메뉴 건너뛰기




Volumn 52, Issue 7, 2004, Pages 2084-2091

4-Hydroxycinnamic Ethyl Ester Derivatives and Related Dehydrodimers: Relationship between Oxidation Potential and Protective Effects against Oxidation of Low-Density Lipoproteins

Author keywords

4 Hydroxycinnamic ethyl ester derivatives; Dehydrodimers; Electrochemical oxidation potential antioxidant activity relationship; Free radical scavenging activity; Low density lipoproteins

Indexed keywords

ANTIOXIDANT; COPPER; DIMER; ESTER DERIVATIVE; FERULIC ACID; LOW DENSITY LIPOPROTEIN; NAPHTHOL DERIVATIVE; PARA COUMARIC ACID; SCAVENGER; SINAPATE; TROLOX C; UNCLASSIFIED DRUG;

EID: 12144288257     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf035068n     Document Type: Article
Times cited : (38)

References (43)
  • 1
    • 0030799043 scopus 로고    scopus 로고
    • Low-density lipoprotein oxidation and its pathobiological significance
    • Steinberg, D. Low-density lipoprotein oxidation and its pathobiological significance. J. Biol. Chem. 1997, 272, 20963-20966.
    • (1997) J. Biol. Chem. , vol.272 , pp. 20963-20966
    • Steinberg, D.1
  • 2
    • 0029883764 scopus 로고    scopus 로고
    • The role of oxidized lipoproteins in atherogenesis
    • Berliner, J. A.; Heinecke, J. W. The role of oxidized lipoproteins in atherogenesis. Free Radic. Biol. Med. 1996, 20, 707-727.
    • (1996) Free Radic. Biol. Med. , vol.20 , pp. 707-727
    • Berliner, J.A.1    Heinecke, J.W.2
  • 3
    • 0038408778 scopus 로고    scopus 로고
    • Phenolic acids in foods: An overview of analytical methodology
    • Robbins, R. J. Phenolic acids in foods: an overview of analytical methodology. J. Agric. Food Chem. 2003, 51, 2866-2887.
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 2866-2887
    • Robbins, R.J.1
  • 4
    • 0033929360 scopus 로고    scopus 로고
    • Content of phenolic acids and ferulic acid dehydrodimers in 17 rye (Secale cereale L.) varieties
    • Andreasen, M. F.; Christensen, L. P.; Meyer, A. S.; Hansen, A. Content of phenolic acids and ferulic acid dehydrodimers in 17 rye (Secale cereale L.) varieties. J. Agric. Food Chem. 2000, 48, 2837-2842.
    • (2000) J. Agric. Food Chem. , vol.48 , pp. 2837-2842
    • Andreasen, M.F.1    Christensen, L.P.2    Meyer, A.S.3    Hansen, A.4
  • 5
    • 0029132922 scopus 로고
    • Inhibition of human low-density lipoprotein oxidation by caffeic acid and other hydroxycinnamic acid derivatives
    • Nardini, M.; D'Aquino, M.; Tomassi, G.; Gentili, V.; Di Felice, M.; Scaccini, C. Inhibition of human low-density lipoprotein oxidation by caffeic acid and other hydroxycinnamic acid derivatives. Free Radic. Biol. Med. 1995, 19, 541-552.
    • (1995) Free Radic. Biol. Med. , vol.19 , pp. 541-552
    • Nardini, M.1    D'Aquino, M.2    Tomassi, G.3    Gentili, V.4    Di Felice, M.5    Scaccini, C.6
  • 7
    • 33745044318 scopus 로고
    • Identification and synthesis of new ferulic acid dehydrodimers present in grass cell walls
    • Ralph, J.; Quideau, S.; Grabber, J. H.; Hatfield, R. D. Identification and synthesis of new ferulic acid dehydrodimers present in grass cell walls. J. Chem. Soc., Perkin Trans. 1 1994, 3485-3498.
    • (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 3485-3498
    • Ralph, J.1    Quideau, S.2    Grabber, J.H.3    Hatfield, R.D.4
  • 8
    • 0033059228 scopus 로고    scopus 로고
    • Ferulic acid and diferulic acids as components of sugar-beet pectins and maize bran heteroxylans
    • Saulnier, L.; Thibault, J. F.; Ferulic acid and diferulic acids as components of sugar-beet pectins and maize bran heteroxylans. J. Sci. Food Agric. 1999, 79, 396-402.
    • (1999) J. Sci. Food Agric. , vol.79 , pp. 396-402
