Skip to main content
Log in

Binding Interaction of Glycated, Fructated and Native Human Hemoglobin with Bulk Propolis

  • Research Paper
  • Published:
Iranian Journal of Science and Technology, Transactions A: Science Aims and scope Submit manuscript

Abstract

Recently, the great interests in application of natural product have led to focus on the potential impact on bio macromolecules. Propolis is one of the natural products with various biological activities such as anti-diabetic effect. Under hyperglycemia, hemoglobin (Hb) frequently undergoes non-enzymatic glycation which affect its structure and function. In this study, the binding interaction between bulk propolis and three forms of Hb, native Hb, glycated Hb (GHb) and fructated Hb (FHb), in two temperatures of 25 and 37 °C have been examined and compared with our previous study (interaction of propolis nanoparticles with Hb, GHb and FHb). The binding studied with applying fluorescence and far UV circular dichroism spectroscopic techniques. Bulk Propolis possess the ability to quench the intrinsic fluorescence of the different types Hb like propolis nanoparticles. The mechanism of interaction bulk propolis with different types Hb was similar to the propolis nanoparticles, dynamic quenching in native Hb and static quenching in glycated and fructated Hb. According to the modified Stern–Volmer equation, the binding constant and number of binding sites were obtained. The result suggested that propolis nanoparticles have more quenching rate constant (kq) in compared to the bulk propolis in interaction different types Hb. In addition, the values of binding constant (Kb) revealed that nanopropolis has more binding affinity in compared to the bulk propolis. Data obtained from thermodynamic parameters implied more portion of electrostatic forces in GHb-propolis than native Hb-propolis and more hydrophobic portion in FHb-propolis. The CD spectra of Hb, GHb and FHb displayed no significant changes in secondary structure after incubated with propolis. These data are agreement with propolis nanoparticles. Results showed that propolis nanoparticles are a stronger quencher and bound to Hb, GHb and FHb with higher affinity than bulk propolis.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  • Abd El Megid AD, Khaled M, Emam MA, Adel A (2018) Biochemical role of zinc oxide and propolis nanoparticles in protection rabbits against coccidiosis. Benha Veterinary Medical Journal 34(1):314–328

    Article  Google Scholar 

  • Ahmed N, Thornalley PJ (2007) Advanced glycation endproducts: what is their relevance to diabetic complications? Diabetes Obes Metab 9(3):233–245

    Article  Google Scholar 

  • Ahmed N (2005) Advanced glycation endproducts—role in pathology of diabetic complications. Diabetes Res Clin Pract 67(1):3–21

    Article  Google Scholar 

  • Ahn MR, Kumazawa S, Usui Y, Nakamura J, Matsuka M, Zhu F, Nakayama T (2007) Antioxidant activity and constituents of propolis collected in various areas of China. Food Chem 101(4):1383–1392

    Article  Google Scholar 

  • Anjum SI, Ullah A, Khan KA, Attaullah M, Khan H, Ali H, Bashir MA, Tahir M, Ansari MJ, Ghramh HA, Adgaba N (2019) Composition and functional properties of propolis (bee glue): A review. Saudi Journal of Biological Sciences 26(7):1695–1703

    Article  Google Scholar 

  • Ayodhya D, Veerabhadram G (2016) Green synthesis, optical, structural, photocatalytic, fluorescence quenching and degradation studies of ZnS nanoparticles. J Fluoresc 26(6):2165–2175

    Article  Google Scholar 

  • Bose T, Bhattacherjee A, Banerjee S, Chakraborti AS (2013) Methylglyoxal-induced modifications of hemoglobin: structural and functional characteristics. Arch Biochem Biophys 529(2):99–104

    Article  Google Scholar 

  • Bose T, Chakraborti AS (2008) Fructose-induced structural and functional modifications of hemoglobin: implication for oxidative stress in diabetes mellitus. Biochimica et Biophysica Acta (BBA)-General Subjects1780(5):800–8.

  • Chakraborty S, Chaudhuri S, Pahari B, Taylor J, Sengupta PK, Sengupta B (2012) A critical study on the interactions of hesperitin with human hemoglobin: Fluorescence spectroscopic and molecular modeling approach. J Lumin 132(6):1522–1528

    Article  Google Scholar 

  • Cho N, Shaw JE, Karuranga S, Huang Y, da Rocha Fernandes JD, Ohlrogge AW, Malanda B (2013) IDF Diabetes Atlas: Global estimates of diabetes prevalence for 2017 and projections for 2045. Diabetes Res Clin Pract 138:271–281

    Article  Google Scholar 

  • Corrêa DH, Ramos CH (2009) The use of circular dichroism spectroscopy to study protein folding, form and function. Afr J Biochem Res 3(5):164–173

    Google Scholar 

  • Darshan TR (2012) An overview of propolis as potential of new drug development. Journal of Pharmacy Education and Research 3(2):113–119

    Google Scholar 

  • Esfandfar P, Falahati M, Saboury A (2016) Spectroscopic studies of interaction between CuO nanoparticles and bovine serum albumin. J Biomol Struct Dyn 34(9):1962–1968

    Article  Google Scholar 

  • GhoshMoulick R, Bhattacharya J, Roy S, Basak S, Dasgupta AK (2007) Compensatory secondary structure alterations in protein glycation. Biochimica et Biophysica Acta (BBA)-Proteins and Proteomics 1774(2):233–42.

