the substrate specificity of prostaglandin hydroxylases of monkey seminal vesicles and sheep vesicular glands PubMed ID:2912490 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 1001 PAGE : 107-110 (1989) |
| AUTHOR | : | Oliw, E. H., Fahlstadius, P., and Hamberg, M. |
| TITLE | : | Isolation and biosynthesis of 20-hydroxyprostaglandins E1 and E2 in ram seminal fluid PubMed ID:3087990 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 261 PAGE : 9216-9221 (1986) |
| AUTHOR | : | Etingin, O. R., Weksler, B. B., and Hajjar, D. P. |
| TITLE | : | Cholesterol metabolism is altered by hydrolytic metabolites of prostacyclin in arterial smooth muscle cells PubMed ID:3016132 |
| JOURNAL | : | J Lipid Res. |
| VOL | : | 27 PAGE : 530-536 (1986) |
| AUTHOR | : | Sorensen, P. W., Hara, T. J., Stacey, N. E., and Goetz, F. W. |
| TITLE | : | F prostaglandins function as potent olfactory stimulants that comprise the postovulatory female sex pheromone in goldfish PubMed ID:3219377 |
| JOURNAL | : | Biol Reprod. |
| VOL | : | 39 PAGE : 1039-1050 (1988) |
| AUTHOR | : | Taylor, P. L., and Kelly, R. W. |
| TITLE | : | The occurrence of 19-hydroxy F prostaglandins in human semen PubMed ID:1175775 |
| JOURNAL | : | FEBS Lett. |
| VOL | : | 57 PAGE : 22-25 (1975) |
| AUTHOR | : | Liston, T. E., and Roberts, L. J., 2nd |
| TITLE | : | Transformation of prostaglandin D2 to 9 alpha, 11 beta-(15S)-trihydroxyprosta-(5Z,13E)-dien-1-oic acid (9 alpha, 11 beta-prostaglandin F2): a unique biologically active prostaglandin produced enzymatically in vivo in humans PubMed ID:3862115 |
| JOURNAL | : | Proc Natl Acad Sci U S A. |
| VOL | : | 82 PAGE : 6030-6034 (1985) |
| AUTHOR | : | Samuelsson, B., Goldyne, M., Granstrom, E., Hamberg, M., Hammarstrom, S., and Malmsten, C. |
| TITLE | : | Prostaglandins and thromboxanes PubMed ID:209733 |
| JOURNAL | : | Annu Rev Biochem. |
| VOL | : | 47 PAGE : 997-1029 (1978) |
| AUTHOR | : | Miller,W.L. and Sutton,M.J. |
| TITLE | : | Relative biological activity of certain prostaglandins and their enantiomers. PubMed ID:1257501 |
| JOURNAL | : | Prostaglandins |
| VOL | : | 11 PAGE : 77-84 (1976) |
| AUTHOR | : | Devereux, T. R., Fouts, J. R., and Eling, T. E. |
| TITLE | : | Metabolism of prostaglandin PG-F2 alpha by freshly isolated alveolar type II cells from lungs of adult male or pregnant rabbits PubMed ID:3473507 |
| JOURNAL | : | Prostaglandins Leukot Med. |
| VOL | : | 27 PAGE : 43-52 (1987) |
| AUTHOR | : | Jones,D.A.,Fitzpatrick,F.A. |
| TITLE | : | ..Suicide.. inactivation of thromboxane A2 synthase. Characteristics of mechanism-based inactivation with isolated enzyme and intact platelets. PubMed ID:2243085 |
| JOURNAL | : | J.Biol.Chem. |
| VOL | : | 265 PAGE : 20166-20171 (1990) |
| AUTHOR | : | Mann, N. J., Warrick, G. E., O'Dea, K., Knapp, H. R., and Sinclair, A. J. |
| TITLE | : | The effect of linoleic, arachidonic and eicosapentaenoic acid supplementation on prostacyclin production in rats PubMed ID:8170284 |
| JOURNAL | : | Lipids. |
| VOL | : | 29 PAGE : 157-162 (1994) |
| AUTHOR | : | Fitzpatrick,F.A. and Wynalda,M.A. |
| TITLE | : | Albumin-catalyzed metabolism of prostaglandin D2. Identification of products formed in vitro. PubMed ID:6578214 |
| JOURNAL | : | J.Biol.Chem. |
| VOL | : | 258 PAGE : 11713-11718 (1983) |
| AUTHOR | : | Kato,T.,Fukushima,M.,Kurozumi,S. |
| TITLE | : | Antitumor activity of D7-prostaglandin A1 and D12-prostaglandin J2 in vitro and in vivo. PubMed ID:3708585 |
| JOURNAL | : | Cancer Res. |
| VOL | : | 46 PAGE : 3538-3542 (1986) |
| AUTHOR | : | Andersen, N. H., Imamoto, S., Subramanian, N., Picker, D. H., Ladner, D. W., De, B., Tynan, S. S., Eggerman, T. L., Harker, L. A., Robertson, R. P., et al. |
| TITLE | : | Molecular basis for prostaglandin potency. III. Tests of the significance of the "hairpin conformation" in biorecognition phenomena PubMed ID:6949211 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 22 PAGE : 841-856 (1981) |
| AUTHOR | : | Kliewer, S. A., Lenhard, J. M., Willson, T. M., Patel, I., Morris, D. C., and Lehmann, J. M. |
| TITLE | : | A prostaglandin J2 metabolite binds peroxisome proliferator-activated receptor gamma and promotes adipocyte differentiation PubMed ID:8521498 |
| JOURNAL | : | Cell. |
| VOL | : | 83 PAGE : 813-819 (1995) |
| AUTHOR | : | Kiriyama, M., Ushikubi, F., Kobayashi, T., Hirata, M., Sugimoto, Y., and Narumiya, S. |
| TITLE | : | Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells PubMed ID:9313928 |
| JOURNAL | : | Br J Pharmacol. |
| VOL | : | 122 PAGE : 217-224 (1997) |
| AUTHOR | : | Alm, A., Villumsen, J., Tornquist, P., Mandahl, A., Airaksinen, J., Tuulonen, A., Marsk, A., Resul, B., and Stjernschantz, J. |
| TITLE | : | Intraocular pressure-reducing effect of PhXA41 in patients with increased eye pressure. A one-month study PubMed ID:8371917 |
| JOURNAL | : | Ophthalmology. |
| VOL | : | 100 PAGE : 1312-1316; discussion 1316 (1993) |
| AUTHOR | : | Yokotani, K., Nishihara, M., Murakami, Y., Hasegawa, T., Okuma, Y., and Osumi, Y. |
| TITLE | : | Elevation of plasma noradrenaline levels in urethane-anaesthetized rats by activation of central prostanoid EP3 receptors PubMed ID:7582489 |
| JOURNAL | : | Br J Pharmacol. |
| VOL | : | 115 PAGE : 672-676 (1995) |
| AUTHOR | : | Hughes-Fulford, M., McGrath, M. S., Hanks, D., Erickson, S., and Pulliam, L. |
| TITLE | : | Effects of dimethyl prostaglandin A1 on herpes simplex virus and human immunodeficiency virus replication PubMed ID:1332592 |
| JOURNAL | : | Antimicrob Agents Chemother. |
| VOL | : | 36 PAGE : 2253-2258 (1992) |
| AUTHOR | : | Bundy,G.L.,Morton,D.R.,Peterson,D.C.,Nishizawa,E.E.,Miller,W.L. |
| TITLE | : | Synthesis and platelet aggregation inhibiting activity of prostaglandin D analogues.PubMed ID:6854581 |
| JOURNAL | : | J. Med. Chem. |
| VOL | : | 26 PAGE : 790-799 (1983) |
| AUTHOR | : | Robert, A., Schultz, J. R., Nezamis, J. E., and Lancaster, C. |
| TITLE | : | Gastric antisecretory and antiulcer properties of PGE2, 15-methyl PGE2, and 16, 16-dimethyl PGE2. Intravenous, oral and intrajejunal administration PubMed ID:174967 |
| JOURNAL | : | Gastroenterology. |
| VOL | : | 70 PAGE : 359-370 (1976) |
| AUTHOR | : | Nizankowska, E., Sheridan, A. Q., Maile, M. H., Cross, C. J., Nizankowski, R., Prochowska, K., and Szczeklik, A. |
| TITLE | : | Bronchodilatory properties of 2-decarboxy-2-hydroxymethyl prostaglandin E1 PubMed ID:3858912 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 29 PAGE : 349-362 (1985) |
| AUTHOR | : | Hall,D.W.R. and Jaitly,K.D. |
| TITLE | : | Structure-activity relationships in a series of 11-deoxy prostaglandins.PubMed ID:948628 |
| JOURNAL | : | Prostaglandins |
| VOL | : | 11 PAGE : 573-587 (1976) |
| AUTHOR | : | Jarabak, J., and Braithwaite, S. S. |
| TITLE | : | Kinetic studies on a 15-hydroxyprostaglandin dehydrogenase from human placenta PubMed ID:187123 |
| JOURNAL | : | Arch Biochem Biophys. |
| VOL | : | 177 PAGE : 245-254 (1976) |
