Zusammenfassung
Durch die Maillard-Reaktion werden in Lebensmitteln und im menschlichen Körper reduzierende Zucker sowie Aminosäuren und Proteine verändert. Es lassen sich einige allgemeine und auch spezielle Abbauwege für Pentosen, Mono- und Disaccharide formulieren. Die Produktbildung wird u.a. durch die Art des Amins (primär oder sekundär) beeinflußt. Im Verlauf der Abbaureaktionen kann es zu C-C-Spaltungsreaktionen bei den Zuckern und bei Aminosäuren (Streckerabbau) kommen. Einige Maillard-Produkte sind als Indikatorsubstanzen zum Nachweis des Umfangs der Maillard-Reaktion geeignet.
Summary
Through the Maillard reaction, occurring in food and in the human body, reducing sugars, amino acids and proteins are transformed. Some general and also specific degradation pathways for pentoses, mono- and disaccharides can be defined. The structures of the products are influenced by the type of amine (primary or secondary). During the degradation reactions C-C fissions of the sugars and amino acids (Strecker degradation) can be observed. Some Maillard products are suited as indicator substances to determine the extent of the Maillard reaction.
Literatur
Ahmed MU, Thorpe SR, Baynes J (1985) Identification of N-carboxymethyllysine, a modified amino acid formed by decomposition of fructose-lysine in glycated proteins. Fed Proc 44:1621
Anet EFLJ (1960) Degradation of carbohydrates I. Isolation of 3-deoxyosones. Aust J Chem 13:369–403
Anet EFLJ (1964) 3-Deoxyglucosuloses(3-deoxyglycosones) and the degradation of carbohydrates. Adv Carbohyd Chem 19:181–218
Anet EFLJ, Ingles DL (1964) Mechanism of inhibition of nonenzymatic browning by sulphite. Chem Ind (London), p 1319
Baynes JW, Monnier VM (eds) (1989) The Maillard reaction in aging, diabetes and nutrition. AR Liss, New York, pp 1–393
Beck J, Ledl F, Sengl M, Severin Th (1990) Formation of acids, lactones and esters through the Maillard reaction. Z Lebensm Unters Forsch 190:212–216
Beck J, Ledl F, Severin Th (1988) Formation of 1-deoxy-erythro-2,3-hexodiulose from Amadori compounds. Carbohydr Res 177:240–243
Beck J, Ledl F, Severin Th (1989) Formation of glucosyl-deoxyosones from Amadori compounds of maltose. Z Lebensm Unters Forsch 188:118–121
Brand J (1894) Über Maltol. Chem Ber 27:806–810
Brüggemann J, Erbersdobler H (1968) Fructoselysin als wichtigstes Reaktions-produkt von Lysin mit Glucose bei Hitzeschädigung von Lebens- und Futtermitteln. Z Lebensm Unters Forsch 137:137–143
Bunn HF, Haney DN, Kamin S, Gabbay KH, Gallop PM (1976) Biosynthesis of human hemoglobin AIc: slow glycosylation of hemoglobin in vivo. J Clin Invest 57:1652–1659
Ciner-Doruk M, Eichner K (1979) Bildung und Stabilität von Amadori-Verbindungen in wasserarmen Lebensmitteln. Z Lebensm Unters Forsch 168:9–20
Droß A, Hardt R, Baltes W (1987) Nachweis und Identifizierung von Zuckercouleuren in einigen flüssigen Lebensmitteln. Fresenius Z Anal Chem 328:495–498
Erbersdobler H, Zucker H (1966) Untersuchungen zum Gehalt an Lysin und verfügbarem Lysin in Trockenmagermilch. Milchwissenschaft 21:564
Eriksson C (ed) (1981) Maillard reactions in food. Prog Fd Nutr Sci 5:1–501 Pergamon Press, Oxford
Estendorfer S, Ledl F, Severin Th (1990) Bildung eines Aminoreduktons aus Glucose. Angew Chem 102:547–548
