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4-Hydroxybenzyl-substituted glutathione derivatives from Gastrodia elata

Guo, Qing-Lan, Wang, Ya-Nan, Zhu, Cheng-Gen, Chen, Ming-Hua, Jiang, Zhi-Bo, Chen, Nai-Hong, Song, Xiu-Yun, Zhang, Mei-Jin, Shi, Jian-Gong
Journal of Asian natural products research 2015 v.17 no.5 pp. 439-454
Gastrodia elata, blood serum, cysteine, glutathione, iron, lipid peroxidation, liver, nuclear magnetic resonance spectroscopy, rats, rhizomes, spectral analysis, stereoisomers
Seven new 4-hydroxybenzyl-substituted glutathione derivatives (2 – 8), together with a known analogue (1), were isolated from the aqueous extract of Gastrodia elata Blume rhizomes. Their structures were determined by using spectroscopic and chemical methods. The absolute configurations of 1 – 8 were assigned by using Marfey's method, combined with comparing the NMR and CD spectroscopic data of sulfoxide moieties in 3 – 6 with those of S -(4-hydroxybenzyl)cysteine sulfoxide stereoisomers (9 – 12) synthesized as authentic samples. The configurations of 9 – 12 were confirmed by electronic CD calculations based on the quantum-mechanical time-dependent density functional theory. Furthermore, the structures of 1 , 3 , 5 , 7 , and 8 were verified by synthesis. Compound 3 was active against serum deprivation-induced PC12 cell damage and synthetic 9 – 14 exhibited activity against Fe ²⁺-cysteine induced rat liver microsomal lipid peroxidation.