Bioassay-Guided Isolation of Flavonoids from 𝐹�𝑙�𝑒�𝑚�𝑖�𝑛�𝑔�𝑖�𝑎� 𝑚�𝑎�𝑐�𝑟�𝑜�𝑝�ℎ𝑦�𝑙�𝑙�𝑎� and Their Cytotoxic and Antioxidant Activities

Abstract

Chalcone derivatives are one of the main flavonoid groups in the genus Flemingia. Generally, Flemingia chalcones have unusual oxygenation patterns, prenyl, and geranyl chains and exhibit cytotoxic and antioxidant activities. The research aims to isolate geranylated chalcone from Flemingia macrophylla leaves and evaluate the cytotoxic and radical scavenging activities. Extraction of geranylated chalcones from F. macrophylla leaves using maceration with methanol. Separation and purification process using gravity column and planar radial chromatography resulted in deoxyhomofleminigin and 3-hydroxyflemingin A. HR-ESI-MS, UV, 1D, and 2D NMR determined the structure of geranylated chalcones. 3-Hydroxyflemingin A shows high activity toward Hela and T47D cells (IC50 values 1.98 and 0.20 µg/mL, respectively). The antioxidant effects of deoxyhomofleminigin and 3-hydroxyflemingin A against DPPH radicals also demonstrated strong activity.