    • Saulnier, L.1    Thibault, J.F.2
  • 10
    • 0030835479 scopus 로고    scopus 로고
    • Ferulic acid dehydrodimers in the cell walls of Beta vulgaris and their possible role in texture
    • Wadron, K. W.; Ng, A.; Parker, M. L.; Parr, A. J. Ferulic acid dehydrodimers in the cell walls of Beta vulgaris and their possible role in texture. J. Sci. Food Agric. 1997, 74, 221-228.
    • (1997) J. Sci. Food Agric. , vol.74 , pp. 221-228
    • Wadron, K.W.1    Ng, A.2    Parker, M.L.3    Parr, A.J.4
  • 11
    • 52849091880 scopus 로고    scopus 로고
    • Ferulic acid dehydrodimers as structural elements in cereal dietary fibre
    • Renger, A.; Steinhart, H. Ferulic acid dehydrodimers as structural elements in cereal dietary fibre. Eur. Food Res. Technol. 2000, 211, 422-428.
    • (2000) Eur. Food Res. Technol. , vol.211 , pp. 422-428
    • Renger, A.1    Steinhart, H.2
  • 13
    • 0035873049 scopus 로고    scopus 로고
    • Diferulates as structural components in soluble and insoluble cereal dietary fibre
    • Bunzel, M.; Ralph, J.; Marita, J. M.; Hatfield, R. D.; Steinhart, H. Diferulates as structural components in soluble and insoluble cereal dietary fibre. J. Sci. Food Agric. 2001, 81, 653-660.
    • (2001) J. Sci. Food Agric. , vol.81 , pp. 653-660
    • Bunzel, M.1    Ralph, J.2    Marita, J.M.3    Hatfield, R.D.4    Steinhart, H.5
  • 15
    • 0029888128 scopus 로고    scopus 로고
    • Structure-antioxidant activity relationships of flavonoids and phenolic acids
    • Rice-Evans, C. A.; Miller, N. J.; Paganga, G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 1996, 20, 933-956.
    • (1996) Free Radic. Biol. Med. , vol.20 , pp. 933-956
    • Rice-Evans, C.A.1    Miller, N.J.2    Paganga, G.3
  • 17
    • 0032949341 scopus 로고    scopus 로고
    • Benzoic and cinnamic acid derivatives as antioxidants: Structure-activity relation
    • Natella, F.; Nardini, M.; Di Felice, M.; Scaccini, C. Benzoic and cinnamic acid derivatives as antioxidants: structure-activity relation. J. Agric. Food. Chem. 1999, 47, 1453-1459.
    • (1999) J. Agric. Food. Chem. , vol.47 , pp. 1453-1459
    • Natella, F.1    Nardini, M.2    Di Felice, M.3    Scaccini, C.4
  • 18
    • 0242500948 scopus 로고    scopus 로고
    • Structure-antioxidant activity relationship of ferulic acid derivatives: Effect of carbon side chain characteristic groups
    • Nenadis, N.; Zhang, H.-Y.; Tsimidou, M. Z. Structure-antioxidant activity relationship of ferulic acid derivatives: effect of carbon side chain characteristic groups. J. Agric. Food Chem. 2003, 51, 1874-1879.
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 1874-1879
    • Nenadis, N.1    Zhang, H.-Y.2    Tsimidou, M.Z.3
  • 21
    • 0033028154 scopus 로고    scopus 로고
    • Antioxidant properties of 4,4′-dihydroxy-3,3′ -dimethoxy-β,β′-bicinnamic acid (8-8-diferulic acid, non cyclic form)
    • García-Conesa, M. T.; Wilson, G. W.; Plumb, G. W.; Ralph, J.; Williamson, G. Antioxidant properties of 4,4′-dihydroxy-3,3′ -dimethoxy-β,β′-bicinnamic acid (8-8-diferulic acid, non cyclic form). J. Sci. Food Agric. 1999, 79, 379-384.
    • (1999) J. Sci. Food Agric. , vol.79 , pp. 379-384
    • García-Conesa, M.T.1    Wilson, G.W.2    Plumb, G.W.3    Ralph, J.4    Williamson, G.5
  • 22
    • 0034850886 scopus 로고    scopus 로고
    • Antioxidant effects of phenolic rye (Secale cereale L.) extracts, monomeric hydroxycinnamates, and ferulic acid dehydrodimers on human low-density lipoproteins
    • Andreasen, M. F.; Landbo, A.-K.; Christensen, L. P.; Hansen, A.; Meyer, A. S. Antioxidant effects of phenolic rye (Secale cereale L.) extracts, monomeric hydroxycinnamates, and ferulic acid dehydrodimers on human low-density lipoproteins. J. Agric. Food Chem. 2001, 49, 4090-4096.
