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Volumn 65, Issue PA, 2014, Pages 13-19

Possibilities and limitations in the analysis of covalent interactions between phenolic compounds and proteins

Author keywords

Innovative analytical strategies and methodologies; Non covalent and covalent interactions; Oxidation; Plant phenolic compounds; Structure reactivity relationships

Indexed keywords


EID: 84908690670     PISSN: 09639969     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodres.2014.05.042     Document Type: Article
Times cited : (132)

References (65)
  • 1
    • 0018536145 scopus 로고
    • Determination of the degree of hydrolysis of food protein hydrolysates by trinitrobenzenesulfonic acid
    • Adler-Nissen J. Determination of the degree of hydrolysis of food protein hydrolysates by trinitrobenzenesulfonic acid. Journal of Agricultural and Food Chemistry 1972, 27:1256-1262.
    • (1972) Journal of Agricultural and Food Chemistry , vol.27 , pp. 1256-1262
    • Adler-Nissen, J.1
  • 2
    • 50549205473 scopus 로고
    • On enzyme inhibition by oxidized chlorogenic acid
    • Alberghina F.A. On enzyme inhibition by oxidized chlorogenic acid. Life Sciences 1964, 3:49-54.
    • (1964) Life Sciences , vol.3 , pp. 49-54
    • Alberghina, F.A.1
  • 3
    • 33750429314 scopus 로고    scopus 로고
    • Improved online coupling of planar chromatography with electrospray mass spectrometry: Extraction of zones from glass plates
    • Alpmann A., Morlock G. Improved online coupling of planar chromatography with electrospray mass spectrometry: Extraction of zones from glass plates. Analytical and Bioanalytical Chemistry 2006, 386:1543-1551.
    • (2006) Analytical and Bioanalytical Chemistry , vol.386 , pp. 1543-1551
    • Alpmann, A.1    Morlock, G.2
  • 4
    • 14744283556 scopus 로고    scopus 로고
    • Oxidation of caffeic acid in the presence of l-cysteine: Isolation of 2-s-cysteinylcaffeic acid and evaluation of its antioxidant properties
    • Bassil D., Makris D.P., Kefalas P. Oxidation of caffeic acid in the presence of l-cysteine: Isolation of 2-s-cysteinylcaffeic acid and evaluation of its antioxidant properties. Food Research International 2005, 38:395-402.
    • (2005) Food Research International , vol.38 , pp. 395-402
    • Bassil, D.1    Makris, D.P.2    Kefalas, P.3
  • 5
    • 79952538863 scopus 로고    scopus 로고
    • Honey melanoidins: Analysis of the compositions of the high molecular weight melanoidins exhibiting radical-scavenging activity
    • Brudzynski K., Miotto D. Honey melanoidins: Analysis of the compositions of the high molecular weight melanoidins exhibiting radical-scavenging activity. Food Chemistry 2011, 127:1023-1030.
    • (2011) Food Chemistry , vol.127 , pp. 1023-1030
    • Brudzynski, K.1    Miotto, D.2
  • 6
    • 84883328635 scopus 로고    scopus 로고
    • A new look on protein-polyphenol complexation during honey storage: Is this a random or organized event with the help of dirigent-like proteins?
    • Brudzynski K., Sjaarda C., Maldonado-Alvarez L. A new look on protein-polyphenol complexation during honey storage: Is this a random or organized event with the help of dirigent-like proteins?. PLoS One 2013, 30(8):e72897.
    • (2013) PLoS One , vol.30 , Issue.8 , pp. e72897
    • Brudzynski, K.1    Sjaarda, C.2    Maldonado-Alvarez, L.3
  • 8
    • 33751500205 scopus 로고
    • Characterization of the products of nonenzymic autoxidative phenolic reactions in a caffeic acid model system
    • Cilliers J.J.L., Singleton V.L. Characterization of the products of nonenzymic autoxidative phenolic reactions in a caffeic acid model system. Journal of Agricultural and Food Chemistry 1991, 39:1298-1303.
