Carijodienone from the Octocoral Carijoa multiflora. A Spiropregnane-Based Steroid

被引:48
作者
Diaz-Marrero, Ana R. [1 ]
Porras, Gina [1 ]
Aragon, Zulma [1 ]
de la Rosa, Jose M. [1 ]
Dorta, Enrique [1 ]
Cueto, Mercedes [1 ]
D'Croz, Luis [2 ]
Mate, Juan [3 ]
Darias, Jose [1 ]
机构
[1] CSIC, Inst Prod Nat & Agrobiol, Tenerife 38206, Spain
[2] Univ Panama, Dept Biol Marina & Limnol, Panama City, Panama
[3] Smithsonian Trop Res Inst, Balboa, Panama
来源
JOURNAL OF NATURAL PRODUCTS | 2011年 / 74卷 / 02期
关键词
T76 SCENEDESMUS QUADRICAUDA; SOFT CORAL; TELESTO-RIISEI; ELYSIAPYRONES; BIOSYNTHESIS; PUNAGLANDINS; PREGNANES; CULTURES; CHAIN;
D O I
10.1021/np1007608
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Two new steroids (1 and 2) and the known pregna-1,4,20-trien-3-one (3) have been isolated from the Pacific octocoral Carijoa multiflora. Compound 1 possesses a novel spiropregnane-based steroidal skeleton. The photochemical transformation of 3 into 1. allowed the assignment of the absolute configuration at C-10 of 1. The antibacterial activities of compounds 1 and 3 were evaluated against a panel of bacterial strains.
引用
收藏
页码:292 / 295
页数:4
相关论文
共 26 条
[1]   PUNAGLANDINS - HALOGENATED ANTITUMOR EICOSANOIDS FROM THE OCTOCORAL TELESTO-RIISEI [J].
BAKER, BJ ;
OKUDA, RK ;
YU, PTK ;
SCHEUER, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (10) :2976-2977
[2]   PHOTOCHEMICAL PATHWAYS FOR THE INTERCONVERSION OF NOOTKATANE AND SPIROVETIVANE SESQUITERPENES [J].
CAINE, D ;
CHU, CY ;
GRAHAM, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (19) :3790-3797
[3]   New C21 Δ20 pregnanes, inhibitors of mitochondrial respiratory chain, from Indopacific octocoral Carijoa sp. [J].
Ciavatta, ML ;
Gresa, MPL ;
Manzo, E ;
Gavagnin, M ;
Wahidulla, S ;
Cimino, G .
TETRAHEDRON LETTERS, 2004, 45 (41) :7745-7748
[4]   Elysiapyrones from Elysia diomedea.: Do such metabolites evidence an enzymatically assisted electrocyclization cascade for the biosynthesis of their bicyclo[4.2.0]octane core? [J].
Cueto, M ;
D'Croz, L ;
Maté, JL ;
San-Martín, A ;
Darias, J .
ORGANIC LETTERS, 2005, 7 (03) :415-418
[5]   POLYOXYGENATED STEROIDS OF MARINE ORIGIN [J].
DAURIA, MV ;
MINALE, L ;
RICCIO, R .
CHEMICAL REVIEWS, 1993, 93 (05) :1839-1895
[6]   Rearrangements of exogenus 17 beta-hydroxy-17 alpha-methylandrosta-1,4-dien-3-one in cultures of the green alga T76 Scenedesmus quadricauda [J].
DellaGreca, M ;
Fiorentino, A ;
Pinto, G ;
Pollio, A ;
Previtera, L .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) :7178-7179
[7]   Bioconversion of 17 beta-hydroxy-17 alpha-methyl-androsta-1,4-dien-3-one and androsta-1,4-diene-3,17-dione in cultures of the green alga T76 Scenedesmus quadricauda [J].
DellaGreca, M ;
Previtera, L ;
Fiorentino, A ;
Pinto, G ;
Pollio, A .
TETRAHEDRON, 1996, 52 (44) :13981-13990
[8]   Validating an endoperoxide as a key intermediate in the biosynthesis of elysiapyrones [J].
Diaz-Marrero, Ana R. ;
Cueto, Mercedes ;
D'Croz, Luis ;
Darias, Jose .
ORGANIC LETTERS, 2008, 10 (14) :3057-3060
[9]   Carijenone, a novel class of bicyclic prostanoid from the eastern Pacific octocoral Carijoa multiflora [J].
Dorta, E ;
Díaz-Marrero, AR ;
Cueto, M ;
D'Croz, L ;
Maté, JL ;
Darlas, J .
ORGANIC LETTERS, 2004, 6 (13) :2229-2232
[10]  
Fabricius K.K., 2001, SOFT CORALS SEA FANS, P1