Abstract
The purpose of this research was to investigate the composition of ginsenosides and to identify the chemical structures of ginsenosides generated from red ginseng by citric acid pre-treatment (RGC). The amount and the composition of ginsenosides in red ginseng (RG) and RGC were determined by high performance liquid chromatography (HPLC) analysis. The content of Rg3, a well-known bioactive ginsenoside in RGC increased significantly (p<0.05) over 2 fold (0.411 mg/g) when compared with RG (0.186 mg/g). Moreover, the structures of 5 novel ginsenosides in RGC were investigated by liquid chromatography/mass spectrometry (LC/MS/MS) analysis. Three peaks were completely fragmentized from their mother ions to aglycones and suggested to be less polar ginsenosides Rk3/Rh4, Rk1, and Rg5. This study suggested that by processing red ginseng with citric acid it is possible to enhance the yield of both ginsenoside Rg3 and less polar ginsenosides.
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Grandhi A, Mujumdar AM, Patwardhan B. A comparative pharmacological investigation of ashwagandha and ginseng. J. Ethnopharmacol. 44: 131–135 (1994)
Rausch WD, Liu S, Gille G, Radad K. Neuroprotective effects of ginsenosides. Acta Neurobiol. Exp. 66: 369–375 (2006)
Hikino H, Oshima Y, Suzuki Y, Konno C. Isolation and hypoglycemic activity of panaxans F, G, H, I, J, K, and L, glycans of Panax ginseng roots. Shoyakigaku Zasshi 39: 331–337 (1985)
Surh YJ, Na HK, Lee JY, Keum YS. Molecular mechanisms underlying anti-tumor promoting activities of heat-processed Panax ginseng C.A. Meyer. J. Korean Med. Sci. 16: 38–41 (2001)
Kim JS, Yoon KS, Lee YS. Antioxidant activity of main and fine roots of ginseng (Panax ginseng C.A. Meyer) extracted with various solvents. Food Sci. Biotechnol. 17: 46–51 (2008)
Fuzzati N. Analysis methods of ginsenosides. J. Chromatogr. B 812: 119–133 (2004)
Kim WY, Kim JM, Han SB, Lee SK, Kim ND, Park MK, Kim CK, Park JH. Steaming of ginseng at high temperature enhances biological activity. J. Nat. Prod. 63: 1702–1704 (2000)
Kim SI, Park JH, Ryu JH, Park JD, Lee YH, Park JH, Kim TH, Kim JM, Beak NI. Ginsenoside Rg5, a genuine dammarane glycoside from Korean red ginseng. Arch. Pharm. Res. 19: 551–553 (1996)
Ryu JH, Park JH, Kim TH, Sohn DH, Kim JM, Park JH. A genuine dammarane glycoside, (20E)-ginsenoside F4 from Korean red ginseng. Arch. Pharm. Res. 19: 335–336 (1996)
Park JD, Lee YH, Kim SI. Ginsenoside Rf2, a new dammarane glycoside from Korean red ginseng (Panax ginseng). Arch. Pharm. Res. 21: 615–617 (1998)
Beak NI, Kim DS, Lee YH, Park JD, Lee CB, Kim SI. Ginsenoside Rh4, a genuine dammarane glycoside from Korean red ginseng. Planta Med. 62: 86–87 (1996)
Park IH, Kim NY, Han SB, Kim JM, Kwon SW, Kim HJ, Park MK, Park JH. Three new dammarane glycosides from heat processed ginseng. Arch. Pharm. Res. 25: 428–432 (2002)
Bao HY, Zhang J, Yeo SJ, Myung CS, Kim HM, Kim JM, Park JH, Cho J, Kang JS. Memory enhancing and nueroprotective effects of selected ginsenosides. Arch. Pharm. Res. 28: 335–342 (2005)
Kang KS, Kim HY, Yamabe N, Yokozawa T. Stereospecificity in hydroxyl radical scavenging activities of four ginsenosides produced by heat processing. Bioorg. Med. Chem. Lett. 16: 5028–5031 (2006)
Keum YS, Park KK, Lee JM, Chun KS, Park JH, Lee SK, Kwon H, Surh YJ. Antioxidant and anti-tumor promoting activities of the methanol extract of heat-processed ginseng. Cancer Lett. 150: 41–48 (2000)
Beak SH, Piao XL, Lee UJ, Kim HY, Park JH. Reduction of cisplatin-induced nephrotoxicity by ginsenosides isolated from processed ginseng in cultured renal tubular cells. Biol. Pharm. Bull. 29: 2051–2055 (2006)
Kwon SW, Han SB, Park IH, Kim JM, Park MK, Park JH. Liquid chromatographic determination of less polar ginsenosides in processed ginseng. J. Chromatogr. A 921: 335–339 (2001)
Ko SK, Lee KH, Hong JK, Kang SA, Sohn UD, Im BO, Han ST, Yang BW, Chung SH, Lee BY. Change of ginsenoside composition in ginseng extract by vinegar process. Food Sci. Biotechnol. 14: 509–513 (2005)
Ando T, Tanaka O, Shibata S. Chemical studies on the oriental plant drugs (XXV). Comparative studies on the saponins and sapogenins of ginseng and related crude drugs. Syoyakugaku Zasshi 25: 28–32 (1971)
Kim SN, Ha YW, Shin H, Son SH, Wu SJ, Kim YS. Simultaneous quantification of 14 ginsenosides in Panax ginseng C.A. Meyer (Korean red ginseng) by HPLC-ELSD and its application to quality control. J. Pharmaceut. Biomed. 45: 164–170 (2007)
Keum YS, Han SS, Chun KS, Park KK, Park JH, Lee SK, Surh YJ. Inhibitory effects of the ginsenoside Rg3 on phorbol ester-induced cyclooxygenase-2 expression, NF-kB activation and tumor promotion. Mutat. Res. 523–524: 75–85 (2003)
Kim SW, Kwon HY, Chi DW, Shim JH, Park JD, Lee YH, Pyo S, Rhee DK. Reversal of P-glycoprotein-mediated multidrug resistance by ginsenoside Rg3. Biochem. Pharmacol. 65: 75–82 (2003)
Ko SK, Cho OS, Be HM, Sohn UD, Im BO, Cho SH, Yang BW, Chung SH, Shin WS, Lee BY. Ginsonoside composition changes in ginseng extracts by different ascorbic acid treatments. Food Sci. Biotechnol. 17: 883–887 (2008)
Popovich DG, Kitts DD. Structure-function relationship exists for ginsenosides in reducing cell proliferation and inducing apoptosis in the human leukemia (THP-1) cell line. Arch. Biochem. Biophys. 406: 1–8 (2002)
Shibata S, Tanaka T, Ando T, Sado M, Tsushima S, Ohsawa T. Chemical studies on oriental plant drugs (XIV). Protopanaxadiol, a genuine sapogenin of ginseng saponins. Chem. Pharm. Bull. 14: 595–600 (1966)
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Yi, JH., Kim, MY., Kim, YC. et al. Change of ginsenoside composition in red ginseng processed with citric acid. Food Sci Biotechnol 19, 647–653 (2010). https://doi.org/10.1007/s10068-010-0091-1
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DOI: https://doi.org/10.1007/s10068-010-0091-1