N-甲基十氢喹啉：一类源自亚马逊箭毒蛙（树蛙科）的意想不到的生物碱。
N-methyldecahydroquinolines: an unexpected class of alkaloids from Amazonian poison frogs (Dendrobatidae).
作者信息
Daly John W, Ware Nathaniel, Saporito Ralph A, Spande Thomas F, Garraffo H Martin
机构信息
Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland 20892-0820, USA.
出版信息
J Nat Prod. 2009 Jun;72(6):1110-4. doi: 10.1021/np900094v.
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.
此前在箭毒蛙属的亚马逊树棘蛙皮肤提取物中鉴定出的主要生物碱是箭毒蛙毒素和2,5-二取代十氢喹啉。对来自玻利维亚的彩纹箭毒蛙皮肤提取物中的生物碱进行分析后发现，之前报道为2,5-二取代十氢喹啉的生物碱257A是一种N-甲基-2,5-二取代十氢喹啉。我们对最近归入箭毒蛙属的25多个物种中的另外12个物种的生物碱进行了表征，并鉴定出另外5种N-甲基十氢喹啉。在某些情况下，通过与由已知相对构型的相应2,5-二取代十氢喹啉制备的N-甲基化产物进行比较，确定了N-甲基十氢喹啉的相对构型。N-甲基十氢喹啉的饮食来源尚不清楚；然而，蚁科蚂蚁可能是2,5-二取代十氢喹啉的来源。对亚马逊毒蛙另一个属的三种物种的皮肤提取物中的生物碱也进行了表征，但未检测到N-甲基十氢喹啉。
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