Hybrid flavan-flavanones from Friesodielsia desmoides and their inhibitory activities against nitric oxide production

Authors

Pornphimol Meesakul, Mae Fah Luang University
Khanith Pudhom, Chulalongkorn University
Stephen G. Pyne, University of WollongongFollow
Surat Laphookhieo, Mae Fah Luang UniversityFollow

RIS ID

113047

Publication Details

Meesakul, P., Pudhom, K., Pyne, S. G. & Laphookhieo, S. (2017). Hybrid flavan-flavanones from Friesodielsia desmoides and their inhibitory activities against nitric oxide production. RSC Advances: an international journal to further the chemical sciences, 7 (28), 17545-17550.

Abstract

The first phytochemical investigation of Friesodielsia desmoides leaves and twigs led to the isolation and identification of three new hybrid flavan-flavanones, friesodielsones A-C (1-3), together with 18 known compounds (4-21). The structures of compounds 1-3 were elucidated through intensive analysis of spectroscopic data and their absolute configurations at C-2 and C-4 were determined by a combination of ¹H NMR and CD spectroscopy. The configuration at C-2′′ is tentatively assigned as 2′′S based on biosynthesis considerations. Compounds 2 and 15 significantly inhibited NO production with IC₅₀ values of 10.21 ± 0.074 and 7.56 ± 0.087 μM, respectively, whereas compounds 11 (IC₅₀ = 28.14 ± 0.024 μM) and 12 (IC₅₀ = 37.21 ± 0.017 μM) were moderate inhibitors.