Advertisement

Journal of Natural Medicines

, Volume 71, Issue 1, pp 139–147 | Cite as

Rapid and simple determination of polyphyllin I, II, VI, and VII in different harvest times of cultivated Paris polyphylla Smith var. yunnanensis (Franch.) Hand.-Mazz by UPLC-MS/MS and FT-IR

  • Zhe Wu
  • Ji Zhang
  • Furong Xu
  • Yuanzhong Wang
  • Jinyu Zhang
Original Paper

Abstract

Paris Polyphylla Smith var. yunnanensis (Franch.) Hand.-Mazz (“Dian Chonglou” in Chinese) is a famous herbal medicine in China, which is usually well known for activities of anti-cancer, hemolysis, and cytotoxicity. In this study, Fourier transform infrared (FT-IR) spectroscopy coupled with principal component analysis (PCA) and partial least-squares regression (PLSR) was applied to discriminate samples of P. polyphylla var. yunnanensis harvested in different years and determine the content of polyphyllin I, II, VI, and VII in P. polyphylla var. yunnanensis. Meanwhile, ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) was used to study the dynamic changes of P. polyphylla var. yunnanensis harvested in different years (4, 5, 7, 8, 9, 12, and 13 years old). According to the UPLC-MS/MS result, the optimum harvest time of P. polyphylla var. yunnanensis is 8 years, due to the highest yield of four active components. By the PCA model, P. polyphylla var. yunnanensis could be exactly discriminated, except that two 8-year-old samples were misclassified as 9-year-old samples. For the prediction of polyphyllin I, II, VI, and VII, the quantitative results are satisfactory, with a high value for the determination coefficient (R 2) and low values for the root-mean-square error of estimation (RMSEE), root-mean-square error of cross-validation (RMSECV), and root-mean-square error of prediction (RMSEP). In conclusion, FT-IR combined with chemometrics is a promising method to accurately discriminate samples of P. polyphylla var. yunnanensis harvested in different years and determine the content of polyphyllin I, II, VI, and VII in P. polyphylla var. yunnanensis.

Keywords

Paris polyphylla Smith var. yunnanensis (Franch.) Hand.-Mazz Fourier transform infrared (FT-IR) spectroscopy Harvest times Discrimination Determination 

Notes

Acknowledgments

This work was sponsored by the Natural Science Foundation of the People’s Republic of China (81460584) and the Special Fund for Agro-scientific Research in the Public Interest (201303117).

Supplementary material

11418_2016_1043_MOESM1_ESM.doc (32 kb)
Supplementary material 1 (DOC 32 kb)

