THE ACTIVITY OF INTERMOLECULAR HYDROGEN COMPLEXES OF QUERCETIN WITH GLUCOSE IN REAC-TIONS WITH COTTON OIL PEROXY RADICALS

UDC 547.565:544.421:544.43

  • Natal'ya Ivanovna Belaya Donetsk National University https://orcid.org/0000-0003-3359-3239 Email: nat.iv.belaya@gmail.com
  • Aleksandr Vladimirovich Belyy Donetsk National University Email: a.v.belyj@gmail.com
  • Galina Anatol'yevna Tikhonova Donetsk National University Email: tixonovagala@ya.ru
  • Yaroslav Sergeyevich Udalov Donetsk National University Email: yarikzbest@mail.ru
Keywords: quercetin, glucose, radical, antioxidant, synergism

Abstract

The presence of a strong synergistic effect of the binary quercetin–glucose composition in the reaction with peroxyl radicals generated during the auto- and initiated oxidation of cottonseed oil was established. The highest antiradical activity showed the synergistic compositions at a ratio of 60 : 40%. The established synergism refers to the type when products, formed during reaction, interacts with peroxy radicals more effectively than the original individual substances. Such products may be intermolecular hydrogen-bonded complexes of quercetin and glucose, the existence of such complexes confirmed by NMR spectroscopy. DFT method showed that the most stable is the donor H-complex, where quercetin acts as a hydrogen donor. A quantitative measure of the electron-donating properties of H complexes – the ionization potential – was calculated in the gas phase. The ionization potential of the donor complex is lower so its reducing ability in reaction with radicals is higher than that of the monomeric antioxidant.This can explain the presence of the maximum synergistic effect in the quercetin-glucose mixture at the ratio of 60 : 40%, when, probably, the proportion of donor H-complexes in the reaction mixture is maximum. Obtained results make it possible to carry out a targeted search for effective antioxidant synergistic flavonoid–carbohydrate compositions in plant extracts.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

Author Biographies

Natal'ya Ivanovna Belaya, Donetsk National University

кандидат химических наук, доцент, доцент кафедры физической химии

Aleksandr Vladimirovich Belyy, Donetsk National University

кандидат химических наук, доцент, декан химического факультета

Galina Anatol'yevna Tikhonova, Donetsk National University

младший научный сотрудник НИЧ кафедры физической химии

Yaroslav Sergeyevich Udalov, Donetsk National University

бакалавр

References

Kostyuk V.A. Bioradikaly i bioantioksidanty: monografiya. [Bioradicals and bioantioxidants: monograph]. Minsk, 2004, 179 p. (in Russ.).

Vermerris W. Phenolic Compound Biochemistry, Dodrecht, 2006, 275 p.

Zheng Y.Z., Deng G., Guo R., Chen D.F., Fu Z.M. Int. J. Mol. Sci., 2019, vol. 20, no. 2, pp. 1‒11. DOI: 10.3390/ijms20020397.

Son N.T., Mai Thanh D.T., Van Trang N. J. Mol. Struct., 2019, vol. 1193, pp. 76–88. DOI: 10.1016/j.molstruc.2019.05.016.

Wang J., Hu S., Nie S., Yu Q., Xie M. Oxidative Medicine and Cellular Longevity, 2016, vol. 64, pp. 1–13. DOI: 10.1155/2016/5692852.

Thondre P.S., Ryan L., Henry C.J.K. Food Chemistry, 2011, vol. 126, no. 1, pp. 72–77. DOI: 10.1016/j.foodchem.2010.10.074.

Siu K.C., Chen X., Wu J.Y. Journal of Functional Foods, 2014, vol. 11, pp. 548–556. DOI: 10.1016/j.jff.2014.08.012.

Rogov I.A. Khimiya pishchi. [Food chemistry]. Moscow, 2007, 853 p. (in Russ.).

Kaleem A., Aziz S., Iqtedar M., Abdullah R., Aftab M., Rashid F., Shakoori F.R., Naz R. Fuuast J. Biol., 2015, vol. 5, no. 2, pp. 191–196.

