Skip to main content

Advertisement

Log in

Protein-bound advanced glycation endproducts (AGEs) as bioactive amino acid derivatives in foods

  • Review Article
  • Published:
Amino Acids Aims and scope Submit manuscript

Summary.

The Maillard reaction or nonenzymatic browning is of outstanding importance for the formation of flavour and colour of heated foods. Corresponding reactions, also referred to as “glycation”, are known from biological systems, where the formation of advanced glycation endproducts (AGEs) shall play an important pathophysiological role in diabetes and uremia. In this review, pathways leading to the formation of individual protein-bound lysine and arginine derivatives in foods are described and nutritional consequences resulting from this posttranslational modifications of food proteins are discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • EC Abraham MS Swamy RE Perry (1989) ArticleTitleNonenzymatic glycosylation (glycation) of lens crystallins in diabetes and aging. Prog Clin Biol Res 304 123–139 Occurrence Handle2780679 Occurrence Handle1:STN:280:DyaL1Mzos12lug%3D%3D

    PubMed  CAS  Google Scholar 

  • MU Ahmed JA Dunn MD Walla SR Thorpe JW Baynes (1986) ArticleTitleIdentification of N-epsilon-carboxymethyllysine as a degradation product of fructoselysine in glycated protein. J Biol Chem 263 8816–8821

    Google Scholar 

  • M Amadori (1929) ArticleTitleThe condensation product of glucose and p-anisidine. Atti della Accademia Nazionale dei Lincei 9 226–230 Occurrence Handle1:CAS:528:DyaB1MXivFantA%3D%3D

    CAS  Google Scholar 

  • EFLJ Anet (1960) ArticleTitleDegradation of carbohydrates I. Isolation of 3-deoxyhexosones. Australian J Chem 13 396–403 Occurrence Handle1:CAS:528:DyaF3MXit1CnsQ%3D%3D Occurrence Handle10.1071/CH9600396

    Article  CAS  Google Scholar 

  • HE Berg MAJS van Boekel (1994) ArticleTitleDegradation of lactose during heating of milk. Neth Milk Dairy J 48 157–175 Occurrence Handle1:CAS:528:DyaK2MXivFSltL0%3D

    CAS  Google Scholar 

  • R Bergmann R Helling C Heichert M Scheunemann P Mading H Wittrisch B Johannsen T Henle (2001) ArticleTitleRadio fluorination and positron emission tomography (PET) as a new approach to study the in vivo distribution and elimination of the advanced glycation endproducts N-epsilon-carboxymethyllysine (CML) and N-epsilon-carboxyethyllysine (CEL). Nahrung/Food 45 182–188 Occurrence Handle1:CAS:528:DC%2BD3MXltFarsbg%3D Occurrence Handle10.1002/1521-3803(20010601)45:3<182::AID-FOOD182>3.0.CO;2-Q

    Article  CAS  Google Scholar 

  • KM Biemel HP Buhler O Reihl MO Lederer (2001) ArticleTitleIdentification and quantitative evaluation of the lysine-arginine crosslinks GODIC, MODIC, DODIC, and glucosepan in foods. Nahrung/Food 45 210–214 Occurrence Handle1:CAS:528:DC%2BD3MXltFartr8%3D Occurrence Handle10.1002/1521-3803(20010601)45:3<210::AID-FOOD210>3.0.CO;2-L

    Article  CAS  Google Scholar 

  • RC Borrelli A Visconti C Mennella M Anese V Fogliano (2002) ArticleTitleChemical characterization and antioxidant properties of coffee melanoidins. J Agric Food Chem 50 6527–6533 Occurrence Handle12381145 Occurrence Handle1:CAS:528:DC%2BD38XntFegs7Y%3D Occurrence Handle10.1021/jf025686o

    Article  PubMed  CAS  Google Scholar 

  • RC Borrelli C Mennella F Barba M Russo GL Russo K Krome HMF Erbersdobler V Faist V Fogliano (2003) ArticleTitleCharacterization of coloured compounds obtained by enzymatic extraction of bakery products. Food Chem Toxicol 41 1367–1374 Occurrence Handle12909270 Occurrence Handle1:CAS:528:DC%2BD3sXlvFGhsL0%3D

    PubMed  CAS  Google Scholar 

  • M Brownlee H Vlassara A Cerami (1983) ArticleTitleNonenzymatic glycosylation reduces the susceptibility of fibrin to degradation by plasmin. Diabetes 32 680–684 Occurrence Handle6222931 Occurrence Handle1:CAS:528:DyaL3sXltlGrsb8%3D

    PubMed  CAS  Google Scholar 

  • M Brownlee H Vlassara A Cerami (1984) ArticleTitleNonenzymatic glycosylation and the pathogenesis of diabetic complications. Ann Intern Med 101 527–537 Occurrence Handle6383165 Occurrence Handle1:CAS:528:DyaL2cXmtVygtbs%3D

    PubMed  CAS  Google Scholar 

  • KJ Carpenter FH Steinke GL Catignani HE Swaisgood MC Allred JL MacDonald M Schelstraete (1989) ArticleTitleThe estimation of ‘available lysine’ in human foods by three chemical procedures. Plant Foods Hum Nutr 39 129–135 Occurrence Handle2496402 Occurrence Handle1:CAS:528:DyaL1MXkt1ahur8%3D Occurrence Handle10.1007/BF01092409

    Article  PubMed  CAS  Google Scholar 

  • T Chavakis A Bierhaus PP Nawroth (2004) ArticleTitleRAGE (receptor for advanced glycation end products): a central player in the inflammatory response. Microbes Infect 6 1219–1225 Occurrence Handle15488742 Occurrence Handle1:CAS:528:DC%2BD2cXos1Chur0%3D Occurrence Handle10.1016/j.micinf.2004.08.004

