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

Volumn 8, Issue 8, 2013, Pages

  Brudzynski, Katrina ^a,b   Sjaarda, Calvin ^a,b   Maldonado Alvarez, Liset ^b  

^a Bee Biomedicals Inc   (Canada)

^b BROCK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

NITROBLUE TETRAZOLIUM; POLYPHENOL; PROTEIN; PYROXYLIN; QUINONE DERIVATIVE;

ARTICLE; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; COVALENT BOND; ELECTROSPRAY QUADRUPOLE TIME OF FLIGHT MASS SPECTROMETRY; GEL PERMEATION CHROMATOGRAPHY; HONEY; MOLECULAR SIZE; POLYACRYLAMIDE GEL ELECTROPHORESIS; POLYMERIZATION; PROTEIN BINDING; PROTEIN CONTENT; PROTEIN CROSS LINKING; PROTEIN MODIFICATION; QUALITATIVE ANALYSIS; QUANTITATIVE ANALYSIS; STOICHIOMETRY; STORAGE; TEMPERATURE; TIME OF FLIGHT MASS SPECTROMETRY;

AMINO ACID SEQUENCE; CHROMATOGRAPHY, GEL; HONEY; MOLECULAR SEQUENCE DATA; MOLECULAR WEIGHT; PEPTIDES; PLANT PROTEINS; POLYPHENOLS; PRESERVATION, BIOLOGICAL; QUINONES; SEQUENCE HOMOLOGY, AMINO ACID; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STAINING AND LABELING; TEMPERATURE; TETRAZOLIUM SALTS;

EID: 84883328635     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0072897     Document Type: Article

References (48)

