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

Kevin Huvaere, Bart Sinnaeve, Jan Van Bocxlaer UGent and Leif H Skibsted (2012) JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. 60(36). p.9261-9272
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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
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
journal title
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
J. Agric. Food Chem.
volume
60
issue
36
pages
9261 - 9272
Web of Science type
Article
Web of Science id
000308574900061
JCR category
AGRICULTURE, MULTIDISCIPLINARY
JCR impact factor
2.906 (2012)
JCR rank
1/56 (2012)
JCR quartile
1 (2012)
ISSN
0021-8561
DOI
10.1021/jf301823h
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
3164432
handle
http://hdl.handle.net/1854/LU-3164432
date created
2013-03-14 09:24:41
date last changed
2016-12-19 15:45:59
@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},
}

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.