    Article  PubMed  CAS  Google Scholar 

  • MP Cohen RS Clements (1999) ArticleTitleMeasuring glycated proteins: clinical and methodological aspects. Diabetes Technol Therapeutics 1 57–70 Occurrence Handle1:CAS:528:DyaK1MXmtFaru7w%3D

    CAS  Google Scholar 

  • M Daglia M Racchi A Papetti C Lanni S Govoni G Gazzani (2004) ArticleTitleIn vitro and ex vivo antihydroxyl radical activity of green and roasted coffee. J Agric Food Chem 52 1700–1704 Occurrence Handle15030233 Occurrence Handle1:CAS:528:DC%2BD2cXhsVKktbc%3D Occurrence Handle10.1021/jf030298n

    Article  PubMed  CAS  Google Scholar 

  • R Dittrich F El-Massry K Kunz F Rinaldi CC Peich MW Beckmann M Pischetsrieder (2003) ArticleTitleMaillard reaction products inhibit oxidation of human low-density lipoproteins in vitro. J Agric Food Chem 51 3900–3904 Occurrence Handle12797763 Occurrence Handle1:CAS:528:DC%2BD3sXjsl2hsLc%3D

    PubMed  CAS  Google Scholar 

  • M Dolores del Castillo N Corzo A Olano (1999) ArticleTitleEarly stages of Maillard reaction in dehydrated orange juice. J Agric Food Chem 47 4388–4390 Occurrence Handle1:CAS:528:DyaK1MXmtVCisbg%3D

    CAS  Google Scholar 

  • S Drusch V Faist HF Erbersdobler (1999) ArticleTitleDetermination of N-ɛ-carboxymethyllysine in milk products by a modified reversed-phase HPLC method. Food Chem 65 547–553 Occurrence Handle1:CAS:528:DyaK1MXisFKgsrg%3D Occurrence Handle10.1016/S0308-8146(98)00244-1

    Article  CAS  Google Scholar 

  • K Eichner (1982) ArticleTitleAnalytical detection of thermally induced qualitative changes in vegetables and fruits. Z Lebensm Unters Forsch 36 101–104 Occurrence Handle1:CAS:528:DyaL38XmtFCmsrY%3D

    CAS  Google Scholar 

  • H Erbersdobler G Bock (1967) ArticleTitleStudies on the identification of a demonstrably ninhydrin-positive substance in hydrolysates of heat-damaged proteins. Naturwiss 54 648 Occurrence Handle5590205 Occurrence Handle1:CAS:528:DyaF1cXls1Gnug%3D%3D Occurrence Handle10.1007/BF01142431

    Article  PubMed  CAS  Google Scholar 

  • H Erbersdobler I Gunsser G Weber (1970) ArticleTitleDegradation of fructoselysine by the intestinal flora. Zentralbl Veterinaermed 17 573–575 Occurrence Handle1:CAS:528:DyaE3cXltFOnuro%3D

    CAS  Google Scholar 

  • HF Erbersdobler B Dehn A Nangpal H Reuter (1987) ArticleTitleDetermination of furosine in heated milk as a measure of heat intensity during processing. J Dairy Res 54 147–151 Occurrence Handle1:CAS:528:DyaL2sXmsF2iuw%3D%3D Occurrence Handle10.1017/S0022029900025255

    Article  CAS  Google Scholar 

  • HF Erbersdobler M Lohmann K Buhl (1991) ArticleTitleUtilization of early Maillard reaction products by humans. Adv Exp Med Biol 289 363–370 Occurrence Handle1910249 Occurrence Handle1:CAS:528:DyaK38XhtVCrsrY%3D

    PubMed  CAS  Google Scholar 

  • PA Finot J Mauron (1972) ArticleTitleBlockage of lysine by Mallard’s reaction. II. Chemical properties of derivatives N-(deoxy-1-D-fructosyl-1) and N-(deoxy-1-D-lactulosyl-1) lysine. Helvetica Chimica Acta 55 1153–1164 Occurrence Handle5036612 Occurrence Handle1:CAS:528:DyaE38Xks1ahu7k%3D Occurrence Handle10.1002/hlca.19720550411

    Article  PubMed  CAS  Google Scholar 

  • PA Finot E Magnenat (1981) ArticleTitleMetabolic transit of early and advanced Maillard products. Prog Food Nutr Sci 5 193–207 Occurrence Handle6798629 Occurrence Handle1:CAS:528:DyaL38XosVCmuw%3D%3D

    PubMed  CAS  Google Scholar 

  • PA Finot J Bricout R Viani J Mauron (1968) ArticleTitleIdentification of a new lysine derivative obtained upon acid hydrolysis of heated milk. Experientia 24 1097–1099 Occurrence Handle5756467 Occurrence Handle1:CAS:528:DyaF1MXislOgtg%3D%3D Occurrence Handle10.1007/BF02147778

    Article  PubMed  CAS  Google Scholar 

  • PA Finot E Bujard F Mottu J Mauron (1977) ArticleTitleAvailability of the true Schiff’s bases of lysine. Chemical evaluation of the Schiff’s base between lysine and lactose in milk. Adv Exp Med Biol 86B 343–365 Occurrence Handle906923 Occurrence Handle1:CAS:528:DyaE1cXkvFWhtA%3D%3D

    PubMed  CAS  Google Scholar 

  • PA Finot R Deutsch E Bujard (1981) ArticleTitleThe extent of the Maillard reaction during the processing of milk. Prog Food Nutr Sci 5 345–355 Occurrence Handle1:CAS:528:DyaL38XmslCgsw%3D%3D

