Conditions for the Formation of Dilysyl-Dipyrrolones A and B, and Novel Yellow Dipyrrolone Derivatives Formed from Xylose and Amino Acids in the Presence of Lysine

Nomi, Yuri; Sakamoto, Junko; Takenaka, Makiko; Ono, Hiroshi; Murata, Masatsune

doi:10.1271/bbb.100390

Cited by 16 publications

(6 citation statements)

References 17 publications

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“…DLDPs A, B, and C ( Fig. 1) are reported as the major low-molecular-weight Maillard pigments in the xylose-lysine system under weakly acidic conditions (Sakamoto et al, 2011;Nomi et al, 2013). Figure 3 shows the reversed-phase HPLC profiles of the reaction solutions consisting of different buffers.…”

Section: Resultsmentioning

confidence: 99%

“…1), significantly contributed to the browning or color of a heated solution of xylose and lysine under weakly acidic conditions (Sakamoto et al, 2009;Nomi et al, 2011;Nomi et al, 2013). This result suggests that low-molecular-weight pigments in addition to melanoidins, high-molecular-weight brown compounds, should be considered in the color regulation of solutions containing sugars and amino acids.…”

Section: Introductionmentioning

confidence: 94%

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Effects of Sugar and Buffer Types, and pH on Formation of Maillard Pigments in the Lysine Model System

Mikami

Murata

2015

FSTR

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Effects of the types of sugars and buffers, and pH on the formation of Maillard reaction pigments were investigated using the xylose-lysine and glucose-lysine model systems. Sugars (13.3 mM) and lysine (34 mM) were dissolved in acetate, phosphate, and tris(hydroxymethyl)aminomethane (Tris) buffers and heated at 100℃ for 60 min. The profiles of browning, reversed-phase HPLC, sugar-decrease, and gel permeation chromatography of each sample were examined. Browning was stimulated by phosphate and inhibited by Tris. With the rise in pH value, browning occurred more intensively, more sugars decreased, and more melanoidins were formed. Xylose samples turned darker brown than glucose ones. The ratio of absorbance at 400 nm to that at 450 or 500 nm increased in the xylose system with the rise in pH value, while that in the glucose system decreased. Low-molecular-weight pigments, dilysyldipyrrolones, were formed only in the xylose system, while melanoidins were formed in both systems. Lysine stimulated the degradation of sugars, polymerization, and browning in both systems, although more intensively in the xylose system than in the glucose one.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 94%

Effects of Sugar and Buffer Types, and pH on Formation of Maillard Pigments in the Lysine Model System

Mikami

Murata

2015

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“…Hayase et al and Shirahashi et al reported blue and red pigments formed from glycine and xylose. Our group also reported some yellow pigments such as furpipate, , dilysyldipyrrolones, − 2,4-dihydroxy-2,5-dimethyl-3(2 H )-thiophenone, , pyrrolothiazolate, , and pyrrolooxazolates . Although there was only a small amount of these pigments in foods, , it is important to analyze these pigments.…”

Section: Introductionmentioning

confidence: 89%

Novel Maillard Pigment, Furpenthiazinate, Having Furan and Cyclopentathiazine Rings Formed by Acid Hydrolysis of Protein in the Presence of Xylose or by Reaction between Cysteine and Furfural under Strongly Acidic Conditions

Noda

Masuzaki

Terauchi

et al. 2018

J. Agric. Food Chem.

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A novel Maillard pigment having partial structures of furan and cyclopentathiazine, named furpenthiazinate, was isolated and identified. Although this pigment was found in an acid hydrolysate of a Maillard reaction solution between soy protein and xylose, the same pigment was also formed by the Maillard reaction under strongly acidic conditions between soy protein and xylose and cysteine and furfural. The structure of its reduced form by NaBH4 was determined by MS, NMR, and X-ray analysis and identified as 7-(2-furanyl)-2,3,4,4a,5,6-hexahydrocyclopenta[b][1,4]thiazin-4-ium-3-carboxylate, indicating that the chemical structure of furpenthiazinate is 7-(2-furanyl)-2,3,5,6-tetrahydrocyclopenta[b][1,4]thiazine-3-carboxylic acid. Furpenthiazinate showed an absorption maximum at 400 nm and strong yellow color under acidic and neutral conditions. The color contribution of furpenthiazinate was estimated to be more than 60% in a reaction solution prepared from cysteine and furfural.

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“…Our group also reported some yellow Maillard pigments such as furpipate 6,7) and dilysyldipyrrolones. [8][9][10] These pigments are known to have antioxidative activity. 10,11) Although the amount of low-molecular weight pigments is less than that of melanoidins, color intensity is cumulative and lowmolecular weight pigments often form high-molecular weight pigments or melanoidins.…”

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Two novel pyrrolooxazole pigments formed by the Maillard reaction between glucose and threonine or serine

Noda

Murata

2017

Bioscience, Biotechnology, and Biochemistry

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Pyrrolothiazolate formed by the Maillard reaction between l-cysteine and d-glucose has a pyrrolothiazole skeleton as a chromophore. We searched for a Maillard pigment having a pyrrolooxazole skeleton formed from l-threonine or l-serine instead of l-cysteine in the presence of d-glucose. As a result, two novel yellow pigments, named pyrrolooxazolates A and B, were isolated from model solutions of the Maillard reaction containing l-threonine and d-glucose, and l-serine and d-glucose, respectively, and identified as (2R,3S,7aS)-2,3,7,7a-tetrahydro-6-hydroxy-2,5,7a-trimethyl-7-oxo-pyrrolo[2,1-b]oxazole-3-calboxylic acid and (3S,7aS)-2,3,7,7a-tetrahydro-6-hydroxy-5,7a-dimethyl-7-oxo-pyrrolo[2,1-b]oxazole-3-calboxylic acid by instrumental analyses. These compounds were pyrrolooxazole derivatives carrying a carboxy group, and showed the absorption maxima at 300-360 nm under acidic and neutral conditions and at 320-390 nm under alkaline conditions.

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Conditions for the Formation of Dilysyl-Dipyrrolones A and B, and Novel Yellow Dipyrrolone Derivatives Formed from Xylose and Amino Acids in the Presence of Lysine

Cited by 16 publications

References 17 publications

Effects of Sugar and Buffer Types, and pH on Formation of Maillard Pigments in the Lysine Model System

Effects of Sugar and Buffer Types, and pH on Formation of Maillard Pigments in the Lysine Model System

Novel Maillard Pigment, Furpenthiazinate, Having Furan and Cyclopentathiazine Rings Formed by Acid Hydrolysis of Protein in the Presence of Xylose or by Reaction between Cysteine and Furfural under Strongly Acidic Conditions

Two novel pyrrolooxazole pigments formed by the Maillard reaction between glucose and threonine or serine

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