BROMINATED ACETYLENIC FATTY-ACIDS FROM XESTOSPONGIA SP, A MARINE SPONGE-BACTERIA ASSOCIATION

被引:55
作者
BRANTLEY, SE
MOLINSKI, TF
PRESTON, CM
DELONG, EF
机构
[1] UNIV CALIF DAVIS,DEPT CHEM,DAVIS,CA 95616
[2] UNIV CALIF SANTA BARBARA,INST MARINE SCI,SANTA BARBARA,CA 93106
基金
美国国家科学基金会; 美国国家卫生研究院; 美国海洋和大气管理局;
关键词
D O I
10.1016/0040-4020(95)00405-W
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three new brominated fatty acids, (5E, 11E, 15E, 19E)-20-bromoeicosa-5, 11, 15, 19-tetraene-9, 17-diynoic acid (1), (5Z, 11E, 15E, 19E)-6, 20-dibromoeicosa-5, 11, 15, 19-tetraene-9, 17-diynoic acid (2) and (Z E)-14, 14-dibromo-4, 6, 13-tetradecatrienoate, characterized as the methyl ester, 3, were isolated from Xestospongia sp. from the Indian Ocean. Compounds 1 -2 (C-20) and 3 (C-14) are brominated fatty acids of unusual carbon number that have not been encountered previously in marine invertebrates. Xestospongia sp. is an association of sponge cells and bacteria, the latter accounting for ca. 50% of cellular mass.
引用
收藏
页码:7667 / 7672
页数:6
相关论文
共 23 条
[11]   REGEL ZUR ABSCHATZUNG DER CHEMISCHEN VERSCHIEBUNG VON PROTONEN AN EINER DOPPELBINDUNG [J].
PASCUAL, C ;
MEIER, J ;
SIMON, W .
HELVETICA CHIMICA ACTA, 1966, 49 :164-&
[12]   BROMINATED POLYACETYLENIC ACIDS FROM THE MARINE SPONGE XESTOSPONGIA-MUTA - INHIBITORS OF HIV PROTEASE [J].
PATIL, AD ;
KOKKE, WC ;
COCHRAN, S ;
FRANCIS, TA ;
TOMSZEK, T ;
WESTLEY, JW .
JOURNAL OF NATURAL PRODUCTS, 1992, 55 (09) :1170-1177
[13]   FURTHER ACETYLENIC ACIDS FROM THE MARINE SPONGE XESTOSPONGIA-TESTUDINARIA [J].
QUINN, RJ ;
TUCKER, DJ .
JOURNAL OF NATURAL PRODUCTS, 1991, 54 (01) :290-294
[14]   A BROMINATED BISACETYLENIC ACID FROM THE MARINE SPONGE XESTOSPONGIA-TESTUDINARIA [J].
QUINN, RJ ;
TUCKER, DJ .
TETRAHEDRON LETTERS, 1985, 26 (13) :1671-1672
[15]  
SCHMITZ FJ, 1978, TETRAHEDRON LETT, V39, P3637
[16]   CONFIGURATIONAL ANALYSIS OF NEW FURANOSESQUITERPENES FROM DYSIDEA-HERBACEA - ASSIGNMENT OF ABSOLUTE STEREOCHEMISTRY [J].
SEARLE, PA ;
JAMAL, NM ;
LEE, GM ;
MOLINSKI, TF .
TETRAHEDRON, 1994, 50 (13) :3879-3888
[17]   STRUCTURE AND ABSOLUTE-CONFIGURATION OF (R)-(E)-1-AMINOTRIDEC-5-EN-2-OL, AN ANTIFUNGAL AMINO ALCOHOL FROM THE ASCIDIAN DIDEMNUM SP [J].
SEARLE, PA ;
MOLINSKI, TF .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7578-7580
[18]   LOW-TEMPERATURE C-13-NMR - SPECTROSCOPY OF ORGANO-LITHIUM DERIVATIVES - C-13,LI-6-COUPLING, A POWERFUL STRUCTURAL INFORMATION [J].
SEEBACH, D ;
HASSIG, R ;
GABRIEL, J .
HELVETICA CHIMICA ACTA, 1983, 66 (01) :308-337
[19]  
Stahl D. A., 1991, NUCL ACID TECHNIQUES, P205
[20]   USE OF PHYLOGENETICALLY BASED HYBRIDIZATION PROBES FOR STUDIES OF RUMINAL MICROBIAL ECOLOGY [J].
STAHL, DA ;
FLESHER, B ;
MANSFIELD, HR ;
MONTGOMERY, L .
APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1988, 54 (05) :1079-1084