    CAS  Google Scholar 

  • A Förster T Henle (2003) ArticleTitleGlycation in food and metabolic transit of dietary AGEs: studies on urinary excretion of pyrraline. Biochem Soc Trans 31 1383–1385

    Google Scholar 

  • M Friedman (1996) ArticleTitleFood browning and its prevention. J Agric Food Chem 44 631–653 Occurrence Handle1:CAS:528:DyaK28Xht1ylsrs%3D

    CAS  Google Scholar 

  • MX Fu JR Requena AJ Jenkins TJ Lyons JW Baynes SR Thorpe (1996) ArticleTitleThe advanced glycation end product, N-epsilon-(carboxymethyl)lysine, is a product of both lipid peroxidation and glycoxidation reactions. J Biol Chem 271 9982–9986 Occurrence Handle8626637 Occurrence Handle1:CAS:528:DyaK28XisFGqtbs%3D Occurrence Handle10.1074/jbc.271.33.19641

    Article  PubMed  CAS  Google Scholar 

  • MA Glomb C Pfahler (2000) ArticleTitleSynthesis of 1-deoxy-D-erythro-hexo-2,3-diulose, a major hexose Maillard intermediate. Carbohydr Res 329 515–523 Occurrence Handle11128581 Occurrence Handle1:CAS:528:DC%2BD3cXotlCntL4%3D Occurrence Handle10.1016/S0008-6215(00)00219-6

    Article  PubMed  CAS  Google Scholar 

  • MA Glomb R Tschirnich (2001) ArticleTitleDetection of alpha-dicarbonyl compounds in Maillard reaction systems and in vivo. J Agric Food Chem 49 5543–5550 Occurrence Handle11714357 Occurrence Handle1:CAS:528:DC%2BD3MXnvVOltrs%3D

    PubMed  CAS  Google Scholar 

  • MA Glomb D Rosch RH Nagaraj (2001) ArticleTitleN(delta)-(5-hydroxy-4,6-dimethylpyrimidine-2-yl)-l-ornithine, a novel methylglyoxal-arginine modification in beer. J Agric Food Chem 49 366–372 Occurrence Handle11170600 Occurrence Handle1:CAS:528:DC%2BD3cXosFWmtL0%3D

    PubMed  CAS  Google Scholar 

  • T Goldberg W Cai M Peppa V Dardaine BS Baliga J Uribarri H Vlassara (2004) ArticleTitleAdvanced glycoxidation end products in commonly consumed foods. J Am Diet Assoc 104 1287–1291 Occurrence Handle15281050 Occurrence Handle1:CAS:528:DC%2BD2cXntV2ktL4%3D

    PubMed  CAS  Google Scholar 

  • J Hartkopf HF Erbersdobler (1994) ArticleTitleModel experiments of the formation of N epsilon-carboxymethyllysine in food products. Z Lebensm Unters Forsch 198 15–19 Occurrence Handle8171913 Occurrence Handle1:CAS:528:DyaK2cXmtVelt7c%3D Occurrence Handle10.1007/BF01195275

    Article  PubMed  CAS  Google Scholar 

  • K Hasenkopf B Ubel T Bordiehn M Pischetsrieder (2001) ArticleTitleDetermination of the Maillard product oxalic acid monolysinylamide (OMA) in heated milk products by ELISA. Nahrung/Food 45 206–209 Occurrence Handle1:CAS:528:DC%2BD3MXltFartr4%3D Occurrence Handle10.1002/1521-3803(20010601)45:3<206::AID-FOOD206>3.0.CO;2-1

    Article  CAS  Google Scholar 

  • T Hayashi M Namiki (1980) ArticleTitleFormation of two-carbon sugar fragment at an early stage of the browning reaction of sugar with amine. Agric Biol Chem 44 2575–2580 Occurrence Handle1:CAS:528:DyaL3MXot1GgsA%3D%3D

    CAS  Google Scholar 

  • C He J Sabol T Mitsuhashi H Vlassara (1999) ArticleTitleDietary glycotoxins: inhibition of reactive products by aminoguanidine facilitates renal clearance and reduces tissue sequestration. Diabetes 48 1308–1315 Occurrence Handle10342821 Occurrence Handle1:CAS:528:DyaK1MXjsFSgtrk%3D

    PubMed  CAS  Google Scholar 

  • T Henle (2003) ArticleTitleAGEs in food – do they play a role in uremia? Kidney Int 63 IssueIDs84 145–147 Occurrence Handle10.1046/j.1523-1755.63.s84.16.x

    Article  Google Scholar 

  • T Henle H Klostermeyer (1993) ArticleTitleDetermination of protein-bound 2-amino-6-(2-formyl-2-hydroxymethyl-1-pyrrolyl)-hexanoic acid (“pyrraline”) by ion-exchange chromatography and photodiode array detection. Z Lebensm Unters Forsch 196 1–4 Occurrence Handle1:CAS:528:DyaK3sXlsl2msLo%3D Occurrence Handle10.1007/BF01192975

    Article  CAS  Google Scholar 

  • T Henle T Miyata (2003) ArticleTitleAdvanced glycation end products in uremia. Adv Ren Repl Ther 10 321–331

    Google Scholar 

  • T Henle H Walter H Klostermeyer (1991) ArticleTitleEvaluation of the extent of the early Maillard-reaction in milk products by direct measurement of the Amadori-product lactuloselysine. Z Lebensm Unters Forsch 193 119–122 Occurrence Handle1781225 Occurrence Handle1:CAS:528:DyaK3MXmslyhurc%3D Occurrence Handle10.1007/BF01193359

