INVESTIGADORES
FERRER Evelina Gloria
artículos
Título:
Theoretical investigation of the conformational space of baicalin
Autor/es:
J.J. MARTÍNEZ MEDINA; E.G.FERRER; P.A.M. WILLIAMS; N.B. OKULIK
Revista:
JOURNAL OF MOLECULAR GRAPHICS & MODELLING.
Editorial:
ELSEVIER SCIENCE INC
Referencias:
Lugar: Amsterdam; Año: 2017 vol. 76 p. 181 - 191
ISSN:
1093-3263
Resumen:
Flavonoids are a large group of polyphenolic compounds ubiquitously present in plants. They are impor-tant components of human diet. They are recognized as potential drug candidates to be used in thetreatment and prevention of a lot of pathological disorders, due to their protective effects. Baicalin (7-glucuronic acid 5, 6-dihydroxyflavone) is one of the main single active constituents isolated from thedried roots of Scutellaria baicalensis Georgi. The great interest on this flavonoid is due to its various phar-macological properties, such as antioxidant, antimicrobial, anti-inflammatory, anticancer and so on, andits high accumulation in the roots of S. baicalensis. The aim of our work was to analyze the geomet-ric and electronic properties of baicalin conformers (BCL), thus performing a complete search on theconformational space of this flavonoid in gas phase and in aqueous solution. The results indicate thatthe conformational space of baicalin is formed by eight conformers in gas phase and five conformers inaqueous solution optimized at B3LYP/6-311++G** theory level. BCLa2TTand BCLa1TTconformers have lowstability in gas phase and very high stability in aqueous solution. This variation is related to a modificationin the 1angle that represents the relative position of the glucuronide unit respect to the central rings ofthe flavan nucleus (A and C). This modification was successfully explained by examining the changes inthe hydrogen bond (HB) interactions that occur in the region around the hydroxyl group located in posi-tion 6 of ring A. Besides, the molecular electrostatic potential (MEP) and frontier molecular orbital (FMO)analyses indicate that BCLa2TTand BCLa1TTconformers are the most favorable conformers for interactingwith positively charged species (such as metal ions) in aqueous media (such as biological fluids).