Title
Gastrolatathioneine, an unusual ergothioneine derivative from an aqueous extract of “Tian ma”: A natural product co-produced by plant and symbiotic fungus
Author
Qing-Lan Guo, Sheng Lin, Ya-Nan Wang, Cheng-Gen Zhu, Cheng-Bo Xu, Jian-Gong Shi
Year
2016
Journal
Chinese Chemical Letters
Abstract
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 1 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-producers of 1.
Instrument
J-810
Keywords
Circular dichroism, Absolute configuration, Medicinal