A New Ellagic Acid From the Leaves and Twigs of Irvingia malayana

A phytochemical investigation of the leaves and twigs of Irvingia malayana led to the isolation of a new 3,3′,4′-tri-O-methylellagic acid-6″-acetoxy-4-O-β-glucoside (1), along with 3,3′,4′-tri-O-methylellagic acid (2), 3,3′-di-O-methylellagic acid-4-O-β-xyloside (3), 3,3′,4′-tri-O-methylellagic acid-4-β-O-glucoside (4), friedelin (5), friedelinol (6), methyl-3,4,5-trihydroxybenzoate (7), 5,7,4′-trihydroxyflavone-8-C-β-glucopyranoside (8), 5,7,3′,4′-tetrahydroxyflavone-8-C-β-glucopyranoside (9), and 5,3′,4′-trihydroxyflavone-6-C-β-glucopyranoside (10). Their structures were elucidated by means of spectroscopic techniques and direct comparison with literature data. Compounds 4 and 7 showed weak cytotoxic activity against a panel of mammalian cancerous cell lines. Furthermore, compounds 1, 2, 4, and 9 exhibited significant inhibitory activity in the syncytium inhibition assay, whereas compounds 8 and 9 displayed moderate activity in the HIV 1 reverse transcriptase assay.