Novel tirucallane-type triterpenoids from Aphanamixis grandifolia

Abstract

Phytochemical investigation on the stem bark of Aphanamixis grandifolia afforded five novel tirucallane-type triterpenoids, (13α,14β,17α,23Z)-25-methoxy-21,23-epoxylanosta-7,20(22),23-triene-3,21-dione (1), (13α,14β,17α,23Z)-21,23-epoxylanosta-7,20(22),23,25-tetraene-3,21-dione (2), (3R,5R, 9R,10R,13S,14S,17S)-17-{(2R,3S,5R)-5-[(2S)-3,3-dimethyloxiran-2-yl]-2,3,4,5-tetrahydro-2,5-dimethoxyfuran-3-yl}-4,4,10,13,14-pentamethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol (3), (5R,9R,10R,13S,14S,17S)-17-{(2R,3S,5R)-5-[(2S)-3,3-dimethyloxiran-2-yl]-2,5-dimethoxytetrahydrofuran-3-yl}-1,2,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-4,4,10,13,14-pentamethyl-3H-cyclopenta[a]phenanthren-3-one (4), and (3α,13α,14β,17α,20S,23R)-23-ethoxy-3-hydroxy-21,23-epoxylanost-7-en-24-one (5). The (1) H- and (13) C-NMR spectra of all compounds were fully assigned using a combination of 2D-NMR experiments, including HSQC, HMBC, and ROESY sequences. The structure of 1 with the absolute configuration was determined by ECD calculation. Compounds 3 and 4 showed moderate activities against human MCF-7 and HeLa cancer cells.