Meciadanol
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Meciadanol
Meciadanol is a synthetic O-methylated flavanol. It is the 3-''O''-methylation of catechin. It inhibits histidine decarboxylase The enzyme histidine decarboxylase (, HDC) is transcribed on chromosome 15, region 21.2, and catalyzes the decarboxylation of histidine to form histamine. In mammals, histamine is an important biogenic amine with regulatory roles in neurotransmi ... in rats. References Flavanols Catechols Resorcinols Histidine decarboxylase inhibitors {{aromatic-stub ...
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O-methylated Flavanol
The O-methylated flavonoids or methoxyflavonoids are flavonoids with methylations on hydroxyl groups ( methoxy bonds). O-methylation has an effect on the solubility of flavonoids. Enzymes O-methylated flavonoids formation implies the presence of specific O-methyltransferase (OMT) enzymes which accept a variety of substrates. Those enzymes mediate the O-methylation on a specific hydroxyl group, like on 4' (example in '' Catharanthus roseus'') or 3' (example in rice) positions. Those positions can be ortho, meta, para and there can be a special 3-O-methyltransferase for the 3-OH position. Calamondin orange ('' Citrus mitis'') exhibits all of those activities. Plant enzymes * Apigenin 4'-O-methyltransferase * 8-hydroxyquercetin 8-O-methyltransferase * Isoflavone 4'-O-methyltransferase * Isoflavone 7-O-methyltransferase * Isoliquiritigenin 2'-O-methyltransferase * Isoorientin 3'-O-methyltransferase * Kaempferol 4'-O-methyltransferase * Luteolin O-methyltransferase * Methylquercetageti ...
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Catechin
Catechin is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids. The name of the catechin chemical family derives from ''catechu'', which is the tannic juice or boiled extract of ''Mimosa catechu'' (''Acacia catechu'' L.f). Chemistry Catechin possesses two benzene ring Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atom ...s (called the A- and B-rings) and a dihydropyran heterocycle (the C-ring) with a hydroxyl group on carbon 3. The A-ring is similar to a resorcinol moiety while the B-ring is similar to a catechol moiety. There are two chirality (chemistry), chiral centers on the molecule on carbons 2 and 3. Therefore, it has four diastereoisomers. Two of the isomers are in trans configura ...
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Histidine Decarboxylase
The enzyme histidine decarboxylase (, HDC) is transcribed on chromosome 15, region 21.2, and catalyzes the decarboxylation of histidine to form histamine. In mammals, histamine is an important biogenic amine with regulatory roles in neurotransmission, gastric acid secretion and immune response. Histidine decarboxylase is the sole member of the histamine synthesis pathway, producing histamine in a one-step reaction. Histamine cannot be generated by any other known enzyme. HDC is therefore the primary source of histamine in most mammals and eukaryotes. The enzyme employs a pyridoxal 5'-phosphate (PLP) cofactor, in similarity to many amino acid decarboxylases. Eukaryotes, as well as gram-negative bacteria share a common HDC, while gram-positive bacteria employ an evolutionarily unrelated pyruvoyl-dependent HDC. In humans, histidine decarboxylase is encoded by the ''HDC'' gene. Structure Histidine decarboxylase is a group II pyridoxal-dependent decarboxylase, along with aromatic- ...
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Flavanols
Flavan-3-ols (sometimes referred to as flavanols) are a subgroup of flavonoids. They are derivatives of flavans that possess a 2-phenyl-3,4-dihydro-2''H''-chromen-3-ol skeleton. Flavan-3-ols are structurally diverse and include a range of compounds, such as catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, proanthocyanidins, theaflavins, thearubigins. They are found in most plants and have a role in plant defense. Chemical structure The single-molecule (monomer) catechin, or isomer epicatechin (see diagram), adds four hydroxyls to flavan-3-ol, making building blocks for concatenated polymers (proanthocyanidins) and higher order polymers (anthocyanidins). Flavan-3-ols possess two chiral carbons, meaning four diastereoisomers occur for each of them. They are distinguished from the yellow, ketone-containing flavonoids such as quercitin and rutin, which are called flavonol, flavonols. Early use of the term bioflavonoid was imprecisely applied to include ...
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Catechols
Catechol ( or ), also known as pyrocatechol or 1,2-dihydroxybenzene, is a toxic organic compound with the molecular formula . It is the ''ortho'' isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol are now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances. Catechol occurs as feathery white crystals that are very rapidly soluble in water. Isolation and synthesis Catechol was first isolated in 1839 by Edgar Hugo Emil Reinsch (1809–1884) by distilling it from the solid tannic preparation catechin, which is the residuum of catechu, the boiled or concentrated juice of ''Mimosa catechu'' (''Acacia catechu''). Upon heating catechin above its decomposition point, a substance that Reinsch first named ''Brenz-Katechusäure'' (burned catechu acid) ...
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Resorcinols
Resorcinol (or resorcin) is an organic compound with the formula C6H4(OH)2. It is one of three isomeric benzenediols, the 1,3-isomer (or ''meta''-isomer). Resorcinol crystallizes from benzene as colorless needles that are readily soluble in water, alcohol, and ether, but insoluble in chloroform and carbon disulfide. Production Resorcinol is produced in several steps from benzene, starting with dialkylation with propylene to give 1,3-diisopropylbenzene. Oxidation and Hock rearrangement of this disubstituted arene gives acetone and resorcinol. Resorcinol is an expensive chemical, produced in only a very few locations around the world (to date only four commercial plants are known to be operative: in the United States, Germany,China and Japan), and as such it is the determining factor in the cost of PRF adhesives. Many additional routes exist for resorcinol. It was formerly produced by disulfonation of benzene followed by hydrolysis of the 1,3-disulfonate. This method has ...
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