Biogenic Amines in Fish: Roles in Intoxication, Spoilage, and Nitrosamine Formation—A Review

Abstract

Biogenic amines are non-volatile amines formed by decarboxylation of amino acids. Although many biogenic amines have been found in fish, only histamine, cadaverine, and putrescine have been found to be significant in fish safety and quality determination. Despite a widely reported association between histamine and scombroid food poisoning, histamine alone appears to be insufficient to cause food toxicity. Putrescine and cadaverine have been suggested to potentiate histamine toxicity. With respect to spoilage on the other hand, only cadaverine has been found to be a useful index of the initial stage of fish decomposition. The relationship between biogenic amines, sensory evaluation, and trimethylamine during spoilage are influenced by bacterial composition and free amino acid content. A mesophilic bacterial count of log 6-7 cfu/g has been found to be associated with 5 mg histamine/100 g fish, the Food and Drug Administration (FDA) maximum allowable histamine level. In vitro studies have shown the involvement of cadaverine and putrescine in the formation of nitrosamines, nitrosopiperidine (NPIP), and nitrosopyrrolidine (NPYR), respectively. In addition, impure salt, high temperature, and low pH enhance nitrosamine formation, whereas pure sodium chloride inhibits their formation. Understanding the relationships between biogenic amines and their involvement in the formation of nitrosamines could explain the mechanism of scombroid poisoning and assure the safety of many fish products.

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“…Although various causes have been indicated with the formation of nitrosamines in foods, the mechanisms of nitrosamine formation in fish products and factors influencing their formation have not been clearly elucidated. Nitrosamines are generally formed through reactions between secondary and tertiary amines and nitrite under certain conditions (Al Bulushi et al, 2009). The presence of secondary amines such as dimethylamine (DMA) and tertiary amines such as TMA has been found to be implicated in nitrosamine formation.…”

“…In fish products such as salted, pickled, smoked, fermented and canned fish, the presence of nitrosodimethylamine (NDMA) which is formed from DMA and nitrite, has been widely reported (Mitacek et al, 1999). Primary amines such as putrescine and cadaverine have been suggested to cyclize during heating to secondary amines such as pyrrolidine and piperidine, which react with nitrite to form carcinogenic nitrosamines (Al Bulushi et al, 2009). The International Agency for Research on Cancer (IARC, 1978) classified a number of NAs with respect to the cancer risk for humans.…”

“…Al Bulushi et al (2009) reviewed the nitrosamine levels in traditional products originated from various countries (China, Estonia, Poland, Thailand and South Korea) and reported that NDMA accounted for 86% of the total N-nitrosamines in salted fish in China. Yurchenko and Mölder (2006) found varying nitrosamine levels in Estonian fish samples including TFPs.…”

“…The IARC considers NDMA and N-nitrosodiethylamine (NDEA) into the group of probably carcinogenic to human, and N-nitrosodibutylamine (NDBA), N-nitrosopiperidine (NPIP) and N-nitrosopyrrolidine (NPYR) into the group of possibly carcinogenic to human (Yurchenko and Mölder, 2006). The USA has set 10 µg/kg NPYR as the maximum allowable limit in bacon (DomanskaBlicharz et al, 2005;Al Bulushi et al, 2009) while not many countries including the EU regulations set regulations for nitrosamines originated from food. Estonian government has maximum permitted concentration of the sum of two NAs (NDMA and NDEA) in fresh and smoked fish, which is 3 μg/kg (Yurchenko and Mölder, 2006).…”

“…TFPs usually carry all these health risks although some of them are specific to other seafoods such as shellfish (e.g., paralytic shellfish poisoning) (FDA, 2001;Huss et al, 2003;Stolyhwo and Sikorski, 2005;Yurchenko and Molder, 2006;Karl, 2008;Al Bulushi et al, 2009).…”