New antifeedant triterpene glycosides from the caribbean sponge Erylus formosus

被引:16
作者
Kubanek, J
Fenical, W
Pawlik, JR
机构
[1] Univ Calif San Diego, Scripps Inst Oceanog, Ctr Marine Biotechnol, La Jolla, CA 92093 USA
[2] Univ N Carolina, Ctr Marine Sci, Wilmington, NC 28409 USA
来源
NATURAL PRODUCT LETTERS | 2001年 / 15卷 / 04期
基金
美国国家科学基金会; 加拿大自然科学与工程研究理事会;
关键词
sponge; chemical defense; formoside; Erylus formosus;
D O I
10.1080/10575630108041292
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
Two groups of antifeedant triterpene glycosides were identified from the Caribbean sponge Erylus formosus. The structure of formoside B, a novel N-acetyl amino derivative of the known penasterol tetrasaccharide formoside, was elucidated using NMR and mass spectral data. Four triterpene hexasaccharides and two triterpene trisaccharides, characterized by a 31-carbon aglycone, proved difficult to isolate and therefore only the structure of their aglycone was determined. Gas chromatographic analysis of derivatized saccharides from these mixtures established the carbohydrate content of these compounds. All of the triterpene glycosides isolated contributed to the chemical defenses of this sponge, although with differing activities.
引用
收藏
页码:275 / 285
页数:11
相关论文
共 9 条
[1]  
Applebaum S. W., 1979, Herbivores: their interaction with secondary plant metabolites, P539
[2]  
Cafieri F, 1999, EUR J ORG CHEM, V1999, P231
[3]   ERYLOSIDE-E FROM AN ATLANTIC SPONGE ERYLUS-GOFFRILLERI [J].
GULAVITA, NK ;
WRIGHT, AE ;
KELLYBORGES, M ;
LONGLEY, RE ;
YARWOOD, D ;
SILLS, MA .
TETRAHEDRON LETTERS, 1994, 35 (25) :4299-4302
[4]   A TRITERPENE TETRASACCHARIDE, FORMOSIDE, FROM THE CARIBBEAN CHORISTIDA SPONGE ERYLUS-FORMOSUS [J].
JASPARS, M ;
CREWS, P .
TETRAHEDRON LETTERS, 1994, 35 (41) :7501-7504
[5]   Triterpene glycosides defend the Caribbean reef sponge Erylus formosus from predatory fishes [J].
Kubanek, J ;
Pawlik, JR ;
Eve, TM ;
Fenical, W .
MARINE ECOLOGY PROGRESS SERIES, 2000, 207 :69-77
[6]   DEFENSES OF CARIBBEAN SPONGES AGAINST PREDATORY REEF FISH .1. CHEMICAL DETERRENCY [J].
PAWLIK, JR ;
CHANAS, B ;
TOONEN, RJ ;
FENICAL, W .
MARINE ECOLOGY PROGRESS SERIES, 1995, 127 (1-3) :183-194
[7]   Eryloside F, a novel penasterol disaccharide possessing potent thrombin receptor antagonist activity [J].
Stead, P ;
Hiscox, S ;
Robinson, PS ;
Pike, NB ;
Sidebottom, PJ ;
Roberts, AD ;
Taylor, NL ;
Wright, AE ;
Pomponi, SA ;
Langley, D .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (07) :661-664
[8]  
WIEDENMAYER F, 1977, EXPT S, V28
[9]  
WRIGTH A, COMMUNICATION