    • (2001) J. Agric. Food Chem. , vol.49 , pp. 4090-4096
    • Andreasen, M.F.1    Landbo, A.-K.2    Christensen, L.P.3    Hansen, A.4    Meyer, A.S.5
  • 24
    • 0034847274 scopus 로고    scopus 로고
    • Regioselective dimerization of ferulic acid in a micellar solution
    • Larsen, E.; Andreasen, M. F.; Christensen, L. P. Regioselective dimerization of ferulic acid in a micellar solution. J. Agric. Food Chem. 2001, 49, 3471-3475.
    • (2001) J. Agric. Food Chem. , vol.49 , pp. 3471-3475
    • Larsen, E.1    Andreasen, M.F.2    Christensen, L.P.3
  • 25
    • 37049079982 scopus 로고
    • Horseradish peroxidase-catalysed oxidative coupling of methyl sinapate to give diastereoisomeric spiro dimers
    • Setälä, H.; Pajunen, A.; Kilpeläinen, I.; Brunow, G. Horseradish peroxidase-catalysed oxidative coupling of methyl sinapate to give diastereoisomeric spiro dimers. J. Chem. Soc., Perkin Trans. 1 1994, 1163-1165.
    • (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 1163-1165
    • Setälä, H.1    Pajunen, A.2    Kilpeläinen, I.3    Brunow, G.4
  • 26
    • 0033619997 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of dihydrobenzofuran lignans and related compounds as potential antitumor agents that inhibit tubulin polymerization
    • Pieters, L.; Van Dyck, S.; Gao, M.; Bai, R.; Hamel, E.; Vlietinck, A.; Lemière, G. Synthesis and biological evaluation of dihydrobenzofuran lignans and related compounds as potential antitumor agents that inhibit tubulin polymerization. J. Med. Chem. 1999, 42, 5475-5481.
    • (1999) J. Med. Chem. , vol.42 , pp. 5475-5481
    • Pieters, L.1    Van Dyck, S.2    Gao, M.3    Bai, R.4    Hamel, E.5    Vlietinck, A.6    Lemière, G.7
  • 27
    • 0036214862 scopus 로고    scopus 로고
    • Anodic oxidation of phenols towards the synthesis of bioactive natural products
    • and references therein.
    • Yamamura, S.; Nishiyama, S. Anodic oxidation of phenols towards the synthesis of bioactive natural products. Synlett 2002, 4, 533-543 and references therein.
    • (2002) Synlett , vol.4 , pp. 533-543
    • Yamamura, S.1    Nishiyama, S.2
  • 28
    • 0141516603 scopus 로고    scopus 로고
    • Electrochemical oxidative coupling of 4-hydroxycinnamic ester derivatives: A convenient methodology for the biomimetic synthesis of lignin precursors
    • Neudorffer, A.; Deguin, B.; Hamel, C.; Fleury, M.-B.; Largeron, M. Electrochemical oxidative coupling of 4-hydroxycinnamic ester derivatives: a convenient methodology for the biomimetic synthesis of lignin precursors. Collect. Czech. Chem. Commun. 2003, 68, 1515-1530.
    • (2003) Collect. Czech. Chem. Commun. , vol.68 , pp. 1515-1530
    • Neudorffer, A.1    Deguin, B.2    Hamel, C.3    Fleury, M.-B.4    Largeron, M.5
  • 29
    • 0033518227 scopus 로고    scopus 로고
    • Synthesis and in vitro evaluation of new 8-amino-1,4-benzoxazine derivatives as neuroprotective antioxidants
    • Largeron, M.; Lockhart, B.; Pfeiffer, B.; Fleury, M.-B. Synthesis and in vitro evaluation of new 8-amino-1,4-benzoxazine derivatives as neuroprotective antioxidants. J. Med. Chem. 1999, 42, 5043-5052.
    • (1999) J. Med. Chem. , vol.42 , pp. 5043-5052
    • Largeron, M.1    Lockhart, B.2    Pfeiffer, B.3    Fleury, M.-B.4
  • 31
    • 0034678787 scopus 로고    scopus 로고
    • A convenient extension of the Wessely-Moser rearrangement for the synthesis of substituted alkylaminoflavones as neuroprotective agents in vitro
    • Larget, R.; Lockhart, B.; Renard, P.; Largeron, M. A convenient extension of the Wessely-Moser rearrangement for the synthesis of substituted alkylaminoflavones as neuroprotective agents in vitro. Bioorg. Med. Chem. Lett. 2000, 10, 835-838.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 835-838
