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Separation of three flavonoid glycosides from Polygonum multiflorum Thunb. leaves using HSCCC and their antioxidant activities

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Abstract

Polygonum multiflorum Thunb. is a traditional herb which was widely distributed in China. The leaves of P. multiflorum (PML), which contains lots of antioxidant constituents, are often used for tea. In this study, three flavonoid glycosides were successfully separated and characterized from the ethyl acetate fraction of 80% ethanol extracts of PML by high-speed counter-current chromatography (HSCCC). The biphasic solvent system which can isolate purified myricitrin (44.5 mg), quercitrin (23.86 mg) and afzelin (14.39 mg) from 110 mg of the ethyl acetate fraction of PML was composed of n-hexane–ethyl acetate–methanol–water (0.5:3:1:2, v/v/v/v). Moreover, the purities of each compound were 94.9, 97.0, and 95.7% as determined by high-performance liquid chromatography (HPLC), respectively. Three flavonoid glycosides were obtained using only one-step HSCCC separation for the first time and the chemical structures of these three compounds were identified using the techniques of NMR and ESI–MS. The antioxidant activities of these three compounds, ethyl acetate fraction, and crude extract were evaluated by three antioxidant assays. The results of antioxidation assays showed that myricitrin and quercitrin have strong antioxidant activity and the two components may be the material basis of the antioxidant potential of PML. This work confirmed the feasibility of HSCCC to separate compounds from complex samples and it suggests that PML have pharmaceutical potential as natural antioxidant agents.

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References

  1. Kumar S, Sharma S, Vasudeva N (2017) Review on antioxidants and evaluation procedures. Chin J Integr Med. https://doi.org/10.1007/s11655-017-2414-z

    Article  PubMed  Google Scholar 

  2. Nile SH, Park SW (2014) Edible berries: Bioactive components and their effect on human health. Nutrition 30(2):134–144. https://doi.org/10.1016/j.nut.2013.04.007

    Article  PubMed  CAS  Google Scholar 

  3. Si C-L, Shen T, Jiang Y-Y, Wu L, Yu G-J, Ren X-D (2013) Antioxidant properties and neuroprotective effects of isocampneoside II on hydrogen peroxide-induced oxidative injury in PC12 cells. Food Chem Toxicol 59:145–152. https://doi.org/10.1016/j.fct.2013.05.051

    Article  PubMed  CAS  Google Scholar 

  4. Liang ZT, Shi YX, Chen HB, Zhao ZZ (2011) Histochemical analysis of the root tuber of Polygonum multiflorum Thunb. (Fam. Polygonaceae). Microsc Res Tech 74(6):488–495. https://doi.org/10.1002/jemt.20936

    Article  PubMed  CAS  Google Scholar 

  5. Bounda G-A, Feng Y (2015) Review of clinical studies of Polygonum multiflorum Thunb. and its isolated bioactive compounds. Pharmacogn Res 7(3):225. https://doi.org/10.4103/0974-8490.157957

    Article  CAS  Google Scholar 

  6. Lin L, Ni B, Lin H, Zhang M, Li X, Yin X (2015) Traditional usages, botany, phytochemistry, pharmacology and toxicology of Polygonum multiflorum Thunb.: a review. J Ethnopharmacol 159:158–183. https://doi.org/10.1016/j.jep.2014.11.009

    Article  PubMed  CAS  Google Scholar 

  7. Yang J-B, Li W-F, Liu Y, Wang Q, Cheng X-L, Wei F (2018) Acute toxicity screening of different extractions, components and constituents of Polygonum multiflorum Thunb. on zebrafish (Danio rerio) embryos in vivo. Biomed Pharmacother 99:205–213. https://doi.org/10.1016/j.biopha.2018.01.033

    Article  PubMed  CAS  Google Scholar 

  8. Yang J, He Y, Zou J, Xu L, Fan F, Ge Z (2019) Effect of Polygonum Multiflorum Thunb on liver fatty acid content in aging mice induced by d-galactose. Lipids Health Dis 18(1):1–8. https://doi.org/10.1186/s12944-019-1055-y

    Article  CAS  Google Scholar 

  9. Lv L, Shao X, Wang L, Huang D, Ho C-T, Sang S (2010) Stilbene glucoside from Polygonum multiflorum Thunb.: a novel natural inhibitor of advanced glycation end product formation by trapping of methylglyoxal. J Agric Food Chem 58(4):2239–2245. https://doi.org/10.1021/jf904122q

    Article  PubMed  CAS  Google Scholar 

  10. Park H-J, Zhang N, Park DK (2011) Topical application of Polygonum multiflorum extract induces hair growth of resting hair follicles through upregulating Shh and β-catenin expression in C57BL/6 mice. J Ethnopharmacol 135(2):369–375. https://doi.org/10.1016/j.jep.2011.03.028

