(−)-citrinin

Citrinin is a mycotoxin which is often found in food. It is a secondary metabolite produced by fungi that contaminates long-stored food and it can cause a variety of toxic effects, including kidney, liver and cell damage. Citrinin is mainly found in stored grains, but sometimes also in fruits and other plant products.

== History == Citrinin was one of the many mycotoxins discovered by H. Raistrick and A.C. Hetherington in the 1930s. In 1941 H. Raistrick and G. Smith identified citrinin to have a broad antibacterial activity. After this discovery the interest in citrinin rose. However, in 1946 A.M. Ambrose and F. DeEds demonstrated that citrinin was toxic to mammals. As a result, the interest in citrinin decreased, but there still was a lot of research. In 1948 the chemical structure was found by W.B. Whalley and coworkers. Citrinin is a natural compound and it was first isolated from Penicillium citrinum, but is also produced by other Penicillium species, such as the Monascus species and the Aspergillus species, which are both fungi. During the 1950s W.B. Whalley, A.J. Birch and others identified citrinin as a polyketide and investigated its biosynthesis using radioisotopes. During the 1980s and 1990s J. Staunton, U. Sankawa and others also investigated its biosynthesis using stable isotopes and NMR. The gene cluster expression system for citrinin was reported in 2008.