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광규 서
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1 ginsenoside 33 DOI : /KPI ginsenoside Received : Revised : Accepted : Key Words: ginsenoside, cultivated ginseng, mountain ginseng, red ginseng, fermentation Component analysis of cultivated ginseng and mountain ginseng to the change of ginsenoside components in the process of heating and fermentation. Bae -Cheon Cha 1), Hye -Chul Yoon 2), Dae-Ho Lee 3), Jae-Seuk Park 2), Ki-Rok Kwon 2) 1) Pharmaceutical Engineering, Health of Science, Sangji Univ. 2) College of Oriental medicine, Sangji Univ. 3) G&V Company. ABSTRACT Objectives: The aim of this experiment is to provide an objective differentiation of cultivated ginseng, mountain ginseng through component analysis, and to know the change of ginsenoside components in the process of heating and fermentation. Methods: Comparative analyses of ginsenoside Rb1, Rb2, Rc, Rd, Re, Rf, Rg1, Rg3, Rh1 and Rh2 from the cultivated ginseng 4 and 6 years, and mountain cultivated ginseng were conducted using HPLC (High Performance Liquid Chromatography, hereafter HPLC). And the same analyses were conducted in the process of heating and fermentation using mixed Lactobacillus rhamnosus, Lactobacillus plantarum, Bifidobacterium lactis for 7 days. Results: The change of ginsenosides to the process of red ginseng and fermentation, cultivated ginseng and mountain cultivated ginseng were showed another results. Mountain ginseng showed a lot of change compared with cultivated ginsengs. In the 7 days of fermentation, mountain ginseng showed that ginsenoside Rg1, Rb1, Rb2, Rc, and Rd were decreased and increased ginsenoside Re, Rf, Rg3 and Rh1 were increased compared with cultivated ginseng. Conclusions: It seemed that ginsenosides of mountain cultivated ginseng was better resolved than cultivated ginseng because the difference of structure or distribution of ginsenosides in the condition of fermentation. I Panax Ginseng C. A. Meyer Araliaceae 1123 Corresponding author : Ki- Rok Kwon, Dept. of Acupuncture & Moxibustion, College of Korean Medicine, Sangji University 283, Woosan-dong, Wonju-si, Kangwon-do, , South Korea. Tel: beevenom@paran.com This study was supported by Technology Development Program for Agriculture and Forestry( CG000), Ministry for Agriculture, Forestry and Fisheries, Republic of korea.

2 34 Journal of Pharmacopuncture micelles caramel ginsenoside Rh2, ginsenoside Rg3 acid ginsenoside Rh2, ginsenoside Rg3 ginsenoside HPLC High Performance Liquid Chromatography, HPLC 10 ginsenosides II Rotary vacuum evaporator Eyela Tokyo Co. HPLC Varian 9012 Solvent Delivery System, Varian Variable Wavelength 9050 UV-VIS detector, Autos-ampler Varian 9300 AcCN, MeOH HPLC 1 2, 4, 7 ginsenoside Rb1, Rb2, Rc, Rd, Re, Rf, Rg1, Rg3, Rh1 Rh MeOH MeOH 80 MeOH n-hexane, EtOAc n-buoh n-buoh n-buoh Fig. 1 1 HPLC HPLC column Capcell Pak C Shiseido Co. 1 min, column UV

