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Current Analytical Chemistry

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ISSN (Print): 1573-4110
ISSN (Online): 1875-6727

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Research Article

Isolation and Purification of Kudinosides from Kuding Tea by Semi-Preparative HPLC Combined with MCI-GEL Resin

Author(s): Ji Tian, Xuanyuan Wang, Qingxin Shi, Xingliang Xiang, Chao Su, Yun Xie, Shuna Jin, Rongzeng Huang* and Chengwu Song*

Volume 16, Issue 7, 2020

Page: [914 - 923] Pages: 10

DOI: 10.2174/1573411015666191031153352

Price: $65

Abstract

Background: Kuding tea, a Traditional Chinese drink, has a history of thousands of years in China. Triterpenoid saponins in Kuding tea are regarded as one of the major functional ingredients.

Objective: The aim of this paper was to establish separation progress for the isolation and purification of five triterpenoid saponins (kudinoside A, C, D, F, G) from Kuding tea.

Methods: Nine types of resins, including seven macroporous resins and two MCI-GEL resins, were firstly used for purifying triterpenoid saponins by the adsorption and desorption tests. Further dynamic adsorption/desorption experiments were carried out to obtain the optimal parameters for the five targeted saponins. Then the purification of five triterpenoid saponins (kudinoside A, C, D, F, G) was completed by semi-preparative high-performance liquid chromatography (semi-pHPLC).

Results: As of optimized results, the HP20SS MCI-GEL was selected as the optimal one. The data also showed that 65.24 mg of refined extract including 7.04 mg kudinoside A, 3.52 mg kudinoside C, 4.04 mg kudinoside D, 4.13 mg kudinoside F, and 34.45 mg kudinoside G, could be isolated and purified from 645.90 mg of crude extract in which the content of five saponins was 81.51% and the average recovery reached 69.76%. The final contents of five saponins increased 6.91-fold as compared to the crude extract.

Conclusion: The established separation progress was highly efficient, making it a potential approach for the large-scale production in the laboratory and providing several markers of triterpenoid saponins for quality control of Kuding tea or its processing products.

Keywords: Enrichment, kuding tea, kudinoside, resin, semi-preparative HPLC, triterpenoid saponins.

