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A highly selective C-rhamnosyltransferase from Viola tricolor and insights into its mechanisms
Acta Pharmaceutica Sinica B ; (6): 3535-3544, 2023.
Article en En | WPRIM | ID: wpr-1011113
Biblioteca responsable: WPRO
ABSTRACT
C-Glycosides are important natural products with various bioactivities. In plant biosynthetic pathways, the C-glycosylation step is usually catalyzed by C-glycosyltransferases (CGTs), and most of them prefer to accept uridine 5'-diphosphate glucose (UDP-Glc) as sugar donor. No CGTs favoring UDP-rhamnose (UDP-Rha) as sugar donor has been reported, thus far. Herein, we report the first selective C-rhamnosyltransferase VtCGTc from the medicinal plant Viola tricolor. VtCGTc could efficiently catalyze C-rhamnosylation of 2-hydroxynaringenin 3-C-glucoside, and exhibited high selectivity towards UDP-Rha. Mechanisms for the sugar donor selectivity of VtCGTc were investigated by molecular dynamics (MD) simulations and molecular mechanics with generalized Born and surface area solvation (MM/GBSA) binding free energy calculations. Val144 played a vital role in recognizing UDP-Rha, and the V144T mutant could efficiently utilize UDP-Glc. This work provides a new and efficient approach to prepare flavonoid C-rhamnosides such as violanthin and iso-violanthin.
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Texto completo: 1 Índice: WPRIM Idioma: En Revista: Acta Pharmaceutica Sinica B Año: 2023 Tipo del documento: Article
Texto completo: 1 Índice: WPRIM Idioma: En Revista: Acta Pharmaceutica Sinica B Año: 2023 Tipo del documento: Article