Antimalarial beta-carbolines from the New Zealand ascidian Pseudodistoma opacum

Chan, S. T. and Pearce, A. N. and Page, M. J. and Kaiser, M. and Copp, B. R.. (2011) Antimalarial beta-carbolines from the New Zealand ascidian Pseudodistoma opacum. Journal of natural products, Vol. 74, H. 9. pp. 1972-1979.

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Official URL: http://edoc.unibas.ch/dok/A6002109

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One tetrahydro-beta-carboline, (-)-7-bromohomotrypargine (1), and three alkylguanidine-substituted beta-carbolines, opacalines A, B, and C (2-4), have been isolated from the New Zealand ascidian Pseudodistoma opacum. The structures of the metabolites were determined by analysis of mass spectrometric and 2D NMR spectroscopic data. Natural products 2 and 3, synthetic debromo analogues 8 and 9, and intermediate 16 exhibited moderate antimalarial activity toward a chloroquine-resistant strain of Plasmodium falciparum, with an IC(50) range of 2.5-14 muM. The biosynthesis of 1-4 is proposed to proceed via a Pictet-Spengler condensation of 6-bromotryptamine and the alpha-keto acid transamination product of either arginine or homoarginine. Cell separation and (1)H NMR analysis of P. opacum identified tetrahydro-beta-carboline 1 to be principally located in the zooids, while fully aromatized analogues 2-4 were localized to the test
Faculties and Departments:09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology (MPI) > Parasite Chemotherapy (Mäser)
UniBasel Contributors:Kaiser, Marcel
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Society of Pharmacognosy
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:08 Nov 2012 16:22
Deposited On:08 Nov 2012 16:09

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