Hexanal synthesis in isolated soy proteins

JAOCS, Journal of the American Oil Chemists' Society

Volumn 84, Issue 3, 2007, Pages 249-257

  Boatright, W L ^a   Lu, G ^a  

^a UNIVERSITY OF KENTUCKY   (United States)

Author keywords

Erythrobate; Hexanal; Linoleic acid; Reducing agents; Soy protein

Indexed keywords

ALDEHYDES; AMINO ACIDS; BIOSYNTHESIS; MIXTURES; PROTEINS; REDUCING AGENTS; SEED;

CYSTEINE; ERYTHROBATE; HEXANAL; SOY PROTEIN;

FATTY ACIDS;

GLYCINE MAX;

EID: 34250644950     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-007-1036-6     Document Type: Article

References (55)

1. McLeod G, Ames J (1988) Soy flavor and its improvement. Crit Rev Food Sci Nutr 27:219-402
2. Wilson LA, Johnson LA, Hayenga ML, Love MH (1990) Protein used for food and industrial products. In: Greiner CA (ed) Economic implications of modified soybean traits. Iowa Agricultural and Home Economics Experiment Station, Ames, pp 11-19
3. Rah JH, Hasler CM, Painter JE, Chapman-Novakofske KM (2004) Applying the theory of planned behavior to women's behavioral attitudes on and consumption of soy products. J Nutr Educ Behav 36:238-244
4. He Y, Segranek JG (1996) Frankfurters with lean finely textured tissue as affected by ingredients. J Food Sci 61:1275-1280
5. Lecomte NB, Zayas JF, Kastner CL (1993) Soya protein functional and sensory characteristics improved in comminuted meats. J Food Sci 58:464-466
6. Matulis RJ, Floyd FK, Sutherland JW, Brewer MS (1995) Sensory characteristics of frankfurters as affected by salt, fat, soy protein, and carrageenan. J Food Sci 60:48-54
7. Wolf WJ, Cowan JC (1971) Soybeans as a food source. CRC, Boca Raton, pp 33-77
8. Sessa DJ, Rackis JJ (1977) Lipid-derived flavors of legume protein products. J Am Oil Chem Soc 54:468
9. Boatright WL, Lei Q (1999) Compounds contributing to the "beany" odor of aqueous solutions of soy protein isolates. J Food Sci 64:667-670
10. Boatright WL, Lei Q (2000) Headspace evaluation of methanethol and dimethyl trisulfide in aqueous solutions of soyprotein isolates. J Food Sci 65:819-821
11. Lei Q, Boatright WL (2001) Compounds contributing to the odor of aqueous slurries of soy protein concentrates. J Food Sci 66:1306-1310
12. Lei Q, Boatright WL (2001) Development of a new methanethiol quantification method using ethanethiol as an internal standard. J Agric Food Chem 49:3567-3572
13. Boatright WL (2002) Effect of gallic acid on the aroma constituents of soymilk and soy protein isolates. J Am Oil Chem Soc 79:317-323
14. King JM, Chin SM, Svendsen LK, Reitmeier CA, Johnson LA, Fehr WR (2001) Processing of lipoxygenase-free soybeans and evaluation in foods. J Am Oil Chem Soc 78:353-360
15. Maheshwari P, Murphy PA, Nikolov ZL (1997) Characterization and application of porcine liver aldehyde oxidase in the off-flavor reduction of soy proteins. J Agric Food Chem 45:2488-2494
16. Matoba T, Hidaka H, Kitamura K, Kaizuma N, Kito M (1985) Contribution of hydroperoxide lyase activity to n-hexanal formation in soybeans. J Agric Food Chem 33:856-858
17. Matoba T, Takamura H, Kitamura K (1996) Mechanism of beany flavor formation in lipoxygenase-deficient soybean. Rep Soy Protein Res Commun Jpn 17:29-32
18. Boatright WL, Stine CJ (2004) Residual sulfur metabolites in isolated soy proteins: sulfite to cysteine. J Food Sci 69:200-205
19. Monma M, Sugimoto T, Hashizume K, Saio K (1990) Lipoxygenase activities in soybean homogenate. Nippon Shokuhin Kogyo Gakkaishi 37:625-627
20. Kemal C, Louis-Flamberg P, Krupinski-Olsen P, Shorter AL (1987) Reductive inactivation of soybean lipoxygenase 1 by catechols: a possible mechanism for regulation of lipoxygenase activity. Biochemistry 26:7064-7072
21. Zamora R, Macias P, Mesias JL (1988) Carotene cooxidation activity of tomato lipoxygenase-2. Nahrung 32:965-969
22. Rehbock B, Berger RG (1988) Covalent immobilization of a hydroperoxide lyase from mung beans (Phaseolus radiatus L.). Biotechnol Tech 12:539-544
23. Matsui K, Kajiwara T, Hatanaka A (1992) Inactivation of tea leaf hydroperoxide lyase by fatty acid hydroperoxide. J Agric Food Chem 40:175-178
24. Noordermeer NA, Veldink GA, Vliegenthart JFG (2001) Fatty acid hydroperoxide lyase: a plant cytochrome P450 enzyme involved in wound healing and pest resistance. Chembiochem 2:494-504