    • (1991) Journal of Agricultural and Food Chemistry , vol.39 , pp. 1298-1303
    • Cilliers, J.J.L.1    Singleton, V.L.2
  • 9
    • 68149124472 scopus 로고    scopus 로고
    • Dietary phenolics: Chemistry, bioavailability and effects on health
    • Crozier A., Jaganath I.B., Clifford M.N. Dietary phenolics: Chemistry, bioavailability and effects on health. Natural Product Reports 2009, 26:1001-1043.
    • (2009) Natural Product Reports , vol.26 , pp. 1001-1043
    • Crozier, A.1    Jaganath, I.B.2    Clifford, M.N.3
  • 10
    • 0017915141 scopus 로고
    • Bound quinic acid as a measure of coupling of leaf and sunflower-seed proteins with chlorogenic acid congeners: Loss of availability of lysine
    • Davies A.M., Newby V.K., Synge R.L. Bound quinic acid as a measure of coupling of leaf and sunflower-seed proteins with chlorogenic acid congeners: Loss of availability of lysine. Journal of the Science of Food and Agriculture 1978, 29:33-41.
    • (1978) Journal of the Science of Food and Agriculture , vol.29 , pp. 33-41
    • Davies, A.M.1    Newby, V.K.2    Synge, R.L.3
  • 11
    • 0028829961 scopus 로고
    • Stress-induced phenylpropanoid metabolism
    • Dixon R.A., Paiva N.L. Stress-induced phenylpropanoid metabolism. Plant Cell 1995, 7:1085-1097.
    • (1995) Plant Cell , vol.7 , pp. 1085-1097
    • Dixon, R.A.1    Paiva, N.L.2
  • 12
    • 0033054548 scopus 로고    scopus 로고
    • Determination of the affinity of drugs toward serum albumin by measurement of the quenching of the intrinsic tryptophan fluorescence of the protein
    • Epps D.E., Raub T.J., Caiolfa V., Chiari A., Zamai M. Determination of the affinity of drugs toward serum albumin by measurement of the quenching of the intrinsic tryptophan fluorescence of the protein. Journal of Pharmacy and Pharmacology 1999, 51:41-48.
    • (1999) Journal of Pharmacy and Pharmacology , vol.51 , pp. 41-48
    • Epps, D.E.1    Raub, T.J.2    Caiolfa, V.3    Chiari, A.4    Zamai, M.5
  • 15
    • 0642271751 scopus 로고    scopus 로고
    • Chemistry, biochemistry, and dietary role of potato polyphenols. A review
    • Friedman M. Chemistry, biochemistry, and dietary role of potato polyphenols. A review. Journal of Agricultural and Food Chemistry 1997, 45:1523-1540.
    • (1997) Journal of Agricultural and Food Chemistry , vol.45 , pp. 1523-1540
    • Friedman, M.1
  • 16
    • 0000047214 scopus 로고
    • Phenolic substances and plant disease
    • Friend J. Phenolic substances and plant disease. Recent Advances in Phytochemistry 1979, 12:557-588.
    • (1979) Recent Advances in Phytochemistry , vol.12 , pp. 557-588
    • Friend, J.1
  • 18
    • 34548451745 scopus 로고    scopus 로고
    • Sunflower proteins: Overview of their physicochemical, structural and functional properties
    • Gonzalez-Perez S., Vereijken J.M. Sunflower proteins: Overview of their physicochemical, structural and functional properties. Journal of the Science of Food and Agriculture 2007, 87:2173-2191.
    • (2007) Journal of the Science of Food and Agriculture , vol.87 , pp. 2173-2191
    • Gonzalez-Perez, S.1    Vereijken, J.M.2
  • 19
    • 0035342444 scopus 로고    scopus 로고
    • Protein-flavonol interaction: Fluorescence spectroscopic study
    • Guharay J., Sengupta B., Sengupta P.K. Protein-flavonol interaction: Fluorescence spectroscopic study. Proteins 2001, 43:75-81.
    • (2001) Proteins , vol.43 , pp. 75-81
    • Guharay, J.1    Sengupta, B.2    Sengupta, P.K.3
  • 20
    • 0029067901 scopus 로고
    • Thin-layer chromatography combined with matrix-assisted laser-desorption ionization mass-spectrometry
    • Gusev A.I., Proctor A., Rabinovich Y.I., Hercules D.M. Thin-layer chromatography combined with matrix-assisted laser-desorption ionization mass-spectrometry. Analytical Chemistry 1995, 67:1805-1814.
