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Biogenic amine

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A biogenic amine is a biogenic substance with one or more amine groups. They are basic nitrogenous compounds formed mainly by decarboxylation of amino acids or by amination and transamination of aldehydes and ketones. Biogenic amines are organic bases with low molecular weight and are synthesized by microbial, vegetable and animal metabolisms. In food and beverages they are formed by the enzymes of raw material or are generated by microbial decarboxylation of amino acids.

Contents

Importance in food

Biogenic amines can be found in all foods containing proteins or free amino acids and are found in a wide range of food products including fish products, meat products, dairy products, wine, beer, vegetables, fruits, nuts and chocolate. In non-fermented foods the presence of biogenic amines is mostly undesired and can be used as indication for microbial spoilage. In fermented foods, one can expect the presence of many kinds of microorganisms, some of them being capable of producing biogenic amines.

They play an important role as source of nitrogen and precursor for the synthesis of hormones, alkaloids, nucleic acids, proteins, amines and food aroma components. However, food containing high amounts of biogenic amines may have toxicological effects.

Monoamines

Some prominent examples of biogenic monoamines include:

Monoamine neurotransmitters

  • Histamine - a substance derived from the amino acid histidine that acts as a neurotransmitter mediating arousal and attention, as well as a pro-inflammatory signal released from mast cells in response to allergic reactions or tissue damage. Histamine is also an important stimulant of HCl secretion by the stomach through histamine H2 receptors.
  • Serotonin - a central nervous system neurotransmitter derived from the amino acid tryptophan involved in regulating mood, sleep, appetite, and sexuality.
  • The three catecholamine neurotransmitters:
  • Norepinephrine (noradrenaline) - a neurotransmitter involved in sleep and wakefulness, attention, and feeding behavior, as well as a stress hormone released by the adrenal glands that regulates the sympathetic nervous system.
  • Epinephrine (adrenaline) - an adrenal stress hormone, as well as a neurotransmitter present at lower levels in the brain.
  • Dopamine - a neurotransmitter involved in motivation, reward, addiction, behavioral reinforcement, and coordination of bodily movement.

    • Trace amines (endogenous amines that activate the human TAAR1 receptor)

  • Phenethylamines (related to catecholamines):
  • Phenethylamine (PEA)
  • N-Methylphenethylamine (endogenous amphetamine isomer)
  • Phenylethanolamine
  • m-Tyramine
  • p-Tyramine
  • 3-Methoxytyramine
  • N-Methyltyramine
  • m-Octopamine
  • p-Octopamine
  • Synephrine
  • Thyronamine compounds:
  • 3-Iodothyronamine
  • Tryptamine

    • Tryptamines

  • N-Methyltryptamine
  • N,N-Dimethyltryptamine

    • Other monoamines

  • Trimethylamine
  • Trimethylamine N-oxide

    • Polyamines

    Examples of notable biogenic polyamines include:

  • Agmatine
  • Cadaverine
  • Putrescine
  • Spermine
  • Spermidine

    • Physiological importance

    There is a distinction between endogenous and exogenous biogenic amines. Endogenous amines are produced in many different tissues (for example: adrenaline in adrenal medulla or histamine in mast cells and liver). The amines are transmitted locally or via the blood system. The exogenous amines are directly absorbed from food in the intestine. Alcohol can increase the absorption rate. Monoamine oxidase (MAO) breaks down biogenic amines and prevents excessive resorption. MAO inhibitors (MAOIs) are also used as medications for the treatment of depression to prevent MAO from breaking down amines important for positive mood.

    References

    Biogenic amine Wikipedia
    (Text) CC BY-SA