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Remarkable impact of amino acids on ginsenoside transformation from fresh ginseng to red ginseng

  • Liu, Zhi (College of Chinese Medicinal Materials, Jilin Agricultural University) ;
  • Wen, Xin (College of Chinese Medicinal Materials, Jilin Agricultural University) ;
  • Wang, Chong-Zhi (Tang Center for Herbal Medicine Research and The Pritzker School of Medicine, University of Chicago) ;
  • Li, Wei (College of Chinese Medicinal Materials, Jilin Agricultural University) ;
  • Huang, Wei-Hua (Tang Center for Herbal Medicine Research and The Pritzker School of Medicine, University of Chicago) ;
  • Xia, Juan (College of Chinese Medicinal Materials, Jilin Agricultural University) ;
  • Ruan, Chang-Chun (Institute of Agricultural Modernization, Jilin Agricultural University) ;
  • Yuan, Chun-Su (Tang Center for Herbal Medicine Research and The Pritzker School of Medicine, University of Chicago)
  • Received : 2018.03.27
  • Accepted : 2019.04.05
  • Published : 2020.05.15

Abstract

Background: Amino acids are one of the major constituents in Panax ginseng, including neutral amino acid, acidic amino acid, and basic amino acid. However, whether these amino acids play a role in ginsenoside conversion during the steaming process has not yet been elucidated. Methods: In the present study, to elucidate the role of amino acids in ginsenoside transformation from fresh ginseng to red ginseng, an amino acids impregnation pretreatment was applied during the steaming process at 120℃. Acidic glutamic acid and basic arginine were used for the acid impregnation treatment during the root steaming. The ginsenosides contents, pH, browning intensity, and free amino acids contents in untreated and amino acid-treated P. ginseng samples were determined. Results: After 2 h of steaming, the concentration of less polar ginsenosides in glutamic acid-treated P. ginseng was significantly higher than that in untreated P. ginseng during the steaming process. However, the less polar ginsenosides in arginine-treated P. ginseng increased slightly. Meanwhile, free amino acids contents in fresh P. ginseng, glutamic acid-treated P. ginseng, and arginine-treated P. ginseng significantly decreased during steaming from 0 to 2h. The pH also decreased in P. ginseng samples at high temperatures. The pH decrease in red ginseng was closely related to the decrease in basic amino acids levels during the steaming process. Conclusion: Amino acids can remarkably affect the acidity of P. ginseng sample by altering the pH value. They were the main influential factors for the ginsenoside transformation. These results are useful in elucidating why and how steaming induces the structural change of ginsenoside inP. ginseng and also provides an effective and green approach to regulate the ginsenoside conversion using amino acids during the steaming process.

