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Volumn 21, Issue 8, 2012, Pages 1905-1911

Synthesis of N-hydroxycinnamoyl amino acid ester analogues and their free radical scavenging and antioxidative activities

Author keywords

Amide; Amino acid; Antioxidant; DPPH; Haemolysis; Hydroxycinnamic acid

Indexed keywords

AMINO ACID DERIVATIVE; ANTIOXIDANT; ASCORBIC ACID; CAFFEIC ACID; ETHYL CAFFEATE; ETHYL FERULATE; ETHYL N [3 (3,4 DIHYDROXYPHENYL) 1 OXO 2 PROPEN 1 YL] PHENYLALANINATE; ETHYL N [3 (3,4 DIHYDROXYPHENYL) 1 OXO 2 PROPENY YL]GLYCINATE; ETHYL N [3 (4 HYDROXY 3 METHOXYPHENYL) 1 OXO 2 PROPEN 1 YL] GLYCINATE; ETHYL N [3 (4 HYDROXY 3 METHOXYPHENYL) 1 OXO 2 PROPEN 1 YL] PHENYLALANINATE; ETHYL N [3 (4 HYDROXY 3 METHOXYPHENYL) 1 OXO 2 PROPEN 1 YL] VALINATE; ETHYL N [3 (4 HYDROXYPHENYL) 1 OXO 2 PROPEN 1 YL] GLYCINATE; ETHYL N [3 (4 HYDROXYPHENYL) 1 OXO 2 PROPEN 1 YL] PHENYLALANINATE; FERULIC ACID; METHYL N [3 (4 HYDROXYPHENYL) 1 OXO 2 PROPEN 1 YL] TYROSINATE; N HYDROXYCINNAMOYL AMINO ACID ESTER DERIVATIVE; PARA COUMARIC ACID ETHYL ESTER; SCAVENGER; UNCLASSIFIED DRUG;

EID: 84866137236     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9713-2     Document Type: Article
Times cited : (15)

