BIOGENETICALLY DIVERSE, BIOACTIVE CONSTITUENTS OF A SPONGE, ORDER VERONGIDA - BROMOTYRAMINES AND SESQUITERPENE-SHIKIMATE DERIVED METABOLITES

被引:141
作者
HAMANN, MT
SCHEUER, PJ
KELLYBORGES, M
机构
[1] UNIV HAWAII MANOA,DEPT CHEM,HONOLULU,HI 96822
[2] HARBOR BRANCH OCEANOG INST INC,DIV BIOMED MARINE RES,FT PIERCE,FL 34946
关键词
D O I
10.1021/jo00076a012
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
From a Verongid sponge, family Aplysinellidae and most likely a member of an undescribed genus, we have isolated respectable quantities of a bromotyramine derivative, moloka'iamine (1) and of puupehenone (5) related compounds. When broken apart, the animal emits hydrogen cyanide. The structures were determined spectrally and by comparison with published data. Puupehenone-related metabolites 2 and 4-8 exhibit a variety of biological activities (cyotoxicity, antiviral, antifungal, immunomodulatory) to varying degrees. 1, 6-Addition to the conjugated dienone system of puupehenone (5) enhances some of the activities.
引用
收藏
页码:6565 / 6569
页数:5
相关论文
共 17 条
[1]   A DIMER OF PUUPEHENONE [J].
AMADE, P ;
CHEVELOT, L ;
PERZANOWSKI, HP ;
SCHEUER, PJ .
HELVETICA CHIMICA ACTA, 1983, 66 (06) :1672-1675
[2]  
BERGQUIST PR, 1983, MARINE NATURAL PRODU, V5, P1
[3]  
BLUNT JW, DATABASE LITERATURE
[4]  
DEVANEY DM, 1977, REEF SHORE FAUNA HAW, P58
[5]  
GIBBSTOWN NJ, HYDROGEN CYANIDE CON
[6]   CYANOPUUPEHENOL, AN ANTIVIRAL METABOLITE OF A SPONGE OF THE ORDER VERONGIDA [J].
HAMANN, MT ;
SCHEUER, PJ .
TETRAHEDRON LETTERS, 1991, 32 (41) :5671-5672
[7]   NOVEL MARINE SPONGE DERIVED AMINO-ACIDS .13. ADDITIONAL PSAMMAPLIN DERIVATIVES FROM PSAMMAPLYSILLA-PURPUREA [J].
JIMENEZ, C ;
CREWS, P .
TETRAHEDRON, 1991, 47 (12-13) :2097-2102
[8]  
MINALE L, 1974, Tetrahedron Letters, V38, P3401
[9]  
PATAI S, 1974, CHEM QUINOID COMPOUN, P238
[10]  
PRETSCH E, 1983, TABLES SPECTRAL DATA, pC120