Skip to main content
SpringerLink
Log in

An investigation into the preparation, characterization and antioxidant activity of puerarin/cyclodextrin inclusion complexes

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

The inclusion complexes between puerarin and three cyclodextrins (CDs), namely β-cyclodextrin (β-CD), (2-hydroxy)propyl-β-cyclodextrin (HP-β-CD, DS = 4.2) and methyl-β-cyclodextrin (Me-β-CD, DS = 12.5) were prepared. The effects of the complexation on the stability of puerarin were investigated in both solution and the solid state by methods of phase solubility study, XRD, DSC and SEM. Furthermore, the antioxidant activities of puerarin and puerarin/CDs inclusion complexes were determined by reducing power and 1,1-diphenyl-2-picryl-hydrazyl methods. Results showed that puerarin formed 1:1 stoichiometric inclusion complexes with β-CD, HP-β-CD and Me-β-CD. Additionally, the solubility and thermal stability of puerarin was improved after encapsulating by CDs. Antioxidant activity studies showed that the antioxidant performance of the inclusion complex was better than the native puerarin, and puerarin/Me-β-CD complex was the most effective form. It can be a potentially promising way to develop a new formulation of puerarin for herbal medicine or healthcare products.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Prasain, J.K., Jones, K., Kirk, M., Wilson, L., Smith-Johnson, M., Weaver, C., Barnes, S.: Profiling and quantification of isoflavonoids in kudzu dietary supplements by high performance liquid chromatography and electrospray ionizationtandem mass spectrometry. J. Agric. Food Chem. 51, 4213–4218 (2003)

    Article  CAS  Google Scholar 

  2. Prasain, J.K., Peng, N., Rajbhandari, R., Wyss, J.M.: The Chinese pueraria root extract (Pueraria lobata) ameliorates impaired glucose and lipid metabolism in obese mice. Phytomedicine 20, 17–23 (2012)

    Article  CAS  Google Scholar 

  3. Kim, K.M., Jung, D.H., Jang, D.S., Kim, Y.S., Kim, J.M., Kim, H.N., Surth, Y.J., Kim, J.S.: Puerarin suppresses AGEs-induced inflammation in mouse mesangial cells: a possible pathway through the induction of heme oxygenase-1 expression. Toxicol. Appl. Pharmcol. 244, 106–113 (2010)

    Article  CAS  Google Scholar 

  4. Chung, M.J., Sung, N.J., Park, C.S., Kweon, D.K., Mantovani, A., Moon, T.W., Lee, S.J., Park, K.H.: Antioxidative and hypocholesterolemic activities of water-soluble puerarin glycosides in HepG2 cells and in C57 BL/6 J mice. Eur. J. Pharmacol. 578, 159–170 (2008)

    Article  CAS  Google Scholar 

  5. Hwang, Y.P., Jeong, H.G.: Mechanism of phytoestrogen puerarin-mediated cytoprotection following oxidative injury: estrogen receptor-dependent up-regulation of PI3 K/Akt and HO-1. Toxicol. Appl. Pharmacol. 233(3), 371–381 (2008)

    Article  CAS  Google Scholar 

  6. Zhang, N.B., Huang, Z.G., Cui, W.D., Ding, B.P.: Effects of puerarin on expression of cardiac Smad3 and Smad7 mRNA in spontaneously hypertensive rat. J. Ethnopharmacol. 138, 737–740 (2011)

    Article  CAS  Google Scholar 

  7. Lin, Y.J., Hou, Y.C., Lin, C.H., Hsu, Y.A., Sheu, J.J., Lai, C.H., Chen, B.H., Lee Chao, P.D., Wan, L., Tsai, F.J.: Puerariae radix isoflavones and their metabolites inhibit growth and induce apoptosis in breast cancer cells. Biochem. Biophys. Res. Commun. 378, 683–688 (2009)

    Article  CAS  Google Scholar 

  8. Sarkar, F.H., Li, Y.: Soy isoflavones and cancer prevention. Cancer Invest. 21, 744–757 (2003)

    Article  CAS  Google Scholar 

  9. Cheng, Y.F., Zhu, G.Q., Wang, M., Cheng, H., Zhou, A., Wang, N., Fang, N., Wang, X.C., Xio, X.Q., Chen, Z.W., Ql, L.I.: Involvement of ubiquitin proteasome system in protective mechanisms of puerarin to MPP(+)-elicited apoptosis. Neurosci. Res. 63, 52–58 (2009)

