Diterpenoids from Lycopus europaeus and Nepeta septemcrenata:: Revised structures and new isopimarane derivatives

被引:15
作者
Hussein, AA
Rodríguez, B
Martínez-Alcázar, MD
Cano, FH
机构
[1] CSIC, Inst Quim Organ, E-28006 Madrid, Spain
[2] Univ San Pablo, CEU, Fac Ciencias Expt & Tecn, Dept Ciencias Basica, E-28668 Madrid, Spain
[3] CSIC, Inst Rocasolano, Dept Cristalog, E-28006 Madrid, Spain
关键词
terpenes; isopimaranes; stereochemistry; X-ray crystal structure;
D O I
10.1016/S0040-4020(99)00361-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Seven isopimarane diterpenoids have been isolated from Nepeta septemcrenata (3) and Lycopus europaeus (4-9), both species belonging to the Labiatae family. Compound 3 had been reported as the sole diterpene constituent of N, septemcrenata, whereas the physical and spectroscopic data of 4 were identical to those of a compound previously isolated from L. europaeus to which structure 1 had been attributed. As a result of exhaustive spectroscopic studies and some chemical correlations between 3 and 4, we definitely conclude that structure 1 must be amended to 4. In addition. the structures of five new diterpenoids found in L. europaeus (5-9) were established by chemical and spectroscopic means, and a normal isopimarane absolute configuration for all the isolated compounds, except for 7, was supported by CD data, application of the Horeau's method and chemical correlations. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7375 / 7388
页数:14
相关论文
共 16 条
[1]  
Altomare A., 1992, SIR92
[2]  
[Anonymous], 1992, INT TABLES XRAY CRYS, VC
[3]   THE CHEMISTRY OF THE TRITERPENES AND RELATED COMPOUNDS .18. ELUCIDATION OF THE STRUCTURE OF POLYPORENIC ACID-C [J].
BOWERS, A ;
HALSALL, TG ;
JONES, ERH ;
LEMIN, AJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1953, (SEP) :2548-2560
[4]  
CONNOLLY JD, 1991, DICT TERPENOIDS, V2, P857
[5]   CRYSTAL-STRUCTURE OF ISOVIRESCENOL B, C20O2H32 [J].
CORAZZA, E .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1975, 31 (MAY15) :1445-1450
[6]  
CRABBE P, 1968, APPL DISPERSION ROTA, P193
[7]  
HALL SR, 1994, XTAL 3 2 REFERENCE M
[8]  
HOREAU A, 1971, TETRAHEDRON LETT, V12, P1939
[9]   A NOVEL PIMARA-8(9),15-DIENE FROM LYCOPUS-EUROPAEUS [J].
JEREMIC, D ;
MACURA, S ;
MILOSAVLJEVIC, S ;
VAJS, V .
TETRAHEDRON, 1985, 41 (02) :357-364
[10]   A diterpene from Nepeta septemcrenata [J].
Khalil, AT ;
Gedara, SR ;
Lahloub, MF ;
Halim, AF ;
Voehler, M .
PHYTOCHEMISTRY, 1997, 44 (03) :475-478