| AUTHOR | : | Karim, S. M., Adaikan, P. G., and Kottegoda, S. R. |
| TITLE | : | Prostaglandins and human respiratory tract smooth muscle: structure activity relationship PubMed ID:7369062 |
| JOURNAL | : | Adv Prostaglandin Thromboxane Res. |
| VOL | : | 7 PAGE : 969-980 (1980) |
| AUTHOR | : | Coleman, R. A., Smith, W. L., and Narumiya, S. |
| TITLE | : | International Union of Pharmacology classification of prostanoid receptors: properties, distribution, and structure of the receptors and their subtypes PubMed ID:7938166 |
| JOURNAL | : | Pharmacol Rev. |
| VOL | : | 46 PAGE : 205-229 (1994) |
| AUTHOR | : | Bundy, G. L., Kimball, F. A., Robert, A., Aiken, J. W., Maxey, K. M., Sebek, O. K., Nelson, N. A., Sih, J. C., Miller, W. L., and Hsi, R. S. |
| TITLE | : | Synthesis and biological activity of 9-deoxo-9-methylene and related prostaglandins PubMed ID:7386275 |
| JOURNAL | : | Adv Prostaglandin Thromboxane Res. |
| VOL | : | 6 PAGE : 355-363 (1980) |
| AUTHOR | : | Wilks, J. W. |
| TITLE | : | Pregnancy interception with a combination of prostaglandins: studies in monkeys PubMed ID:6612350 |
| JOURNAL | : | Science. |
| VOL | : | 221 PAGE : 1407-1409 (1983) |
| AUTHOR | : | Raisz, L. G., and Woodiel, F. N. |
| TITLE | : | Effect of alterations in the cyclopentane ring on bone resorptive activity of prostaglandin PubMed ID:2727307 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 37 PAGE : 229-235 (1989) |
| AUTHOR | : | Lippmann, W. |
| TITLE | : | Inhibition of gastric acid secretion and ulcer formation in the rat by orally-administered 11-deoxyprostaglandin analogues: 15-hydroxy-16,16-dimethyl-9-oxoprost-5,13-dienoic acids PubMed ID:4413891 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 7 PAGE : 231-246 (1974) |
| AUTHOR | : | Takanashi, H., and Itoh, Z. |
| TITLE | : | Gastric antisecretory activity of 15(R)-15-methylprostaglandin E2, arbaprostil, in dogs PubMed ID:1813671 |
| JOURNAL | : | Jpn J Pharmacol. |
| VOL | : | 57 PAGE : 447-451 (1991) |
| AUTHOR | : | Kimball, F. A., Kirton, K. T., Spilman, C. H., and Wyngarden, L. J. |
| TITLE | : | Prostaglandin E1 specific binding in human myometrium PubMed ID:816397 |
| JOURNAL | : | Biol Reprod. |
| VOL | : | 13 PAGE : 479-489 (1975) |
| AUTHOR | : | Johnson, M. R., Schaaf, T. K., Constantine, J. W., and Hess, H. J. |
| TITLE | : | Structure activity studies leading to a tissue-selective hypotensive prostaglandin analog, 13,14-dihydro-16-phenyl-omega-tetranor PGE2 PubMed ID:7422897 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 20 PAGE : 515-520 (1980) |
| AUTHOR | : | Miller, W. L., Weeks, J. R., Lauderdale, J. W., and Kirton, K. T. |
| TITLE | : | Biological activities of 17-phenyl-18,19,20-trinorprostaglandins PubMed ID:806103 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 9 PAGE : 9-18 (1975) |
| AUTHOR | : | Lippmann, W. |
| TITLE | : | Inhibition of gastric acid secretion in the rat by synthetic prostaglandins PubMed ID:4390134 |
| JOURNAL | : | J Pharm Pharmacol. |
| VOL | : | 21 PAGE : 335-336 (1969) |
| AUTHOR | : | Broughton, B. J., Caton, M. P., Christmas, A. J., Coffee, E. C., and Hambling, D. J. |
| TITLE | : | Uterine stimulant action of some omega-chain modified (+)-11-deoxyprostaglandins PubMed ID:7291596 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 22 PAGE : 53-64 (1981) |
| AUTHOR | : | Brookes,L.G.,Marshall,R.C. |
| TITLE | : | Proceedings: The effects of some prostaglandins on respiration in the rabbit.PubMed ID:4156762 |
| JOURNAL | : | J. Pharm. Pharmacol. |
| VOL | : | 26 PAGE : 80-81 (1974) |
| AUTHOR | : | Bundy, G. L., Peterson, D. C., Cornette, J. C., Miller, W. L., Spilman, C. H., and Wilks, J. W. |
| TITLE | : | Synthesis and biological activity of prostaglandin lactones PubMed ID:6876076 |
| JOURNAL | : | J Med Chem. |
| VOL | : | 26 PAGE : 1089-1099 (1983) |
| AUTHOR | : | Spilman, C. H., Beuving, D. C., Forbes, A. D., and Kimball, F. A. |
| TITLE | : | Effects of PGF2alpha and PGF2alpha, 1-15 lactone on the corpus luteum and on early pregnancy in the rhesus monkey PubMed ID:410075 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 14 PAGE : 477-488 (1977) |
| AUTHOR | : | Woodward,D.F.,Chan,M.F. |
| TITLE | : | Preparation of PGF-1 alcohols as ocular hypotensives. |
| JOURNAL | : | CA/USA |
| VOL | : | 38204 PAGE : 1-12 (1993) |
| AUTHOR | : | Woodward, D.F.,Tang-Liu,D.D.S.,Madhu,C. |
| TITLE | : | Prostaglandin F2a (PGF2a) 1-ethanolamide: A pharmacologically unique local hormone biosynthesized from anandamide. |
| JOURNAL | : | 11th Internatilnal Conference on Advances in Prostaglandin and Leukotrienen Research: Basic Science and New Clinical Applications. |
| VOL | : | PAGE : - (2000) |
| AUTHOR | : | Crawford, K. S., and Kaufman, P. L. |
| TITLE | : | Dose-related effects of prostaglandin F2 alpha isopropylester on intraocular pressure, refraction, and pupil diameter in monkeys PubMed ID:1878020 |
| JOURNAL | : | Invest Ophthalmol Vis Sci. |
| VOL | : | 32 PAGE : 510-519 (1991) |
| AUTHOR | : | Jones, R. L., Peesapati, V., and Wilson, N. H. |
| TITLE | : | Antagonism of the thromboxane-sensitive contractile systems of the rabbit aorta, dog saphenous vein and guinea-pig trachea PubMed ID:6286023 |
| JOURNAL | : | Br J Pharmacol. |
| VOL | : | 76 PAGE : 423-438 (1982) |
| AUTHOR | : | Wilks,J.W. |
| TITLE | : | Inhibition of the monkey corpus luteum with 15-methyl prostaglandins.PubMed ID:7465867 |
| JOURNAL | : | Prostaglandins |
| VOL | : | 20 PAGE : 793-805 (1980) |
| AUTHOR | : | Lindblom,B.,K$auml;llfelt,B.,Hahlin,M. ,Hamberger, L. |
| TITLE | : | Local prostaglandin F2a injection for termination of ectopic pregnancy.PubMed ID:2882185 |
| JOURNAL | : | Lancet |
| VOL | : | 1 PAGE : 776-777 (1987) |
| AUTHOR | : | Rosenthale, M. E., Dervinis, A., Kassarich, J., Blumenthal, A., and Gluckman, M. I. |
| TITLE | : | Bronchodilating properties of the prostaglandin f2 in the guinea pig and cat PubMed ID:4729601 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 3 PAGE : 767-772 (1973) |
| AUTHOR | : | Allegra,L.,Bianco,S. |
| TITLE | : | Prostanoids preventing induced bronchospasm. |
| JOURNAL | : | Prog. Resp. Res. |
| VOL | : | 14 PAGE : 215-223 (1980) |
| AUTHOR | : | ElAttar, T. M., and Virji, A. S. |
| TITLE | : | Inhibition of growth in oral squamous carcinoma cells by cyclopentenone prostaglandins: comparison with chemotherapeutic agents PubMed ID:9223658 |
| JOURNAL | : | Prostaglandins Leukot Essent Fatty Acids. |
| VOL | : | 56 PAGE : 461-465 (1997) |
| AUTHOR | : | Marini, S., Palamara, A. T., Garaci, E., and Santoro, M. G. |
| TITLE | : | Growth inhibition of Friend erythroleukaemia cell tumours in vivo by a synthetic analogue of prostaglandin A: an action independent of natural killer-activity PubMed ID:2328205 |
| JOURNAL | : | Br J Cancer. |
| VOL | : | 61 PAGE : 394-399 (1990) |
| AUTHOR | : | Flower, R. J., and Kingston, W. P. |
| TITLE | : | Proceedings: Prostaglandin D1 inhibits the increase in vascular permeability in rat skin produced by prostaglandin E1, E2 and D2 PubMed ID:1201383 |
