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(Figure 2). In plants and some microorganisms, an

alternative pathway exists to produce putrescine

from arginine via agmatine (see dotted lines).

Physiological Importance of Amines

0007 Amines participate in important metabolic and

physiological functions in living organisms. Polya-

mines are essential for cell proliferation, growth, re-

newal, and metabolism. They are involved in nearly

every step of DNA, RNA, and protein synthesis, and

regulate the permeability and stability of cellular

membranes. Polyamines play indispensable roles in

living cells. Therefore, they are important in health

and disease. Polyamine requirements are higher in the

young during periods of intense growth. In healthy

adults, however, these should not be as high, because

polyamines are needed only to replace cells and

mediate the action of hormones and growth factors.

Polyamines are also essential for the maintenance

of the high metabolic activity of the normally

functioning and healthy gut, repairing the damage

caused by deleterious components in food or by

bacteria.

0008Biogenic amines are generally either psychoactive

or vasoactive. Psychoactive amines, such as histamine

and serotonin, act on the neural transmitters in the

central nervous system. Vasoactive amines act dir-

ectly or indirectly on the vascular system. Pressor

amines – tyramine, tryptamine, and phenylethyla-

mine – cause a rise in blood pressure by constricting

the vascular system and increasing the heart rate and

contraction force. Serotonin is vaso- and broncocon-

strictor, reduces the volume and acidity of the gastric

juice, has an antidiuretic effect, stimulates smooth

muscle, and affects carbohydrate metabolism. Hista-

mine can exert many responses within the body. It can

directly stimulate the heart, cause contraction or re-

laxation of extravascular smooth muscle, stimulate

both motor and sensorial neurons, and control gastric

secretion. It also mediates primary and immediate

symptoms in allergic responses.

Tyrosine Tyramine

Tryptophan Tryptamine

Phenylalanine Phenylethylamine

Histidine Histamine

NCH

Lysine Cadaverine

fig0001 Figure 1 Synthesis of biogenic amines.

174 AMINES

Toxicology of biologically active amines

0009 Three sources of amines have been identified: biosyn-

thesis in situ from amino acids, direct ingestion from

the diet, and synthesis and release by the bacterial

flora resident in the gastrointestinal tract of the indi-

vidual. It is now clear that the diet is an important

source, supplying a significant part of the polyamines

required to sustain normal metabolism.

0010 Because of their biological activity, surplus amines

need to be eliminated. Healthy individuals can detox-

ify amines present in foods by acetylation and

oxidation. Biogenic amines are oxidized by mono-

aminoxidases (MAO; EC 1.4.3.4) and diaminoxi-

dases (DAO; EC 1.4.3.6). Polyamines are usually

acetylated first, then oxidized by polyaminoxidases

(PAO; EC 1.5.3.11).

0011 Amines in foods do not usually represent any

health hazard to individuals, unless excessive

amounts are ingested, or the natural mechanism for

the catabolism of amines is genetically deficient or

impaired by diseases. Individuals with respiratory

and coronary problems, hypertension, or vitamin

deficiency are at risk because they are sensitive

to lower amounts of amines. People with gastrointest-

inal problems (gastritis, irritable bowel syndrome,

Crohn’s disease, stomach and colonic ulcers) are

also at risk because the activity of oxidases in their

intestines is usually lower than that in healthy indi-

viduals. Patients taking medication that acts as inhibi-

tors of MAO, DAO, and PAO activity also can be

affected, as such drugs prevent the catabolism of

amines. These MAO and DAO inhibitors are used

for the treatment of stress, depression, Alzheimer’s

and Parkinson’s diseases, pulmonary tuberculosis,

malaria, panic syndrome, and social phobia. The

toxic effect of some amines also can be potentiated

by the presence of ethanol and of amines includ-

ing putrescine, cadaverine, tyramine, tryptamine,

2-phenylethylamine, agmatine, serotonin, spermi-

dine, and spermine. Most of them act by inhibition

of amine metabolizing enzymes, whereas spermine

causes liberation of endogenous histamine in the

intestine.