    Article  PubMed  CAS  Google Scholar 

  • Henle T, Walter AW, Klostermeyer H (1994a) Simultaneous determination of protein-bound Maillard products by ion-exchange chromatography and photodiode array detection. – In: Labuza TP, Reineccius GA, Monnier VM, O’Brien J, Baynes JW (eds) Maillard reactions in chemistry, food, and health. The Royal Society of Chemistry, pp 195–200

  • T Henle AW Walter R Haessner H Klostermeyer (1994b) ArticleTitleIsolation and identification of a protein-bound imidazolone resulting from the reaction of arginine residues and methylglyoxal. Z Lebensm Unters Forsch 199 55–58 Occurrence Handle1:CAS:528:DyaK2cXltlamur8%3D Occurrence Handle10.1007/BF01192954

    Article  CAS  Google Scholar 

  • T Henle G Zehetner H Klostermeyer (1995) ArticleTitleFast and sensitive determination of furosine. Z Lebensm Unters Forsch 200 235–238 Occurrence Handle7785351 Occurrence Handle1:CAS:528:DyaK2MXltVKjs7o%3D Occurrence Handle10.1007/BF01190503

    Article  PubMed  CAS  Google Scholar 

  • Henle T, Schwarzenbolz U, Klostermeyer H (1996) Irreversible crosslinking of casein during storage of UHT-treated skim milk. Int Dairy Fed Special Issue No. 9602: 290–298

  • T Henle U Schwarzenbolz H Klostermeyer (1997) ArticleTitleDetection and quantification of pentosidine in foods. Z Lebensm Unters Forsch 204 95–98 Occurrence Handle1:CAS:528:DyaK2sXht1Cjt7Y%3D Occurrence Handle10.1007/s002170050043

    Article  CAS  Google Scholar 

  • T Henle V Schwenger E Ritz (2000) ArticleTitleStudies on the renal handling of lactuloselysine from milk products. Czech J Food Sci 18 IssueIDSpec Issue 101–102 Occurrence Handle1:CAS:528:DC%2BD3cXovVemtrg%3D

    CAS  Google Scholar 

  • K Heyns KH Meinecke (1953) ArticleTitleThe formation and preparation of D-glucosamine from fructose and ammonia. Chem Ber 86 1453–1562 Occurrence Handle1:CAS:528:DyaG2MXhtFyjsw%3D%3D

    CAS  Google Scholar 

  • JE Hodge (1953) ArticleTitleBrowning reactions in model systems. J Agric Food Chem 1 928–943 Occurrence Handle1:CAS:528:DyaG2cXht1Gjsg%3D%3D Occurrence Handle10.1021/jf60015a004

    Article  CAS  Google Scholar 

  • A Hoellnagel LW Kroh (1998) ArticleTitleFormation of alpha-dicarbonyl fragments from mono- and disaccharides under caramelization and Maillard reaction conditions. Z Lebensm Unters Forsch 207 50–54

    Google Scholar 

  • SM Hofmann HJ Dong Z Li W Cai J Altomonte SN Thung F Zeng EA Fisher H Vlassara (2002) ArticleTitleImproved insulin sensitivity is associated with restricted intake of dietary glycoxidation products in the db/db mouse. Diabetes 51 2082–2089 Occurrence Handle12086936 Occurrence Handle1:CAS:528:DC%2BD38Xlt1Wlt7w%3D

    PubMed  CAS  Google Scholar 

  • T Hofmann (1998a) ArticleTitleStudies on melanoidin-type colorants generated from the Maillard reaction of protein-bound lysine and furan-2-carboxaldehyde – chemical characterisation of a red coloured domaine. Z Lebensm Unters Forsch 206 251–258 Occurrence Handle1:CAS:528:DyaK1cXisVKqur0%3D Occurrence Handle10.1007/s002170050253

    Article  CAS  Google Scholar 

  • T Hofmann (1998b) ArticleTitle4-Alkylidene-2-imino-5-[4-alkylidene-5-oxo-1,3-imidazol-2-inyl]azamethylidene-1,3-imidazolidines – a novel colored substructure in melanoidins formed by Maillard reactions of bound arginine with glyoxal and furan-2-carboxaldehyde. J Agric Food Chem 46 3896–3901 Occurrence Handle1:CAS:528:DyaK1cXlvVOjtLg%3D

    CAS  Google Scholar 

  • BI Hudson AM Schmidt (2004) ArticleTitleRAGE: a novel target for drug intervention in diabetic vascular disease. Pharm Res 21 1079–1086 Occurrence Handle15290845 Occurrence Handle1:CAS:528:DC%2BD2cXltF2gt7k%3D Occurrence Handle10.1023/B:PHAM.0000032992.75423.9b

    Article  PubMed  CAS  Google Scholar 

  • A Ishizu B Lindberg O Theander (1967) ArticleTitle1-Deoxy-D-erythro-2,3-hexodiulose, an intermediate in the formation of D-glucosaccharinic acid. Carbohydr Res 5 329–334 Occurrence Handle1:CAS:528:DyaF1cXit1WmtA%3D%3D Occurrence Handle10.1016/S0008-6215(00)80507-8

    Article  CAS  Google Scholar 

  • H Jing DD Kitts (2004) ArticleTitleChemical characterization of different sugar-casein Maillard reaction products and protective effects on chemical-induced cytotoxicity of Caco-2 cells. Food Chem Toxicol 42 1833–1844 Occurrence Handle15350681 Occurrence Handle1:CAS:528:DC%2BD2cXntlGgtLY%3D