| JOURNAL | : | Br J Pharmacol. |
| VOL | : | 55 PAGE : 239P-240P (1975) |
| AUTHOR | : | Monneret, G., Li, H., Vasilescu, J., Rokach, J., and Powell, W. S. |
| TITLE | : | 15-Deoxy-delta 12,14-prostaglandins D2 and J2 are potent activators of human eosinophils PubMed ID:11907120 |
| JOURNAL | : | J Immunol. |
| VOL | : | 168 PAGE : 3563-3569 (2002) |
| AUTHOR | : | Ward, C., Dransfield, I., Murray, J., Farrow, S. N., Haslett, C., and Rossi, A. G. |
| TITLE | : | Prostaglandin D2 and its metabolites induce caspase-dependent granulocyte apoptosis that is mediated via inhibition of I kappa B alpha degradation using a peroxisome proliferator-activated receptor-gamma-independent mechanism PubMed ID:12055237 |
| JOURNAL | : | J Immunol. |
| VOL | : | 168 PAGE : 6232-6243 (2002) |
| AUTHOR | : | Dumont, I., Hou, X., Hardy, P., Peri, K. G., Beauchamp, M., Najarian, T., Molotchnikoff, S., Varma, D. R., and Chemtob, S. |
| TITLE | : | Developmental regulation of endothelial nitric oxide synthase in cerebral vessels of newborn pig by prostaglandin E(2) PubMed ID:10525081 |
| JOURNAL | : | J Pharmacol Exp Ther. |
| VOL | : | 291 PAGE : 627-633 (1999) |
| AUTHOR | : | Word, R. A., Kamm, K. E., and Casey, M. L. |
| TITLE | : | Contractile effects of prostaglandins, oxytocin, and endothelin-1 in human myometrium in vitro: refractoriness of myometrial tissue of pregnant women to prostaglandins E2 and F2 alpha PubMed ID:1400867 |
| JOURNAL | : | J Clin Endocrinol Metab. |
| VOL | : | 75 PAGE : 1027-1032 (1992) |
| AUTHOR | : | Rampart, M., and Williams, T. J. |
| TITLE | : | Polymorphonuclear leukocyte-dependent plasma leakage in the rabbit skin is enhanced or inhibited by prostacyclin, depending on the route of administration PubMed ID:3524253 |
| JOURNAL | : | Am J Pathol. |
| VOL | : | 124 PAGE : 66-73 (1986) |
| AUTHOR | : | De Vries, G. W.,Guarino, P.,McLaughlin,A.Chen,J.,Andrews,S.,Woodward,D.F. |
| TITLE | : | An EP receptor with a novel pharmacological profile in the T-cell line Jurkat PubMed ID:7582550 |
| JOURNAL | : | Br. J. Pharmacol |
| VOL | : | 115 PAGE : 1231-1234 (1995) |
| AUTHOR | : | Suzuki, K., Araki, H., Komoike, Y., and Takeuchi, K. |
| TITLE | : | Permissive role of neutrophils in pathogenesis of indomethacin-induced gastric lesions in rats PubMed ID:11208431 |
| JOURNAL | : | Med Sci Monit. |
| VOL | : | 6 PAGE : 908-914 (2000) |
| AUTHOR | : | Hughes-Fulford, M. |
| TITLE | : | Cell cycle arrest by prostaglandin A1 at the G1/S phase interface with up-regulation of oncogenes in S-49 cyc- cells PubMed ID:8200906 |
| JOURNAL | : | J Cell Biochem. |
| VOL | : | 54 PAGE : 265-272 (1994) |
| AUTHOR | : | Santoro, M. G., Favalli, C., Mastino, A., Jaffe, B. M., Esteban, M., and Garaci, E. |
| TITLE | : | Antiviral activity of a synthetic analog of prostaglandin A in mice infected with influenza A virus PubMed ID:3355375 |
| JOURNAL | : | Arch Virol. |
| VOL | : | 99 PAGE : 89-100 (1988) |
| AUTHOR | : | Spannhake, E. W., Levin, J. L., Hyman, A. L., and Kadowitz, P. J. |
| TITLE | : | In vivo metabolism of dihomo-gamma-linolenic acid to bronchoactive products in the canine lung PubMed ID:6405393 |
| JOURNAL | : | Prostaglandins Leukot Med. |
| VOL | : | 10 PAGE : 123-132 (1983) |
| AUTHOR | : | Soderstrom, M., Wigren, J., Surapureddi, S., Glass, C. K., and Hammarstrom, S. |
| TITLE | : | Novel prostaglandin D(2)-derived activators of peroxisome proliferator-activated receptor-gamma are formed in macrophage cell cultures PubMed ID:12573447 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 1631 PAGE : 35-41 (2003) |
| AUTHOR | : | De Vries, G.W., Guarino, P., McLaughlin, A., Chen, J., Andrews, S., Woodward, D.F., |
| TITLE | : | An EP receptor with a novel pharmacological profile in the T-cell line Jurkat . PubMed ID:7582550 |
| JOURNAL | : | Br J Pharmacol. |
| VOL | : | 115 PAGE : 1231-1234 (1995) |
| AUTHOR | : | Besse, A., Trimoreau, F., Faucher, J. L., Praloran, V., and Denizot, Y. |
| TITLE | : | Prostaglandin E2 regulates macrophage colony stimulating factor secretion by human bone marrow stromal cells PubMed ID:10395955 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 1450 PAGE : 444-451 (1999) |
| AUTHOR | : | Noguchi, K., Shitashige, M., Endo, H., Kondo, H., and Ishikawa, I. |
| TITLE | : | Binary regulation of interleukin (IL)-6 production by EP1 and EP2/EP4 subtypes of PGE2 receptors in IL-1beta-stimulated human gingival fibroblasts PubMed ID:11842936 |
| JOURNAL | : | J Periodontal Res. |
| VOL | : | 37 PAGE : 29-36 (2002) |
| AUTHOR | : | Halm, D. R., and Halm, S. T. |
| TITLE | : | Prostanoids stimulate K secretion and Cl secretion in guinea pig distal colon via distinct pathways PubMed ID:11557519 |
| JOURNAL | : | Am J Physiol Gastrointest Liver Physiol. |
| VOL | : | 281 PAGE : G984-996 (2001) |
| AUTHOR | : | Caillon, P., and Saffar, J. L. |
| TITLE | : | Improvement of gingival and alveolar bone status in periodontitis-affected hamsters treated with 15-methyl prostaglandin E1 PubMed ID:8158502 |
| JOURNAL | : | J Periodontal Res. |
| VOL | : | 29 PAGE : 138-145 (1994) |
| AUTHOR | : | Ohia, S. E., and Jumblatt, J. E. |
| TITLE | : | Prejunctional inhibitory effects of prostanoids on sympathetic neurotransmission in the rabbit iris-ciliary body PubMed ID:2170622 |
| JOURNAL | : | J Pharmacol Exp Ther. |
| VOL | : | 255 PAGE : 11-16 (1990) |
| AUTHOR | : | Bito, L. Z. |
| TITLE | : | Comparison of the ocular hypotensive efficacy of eicosanoids and related compounds PubMed ID:6370708 |
| JOURNAL | : | Exp Eye Res. |
| VOL | : | 38 PAGE : 181-194 (1984) |
| AUTHOR | : | Morrow, J. D., Minton, T. A., and Roberts, L. J., 2nd |
| TITLE | : | The F2-isoprostane, 8-epi-prostaglandin F2 alpha, a potent agonist of the vascular thromboxane/endoperoxide receptor, is a platelet thromboxane/endoperoxide receptor antagonist PubMed ID:1438879 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 44 PAGE : 155-163 (1992) |
| AUTHOR | : | Morrow, J. D., Harris, T. M., and Roberts, L. J., 2nd |
| TITLE | : | Noncyclooxygenase oxidative formation of a series of novel prostaglandins: analytical ramifications for measurement of eicosanoids PubMed ID:2321745 |
| JOURNAL | : | Anal Biochem. |
| VOL | : | 184 PAGE : 1-10 (1990) |
| AUTHOR | : | Cranshaw, J. H., Evans, T. W., and Mitchell, J. A. |
| TITLE | : | Characterization of the effects of isoprostanes on platelet aggregation in human whole blood PubMed ID:11309241 |
| JOURNAL | : | Br J Pharmacol. |
| VOL | : | 132 PAGE : 1699-1706 (2001) |
| AUTHOR | : | Cracowski, J. L., Camus, L., Durand, T., Devillier, P., Guy, A., Hardy, G., Stanke-Labesque, F., Rossi, J. C., and Bessard, G. |
| TITLE | : | Response of rat thoracic aorta to F(2)-isoprostane metabolites PubMed ID:11862119 |
| JOURNAL | : | J Cardiovasc Pharmacol. |
| VOL | : | 39 PAGE : 396-403 (2002) |
| AUTHOR | : | Wilks, J. W. |
| TITLE | : | Inhibition of the monkey corpus luteum with 15-methyl prostaglandins. PubMed ID:7465867 |