  • Goodarzi M, Moosavi-Movahedi AA, Habibi-Rezaei M, Shourian M, Ghourchian H, Ahmad F, Farhadi M, Saboury AA, Sheibani N (2014) Hemoglobin fructation promotes heme degradation through the generation of endogenous reactive oxygen species. Spectrochim Acta Part A Mol Biomol Spectrosc 130:561–567

    Article  Google Scholar 

  • Guariguata L, Whiting DR, Hambleton I, Beagley J, Linnenkamp U, Shaw JE (2014) Global estimates of diabetes prevalence for 2013 and projections for 2035. Diabetes Res Clin Pract 103(2):137–149

    Article  Google Scholar 

  • Gugliucci A (2017) Formation of fructose-mediated advanced glycation end products and their roles in metabolic and inflammatory diseases. Advances in nutrition 8(1):54–62

    Article  Google Scholar 

  • Jianrong C, Yuqing M, Nongyue H, Xiaohua W, Sijiao L (2004) Nanotechnology and biosensors. Biotechnol Adv 22(7):505–518

    Article  Google Scholar 

  • Kar M, Roy A, Bose T, Chakraborti AS (2006) Effect of glycation of hemoglobin on its interaction with trifluoperazine. Protein J 25(3):202–211

    Article  Google Scholar 

  • Kazemi F, Divsalar A, Saboury AA (2018) Structural analysis of the interaction between free, glycated and fructated hemoglobin with propolis nanoparticles: A spectroscopic study. Int J Biol Macromol 109:1329–1337

    Article  Google Scholar 

  • Koohshekan B, Divsalar A (2017) In vitro glycation of bovine liver catalase by glucose and fructose and antigycation effects of aspirin: a spectroscopic study. J Biomol Struct Dyn 35(14):3061–3069

    Article  Google Scholar 

  • Mahmoudi M, Lynch I, Ejtehadi MR, Monopoli MP, Bombelli FB, Laurent S (2011) Protein− nanoparticle interactions: opportunities and challenges. Chem Rev 111(9):5610–5637

    Article  Google Scholar 

  • Maji A, Beg M, Mandal AK, Das S, Jha PK, Kumar A, Sarwar S, Hossain M, Chakrabarti P (2017) Spectroscopic interaction study of human serum albumin and human hemoglobin with Mersilea quadrifolia leaves extract mediated silver nanoparticles having antibacterial and anticancer activity. J Mol Struct 1141:584–592

    Article  Google Scholar 

  • Naeeminejad S, Assaran Darban R, Beigoli S, Saberi MR, Chamani J (2017) Studying the interaction between three synthesized heterocyclic sulfonamide compounds with hemoglobin by spectroscopy and molecular modeling techniques. J Biomol Struct Dyn 35(15):3250–3267

    Article  Google Scholar 

  • Naveenraj S, Anandan S (2013) Binding of serum albumins with bioactive substances–nanoparticles to drugs. J Photochem Photobiol, C 14:53–71

    Article  Google Scholar 

  • Nna VU, Bakar AB, Lazin MR, Mohamed M (2018) Antioxidant, anti-inflammatory and synergistic anti-hyperglycemic effects of Malaysian propolis and metformin in streptozotocin–induced diabetic rats. Food Chem Toxicol 120:305–320

    Article  Google Scholar 

  • Ojha B, Das G (2010) The interaction of 5-(alkoxy) naphthalen-1-amine with bovine serum albumin and its effect on the conformation of protein. J Phys Chem B 114(11):3979–3986

    Article  Google Scholar 

  • Rashidipour S, Naeeminejad S, Chamani J (2016) Study of the interaction between DNP and DIDS with human hemoglobin as binary and ternary systems: spectroscopic and molecular modeling investigation. J Biomol Struct Dyn 34(1):57–77

    Article  Google Scholar 

  • Ross PD, Subramanian S (1981) Thermodynamics of protein association reactions: forces contributing to stability. Biochemistry 20(11):3096–3102