Estendorfer S, Ledl F, Severin Th (1990) Formation of 4,5-dihydroxy-2-α-D-glucopyranosyloxy-5-methyl-2-cyclopenten-1-one in the Maillard reaction of maltose. Tetrahedron 46:5617–5620
Farmar JG, Ulrich PC, Cerami A (1988) Novel pyrroles from sulfite-inhibited Maillard reactions: Insight into the mechanism of inhibition. J Org Chem 53:2346–2349
Finot P-A, Mauron J (1969) Le blocage de la lysine par la réaction de Maillard. I. Synthèse de N-(deoxy-1-D-fructosyl-1) et N-(deoxy-1-D-lactulosyl-1)-L-lysines. Helv Chim Acta 52:1488–1495
Finot PA, Aeschbacher HU, Hurrel RF, Liardon R (1990) The Maillard reaction in food processing, human nutrition and physiology. Birkhäuser Verlag Basel, Brüssel, Berlin, pp 1–516
Finot PA, Viani R, Bricont J, Mauron J (1968) Identification of a new lysine derivative obtained upon acid hydrolysis of heated milk. Experientia 24:1097–1099
Fors S (1983) Sensory properties of volatile Maillard reaction products and related compounds. In: Lit 15 S 185–286
Fujimaki M, Namiki M, Kato M (eds) (1986) Amino-carbonyl reactions in food and biological systems. Dev Food Sci 13:1–579
Goodwin JC (1983) Isolation of 3-O-α-D-gluco- and 3-O-β-D-galacto-pyranosyloxy-2-furylmethylketones from nonenzymic browning of maltose and lactose with secondary amino acids. Carbohydr Res 115:281–287
Hayase F, Nagaraj R, Miyata S, Njoroge G, Monnier VM (1989) Aging of proteins: immunological detection of a glucose-derived pyrrole formed during the Maillard reaction in vivo. J Biol Chem 264:3758–3764
Helak B, Kersten E, Spengler K, Tressl R, Rewicki D (1989) Formation of furylpyrrolidines and -piperidines on heating L-proline with reducing sugars and furancarboxaldehydes. J Agric Food Chem 37:405–410
Helak B, Spengler K, Tressl R, Rewicki D (1989) Formation of 7H-cyclopenta[b]pyridin-7-ones as proline-specific Maillard products. J Agric Food Chem 37:400–404
Heyns K, Heukeshoven J, Brose KH (1968) Der Abbau von Fruktoseaminosäuren zu N-(z-Furoylmethyl)-Aminosäuren. Angew Chem 80:627
Hiebl J, Ledl F, Severin Th (1987) Isolation of 4-hydroxy-2-(hydroxymethyl)-5-methyl-3(2H)-furanone from sugar amino acid reaction mixtures. J Agric Food Chem 35:990–993
Hodge JE (1963) Dicarbonyls, reductones and heterocyclics produced by reactions of reducing sugars with secondary amine salts. Am Soc Brewing Chemistry Proc 84–92
Hodge JE, Nelson EC (1961) Preparation and properties of galactosylisomaltol and isomaltol. Cereal Chem 38:207–228
Huber B, Ledl F (1990) Formation of 1-amino-1,4-dideoxy-2,3-hexodiuloses and 2-aminoacetylfurans in the Maillard reaction. Carbohydr Res 204:215–220
Jurch GR, Tatum JH (1970) Degradation of D-glucose with acetic acid and methylamine. Carbohydr Res 15:233–239
Kasai H, Yamaizumi Z, Wakabayashi K, Nagao M, Sugimura T, Yokohama S, Miyazawa T, Nishimura S (1980) Structure and chemical synthesis of Me-IQ, a potent mutagen isolated from boiled fish. Chem Lett 1391–1394
Kato H (1960) Studies on browning reactions between sugars and amino acids. V. Isolation and characterization of new carbonyl compounds, 3-deoxyosones formed from N-glycosides and their significance for browning reaction. Bull Agr Chem Soc Japan 24:1–12