25. Salch YP, Grove MJ, Takamura H, Gardner HW (1995) Characterization of a C-5,13-cleaving enzyme of 13(S)-hydroperoxide of linolenic acid by soybean seed. Plant Physiol 108:1211-1218
26. Bligh EG, Dyer WJ (1959) A rapid method of total lipid extraction and purification. Can J Biochem Phys 37:911-917
27. Boatright WL, Snyder HE (1993) Soybean protein bodies: phospholipids and phospholipase D activity. J Am Oil Chem Soc 70:623-628
28. Boatright WL, Crum AD (1997) Nonpolar-volatile lipids from soy protein isolates and hexane-defatted flakes. J Am Oil Chem Soc 74:461-467
29. Hick M, Gebicki JM (1979) A spectrophotometric method for the determination of lipid hydroperoxides. Anal Biochem 99:249-253
30. Privett OS, Dougherty KA, Castell JD (1971) Quantitative analysis of lipid classes. Am J Clin Nutr 24:1265
31. Blank ML, Schmit JA, Privett OS (1964) Quantitative analysis of lipids by thin-layer chromatography. J Am Oil Chem Soc 41:371
32. Skipski VV, Barclay M (1969) In: Lowenstein JM (ed) Methods in enzymology, vol IV. Academic, New York, p 542
33. Lepage M (1967) Identification and composition of turnip root lipids. Lipids 2:244-250
34. SAS Institute (1995) JMP® user's guide. Statistical Analysis System Institute, Cary
35. Mounts TL, Abidi SL, Rennick KA (1996) Effect of genetic modification on the content and composition of bioactive constituents of soybean oil. J Am Oil Chem Soc 73:581-586
36. Mukhamedova KS, Glushenkova AI (1998) Molecular composition of soybean phospholipids. Chem Nat Compd 33:693-694
37. Boatright WL, Hettiarachchy NS (1995) Effect of Lipids on soy protein isolate solubility. J Am Oil Chem Soc 72:1439
38. Erdahl WL, Stolyhwo A, Privett OS (1973) Analysis of soybean lecithin by thin layer and analytical liquid chromatography. J Am Oil Chem Soc 50:513
39. Wedzicha BL (1984) Principles and reactions. In: Wedzicha BL (ed) Chemistry of sulphur dioxide in foods. Elsevier, London, pp 69-78
40. Murugesan N, Hecht SM (1985) Bleomycin as an oxene transferase: catalytic oxygen transfer to oleins. J Am Chem Soc 107:493-500
41. Hlavica P (2004) Models and mechanisms of O-O bond activation by cytochrome P450: a critical assessment of the potential role of multiple active intermediates in oxidative catalysis. Eur J Biochem 271:4335-4360
42. Anthon GE, Barrett DM (2002) Kinetic parameters for the thermal inactivation of quality-related enzymes in carrot and potatoes. J Agric Food Chem 50:4119-4125
43. Salazar O, Cirino PC, Arnold FH (2003) Thermostabilization of cytochrom P450 peroxygenase. Chembiochem 4:891-893
44. Machado MF, Saraiva J (2002) Inactivation and reactivation kinetics of horseradish peroxidase in phosphate buffer and buffer-dimethylformamide solutions. Mol Catal B 19-20:451-457
45. Lee M-K, Kil J-O, Park I (1999) Thermostability and reactivation of peroxidase from soybean sprouts. Yongyan Kwahak Hoechi 28:81-86
46. Woycechowsky KJ, Raines RT (2000) Native disulfide bond formation in proteins. Curr Opin Chem Biol 4:533-539
47. Smith AK, Circle SJ (1972) Protein products as food ingredients. Soybeans Chem Technol 1:339-388
48. Song W-C, Brash AR (1991) Purification of and allene oxide synthase and identification of the enzyme as a cytochrome P450. Science 253:781-784
49. Chapple C (1998) Molecular-genetic analysis of plant cytochrome P450-dependent monooxygenases. Annu Rev Plant Physiol Plant Mol Biol 49:311-343
50. Itoh A, Vick BA (1999) The purification and characterization of fatty acid hydroperoxide lyase in sunflower. Biochim Biohphys Acta 1436:531-540
51. Olias J.M., J.J. Rios M. Valle, Manuel R. Zamora L.C. Sanz B. Axelrod (1990) Fatty acid hydroperoxide lyase in germinating soybean seedlings. J Agric Food Chem 38:624-630
52. Kondo Y, Haskidoko Y, Mizutani J (1995) An enzymatic formation of 13-oxo-trideca-9,11-dienoic acid from 13-hydroperoxylinolenic acid by a hemolytic hydroperoxide lyase in elicitor-treated soybean cotyledons. Biochim Biophys Acta 1255:9-15
53. Sekiya J, Monma T, Kajiwara T, Hatanaka A (1986) Changes in activities of lipoxygenase and hydroperoxide lyase during seed development of soybeans. Agric Biol Chem 50:521-522
54. Gardner H, Weisleder D, Plattner RD (1991) Hydroperoxide lyase and other hydroperoxide-metabolizing activity in tissues of soybean, Glycine max. Plant Physiol 97:1059-1072
55. Zhuang H, Hamilton-Kemp TR, Anderson RA, Hildebrand DF (1992) Developmental changes in C6-aldehyde formation by soybean leaves. Plant Physiol 100:80-87