New terpenoid constituents from Eunicea pinta

被引:35
作者
Shi, YP [1 ]
Rodríguez, AD [1 ]
Barnes, CL [1 ]
Sánchez, JA [1 ]
Raptis, RG [1 ]
Baran, P [1 ]
机构
[1] Univ Puerto Rico, Dept Chem, Rio Piedras, PR 00931 USA
来源
JOURNAL OF NATURAL PRODUCTS | 2002年 / 65卷 / 09期
关键词
D O I
10.1021/np0200820
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
The secondary metabolite composition of the gorgonian octocoral Eunicea pinta from San Andres Island, Colombia, is described for the first time. This investigation has resulted in the isolation of eight now gamma-cembranolide-type diterpenes, namely, compounds 3-10, and a new saponin, 13, possessing a pregnene-derived aglycon. In addition, two previously known alpha-methylene-gamma-lactone cembranolides, euniolide (1) and succinolide (2), were also isolated. Their structures were determined on the basis of the results of spectroscopic analysis, X-ray diffraction analysis, and chemical conversions. The discovery of cembranolides 3-10 has prompted us to conclude that the structures proposed earlier for several uprolide-type cembranolides need revision and that a minor stereochemical correction is also in order for succinolide. Cytotoxicity of compounds 3, 4, and 13 toward various cancer cell lines and results of an anti mycobacterial screening for 2, 4, and 13 also are described.
引用
收藏
页码:1232 / 1241
页数:10
相关论文
共 23 条
[1]  
[Anonymous], 1992, INT TABLES CRYSTALLO, VC
[2]   ISOLATION OF THE MURICINS - EVIDENCE OF A CHEMICAL ADAPTATION AGAINST FOULING IN THE MARINE OCTOCORAL MURICEA-FRUTICOSA (GORGONACEA) [J].
BANDURRAGA, MM ;
FENICAL, W .
TETRAHEDRON, 1985, 41 (06) :1057-1065
[3]  
Bayer F. M., 1961, SHALLOW WATER OCTOCO
[4]  
BAYER FREDERICK M., 1958, BULL MARINE SCI GULF AND CARIBBEAN, V8, P224
[5]   ANTIMICROBIAL ACTIVITY OF HORNY CORALS [J].
BURKHOLDER, PR ;
BURKHOLDER, LM .
SCIENCE, 1958, 127 (3307) :1174-1175
[6]   A new steroidal glycoside from a Caribbean gorgonian, Eunicea sp. [J].
Cobar, OM ;
Rodriguez, AD ;
Padilla, OL .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (11) :1186-1188
[7]   MARINE NATURAL-PRODUCTS - NOVEL C-21 DELTA-20 PREGNANES FROM THE SEA RASPBERRY (GERSEMIA-RUBIFORMIS) [J].
KINGSTON, JF ;
GREGORY, B ;
FALLIS, AG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (08) :2064-2068
[8]   CONFORMATIONAL PROPERTIES OF GLYCOSIDIC LINKAGES [J].
LEMIEUX, RU ;
KOTO, S .
TETRAHEDRON, 1974, 30 (13) :1933-1944
[9]   THE SECO-PSEUDOPTEROSINS, NEW ANTIINFLAMMATORY DITERPENE-GLYCOSIDES FROM A CARIBBEAN GORGONIAN OCTOCORAL OF THE GENUS PSEUDOPTEROGORGIA [J].
LOOK, SA ;
FENICAL, W .
TETRAHEDRON, 1987, 43 (15) :3363-3370
[10]   THE PSEUDOPTEROSINS - A NEW CLASS OF ANTIINFLAMMATORY AND ANALGESIC DITERPENE PENTOSIDES FROM THE MARINE SEA WHIP PSEUDOPTEROGORGIA-ELISABETHAE (OCTOCORALLIA) [J].
LOOK, SA ;
FENICAL, W ;
MATSUMOTO, GK ;
CLARDY, J .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5140-5145