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Flavonoid deactivation of excited state flavins: reaction monitoring by mass spectrometry

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Abstract
Flavin mononucleotide (FMN, as a B-2 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 C-3-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.
Keywords
ANTIOXIDANT PROPERTIES, OXIDATION-PRODUCTS, FLUORESCENCE DETECTION, PERFORMANCE LIQUID-CHROMATOGRAPHY, photooxidation, mass spectrometry, flavonoids, flavins, antioxidants, LIGHTSTRUCK FLAVOR, SINGLET OXYGEN, BROWNISH SCALE, LIGHT EXPOSURE, AMINO-ACIDS, RIBOFLAVIN

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Citation

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Chicago
Huvaere, Kevin, Bart Sinnaeve, Jan Van Bocxlaer, and Leif H Skibsted. 2012. “Flavonoid Deactivation of Excited State Flavins: Reaction Monitoring by Mass Spectrometry.” Journal of Agricultural and Food Chemistry 60 (36): 9261–9272.
APA
Huvaere, K., Sinnaeve, B., Van Bocxlaer, J., & Skibsted, L. H. (2012). Flavonoid deactivation of excited state flavins: reaction monitoring by mass spectrometry. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 60(36), 9261–9272.
Vancouver
1.
Huvaere K, Sinnaeve B, Van Bocxlaer J, Skibsted LH. Flavonoid deactivation of excited state flavins: reaction monitoring by mass spectrometry. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. 2012;60(36):9261–72.
MLA
Huvaere, Kevin, Bart Sinnaeve, Jan Van Bocxlaer, et al. “Flavonoid Deactivation of Excited State Flavins: Reaction Monitoring by Mass Spectrometry.” JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 60.36 (2012): 9261–9272. Print.
@article{3164432,
  abstract     = {Flavin mononucleotide (FMN, as a B-2 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 C-3-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.},
  author       = {Huvaere, Kevin and Sinnaeve, Bart and Van Bocxlaer, Jan and Skibsted, Leif H},
  issn         = {0021-8561},
  journal      = {JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY},
  keyword      = {ANTIOXIDANT PROPERTIES,OXIDATION-PRODUCTS,FLUORESCENCE DETECTION,PERFORMANCE LIQUID-CHROMATOGRAPHY,photooxidation,mass spectrometry,flavonoids,flavins,antioxidants,LIGHTSTRUCK FLAVOR,SINGLET OXYGEN,BROWNISH SCALE,LIGHT EXPOSURE,AMINO-ACIDS,RIBOFLAVIN},
  language     = {eng},
  number       = {36},
  pages        = {9261--9272},
  title        = {Flavonoid deactivation of excited state flavins: reaction monitoring by mass spectrometry},
  url          = {http://dx.doi.org/10.1021/jf301823h},
  volume       = {60},
  year         = {2012},
}

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