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生物测定导向分离藤黄属植物叶中的prenylated xanthone 衍生物。

Bioassay-Guided Isolation of Prenylated Xanthone Derivatives from the Leaves of Garcinia oligantha.

机构信息

School of Pharmacy, Shanghai University of Traditional Chinese Medicine , Shanghai 201203, People's Republic of China.

Engineering Research Center of Shanghai Colleges for TCM New Drug Discovery , Shanghai 201203, People's Republic of China.

出版信息

J Nat Prod. 2016 Jul 22;79(7):1752-61. doi: 10.1021/acs.jnatprod.6b00137. Epub 2016 Jun 22.

DOI:10.1021/acs.jnatprod.6b00137
PMID:27329938
Abstract

Four new dihydroxanthone derivatives (1-4), four new tetrahydroxanthone derivatives (5-8), two new xanthone derivatives (9 and 10), and two known caged tetrahydroxanthones were isolated from extracts of the leaves of Garcinia oligantha by bioassay-guided fractionation. These structures of the new compounds were elucidated by NMR and MS spectroscopic data analysis, and the absolute configurations of compounds 1 and 5-7 were determined by electronic circular dichroism and/or single-crystal X-ray diffraction analysis. Compounds 6-9 were shown to be unusual xanthone derivatives with an isopropyl group, which was confirmed by the X-ray crystallographic structure of compound 8. The inhibitory activities of these isolates against four human tumor cell lines (A549, HepG2, HT-29, and PC-3) were assayed, and compounds 1, 2, 5, 11, and 12 showed inhibitory effects on tumor cell growth, with IC50 values ranging from 2.1 to 8.6 μM.

摘要

从窄叶藤黄的叶提取物中,通过生物测定指导的分段分离,分离出四个新的二羟基蒽酮衍生物(1-4)、四个新的四羟基蒽酮衍生物(5-8)、两个新的蒽酮衍生物(9 和 10)和两个已知的笼状四羟基蒽酮。通过 NMR 和 MS 光谱数据分析阐明了这些新化合物的结构,并且通过电子圆二色性和/或单晶 X 射线衍射分析确定了化合物 1 和 5-7 的绝对构型。化合物 6-9 被证明是具有异丙基的不寻常的蒽酮衍生物,这通过化合物 8 的 X 射线晶体结构得到证实。这些分离物对四种人肿瘤细胞系(A549、HepG2、HT-29 和 PC-3)的抑制活性进行了测定,化合物 1、2、5、11 和 12 显示出对肿瘤细胞生长的抑制作用,IC50 值范围为 2.1 到 8.6 μM。

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