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Revision as of 14:39, 12 May 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit Latest revision as of 20:24, 29 January 2023 edit undoOAbot (talk | contribs)Bots439,234 editsm Open access bot: doi added to citation with #oabot. 
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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 387472331
| Watchedfields = changed
⚫ | verifiedrevid = 428761527
| Name = Roquefortine C | Name = Roquefortine C
| ImageFile = Roquefortine.svg | ImageFile = Structure of Roquefortine C.svg
| ImageSize = 250px | ImageSize = 200px
| ImageName = Chemical structure of roquefortine C | ImageName = Chemical structure of roquefortine C
| ImageAlt = Chemical structure of roquefortine C | ImageAlt = Chemical structure of roquefortine C
| PIN = (3''E'',5a''S'',10b''R'',11a''S'')-3--10b-(2-methylbut-3-en-2-yl)-6,10b,11,11a-tetrahydro-2''H''-pyrazinopyrroloindole-1,4(3''H'',5a''H'')-dione
| IUPACName =
| OtherNames = <!-- <br> --> | OtherNames = <!-- <br> -->
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|PubChem}}
| CASNo = 58735-64-1
| CASNo_Ref = | CASNo = 58735-64-1
| CASOther = | ChEMBL = 517788
| PubChem = | PubChem = 21608802
| UNII_Ref = {{fdacite|correct|FDA}}
| SMILES =
| InChI = | UNII = 4VW6U94XFK
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10246629
| SMILES = CC(C)(C=C)12C3C(=O)N/C(=C/c4cnc4)/C(=O)N31Nc5c2cccc5
| 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 = | MeSHName =
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>22</sub>H<sub>23</sub>N<sub>5</sub>O<sub>2</sub> | Formula = C<sub>22</sub>H<sub>23</sub>N<sub>5</sub>O<sub>2</sub>
| MolarMass = 389.5 g/mol | MolarMass = 389.5 g/mol
| ExactMass = <!-- u -->
| Appearance = White to off-white solid | Appearance = White to off-white solid
| Density = | Density =
| MeltingPt = <!-- °C --> | MeltingPt =
| BoilingPt = <!-- °C --> | BoilingPt =
| Solubility = Soluble in ethanol, methanol, DMF or DMSO | Solubility = Soluble in ethanol, methanol, DMF or DMSO
}} }}
}} }}
'''Roquefortin C''' is a ] produced by various ], particularly species from the '']'' genus.<ref name="pmid15734568">{{cite journal |author=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 |month=|pmid=15734568 |doi=10.1016/j.ijfoodmicro.2004.08.014 |url=http://linkinghub.elsevier.com/retrieve/pii/S0168-1605(04)00433-7}}</ref> It was first isolated from a strain of '']'', a species commercially used to make ]. '''Roquefortine C''' is a ] that belongs to a class of naturally occurring ]s<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 ], particularly species from the genus '']''.<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 '']'', a species commercially used as a source of proteolytic and lipolytic enzymes during maturation of the blue-veined cheeses, ], ], ] and ].


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 ]<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}}</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 ] enzymes.<ref name=" pmid111559041" /> In addition to these toxic properties, roquefortine C reportedly possesses ] activity against ],<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 ]s.<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>
⚫ ==References==

Roquefortine C contains the unusual E-dehydrohistidine moiety, a system that typically undergoes facile ] under acidic, basic, or photochemical conditions to isoroquefortine C, the 3,12 double-bond ] 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>
]
However isoroquefortine C is not a natural product and in contrast to roquefortine C does not bind iron. Both have been synthesised.<ref name="pmid18412344" />

== Related compounds ==
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⚫ == References ==
{{reflist}} {{reflist}}
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==External links==
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