What is Aflatoxin B1?

Aflatoxins are naturally occurring mycotoxins that are produced by many species of Aspergillus, a fungus, the most notable ones being Aspergillus flavus and Aspergillus parasiticus. Their name is derived from the early work that discovered Aspergillus Flavus toxins. Aflatoxins are toxic and among the most carcinogenic substances known. After entering the body, aflatoxins may be metabolized by the liver to a reactive epoxide intermediate or hydroxylated to become the less harmful aflatoxin M1.
Aflatoxin B1 is derived from both a dedicated fatty acid synthase (FAS) and a polyketide synthase (PKS), together known as norsolorinic acid synthase. The biosynthesis begins with the synthesis of hexanoate by the FAS, which then becomes the starter unit for the iterative type I PKS. The PKS adds seven malonyl-CoA extenders to the hexanoate to form the C20 polyketide compound. The PKS folds the polyketide in a particular way to induce cyclization to form the anthraquinone norsolorinic acid. A reductase(E1) then catalyzes the reduction of the ketone on the norsolorinic acid side-chain to yield averantin. Averantin is converted to averufin via a two different enzymes, a hydroxylase (E2) and an alcohol dehydrogenase (E3). This will oxygenate and cyclize averantin's side chain to form the ketal in averufin.
From this point on the biosynthetic pathway of aflatoxin B1 becomes much more complicated, with several major skeletal changes. Most of the enzymes have not been characterized and there may be several more intermediates that are still unknown. However, what is known is that averufin is oxidized by a P450-oxidase, AvfA (E4), in a Baeyer-Villiger oxidation. This opens the ether rings and upon rearrangement versiconal acetate is formed. Now an esterase, EstA (E5), catalyzes the hydrolysis of the acetyl, forming the primary alcohol in versiconal. The acetal in versicolorin A is formed from the cyclization of the side-chain in versiconal, which is catalyzed by VERB synthase (E6), and then VerB, a desaturase (E7), reduces versicolorin B to form the dihydrobisfuran.
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