References

  1. 1.
    Gad HA, El-Ahmady SH, Abou-Shoer MI, Al-Azizi MM (2013) Application of chemometrics in authentication of herbal medicines: a review. Phytochem Anal 24:1–24. doi: 10.1002/pca.2378 CrossRefPubMedGoogle Scholar
  2. 2.
    Liu DG, Mei Q, Wan XL, Que HL, Li LY, Wan DR (2015) Determination of rutin and isoquercetin contents in Hibisci mutabilis folium in different collection periods by HPLC. J Chromatogr Sci 53:1680–1684. doi: 10.1093/chromsci/bmv071 CrossRefPubMedGoogle Scholar
  3. 3.
    Li H (1998) The genus Paris (Trilliaceae). Science Press, Beijing, p 23Google Scholar
  4. 4.
    The State Pharmacopoeia Commission (2015) Chinese pharmacopoeia. The State Pharmacopoeia Commission, Beijing, pp 260–261Google Scholar
  5. 5.
    Zhang JY, Wang YZ, Zhao YL, Yang SB, Zuo ZT, Yang MQ, Zhang J, Yang WZ, Yang TM, Jin H (2011) Phytochemicals and bioactivities of Paris species. J Asian Nat Prod Res 13:670–681. doi: 10.1080/10286020.2011.578247 CrossRefGoogle Scholar
  6. 6.
    Li YY, Man SL, Li J, Chai HY, Fan W, Liu Z, Gao WY (2014) The antitumor effect of formosanin C on HepG2 cell as revealed by 1H-NMR based metabolic profiling. Chem Biol Interact 220:193–199. doi: 10.1016/j.cbi.2014.06.023 CrossRefPubMedGoogle Scholar
  7. 7.
    Liu Z, Gao WY, Jing SS, Zhang Y, Man SL, Wang Y, Zhang JZ, Liu CX (2013) Correlation among cytotoxicity, hemolytic activity and the composition of steroidal saponins from Paris L. J Ethnopharmacol 149:422–430. doi: 10.1016/j.jep.2013.06.033 CrossRefPubMedGoogle Scholar
  8. 8.
    Wen YS, Ni W, Qin XJ, Yan H, Chen CX, Hua Y, Cheng YC, He L, Liu HY (2015) Steroidal saponins with cytotoxic activity from the rhizomes of Paris polyphylla var. yunnanensis. Phytochem Lett 12:31–34. doi: 10.1016/j.phytol.2015.02.011 CrossRefGoogle Scholar
  9. 9.
    Zhao JL, Mou Y, Shan TJ, Li Y, Zhou LG, Wang MG, Wang JG (2010) Antimicrobial metabolites from the endophytic fungus Pichia guilliermondii isolated from Paris polyphylla var. yunnanensis. Molecules 15:7961–7970. doi: 10.3390/molecules15117961 CrossRefPubMedGoogle Scholar
  10. 10.
    Wu SS, Gao WY, Duan HQ, Jia W (2004) Advances in studies on chemical constituents and pharmacological activities of Rhizoma Paridis. Chin Tradit Herbal Drugs 35:344–347Google Scholar
  11. 11.
    Wang GX, Han J, Zhao LW, Jiang DX, Liu YT, Liu XL (2010) Anthelmintic activity of steroidal saponins from Paris polyphylla. Phytomedicine 17:1102–1105. doi: 10.1016/j.phymed.2010.04.012 CrossRefPubMedGoogle Scholar
  12. 12.
    Man SL, Fan W, Liu Z, Gao WY, Li YY, Zhang LM, Liu CX (2014) Antitumor pathway of Rhizoma Paridis Saponins based on the metabolic regulatory network alterations in H22 hepatocarcinoma mice. Steroids 84:17–21. doi: 10.1016/j.steroids.2014.03.005 CrossRefPubMedGoogle Scholar
  13. 13.
    Teng WJ, Chen P, Zhu FY, Di K, Zhou C, Zhuang J, Cao XJ, Yang J, Deng LJ, Sun CG (2015) Effect of Rhizoma paridis total saponins on apoptosis of colorectal cancer cells and imbalance of the JAK/STAT3 molecular pathway induced by IL-6 suppression. Genet Mol Res 14:5793–5803. doi: 10.4238/2015.May.29.11 CrossRefPubMedGoogle Scholar
  14. 14.
    Ong RCY, Lei J, Lee RKY, Cheung JYN, Fung KP, Lin C, Ho HP, Yu B, Li M, Kong SK (2008) Polyphyllin D induces mitochondrial fragmentation and acts directly on the mitochondria to induce apoptosis in drug-resistant HepG2 cells. Cancer Lett 261:158–164. doi: 10.1016/j.canlet.2007.11.005 CrossRefPubMedGoogle Scholar