    Article  PubMed  Google Scholar 

  11. Xu M-L, Zheng MS, Lee Y-K, Moon D-C, Lee C-S, Woo M-H (2006) A new stilbene glucoside from the roots of Polygonum multiflorum Thunb. Arch Pharmacal Res 29(11):946–951. https://doi.org/10.1007/BF02969276

    Article  CAS  Google Scholar 

  12. Yang J-B, Liu Y, Wang Q, Ma S-C, Wang A-G, Cheng X-L (2019) Characterization and identification of the chemical constituents of Polygonum multiflorum Thunb. by high-performance liquid chromatography coupled with ultraviolet detection and linear ion trap FT-ICR hybrid mass spectrometry. J Pharm Biomed Anal 172:149–166. https://doi.org/10.1016/j.jpba.2019.03.049

    Article  PubMed  CAS  Google Scholar 

  13. Begum S, Gu L-J, Lee M-R, Li Z, Li J-J, Hossain MJ (2015) In vivo hair growth-stimulating effect of medicinal plant extract on BALB/c nude mice. Pharm Biol 53(8):1098–1103. https://doi.org/10.3109/13880209.2014.959614

    Article  PubMed  Google Scholar 

  14. Meng Y-K, Li C-Y, Li R-Y, He L-Z, Cui H-R, Yin P (2017) Cis-stilbene glucoside in Polygonum multiflorum induces immunological idiosyncratic hepatotoxicity in LPS-treated rats by suppressing PPAR-γ. Acta Pharmacol Sin 38(10):1340–1352. https://doi.org/10.1038/aps.2017.32

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  15. Ahn SM, Kim HN, Kim YR, Choi YW, Kim CM, Shin HK (2016) Emodin from Polygonum multiflorum ameliorates oxidative toxicity in HT22 cells and deficits in photothrombotic ischemia. J Ethnopharmacol 188:13–20. https://doi.org/10.1016/j.jep.2016.04.058

    Article  PubMed  CAS  Google Scholar 

  16. Lv L, Cheng Y, Zheng T, Li X, Zhai R (2014) Purification, antioxidant activity and antiglycation of polysaccharides from Polygonum multiflorum Thunb. Carbohyd Polym 99:765–773. https://doi.org/10.1016/j.carbpol.2013.09.007

    Article  CAS  Google Scholar 

  17. Rui W, Xia W, Zhao W, Li B, Li J, Feng Y (2020) Differential constituents in roots, stems and leaves of Polygonum multiflorum thumb. screened by UPLC/ESI-Q-TOF-MS and multivariate statistical analysis. J Chromatogr Sci 58(2):136–143. https://doi.org/10.1093/chromsci/bmz086

    Article  PubMed  CAS  Google Scholar 

  18. Calassara LL, Pinto SC, Condack CPM, Leite BF, Nery LCDES, Tinoco LW (2020) Isolation and characterization of flavonoids from Tapirira guianensis leaves with vasodilatory and myeloperoxidase-inhibitory activities. Nat Prod Res. https://doi.org/10.1080/14786419.2020.1784170

    Article  PubMed  Google Scholar 

  19. Ma RY, Zhou RR, Tong RN, Shi SY, Chen XQ (2017) At-line hyphenation of high-speed countercurrent chromatography with Sephadex LH-20 column chromatography for bioassay-guided separation of antioxidants from vine tea (Ampelopsis grossedentata). J Chromatogr B 1040:112–117. https://doi.org/10.1016/j.jchromb.2016.11.037

    Article  CAS  Google Scholar 

  20. Wu L, Xiong W, Hu J-w, Gu Z, Xu J-g, Si C-l (2018) Purification of four flavonoid glycosides from Lotus (Nelumbo nucifera Gaertn) plumule by Macroporous resin combined with HSCCC. J Chromatogr Sci 56(2):108–114. https://doi.org/10.1093/chromsci/bmx088

    Article  PubMed  CAS  Google Scholar 

  21. Li CX, Zhao XH, Zuo WF, Zhang TL, Zhang ZY, Chen XS (2020) Phytochemical profiles, antioxidant, and antiproliferative activities of four red-fleshed apple varieties in China. J Food Sci 85(3):718–726. https://doi.org/10.1111/1750-3841.15056

    Article  PubMed  CAS  Google Scholar 

  22. Zheng L, Chen L, Li J, Liang L, Fan Y, Qiu L (2019) Two kaempferol glycosides separated from camellia oleifera meal by high-speed countercurrent chromatography and their possible application for antioxidation. J Food Sci 84(10):2805–2811. https://doi.org/10.1111/1750-3841.14765

    Article  PubMed  CAS  Google Scholar 

  23. Andarwulan N, Batari R, Sandrasari DA, Bolling B, Wijaya H (2010) Flavonoid content and antioxidant activity of vegetables from Indonesia. Food Chem 121(4):1231–1235. https://doi.org/10.1016/j.foodchem.2010.01.033

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  24. Chen B, Peng Y, Wang X, Li Z, Sun Y (2017) Preparative separation and purification of four glycosides from Gentianae radix by high-speed counter-current chromatography and comparison of their anti-NO production effects. Molecules 22(11):2002. https://doi.org/10.3390/molecules22112002

