Phantasmidine: An Epibatidine Congener from the Ecuadorian Poison Frog Epipedobates anthonyi

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• 作者：Richard W. Fitch ; Thomas F. Spande ; H. Martin Garraffo ; Herman J. C. Yeh ; John W. Daly
• 刊名：Journal of Natural Products
• 出版年：2010
• 出版时间：March 26, 2010
• 年：2010
• 卷：73
• 期：3
• 页码：331-337
• 全文大小：151K
• 年卷期：v.73,no.3(March 26, 2010)
• ISSN：1520-6025

文摘

The skin of the Ecuadorian poison frog Epipedobates anthonyi contains the potent nicotinic agonists epibatidine (1) and N-methylepibatidine (3). In addition, a condensed tetracyclic epibatidine congener has been identified with activity at nicotinic acetylcholine receptors, but different selectivity than epibatidine. This rigid tetracycle has been named phantasmidine (4). Phantasmidine has a molecular formula of C₁₁H₁₁N₂OCl, shares a chloropyridine moiety with 1, and also contains furan, pyrrolidine, and cyclobutane rings. A combination of GC-MS and GC-FTIR analysis with on-column derivatization, 1D NMR spectroscopy with selective irradiation, and spectral simulation, along with 2D NMR, were used to elucidate the structure from a total sample of 20 μg of HPLC-purified 4 and its corresponding acetamide (5). After synthesis, this novel rigid agonist may serve as a selective probe for β4-contaning nicotinic receptors and potentially lead to useful pharmaceuticals.