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Comparative metabolome-based classification of Senna drugs: a prospect for phyto-equivalency of its different commercial products

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Abstract

Introduction

The demand to develop efficient and reliable analytical methods for the quality control of nutraceuticals is on the rise, together with an increase in the legal requirements for safe and consistent levels of its active principles.

Objective

To establish a reliable model for the quality control of widely used Senna preparations used as laxatives and assess its phyto-equivalency.

Methods

A comparative metabolomics approach via NMR and MS analyses was employed for the comprehensive measurement of metabolites and analyzed using chemometrics.

Results

Under optimized conditions, 30 metabolites were simultaneously identified and quantified including anthraquinones, bianthrones, acetophenones, flavonoid conjugates, naphthalenes, phenolics, and fatty acids. Principal component analysis (PCA) was used to define relative metabolite differences among Senna preparations. Furthermore, quantitative 1H NMR (qHNMR) was employed to assess absolute metabolites levels in preparations. Results revealed that 6-hydroxy musizin or tinnevellin were correlated with active metabolites levels, suggesting the use of either of these naphthalene glycosides as markers for official Senna drugs authentication.

Conclusion

This study provides the first comparative metabolomics approach utilizing NMR and UPLC–MS to reveal for secondary metabolite compositional differences in Senna preparations that could readily be applied as a reliable quality control model for its analysis.

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References

  • Burnett, A. R., & Thomson, R. H. (1968). Naturally occurring quinones. Part XIII. Anthraquinones and related naphthalenic compounds in Galium spp. and in Asperula odorata. Journal of the Chemical Society C, 854–857. https://doi.org/10.1039/J39680000854.

  • Demirezer, L. O., Karahan, N., Ucakturk, E., Kuruuzum-Uz, A., Guvenalp, Z., & Kazaz, C. (2011). HPLC fingerprinting of sennosides in laxative drugs with isolation of standard substances from some Senna leaves. Records of Natural Products, 5(4), 261–270.

    CAS  Google Scholar 

  • El-Ahmady, S. H., & Ashour, M. L. (2016). 24—Advances in testing for adulteration of food supplements—Downey, Gerard, advances in food authenticity testing (pp. 667–699). Sawston: Woodhead Publishing.

    Google Scholar 

  • Farag, M. A. (2014). Comparative mass spectrometry & nuclear magnetic resonance metabolomic approaches for nutraceuticals quality control analysis: A brief review. Recent Patents on Biotechnology, 8(1), 17–24.

    Article  CAS  PubMed  Google Scholar 

  • Farag, M. A., Otify, A., Porzel, A., Michel, C. G., Elsayed, A., & Wessjohann, L. A. (2016a). Comparative metabolite profiling and fingerprinting of genus Passiflora leaves using a multiplex approach of UPLC-MS and NMR analyzed by chemometric tools. Analytical and Bioanalytical Chemistry, 408(12), 3125–3143.

    Article  CAS  PubMed  Google Scholar 

  • Farag, M. A., Porzel, A., Mahrous, E. A., El-Massry, M. M., & Wessjohann, L. A. (2015). Integrated comparative metabolite profiling via MS and NMR techniques for Senna drug quality control analysis. Analytical and Bioanalytical Chemistry, 407(7), 1937–1949.

    Article  CAS  PubMed  Google Scholar 

  • Farag, M. A., Rasheed, D. M., Kropf, M., & Heiss, A. G. (2016b). Metabolite profiling in Trigonella seeds via UPLC-MS and GC-MS analyzed using multivariate data analyses. Analytical and Bioanalytical Chemistry, 408(28), 8065–8078.

    Article  CAS  PubMed  Google Scholar 

  • Gad, H. A., El-Ahmady, S. H., Abou-Shoer, M. I., & Al-Azizi, M. M. (2013). Application of chemometrics in authentication of herbal medicines: A review. Phytochemical Analysis: PCA, 24(1), 1–24.

    Article  CAS  PubMed  Google Scholar 

  • Ganapaty, S., Thomas, P. S., Ramana, K. V., Vidyadhar, K., & Chakradhar, V. (2002). A review of phytochemical studies of Cassia species. Journal of Natural Remedies, 2(2), 102–120.

    CAS  Google Scholar 

  • Gautam, R., Srivastava, A., & Jachak, S. M. (2011). Simultaneous determination of naphthalene and anthraquinone derivatives in Rumex nepalensis Spreng roots by HPLC: Comparison of different extraction methods and validation. Phytochemical Analysis: PCA, 22(2), 153–157.

    Article  CAS  PubMed  Google Scholar 

  • Kim, H. K., Choi, Y. H., & Verpoorte, R. (2011). NMR-based plant metabolomics: Where do we stand, where do we go? Trends in Biotechnology, 29(6), 267–275.

    Article  CAS  PubMed  Google Scholar 

  • Korulkin, D. Y., & Muzychkina, R. A. (2014). Biosynthesis and metabolism of anthraquinone derivatives. International Journal of Medical, Health, Biomedical, Bioengineering and Pharmaceutical Engineering, 8(7), 454–457.