0012The toxic effects caused by amines are summarized

in Table 1. The most frequent foodborne intoxication

caused by amines involves histamine. Histamine in-

toxication is also referred to as ‘scombroid poisoning’

because of the association of this illness with the

consumption of scombroid fish. The disease mani-

fests several minutes to 3 h after ingestion of the

histamine-containing food. At first, a flushing of

the face and neck is usually observed, accompanied

by a feeling of heat and general discomfort. Often,

this is followed by an intense throbbing headache.

Other symptoms may be: cardiac palpitations, dizzi-

ness, faintness, itching, rapid and weak pulse, and

gastrointestinal complaints (abdominal cramps,

nausea, diarrhea). In severe cases, bronchospasms,

suffocation, and severe respiratory distress are

reported. However, the illness usually has a mild

character, and symptoms do not last long. In most

cases, the illness is not recognized as such. It is also

possible that the symptoms are falsely attributed to a

food allergy.

0013In the literature, many cases of food intoxication

have been attributed to high histamine levels in foods

or to low histamine levels in food containing other

amines that can potentiate the toxic effect of hista-

mine. Foods implicated in outbreaks of histamine

intoxication include scombroid (tuna, bonito, mack-

erel, skipjack, herring) and other fish (sardine, an-

chovy, mahi-mahi), cheese (Gouda, Swiss, Gruye

re,

Cheddar, Cheshire), sauerkraut, sausage, and red

wines.

0014When foods containing high tyramine levels are

ingested, large amounts of nonmetabolized tyramine

can reach the blood stream. This causes release of

noradrenaline from the sympathetic nervous system,

Glutamine

Proline Ornithine Arginine

(CH

)

Agmatine

NCH

Putrescine

Propylamine

(CH

)

(CH

)

S-Adenosil

Methionine

Spermidine

Propylamine

NNHNHNH

(CH

)

(CH

)

(CH

)

Methionine

Spermine

fig0002 Figure 2 Pathways for the biosynthesis of polyamines.

AMINES 175

leading to a variety of physiological reactions. There

is an increase in blood pressure by peripheral vaso-

constriction and by increasing the cardiac output.

Tyramine also can dilate the pupils and the palpebral

tissue, cause lacrimation and salivation, and increase

respiration.

0015 Ingestion of foods rich in tyramine by individuals

under MAO inhibitor drugs treatment results in

a dangerous intoxication known as the ‘cheese

reaction,’ so called because most of the cases involved

cheese. However, it is not the only type of food in-

criminated, since cases have also been reported

with yeast extracts (marmite), pickled herring, dry

sausage, alcoholic beverages, broad beans, etc. The

cheese reaction involves a hypertensive crisis, usually

accompanied by a severe headache. There can be

visual alterations, nausea, vomit, muscle contraction,

mental confusion, or excitation. It can lead also to

cerebral hemorrhage, neuronal sequel, cardiac fail-

ure, and pulmonary edema. Fatal incidents have

been reported in the literature.

0016Several amines, such as tyramine, tryptamine, and

phenylethylamine, are considered precipitants of

attacks in migraine sufferers.

0017Even though putrescine and cadaverine have

less pharmacological activity than the aromatic

amines, after ingestion of very large amounts of

these compounds, toxic effects have been observed.

Intoxication symptoms reported are hypotension,

bradycardia, dyspnea, lockjaw, and paresis of the

extremities. However, the most important conse-

quence of these compounds in food is probably the

potentiation effect of the toxicity of other amines.

0018Determination of the exact toxicity threshold of

amines is extremely difficult. The toxic dose is de-

pendent on the efficiency of the detoxification mech-

anism of different individuals. Upper limits of 10 mg

of histamine, 10 mg of tyramine, and 3 mg of

2-phenylethylamine in 100 g of foods have been sug-

gested. In the case of alcoholic beverages, the pro-

posed limits are 2–8 mg of histamine and 8 mg of

tyramine per liter. Individuals taking MAO inhibitor

tbl0001 Table 1 Toxic effects of biologically active amines

Toxic effects Aminesinvolved Food associated Symptoms

Histamine intoxication or

scombroid poisoning

Histamine

(Toxic effect is potentiated

by putrescine, cadaverine,

spermine, tryptamine,

tyramine,

phenylethylamine,

ethanol)

