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来自葱莲的具有潜在抗炎活性的黄烷类化合物。

Flavans with potential anti-inflammatory activities from Zephyranthes candida.

作者信息

Zhan Guanqun, Zhou Junfei, Liu Tingting, Zheng Guijuan, Aisa Haji Akber, Yao Guangmin

机构信息

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.

The Key Laboratory of Plant Resources and Chemistry of Arid Zone and State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, People's Republic of China.

出版信息

Bioorg Med Chem Lett. 2016 Dec 15;26(24):5967-5970. doi: 10.1016/j.bmcl.2016.10.081. Epub 2016 Oct 28.

DOI:10.1016/j.bmcl.2016.10.081
PMID:27825545
Abstract

Three new flavans, (2R,3R)-7-methoxy-flavan-3-ol (1), (2S)-7,3'-dihydroxy-4'-methoxyflavan 3'-O-β-d-glucopyranoside (2), (2S)-7,3'-dihydroxy-4'-methoxyflavan 7-O-β-d-glucopyranoside (3), and one known flavan (4) were isolated from the whole plants of Zephyranthes candida (Amaryllidacea). The structures of the new flavans 1-3 were determined by extensive spectroscopic analyses including HRESIMS, NMR, and electronic circular dichroism (ECD), and the absolute configuration of 1 was confirmed by single-crystal X-ray diffraction analysis with Cu Kα irradiation. Flavans 1-3 displayed significant inhibitory effects on the LPS-induced NO production in RAW264.7 mouse macrophages with IC values of 17.34, 16.14, and 21.52μM, respectively, suggesting their potentials for anti-inflammatory agents.

摘要

从葱莲(石蒜科)全草中分离得到三种新的黄烷类化合物,即(2R,3R)-7-甲氧基黄烷-3-醇(1)、(2S)-7,3'-二羟基-4'-甲氧基黄烷3'-O-β-D-吡喃葡萄糖苷(2)、(2S)-7,3'-二羟基-4'-甲氧基黄烷7-O-β-D-吡喃葡萄糖苷(3)以及一种已知的黄烷类化合物(4)。通过包括高分辨电喷雾电离质谱(HRESIMS)、核磁共振(NMR)以及电子圆二色光谱(ECD)等广泛的光谱分析确定了新黄烷类化合物1-3的结构,并且通过Cu Kα辐射的单晶X射线衍射分析证实了1的绝对构型。黄烷类化合物1-3对脂多糖(LPS)诱导的RAW264.7小鼠巨噬细胞中一氧化氮(NO)的产生显示出显著的抑制作用,其半数抑制浓度(IC)值分别为17.34、16.14和21.52μM,表明它们具有作为抗炎剂的潜力。

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