Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase
Identifieur interne : 001621 ( Pmc/Curation ); précédent : 001620; suivant : 001622Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase
Auteurs : Gilles Ferry [France] ; Caroline Ubeaud [France] ; Pierre-Hervé Lambert [France] ; Sophie Bertin [France] ; Francis Cogé [France] ; Pascale Chomarat [France] ; Philippe Delagrange [France] ; Bernard Serkiz [France] ; Jean-Paul Bouchet [France] ; Roger J. W. Truscott [Australie] ; Jean A. Boutin [France]Source :
- Biochemical Journal [ 0264-6021 ] ; 2005.
Abstract
The catabolism of melatonin, whether naturally occurring or ingested, takes place via two pathways: ∼70% can be accounted for by conjugation (sulpho- and glucurono-conjugation), and ∼30% by oxidation. It is commonly thought that the interferon-induced enzyme indoleamine 2,3-dioxygenase (EC 1.13.11.42), which oxidizes tryptophan, is also responsible for the oxidation of 5-hydroxytryptamine (serotonin) and its derivative, melatonin. Using the recombinant enzyme expressed in
Url:
DOI: 10.1042/BJ20042075
PubMed: 15636586
PubMed Central: 1186709
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<front><div type="abstract" xml:lang="en"><p>The catabolism of melatonin, whether naturally occurring or ingested, takes place via two pathways: ∼70% can be accounted for by conjugation (sulpho- and glucurono-conjugation), and ∼30% by oxidation. It is commonly thought that the interferon-induced enzyme indoleamine 2,3-dioxygenase (EC 1.13.11.42), which oxidizes tryptophan, is also responsible for the oxidation of 5-hydroxytryptamine (serotonin) and its derivative, melatonin. Using the recombinant enzyme expressed in <italic>Escherichia coli</italic>
, we show in the present work that indoleamine 2,3-dioxygenase indeed cleaves tryptophan; however, under the same conditions, it is incapable of cleaving the two other indoleamines. By contrast, myeloperoxidase (EC 1.11.1.7) is capable of cleaving the indole moiety of melatonin. However, when using the peroxidase conditions of assay – with H<sub>2</sub>
O<sub>2</sub>
as co-substrate – indoleamine 2,3-dioxygenase is able to cleave melatonin into its main metabolite, a kynurenine derivative. The present work establishes that the oxidative metabolism of melatonin is due, in the presence of H<sub>2</sub>
O<sub>2</sub>
, to the activities of both myeloperoxidase and indoleamine 2,3-dioxygenase (with lower potency), since both enzymes have <italic>K</italic>
<sub>m</sub>
values for melatonin in the micromolar range. Under these conditions, several indolic compounds can be cleaved by both enzymes, such as tryptamine and 5-hydroxytryptamine. Furthermore, melatonin metabolism results in a kynurenine derivative, the pharmacological action of which remains to be studied, and could amplify the mechanisms of action of melatonin.</p>
</div>
</front>
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<front><journal-meta><journal-id journal-id-type="nlm-ta">Biochem J</journal-id>
<journal-id journal-id-type="publisher-id">BJ</journal-id>
<journal-title>Biochemical Journal</journal-title>
<issn pub-type="ppub">0264-6021</issn>
<issn pub-type="epub">1470-8728</issn>
<publisher><publisher-name>Portland Press Ltd.</publisher-name>
</publisher>
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<article-meta><article-id pub-id-type="pmid">15636586</article-id>
<article-id pub-id-type="pmc">1186709</article-id>
<article-id pub-id-type="publisher-id">bj3880205</article-id>
<article-id pub-id-type="doi">10.1042/BJ20042075</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Research Article</subject>
</subj-group>
</article-categories>
<title-group><article-title>Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase</article-title>
<alt-title alt-title-type="right-running-head">Melatonin oxidative catabolism by indoleamine 2,3-dioxygenase and myeloperoxidase</alt-title>
<alt-title alt-title-type="left-running-head">G. Ferry and others</alt-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Ferry</surname>
<given-names>Gilles</given-names>
</name>
<xref rid="A1" ref-type="aff">*</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Ubeaud</surname>
<given-names>Caroline</given-names>
</name>
<xref rid="A1" ref-type="aff">*</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Lambert</surname>
<given-names>Pierre-Hervé</given-names>
</name>
<xref rid="A2" ref-type="aff">†</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Bertin</surname>
<given-names>Sophie</given-names>
</name>
<xref rid="A2" ref-type="aff">†</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Cogé</surname>
<given-names>Francis</given-names>
</name>
<xref rid="A1" ref-type="aff">*</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Chomarat</surname>