    • (1995) Analytical Chemistry , vol.67 , pp. 1805-1814
    • Gusev, A.I.1    Proctor, A.2    Rabinovich, Y.I.3    Hercules, D.M.4
  • 21
    • 0001198223 scopus 로고
    • Imaging of thin-layer chromatograms using matrix/assisted laser desorption/ionization mass-spectrometry
    • Gusev A.I., Vasseur O.J., Proctor A., Sharkey A.G., Hercules D.M. Imaging of thin-layer chromatograms using matrix/assisted laser desorption/ionization mass-spectrometry. Analytical Chemistry 1995, 67:4565-4570.
    • (1995) Analytical Chemistry , vol.67 , pp. 4565-4570
    • Gusev, A.I.1    Vasseur, O.J.2    Proctor, A.3    Sharkey, A.G.4    Hercules, D.M.5
  • 23
  • 24
    • 0021117986 scopus 로고
    • Nutritional consequences of the reactions between proteins and oxidized polyphenolic acids
    • Hurrell R.F., Finot P.A. Nutritional consequences of the reactions between proteins and oxidized polyphenolic acids. Advances in Experimental Medicine and Biology 1984, 177:423-435.
    • (1984) Advances in Experimental Medicine and Biology , vol.177 , pp. 423-435
    • Hurrell, R.F.1    Finot, P.A.2
  • 25
    • 0000887242 scopus 로고
    • Ultraviolet absorption and fluorescence properties of whey-potato and whey-pea protein composites
    • Jackman J.L., Yada R.Y. Ultraviolet absorption and fluorescence properties of whey-potato and whey-pea protein composites. Canadian Institute of Food Science and Technology Journal 1989, 22:252-259.
    • (1989) Canadian Institute of Food Science and Technology Journal , vol.22 , pp. 252-259
    • Jackman, J.L.1    Yada, R.Y.2
  • 26
    • 84985372260 scopus 로고
    • The rapid determination of chemically reactive lysine in the presence of carbohydrates by a modified trinitrobenzenesulphonic acid procedure
    • James N.A., Ryley J. The rapid determination of chemically reactive lysine in the presence of carbohydrates by a modified trinitrobenzenesulphonic acid procedure. Journal of the Science of Food and Agriculture 1986, 37:151-156.
    • (1986) Journal of the Science of Food and Agriculture , vol.37 , pp. 151-156
    • James, N.A.1    Ryley, J.2
  • 27
    • 0242657803 scopus 로고    scopus 로고
    • A review. Reactions of plant phenolics with food proteins and enzymes under special consideration of covalent bonds
    • Kroll J., Rawel H.M., Rohn S. A review. Reactions of plant phenolics with food proteins and enzymes under special consideration of covalent bonds. Food Science & Technology Research 2003, 9:205-218.
    • (2003) Food Science & Technology Research , vol.9 , pp. 205-218
    • Kroll, J.1    Rawel, H.M.2    Rohn, S.3
  • 28
    • 0033748390 scopus 로고    scopus 로고
    • Effects of laccase and ferulic acid on wheat flour doughs
    • Labat E., Morel M.H., Rouau X. Effects of laccase and ferulic acid on wheat flour doughs. Cereal Chemistry 2000, 77:823-828.
    • (2000) Cereal Chemistry , vol.77 , pp. 823-828
    • Labat, E.1    Morel, M.H.2    Rouau, X.3
  • 29
    • 84857382394 scopus 로고    scopus 로고
    • Interactions between polyphenols and macromolecules: Quantification methods and mechanisms
    • Le Bourvellec C., Renard C.M. Interactions between polyphenols and macromolecules: Quantification methods and mechanisms. Critical Reviews in Food Science and Nutrition 2012, 52:213-248.
