Desmoschinensisflavones A and B, two rare flavones having a hybrid benzyl benzoate ester-flavone structural framework from Desmos chinensis Lour

Abstract

Two rare flavones having a hybrid benzyl benzoate ester-flavone structural framework, desmoschinensisflavones A and B (1 and 2), together with 12 known compounds (3–14) were isolated from the fruit, leaf, and twig extracts of Desmos chinensis (red flower). The new structures were characterized by UV, IR, NMR, and HRESITOFMS data. Desmoschinensisflavones A and B have a distinctive skeleton of benzoate ester-flavones with a C-4′′ and C-6 and C-8 connection via a methylene group, respectively. Plausible biosynthesis pathways to compounds 1 and 2 are proposed based on an intermolecular nucleophilic 1,4-addition to ortho-quinone intermediates. Compounds 6–8 and 12 showed weakly antioxidant inhibition with IC₅₀ values in the range of 65.4–74.6 μM.