<em>4</em>-Hydroxybenzyl-substituted amino acid derivatives from Gastrodia elata

• 作者: Chengbo Xu Chenggen Zhu Dan Zhang Huailing Wei Jiangong Shi Minghua Chen Qinglan Guo Sheng Lin Yanan Wang Zhibo Jiang
• 来源期刊: 药学学报:英文版
• 学科: 医学
• 关键词: Gastrodia elata Blume Orchidaceae 4-Hydroxybenzyl substituted amino acid derivates Pyroglutamate derivatives Inhibitory activity
• 年，卷（期）: 2015,（4）
• 页码范围: 350-357
• 页数: 8页
• 分类号: R284
• 语种: 中文

摘要

Seven new 4-hydroxybenzyl-substituted amino acid derivatives(1-7), together with 11 known compounds, were isolated from an aqueous extract of the rhizomes of Gastrodia elata Blume.Their structures were determined by spectroscopic and chemical methods. Compounds 1-3 are pyroglutamate derivatives containing 4-hydroxybenzyl units at the N atom and 4-7 are the first examples of natural products with the 4-hydroxybenzyl unit linked via a thioether bond to 2-hydroxy-3-mercaptopropanoic acid(4-6) and 2-hydroxy-4-mercaptobutanoic acid(7), which would be biogenetically derived from cysteine and homocysteine, respectively. The structures of 1 and 2 were verified by synthesis, while the absolute configurations of 4, 5 and 7 were assigned using Mosher's method based on the MPA determination rule of ΔδRS values. The known compound 4-(hydroxymethyl)-5-nitrobenzene-1,2-diol(8) exhibited activity against Fe2+-cysteine induced rat liver microsomal lipid peroxidation with IC50 values of 9.99*10-6 mol/L.