Amines, biogenic

Author: Prof. Dr. med. Peter Altmeyer

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Last updated on: 29.10.2020

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Synonym(s)

biogenic amines

Definition
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Primary amines (nitrogen compounds) naturally occurring in plants and animals, which are formed from amino acids by enzymatic decarboxylation. A distinction is made between endogenous and exogenous biogenic amines.

Endogenous amines are produced in the organism in various organs and tissues (adrenalin: adrenal medulla, histamine: liver, mast cells), phenethylamine (brain from the AS phenylalanine).

Exogenous amines are supplied nutritively (e.g. so-called wine allergy).

Biogenic amines themselves are synthesis precursors of biologically relevant substances such as alkaloids (e.g. cadaverine as a decarboxylation product of lysine) or hormones(histamine via histidine decarboxylase from histidine). Furthermore biogenic amines serve as starting products for the synthesis of coenzymes, vitamins and phospholipids.

Some biogenic amines themselves have physiological effects, for example as neurotransmitters (dopamine and noradrenalin from the amino acid DOPA; serotonin from the amino acid 5-hydroxytryptophan; tyramine from the amino acid tyrosine).

General information
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Biogenic amines are only obligatory toxic for humans in higher doses. At lower doses, individual tolerance is crucial. This is presumably caused by various factors. This tolerance is probably influenced by various diseases (e.g. by liver dysfunction), but also by the different activities of the enzymes diamine oxidase (DAO) in the intestinal tract and histamine methyltransferase in the liver. A delayed histamine catabolism has been demonstrated in a proportion of patients with chronic urticaria. The biogenic amines putrescine (formed by decarboxylation from the amino acid ornithine) and tyramine (formed by decarboxylation from the amino acid tyrosine) are competitive inhibitors of DAO.

Occurrence
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Exogenous biogenic amines are found in smaller amounts in almost all foods, especially in tropical fruits(pineapple, avocado, bananas, citrus fruits), but also in tomatoes, walnuts, raspberries, plums and spinach. Larger, possibly toxic quantities can be produced during the microbial decomposition of fish and meat. Furthermore, larger amounts can also be found in foods produced by microbial (bacteria or fungi) processes, such as certain types of cheese, sauerkraut and wine.

Clinical picture
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After consumption of food containing large amounts of biogenic amines, acute pseudoallergic reactions (see intolerance reaction below) may occur a few minutes to hours after ingestion, such as: flushing erythema, itching, urticaria, angioedema up to anaphylactic shock, acute rhinitis, acute asthma, diarrhoea symptoms, headaches.

Literature
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  1. Edmondson DE et al (2004) Structure and mechanism of monoamine oxidase. Curr Med Chem 11: 1983-1993
  2. Häberle M (1987) Biogenic amine clinical and food chemistry aspects. Zbl skin 153: 157-168
  3. Jansen SC et al (2003) Intolerance to dietary biogenic amines: a review. Ann Allergy Asthma Immunol 91: 233-240
  4. Moreno-Arribas MV et al (2003) Screening of biogenic amine production by lactic acid bacteria isolated from grape must and wine. Int J Food Microbiol 84: 117-123
  5. Suzzi G (2003) Biogenic amines in dry fermented sausages: a review. Int J Food Microbiol 88: 41-54

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Last updated on: 29.10.2020