  15. 15.
    Man SL, Fan W, Gao WY, Li YY, Wang Y, Liu Z, Li HF (2014) Anti-fibrosis and anti-cirrhosis effects of Rhizoma paridis saponins on diethylnitrosamine induced rats. J Ethnopharmacol 151:407–412. doi: 10.1016/j.jep.2013.10.051 CrossRefPubMedGoogle Scholar
  16. 16.
    Jiang H, Zhao PJ, Feng JG, Su D, Ma SL (2014) Effect of Paris saponin I on radiosensitivity in a gefitinib-resistant lung adenocarcinoma cell line. Oncol Lett 7:2059–2064. doi: 10.3892/ol.2014.2020 CrossRefPubMedPubMedCentralGoogle Scholar
  17. 17.
    Shi YM, Yang L, Geng YD, Zhang C, Kong LY (2015) Polyphyllin I induced-apoptosis is enhanced by inhibition of autophagy in human hepatocellular carcinoma cells. Phytomedicine 22:1139–1149. doi: 10.1016/j.phymed.2015.08.014 CrossRefPubMedGoogle Scholar
  18. 18.
    Yue GF, Wei J, Qian XP, Yu LX, Zou ZY, Guan WX, Wang H, Shen J, Liu BR (2013) Synergistic anticancer effects of polyphyllin I and evodiamine on freshly-removed human gastric tumors. PLoS One 8:e65164. doi: 10.1371/journal.pone.0065164 CrossRefPubMedPubMedCentralGoogle Scholar
  19. 19.
    Yang M, Zou J, Zhu HG, Liu SL, Wang H, Bai P, Xiao X (2015) Paris saponin II inhibits human ovarian cancer cell-induced angiogenesis by modulating NF-κB signaling. Oncol Rep 33:2190–2198. doi: 10.3892/or.2015.3836 CrossRefPubMedGoogle Scholar
  20. 20.
    Ning LH, Zhou B, Zhang YX, Li XP (2015) Study on hemolytic mechanism of polyphyllin II. China J Chin Mater Med 40:3623–3629. doi: 10.4268/cjcmm20151820 Google Scholar
  21. 21.
    Zhang WJ, Zhang D, Ma X, Liu ZY, Li F, Wu DN (2014) Paris saponin VII suppressed the growth of human cervical cancer Hela cells. Eur J Med Res 19:41. http://www.eurjmedres.com/content/19/1/41 CrossRefPubMedPubMedCentralGoogle Scholar
  22. 22.
    Feng LL, Zhang L, Li HF, Zhang CG (2015) Metabolism rule of secondary metabolites, steroidal saponins active ingredients, in Paris polyphylla var. yunnanensis Franch. J Chin Pharm Sci 50:664–670Google Scholar
  23. 23.
    Zhao TZ, Wang BQ, Ma Q, Fan QL (2014), Study on best harvesting time of Paris polyphylla var. yunnanensis. Chin Wild Plant Resour 33:61–63. doi: 10.3969/j.issn.1006-9690.05.017 Google Scholar
  24. 24.
    Zhu Y, Xu CH, Huang J, Li GY, Liu XH, Sun SQ, Wang JH (2014) Rapid discrimination of cultivated Codonopsis lanceolata in different ages by FT-IR and 2DCOS-IR. J Mol Struct 1069:272–279. doi: 10.1016/j.molstruc.2014.01.069 CrossRefGoogle Scholar
  25. 25.
    Chen SL, Guo BL, Zhang GJ, Yan ZY, Luo GM, Sun SQ, Wu HZ, Huang LF, Pang XH, Chen JB (2012) Advances of studies on new technology and method for identifying traditional Chinese medicinal materials. China J Chin Mater Med 37:1043–1055. doi: 10.4268/cjcmm20120801 Google Scholar
  26. 26.
    McGoverin CM, September DJF, Geladi P, Manley M (2012) Near infrared and mid-infrared spectroscopy for the quantification of adulterants in ground black pepper. J Near Infrared Spectrosc 20:521–528. doi: 10.1255/jnirs.1008 CrossRefGoogle Scholar
  27. 27.
    Kaniu MI, Angeyo KH, Mwala AK, Mangala MJ (2012) Direct rapid analysis of trace bioavailable soil macronutrients by chemometrics-assisted energy dispersive X-ray fluorescence and scattering spectrometry. Anal Chim Acta 729:21–25. doi: 10.1016/j.aca.2012.04.007 CrossRefPubMedGoogle Scholar