| JOURNAL | : | Prostaglandins |
| VOL | : | 20 PAGE : 793-805 (1980) |
| AUTHOR | : | Carlan, S. J., Gushwa, J. P., O'Brien, W. F., and Vu, T. |
| TITLE | : | Effect of intramuscular 15-methyl prostaglandin F2 alpha after second-trimester delivery PubMed ID:8990427 |
| JOURNAL | : | Obstet Gynecol. |
| VOL | : | 89 PAGE : 5-9 (1997) |
| AUTHOR | : | Lindblom, B., Kallfelt, B., Hahlin, M. |
| TITLE | : | Local prostaglandin F2a injection for termination of ectopic pregnancy. PubMed ID:2882185 |
| JOURNAL | : | Lancet |
| VOL | : | PAGE : 776-777 (1987) |
| AUTHOR | : | Adaikan, P. G., Prasad, R. N., Kottegoda, S. R., and Ratnam, S. S. |
| TITLE | : | Effect of indomethacin on the injection-abortion interval of 15(S) 15 methyl PGF2 alpha-induced mid-trimester abortions--a randomized study PubMed ID:3475725 |
| JOURNAL | : | Prostaglandins Leukot Med. |
| VOL | : | 27 PAGE : 161-167 (1987) |
| AUTHOR | : | Woodward, D. F., Krauss, A. H., Chen, J., Lai, R. K., Spada, C. S., Burk, R. M., Andrews, S. W., Shi, L., Liang, Y., Kedzie, K. M., et al. |
| TITLE | : | The pharmacology of bimatoprost (Lumigan) PubMed ID:11434936 |
| JOURNAL | : | Surv Ophthalmol. |
| VOL | : | 45 Suppl 4 PAGE : S337-345 (2001) |
| AUTHOR | : | Resul, B., Stjernschantz, J., Selen, G., and Bito, L. |
| TITLE | : | Structure-activity relationships and receptor profiles of some ocular hypotensive prostanoids PubMed ID:9154276 |
| JOURNAL | : | Surv Ophthalmol. |
| VOL | : | 41 Suppl 2 PAGE : S47-52 (1997) |
| AUTHOR | : | Oliveira, L., Stallwood, N. A., and Crankshaw, D. J. |
| TITLE | : | Effects of some isoprostanes on the human umbilical artery in vitro PubMed ID:10711349 |
| JOURNAL | : | Br J Pharmacol. |
| VOL | : | 129 PAGE : 509-514 (2000) |
| AUTHOR | : | Pratico, D., Smyth, E. M., Violi, F., and FitzGerald, G. A. |
| TITLE | : | Local amplification of platelet function by 8-Epi prostaglandin F2alpha is not mediated by thromboxane receptor isoforms PubMed ID:8663015 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 271 PAGE : 14916-14924 (1996) |
| AUTHOR | : | Hamberg, M., Svensson, J., Wakabayashi, T. |
| TITLE | : | Isolation and structure of two prostaglandin endoperoxides that cause platelet aggregation. PubMed ID:4521806 |
| JOURNAL | : | Proc. Natl. Acad. Sci. USA |
| VOL | : | 71 PAGE : 345-349 (1974) |
| AUTHOR | : | Jones, D. A., Fitzpatrick, F. A. |
| TITLE | : | ""Suicide"" inactivation of thromboxane A2 synthase. Characteristics of mechanism-based inactivation with isolated enzyme and intact platelets. PubMed ID:2243085 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 265 PAGE : 20166-20171 (1990) |
| AUTHOR | : | Leighton, J. K., DeBrunner-Vossbrinck, B. A., and Kemper, B. |
| TITLE | : | Isolation and sequence analysis of three cloned cDNAs for rabbit liver proteins that are related to rabbit cytochrome P-450 (form 2), the major phenobarbital-inducible form PubMed ID:6546520 |
| JOURNAL | : | Biochemistry. |
| VOL | : | 23 PAGE : 204-210 (1984) |
| AUTHOR | : | Whittle, B. J., and Moncada, S. |
| TITLE | : | Prostacyclin and its analogues for the therapy of thromboembolic disorders PubMed ID:6364707 |
| JOURNAL | : | Adv Exp Med Biol. |
| VOL | : | 164 PAGE : 193-209 (1984) |
| AUTHOR | : | Whittle, B. J., Moncada, S., Whiting, F., and Vane, J. R. |
| TITLE | : | Carbacyclin--a potent stable prostacyclin analogue for the inhibition of platelet aggregation PubMed ID:6992234 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 19 PAGE : 605-627 (1980) |
| AUTHOR | : | Falcone, R. C., and Aharony, D. |
| TITLE | : | Modulation of ligand binding to leukotriene B4 receptors on guinea pig lung membranes by sulfhydryl modifying reagents PubMed ID:2173748 |
| JOURNAL | : | J Pharmacol Exp Ther. |
| VOL | : | 255 PAGE : 565-571 (1990) |
| AUTHOR | : | Shimazaki, T., Kobayashi, Y., Sato, F., Iwama, T., and Shikada, K. |
| TITLE | : | Some newly synthesized leukotriene B4 analogs inhibit LTB4-induced lysozyme release from rat polymorphonuclear leukocytes PubMed ID:2160678 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 39 PAGE : 459-467 (1990) |
| AUTHOR | : | Showell, H. J., Otterness, I. G., Marfat, A., and Corey, E. J. |
| TITLE | : | Inhibition of leukotriene B4-induced neutrophil degranulation by leukotriene B4-dimethylamide PubMed ID:6288032 |
| JOURNAL | : | Biochem Biophys Res Commun. |
| VOL | : | 106 PAGE : 741-747 (1982) |
| AUTHOR | : | McHugh, D., McMaster, S., Ross, R. |
| TITLE | : | Pharmacological characterisation of LTB4 ethanolamide: Interaction with leukotriene and Vanilloid receptors. |
| JOURNAL | : | 13th Annual ICRS Cannabinoid SYmposium |
| VOL | : | PAGE : 121- (2003) |
| AUTHOR | : | Fretland, D. J., Widomski, D. L., Anglin, C. P., Walsh, R. E., Levin, S., and Gaginella, T. S. |
| TITLE | : | 6-trans-leukotriene B4 is a neutrophil chemotaxin in the guinea pig dermis PubMed ID:1847716 |
| JOURNAL | : | J Leukoc Biol. |
| VOL | : | 49 PAGE : 283-288 (1991) |
| AUTHOR | : | Borgeat, P., and Samuelsson, B. |
| TITLE | : | Metabolism of arachidonic acid in polymorphonuclear leukocytes. Structural analysis of novel hydroxylated compounds PubMed ID:468794 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 254 PAGE : 7865-7869 (1979) |
| AUTHOR | : | Borgeat. P, Samuelsson, B. |
| TITLE | : | Arachidonic acid metabolism in polymorphonuclear leukotcytes: Unstable intermediate in formation of dihydroxy acids. PubMed ID:290996 |
| JOURNAL | : | Proc. Natl. Acad. Sci. USA |
| VOL | : | 76 PAGE : 3213-3217 (1979) |
| AUTHOR | : | Lee, T. H., Menica-Huerta, J. M., Shih, C., Corey, E. J., Lewis, R. A., and Austen, K. F. |
| TITLE | : | Characterization and biologic properties of 5,12-dihydroxy derivatives of eicosapentaenoic acid, including leukotriene B5 and the double lipoxygenase product PubMed ID:6321468 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 259 PAGE : 2383-2389 (1984) |
| AUTHOR | : | Yokomizo, T., Kato, K., Hagiya, H., Izumi, T., and Shimizu, T. |
| TITLE | : | Hydroxyeicosanoids bind to and activate the low affinity leukotriene B4 receptor, BLT2 PubMed ID:11278893 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 276 PAGE : 12454-12459 (2001) |
| AUTHOR | : | Hansson, G., Lindgren, J. A., Dahlen, S. E., Hedqvist, P., and Samuelsson, B. |
| TITLE | : | Identification and biological activity of novel omega-oxidized metabolites of leukotriene B4 from human leukocytes PubMed ID:6793392 |
| JOURNAL | : | FEBS Lett. |
| VOL | : | 130 PAGE : 107-112 (1981) |
| AUTHOR | : | Feinmark, S. J., Lindgren, J. A., Claesson, H. E., Malmsten, C., and Samuelsson, B. |
| TITLE | : | Stimulation of human leukocyte degranulation by leukotriene B4 and its omega-oxidized metabolites PubMed ID:6274698 |
| JOURNAL | : | FEBS Lett. |
| VOL | : | 136 PAGE : 141-144 (1981) |
| AUTHOR | : | Wang, S., Gustafson, E., Pang, L., Qiao, X., Behan, J., Maguire, M., Bayne, M., and Laz, T. |
