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来自中华木瓜嫩枝的生物活性三萜类化合物。

Bioactive Triterpenoids from the Twigs of Chaenomeles sinensis.

作者信息

Kim Chung Sub, Subedi Lalita, Oh Joonseok, Kim Sun Yeou, Choi Sang Un, Lee Kang Ro

机构信息

Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University , Suwon 16419, Republic of Korea.

Gachon Institute of Pharmaceutical Science, Gachon University , Incheon 21936, Republic of Korea.

出版信息

J Nat Prod. 2017 Apr 28;80(4):1134-1140. doi: 10.1021/acs.jnatprod.7b00111. Epub 2017 Mar 30.

Abstract

Chaenomeles sinensis has been consumed traditionally for the treatment of throat diseases, diarrhea, inflammatory diseases, and dry beriberi. Repeated chromatography of the CHCl-soluble fraction from the 80% MeOH extract of C. sinensis twigs led to the isolation of three new triterpenoids, sinenic acid A (1), 3β-O-cis-feruloyl-2α,19α-dihydroxyurs-12-en-28-oic acid (2), and 3β-O-cis-caffeoylbetulin (3), together with 20 analogues. The chemical structures of 1-3 were determined using diverse NMR techniques and HRMS data analysis, chemical methods, and computational approaches supported by advanced statistics (CP3). All the purified compounds were evaluated not only for their cytotoxicity against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) but for their potential neuroprotective effects through induction of nerve growth factor in C6 glioma cells. Their anti-inflammatory effects were also assessed by measuring nitric oxide levels in lipopolysaccharide-insulted murine microglia BV2 cells.

摘要

传统上,人们食用中华木瓜来治疗咽喉疾病、腹泻、炎症性疾病和干性脚气病。对中华木瓜嫩枝80%甲醇提取物的氯仿可溶部分进行反复色谱分离,得到了三种新的三萜类化合物,即中华酸A(1)、3β-O-顺式阿魏酰基-2α,19α-二羟基乌苏-12-烯-28-酸(2)和3β-O-顺式咖啡酰桦木醇(3),以及20种类似物。通过多种核磁共振技术和高分辨质谱数据分析、化学方法以及先进统计学支持的计算方法(CP3)确定了1-3的化学结构。所有纯化的化合物不仅针对四种人类肿瘤细胞系(A549、SK-OV-3、SK-MEL-2和HCT-15)评估了其细胞毒性,还通过在C6胶质瘤细胞中诱导神经生长因子评估了其潜在的神经保护作用。还通过测量脂多糖刺激的小鼠小胶质细胞BV2细胞中的一氧化氮水平来评估它们的抗炎作用。

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