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

Kevin André Jurgen Huvaere; Bart Sinnaeve; Jan Van Bocxlaer; Leif Horsfelt Skibsted

doi:10.1021/jf301823h

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

Kevin André Jurgen Huvaere, Bart Sinnaeve, Jan Van Bocxlaer, Leif Horsfelt Skibsted

17 Citationer (Scopus)

Abstract

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.

Originalsprog	Engelsk
Tidsskrift	Journal of Agricultural and Food Chemistry
Vol/bind	60
Udgave nummer	36
Sider (fra-til)	9261-9272
Antal sider	12
ISSN	0021-8561
DOI	https://doi.org/10.1021/jf301823h
Status	Udgivet - 12 sep. 2012

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10.1021/jf301823h

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title = "Flavonoid deactivation of excited state flavins: reaction monitoring by mass spectrometry",

abstract = "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.",

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T1 - Flavonoid deactivation of excited state flavins

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AU - Huvaere, Kevin André Jurgen

AU - Sinnaeve, Bart

AU - Bocxlaer, Jan Van

AU - Skibsted, Leif Horsfelt

PY - 2012/9/12

Y1 - 2012/9/12

N2 - 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.

AB - 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.

U2 - 10.1021/jf301823h

DO - 10.1021/jf301823h

M3 - Journal article

C2 - 22889117

SN - 0021-8561

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SP - 9261

EP - 9272

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

IS - 36

ER -

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

Abstract

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