Journal of Food Science and Technology

, Volume 54, Issue 6, pp 1467–1475 | Cite as

Antioxidant and iron-chelating properties of taxifolin and its condensation product with glyoxylic acid

Original Article

Abstract

The condensation of taxifolin with glyoxylic acid was examined, and the properties of the resulting product were compared with those of taxifolin. The structure of the product was determined by NMR spectroscopy. The ability of the polyphenols to scavenge reactive oxygen species (ROS) was estimated by luminol-dependent chemiluminescence. The iron-chelating and iron-reducing activities were studied using absorption spectrophotometry. It was shown that the condensation leads to the formation of a dimer consisting of two taxifolin units linked through a carboxymethine bridge at the C-6 and C-8 positions of the A ring. The dimer exhibited a somewhat higher ROS scavenging activity than taxifolin. The iron-binding capacity of the compounds was proportional to the number of polyphenol units. The iron-reducing ability of the dimer was lower than that of taxifolin. Thus, the dimer possessed a higher antioxidant activity than the parent flavonoid. The data obtained may be useful for a better understanding of processes occurring in foods and beverages and in a search for new active compounds.

Keywords

Taxifolin Glyoxylic acid Condensation ROS scavenging activity Iron-chelating and iron-reducing activities 

References

  1. Baderschneider B, Winterhalter P (2001) Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from Riesling wine and screening for antioxidant activity. J Agric Food Chem 49:2788–2798. doi:10.1021/jf010396d CrossRefGoogle Scholar
  2. Cerezo AB, Tesfaye W, Soria-Díaz ME et al (2010) Effect of wood on the phenolic profile and sensory properties of wine vinegars during ageing. J Food Compos Anal 23:175–184. doi:10.1016/j.jfca.2009.08.008 CrossRefGoogle Scholar
  3. Chen ZY, Chan PT, Ho KY et al (1996) Antioxidant activity of natural flavonoids is governed by number and location of their aromatic hydroxyl groups. Chem Phys Lipids 79:157–163. doi:10.1016/0009-3084(96)02523-6 CrossRefGoogle Scholar
  4. De Simón BF, Sanz M, Cadahía E et al (2014) Polyphenolic compounds as chemical markers of wine ageing in contact with cherry, chestnut, false acacia, ash and oak wood. Food Chem 143:66–76. doi:10.1016/j.foodchem.2013.07.096 CrossRefGoogle Scholar
  5. Drinkine J, Lopes P, Kennedy JA et al (2007) Ethylidene-bridged flavan-3-ols in red wine and correlation with wine age. J Agric Food Chem 55:6292–6299. doi:10.1021/jf070038w CrossRefGoogle Scholar
  6. Es-Safi NE, Cheynier V, Moutounet M (2000) Study of the reactions between (+)-catechin and furfural derivatives in the presence or absence of anthocyanins and their implication in food color change. J Agric Food Chem 48:5946–5954. doi:10.1021/jf000394d CrossRefGoogle Scholar
  7. Es-Safi N-E, Cheynier V, Moutounet M (2002) Role of aldehydic derivatives in the condensation of phenolic compounds with emphasis on the sensorial properties of fruit-derived foods. J Agric Food Chem 50:5571–5585. doi:10.1021/jf025503y CrossRefGoogle Scholar
  8. Foti M, Piattelli M, Baratta MT, Ruberto G (1996) Flavonoids, coumarins, and cinnamic acids as antioxidants in a micellar system. Structure–activity relationship. J Agric Food Chem 44:497–501. doi:10.1021/jf950378u CrossRefGoogle Scholar
  9. Gunda SK, Narasimha SKM, Shaik M (2014) P56lck kinase inhibitor studies: a 3D QSAR approach towards designing new drugs from flavonoid derivatives. Int J Comput Biol Drug Des 7:278–294. doi:10.1504/IJCBDD.2014.061648 CrossRefGoogle Scholar
  10. Hoefnagel AJ (1993) Glyoxylic acid: a key chemical. TU Delft, Delft University of Technology, DelftGoogle Scholar
  11. Ivanova SZ, Gorshkov AG, Kuzmin AV et al (2012) Phenolic compounds of Siberian and Dahurian larch phloem. Russ J Bioorganic Chem 38:769–774. doi:10.1134/S1068162012070096 CrossRefGoogle Scholar
  12. Jerez M, Touriño S, Sineiro J et al (2007) Procyanidins from pine bark: relationships between structure, composition and antiradical activity. Food Chem 104:518–527. doi:10.1016/j.foodchem.2006.11.071 CrossRefGoogle Scholar
  13. Jomova K, Valko M (2011) Advances in metal-induced oxidative stress and human disease. Toxicology 283:65–87CrossRefGoogle Scholar
  14. Jung H, Shin SY, Jung Y et al (2015) Quantitative relationships between the cytotoxicity of flavonoids on the human breast cancer stem-like cells MCF7-SC and their structural properties. Chem Biol Drug Des. doi:10.1111/cbdd.12512 Google Scholar
