Histamine and histidine

Histidine, y9-4(5)-imidazolyl-a-aminopropionic acid (777), is one of the essential amino acids. From the pharmacological point of view, it is of particular importance as it is the immediate precursor of the highly active amine histamine, j8-4(5) imidazolylethylamine (7F). 

Histamine, which is widely distributed in nature, is formed by the decarboxylation of L-histidine by the enzyme histidine decarboxylase. Non-enzymic decarboxylation of histidine hais also been observed but the conditions under which this occurs render the reaction of little physiological interest. 

In view of its extremely high biological activity and the fact that it appears to be implicated in a variety of pathological conditions in man, histamine has been studied much more extensively than the enzyme which gives rise to it. It is only recently that histidine decarboxylase has been subjected to detailed study. Various aspects of this work are now surveyed. 

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Fletcher, G. C., Summers, G., Winchester, R. V., and Wong, R. J. (1995). Histamine and histidine in New Zealand marine fish and shellfish species, particularly Kahawai (Arripis trutta). J. Aquat. Food Prod. Technol. 4(2), 53-74. 

Cohen and co-workers have reported a facile synthesis of 2-(trifluoro-methyl)histamine and 2-(trifluoromethyl)-L-histidine using histamine and L-histidine as starting materials, repectively. The desire to use histamine and histidine was mainly due to ready availability, which would lead to rapid synthetic sequences and a direct entry into the fluorinated L-amino acid series. cw-l,2-Dibenzamido-l-alkenes (34) prepared by the Bamberger imidazole cleavage of corresponding imidazoles (33) were condensed with trifluoroacetic anhydride at reflux (40 °C) to yield 2-trifluoromethyl substituted imidazoles (35) in about 70% yield. 

A preliminary separation is thus necessary for the analysis of mixtures of amino acids. Hence, in mixtures of histamine and histidine, the corresponding dithiocarbaminocarbonic acids were first separated by paper electrophoresis. After elution, the anodic waves for dithiocarbaminocarbonic acids give the content of histamine and histidine in the mixture. 

Yoshida, H. Ichinose, K Yoshitake, T. Nakano, Y Todoroki, K. Nohta, H. Yamaguchi, M. Simultaneous determination of histamine and histidine by liquid chromatography following intramolecular excimer-forming fluorescence derivatization with pyrene-labeling reagent. Anal Sci. 2004, 20, 557-559. 

Frattini V, Lionetti C (1988) Histamine and histidine determination in tuna fish samples using high-performance liquid chromatography derivatization with o-phthalaldehyde and fluorescence detection or UV detection of free species. J Orromatogr A 809 241-245... 

Histamine AND histamine antagonists). It is formed from histidine by the enzyme L-histidine decarboxylase. In the periphery, histamine is stored ia mast cells, basophils, cells of the gastric mucosa, and epidermal cells. In the CNS, histamine is released from nerve cells and acts as a neurotransmitter. The actions of histamine ate terrninated by methylation and subsequent oxidation via the enzymes histamine-/V-methyltransferase and monoamine oxidase. 

Decarboxylation of histidine forms histamine, and several dipeptides are derived from histidine and P-alanine. 

A calorimetric study has been made (97) of the oxygenation of the cobalt (II) complexes formed with histidine, histamine and ethylenediamine in aqueous media at 25 °C. 

Noszal, B. Rabenstein, D. L., Nitrogen-protenation microequilibria and C(2)-depro-tonation microkinetics of histidine, histamine and related compounds, J. Phys. Chem. 95, 4761 1765 (1991). 

Biosynthesis is performed in one step by the enzyme L-histidine decarboxylase (HDC, E.C. 4.1.1.22). Histamine metabolism occurs mainly by two pathways. Oxidation is carried out by diamine oxidase (DAO, E.C. 1.4.3.6), leading to imidazole acetic acid (IAA), whereas methyla-tion is effected by histamine N-methyltransferase (HMT, E.C. 2.1.1.8), producing fe/e-methylhistamine (t-MH). IAA can exist as a riboside or ribotide conjugate. t-MH is further metabolized by monoamine oxidase (MAO)-B, producing fe/e-methylimidazole acetic acid (t-MIAA). Note that histamine is a substrate for DAO but not for MAO. Aldehyde intermediates, formed by the oxidation of both histamine and t-MH, are thought to be quickly oxidized to acids under normal circumstances. In the vertebrate CNS, histamine is almost exclusively methylated... 

