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Re-evaluation of physicochemical and NMR data of triol ginsenosides Re, Rf, Rg2, and 20-gluco-Rf from Panax ginseng roots

  • Cho, Jin-Gyeong (Graduate School of Biotechnology and Department of Oriental Medicinal Materials and Processing, Kyung Hee University) ;
  • In, Seo-Ji (Graduate School of Biotechnology and Department of Oriental Medicinal Materials and Processing, Kyung Hee University) ;
  • Jung, Ye-Jin (Graduate School of Biotechnology and Department of Oriental Medicinal Materials and Processing, Kyung Hee University) ;
  • Cha, Byeong-Ju (Graduate School of Biotechnology and Department of Oriental Medicinal Materials and Processing, Kyung Hee University) ;
  • Lee, Dae-Young (Department of Herbal Crop Research, National Institute of Horticultural and Herbal Science, Rural Development Administration) ;
  • Kim, Yong-Bum (Technology Services Division, National Institute of Horticultural and Herbal Science, Rural Development Administration) ;
  • Yeom, Myeonghun (Amorepacific Corporation Research and Development Center) ;
  • Baek, Nam-In (Graduate School of Biotechnology and Department of Oriental Medicinal Materials and Processing, Kyung Hee University)
  • Received : 2013.08.31
  • Accepted : 2013.12.22
  • Published : 2014.04.15

Abstract

Ginseng roots were extracted with aqueous methanol, and extracts were suspended in water and extracted successively with ethyl acetate and n-butanol. Column chromatography using the n-butanol fraction yielded four purified triol ginseng saponins: the ginsenosides Re, Rf, Rg2, and 20-gluco-Rf. The physicochemical, spectroscopic, and chromatographic characteristics of the ginsenosides were measured and compared with reports from the literature. For spectroscopic analysis, two-dimensional nuclear magnetic resonance (NMR) methods such as $^1H$-$^1H$ correlation spectroscopy, nuclear Overhauser effect spectroscopy, heteronuclear single quantum correlation, and heteronuclear multiple bond connectivity were employed to identify exact peak assignments. Some peak assignments for previously published $^1H$-and $^{13}C$-NMR spectra were found to be inaccurate. This study reports the complete NMR assignment of 20-gluco-Rf for the first time.

