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

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. [ABSTRACT FROM AUTHOR]