Biogenic amines

Biogenic amines are primary amines that are formed in the metabolism (of microorganisms , plants, animals and humans) through the enzymatic decarboxylation of amino acids . Due to the presence of amino groups , biogenic amines react like ammonia as proton acceptors in a basic manner . Biogenic amines are often synthesis precursors of alkaloids or hormones . They also serve as building blocks for the synthesis of coenzymes , vitamins and phospholipids . Some free biogenic amines themselves develop physiological effects, for example as neurotransmitters .

Examples

Biogenic amines, origin and function

Biogenic amine	from the amino acid	Occurrence and meaning
Agmatine	Arginine	Bacteria (intestinal flora), a precursor for putrescine in some organisms
β-alanine	Aspartic acid	Part of coenzyme A , precursor for pantothenic acid
Aminoacetone	2-aminoacetoacetic acid	Precursor for cobalamins (vitamin B 12 )
γ-aminobutyric acid	Glutamic acid	Brain, neurotransmitter
5-amino-4-oxovaleric acid	Succinyl glycine	Precursor for porphyrins
Isopropanolamine	Threonine
Cadaverine	Lysine	Ribosomes, bacteria, alkaloid precursor
Cysteamine	Cysteine	Part of coenzyme A, precursor of taurine
Dopamine	DOPA	Neurotransmitter, precursor for the catecholamines noradrenaline and adrenaline , alkaloid precursor
Ethanolamine	Serine	Phosphatides , precursors for hormones and choline , neurotransmitters
histamine	Histidine	Tissue hormone
Isoamylamine	Leucine
Octopamine	Tyrosine	Neurotransmitters ( invertebrates )
Phenethylamine	Phenylalanine	Occurrence in the brain
Putrescine	Ornithine	Ribosomes , bacteria, precursor for spermidine and other polyamines
Serotonin	5-hydroxytryptophan	Neurotransmitter, precursor of the hormone melatonin and the toad poison bufotenin
Spermidine	Ornithine over putrescine	Growth factor in the seed u. a. Cells, precursor for spermine in ribosomes, DNA, sperm
Tryptamine	Tryptophan	causes contraction of the smooth muscles, which promotes growth in plants
Tyramine	Tyrosine	causes the smooth muscles to contract
Norepinephrine	DOPA	Neurotransmitter, catecholamine, causes blood vessels to constrict and blood pressure to increase

Amino acids (above) and the biogenic amines derived from them (below):

Lysine	Serine	Tyrosine	Histidine
Cadaverine	Ethanolamine	Tyramine	histamine

Physiological importance

A distinction is made between endogenous and exogenous biogenic amines. Endogenous amines are produced in many different tissues (eg. B .: adrenaline in the adrenal medulla or histamine in nerve cells, basophilic leukocytes and mast cells ). It is released locally or via the blood system. The exogenous amines are absorbed directly from food in the intestine. Alcohol can increase the rate of absorption. The diamine oxidase (DAO) as well as the monoamine oxidase (MAO) build (z. B. methyltransferases as the histamine-N-methyltransferase = among other enzymes HNMT or catechol-O-methyltransferase COMT ) biogenic amines, and so prevent an excessive absorption or an excess in the tissue. In sensitive people, DAO, MAO or other enzymes are accordingly not sufficiently available or are also inhibited. DAO inhibitors as well as MAO inhibitors are z. B. in drugs for the treatment of depression or in nutmegs . Some biogenic amines also act as inhibitors of enzymes (e.g. tyramine inhibits DAO as well as HNMT and thus the breakdown of histamine). In addition, the degradation of biogenic amines may also be inhibited via feedback above a certain amount of degradation metabolites. A combined intake of biogenic amines and substances that increase or slow down absorption (alcohol) can lead to an allergic or pseudoallergic reaction.

Consumer protection

Since the concentration of certain biogenic amines indicates microbial spoilage , scientists at the Fraunhofer Institute are working on equipping prepackages for food with the appropriate indicator film. This idea dates back to 2011 and received some media attention due to the rotten meat scandal in 2010.

literature

• Ahmed Askar, Hans Treptow: Biogenic amines in food: Occurrence, meaning and determination. Published by E. Ulmer, 1986
• Dorothea M. Beutling (ed.): Biogenic amines in nutrition. Published by Springer, 1996

Individual evidence

1. ↑ Dietrich Frohne, Uwe Jensen: Systematics of the Plant Kingdom with Special Consideration of Chemical Characteristics and Plant Drugs, 4th Edition, Gustav Fischer Verlag Stuttgart, Jena, New York, ISBN 3-437-20486-6 , p. 313.
2. ↑ Entry on Biogenic Amines. In: Römpp Online . Georg Thieme Verlag, accessed December 10, 2014.
3. ↑ Sensor film warns of rotten meat April 4, 2011.