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Unusual antimalarial meroditerpenes from tropical red macroalgae

Stout, E.P. and Prudhomme, J. and Le Roch, K. and Fairchild, C.R. and Franzblau, S.G. and Aalbersberg, William G.L. and Hay, M.E. and Kubanek, J. (2010) Unusual antimalarial meroditerpenes from tropical red macroalgae. Bioorganic & Medicinal Chemistry Letters, 20 (19). pp. 5662-5665. ISSN 0960-894X

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Three antimalarial meroditerpenes have been isolated from two Fijian red macroalgae. The absolute stereochemistry of callophycolide A (1), a unique macrolide from Callophycus serratus, was determined using a combination of Mosher’s ester analysis, circular dichroism analysis with a dimolybdenum tetraacetate complex, and conformational analysis using NOEs. In addition, two known tocopherols, β-tocopherylhydroquinone (4) and δ-tocopherylhydroquinone (5), were isolated from Amphiroa crassa. By oxidizing 5 to the corresponding δ-tocopherylquinone (6), antimalarial activity against the human malaria parasite Plasmodium falciparum was increased by more than 20-fold.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science, Technology and Environment (FSTE) > Institute of Applied Science
Depositing User: Ms Mereoni Camailakeba
Date Deposited: 29 Nov 2010 19:53
Last Modified: 18 Jul 2012 07:09

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