Sulfite-radical anions in isolated soy proteins

Journal of Food Science

Volumn 72, Issue 5, 2007, Pages

  Lei, Q ^a   Boatright, W L ^a  

^a UNIVERSITY OF KENTUCKY   (United States)

Author keywords

Manganese; Methanethiol; Soy protein; Sulfate free radical; Sulfite free radical

Indexed keywords

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; 5,5-DIMETHYL-1-PYRROLINE-1-OXIDE; AMINE OXIDE; ANION; FREE RADICAL; MANGANESE; METHANETHIOL; METHIONINE; REACTIVE OXYGEN METABOLITE; SCAVENGER; SOYBEAN PROTEIN; SULFITE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ANALYSIS OF VARIANCE; ARTICLE; CHEMISTRY; ELECTRON SPIN RESONANCE; MASS FRAGMENTOGRAPHY; METABOLISM; OXIDATION REDUCTION REACTION; SPIN TRAPPING;

ANALYSIS OF VARIANCE; ANIONS; CYCLIC N-OXIDES; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICAL SCAVENGERS; FREE RADICALS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MANGANESE; METHIONINE; OXIDATION-REDUCTION; REACTIVE OXYGEN SPECIES; SOYBEAN PROTEINS; SPIN TRAPPING; SULFHYDRYL COMPOUNDS; SULFITES;

GLYCINE MAX;

EID: 34250888681     PISSN: 00221147     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1750-3841.2007.00395.x     Document Type: Article

References (41)