Scombroid fish: tuna,

bonito, mackerel,

skipjack, herring

Gastrointestinal: nausea,

vomiting, diarrhea,

cramps

Other fish: sardines,

anchovy, mahi-mahi

Neurological: headache,

palpitation, face and neck

flushing, burning throat,

itching, rapid and weak pulse,

dizziness, faintness

Cheese: Swiss, Gouda,

Cheddar, Gruye

re,

Cheshire

Hemodynamic: hypotensionSauerkraut; sausage; wine

Cutaneous: rash, urticaria,

edema, localized inflammation

Severe cases: bronchospasms,

suffocation, severe respiratory

distress

Tyramine intoxication Tyramine Cheese Headache, fever, increased

blood pressure, vomiting,

perspiration, pupils and

palpebral tissue dilatation,

salivation, lacrimation,

increased respiration,

palpitation, dyspnea

Beer

Wine

Cheese reaction

hypertensive crisis

(associated with patients

under MAOI drugs)

Tyramine Cheese: Gouda, Swiss,

Gruye

re, Cheddar

Hypertensive crisis, severe

headache, cerebral

hemorrhage, neuronal

sequel, cardiac failure,

pulmonary edema, visual

alterations, palpitation, nausea,

sweat, vomit, muscle

contractions, excitation, and

mental confusion

2-Phenylethylamine

Beer, wine, yeast extract,

Pickled herring, dry

Sausage, broad beans

Migraine Tyramine Cheese Throbbing headache,

migraine attack2-Phenylethylamine Chocolate

Tryptamine Beer

Serotonin Wine

MAOI, monoaminoxidase inhibitors.

176 AMINES

drugs should limit tyramine intake to 6 mg per 100 g

of foods.

0019 As mentioned before, polyamines play important

roles in cellular metabolism and growth. However,

the importance of putrescine, spermine, and spermi-

dine in tumor growth is widely recognized, and the

inhibition of polyamines biosynthesis in tumor-

bearing individuals is a major target of cancer therapy

research. A new direction being investigated to inhibit

tumor growth is to limit polyamine uptake.

0020 Furthermore, putrescine and cadaverine can be

converted to pyrrolidine and piperidine, respectively.

These compounds, as well as spermidine, spermine

and agmatine, can react with nitrite to form carcino-

genic nitrosamines in foods or in vivo, in the gastro-

intestinal tract.

Occurrence of Amines in Foods

0021 Biologically active amines are inherent to living or-

ganisms and, therefore, are present in plants, meat,

and dairy products. The amount and type of amines

in foods depend on the nature and origin of the com-

modity. However, it can change during processing,

fermentation, and storage. It can be affected also by

hygienic conditions. Amines are resistant to heat

treatment employed in food processing. Based on

these findings, amines have been considered good

indicators of the freshness, spoilage, and degree of

quality of fresh and canned food products.

0022It is evident that all types of food, whether they

originate from plants or animals, contain putrescine

and spermidine. In addition to these most common

compounds, other amines also may occur naturally.

When the food is spoiled by bacteria, the spermine

content often decreases, because it can be used as a

nitrogen source by some microorganisms. There is

also formation and accumulation of different types

of biogenic amines.

0023Much still remains unknown about the concentra-

tion of amines in food products. Most data available

relate to specific amines, mainly histamine and tyr-

amine in fish, cheese, meat, and alcoholic beverages.

A comprehensive study of levels of all amines would

be useful from both a toxicological and technological

point of view. This is obviously an area deserving

further detailed investigation.

Fish

0024Under normal physiological conditions, fish muscle

contains high levels of spermidine and spermine and

low levels of histamine and putrescine (Table 2).

During storage and deterioration of fish, the levels

of spermine and spermidine decrease, levels of putres-

cine, histamine, and cadaverine increase, and, in some

species of fish, the presence of tyramine and trypta-

mine can be detected also. Based on these findings, a

chemical index, calculated by the levels of putrescine,

histamine, and cadaverine divided by those of sper-

mine and spermidine, was proposed to evaluate the

tbl0002 Table 2 Mean levels of biologically active amines in different fresh, stored, and deteriorated fish, meat, and meat products

Food Mean amine level (mg per 100 g)