| TITLE | : | A novel hepatointestinal leukotriene B4 receptor. Cloning and functional characterization PubMed ID:11006272 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 275 PAGE : 40686-40694 (2000) |
| AUTHOR | : | Tanaka, Y., Klauck, T. M., Jubiz, W., Taguchi, T., Hanzawa, Y., Igarashi, A., Inazawa, K., Kobayashi, Y., and Briggs, R. G. |
| TITLE | : | Biosynthesis of 20,20,20-trifluoroleukotriene B4 from 20,20,20-trifluoroarachidonic acid: a metabolically stable analog of leukotriene B4 and its application to a study of stimulation of leukotriene B4 synthesis by immunoglobulin G1,2 PubMed ID:2835934 |
| JOURNAL | : | Arch Biochem Biophys. |
| VOL | : | 263 PAGE : 178-190 (1988) |
| AUTHOR | : | Tsai, B. S., Keith, R. H., Villani-Price, D., Haack, R. A., Bauer, R. F., Leonard, R., Abe, Y., and Nicolaou, K. C. |
| TITLE | : | Differential effects of 20-trifluoromethyl leukotriene B4 on human neutrophil functions PubMed ID:2543037 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 37 PAGE : 287-302 (1989) |
| AUTHOR | : | Nilsson, E., Gyllenhammar, H., Lerner, R., Palmblad, J., and Ringertz, B. |
| TITLE | : | The effect of 20-trifluoromethyl leukotriene B4 on neutrophil functional responses PubMed ID:1850167 |
| JOURNAL | : | Scand J Immunol. |
| VOL | : | 33 PAGE : 357-363 (1991) |
| AUTHOR | : | Jorg, A., Henderson, W. R., Murphy, R. C., and Klebanoff, S. J. |
| TITLE | : | Leukotriene generation by eosinophils PubMed ID:6120203 |
| JOURNAL | : | J Exp Med. |
| VOL | : | 155 PAGE : 390-402 (1982) |
| AUTHOR | : | Macchia, L., Hamberg, M., Kumlin, M., Butterfield, J. H., and Haeggstrom, J. Z. |
| TITLE | : | Arachidonic acid metabolism in the human mast cell line HMC-1: 5-lipoxygenase gene expression and biosynthesis of thromboxane PubMed ID:7599181 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 1257 PAGE : 58-74 (1995) |
| AUTHOR | : | Dahlen, S. E., Hedqvist, P., and Hammarstrom, S. |
| TITLE | : | Contractile activities of several cysteine-containing leukotrienes in the guinea-pig lung strip PubMed ID:6297932 |
| JOURNAL | : | Eur J Pharmacol. |
| VOL | : | 86 PAGE : 207-215 (1982) |
| AUTHOR | : | Sala, A., Civelli, M., Oliva, D., Spur, B., Crea, A. E., Folco, G. C., and Nicosia, S. |
| TITLE | : | Contractile and binding activities of structural analogues of LTC4 in the longitudinal muscle of guinea-pig ileum PubMed ID:2206559 |
| JOURNAL | : | Eicosanoids. |
| VOL | : | 3 PAGE : 105-110 (1990) |
| AUTHOR | : | Baker, S. R., Boot, J. R., Jamieson, W. B., Osborne, D. J., and Sweatman, W. J. |
| TITLE | : | The comparative in vitro pharmacology of leukotriene D4 and its isomers PubMed ID:6895848 |
| JOURNAL | : | Biochem Biophys Res Commun. |
| VOL | : | 103 PAGE : 1258-1264 (1981) |
| AUTHOR | : | Tsai, B. S., Bernstein, P., Macia, R. A., Conaty, J., and Krell, R. D. |
| TITLE | : | Comparative potency and pharmacology of isomers of leukotriene D4 on guinea-pig trachea: requirement for a 5(S)6(R) configuration PubMed ID:6896758 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 23 PAGE : 489-506 (1982) |
| AUTHOR | : | Hammarstrom, S., Orning, L., Bernstrom, K. |
| TITLE | : | Meteabolism of leukotrienes. PubMed ID:3001504 |
| JOURNAL | : | Mol. Cell. Biochem. |
| VOL | : | 69 PAGE : 7-16 (1985) |
| AUTHOR | : | Kato, T., Fukushima, M., Kurozumi, S. |
| TITLE | : | Antitumor activity of d7-prostasglandin A1 and d12-prostaglandin J2 in vitro and in vivo. PubMed ID:3708585 |
| JOURNAL | : | Cancer Res. |
| VOL | : | 46 PAGE : 3538-3542 (1986) |
| AUTHOR | : | Fukushima, M. |
| TITLE | : | Prostaglandin J2 - antitumor and anti-viral acitivities and the mechanisms involved. PubMed ID:2073399 |
| JOURNAL | : | Eicosanoids |
| VOL | : | 3 PAGE : 189-199 (1990) |
| AUTHOR | : | Giles, H., Leff, P., Bolofo, M. L., Kelly, M. G., and Robertson, A. D. |
| TITLE | : | The classification of prostaglandin DP-receptors in platelets and vasculature using BW A868C, a novel, selective and potent competitive antagonist PubMed ID:2924081 |
| JOURNAL | : | Br J Pharmacol. |
| VOL | : | 96 PAGE : 291-300 (1989) |
| AUTHOR | : | Torisawa, Y., Yamaguchi, T., Sakata, S. |
| TITLE | : | Synthesis of 11-deoxy-11-methylene-prostaglandin D2 and its derivatives. |
| JOURNAL | : | Chem. Pharm. Bull. |
| VOL | : | 3310 PAGE : 4625-4628 (1985) |
| AUTHOR | : | Hirai, H., Tanaka, K., Yoshie, O., Ogawa, K., Kenmotsu, K., Takamori, Y., Ichimasa, M., Sugamura, K., Nakamura, M., Takano, S., et al. |
| TITLE | : | Prostaglandin D2 selectively induces chemotaxis in T helper type 2 cells, eosinophils, and basophils via seven-transmembrane receptor CRTH2 PubMed ID:11208866 |
| JOURNAL | : | J Exp Med. |
| VOL | : | 193 PAGE : 255-261 (2001) |
| AUTHOR | : | Monneret, G., Cossette, C., Gravel, S., Rokach, J., and Powell, W. S. |
| TITLE | : | 15R-methyl-prostaglandin D2 is a potent and selective CRTH2/DP2 receptor agonist in human eosinophils PubMed ID:12490611 |
| JOURNAL | : | J Pharmacol Exp Ther. |
| VOL | : | 304 PAGE : 349-355 (2003) |
| AUTHOR | : | Ramwell, P. W., Shaw, J. E., Corey, E. J., and Andersen, N. |
| TITLE | : | Biological activity of synthetic prostaglandins PubMed ID:5813101 |
| JOURNAL | : | Nature. |
| VOL | : | 221 PAGE : 1251-1253 (1969) |
| AUTHOR | : | Taylor, P. L. |
| TITLE | : | The 8-isoprostaglandins: evidence for eight compounds in human semen PubMed ID:441435 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 17 PAGE : 259-267 (1979) |
| AUTHOR | : | Nakano, J., and Kessinger, J. M. |
| TITLE | : | Effects of 8-isoprostaglandin E1 on the systemic and pulmonary circulations in dogs PubMed ID:5440421 |
| JOURNAL | : | Proc Soc Exp Biol Med. |
| VOL | : | 133 PAGE : 1314-1317 (1970) |
| AUTHOR | : | Dennis, E. A. |
| TITLE | : | Diversity of group types, regulation, and function of phospholipase A2 PubMed ID:8175726 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 269 PAGE : 13057-13060 (1994) |
| AUTHOR | : | Miller, W. L., Sutton, M. J. |
| TITLE | : | Relative biological activity of certain prostaglandins and their enantiomers. PubMed ID:1257501 |
| JOURNAL | : | Prostaglandins |
| VOL | : | 11 PAGE : 77-84 (1976) |
| AUTHOR | : | Longmire, A. W., Roberts, L. J., and Morrow, J. D. |
| TITLE | : | Actions of the E2-isoprostane, 8-ISO-PGE2, on the platelet thromboxane/endoperoxide receptor in humans and rats: additional evidence for the existence of a unique isoprostane receptor PubMed ID:7878192 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 48 PAGE : 247-256 (1994) |
| AUTHOR | : | Pace-Asciak, C . R., |
| TITLE | : | Isolation, structure, and biosynthesis of 6-ketoprostaglandin F1a in the rat stomach. PubMed ID:1254872 |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 98 PAGE : 2348-2349 (1976) |
| AUTHOR | : | Brookes, L. G., Marshall, R. C. |
| TITLE | : | The effects of some prostagloandins on respiration in the rabbit. PubMed ID:4156762 |
| JOURNAL | : | J. Pharm. Pharmacol. |
| VOL | : | 26 PAGE : 80-81 (1974) |
| AUTHOR | : | Hall, D. W. R., Jaitly, K. D. |
