Antimalarial 尾-Carbolines from the New Zealand Ascidian Pseudodistoma opacum

详细信息    查看全文

• 作者：Susanna T. S. Chan ; A. Norrie Pearce ; Michael J. Page ; Marcel Kaiser ; Brent R. Copp
• 刊名：Journal of Natural Products
• 出版年：2011
• 出版时间：September 23, 2011
• 年：2011
• 卷：74
• 期：9
• 页码：1972-1979
• 全文大小：851K
• 年卷期：v.74,no.9(September 23, 2011)
• ISSN：1520-6025

文摘

One tetrahydro-尾-carboline, (鈭?-7-bromohomotrypargine (1), and three alkylguanidine-substituted 尾-carbolines, opacalines A, B, and C (2鈥?b>4), have been isolated from the New Zealand ascidian Pseudodistoma opacum. The structures of the metabolites were determined by analysis of mass spectrometric and 2D NMR spectroscopic data. Natural products 2 and 3, synthetic debromo analogues 8 and 9, and intermediate 16 exhibited moderate antimalarial activity toward a chloroquine-resistant strain of Plasmodium falciparum, with an IC₅₀ range of 2.5鈥?4 渭M. The biosynthesis of 1鈥?b>4 is proposed to proceed via a Pictet鈥揝pengler condensation of 6-bromotryptamine and the 伪-keto acid transamination product of either arginine or homoarginine. Cell separation and ¹H NMR analysis of P. opacum identified tetrahydro-尾-carboline 1 to be principally located in the zooids, while fully aromatized analogues 2鈥?b>4 were localized to the test.