Journal
PHYTOCHEMISTRY
Volume 86, Issue -, Pages 121-126Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2012.09.019
Keywords
Goniothalamus australis; Annonaceae; Alkaloid; Pyridocoumarin; Aristolactam; Aporphine; Styryl-lactone; Goniothaline
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Funding
- The Australian Research Council [LE0668477, LE0237908]
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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 mu M, respectively. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.
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