<given-names>Pascale</given-names>
</name>
<xref rid="A1" ref-type="aff">*</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Delagrange</surname>
<given-names>Philippe</given-names>
</name>
<xref rid="A1" ref-type="aff">*</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Serkiz</surname>
<given-names>Bernard</given-names>
</name>
<xref rid="A2" ref-type="aff">†</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Bouchet</surname>
<given-names>Jean-Paul</given-names>
</name>
<xref rid="A2" ref-type="aff">†</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Truscott</surname>
<given-names>Roger J. W.</given-names>
</name>
<xref rid="A3" ref-type="aff">‡</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Boutin</surname>
<given-names>Jean A.</given-names>
</name>
<xref rid="A1" ref-type="aff">*</xref>
<xref ref-type="corresp" rid="COR1"><sup>1</sup>
</xref>
</contrib>
<aff id="A1">*Pharmacologie Moléculaire et Cellulaire, Institut de Recherches SERVIER 125, chemin de Ronde 78290, Croissy-sur-Seine, France</aff>
<aff id="A2">†Physico-chimie analytique, Institut de Recherches SERVIER 11, rue des Moulineaux, 92150 Suresnes, France</aff>
<aff id="A3">‡Australian Cataract Research Foundation and Department of Chemistry, University of Wollongong, New South Wales 2522, Australia</aff>
</contrib-group>
<author-notes><corresp id="COR1"><sup>1</sup>
To whom correspondence should be addressed (email <email>jean.boutin@fr.netgrs.com</email>
).</corresp>
</author-notes>
<pub-date pub-type="epreprint"><day>7</day>
<month>1</month>
<year>2005</year>
</pub-date>
<pub-date pub-type="epub"><day>10</day>
<month>5</month>
<year>2005</year>
</pub-date>
<pub-date pub-type="ppub"><day>15</day>
<month>5</month>
<year>2005</year>
</pub-date>
<volume>388</volume>
<issue>Pt 1</issue>
<fpage>205</fpage>
<lpage>215</lpage>
<history><date date-type="received"><day>15</day>
<month>12</month>
<year>2004</year>
</date>
<date date-type="rev-recd"><day>6</day>
<month>1</month>
<year>2005</year>
</date>
<date date-type="accepted"><day>7</day>
<month>1</month>
<year>2005</year>
</date>
</history>
<copyright-statement>The Biochemical Society, London</copyright-statement>
<copyright-year>2005</copyright-year>
<abstract><p>The catabolism of melatonin, whether naturally occurring or ingested, takes place via two pathways: ∼70% can be accounted for by conjugation (sulpho- and glucurono-conjugation), and ∼30% by oxidation. It is commonly thought that the interferon-induced enzyme indoleamine 2,3-dioxygenase (EC 1.13.11.42), which oxidizes tryptophan, is also responsible for the oxidation of 5-hydroxytryptamine (serotonin) and its derivative, melatonin. Using the recombinant enzyme expressed in <italic>Escherichia coli</italic>
, we show in the present work that indoleamine 2,3-dioxygenase indeed cleaves tryptophan; however, under the same conditions, it is incapable of cleaving the two other indoleamines. By contrast, myeloperoxidase (EC 1.11.1.7) is capable of cleaving the indole moiety of melatonin. However, when using the peroxidase conditions of assay – with H<sub>2</sub>
O<sub>2</sub>
as co-substrate – indoleamine 2,3-dioxygenase is able to cleave melatonin into its main metabolite, a kynurenine derivative. The present work establishes that the oxidative metabolism of melatonin is due, in the presence of H<sub>2</sub>
O<sub>2</sub>
, to the activities of both myeloperoxidase and indoleamine 2,3-dioxygenase (with lower potency), since both enzymes have <italic>K</italic>
<sub>m</sub>
values for melatonin in the micromolar range. Under these conditions, several indolic compounds can be cleaved by both enzymes, such as tryptamine and 5-hydroxytryptamine. Furthermore, melatonin metabolism results in a kynurenine derivative, the pharmacological action of which remains to be studied, and could amplify the mechanisms of action of melatonin.</p>
</abstract>
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<kwd>indole ring</kwd>
<kwd>kynurenine</kwd>
<kwd>melatonin</kwd>
<kwd>myeloperoxidase</kwd>
<kwd>oxidative catabolism</kwd>
</kwd-group>
<kwd-group kwd-group-type="abbr"><kwd>AFMK, <italic>N</italic>
<sup>1</sup>
-acetyl-<italic>N</italic>
<sup>2</sup>
-formyl-5-methoxykynurenine</kwd>
<kwd>AMK, <italic>N</italic>
<sup>1</sup>
-acetyl-5-methoxykynurenine</kwd>
<kwd>IndoDO, indoleamine 2,3-dioxygenase</kwd>
<kwd>MyelPO, myeloperoxidase</kwd>
<kwd>TFA, trifluoroacetic acid</kwd>
<kwd>TrypDO, tryptophan 2,3-dioxygenase</kwd>
</kwd-group>
<counts><fig-count count="12"></fig-count>
<table-count count="2"></table-count>
<ref-count count="51"></ref-count>
<page-count count="11"></page-count>
</counts>
</article-meta>
</front>
</pmc>
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