Summary
In order to verify the formation of endogenous 3-deoxyglucosone (3-DG), an intermediate compound in the Maillard reaction, we tried to detect 3-deoxyfructose (3-DF) which is main metabolite of 3-DG. Endogenous 3-DF was detected in the urine of normal and diabetic rats by the oral administration of 3-DG-free feed. Metabolizing activities of crude extracts prepared from porcine organs were examined using methylglyoxal (MG) and 3-DG as substrates. NAD- or NADP-dependent 2-oxoaldehyde dehydrogenase activity was detected in liver, kidney, small intestine and lung. On the other hand, NADH- or NADPH-dependent 2-oxoaldehyde reductase activity was detected in all porcine organs in which liver and kidney contained higher activity of NADPH-dependent enzyme than the other organs. The reductase which catalyzes the reduction of 3-DG to 3-DF and MG to acetol, was purified and characterized from porcine kidney. The enzyme was the same to NADPH-dependent-2-oxoaldehyde reductase from porcine liver, which is speculated to prevent the advanced stage of the Maillard reaction as a self-defense enzyme.
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References
Attwood MA, Doughty C (1974) Biochim Biophys Acta 370: 358–368
Cerami A (1985) J Am Geriatr Sci 33: 626–634
Együd LG, Szent-Györgyi A (1966) Proc Natl Acad Sci USA 55: 388–393
Hamilton JK, Smith F (1952) J Am Chem Soc 74: 5162–5163
Hayase F, Nagaraj RH, Miyata S, Njoroge FG, Monnier VM (1989) J Biol Chem 264: 3758–3764
Horiuchi S, Tanaka K, Araki N, Morino Y (1990) In: Finot PA, Aeschbacher HU, Hurrell RF, Liardon R (eds) The Maillard reaction in food processing, human nutrition and physiology. Birkhäuser, Basel, pp 455–460
Huff E, Rudney H (1959) J Biol Chem 234: 1060–1064
Jellum E (1968) Biochim Biophys Acta 165: 357–363
Kato H, Yamada Y, Izaka K, Sakurai Y (1961) J Agr Chem Soc Japan 35: 412–415
Kato H, Ichihata H, Fujimaki M (1963) J Agr Chem Soc Japan 37: 220–225
Kato H, Tsusaka N, Fujimaki M (1970) Agric Biol Chem 34: 1541–1548
Kato H, Cho RK, Okitani A, Hayase F (1987a) Agric Biol Chem 51: 683–689
Kato H, Shin DB, Hayase F (1987b) Agric Biol Chem 51: 2009–2011
Kato H, Miyauchi Y, Nishimura T, Liang ZQ (1988) Agric Biol Chem 52: 2641–2642
Kato H, Hayase F, Shin DB, Oimomi M. Baba S (1989) Prog Clin Biol Res 304: 69–84
Kato H, Chuyen NV, Shinoda T, Sekiya F, Hayase F (1990) Biochim Biophys Acta 1035: 71–76
Liang ZQ, Hayase F, Nishimura T, Kato H (1990a) Agric Biol Chem 54: 319–328
Liang ZQ, Hayase F, Nishimura T, Kato H (1990b) Agric Biol Chem 54: 2727–2729
Liang ZQ, Hayase F, Kato H (1990c) J Japan Soc Biosci Biotech Agrochem (Japan) 64: 758 (Abstracts in 1990 Meeting of Japan Soc Biosci Biotech and Agrochem)
Liang ZQ, Hayase F, Kato H (1991) Eur J Biochem 197: 373–379
Lowry OH, Rosebrough NJ, Farr AL, Randall RJ (1951) J Biol Chem 193: 265–275
Monnier VM, Vishwanath V, Frank KE, Elmets CA, Dauchot P, Kohn RR (1986) N Engl J Med 314: 403–408
Shin DB, Hayase F, Kato H (1988) Agric Biol Chem 52: 1451–1458
Shin HS, Nishimura T, Hayase F, Kato H (1991) Agric Biol Chem 55: 957–966
Shinoda T, Chuyen NV, Hayase F, Kato H (1990) In: Finot PA, Aeschbacher HU, Hurrell RF, Liardon R (eds) The Maillard reaction in food processing, human nutrition and physiology. Birkhäuser, Basel, pp 309–314
Shinoda T, Hayase F, Chuyen NV, Kato H (1991) J Japan Soc Biosci Biotech Agrochem (Japan) 65: 523 (Abstracts in 1991 Meeting of Japan Soc Biosci Biotech and Agrochem)
Suzuki Y, Shinoda T, Hayase F, Chuyen NV, Kato H (1991) J Japan Soc Biosci Biotech Agrochem Japan 65: 371 (Abstracts in 1991 Meeting of Japan Soc Biosci Biotech and Agrochem)
Szent-Györgyi A, Hegyeli A, McLaughlin JA (1963) Science 140: 1391–1392
Szent-Györgyi A, Együd LG, McLaughlin JA (1967) Science 155: 539–541
Szwergold BS, Kappler F, Brown TR (1990) Science 247: 451–454
Vlassara H, Brownlee M, Cerami A (1989) In: Baynes JW, Monnier VM (eds) The Maillard reaction in aging, diabetes and nutrition, Bethesda 1988. Alan R Liss, New York (Prog Clin Biol Res 304: 69–84)
Weber K, Osborn M (1969) J Biol Chem 244: 4406–4412
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Hayase, F., Liang, Z.Q., Suzuki, Y. et al. Enzymatic metabolism of 3-deoxyglucosone, a Maillard intermediate. Amino Acids 1, 307–318 (1991). https://doi.org/10.1007/BF00814000
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DOI: https://doi.org/10.1007/BF00814000