Knowles ME (1971) Inhibition of non-enzymatic browning by sulphite: Identification of sulphonated products. Chem Ind (London), pp 910–911
Komoto M, Tsuchida H (1980) Formation of 2,5-bis-(D-threo-trihydroxypropyl)-pyrazine and its 6-isomer by the oxidative browning reaction of xylose with ammonium acetate in a methanolic medium. Agric Biol Chem 44:1189–1190
Kontoghiorghes GJ, Evans RW (1985) Site specificity of iron removal from transferrin by ketohydroxypyridine chelators. FEBS Lett 189:141–144
Krönig U, Severin Th (1973) Bildung von Pyrrolderivaten aus Pentosen und Alkylammoniumsalzen. Chem Mikrobiol Technol Lebensm 2:49–51
Kröplin U, Rosdorfer J, van der Greef J, Long RC, Goldstein JH (1985) 2-Acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole: detection in commercial caramel colour III and preparation by a model browning reaction. J Org Chem 50:1131–1133
Ledl F (1984) Bildung von Aminoreduktonen aus Disacchariden. Z Lebensm Unters Forsch 179:381–384
Ledl F (1987) Analytik flüchtiger Zuckerabbauprodukte. Lebensmittelchem Gerichtl Chem 41:83–87
Ledl F, Ellrich G, Klostermeyer H (1986) Nachweis und Identifizierung einer neuen Maillard-Verbindung in erhitzter Milch. Z Lebensm Unters Forsch 182:19–24
Ledl F, Fritsch G (1984) Bildung von Pyrrolinonreduktonen beim Erhitzen von Hexosen mit Aminosäuren. Z Lebensm Unters Forsch 178:41–44
Ledl F, Krönig U, Severin Th, Lotter H (1983) Untersuchungen zur Maillard-Reaktion. XVIII. Isolierung N-haltiger farbiger Verbindungen. Z Lebensm Unters Forsch 177:267–270
Ledl F, Osiander H, Pachmayr O, Severin Th (1989) Formation of maltosine, a product of the Maillard reaction with a pyridone structure. Z Lebensm Unters Forsch 188:207–211
Ledl F, Schleicher E (1990) Die Maillard-Reaktion in Lebensmitteln und im menschlichen Körper — neue Ergebnisse zu Chemie, Biochemie und Medizin. Angew Chem 102:597–626
Ledl F, Schnell W, Severin Th (1976) Nachweis von 2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-on in Lebensmitteln. Untersuchungen zur Maillard-Reaktion. XI. Z Lebensm Unters Forsch 160:367–370
Liardon R, de Weck-Goudard D, Philippossian G, Finot P-A (1987) Identification of Nε-carboxymethyllysine: A new Maillard reaction product, in rat urine. J Agric Food Chem 35:427–431
Lindberg B, Tanaka J, Theander O (1964) Reaction between D-glucose and sulphite. Acta Chem Scand 18:1164–1170
Maillard LC (1912) Action des acides aminés sur les sucres; formation des melanoidines par voie methodique. C R Acad Sci 154:66–68
Matsuura H, Hirao Y, Yoshida S, Kunihiro K, Fuwa T, Kasai R, Tanaka O (1984) Study of red ginseng: new glucosides and a note on the occurrence of maltol. Chem Pharm Bull 32:4674–4677
Mills FD, Weisleder D, Hodge JE (1970) 2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one, a novel nonenzymatic browning product. Tetrahedron Lett 5:1243–1246
Monnier VM; persönliche Mitteilung
Nedvidek W, Ledl F; unveröffentlicht
Nelson WO, Rettig SJ, Orvig C (1987) The exoclathrate Al(C7H8NO2)3 12H2O. A facial geometry imposed by extensive hydrogen bonding with the ice I structure. J Am Chem Soc 109:4121–4123
Njoroge FG, Fernandes AA, Monnier VM (1987) 3-(D-erythro-Trihydroxypropyl)-1-neopentylpyrrole-2-carboxaldehyde, a novel nonenzymatic browning product of glucose. J Carbohydr Chem 6:553–568
