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Kinetic study of radical scavenging activity of phenolic antioxidants

Research Project

Project/Area Number 14571859
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 補綴理工系歯学
Research InstitutionMeikai University

Principal Investigator

FUJISAWA Seiichiro  Meikai University, School of Dentistry, Professor, 歯学部, 教授 (40014162)

Co-Investigator(Kenkyū-buntansha) ATSUMI Toshiko  Meikai University, School of Dentistry, Associate Professor, 歯学部, 助教授 (60049385)
ISHIHARA Mariko  Meikai University, School of Dentistry, Lecture, 歯学部, 講師 (50095329)
KADOMA Yoshinori  Tokyo Medical & Dental University, Institute of Biomaterials and Bioengeneering, Associate Professor, 生体材料工学研究所, 助教授 (00092403)
Project Period (FY) 2002 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,900,000)
Fiscal Year 2004: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2003: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 2002: ¥1,800,000 (Direct Cost: ¥1,800,000)
Keywordsmonophenols / polyphenols / thiol / induction period / antioxidant-activity / PM III calculation / radical species / bond-dissociation energy / monophenol / alkyl radical / peroxy radical / PM 3 calculation / t-butyl-alkyl phenol / 過酸化ベンゾイル / アゾビスイソブチロニトリル / MMAラジカル重合 / Stoichiometric factor / inhibition rate constant / quinone / 半経験的分子軌道法 / フェノール / ポリフェノール / 過酸化ベンゾイルラジカル / ラジカル捕捉 / stoichiometric factor / HOMO / SOMO / 半経験的分子規道法
Research Abstract

Phenolic compounds show anti-inflammatory and anticancer activity. These compounds act as non-steroidal anti-inflammatory drugs (NSAI Ds), possibly due to the high antioxidant activity. To clarify the radical scavenging activity of phenolic compounds, in the present study, we investigate their radical scavenging activity using the induction period (IP) method in the polymerization of methyl methacrylate (MMA) initiated from azobisisobutyronitrile (AIBN) and benzoyl peroxide (BPO). Polymerization of MMA was performed using a differential scanning calorimetry (DSC) at 70℃. Time-exotherm curves were used to determine time-conversion curves, and IP, initial rate of polymerization of control and antioxidants (Rp_<con> and Rp_<inh>) were determined. Since glutathione, a thiol is a potent antioxidant, synergistic interactions between mcrcapto-1-methylimidazole (MMI) and phenolic compounds were investigated. The combination of catecin and MMI significantly reduced IP values than catechin or MM … More I alone, suggesting an oxygen uptake, because a mall quantity of molecular oxygen contained in the present system. Resveratrol and curcumin were similar oxygen uptake. In contrast, the combination of eugenol and MMI increased IP values, suggesting the formation of new antioxidant product, possibly due to the Michael reaction between two compounds. Oxygen uptake of polyphenols in the presence of thiols suggested events of the formation of reactive oxygen species (ROS) in biological systems. Radical scavenging activities of phenolic compounds are connected with the bond dissociation energy (BDE) of phenol O-H-group. We calculated BDE using the PM3 semiempirical method. The radical scavenging activity was correlated with the BDE. The interaction of polyphenols with AIBN radicals (alkyl radicals) was different from that with BPO radicals (peroxy radicals). Also, we investigated the interaction quinone compounds with radical species, indicating that quinone compounds suppress the growing MMA radical, although their IP was small. Less

Report

(4 results)
  • 2004 Annual Research Report   Final Research Report Summary
  • 2003 Annual Research Report
  • 2002 Annual Research Report

Research Products

(29 results)

All 2005 2004 Other

All Journal Article (18 results) Publications (11 results)

  • [Journal Article] Dimerization, ROS formation, and biological activity of o-methoxyphenols2005

    • Author(s)
      Fujisawa S, Atsumi T, Murakami Y, Kadoma Y
    • Journal Title

      Arch Immunol Ther Exp 53

      Pages: 28-38

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Dimerization, ROS formationan and Biological activity of o-methoxyphenol2005

    • Author(s)
      Fujisawa S, Atsumi T, Kadoma
    • Journal Title

      Arch Immunol Ther Exp 53

      Pages: 23-38

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Dehydrodiisoeugenol, anisoeugenoldimer, inhibitslipopolysaccharide-stimulatednuclearfactorkappaBactivationandcyclooxygenase-2expressioninmacrophageson2005

    • Author(s)
      MurakamiY, ShojiM, HirataA, TANAKAS, YokoeIanfFujisawaS
    • Journal Title

      ArchBiochemBiophys 434

      Pages: 326-332

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Radical scavenging activity of butylated hydroxytoluene (BHT) and its methabolites2004

    • Author(s)
      Fujisawa S, Kadoma Y, Yokoe I
    • Journal Title

      Chem Phys Lipid 130

      Pages: 189-195

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Kinetic studies of the radical-scavenging activity of estrogens and antiestrogens2004

    • Author(s)
      Fujisawa S, Kadoma Y
    • Journal Title

      Anticancer Res 24

      Pages: 3931-3938

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Kinetics of the radical scavenging activity of-beta-carotene-related compounds2004

    • Author(s)
      Fujisawa S, Ishikawa M, Kadoma Y
    • Journal Title

      SAR, QSAR.Environ Res 15

      Pages: 33-41

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Cytotoxicity, ROS-generationactivity and radical-scavenging activity of curcumin and related compounds2004