References (27)
  • 1
    • 0034898105 scopus 로고    scopus 로고
    • Green tea catechins partially protect DNA from •oH radical-induced strand breaks and base damage through fast chemical repair of DNA radicals
    • Anderson RF, Fisher LJ, Hara Y, Harris T, Mak B, Melton LD, Packer JE (2001) Green tea catechins partially protect DNA from •OH radical-induced strand breaks and base damage through fast chemical repair of DNA radicals. Carcinogenesis 22:1189-1193
    • (2001) Carcinogenesis , vol.22 , pp. 1189-1193
    • Anderson, R.F.1    Fisher, L.J.2    Hara, Y.3    Harris, T.4    Mak, B.5    Melton, L.D.6    Packer, J.E.7
  • 2
    • 4344692590 scopus 로고    scopus 로고
    • Conformational analysis: A tool for the elucidation of the antioxidant properties of ferulic acid derivatives in membrane models
    • Anselmi C, Centini M, Andreassi M, Buonocore A, Rosa CL, Facino RM, Sega A, Tsuno F (2004) Conformational analysis: a tool for the elucidation of the antioxidant properties of ferulic acid derivatives in membrane models. J Pharm Biomed Anal 35:1241-1249
    • (2004) J Pharm Biomed Anal , vol.35 , pp. 1241-1249
    • Anselmi, C.1    Centini, M.2    Andreassi, M.3    Buonocore, A.4    Rosa, C.L.5    Facino, R.M.6    Sega, A.7    Tsuno, F.8
  • 3
    • 33646595370 scopus 로고    scopus 로고
    • Design, synthesis, and biological evaluation of chicoric acid analogs as inhibitors of HIV-1 integrase
    • Charvat T, Lee DJ, Robinson WE (2006) Design, synthesis, and biological evaluation of chicoric acid analogs as inhibitors of HIV-1 integrase. Bioorg Med Chem 14:4552-4567
    • (2006) Bioorg Med Chem , vol.14 , pp. 4552-4567
    • Charvat, T.1    Lee, D.J.2    Robinson, W.E.3
  • 4
    • 33646812939 scopus 로고    scopus 로고
    • Structure-activity relationship studies of resveratrol and its analogues by the reaction kinetics of low density lipoprotein peroxidation
    • Cheng JC, Fang JG, Chen WF, Zhou B, Yang L, Liu ZL (2006) Structure-activity relationship studies of resveratrol and its analogues by the reaction kinetics of low density lipoprotein peroxidation. Bioorg Chem 34:142-157
    • (2006) Bioorg Chem , vol.34 , pp. 142-157
    • Cheng, J.C.1    Fang, J.G.2    Chen, W.F.3    Zhou, B.4    Yang, L.5    Liu, Z.L.6
  • 5
    • 0035137858 scopus 로고    scopus 로고
    • Kinetic solvent effects on phenolic antioxidant determined by spectrophotometric measurements
    • Foti M, Ruberto G (2001) Kinetic solvent effects on phenolic antioxidant determined by spectrophotometric measurements. J Agric Food Chem 49:342-348
    • (2001) J Agric Food Chem , vol.49 , pp. 342-348
    • Foti, M.1    Ruberto, G.2
  • 6
    • 0037471582 scopus 로고    scopus 로고
    • Quantitative kinetic analysis of hydrogen transfer reactions from dietary polyphenols to the DPPH radical
    • Goupy P, Dufour C, Loonis M, Dangles O (2003) Quantitative kinetic analysis of hydrogen transfer reactions from dietary polyphenols to the DPPH radical. J Agric Food Chem 51:615-622
    • (2003) J Agric Food Chem , vol.51 , pp. 615-622
    • Goupy, P.1    Dufour, C.2    Loonis, M.3    Dangles, O.4
  • 7
    • 57749084378 scopus 로고    scopus 로고
    • Synthesis of tyrosinase inhibitory (4-oxo-4H-yran-2-yl)acrylic acidester derivatives
    • Kang SS, Kim HJ, Jin C, Lee YS (2009) Synthesis of tyrosinase inhibitory (4-oxo-4H-yran-2-yl)acrylic acidester derivatives. Bioorg Med Chem Lett 19:188-191
    • (2009) Bioorg Med Chem Lett , vol.19 , pp. 188-191
    • Kang, S.S.1    Kim, H.J.2    Jin, C.3    Lee, Y.S.4
  • 9
    • 0032522304 scopus 로고    scopus 로고
    • Electron transport-linked ubiquinonedependent recycling of a-tocopherol inhibits autooxidation of mitochondrial membranes
    • Lass A, Sohal RS (1998) Electron transport-linked ubiquinonedependent recycling of a-tocopherol inhibits autooxidation of mitochondrial membranes. Arch Biochem Biophys 352:229-236
    • (1998) Arch Biochem Biophys , vol.352 , pp. 229-236
    • Lass, A.1    Sohal, R.S.2
  • 11
    • 8544221890 scopus 로고    scopus 로고
    • Synthesis of cinnamic acid derivatives and their inhibitory effects on LDL-oxidation, acyl-CoA: Cholesterol acyltransferase-1 and-2 activity, and decrease of HDL-article size
    • Lee S, Han JM, Kim H, Kim E, Jeong TS, Lee WS, Cho KH (2004) Synthesis of cinnamic acid derivatives and their inhibitory effects on LDL-oxidation, acyl-CoA: cholesterol acyltransferase-1 and-2 activity, and decrease of HDL-article size. Bioorg Med Chem Lett 14:4677-4681
    • (2004) Bioorg Med Chem Lett , vol.14 , pp. 4677-4681
    • Lee, S.1    Han, J.M.2    Kim, H.3    Kim, E.4    Jeong, T.S.5    Lee, W.S.6    Cho, K.H.7
  • 12
    • 0037039923 scopus 로고    scopus 로고
    • Bond dissociation enthalpies of polyphenols: The importance of cooperative effects
    • Lucarini M, Mugnaini V, Pedulli GF (2002) Bond dissociation enthalpies of polyphenols: the importance of cooperative effects. J Org Chem 67:928-931
    • (2002) J Org Chem , vol.67 , pp. 928-931
    • Lucarini, M.1    Mugnaini, V.2    Pedulli, G.F.3
  • 13
    • 4644257234 scopus 로고    scopus 로고
    • Esters, amides and substituted derivatives of cinnamic acid: Synthesis, antimicrobial activity and QSAR investigations
    • Narasimhan B, Belsare D, Pharande D, Mourya V, Dhake A (2004) Esters, amides and substituted derivatives of cinnamic acid: synthesis, antimicrobial activity and QSAR investigations. Eur J Med Chem 39:827-834
