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利用 DFT 计算和 POM 分析研究侧柏黄酮类化合物对细胞的毒性:药效团的对接和鉴定。

DFT calculations and POM analyses of cytotoxicity of some flavonoids from aerial parts of Cupressus sempervirens: Docking and identification of pharmacophore sites.

机构信息

Chemistry Department, Faculty of Science, Northern Borders University, Arar, Saudi Arabia; Ecophysiology Unit, Plant Ecology and Ranges Department, Desert Research Center, Cairo, Egypt.

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Umm AlQura University, Makkah 21955, Saudi Arabia.

出版信息

Bioorg Chem. 2020 Jul;100:103850. doi: 10.1016/j.bioorg.2020.103850. Epub 2020 Apr 25.

DOI:10.1016/j.bioorg.2020.103850
PMID:32460177
Abstract

Two known polyphenols named apigenin 7-O-β-d-glucopyranoside (S1) and querctine-3-O-glucoside (S2), along with another two new compounds apigenin 4'-geranyl-8-glucopyranosyl-7-O-α-glucopyranoside (S3) and apigenin 4'-pernyl-8-glucopyranosyl -7-O-α-glucopyranoside (S4), were isolated from the leaves of Cupressus sempervirens. Structure elucidation of the isolated polyphenols was established on the basis of detailed spectroscopic analysis like 1D and 2D NMR analyses including H NMR, C NMR, COSY, DEPT, HMQC, UV, and Electron Spray Ionization Mass Spectroscopy (ESI-MS). Density Functional Theory (DFT) of computational, Petra/Osiris/Molinspiration (POM), and docking analyses methods were applied in the structural validation of new isolated compounds. The isolated compounds S1-S4 showed significant cytotoxicity against human hepatocellular liver carcinoma HepG2 cells, MCF-7, HC116 and A549.

摘要

从柏树叶中分离得到两种已知的多酚,分别为芹菜素 7-O-β-d-吡喃葡萄糖苷(S1)和槲皮素-3-O-葡萄糖苷(S2),以及另外两种新化合物芹菜素 4'-香叶基-8-吡喃葡萄糖基-7-O-α-吡喃葡萄糖苷(S3)和芹菜素 4'-对伞花烃基-8-吡喃葡萄糖基-7-O-α-吡喃葡萄糖苷(S4)。通过详细的光谱分析,如 1D 和 2D NMR 分析(包括 1H NMR、13C NMR、COSY、DEPT、HMQC、UV 和电喷雾电离质谱(ESI-MS)),确定了分离得到的多酚的结构。应用密度泛函理论(DFT)的计算、Petra/Osiris/Molinspiration(POM)和对接分析方法对新分离化合物的结构进行了验证。分离得到的化合物 S1-S4 对人肝癌 HepG2 细胞、MCF-7、HC116 和 A549 具有显著的细胞毒性。

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