1. Turkmen N, Sari F, Poyrazoglu ES, Velioglu YS, (2006) Effects of prolonged heating on antioxidant activity and color of honey. Food Chem 95: 653-657.
2. Brudzynski K, Miotto D, (2011) Honey melanoidins. Analysis of a composition of the high molecular weight melanoidin fractions exhibiting radical scavenging capacity. Food Chem 127: 1023-1030.
3. Hodge JE, (1953) Chemistry of browning reactions in model systems. J Agric Food Chem 1: 928-943.
4. Fayle SE, Gerrard JA (2002) The Maillard Reaction. Royal Society of Chemistry (Great Britain).
5. Tressl R, Wondrak TG, Garbe L-A, (1998) Pentoses and hexoses as source of new melanoidin-like Maillard polymers. J Agric Food Chem 46: 1765-1776.
6. Borrelli RC, Fogliano V, Monti SM, Ames JM, (2002) Characterization of melanoidins from a glucose-glycine model system. Eur Food Res Technol 215: 210-215.
7. Kroh L, Fiedler T, Wagner J, (2008) α- Dicarbonyl compounds-Key intermediates for the formation of carbohydrate-based melanoidins. Ann N.Y Acad Sci 1126: 210-215.
8. Henle T, (2005) Protein-bound advanced glycation endproducts (AGEs) as bioactive amino acid derivatives in foods. Amino Acids 29: 313-322.
9. Nunes FM, Reis A, Domingues MRM, Coimbra MA, (2006) Characterization of galactomannan derivatives in roasted coffee beverages. J Agric Food Chem 54: 3428-3439.
10. Bekedam EK, De Laat MPFC, Schols HA, Van Boekel MAJS, Smit G, (2007) Arabinogalactan proteins are incorporated in negatively charged coffee brew melanoidins. J Agric Food Chem 55: 761-768.
11. Brudzynski K, Miotto D, (2011) The recognition of high molecular weight melanoidins as the main components responsible for radical-scavenging capacity of unheated and heat-treated Canadian honeys. Food Chem 125: 570-575.
12. Brudzynski K, Kim L, (2011) Storage-induced chemical changes in active components of honey de-regulate its antibacterial activity. Food Chem 126: 1155-1163.
13. White JW, Kushnir I, Subers MH, (1964) Effect of storage and processing temperatures on honey quality. Food Technol 18: 555-8.
14. Persano Oddo L, Piazza LG, Pulcini P, (1999) Invertase activity in honey. Apidologie 30: 57-65.
15. Karabournioti S, Zervalaki P, (2001) The effect of heating on honey HMF and invertase. Apiacta 36: 177-181.
16. Semkiw P, Skowronek W, Skubida P, Rybak-Chmielewska H, Szczesna T, (2010) Changes occurring in honey during ripening under controlled conditions based on α-amylase activity, acidity and 5-hydroxymethylfurfural content. J Apic Sci 54: 55-64.
17. Siebert KJ, (1999) Effect of protein-polyphenol interactions on beverage haze, stabilization, and analysis. J Agric Food Chem 47: 353-362.
18. Wu LC, Siebert KJ, (2002) Characterization of haze-active proteins in apple juice. J Agric Food Chem 50: 3828-34.
19. Paine HS, Gertler SI, Lothrop RE, (1934) Colloidal constituents of honey. Influence on properties and commercial value. Ind Eng Chem 26: 73-81.
20. Hurrell RF, Finot PA, Cuq JL, (1982) Protein-polyphenol reactions.1. Nutritional and metabolic consequences of the reaction between oxidized caffeic acid and the lysine residues of casein. Br J Nutr 47: 191-211.
21. Spencer CM, Cai Y, Martin R, Gaffney SH, Goulding PN, et al. (1988) Polyphenol complexation-some thoughts and observations. Phytochem 27: 2397-2409.
22. Charlton AJ, Baxter NJ, Khan ML, Moir AJG, Haslam E, et al. (2002) Polyphenol/peptide binding and precipitation. J. Agric. Food Chem. 50: 1593-1601.
23. Rawel MH, Rohn S, (2010) Nature of hydroxycinnamate-protein interactions. Phytochem Rev 9: 93-109.
24. Brudzynski K, Abubaker K, Miotto D, (2012) Unraveling a mechanism of honey antibacterial action: Polyphenol/H2O2-induced oxidative effect on bacterial cell growth and on DNA degradation. Food Chem 133: 329-336.
25. Brudzynski K, Lannigan R, (2012) Mechanism of honey bacteriostatic action against MRSA and VRE involves hydroxyl radicals generated from honey's hydrogen peroxide. Front. Microbiol 3: a36.
26. Brudzynski K. Abubaker K, St-Martin L, Castle A, (2012) Re-examining the role of hydrogen peroxide in bacteriostatic and bactericidal activities of honey. Front. Microbiol 2: a213.
27. Brudzynski K, Abubaker K, Wang T, (2012) Powerful bacterial killing by buckwheat honey is concentration -dependent, involves complete DNA degradation and requires hydrogen peroxide. Front Microbiol 3: a242.
28. Pourcel L, Routaboul JM, Cheynier V, Lepiniec L, Debeaujon I, (2006) Flavonoids oxidation in plants: from biochemical properties to physiological functions. Trends Plant Sci 12: 29-36.
29. Fukumoto LR, Mazza G, (2000) Assessing antioxidant and pro-oxidant activities of phenolic compounds. J Agric Food Chem 48: 3597-3604.
30. Sakihama Y, Cohen MF, Grace SC, Yamasaki H, (2002) Plant phenolic antioxidant and pro-oxidant activities: phenolics-induced oxidative damage mediated by metals in plants. Toxicol 177: 67-80.
31. Labenski MT, Fisher AA, Lo HH, Monks TJ, Lau SS, (2009) Protein Electrophile-Binding Motifs: Lysine-Rich Proteins Are Preferential Targets of Quinones. DMD 37: 1211-1218.
32. Prigent SVE, Voragen AGJ, Visser AJVG, van Koningsveld GA, Gruppen H, (2007) Covalent interactions between proteins and oxidation products of caffeolyquinic acid (chlorogenic acid). J Agric Food Chem 87: 2502-2510.
33. Ito S, (2003) A Chemist's View of Melanogenesis. Pigment Cell Res 16: 230-236.
34. Pryor MGM, (1940) On the hardening of the cuticle of insects. Proc R Soc Lond B 128: 393-407.
35. Andersen SO, (2010) Insect cuticular sclerotization: A review. Insect Biochem Mol Biol 40: 166-178.
36. Ralph J, Lunquist K, Brunow G, Lu F, Kim H, et al. (2004) Lignins: Natural polymers from oxidative coupling of 4-hydroxyphenyl propanoids. Phytochem. Rev 3: 29-60.
37. Davin LB, Lewis NG, (2005) Dirigent phenoxy radical coupling: advances and challenges. Cur Opin Biotech 16: 398-406.
38. Davin LB, Wang HB, Crowell AL, Bedgar DL, Martin DM, et al. (1997) Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center. Science 275: 362-366.
39. Bradford MM, (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72: 248-254.
40. Singleton VL, Rossi JA, (1965) Colorimetry of Total Phenolics with Phosphomolybdic-Phosphotungstic Acid Reagents. Am J Enol Vitic 16: 144-158.
41. Laemmli UK, (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage. Nature 227 (5259): 680-685.
42. Paz MA, Fluckiger R, Boak A, Kagan HM, Gallop PM, (1991) Specific detection of quinoproteins by red-ox cycling staining. J Biol Chem 266: 689-692.
43. Pierpoint WS, (1969) o-Quinones formed in plant extracts. Their reaction with bovine serum albumin. Biochem J 112: 619-629.
44. Leatham GF, King V, Stahmann MA, (1980) In vitro protein polymerization by quinones or free radicals generated by plant or fungal oxidative enzymes. Phytopathol 70: 1134-1140.
45. Cheyner V, Osse C, Rigaud J, (1988) Oxidation of grapes juice phenolic compounds in model solution. J Food Sci 53: 1729-1732.
46. Namiki M, Yabuta G, Koizumi Y, Yano M, (2001) Development of free radical products during the greening reaction of caffeic acid esters (or chlorogenic acid) and a primary amino compound. Biosci Biotechnol Biochem 65: 2131-2136.
47. Fristensky B, Horovitz D, Hadwiger LA, (1988) cDNA sequences for pea disease resistance response genes. Plant Mol Biol 11: 713-715.
48. Hückelhoven R, (2007) Cell Wall-Associated Mechanisms of Disease Resistance and Susceptibility. Annu Rev of Phytopath 45: 101-127.