Interactions between (+)-Catechin and Quercetin during Their Oxidation by Nitrite under the Conditions Simulating the Stomach
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2014
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Metapodaci
Prikaz svih podataka o dokumentuApstrakt
When foods that contain catechins and quercetin glycosides are ingested, quercetin glycosides are hydrolyzed to quercetin during mastication by hydrolytic enzymes derived from oral bacteria and the generated quercetin aglycone is mixed with catechins in saliva. The present study deals with the interactions between (+)-catechin and quercetin during their reactions with nitrous acid under the conditions simulating the gastric lumen. Nitrous acid reacted with (+)-catechin producing 6,8-dinitrosocatechin, and quercetin partially suppressed the dinitrosocatechin formation. Nitric oxide, which was produced by not only (+)-catechin/nitrous acid but also quercetin/nitrous acid systems, was used to produce 6,8-dinitrosocatechin. Furthermore, 6,8-dinitrosocatechin was oxidized by nitrous acid to the quinone form. The quinone formation was significantly suppressed by quercetin. Quercetin-dependent suppression of the above reactions accompanied the oxidation of quercetin, which was observed with t...he formation of 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone. Taking the above results into account, we proposed a possible mechanism of 6,8-dinitrosocatechin formation and discuss the importance of quercetin to prevent the quinone formation from 6,8-dinitrosocatechin in the gastric lumen, taking the interactions between quercetin and catechins into account.
Ključne reči:
redox reaction / quercetin / nitrous acid / nitrosation / acidic conditions / (+)-catechinIzvor:
Journal of Agricultural and Food Chemistry, 2014, 62, 21, 4951-4959Izdavač:
- Amer Chemical Soc, Washington
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)
- Grants-in-Aid for Scientific ResearchMinistry of Education, Culture, Sports, Science and Technology, Japan (MEXT)Japan Society for the Promotion of ScienceGrants-in-Aid for Scientific Research (KAKENHI) [23500968] Funding Source: KAKEN
DOI: 10.1021/jf500860s
ISSN: 0021-8561
PubMed: 24785370
WoS: 000336635600017
Scopus: 2-s2.0-84901599373
Institucija/grupa
Institut za multidisciplinarna istraživanjaTY - JOUR AU - Veljović-Jovanović, Sonja AU - Morina, Filis AU - Yamauchi, Ryo AU - Hirota, Sachiko AU - Takahama, Umeo PY - 2014 UR - http://rimsi.imsi.bg.ac.rs/handle/123456789/753 AB - When foods that contain catechins and quercetin glycosides are ingested, quercetin glycosides are hydrolyzed to quercetin during mastication by hydrolytic enzymes derived from oral bacteria and the generated quercetin aglycone is mixed with catechins in saliva. The present study deals with the interactions between (+)-catechin and quercetin during their reactions with nitrous acid under the conditions simulating the gastric lumen. Nitrous acid reacted with (+)-catechin producing 6,8-dinitrosocatechin, and quercetin partially suppressed the dinitrosocatechin formation. Nitric oxide, which was produced by not only (+)-catechin/nitrous acid but also quercetin/nitrous acid systems, was used to produce 6,8-dinitrosocatechin. Furthermore, 6,8-dinitrosocatechin was oxidized by nitrous acid to the quinone form. The quinone formation was significantly suppressed by quercetin. Quercetin-dependent suppression of the above reactions accompanied the oxidation of quercetin, which was observed with the formation of 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone. Taking the above results into account, we proposed a possible mechanism of 6,8-dinitrosocatechin formation and discuss the importance of quercetin to prevent the quinone formation from 6,8-dinitrosocatechin in the gastric lumen, taking the interactions between quercetin and catechins into account. PB - Amer Chemical Soc, Washington T2 - Journal of Agricultural and Food Chemistry T1 - Interactions between (+)-Catechin and Quercetin during Their Oxidation by Nitrite under the Conditions Simulating the Stomach EP - 4959 IS - 21 SP - 4951 VL - 62 DO - 10.1021/jf500860s ER -
@article{ author = "Veljović-Jovanović, Sonja and Morina, Filis and Yamauchi, Ryo and Hirota, Sachiko and Takahama, Umeo", year = "2014", abstract = "When foods that contain catechins and quercetin glycosides are ingested, quercetin glycosides are hydrolyzed to quercetin during mastication by hydrolytic enzymes derived from oral bacteria and the generated quercetin aglycone is mixed with catechins in saliva. The present study deals with the interactions between (+)-catechin and quercetin during their reactions with nitrous acid under the conditions simulating the gastric lumen. Nitrous acid reacted with (+)-catechin producing 6,8-dinitrosocatechin, and quercetin partially suppressed the dinitrosocatechin formation. Nitric oxide, which was produced by not only (+)-catechin/nitrous acid but also quercetin/nitrous acid systems, was used to produce 6,8-dinitrosocatechin. Furthermore, 6,8-dinitrosocatechin was oxidized by nitrous acid to the quinone form. The quinone formation was significantly suppressed by quercetin. Quercetin-dependent suppression of the above reactions accompanied the oxidation of quercetin, which was observed with the formation of 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone. Taking the above results into account, we proposed a possible mechanism of 6,8-dinitrosocatechin formation and discuss the importance of quercetin to prevent the quinone formation from 6,8-dinitrosocatechin in the gastric lumen, taking the interactions between quercetin and catechins into account.", publisher = "Amer Chemical Soc, Washington", journal = "Journal of Agricultural and Food Chemistry", title = "Interactions between (+)-Catechin and Quercetin during Their Oxidation by Nitrite under the Conditions Simulating the Stomach", pages = "4959-4951", number = "21", volume = "62", doi = "10.1021/jf500860s" }
Veljović-Jovanović, S., Morina, F., Yamauchi, R., Hirota, S.,& Takahama, U.. (2014). Interactions between (+)-Catechin and Quercetin during Their Oxidation by Nitrite under the Conditions Simulating the Stomach. in Journal of Agricultural and Food Chemistry Amer Chemical Soc, Washington., 62(21), 4951-4959. https://doi.org/10.1021/jf500860s
Veljović-Jovanović S, Morina F, Yamauchi R, Hirota S, Takahama U. Interactions between (+)-Catechin and Quercetin during Their Oxidation by Nitrite under the Conditions Simulating the Stomach. in Journal of Agricultural and Food Chemistry. 2014;62(21):4951-4959. doi:10.1021/jf500860s .
Veljović-Jovanović, Sonja, Morina, Filis, Yamauchi, Ryo, Hirota, Sachiko, Takahama, Umeo, "Interactions between (+)-Catechin and Quercetin during Their Oxidation by Nitrite under the Conditions Simulating the Stomach" in Journal of Agricultural and Food Chemistry, 62, no. 21 (2014):4951-4959, https://doi.org/10.1021/jf500860s . .