    Article  CAS  Google Scholar 

  10. Wang, L.H., Cheng, Y.Y.: Solubility of puerarin in water, ethanol, and acetone from (288.2 to 328.2) K. J. Chem. Eng. Data 50, 1375–1376 (2005)

    Article  CAS  Google Scholar 

  11. Zhao, L.X., Liu, A.C., Sun, M., Gu, J.S., Wang, H.G., Wang, S., Zhang, J., Guo, C.Y., Duan, R., Zhai, G.X.: Enhancement of oral bioavailability of puerarin by polybutylcyanoacrylate nanoparticles. J. Nanomater. (2011). doi:10.1155/2011/126562. Article ID 126562

    Google Scholar 

  12. Bertrand, A., Morel, S., Lefoulon, F., Rolland, Y., Monsana, P., Remaud-Simeona, M.: Leuconostocmesenteroides glucansucrase synthesis of flavonoid glucosides by acceptor reactions in aqueous-organic solvents. Carbohydr. Res. 341, 855–863 (2006)

    Article  CAS  Google Scholar 

  13. Jiang, J.R., Yuan, S., Ding, J.F., Zhu, S.C., Xu, H.D., Chen, T., Cong, X.D., Xu, W.P., Ye, H., Dai, Y.J.: Conversion of puerarin into its 7-O-glycoside derivatives by microbacterium oxydans (CGMCC 1788) to improve its water solubility and pharmacokinetic properties. Appl. Microbiol. Biotechnol. 81, 647–657 (2008)

    Article  CAS  Google Scholar 

  14. Sansone, F., Picerno, P., Mencherini, T., Villecco, F., D’Ursi, A.M., Aquino, R.P., Lauro, M.R.: Flavonoid microparticles by spraydrying: influence of enhancers of the dissolution rate on properties and stability. J. Food Eng. 103, 188–196 (2001)

    Article  Google Scholar 

  15. Oidtmann, J., Schantz, M., Mäder, K., Baum, M., Berg, S., Betz, M., Kulozik, U., Leick, S., Rehage, H., Schwarz, K., Richling, E.: Preparation and comparative release characteristics of three anthocyanin encapsulation systems. J. Agric. Food Chem. 60, 844–851 (2012)

    Article  CAS  Google Scholar 

  16. Stella, V.J., Rajewski, R.A.: Cyclodextrins: their future in drug formulation and delivery. Pharm. Res. 14, 556–567 (1997)

    Article  CAS  Google Scholar 

  17. Tablet, C., Minea, L., Dumitrache, L., Hillebrand, M.: Experimental and theoretical study of the inclusion complexes of 3-carboxycoumarin acid with β- and 2-hydroxypropyl-β-cyclodextrins. Spectrochim. Acta 92, 56–63 (2012)

    Article  CAS  Google Scholar 

  18. Yang, L.J., Ma, S.X., Zhou, S.Y., Chen, W., Yuan, M.W., Yin, Y.Q., Yang, X.D.: Preparation and characterization of inclusion complexes of naringenin with β-cyclodextrin or its derivative. Carbohydr. Polym. 98, 861–869 (2013)

    Article  CAS  Google Scholar 

  19. Xiao, C.F., Li, K., Huang, R., He, G.J., Zhang, J.Q., Zhu, L., Yang, Q.Y., Jiang, K.M., Jin, Y., Lin, J.: Investigation of inclusion complex of epothilone A with cyclodextrins. Carbohydr. Polym. 102, 297–305 (2014)

    Article  CAS  Google Scholar 

  20. Blanch, G.P., del Ruiz Castillo, M.L., Caja, M.M., Perez-Mendez, M., Sanchez-Cortes, S.: Stabilization of all-trans-lycopene from tomato by encapsulation using cyclodextrins. Food Chem. 105(4), 1335–1341 (2007)

    Article  CAS  Google Scholar 

  21. Szejtli, J.: Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743–1754 (1998)

    Article  CAS  Google Scholar 

  22. Laura, G.Y., Michela, L., Francesco, S., Carmen, O.M., Alessandro, C., Jose, M.G.F.: Glycoligand-targeted core-shell nanospheres with tunable drug release profiles from calixarene-cyclodextrin heterodimers. Chem. Commun. (Camb.) 50(56), 7440–7443 (2014)