    Article  PubMed Central  CAS  Google Scholar 

  25. Chen Y, Du F, Wang W, Li Q, Zheng D, Zhang W (2017) Large-scale isolation of high-purity anthocyanin monomers from mulberry fruits by combined chromatographic techniques. J Sep Sci 40(17):3506–3512. https://doi.org/10.1002/jssc.201700471

    Article  PubMed  CAS  Google Scholar 

  26. Jiang J, Dong H, Wang T, Zhao R, Mu Y, Geng Y (2017) A strategy for preparative separation of 10 lignans from Justicia procumbens L. by high-speed counter-current chromatography. Molecules 22(12):2024. https://doi.org/10.3390/molecules22122024

    Article  PubMed Central  CAS  Google Scholar 

  27. Zhang L, Yue H-L, Zhao X-H, Li J, Shao Y (2015) Separation of four phenylpropanoid glycosides from a Chinese herb by HSCCC. J Chromatogr Sci 53(6):860–865. https://doi.org/10.1093/chromsci/bmu130

    Article  PubMed  CAS  Google Scholar 

  28. Zhang ZZ, ElSohly HN, Li XC, Khan SI Jr, SEB, Raulli RE, (2003) Phenolic Compounds from Nymphaea o dorata. J Nat Prod 66(4):548–550. https://doi.org/10.1021/np020442

    Article  PubMed  CAS  Google Scholar 

  29. Yang F, Qi Y, Liu W, Li J, Wang D, Fang L (2019) Separation of five flavonoids from aerial parts of salvia miltiorrhiza bunge using HSCCC and their antioxidant activities. Molecules 24(19):3448. https://doi.org/10.3390/molecules24193448

    Article  PubMed Central  CAS  Google Scholar 

  30. Lu Q, Sun Y, Shu Y, Tan S, Yin L, Guo Y (2016) HSCCC separation of the two iridoid glycosides and three phenolic compounds from Veronica ciliata and their in vitro antioxidant and anti-hepatocarcinoma activities. Molecules 21(9):1234. https://doi.org/10.3390/molecules21091234

    Article  PubMed Central  CAS  Google Scholar 

  31. Benmerache A, Benteldjoune M, Alabdul MA, Abedini A, Berrehal D, Kabouche A (2017) Chemical composition, antioxidant and antibacterial activities of Tamarix balansae J. Gay Aerial Parts. Nat Prod Res 31(24):2828–2835. https://doi.org/10.1080/14786419.2017.1299729

    Article  PubMed  CAS  Google Scholar 

  32. Choe KI, Kwon JH, Park KH, Oh MH, Kim MH, Kim HH (2012) The antioxidant and anti-inflammatory effects of phenolic compounds isolated from the root of Rhodiola sachalinensis A. BOR Molecules 17(10):11484–11494. https://doi.org/10.3390/molecules171011484

    Article  PubMed  CAS  Google Scholar 

  33. Arora A, Nair MG, Strasburg GM (1998) Structure–activity relationships for antioxidant activities of a series of flavonoids in a liposomal system. Free Radical Biol Med 24(9):1355–1363. https://doi.org/10.1016/S0891-5849(97)00458-9

    Article  CAS  Google Scholar 

  34. Li ZH, Lv WL, Lin H, Hu HB, Du GH (2019) Analysis of major constituents in Polygonum multiflorum Thunb leaf by HPLC-qTOF MS method. Central South Pharmacy 17(07):1115–1118

    Google Scholar 

  35. Ma JQ, Luo RZ, Jiang HX, Liu CM (2016) Quercitrin offers protection against brain injury in mice by inhibiting oxidative stress and inflammation. Food Funct 7(1):549–556. https://doi.org/10.1039/C5FO00913H

    Article  PubMed  CAS  Google Scholar 

  36. Meotti FC, Posser T, Missau FC, Pizzolatti MG, Leal RB, Santos AR (2007) Involvement of p38MAPK on the antinociceptive action of myricitrin in mice. Biochem Pharmacol 74(6):924–931. https://doi.org/10.1016/j.bcp.2007.06.024

    Article  PubMed  CAS  Google Scholar 

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Funding

This work was supported by the Key Project of Scientific and Technical supporting plan programs Foundation of Jiangxi (No. 2021YSBG21016 and 20202BBFL63035), the Fund for Distinguished Young Scholars of Jiangxi Province (20192BCB23027 and 2021YSBG50005), and the Science and Technology Major Project Foundation of Jiangxi Academy of Sciences (2020-YZD-1).

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Correspondence to Lei Wu or Ju-wu Hu.

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Cao, My., Wu, J., Wu, L. et al. Separation of three flavonoid glycosides from Polygonum multiflorum Thunb. leaves using HSCCC and their antioxidant activities. Eur Food Res Technol 248, 129–139 (2022). https://doi.org/10.1007/s00217-021-03865-0

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