Enhancement of the antiplasmodial activity of quassin by transformation into a gamma-lactone

Lang'At-Thoruwa, C; Kirby, GC; Phillipson, JD; Warhurst, DC; Watt, RA; Wright, CW; (2003) Enhancement of the antiplasmodial activity of quassin by transformation into a gamma-lactone. Journal of natural products, 66 (11). pp. 1486-1489. ISSN 0163-3864 DOI: https://doi.org/10.1021/np030107a

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The naturally occurring bitter principle quassin (1) was converted chemically into the gamma-lactone quassilactone (13) in an attempt to enhance, its antiplasmodial activity. The in vitro antiplasmodial activity of 13 against Plasmodium falciparum (K1) (IC50 = 23 muM) was 40-fold greater than that of 1. However, one of the intermediates, compound 8, the 15beta-hydroxy,16-O-m-chlorobenzoyl analogue of 1, was 506-fold more active than I against P. falciparum (IC50 = 1.8 muM) and only 3-fold less potent than chloroquine. In addition, 8 displayed the best cytotoxic/antiplasmodial ratio (112) of all of the compounds tested. In the course of this work a dimer, neoquassin ether (6), linked at C-16 was also prepared; 6 was found to have weak antiplasmodial activity (IC50 = 9.7 muM).

Item Type: Article
Keywords: Semisynthetic derivatives
Faculty and Department: Faculty of Infectious and Tropical Diseases > Dept of Pathogen Molecular Biology
Research Centre: Malaria Centre
PubMed ID: 14640524
Web of Science ID: 186912400016
URI: http://researchonline.lshtm.ac.uk/id/eprint/15170


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