Mn2+, D.F.P.-ase is further activated by cysteine, histidine, thiolhistidine, and serine, histamine and 2 2 -dipyridyl. Reagents reacting with metal ions, SH groups and carbonyl groups inhibit D.F.P.-ase activity. Work is proceeding on the further elucidation of such mechanisms.1 In a somewhat similar connexion attention is called to the fact that the non-enzymic hydrolysis of D.F.P. is accelerated by heavy metals and their complexes, in particular by copper chelates of ethylene diamine, o-phenanthroline, 2 2 -dipyridyl and histidine.2... 

Knowing the equilibrium constants for the protonation of the amino and imidazole nitrogens, and the kinetics of deprotonation of the C(2) carbon of imidazole, it was possible to investigate nitrogen-protonation microequilibria and the C(2)-deprotonation microkinetics of histidine, histamine and other related compounds164. 

This enzyme [EC 4.1.1.22] catalyzes the conversion of histidine to histamine and carbon dioxide. The enzyme requires either pyridoxal phosphate or pyruvate as a cofactor. 

Examples of amines that frequently occur in fish muscle include cadaverine from lysine, putrescine from ornithine and histamine from histidine. Histamine, because of its involvement in Scombroid food poisoning (histamine intoxication), has been extensively studied with respect to factors influencing its formation in many different fish species. Tuna and other fish from the families Scomberesocidae and Scombridae and a non-scombroid fish, mahi-mahi (dolphin fish) have been most... 

Edmunds and Eitenmiller (38) in a study of the effect of storage time and temperature on histamine content and histidine decarboxylase activity of several fresh water and marine species... 

Clostridium perfringens. Several isolates were used to determine if histamine-forming bacteria could grow and if whole cell suspensions could decarboxylate histidine at low temperatures. At 4 C Klebsiella pneumoniae grew in skipjack infusion broth and its resting cells produced histamine from histidine. 

In addition, flavones,140 aromatic urea derivatives (45, Scheme 14),141 lipophilic histidines (46), and histamines and imidazoles (47-50) have been reported as glycosidase inhibitors.142-144... 

Solid phase attachment of histidine-containing peptides by anchoring the imidazole ring to trityl resins has been developed for combinatorial library preparation of diketopiperazines <99TL809>. Histidine, histamine, and urocanic acid are edl imidazole-containing molecules that have been attached to a trityl-type resin to allow their application to combinatorial chemistry <99TL2825>. 

Histamine is formed by decarboxylation of the amino acid l -histidine, a reaction catalyzed in mammalian tissues by the enzyme histidine decarboxylase. Once formed, histamine is either stored or rapidly inactivated. Very little histamine is excreted unchanged. The major metabolic pathways involve conversion to /V-methylhistamine, methylimidazoleacetic acid, and imidazoleacetic acid (IAA). Certain neoplasms (systemic mastocytosis, urticaria pigmentosa, gastric carcinoid, and occasionally myelogenous leukemia) are associated with increased numbers of mast cells or basophils and with increased excretion of histamine and its metabolites. 

Decarboxylative enzymes may react specifically with amino acids having free polar groups al the a> position. Cadaverine can be produced from lysine, histamine from histidine, and tyramine from tyrosine. 

In addition to histamine release, histamine synthesis is also inhibited presynaptically by histamine, and the H3 receptor is linked to this effect [31]. In the cerebral cortex of rats injected with the radiolabelled precursor of histamine, [3H]L-histidine, [3H]histamine synthesis decreased significantly in a dose-dependent manner after systemic administration of RAMH [25]. This inhibition could be reversed by intraperitoneal administration of thioperamide [18, 25]. Interestingly, administration of thioperamide alone produced a marked increase in histamine synthesis, indicative of the presence of a degree of tonic inhibition elicited by H3-receptors [18]. 

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