    PubMed  CAS  Google Scholar 

  • T Koschinsky CJ He T Mitsuhashi R Bucala C Liu C Buenting K Heitmann H Vlassara (1997) ArticleTitleOrally absorbed reactive glycation products (glycotoxins): an environmental risk factor in diabetic nephropathy. Proc Natl Acad Sci USA 94 6474–6479 Occurrence Handle9177242 Occurrence Handle1:CAS:528:DyaK2sXjvFGhu7g%3D Occurrence Handle10.1073/pnas.94.12.6474

    Article  PubMed  CAS  Google Scholar 

  • R Krause K Knoll T Henle (2003) ArticleTitleStudies in the formation of furosine and pyridosine during acid hydrolysis of different Amadori products of lysine. Eur Food Res Technol 216 277–283 Occurrence Handle1:CAS:528:DC%2BD3sXisleqsLY%3D

    CAS  Google Scholar 

  • R Krause J Kühn I Penndorf T Henle (2004) ArticleTitleN-terminal pyrazinones: a new class of peptide-bound advanced glycation end-products. Amino Acids 27 9–18 Occurrence Handle15309567 Occurrence Handle1:CAS:528:DC%2BD2cXmsVKktLk%3D Occurrence Handle10.1007/s00726-004-0102-8

    Article  PubMed  CAS  Google Scholar 

  • S Lauber H Klostermeyer T Henle (2001) ArticleTitleOn the influence of non-enzymatic crosslinking of caseins on the gel strength of yoghurt. Nahrung/Food 45 215–217 Occurrence Handle1:CAS:528:DC%2BD3MXltFartrw%3D Occurrence Handle10.1002/1521-3803(20010601)45:3<215::AID-FOOD215>3.0.CO;2-1

    Article  CAS  Google Scholar 

  • F Ledl E Schleicher (1990) ArticleTitleNew aspects of the Maillard reaction in food and in the human body. Angew Chem Int Ed Engl 29 565–594 Occurrence Handle10.1002/anie.199005653

    Article  Google Scholar 

  • M Lindenmeier T Hofmann (2004) ArticleTitleInfluence of baking conditions and precursor supplementation on the amounts of the antioxidant pronyl-L-lysine in bakery products. J Agric Food Chem 52 350–354 Occurrence Handle14733520 Occurrence Handle1:CAS:528:DC%2BD3sXpvVCnt7k%3D Occurrence Handle10.1021/jf0346657

    Article  PubMed  CAS  Google Scholar 

  • M Lindenmeier V Faist T Hofmann (2002) ArticleTitleStructural and functional characterization of pronyl-lysine, a novel protein modification in bread crust melanoidins showing in vitro antioxidative and phase I/II enzyme modulating activity. J Agric Food Chem 50 6997–7006 Occurrence Handle12428950 Occurrence Handle1:CAS:528:DC%2BD38XnvVOjurw%3D Occurrence Handle10.1021/jf020618n

    Article  PubMed  CAS  Google Scholar 

  • AR Ling (1909) ArticleTitleMalting. J Institute of Brewing 14 494–515 Occurrence Handle1:CAS:528:DyaD1MXktFc%3D

    CAS  Google Scholar 

  • M Lu M Kuroki S Amano M Tolentino K Keough I Kim R Bucala AP Adamis (1998) ArticleTitleAdvanced glycation end products increase retinal vascular endothelial growth factor expression. J Clin Invest 101 1219–1224 Occurrence Handle9502762 Occurrence Handle1:CAS:528:DyaK1cXitVWjt74%3D

    PubMed  CAS  Google Scholar 

  • LC Maillard (1912) ArticleTitleAction of amino acids on sugars. Formation of melanoidins in a methodical way. Compt Rend 154 66–68 Occurrence Handle1:CAS:528:DyaC38Xnt1Ck

    CAS  Google Scholar 

  • Z Makita S Radoff EJ Rayfield Z Yang E Skolnik V Delaney EA Friedman (1991) ArticleTitleAdvanced glycosylation endproducts in patients with diabetic nephropathy. N Engl J Med 325 836–842 Occurrence Handle1875967 Occurrence Handle1:STN:280:DyaK3Mzkt1OisQ%3D%3D Occurrence Handle10.1056/NEJM199109193251202

    Article  PubMed  CAS  Google Scholar 

  • D Marko M Kemeny E Bernady M Habermeyer U Weyand S Meiers O Frank T Hofmann (2002) ArticleTitleStudies on the inhibition of tumor cell growth and microtubule assembly by 3-hydroxy-4-[(E)-(2-furyl)methylidene]methyl-3-cyclopentene-1,2-dione, an intensively coloured Maillard reaction product. Food Chem Toxicol 40 9–18 Occurrence Handle11731031 Occurrence Handle1:CAS:528:DC%2BD3MXos1Gqs74%3D

    PubMed  CAS  Google Scholar 

  • D Marko M Habermeyer M Kemeny U Weyand E Niederberger O Frank T Hofmann (2003) ArticleTitleMaillard reaction products modulating the growth of human tumor cells in vitro. Chem Res Toxicol 16 48–55 Occurrence Handle12693030 Occurrence Handle1:CAS:528:DC%2BD38Xpt1ynurY%3D Occurrence Handle10.1021/tx025531a

    Article  PubMed  CAS  Google Scholar 

  • J Mauron (1990) ArticleTitleInfluence of processing on protein quality. J Nutr Sci Vitaminol (Tokyo) 36 S57–S69

    Google Scholar 

  • E Mavric Y Kumpf K Schuster O Kappenstein D Scheller T Henle (2004) ArticleTitleA new imidazolinone resulting from the reaction of peptide-bound arginine and oligosaccharides with 1,4-glycosidic linkages. Eur Food Res Technol 218 213–218 Occurrence Handle1:CAS:528:DC%2BD2cXhsFWqtbw%3D Occurrence Handle10.1007/s00217-003-0817-x