    • Larget, R.1    Lockhart, B.2    Renard, P.3    Largeron, M.4
  • 33
    • 33745026603 scopus 로고
    • The distribution and chemical composition of ultracentrifugally separated lipoproteins in human serum
    • Havel, R. J.; Eder, H. A.; Bragdon, J. H. The distribution and chemical composition of ultracentrifugally separated lipoproteins in human serum. J. Clin. Invest. 1955, 34, 1345-1353.
    • (1955) J. Clin. Invest. , vol.34 , pp. 1345-1353
    • Havel, R.J.1    Eder, H.A.2    Bragdon, J.H.3
  • 34
    • 0022870712 scopus 로고
    • Urinary protein as measured with a pyrogallol red-molybdate complex, manually and in a Hitachi 726 automated analyzer
    • Watanabe, N.; Kamei, S.; Ohkubo, A.; Yamanaka, M.; Ohsawa, S.; Makino, K.; Tokuda, K. Urinary protein as measured with a pyrogallol red-molybdate complex, manually and in a Hitachi 726 automated analyzer. Clin. Chem. 1986, 32, 1551-1554.
    • (1986) Clin. Chem. , vol.32 , pp. 1551-1554
    • Watanabe, N.1    Kamei, S.2    Ohkubo, A.3    Yamanaka, M.4    Ohsawa, S.5    Makino, K.6    Tokuda, K.7
  • 35
    • 0021288834 scopus 로고
    • Chemical methods for the detection of lipid hydroperoxides
    • Pryor, W. A.; Castel, L. Chemical methods for the detection of lipid hydroperoxides. Methods Enzymol. 1984, 105, 293-299.
    • (1984) Methods Enzymol. , vol.105 , pp. 293-299
    • Pryor, W.A.1    Castel, L.2
  • 36
    • 0024550456 scopus 로고
    • Continuous monitoring of in vitro oxidation of human low-density lipoprotein
    • Esterbauer, H.; Striegl, G.; Puhl, H.; Rotheneder, M. Continuous monitoring of in vitro oxidation of human low-density lipoprotein. Free Radic. Res. Commun. 1989, 6, 67-75.
    • (1989) Free Radic. Res. Commun. , vol.6 , pp. 67-75
    • Esterbauer, H.1    Striegl, G.2    Puhl, H.3    Rotheneder, M.4
  • 37
    • 0023239754 scopus 로고
    • Lipid peroxides and human diseases
    • Yagi, K. Lipid peroxides and human diseases. Chem. Phys. Lipids 1987, 45, 337-351.
    • (1987) Chem. Phys. Lipids , vol.45 , pp. 337-351
    • Yagi, K.1
  • 41
    • 0033917367 scopus 로고    scopus 로고
    • Phenolic acids and derivatives: Studies on the relationship among structure, radical scavenging activity, and physicochemical parameters
    • Silva, F. A. M.; Borges, F.; Guimarães, C.; Lima, J. L. F. C.; Matos, C.; Reis, S. Phenolic acids and derivatives: studies on the relationship among structure, radical scavenging activity, and physicochemical parameters. J. Agric. Food Chem. 2000, 48, 2122-2126.
    • (2000) J. Agric. Food Chem. , vol.48 , pp. 2122-2126
    • Silva, F.A.M.1    Borges, F.2    Guimarães, C.3    Lima, J.L.F.C.4    Matos, C.5    Reis, S.6
  • 42
    • 0035203337 scopus 로고    scopus 로고
    • Structure-hepatoprotective activity relationship of 3, 4-dihydroxycinnamic acid (caffeic acid) derivatives
    • Pérez-Alvarez, V.; Bobadilla, R. A.; Muriel, P. Structure-hepatoprotective activity relationship of 3,4-dihydroxycinnamic acid (caffeic acid) derivatives J. Appl. Toxicol. 2001, 21, 527-531.
    • (2001) J. Appl. Toxicol. , vol.21 , pp. 527-531
    • Pérez-Alvarez, V.1    Bobadilla, R.A.2    Muriel, P.3
  • 43
    • 0033805608 scopus 로고    scopus 로고
    • The problems of using one-dimensional methods to evaluate multifunctional food and biological antioxidants
    • Frankel, E. N.; Meyer, A. S. The problems of using one-dimensional methods to evaluate multifunctional food and biological antioxidants. J. Sci. Food Agric. 2000, 80, 1925-1941.
    • (2000) J. Sci. Food Agric. , vol.80 , pp. 1925-1941
    • Frankel, E.N.1    Meyer, A.S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.