Novel yellow compounds, dilysyldipyrrolones A and B, formed from xylose and lysine by the Maillard reaction.

نویسندگان

  • Junko Sakamoto
  • Makiko Takenaka
  • Hiroshi Ono
  • Masatsune Murata
چکیده

When a solution containing xylose and L-lysine is heated under weakly acidic conditions, it turns brown by the Maillard reaction. We isolated here two novel yellow compounds from a heated solution containing xylose and lysine, and identified pyrrolyl-methylidene-pyrrolone derivatives named dilysyldipyrrolones A and B. Their chemical structures were elucidated by instrumental analyses as 6-[[1-[(S)-5-amino-1-carboxypentyl]-3-hydroxy-pyrrol-2-yl]-(E)-2-methylidene-5-methyl-1,2H-pyrrol-3-one-1-ly]-(S)-2-amino-hexanoic acid (dilysyldipyrrolone A) and 6-[[1-[(S)-5-amino-5-carboxypentyl]-3-hydroxy-pyrrol-2-yl]-(E)-2-methylidene-5-methyl-1,2H-pyrrol-3-one-1-yl]-(S)-2-amino-hexanoic acid (dilysyldipyrrolone B). These were the major pigments in the heated solution.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Two novel beta-carboline compounds from the Maillard reaction between xylose and tryptophan.

Two nonvolatile beta-carboline alkaloids were isolated from the Maillard reaction between xylose and tryptophan by solvent extraction and flash silica gel column chromatography. Their structures were elucidated by spectral methods (UV, MS, and NMR) as 1-(1,4-dihydroxybutyl)-beta-carboline and 1-(1,3, 4-trihydroxybutyl)-beta-carboline.

متن کامل

Antioxidative and Prooxidative Actions of Xylose-Lysine Maillard Reaction Products.

Maillard reaction products were prepared by heating xylose and lysine at pH 9.0 and 100°C for 3 h, and then fractionated by ethyl ether and ethanol into acidic, neutral and basic low-molecular-weight, ethanol-soluble and ethanol-insoluble fractions. The ethanol-soluble and -insoluble fractions were the major fractions of the xylose-lysine Maillard reaction products (XL MRPs), contributing 79.5%...

متن کامل

Contribution of sulfur-containing compounds to the colour-inhibiting effect and improved antioxidant activity of Maillard reaction products of soybean protein hydrolysates.

BACKGROUND Light-coloured and savoury-tasting flavour enhancers are attractive to both consumers and food producers. The aim of this study was to investigate the colour-inhibiting effect of L-cysteine and thiamine during the Maillard reaction of soybean peptide and D-xylose. The correlation between volatile compounds and antioxidant activity of the corresponding products was also studied. RES...

متن کامل

Triosidines: novel Maillard reaction products and cross-links from the reaction of triose sugars with lysine and arginine residues.

The role of the highly reactive triose sugars glyceraldehyde and glyceraldehyde-3-phosphate in protein cross-linking and other amino acid modifications during the Maillard reaction was investigated. From the incubation of glyceraldehyde with N (alpha)-acetyl-L-lysine and N (alpha)-acetyl-L-arginine, we isolated four new Maillard reaction pyridinium compounds named 'triosidines'. Two of them, 'l...

متن کامل

Role of the Maillard reaction in aging of tissue proteins. Advanced glycation end product-dependent increase in imidazolium cross-links in human lens proteins.

Dicarbonyl compounds such as glyoxal and methylglyoxal are reactive dicarbonyl intermediates in the nonenzymatic browning and cross-linking of proteins during the Maillard reaction. We describe here the quantification of glyoxal and methylglyoxal-derived imidazolium cross-links in tissue proteins. The imidazolium salt cross-links, glyoxal-lysine dimer (GOLD) and methylglyoxal-lysine dimer (MOLD...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Bioscience, biotechnology, and biochemistry

دوره 73 9  شماره 

صفحات  -

تاریخ انتشار 2009