Structural features of two taxoids from Taxus baccata L. growing in Turkey

被引:12
|
作者
Erdemoglu, N [1 ]
Sener, B
Ide, S
机构
[1] Gazi Univ, Fac Pharm, Dept Pharmacognosy, TR-06330 Ankara, Turkey
[2] Hacettepe Univ, Dept Engn Phys, TR-06532 Ankara, Turkey
关键词
Taxus baccata; taxoids; spectral data; conformations; molecular mechanic calculations;
D O I
10.1016/S0022-2860(00)00722-5
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
As a part of our ongoing research of the taxane-type constituents from T. baccata L. (Taxaceae) recorded in the Flora of Turkey, 2 alpha, 5 alpha, 10 beta -triacetoxy-14 beta-(2-methyl)-butryloxy-4(20),11-taxadiene (I) and taxusin (II) were isolated from the heartwood, in addition to the other taxoids. Their structures were elucidated using extensive spectroscopic techniques (IR, H-1 NMR, C-13 NMR, DEFT 135, H-1 H-1 COSY, HMQC, HMBC and MS). Molecular mechanic calculations and conformational analysis of I and II have been established using the MM3 program. The most probable conformation for compound I was obtained using semi-empirical molecular orbital methods and X-ray crystal structure results of II. Molecular orbital calculations of the derivative compound 4(20), 11-taxadiene (III) have been carried out to compare semi-empirical and experimental knowledge about molecular geometries in gas phase and solid state. (C) 2001 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:227 / 233
页数:7
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