Spermine Spermidine Putrescine Cadaverine Histamine Tyramine

Tu n a f i s h

Fresh 0.95 0.44 0.12 0.15 0.38 –

Decomposed 0.12 0.07 0.25 1.93 25.3 –

Snapper

Fresh 0.72 0.68 0.99 nd nd nd

Spoiled 0.52 1.52 3.32 9.33 0.44 nd

Pork

Fresh 6.71 0.70 0.78 1.33 0.47 –

15 days/5



C 3.12 0.31 1.89 4.30 0.99 –

Beef

2.27 0.61 0.51 0.95 0.57 1.07

Chicken

Fresh 1.79 0.73 0.02 nd nd nd

15 days/4



C 1.12 0.87 2.04 0.43 1.03 1.74

Hot dog 1.08 1.58 0.06 0.04 0.09 0.01

Sausage 1.03 0.66 1.51 0.80 1.35 0.74

nd, not detectable; –, not determined.

Snapper – Piaractus mesopotamicus.

Mean of 62 samples.

From Sayem-El-Daher N, Simard RE, Fillion J and Roberge AG (1984) Extraction and determination of biogenic amines in ground beef and their relation to

microbial quality. Lebensm. Wiss.Technol. 17: 20–23; Hala

sz A, Bara

th A, Simon-Sarkadi L and Holzapfel W (1994) Biogenic amines and their production by

microorganisms in food. Trends in Food Science and Technology 51: 42–49; Silva and Glo

ria (2002) Bioactive amines in chicken breast and thigh after

slaughter and during storage at 4 1



C and in chicken-based meat products. Foods Chemistry 78: 241–248.

AMINES 177

quality of tuna fish. This index was considered ad-

equate to evaluate the quality or freshness of tuna and

other types of fish and seafood, among them, salmon,

rockfish, snapper, lobster, and shrimp.

0025 Amine formation and build-up in fish normally

occur during decomposition or spoilage processes as

a result of the liberation of free amino acids through

proteolysis together with bacterial production and

action of amino acid decarboxylase. Several investi-

gations have demonstrated that storage temperature

is a critical factor influencing histamine and other

amines formation in fish muscle. The requirement

for rapid and uninterrupted refrigeration after catch

cannot be overemphasized. The US Food and Drug

Administration (FDA) established a guidance level for

histamine in fish at the dock or before processing

of 5 mg per 100 g. The FDA also states that rapid

chilling of fish immediately after catch is the most

important strategy to limit histamine formation. The

internal temperature of the fish should be brought to



C or below within 6 h of death. Chilling from

10 to 4.4



C or less should take no longer than 18 h.

Any period of time at a temperature above 4



C sig-

nificantly reduces the expected safe shelf-life. A max-

imum average histamine content of 10 mg per 100 g

has been established by several countries and commu-

nities for acceptance of canned tuna and other fish

belonging to the Scombridae and Scomberesocidae

families. Because of the potentiating effect of other

amines on the toxic effect of histamine, European

regulation recommends the use of high-performance

liquid chromatography (HPLC) techniques for the

determination of the amines.

0026 Scombroid fish, such as tuna, bonito, mackerel,

yellowfin, and bluefin, have been involved more fre-

quently in histamine intoxication incidents. Scom-

broid fish are particularly susceptible to histamine

formation, since they contain large amounts of free

histidine. However, other fishes have also been impli-

cated, including Scomberesocidae, Pomatomidae,

Coryhaenidae, Carangidae, Clupeidae, and Engrauli-

dae. Even though several fish bacteria, either natural

or contaminants, are capable of producing histamine,

Morganella morganii, Hafnia alvei,andKlebsiella

pneumoniae are the only histamine-producing bac-

teria that have been isolated from fish implicated in

outbreaks.

Meat and Meat Products

0027 Putrescine, spermine, and spermidine occur naturally

in meat, where they serve as growth factors and are

involved in a number of vital processes. Compared

with fish, meat contains higher spermine levels.

Meat products are also susceptible to proteolysis

by enzymes (endogenous or from microbial

contaminants), liberation of amino acids, and amine

formation by amino acid decarboxylation. Amine

levels in different types of fresh and stored meat are

listed in Table 2. During storage and putrefaction of

pork meat, there is a significant increase in putrescine

and cadaverine. A significant correlation has been

observed between these amines and total microbial

counts.

