Imidazole-4-acetaldehyde
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Imidazole-4-acetaldehyde
Imidazole-4-acetaldehyde is a metabolite of histamine in biological species. Biological inactivation of histamine The process of histamine inactivation in biological species involves its metabolism through the oxidative deamination of its primary amino group. This reaction is catalyzed by the enzyme diamine oxidase (DAO). The metabolite produced from this reaction is imidazole-4-acetaldehyde. Imidazole-4-acetaldehyde is then further oxidized by a NAD-dependent aldehyde dehydrogenase, leading to imidazole-4-acetic acid. Synthesis under prebiotic conditions Under prebiotic conditions, imidazole-4-acetaldehyde can be synthesized from erythrose, formamidine, formaldehyde, and ammonia. Role in fungal amine oxidase and bacterial aldehyde oxidase In a study of imidazole-4-acetaldehyde presence in the reaction mixture during the coupling reaction of fungal amine oxidase and bacterial aldehyde oxidase for histamine elimination, imidazole 4-acetaldehyde was not detected, which suggest ...
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Diamine Oxidase
Diamine oxidase (DAO), also known "amine oxidase, copper-containing, 1" (AOC1), formerly called histaminase, is an enzyme () involved in the metabolism, oxidation, and inactivation of histamine and other polyamines such as putrescine or spermidine. The enzyme belongs to the amine oxidase (copper-containing) (AOC) family of amine oxidase enzymes. The enzyme is expressed in bilateria, a biological group of animals. The enzyme is encoded by the ''AOC1'' gene. This gene is highly conserved across the bilateria group which includes mammals, birds, reptiles, fish and insects, to name a few. Chemical activity Histamine metabolites Histamine, a biogenic amine, undergoes metabolism through three distinct enzymatic pathways: # The first pathway (see the reaction illustrated below) involves the deamination of histamine by the enzyme diamine oxidase to form imidazole acetaldehyde. # In the second pathway, histamine is metabolized into NĪ„-methylhistamine (also known as 1-Methylhistamine ...
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Metabolite
In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, catalytic activity of their own (usually as a cofactor to an enzyme), defense, and interactions with other organisms (e.g. pigments, odorants, and pheromones). A primary metabolite is directly involved in normal "growth", development, and reproduction. Ethylene exemplifies a primary metabolite produced large-scale by industrial microbiology. A secondary metabolite is not directly involved in those processes, but usually has an important ecological function. Examples include antibiotics and pigments such as resins and terpenes etc. Some antibiotics use primary metabolites as precursors, such as actinomycin, which is created from the primary metabolite tryptophan. Some sugars are metabolites, such as fructose or glucose, which ar ...
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Formaldehyde
Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as aqueous solutions (formalin), which consists mainly of the hydrate CH2(OH)2. It is the simplest of the aldehydes (). As a precursor to many other materials and chemical compounds, in 2006 the global production of formaldehyde was estimated at 12 million tons per year. It is mainly used in the production of industrial resins, e.g., for particle board and coatings. Formaldehyde also occurs naturally. It is derived from the degradation of serine, dimethylglycine, and lipids. Demethylases act by converting N-methyl groups to formaldehyde. Formaldehyde is classified as a group 1 carcinogen and can cause respiratory and skin irritation upon exposure. Forms Formaldehyde is more complicated than many simple carbon compounds in that i ...
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Histamine
Histamine is an organic nitrogenous compound involved in local immune responses communication, as well as regulating physiological functions in the gut and acting as a neurotransmitter for the brain, spinal cord, and uterus. Discovered in 1910, histamine has been considered a local hormone ( autocoid) because it is produced without involvement of the classic endocrine glands; however, in recent years, histamine has been recognized as a central neurotransmitter. Histamine is involved in the inflammatory response and has a central role as a mediator of itching. As part of an immune response to foreign pathogens, histamine is produced by basophils and by mast cells found in nearby connective tissues. Histamine increases the permeability of the capillaries to white blood cells and some proteins, to allow them to engage pathogens in the infected tissues. It consists of an imidazole ring attached to an ethylamine chain; under physiological conditions, the amino grou ...
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Imidazoles
Imidazole (ImH) is an organic compound with the formula . It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. It can be classified as a heterocycle, specifically as a diazole. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam. When fused to a pyrimidine ring, it forms a purine, which is the most widely occurring nitrogen-containing heterocycle in nature. The name "imidazole" was coined in 1887 by the German chemist Arthur Rudolf Hantzsch (1857–1935). Structure and properties Imidazole is a planar 5-membered ring, that exists in two equivalent tautomeric forms because hydro ...
