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Título

Naturally-occurring tetrahydro-β-carboline alkaloids derived from tryptophan are oxidized to bioactive β-carboline alkaloids by heme peroxidases

Autor Herraiz Tomico, Tomás ; Galisteo, Juan
Palabras clave β-Carboline
Lactoperoxidase
Tetrahydro-β-carboline
Horseradish peroxidase
Myeloperoxidase
Alkaloids
Fecha de publicación 2014
EditorElsevier
Citación Biochemical and Biophysical Research Communications 451: 42- 47 (2014)
Resumenβ-Carbolines are indole alkaloids that occur in plants, foods, and endogenously in mammals and humans, and which exhibit potent biological, psychopharmacological and toxicological activities. They form from naturally-occurring tetrahydro-β-carboline alkaloids arising from tryptophan by still unknown way and mechanism. Results in this research show that heme peroxidases catalyzed the oxidation of tetrahydro-β-carbolines (i.e. 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid) into aromatic β-carbolines (i.e. norharman and harman, respectively). This oxidation followed a typical catalytic cycle of peroxidases through redox intermediates I, II, and ferric enzyme. Both, plant peroxidases (horseradish peroxidase, HRP) and mammalian peroxidases (myeloperoxidase, MPO and lactoperoxidase, LPO) catalyzed the oxidation in an efficient manner as determined by kinetic parameters (VMAX and KM). Oxidation of tetrahydro-β-carbolines was inhibited by peroxidase inhibitors such as sodium azide, ascorbic acid, hydroxylamine and excess of H2O 2. The formation of aromatic β-carbolines by heme peroxidases can help to explain the presence and activity of these compounds in biological systems. © 2014 Elsevier Inc. All rights reserved.
URI http://hdl.handle.net/10261/103122
DOI10.1016/j.bbrc.2014.07.047
Identificadoresdoi: 10.1016/j.bbrc.2014.07.047
issn: 1090-2104
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