  15. Kiehlmann E, Li EPM (1995) Isomerization of dihydroquercetin. J Nat Prod 58:450–455. doi:10.1021/np50117a018 CrossRefGoogle Scholar
  16. Li A-N, Li S, Zhang Y-J et al (2014) Resources and biological activities of natural polyphenols. Nutrients 6:6020–6047. doi:10.3390/nu6126020 CrossRefGoogle Scholar
  17. Mira L, Fernandez MT, Santos M et al (2002) Interactions of flavonoids with iron and copper ions: a mechanism for their antioxidant activity. Free Radic Res 36:1199–1208. doi:10.1080/1071576021000016463 CrossRefGoogle Scholar
  18. Mladěnka P, Macáková K, Filipský T et al (2011) In vitro analysis of iron chelating activity of flavonoids. J Inorg Biochem 105:693–701. doi:10.1016/j.jinorgbio.2011.02.003 CrossRefGoogle Scholar
  19. Navas Díaz A, García Sánchez F, González Garcia JA (1998) Phenol derivatives as enhancers and inhibitors of luminol-H2O2-horseradish peroxidase chemiluminescence. J Biolumin Chemilumin 13:75–84. doi:10.1002/(SICI)1099-1271(199803/04)13:2%3C75::AID-BIO469%3E3.0.CO;2-7
  20. Ostronkov V, Lashin S (2012) Method for producing dihydroquercetin. Patent WO 2012064229.Google Scholar
  21. Pazos M, Gallardo JM, Torres JL, Medina I (2005) Activity of grape polyphenols as inhibitors of the oxidation of fish lipids and frozen fish muscle. Food Chem 92:547–557. doi:10.1016/j.foodchem.2004.07.036 CrossRefGoogle Scholar
  22. Rice-Evans CA, Miller NJ, Paganga G (1996) Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 20:933–956CrossRefGoogle Scholar
  23. Říha M, Karlíčková J, Filipský T et al (2014) In vitro evaluation of copper-chelating properties of flavonoids. RSC Adv 4:32628. doi:10.1039/C4RA04575K CrossRefGoogle Scholar
  24. Rødtjer A, Skibsted LH, Andersen ML (2006) Identification and quantification of phenolics in aromatic bitter and cherry liqueur by HPLC with electrochemical detection. Eur Food Res Technol 223:663–668. doi:10.1007/s00217-005-0250-4 CrossRefGoogle Scholar
  25. Rohdewald P (2002) A review of the French maritime pine bark extract (Pycnogenol), a herbal medication with a diverse clinical pharmacology. Int J Clin Pharmacol Ther 40:158–168. doi:10.5414/CPP40158 CrossRefGoogle Scholar
  26. Roy K, Mitra I (2009) Advances in quantitative structure–activity relationship models of antioxidants. Expert Opin Drug Discov 4:1157–1175CrossRefGoogle Scholar
  27. Saucier C, Guerra C, Pianet I et al (1997) (+)-Catechin—acetaldehyde condensation products in relation to wine-ageing. Phytochemistry 46:229–234. doi:10.1016/S0031-9422(97)00268-9 CrossRefGoogle Scholar
  28. Shatalin IV, Shmarev AN (2010) Peroxidation of lecithin in the presence of dihydroquercetin and its complex with ferrous iron ions. Biofizika 55:75–82. doi:10.1134/S0006350910010112 Google Scholar
  29. Shatalin YV, Shubina VS (2014) Partitioning of taxifolin-iron ions complexes in octanol-water system. Biophysics (Oxf) 59:351–356. doi:10.1134/S000635091403021X CrossRefGoogle Scholar
  30. Shubina VS, Shatalin YV (2013) Absorption spectroscopy study of acid-base and metal-binding properties of flavanones. J Appl Spectrosc 80:761–766. doi:10.1007/s10812-013-9838-9 CrossRefGoogle Scholar
  31. Teixeira S, Siquet C, Alves C et al (2005) Structure-property studies on the antioxidant activity of flavonoids present in diet. Free Radic Biol Med 39:1099–1108. doi:10.1016/j.freeradbiomed.2005.05.028 CrossRefGoogle Scholar
  32. Vauzour D, Rodriguez-Mateos A, Corona G et al (2010) Polyphenols and human health: prevention of disease and mechanisms of action. Nutrients 2:1106–1131CrossRefGoogle Scholar
  33. Wang HX, Ng TB (1999) Natural products with hypoglycemic, hypotensive, hypocholesterolemic, antiatherosclerotic and antithrombotic activities. Life Sci 65:2663–2677. doi:10.1016/S0024-3205(99)00253-2 CrossRefGoogle Scholar
  34. Weidmann AE (2012) Dihydroquercetin: more than just an impurity? Eur J Pharmacol 684:19–26CrossRefGoogle Scholar
  35. Wollmann N, Hofmann T (2013) Compositional and sensory characterization of red wine polymers. J Agric Food Chem 61:2045–2061. doi:10.1021/jf3052576 CrossRefGoogle Scholar
  36. Zhou H-C, Tam NF, Lin Y-M et al (2014) Relationships between degree of polymerization and antioxidant activities: a study on proanthocyanidins from the leaves of a medicinal mangrove plant Ceriops tagal. PLoS ONE 9:e107606. doi:10.1371/journal.pone.0107606 CrossRefGoogle Scholar

Copyright information

© Association of Food Scientists & Technologists (India) 2017

Authors and Affiliations

  1. 1.Institute of Theoretical and Experimental BiophysicsRussian Academy of SciencesMoscow RegionRussia

Personalised recommendations