Shlyapintokh V.Ya., Karpukhin O.N., Postnikov L.M., Zakharov I.P., Vichutinskiy A.A., Tsepalov V.F. Khemilyuminestsentnyye metody issledovaniya medlennykh khimicheskikh protsessov. [Chemiluminescent methods for the study of slow chemical processes]. Moscow, 1966, 300 p. (in Russ.).

Belyakov V.A., Vasil'yev R.F., Fedorova G.F. Kinetika i kataliz, 2004, vol. 45, no. 3, pp. 355–362. (in Russ.).

Veprintsev T.L., Naumov V.V., Trofimov A.V. Butlerovskiye soobshcheniya, 2011, vol. 25, no. 5, pp. 96–100. (in Russ.).

Arslan F.N., Sapci A.N., Duru F., Kara H. Internat. J. Food Prop., 2017, vol. 20, no. 3, pp. 704–717. DOI: 10.1080/10942912.2016.1177544.

Vasil'yev R.F., Veprintsev T.L., Dolmatova L.S., Naumov V.V., Trofimov A.V., Tsaplev Yu.B. Kinetika i kataliz, 2014, vol. 55, no. 2, pp. 157–162. (in Russ.).

Zheng Y.-Z., Deng G., Liang Q., Chen D.-F., Guo R., Lai R.-C. Sci. Reports, 2017, vol. 7, pp. 1–11. DOI: 10.1038/s41598-017-08024-8.

Marković Z.S., Dimitrić Marković J.M., Doličanin Ć.B. Theor. Chem. Acc., 2010, vol. 127, pp. 69–80. DOI: 10.1007/s00214-009-0706-x.

Pogodaeva N.N., Medvedeva S.A., Sukhov B.G., Larina L.I. Chem. Nat. Comp., 2012, vol. 48, no. 5, pp. 723–727. DOI: 10.1007/s10600-012-0368-0.

Belaya N.I., Belyi A.V., Zarechnaya O.M., Scherbakov I.N., Doroshkevich V.S. Russian Journal of General Chemis-try, 2018, vol. 88, no. 7, pp. 1351–1362. DOI: 10.1134/S013434751807001X.

Weinberg D.R., Gagliardi C.J., Hull J.F., Murphy C.F., Kent C.A., Westlake B., Paul A., Ess D.H., McCafferty G.D., Meyer T.J. Chem Rev., 2007, vol. 107, no. 11, pp. 5004–5064. DOI: 10.1021/cr0500030.

Arunan E., Desiraju G.R., Klein R.A., Sadlej J., Scheiner S., Alkorta I., Clary D.C., Crabtree R.H., Dannenberg J.J., Hobza P., Kjaergaard H.G., Legon A.C., Mennucci B., Nesbitt D.J. Pure Appl. Chem., 2011, vol. 83, no. 8, pp. 1637–1641. DOI: 10.1351/PAC-REC-10-01-02.

Ahn D.-S., Jeon I.-S., Jang S.-H., Park S.-W., Lee S., Cheong W. Bull. Korean Chem. Soc., 2003, vol. 24, no. 6, pp. 695–702. DOI: 10.5012/bkcs.2003.24.6.695.

Yamabe S., Yamazaki S. Int. J. Quantum Chem., 2017, vol. 118, no. 6, pp. 1–14. DOI: 10.1002/qua.25510.

Derou E. Sovremennyye metody YaMR dlya khimicheskikh issledovaniy. [Modern NMR methods for chemical research]. Moscow, 1992, 403 p. (in Russ.).

Published
2020-10-22
How to Cite
1. Belaya N. I., Belyy A. V., Tikhonova G. A., Udalov Y. S. THE ACTIVITY OF INTERMOLECULAR HYDROGEN COMPLEXES OF QUERCETIN WITH GLUCOSE IN REAC-TIONS WITH COTTON OIL PEROXY RADICALS // chemistry of plant raw material, 2020. № 3. P. 57-65. URL: http://journal.asu.ru/cw/article/view/6631.
Section
Low-molecular weight compounds