3 ginsenoside Table 1. ginsenoside Rb1, Rb2, Rc, Rd, Re, Rf, Rg1, Rg3, Rh1 Rh MeOH membrane filter n-buoh 10 MeOH membrane filter ginsenoside Rb1, Rb2, Rc, Rd, Re, Rf, Rg1, Rg3, Rh1 Rh , 400, 300, 200, 100, 50 ginsenoside X Y ginsenoside R 2 Table HPLC chromatogram chromatogram HPLC ginsenoside Rb1, Rb2, Rc, Rd, Re, Rf, Rg1, Rg3, Rh1 Rh2 chromatogram ginsenoside cellbiotec ATP Lactobacillus rhamnosus, Lactobacillus plantarum, Bifidobacteri-um lactis 1 37 clean banch 7 1, 2, 4, 7 HPLC 10 ginsenoside 2 ginsenoside Rg1, Re, Rf, HPLC ginsenoside Rc, Rb2, Rd, Rg3 ginsenoside Rh2 III 1 ginsenosides ginsenoside Fig ginsenoside Rb1, Rb2, Rc, Rd, Re, Rf, Rg1 Rh1 Re Rf 2 Rg3 6 ginsenoside Rb1, Rb2, Re, Rg1 Rc, Rd, Rf, Rg3 Rh1 ginsenoside Re, Rf, Rg1, Rg3 Rh1 ginsenoside Rb1, Rb2, Rc ginsenoside Rd 2 ginsenoside Rb1

4 36 Journal of Pharmacopuncture ginsenoside Rb Fig. 3 3 ginsenoside Rb2 ginsenoside Rb Fig. 4 4 ginsenoside Rc ginsenoside Rc Fig. 5 5 ginsenoside Rd ginsenoside Rd Fig. 6 6 ginsenoside Re ginsenoside Re

5 ginsenoside 37 Fig. 7 7 ginsenoside Rf ginsenoside Rf Fig. 8 8 ginsenoside Rg1 ginsenoside Rg Fig Fig ginsenoside Rh1 ginsenoside Rh Fig ginsenoside Rh2 ginsenoside Rh2 9 ginsenoside Rg3 ginsenoside Rg IV Panax

6 38 Journal of Pharmacopuncture Brekhman Shibata ginsenoside 30 ginsenoside phenol polysaccharide triterpenoid steroid oleanane Shibata Tanaka oleanane dammarane triterpenoid ginsenoside triterpenoid dammarane glucose, arabinose, xylose, rhamnose ginsenoside oleanane ginsenoside Ro 1 protopanaxadiol ginsenoside Ra1, Ra2, Ra3, Rb1, Rb2, Rb3, Rc, Rd, Rg3, Rh2 10 protopanaxatriol ginsenoside Re, Rf, 20-gluco-Rf, Rg1, Rg2 Rh1 ginsenoside ginsenoside ginsenoside Rb1 ginsenoside Rb2 ginsenoside Rc ginsenoside Rd ginsenoside-rg3 ginsenoside-rh2 caramel ginsenoside 2 ginsenoside Rg3 3,000 Lactobacilli Bifidobacterium ginsenoside Fig. 12 ginsenoside Lactobacillus rhamnosus, Lactobacillus plantarum, Bifidobacterium lactis ginsenoside-rg3 ginsenoside-rh2 1, 2, 4, 7 HPLC

7 ginsenoside 39 ginsenoside Rb1, Rb2, Rc, Rd, Re, Rf, Rg1, Rg.3, Rh1 Rh2 10 ginsenoside 4 6 ginsenoside Rb1, ginsenoside Rg3 ginsenoside Rh2 Rb2, Rc, Rd, Rg3, Rh1 Re Rg1 ginsenoside Rb1, Rb2 Rc, Rd Re Rf, Rg1 Rg3, Rh1 ginsenoside 4 ginsenoside Re, Rg1 Rb1, Rd, Rg3, Rh1 6 ginsenoside Rb1, Rb2, Rc, Rd, Re, Rf, Rg1 Rg3 4 6 ginsenoside Rb1, Rb2, Rc, Rd, Rg1 Re, Rf, Rg3 ginsenoside Rg3 7 ginsenoside Rh2 ginsenosides Fig ginsenosides ginsenosides ginsenoside-rg3 ginsenoside-rh2 4 6 V ginsenoside Lactobacillus rhamnosus HPLC ginsenoside Rb1, Rb2, Rc, Rd, Re, Rf, Rg1, Rg3, Rh1 Rh ginsenoside Rb1, Rb2 Rc, Rd Re Rf, Rg1 Rg3, Rh1 2. ginsenoside 4 ginsenoside Re, Rg1 Rb1, Rd, Rg3 Rh1 3. ginsenoside 6 ginsenoside Rb1, Rb2, Rc, Rd, Re, Rf, Rg1 Rg3 4. ginsenoside ginsenoside Rb1, Rb2, Rc, Rd, Rg1 Re, Rf, Rg3 5. ginsenoside 4 6 6

