ISOLATION AND STRUCTURE OF CONSTANOLACTONE-A AND CONSTANOLACTONE-B, NEW CYCLOPROPYL HYDROXYEICOSANOIDS FROM THE TEMPERATE RED ALGA CONSTANTINEA-SIMPLEX

被引：68

作者：

NAGLE, DG ^{[1
]}

GERWICK, WH ^{[1
]}

机构：

[1] OREGON STATE UNIV,COLL PHARM,CORVALLIS,OR 97331

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 21期

关键词：

D O I：

10.1016/S0040-4039(00)89007-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new cyclopropyl and lactone containing eicosanoids, constanolactone A and B, were isolated as synthetic diacetate derivatives from the temperate red alga Constantinea simplex and their structures determined by spectroscopic means. A hydrolysis product of one of these helped to define the lactone size in these new eicosanoids. The co-occurrence of three known 12-lipoxygenase metabolites, 12-S-HETE, 12-S-HEPE, and 12-oxododeca-5(Z), 8(E), 10(E)-trienoic acid, supports a 12-1ipoxygenase origin for the new compounds. © 1990.

引用

页码：2995 / 2998

页数：4

共 19 条

[1] FORMATION OF A CYCLOPROPYL EICOSANOID VIA AN ALLENE OXIDE IN THE CORAL PLEXAURA-HOMOMALLA - IMPLICATIONS FOR THE BIOSYNTHESIS OF 5,6-TRANS-PROSTAGLANDIN-A2
BAERTSCHI, SW
BRASH, AR
HARRIS, TM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) : 5003 - 5005
[2] ISOLATION OF 12-(S)-HEPE FROM THE RED MARINE ALGA MURRAYELLA-PERICLADOS AND REVISION OF STRUCTURE OF AN ACYCLIC ICOSANOID FROM LAURENCIA-HYBRIDA - IMPLICATIONS TO THE BIOSYNTHESIS OF THE MARINE PROSTANOID HYBRIDALACTONE
BERNART, M
GERWICK, WH
[J]. TETRAHEDRON LETTERS, 1988, 29 (17) : 2015 - 2018
[3] BERNART M, UNPUB
[4] FORMATION OF AN ALLENE OXIDE FROM (8R)-8-HYDROPEROXYEICOSATETRAENOIC ACID IN THE CORAL PLEXAURA-HOMOMALLA
BRASH, AR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (05) : 1891 - 1892
[5] BRASH AR, 1987, J BIOL CHEM, V262, P15829
[6] THE STEREOCHEMISTRY AND BIOSYNTHESIS OF HYBRIDALACTONE, AN EICOSANOID FROM LAURENCIA-HYBRIDA
COREY, EJ
DE, B
PONDER, JW
BERG, JM
[J]. TETRAHEDRON LETTERS, 1984, 25 (10) : 1015 - 1018
[7] IDENTIFICATION OF A NEW EICOSANOID FROM INVITRO BIOSYNTHETIC EXPERIMENTS WITH CLAVULARIA-VIRIDIS - IMPLICATIONS FOR THE BIOSYNTHESIS OF CLAVULONES
COREY, EJ
LANSBURY, PT
YAMADA, Y
[J]. TETRAHEDRON LETTERS, 1985, 26 (35) : 4171 - 4174
[8] 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
COREY, EJ
DALARCAO, M
MATSUDA, SPT
LANSBURY, PT
YAMADA, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (01) : 289 - 290
[9] BIOSYNTHESIS OF 8-R-HPETE AND PRECLAVULONE-A FROM ARACHIDONATE IN SEVERAL SPECIES OF CARIBBEAN CORAL - A WIDESPREAD ROUTE TO MARINE PROSTANOIDS
COREY, EJ
MATSUDA, SPT
NAGATA, R
CLEAVER, MB
[J]. TETRAHEDRON LETTERS, 1988, 29 (21) : 2555 - 2558
[10] GERWICK WH, 1990, IN PRESS 13 P INT SE, V13

← 1 2 →