Unusual antimalarial meroditerpenes from tropical red macroalgae

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

卷:20

Article

Stout, E. Paige¹  Prudhomme, Jacques³  Le Roch, Karine³  Fairchild, Craig R.⁴  Franzblau, Scott G.⁵  Aalbersberg, William⁶  Hay, Mark E.²  Kubanek, Julia^1,2 

[1] Georgia Inst Technol, Sch Chem & Biochem, Atlanta, GA 30332 USA

[2] Georgia Inst Technol, Sch Biol, Atlanta, GA 30332 USA

[3] Univ Calif Riverside, Dept Cell Biol & Neurosci, Riverside, CA 92521 USA

[4] Bristol Myers Squibb Pharmaceut Res Inst, Princeton, NJ 08543 USA

[5] Univ Illinois, Coll Pharm, Inst TB Res, Chicago, IL 60612 USA

[6] Univ S Pacific, Inst Appl Sci, Suva, Fiji

关键词: Callophycus serratus;    Amphiroa crassa;    Natural product;    Drug discovery;    Red macroalgae;   

DOI  :  10.1016/j.bmcl.2010.08.031

来源: Elsevier

【 摘 要 】

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, beta-tocopherylhydroquinone (4) and delta-tocopherylhydroquinone (5), were isolated from Amphiroa crassa. By oxidizing 5 to the corresponding delta-tocopherylquinone (6), antimalarial activity against the human malaria parasite Plasmodium falciparum was increased by more than 20-fold. (C) 2010 Elsevier Ltd. All rights reserved.

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