Withanolides from Withania aristata and their cytotoxic activity

Withanolides from Withania aristata and their cytotoxic activity
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DOI:
10.1016/j.steroids.2010.06.001
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发表时间:
2010-12-01
期刊:
影响因子:
2.7
通讯作者:
Bazzocchi, Isabel L.
Bazzocchi, Isabel L.
中科院分区:
医学3区
文献类型:
--
作者:
LLanos, Gabriel G.;Araujo, Liliana M.;Bazzocchi, Isabel L.

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从刺剑藤(Withania aristata)叶中分离得到7个新的睡茄内酯(1-7),其中沿着3个已知的睡茄内酯(8-10)。根据光谱分析(包括二维核磁共振实验和光谱技术)阐明了它们的结构,并通过CD分析确定了1和2的绝对构型。在从紫藤属物种中寻找新的细胞毒性化合物的过程中,测定了分离的化合物1-9,沿着两种衍生物对HeLa、MCF-7和A-549人肿瘤细胞系的细胞毒性。衍生物(4S,20 R,22 R)-27-乙酰氧基-4-对-溴苯甲酰氧基-1-氧代-witha-2,5,16,24-四烯丙基酮(13)对所有测定的细胞系显示出细胞毒性,IC(50)值范围为2.8 - 3.6 μ M,(4S,20 R,22 R)-4,27-二乙酰氧基-4-羟基-1-氧代-witha-2,5,16,24-四烯并吡喃(12)对MCF-7细胞系显示出5.4 μ M的IC(50)值。(C)2010年爱思唯尔公司版权所有© 2016
Seven new withanolides (1-7), along with three known ones (8-10), were isolated from the leaves of Withania aristata. Their structures were elucidated on the basis of spectroscopic analysis, including 2D NMR experiments and spectrometric techniques, and the absolute configuration of 1 and 2 was established by CD analysis. In the search for new cytotoxic compounds from Withania species, the isolated compounds 1-9, along with two derivatives, were assayed for their cytotoxicity against HeLa, MCF-7 and A-549 human tumor cell lines. Derivative (4S,20R,22R)-27-acetoxy-4-p-bromobenzoyloxy-1-oxo-witha-2,5,16,24-tetraenolide (13) showed cytotoxicity against all the cell lines assayed with IC(50) values ranging from 2.8 to 3.6 mu M, and (4S,20R,22R)-4,27-diacetoxy-4-hydroxy-1-oxo-witha-2,5,16,24-tetraenolide (12) exhibited an IC(50) value of 5.4 mu M on the MCF-7 cell line. (C) 2010 Elsevier Inc. All rights reserved,