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考地迪辛是一种从毕赤酵母中提取的潜在新型抗 HIV 留体。

Cordidepsine is A Potential New Anti-HIV Depsidone from , Baker.

机构信息

Department of Organic Chemistry, University of Yaoundé I, Faculty of Science, P.O. Box 812 Yaoundé, Cameroon.

International Center for Chemical and Biological Sciences, H.E.J Research Institute of Chemistry, University of Karachi, Karachi-75270, Pakistan.

出版信息

Molecules. 2019 Sep 3;24(17):3202. doi: 10.3390/molecules24173202.

DOI:10.3390/molecules24173202
PMID:31484419
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6749241/
Abstract

Chemical investigation of Baker resulted in the isolation of a new depsidone, cordidepsine (), along with twelve known compounds including cyclooctasulfur (), lup-20(29)-en-3-triacontanoate (), 1-(26-hydroxyhexacosanoyl)glycerol (), glyceryl-1-hexacosanoate () betulinic acid (), lupenone (), -amyrone (), lupeol (), -amyrin (), allantoin (), 2'-(4-hydroxyphenyl)ethylpropanoate () and stigmasterol glycoside (). Hemi-synthetic reactions were carried out on two isolated compounds ( and ) to afford two new derivatives, that is, cordicerol A () and cordicerol B (), respectively. The chemical structures of all the compounds were established based on analysis and interpretation of spectroscopic data such as electron ionization mass spectrometry (EI-MS), high resolution electrospray ionization mass spectrometry (HR-ESI-MS), fast atom bombardment mass spectrometry (FAB-MS), one dimension and two dimension nuclear magnetic resonance (1D and 2D-NMR) spectral data as well as X-ray crystallography (XRC). Lupeol ester derivatives [Lup-20(29)-en-3-triacontanoate ()], monoglycerol derivatives [1-(26-hydroxyhexacosanoyl)glycerol () and glyceryl-1 hexacosanoate ()] were isolated for the first time from genus while sulfur allotrope [cyclooctasulfur ()] was isolated for the first time from plant origin. Biological assays cordidepsine () exhibited significant anti-HIV integrase activity with IC = 4.65 μM; EtOAc extract of stem barks, EtOAc fraction of roots and leaves were not toxic against 3T3 cells.

摘要

贝克的化学成分研究导致了一种新的去甲二萜 cordidepsine () 的分离,以及包括环八硫 (), lup-20(29)-en-3-三十烷酸酯 (), 1-(26-羟基二十六烷酰基)甘油 (), 甘油-1-二十六烷酸酯 () 在内的 12 种已知化合物的分离。白桦脂酸 (), lupenone (), -amyrone (), lupeol (), -amyrin (), 尿囊素 (), 2'-(4-羟基苯基)乙基丙氨酸 () 和豆甾醇糖苷 (). 对半合成化合物 ( 和 ) 进行了反应,得到了两种新的衍生物,即 cordicerol A () 和 cordicerol B (). 所有化合物的化学结构都是基于电子电离质谱 (EI-MS)、高分辨率电喷雾电离质谱 (HR-ESI-MS)、快原子轰击质谱 (FAB-MS)、一维和二维核磁共振 (1D 和 2D-NMR) 谱数据以及 X 射线晶体学 (XRC) 等光谱数据分析和解释确定的。首次从 属中分离出了羽扇醇酯衍生物 [Lup-20(29)-en-3-三十烷酸酯 ()]、单甘油酯衍生物 [1-(26-羟基二十六烷酰基)甘油 () 和甘油-1-二十六烷酸酯 ()],首次从植物来源中分离出了硫同素异位体 [环八硫 ()]. cordidepsine () 表现出显著的抗 HIV 整合酶活性,IC = 4.65 μM;茎皮的乙酸乙酯提取物、根和叶的乙酸乙酯部分对 3T3 细胞没有毒性。

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