Synthesis, characterization and study of antioxidant activity of quercetin–magnesium complex

Ghosh, Nilanjan; Chakraborty, Tania; Mallick, Sougata; Mana, Supriya; Singha, Deepanwita; Ghosh, Balaram; Roy, Subhas Chandra

doi:10.1016/j.saa.2015.07.050

Cited by 97 publications

(73 citation statements)

References 30 publications

(28 reference statements)

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“…2 Second, compared with C(5) OH, delocalization of the oxygen lone pair electrons of C(3) OH group occurs more easily, which facilitates delocalization of the π electrons throughout the whole A, C, and B rings. 1,[6][7][8]13,36,38 Again, this spectral change of IR spectra indicates clearly that metal ions chelate the site 1 or 3. If a metal:ligand complex is formed at a ratio of 2:1, the second metal ion can be coordinated at site 2.…”

Section: Spectroscopic Properties Of the Quercetin-metal Complexesmentioning

confidence: 81%

“…[6][7][8][9][10] Flavonoids are regarded as antioxidants because the compounds can scavenge free radicals. 1,7,8,13 Due to the presence of carbonyl and hydroxyl groups, QCT can effectively coordinate with metal ions to form complexes. [11][12][13] Quercetin (QCT, 3,3 0 ,4 0 ,5,7-pentahydroxyflavone) is one of the most bioactive and commonly known dietary flavonoids.…”

Section: Introductionmentioning

confidence: 99%

“…Another mechanism is related to interactions between flavonoids and transition metal ions to form a complex that inhibits the participation of metal ions in free radical-generating processes. [6][7][8]14,15 Chelation of metal ions, particularly transition metals which are involved in processes that form radicals, is widely considered to be another mechanism of the antioxidant activity of flavonoids. Owing to its biological and pharmaceutical properties, QCT has attracted great attention of many researchers.…”

Section: Introductionmentioning

confidence: 99%

“…[11][12][13] Quercetin (QCT, 3,3 0 ,4 0 ,5,7-pentahydroxyflavone) is one of the most bioactive and commonly known dietary flavonoids. [6][7][8][9]11,16,17 Also, flavonoids play a valuable role in both the bioavailability of metal ions, which are present at low levels in the human body, and the toxicity of a variety of toxic metals. 1,7,8,13 Due to the presence of carbonyl and hydroxyl groups, QCT can effectively coordinate with metal ions to form complexes.…”

Section: Introductionmentioning

confidence: 99%

“…Owing to its biological and pharmaceutical properties, QCT has attracted great attention of many researchers. 8,18 This work aims to study the chelation of various divalent metal cations (Cu 2+ , Ni 2+ , Co 2+ , Mn 2+ , Zn 2+ , Mg 2+ , Ca 2+ ) Scheme 1. QCT has three potential chelating sites in competition between: (1) 3-hydroxyl and 4-carbonyl groups (site 1), (2) 3 0 and 4 0 -hydroxyl groups (catechol) in B ring (site 2), and (3) 5-hydroxyl and 4-carbonyl groups (site 3) (see Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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Spectroscopic Properties of the Quercetin–Divalent Metal Complexes in Hydro‐Organic Mixed Solvent

Park

Kim

et al. 2018

Bulletin Korean Chem Soc

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The formation and spectroscopic properties of quercetin (QCT)-divalent metal complexes were studied using Cu 2+ , Ni 2+ , Co 2+ , Mn 2+ , Zn 2+ , Mg 2+ , and Ca 2+ in a hydro-organic mixed solvent. The change of UV/visible absorption spectra of QCT due to addition of a metal showed the complex formation. The intensity of fluorescence spectra increased gradually with titration of the metal. The experimental data and theoretical calculation suggest that Cu 2+ , Ni 2+ , Co 2+ , and Mn 2+ coordinate the site between C(3) OH and C(4) O but Zn 2+ prefers to bind to the site between C(5) OH and C(4) O. QCT-Cu 2+ , QCT-Ni 2+ , QCT-Co 2+ , and QCT-Mn 2+ complexes exhibit S 2 ! S 0 fluorescence only as S 1 ! S 0 emission is absent due to the excited-state intramolecular proton transfer (ESIPT) at the S 1 state. As this ESIPT cannot occur at the QCT-Zn 2+ due to the chelation of Zn 2+ at a different site, QCT-Zn 2+ can produce characteristic S 2 ! S 0 and S 1 ! S 0 dual fluorescence.

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Section: Spectroscopic Properties Of the Quercetin-metal Complexesmentioning

confidence: 81%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Spectroscopic Properties of the Quercetin–Divalent Metal Complexes in Hydro‐Organic Mixed Solvent

Park

Kim

et al. 2018

Bulletin Korean Chem Soc

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Reactivities of quercetin and metallo‐quercetin with superoxide anion radical and molecular oxygen

Lewis

Wallace

Peterson

et al. 2021

Electrochemical Science Adv

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This work describes the differential quenching of molecular oxygen and superoxide anion radical (O2˙–) by (metallo)‐quercetin (QCR) complexes. The in situ complexes were more reactive with molecular oxygen than preformed complexes. By adjusting the potential range, it was determined that Cu2+ complexes exhibited similar superoxide anion radical (O2˙–) quenching ability as free QCR. The Fe3+ complexes were less reactive than free QCR or Cu2+ complexes. The data indicate that metal ions significantly modulated reactivity of QCR with O2˙– or molecular oxygen, and may regulate antioxidant activity and reactive oxygen species levels in a complex biological setting.

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Quercetin protected against isoniazide‐induced HepG2 cell apoptosis by activating the SIRT1/ERK pathway

Zhang

Tao

et al. 2019

J Biochem & Molecular Tox

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Isoniazid (INH) is one of the most commonly used antituberculosis drugs, but its clinical applications have been limited by severe hepatic toxicity. Quercetin (Que), a natural flavonoid, has been proved to have many medicinal properties. This study aimed to clarify the possible protective effects of Que against INH‐induced hepatotoxicity using HepG2 cells. Our results indicated that Que significantly increased cell viability, superoxide dismutase, and GSH levels, while decreased alanine aminotransferase/aspartate aminotransferase levels. Besides, Que significantly abrogated INH‐induced cell apoptosis by upregulating the expression levels of Bcl‐2 and decreasing the levels of Bax, cleaved caspase‐3, and cleaved caspase‐9. Furthermore, Que obviously reversed the inhibition of INH on Sirtuin 1 (SIRT1) expression and extracellular signal‐regulated kinase (ERK) phosphorylation. Next, the SIRT1 inhibitor EX527 blocked the enhancement of Que upon ERK phosphorylation. Notably, EX527 partially abolished the beneficial effects of Que. In brief, our results provided the first evidence that Que protected against INH‐induced HepG2 cells by regulating the SIRT1/ERK pathway.

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Synthesis, characterization and study of antioxidant activity of quercetin–magnesium complex

Cited by 97 publications

References 30 publications

Spectroscopic Properties of the Quercetin–Divalent Metal Complexes in Hydro‐Organic Mixed Solvent

Spectroscopic Properties of the Quercetin–Divalent Metal Complexes in Hydro‐Organic Mixed Solvent

Reactivities of quercetin and metallo‐quercetin with superoxide anion radical and molecular oxygen

Quercetin protected against isoniazide‐induced HepG2 cell apoptosis by activating the SIRT1/ERK pathway

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