    Article  Google Scholar 

  • Roy S, Das TK (2015) Study of interaction between tryptophan, tyrosine, and phenylalanine separately with silver nanoparticles by fluorescence quenching method. J Appl Spectrosc 82(4):598–606

    Article  Google Scholar 

  • Sahebi U, Divsalar A (2016) Synergistic and inhibitory effects of propolis and aspirin on structural changes of human hemoglobin resulting from glycation: an in vitro study. J Iran Chem Soc 13(11):2001–2011

    Article  Google Scholar 

  • Sarzehi S, Chamani J (2010) Investigation on the interaction between tamoxifen and human holo-transferrin: determination of the binding mechanism by fluorescence quenching, resonance light scattering and circular dichroism methods. Int J Biol Macromol 47(4):558–569

    Article  Google Scholar 

  • Sen S, Bose T, Roy A, Chakraborti AS (2007) Effect of non-enzymatic glycation on esterase activities of hemoglobin and myoglobin. Mol Cell Biochem 301(1–2):251–257

    Article  Google Scholar 

  • Sen S, Kar M, Roy A, Chakraborti AS (2005) Effect of nonenzymatic glycation on functional and structural properties of hemoglobin. Biophys Chem 113(3):289–298

    Article  Google Scholar 

  • Sengupta B, Swenson J (2005) Properties of normal and glycated human hemoglobin in presence and absence of antioxidant. Biochem Biophys Res Commun 334(3):954–959

    Article  Google Scholar 

  • Sforcin JM, Bankova V (2011) Propolis: is there a potential for the development of new drugs? J Ethnopharmacol 133(2):253–260

    Article  Google Scholar 

  • Shibata T, Shibata S, Shibata N, Kiyokawa E, Sasaki H, Singh DP, Kubo E (2016) Propolis, a Constituent of Honey, Inhibits the Development of Sugar Cataracts and High-Glucose-Induced Reactive Oxygen Species in Rat Lenses. Journal of ophthalmology 2016:1–6

    Article  Google Scholar 

  • Shao Q, Wu P, Gu P, Xu X, Zhang H, Cai C (2011) Electrochemical and spectroscopic studies on the conformational structure of hemoglobin assembled on gold nanoparticles. J Phys Chem B 115(26):8627–8637

    Article  Google Scholar 

  • Siddiqui Z, Ishtikhar M, Ahmad S (2018) d-Ribose induced glycoxidative insult to hemoglobin protein: An approach to spot its structural perturbations. Int J Biol Macromol 112:134–147

    Article  Google Scholar 

  • Sreedhanya S, Jeena VR, Ammu S, Aravindakumar CT, Aravind UK (2020) Spectroscopic and theoretical methods to probe protein–ligand binding. Materials Today: Proceedings 1–6.

  • Sun Y, Wei S, Yin C, Liu L, Hu C, Zhao Y, Ye Y, Hu X, Fan J (2011) Synthesis and spectroscopic characterization of 4-butoxyethoxy-N-octadecyl-1, 8-naphthalimide as a new fluorescent probe for the determination of proteins. Bioorg Med Chem Lett 21(12):3798–3804

    Article  Google Scholar 

  • Vasan S, Foiles P, Founds H (2003) Therapeutic potential of breakers of advanced glycation end product–protein crosslinks. Arch Biochem Biophys 419(1):89–96

    Article  Google Scholar 

  • Wang C, Liu B, Bian G, Ma L (2017) Investigation on the interaction of glipizide with bovine hemoglobin by spectroscopy and molecular docking. Spectroscopy Letter 50(9):476–481

    Article  Google Scholar 

  • Zeinabad HA, Kachooei E, Saboury AA, Kostova I, Attar F, Vaezzadeh M, Falahati M (2016) Thermodynamic and conformational changes of protein toward interaction with nanoparticles: a spectroscopic overview. RSC advances 6(107):105903–105919

    Article  Google Scholar 

  • Zolghadri S, Saboury AA, Golestani A, Divsalar A, Rezaei-Zarchi S, Moosavi-Movahedi AA (2009) Interaction between silver nanoparticle and bovine hemoglobin at different temperatures. J Nanopart Res 11(7):1751

    Article  Google Scholar 

Download references

Acknowledgements

The authors would like to thank the respectful Research Council of Kharazmi University (Grant No. 1397) for their financial support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Adeleh Divsalar.

Ethics declarations

Conflict of interest

The authors strictly state that the content of this paper has no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kazemi, F., Divsalar, A. & Saboury, A.A. Binding Interaction of Glycated, Fructated and Native Human Hemoglobin with Bulk Propolis. Iran J Sci Technol Trans Sci 45, 785–793 (2021). https://doi.org/10.1007/s40995-021-01108-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40995-021-01108-1

Keywords

Navigation