Journal of Ginseng Research

The Korean Society of Ginseng (고려인삼학회)
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The Chemical and 1,1-Diphenyl-2-Picrylhydrazyl Radical Scavenging Activity Changes of Ginsenosides Rb1 and Rg1 by Maillard Reaction

  • Yamabe, Noriko (Institute of Natural Medicine, University of Toyama) ;
  • Lee, Jin-Gyun (Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University) ;
  • Lee, Yong-Jae (Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University) ;
  • Park, Chan-Hum (Institute of Natural Medicine, University of Toyama) ;
  • Kim, Hyun-Young (Department of Food Science, Jinju National University) ;
  • Park, Jeong-Hill (Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University) ;
  • Yokozawa, Takako (Institute of Natural Medicine, University of Toyama) ;
  • Kang, Ki-Sung (Institute of Natural Medicine, University of Toyama)
  • Received : 2010.10.14
  • Accepted : 2011.01.17
  • Published : 2011.03.29
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Abstract

The chemical and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity changes of ginsenoside $Rb_1$-glycine and ginsenoside $Rg_1$-glycine mixtures by Maillard reaction were investigated to identify the role of Maillard reaction in the increased antioxidant activity of ginseng by heat-processing. The DPPH radical scavenging activity of $Rg_1$-glycine mixture was more strongly increased by heat-processing than that of $Rb_1$-glycine mixture. From the analyses of ginsenosides, $Rb_1$ was gradually changed into 20(S)-$Rg_3$, 20(R)-$Rg_3$, $Rk_1$ and $Rg_5$ by heat-processing. $Rg_1$ was gradually changed into 20(S)-$Rh_1$, 20(R)-$Rh_1$, $Rk_3$ and $Rh_4$ by heat-processing. However, the generation of these less-polar ginsenosides was not related to the increased DPPH radical scavenging activity of $Rb_1$-glycine and $Rg_1$-glycine mixtures because their DPPH radical scavenging activities were already significantly increased when dried at $50^{\circ}C$, which temperature induce no structural changes of ginsenosides. In the comparison of browning compound levels of $Rg_1$-glycine and $Rb_1$-glycine mixtures, the extents of Maillard reaction were positively correlated with their increased free radical scavenging activities. Based on the chemical and DPPH radical scavenging activity changes of $Rg_1$-glycine and $Rb_1$-glycine mixtures by heat-processing, we clearly identified that the increased free radical scavenging activity of ginsenoside is mediated by the Maillard reaction between sugar moiety of ginsenoside and amino acid.