Nyhammar T, Olsson K, Pernemalm PA (1983) On the formation of 2-acylpyrroles and 3-pyridinols in the Maillard reaction through Strecker degradation. Acta Scand Chem B 37:879–889
Olsson K, Pernemalm PA, Theander O (1978) Formation of aromatic compounds from carbohydrates. VII. Reaction of D-glucose and glycine in slightly acidic, aqueous solution. Acta Chem Scand B 32:249–256
Pabst HME, Ledl F, Belitz HD (1984) Bitterstoffe beim Erhitzen von Saccharose und Prolin. Z Lebensm Unters Forsch 178:356–360 und (1985) Bitterstoffe beim Erhitzen von Saccharose, Maltose und Prolin 181:386–390
Pabst HME, Lotter H, Belitz HD (1988) Bitterstoffe beim Erhitzen von Prolin und Saccharose. Z Lebensm Unters Forsch 186:311–314
Pachmayr O, Ledl F, Severin Th (1986) Bildung von 1-Alkyl-3-oxopyridiniumbetainen aus Zuckern. Z Lebensm Unters Forsch 182:294–297
Parliment Th, McGorrin RJ, Ho CT (1989) Thermal generation of aromas. ACS Symp Ser 409:1–532, ACS Washington DC
Patton S (1950) The formation of maltol in certain carbohydrate-glycine systems. J Biol Chem 184:131–134
Paulsen H, Pflughaupt KW (1980) Glycosylamines. In: Pigman W, Horton D (eds) Carbohydrates IB. Academic Press, New York London Toronto Sydney San Francisco, pp 881–927
Pigman W, Anet EFLJ (1972) Mutarotations and actions of acids and bases. In: Pigman W, Horton D (eds) Carbohydrates IA. Academic Press, New York London Toronto Sydney San Francisco, pp 165–194
Rodin JO, Himel CM, Silverstein RM, Leeper RW, Gartner WA (1965) Volatile flavor and aroma components of pinapple. I. Isolation and tentative identification of 2,5-dimethyl-4-hydroxy-3(2H)-furanone. J Food Sci 30:280–285
Schönberg A, Moubacher R (1952) The Strecker degradation of α-amino acids. Chem Revs 50:261–277
Schüßler U, Ledl F (1989) Direct determination of 2-amino-6-(2-formyl-5-hydroxymethyl-1-pyrrolyl)-hexanoic acid in hydrolyzed protein by reversedphase HPLC. Z Lebensm Unters Forsch 189:32–35
Schüßler U, Ledl F (1989) Synthesis of 2-amino-6-(2-formyl-5-hydroxymethyl-1-pyrrolyl-)-hexanoic acid. Z Lebensm Unters Forsch 189:138–140
Sell DR, Monnier VM (1989) Structure elucidation of a senescence cross-link from human extracellular matrix. Implication of pentoses in the aging process. J Biol Chem 264:21597–21602
Sengl M, Ledl F, Severin Th (1989) Maillard-Reaktion von Rinderserumalbumin mit Glucose. HPLC-Nachweis des 2-Formyl-5-(hydroxymethyl)pyrrol-1-norleucins nach alkalischer Hydrolyse. J Chromatography 463:119–125
Severin Th, Krönig U (1973) Kondensation von Xylose mit Methylammoniumacetat. Z Lebensm Unters Forsch 152:42–46
Severin Th, Loidl A (1976) Bildung eines Pyridon-Derivates aus Maltose und Laktose. Z Lebensm Unters Forsch 161:119–124
Severin Th, Seilmeier W (1967) Umwandlung von Pentosen unter dem Einfluß von Aminacetaten. Z Lebens Unters Forsch 134:230–232
Severin Th, Seilmeier W (1968) Studien zur Maillard-Reaktion. III. Mitteilung. Umwandlung von Glucose unter dem Einfluß von Methylammoniumacetat. Z Lebensm Unters Forsch 137:4–6
Shaw PE, Berry RE (1977) Hexose-amino acid degradation studies involving formation of pyrroles, furans, and other low molecular weight products. J Agric Food Chem 25:641–644
