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Formation of stable radicals in catechin/nitrous acid systems: Participation of dinitrosocatechin

Authorized Users Only
2016
Authors
Morina, Filis
Takahama, Umeo
Mojović, Miloš
Popovic-Bijelic, Ana
Veljović-Jovanović, Sonja
Article (Published version)
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Abstract
Catechins are transformed into dinitrosocatechins (diNOcats) and then oxidized to the quinones by salivary nitrite under conditions simulating the stomach. This manuscript deals with formation of stable radicals in the NO group of diNOcat during nitrite-induced oxidation of (+)-catechin and diNOcat at pH 2. We postulated two mechanisms for the stable radical formation; one is nitrous acid-induced oxidation of diNOcat in the A-ring, and the other intermolecular charge transfer from the A-ring of diNOcat and/or diNOcat quinone to the quinone moiety of the B-ring of diNOcat quinone. In addition, an unstable phenoxyl radical, which might be transformed into quinone, was also produced, accompanying the formation of the stable radical on the NO group. Taking the above results into account, we mainly focus on the adverse effects of the radicals and quinone, which may be produced from (+)-catechin in the stomach under the conditions of high salivary nitrite concentrations.
Keywords:
Stomach / Nitroxyl radical / Nitrous acid / Charge transfer complex / 6,8-Dinitrosocatechin / (+)-Catechin
Source:
Food Chemistry, 2016, 194, 1116-1122
Publisher:
  • Elsevier Sci Ltd, Oxford
Funding / projects:
  • Kyushu Dental University
  • Modulation of antioxidative metabolism in plants for improvement of plant abiotic stress tolerance and identification of new biomarkers for application in remediation and monitoring of degraded biotopes (RS-43010)

DOI: 10.1016/j.foodchem.2015.08.081

ISSN: 0308-8146

PubMed: 26471661

WoS: 000364248900143

Scopus: 2-s2.0-84940922086
[ Google Scholar ]
9
6
URI
http://rimsi.imsi.bg.ac.rs/handle/123456789/939
Collections
  • Radovi istraživača / Researchers’ publications
Institution/Community
Institut za multidisciplinarna istraživanja
TY  - JOUR
AU  - Morina, Filis
AU  - Takahama, Umeo
AU  - Mojović, Miloš
AU  - Popovic-Bijelic, Ana
AU  - Veljović-Jovanović, Sonja
PY  - 2016
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/939
AB  - Catechins are transformed into dinitrosocatechins (diNOcats) and then oxidized to the quinones by salivary nitrite under conditions simulating the stomach. This manuscript deals with formation of stable radicals in the NO group of diNOcat during nitrite-induced oxidation of (+)-catechin and diNOcat at pH 2. We postulated two mechanisms for the stable radical formation; one is nitrous acid-induced oxidation of diNOcat in the A-ring, and the other intermolecular charge transfer from the A-ring of diNOcat and/or diNOcat quinone to the quinone moiety of the B-ring of diNOcat quinone. In addition, an unstable phenoxyl radical, which might be transformed into quinone, was also produced, accompanying the formation of the stable radical on the NO group. Taking the above results into account, we mainly focus on the adverse effects of the radicals and quinone, which may be produced from (+)-catechin in the stomach under the conditions of high salivary nitrite concentrations.
PB  - Elsevier Sci Ltd, Oxford
T2  - Food Chemistry
T1  - Formation of stable radicals in catechin/nitrous acid systems: Participation of dinitrosocatechin
EP  - 1122
SP  - 1116
VL  - 194
DO  - 10.1016/j.foodchem.2015.08.081
ER  - 
@article{
author = "Morina, Filis and Takahama, Umeo and Mojović, Miloš and Popovic-Bijelic, Ana and Veljović-Jovanović, Sonja",
year = "2016",
abstract = "Catechins are transformed into dinitrosocatechins (diNOcats) and then oxidized to the quinones by salivary nitrite under conditions simulating the stomach. This manuscript deals with formation of stable radicals in the NO group of diNOcat during nitrite-induced oxidation of (+)-catechin and diNOcat at pH 2. We postulated two mechanisms for the stable radical formation; one is nitrous acid-induced oxidation of diNOcat in the A-ring, and the other intermolecular charge transfer from the A-ring of diNOcat and/or diNOcat quinone to the quinone moiety of the B-ring of diNOcat quinone. In addition, an unstable phenoxyl radical, which might be transformed into quinone, was also produced, accompanying the formation of the stable radical on the NO group. Taking the above results into account, we mainly focus on the adverse effects of the radicals and quinone, which may be produced from (+)-catechin in the stomach under the conditions of high salivary nitrite concentrations.",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "Food Chemistry",
title = "Formation of stable radicals in catechin/nitrous acid systems: Participation of dinitrosocatechin",
pages = "1122-1116",
volume = "194",
doi = "10.1016/j.foodchem.2015.08.081"
}
Morina, F., Takahama, U., Mojović, M., Popovic-Bijelic, A.,& Veljović-Jovanović, S.. (2016). Formation of stable radicals in catechin/nitrous acid systems: Participation of dinitrosocatechin. in Food Chemistry
Elsevier Sci Ltd, Oxford., 194, 1116-1122.
https://doi.org/10.1016/j.foodchem.2015.08.081
Morina F, Takahama U, Mojović M, Popovic-Bijelic A, Veljović-Jovanović S. Formation of stable radicals in catechin/nitrous acid systems: Participation of dinitrosocatechin. in Food Chemistry. 2016;194:1116-1122.
doi:10.1016/j.foodchem.2015.08.081 .
Morina, Filis, Takahama, Umeo, Mojović, Miloš, Popovic-Bijelic, Ana, Veljović-Jovanović, Sonja, "Formation of stable radicals in catechin/nitrous acid systems: Participation of dinitrosocatechin" in Food Chemistry, 194 (2016):1116-1122,
https://doi.org/10.1016/j.foodchem.2015.08.081 . .

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