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

Tapiolas, Diane, Bowden, Bruce, Abou-Mansour, Eliane, Willis, Rick, Doyle, Jason, Muirhead, Andrew, Liptrot, Cathy, Llewellyn, Lyndon, Wolff, Carsten, Wright, Anthony, and Motti, Cherie (2009) Eusynstyelamides A, B, and C, nNOS Inhibitors, from the Ascidian Eusynstyela latericius. Journal of Natural Products, 72 (6). pp. 1115-1120.

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Abstract

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).

Item ID: 10041
Item Type: Article (Refereed Research - C1)
Keywords: Eusynstyela, eusynstyelamides, nNOS inhibitor, ascidian
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ISSN: 1520-6025
Date Deposited: 21 Apr 2010 04:42
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030502 Natural Products Chemistry @ 90%
11 MEDICAL AND HEALTH SCIENCES > 1115 Pharmacology and Pharmaceutical Sciences > 111501 Basic Pharmacology @ 10%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
Citation Count from Scopus Scopus 23
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