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Unusual antimalarial meroditerpenes from tropical red macroalgae.


ABSTRACT: 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, ?-tocopherylhydroquinone (4) and ?-tocopherylhydroquinone (5), were isolated from Amphiroa crassa. By oxidizing 5 to the corresponding ?-tocopherylquinone (6), antimalarial activity against the human malaria parasite Plasmodium falciparum was increased by more than 20-fold.

SUBMITTER: Stout EP 

PROVIDER: S-EPMC2939151 | biostudies-literature | 2010 Oct

REPOSITORIES: biostudies-literature

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Unusual antimalarial meroditerpenes from tropical red macroalgae.

Stout E Paige EP   Prudhomme Jacques J   Roch Karine Le KL   Fairchild Craig R CR   Franzblau Scott G SG   Aalbersberg William W   Hay Mark E ME   Kubanek Julia J  

Bioorganic & medicinal chemistry letters 20100810 19


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 oxid  ...[more]

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