Home Life Sciences Flavonoids inhibiting glycation of bovine serum albumin: affinity–activity relationship
Article
Licensed
Unlicensed Requires Authentication

Flavonoids inhibiting glycation of bovine serum albumin: affinity–activity relationship

  • , and
Published/Copyright: December 30, 2014
Become an author with De Gruyter Brill

Abstract

Protein glycation leads to the formation of advanced glycation end-products (AGEs), which contribute to the pathogenesis of diabetic complications. The structure-activity relationship of dietary flavonoids for inhibiting the glycation of bovine serum albumin (BSA) in vitro was subjected to a detailed investigation. The structure-activity relationship revealed that: 1) the hydroxylation on ring B of the flavones enhanced the inhibition and the hydroxyl groups at the C-5 and C-7 positions of flavones favoured the inhibition; 2) the optimal number of hydroxyl groups on ring B of the flavonols was one (at the C-3 position) and the methylation of flavonols weakened the inhibition; 3) the methoxylation at the C-6 position and methylation at C-4' position of genistein clearly enhanced the inhibition; 4) the hydroxyl groups at the C-5 and C-7 positions of flavanones were in favour of the inhibition; 5) the glycosylation of flavonoids significantly weakened the inhibition. Obvious linear affinity-activity relationships exist between the BSA-flavonoid interaction and flavonoids as BSA glycation inhibitors (R2 = 0.76585). The flavonoids with a higher affinity to BSA exhibited a stronger inhibition of the glycation of BSA.

References

Andrae-Marobela, K., Ghislain, F. W., Okatch, H., & Majinda, R. R. T. (2013). Polyphenols: A diverse class of multi-target anti-HIV-1 agents. Current Drug Metabolism, 14, 392-413. DOI: 10.2174/13892002113149990095. 10.2174/13892002113149990095Search in Google Scholar PubMed

Barnaby, O. S., Cerny, R. L., Clarke, W., & Hage, D. S. (2011). Comparison of modification sites formed on human serum albumin at various stages of glycation. Clinica Chimica Acta, 412, 277-285. DOI: 10.1016/j.cca.2010.10.018. 10.1016/j.cca.2010.10.018Search in Google Scholar PubMed PubMed Central

Cao, H., Shi, Y. J., & Chen, X. Q. (2013). Advances on the interaction between tea catechins and plasma proteins: Structureaffinity relationship, influence on antioxidant activity, and molecular docking aspects. Current Drug Metabolism, 14, 446-450. DOI: 10.2174/1389200211314040007.10.2174/1389200211314040007Search in Google Scholar PubMed

Deng, G. F., Xu, X. R., Zhang, Y., Li, D., Gan, R. Y., & Li, H. B. (2013). Phenolic compounds and bioactivities of pigmented rice. Critical Reviews in Food Science and Nutrition, 53, 296-306. DOI: 10.1080/10408398.2010.529624.10.1080/10408398.2010.529624Search in Google Scholar PubMed

Hughes, L. A. E., Arts, I. C.W., Ambergen, T., Brants, H. A. M., Dagnelie, P. C., Goldbohm, R. A., van den Brandt, P. A., & Weijenberg, M. P. (2008). Higher dietary flavone, flavonol, and catechin intakes are associated with less of an increase in BMI over time in women: a longitudinal analysis from the Netherlands Cohort Study. The American Journal of Clinical Nutrition, 88, 1341-1352. DOI: 10.3945/ajcn.2008.26058.Search in Google Scholar

Jang, D. S., Lee, Y. M., Jeong, I. H., & Kim, J. S. (2010). Constituents of the flowers of Platycodon grandiflorum with inhibitory activity on advanced glycation end products and rat lens aldose reductase in vitro. Archives of Pharmacal Research, 33, 875-880. DOI: 10.1007/s12272-010-0610-x.10.1007/s12272-010-0610-xSearch in Google Scholar PubMed

Johnson, M. H., Gonzalez de Mejia, E., Fan, J. F., Lila, M. A., & Yousef, G. G. (2013). Anthocyanins and proanthocyanidins from blueberry-blackberry fermented beverages inhibit markers of inflammation in macrophages and carbohydrateutilizing enzymes in vitro. Molecular Nutrition & Food Research, 57, 1182-1197. DOI: 10.1002/mnfr.201200678.10.1002/mnfr.201200678Search in Google Scholar PubMed

