Unusual antimalarial meroditerpenes from tropical red macroalgae.
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.
Stout
E Paige
EP
School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332, USA.
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
D000962:Antimalarials / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D002942:Circular Dichroism; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D010963:Plasmodium falciparum / Q000187:drug effects; D012624:Seaweed / Q000737:chemistry*
D000962:Antimalarials; D004224:Diterpenes
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