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从木通中分离得到三种具有白细胞介素-6抑制活性的新木脂素糖苷。

Three new lignan glycosides with IL-6 inhibitory activity from Akebia quinata.

作者信息

Jin Hong-Guang, Kim A Ryun, Ko Hae Ju, Lee Sang Kook, Woo Eun-Rhan

机构信息

College of Pharmacy, Chosun University.

出版信息

Chem Pharm Bull (Tokyo). 2014;62(3):288-93. doi: 10.1248/cpb.c13-00668.

Abstract

Three new lignan glycosides, akeqintoside A [(7S,8S)-7,8-dihydro-8-hydroxymethyl-7-(4-hydroxy-3-methoxyphenyl)-1'-benzofuranpropanol 2'-O-β-D-glucopyranoside] (1), akeqintoside B [(7R,8R)-7,8-dihydro-8-hydroxymethyl-7-(4-hydroxy-3-methoxyphenyl)-1'-(9'-methoxy-7'-propenyl) benzofuran 2'-O-β-D-glucopyranoside] (2), and akequintoside C [7R*,8R*-dihydroxy-7-(4-hydroxy-3-methoxyphenyl)-glycerol 9-O-β-D-(6'-O-caffeoyl)-glucopyranoside] (3) were isolated from Akebia quinata along with five known compounds, syringin (4), vanilloloside (5), salidroside (6), 3,4-dihydroxyphenylethyl alcohol 8-O-β-D-glucopyranoside (7), and calceolarioside B (8). The structures of the compounds were identified based on one dimensional (1D)- and 2D-NMR, including (1)H-(1)H correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC) and nuclear Overhauser effect spectroscopy (NOESY) spectroscopic analyses. The inhibitory activity of these isolated compounds against interleukin-6 (IL-6) production in tumor necrosis factor-alpha (TNF-α) stimulated MG-63 cells was also examined.

摘要

从木通中分离得到3个新的木脂素糖苷,即木通苷A [(7S,8S)-7,8-二氢-8-羟甲基-7-(4-羟基-3-甲氧基苯基)-1'-苯并呋喃丙醇2'-O-β-D-吡喃葡萄糖苷](1)、木通苷B [(7R,8R)-7,8-二氢-8-羟甲基-7-(4-羟基-3-甲氧基苯基)-1'-(9'-甲氧基-7'-丙烯基)苯并呋喃2'-O-β-D-吡喃葡萄糖苷](2)和木通苷C [7R*,8R*-二羟基-7-(4-羟基-3-甲氧基苯基)-甘油9-O-β-D-(6'-O-咖啡酰基)-吡喃葡萄糖苷](3),以及5个已知化合物,紫丁香苷(4)、香草醇苷(5)、红景天苷(6)、3,4-二羟基苯乙醇-8-O-β-D-吡喃葡萄糖苷(7)和柳穿鱼苷B(8)。通过一维(1D)和二维(2D)核磁共振,包括氢-氢相关光谱(COSY)、异核单量子相干(HSQC)、异核多键连接(HMBC)和核Overhauser效应光谱(NOESY)光谱分析确定了这些化合物的结构。还检测了这些分离化合物对肿瘤坏死因子-α(TNF-α)刺激的MG-63细胞中白细胞介素-6(IL-6)产生的抑制活性。

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