Jung, S. H., Lee, J. M., Lee, H. J., Kim, C. Y., Lee, E. H., & Um, B. H. (2007). Aldose reductase and advanced glycation endproducts inhibitory effect of Phyllostachys nigra. Biological and Pharmaceutical Bulletin, 30, 1569-1572. DOI: 10.1248/bpb.30.1569.10.1248/bpb.30.1569Search in Google Scholar PubMed

Liu, Y. J., Zhan, J., Liu, X. L., Wang, Y., Ji, J., & He, Q. Q. (2014). Dietary flavonoids intake and risk of type 2 diabetes: A meta-analysis of prospective cohort studies. Clinical Nutrition, 33, 59-63. DOI: 10.1016/j.clnu.2013.03.011.10.1016/j.clnu.2013.03.011Search in Google Scholar PubMed

Matsuda, H., Wang, T., Managi, H., & Yoshikawa, M. (2003). Structural requirements of flavonoids for inhibition of protein glycation and radical scavenging activities. Bioorganic & Medicinal Chemistry, 11, 5317-5323. DOI: 10.1016/j.bmc. 2003.09.045.Search in Google Scholar

Rondeau, P., & Bourdon, E. (2011). The glycation of albumin: Structural and functional impacts. Biochimie, 93, 645-658. DOI: 10.1016/j.biochi.2010.12.003.10.1016/j.biochi.2010.12.003Search in Google Scholar PubMed

Thornalley, P. J., Langborg, A., & Minhas, H. S. (1999). Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the glycation of proteins by glucose. Biochemical Journal, 344, 109-116. 10.1042/bj3440109Search in Google Scholar

van Dam, R. M., Naidoo, N., & Landberg, R. (2013). Dietary flavonoids and the development of type 2 diabetes and cardiovascular diseases: review of recent findings. Current Opinion on Lipidology, 24, 25-33. DOI: 10.1097/MOL.0b013e32835bcdff.10.1097/MOL.0b013e32835bcdffSearch in Google Scholar PubMed

Wang, Y. L., Zhao, Y., Yang, F., Yuan, Y. M., Wang, H., & Xiao, J. B. (2012). Influences of glucose on the dietary hydroxyflavonoids-plasma proteins interaction. Journal of Agricultural & Food Chemistry, 60, 12116-12221. DOI: 10.1021/jf303094e.10.1021/jf303094eSearch in Google Scholar PubMed

Wedick, N. M., Pan, A., Cassidy, A., Rimm, E. B., Sampson, L., Rosner, B.,Willett,W., Hu, F. B., Sun, Q., & van Dam, R.M. (2012). Dietary flavonoid intakes and risk of type 2 diabetes in US men and women. The American Journal of Clinical Nutrition, 95, 925-933. DOI: 10.3945/ajcn.111.028894.10.3945/ajcn.111.028894Search in Google Scholar PubMed PubMed Central

Wild, S., Roglic, G., Green, A., Sicree, R., & King, H. (2004). Global prevalence of diabetes: Estimates for the year 2000 and projections for 2030. Diabetes Care, 27, 1047-1053. DOI: 10.2337/diacare.27.5.1047.10.2337/diacare.27.5.1047Search in Google Scholar PubMed

World Health Organization (2013). Diabetes. Fact sheet no. 312. Retrieved March 2013, from http://www.who.int/mediacentre/factsheets/fs312/en/index.html Search in Google Scholar

Xiao, J. B., & Kai, G. Y. (2012). A review of dietary polyphenolplasma protein interactions: Characterization, influence on the bioactivity, and structure-affinity relationship. Critical Reviews in Food Science and Nutrition, 52, 85-101. DOI: 10.1080/10408398.2010.499017.10.1080/10408398.2010.499017Search in Google Scholar PubMed

Xiao, J. B. (2013). Polyphenol-plasma proteins interaction: Its nature, analytical techniques, and influence on bioactivities of polyphenols. Current Drug Metabolism, 14, 367-368. DOI: 10.2174/1389200211314040001.10.2174/1389200211314040001Search in Google Scholar PubMed

