{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 428761527 | Name = Roquefortine C | ImageFile = Structure of Roquefortine C.svg | ImageSize = 200px | ImageName = Chemical structure of roquefortine C | ImageAlt = Chemical structure of roquefortine C | PIN = (3''E'',5a''S'',10b''R'',11a''S'')-3-[(1''H''-Imidazol-5-yl)methylidene]-10b-(2-methylbut-3-en-2-yl)-6,10b,11,11a-tetrahydro-2''H''-pyrazino[1′,2′:1,5]pyrrolo[2,3-''b'']indole-1,4(3''H'',5a''H'')-dione | OtherNames = <!-- <br> --> |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|PubChem}} | CASNo = 58735-64-1 | ChEMBL = 517788 | PubChem = 21608802 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 4VW6U94XFK | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 10246629 | SMILES = CC(C)(C=C)[C@@]12C[C@H]3C(=O)N/C(=C/c4cnc[nH]4)/C(=O)N3[C@@H]1Nc5c2cccc5 | InChI = 1/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9+/t17-,20-,22+/m0/s1 | InChIKey = SPWSUFUPTSJWNG-JJUKSXGLBA | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9+/t17-,20-,22+/m0/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = SPWSUFUPTSJWNG-JJUKSXGLSA-N | MeSHName = }} |Section2={{Chembox Properties | Formula = C<sub>22</sub>H<sub>23</sub>N<sub>5</sub>O<sub>2</sub> | MolarMass = 389.5 g/mol | Appearance = White to off-white solid | Density = | MeltingPt = | BoilingPt = | Solubility = Soluble in ethanol, methanol, DMF or DMSO }} }} '''Roquefortine C''' is a mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines<ref>{{Cite journal | title = 2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products | author = Borthwick AD | journal = Chemical Reviews | year = 2012 | volume = 112 | issue = 7 | pages = 3641–3716 | doi = 10.1021/cr200398y | pmid = 22575049}}</ref> produced by various fungi, particularly species from the genus ''Penicillium''.<ref name="pmid15734568">{{cite journal |vauthors=Kokkonen M, Jestoi M, Rizzo A |title=The effect of substrate on mycotoxin production of selected ''Penicillium'' strains |journal=International Journal of Food Microbiology |volume=99 |issue=2 |pages=207–14 |year=2005 |pmid=15734568 |doi=10.1016/j.ijfoodmicro.2004.08.014 }}</ref> 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.<ref name="pmid25629623">{{cite journal |vauthors=Borthwick AD, Da Costa NC | title = 2,5-Diketopiperazines in Food and Beverages: Taste and Bioactivity | journal = Critical Reviews in Food Science and Nutrition | volume = 57 | issue = 4 | pages = 718–742 | date= 2017 | pmid = 25629623 | doi = 10.1080/10408398.2014.911142| s2cid = 1334464 }}</ref> At high doses roquefortine C is classified as a toxic compound.<ref name="pmid111559041">{{cite journal |vauthors=Aninat C, Hayashi Y, André F, Delaforge M | title = Molecular requirements for inhibition of cytochrome P450 activities by roquefortine | journal = Chemical Research in Toxicology | volume = 14 | issue = 9 | pages = 1259–1265| date= July 2001 | pmid = 11559041 | doi = 10.1021/tx015512l }}</ref> Although it is a potent neurotoxin<ref>{{cite journal |author=SCBT |title=Roquefortine - A potent neurotoxin produced most notably by ''Penicillium'' species |url=http://www.scbt.com/datasheet-202323-roquefortine-c.html}}</ref><ref>{{cite journal |author=EPA |title=''Penicillium roqueforti'' Final Risk Assessment |url=http://www.epa.gov/oppt/biotech/pubs/fra/fra008.htm|archive-url=https://web.archive.org/web/20130401070519/http://www.epa.gov/oppt/biotech/pubs/fra/fra008.htm|url-status=dead|archive-date=April 1, 2013}}</ref> at high doses, at low concentrations of 0.05 to 1.47&nbsp;mg/kg that occur in domestic cheeses, it was found to be "safe for the consumer".<ref>{{cite journal |vauthors=Finoli C, Vecchio A, Galli A, Dragoni I |title=Roquefortine C occurrence in blue cheese. |pmid=11271775 | volume=64 |issue=2 |date=February 2001 |journal=J. Food Prot. |pages=246–51 |doi=10.4315/0362-028x-64.2.246|doi-access=free }}</ref> The mechanisms underlying its toxicity and metabolism have been investigated by studying its interaction with mammalian cytochrome P450 enzymes.<ref name=" pmid111559041" /> In addition to these toxic properties, roquefortine C reportedly possesses bacteriostatic activity against gram-positive bacteria,<ref name="pmid2231314">{{cite journal |vauthors=Kopp-Holtwiesche B, Rehm HJ | title = Antimicrobial action of roquefortine | journal = Journal of Environmental Pathology, Toxicology and Oncology | volume = 10 | issue = 1–2 | pages = 41–44| date= December 1989 | pmid = 2231314 }}</ref> but only in those organisms containing haemoproteins.<ref name=" pmid111559041" /><ref name="pmid16019806">{{cite journal |vauthors=Aninat C, Andre F, Delaforge M | title = Oxidative metabolism by P450 and function coupling to efflux systems: modulation of mycotoxin toxicity | journal = Food Additives and Contaminants | volume = 22 | issue = 4 | pages = 361–368| date= April 2005 | pmid = 16019806 | doi = 10.1080/02652030500073287 | s2cid = 9880652 }}</ref>

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.<ref name="pmid18412344">{{cite journal |vauthors=Shangguan N, Hehre WJ, Ohlinger WS, Beavers MP, Joullie MM | title = The total synthesis of roquefortine C and a rationale for the thermodynamic stability of isoroquefortine C over roquefortine C | journal = Journal of the American Chemical Society | volume = 130 | issue = 19 | pages = 6281–6287| date= April 2008 | pmid = 18412344 | doi = 10.1021/ja800067q }}</ref> centre|400px|Isomerisation of Roquefortine C to Isoroquefortine C However isoroquefortine C is not a fungal product and in contrast to roquefortine C does not bind iron. Both have been synthesised.<ref name="pmid18412344" />

== Related compounds == * Aristolochene * Aflatoxin * Patulin

== References == {{reflist}}

==External links== * [https://www.scbt.com/scbt/product/roquefortine-c-58735-64-1 Roquefortine C on https://www.scbt.com]

Category:Mycotoxins Category:Penicillium Category:Imidazoles Category:Lactams Category:Nitrogen heterocycles Category:Diketopiperazines