Unusual antimalarial meroditerpenes from tropical red macroalgae
详细信息 查看全文
- 作者：E. Paige Stout ; Jacques Prudhomme ; Karine Le Roch ; Craig R. Fairchild ; Scott G. Franzblau ; William Aalbersberg ; Mark E. Hay ; Julia Kubanek
- 关键词：Callophycus serratus ; Amphiroa crassa ; Natural product ; Drug discovery ; Red macroalgae
- 刊名：Bioorganic and Medicinal Chemistry Letters
- 出版年：2010
- 出版时间：1 October 2010
- 年：2010
- 卷：20
- 期：19
- 页码：5662-5665
- 全文大小：290 K
文摘
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.