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Indole-, imidazole- and phenyl-alkylamines in the skin of one hundred and forty american amphibian species other than bufonids
Institution:1. Institutes of Medical Pharmacology and of Pharmacology and Pharmacognosy, 1st University of Rome, 1-00100 Rome, Italy. Telephone: (06)4940094;2. Department of Natural Sciences, National University of Rio Cuarto, 5800 Rio Cuarto, Cordoba, Argentina;1. Leibniz-Forschungsinstitut für Molekulare Pharmakologie, 13125, Berlin, Germany;2. Department of Biochemistry, Weill Cornell Medicine, New York, NY, 10065, USA;1. School of Pharmaceutical Sciences, Taizhou University, Taizhou, 318000, PR China;2. School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, China;1. LAQV@REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre s/n, 4169-007 Porto, Portugal;1. Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai, 200237, China;2. State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai, 200237, China;3. Shanghai Frontier Science Research Base of Optogenetic Techniques for Cell Metabolism, School of Pharmacy, East China University of Science and Technology, Shanghai, 200237, China;4. Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai, 200237, China
Abstract:
  • 1.1. Extracts prepared from dried or fresh skins of 140 American amphibian species, other than bufonids, were subjected to chemical and biological screening in order to determine the presence and concentrations of aromatic biogenic amines.
  • 2.2. The most frequent and abundantly occurring amine category was that of indolealkylamines, represented by their prototype 5-hydroxytryptamine and its N-methylated derivatives. Conjugated and cyclized indolealkylamines, typical for the toad skin, were apparently lacking.
  • 3.3. Phenylalkylamines were represented by two quaternary ammonium bases: leptodactyline and, very rarely, candicine. Leptodactyline was particularly abundant in leptodactylid frogs of the genus Leptodactylus.
  • 4.4. Histamine occurred in trace amounts in different species, in large amounts only in some Leptodactylus species of the “pachypus” section. On the other hand, N-methylated histamines and cyclized histamines (spinaceamines) were confined to the skin of Leptodactylus pentadactylus labyrinthicus.
  • 5.5. The possible taxonomical and evolutionary significance of amphibian skin amines is pointed out.
Keywords:
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