Spain – Enniatins, mycotoxins of emerging interest

ACSA

Molecular structure of enniatins

Origin and chemical structure

Enniatins (ENN) are a group of emerging mycotoxins produced by species of the genus Fusarium. They have a cyclic hexadepsipeptide structure that has three d-2 hydrocarboxylic amino acids and three N-methylamino amino acids linked alternately.

Enniatins have been found predominantly in cereal grains, such as barley, corn, oats, wheat, and rice, but they have also been found in nuts, dried fruit, bananas, Chinese medicinal herbs, and river water. Up to 29 natural analogs of enniatins are known, but only seven (A, A1, A2, B, B1, B2 and B3) have been detected in cereals and their derivatives, and enniatins A, A1, B and B1 are the findings most frequently in food and feed.

Table Functional groups that occupy the R positions in the figure and that determine enniatin.

Enniatina R1 R2 R3 R4 R5 R6
TO sec -butyl sec -butyl sec -butyl CH3 CH3 CH3
A1 iso- propyl sec -butyl sec -butyl CH3 CH3 CH3
A2 iso- propyl sec -butyl iso- propyl CH3 CH3 CH3
B iso- propyl iso- propyl iso- propyl CH3 CH3 CH3
B1 iso- propyl iso- propyl sec -butyl CH3 CH3 CH3
B2 iso- propyl iso- propyl iso- propyl H CH3 CH3
B3 iso- propyl iso- propyl iso- propyl H H CH3
B4 iso- propyl iso- propyl iso -butyl CH3 CH3 CH3
Beauvericin benzyl benzyl benzyl CH3 CH3 CH3

Since they originate from the same fungal species, enniatins are found concomitantly in food with other Fusarium mycotoxins , such as deoxynivalenol, moniliformin and fumonisins, and especially with beauvericin, another mycotoxin of emerging interest, since, in addition, it also shares the hexadipepsidic structure. This coincidence of origin and structural means that beauvericin is grouped analytically and toxicologically with the enniatins. Furthermore, analytical data show a high concomitance between enniatins and beauvericin in cereal grains.

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