Cytotoxic flavonol-diamide [3+2] adducts from the leaves of Aglaia odorata

Abstract

Nine new flavaglines that are flavonol-diamide [3+2] adducts as well as 12 known flavaglines were isolated from the leaves of Aglaia odorata (Meliaceae). The new compounds included eight 2,3,4,5-tetrahydro-2,5-methanobenzo[b]oxepine derivatives, aglaodoratins A–H (1–8), and a tetrahydro-cyclopenta[b]benzofuran derivative, aglaodoratin I (9). X-ray single crystallographic analysis of compound 1 confirmed the structure and absolute configuration of 1. The absolute configuration of aglaodoratin I (9) was elucidated from ECD data. Aglaodoratin C (3), a rare C-10 carbonylated aglain-type derivative, demonstrated inhibition of HepG2 liver carcinoma cell proliferation via G2/M arrest and induced apoptotic cell death at a concentration of 25 μM.