4-Hydroxybenzyl-substituted glutathione derivatives from Gastrodia elata.
J Asian Nat Prod Res
; 17(5): 439-54, 2015 May.
Article
em En
| MEDLINE
| ID: mdl-26013819
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.
Palavras-chave
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Gastrodia
/
Glutationa
Limite:
Animals
Idioma:
En
Revista:
J Asian Nat Prod Res
Assunto da revista:
BOTANICA
/
QUIMICA
Ano de publicação:
2015
Tipo de documento:
Article
País de afiliação:
China