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Roquefortine C

February 16, 2024

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
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)
  • Interactive image
ChEMBL
  • ChEMBL517788
ChemSpider
  • 10246629 Y
  • 21608802
UNII
  • 4VW6U94XFK Y
  • DTXSID20891816
  • 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
  • CC(C)(C=C)[C@@]12C[C@H]3C(=O)N/C(=C/c4cnc[nH]4)/C(=O)N3[C@@H]1Nc5c2cccc5
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).
N verify (what is YN ?)

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 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. S2CID 1334464.
  4. ^ a b c Aninat C, Hayashi Y, André F, Delaforge M (July 2001). "Molecular requirements for inhibition of cytochrome 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". {{cite journal}}: Cite journal requires |journal= (help)
  6. ^ EPA. "Penicillium roqueforti Final Risk Assessment". {{cite journal}}: Cite journal requires |journal= (help)
  7. ^ Finoli C, Vecchio A, Galli A, Dragoni I (February 2001). "Roquefortine C occurrence in blue cheese". J. Food Prot. 64 (2): 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. 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. S2CID 9880652.
  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

  • Roquefortine C on https://www.scbt.com

February 16, 2024
roquefortine, mycotoxin, that, belongs, class, naturally, occurring, diketopiperazines, produced, various, fungi, particularly, species, from, genus, penicillium, first, isolated, from, strain, penicillium, roqueforti, species, commercially, used, source, prot. 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 NamesPreferred 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 dioneIdentifiersCAS Number 58735 64 1 Y PubChem 3D model JSmol Interactive imageChEMBL ChEMBL517788ChemSpider 10246629 YPubChem CID 21608802UNII 4VW6U94XFK YCompTox Dashboard EPA DTXSID20891816InChI 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 NKey SPWSUFUPTSJWNG JJUKSXGLSA N NInChI 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 s1Key SPWSUFUPTSJWNG JJUKSXGLBASMILES CC C C C C 12C C H 3C O N C C c4cnc nH 4 C O N3 C H 1Nc5c2cccc5PropertiesChemical formula C22H23N5O2Molar mass 389 5 g molAppearance White to off white solidSolubility in water Soluble in ethanol methanol DMF or DMSOExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N 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 CHowever isoroquefortine C is not a natural product and in contrast to roquefortine C does not bind iron Both have been synthesised 10 Related compounds editAristolochene Aflatoxin PatulinReferences edit 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 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 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 S2CID 1334464 a b c Aninat C Hayashi Y Andre F Delaforge M July 2001 Molecular requirements for inhibition of cytochrome P450 activities by roquefortine Chemical Research in Toxicology 14 9 1259 1265 doi 10 1021 tx015512l PMID 11559041 SCBT Roquefortine A potent neurotoxin produced most notably by Penicillium species a href Template Cite journal html title Template Cite journal cite journal a Cite journal requires journal help EPA Penicillium roqueforti Final Risk Assessment a href Template Cite journal html title Template Cite journal cite journal a Cite journal requires journal help Finoli C Vecchio A Galli A Dragoni I February 2001 Roquefortine C occurrence in blue cheese J Food Prot 64 2 246 51 doi 10 4315 0362 028x 64 2 246 PMID 11271775 Kopp Holtwiesche B Rehm HJ December 1989 Antimicrobial action of roquefortine Journal of Environmental Pathology Toxicology and Oncology 10 1 2 41 44 PMID 2231314 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 S2CID 9880652 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 editRoquefortine C on https www scbt com Retrieved from https en wikipedia org w index php title Roquefortine C amp oldid 1136323705, wikipedia, wiki, book, books, library,

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