    • Author(s)
      Fujisawa S, Atsumi T, Ishihara M, Kadoma Y
    • Journal Title

      Anticancer Res 24

      Pages: 563-570

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Kinetic radical scavenging activity and cytotoxicity of 2-methoxy-and 2-t-butyl-substituted phenols and their dimers.2004

    • Author(s)
      Fujisawa S, Atsumi T, Kadoma Y, Ishihara M, Ito S, Yokoe I
    • Journal Title

      Anticancer Res 24

      Pages: 3019-3026

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Kinetic studies of the radical-scavenging activity of Estrogen and antiestrogen2004

    • Author(s)
      Fujisawa S, Kadoma Y
    • Journal Title

      Anticancer Res 24

      Pages: 3931-3938

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Kinetics of the radical scavenging activity of eta-carotene-related compounds2004

    • Author(s)
      Fujisawa S, Ishihara M, kadoma Y
    • Journal Title

      QSAR, SAR. Environ Res 15

      Pages: 33-41

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Cytotoxicity, ROS-generation and radical-scavengingactivity Ofcurcuminabdrelated compounds2004

    • Author(s)
      Fujisawa S, Atsumi T, Ishihara M, kadoma Y
    • Journal Title

      Anticancer Res 24

      Pages: 563-570

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Kinetic radical scavenging activity and cytotoxicity of 2-methoxy-and2-t-butyl-substituted Phenolsandtheirdimers2004

    • Author(s)
      Fujisawa S, Atsumi T, Kadoma Y, Ishihara M, Ito S, Yokoe I
    • Journal Title

      Anticancer Res 24

      Pages: 3019-3026

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Radical scavenging activity of butylated hydroxytoluene(BHT) and its metabolites2004

    • Author(s)
      Fujisawa S, Kadoma Y, Yokoe I
    • Journal Title

      Chem phys Lipid 130

      Pages: 189-195

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Comparativeradicalproductionandcytotoxicityinducedbycamphorquinone and 9-fluorenoneagainsthumanpulpfibroblast2004

    • Author(s)
      AtsumiT, IshiharaM, KadomaY, TonosakiK, FujisawaS
    • Journal Title

      J Oral Rehab 31

      Pages: 1115-1164

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Dipalmitoylphosphatidylcholine (DPPC) andDPPC/Cholesterolliposomesa spredictorsofthecytotoxicityofbis-GMArelatedcompounds2004

    • Author(s)
      FujisawaS, Atsumit, KadomaY, Ishihara M, YokoeI
    • Journal Title

      JliposomeRes 14・1

      Pages: 39-49

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Cytotoxicity, ROS-generation activityandradical-scavengingactivityofcurcuminandrelatedcompounds2004

    • Author(s)
      FujisawaS, AtsumiT, Ishiharam, KadomaY
    • Journal Title

      AnticancerRes 24

      Pages: 563-570

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Kineticradicalscavengingactivityandcytotoxicityof2-methoxy-and2- substitutedt-butylphenolsandtheirdimers2004

    • Author(s)
      FujisawaS, AtsumiT, KadomaY, Ishiharam, ItoS, YokoeI
    • Journal Title

      AnticancerRes 24

      Pages: 3019-3026

    • Related Report
      2004 Annual Research Report
  • [Journal Article] CytotoxicityofA4-META/MMA-TBBOresinagainsthumanpulpfibroblast2004

    • Author(s)
      FujisawaS, AtsumiT
    • Journal Title

      DentMaterJ 23・2

      Pages: 106-108

    • Related Report
      2004 Annual Research Report
  • [Publications] Saito, M., Sakagami, H., Fujisawa, S.: "Cytotoxicity and apoptosis induction by butylated hydroxyanisole (BHA) and butylate hydroxyroluene (BHT)"Anticancer Res. 23. 4673-4702 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Fujisawa, S., Ishihara, M., Kadoma, Y.: "Kinetics of the radical scavenging activity of b-carotene-related compounds"SAR.QSAR.Environ Res. 15. 33-41 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Fujisawa S, 5番目: "Preventive effect of bis-eugenol, a eugenol orthodimer, on lipopolysaccharide-stimulated nuclear factor kappa B activation and inflammatory cytokine expression in macrophages"Biochem Pharmacology. 66. 1061-1066 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] 藤沢盛一郎, 熱海智子, 門磨義則: "レジン重合開始剤の特性-diphenylpicrylhydrazyl, galvinoxyl method"歯科材料・器械 Special Issue. 22. 129 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] 藤沢盛一郎, 熱海智子, 門磨義則: "Camphorquinoneの光酸化作用"歯科材料・器械 Special Issue. 22. 350 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Ogiwara T. et al.: "Radical scavenging activity and cytotoxicity of ferulic acid"Anticancer Res.. 22. 2711-2718 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Fujisawa S, Ishihara M, Kadoma Y.: "Kinetics evaluation of the reactivity of flavonoids as radical scavengers"SAR, QSAR Environ Res.. 13. 617-627 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Fujisawa S. et al.: "Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity"Toxicology. 177. 39-54 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Fujisawa S. et al.: "Interaction between 2-ethoxybenzoic acid (EBA) and eugenol and related cytotoxicity"J Dent Res.. 82. 43-47 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] 藤沢盛一郎, 他2名: "Eugenol関連化合物のstoichiometric factorと細胞毒性の関係"歯科材料・器械. 21(39). 86 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 藤沢盛一郎, 他2名: "Camphorguinoneの光酸化作用"歯科材料・器械. 21(40). 19 (2002)

    • Related Report
      2002 Annual Research Report

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Published: 2002-03-31   Modified: 2016-04-21  

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