1. Boatright WL. 2002. Effect of gallic acid on the aroma constituents of soymilk and soy protein isolates. J Am Oil Chem Soc 79 (4 317 23.
2. Boatright WL. 2006. Modified soy products and methods for reducing odor and improving flavor of soy products. U.S. Patent Nr 7147878.
3. Boatright WL, Stine CJ. 2004. Residual sulfur metabolites in isolated soy proteins: sulfite to cysteine. J Food Sci 69 (3 200 5.
4. Boatright WL, Lei Q, Stine CJ. 2006. Sulfite formation in isolated soy proteins. J Food Sci 71 (3 115 9.
5. Chatgilialoglu C, Ferreri C, Ballestri M, Mulazzani QG, Landi L. 2000. Cis-trans isomerization of monosaturated fatty acid residues in phospholipids by thiyl. Radicals 122 : 4593 601.
6. Choi J, Sullards MC, Olzmann JA, Rees HD, Weintraub ST, Bostwick DE, Gearing M, Levey AI, Chin L-S, Li L. 2006. Oxidative damage of DJ-1 is linked to sporadic Parkinson and Alzheimer diseases. J Bio Chem 281 (16 10816 24.
7. Clementi ME, Pezzotti M, Orsini F, Sampaolese B, Mezzogori D, Grassi C, Giardina B, Misiti F. 2006. Alzheimer's amyloid β-peptide (1-42) induces cell death in human neuroblastoma via bax/bcl-2 ratio increase: an intriguing role for methionine 35. Biochem Biophys Res Commun 342 (1 206 13.
8. Eberson L. 1982. Electron-transfer reactions in organic chemistry. Adv Phys Org Chem 18 : 79 185.
9. Erben-Russ M, Michel C, Bors W, Saran M. 1987. Determination of sulfite radical (SO 3-) reaction rate constants by means of competition kinetics. Radiat Environ Biophys 26 (4 289 94.
10. Ermakov AN, Purmal AP. 2002. Catalysis of HSO3-/SO32-oxidation by manganese ions. Kinet Catal 43 (2 249 60.
11. Ferreri C, Manco I, Faraone-Mennella MR, Torreggiani A, Tamba M, Manara S, Chatgilialogu C. 2006. The reaction of hydrogen atoms with methionine residues: a model of reductive radical stress causing tandem protein-lipid damage. Chembiochem 7 : 1738 44.
12. Gaosheng C, Jiafu GXC, Side Y, Zhicheng Z. 1999. Laser flash photolysis study on the oxidation of methionine by SO4-C in aqueous solution. Radiat Phys Chem 54 : 449 53.
13. Hendrixson WS. 1925. The action of some oxidizing agents on sulfite and its determination with iodate. J Am Chem Soc 47 : 1319 25.
14. Hird FJR, Yates JR. 1961. The oxidation of cysteine, glutathione and thioglycollate by iodate, bromate, persulfate and air. J Sci Food Agric 12 : 89 95.
15. Hug GL, Bobrowski K, Kozubek H. Marciniak B. 2000. Photo-oxidation of methionine-containing peptides by the 4-carboxybenzophenone triplet state in aqueous solution. Competition between intramolecular two-centered three-electron bonded (S...S)+ and (S...N)+ formation. Photochem Photobiol 72 (1 1 9.
16. Huie RE, Neta P. 1984. Chemical behavior of SO3- and SO5-radicals in aqueous solutions. J Phys Chem 88 (23 5665 9.
17. Ito K, Kawanishi S. 1991. Site-specific fragmentation and modification of albumin by sulfite in the presence of metal ions or peroxidase/hydrogen peroxide: role of sulfate radical. Biochem Biophys Res Commun 176 (3 1306 12.
18. Jameton RA, Muller JG, Burrows CJ. 2002. Oxidative DNA damage from sulfite autoxidation catalyzed by manganese (III). C R Chimie 5 : 461 6.
19. Julian PL, Engstrom AG. 1941. Protein materials derived from soybeans or the like. U.S. Patent Nr 2238329.
20. Julian PL, Malter BT. 1941. Preparing a soybean protein or other seed protein suitable for use in coating paper, etc. U.S. Patent Nr 2246466.
21. Julian PL, Oberg EB. 1941. Protein composition suitable for molding, coating paper, etc. U.S. Patent Nr 2249003.
22. Laggner H, Hermann M, Sturm B, Gmeiner BMK, Kapiotis S. 2005. Sulfite facilitates LDL lipid oxidation by transition metal ions: a pro-oxidant in wine? FEBS Lett 579 (28 6486 92.
23. Lei Q, Boatright WL. 2006. Methionine is the methyl group donor for sulfite-associated methanethiol formation in isolated soy proteins. J Food Sci 71 (9 C527 31.
24. McLeod G, Ames J. 1988. Soy flavor and its improvement. Crit Rev Food Sci Nutr 27 : 219 402.
25. Miller BL, Kuczera K, Schoeneich C. 1998. One-electron photooxidation of N-methionyl peptides. Mechanism of sulfoxide and azasulfonium diastereomer formation through reaction of sulfide radical cation complexes with oxygen or superoxide. J Am Chem Soc 120 (14 3345 56.
26. Moore J, Yin J-J, Yu L. 2006. Novel fluorometric assay for hydroxyl radical scavenging capacity (HOSC) estimation. J Agric Food Chem 54 (3 617 26.
27. Moya HD, Neves EA, Coichev N, Niewahner J. 1999. A further demonstration of sulfite-induced redox cycling of metal ions initiated by shaking. J Chem Educ 76 (7 930 2.
28. Neta P, Huie RE. 1985. Free-radical chemistry of sulfite. Environ Health Perspect 64 : 209 17.
29. Pogocki D, Ghezzo-Schoneich E, Schoneich C. 2001 Conformational flexibility controls proton transfer between the methionine hydroxyl sulfuranyl radical and the N-terminal amino group in Thr-(X)n-met peptides. J Phys Chem B 105 : 1250 9.
30. Rah JH, Hasler CM, Painter JE, Chapman-Novakofske KM. Chapman-Novakofski KM, 2004. Applying the theory of planned behavior to women's behavioral attitudes on and consumption of soy products. J Nutr Educ Behav 36 (5) : 238 44.
31. SAS 1995. JMP® user's guide. SAS Inst., Cary, N.C.
32. Schoneich C, Zhao F, Madden KP, Bobrowski K. 1994. Side chain fragmentation of N-terminal threonine or serine residue induced through intramolecular proton transfer to hydroxyl sulfuranyl radical formed at neighboring methionine in dipeptides. J Am Chem Soc 116 : 4641 52.
33. Shi XL, Mao Y. 1994. 8-Hydroxy-2′-deoxyguanosine formation and DNA damage induced by sulfur trioxide anion radicals. Biochem Biophys Res Commun 205 (1 141 7.
34. Stine CJ, Boatright WL, Lu G. 2004. Intrinsic sulfite content of isolated soy proteins. J Am Oil Chem Soc 81 (9 829 33.
35. Waggle DH, Kolar DW. 1979. Types of soy products, in soy protein and human nutrition. New York : Academic Press. 41 p.
36. Wainwright T, McMahon JF, McDowell J. 1972. Formation of methional and methanethiol from methionine. J Sci Food Agric 23 (7 911 4.
37. Wedzicha BL. 1984. Principles, properties and reactions. In : Wedzicha BL, editor. Chemistry of sulphur dioxide in foods. London, New York : Elsevier Applied Science Publishers. p 69 78.
38. Wilson LA, Johnson LA, Hayenga ML, Love MH. 1990. Protein used for food and industrial products. In editor C.A. Greiner : Economic implications of modified soybean traits. Ames, Iowa : Iowa Agricultural and Home Economics Experiment Station. p 11 9.
39. Wilson S, Wilson GS, Glass RS. 1994. The effect of pH and complexation of amino acid functionality on the redox chemistry of methionine and X-ray structure of [Co(en)2(L-Met)](ClO4)2.H2O. J Inorg Biochem 55 : 87 99.
40. Yang SF. 1970. Sulfoxide formation from methionine or its sulfide analogs during aerobic oxidation of sulfite. Biochemistry 9 (25 5008 14.
41. Yang SF. 1973. Destruction of tryptophan during the aerobic oxidation of sulfite ions. Environ Res 6 (4 395 402.