| Horseradish peroxidase-catalyzed conjugation of eugenol with basic amino acids. | |
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MedLine Citation:
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PMID: 8814439 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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L-Lysine is shown to yield an adduct with the quinone methide intermediate formed during the horseradish peroxidase (HRP)-catalyzed aerobic oxidation of eugenol (4-allyl-2-methoxyphenol). Adduct formation is evidenced by (i) lysine quenching of the characteristic quinone methide absorption band measured at 350 nm; arginine and gamma-aminobutyric acid, but not alanine or propionic acid showed similar behaviour (ii) lysine-promoted a 400 mV decrease of the eugenol oxidation voltammetric wave (1.00 V), concomitantly with an increase in current intensity and (iii) reverse phase HPLC isolation of the lysine eugenol adduct, followed by GC-MS analysis. The MS spectrum is consistent with a 2:1 lysine:eugenol adduct (MW = 455). If operative in vivo, binding of lysine to eugenol might lead to protein inactivation and possibly be involved in eugenol toxicity. |
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Authors:
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M H Medeiros; P Di Mascio; A P Pinto; R R Vargas; E J Bechara |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Free radical research Volume: 25 ISSN: 1071-5762 ISO Abbreviation: Free Radic. Res. Publication Date: 1996 Jul |
Date Detail:
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Created Date: 1996-12-10 Completed Date: 1996-12-10 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 9423872 Medline TA: Free Radic Res Country: SWITZERLAND |
Other Details:
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Languages: eng Pagination: 5-12 Citation Subset: IM |
Affiliation:
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Instituto de Química da Universidade de Säo Paulo, Brazil. mhgdmede@quim.iq.usp.br |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
/
chemistry,
metabolism* Chromatography, High Pressure Liquid Electrochemistry / methods Eugenol / chemistry*, metabolism* Horseradish Peroxidase / metabolism* Lysine / chemistry, metabolism Mass Spectrometry / methods Proteins / metabolism Spectrophotometry |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Proteins; 56-87-1/Lysine; 97-53-0/Eugenol; EC 1.11.1.-/Horseradish Peroxidase |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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