Selective reactivity of 2-mercaptoethanol with 5β,6β-epoxide in steroids from Withania somnifera

被引：45
|
作者：
Misra, Laxminarain [1 ]
Lai, Payare [1 ]
Chaurasia, Narayan D. [1 ]
Sangwan, Rajender S. [1 ]
Sinha, Sudhir [2 ]
Tuli, Rakesh [3 ]
机构：
[1] Cent Inst Med & Aromat Plants, Lucknow 226015, Uttar Pradesh, India
[2] Cent Drug Res Inst, Drug Target Discovery & Dev Div, Lucknow 226001, Uttar Pradesh, India
[3] Natl Bot Res Inst, Lucknow 226001, Uttar Pradesh, India
来源：
STEROIDS | 2008年 / 73卷 / 03期
关键词：
Withania somnifera L; ashwagandha; withasteroids; withanolides; mercaptoethanol; epoxide;
D O I：
10.1016/j.steroids.2007.10.006
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：
2-Mercaptoethanol reacts selectively with the 5 beta,6 beta-epoxy steroids isolated from Withania somnifera substituting the epoxide by a six-membered oxyethylene-2'-thio ring whereas it failed to show such reactivity on 6 alpha,7 alpha-epoxy withasteroids. The structure of the product has been elucidated by spectroscopic methods, especially applying extensive 2D NMR methods. The anticancer activity of withaferin A was lost in the reaction product indicating that its activity is also linked to the free 5 beta,6 beta-epoxide functional group. (C) 2007 Elsevier Inc. All rights reserved.
引用
收藏
页码：245 / 251
页数：7
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