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Effect of chlorogenic acid on hydroxyl radical

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Abstract

Chlorogenic acid (CGA) is considered to act as an antioxidant. However, the inhibitory effects of CGA on specific radical species are not well understood. Electron spin resonance (ESR) in combination with spin trapping techniques was utilized to detect free radicals. 5,5-Dimethyl-1-pyrroline-N-oxide (DMPO) was used as a spin trapping reagent while the Fenton reaction was used as a source of hydroxyl radical (·OH). We found that CGA scavenges ·OH in a dose-dependent manner. The kinetic parameters, IC50 and Vmax, for CGA scavenging of ·OH were 110 and 1.27 μM/sec, respectively. The rate constant for the scavenging of ·OH by CGA was 7.73 × 109 M−1 sec−1. Our studies suggest that the antioxidant properties of CGA may involve a direct scavenging effect of CGA on ·OH.

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References

  1. Matheis G, Belitz HD: [Studies on enzymic browning of potatoes (Solanum tuberosum). II. The quantitative relationship between browning and its causative factors] (author's translation). Z Lebensm Unters Forsch 163: 186-190, 1977

    Google Scholar 

  2. Kichne A, Engelhardt UH: Thermospray-LC-MS analysis of various groups of polyphenols in tea. II: Chlorogenic acids, theaflavins and thearubigins. Z Lebensm Unters. Forsch 202: 299-302, 1996

    Google Scholar 

  3. Escarpa A, Gonzalez MC: High-performance liquid chromatography with diode-array detection for the determination of phenolic compounds in peel and pulp from different apple varieties. J Chromatogr A 823: 331-337, 1998

    Google Scholar 

  4. Obermeyer WR, Musser SM, Betz JM, Casey RE, Pohland AE, Page SW: Chemical studies of phytoestrogens and related compounds in dietary supplements: flax and CGA. PSEBM 208: 6-12, 1995

    Google Scholar 

  5. Jung HA, Park JC, Chung HY, Kim J, Choi JS: Antioxidant flavonoids and chlorogenic acid from the leaves of Eriobotrya japonica. Arch Pharm Res 22: 213-218, 1999

    Google Scholar 

  6. Yoshino M, Murakami K: Interaction of iron with polyphenolic compounds: Application to antioxidant characterization. Anal Biochem 257: 40-44, 1998

    Google Scholar 

  7. Iwahashi H, Ishii T, Sugata R, Kido R: The effects of caffeic acid and its related catechols on hydroxyl radical formation by 3-hydroxy-anthranilic acid, ferric chloride, and hydrogen peroxide. Arch Biochem Biophys 276: 242-247, 1990

    Google Scholar 

  8. Challis BC, Bartlett CD: Possible cocarcinogenic effects of coffee constituents. Nature 254: 532-533, 1975

    Google Scholar 

  9. Paganga G, Miller N, Rice-Evans CA: The polyphenolic content of fruit and vegetables and their antioxidant activities. What does a serving constitute? Free Radic Res 30: 153-162, 1999

    Google Scholar 

  10. Tsuchiya T, Suzuki O, Igarashi K: Protective effects of chlorogenic acid on paraquat-induced oxidative stress in rats. Biosci Biotechnol Biochem 60: 765-768, 1996

    Google Scholar 

  11. Kono Y, Kobayashi K, Tagawa S, Adachi K, Ueda A, Sawa Y, Shibata H: Antioxidant activity of polyphenolics in diets. Rate constants of reactions of chlorogenic acid and caffeic acid with reactive species of oxygen and nitrogen. Biochim Biophys Acta 1335: 335-342, 1997

    Google Scholar 

  12. Iwahashi H, Morishita H, Ishii T, Sugata R, Kido R: Enhancement by catechols of hydroxyl-radical formation in the presence of ferric ions and hydrogen peroxide. J Biochem 105: 429-434, 1989

    Google Scholar 

  13. Fenton HJH: LXXIIL — Oxidation of tartaric acid in presence of iron. J Am Chem Soc 65: 899-910, 1894

    Google Scholar 

  14. Harbour JR, Hair ML: Detection of superoxide ions in nonaqueous media. Generation by photolysis of pigment dispersions. J Phys Chem 82: 1397-1399, 1978

    Google Scholar 

  15. Zang LY, Misra HP: Generation of reactive oxygen species during the monoamine oxidase — catalyzed oxidation of the neurotoxicant, 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. J Biol Chem 268: 16504-16512, 1993

    Google Scholar 

  16. Zang LY, Stone K, Pryor WA: Detection of free radicals in aqueous extracts of cigarette tar by electron spin resonance. Free Radic Biol Med 19: 161-167, 1995

    Google Scholar 

  17. Finkelstein E, Rosen GM, Anggard E: Spin trapping, kinetics of the reaction of superoxide and hydroxyl radicals with nitrones. J Am Chem Soc 102: 4994-4999, 1980

    Google Scholar 

  18. Buettner GR, Motten AG, Hall RD, Chignell CF: Free radical production by chlorpromazine sulfoxide, an ESR spin-trapping and flash photolysis study. Photochem Photobiol 44: 5-10, 1986

    Google Scholar 

  19. Foote CS, Ching TY: Chemistry of singlet oxygen. XXI. Kinetics of bilirubin photooxygenation. J Am Chem 97: 6209-6214, 1975

    Google Scholar 

  20. Zang LY, van Kuijk FJ, Misra BR, Misra HP: The specificity and product of quenching singlet oxygen by 2,2,6,6-tetramethylpiperidine. Biochem Mol Biol Int 37: 283-293, 1995

    Google Scholar 

  21. Kono Y, Kashine S, Yoneyama T, Sakamoto Y, Matsui Y, Shibata H: Iron chelation by chlorogenic acid as a natural antioxidant. Biosci Biotechnol Biochem 62: 22-27, 1998

    Google Scholar 

  22. Halliwell B, Aruoma OI: DNA damage by oxygen-derived species. Its mechanism and measurement in mammalian systems. FEBS Lett 281: 9-19, 1991

    Google Scholar 

  23. Wiseman H, Halliwell B: Damage to DNA by reactive oxygen and nitrogen species: Role in inflammatory disease and progression to cancer. Biochem J 313: 17-29, 1996

    Google Scholar 

  24. Halliwell B, Gutteridge JM: The antioxidants of human extracellular fluids. Arch Biochem Biophys 280: 1-8, 1990

    Google Scholar 

  25. Zang LY, Misra BR, Misra HP: Generation of free radicals during photosensitization of hypocrellin A and their effects on cardiac membranes. Photochem Photobiol 56: 453-462, 1992

    Google Scholar 

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Zhang, LY., Cosma, G., Gardner, H. et al. Effect of chlorogenic acid on hydroxyl radical. Mol Cell Biochem 247, 205–210 (2003). https://doi.org/10.1023/A:1024103428348

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