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Analytical evaluation of steviol glycosides by capillary electrophoresis supported with molecular docking studies

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Abstract

This paper reports on a newly developed electrokinetic chromatographic method for the simultaneous separation and determination of steviol glycosides in real stevia samples by capillary electrophoresis and supported by molecular docking studies. Our results obtained using 30-mM heptakis-(2,3,6-tri-o-methyl betacyclodextrin) as a separating agent, suggest that at optimum experimental conditions the detection limits of 2.017 × 10−5 and 7.386 × 10−5 M and relative standard deviations (n = 5) of 1.10 and 1.17 were obtained for rebaudioside-A and stevioside, respectively. In addition, the molecular docking studies explained to a certain extent why the separation was successful. The calculated binding free energy results for the rebaudioside-A and stevioside complexes formed with the separating agent showed that although both ligands penetrated deeply into the hydrophobic cavity of the separating agent, the presence of additional hydrogen bonding in the case of stevioside is probably responsible for its stronger binding affinity than that of rebaudioside-A.

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References

  1. D.J. Midmore, A.H. Rank, A new rural industry—stevia—to replace imported chemical sweeteners. A report for Rural Industries Research and Development Corporation RIRDC Web, Publication No. W02/022 RIRDC Project No. UCQ-16A (2002)

  2. J. Liu, C.P. Ong, S.F.Y. Li, J. Chromatogr. Sci. 35, 446 (1997)

    Article  CAS  Google Scholar 

  3. J.M.C. Geuns, Stevia and Steviol Glycosides (Euprint Ed., Heverlee, 2010)

  4. Regulations relating to the use of sweeteners in foodstuffs. Foodstuffs, cosmetics and disinfectants act (1972), http://www.doh.gov.za/docs/foodcontrol/additives/2012/regr733

  5. U. Woelwer-Rieck, J. Agric. Food Chem. 60, 886 (2012)

    Article  CAS  Google Scholar 

  6. M.B. Tadhani, V.H. Patel, R. Subhash, J. Food Compos. Anal. 20, 323 (2007)

    Article  CAS  Google Scholar 

  7. P. Mauri, G. Catalano, C. Gardana, P. Pietta, Electrophoresis 17, 367 (1996)

    Article  CAS  Google Scholar 

  8. M.S. Melis, J. Nat. Prod. 55, 688 (1992)

    Article  CAS  Google Scholar 

  9. M.S. Melis, J. Ethnopharmacol. 36, 213 (1992)

    Article  CAS  Google Scholar 

  10. P.M. Kuznesof, The 68th JECFA Steviolglycosides (CTA) (2007), pp. 1–8

  11. H.C. Makapugay, N.P.D. Nanayakkara, A.D. Kinghorn, J. Chromatogr. 283, 390 (1984)

    Article  CAS  Google Scholar 

  12. J.M.C. Geuns, Analysis of steviol glycosides: validation of the methods, in Proceedings of the 2nd Stevia Symposium, ed. by J.M.C. Geuns (Euprint ed., Leuven, 2008), pp. 59–78

  13. J.M.C. Geuns, T. Struyf, EUSTAS round robin testing of steviol glycosides, in Proceedings of the 3rd Stevia Symposium, ed. by J.M.C. Geuns (Euprint, Leuven, 2009), pp. 35–48

    Google Scholar 

  14. B. Hoekstra, J. Traub, K. Chamberlain, S. Baugh, S.K. Venkataraman, Planta Med. 75, 1003 (2009)

    Article  Google Scholar 

  15. N. Kolb, J.L. Herrera, D.J. Ferreyra, R.F. Uliana, J. Agric. Food Chem. 49, 4538 (2001)

    Article  CAS  Google Scholar 

  16. N.A. Samah, A.D.A. Hisham, S.A. Rahim, Int. J. Chem. Environ. Eng. 332, 1 (2012)

    Google Scholar 

  17. C. Tianhong, Z. Yang, L. Xiaohang, S. Zuoqing, S. Juntan, H. Binglin, Sci. China 42, 277 (1999)

    Article  Google Scholar 

  18. V. Jaitak, A.P. Gupta, V.K. Kaul, P.S. Ahuja, J. Pharm. Biomed. Anal. 47, 790 (2008)

    Article  CAS  Google Scholar 

  19. U. Woelwer-Rieck, C. Lankes, A. Wawrzun, M. Wust, Eur. Food Res. Tech. 231, 581 (2010)

    Article  CAS  Google Scholar 

  20. B.F. Zimmermann, U. Woelwer-Rieck, M. Papagiannopoulos, Food Anal. Methods 5, 266 (2011)

    Article  Google Scholar 

  21. D. Hurum, J. Rohrer, Steviol glycoside determination by HPLC with charged aerosol and UV detections using the acclaim trinity P1 column, Application Note: 293 (2011)

