In vitro and Cellular Antioxidant Activity of Arginyl-fructose and Arginyl-fructosyl-glucose

  • 발행 : 2009.12.31


Arginyl-fructose (AF) and arginyl-fructosyl-glucose (AFG) were chemically synthesized and purified. Their in vitro and cellular antioxidant activity was investigated using oxygen radical absorbance capacity (ORAC) and cellular antioxidant activity assay, respectively. The peroxyl radical scavenging activity of AF was much higher than that of AFG, which was in good agreement with their reduction capacity to donate electrons or hydrogen atoms. On the other hand, the hydroxyl radical scavenging activity of AF was weaker than that of AFG, which was consistent with their metal chelating activity, suggesting that AFG-$Cu^{2+}$ complex may be less redox-active than AF-$Cu^{2+}$ complex due to 1 glucose molecule attached. The cellular antioxidant activity of AF and AFG appeared to depend on both their permeability into cell membrane and the scavenging activity on peroxyl or hydroxyl radicals. These results indicate that AF and AFG, Maillard reaction products, may have a high potential as a material for the development of nutraceutical food with antioxidant activity.



  1. Halliwell B, Aeschbach R, Loliger J, Aruoma OI. The characterization of antioxidants. Food Chem. Toxicol. 33: 601-617 (1995)
  2. Droge W. Free radicals in the physiological control of cell function. Physiol. Rev. 82: 47-95 (2001)
  3. Pieta PG. Flavonoid as antioxidants. J. Nat. Prod. 63: 1035-1042 (2000)
  4. Moure A, Cruz JM, Franco D, Domingues JM, Sineiro J, Domingues H, Nunez MJ, Parajo JC. Natural antioxidants from residual sources. Food Chem. 72: 145-171 (2001)
  5. Matsuura Y, Zheng Y, Takaku T, Kameda K, Okuda H. Isolation and physiological activities of a new amino acid derivative from Korean red ginseng. Korean J. Ginseng Sci. 18: 204-211 (1994)
  6. Suzuki Y, Choi KJ, Uchida K, Ko SR, Sohn HJ, Park JD. Arginylfructosyl-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. 28: 143-148 (2004)
  7. 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. 107: 876-882 (2008)
  8. Keum YS, Park KK, Lee JM, Chun KS, Park HP, Lee SK, Kwon HJ, Surh YJ. Antioxidant and anti-tumor promoting activities of the methanol extract of heat-processed ginseng. Cancer Lett. 150: 41-48 (2000)
  9. Yoo BC, Park GH, Okuda H, Kim S, Hwang WI. Inhibitory effect of arginine-derivatives from ginseng extract and basic amino acids on protein-arginine N-methyltransferase. Amino Acids 17: 391-400 (1999)
  10. Joo KM, Park CW, Jeong HJ, Lee SJ, Chang IS. Simultaneous determination of two Amadori compounds in Korean red ginseng (Panax ginseng) extracts and rat plasma by high-performance anion-exchange chromatography with pulsed amperometric detection. J. Chromatogr. B 865: 159-166 (2008)
  11. Kurihara H, Fukami H, Asami S, Totoda Y, Nakai M, Shibata H, Yao XS. Effects of oolong tea on plasma antioxidative capacity in mice loaded with restraint stress assessed using the oxygen radical absorbance capacity (ORAC) assay. Biol. Pharm. Bull. 27: 1093-1098 (2004)
  12. Cao G, Sofic E, Prior RL. Antioxidant and prooxidant behavior of flavonoids: Structure-activity relationships. Free Radical Bio. Med. 22: 749-760 (1997)
  13. Aruoma OI, Murcia A, Butler J, Halliwell B. Evaluation of the antioxidant and prooxidant action of gallic acid and its derivatives. J. Agr. Food Chem. 41: 1880-1885 (1993)
  14. Argirova AD, Ortwerth BJ. Activation of protein-bound copper ions during early glycation: Study on two proteins. Arch. Biochem. Biophys. 420: 176-184 (2003)
  15. Lautraite S, Bigot-Lasserre D, Bars R, Carmichael N. Optimization of cell-based assays for medium through screening of oxidative stress. Toxicol. In Vitro 17: 207-220 (2003)
  16. Tenopoulou M, Kurz T, Doulias PT, Galaris D, Brunk UT. Does the Calcein-AM method assay the total cellular 'labile iron pool' or only a fraction of it? Biochem. J. 403: 261-266 (2007)
  17. Cao G, Alessio HM, Cutler R. Oxygen-radical absorbance capacity assay for antioxidants. Free Radical Bio. Med. 14: 303-311 (1993)
  18. Prior R, Hoang H, Gu L, Wu X, Bacchiocca M, Howard L, Hampsci-Woodill M, Huang D, Ou B, Jacob R. Assays for hydrophilic and lipophilic antioxidant capacity (oxygen radical absorbance capacity (ORACFL) of plasma and other biological and food samples. J. Agr. Food Chem. 51: 3273-3279 (2003)
  19. Wu X, Beecher GR, Holden JM, Haytowitz DB, Gebhardt SE, Prior RL. Lipophilic and hydrophilic capacities of common foods in the United States. J. Agr. Food Chem. 52: 4026-4037 (2004)
  20. Nam KY. The comparative understanding between red ginseng and white ginsengs, processed ginsengs (Panax ginseng C.A. Meyer). J. Ginseng Res. 29: 1-18 (2005)
  21. Kang KS, Kim HY, Pyo JS, Yokozawa T. Increase in the free radical scavenging activity of ginseng by heat-processing. Biol. Pharm. Bull. 29: 750-754 (2006)
  22. Kim YK, Guo Q, Packer L. Free radical scavenging activity of red ginseng aqueous extracts. Toxicology 172: 149-156 (2002)
  23. Hollman PCH, van Trijp JMP, Buysman MNCP, Gaag MSvd, Mengelers MJB, de Vries JHM, Katan MB. Relative bioavailability of the antioxidant flavonoid quercetin from various foods in man. FEBS Lett. 418: 152-156 (1997)
  24. Morand C, Manach C, Crespy V, Remesy C. Respective bioavailability of quercetin aglycone and its glycosides in a rat model. Biofactors 12: 169-174 (2000)