New diterpenoids from the alga Dictyota dichotoma

被引:51
作者
Duran, R [1 ]
Zubia, E [1 ]
Ortega, MJ [1 ]
Salva, J [1 ]
机构
[1] FAC CIENCIAS MAR,DEPT QUIM ORGAN,PUERTO REAL 11510,CADIZ,SPAIN
关键词
D O I
10.1016/S0040-4020(97)00537-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The marine alga Dictyota dichotoma from Cortadura (Cadiz, Spain) contains, in addition to nineteen known diterpenes (8-26), the new dolabellanes, (1R,2E,4S,5R,6S,7E,10S,11S,12R)-5,6,18-triacetoxy-10-hydroxy-2,7-dolabelladiene (1), (1R,2E,4R,7E,10S,11S,12R)-18-acetoxy-10-hydroxy-2,7-dolabelladiene (2), (1R,2E,4S,5R,7E,10S,11S,12R)-5-acetoxy-10,18-dihydroxy-2,7-dolabelladiene (3), (1R*,3E,7S*,8S*,11S*,12R*)-7,8-epoxy-3,18-dolabelladiene (4), and (1R*,2E,4R*,7E,11S*,12R*)-18-acetoxy-2,7-dolabelladiene (5) together with two new hydroazulene diterpenes, isopachydictyol A (6) and dictyotatriol A (7). The structures of the new compounds were elucidated by interpretation of spectroscopic data and the absolute configurations of compounds 3, 7 and 10 were established using the Mosher's method and of compounds 1, 2, and 11 by chemical interconversions. The new diterpenes isolated from D. dichotoma showed mild cytotoxicity against four tumor cell lines excepting compounds 1 and 7 that were inactive. Dolabellane 2 exhibited the greatest activity. (C) 1997 Elsevier Science Ltd.
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页码:8675 / 8688
页数:14
相关论文
共 25 条
[1]   18-HYDROXY-3,7-DOLABELLADIENE FROM THE BROWN ALGA, DICTYOTA-DICHOTOMA [J].
AMICO, V ;
CURRENTI, R ;
ORIENTE, G ;
PIATTELLI, M ;
TRINGALI, C .
PHYTOCHEMISTRY, 1981, 20 (04) :848-849
[2]   DILOPHOL, A NEW 10-MEMBERED-RING DITERPENE ALCOHOL FROM BROWN ALGA DILOPHUS-LIGULATUS [J].
AMICO, V ;
ORIENTE, G ;
PIATTELLI, M ;
TRINGALI, C ;
FATTORUSSO, E ;
MAGNO, S ;
MAYOL, L .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (24) :1024-1025
[3]  
AMICO V, 1979, PHYTOCHEMISTRY, P1895
[4]   ABSOLUTE-CONFIGURATION OF HYDROAZULENOID DITERPENES BASED ON CIRCULAR-DICHROISM [J].
ARROYO, P ;
NORTE, M ;
VAZQUEZ, JT ;
NAKANISHI, K .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2671-2675
[5]   FURTHER PERHYDROAZULENE DITERPENES FROM MARINE ORGANISMS [J].
DANISE, B ;
MINALE, L ;
RICCIO, R ;
AMICO, V ;
ORIENTE, G ;
PIATTELLI, M ;
TRINGALI, C ;
FATTORUSSO, E ;
MAGNO, S ;
MAYOL, L .
EXPERIENTIA, 1977, 33 (04) :413-415
[6]   CHEMICAL STUDIES OF NORTH ADRIATIC SEAWEEDS .2. HYDROAZULENOID DITERPENES FROM THE BROWN ALGA DICTYOTA-DICHOTOMA VAR IMPLEXA [J].
DEROSA, S ;
DESTEFANO, S ;
ZAVODNIK, N .
PHYTOCHEMISTRY, 1986, 25 (09) :2179-2181
[7]   CHEMICAL STUDIES OF NORTH ADRIATIC SEAWEEDS .1. NEW DOLABELLANE DITERPENES FROM THE BROWN ALGA DILOPHUS-FASCIOLA [J].
DEROSA, S ;
DESTEFANO, S ;
MACURA, S ;
TRIVELLONE, E ;
ZAVODNIK, N .
TETRAHEDRON, 1984, 40 (23) :4991-4995
[8]   ABSOLUTE-CONFIGURATION AND CONFORMATIONAL MOBILITY OF DILOPHOL AND 3-ACETOXYACETYLDILOPHOL [J].
ENOKI, N ;
SHIRAHAMA, H ;
FURUSAKI, A ;
SUEHIRO, K ;
OSAWA, E ;
ISHIDA, R ;
MATSUMOTO, T .
CHEMISTRY LETTERS, 1984, (03) :459-462
[9]   Marine natural products [J].
Faulkner, DJ .
NATURAL PRODUCT REPORTS, 1996, 13 (02) :75-125
[10]  
FAULKNER DJ, 1993, CHEM REV, V93, P1671