Roquefortine C

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Roquefortine C
Chemical structure of roquefortine C
Identifiers
3D model (JSmol)
ChemSpider
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).
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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 Penicillium genus.[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 as 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.[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[edit]

References[edit]

  1. ^ 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. 
  2. ^ 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. 
  3. ^ 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. 
  4. ^ a b c Aninat C, Hayashi Y, André F, Delaforge M (July 2001). "Molecular requirements for inhibition of cytochromes P450 activities by roquefortine". Chemical research in toxicology. 14 (9): 1259–1265. doi:10.1021/tx015512l. PMID 11559041. 
  5. ^ SCBT. "Roquefortine - A potent neurotoxin produced most notably by Penicillium species". 
  6. ^ EPA. "Penicillium roqueforti Final Risk Assessment". 
  7. ^ Finoli C, Vecchio A, Galli A, Dragoni I (February 2001). "Roquefortine C occurrence in blue cheese". J. Food Prot. 64: 246–51. doi:10.4315/0362-028x-64.2.246. PMID 11271775. 
  8. ^ Kopp-Holtwiesche B, Rehm HJ (December 1989). "Antimicrobial action of roquefortine". Journal of environmental pathology, toxicology and oncology: official organ of the International Society for Environmental Toxicology and Cancer. 10 (1-2): 41–44. PMID 2231314. 
  9. ^ 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. 
  10. ^ a b Shangguan 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. 

External links[edit]