0028In poultry, immediately after slaughter, high levels

of spermine and spermidine and traces of putrescine

have been detected. During storage at 4



C, there is a

decrease in spermine levels, whereas spermidine levels

remain constant. The levels of putrescine, cadaverine,

histamine, and tyramine increase significantly on the

15th day with higher levels found in breast

than in thighs. The amine levels in chicken-based

products listed in Table 2 indicate that the ingredients

can affect the amine profile. Chicken-based hot dog

contains significantly higher spermidine levels than

the meat, probably because of the addition of soybean

in the formulation. Significantly higher biogenic

amine levels have been observed in chicken-based

sausages, which could be indicative of the use of

low-quality raw material, or of contamination during

processing and storage.

0029Sausages have been implicated in histamine intoxi-

cation and hypertensive crisis episodes. Moreover,

several reports have shown a wide range and high

contents of biogenic amines in sausages. The manu-

facture of sausages offers favorable conditions for the

formation of biogenic amines. The microbial count

can be high and the production process lengthy,

allowing a certain degree of proteolysis and yielding

the amine precursor amino acids. Raw material qual-

ity, thawing conditions, ripening temperature and

addition of a properly selected starter culture can

affect the formation and accumulation of tyramine

and histamine and, therefore, are important critical

control points in preventing amine formation.

Dairy Products

0030The polyamine content in milk and dairy products

is low, but the biogenic amine levels in cheese can

be high. In fact, cheese is one of the foods with the

highest amine content. A variety of amines have been

found in different types of cheese (Table 3). In gen-

eral, spermine and spermidine are present at low

levels. The levels of other types of amines vary widely.

High histamine and tyramine levels have been

reported in several types of cheese.

0031Cheeses represent an ideal environment for amine

production. The major factors that affect the forma-

tion, accumulation, and type of amines in cheese are

the availability of amino acids (and hence proteolysis

of cheese) and the presence of microorganisms, either

178 AMINES

added or as a contaminant, capable of decarboxylat-

ing amino acids. Several factors may contribute also,

such as pH, salt concentration, water activity,

ripening temperature and time, storage temperature,

bacterial density, and activity of amine catabolic

enzymes by means of mono- and diaminoxidase.

0032 The longer the aging process, the higher the bio-

genic amine content. Amines concentrate on the rind

of cheese. Numerous bacteria, both intentional (star-

ter cultures) and adventitious, have been reported as

being capable of amine production. Lactobacillus

spp. play a major role in histamine, tyramine, and

putrescine accumulation. Enterococcus spp. are no-

torious tyramine formers. Representatives of the

Enterobacteriaceae, even at low densities, can cause

cadaverine and putrescine build-up.

0033 Several outbreaks of histamine intoxication have

occurred following the consumption of cheese, par-

ticularly Swiss and Cheddar, containing high levels of

histamine. Migraine headaches have been observed

after ingestion of cheese with high levels of tyramine,

tryptamine, or phenylethylamine. Hypertensive crisis

has been observed after consumption of Swiss, Ched-

dar, Gouda, and Gruye

re cheeses with high tyramine

levels. Therefore, susceptible individuals should be

advised to consume cheese with a low biogenic

amine content. Furthermore, efforts should be made

to elucidate amine formation in cheese in order to

optimize the technology and secure low amine levels.

Fermented Beverages

0034 Although tyramine and histamine are the major

amines investigated in wine and beer, several different

amines have been detected. The type and concentra-

tion of amines in wines vary widely (Table 4). In

general, red wines contain significantly higher amine

levels compared with white. Some amines are normal

constituents of grapes, with levels varying with var-

iety and degree of ripening as well as with soil type

and composition. Among amines detected in grapes,

putrescine and spermidine are usually abundant,

whereas agmatine, cadaverine, spermine, and hista-

mine have been found in smaller amounts. During

wine-making, several amines can be formed and

accumulate. Several factors can affect amine forma-

tion, including the presence of precursor free amino

acids, must treatment, contact time of must and grape

skin, initial microbial population present on the fruit,

alcohol content, sulfur dioxide concentration, added

nutrients, pH, temperature, quantity and type of fin-

ings, and bacterial contamination in wineries. A

number of researchers have demonstrated that the

amine content increases with microbial growth.

