Investigation of reaction between quercetin and Au(III) in acidic media: mechanism and identification of reaction products
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2013
Authors
Bondžić, Aleksandra M.
Lazarević-Pašti, Tamara D.

Bondžić, Bojan

Čolović, Mirjana B.

Jadranin, Milka

Vasić, Vesna M.

Article (Published version)

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The aim of the present paper was to investigate the reaction of quercetin, the flavonol very often used as a dietary supplement, with [AuCl4](-) ions. The reaction was studied spectrophotometrically using the equimolar solutions in 1 : 1 water-methanol at pH similar to 2. The spectrophotometric data indicated the formation of the products with an absorption maximum at 295 nm in all cases, characteristic of the oxidized forms of quercetin. HPLC coupled with DAD and LC-MS analysis of the reaction products suggested that the oxidation of quercetin resulted in the generation of similar metabolites including quinone and various oxidized quercetin-solvent adducts. In addition, cyclic voltammetric measurements confirmed that under applied experimental conditions, the reduction of Au(III) to Au(0) took place. The reduction species in the reaction mixture were Au(III) ions, while Au(I) disproportionates back to Au(III) and Au(0). The newly generated Au(III) ions further oxidized 3'-4'-dihydroxy... groups of quercetin adducts obtained after first 2e(-) oxidation, giving the final reaction products. Based on the identification of reaction products, the reaction mechanism for the oxidation of quercetin in the presence of Au(III) which involves two 2e(-) transfer processes was proposed.
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New Journal of Chemistry, 2013, 37, 4, 901-908Publisher:
- Royal Soc Chemistry, Cambridge
Funding / projects:
DOI: 10.1039/c2nj40742f
ISSN: 1144-0546
WoS: 000316225300008
Scopus: 2-s2.0-84878039502
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IHTMTY - JOUR AU - Bondžić, Aleksandra M. AU - Lazarević-Pašti, Tamara D. AU - Bondžić, Bojan AU - Čolović, Mirjana B. AU - Jadranin, Milka AU - Vasić, Vesna M. PY - 2013 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1293 AB - The aim of the present paper was to investigate the reaction of quercetin, the flavonol very often used as a dietary supplement, with [AuCl4](-) ions. The reaction was studied spectrophotometrically using the equimolar solutions in 1 : 1 water-methanol at pH similar to 2. The spectrophotometric data indicated the formation of the products with an absorption maximum at 295 nm in all cases, characteristic of the oxidized forms of quercetin. HPLC coupled with DAD and LC-MS analysis of the reaction products suggested that the oxidation of quercetin resulted in the generation of similar metabolites including quinone and various oxidized quercetin-solvent adducts. In addition, cyclic voltammetric measurements confirmed that under applied experimental conditions, the reduction of Au(III) to Au(0) took place. The reduction species in the reaction mixture were Au(III) ions, while Au(I) disproportionates back to Au(III) and Au(0). The newly generated Au(III) ions further oxidized 3'-4'-dihydroxy groups of quercetin adducts obtained after first 2e(-) oxidation, giving the final reaction products. Based on the identification of reaction products, the reaction mechanism for the oxidation of quercetin in the presence of Au(III) which involves two 2e(-) transfer processes was proposed. PB - Royal Soc Chemistry, Cambridge T2 - New Journal of Chemistry T1 - Investigation of reaction between quercetin and Au(III) in acidic media: mechanism and identification of reaction products VL - 37 IS - 4 SP - 901 EP - 908 DO - 10.1039/c2nj40742f ER -
@article{ author = "Bondžić, Aleksandra M. and Lazarević-Pašti, Tamara D. and Bondžić, Bojan and Čolović, Mirjana B. and Jadranin, Milka and Vasić, Vesna M.", year = "2013", abstract = "The aim of the present paper was to investigate the reaction of quercetin, the flavonol very often used as a dietary supplement, with [AuCl4](-) ions. The reaction was studied spectrophotometrically using the equimolar solutions in 1 : 1 water-methanol at pH similar to 2. The spectrophotometric data indicated the formation of the products with an absorption maximum at 295 nm in all cases, characteristic of the oxidized forms of quercetin. HPLC coupled with DAD and LC-MS analysis of the reaction products suggested that the oxidation of quercetin resulted in the generation of similar metabolites including quinone and various oxidized quercetin-solvent adducts. In addition, cyclic voltammetric measurements confirmed that under applied experimental conditions, the reduction of Au(III) to Au(0) took place. The reduction species in the reaction mixture were Au(III) ions, while Au(I) disproportionates back to Au(III) and Au(0). The newly generated Au(III) ions further oxidized 3'-4'-dihydroxy groups of quercetin adducts obtained after first 2e(-) oxidation, giving the final reaction products. Based on the identification of reaction products, the reaction mechanism for the oxidation of quercetin in the presence of Au(III) which involves two 2e(-) transfer processes was proposed.", publisher = "Royal Soc Chemistry, Cambridge", journal = "New Journal of Chemistry", title = "Investigation of reaction between quercetin and Au(III) in acidic media: mechanism and identification of reaction products", volume = "37", number = "4", pages = "901-908", doi = "10.1039/c2nj40742f" }
Bondžić, A. M., Lazarević-Pašti, T. D., Bondžić, B., Čolović, M. B., Jadranin, M.,& Vasić, V. M.. (2013). Investigation of reaction between quercetin and Au(III) in acidic media: mechanism and identification of reaction products. in New Journal of Chemistry Royal Soc Chemistry, Cambridge., 37(4), 901-908. https://doi.org/10.1039/c2nj40742f
Bondžić AM, Lazarević-Pašti TD, Bondžić B, Čolović MB, Jadranin M, Vasić VM. Investigation of reaction between quercetin and Au(III) in acidic media: mechanism and identification of reaction products. in New Journal of Chemistry. 2013;37(4):901-908. doi:10.1039/c2nj40742f .
Bondžić, Aleksandra M., Lazarević-Pašti, Tamara D., Bondžić, Bojan, Čolović, Mirjana B., Jadranin, Milka, Vasić, Vesna M., "Investigation of reaction between quercetin and Au(III) in acidic media: mechanism and identification of reaction products" in New Journal of Chemistry, 37, no. 4 (2013):901-908, https://doi.org/10.1039/c2nj40742f . .