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Biogenic Amines
A biogenic amine is a biogenic substance with one or more amine groups. They are basic nitrogenous compounds formed mainly by decarboxylation of amino acids or by amination and transamination of aldehydes and ketones. Biogenic amines are organic bases with low molecular weight and are synthesized by microbial, vegetable and animal metabolisms. In food and beverages they are formed by the enzymes of raw material or are generated by microbial decarboxylation of amino acids. List of notable biogenic amines Monoamines Some prominent examples of biogenic monoamines include: Monoamine neurotransmitters * Imidazoleamines ** Histamine – a substance derived from the amino acid histidine that acts as a neurotransmitter mediating arousal and attention, as well as a pro-inflammation, inflammatory signal released from mast cells in response to allergy, allergic reactions or tissue damage. Histamine is also an important stimulant of HCl secretion by the stomach through histamine H2 recept ...
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Gastric Cancer
Stomach cancer, also known as gastric cancer, is a malignant tumor of the stomach. It is a cancer that develops in the lining of the stomach. Most cases of stomach cancers are gastric carcinomas, which can be divided into a number of subtypes, including gastric adenocarcinomas. Lymphomas and mesenchymal tumors may also develop in the stomach. Early symptoms may include heartburn, upper abdominal pain, nausea, and loss of appetite. Later signs and symptoms may include weight loss, yellowing of the skin and whites of the eyes, vomiting, difficulty swallowing, and blood in the stool, among others. The cancer may spread from the stomach to other parts of the body, particularly the liver, lungs, bones, lining of the abdomen, and lymph nodes. The bacterium ''Helicobacter pylori'' accounts for more than 60% of cases of stomach cancer. Certain strains of ''H. pylori'' have greater risks than others. Smoking, dietary factors such as pickled vegetables and obesity are other ris ...
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Amine Oxidase
An amine oxidase is an enzyme that catalyzes the oxidative cleavage of alkylamines into aldehydes and ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...: :RCH2NH2 + H2O + O2 \rightleftharpoons RCHO + NH3 + H2O2 Amine oxidases are divided into two subfamilies based on the cofactor they contain: References External links * {{oxidoreductase-stub EC 1.4.3 ...
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Aldehyde Oxidase
Aldehyde oxidase (AO) is a metabolizing enzyme, located in the cytosolic compartment of tissues in many organisms. AO catalyzes the oxidation of aldehydes into carboxylic acid, and in addition, catalyzes the hydroxylation of some heterocycles. It can also catalyze the oxidation of both cytochrome P450 and monoamine oxidase (MAO) intermediate products. AO plays an important role in the metabolism of several drugs. Reaction AO catalyzes the conversion of an aldehyde in the presence of oxygen and water to an acid and hydrogen peroxide. * an aldehyde + H2O + O2 ⇌ a carboxylate + H2O2 + H+ Though the enzyme uses molecular oxygen as an electron acceptor, the oxygen atom that is incorporated into the carboxylate product is from water; however, the exact mechanism of reduction is still not known for AO. The AO also catalyzes the oxidation of heterocycles, which involves a nucleophilic attack located at the carbon atom beside the heteroatom. This means that susceptibility to nucl ...
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Bacteria
Bacteria (; : bacterium) are ubiquitous, mostly free-living organisms often consisting of one Cell (biology), biological cell. They constitute a large domain (biology), domain of Prokaryote, prokaryotic microorganisms. Typically a few micrometres in length, bacteria were among the first life forms to appear on Earth, and are present in most of its habitats. Bacteria inhabit the air, soil, water, Hot spring, acidic hot springs, radioactive waste, and the deep biosphere of Earth's crust. Bacteria play a vital role in many stages of the nutrient cycle by recycling nutrients and the nitrogen fixation, fixation of nitrogen from the Earth's atmosphere, atmosphere. The nutrient cycle includes the decomposition of cadaver, dead bodies; bacteria are responsible for the putrefaction stage in this process. In the biological communities surrounding hydrothermal vents and cold seeps, extremophile bacteria provide the nutrients needed to sustain life by converting dissolved compounds, suc ...
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Fungus
A fungus (: fungi , , , or ; or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and mold (fungus), molds, as well as the more familiar mushrooms. These organisms are classified as one of the kingdom (biology)#Six kingdoms (1998), traditional eukaryotic kingdoms, along with Animalia, Plantae, and either Protista or Protozoa and Chromista. A characteristic that places fungi in a different kingdom from plants, bacteria, and some protists is chitin in their cell walls. Fungi, like animals, are heterotrophs; they acquire their food by absorbing dissolved molecules, typically by secreting digestive enzymes into their environment. Fungi do not photosynthesize. Growth is their means of motility, mobility, except for spores (a few of which are flagellated), which may travel through the air or water. Fungi are the principal decomposers in ecological systems. These and other differences place fungi in a single group of related o ...
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Ammonia
Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pungent smell. It is widely used in fertilizers, refrigerants, explosives, cleaning agents, and is a precursor for numeous chemicals. Biologically, it is a common nitrogenous waste, and it contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to fertilisers. Around 70% of ammonia produced industrially is used to make fertilisers in various forms and composition, such as urea and diammonium phosphate. Ammonia in pure form is also applied directly into the soil. Ammonia, either directly or indirectly, is also a building block for the synthesis of many chemicals. In many countries, it is classified as an List of extremely hazardous substances, extremely hazardous substance. Ammonia is toxic, cau ...
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