Sterols of the marine sponge Petrosia weinbergi:: implications for the absolute configurations of the antiviral orthoesterols and weinbersterols

被引：17

作者：

Giner, JL ^{[1
]}

Gunasekera, SP

Pomponi, SA

机构：

[1] SUNY Syracuse, Dept Chem, Syracuse, NY 13210 USA

[2] Harbor Branch Oceanog Inst Inc, Div Biomed Marine Res, Ft Pierce, FL 34946 USA

来源：

STEROIDS | 1999年 / 64卷 / 12期

关键词：

sterols; cyclopropyl sterols; marine natural products; antiviral steroids; Petrosia weinbergi;

D O I：

10.1016/S0039-128X(99)00068-9

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The marine sponge Petrosia weinbergi was found to contain isofucosterol and clionasterol as its major sterols. The rare cyclopropyl sterol (24S,28S)-24,28-methylenestigmast-5-en-3 beta-ol, previously detected as only 0.07% of the total sterols of a pelagophytic alga Pulvinaria sp., made up 6.6% of the total sterols. These sterols are believed to be the biosynthetic precursors of the antiviral orthoesterols and weinbersterols found in the same sponge. Based on the side chains of the isolated sterols, the absolute configurations of the antiviral steroid side chains are assigned to be (24R,28S)- for orthoesterol B, (24R)- for orthoesterol C, and (24S,28S)- for weinbersterols A and B. (C) 1999 Elsevier Science Inc. All rights reserved.

引用

收藏

页码：820 / 824

页数：5

相关论文

共 27 条

[1] NOVEL HIV-INHIBITORY HALISTANOL SULFATES F-H FROM A MARINE SPONGE, PSEUDOAXINISSA-DIGITATA [J].

BIFULCO, G ;

BRUNO, I ;

MINALE, L ;

RICCIO, R .

JOURNAL OF NATURAL PRODUCTS, 1994, 57 (01) :164-167

[2] SPONGE STEROLS - ORIGIN AND BIOSYNTHESIS [J].

DJERASSI, C ;

SILVA, CJ .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (12) :371-378

[3] TOPSENTIASTEROL SULFATES, ANTIMICROBIAL STEROL SULFATES POSSESSING NOVEL SIDE-CHAINS, FROM A MARINE SPONGE, TOPSENTIA SP [J].

FUSETANI, N ;

TAKAHASHI, M ;

MATSUNAGA, S .

TETRAHEDRON, 1994, 50 (26) :7765-7770

[4] BIOACTIVE MARINE METABOLITES .2. HALISTANOL SULFATE, AN ANTI-MICROBIAL NOVEL STEROID SULFATE FROM THE MARINE SPONGE HALICHONDRIA CF MOOREI BERGQUIST [J].

FUSETANI, N ;

MATSUNAGA, S ;

KONOSU, S .

TETRAHEDRON LETTERS, 1981, 22 (21) :1985-1988

[5] SYNTHESIS OF (24R,28R)-24,28-METHYLENE-5-STIGMASTEN-3-BETA-OL AND (24S,28S)-24,28-METHYLENE-5-STIGMASTEN-3-BETA-OL AND BIOSYNTHETIC IMPLICATIONS OF CYCLOPROPYL CLEAVAGE TO 24-SUBSTITUTED CHOLESTEROLS [J].

GINER, JL ;

ZIMMERMAN, MP ;

DJERASSI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (25) :5895-5902

[6] BIOSYNTHETIC-STUDIES OF MARINE LIPIDS .31. EVIDENCE FOR A PROTONATED CYCLOPROPYL INTERMEDIATE IN THE BIOSYNTHESIS OF 24-PROPYLIDENECHOLESTEROL [J].

GINER, JL ;

DJERASSI, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) :1386-1393

[7] ARAGUSTEROL-A - A POTENT ANTITUMOR MARINE STEROID FROM THE OKINAWAN SPONGE OF THE GENUS, XESTOSPONGIA [J].

IGUCHI, K ;

FUJITA, M ;

NAGAOKA, H ;

MITOME, H ;

YAMADA, Y .

TETRAHEDRON LETTERS, 1993, 34 (39) :6277-6280

[8] BIOACTIVE MARINE METABOLITES .42. HALISTANOL SULFATES-A-E, NEW STEROID SULFATES, FROM A MARINE SPONGE, EPIPOLASIS-SP [J].

KANAZAWA, S ;

FUSETANI, N ;

MATSUNAGA, S .

TETRAHEDRON, 1992, 48 (26) :5467-5472

[9]

KHALIL MW, 1980, STEROIDS, V35, P707

[10] EFFECTIVE SEPARATION AND C-24 STEREOCHEMICAL ASSIGNMENT OF EPIMERIC 24-ISOPROPENYLCHOLESTEROLS [J].

KIKUCHI, T ;

KADOTA, S ;

SHIMA, T .

TETRAHEDRON LETTERS, 1985, 26 (32) :3817-3820