4-Hydroxybenzyl-substituted amino acid derivatives from Gastrodia elata.

Qinglan Guo; Yanan Wang; Sheng Lin; Chenggen Zhu; Minghua Chen; Zhibo Jiang; Chengbo XU; Dan Zhang; Huailing Wei; Jiangong Shi

Return

4-Hydroxybenzyl-substituted amino acid derivatives from Gastrodia elata.

Author: Qinglan GUO ¹ ; Yanan WANG ¹ ; Sheng LIN ¹ ; Chenggen ZHU ¹ ; Minghua CHEN ¹ ; Zhibo JIANG ¹ ; Chengbo XU ¹ ; Dan ZHANG ¹ ; Huailing WEI ¹ ; Jiangong SHI ¹
Author Information

1. State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
Publication Type:Journal Article
Keywords: 4-Hydroxybenzyl- substituted amino acid derivatives; Gastrodia elata Blume; Inhibitory activity; Orchidaceae; Pyroglutamate deriva tives
From: Acta Pharmaceutica Sinica B 2015;5(4):350-357
CountryChina
Language:English
Abstract: 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 Δδ RS values. The known compound 4-(hydroxymethyl)-5-nitrobenzene-1,2-diol (8) exhibited activity against Fe(2+)-cysteine induced rat liver microsomal lipid peroxidation with IC50 values of 9.99×10(-6) mol/L.