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[1]
Song, C.; Yu, Q.; Li, X.; Jin, S.; Li, S.; Zhang, Y.; Jia, S.; Chen, C.; Xiang, Y.; Jiang, H. The hypolipidemic effect of total saponins from kuding tea in high-fat diet-induced hyperlipidemic mice and its composition characterized by UPLC-QTOF-MS/MS. J. Food Sci., 2016, 81(5), 1313-1319.
[http://dx.doi.org/10.1111/1750-3841.13299] [PMID: 27074384]
[2]
Thuong, P.T.; Su, N.D.; Ngoc, T.M.; Hung, T.M.; Dang, N.H.; Thuan, N.D.; Bae, K.; Oh, W.K. Antioxidant activity and principles of Vietnam bitter tea Ilex kudingcha. Food Chem., 2009, 113(1), 139-145.
[http://dx.doi.org/10.1016/j.foodchem.2008.07.041]
[3]
Liu, A.; Luo, Y.; Lin, Y. A review of the study on kudingcha. J. Chin. Med. Mater., 2002, 25(2), 148-150.
[PMID: 14740664]
[4]
Yang, M.; Zou, F.; Shi, Q.; Ji, S.; Wang, X.; Xiang, X.; Li, W.; Jin, S.; Huang, R.; Song, C. An efficient approach for enrichment of three isochlorogenic acids from Kuding tea using MCI-GEL resin. J. Liq. Chromatogr. Relat. Technol., 2018, 41(4), 188-195.
[http://dx.doi.org/10.1080/10826076.2018.1431276]
[5]
Fan, S.; Zhang, Y.; Hu, N.; Sun, Q.; Ding, X.; Li, G.; Zheng, B.; Gu, M.; Huang, F.; Sun, Y.Q.; Zhou, Z.; Lu, X.; Huang, C.; Ji, G. Extract of Kuding tea prevents high fat diet induced metabolic disorders in C57BL/6 mice via liver X receptor (LXR) β antagonism. PLoS One, 2012, 7(12) e51007
[http://dx.doi.org/10.1371/journal.pone.0051007] [PMID: 23226556]
[6]
Li, L.; Xu, L.J.; Ma, G.Z.; Dong, Y.M.; Peng, Y.; Xiao, P.G. The large-leaved Kudingcha (Ilex latifolia Thunb and Ilex kudingcha C.J. Tseng): a traditional Chinese tea with plentiful secondary metabolites and potential biological activities. J. Nat. Med., 2013, 67(3), 425-437.
[http://dx.doi.org/10.1007/s11418-013-0758-z] [PMID: 23529541]
[7]
Song, J.L.; Qian, Y.; Li, G.J.; Zhao, X. Anti-inflammatory effects of kudingcha methanol extract (Ilex kudingcha C.J. Tseng) in dextran sulfate sodium-induced ulcerative colitis. Mol. Med. Rep., 2013, 8(4), 1256-1262.
[http://dx.doi.org/10.3892/mmr.2013.1635] [PMID: 23969782]
[8]
Song, C.; Xie, C.; Zhou, Z.; Yu, S.; Fang, N. Antidiabetic effect of an active components group from ilex kudingcha and its chemical composition. Evid. Based Complement. Alternat. Med., 2012, 2012 423690
[http://dx.doi.org/10.1155/2012/423690] [PMID: 22474502]
[9]
Zhao, X.; Wang, Q.; Qian, Y.; Song, J.L. Ilex kudingcha C.J. Tseng (Kudingcha) has in vitro anticancer activities in MCF-7 human breast adenocarcinoma cells and exerts anti-metastatic effects in vivo. Oncol. Lett., 2013, 5(5), 1744-1748.
[http://dx.doi.org/10.3892/ol.2013.1253] [PMID: 23760150]
[10]
Zhu, K.; Li, G.; Sun, P.; Wang, R.; Qian, Y.; Zhao, X. In vitro and in vivo anti-cancer activities of Kuding tea (Ilex kudingcha C.J. Tseng) against oral cancer. Exp. Ther. Med., 2014, 7(3), 709-715.
[http://dx.doi.org/10.3892/etm.2013.1450] [PMID: 24520272]
[11]
Montoya, G.; Arango, G.J.; Unger, M.; Holzgrabe, U. O-glycoside sequence of pentacyclic triterpene saponins from Phytolacca bogotensis using HPLC-ESI/multi-stage tandem mass spectrometry. Phytochem. Anal., 2009, 20(6), 465-474.
[http://dx.doi.org/10.1002/pca.1148] [PMID: 19629957]
[12]
Liu, W.Y.; Feng, F.; Yu, C.X.; Xie, N. Qualitative and quantitative analysis of the main constituents of Radix Ilicis Pubescentis by LC-coupled with DAD and ESI-MS detection. Nat. Prod. Commun., 2010, 5(1), 23-26.
[http://dx.doi.org/10.1177/1934578X1000500106] [PMID: 20184013]
[13]
Qian, Z.M.; Lu, J.; Gao, Q.P.; Li, S.P. Rapid method for simultaneous determination of flavonoid, saponins and polyacetylenes in folium ginseng and radix ginseng by pressurized liquid extraction and high performance liquid chromatography coupled with diode array detection and mass spectrometry. J. Chromatogr. A, 2009, 1216(18), 3825-3830.
[http://dx.doi.org/10.1016/j.chroma.2009.02.065] [PMID: 19272605]
[14]
Capriotti, A.L.; Cavaliere, C.; Crescenzi, C.; Foglia, P.; Nescatelli, R.; Samperi, R.; Laganà, A. Comparison of extraction methods for the identification and quantification of polyphenols in virgin olive oil by ultra-HPLC-QToF mass spectrometry. Food Chem., 2014, 158(1), 392-400.
