4-Hydroxybenzyl-substituted glutathione derivatives from Gastrodia elata

Abstract

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 Fe²⁺-cysteine induced rat liver microsomal lipid peroxidation.

Keywords::

• Gastrodia elata
• Orchidaceae
• 4-hydroxybenzyl-substituted glutathione derivatives
• determination of the absolute configurations
• S-(4-hydroxybenzyl)cysteine sulfoxide stereoisomers
• synthesis

Acknowledgement

We thank the Chinese Academy of Medical Sciences & Peking Union Medical College High Performance Computing Platform for the calculation of the ECD spectra.

Disclosure statement

No potential conflict of interest was reported by the authors.

Supplemental data

The supplemental data for this article can be accessed at http://dx.doi.org/10.1080/10286020.2015.1040000

Notes

We dedicate this paper to Prof. Xin-Sheng Yao on the occasion of his 80th birthday

Additional information

Funding

Financial support from the National Natural Sciences Foundation of China (NNSFC; [grant number 30825044] and [grant number 20932007]), the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT, [grant number IRT1007]), and the National Science and Technology Project of China ([grant number 2012ZX09103101-001] and [grant number 2012ZX09301002-002]) is acknowledged.