    Article  Google Scholar 

  23. Wang, K., Liu, Y., Li, C., Cheng, S.X., Zhuo, R.X., Zhang, X.Z.: Cyclodextrin-responsive micelles based on poly(ethylene glycol)-polypeptide hybrid copolymers as drug carriers. ACS Macro Lett. 2(3), 201–205 (2013)

    Article  Google Scholar 

  24. He, X., Tan, T., Xu, B., Janson, J.C.: Separation and purification of puerarin using β-cyclodextrin coupled agarose gel media. J. Chromatogr. A 1022, 77–82 (2004)

    Article  CAS  Google Scholar 

  25. He, X., Tan, T., Janson, J.C.: Purification of the isoflavonoid puerarin by adsorption chromatography on cross-linked 12 % agarose. J. Chromatogr. A 1057, 95–100 (2004)

    Article  CAS  Google Scholar 

  26. Higuchi, T., Connors, K.A.: Phase solubility techniques. Adv. Anal. Chem. Instrum. 4, 117–212 (1965)

    CAS  Google Scholar 

  27. Oyaizu, M.: Studies on products of browning reactions: antioxidative activities of products of browning reaction prepared from glucosamine. Jpn. J. Nutr. 44, 307–315 (1986)

    Article  CAS  Google Scholar 

  28. Wang, B.S., Li, B.S., Zeng, Q.X., Liu, H.X.: Antioxidant and free radical scavenging activities of pigments extracted from molasses alcohol waste water. Food Chem. 107, 1198–1204 (2008)

    Article  CAS  Google Scholar 

  29. Zhao, R., Tan, T.W., Sandström, C.: NMR studies on puerarin and its interaction with beta-cyclodextrin. J. Biol. Phys. 37, 387–400 (2011)

    Article  CAS  Google Scholar 

  30. Yang, L., Zhang, H.Y., Tan, T.W., Rahman, A.U.: Thermodynamic and NMR investigations on the adsorption mechanism of puerarin with oligo-β-cyclodextrin-coupled polystyrene-based matrix. J. Chem. Technol. Biotechnol. 84, 611–617 (2009)

    Article  CAS  Google Scholar 

  31. Yuan, C., Du, L., Jin, Z., Xu, X.: Storage stability and antioxidant activityof complex of astaxanthin with hydroxypropyl-β-cyclodextrin. Carbohydr. Polym. 91, 385–389 (2013)

    Article  CAS  Google Scholar 

  32. Gharibzahedi, S.M.T., Razavi, S.H., Mousavi, M.: Characterizing the natural canthaxanthin/2-hydroxypropyl-β-cyclodextrin inclusion complex. Carbohydr. Polym. 101, 1147–1153 (2014)

    Article  CAS  Google Scholar 

  33. Jullian, C., Orosteguis, T., Pérez-Cruz, F., Sánchez, P., Mendizabal, F., Olea-Azar, C.: Complexation of morin with three kinds of cyclodextrin A thermodynamic and reactivity study. Spectrochim. Acta 71, 269–275 (2008)

    Article  Google Scholar 

  34. Strazisar, M., Andrensek, S., Smidovnik, A.: Effect of β-cyclodextrin on antioxidant activity of coumaric acids. Food Chem. 110, 636–642 (2008)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work is financially supported by Beijing Natural Science Foundation (2144047, 2143040); Beijing Higher Education Young Elite Teacher Project YETP1444; The Project-sponsored by SRF for ROCS, SEM.

Author information

Authors and Affiliations

  1. Department of Chemistry, School of Science, Beijing Technology and Business University, Beijing, 100048, People’s Republic of China

    Shujing Li, Junzhi Yue & Wei Zhou

  2. Beijing Key Laboratory of Plant Resources Research and Development, Beijing Technology and Business University, Beijing, 100048, People’s Republic of China

    Li Li

Authors
  1. Shujing Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Junzhi Yue
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Wei Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Li Li
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Shujing Li.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 2320 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Li, S., Yue, J., Zhou, W. et al. An investigation into the preparation, characterization and antioxidant activity of puerarin/cyclodextrin inclusion complexes. J Incl Phenom Macrocycl Chem 82, 453–460 (2015). https://doi.org/10.1007/s10847-015-0516-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-015-0516-9

Keywords

Search

Navigation