[http://dx.doi.org/10.1016/j.foodchem.2014.02.130] [PMID: 24731360]
[15]
Brusotti, G.; Cesari, I.; Dentamaro, A.; Caccialanza, G.; Massolini, G. Isolation and characterization of bioactive compounds from plant resources: the role of analysis in the ethnopharmacological approach. J. Pharm. Biomed. Anal., 2014, 87(1634), 218-228.
[http://dx.doi.org/10.1016/j.jpba.2013.03.007] [PMID: 23591140]
[16]
Zhou, Y.; Gao, X.; Fu, Q.; Guo, P.; Xu, X.; Zhang, T.; Ge, Y.; Zhang, B.; Wang, M.; Zeng, A.; Luo, Z.; Chang, C. Enrichment of total steroidal saponins from the extracts of Trillium tschonoskii Maxim by macroporous resin and the simultaneous determination of eight steroidal saponins in the final product by HPLC. J. Sep. Sci., 2017, 40(5), 1115-1124.
[http://dx.doi.org/10.1002/jssc.201600884] [PMID: 28044421]
[17]
Qi, X.L.; Peng, X.; Huang, Y.Y.; Li, L.; Wei, Z.F.; Zu, Y.G.; Fu, Y.J. Green and efficient extraction of bioactive flavonoids from Equisetum palustre L. by deep eutectic solvents-based negative pressure cavitation method combined with macroporous resin enrichment. Ind. Crops Prod., 2015, 70, 142-148.
[http://dx.doi.org/10.1016/j.indcrop.2015.03.026]
[18]
Sun, Y.; Yuan, H.; Hao, L.; Min, C.; Cai, J.; Liu, J.; Cai, P.; Yang, S. Enrichment and antioxidant properties of flavone C-glycosides from trollflowers using macroporous resin. Food Chem., 2013, 141(1), 533-541.
[http://dx.doi.org/10.1016/j.foodchem.2013.03.030] [PMID: 23768390]
[19]
Yang, W.Z.; Bo, T.; Ji, S.; Qiao, X.; Guo, D.A.; Ye, M. Rapid chemical profiling of saponins in the flower buds of Panax notoginseng by integrating MCI gel column chromatography and liquid chromatography/mass spectrometry analysis. Food Chem., 2013, 139(1-4), 762-769.
[http://dx.doi.org/10.1016/j.foodchem.2013.01.051] [PMID: 23561171]
[20]
Chen, F.; Luo, J.; Kong, L. Fast isolation of ginsenosides Re and Rg1 from the roots of by HSCCC-ELSD combined with MCI GEL CC guided by HPLC-MS. J. Liq. Chromatogr. Relat. Technol., 2012, 35(7), 912-923.
[http://dx.doi.org/10.1080/10826076.2011.613144]
[21]
Nie, W.; Luo, J.G.; Wang, X.B.; Wan, X.; Kong, L.Y. An insight into enrichment and separation of oleanane-type triterpenoid saponins by various chromatographic materials. Separ. Purif. Tech., 2009, 65(3), 243-247.
[http://dx.doi.org/10.1016/j.seppur.2008.10.042]
[22]
Li, C.; Zheng, Y.; Wang, X.; Feng, S.; Di, D. Simultaneous separation and purification of flavonoids and oleuropein from Olea europaea L. (olive) leaves using macroporous resin. J. Sci. Food Agric., 2011, 91(15), 2826-2834.
[http://dx.doi.org/10.1002/jsfa.4528] [PMID: 21744357]
[23]
Silva, E.M.; Pompeu, D.R.; Larondelle, Y.; Rogez, H. Optimisation of the adsorption of polyphenols from Inga edulis leaves on macroporous resins using an experimental design methodology. Separ. Purif. Tech., 2007, 53(3), 274-280.
[http://dx.doi.org/10.1016/j.seppur.2006.07.012]
[24]
Li, J.; Chase, H.A. Development of adsorptive (non-ionic) macroporous resins and their uses in the purification of pharmacologically-active natural products from plant sources. Nat. Prod. Rep., 2010, 27(10), 1493-1510.
[http://dx.doi.org/10.1039/c0np00015a] [PMID: 20820638]
[25]
Feng, J.; He, X.; Zhou, S.; Peng, F.; Liu, J.; Hao, L.; Li, H.; Ao, G.; Yang, S. Preparative separation of crocins and geniposide simultaneously from gardenia fruits using macroporous resin and reversed phase chromatography. J. Sep. Sci., 2014, 37(3), 314-322.
[http://dx.doi.org/10.1002/jssc.201300601] [PMID: 24259446]
[26]
Wang, R.; Peng, X.; Wang, L.; Tan, B.; Liu, J.; Feng, Y.; Yang, S. Preparative purification of peoniflorin and albiflorin from peony rhizome using macroporous resin and medium-pressure liquid chromatography. J. Sep. Sci., 2012, 35(15), 1985-1992.
[http://dx.doi.org/10.1002/jssc.201200120] [PMID: 22674837]
[27]
