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N-methyldecahydroquinolines: an unexpected class of alkaloids from Amazonian poison frogs (Dendrobatidae).

ABSTRACT: 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.

SUBMITTER: Daly JW

PROVIDER: S-EPMC3290094 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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N-methyldecahydroquinolines: an unexpected class of alkaloids from Amazonian poison frogs (Dendrobatidae).

Daly John W JW Ware Nathaniel N Saporito Ralph A RA Spande Thomas F TF Garraffo H Martin HM

Journal of natural products 20090601 6

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 A ...[more]

PMID: 19432407

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Project description:BackgroundThe consumption of conspecific young by adult individuals is a common phenomenon across various animal taxa. Possible adaptive benefits of such behaviour include the acquisition of nutrients, decreased competition for one's own offspring, and/or increased mating opportunities. Clutch cannibalism has occasionally been observed in several species of Neotropical poison frogs, but the circumstances under which this behaviour occurs has rarely been investigated experimentally. Recent experiments with the poison frog Allobates femoralis have shown that males indiscriminately transport all clutches located inside their own territory to bodies of water, but become highly cannibalistic when taking over a new territory. Females are able to indirectly discriminate between their own and foreign clutches by location and take over transport duties of their own clutches only in the absence of the father. Cannibalism by A. femoralis females has not been previously observed. We thus asked if, and under which circumstances, cannibalism of unrelated clutches by female A. femoralis would occur, by manipulating the presence of the clutch's father, the female's own reproductive state, and the female's familiarity with the environment.ResultsFemales clearly cannibalize foreign clutches. Cannibalism was most pronounced when the female had not recently produced her own clutch and the father of the foreign clutch was absent. The female's familiarity with the area had no significant influence on the likelihood of cannibalism to occur.ConclusionsOur data indicate that both previous oviposition and the father's presence reduce cannibalistic behaviour in A. femoralis females. Cannibalistic females may gain nutritional benefits or enhanced inclusive fitness by preying on other females' offspring. The finding that the father's presence at the clutch site/territory was sufficient to reduce cannibalism by females suggests a prominent role of male territoriality for the evolution of male parental care.

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N-methyldecahydroquinolines: an unexpected class of alkaloids from Amazonian poison frogs (Dendrobatidae).

Publications

N-methyldecahydroquinolines: an unexpected class of alkaloids from Amazonian poison frogs (Dendrobatidae).

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