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Methylglyoxal-derived β-carbolines formed from tryptophan and its derivates in the Maillard reaction

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Summary.

Reaction of tryptophan, tryptophan methyl ester and tryptamine with methylglyoxal (a physiological α-oxoaldehyde), which resulted in β-carboline formation, showed that this type of nonenzymatic (Maillard) reaction could spontaneously occur in living organisms or during commercial or domestic food processing and storage.

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References

  • F Bracher D Hilderbrand H Häberlein (2004) ArticleTitle1-Substituted β-carboline-3-carboxylates with high affinities to the benzodiazepine recognition site Nat Prod Res 18 391–396 Occurrence Handle15248604 Occurrence Handle10.1080/14786410310001630483 Occurrence Handle1:CAS:528:DC%2BD2cXlsFensr0%3D

    Article  PubMed  CAS  Google Scholar 

  • M Brownlee (2005) ArticleTitleThe pathobiology of diabetic complications – A unifying mechanism Diabetes 54 1615–1625 Occurrence Handle15919781 Occurrence Handle1:CAS:528:DC%2BD2MXltVaisbk%3D

    PubMed  CAS  Google Scholar 

  • F Faini M Castillo R Torres (1978) ArticleTitleA new β-carboline alkaloid from Vestia lycioides Phytochemistry 17 338–338 Occurrence Handle10.1016/S0031-9422(00)94190-6 Occurrence Handle1:CAS:528:DyaE1cXhslSgtb0%3D

    Article  CAS  Google Scholar 

  • BS Joshi VN Kamat DH Gawad (1977) ArticleTitleSome β-carboline alkaloids of Ailanthus malabarica DC Heterocycles 7 193–200 Occurrence Handle1:CAS:528:DyaE1cXjsVCqsQ%3D%3D Occurrence Handle10.3987/S-1977-01-0193

    Article  CAS  Google Scholar 

  • MP Kalapos (1999) ArticleTitleMethylglyoxal in living organisms; chemistry, biochemistry, toxicology and biological implications Toxicol Lett 110 145–175 Occurrence Handle10597025 Occurrence Handle10.1016/S0378-4274(99)00160-5 Occurrence Handle1:CAS:528:DC%2BD3cXhs1Gj

    Article  PubMed  CAS  Google Scholar 

  • AC McLellan SA Phillips PJ Thornalley (1992) ArticleTitleThe assay of methylglyoxal in biological systems by derivatization with 1,2-diamino-4,5-dimethoxybenzene Anal Biochem 344 109–116

    Google Scholar 

  • I Nemet Z Turk L Duvnjak N Car L Varga-Defterdarović (2005) ArticleTitleHumoral methylglyoxal level reflects glycemic fluctuation Clin Biochem 38 379–383 Occurrence Handle15766739 Occurrence Handle10.1016/j.clinbiochem.2004.12.008 Occurrence Handle1:CAS:528:DC%2BD2MXit1Ciurg%3D

    Article  PubMed  CAS  Google Scholar 

  • I Nemet L Varga-Defterdarović Z Turk (2004) ArticleTitlePreparation and quantification of methylglyoxal in human plasma using reverse-phase high-performance liquid chromatography Clin Biochem 37 875–881 Occurrence Handle15369718 Occurrence Handle10.1016/j.clinbiochem.2004.05.024 Occurrence Handle1:CAS:528:DC%2BD2cXnsFGlu74%3D

    Article  PubMed  CAS  Google Scholar 

  • A Previero L-G Barry J Torreilles (1984) ArticleTitleAromatization of 3,4-dihydro-β-carboline-3-carboxylic acid and its derivates through a carbanion intermediate: mechanistic study and use in chemical synthesis Tetrahedron 40 221–234 Occurrence Handle10.1016/0040-4020(84)85124-8 Occurrence Handle1:CAS:528:DyaL2cXktVKhtLg%3D

    Article  CAS  Google Scholar 

  • B Proksa D Uhrin M Šurdíková J Fuska (2004) ArticleTitle1-Acetyl-β-carboline, a new metabolite of Streptomyces kasugaensis Acta Biotechnol 10 337–340 Occurrence Handle10.1002/abio.370100405

    Article  Google Scholar 

  • T-S Zhou W-C Ye Z-T Wang C-T Che R-H Zhou G-J Xu L-S Xu (1998) ArticleTitleβ-Carboline alkaloids from Hypodematium squamuloso-pilosum Phytochemistry 49 1807–1809 Occurrence Handle11711107 Occurrence Handle10.1016/S0031-9422(98)00232-5 Occurrence Handle1:CAS:528:DyaK1cXotFCmtbo%3D

    Article  PubMed  CAS  Google Scholar 

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Authors and Affiliations

  1. Division of Organic Chemistry and Biochemistry, Ruđjer Bošković Institute, Zagreb, Croatia

    I. Nemet & L. Varga-Defterdarović

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  1. I. Nemet
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  2. L. Varga-Defterdarović
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Nemet, I., Varga-Defterdarović, L. Methylglyoxal-derived β-carbolines formed from tryptophan and its derivates in the Maillard reaction. Amino Acids 32, 291–293 (2007). https://doi.org/10.1007/s00726-006-0337-7

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  • DOI: https://doi.org/10.1007/s00726-006-0337-7