Chemistry: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 | |
3D model (JSmol)
|
|
| ChEMBL | |
| ChemSpider | |
PubChem CID
|
|
| UNII | |
| |
| |
| Properties | |
| C22H23N5O2 | |
| Molar mass | 389.5 g/mol |
| Appearance | White to off-white solid |
| 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). | |
 verify (what is   ?)
| |
| Infobox references | |
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]
Related compounds
References
- ↑ 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.
- ↑ "The effect of substrate on mycotoxin production of selected Penicillium strains". International Journal of Food Microbiology 99 (2): 207–14. 2005. doi:10.1016/j.ijfoodmicro.2004.08.014. PMID 15734568.
- ↑ "2,5-Diketopiperazines in Food and Beverages: Taste and Bioactivity". Critical Reviews in Food Science and Nutrition 57 (4): 718–742. 2017. doi:10.1080/10408398.2014.911142. PMID 25629623.
- ↑ 4.0 4.1 4.2 "Molecular requirements for inhibition of cytochrome P450 activities by roquefortine". Chemical Research in Toxicology 14 (9): 1259–1265. July 2001. doi:10.1021/tx015512l. PMID 11559041.
- ↑ SCBT. Roquefortine - A potent neurotoxin produced most notably by Penicillium species. http://www.scbt.com/datasheet-202323-roquefortine-c.html.
- ↑ EPA. Penicillium roqueforti Final Risk Assessment. http://www.epa.gov/oppt/biotech/pubs/fra/fra008.htm.
- ↑ "Roquefortine C occurrence in blue cheese.". J. Food Prot. 64 (2): 246–51. February 2001. doi:10.4315/0362-028x-64.2.246. PMID 11271775.
- ↑ "Antimicrobial action of roquefortine". Journal of Environmental Pathology, Toxicology and Oncology 10 (1–2): 41–44. December 1989. PMID 2231314.
- ↑ "Oxidative metabolism by P450 and function coupling to efflux systems: modulation of mycotoxin toxicity". Food Additives and Contaminants 22 (4): 361–368. April 2005. doi:10.1080/02652030500073287. PMID 16019806.
- ↑ 10.0 10.1 "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. April 2008. doi:10.1021/ja800067q. PMID 18412344.
External links
 |  |