    • (2012) Critical Reviews in Food Science and Nutrition , vol.52 , pp. 213-248
    • Le Bourvellec, C.1    Renard, C.M.2
  • 30
    • 0011281462 scopus 로고
    • Cinnamyl and p-coumaryl esters as intermediates in the biosynthesis of chlorogenic acid
    • Levy C.C., Zucker M. Cinnamyl and p-coumaryl esters as intermediates in the biosynthesis of chlorogenic acid. Journal of Biological Chemistry 1960, 235:2418-2425.
    • (1960) Journal of Biological Chemistry , vol.235 , pp. 2418-2425
    • Levy, C.C.1    Zucker, M.2
  • 31
    • 0016362991 scopus 로고
    • Overcoming problems of phenolics and quinones in the isolation of plant enzymes and organelles
    • Loomis W.D. Overcoming problems of phenolics and quinones in the isolation of plant enzymes and organelles. Methods in Enzymology 1974, 31:528-544.
    • (1974) Methods in Enzymology , vol.31 , pp. 528-544
    • Loomis, W.D.1
  • 32
    • 0000476953 scopus 로고
    • The reaction of quinones with protamine and nucleoprotamine: N-terminal proline
    • Mason H.S., Peterson E.W. The reaction of quinones with protamine and nucleoprotamine: N-terminal proline. Journal of Biological Chemistry 1955, 212:485-493.
    • (1955) Journal of Biological Chemistry , vol.212 , pp. 485-493
    • Mason, H.S.1    Peterson, E.W.2
  • 33
    • 84986520447 scopus 로고
    • Modification of proteins by polyphenol oxidase and peroxidase and their products
    • Matheis G., Whitaker J.R. Modification of proteins by polyphenol oxidase and peroxidase and their products. Journal of Food Biochemistry 1984, 8:137-162.
    • (1984) Journal of Food Biochemistry , vol.8 , pp. 137-162
    • Matheis, G.1    Whitaker, J.R.2
  • 35
  • 36
    • 33846816854 scopus 로고    scopus 로고
    • New coupling of planar chromatography with direct analysis in real time mass spectrometry
    • Morlock G., Ueda Y. New coupling of planar chromatography with direct analysis in real time mass spectrometry. Journal of Chromatography A 2007, 1143:243-251.
    • (2007) Journal of Chromatography A , vol.1143 , pp. 243-251
    • Morlock, G.1    Ueda, Y.2
  • 37
    • 0035488585 scopus 로고    scopus 로고
    • Development of free radical products during the greening reaction of caffeic acid esters (or chlorogenic acid) and a primary amino compound
    • Namiki M., Yabuta G., Koizumi Y., Yano M. Development of free radical products during the greening reaction of caffeic acid esters (or chlorogenic acid) and a primary amino compound. Bioscience, Biotechnology, and Biochemistry 2001, 65:2131-2136.
    • (2001) Bioscience, Biotechnology, and Biochemistry , vol.65 , pp. 2131-2136
    • Namiki, M.1    Yabuta, G.2    Koizumi, Y.3    Yano, M.4
  • 38
    • 0036823831 scopus 로고    scopus 로고
    • Detection of bound phenolic acids: Prevention by ascorbic acid and ethylenediaminetetraacetic acid of degradation of phenolic acids during alkaline hydrolysis
    • Nardini M., Cirillo E., Natella F., Mencarelli D., Comisso A., Scaccini C. Detection of bound phenolic acids: Prevention by ascorbic acid and ethylenediaminetetraacetic acid of degradation of phenolic acids during alkaline hydrolysis. Food Chemistry 2002, 79:119-124.
    • (2002) Food Chemistry , vol.79 , pp. 119-124
    • Nardini, M.1    Cirillo, E.2    Natella, F.3    Mencarelli, D.4    Comisso, A.5    Scaccini, C.6
  • 40
    • 0028143645 scopus 로고
    • Quantitative electrophoretic analysis of proteins labeled with monobromobimane
    • O'Keefe D.O. Quantitative electrophoretic analysis of proteins labeled with monobromobimane. Analytical Biochemistry 1994, 222:86-94.