    Article  CAS  Google Scholar 

  • EV McCollum M Davis (1915) ArticleTitleThe cause of the loss of nutritive efficiency of heated milk. J Biol Chem 23 247–254 Occurrence Handle1:CAS:528:DyaC28XjtFGh

    CAS  Google Scholar 

  • JA Miller E Gravallese HF Bunn (1980) ArticleTitleNonenzymatic glycosylation of erythrocyte membrane proteins. Relevance to diabetes. J Clin Invest 65 896–901 Occurrence Handle7358849 Occurrence Handle1:CAS:528:DyaL3cXktVGht7s%3D Occurrence Handle10.1172/JCI109743

    Article  PubMed  CAS  Google Scholar 

  • T Miyata R Inagi Y Iida M Sato N Yamada O Oda K Maeda H Seo (1991) ArticleTitleInvolvement of β2-microglobulin modified with advanced glycation end products in the pathogenesis of hemodialysis-associated amyloidosis: Induction of human monocyte chemotaxis and macrophagesecretion of tumor necrosis factor and interleukin 1. J Clin Invest 93 521–528

    Google Scholar 

  • AB Moeller AT Andrews GC Cheeseman (1977) ArticleTitleChemical changes in ultra-heat-treated milk during storage. II. Lactuloselysine and fructoselysine formation by the Maillard reaction. J Dairy Res 44 267–275 Occurrence Handle1:CAS:528:DyaE2sXlsFSgsL0%3D

    CAS  Google Scholar 

  • LA Mucci PW Dickman G Steineck HO Adami K Augustsson (2003) ArticleTitleDietary acrylamide and cancer of the large bowel, kidney, and bladder: absence of an association in a population-based study in Sweden. Br J Cancer 88 84–89 Occurrence Handle12556964 Occurrence Handle1:CAS:528:DC%2BD3sXntFSnsw%3D%3D Occurrence Handle10.1038/sj.bjc.6600726

    Article  PubMed  CAS  Google Scholar 

  • LA Mucci P Lindblad G Steineck HO Adami (2004) ArticleTitleDietary acrylamide and risk of renal cell cancer. Int J Cancer 109 774–776 Occurrence Handle14999788 Occurrence Handle1:CAS:528:DC%2BD2cXivFCksr4%3D Occurrence Handle10.1002/ijc.20011

    Article  PubMed  CAS  Google Scholar 

  • M Nagao Y Fujita K Wakabayashi H Nukaya T Kosuge T Sugimura (1986) ArticleTitleMutagens in coffee and other beverages. Environ Health Perspect 67 89–91 Occurrence Handle3757962 Occurrence Handle1:CAS:528:DyaL28XlslSkur0%3D

    PubMed  CAS  Google Scholar 

  • T Nakayama F Hayase H Kato (1980) ArticleTitleFormation of epsilon-(2-formyl-5-hydroxy-methyl-pyrrol-1-yl)-L-norleucin in the Maillard reaction between D-glucose and L-lysine. Agric Biol Chem 44 1201–1202 Occurrence Handle1:CAS:528:DyaL3cXkvFGltrY%3D

    CAS  Google Scholar 

  • M Peppa J Uribarri H Vlassara (2002) ArticleTitleAdvanced glycoxidation. A new risk factor for cardiovascular disease? Cardiovasc Toxicol 2 275–287 Occurrence Handle12665661 Occurrence Handle1:CAS:528:DC%2BD3sXjsVWju74%3D

    PubMed  CAS  Google Scholar 

  • M Peppa J Uribarri W Cai M Lu H Vlassara (2004a) ArticleTitleGlycoxidation and inflammation in renal failure patients. Am J Kidney Dis 43 690–695 Occurrence Handle1:CAS:528:DC%2BD2cXjsFegt7Y%3D Occurrence Handle10.1053/j.ajkd.2003.11.022

    Article  CAS  Google Scholar 

  • M Peppa J Uribarri H Vlassara (2004b) ArticleTitleThe role of advanced glycation end products in the development of atherosclerosis. Curr Diab Rep 4 31–36

    Google Scholar 

  • SA Phillips PJ Thornalley (1993) ArticleTitleThe formation of methylglyoxal from triose phosphates. Investigation using a specific assay for methylglyoxal. Eur J Biochem 212 101–105 Occurrence Handle8444148 Occurrence Handle1:CAS:528:DyaK3sXhs1ensr0%3D Occurrence Handle10.1111/j.1432-1033.1993.tb17638.x

    Article  PubMed  CAS  Google Scholar 

  • AM Pischetsrieder C Schroeter T Severin (1998) ArticleTitleFormation of an aminoreductone during the Maillard reaction of lactose with N-α-acetyllysine or proteins. J Agric Food Chem 46 928–931 Occurrence Handle1:CAS:528:DyaK1cXhslakurk%3D

    CAS  Google Scholar 

  • S Rahbar O Blumenfeld HM Ranney (1969) ArticleTitleStudies of an unusual hemoglobin in patients with diabetes mellitus. Biochem Biophys Res Commun 36 838–843 Occurrence Handle5808299 Occurrence Handle1:CAS:528:DyaF1MXkvF2ksLw%3D Occurrence Handle10.1016/0006-291X(69)90685-8

    Article  PubMed  CAS  Google Scholar 

  • DS Raj D Choudhury TC Welbourne M Levi (2000) ArticleTitleAdvanced glycation end products: a Nephrologist’s perspective. Am J Kidney Dis 35 365–380 Occurrence Handle10692262 Occurrence Handle1:CAS:528:DC%2BD3cXhvFGiu74%3D

