A Novel Yellow Compound and Furpipate Derivatives Formed from Furfural or 5-Hydroxymethylfurfural in the Presence of Lysine

Totsuka, Hana; Tokuzen, Konomi; Ono, Hiroshi; Murata, Masatsune

doi:10.3136/fstr.15.45

Cited by 20 publications

(29 citation statements)

References 21 publications

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“…In previous work, Totsuka et. al 28 NO Inhibitory Effects in Caco-2 Cells. The NO inhibitory effects of separated F3-AC19 and synthesized F3-AS were tested using Caco-2 cells.…”

Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 99%

Elucidation of the Chemical Structure and Determination of the Production Conditions for a Bioactive Maillard Reaction Product, [5-(5,6-Dihydro-4H-pyridin-3-ylidenemethyl)furan-2-yl]methanol, Isolated from a Glucose–Lysine Heated Mixture

Chen

et al. 2015

J. Agric. Food Chem.

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We previously isolated a bioactive molecule, named F3-A, from an aqueous glucose (Glc) and lysine (Lys) Maillard reaction (MR) model system. Herein, F3-A was verified as [5-(5,6-dihydro-4H-pyridin-3-ylidenemethyl)furan-2-yl]methanol (5) and was subsequently synthesized for confirmation of bioactivity. Using Taguchi and factorial designs, we determined that the conditions which best increased the yield of F3-A were at pH 6 with a sugar:amino acid ratio of 2:1 and heating time of 12 h at 100 °C. The MR mixtures containing glucose produced highest yield, compared to fructose, lactose, and sucrose. Both the F3-A recovered from Glc-Lys MR mixture and the synthesized product exhibited significant (P < 0.05), dose dependent, nitric oxide (NO) inhibitory activity in Caco-2 cells that was comparable to aminoguanidine (AG) and pyrrolidine dithiocarbamate (PDTC), respectively. Finally, an additional inhibitory effect of F3-A was determined when coincubated with AG in cytokine-induced Caco-2 cells. This bioactivity points to a potential role in preventing intestinal inflammation.

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“…In previous work, Totsuka et. al 28 NO Inhibitory Effects in Caco-2 Cells. The NO inhibitory effects of separated F3-AC19 and synthesized F3-AS were tested using Caco-2 cells.…”

Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 99%

Elucidation of the Chemical Structure and Determination of the Production Conditions for a Bioactive Maillard Reaction Product, [5-(5,6-Dihydro-4H-pyridin-3-ylidenemethyl)furan-2-yl]methanol, Isolated from a Glucose–Lysine Heated Mixture

Chen

et al. 2015

J. Agric. Food Chem.

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“…For example, Hayase et al 4) and Shirahashi et al 5) reported blue and red Maillard pigments formed from glycine and xylose. 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.…”

mentioning

confidence: 62%

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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“…For example, Hayase et al 2) and Shirahashi et al 3) reported a blue and red Maillard pigments formed from a glycine-xylose model solution. Our group also reported some yellow Maillard pigments such as furpipate 4,5) and dilysyldipyrrolones. 6−8) Even if the contribution of each low-molecular-weight colored compound to total color is small, it is meaningful to identify lowmolecular-weight colored compounds in foods and solutions of the Maillard reaction to understand and regulate the Maillard pigments, because various compounds are formed by the Maillard reaction and each compound is considered to cumulatively contribute to the total color.…”

mentioning

confidence: 62%

Isolation, identification, and formation conditions of a novel Maillard yellowish pigment, pyrrolothiazolate

Noda

Yamada

Murata

2015

Bioscience, Biotechnology, and Biochemistry

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We isolated a novel yellow pigment from a model Maillard reaction system containing l-cysteine, l-lysine, and glucose and identified it as 6-hydroxy-3[R],7a[S]-dimethyl-7-oxo-2,3-dihydropyrrolo[2,1-b]thiazole-3-calboxylic acid. This compound was a novel pyrrolothiazole derivative carrying a carboxy group and was named pyrrolothiazolate. This compound showed the absorption maxima at 300 and 360 nm under acidic and neutral conditions, while 320 and 400 nm did under alkaline conditions. Pyrrolothiazolate formed from cysteine and glucose was the major low-molecular-weight Maillard pigment in the reaction mixture, and its formation was stimulated by adding lysine to the reaction cocktail. After heating at 110 °C for 2 h, 1-2 mg/mL of pyrrolothiazolate was formed in a reaction mixture containing 100 mM cysteine, 200 mM lysine, and 300 mM glucose dissolved in 0.5 m acetate buffer (pH 6.0) or 0.5 m phosphate buffer (pH 6.5).

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A Novel Yellow Compound and Furpipate Derivatives Formed from Furfural or 5-Hydroxymethylfurfural in the Presence of Lysine

Cited by 20 publications

References 21 publications

Elucidation of the Chemical Structure and Determination of the Production Conditions for a Bioactive Maillard Reaction Product, [5-(5,6-Dihydro-4H-pyridin-3-ylidenemethyl)furan-2-yl]methanol, Isolated from a Glucose–Lysine Heated Mixture

Elucidation of the Chemical Structure and Determination of the Production Conditions for a Bioactive Maillard Reaction Product, [5-(5,6-Dihydro-4H-pyridin-3-ylidenemethyl)furan-2-yl]methanol, Isolated from a Glucose–Lysine Heated Mixture

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

Isolation, identification, and formation conditions of a novel Maillard yellowish pigment, pyrrolothiazolate

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