    Google Scholar 

  • Lee, J.-E., Lee, B.-J., Chung, J.-O., Hwang, J.-A., Lee, S.-J., Lee, C.-H., et al. (2010). Geographical and climatic dependencies of green tea (Camellia sinensis) metabolites: A 1H NMR-based metabolomics study. Journal of Agricultural and Food Chemistry, 58(19), 10582–10589.

    Article  CAS  PubMed  Google Scholar 

  • Lemli, J., Toppet, S., Cuveele, J., & Janssen, G. (1981). Naphthalene glycosides in Cassia senna and Cassia angustifolia. Planta Medica, 43(1), 11–17.

    Article  CAS  PubMed  Google Scholar 

  • Liu, J., Liu, Y., Zhao, L., Zhang, Z.-H., & Tang, Z.-H. (2016). Profiling of ginsenosides in the two medicinal Panax herbs based on ultra-performance liquid chromatography-electrospray ionization–mass spectrometry. SpringerPlus, 5(1), 1770.

    Article  PubMed  PubMed Central  Google Scholar 

  • Mahrous, E. A., & Farag, M. A. (2015). Two dimensional NMR spectroscopic approaches for exploring plant metabolome: A review. Journal of Advanced Research, 6(1), 3–15.

    Article  CAS  PubMed  Google Scholar 

  • Seethapathy, G. S., Ganesh, D., Santhosh Kumar, J. U., Senthilkumar, U., Newmaster, S. G., Ragupathy, S., et al. (2015). Assessing product adulteration in natural health products for laxative yielding plants, Cassia, Senna, and Chamaecrista, in Southern India using DNA barcoding. International Journal of Legal Medicine, 129(4), 693–700.

    Article  PubMed  Google Scholar 

  • Shelar, P. A., Jawlikar, B. V., Mohite, M. S., Raje, V. N., Thorata, M. B., & Tikole, S. S. (2013). Comparative study of isolated moiety from Senna leaves, pods and powder. Current Pharma Research, 3(4), 1019–1022.

    Article  Google Scholar 

  • Sun, S.-W., & Su, H.-T. (2002). Validated HPLC method for determination of sennosides A and B in senna tablets. Journal of Pharmaceutical and Biomedical Analysis, 29(5), 881–894.

    Article  PubMed  Google Scholar 

  • Takahashi, M., Sakurai, K., Fujii, H., & Saito, K. (2012). Discrimination of Cassia plants in health tea. Japanese Journal of Food Chemistry and Safety, 19(2), 149–154.

    Google Scholar 

  • Takahashi, M., Sakurai, K., Fujii, H., & Saito, K. (2014). Identification of indicator components for the discrimination of Cassia plants in health teas and development of analytical method for the components. Journal of AOAC International, 97(4), 1195–1201.

    Article  CAS  PubMed  Google Scholar 

  • Terreaux, C., Wang, Q., Ioset, J. R., Ndjoko, K., Grimminger, W., & Hostettmann, K. (2002). Complete LC/MS analysis of a Tinnevelli senna pod extract and subsequent isolation and identification of two new benzophenone glucosides. Planta Medica, 68(4), 349–354.

    Article  CAS  PubMed  Google Scholar 

  • Yao, S., Li, Y., & Kong, L. (2006). Preparative isolation and purification of chemical constituents from the root of Polygonum multiflorum by high-speed counter-current chromatography. Journal of Chromatography A, 1115(1), 64–71.

    Article  CAS  PubMed  Google Scholar 

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Acknowledgments

Prof. Mohamed A. Farag thanks The American University in Cairo Research Support Grant (SSE-CHEM-MF-FY18-FY19-RG-(1-18)-2017-10-16-26-34) and Alexander von Humboldt Foundation, Germany, for financial support.

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Authors and Affiliations

  1. Pharmacognosy Department, College of Pharmacy, Cairo University, Cairo, Egypt

    Mohamed A. Farag & Amira S. El Senousy

  2. Department of Chemistry, School of Sciences & Engineering, The American University in Cairo, Cairo, Egypt

    Mohamed A. Farag

  3. Pharmacognosy Department, College of Pharmacy, Ain Shams University, Cairo, Egypt

    Sherweit H. El-Ahmady

  4. Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120, Halle (Saale), Germany

    Andrea Porzel & Ludger A. Wessjohann

Authors
  1. Mohamed A. Farag
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  2. Amira S. El Senousy
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  3. Sherweit H. El-Ahmady
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  4. Andrea Porzel
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  5. Ludger A. Wessjohann
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Contributions

MAF conducted the experiments; MAF performed the data analysis, ASS, SEA co-wrote the manuscript; ASS and AP analysed NMR results and revised assignments, MAF and LAW designed the study and edited the manuscript. All authors approved the final version of the manuscript.

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Correspondence to Mohamed A. Farag.

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Farag, M.A., El Senousy, A.S., El-Ahmady, S.H. et al. Comparative metabolome-based classification of Senna drugs: a prospect for phyto-equivalency of its different commercial products. Metabolomics 15, 80 (2019). https://doi.org/10.1007/s11306-019-1538-x

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