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朝鲜连翘花中的新木脂素及其对MOVAS细胞中VCAM-1表达的抑制作用。

New Lignans from the Flower of Forsythia koreana and Their Suppression Effect on VCAM-1 Expression in MOVAS Cells.

作者信息

Lee Yeong-Geun, Jang Seon-A, Seo Kyeong-Hwa, Gwag Jung Eun, Kim Hyoung-Geun, Ko Jung-Hwan, Ji So-Ae, Kang Se-Chan, Lee Dae Young, Baek Nam-In

机构信息

Graduate School of Biotechnology, Kyung Hee University, Yongin, 17104, Korea.

Biological and Genetic Resources Utilization Division, National Institute of Biological Resources, Incheon, 22689, Korea.

出版信息

Chem Biodivers. 2018 Apr;15(4):e1800026. doi: 10.1002/cbdv.201800026. Epub 2018 Apr 17.

Abstract

Six lignans including two new lignans were obtained as the principal components of the Forsythia koreana flowers via silica gel (SiO ), octadecyl SiO (ODS) as well as Sephadex LH-20 column chromatography. In addition to two new lignans, named koreanaside A ((7R,8S,7'R,8'S)-7,7'-diepoxy-5'-hydroxy-3,3'-dimethoxylignan 4-O-β-d-glucopyranoside) and koreanaside B ((7R,8S,7'S,8'R)-7,9'-epoxy-9,5',7'-trihydroxy-3,3'-dimethoxylignan 4-O-β-d-glucopyranoside), four known lignans were identified to be (+)-phylligenin, (-)-epipinoresinol, pinoresinol, and tinosposide A. The structures and absolute configurations of koreanasides A and B were established by means of analysis of spectroscopic data (NMR, IR, FAB-MS, and CD), whereas the structures of known lignans were identified by comparison their NMR and MS values with those in the reported literature. Their chemical structures including configuration were established by means of analysis of spectroscopic data (NMR, IR, FAB-MS, and CD) but also comparison of their NMR and MS values with those in the reported literature. This is the first article for isolation of six lignans of F. koreana flowers. Koreanasides A and B showed high radical scavenging activity with oxygen radical absorbance capacity (ORAC) values of 0.97 ± 0.01 and 1.02 ± 0.01, respectively. Koreanaside A also prohibited expressing VCAM-1 in MOVAS cells with 80.5% at 25 mg/mL.

摘要

通过硅胶(SiO₂)、十八烷基硅胶(ODS)以及葡聚糖凝胶LH - 20柱色谱法,从连翘花中获得了六种木脂素,其中包括两种新木脂素,它们是连翘花的主要成分。除了两种新木脂素,分别命名为连翘苷A((7R,8S,7'R,8'S)-7,7'-二环氧-5'-羟基-3,3'-二甲氧基木脂素4 - O-β - D - 吡喃葡萄糖苷)和连翘苷B((7R,8S,7'S,8'R)-7,9'-环氧-9,5',7'-三羟基-3,3'-二甲氧基木脂素4 - O-β - D - 吡喃葡萄糖苷)外,还鉴定出四种已知木脂素为(+)-叶下珠素、(-)-表松脂醇、松脂醇和锡诺普苷A。连翘苷A和B的结构及绝对构型通过光谱数据分析(核磁共振、红外光谱、快原子轰击质谱和圆二色光谱)得以确定,而已知木脂素的结构则通过将其核磁共振和质谱值与文献报道的值进行比较来鉴定。它们的化学结构包括构型不仅通过光谱数据分析(核磁共振、红外光谱、快原子轰击质谱和圆二色光谱)得以确定,还通过将其核磁共振和质谱值与文献报道的值进行比较来确定。这是关于从连翘花中分离出六种木脂素的第一篇文章。连翘苷A和B表现出较高的自由基清除活性,氧自由基吸收能力(ORAC)值分别为0.97±0.01和1.02±0.01。连翘苷A在25mg/mL时还能抑制MOVAS细胞中血管细胞黏附分子-1(VCAM - 1)的表达,抑制率为80.5%。

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