| TITLE | : | Structure-activity relationships in a series of 11-deoxy prostaglandins. PubMed ID:948628 |
| JOURNAL | : | Prostaglandins |
| VOL | : | 11 PAGE : 573-587 (1976) |
| AUTHOR | : | Woodward, D. F., Can, M. F. |
| TITLE | : | Preparation of PGF-1 alcohols as ocular hypotensives. |
| JOURNAL | : | CA/USA |
| VOL | : | 5 PAGE : 238-961 (1993) |
| AUTHOR | : | Woodward, D. F., Krauss, A. H., Chen, J., Gil, D. W., Kedzie, K. M., Protzman, C. E., Shi, L., Chen, R., Krauss, H. A., Bogardus, A., et al. |
| TITLE | : | Replacement of the carboxylic acid group of prostaglandin f(2alpha) with a hydroxyl or methoxy substituent provides biologically unique compounds PubMed ID:10952685 |
| JOURNAL | : | Br J Pharmacol. |
| VOL | : | 130 PAGE : 1933-1943 (2000) |
| AUTHOR | : | Maddox, Y. T., Ramwell, P. W., Shiner, C. S., and Corey, E. J. |
| TITLE | : | Amide and i-amino derivatives of F prostaglandins as prostaglandin antagonists PubMed ID:661964 |
| JOURNAL | : | Nature. |
| VOL | : | 273 PAGE : 549-552 (1978) |
| AUTHOR | : | Yokomizo, T.,Izumi, T., Takahashi, T., Kasama, T., Kobayashi, Y., Sato, F., Taketani, Y., Shimizu, T. |
| TITLE | : | Enzymatic inactivation of leukotriene B4 by a novel enzyme found in the porcine kidney. Purification and properties of leukotriene B4 12- hydroxydehydrogenase. PubMed ID:8394361 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 268 PAGE : 18128-18135 (1993) |
| AUTHOR | : | Yokomizo,T., Ogawa,Y., Uozumi,N., Kume,K., Izumi,T. , Shimizu,T. |
| TITLE | : | cDNA cloning, expression, and mutagenesis study of leukotriene B4 12-hydroxydehydrogenase. PubMed ID:8576264 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 271 PAGE : 2844-2850 (1996) |
| AUTHOR | : | Ensor, C. M., Zhang, H., and Tai, H. H. |
| TITLE | : | Purification, cDNA cloning and expression of 15-oxoprostaglandin 13-reductase from pig lung PubMed ID:9461497 |
| JOURNAL | : | Biochem J. |
| VOL | : | 330 (Pt 1) PAGE : 103-108 (1998) |
| AUTHOR | : | Primiano, T., Gastel, J. A., Kensler, T. W., and Sutter, T. R. |
| TITLE | : | Isolation of cDNAs representing dithiolethione-responsive genes PubMed ID:8968041 |
| JOURNAL | : | Carcinogenesis. |
| VOL | : | 17 PAGE : 2297-2303 (1996) |
| AUTHOR | : | Sheskin, T., Hanus, L., Slager, J., Vogel, Z., and Mechoulam, R. |
| TITLE | : | Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor PubMed ID:9057852 |
| JOURNAL | : | J Med Chem. |
| VOL | : | 40 PAGE : 659-667 (1997) |
| AUTHOR | : | Matsuda, L. A., Lolait, S. J., Brownstein, M. J., Young, A. C., and Bonner, T. I. |
| TITLE | : | Structure of a cannabinoid receptor and functional expression of the cloned cDNA PubMed ID:2165569 |
| JOURNAL | : | Nature. |
| VOL | : | 346 PAGE : 561-564 (1990) |
| AUTHOR | : | Munro, S., Thomas, K. L., and Abu-Shaar, M. |
| TITLE | : | Molecular characterization of a peripheral receptor for cannabinoids PubMed ID:7689702 |
| JOURNAL | : | Nature. |
| VOL | : | 365 PAGE : 61-65 (1993) |
| AUTHOR | : | Shire, D., Carillon, C., Kaghad, M., Calandra, B., Rinaldi-Carmona, M., Le Fur, G., Caput, D., and Ferrara, P. |
| TITLE | : | An amino-terminal variant of the central cannabinoid receptor resulting from alternative splicing PubMed ID:7876112 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 270 PAGE : 3726-3731 (1995) |
| AUTHOR | : | Sugiura, T., Kondo, S., Sukagawa, A., Tonegawa, T., Nakane, S., Yamashita, A., Ishima, Y., and Waku, K. |
| TITLE | : | Transacylase-mediated and phosphodiesterase-mediated synthesis of N-arachidonoylethanolamine, an endogenous cannabinoid-receptor ligand, in rat brain microsomes. Comparison with synthesis from free arachidonic acid and ethanolamine PubMed ID:8797835 |
| JOURNAL | : | Eur J Biochem. |
| VOL | : | 240 PAGE : 53-62 (1996) |
| AUTHOR | : | Devane, W. A., Hanus, L., Breuer, A., Pertwee, R. G., Stevenson, L. A., Griffin, G., Gibson, D., Mandelbaum, A., Etinger, A., and Mechoulam, R. |
| TITLE | : | Isolation and structure of a brain constituent that binds to the cannabinoid receptor PubMed ID:1470919 |
| JOURNAL | : | Science. |
| VOL | : | 258 PAGE : 1946-1949 (1992) |
| AUTHOR | : | Desarnaud, F., Cadas, H., and Piomelli, D. |
| TITLE | : | Anandamide amidohydrolase activity in rat brain microsomes. Identification and partial characterization PubMed ID:7890734 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 270 PAGE : 6030-6035 (1995) |
| AUTHOR | : | Sugiura, T., Kondo, S., Sukagawa, A., Tonegawa, T., Nakane, S., Yamashita, A., and Waku, K. |
| TITLE | : | Enzymatic synthesis of anandamide, an endogenous cannabinoid receptor ligand, through N-acylphosphatidylethanolamine pathway in testis: involvement of Ca(2+)-dependent transacylase and phosphodiesterase activities PubMed ID:8573114 |
| JOURNAL | : | Biochem Biophys Res Commun. |
| VOL | : | 218 PAGE : 113-117 (1996) |
| AUTHOR | : | Seltzman, H. H., Fleming, D. N., Thomas, B. F., Gilliam, A. F., McCallion, D. S., Pertwee, R. G., Compton, D. R., and Martin, B. R. |
| TITLE | : | Synthesis and pharmacological comparison of dimethylheptyl and pentyl analogs of anandamide PubMed ID:9357529 |
| JOURNAL | : | J Med Chem. |
| VOL | : | 40 PAGE : 3626-3634 (1997) |
| AUTHOR | : | Adams, I. B., Ryan, W., Singer, M., Thomas, B. F., Compton, D. R., Razdan, R. K., and Martin, B. R. |
| TITLE | : | Evaluation of cannabinoid receptor binding and in vivo activities for anandamide analogs PubMed ID:7791088 |
| JOURNAL | : | J Pharmacol Exp Ther. |
| VOL | : | 273 PAGE : 1172-1181 (1995) |
| AUTHOR | : | Ryan, W. J., Banner, W. K., Wiley, J. L., Martin, B. R., and Razdan, R. K. |
| TITLE | : | Potent anandamide analogs: the effect of changing the length and branching of the end pentyl chain PubMed ID:9357528 |
| JOURNAL | : | J Med Chem. |
| VOL | : | 40 PAGE : 3617-3625 (1997) |
| AUTHOR | : | Abadji, V., Lin, S., Taha, G., Griffin, G., Stevenson, L. A., Pertwee, R. G., and Makriyannis, A. |
| TITLE | : | (R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability PubMed ID:8021930 |
| JOURNAL | : | J Med Chem. |
| VOL | : | 37 PAGE : 1889-1893 (1994) |
| AUTHOR | : | T. Sugiura, S. Kondo, A. Sukagawa, S. Nakane, A. Shinoda, K. Itoh, A. Yamashita and K. Waku |
| TITLE | : | 2-Arachidonoylglycerol: A Possible Endogenous Cannabinoid Receptor Ligand in Brain. PubMed ID:7575630 |
| JOURNAL | : | Biochem. biophys. Res. Commun. |
| VOL | : | 215 PAGE : 89-97 (1995) |
| AUTHOR | : | T. Sugiura, T. Kodaka, S. Nakane, T. Miyashita, S. Kondo, Y. Suhara, H. Takayama, K. Waku, C. Seki, N. Baba et al. |
| TITLE | : | Evidencethat the Cannabinoid CBl Receptor is a 2-Arachidonoylglycerol Receptor: Structure-Activity Relationship of 2-Arachidonoylglycerol, Ether-linked Analogues and Related Compounds. PubMed ID:9915812 |
| JOURNAL | : | J. Biol. Chem. |
| VOL | : | 274 PAGE : 2794-2801 (1999) |
| AUTHOR | : | Mechoulam, R., Ben-Shabat, S., Hanus, L., Ligumsky, M., Kaminski, N. E., Schatz, A. R., Gopher, A., Almog, S., Martin, B. R., Compton, D. R., et al. |
