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...
| Autores principales: | , , , |
|---|---|
| Formato: | Articulo |
| Lenguaje: | Inglés |
| Publicado: |
1967
|
| Materias: | |
| Acceso en línea: | http://sedici.unlp.edu.ar/handle/10915/88423 |
| Aporte de: |
| id |
I19-R120-10915-88423 |
|---|---|
| record_format |
dspace |
| institution |
Universidad Nacional de La Plata |
| institution_str |
I-19 |
| repository_str |
R-120 |
| collection |
SEDICI (UNLP) |
| language |
Inglés |
| topic |
Ciencias Naturales Bufo alvarius Piel |
| spellingShingle |
Ciencias Naturales Bufo alvarius Piel Erspamer, V. Vitali, T. Roseghini, M. Cei, José Miguel Alfredo María 5-Methoxy- and 5-Hydroxyindoles in the skin of <i>Bufo alvarius</i> |
| topic_facet |
Ciencias Naturales Bufo alvarius Piel |
| description |
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. |
| format |
Articulo Articulo |
| author |
Erspamer, V. Vitali, T. Roseghini, M. Cei, José Miguel Alfredo María |
| author_facet |
Erspamer, V. Vitali, T. Roseghini, M. Cei, José Miguel Alfredo María |
| author_sort |
Erspamer, V. |
| title |
5-Methoxy- and 5-Hydroxyindoles in the skin of <i>Bufo alvarius</i> |
| title_short |
5-Methoxy- and 5-Hydroxyindoles in the skin of <i>Bufo alvarius</i> |
| title_full |
5-Methoxy- and 5-Hydroxyindoles in the skin of <i>Bufo alvarius</i> |
| title_fullStr |
5-Methoxy- and 5-Hydroxyindoles in the skin of <i>Bufo alvarius</i> |
| title_full_unstemmed |
5-Methoxy- and 5-Hydroxyindoles in the skin of <i>Bufo alvarius</i> |
| title_sort |
5-methoxy- and 5-hydroxyindoles in the skin of <i>bufo alvarius</i> |
| publishDate |
1967 |
| url |
http://sedici.unlp.edu.ar/handle/10915/88423 |
| work_keys_str_mv |
AT erspamerv 5methoxyand5hydroxyindolesintheskinofibufoalvariusi AT vitalit 5methoxyand5hydroxyindolesintheskinofibufoalvariusi AT roseghinim 5methoxyand5hydroxyindolesintheskinofibufoalvariusi AT ceijosemiguelalfredomaria 5methoxyand5hydroxyindolesintheskinofibufoalvariusi |
| bdutipo_str |
Repositorios |
| _version_ |
1764820489921888258 |