0035The presence of biogenic amines in wines is also of

interest from a toxicological point of view. Histamine

has been considered the causative agent of physio-

logical distress experienced by individuals following

the consumption of red wines. However, reports

have demonstrated that tyramine, tryptamine, 2-

phenylethylamine, and serotonin may play an

important role as well as the simultaneous presence

of potentiating compounds in wines, such as ethanol,

aldehydes, and polyamines. Upper limits for hista-

mine in wine have been recommended in Germany

(2 mg l

1

), Belgium (5–6mgl

1

), France (8 mg l

1

)

and Switzerland (10 mg l

1

0036Since beer is generally consumed in greater

amounts than wine, it has been suggested that beer

might be more of a hazard to the consumer. Mainly,

raw materials, brewing techniques, and microbial

contamination during brewing affect the types and

levels of amines in beers. High levels of putrescine,

agmatine, spermine, and spermidine and low levels of

histamine, tryptamine, 2-phenylethylamine, and

cadaverine are usually found in malt. Tyramine,

putrescine, spermine, spermidine, and agmatine have

been detected in barley. Relatively high levels of

tyramine, 2-phenylethylamine, putrescine, spermine,

tbl0003 Table 3 Levels of biologically active amines in different types of cheese

Type of cheese Range of amine levels (mg per100 g)

Spermine Spermidine Putrescine Cadaverine Histamine Tyramine Tryptamine

Blue cheese – – 9.6–23.7 42.3–227 nd–409 2.2–166 nd–110

Cheddar – – nd–99.6 nd–40.8 nd–154 nd–153 nd–30

Gorgonzola – – 1.2–124 5.8–428 1.7–191 8.9–255 2.4–43

Gouda nd–1.13 nd–1.35 nd–107 nd–99.5 nd–30.5 nd–67 nd–88

Mozzarella nd–1.31 nd–1.06 nd–1.37 nd–2.34 nd–11.3 nd–41 nd–10

Parmesan 0.07–0.09 nd–0.15 nd–4.30 nd–9.80 nd–27.2 nd–29 nd–1.70

Provolone 0.07–0.97 nd–2.38 nd–8.70 nd–111 nd–8.2 nd–10.9 nd–1.08

Swiss – – – – nd–250 nd–180 nd–1.60

nd, not detectable; –, not determined.

From Stratton JE, Hutkins RW and Taylor SL (1991) Biogenic amines in cheese and other fermented foods: a review. Journal of Food Protection 54:

460–470; Hala

sz A, Bara

th A, Simon-Sarkadi L and Holzapfel W (1994) Biogenic amines and their production by microorganisms in food. Trends in Food

Science and Technology 51: 42–49; Vale S and Glo

ria MBA (1998) Biogenic amines in Brazilian cheeses. Food Chemistry 63(3): 343–348.

AMINES 179

and spermidine have been detected in hops. However,

their contribution to amine levels in beer is not sig-

nificant, since the amount used is very small. The use

of adjunct cereals such as rice has been found to be

useful in reducing biogenic amine levels in wort and

beer. Beers with a higher acidity usually have higher

amine contents.

0037 During beer production, several amines can be

formed and accumulate. Tyramine and agmatine can

accumulate during mashing and wort boiling, as a

result of thermal amino acid decarboxylation and

possibly enzymatic activity in the malt. Moreover,

amines can be formed during fermentation by con-

taminating lactic acid bacteria. Therefore, biogenic

amines could be associated with hygienic conditions

during brewing.

0038 In general, putrescine, agmatine, and spermidine

are inherent to beers (Table 4). Large variations in

the levels of histamine, tyramine, tryptamine, and

cadaverine have been observed. These amines are

formed mainly during brewing. Higher total amine

levels have been detected in stout and lower in ice beer.

Plant Foods

0039 In plants, putrescine, spermidine, and spermine are

implicated in a number of physiological processes,

such as cell division, flowering, fruit development,

response to stress, and senescence. Polyamines are

known to stimulate growth and inhibit ethylene pro-

duction, and therefore inhibit senescence. Amines are

also intermediates in alkaloids synthesis.

0040 The polyamines putrescine, agmatine, spermidine,

and spermine are often detected in plants, but sper-

midine is the prevalent amine, especially in seeds

and tissues undergoing growth. In conditions of

potassium and magnesium deficiency and high am-

monium concentration, putrescine and agmatine can

accumulate. Putrescine also builds up in plants sub-

jected to a wide range of stress conditions such as

osmotic shock, acidification, high salinity, drought,

desiccation, and temperature change.

