The chemistry of poisons in amphibian skin.
Poisons are common in nature, where they often serve the organism in chemical defense. Such poisons either are produced de novo or are sequestered from dietary sources or symbiotic organisms. Among vertebrates, amphibians are notable for the wide range of noxious agents that are contained in granular skin glands. These compounds include amines, peptides, proteins, steroids, and both water-soluble and lipid-soluble alkaloids. With the exception of the alkaloids, most seem to be produced de novo by the amphibian. The skin of amphibians contains many structural classes of alkaloids previously unknown in nature. These include the batrachotoxins, which have recently been discovered to also occur in skin and feathers of a bird, the histrionicotoxins, the gephyrotoxins, the decahydroquinolines, the pumiliotoxins and homopumiliotoxins, epibatidine, and the samandarines. Some amphibian skin alkaloids are clearly sequestered from the diet, which consists mainly of small arthropods. These include pyrrolizidine and indolizidine alkaloids from ants, tricyclic coccinellines from beetles, and pyrrolizidine oximes, presumably from millipedes. The sources of other alkaloids in amphibian skin, including the batrachotoxins, the decahydroquinolines, the histrionicotoxins, the pumiliotoxins, and epibatidine, are unknown. While it is possible that these are produced de novo or by symbiotic microorganisms, it appears more likely that they are sequestered by the amphibians from as yet unknown dietary sources.
Daly
J W
JW
Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institute of Health, Bethesda, MD 20892.
D000664:Amphibian Venoms / Q000737:chemistry* / Q000633:toxicity; D000663:Amphibians / Q000502:physiology*; D000818:Animals; D001717:Birds; D001643:Bridged Bicyclo Compounds / Q000737:chemistry / Q000633:toxicity; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007448:Invertebrates; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry / Q000633:toxicity; D012879:Skin Physiological Phenomena
D000664:Amphibian Venoms; D001643:Bridged Bicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D011725:Pyridines; C082748:epibatidine; C007948:histrionicotoxin