8 40 Journal of Pharmacopuncture VI. References 1. Nam Ki Yeul. The comparative understanding between red ginseng and white ginsengs, processed ginsengs. j. ginseng res. 2005; 29(1): Matsuda H. Study on efficacy of processed ginseng, red ginseng. Natural Medicines. 1999; 53: Kitagawa L, Yoshikawa M, Yoshihara M, Hayashi T. and Taniyama, T. Chemical studies of crude drugs (1). Constituents of ginseng radix rubra. 1983; 103(6): Han BH, Pakr MH, and Han YN. Degradation of ginseng under mild acidic condition. Planta Med. 1982; 44: Suzuki Y, Ko SR, Choi KJ, Uchida K, Lee YG and Kim YH. Enzymatic glycosylation and hydrosis of ginseng saponins. Proc. 7th Symp. 1998; Hasegawa H, Sung JH, Matsumiya S and Uchiyama M. Main ginseng saponin metabolites formed intestinal Prevotella oris in hydrolyzing ginseng saponins. Planta Med. 1997; 63(5): Kong BM, Park MJ, Min JW, Kim HB, Kim SH, Kim SY and Yang DC. Physico-chemical characteristics of white fermented and red ginseng extracts. J. ginseng Res. 2008; 32(3): Wang W, Zhao Y, Rayburn ER, Hill DL, Wang H and Zhang R. In vitro anti-cancer activity and structure-activity relationships of natural products isolated from fruits of Panax ginseng. Cancer Chemoth Pharmacol. 2007; 59: LY Wu J. Inhibitory effect of 20(S)-ginsenoside Rg3 on growth and metasis of Lewis pulmonary carcinoma. Zhonggliu Fangzhi Yanjiu. 2006; 33: David GP and David DK. Ginsenosides 20(S)- protopanaxadiol and Rh2 reduce cell proliferation and increase sub-g1 cells in two cultured intestinal cell lines, Int-407 and Caco-2. Can. J Physiol. Pharmacol. 2004; 82: Park SJ, Kim DH, Paek NS and Kim SS. Preparation and quality characteristics of the fermentation product of ginseng by lactic acid bacteria. J. Ginseng Res. 2006; 30(2): Brekhman. II. Panax ginseng, Gosudarst Isdat et Med, Lit. Leningard, 1957; Shibata, S., Tanaka, O., Soma, K., lita, Y., Ando, T. and Nakamura, H. Studies on saponins and sapogenins of ginseng. The structure of panaxatriol. Tetrahedron Lett., 1965; 3: Nam Ki Yeul. Contemporary Korean Ginseng. Korean Ginseng & Tobacco Research Institute. 1996; Park JD. Rescent studies on the chemical constituents of Korean Ginseng. Korean J. Ginseng Sci. 1996: 20(4): Jeong CS, Hyun JE and Kim YS. Anti-oxidative effect of ginsenoside Rb1 on the H, ethanol-induced gastric tissue in rats. Kor. J Pharmacogn. 2002; 33(3): Choi KJ. The constituent of material ginseng and management of quality. Korean J Ginseng Sci. 1991; 15(3): Hideo H, Seong JH, Yasatosi M, Masamori W and Hur JD. Metabolites of ginseng saponin by enterobacteria and anti cancer substance include it's useful constituent. Korea Plant. 1998; No Choi SS, Lee JK, Han KJ, Lee HK, Lee J and Suh HW. Effects of ginsenoside Rd on nitric oxide system induced by lipopolysaccharide plus TNF- in C6 rat glioma cells. Arch Pharm. Res. 2003; 26:

ginsenoside 41 20. Yokozawa T and Liu ZW. The role of ginsenoside Rd in cisplatin-induces acute renal failure. Ren. Fail. 2000; 22: 115-127. 21. Goldin BR. Health benefits of probitics. Br. J. Nutr.

