INTEGRIFOLIAN-1,5-DIONE AND A REVISED STRUCTURE FOR AFRICANONE, BIOGENETICALLY RELATED SESQUITERPENE KETONES FROM LIPPIA-INTEGRIFOLIA

被引:17
作者
CATALAN, CAN [1 ]
DEFENIK, IJS [1 ]
DARTAYET, GH [1 ]
GROS, EG [1 ]
机构
[1] UNIV BUENOS AIRES,FAC CIENCIAS EXACTAS & NAT,DEPT QUIM ORGAN,RA-1428 BUENOS AIRES,ARGENTINA
关键词
LIPPIA-INTEGRIFOLIA; VERBENACEAE; SESQUITERPENE KETONES; STEREOCHEMISTRY; STRUCTURE; X-RAY ANALYSIS;
D O I
10.1016/S0031-9422(00)95227-0
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The fusion of the bicyclo [8.1.0]undecane system in the unique sesquiterpene diketone integrifolian-1,5-dione was found to be cis by X-ray analysis. A revised structure was derived for 'africanone' after reconsideration of the mass spectral data. The revised structure is based on a novel sesquiterpene skeleton and was confirmed by a biomimetic synthesis from integrifolian-1,5-dione.
引用
收藏
页码:1323 / 1326
页数:4
相关论文
共 6 条
[1]   NATURALLY-OCCURRING TERPENE DERIVATIVES .385. HUMULENE DERIVATIVES FROM ACRITOPAPPUS-PRUNIFOLIUS [J].
BOHLMANN, F ;
ZDERO, C ;
KING, RM ;
ROBINSON, H .
PHYTOCHEMISTRY, 1982, 21 (01) :147-150
[2]   A SESQUITERPENE DIKETONE FROM LIPPIA-INTEGRIFOLIA [J].
CATALAN, CA ;
IGLESIAS, DI ;
RETAMAR, JA ;
ITURRASPE, JB ;
DARTAYET, GH ;
GROS, EG .
PHYTOCHEMISTRY, 1983, 22 (06) :1507-1508
[3]   SESQUITERPENOIDS FROM LIPPIA-INTEGRIFOLIA - AFRICANONE, A TRICYCLIC SESQUITERPENE KETONE [J].
DARTAYET, GH ;
CATALAN, CA ;
RETAMAR, JA ;
GROS, EG .
PHYTOCHEMISTRY, 1984, 23 (03) :688-689
[4]   (+)-BICYCLOHUMULENONE, A NOVEL SESQUITERPENE KETONE OF THE HUMULANE GROUP FROM PLAGIOCHILA-ACANTHOPHYLLA SUBSP JAPONICA (LIVERWORT) - X-RAY CRYSTAL AND MOLECULAR-STRUCTURE OF THE PARA-BROMOBENZOATE DERIVATIVE [J].
MATSUO, A ;
NOZAKI, H ;
NAKAYAMA, M ;
KUSHI, Y ;
HAYASHI, S ;
KOMORI, T ;
KAMIJO, N .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (04) :174-175
[5]  
RETAMAR JA, 1981, ESSENZE DERIV AGRUM, V51, P40
[6]  
SHIRAHAMA H, 1980, Journal of the American Chemical Society, V102, P3208, DOI 10.1021/ja00529a052