Levrier, Claire and Balastrier, Melodie and Beattie, Karren D. and Carroll, Anthony R. and Martin, Frederic and Choomuenwai, Vanida and Davis, Rohan A. (2013) Pyridocoumarin, aristolactam and aporphine alkaloids from the Australian rainforest plant Goniothalamus australis. Phytochemistry, 86. pp. 121-126. ISSN 0031-9422
Abstract
Chemical investigation of the CH2Cl2/CH3OH extracts from aerial parts of the Australian plant Goniothalamus australis has resulted in the isolation of two pyridocoumarin alkaloids, goniothalines A (1) and B (2) as well as eight known natural products, aristolactam AII (3), enterocarpam II (4), caldensine (5), sauristolactam (6), (−)-anonaine (7), asimilobine (8), altholactone (9) and (+)-goniofufurone (10). The chemical structures of all compounds were determined by extensive spectroscopic and spectrometric analysis. Methylation of 2 using TMS-diazomethane afforded 1, which unequivocally established that both 1 and 2 possessed a 10-methyl-2H-pyrano[2,3-f]quinolin-2-one skeleton. These pyridocoumarin alkaloids are putatively proposed to arise biosynthetically from an aporphinoid precursor. Compounds 1–10 were evaluated for in vitro antimalarial activity against a chloroquine-sensitive Plasmodium falciparum line (3D7). Sauristolactam (6) and (−)-anonaine (7) exhibited the most potent antiparasitic activity with IC50 values of 9 and 7 μM, respectively.
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