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

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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Item Type: Article (Commonwealth Reporting Category C)
Refereed: Yes
Item Status: Live Archive
Additional Information: © 2012 Elsevier Ltd. Permanent restricted access to published version due to publisher copyright policy.
Faculty/School / Institute/Centre: Historic - Faculty of Health, Engineering and Sciences - School of Agricultural, Computational and Environmental Sciences (1 Jul 2013 - 5 Sep 2019)
Faculty/School / Institute/Centre: Historic - Faculty of Health, Engineering and Sciences - School of Agricultural, Computational and Environmental Sciences (1 Jul 2013 - 5 Sep 2019)
Date Deposited: 09 Aug 2014 08:46
Last Modified: 06 Mar 2017 05:50
Uncontrolled Keywords: Goniothalamus australis; Annonaceae; alkaloid; Pyridocoumarin; Aristolactam; Aporphine; Styryl-lactone; Goniothaline
Fields of Research (2008): 11 Medical and Health Sciences > 1115 Pharmacology and Pharmaceutical Sciences > 111504 Pharmaceutical Sciences
03 Chemical Sciences > 0306 Physical Chemistry (incl. Structural) > 030606 Structural Chemistry and Spectroscopy
03 Chemical Sciences > 0304 Medicinal and Biomolecular Chemistry > 030401 Biologically Active Molecules
03 Chemical Sciences > 0305 Organic Chemistry > 030502 Natural Products Chemistry
Fields of Research (2020): 32 BIOMEDICAL AND CLINICAL SCIENCES > 3214 Pharmacology and pharmaceutical sciences > 321405 Pharmaceutical sciences
34 CHEMICAL SCIENCES > 3403 Macromolecular and materials chemistry > 340399 Macromolecular and materials chemistry not elsewhere classified
34 CHEMICAL SCIENCES > 3404 Medicinal and biomolecular chemistry > 340401 Biologically active molecules
34 CHEMICAL SCIENCES > 3405 Organic chemistry > 340502 Natural products and bioactive compounds
Socio-Economic Objectives (2008): E Expanding Knowledge > 97 Expanding Knowledge > 970103 Expanding Knowledge in the Chemical Sciences
E Expanding Knowledge > 97 Expanding Knowledge > 970111 Expanding Knowledge in the Medical and Health Sciences
C Society > 92 Health > 9201 Clinical Health (Organs, Diseases and Abnormal Conditions) > 920109 Infectious Diseases
Identification Number or DOI: https://doi.org/10.1016/j.phytochem.2012.09.019
URI: http://eprints.usq.edu.au/id/eprint/25715

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