Eusynstyelamides A, B, and C, nNOS Inhibitors, from the Ascidian Eusynstyela latericius

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• 作者：Dianne M. Tapiolas ; Bruce F. Bowden ; Eliane Abou-Mansour ; Richard H. Willis ; Jason R. Doyle ; Andrew N. Muirhead ; Catherine Liptrot ; Lyndon E. Llewellyn ; Carsten W. W. Wolff ; Anthony D. Wright ; Cherie A
• 刊名：Journal of Natural Products
• 出版年：2009
• 出版时间：June 26, 2009
• 年：2009
• 卷：72
• 期：6
• 页码：1115-1120
• 全文大小：130K
• 年卷期：v.72,no.6(June 26, 2009)
• ISSN：1520-6025

文摘

Eusynstyelamides A−C (1−3) were isolated from the Great Barrier Reef ascidian Eusynstyela latericius, together with the known metabolites homarine and trigonelline. The structures of 1−3, with relative configurations, were elucidated by interpretation of their spectroscopic data (NMR, MS, UV, IR, and CD). The NMR data of 1 were found to be virtually identical to that reported for eusynstyelamide (4), isolated from E. misakiensis, indicating that a revision of the structure of 4 is needed. Eusynstyelamides A−C exhibited inhibitory activity against neuronal nitric oxide synthase (nNOS), with IC₅₀ values of 41.7, 4.3, and 5.8 μM, respectively, whereas they were found to be nontoxic toward the three human tumor cell lines MCF-7 (breast), SF-268 (CNS), and H-460 (lung). Compounds 1 and 2 displayed mild inhibitory activity toward Staphylococcus aureus (IC₅₀ 5.6 and 6.5 mM, respectively) and mild inhibitory activity toward the C₄ plant regulatory enzyme pyruvate phosphate dikinase (PPDK) (IC₅₀ values of 19 and 20 mM, respectively).