Keywords

References

  1. Park JD. Recent studies on the chemical constituents of Korean ginseng (Panax ginseng C. A. Meyer). Korean J Ginseng Sci 1996;20:389-415.
  2. Yokozawa T, Kang KS, Yamabe N, Kim HY. Therapeutic potential of heat-processed Panax ginseng with respect to oxidative tissue damage. Drug Discov Ther 2007;1:30-44.
  3. Kasai R, Besso H, Tanaka O, Saruwatari Y, Fuwa T. Saponins of red ginseng. Chem Pharm Bull 1983;31:2120-2125. https://doi.org/10.1248/cpb.31.2120
  4. Nocerino E, Amato M, Izzo AA. The aphrodisiac and adaptogenic properties of ginseng. Fitoterapia 2000;71 Suppl 1:S1-S5. https://doi.org/10.1016/S0367-326X(00)00170-2
  5. Yun TK. Brief introduction of Panax ginseng C. A. Meyer. J Korean Med Sci 2001;16 Suppl:S3-S5. https://doi.org/10.3346/jkms.2001.16.S.S3
  6. Matsuura H, Hirao Y, Yoshida S, Kunihiro K, Fuwa T, Kasai R, Tanaka O. Study of red ginseng: new glucosides and a note on the occurrence of maltol. Chem Pharm Bull 1984;32:4674-4677. https://doi.org/10.1248/cpb.32.4674
  7. Oh CH, Kang PS, Kim JW, Kwon J, Oh SH. Water extracts of cultured mountain ginseng stimulate immune cells and inhibit cancer cell proliferation. Food Sci Biotechnol 2006;15:369-373.
  8. Jia L, Zhao Y. Current evaluation of the millennium phytomedicine- ginseng (I): etymology, pharmacognosy, phytochemistry, market and regulations. Curr Med Chem 2009;16:2475-2484. https://doi.org/10.2174/092986709788682146
  9. Park JH, Kim JM, Han SB, Kim NY, Surh YJ, Lee SK, Kim ND, Park MK. A new processed ginseng with fortifi ed activity. In: Huh H, Choi KJ, Kim YC, eds. Advances in ginseng research. Seoul: Korean Society of Ginseng, 1998. p.146-159.
  10. 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 2000;63:1702-1704. https://doi.org/10.1021/np990152b
  11. 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 2001; 921:335-339. https://doi.org/10.1016/S0021-9673(01)00869-X
  12. Wijewickreme AN, Krejpcio Z, Kitts DD. Hydroxyl scavenging activity of glucose, fructose, and ribose-lysine model Maillard products. J Food Sci 1999;64:457-461. https://doi.org/10.1111/j.1365-2621.1999.tb15062.x
  13. Bekedam EK, Schols HA, Cammerer B, Kroh LW, van Boekel MA, Smit G. Electron spin resonance (ESR) studies on the formation of roasting-induced antioxidative structures in coffee brews at different degrees of roast. J Agric Food Chem 2008;56:4597-4604. https://doi.org/10.1021/jf8004004
  14. Chen XM, Kitts DD. Antioxidant activity and chemical properties of crude and fractionated Maillard reaction products derived from four sugar-amino acid Maillard reaction model systems. Ann N Y Acad Sci 2008;1126:220-224. https://doi.org/10.1196/annals.1433.028
  15. Wang CZ, Zhang B, Song WX, Wang A, Ni M, Luo X, Aung HH, Xie JT, Tong R, He TC, et al. Steamed American ginseng berry: ginsenoside analyses and anticancer activities. J Agric Food Chem 2006;54:9936-9942. https://doi.org/10.1021/jf062467k
  16. Shoji J. The saponins of ginseng. In: Shibata S, Ohtsuka Y, Sato S, eds. Recent advances in ginseng studies. Tokyo: Hirokawa Publishing, 1990. p.11-31.
  17. Kang KS, Kim HY, Yamabe N, Yokozawa T. Stereospecifi city in hydroxyl radical scavenging activities of four ginsenosides produced by heat processing. Bioorg Med Chem Lett 2006;16:5028-5031. https://doi.org/10.1016/j.bmcl.2006.07.071
  18. Kang KS, Kim HY, Baek SH, Yoo HH, Park JH, Yokozawa T. Study on the hydroxyl radical scavenging activity changes of ginseng and ginsenoside-Rb2 by heat processing. Biol Pharm Bull 2007;30:724-728. https://doi.org/10.1248/bpb.30.724
  19. Kang KS, Yokozawa T, Yamabe N, Kim HY, Park JH. ESR study on the structure and hydroxyl radical-scavenging activity relationships of ginsenosides isolated from Panax ginseng C. A. Meyer. Biol Pharm Bull 2007;30:917-921. https://doi.org/10.1248/bpb.30.917
  20. Lee YJ, Kim HY, Kang KS, Lee JG, Yokozawa T, Park JH. The chemical and hydroxyl radical scavenging activity changes of ginsenoside-Rb1 by heat processing. Bioorg Med Chem Lett 2008;18:4515-4520. https://doi.org/10.1016/j.bmcl.2008.07.056
  21. Kang KS, Lee YJ, Park JH, Yokozawa T. The effects of glycine and L-arginine on heat stability of ginsenoside Rb1. Biol Pharm Bull 2007;30:1975-1978. https://doi.org/10.1248/bpb.30.1975
  22. Oura H, Hiai S, Odaka Y, Yokozawa T. Studies on the biochemical action of ginseng saponin. I. Purification from ginseng extract of the active component stimulating serum protein biosynthesis. J Biochem 1975;77:1057-1065. https://doi.org/10.1093/oxfordjournals.jbchem.a130806
  23. Kayano S, Kikuzaki H, Fukutsuka N, Mitani T, Nakatani N. Antioxidant activity of prune (Prunus domestica L.) constituents and a new synergist. J Agric Food Chem 2002;50:3708-3712. https://doi.org/10.1021/jf0200164
  24. Chiou WF, Jan WC, Chou CJ, Chen CF. Non major ginsenosides contribute to the relaxation of Panax ginseng in rabbit corpus cavernosum. J Chin Med 2000;11:197-204.
  25. Samaras TS, Camburn PA, Chandra SX, Gordon MH, Ames JM. Antioxidant properties of kilned and roasted malts. J Agric Food Chem 2005;53:8068-8074. https://doi.org/10.1021/jf051410f
  26. Hatano T, Edamatsu R, Hiramatsu M, Mori A, Fujita Y, Yasuhara T, Yoshida T, Okuda T. Effects of the interaction of tannins with co-existing substances. VI. Effects of tannins and related polyphenols on superoxide anion radical, and on 1,1-diphenyl-2-picrylhydrazyl radical. Chem Pharm Bull 1989;37:2016-2021. https://doi.org/10.1248/cpb.37.2016
  27. Kang KS, Kim HY, Pyo JS, Yokozawa T. Increase in the free radical scavenging activity of ginseng by heatprocessing. Biol Pharm Bull 2006;29:750-754. https://doi.org/10.1248/bpb.29.750
  28. Li X, Zheng Y, Liu M, Zhang L. A study on maillard reaction and its products during processing of red ginseng. Zhongguo Zhong Yao Za Zhi 1999;24:274-278.
  29. Suzuki Y, Choi KJ, Uchida K, Ko SR, Sohn HJ, Park JD. Arginyl-fructosyl-glucose and arginyl-fructose, compounds related to browning reaction in the model system of steaming and heat-drying processes for the preparation of red ginseng. J Ginseng Res 2004;28:143-148. https://doi.org/10.5142/JGR.2004.28.3.143

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