Roquefortine C

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

Chemical structure of roquefortine C
Names
Preferred IUPAC name (3E,5aS,10bR,11aS)-3-[(1H-Imidazol-5-yl)methylidene]-10b-(2-methylbut-3-en-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione
Identifiers
CAS Number	58735-64-1 Y[PubChem]
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL517788
ChemSpider	10246629 Y
PubChem CID	21608802
UNII	4VW6U94XFK Y
CompTox Dashboard (EPA)	DTXSID20891816
InChI InChI=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 N Key: SPWSUFUPTSJWNG-JJUKSXGLSA-N N 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 Key: SPWSUFUPTSJWNG-JJUKSXGLBA
SMILES CC(C)(C=C)[C@@]12C[C@H]3C(=O)N/C(=C/c4cnc[nH]4)/C(=O)N3[C@@H]1Nc5c2cccc5
Properties
Chemical formula	C22H23N5O2
Molar mass	389.5 g/mol
Appearance	White to off-white solid
Solubility in water	Soluble in ethanol, methanol, DMF or DMSO
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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]

Isomerisation of 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.^[10]

Related compounds

• Aristolochene
• Aflatoxin
• Patulin