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, 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.

• Authors: E Paige Stout, Jacques Prudhomme, Karine Le Roch, Craig R Fairchild, Scott G Franzblau, William Aalbersberg, Mark E Hay, Julia Kubanek
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 20 Issue 19 Pg. 5662-5 (Oct 01 2010) ISSN: 1464-3405 [Electronic] England
• PMID: 20801038 (Publication Type: Journal Article, Research Support, N.I.H., Extramural)
• Copyright: Copyright (c) 2010 Elsevier Ltd. All rights reserved.

Chemical References

• Antimalarials
• Diterpenes

Topics

• Antimalarials (chemistry, isolation & purification, pharmacology)
• Circular Dichroism
• Diterpenes (chemistry, isolation & purification, pharmacology)
• Humans
• Plasmodium falciparum (drug effects)
• Seaweed (chemistry)