Spingarn NE, Kasai H, Vuolo U, Nishimura S, Yamaizumi Z, Sugimura T, Matsushima T, Weisburger JH (1980) Formation of mutagens in cooked foods. III. Isolation of a potent mutagen from beef. Cancer Lett 9:177–183
Sugimura T, Kawachi M, Gajao T, Gagaki T, Seino Y, Okamoto T, Shodo K, Kosuge T, Tsuji K, Watabayashi K, Jitaka Y, Itai A (1977) Mutagenic principle(s) in tryptophan and phenylalanine pyrolysis products. Proc Jpn Acad 53:58–61
Tonsbeek CHT, Plancken AJ, van de Weerdhof TJ (1968) Components contributing to beef flavour. Isolation of 4-hydroxy-5-methyl-3(2H)-furanone and its 2,5-dimethyl homolog from beef broth. J Agric Food Chem 16:1016–1021
Tressl R, Grünewald KG, Kersten E, Rewicki D (1985) Formation of pyrroles and tetrahydro-indolizin-6-ones as hydroxyproline-specific Maillard products from glucose and rhamnose. J Agric Food Chem 34:347–350
Tressl R, Grünewald KG, Kersten E, Rewicki D (1986) Formation of pyrroles and tetrahydroindolizin-6-ones as hydroxyproline-specific Maillard products from erythrose and arabinose. J Agric Food Chem 34:347–350
Tressl R, Helak B, Kamperschröer H, Rewicki D (1985) Formation of pyrrolidines on heating L-proline with reducing sugars. J Agric Food Chem 33:924–928
Tressl R, Helak B, Kamperschröer M, Martin N, Rewicki D (1985) Formation of 2,3-dihydro-1H-pyrrolizines as proline specific Maillard products. J Agric Food Chem 33:919–923
Tressl R, Helak B, Köppler H, Rewicki D (1985) Formation of 2-(1-pyrrolidinyl)-2-cyclopentenones and cyclopent[b]azepin-8(1H)-ones as proline specific Maillard products. J Agric Food Chem 33:1132–1137
Tressl R, Helak B, Rewicki D (1982) Malzoxazin, eine tricyclische Verbindung aus Gerstenmalz. Helv Chim Acta 65:483–489
Tressl R, Helak B, Sprengler K, Schröder A, Rewicki D (1985) Cyclopent[b]azepin-Derivate, neue Prolin-spezifische Maillard-Produkte. Liebigs Ann Chem 2017–2027
Tsuchida H, Komoto M, Kato K, Fujimaki M (1973) Formation of deoxyfructosazine and its 6-isomer on the browning reaction between glucose and ammonia in weak acid medium. Agric Biol Chem 37:2571–2578
Tsuchida H, Tachibana S, Komoto M (1976) Isolation and identification of 2-(D-threo-trihydroxypropyl)-5-(D-glycero-2′,3′-dihydroxypropyl)pyrazine and its 6-isomer from the browning reaction between xylose and ammonium formate. Agric Biol Chem 40:1241–1242
Uhde WJ, Macholz R (1986) Mutagene Substanzen in Aminosäure-und Proteinpyrolysaten sowie hitzebehandelten Lebensmitteln. Nahrung 30:59–73
Waller Gr, Feather M (eds) (1983) Maillard reactions in food and nutrition. ACS Symp Ser 215:1–564 ACS Washington DC
Wedzicha BL (ed) (1984) Chemistry of sulphur dioxide in foods. Elsevier Applied Science, London New York, pp 1–381
Weygand F, Simon H, Bitterlich W, Hodge JE, Fischer BE (1958) Structure of piperidino-hexose-reductone. Tetrahedron 6:123–138
Wittmann R, Eichner K (1989) Nachweis von Maillard-Produkten in Malzen, Bieren und Braucouleuren. Z Lebensm Unters Forsch 188:212–220
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Ledl, F. Der Abbau von reduzierenden Zuckern und Aminen bei der Maillard-Reaktion. Z Ernährungswiss 30, 4–17 (1991). https://doi.org/10.1007/BF01910728
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DOI: https://doi.org/10.1007/BF01910728