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槲寄生中的二芳基庚烷类化合物和类黄酮通过抑制 LPS 刺激的骨髓来源树突状细胞产生促炎细胞因子。

Diarylheptanoids and flavonoids from viscum album inhibit LPS-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells.

机构信息

College of Pharmacy, Yonsei Institute of Pharmaceutical Sciences, Yonsei University, Incheon 406-840, Korea.

出版信息

J Nat Prod. 2013 Apr 26;76(4):495-502. doi: 10.1021/np300490v. Epub 2013 Mar 13.

DOI:10.1021/np300490v
PMID:23484668
Abstract

Three new diarylheptanoids, (3S,5R)-3-hydroxy-5-methoxy-1,7-bis(4-hydroxyphenyl)-6E-heptene (1), (3S,5S)-3-hydroxy-5-methoxy-1,7-bis(4-hydroxyphenyl)-6E-heptene (2), and (3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one (3), four new flavonoid glycosides, 3,7,3'-tri-O-methylquercetin-4'-O-β-d-apiofuranosyl-(1→2)-O-β-d-glucopyranoside (4), 7,3'-di-O-methylquercetin-4'-O-β-d-glucopyranosyl-3-O-[6‴-(3-hydroxy-3-methylglutaroyl)]-α-d-glucopyranoside (5), 7,3'-di-O-methylquercetin-4'-O-β-d-glucopyranosyl-3-O-[(6'''''→5'''')-O-1'''''-(sinap-4-yl)-β-d-glucopyranosyl-6‴-(3-hydroxy-3-methylglutaroyl)]-α-d-glucopyranoside (6), and (2S)-5-hydroxy-7,3'-dimethoxyflavanone-4'-O-β-d-apiofuranosyl-(1→5)-O-β-d-apiofuranosyl-(1→2)-O-β-d-glucopyranoside (9), and 17 known compounds were isolated from the leaves and twigs of Viscum album. Compounds 1, 4, and 19 significantly inhibited LPS-stimulated production of TNF-α, IL-6, and IL-12p40 with IC50 values ranging from 0.09 ± 0.01 to 8.96 ± 0.45 μM. (+)-Medioresinol (13) showed inhibitory effects on LPS-stimulated production of IL-12p40 with an IC50 value of 2.00 ± 0.15 μM.

摘要

三种新的二芳基庚烷类化合物,(3S,5R)-3-羟基-5-甲氧基-1,7-双(4-羟基苯基)-6E-庚烯(1)、(3S,5S)-3-羟基-5-甲氧基-1,7-双(4-羟基苯基)-6E-庚烯(2)和(3S)-3-羟基-1,7-双(4-羟基苯基)-6E-庚烯-5-酮(3),四种新的类黄酮糖苷,3,7,3'-三-O-甲基槲皮素-4'-O-β-D-阿洛呋喃糖基-(1→2)-O-β-D-吡喃葡萄糖苷(4)、7,3'-二-O-甲基槲皮素-4'-O-β-D-吡喃葡萄糖基-3-O-[6‴-(3-羟基-3-甲基戊二酰基)]-α-D-吡喃葡萄糖苷(5)、7,3'-二-O-甲基槲皮素-4'-O-β-D-吡喃葡萄糖基-3-O-[(6'''→5'''')-O-1'''''-(芥子酰基)-β-D-吡喃葡萄糖基-6‴-(3-羟基-3-甲基戊二酰基)]-α-D-吡喃葡萄糖苷(6)和(2S)-5-羟基-7,3'-二甲氧基黄烷酮-4'-O-β-D-阿洛呋喃糖基-(1→5)-O-β-D-阿洛呋喃糖基-(1→2)-O-β-D-吡喃葡萄糖苷(9),以及 17 种已知化合物从槲寄生的叶子和小枝中分离得到。化合物 1、4 和 19 对 LPS 刺激的 TNF-α、IL-6 和 IL-12p40 的产生具有显著的抑制作用,IC50 值范围为 0.09 ± 0.01 至 8.96 ± 0.45 μM。(+)-medioresinol (13)对 LPS 刺激的 IL-12p40 产生具有抑制作用,IC50 值为 2.00 ± 0.15 μM。

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