| TITLE | : | Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors PubMed ID:7605349 |
| JOURNAL | : | Biochem Pharmacol. |
| VOL | : | 50 PAGE : 83-90 (1995) |
| AUTHOR | : | Di Marzo, V., Fontana, A., Cadas, H., Schinelli, S., Cimino, G., Schwartz, J. C., and Piomelli, D. |
| TITLE | : | Formation and inactivation of endogenous cannabinoid anandamide in central neurons PubMed ID:7990962 |
| JOURNAL | : | Nature. |
| VOL | : | 372 PAGE : 686-691 (1994) |
| AUTHOR | : | Ueda N, Yamanaka K, Terasawa Y, Yamamoto S |
| TITLE | : | An acid amidase hydrolyzing anandamide as an endogenous ligand for cannabinoid receptors. PubMed ID:11700558 |
| JOURNAL | : | FEBS Lett. |
| VOL | : | 454 PAGE : 267-270 (1999) |
| AUTHOR | : | Rodriguez de Fonseca F, Navarro M, Gomez R, Escuredo L, Nava F, Fu J, Murillo-Rodriguez E, Giuffrida A, LoVerme J, Gaetani S, Kathuria S, Gall C, Piomelli D |
| TITLE | : | An anorexic lipid mediator regulated by feeding. PubMed ID:11700558 |
| JOURNAL | : | Nature |
| VOL | : | 414 PAGE : 209-212 (2001) |
| AUTHOR | : | Giuffrida, A., Rodriguez de Fonseca, F., and Piomelli, D. |
| TITLE | : | Quantification of bioactive acylethanolamides in rat plasma by electrospray mass spectrometry PubMed ID:10805525 |
| JOURNAL | : | Anal Biochem. |
| VOL | : | 280 PAGE : 87-93 (2000) |
| AUTHOR | : | Kikuchi,H., Tsukitani,Y., Iguchi,K., and Yamada,Y. |
| TITLE | : | Clavulones, New Type of Prostanoids from the Stolonifer Clavularia viridis Quoy and Gaimard. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 23 PAGE : 5171-5174 (1982) |
| AUTHOR | : | Kobayashi,M., Yasuzawa,T., Yoshihara,M., Akutsu,H., Kyogoku,Y., and Kitagawa,I. |
| TITLE | : | Four New Prostanoids: Claviridenone-a, -b, -c, and -d from the Okinawan Soft Coral Clavularia viridis. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 23 PAGE : 5331-5334 (1982) |
| AUTHOR | : | Kikuchi,H., Tsukitani,Y., Iguchi,K., and Yamada,Y. |
| TITLE | : | Absolute Stereochemistry of New Prostanoids Clavulone I, II, and III, from Clavularia viridis Quoy and Gaimard. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 24 PAGE : 1549-1552 (1983) |
| AUTHOR | : | Corey,E.J. |
| TITLE | : | A Proposal for the Biosynthesis of the Clavulones, a New Family of Eicosanoids. |
| JOURNAL | : | Experientia |
| VOL | : | 39 PAGE : 1084-1085 (1983) |
| AUTHOR | : | Corey,E.J., Schmidt,G., and Shimoji,K. |
| TITLE | : | Formation of a, b-epoxy Systems from b-epoxy Carbon Free Radicals. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 24 PAGE : 3169-3170 (1983) |
| AUTHOR | : | Kobayashi,M., Yasuzawa,T., Yoshihara,M., Son,B.W., Kyogoku,Y., and Kitagawa,I. |
| TITLE | : | Absolute Stereostructures of Claviridenone-a,b,c, and -d Four Prostanoids from the Okinawan Soft Coral Clavuraria viridis. |
| JOURNAL | : | Chem.Pharm.Bull. |
| VOL | : | 31 PAGE : 1440-1443 (1983) |
| AUTHOR | : | Corey,E.J., and Mehrotra,M.M. |
| TITLE | : | Total Synthesis of ()-Clavulones. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 106 PAGE : 3384-3384 (1984) |
| AUTHOR | : | Nagaoka,H., Miyakoshi,T., and Yamada,Y. |
| TITLE | : | Total Synthesis of Marine Prostanoids: Clavulones. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 25 PAGE : 3621-3624 (1984) |
| AUTHOR | : | Honda, A., Yamamoto, Y., Mori, Y., Yamada, Y., and Kikuchi, H. |
| TITLE | : | Antileukemic effect of coral-prostanoids clavulones from the stolonifer Clavularia viridis on human myeloid leukemia (HL-60) cells PubMed ID:2862864 |
| JOURNAL | : | Biochem Biophys Res Commun. |
| VOL | : | 130 PAGE : 515-523 (1985) |
| AUTHOR | : | Hashimoto,S., Arai,Y., and Hamanaka,N. |
| TITLE | : | Synthesis of Clavulones (Claviridenones). |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 26 PAGE : 2679-2682 (1985) |
| AUTHOR | : | Shibasaki,M., and Ogawa,Y. |
| TITLE | : | Total Synthesis of Clavulones. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 26 PAGE : 3841-3844 (1985) |
| AUTHOR | : | Corey,E.J., Lansbury,Jr.,P.T., and Yamada,Y. |
| TITLE | : | Identification of a New Eicosanoid from in vitro Biosynthetic Experiments with Clavularia viridis. Implications for the biosynthesis of Clavulones. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 26 PAGE : 4171-4174 (1985) |
| AUTHOR | : | Corey,E.J., D'Alarcao,M., Matsuda,S., Lansbury,P.T.Jr., and Yamada,Y. |
| TITLE | : | Intermediacy of 8-(R)-HPETE in the Conversion of Arachidonic Acid to Pre-clavulone a by Clavularia viridis. Implications for the Biosynthesis of Marine Prostanoids. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 109 PAGE : 289-290 (1987) |
| AUTHOR | : | Honda, A., Hong, S., Yamada, Y., and Mori, Y. |
| TITLE | : | Effect of marine coral prostanoids, clavulones, on spontaneous beating rate of cultured myocardial cells from fetal mouse hearts PubMed ID:1719591 |
| JOURNAL | : | Res Commun Chem Pathol Pharmacol. |
| VOL | : | 72 PAGE : 363-366 (1991) |
| AUTHOR | : | Klunder,A.J.H., Zwanenburg,B., and Liu,Z.Y. |
| TITLE | : | A Stereospecific Formal Synthesis of Clavulones from tricyclo[5.2.1.02.6]decadienone Epoxides. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 32 PAGE : 3131-3132 (1991) |
| AUTHOR | : | Takemoto,M., Koshida.,A., Miyazima,K., Suzuki,K., and Achiwa,K. |
| TITLE | : | Prostanoids and Related Compounds. IV. Total Synthesis of Clavulones. |
| JOURNAL | : | Chem.Pharm.Bull. |
| VOL | : | 39 PAGE : 1106-1111 (1991) |
| AUTHOR | : | Zhu,J., Yang,J.-Y., Klunder,A.J.H., Liu,Z.-Y., and Zwanenburg,B. |
| TITLE | : | A Stereo- and Enantioselective Approach to Clavulones from Tricyclodecadienone using Flash Vacum Thermolysis. |
| JOURNAL | : | Tetrahedron |
| VOL | : | 51 PAGE : 5847-5870 (1995) |
| AUTHOR | : | Takeda,K., Nakajima,A., and Yoshii,E. |
| TITLE | : | Synthesis of Clavulones (Claviridenones) via [3+2] Annulation using Reaction of [b-(phenylthio)acryloyl]silane with Lithium Enolate of Alkyl Methyl Ketone. |
| JOURNAL | : | Synlett |
| VOL | : | PAGE : 255-256 (1997) |
| AUTHOR | : | Honda, A., Mori, Y., Iguchi, K., and Yamada, Y. |
| TITLE | : | Structure requirements for antiproliferative and cytotoxic activities of marine coral prostanoids from the Japanese stolonifer Clavularia viridis against human myeloid leukemia cells in culture PubMed ID:3238009 |
| JOURNAL | : | Prostaglandins. |
| VOL | : | 36 PAGE : 621-630 (1988) |
| AUTHOR | : | Corey E.J., Matsuda, S.P.T., Nagata,R., and Cleaver, M.B. |
| TITLE | : | Biosynthesis of 8-R-HPETE and Preclavulone from Arachidonate in Several Species of Caribbean Coral. A Widespread Route to Marine Prostanoids. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 29 PAGE : 2555-2558 (1988) |
| AUTHOR | : | Honda, A., Mori, Y., Yamada, Y., Nakaike, S., Hayashi, H., and Otomo, S. |
| TITLE | : | Prolonged survival time of sarcoma 180-bearing mice treated with lipid microspheres-entrapped antitumor marine coral prostanoids PubMed ID:3187200 |
| JOURNAL | : | Res Commun Chem Pathol Pharmacol. |
| VOL | : | 61 PAGE : 413-416 (1988) |
