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http://dx.doi.org/10.5142/jgr.2010.34.2.113

Physicochemical Characterization and NMR Assignments of Ginsenosides Rb1, Rb2, Rc, and Rd Isolated from Panax ginseng  

Cho, Jin-Gyeong (Graduate School of Biotechnology and Department of Oriental Medicinal Materials & Processing, Kyung Hee University)
Lee, Min-Kyung (Graduate School of Biotechnology and Department of Oriental Medicinal Materials & Processing, Kyung Hee University)
Lee, Jae-Woong (Department of Horticultural Biotechnology, Kyung Hee University)
Park, Hee-Jung (Graduate School of Biotechnology and Department of Oriental Medicinal Materials & Processing, Kyung Hee University)
Lee, Dae-Young (Graduate School of Biotechnology and Department of Oriental Medicinal Materials & Processing, Kyung Hee University)
Lee, Youn-Hyung (Department of Horticultural Biotechnology, Kyung Hee University)
Yang, Deok-Chun (Graduate School of Biotechnology and Department of Oriental Medicinal Materials & Processing, Kyung Hee University)
Baek, Nam-In (Graduate School of Biotechnology and Department of Oriental Medicinal Materials & Processing, Kyung Hee University)
Publication Information
Journal of Ginseng Research / v.34, no.2, 2010 , pp. 113-121 More about this Journal
Abstract
The fresh ginseng roots were extracted with aqueous methanol, and the obtained extracts were partitioned using ethyl acetate, n-butanol, and water, successively. The repeated silica gel and octadecyl silica gel column chromatogaraphy for n-butanol fraction afforded four diol ginseng saponins, ginsenosides $Rb_1$, $Rb_2$, $R_c$, and Rd. The physicochemical, spectroscopic, and chromatographic characteristics of these ginsenosides were measured and compared with those reported in the literature. Some of the peak assignments in previously published $^1H$- and $^{13}C$-nuclear magnetic resonance (NMR) spectra were inaccurate. This study employed two-dimensional NMR experiments, including $^1H-^1H$ correlation spectroscopy, heteronuclear single quantum correlation, and heteronuclear multiple bond connectivity, to determine exact peak assignments.
Keywords
Diol ginsenoside; Fast atom bombardment/mass spectrometry; High-performance liquid chromatography; Nuclear magnetic resonance;
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Times Cited By KSCI : 3  (Citation Analysis)
Times Cited By Web Of Science : 8  (Related Records In Web of Science)
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1 Karikura M, Miyase T, Tanizawa H, Taniyama T, Takino Y. Studies on absorption, distribution, excretion and metabolism of ginseng saponins. VII. Comparison of the decomposition modes of ginsenoside-Rb1 and -Rb2 in the digestive tract of rats. Chem Pharm Bull 1991;39:2357-2361.   DOI   ScienceOn
2 Sanada S, Kondo N, Shoji J, Tanaka O, Shibata S. Studies on the saponins of ginseng. I. Structures of ginsenoside-Ro, -$Rb_1$, -$Rb_2$, -Rc and -Rd. Chem Pharm Bull 1974;22:421-428.   DOI
3 Yahara S, Kaji K, Tanaka O. Further study on dammarane-type saponins of roots, leaves, flower-buds, and fruits of Panax ginseng C.A. Meyer. Chem Pharm Bull 1979;27:88-92.   DOI
4 Dong A, Ye M, Guo H, Zheng J, Guo D. Microbial transformation of ginsenoside Rb1 by Rhizopus stolonifer and Curvularia lunata. Biotechnol Lett 2003;25:339-344.   DOI   ScienceOn
5 Teng R, Ang C, McManus D, Armstrong D, Mau S, Bacic A. Regioselective acylation of ginsenosides by Novozyme 435 to generate molecular diversity. Helv Chim Acta 2004;87:1860-1872.   DOI   ScienceOn
6 Wang H, Tong YX, Ye WC, Zhao SX. Studies on chemical constituents in roots of Polygala tenuifolia. Zhongguo Zhong Yao Za Zhi 2003;28:828-830.
