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Chemical compound
Roquefortine C is a mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines[1] produced by various fungi, particularly species from the genus Penicillium.[2] It was first isolated from a strain of Penicillium roqueforti, a species commercially used as a source of proteolytic and lipolytic enzymes during maturation of the blue-veined cheeses, Roquefort, Danish Blue, Stilton and Gorgonzola.
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.[3] At high doses roquefortine C is classified as a toxic compound.[4] Although it is a potent neurotoxin[5][6] 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".[7] The mechanisms underlying its toxicity and metabolism have been investigated by studying its interaction with mammalian cytochrome P450 enzymes.[4] In addition to these toxic properties, roquefortine C reportedly possesses bacteriostatic activity against gram-positive bacteria,[8] but only in those organisms containing haemoproteins.[4][9]
Roquefortine C contains the unusual E-dehydrohistidine moiety, a system that typically undergoes facile isomerization under acidic, basic, or photochemical conditions to isoroquefortine C, the 3,12 double-bond Z-isomer of roquefortine C.[10]
However isoroquefortine C is not a natural product and in contrast to roquefortine C does not bind iron. Both have been synthesised.[10]
^Borthwick AD (2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products". Chemical Reviews. 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049.
^Kokkonen M, Jestoi M, Rizzo A (2005). "The effect of substrate on mycotoxin production of selected Penicillium strains". International Journal of Food Microbiology. 99 (2): 207–14. doi:10.1016/j.ijfoodmicro.2004.08.014. PMID 15734568.
^Borthwick AD, Da Costa NC (2017). "2,5-Diketopiperazines in Food and Beverages: Taste and Bioactivity". Critical Reviews in Food Science and Nutrition. 57 (4): 718–742. doi:10.1080/10408398.2014.911142. PMID 25629623. S2CID 1334464.
^ abcAninat C, Hayashi Y, André F, Delaforge M (July 2001). "Molecular requirements for inhibition of cytochrome P450 activities by roquefortine". Chemical Research in Toxicology. 14 (9): 1259–1265. doi:10.1021/tx015512l. PMID 11559041.
^SCBT. "Roquefortine - A potent neurotoxin produced most notably by Penicillium species". {{cite journal}}: Cite journal requires |journal= (help)
^Finoli C, Vecchio A, Galli A, Dragoni I (February 2001). "Roquefortine C occurrence in blue cheese". J. Food Prot. 64 (2): 246–51. doi:10.4315/0362-028x-64.2.246. PMID 11271775.
^Kopp-Holtwiesche B, Rehm HJ (December 1989). "Antimicrobial action of roquefortine". Journal of Environmental Pathology, Toxicology and Oncology. 10 (1–2): 41–44. PMID 2231314.
^Aninat C, Andre F, Delaforge M (April 2005). "Oxidative metabolism by P450 and function coupling to efflux systems: modulation of mycotoxin toxicity". Food Additives and Contaminants. 22 (4): 361–368. doi:10.1080/02652030500073287. PMID 16019806. S2CID 9880652.
^ abShangguan N, Hehre WJ, Ohlinger WS, Beavers MP, Joullie MM (April 2008). "The total synthesis of roquefortine C and a rationale for the thermodynamic stability of isoroquefortine C over roquefortine C". Journal of the American Chemical Society. 130 (19): 6281–6287. doi:10.1021/ja800067q. PMID 18412344.
RoquefortineC is a mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines produced by various fungi, particularly species from...
significantly penicillin. Other secondary metabolites of P. chrysogenum include roquefortineC, meleagrin, chrysogine, 6-MSA YWA1/melanin, andrastatin A, fungisporin...
cells. P. roqueforti also produces the neurotoxin roquefortineC. However, the levels of roquefortineC in cheese made from it is usually too low to produce...
griseofulvin, lichexanthone, roquefortineC, roquefortine D, patulin and chrysogine MycoBank UniProt Wang, L; Zhou, H. B.; Frisvad, J. C.; Samson, R. A. (2004)...
coprophilum is a species of the genus of Penicillium which produces roquefortineC, griseofulvin and oxaline. List of Penicillium species MycoBank UniProt...
species of fungus in the genus Penicillium which produces roquefortineC and roquefortine D. MycoBank UniProt Jan Dijksterhuis; Robert A. Samson (2007)...
marinum is a species in the genus Penicillium which produces patulin and roquefortineC. Wigley, L. J.; Perry, D. A.; Mantle, P. G. (2008). "An experimental...
Penicillium fungi. It is similar to other fungal alkaloids, such as RoquefortineC, which is made as an intermediate in the same biosynthetic pathway....
ranging from tremors, seizures, and hyperthermia to ataxia and nystagmus. RoquefortineC has been commonly detected in documented cases of penitrem A poisoning...
species of the genus of Penicillium which produces pyripyropene A, roquefortineC, penicillic acid and patulin. List of Penicillium species Hu, J; Okawa...
Penicillium which produces patulin, penifulvin A, cyclopiazonic acid, roquefortineC, shikimic acid, griseofulvin, and 6-Methylsalicylic acid (via a polyketide...
species of the genus of Penicillium which produces corymbiferone and roquefortineC. Overy, D. P.; Blunt, J. W. (2004). "Corymbiferan lactones from Penicillium...
in the genus Penicillium which produces xanthomegin, verrucosidin, roquefortineC and penitrem A. Penicillium megasporum occurs in grain MycoBank UniProt...
fungus in the genus Penicillium which produces penicillic acid, roquefortineC, roquefortine D, terrestric acid, glandicoline A, glandicoline B, meleagrin...
the genus of Penicillium which produces penitrem A, penicillin and roquefortineC. List of Penicillium species MycoBank Straininfo of Penicillium flavigenum...
anamorph fungus species of the genus of Penicillium which produces roquefortineC and patulin. List of Penicillium species MycoBank Straininfo of Penicillium...
Penicillium which produces penitrem A, patulin, 2,4,6-trichloroanisole and roquefortineC MycoBank UniProt ATCC John I. Pitt, Ailsa D. Hocking (2009). Fungi and...
radicicola is a species of fungus in the genus Penicillium which produces RoquefortineC and occurs on onions. MycoBank UniProt Jan Dijksterhuis; Robert A. Samson...
been isolated from soil in Australia. Aspergillus brevipes produces roquefortineC, meleagrin and viriditoxin. A. brevipes has been cultivated on both...
produces 1-Octen-3-ol and penipanoid A, penipanoid B, penipanoid C, patulin and roquefortineC MycoBank Straininfo of Penicillium paneum UniProt Chitarra,...
safe for human consumption; however, mycotoxins (e.g., aflatoxins, roquefortineC, patulin, or others) may accumulate because of growth of other fungi...
activity. In addition, P. crustosum can produce thomitrems A and E, and roquefortineC. Consumption of foods spoiled by this mold can cause transient neurological...
Zhou, Han-Bai; C. Frisvad, Jens; A. Samson, Robert (2004). "Penicillium persicinum, a new griseofulvin, chrysogine and roquefortineC producing species...
aspect of blue cheese, produces several mycotoxins. While mycotoxins like roquefortine, isofumigaclavine A, mycophenolic acid and ferrichrome are present at...
important bioactive compounds such as andrastin, chrysogine, fungisporin, roquefortine, and sorbicillins. Belgian microbiologist Philibert Melchior Joseph Ehi...
is the only known species to be able to produce both penitrem A and roquefortine. Although this species does not produce penicillin, it has shown to have...