Flavonoid Deactivation of Excited State Flavins: Reaction Monitoring by Mass Spectrometry

Flavin mononucleotide (FMN, as a B2 vitamin model) was shown to induce dimerization of flavonoids (flavanone, apigenin, naringenin, eriodictyol, taxifolin, catechin, kaempferol, luteolin, quercetin, rutin, and seven smaller model phenols studied) as the major photoreaction, when aqueous solutions we...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2012-09, Vol.60 (36), p.9261-9272
Main Authors: Huvaere, Kevin, Sinnaeve, Bart, Van Bocxlaer, Jan, Skibsted, Leif H
Format: Article
Language:English
Subjects:
antioxidant activity
apigenin
aqueous solutions
astringency
Biological and medical sciences
catechin
cations
color
Dimerization
Flavins - chemistry
Flavonoids - chemistry
Food industries
foods
Fundamental and applied biological sciences. Psychology
kaempferol
luteolin
mass spectrometry
Mass Spectrometry - methods
Molecular Structure
monitoring
naringenin
phenols
quercetin
riboflavin
rutin
Spectrometry, Mass, Electrospray Ionization - methods
taxifolin
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Summary:Flavin mononucleotide (FMN, as a B2 vitamin model) was shown to induce dimerization of flavonoids (flavanone, apigenin, naringenin, eriodictyol, taxifolin, catechin, kaempferol, luteolin, quercetin, rutin, and seven smaller model phenols studied) as the major photoreaction, when aqueous solutions were exposed to visible light using a new, real-time electrospray ionization mass-spectrometric (ESI-MS) technique supported by LC–MS and MS2 analysis. Electrophilic intermediates such as transient radical cations, o-quinones, and p-quinone methide were proposed to be involved in the coupling process. The C3-OH in flavon-3-ols gave rise to atypical compounds such as a depside or a dioxane-linked dimer. Flavonoid dimers, formed in vegetal extracts added to food during storage in light and for which structures are proprosed based on MS and MS2, may affect colloidal stability, color, astringency, and antioxidative capacity.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf301823h