Roquefortine C is a

mycotoxin A mycotoxin (from the Greek μύκης , "fungus" and τοξίνη , "toxin") is a toxic secondary metabolite produced by organisms of kingdom Fungi and is capable of causing disease and death in both humans and other animals. The term 'mycotoxin' ...

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

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

, particularly species from the genus ''

Penicillium ''Penicillium'' () is a genus of ascomycetous 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 the genus produce pe ...

''. 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 blue ...

'', 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 cheese from Southern France, and is one of the world's best known blue cheeses. Though similar cheeses are produced elsewhere, EU law dictates that only those cheeses aged in the natural Combalou caves of Roquefort-sur ...

, Danish Blue,

Stilton Stilton is a village and civil parish in Cambridgeshire, England, about north of Huntingdon in Huntingdonshire, which is a non-metropolitan district of Cambridgeshire as well as a historic county of England. History There is evidence of Neo ...

and

Gorgonzola Gorgonzola (; ) is a veined blue cheese, originally from Italy, made from unskimmed cow's milk. It can be buttery or firm, crumbly and quite salty, with a "bite" from its blue veining. History Historically, gorgonzola has been produced for ...

. 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 nerve tissue (causing neurotoxicity). Neurotoxins are an extensive class of exogenous chemical neurological insultsSpencer 2000 that can adversely affect function in both developing and mature nerv ...

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 (CYPs) are a superfamily of enzymes containing heme as a cofactor that functions as monooxygenases. In mammals, these proteins oxidize steroids, fatty acids, and xenobiotics, and are important for the clearance of various co ...

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, disinfect ...

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. Gram-positive bac ...

, 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 tautomeriz ...

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 poisonous carcinogens and mutagens that are produced by certain molds, particularly ''Aspergillus'' species. The fungi grow in soil, decaying vegetation and various staple foodstuffs and commodities such as hay, sweetcorn ...

Patulin Patulin is an organic compound classified as a polyketide. It is a white powder soluble in acidic water and in organic solvents. It is a lactone that is heat-stable, so it is not destroyed by pasteurization or thermal denaturation.http://www.s ...

References

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External links

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