Biomaterial Database

Interaction pattern of histidine, carnosine and histamine with methylglyoxal and other carbonyl compounds. 2021

Raheleh Ghassem Zadeh, and Varoujan Yaylayan

McGill University, Department of Food Science and Agricultural Cshemistry, 21111 Lakeshore, Ste. Anne de Bellevue, Quebec, Canada.

The ability of histidine to scavenge sugar-derived 1,2-dicarbonyl compounds was investigated using aqueous methanolic model systems containing histidine or histamine in the presence of glucose, methylglyoxal, or glyoxal. The samples were prepared either at room temperature (RT) or at 150 °C and analyzed using ESI-qTOF-MS/MS and isotope labeling technique. Replacing glucose with [U-13C6]glucose allowed the identification of glucose carbon atoms incorporated in the products. Various sugar-generated carbonyl compounds ranging in size from C1 to C6 were captured by histidine or histamine. The majority of the fragments incorporated were either C3 or C2 units originating from glyoxal (C2) or methylglyoxal (C3). The ESI-qTOF-MS/MS analysis indicated that histamine could react with either of the two carbonyl carbons of methylglyoxal utilizing the α-amino group and/or the imidazolium moiety. Furthermore, when histidine was added to 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine (PhIP) generating model system, it completely suppressed the formation of PhIP due to scavenging of phenylacetaldehyde.

UI	MeSH Term	Description	Entries
D007093	Imidazoles	Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons. Chemically reduced ones include IMIDAZOLINES and IMIDAZOLIDINES. Distinguish from 1,2-diazole (PYRAZOLES).
D007553	Isotope Labeling	Techniques for labeling a substance with a stable or radioactive isotope. It is not used for articles involving labeled substances unless the methods of labeling are substantively discussed. Tracers that may be labeled include chemical substances, cells, or microorganisms.	Isotope Labeling, Stable,Isotope-Coded Affinity Tagging,Isotopically-Coded Affinity Tagging,Affinity Tagging, Isotope-Coded,Affinity Tagging, Isotopically-Coded,Isotope Coded Affinity Tagging,Labeling, Isotope,Labeling, Stable Isotope,Stable Isotope Labeling,Tagging, Isotope-Coded Affinity,Tagging, Isotopically-Coded Affinity
D011765	Pyruvaldehyde	An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.	Acetylformaldehyde,Methylglyoxal,Oxopropanal,Pyruvic Aldehyde,Aldehyde, Pyruvic
D002336	Carnosine	A naturally occurring dipeptide neuropeptide found in muscles.	Carnosine Hydrochloride,Carnosine, (D-His)-Isomer,L-Carnosine,beta-Alanylhistidine,Hydrochloride, Carnosine,L Carnosine,beta Alanylhistidine
D005511	Food Handling	Any aspect of the operations in the preparation, processing, transport, storage, packaging, wrapping, exposure for sale, service, or delivery of food.	Food Processing,Handling, Food,Processing, Food
D005947	Glucose	A primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. It is used therapeutically in fluid and nutrient replacement.	Dextrose,Anhydrous Dextrose,D-Glucose,Glucose Monohydrate,Glucose, (DL)-Isomer,Glucose, (alpha-D)-Isomer,Glucose, (beta-D)-Isomer,D Glucose,Dextrose, Anhydrous,Monohydrate, Glucose
D006037	Glyoxal	A 2-carbon aldehyde with carbonyl groups on both carbons.	Ethanedial,Ethanedione
D006632	Histamine	An amine derived by enzymatic decarboxylation of HISTIDINE. It is a powerful stimulant of gastric secretion, a constrictor of bronchial smooth muscle, a vasodilator, and also a centrally acting neurotransmitter.	Ceplene,Histamine Dihydrochloride,Histamine Hydrochloride,Peremin
D006639	Histidine	An essential amino acid that is required for the production of HISTAMINE.	Histidine, L-isomer,L-Histidine,Histidine, L isomer,L-isomer Histidine
D000073893	Sugars	Short chain carbohydrate molecules that have hydroxyl groups attached to each carbon atom unit with the exception of one carbon that has a doubly-bond aldehyde or ketone oxygen. Cyclical sugar molecules are formed when the aldehyde or ketone groups respectively form a hemiacetal or hemiketal bond with one of the hydroxyl carbons. The three dimensional structure of the sugar molecule occurs in a vast array of biological and synthetic classes of specialized compounds including AMINO SUGARS; CARBASUGARS; DEOXY SUGARS; SUGAR ACIDS; SUGAR ALCOHOLS; and SUGAR PHOSPHATES.	Sugar