Keywords

References

  1. Zhao ZZ, Liang ZT, Chan K, Lu GH, Lee ELM, Chen HB, Li L. A unique issue in the standardization of Chinese materia medica: Processing. Planta Med 2010;76:1975-86.
  2. Wang JS, Heijden RVD, Spruit S, Hankermeier T, Chan K, Greef JVD, Xu GW, Wang M. Quality and safety of Chinese herbal medicines guided by a systems biology perspective. J Ethnopharmacol 2009;126:31-41. https://doi.org/10.1016/j.jep.2009.07.040
  3. Liu ZQ. Chemical insights into ginseng as a resource for natural antioxidants. Chem Rev 2012;112:3329-55. https://doi.org/10.1021/cr100174k
  4. Qi LW, Wang CZ, Yuan CS. Ginsenosides from American ginseng: chemical and pharmacological diversity. Phytochemistry 2011;72:689-99. https://doi.org/10.1016/j.phytochem.2011.02.012
  5. Liu Z, Li W, Li X, Zhang M, Chen L, Zheng YN, Sun GZ, Ruan CC. Antidiabetic effects of malonyl ginsenosides from Panax ginseng on type 2 diabetic rats induced by high-fat diet and streptozotocin. J Ethnopharmacol 2013;145:233-40. https://doi.org/10.1016/j.jep.2012.10.058
  6. Kim DY, Park MW, Yuan HD, Lee HJ, Kim SH, Chung SH. Compound K induces apoptosis via CAMK-IV/AMPK pathways in HT-29 colon cancer cells. J Agric Food Chem 2009;57:10573-8.
  7. 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;63:1702-4. https://doi.org/10.1021/np990152b
  8. Nam KY. The comparative understanding between red ginseng and white ginseng, processed ginsengs (Panax ginseng C. A. Meyer). J Ginseng Res 2005;29:1-18. https://doi.org/10.5142/JGR.2005.29.1.001
  9. Xie YY, Luo D, Cheng YJ, Ma JF, Wang YM, Liang QL, Luo GA. Steaminginduced 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
  10. Lee MR, Yun BS, Sung CK. Comparative study of white and steamed black Panax ginseng, P. quinquefolium, and P. notoginseng on cholinesterase inhibitory and antioxidative activity. J Ginseng Res 2012;36:93-101.
  11. Li W, Yan MH, Liu Y, Liu Z, Wang Z, Chen C, Zhang J, Sun YS. Ginsenoside Rg5 ameliorates cisplatin-induced nephrotoxicity in mice through inhibition of inflammation, oxidative stress, and apoptosis. Nutrients 2016;8:566. https://doi.org/10.3390/nu8090566.
  12. Park EH, Kim YJ, Yamabe N, Park SH, Kim HK, Jang HJ, Kim JH, Cheon GJ, Ham J, Kang KS. Stereospecific anticancer effects of ginsenoside Rg3 epimers isolated from heat-processed American ginseng on human gastric cancer cell. J Ginseng Res 2014;38:22-7. https://doi.org/10.1016/j.jgr.2013.11.007
  13. Park EK, Choo MK, Han MJ, Kim DH. Ginsenoside Rh1 possesses antiallergic and anti-inflammatory activities. Int Arch Allergy Immunol 2004;133:113-20. https://doi.org/10.1159/000076383
  14. Qi LW, Wang CZ, Yuan CS. Isolation and analysis of ginseng: advances and challenges. Nat Prod Rep 2011;28:467-95. https://doi.org/10.1039/c0np00057d
  15. Liu Z, Xia J, Wang CZ, Zhang JQ, Ruan CC, Sun GZ, Yuan CS. Remarkable impact of acidic ginsenosides and organic acids on ginsenoside transformation from fresh ginseng go red ginseng. J Agri Food Chem 2016;64:5389-99. https://doi.org/10.1021/acs.jafc.6b00963
  16. Cho EJ, Piao XL, Jang MH, Baek SH, Kim HY, Kang KS, Kwon SW, Park JH. The effect of steaming on the free amino acid contents and antioxidant activity of Panax ginseng. Food Chem 2008;107:876-82. https://doi.org/10.1016/j.foodchem.2007.09.007
  17. Ghafoor K, Kim SO, Lee DU, Seong K, Park J. Effects of high hydrostatic pressure on structure and colour of red ginseng (Panax ginseng). J Sci Food Agric 2012;92:2975-82. https://doi.org/10.1002/jsfa.5710