9 ginsenoside Yokozawa T and Liu ZW. The role of ginsenoside Rd in cisplatin-induces acute renal failure. Ren. Fail. 2000; 22: Goldin BR. Health benefits of probitics. Br. J. Nutr. 1998; 80: Fuller R. Probiotics in man and animals. J. Applied Bacteriology. 1989; 66: Jeong HS, Lim CS, Cha BC, Choi SH, Kwon KR. Component analysis of cultivated ginseng, cultivated wild ginseng, and wild ginseng and the change of ginsenoside components in the process of red ginseng. J. of KPI. 2010; 13(1) Fig. 1 Manufacturing process of crude saponin by extraction and fraction

10 42 Journal of Pharmacopuncture (1) (2) (3) (4) Fig. 2 (1) HPLC chromatogram of standard ginsenosides.; 1: ginsenoside Rg1, 2: ginsenoside Re, 3: ginsenoside Rf, 4: ginsenoside Rh1, 5: ginsenoside Rb1, 6: ginsenoside Rc, 7: ginsenoside Rb2, 8: ginsenoside Rd, 9: ginsenoside Rg3, 10: ginsenoside Rh2. HPLC chromatogram of cultivated ginseng 4 years(2), cultivated ginseng 6 years (3) and cultivated wild ginseng (4) of fermented 7 days by lactic acid and bacteria.

11 ginsenoside 43 1 Fig. 3 Changes of ginsenoside Rb1 contents on various ginsengs in the process of heating and fermentation. 2 Fig. 4 Changes of ginsenoside Rb2 contents on various ginsengs in the process of heating and fermentation.

12 44 Journal of Pharmacopuncture Fig. 5 Changes of ginsenoside Rc contents on various ginsengs in the process of heating and fermentation. Fig. 6 Changes of ginsenoside Rd contents on various ginsengs in the process of heating and fermentation.

13 ginsenoside 45 Fig. 7 Changes of ginsenoside Re contents on various ginsengs in the process of heating and fermentation. Fig. 8 Changes of ginsenoside Rf contents on various ginsengs in the process of heating and fermentation.

14 46 Journal of Pharmacopuncture Fig. 9 Changes of ginsenoside Rg1 contents on various ginsengs in the process of heating and fermentation. 3 Fig. 10 Changes of ginsenoside Rg3 contents on various ginsengs in the process of heating and fermentation.

15 ginsenoside 47 1 Fig. 11 Changes of ginsenoside Rh1 contents on various ginsengs in the process of heating and fermentation.

16 48 Journal of Pharmacopuncture Fig. 12 Proposed Transformation Pathways of Rb2 by Cell-Extracts from Various Food Microorganisms

17 ginsenoside 49 Table 1. HPLC condition for analysis of ginsenosides Instrument Pump 9012 Solvent Delivery System, Varian Co. Detector 9050 Variable Wavelength UV-VIS Detector, Varian Co. Autosampler 9300 Autosampler, Varian Co. Column Capcell Pak C18 ( mm: 5 ), Shiseido Co. Operating condition UV Absorbance Column temp. Injection vol. Mobile phase A Mobile phase B 203 nm Water Acetonitrile Gradient profile Time(min) %A %B Flow( /min) 0: : : : : Table 2. Equation and R 2 value of ginsenosides Sample Equation R 2 Ginsenoside Rb1 y = x Ginsenoside Rb2 y = x Ginsenoside Rc y = x Ginsenoside Rd y = x Ginsenoside Re y = x Ginsenoside Rf y = x Ginsenoside Rg1 y = x Ginsenoside Rg3 y = x Ginsenoside Rh1 y = x Ginsenoside Rh2 y = x

063~078 인삼

063~078 인삼 ginsenoside 63 DOI : 10.3831/KPI.2010.13.1.063 ginsenoside Received : 10. 01. 25 Accepted : 10. 02. 25 Key Words: ginsenoside, cultivated wild ginseng, wild ginseng, cultivated ginseng, HPLC Component