Keywords

References

  1. Jung HK, Lim SK, Park MJ, Bae CS, Yoon KC, Han HJ, Park SH. The protective effect of ginseng saponin against high glucose-induced secretion of insulinlike growth factor (IGF)-I in primary cultured rabbit proximal tubule cells. J Ginseng Res 2009;33:26-32. https://doi.org/10.5142/JGR.2009.33.1.026
  2. Hong HD, Choi SY, Kim YC, Lee YC, Cho CW. Rapid determination of ginsenosides Rb1, Rf, and Rg1 in Korean ginseng using HPLC. J Ginseng Res 2009;33:8-12. https://doi.org/10.5142/JGR.2009.33.1.008
  3. Lee DY, Cho JG, Lee MK, Lee JW, Park HJ, Lee YH, Yang DC, Baek NI. Identification of NMR data for ginsenoside Rg1. J Ginseng Res 2008;32:291-9. https://doi.org/10.5142/JGR.2008.32.4.291
  4. Cho JG, Lee MK, Lee JW, Park HJ, Lee DY, Lee YH, Yang DC, Baek NI. Physicochemical characterization and NMR assignments of ginsenosides Rb1, Rb2, Rc, and Rd isolated from Panax ginseng. J Ginseng Res 2010;34:113-21. https://doi.org/10.5142/jgr.2010.34.2.113
  5. Lu D, Li P, Liu JP. Quinquenoside F6, a new triterpenoid saponin from the fruits of Panax quinquefolium L. Nat Prod Res 2012;26:1395-401. https://doi.org/10.1080/14786419.2011.592833
  6. Kang DI, Jung KW, Kim SK, Lee SA, Jhon GJ, Kim YM. Tertiary structure of ginsenoside Re studied by NMR spectroscopy. Bull Korean Chem Soc 2007;28: 2209-13. https://doi.org/10.5012/bkcs.2007.28.12.2209
  7. Zhang AF, Zhu JH, Yu RM. Isolation and structural elucidation of ginsenosides from the medium of transgenic crown gall of Panax quinquefolium. J Jinan Univ 2008;29:286-9.
  8. Teng RW, Li HZ, Chen JT, Wang DZ, He YN, Yang CR. Spectral assignments and reference data. Magn Reson Chem 2002;40:483-8. https://doi.org/10.1002/mrc.1033
  9. Yang XW, Li LY, Tian JM, Zhang ZW, Ye JM, Gu WF. Ginsenoside-Rg6, a novel triterpenoid saponin from the stem-leaves of Panax ginseng C. A. Mey. Chinese Chem Lett 2000;11:909-12.
  10. Du QZ, Jerz G, Waibel R, Winterhalter P. Isolation of dammarane saponins from Panax notoginseng by high-speed counter-current chromatography. J Chromatogr A 2003;1008:173-80. https://doi.org/10.1016/S0021-9673(03)00988-9
  11. Fujioka N, Kohda H, Yamasaki K, Kasai R, Tanaka O, Shoyama Y, Kishioka I. Dammarane and oleanane saponins from callus tissue of Panax japonicus. Phytochemistry 1989;28:1855-8. https://doi.org/10.1016/S0031-9422(00)97874-9
  12. Sun HX, Chen YH, Ye YP. Ginsenoside Re and notoginsenoside R1: immunologic adjuvants with low haemolytic effect. Chem Biodivers 2006;3:718-21. https://doi.org/10.1002/cbdv.200690074
  13. Park JD, Wee JJ, Kim MW, Lee HJ. Hematopoietic characteristics of the ethylacetate fraction of Panax ginseng and identification of the chemical constituents. J Korean Agric Chem Soc 1989;32:137-42.
  14. Zhou J,WuMZ, Taniyasu S, BessoH, Tanaka O, Saruwatari Y, FuwaT. Dammaranesaponins of Sanchi-ginseng, roots of Panax notoginseng (BURK.) F.H. CHEN (Araliaceae): structures of new saponins, notoginsenosides-R1 and -R2, and identification of ginsenosides-Rg2 and -Rh1. Chem Pharm Bull 1981;29:2844-50. https://doi.org/10.1248/cpb.29.2844
  15. Sanada S, Kondo N, Shoji J, Tanaka O, Shibata S. Studies on the saponins of ginseng Ⅱ. Structures of ginsenoside-Re, -Rf and eRg2. Chem Pharm Bull 1974;22:2407-12. https://doi.org/10.1248/cpb.22.2407
  16. Haijiang Z, YongJiang W, Yiyu C. Analysis of 'SHENMAI' injection by HPLC/MS/ MS. J Pharm Biomed Anal 2003;31:175-83. https://doi.org/10.1016/S0731-7085(02)00565-4
  17. Chan TWD, But PPH, Cheng SW, Kwok IMY, Lau FW, Xu HX. Differentiation and authentication of Panax ginseng, Panax quinquefolius, and ginseng products by using HPLC/MS. Anal Chem 2000;72:1281-7. https://doi.org/10.1021/ac990819z
  18. Xie YY, Luo D, Cheng YJ, Ma JF, Wang IM, Liang QL, Luo GA. Steaming-induced chemical transformations and holistic quality assessment of red ginseng derived from Panax ginseng by means of HPLC-ESI-MS/MSn-based multicomponent quantification fingerprint. J Agric Food Chem 2012;60:8213-24. https://doi.org/10.1021/jf301116x
  19. Sanada S, Shoji J. Studies on the saponins of ginseng III. Structures of ginsenoside- Rb3 and 20-glucoginsenoside-Rf. Chem Pharm Bull 1978;26:1694-7. https://doi.org/10.1248/cpb.26.1694
  20. Li SL, Lai SF, Song JZ, Qiao CF, Liu X, Zhou Y, Cai H, Cai BC, Xu HX. Decoctinginduced chemical transformations and global quality of Du-Shen-Tang, the decoction of ginseng evaluated by UPLC-Q-TOF-MS/MS based chemical profiling approach. J Pharm Biomed Anal 2010;53:946-57. https://doi.org/10.1016/j.jpba.2010.07.001
  21. Ma XQ, Liang XM, Xu Q, Zhang XZ, Xiao HB. Identification of ginsenosides in roots of Panax ginseng by HPLC-APCI/MS. Phytochem Anal 2005;16:181-7. https://doi.org/10.1002/pca.842

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