Chen, T.; Li, H.M.; Zou, D.L.; Du, Y.Z.; Shen, Y.H.; Li, Y. Preparation of two flavonoid glycosides with unique structures from barley seedlings by membrane separation technology and preparative high performance liquid chromatography. J. Sep. Sci., 2014, 37(24), 3760-3766.
[http://dx.doi.org/10.1002/jssc.201400798] [PMID: 25283274]
[28]
Zou, D.; Chen, T.; Chen, C.; Li, H.; Liu, Y.; Li, Y. An efficient protocol for preparation of gallic acid from terminalia bellirica (gaertn.) roxb by combination of macroporous resin and preparative high performance liquid chromatography. J. Chromatogr. Sci., 2016, 54(7), 1220-1224.
[http://dx.doi.org/10.1093/chromsci/bmw054] [PMID: 27076561]
[29]
Chen, T.; Liu, Y.; Zou, D.; Chen, C.; You, J.; Zhou, G.; Sun, J.; Li, Y. Application of an efficient strategy based on liquid-liquid extraction, high-speed counter-current chromatography, and preparative HPLC for the rapid enrichment, separation, and purification of four anthraquinones from Rheum tanguticum. J. Sep. Sci., 2014, 37(1-2), 165-170.
[http://dx.doi.org/10.1002/jssc.201300648] [PMID: 24166848]
[30]
Jin, H.; Liu, Y.; Feng, J.; Guo, Z.; Wang, C.; Zhong, Z.; Peng, X.; Dang, J.; Tao, Y.; Liang, X. Efficient purification of high-purity compounds from the stem of Lonicera japonica Thunb using two-dimensional preparative chromatography. J. Sep. Sci., 2013, 36(15), 2414-2420.
[http://dx.doi.org/10.1002/jssc.201300319] [PMID: 23720435]
[31]
Mangas, I.; Vilanova, E.; Benabent, M.; Estévez, J. Separating esterase targets of organophosphorus compounds in the brain by preparative chromatography. Toxicol. Lett., 2014, 225(1), 167-176.
[http://dx.doi.org/10.1016/j.toxlet.2013.12.003] [PMID: 24355587]
[32]
Yang, P.; Zhou, M.; Zhou, C.; Wang, Q.; Zhang, F.; Chen, J. Separation and purification of both tea seed polysaccharide and saponin from camellia cake extract using macroporous resin. J. Sep. Sci., 2015, 38(4), 656-662.
[http://dx.doi.org/10.1002/jssc.201401123] [PMID: 25491912]
[33]
Zhu, L.; Li, B.; Liu, X.; Meng, X. Purification of two triterpenoids from Schisandra chinensis by macroporous resin combined with high-speed counter-current chromatography. J. Chromatogr. Sci., 2014, 52(9), 1082-1088.
[http://dx.doi.org/10.1093/chromsci/bmt168] [PMID: 24220992]
[34]
Zhu, M.Z.; Wu, W.; Jiao, L.L.; Yang, P.F.; Guo, M.Q. Analysis of flavonoids in lotus (nelumbo nucifera) leaves and their antioxidant activity using macroporous resin chromatography coupled with LC-MS/MS and antioxidant biochemical assays. Molecules, 2015, 20(6), 10553-10565.
[http://dx.doi.org/10.3390/molecules200610553] [PMID: 26060918]
[35]
Shaheen, N.; Yin, L.; Gu, Y.; Rwigimba, E.; Xie, Q.; Wei, Y. Separation of isorhamnetin 3-sulphate and astragalin from Flaveria bidentis (L.) Kuntze using macroporous resin and followed by high-speed countercurrent chromatography. J. Sep. Sci., 2015, 38(11), 1933-1941.
[http://dx.doi.org/10.1002/jssc.201500119] [PMID: 25763770]
[36]
Su, J.W.; Jia, Z.M.; Xie, Y. [Study on ultrasonic extraction and macroporous resin purification techniques of total flavones from Sedum lineare] Zhong Yao Cai, 2013, 36(2), 298-301.
[PMID: 23901658]
[37]
Lu, C.; Luo, X.; Lu, L.; Li, H.; Chen, X.; Ji, Y. Preliminary extraction of tannins by 1-butyl-3-methylimidazole bromide and its subsequent removal from Galla chinensis extract using macroporous resins. J. Sep. Sci., 2013, 36(5), 959-964.
[http://dx.doi.org/10.1002/jssc.201200679] [PMID: 23362230]
[38]
Ouyang, M.A.; Wang, H.Q.; Chen, Z.L.; Yang, C.R. Triterpenoid glycosides from Ilex kudincha. Phytochemistry, 1996, 43(2), 443-445.
[http://dx.doi.org/10.1016/0031-9422(96)00015-5] [PMID: 8862036]
[39]
Ouyang, M.A.; Yang, C.R.; Wu, Z.J. Triterpenoid saponins from the leaves of Ilex kudincha. J. Asian Nat. Prod. Res., 2001, 3(1), 31-42.
[http://dx.doi.org/10.1080/10286020108042836] [PMID: 11355768]
[40]
Ding, Y.; Yang, X.M.; Pan, G.B.; Ma, H.L.; Liu, W.M. Adsorption and enrichment of alkalids from areca nut by means of macroporous resins. Adsorpt. Sci. Technol., 2012, 30(3), 193-204.
[http://dx.doi.org/10.1260/0263-6174.30.3.193]

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