A NEW SCALARANE SESTERTERPENOID FROM THE MARINE SPONGE CACOSPONGIA MOLLIOR

被引:41
作者
DEROSA, S [1 ]
PULITI, R [1 ]
CRISPINO, A [1 ]
DEGIULIO, A [1 ]
MATTIA, CA [1 ]
MAZZARELLA, L [1 ]
机构
[1] UNIV NAPLES,DIPARTIMENTO CHIM,I-80134 NAPLES,ITALY
来源
JOURNAL OF NATURAL PRODUCTS | 1994年 / 57卷 / 02期
关键词
D O I
10.1021/np50104a010
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
A new sesterterpene, 12-deacetoxyscalaradial [2a] has been isolated from the sponge Cacospongia mollior, together with the previously described scalaradial [2b] and furoscalarol [3]. The structure of the new compound, proposed by spectral data, was confirmed by X-ray diffraction analysis. Compound 2a is the first scalarane sesterterpenoid, without a substituent at C-12, to have been identified in nature. It shows high antifeedant activity and is hot to taste for the human tongue. Both 2a and 2b display cytotoxic activity.
引用
收藏
页码:256 / 262
页数:7
相关论文
共 17 条
[1]  
CAFIERI F, 1977, GAZZ CHIM ITAL, V107, P71
[2]   INSECT ANTIFEEDANT ACTIVITY AND HOT TASTE FOR HUMANS OF SELECTED NATURAL AND SYNTHETIC 1,4-DIALDEHYDES [J].
CAPRIOLI, V ;
CIMINO, G ;
COLLE, R ;
GAVAGNIN, M ;
SODANO, G ;
SPINELLA, A .
JOURNAL OF NATURAL PRODUCTS, 1987, 50 (02) :146-151
[3]   ABSOLUTE STEREOCHEMISTRY OF DISIDEIN AND OF 2 NEW RELATED HALOGENATED SESTERTERPENOIDS - TWO-DIMENSIONAL NMR-STUDIES AND X-RAY CRYSTAL-STRUCTURE [J].
CIMINO, G ;
DEROSA, S ;
DESTEFANO, S ;
PULITI, R ;
STRAZZULLO, G ;
MATTIA, CA ;
MAZZARELLA, L .
TETRAHEDRON, 1987, 43 (20) :4777-4784
[4]  
CIMINO G, 1982, COMP BIOCHEM PHYS B, V73, P471
[5]  
CIMINO G, 1974, EXPERIENTIA, V30, P846
[6]   STRUCTURAL STUDY OF A NEW DIALKYLATED SCALARANE FROM A CARTERIOSPONGIA SP [J].
CROFT, KD ;
GHISALBERTI, EL ;
SKELTON, BW ;
WHITE, AH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (01) :155-159
[7]   A NEW 20,24-DIMETHYLSCALARANE DERIVATIVE ISOLATED FROM THE SPONGE CARTERIOSPONGIA-FOLIASCENS, C30H42O6 [J].
DECLERCQ, JP ;
VANMEERSSCHE, M ;
BRAEKMAN, JC ;
DALOZE, D .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1985, 41 (AUG) :1222-1224
[8]   CACOSPONGIONOLIDE - A NEW ANTITUMORAL SESTERTERPENE, FROM THE MARINE SPONGE CACOSPONGIA-MOLLIOR [J].
DEROSA, S ;
DESTEFANO, S .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :5020-5023
[9]  
FRENZ BA, 1985, STRUCTURE DETERMINAT
[10]  
KIKUCHI H, 1981, CHEM PHARM BULL, V29, P1492