Pyridocoumarin, aristolactam and aporphine alkaloids from the Australian rainforest plant Goniothalamus australis

Article

Levrier, Claire, Balastrier, Melodie, Beattie, Karren D., Carroll, Anthony R., Martin, Frederic, Choomuenwai, Vanida and Davis, Rohan A.. 2013. "Pyridocoumarin, aristolactam and aporphine alkaloids from the Australian rainforest plant Goniothalamus australis." Phytochemistry: the international journal of plant chemistry, plant biochemistry and molecular biology. 86, pp. 121-126. https://doi.org/10.1016/j.phytochem.2012.09.019
Article Title

Pyridocoumarin, aristolactam and aporphine alkaloids from the Australian rainforest plant Goniothalamus australis

ERA Journal ID1371
Article CategoryArticle
AuthorsLevrier, Claire (Author), Balastrier, Melodie (Author), Beattie, Karren D. (Author), Carroll, Anthony R. (Author), Martin, Frederic (Author), Choomuenwai, Vanida (Author) and Davis, Rohan A. (Author)
Journal TitlePhytochemistry: the international journal of plant chemistry, plant biochemistry and molecular biology
Journal Citation86, pp. 121-126
Number of Pages6
Year2013
PublisherElsevier
Place of PublicationKidlington, OX. United Kingdom
ISSN0031-9422
1873-3700
Digital Object Identifier (DOI)https://doi.org/10.1016/j.phytochem.2012.09.019
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.

KeywordsGoniothalamus australis; Annonaceae; alkaloid; Pyridocoumarin; Aristolactam; Aporphine; Styryl-lactone; Goniothaline
ANZSRC Field of Research 2020321405. Pharmaceutical sciences
340399. Macromolecular and materials chemistry not elsewhere classified
340401. Biologically active molecules
340502. Natural products and bioactive compounds
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Byline AffiliationsGriffith University
Institution of OriginUniversity of Southern Queensland
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