Histamine biosynthesis

Calles-Enriquez, M., Eriksen, B. H., Andersen, P. S., Rattray, F. R, Johansen, A. H., Fernandez, M., et al. (2010). Sequencing and transcriptional analysis of the Streptococcus thermophilus histamine biosynthesis gene cluster factors that affect differential hdcA expression. Applied and Environmental Microbiology, 76, 6231-6238. http //dx.doi.org/10.1128/AEM.00827-10. 

Landete, J. M., De las Rivas, B., Marcobal, A., Munoz, R. (2008). Updated molecular knowledge about histamine biosynthesis by bacteria. Critical Reviews in Food Science and Nutrition, 48, 697-714. http //dx.doi.org/10.1080/10408390701639041. 

Histamine biosynthesis and accumulation in the secretory vacuoles of the ECL cell. Histidine is taken up and decarboxylated to histamine by HOC. The histamine is accumulated in the vacuole due to the H gradient formed by a V-type ATPase and the presence of a histamine countertransport protein in the vacuolar membrane. 

The ECL cell possesses the enzyme HDC, which is the only enzyme involved in histamine biosynthesis. The enzyme is stimulated in vivo by a gastrininduced increase in gene transcription. It has been proposed that the rapid elevation induced by gastrin in vitro suggests that, besides an increase in gene transcription, there may also be activation of preexisting enzyme, as has been described in the regulation of other decarboxylases. 

Ascorbic acid is involved in carnitine biosynthesis. Carnitine (y-amino-P-hydroxybutyric acid, trimethylbetaine) (30) is a component of heart muscle, skeletal tissue, Uver and other tissues. It is involved in the transport of fatty acids into mitochondria, where they are oxidized to provide energy for the ceU and animal. It is synthesized in animals from lysine and methionine by two hydroxylases, both containing ferrous iron and L-ascorbic acid. Ascorbic acid donates electrons to the enzymes involved in the metabohsm of L-tyrosine, cholesterol, and histamine (128). 

L-Tyrosine metabohsm and catecholamine biosynthesis occur largely in the brain, central nervous tissue, and endocrine system, which have large pools of L-ascorbic acid (128). Catecholamine, a neurotransmitter, is the precursor in the formation of dopamine, which is converted to noradrenaline and adrenaline. The precise role of ascorbic acid has not been completely understood. Ascorbic acid has important biochemical functions with various hydroxylase enzymes in steroid, dmg, andhpid metabohsm. The cytochrome P-450 oxidase catalyzes the conversion of cholesterol to bUe acids and the detoxification process of aromatic dmgs and other xenobiotics, eg, carcinogens, poUutants, and pesticides, in the body (129). The effects of L-ascorbic acid on histamine metabohsm related to scurvy and anaphylactic shock have been investigated (130). Another ceUular reaction involving ascorbic acid is the conversion of folate to tetrahydrofolate. Ascorbic acid has many biochemical functions which affect the immune system of the body (131). 

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... 

Figure 3.5. Biosynthesis of histamine. Histamine is generated from histidine by the action of L-histidine decarboxylase.

The imidazole nucleus (Figure 27) is supplied during alkaloid biosynthesis by L-histamine. Typical alkaloids with the imidazole nucleus include histamine,... 

The biosynthesis of histamine involves decarboxylation of the amino acid histidine. 

Histamine, serotonin and the catecholamines (dopamine, epinephrine and norepinephrine) are synthesized from the aromatic amino acids histidine, tryptophan and phenylalanine, respectively. The biosynthesis of catecholamines in adrenal medulla cells and catecholamine-secreting neurons can be simply summarized as follows [the enzyme catalysing the reaction and the key additional reagents are in square brackets] phenylalanine — tyrosine [via liver phenylalanine hydroxylase + tetrahydrobiopterin] —> i.-dopa (l.-dihydroxyphenylalanine) [via tyrosine hydroxylase + tetrahydrobiopterin] —> dopamine (dihydroxyphenylethylamine) [via dopa decarboxylase + pyridoxal phosphate] — norepinephrine (2-hydroxydopamine) [via dopamine [J-hydroxylasc + ascorbate] —> epinephrine (jV-methyl norepinephrine) [via phenylethanolamine jV-methyltransferase + S-adenosylmethionine]. 

Speculations on the biosynthesis of zapotidine start from the isothiocyanate derivative of histamine (88) that must undergo a ring closure followed by a methylation at N-6. Although not known in biosyntheses, a similar conversion is to be found in the synthesis of goitrine (89) from the isothiocyanate 90 (142). 

In contrast, other authors found that O. oeni is able to significantly contribute to the overall histamine content of wines and also that the ability of this species to produce biogenic amines varies among strains (Coton et al. 1998 Guerrini et al. 2002). Marcobal et al. (2004) isolated and identified a strain of the O. oeni species, a producer of putrescine and the capacity of another 42 strains of this species to produce this amine has also been studied at a molecular level and the gene that encodes biosynthesis of this amine was not present in any of them (Marcobal et al. 2004). These results indicate that although this species may be involved in the production of putrescine in wines, this is not a common property. 

Evidence indicates that steroids affect other cells and substances that modulate inflammation. Exposure of human basophils to steroid in culture inhibits histamine release induced by an IgE-dependent stimulus. Steroids inhibit phospholipase A2, which prevents biosynthesis of arachidonic acid and subsequent formation of prostacyclin, thromboxane A, prostaglandins, and leukotrienes. Steroids also decrease capillary permeability and fibroblast proliferation and the quantity of collagen deposition, thereby influencing tissue regeneration and repair. 

Purines and pyrimidines are derived largely from amino acids. The biosynthesis of these precursors of DNA, RNA, and numerous coenzymes will be discussed in detail in Chapter 25. The reactive terminus of sphingosine, an intermediate in the synthesis of sphingolipids, comes from serine. Histamine, a potent vasodilator, is derived from histidine by decarboxylation. Tyrosine is a precursor of the hormones thyroxine (tetraiodothyronine) and epinephrine and of melanin, a complex polymeric pigment. The neurotransmitter serotonin (5-hydroxytryptamine) and the nicotinamide ring of NAD + are synthesized from tryptophan. Let us now consider in more detail three particularly important biochemicals derived from amino acids. 

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