Quercetin 7-O-glucoside suppresses nitrite-induced formation of dinitrosocatechins and their quinones in catechin/nitrite systems under stomach simulating conditions
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2015
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Metapodaci
Prikaz svih podataka o dokumentuApstrakt
Foods of plant origin contain flavonoids. In the adzuki bean, (+)-catechin, quercetin 3-O-rutinoside (rutin), and quercetin 7-O-beta-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)-N-center dot) and a glucoside of 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone. (+)-Catechin reacted with nitrous acid producing (NO)-N-center dot 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 approximate to 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.
Ključne reči:
Quercetin glucoside / stomach pH / nitrite / HPLC analysisIzvor:
Food & Function, 2015, 6, 1, 219-229Izdavač:
- Royal Soc Chemistry, Cambridge
Finansiranje / projekti:
- Ministry of Education and Science in Japan [22500790, 23500986]
- Modifikacije antioksidativnog metabolizma biljaka sa ciljem povećanja tolerancije na abiotski stres i identifikacija novih biomarkera sa primenom u remedijaciji i monitoringu degradiranih staništa (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-43010)
DOI: 10.1039/c4fo00695j
ISSN: 2042-6496
PubMed: 25375233
WoS: 000347235900021
Scopus: 2-s2.0-84928116878
Institucija/grupa
Institut za multidisciplinarna istraživanjaTY - JOUR AU - Morina, Filis AU - Takahama, Umeo AU - Yamauchi, Ryo AU - Hirota, Sachiko AU - Veljović-Jovanović, Sonja PY - 2015 UR - http://rimsi.imsi.bg.ac.rs/handle/123456789/847 AB - Foods of plant origin contain flavonoids. In the adzuki bean, (+)-catechin, quercetin 3-O-rutinoside (rutin), and quercetin 7-O-beta-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)-N-center dot) and a glucoside of 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone. (+)-Catechin reacted with nitrous acid producing (NO)-N-center dot 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 approximate to 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. PB - Royal Soc Chemistry, Cambridge T2 - Food & Function T1 - Quercetin 7-O-glucoside suppresses nitrite-induced formation of dinitrosocatechins and their quinones in catechin/nitrite systems under stomach simulating conditions EP - 229 IS - 1 SP - 219 VL - 6 DO - 10.1039/c4fo00695j ER -
@article{ author = "Morina, Filis and Takahama, Umeo and Yamauchi, Ryo and Hirota, Sachiko and Veljović-Jovanović, Sonja", year = "2015", abstract = "Foods of plant origin contain flavonoids. In the adzuki bean, (+)-catechin, quercetin 3-O-rutinoside (rutin), and quercetin 7-O-beta-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)-N-center dot) and a glucoside of 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone. (+)-Catechin reacted with nitrous acid producing (NO)-N-center dot 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 approximate to 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.", publisher = "Royal Soc Chemistry, Cambridge", journal = "Food & Function", title = "Quercetin 7-O-glucoside suppresses nitrite-induced formation of dinitrosocatechins and their quinones in catechin/nitrite systems under stomach simulating conditions", pages = "229-219", number = "1", volume = "6", doi = "10.1039/c4fo00695j" }
Morina, F., Takahama, U., Yamauchi, R., Hirota, S.,& Veljović-Jovanović, S.. (2015). Quercetin 7-O-glucoside suppresses nitrite-induced formation of dinitrosocatechins and their quinones in catechin/nitrite systems under stomach simulating conditions. in Food & Function Royal Soc Chemistry, Cambridge., 6(1), 219-229. https://doi.org/10.1039/c4fo00695j
Morina F, Takahama U, Yamauchi R, Hirota S, Veljović-Jovanović S. Quercetin 7-O-glucoside suppresses nitrite-induced formation of dinitrosocatechins and their quinones in catechin/nitrite systems under stomach simulating conditions. in Food & Function. 2015;6(1):219-229. doi:10.1039/c4fo00695j .
Morina, Filis, Takahama, Umeo, Yamauchi, Ryo, Hirota, Sachiko, Veljović-Jovanović, Sonja, "Quercetin 7-O-glucoside suppresses nitrite-induced formation of dinitrosocatechins and their quinones in catechin/nitrite systems under stomach simulating conditions" in Food & Function, 6, no. 1 (2015):219-229, https://doi.org/10.1039/c4fo00695j . .