  22. D. Bergs, B. Burghoff, M. Joehnck, G. Martin, G. Schembecker, J. Verbr. Lebensm. 7, 147 (2012)

    Article  CAS  Google Scholar 

  23. M. Puri, D. Sharma, C.J. Barrow, A.K. Tiwary, Food Chem. 132, 1113 (2012)

    Article  CAS  Google Scholar 

  24. J. Liu, S.F.Y. Li, J. Liq. Chromatogr. 18, 1703 (1995)

    Article  CAS  Google Scholar 

  25. T. Rajasekaran, A. Ramakrishna, K. Udaya Sankar, P. Giridhar, G.A. Ravishankar, Food Biotechnol. 22, 179 (2008)

    Article  CAS  Google Scholar 

  26. J.I. Zhang, X. Li, Z. Ouyang, R.G. Cooks, Analyst 137, 3091 (2012)

    Article  CAS  Google Scholar 

  27. B. Shafii, R. Vismeh, R. Beaudry, R. Warner, A.D. Jones, Anal. Bioanal. Chem. 403, 2683 (2012)

    Article  CAS  Google Scholar 

  28. R. Shah, L.S.D. Jager, T.H. Begley, Food Addit. Contam. A 29, 1861 (2012)

    Article  CAS  Google Scholar 

  29. P. Montoro, I. Molfetta, M. Maldini, L. Ceccarini, S. Piacente, C. Pizza, M. Macchia, Food Chem. 141, 745 (2013)

    Article  CAS  Google Scholar 

  30. Y. Kakigi, T. Suzuki, T. Icho, A. Uyama, N. Mochizuki, Food Addit. Contam. A (2013), http://dx.doi.org/10.1080/19440049.2013.843101

  31. L. Wuhong, L. Changhai, T. Guangguo, Z. Xinrong, Z. Zhenyu, Y.F. Chai, Int. J. Mol. Sci. 13, 710 (2012)

    Article  Google Scholar 

  32. A. Banerjee, E. Mikhailova, S. Cheley, L.Q. Gu, M. Montoya, Y. Nagaoka, E. Gouaux, H. Bayley, Proc. Natl. Acad. Sci. USA 107, 8165 (2010)

    Article  CAS  Google Scholar 

  33. Accelrys, Materials Studio Release Notes, Release 4.1; Accelrys Software, San Diego, CA (2006)

  34. G. Wu, D.H. Robertson, C.L. Brooks III, M. Vieth, J. Comp. Chem. 24, 1549 (2003)

    Article  CAS  Google Scholar 

  35. G. Chen, J. Zhang, J. Ye, J. Chromatogr. A 923, 255 (2001)

    Article  CAS  Google Scholar 

  36. G. Chen, H.W. Zhang, J.N. Ye, Anal. Chim. Acta 423, 69 (2000)

    Article  CAS  Google Scholar 

  37. P. Youyuan, Y. Jianjun, L. Fanghua, Y. Jiannong, J. Pharm. Biomed. Anal. 39, 431 (2005)

    Article  Google Scholar 

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Acknowledgments

KB is grateful for the financial support provided by the Durban University of Technology and National Research Foundation of South Africa for this work. The authors would like to express their acknowledgement to the Centre for High Performance Computing, an initiative supported by the Department of Science and Technology of South Africa.

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Authors and Affiliations

  1. Department of Chemistry, Durban University of Technology, P.O. Box 1334, Durban, 4000, South Africa

    Bathinapatla Ayyappa, Suvardhan Kanchi, Myalowenkosi I. Sabela & Krishna Bisetty

  2. School of Chemistry and Physics, University of KwaZulu Natal, P/Bag X54001, Westville, Durban, 4000, South Africa

    Parvesh Singh

  3. Kerry Ingredients and Flavours, Hillcrest, 3610, KZN, South Africa

    Martin Dovey

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  1. Bathinapatla Ayyappa
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  2. Suvardhan Kanchi
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  3. Parvesh Singh
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  4. Myalowenkosi I. Sabela
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  5. Martin Dovey
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Correspondence to Suvardhan Kanchi or Krishna Bisetty.

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Ayyappa, B., Kanchi, S., Singh, P. et al. Analytical evaluation of steviol glycosides by capillary electrophoresis supported with molecular docking studies. J IRAN CHEM SOC 12, 127–136 (2015). https://doi.org/10.1007/s13738-014-0465-z

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  • DOI: https://doi.org/10.1007/s13738-014-0465-z

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