title: 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 Fe(2+)-cysteine induced rat liver microsomal lipid peroxidation.
authors.affiliation: a 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.
authors.forename: Qing-Lan
authors.initials: QL
authors.lastname: Guo
authors.forename: Ya-Nan
authors.initials: YN
authors.lastname: Wang
authors.forename: Cheng-Gen
authors.initials: CG
authors.lastname: Zhu
authors.forename: Ming-Hua
authors.initials: MH
authors.lastname: Chen
authors.forename: Zhi-Bo
authors.initials: ZB
authors.lastname: Jiang
authors.forename: Nai-Hong
authors.initials: NH
authors.lastname: Chen
authors.forename: Xiu-Yun
authors.initials: XY
authors.lastname: Song
authors.forename: Mei-Jin
authors.initials: MJ
authors.lastname: Zhang
authors.forename: Jian-Gong
authors.initials: JG
authors.lastname: Shi
mesh_terms: D000818:Animals; D031668:Gastrodia / Q000737:chemistry*; D005978:Glutathione / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D015227:Lipid Peroxidation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D016716:PC12 Cells; D051381:Rats; D027343:Rhizome / Q000737:chemistry
chemical_list: D005978:Glutathione
keywords: 4-hydroxybenzyl-substituted glutathione derivatives; Gastrodia elata; Orchidaceae; S-(4-hydroxybenzyl)cysteine sulfoxide stereoisomers; determination of the absolute configurations; synthesis