  28. 28.
    Musingarabwi DM, Nieuwoudt HH, Young PR, Eyéghè-Bickong HA, Vivier MA (2016) A rapid qualitative and quantitative evaluation of grape berries at various stages of development using Fourier-transform infrared spectroscopy and multivariate data analysis. Food Chem 190:253–262. doi: 10.1016/j.foodchem.2015.05.080 CrossRefPubMedGoogle Scholar
  29. 29.
    Zhang SJ, Zhang HH, Zhao YR, Guo W, Zhao HM (2013) A simple identification model for subtle bruises on the fresh jujube based on NIR spectroscopy. Math Comput Model 58:545–550. doi: 10.1016/j.mcm.2011.10.067 CrossRefGoogle Scholar
  30. 30.
    Godinho MS, Blanco MR, Gambarra Neto FF, Lião LM, Sena MM, Tauler R, de Oliveira AE (2014) Evaluation of transformer insulating oil quality using NIR, fluorescence, and NMR spectroscopic data fusion. Talanta 129:143–149. doi: 10.1016/j.talanta.2014.05.021 CrossRefPubMedGoogle Scholar
  31. 31.
    Wang P, Zhang H, Yang HL, Nie L, Zang HC (2015) Rapid determination of major bioactive isoflavonoid compounds during the extraction process of kudzu (Pueraria lobata) by near-infrared transmission spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc 137:1403–1408. doi: 10.1016/j.saa.2014.09.002 CrossRefPubMedGoogle Scholar
  32. 32.
    Yan Q (2013) Analyze and identify Chinese herbal medicine Chonglou and counterfeit medicine Kaikoujian by Fourier transform infrared spectroscopy. J Light Scatt 25:85–91Google Scholar
  33. 33.
    Chen JB, Sun SQ, Ma F, Zhou Q (2014) Vibrational microspectroscopic identification of powdered traditional medicines: chemical micromorphology of Poria observed by infrared and Raman microspectroscopy. Spectrochim Acta A Mol Biomol Spectrosc 128:629–637. doi: 10.1016/j.saa.2014.03.010 CrossRefPubMedGoogle Scholar
  34. 34.
    Cheng CG, Liu J, Cao WQ, Zheng RW, Wang H, Zhang CJ (2010) Classification of two species of Bidens based on discrete stationary wavelet transform extraction of FTIR spectra combined with probability neural network. Vib Spectrosc 54:50–55. doi: 10.1016/j.vibspec.2010.06.004 CrossRefGoogle Scholar
  35. 35.
    Sun SQ, Zhou Q, Chen JB (2010) Analysis of traditional Chinese medicine by infrared spectroscopy. Chemical Industry Press, Beijing, pp 72–75Google Scholar
  36. 36.
    Jolliffe IT, Cadima J (2016) Principal component analysis: a review and recent developments. Philos Trans A Math Phys Eng Sci 374:20150202. doi: 10.1098/rsta.2015.0202 CrossRefPubMedPubMedCentralGoogle Scholar
  37. 37.
    Kennard RW, Stone LA (1969) Computer aided design of experiments. Technometrics 11:137–148. http://www.jstor.org/stable/1266770 CrossRefGoogle Scholar
  38. 38.
    Pande R, Mishra HN (2015) Fourier transform near-infrared spectroscopy for rapid and simple determination of phytic acid content in green gram seeds (Vigna radiata). Food Chem 172:880–884. doi: 10.1016/j.foodchem.2014.09.049 CrossRefPubMedGoogle Scholar

Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan 2016

Authors and Affiliations

  1. 1.Institute of Medicinal PlantsYunnan Academy of Agricultural SciencesKunmingPeople’s Republic of China
  2. 2.Yunnan Technical Center for Quality of Chinese Materia MedicaKunmingPeople’s Republic of China
  3. 3.College of Traditional Chinese MedicineYunnan University of Traditional Chinese MedicineKunmingPeople’s Republic of China

Personalised recommendations