0041Phenylethylamine, serotonin, tryptamine, and his-

tamine may be present also in plants, where they

have a protective role in deterring predators. Trypta-

mine and phenylethylamine are precursors of growth

substances. These amines have been used as a tool for

taxonomic studies. However, microbial contamina-

tion can cause increases in the biogenic amine content

of fruits and vegetables.

0042Besides spermidine, putrescine, and agmatine,

other types of amines have also been detected in

vegetables. Tyramine is present in cabbage, lettuce,

chicory, radish, tomato, potato, green onion, spinach,

and eggplant. Histamine is found in cabbage, egg-

plant, tomato, beet, and spinach. Tomato and

eggplant also have serotonin and tryptamine. Cada-

verine is only found in plants of the Leguminosae

family. Sprouts are usually rich in polyamines. High

levels of tyramine and histamine have been detected

in fermented vegetables such as sauerkraut, table

olives, soy sauce, and miso.

0043Fruits are generally rich in putrescine and spermi-

dine. High amine levels have been found in orange

juice (putrescine, tryptamine, tyramine, synephrine),

plum (serotonin, tryptamine, tyramine), banana, avo-

cado (serotonin, tyramine), pineapple (serotonin),

and raspberry (tyramine).

Other Food Products

0044Chocolate has been observed to contain high pheny-

lethylamine and serotonin levels. Phenylethylamine is

derived from the decarboxylation of phenylalanine

during cocoa bean roasting. Mushrooms also contain

high levels of phenylethylamine.

tbl0004 Table 4 Types and levels of biologically active amine levels in US wines and Brazilian beers

Food (numberof samples) Range of aminelevels (mgl

1

)

Agmatine Spermidine Spermine Putrescine Cadaverine Histamine Tyramine Tryptamine 2-Phenyl-

ethylamine

Wine

Pinot noir (36) nd–8.37 nd–2.35 nd–2.38 2.43–203 nd–2.07 nd–23.98 nd–8.31 nd–5.51 nd–0.89

Cabernet

Sauvignon (23)

nd–1.61 nd–4.03 nd–1.17 3.15–23.6 nd–1.51 nd–10.10 nd–7.53 nd nd–0.14

Beer

Lager (46) 2.10–46.8 nd–6.00 nd–1.41 0.85–9.80 0.15–2.60 nd–0.90 0.30–3.10 nd–0.80 nd–0.70

Stout (10) 2.80–16.8 0.31–1.38 nd–2.05 1.99–5.84 0.30–1.37 nd–0.85 0.48–36.8 nd–10.1 nd–0.69

Ice (5) 3.20–4.00 0.60–0.80 nd–0.30 3.90–4.50 0.10–0.20 nd 0.70–1.40 nd nd

Bock (23) 4.80–35.1 0.25–2.10 nd–1.73 1.55–6.30 0.15–1.72 nd–1.46 0.81–5.05 nd–3.50 nd–1.72

Nonalcoholic (7) 6.35–8.59 1.35–2.30 nd–1.20 2.30–4.95 nd–0.50 nd–0.62 0.60–3.30 nd–1.41 nd–0.32

nd, not detectable.

From Glo

ria MBA, Watson BT, Simon-Sarkadi L and Daeschel MA (1998) A survey of biogenic amines in Orgeon Pinot noir and Cabernet Sauvignon

wines. American Journal of Enology and Viticulture 49(3): 279–282; Glo

ria MBA and Izquierdo-Pulido M (1999) Levels and significance of biogenic amines in

Brazilian beers. Journal of Food Composition and Analysis 12: 129–136.

180 AMINES

0045 There is a clear need for further information on the

nature and quantity of amines in food products.

There is also a need to understand the effect of pro-

duction and processing on amine levels, in order to

optimize the technology and ensure low amine levels

in foods. This will enable food chemists to declare

limiting amine concentrations for certain food prod-

ucts. Furthermore, it will allow dietitians to formu-

late specific diets that are scientifically based, safe,

and practical.

See also: Fish: Tuna and Tuna-like Fish of Tropical

Climates; Spoilage of Seafood; Food Poisoning:

Classification; Histamine; Spoilage: Chemical and

Enzymatic Spoilage; Bacterial Spoilage