5-Methoxy- and 5-Hydroxyindoles in the skin of <i>Bufo alvarius</i>
The skin of <i>Bufo alvarius</i>, a desert toad of Arizona, contains a number of indolealkylamines and their metabolites belonging to the common series of 5-hydroxyindolealkylamines and to the unusual series of 5-methoxyindolealkyIamines. The most abundant representative of 5-hydroxyindo...
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| Autores principales: | , , , |
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| Formato: | Articulo |
| Lenguaje: | Inglés |
| Publicado: |
1967
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| Materias: | |
| Acceso en línea: | http://sedici.unlp.edu.ar/handle/10915/88423 |
| Aporte de: |
| Sumario: | The skin of <i>Bufo alvarius</i>, a desert toad of Arizona, contains a number of indolealkylamines and their metabolites belonging to the common series of 5-hydroxyindolealkylamines and to the unusual series of 5-methoxyindolealkyIamines. The most abundant representative of 5-hydroxyindolealkylamines is, as in numerous other toads, bufotenine (up to 3 mg per g dry skin), the most abundant representative of 5-methoxyindolealkylamines, O-methylbufotenine. In parotoid and coxal glands as much as 5–15 per cent of the dry weight is made up by this compound. Natural O-methylbufotenine has been isolated in a pure form and its identity with synthetic O-methylbufotenine definitely established.
The <i>B. alvarius</i> skin presents three sulphur-containing indolealkylamines: one is bufoviridine, the well known O-sulphate of bufotenine, the other two are completely new compounds with sulphuric acid probably attached to the > NH group of the indole nucleus.
All the hitherto described metabolites arising from the oxidative deamination of 5-hydroxy- and 5-methoxy-indolealkylamines may be found in the <i>B. alvarius</i> skin: 5-hydroxytryptophol, 5-hydroxyindoleacetic acid, 5-methoxytryptophol and 5-methoxyindoleacetic acid.
The occurrence of the above compounds points to the necessary presence in <i>B. alvarius</i> skin of a number of enzymes: tryptophan 5-hydroxylase, catalysing the formation of 5-hydroxytryptophan, aromatic L-aminoacid decarboxylase producing the decarboxylation of 5-hydroxytryptophan to 5-hydroxytryptamine, N-methyl transferase and 5-hydroxyindole-O-methyl transferase giving origin to the N-methyl and O-methylindolealkylamines, and finally sulphoconjugases catalysing the linkage of sulphuric acid to the 5-hydroxy group and the > NH group of the indole nucleus.
The exceptionally rich sample card of indolealkylamines in the skin of <i>B. alvarius</i> seems of interest not only from the point of view of comparative biochemistry, but also from that of comparative enzymology and biochemical taxonomy. |
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