Xiao, J. B., Ni, X. L., Kai, G. Y., & Chen, X. Q. (2013a). A review on structure-activity relationship of dietary polyphenols inhibiting α-amylase. Critical Reviews in Food Science and Nutrition, 53, 497-506. DOI: 10.1080/10408398.2010. 548108.Search in Google Scholar

Xiao, J. B., Kai, G. Y., Yamamoto, K., & Chen, X. Q. (2013b). Advance in dietary polyphenols as α-glucosidases inhibitors: A review on structure-activity relationship aspect. Critical Reviews in Food Science and Nutrition, 53, 818-836. DOI: 10.1080/10408398.2011.561379.10.1080/10408398.2011.561379Search in Google Scholar PubMed

Xiao, J. B., & H¨ogger, P. (2014). Dietary polyphenols and type 2 diabetes: current insights and future perspectives. Current Medicinal Chemistry, 21, 1-16. DOI: 10.2174/0929867321666140706130807.10.2174/0929867321666140706130807Search in Google Scholar PubMed

Xiao, J. B., Chen, T. T., & Cao, H. (2014). Flavonoid glycosylation and biological benefits. Biotechnology Advances, in press. DOI: 10.1016/j.biotechadv.2014.05.004.10.1016/j.biotechadv.2014.05.004Search in Google Scholar PubMed

Xiao, J. B., Ni, X. L., Kai, G. Y., & Chen, X. Q. (2015). Advance in dietary polyphenols as aldose reductases inhibitors: Structure-activity relationship aspect. Critical Reviews in Food Science and Nutrition, 55, 16-31. DOI: 10.1080/10408398.2011.584252.10.1080/10408398.2011.584252Search in Google Scholar PubMed

Xie, Y. X., & Chen, X. Q. (2013). Structures required of polyphenols for inhibiting advanced glycation end products formation. Current Drug Metabolism, 14, 414-431. DOI: 10.2174/1389200211314040005. 10.2174/1389200211314040005Search in Google Scholar PubMed

Received: 2014-5-20
Revised: 2014-7-14
Accepted: 2014-8-5
Published Online: 2014-12-30
Published in Print: 2015-3-1

© 2015 Institute of Chemistry, Slovak Academy of Sciences

Articles in the same Issue

  1. One-step preparation of porous copper nanowires electrode for highly sensitive and stable amperometric detection of glyphosate
  2. Classification of wine distillates using multivariate statistical methods based on their direct GC-MS analysis
  3. Determination of cigarette papers moisture content by gas chromatography
  4. Flavonoids inhibiting glycation of bovine serum albumin: affinity–activity relationship
  5. Treatment of natural rubber latex serum waste by co-digestion with macroalgae, Chaetomorpha sp. and Ulva intestinalis, for sustainable production of biogas
  6. Physicochemical aspects of Trichosporon cutaneum CCY 30-5-10 adhesion and biofilm formation potential on cellophane
  7. Immobilisation of Aspergillus oryzae α-amylase and Aspergillus niger glucoamylase enzymes as cross-linked enzyme aggregates
  8. Dissolution kinetics of cerussite in an alternative leaching reagent for lead
  9. Preparation of quaternary pyridinium salts as possible proton conductors
  10. Stable UV absorption material synthesized by intercalation of squaric acid anion into layered double hydroxides
  11. Electrolytic preparation of nanosized Cu/Ni–Cu multilayered coatings
  12. Efficient solvent-free synthesis of bis(indolyl)methanes on SiO2 solid support under microwave irradiation
  13. Facile and direct synthesis of symmetrical acid anhydrides using a newly prepared powerful and efficient mixed reagent
  14. Practical synthesis of 2,3-dimethoxy-5-hydroxymethyl-6-methyl-1,4-benzoquinone
  15. Conversion of phenylacetonitrile in supercritical alcohols within a system containing small volume of water
Downloaded on 18.3.2026 from https://www.degruyterbrill.com/document/doi/10.1515/chempap-2015-0050/html
Scroll to top button