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Quercetin 7-O-glucoside suppresses nitrite-induced formation of dinitrosocatechins and their quinones in catechin/nitrite systems under stomach simulating conditions.
- Source :
-
Food & function [Food Funct] 2015 Jan; Vol. 6 (1), pp. 219-29. Date of Electronic Publication: 2014 Nov 06. - Publication Year :
- 2015
-
Abstract
- Foods of plant origin contain flavonoids. In the adzuki bean, (+)-catechin, quercetin 3-O-rutinoside (rutin), and quercetin 7-O-β-D-glucopyranoside (Q7G) are the major flavonoids. During mastication of foods prepared from the adzuki bean, the flavonoids are mixed with saliva and swallowed into the stomach. Here we investigated the interactions between Q7G and (+)-catechin at pH 2, which may proceed in the stomach after the ingestion of foods prepared from the adzuki bean. Q7G reacted with nitrous acid producing nitric oxide (˙NO) and a glucoside of 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone. (+)-Catechin reacted with nitrous acid producing ˙NO and 6,8-dinitrosocatechin. The production of the dinitrosocatechin was partly suppressed by Q7G, and the suppression resulted in the enhancement of Q7G oxidation. 6,8-Dinitrosocatechin reacted further with nitrous acid generating the o-quinone, and the quinone formation was effectively suppressed by Q7G. In the flavonoids investigated, the suppressive effect decreased in the order Q7G≈quercetin>kaempferol>quercetin 4'-O-glucoside>rutin. Essentially the same results were obtained when (-)-epicatechin was used instead of (+)-catechin. The results indicate that nitrous acid-induced formation of 6,8-dinitrosocatechins and the o-quinones can be suppressed by flavonols in the stomach, and that both a hydroxyl group at C3 and ortho-hydroxyl groups in the B-ring are required for efficient suppression.
- Subjects :
- Animals
Anticarcinogenic Agents chemistry
Benzofurans chemistry
Benzofurans metabolism
Benzoquinones antagonists & inhibitors
Benzoquinones chemistry
Benzoquinones metabolism
Carcinogens chemistry
Carcinogens metabolism
Catechin antagonists & inhibitors
Catechin chemistry
Catechin metabolism
Dietary Supplements
Fabaceae chemistry
Functional Food analysis
Gastric Juice chemistry
Gastric Juice enzymology
Gastric Juice metabolism
Glucosides chemistry
Humans
Nitric Oxide chemistry
Nitric Oxide metabolism
Nitroso Compounds chemistry
Nitroso Compounds metabolism
Nitrous Acid chemistry
Nitrous Acid metabolism
Quercetin chemistry
Quercetin metabolism
Quinones chemistry
Quinones metabolism
Saliva chemistry
Saliva enzymology
Saliva metabolism
Seeds chemistry
Stereoisomerism
Anticarcinogenic Agents metabolism
Carcinogens antagonists & inhibitors
Catechin analogs & derivatives
Digestion
Glucosides metabolism
Models, Biological
Nitroso Compounds antagonists & inhibitors
Quercetin analogs & derivatives
Subjects
Details
- Language :
- English
- ISSN :
- 2042-650X
- Volume :
- 6
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- Food & function
- Publication Type :
- Academic Journal
- Accession number :
- 25375233
- Full Text :
- https://doi.org/10.1039/c4fo00695j