Gastrolatathioneine,an unusual ergothioneine derivative from an aqueous extract of "tian ma":A natural product co-produced by plant and symbiotic fungus  

作　　者：Qing-Lan Guo Sheng Lin Ya-Nan Wang Cheng-Gen Zhu Cheng-Bo Xu Jian-Gong Shi 

机构地区：[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

出　　处：《Chinese Chemical Letters》2016年第10期1577-1581,共5页中国化学快报（英文版）

基　　金：Financial support from the National Natural Science Foundation of China(Nos.81502942,81522050,30825044);the National Science and Technology Project of China(Nos.2012ZX09301002-002,2011ZX09307-002-01)

摘　　要：Gastrolatathioneine （1）, an unusual natural product derived from ergothioneine, a fungal amino acid containing an imidazole-2-thione moiety, was isolated from an aqueous extract of ＂tian ma＂ （the Gastrodia elata rhizomes）. The structure of 1 including the absolute configuration was determined by extensive spectroscopic data analysis, combined with comparison of an experimental circular dichroism spectrum and calculated electronic circular dichroism spectra of stereoisomers, and confirmed by X-ray crystallography. The natural origin of 1 was proved by HPLC-ESIMS analysis of the crude extract. A biogenetic pathway of I is proposed on the basis of metabolic post-modification of ergothioneine that is biosynthesized by a symbiotic fungus. The plant and symbiotic fungus are co-uroducers of 1.Gastrolatathioneine （1）, an unusual natural product derived from ergothioneine, a fungal amino acid containing an imidazole-2-thione moiety, was isolated from an aqueous extract of ＂tian ma＂ （the Gastrodia elata rhizomes）. The structure of 1 including the absolute configuration was determined by extensive spectroscopic data analysis, combined with comparison of an experimental circular dichroism spectrum and calculated electronic circular dichroism spectra of stereoisomers, and confirmed by X-ray crystallography. The natural origin of 1 was proved by HPLC-ESIMS analysis of the crude extract. A biogenetic pathway of I is proposed on the basis of metabolic post-modification of ergothioneine that is biosynthesized by a symbiotic fungus. The plant and symbiotic fungus are co-uroducers of 1.

关 键 词：Gastrodia elataOrchidaceaeErgothioneine（＋）-L-N N-bis（4-hydroxybenzyl）ergothioneineGastrolatathioneine 

分 类 号：R282.71[医药卫生—中药学]