Roquefortine C is a

mycotoxin A mycotoxin (from the Greek μύκης , "fungus" and τοξικός , "poisonous") is a toxic secondary metabolite produced by fungi and is capable of causing disease and death in both humans and other animals. The term 'mycotoxin' is usually rese ...

that belongs to a class of naturally occurring 2,5-diketopiperazines produced by various

fungi A fungus (: fungi , , , or ; or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and mold (fungus), molds, as well as the more familiar mushrooms. These organisms are classified as one ...

, particularly species from the genus ''

Penicillium ''Penicillium'' () is a genus of Ascomycota, ascomycetous fungus, fungi that is part of the mycobiome of many species and is of major importance in the natural environment, in food spoilage, and in food and drug production. Some members of th ...

''. It was first isolated from a strain of ''

Penicillium roqueforti ''Penicillium roqueforti'' is a common saprotrophic fungus in the genus ''Penicillium''. Widespread in nature, it can be isolated from soil, decaying organic matter, and plants. The major industrial use of this fungus is the production of blu ...

'', a species commercially used as a source of proteolytic and lipolytic enzymes during maturation of the blue-veined cheeses,

Roquefort Roquefort () is a sheep milk blue cheese from southern France. Though similar cheeses are produced elsewhere, European Union law, EU law dictates that only those cheeses aged in the natural Combalou caves of Roquefort-sur-Soulzon may bear the na ...

, Danish Blue, Stilton and

Gorgonzola Gorgonzola (, ) is a famously pungent Italian blue cheese made from unskimmed cow's milk; believed to have been created in the 9th century; now with use of its name controlled under the criteria of a Protected Designation of Origin (PDO). Gorg ...

. Roquefortine C is a cyclodipeptide mycotoxin derived from the diketopiperazine cyclo(Trp-dehydro-His) and is a relatively common fungal metabolite produced by a number of ''Penicillium'' species. It is also considered one of the most important fungal contaminants of carbonated beverages, beer, wine, meats, cheese and bread. At high doses roquefortine C is classified as a toxic compound. Although it is a potent

neurotoxin Neurotoxins are toxins that are destructive to nervous tissue, nerve tissue (causing neurotoxicity). Neurotoxins are an extensive class of exogenous chemical neurological insult (medical), insultsSpencer 2000 that can adversely affect function ...

at high doses, at low concentrations of 0.05 to 1.47 mg/kg that occur in domestic cheeses, it was found to be "safe for the consumer". The mechanisms underlying its toxicity and metabolism have been investigated by studying its interaction with mammalian

cytochrome P450 Cytochromes P450 (P450s or CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that mostly, but not exclusively, function as monooxygenases. However, they are not omnipresent; for examp ...

enzymes. In addition to these toxic properties, roquefortine C reportedly possesses

bacteriostatic A bacteriostatic agent or bacteriostat, abbreviated Bstatic, is a biological or chemical agent that stops bacteria from reproducing, while not necessarily killing them otherwise. Depending on their application, bacteriostatic antibiotics, disinfec ...

activity against

gram-positive bacteria In bacteriology, gram-positive bacteria are bacteria that give a positive result in the Gram stain test, which is traditionally used to quickly classify bacteria into two broad categories according to their type of cell wall. The Gram stain ...

, but only in those organisms containing haemoproteins. Roquefortine C contains the unusual E-dehydrohistidine moiety, a system that typically undergoes facile

isomerization In chemistry, isomerization or isomerisation is the process in which a molecule, polyatomic ion or molecular fragment is transformed into an isomer with a different chemical structure. Enolization is an example of isomerization, as is tautomer ...

under acidic, basic, or photochemical conditions to isoroquefortine C, the 3,12 double-bond Z-isomer of roquefortine C. Roquefortine C to Isoroquefortine C

However isoroquefortine C is not a natural product and in contrast to roquefortine C does not bind iron. Both have been synthesised.

Related compounds

* Aristolochene *

Aflatoxin Aflatoxins are various toxicity, poisonous carcinogens and mutagens that are produced by certain Mold (fungus), molds, especially ''Aspergillus'' species such as ''Aspergillus flavus'' and ''Aspergillus parasiticus''. According to the USDA, "The ...

Patulin Patulin is an organic compound classified as a polyketide. It is named after the fungus from which it was isolated, '' Penicillium patulum''. It is a white powder soluble in acidic water and in organic solvents. It is a lactone that is heat-stabl ...

References

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External links

Roquefortine C on https://www.scbt.com
Mycotoxins Penicillium Imidazoles Lactams Nitrogen heterocycles Diketopiperazines