N-Methyldecahydroquinolines: An Unexpected Class of Alkaloids from Amazonian Poison Frogs (Dendrobatidae)

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• 作者：John W. Daly ; Nathaniel Ware ; Ralph A. Saporito ; Thomas F. Spande ; H. Martin Garraffo
• 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：1110-1114
• 全文大小：102K
• 年卷期：v.72,no.6(June 26, 2009)
• ISSN：1520-6025

文摘

The dominant alkaloids previously identified in skin extracts of Amazonian dendrobatid frogs of the genus Ameerega are histrionicotoxins and 2,5-disubstituted decahydroquinolines. Analysis of alkaloids in skin extracts of Ameerega picta from Bolivia revealed that the alkaloid 257A, previously reported as a 2,5-disubstituted decahydroquinoline, is an N-methyl-2,5-disubstituted decahydroquinoline. We characterized alkaloids of another 12 of the more than 25 species recently assigned to the genus Ameerega, and five additional N-methyldecahydroquinolines were identified. In some cases, the relative configuration of the N-methyldecahydroquinolines was determined by comparison with the N-methylated products prepared from the corresponding 2,5-disubstituted decahydroquinolines of known relative configuration. A dietary source for N-methyldecahydroquinolines is unknown; however, myrmicine ants are the likely source for the 2,5-disubstituted decahydroquinolines. The alkaloids in skin extracts of three species of another genus of Amazonian poison frog, Adelphobates, were also characterized, but N-methyldecahydroquinolines were not detected.