| AUTHOR | : | Kikuchi,H., Tsukitani,Y., Iguchi,K., and Yamada,Y. |
| TITLE | : | Isolation and Structure Elucidation of New Type of Prostanoids Clavulone I, II, III, IV and Their Congeners, from the Okinawan Marine Animal Clavularia viridis Quoy and Gaimard. |
| JOURNAL | : | Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th |
| VOL | : | 26 PAGE : 220-227 (1983) |
| AUTHOR | : | Honda, A., Mori, Y., Iguchi, K., and Yamada, Y. |
| TITLE | : | Antiproliferative and cytotoxic effects of newly discovered halogenated coral prostanoids from the Japanese stolonifer Clavularia viridis on human myeloid leukemia cells in culture PubMed ID:2890095 |
| JOURNAL | : | Mol Pharmacol. |
| VOL | : | 32 PAGE : 530-535 (1987) |
| AUTHOR | : | Iguchi,K., Yamada,Y., Kikuchi,H., and Tsukitani,Y. |
| TITLE | : | Novel C-20-oxygenated Prostanoids, 20-Acetoxyclavulones, from the Stolonifer Clavularia viridis Quoy and Gaimard. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 24 PAGE : 4433-4434 (1983) |
| AUTHOR | : | Iguchi,K., Kaneta,S., Mori,K., Yamada,Y., Honda,A., and Mori,Y. |
| TITLE | : | Chlorovulones, New Halogenated Marine Prostanoids with Antitumor Activity from the Stolonifer Clavularia viridis Quoy and Gaimard. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 26 PAGE : 5787-5790 (1985) |
| AUTHOR | : | Nagaoka,H., Iguchi,K., Miyakoshi,T., Yamada,N., and Yamada,Y. |
| TITLE | : | Determination of Absolute Configuration of Chlorovulones by CD Measurement and by Enantioselective Synthesis of (-)-Chlorovulone II. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 27 PAGE : 223-226 (1986) |
| AUTHOR | : | Iguchi, K., Kaneta, S., Mori, K., and Yamada, Y. |
| TITLE | : | A new marine epoxy prostanoid with an antiproliferative activity from the stolonifer Clavularia viridis Quoy and Gaimard PubMed ID:3435962 |
| JOURNAL | : | Chem Pharm Bull (Tokyo). |
| VOL | : | 35 PAGE : 4375-4376 (1987) |
| AUTHOR | : | Iguchi,K., Kaneta,S., Mori,K., Yamada,Y., Honda, A., and Mori, Y. |
| TITLE | : | Bromovulone I and Iodovulone I, Unprecedented Brominated and Iodinated Marine Prostanoids with Antitumor Activity isolated from the Japanese Stolonifer Clavularia viridis Quoy and Gaimard. |
| JOURNAL | : | J. Chem. Soc., Chem. Commun. |
| VOL | : | PAGE : 981-982 (1986) |
| AUTHOR | : | Baker,B.J., Okuda,R.K., Yu,P.T.K., and Scheuer, P.J. |
| TITLE | : | Punaglandins: Halogenated Antitumor Eicosanoids from the Octocoral Telesto riisei. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 107 PAGE : 2976-2977 (1985) |
| AUTHOR | : | Nagaoka,H.,Miyaoka,H.,Miyakoshi,T., and Yamada,Y. |
| TITLE | : | Synthesis of Punaglandin 3 and 4. Revision of the Structures. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 108 PAGE : 5019-5021 (1986) |
| AUTHOR | : | Suzuki,M.,Morita,Y.,Yanagisawa,A.,Noyori,R.,Baker,B.J., and Scheuer,P.J. |
| TITLE | : | Synthesis of (7E)- and (7Z)-Punaglandin 4. Structural Revision. |
| JOURNAL | : | J. Am. Chem. Soc. |
| VOL | : | 108 PAGE : 5021-5022 (1986) |
| AUTHOR | : | Sasai,H., and Shibasaki,M. |
| TITLE | : | Total Synthesis of Punaglandin 4. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 28 PAGE : 333-336 (1987) |
| AUTHOR | : | Mori,K. and Takeuchi,T. |
| TITLE | : | Synthesis of Punaglandin 4 by Means of Enzymatic Resolution of the Key Chlorocyclopentene Derivative. |
| JOURNAL | : | Tetrahedron |
| VOL | : | 44 PAGE : 333-342 (1988) |
| AUTHOR | : | Suzuki,M.,Morita,Y.,Yanagisawa,A.,Baker,B.J.,Scheuer,P.J., and Noyori,R. |
| TITLE | : | Synthesis and Structural Revision of (7E)- and (7Z)-Punaglandin 4. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 53 PAGE : 286-295 (1988) |
| AUTHOR | : | Iwasaki,G.,Sano,M.,Sodeoka,M.,Yoshida,K., and Shibasaki,M. |
| TITLE | : | Asymmetric Synthesis of (2R)-2-Hydroxy-2-(2(Z)-octenyl)-1-cyclopentanone. |
| JOURNAL | : | J. Org. Chem. |
| VOL | : | 53 PAGE : 4864-4867 (1988) |
| AUTHOR | : | Baker, B. J., and Scheuer, P. J. |
| TITLE | : | The punaglandins: 10-chloroprostanoids from the octocoral Telesto riisei PubMed ID:7857405 |
| JOURNAL | : | J Nat Prod. |
| VOL | : | 57 PAGE : 1346-1353 (1994) |
| AUTHOR | : | Scheuer.P.J. |
| TITLE | : | Marine Natural Products Research: A Look into the Dive Bag. |
| JOURNAL | : | J. Nat.Prod. |
| VOL | : | 58 PAGE : 335-343 (1995) |
| AUTHOR | : | Iwashima, M., Okamoto, K., Konno, F., and Iguchi, K. |
| TITLE | : | New marine prostanoids from the okinawan soft coral, clavularia viridis PubMed ID:10075785 |
| JOURNAL | : | J Nat Prod. |
| VOL | : | 62 PAGE : 352-354 (1999) |
| AUTHOR | : | Iguchi, K., Iwashima, M., and Watanabe, K. |
| TITLE | : | Clavulolactones, New Marine Prostanoids with g-Lactonic Moiety in the a-Side-Chain from the Okinawan Soft Coral, Clavularia viridis. |
| JOURNAL | : | J. Nat. Prod. |
| VOL | : | 58 PAGE : 790-793 (1995) |
| AUTHOR | : | Watanabe, K., Iwashima, M., and Iguchi, K. |
| TITLE | : | New Marine Prostanoid Carboxylate Salts from the Okinawan Soft Coral, Clavularia viridis. |
| JOURNAL | : | J. Nat. Prod. |
| VOL | : | 59 PAGE : 980-982 (1996) |
| AUTHOR | : | Iwashima, M., Watanabe, K., and Iguchi, K. |
| TITLE | : | New Marine Prostanoid, Preclavulone Lactone, from the Okinawan Soft Coral, Clavularia viridis. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 38 PAGE : 8319-8322 (1997) |
| AUTHOR | : | Iwashima, M., Okamoto, K., Miyai, Y., and Iguchi, K. |
| TITLE | : | 4-Epiclavulones, New Marine Prostanoids from the Okinawan Soft Coral, Clavularia viridis. |
| JOURNAL | : | Chem. Pharm. Bull. |
| VOL | : | 47 PAGE : 884-886 (1999) |
| AUTHOR | : | Iwashima, M., Okamoto, K., and Iguchi, K. |
| TITLE | : | Clavirins, a New Type of Marine Oxylipins with Growth-inhibitory Activity from the Okinawan Soft Coral, Clavularia viridis. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 40 PAGE : 6455-6459 (1999) |
| AUTHOR | : | Weinheimer, A. J., and Spraggins, R. L. |
| TITLE | : | The occurrence of two new prostaglandin derivatives (15-epi-PGA2 and its acetate, methyl ester) in the gorgonian Plexaura homomalla chemistry of coelenterates. XV PubMed ID:4391762 |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 59 PAGE : 5185-5188 (1969) |
| AUTHOR | : | Light, R. J., and Samuelsson, B. |
| TITLE | : | Identification of prostaglandins in the gorgonian, Plexaura homomalla PubMed ID:4403575 |
| JOURNAL | : | Eur J Biochem. |
| VOL | : | 28 PAGE : 232-240 (1972) |
| AUTHOR | : | Carmely S., Kashman, Loya, Y. and Benayahu, Y. |
| TITLE | : | New Prostadlandin (PGF) Derivatives from the Soft Coral Lobophyton depressum. |
| JOURNAL | : | Tetrahedron Lett. |
| VOL | : | 21 PAGE : 875-878 (1980) |
| AUTHOR | : | Bundy, G. L., Daniels, E. G., Lincoln, F. H., and Pike, J. E. |
| TITLE | : | Isolation of a new naturally occurring prostaglandin, 5-trans-PGA 2. Synthesis of 5-trans-PGE 2 and 5-trans-PGF 2a PubMed ID:4401384 |
| JOURNAL | : | J Am Chem Soc. |
| VOL | : | 94 PAGE : 2124- (1972) |
=+140
=-61.0
=+30
= -9.6
=-10.9
=+13
= -8.9