title: 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.
abstract: 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.
authors.affiliation: Food, Nutrition, and Health, Faculty of Land and Food Systems, University of British Columbia , 2205 East Mall, Vancouver, British Columbia V6T 1Z4, Canada.
authors.forename: Xiu-Min
authors.initials: XM
authors.lastname: Chen
authors.forename: Gang
authors.initials: G
authors.lastname: Chen
authors.forename: Hongwen
authors.initials: H
authors.lastname: Chen
authors.forename: Yilin
authors.initials: Y
authors.lastname: Zhang
authors.forename: David D
authors.initials: DD
authors.lastname: Kitts
mesh_terms: D018938:Caco-2 Cells; D004095:Dihydropyridines / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D005947:Glucose / Q000737:chemistry*; D006146:Guanidines / Q000494:pharmacology; D006358:Hot Temperature; D006801:Humans; D008239:Lysine / Q000737:chemistry*; D015416:Maillard Reaction; D016328:NF-kappa B / Q000037:antagonists & inhibitors; D009569:Nitric Oxide / Q000037:antagonists & inhibitors / Q000494:pharmacology; D052247:Nitric Oxide Synthase Type II / Q000037:antagonists & inhibitors; D011759:Pyrrolidines / Q000494:pharmacology; D013859:Thiocarbamates / Q000494:pharmacology
chemical_list: C000603435:5-(5,6-dihydro-4H-pyridin-3-ylidenemethyl)furan-2-yl)methanol; D004095:Dihydropyridines; D005663:Furans; D006146:Guanidines; D016328:NF-kappa B; D011759:Pyrrolidines; D013859:Thiocarbamates; C020972:pyrrolidine dithiocarbamic acid; D009569:Nitric Oxide; D052247:Nitric Oxide Synthase Type II; D005947:Glucose; D008239:Lysine; C004479:pimagedine
keywords: Maillard reaction; anti-inflammation; glucose; lysine; nitric oxide