    • (2004) Eur J Med Chem , vol.39 , pp. 827-834
    • Narasimhan, B.1    Belsare, D.2    Pharande, D.3    Mourya, V.4    Dhake, A.5
  • 14
    • 0025082043 scopus 로고
    • Free radical initiators as source of water-or lipidsoluble peroxyl radicals
    • Niki E (1990) Free radical initiators as source of water-or lipidsoluble peroxyl radicals. Methods Enzymol 186:100-108
    • (1990) Methods Enzymol , vol.186 , pp. 100-108
    • Niki, E.1
  • 15
    • 0035819323 scopus 로고    scopus 로고
    • Asymmetric biomimetic oxidations of phenols: The mechanism of the diastereo-and enantioselective synthesis of dehydrodiconiferyl ferulate (DDF) and dehydrodiconiferyl alcohol (DDA)
    • Orlandi M, Rindone B, Molteni G, Rummakko P, Brunow G (2001) Asymmetric biomimetic oxidations of phenols: the mechanism of the diastereo-and enantioselective synthesis of dehydrodiconiferyl ferulate (DDF) and dehydrodiconiferyl alcohol (DDA). Tetrahedron 57:371-378
    • (2001) Tetrahedron , vol.57 , pp. 371-378
    • Orlandi, M.1    Rindone, B.2    Molteni, G.3    Rummakko, P.4    Brunow, G.5
  • 16
    • 0029888128 scopus 로고    scopus 로고
    • Structure antioxidant activity relationships of flavonoids and phenolic acids
    • Rice-Evans CA, Miller NJ, Paganga G (1996) Structure antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Biol Med 20:933-956
    • (1996) Free Radical Biol Med , vol.20 , pp. 933-956
    • Rice-Evans, C.A.1    Miller, N.J.2    Paganga, G.3
  • 17
    • 0038408778 scopus 로고    scopus 로고
    • Phenolic acids in foods: An overview of analytical methodology
    • Robbins RJ (2003) Phenolic acids in foods: an overview of analytical methodology. J Agric Food Chem 51:2866-2887
    • (2003) J Agric Food Chem , vol.51 , pp. 2866-2887
    • Robbins, R.J.1
  • 18
    • 0033863355 scopus 로고    scopus 로고
    • Dietary intake and bioavailability of polyphenols
    • Scalbert A, Williamson G (2000) Dietary intake and bioavailability of polyphenols. J Nutr 130:2073S-2085S
    • (2000) J Nutr , vol.130
    • Scalbert, A.1    Williamson, G.2
  • 19
    • 0000048910 scopus 로고
    • The occurrence and possible function of hydroxycinnamoyl acid amides in plants
    • Tanguy JM (1985) The occurrence and possible function of hydroxycinnamoyl acid amides in plants. Plant Growth Regul 3:381-399
    • (1985) Plant Growth Regul , vol.3 , pp. 381-399
    • Tanguy, J.M.1
  • 20
    • 0001684682 scopus 로고
    • The distribution of hydroxycinnamic acid amides in flowering plants
    • Tanguy JM, Cabanne F, Pedrizet E, Martin C (1978) The distribution of hydroxycinnamic acid amides in flowering plants. Phytochemistry 17:1927-1928
    • (1978) Phytochemistry , vol.17 , pp. 1927-1928
    • Tanguy, J.M.1    Cabanne, F.2    Pedrizet, E.3    Martin, C.4
  • 23
    • 29044433921 scopus 로고    scopus 로고
    • Inhibition of lipid peroxidation and protein oxidation in rat liver mitochondria by curcumin and its analogues
    • Wei QY, Chen WF, Zhou B, Yang L, Liu ZL (2006a) Inhibition of lipid peroxidation and protein oxidation in rat liver mitochondria by curcumin and its analogues. Biochim Biophys Acta 1760: 70-77
    • (2006) Biochim Biophys Acta , vol.1760 , pp. 70-77
    • Wei, Q.Y.1    Chen, W.F.2    Zhou, B.3    Yang, L.4    Liu, Z.L.5
  • 24
    • 27144549217 scopus 로고    scopus 로고
    • Synergistic effect of green tea polyphenols with trolox on free radical-induced oxidative DNA damage
    • Wei QY, Zhou B, Cai YJ, Yang L, Liu ZL (2006b) Synergistic effect of green tea polyphenols with trolox on free radical-induced oxidative DNA damage. Food Chem 96:90-95
    • (2006) Food Chem , vol.96 , pp. 90-95
    • Wei, Q.Y.1    Zhou, B.2    Cai, Y.J.3    Yang, L.4    Liu, Z.L.5
  • 25
    • 0035857407 scopus 로고    scopus 로고
    • Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidant
    • Wright JS, Johnson ER, Dilabio GA (2001) Predicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effects, and application to major families of antioxidant. J Am Chem Soc 123:1173-1183
    • (2001) J Am Chem Soc , vol.123 , pp. 1173-1183
    • Wright, J.S.1    Johnson, E.R.2    Dilabio, G.A.3
  • 26
    • 57749116991 scopus 로고    scopus 로고
    • Synthesis and evaluation of a novel series of pseudo-cinnamic derivatives as antituberculosis agents
    • Yoya GK, Belval FB, Constant P, Duran H, Daffe M, Baltas M (2009) Synthesis and evaluation of a novel series of pseudo-cinnamic derivatives as antituberculosis agents. Bioorg Med Chem Lett 19:341-343
    • (2009) Bioorg Med Chem Lett , vol.19 , pp. 341-343
    • Yoya, G.K.1    Belval, F.B.2    Constant, P.3    Duran, H.4    Daffe, M.5    Baltas, M.6
  • 27
    • 12444259662 scopus 로고    scopus 로고
    • Antioxidative effects of flavonols and their glycosides against the free-radical-induced peroxidation of linoleic acid in solution and in micelles
    • Zhou B, Miao Q, Yang L, Liu ZL (2005) Antioxidative effects of flavonols and their glycosides against the free-radical-induced peroxidation of linoleic acid in solution and in micelles. Chem Eur J 11:680-691
    • (2005) Chem Eur J , vol.11 , pp. 680-691
    • Zhou, B.1    Miao, Q.2    Yang, L.3    Liu, Z.L.4


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