Isolation, characterization, and xanthine oxidase inhibitory activities of flavonoids from the leaves of Perilla frutescens

Phytochemical investigation of the water extract from the leaves ofPerilla frutescens(Lamiaceae) led to the isolation of a new flavanone, a new chalcone, and a new aurone, namely, (2S)-5,7-dimethoxy-8,4'-dihydroxyflavanone (1), 2',4'-dimethoxy-4,5',6'-trihydroxychalcone (2), and (Z)-4,6-dimethoxy-7,4'-dihydroxyaurone (3), respectively. The structures were unambiguously elucidated on the basis of spectroscopic data. And the absolute configuration of1was determined by analysis of electronic circular dichroism spectrum. The isolated compounds were evaluated for their inhibitory effects on xanthine oxidasein vitro. Among them,2showed more potent activity than the positive control allopurinol, a well-known XO inhibitor clinically used for treatment of gout. Lineweaver-Burk transformation of the inhibition kinetics data demonstrated that it was a mixed-type inhibitor. [GRAPHICS] .