  18. Naval MV, Gomez-Serranillos MP, Carretero ME, De Arce C. Value of highperformance liquid chromatographic analysis of amino acids in the determination of Panax ginseng radix extract effect in cultured neurons. J Chromatogr A 2006;1121:242-7. https://doi.org/10.1016/j.chroma.2006.04.051
  19. Sun GZ, Li XG, Liu Z, Wang JY, Zheng YN, Yang XW. Isolation and structure characterization of malonyl-notoginsenoside-R4 from the root of Panax ginseng. Chem J Chinese U 2007;28:1316-8.
  20. Ruan CC, Liu Z, Li X, Liu X, Wang LJ, Pan HY, Zheng YN, Sun GZ, Zhang YS, Zhang LX. Isolation and characterization of a new ginsenoside from the fresh root of Panax Ginseng. Molecules 2010;15:2319-25.
  21. Kitts DD, Chen XM, Jing H. Demonstration of antioxidant and anti-inflammatory bioactivities from sugareamino acid Maillard reaction products. J Agric Food Chem 2012;60:6718-27. https://doi.org/10.1021/jf2044636
  22. Yuan H, Sun LJ, Chen M, Wang J. The comparison of the contents of sugar, amadori, and heyns compounds in fresh and black garlic. J Food Sci 2016;81:1662-8.
  23. Khan JK, Kuo YH, Kebede N, Lambein F. Determination of non-protein amino acids and toxins in Lathyrus by high-performance liquid chromatography with precolumn phenyl isothiocyanate derivatization. J Chromatogr A 1994;687:113-9. https://doi.org/10.1016/0021-9673(94)00777-2
  24. Kim JH, Han IH, Yamabe N, Kim YJ, Lee W, Eom DW, Choi P, Cheon GJ, Jang HJ, Kim SN, et al. Renoprotective effects of Maillard reaction products generated during heat treatment of ginsenoside Re with leucine. Food Chem 2014;143:114-21. https://doi.org/10.1016/j.foodchem.2013.07.075
  25. 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;18:4515-20. https://doi.org/10.1016/j.bmcl.2008.07.056
  26. Bae EA, Han MJ, Kim EJ, Kim DH. Transformation of ginseng saponins to ginsenoside Rh2 by acids and human intestinal bacteria and biological activities of their transformants. Arch Pharm Res 2004;27:61-7. https://doi.org/10.1007/BF02980048
  27. Ma LY, Zhou QL, Yang XW. New SIRT1 activator from alkaline hydrolysate of total saponins in the stems-leaves of Panax ginseng. Bioorg Med Chem Lett 2015;25:5321-5. https://doi.org/10.1016/j.bmcl.2015.09.039
  28. Rufian-Henares JA, Morales FJ. Functional properties of melanoidins: in vitro antioxidant, antimicrobial and antihypertensive activities. Food Res Int 2007;40:995-1002.
  29. Zheng YN, Okuda H, Han LK, Xiang L, Matsuura Y, Takaku T, Kameda K. A new amino acid derivative from red ginseng. J Chinese Pharm Sci 1998;7:7-10.
  30. 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;28:143-8. https://doi.org/10.5142/JGR.2004.28.3.143
  31. Kim GN, Lee JS, Song JH, Oh CH, Kwon YI, Jang HD. Heat Processing decreases Amadori products and increases total phenolic content and antioxidant activity of Korean red ginseng. J Med Food 2010;13:1478-84.
  32. Ha KS, Jo SH, Kang BH, Apostolidis E, Lee MS, Jang HD, Kwon YI. In vitro and in vivo antihyperglycemic effect of 2 amadori rearrangement compounds, arginyl- fructose and arginyl-fructosyl-glucose. J Food Sci 2011;76:H188-93. https://doi.org/10.1111/j.1750-3841.2011.02361.x
  33. Choi IS, Cha HS, Lee YS. Physicochemical and antioxidant properties of black garlic. Molecules 2014;19:16811-23. https://doi.org/10.3390/molecules191016811
  34. Liang TF, Wei FF, Lu Y, Kodani Y, Nakada M, Miyakawa T, Tanokura M. Comprehensive NMR analysis of compositional changes of black garlic during thermal processing. J Agric Food Chem 2015;63:683-91. https://doi.org/10.1021/jf504836d
  35. Zhang XY, Li NY, Lu XM, Liu PL, Qiao XG. Effects of temperature on the quality of black garlic. J Sci Food Agric 2016;96:2366-72. https://doi.org/10.1002/jsfa.7351