Characterization of caffeic acid enzymatic oxidation by-products by liquid chromatography coupled to electrospray ionization tandem mass spectrometry

The products of tyrosinase-catalyzed caffeic acid oxidation at pH 6.5 were investigated using high-performance liquid chromatography (HPLC) coupled to electrospray ionization mass spectrometry (ESI-MS). Aliquots of reaction mixtures were withdrawn at different times, varying from 0 to 24 h, and dire...

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Bibliographic Details
Published in:Journal of Chromatography A 2006-01, Vol.1102 (1), p.184-192
Main Authors: Pati, S., Losito, I., Palmisano, F., Zambonin, P.G.
Format: Article
Language:English
Subjects:
Analytical chemistry
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Caffeic acid oxidation
Caffeic Acids - chemistry
Chemistry
Chromatographic methods and physical methods associated with chromatography
Chromatography, High Pressure Liquid - methods
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
Liquid chromatography-electrospray ionization mass spectrometry
Methods. Procedures. Technologies
Other chromatographic methods
Oxidation-Reduction
Spectrometry, Mass, Electrospray Ionization - methods
Spectrophotometry, Ultraviolet
Tandem mass spectrometry
Tyrosinase-catalyzed oxidation
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Summary:The products of tyrosinase-catalyzed caffeic acid oxidation at pH 6.5 were investigated using high-performance liquid chromatography (HPLC) coupled to electrospray ionization mass spectrometry (ESI-MS). Aliquots of reaction mixtures were withdrawn at different times, varying from 0 to 24 h, and directly analysed by HPLC-ESI-MS and, in the case of 1 and 5 h, by HPLC-ESI-MS/MS to obtain structural information on caffeic acid derivatives. In particular, two different classes of caffeic acid dimers were identified: caffeicins-like structures and dimers originated by C C coupling between the benzene rings. Evidences for the presence of trimeric derivatives of caffeic acid were also obtained from MS data.
ISSN:0021-9673
DOI:10.1016/j.chroma.2005.10.041