    PubMed  CAS  Google Scholar 

  • P Resmini L Pellegrino (1994) ArticleTitleOccurrence of protein-bound lysylpyrrolaldehyde in dried pasta. Cereal Chem 71 254–262 Occurrence Handle1:CAS:528:DyaK2cXmtVersbo%3D

    CAS  Google Scholar 

  • P Resmini L Pellegrino F Masotti A Tirelli F Prati (1992) ArticleTitleDetection of reconstituted milk powder in raw and in pasteurized milk by HPLC of furosine. Scienza e Tecnica Lattiero-Casearia 43 169–186 Occurrence Handle1:CAS:528:DyaK3sXlvVarsA%3D%3D

    CAS  Google Scholar 

  • JA Rodrigues AA Barros PG Rodrigues (1999) ArticleTitleDifferential pulse polarographic determination of alpha-dicarbonyl compounds in foodstuffs after derivatization with o-phenylenediamine. J Agric Food Chem 47 3219–3222 Occurrence Handle10552634 Occurrence Handle1:CAS:528:DyaK1MXksVWktL0%3D Occurrence Handle10.1021/jf980856b

    Article  PubMed  CAS  Google Scholar 

  • JA Rufian-Henares E Guerra-Hernandez B Garcia-Villanova (2004) ArticleTitlePyrraline content in enteral formula processing and storage and model systems. Eur Food Res Technol 219 42–47 Occurrence Handle1:CAS:528:DC%2BD2cXksVSgtbY%3D

    CAS  Google Scholar 

  • N Sakata J Meng S Takebayashi (2000) ArticleTitleEffects of advanced glycation end products on the proliferation and fibronectin production of smooth muscle cells. J Atheroscler Thromb 7 169–176 Occurrence Handle11480459 Occurrence Handle1:CAS:528:DC%2BD3MXktlelsbw%3D

    PubMed  CAS  Google Scholar 

  • ML Sanz MD del Castillo N Corzo A Olano (2001) ArticleTitleFormation of amadori compounds in dehydrated fruits. J Agric Food Chem 49 5228–5231 Occurrence Handle11714308 Occurrence Handle1:CAS:528:DC%2BD3MXns1Kru70%3D

    PubMed  CAS  Google Scholar 

  • ML Sanz MD del Castillo N Corzo A Olano (2003) ArticleTitle2-Furoylmethyl amino acids and aydroxymethylfurfural as indicators of honey quality. J Agric Food Chem 51 4278–4283 Occurrence Handle12848498 Occurrence Handle1:CAS:528:DC%2BD3sXksF2ku7c%3D Occurrence Handle10.1021/jf021235s

    Article  PubMed  CAS  Google Scholar 

  • SB Schwedler T Metzger R Schinzel C Wanner (2002) ArticleTitleAdvanced glycation end products and mortality in hemodialysis patients. Kidney Int 62 301–310 Occurrence Handle12081592 Occurrence Handle1:CAS:528:DC%2BD38XlsFyqu7o%3D Occurrence Handle10.1046/j.1523-1755.2002.00423.x

    Article  PubMed  CAS  Google Scholar 

  • V Schwenger M Zeier T Henle E Ritz (2001) ArticleTitleAdvanced glycation endproducts (AGEs) as uremic toxins. Nahrung/Food 45 172–176 Occurrence Handle1:CAS:528:DC%2BD3MXltFarsbo%3D Occurrence Handle10.1002/1521-3803(20010601)45:3<172::AID-FOOD172>3.0.CO;2-U

    Article  CAS  Google Scholar 

  • IN Shipanova MA Glomb RH Nagaraj (1997) ArticleTitleProtein modification by methylglyoxal: chemical nature and synthetic mechanism of a major fluorescent adduct. Arch Biochem Biophys 344 29–36 Occurrence Handle9244378 Occurrence Handle1:CAS:528:DyaK2sXltVOqtr0%3D Occurrence Handle10.1006/abbi.1997.0195

    Article  PubMed  CAS  Google Scholar 

  • S Shizuuchi F Hayase (2002) ArticleTitleAntioxidative activity of the blue pigment formed in a D-xylose-glycine reaction system. Biosci Biotechnol Biochem 67 54–59

    Google Scholar 

  • V Somoza M Lindenmeier E Wenzel O Frank HF Erbersdobler T Hofmann (2003) ArticleTitleActivity-guided identification of a chemopreventive compound in coffee beverage using in vitro and in vivo techniques. J Agric Food Chem 51 6861–6869 Occurrence Handle14582987 Occurrence Handle1:CAS:528:DC%2BD3sXnslaguro%3D Occurrence Handle10.1021/jf034750e

    Article  PubMed  CAS  Google Scholar 

  • D Stern SD Yan SF Yan AM Schmidt (2002) ArticleTitleReceptor for advanced glycation endproducts: a multiligand receptor magnifying cell stress in diverse pathologic settings. Adv Drug Deliv Rev 54 1615–1625 Occurrence Handle12453678 Occurrence Handle1:CAS:528:DC%2BD38XovFemtL0%3D Occurrence Handle10.1016/S0169-409X(02)00160-6

    Article  PubMed  CAS  Google Scholar 

  • S Sugiyama T Miyata R Inagi K Kurokawa (1998) ArticleTitleImplication of the glycoxidation and lipoxidation reactions in the pathogenesis of dialysis-related amyloidosis. Int J Mol Med 2 561–565 Occurrence Handle9858652 Occurrence Handle1:CAS:528:DyaK1cXnslSmsrc%3D

