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

Journal Article


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.

Publication Date


  • 2020

Citation


  • Polbuppha, I., Suthiphasilp, V., Maneerat, T., Charoensup, R., Limtharakul, T., Cheenpracha, S., . . . Laphookhieo, S. (2020). Desmoschinensisflavones A and B, two rare flavones having a hybrid benzyl benzoate ester-flavone structural framework from: Desmos chinensis Lour. RSC Advances, 10(73), 45076-45080. doi:10.1039/d0ra09985f

Scopus Eid


  • 2-s2.0-85098198342

Start Page


  • 45076

End Page


  • 45080

Volume


  • 10

Issue


  • 73

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.

Publication Date


  • 2020

Citation


  • Polbuppha, I., Suthiphasilp, V., Maneerat, T., Charoensup, R., Limtharakul, T., Cheenpracha, S., . . . Laphookhieo, S. (2020). Desmoschinensisflavones A and B, two rare flavones having a hybrid benzyl benzoate ester-flavone structural framework from: Desmos chinensis Lour. RSC Advances, 10(73), 45076-45080. doi:10.1039/d0ra09985f

Scopus Eid


  • 2-s2.0-85098198342

Start Page


  • 45076

End Page


  • 45080

Volume


  • 10

Issue


  • 73