    • (1994) Analytical Biochemistry , vol.222 , pp. 86-94
    • O'Keefe, D.O.1
  • 44
    • 22244437897 scopus 로고    scopus 로고
    • Identification of dehydro-ferulic acid-tyrosine in rye and wheat: Evidence for a covalent cross-link between arabinoxylans and proteins
    • Piber M., Koehler P. Identification of dehydro-ferulic acid-tyrosine in rye and wheat: Evidence for a covalent cross-link between arabinoxylans and proteins. Journal of Agricultural and Food Chemistry 2005, 53:5276-5284.
    • (2005) Journal of Agricultural and Food Chemistry , vol.53 , pp. 5276-5284
    • Piber, M.1    Koehler, P.2
  • 46
    • 0041524991 scopus 로고    scopus 로고
    • Model studies on reactions of plant phenols with whey proteins
    • Rawel H.M., Kroll J., Hohl U.C. Model studies on reactions of plant phenols with whey proteins. Nahrung 2001, 45:72-81.
    • (2001) Nahrung , vol.45 , pp. 72-81
    • Rawel, H.M.1    Kroll, J.2    Hohl, U.C.3
  • 47
    • 0035238955 scopus 로고    scopus 로고
    • Reactions of phenolic substances with lysozyme - Physicochemical characterisation and proteolytic digestion of the derivatives
    • Rawel H.M., Kroll J., Rohn S. Reactions of phenolic substances with lysozyme - Physicochemical characterisation and proteolytic digestion of the derivatives. Food Chemistry 2001, 72:59-71.
    • (2001) Food Chemistry , vol.72 , pp. 59-71
    • Rawel, H.M.1    Kroll, J.2    Rohn, S.3
  • 48
    • 29344464592 scopus 로고    scopus 로고
    • Surface enhanced laser desorptions ionization-time of flight-mass spectrometry analysis in complex food and biological systems
    • Rawel H.M., Rohn S., Kroll J., Schweigert F.J. Surface enhanced laser desorptions ionization-time of flight-mass spectrometry analysis in complex food and biological systems. Molecular Nutrition & Food Research 2005, 49:1104-1111.
    • (2005) Molecular Nutrition & Food Research , vol.49 , pp. 1104-1111
    • Rawel, H.M.1    Rohn, S.2    Kroll, J.3    Schweigert, F.J.4
  • 49
    • 0036768548 scopus 로고    scopus 로고
    • Structural changes induced in bovine serum albumin by covalent attachment of chlorogenic acid
    • Rawel H.M., Rohn S., Kruse H.P., Kroll J. Structural changes induced in bovine serum albumin by covalent attachment of chlorogenic acid. Food Chemistry 2002, 78:443-455.
    • (2002) Food Chemistry , vol.78 , pp. 443-455
    • Rawel, H.M.1    Rohn, S.2    Kruse, H.P.3    Kroll, J.4
  • 51
    • 33748416859 scopus 로고    scopus 로고
    • Reactions of chlorogenic acid and quercetin with a soy protein isolate - Influence on the in vivo food protein quality in rats
    • Rohn S., Petzke K.J., Rawel H.M., Kroll J. Reactions of chlorogenic acid and quercetin with a soy protein isolate - Influence on the in vivo food protein quality in rats. Molecular Nutrition & Food Research 2006, 50:696-704.
    • (2006) Molecular Nutrition & Food Research , vol.50 , pp. 696-704
    • Rohn, S.1    Petzke, K.J.2    Rawel, H.M.3    Kroll, J.4
  • 52
    • 0037023972 scopus 로고    scopus 로고
    • Inhibitory effects of plant phenols on the activity of selected enzymes
    • Rohn S., Rawel H.M., Kroll J. Inhibitory effects of plant phenols on the activity of selected enzymes. Journal of Agricultural and Food Chemistry 2002, 50:3566-3571.
    • (2002) Journal of Agricultural and Food Chemistry , vol.50 , pp. 3566-3571
    • Rohn, S.1    Rawel, H.M.2    Kroll, J.3
  • 55
    • 23744477534 scopus 로고    scopus 로고
    • Reactions with phenolic substances can induce changes in some physico-chemical properties and activities of bromelain - The consequences for supplementary food products
    • Rohn S., Rawel H.M., Rober M., Kroll J. Reactions with phenolic substances can induce changes in some physico-chemical properties and activities of bromelain - The consequences for supplementary food products. International Journal of Food Science & Technology 2005, 40:771-782.