    PubMed  CAS  Google Scholar 

  • M Takahashi H Hoshino K Kushida K Kawana T Inoue (1996) ArticleTitleDirect quantification of pentosidine in urine and serum by HPLC with column switching. Clin Chem 42 1439–1444 Occurrence Handle8787701 Occurrence Handle1:CAS:528:DyaK28Xls1Sktbw%3D

    PubMed  CAS  Google Scholar 

  • PJ Thornalley (1996) ArticleTitlePharmacology of methylglyoxal: formation, modification of proteins and nucleic acids, and enzymatic detoxification – a role in pathogenesis and antiproliferative chemotherapy. Gen Pharmacol 27 565–573 Occurrence Handle8853285 Occurrence Handle1:CAS:528:DyaK28Xkt1ClsLo%3D

    PubMed  CAS  Google Scholar 

  • PJ Thornalley (1998) ArticleTitleCell activation by glycated proteins. AGE receptors, receptor recognition factors and functional classification of AGEs. Cell Mol Biol (Noisy-le-grand) 44 1013–1023 Occurrence Handle1:CAS:528:DyaK1cXns1Sksrk%3D

    CAS  Google Scholar 

  • J Uribarri M Peppa W Cai T Goldberg M Lu S Baliga JA Vassalotti H Vlassara (2003a) ArticleTitleDietary glycotoxins correlate with circulating advanced glycation end product levels in renal failure patients. Am J Kidney Dis 42 532–538 Occurrence Handle1:CAS:528:DC%2BD3sXnsleisb8%3D Occurrence Handle10.1016/S0272-6386(03)00779-0

    Article  CAS  Google Scholar 

  • J Uribarri M Peppa W Cai T Goldberg M Lu C He H Vlassara (2003b) ArticleTitleRestriction of dietary glycotoxins reduces excessive advanced glycation end products in renal failure patients. J Am Soc Nephrol 14 728–731 Occurrence Handle1:CAS:528:DC%2BD3sXht1KjtrY%3D Occurrence Handle10.1097/01.ASN.0000051593.41395.B9

    Article  CAS  Google Scholar 

  • T Usui S Shizuuchi H Watanabe F Hayase (2004) ArticleTitleProtective effect of Blue-M1 against oxidative stress on COS-1 cells. Biosci Biotechnol Biochem 68 247–249 Occurrence Handle14745194 Occurrence Handle1:CAS:528:DC%2BD2cXhtFKgtLY%3D

    PubMed  CAS  Google Scholar 

  • J Valle-Riestra RH Barnes (1970) ArticleTitleDigestion of heat-damaged egg albumen by the rat. J Nutr 100 873–882 Occurrence Handle5537066 Occurrence Handle1:CAS:528:DyaE3cXltVKrtLo%3D

    PubMed  CAS  Google Scholar 

  • H Vlassara M Brownlee A Cerami (1981) ArticleTitleNonenzymatic glycosylation of peripheral nerve protein in diabetes mellitus. Proc Natl Acad Sci USA 78 5190–5192 Occurrence Handle6946466 Occurrence Handle1:CAS:528:DyaL3MXlsVygsL4%3D

    PubMed  CAS  Google Scholar 

  • H Vlassara W Cai J Crandall T Goldberg R Oberstein V Dardaine M Peppa EJ Rayfield (2002) ArticleTitleInflammatory mediators are induced by dietary glycotoxins, a major risk factor for diabetic angiopathy. Proc Natl Acad Sci USA 99 15596–15601 Occurrence Handle12429856 Occurrence Handle1:CAS:528:DC%2BD3sXjvVyr Occurrence Handle10.1073/pnas.242407999

    Article  PubMed  CAS  Google Scholar 

  • H Weenan (1998) ArticleTitleReactive intermediates and carbohydrate fragmentation in Maillard chemistry. Food Chem 62 393–401

    Google Scholar 

  • KU Weigel T Opitz T Henle (2004) ArticleTitleStudies on the occurrence and formation of 1,2-dicarbonyls in honey. Eur Food Res Technol 218 147–151 Occurrence Handle1:CAS:528:DC%2BD2cXislektQ%3D%3D Occurrence Handle10.1007/s00217-003-0814-0

    Article  CAS  Google Scholar 

  • E Wiame G Delpierre F Collard E Van Schaftingen (2002) ArticleTitleIdentification of a pathway for the utilization of the Amadori product fructoselysine in Escherichia coli. J Biol Chem 277 42523–42529 Occurrence Handle12147680 Occurrence Handle1:CAS:528:DC%2BD38Xos1ensLo%3D Occurrence Handle10.1074/jbc.M200863200

    Article  PubMed  CAS  Google Scholar 

  • R Wittmann K Eichner (1989) ArticleTitleDetection of Maillard products in malts, beers, and brewing colorants. Z Lebensm Unters Forsch 188 212–220 Occurrence Handle1:CAS:528:DyaL1MXksFGksL8%3D Occurrence Handle10.1007/BF02112877

    Article  CAS  Google Scholar 

  • S Yamagishi M Takeuchi Y Inagaki K Nakamura T Imaizumi (2003) ArticleTitleRole of advanced glycation end products (AGEs) and their receptor (RAGE) in the pathogenesis of diabetic microangiopathy. Int J Clin Pharmacol Res 23 129–134 Occurrence Handle15224502 Occurrence Handle1:CAS:528:DC%2BD2cXlvVenu7c%3D

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Henle, T. Protein-bound advanced glycation endproducts (AGEs) as bioactive amino acid derivatives in foods. Amino Acids 29, 313–322 (2005). https://doi.org/10.1007/s00726-005-0200-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00726-005-0200-2

Navigation