Further alkaloids common to ants and frogs: Decahydroquinolines and a quinolizidine
Further alkaloids common to ants and frogs: Decahydroquinolines and a quinolizidine
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DOI：
10.1023/a:1020898229304
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发表时间：
1999-05-01
影响因子：
2.3
通讯作者：
Spande, TF
中科院分区：
文献类型：
--
作者：
Jones, TH;Gorman, JST;Spande, TF
在巴西蚁蚁（Solenopsis (Diplorhoptrum) sp. picea group）的提取物中检测到三种生物碱，即两种少量的十氢喹啉 (DHQ) 和一种主要的喹里西啶。一种 DHQ (3) 与已知的蛙皮生物碱 cis-195A（顺式 5-甲基-2-丙基十氢喹啉）相同，而第二种 DHQ 是 3 的异构体，命名为 195J，根据质谱和红外光谱，被指定为暂定的顺式-2-甲基-5-丙基十氢喹啉结构 (2)。第三种生物碱被证明与蛙皮生物碱 195C 相同，此前尚未提出其结构。质谱和红外光谱分析（包括化学电离串联质谱分析）表明 195C 具有 4-甲基-6-丙基喹啉西啶结构 (1)。合成了四种可能的非对映体，(6Z,10E)-4-甲基-6-丙基喹里西啶非对映体 (1b) 与天然生物碱相同。马达加斯加曼特尔林蛙群体的皮肤提取物除其他生物碱外，还含有少量相同的生物碱三联体 1-3，其中 1 又占主导地位。生物碱 1-3 在蚂蚁和青蛙中的常见存在支持了这样的假设：蚂蚁可能是隔离的青蛙皮生物碱的饮食来源，并且使蚂蚁和青蛙常见的生物碱类别达到六类。
Three alkaloids-two minor decahydroquinolines (DHQs) and a major quinolizidine-were detected in an extract of a Brazilian myrmicine ant (Solenopsis (Diplorhoptrum) sp. picea group). One DHQ (3) was identical to a known frog-skin alkaloid, cis-195A (cis-5-methyl-2-propyldecahydroquinoline), while the second DHQ, an isomer of 3, designated 195J, was assigned a tentative cis-2-methyl-5-propyldecahydroquinoline structure (2) based on mass and infrared spectra. The third alkaloid proved identical to the frog-skin alkaloid 195C, for which a structure had not been previously proposed. Mass and infrared spectral analysis, including chemical ionization tandem mass spectrometry, indicated a 4-methyl-6-propylquinolizidine structure (1) for 195C. The four possible diastereomers were synthesized and the (6Z,10E)-4-methyl-6-propylquinolizidine diastereomer (1b) was identical to the natural alkaloid. Skin extracts of a population of a Madagascan mantelline frog contained, among other alkaloids, minor amounts of the same alkaloid triad 1-3 with 1 again predominating. The common occurrence of alkaloids 1-3 in both ant and frog supports the hypothesis that ants are a likely dietary source for sequestered frog-skin alkaloids and brings to six, the alkaloid classes common to ant and frog.