    • (2005) International Journal of Food Science & Technology , vol.40 , pp. 771-782
    • Rohn, S.1    Rawel, H.M.2    Rober, M.3    Kroll, J.4
  • 57
    • 39749104718 scopus 로고    scopus 로고
    • Characterization of covalent addition products of chlorogenic acid quinone with amino acid derivatives in model systems and apple juice by high-performance liquid chromatography/electrospray ionization tandem mass spectrometry
    • Schilling S., Sigolotto C.I., Carle R., Schieber A. Characterization of covalent addition products of chlorogenic acid quinone with amino acid derivatives in model systems and apple juice by high-performance liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Communications in Mass Spectrometry 2008, 22:441-448.
    • (2008) Rapid Communications in Mass Spectrometry , vol.22 , pp. 441-448
    • Schilling, S.1    Sigolotto, C.I.2    Carle, R.3    Schieber, A.4
  • 58
    • 10244240521 scopus 로고    scopus 로고
    • Characterization of bovine serum albumin/chlorogenic acid solution mixtures by analytical ultracentrifugation
    • Seifert A., Rawel H.M., Harding S.E., Kroll J. Characterization of bovine serum albumin/chlorogenic acid solution mixtures by analytical ultracentrifugation. Progress in Colloid and Polymer Science 2004, 127:83-88.
    • (2004) Progress in Colloid and Polymer Science , vol.127 , pp. 83-88
    • Seifert, A.1    Rawel, H.M.2    Harding, S.E.3    Kroll, J.4
  • 61
    • 0028013536 scopus 로고
    • The structure and function of fungal laccases
    • Thurston C. The structure and function of fungal laccases. Microbiology 1994, 140:19-26.
    • (1994) Microbiology , vol.140 , pp. 19-26
    • Thurston, C.1
  • 62
    • 84883274790 scopus 로고    scopus 로고
    • One- and two-dimensional high-performance thin-layer chromatography as an alternative analytical tool for investigating polyphenol-protein interactions
    • Tscherch K., Biller J., Lehmann M., Trusch M., Rohn S. One- and two-dimensional high-performance thin-layer chromatography as an alternative analytical tool for investigating polyphenol-protein interactions. Phytochemical Analysis 2013, 24:436-445.
    • (2013) Phytochemical Analysis , vol.24 , pp. 436-445
    • Tscherch, K.1    Biller, J.2    Lehmann, M.3    Trusch, M.4    Rohn, S.5
  • 63
    • 0015528246 scopus 로고
    • New reaction of o-benzoquinone at the thioether group of methionine
    • Vithayathil P.J., Murthy G.S. New reaction of o-benzoquinone at the thioether group of methionine. Nature: New Biology 1972, 236:101-103.
    • (1972) Nature: New Biology , vol.236 , pp. 101-103
    • Vithayathil, P.J.1    Murthy, G.S.2
  • 64
    • 84856327592 scopus 로고    scopus 로고
    • A review of dietary polyphenol-plasma protein interactions: Characterization, influence on the bioactivity, and structure-affinity relationship
    • Xiao J., Kai G. A review of dietary polyphenol-plasma protein interactions: Characterization, influence on the bioactivity, and structure-affinity relationship. Critical Reviews in Food Science and Nutrition 2012, 52:85-101.
    • (2012) Critical Reviews in Food Science and Nutrition , vol.52 , pp. 85-101
    • Xiao, J.1    Kai, G.2
  • 65
    • 0035488551 scopus 로고    scopus 로고
    • Structure of green pigment formed by the reaction of caffeic acid esters (or chlorogenic acid) with a primary amino compound
    • Yabuta G., Koizumi Y., Namiki K., Hida M., Namiki M. Structure of green pigment formed by the reaction of caffeic acid esters (or chlorogenic acid) with a primary amino compound. Bioscience, Biotechnology, and Biochemistry 2001, 65:2121-2130.
    • (2001) Bioscience, Biotechnology, and Biochemistry , vol.65 , pp. 2121-2130
    • Yabuta, G.1    Koizumi, Y.2    Namiki, K.3    Hida, M.4    Namiki, M.5


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