7 Cao XL, Tian Y, Zhang TY, Liu QH, Jia LJ, Ito Y. Separation of dammarane-saponins from notoginseng, root of Panax notoginseng. (Burk.) F. H. Chen, by HSCCC coupled with evaporative light scattering detector. J Liq Chromatogr Relat Technol 2003;26:1579-1591.   DOI   ScienceOn
8 Cheng LQ, Kim MK, Lee JW, Lee YJ, Yang DC. Conversion of major ginsenoside Rb1 to ginsenoside F2 by Caulobacter leidyia. Biotechnol Lett 2006;28:1121-1127.   DOI
9 Liu C, Han J, Duan Y, Huang X, Wang H. Purification and quantification of ginsenoside Rb3 and Rc from crude extracts of caudexes and leaves of Panax notoginseng. Sep Purif Technol 2007;54:198-203.   DOI   ScienceOn
10 Ma WG, Mizutani M, Malterud KE, Lu SL, Ducrey B, Tahara S. Saponins from the roots of Panax notoginseng. Phytochemistry 1999;52:1133-1139.   DOI   ScienceOn
11 Wang W, Zhao Y, Rayburn ER, Hill DL, Wang H, Zhang R. In vitro anti-cancer activity and structure-activity relationships of natural products isolated from fruits of Panax ginseng. Cancer Chemother Pharmacol 2007;59:589-601.   DOI
12 Zhao X, Wang J, Li J, Fu L, Gao J, Du X, Bi H, Zhou Y, Tai G. Highly selective biotransformation of ginsenoside Rb1 to Rd by the phytopathogenic fungus Cladosporium fulvum (syn. Fulvia fulva). J Ind Microbiol Biotechnol 2009;36:721-726.   DOI
13 Teng R, Li H, Chen J, Wang D, He Y, Yang C. Spectral assignments and reference data. Magn Reson Chem 2002;40:483-488.   DOI   ScienceOn
14 Oura H, Kumakai A, Shibata S, Takaki K. Chemical constituents of Panax ginseng. In: Panax ginseng: it’s study and progress. Tokyo: Kyoritz Press Ltd., 1981. p. 46-47.
15 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 insulin-like growth factor (IGF)-I in primary cultured rabbit proximal tubule cells. J Ginseng Res 2009;33:26-32.   DOI
16 Hong HD, Choi SY, Kim YC, Lee YC, Cho CW. Rapid determination of ginsenosides Rb1, Rf, and $Rg_1$ in Korean ginseng using HPLC. J Ginseng Res 2009;33:8-12.   DOI
17 Lee DY, Cho JG, Lee MK, Lee JW, Park HJ, Lee YH, Yang DC, Baek NI.　Identification of NMR data for ginsenoside $Rg_1$. J Ginseng Res 2008;32:291-299.   DOI   ScienceOn
18 Kim YH, Lee YG, Choi KJ, Uchida K, Suzuki Y. Transglycosylation to ginseng saponins by cyclomaltodextrin glucanotransferases. Biosci Biotechnol Biochem 2001;65:875-883.   DOI   ScienceOn
19 Dong A, Ye M, Guo H, Zheng J, Guo D. Microbial transformation of ginsenoside $Rb_1$ by Rhizopus stolonifer and Curvularia lunata. Biotechnol Lett 2003;25:339-344.   DOI   ScienceOn
20 Karikura M, Miyase T, Tanizawa H, Taniyama T, Takino Y. Studies on absorption, distribution, excretion and metabolism of ginseng saponin. VI. The decomposition products of ginsenoside Rb2 in the stomach of rats. Chem Pharm Bull 1991;39:400-404.   DOI   ScienceOn
21 Zhao X, Wang J, Li J, Fu L, Gao J, Du X, Bi H, Zhou Y, Tai G. Highly selective biotransformation of ginsenoside Rb1 to Rd by the phytopathogenic fungus Cladosporium fulvum (syn. Fulvia fulva). J Ind Microbiol Biotechnol 2009;36:721-726.   DOI
22 Yang CR, Kasai R, Zhou J, Tanaka O. Dammarane saponins of leaves and seeds of Panax notoginseng. Phytochemistry 1983;22:1473-1478.   DOI   ScienceOn
23 Du Q, Jerz G, Waibel R, Winterhalter P. Isolation of dammarane saponins from Panax notoginseng by high-speed counter-current chromatography. J Chromatogr A 2003;1008:173-180.   DOI   ScienceOn