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SML0406

Sigma-Aldrich

Roquefortine C

≥98% (HPLC), from Penicillium roqueforti

Synonyme(s) :

2H-Pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione, 10b-(1,1-dimethyl-2-propen-1-yl)-6,10b,11,11a-tetrahydro-3-(1H-imidazol-5-ylmethylene)-,(3E,5aS,10bR,11aS)-, Roquefortine from Penicillium roqueforti

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About This Item

Formule empirique (notation de Hill):
C22H23N5O2
Numéro CAS:
Poids moléculaire :
389.45
Code UNSPSC :
12161501
Nomenclature NACRES :
NA.77

Source biologique

Penicillium roqueforti

Niveau de qualité

Essai

≥98% (HPLC)

Solubilité

chloroform: 1 mg/mL
ethyl acetate: 1 mg/mL
DMSO: 10 mg/mL
methanol: 10 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

N21C3Nc4c(cccc4)C3(CC2C(=O)N\C(=C/c5nc[nH]c5)\C1=O)C(C)(C)C=C

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-

Clé InChI

SPWSUFUPTSJWNG-SXGWCWSVSA-N

Catégories apparentées

Application

Roquefortine C has been used as a standard for the quantification of roquefortine C by high-performance liquid chromatography (HPLC). It has also been used as a standard for the quantification of roquefortine C by liquid chromatography-mass spectrometry (LC−MS/MS).

Actions biochimiques/physiologiques

Roquefortine C is a paralytic neurotoxin of a dioxopiperazine structure produced by a diverse range of fungi, most notably Penicillium species.
Roquefortine C is a paralytic neurotoxin of a dioxopiperazine structure produced by a diverse range of fungi, most notably Penicillium species. It has been found in blue cheese and in many other food products due to natural occurrence and contamination. Roquefortine C was found to be active on a wide range of organisms. It inhibits the growth of Gram-positive bacteria, and cockerels treated with roquefortine lost their righting reflex and died within 8-12 hours. Mice injected with roquefortine C experienced neurotoxic properties. Roquefortine C was also reported to inhibit cytochrome P450 as well as tubulin polymerization.

Notes préparatoires

Soluble in methanol (10 mg/mL), DMSO (10 mg/mL), ethyl acetate (1 mg/mL) and chloroform (1 mg/mL). DMSO solution at 10 mg/mL is stable for 3 months at −20 °C.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Consulter la Bibliothèque de documents

Songul Cakmakci et al.
Journal of food protection, 75(11), 2045-2049 (2012-11-07)
Moldy Civil is a mold-ripened variety of cheese produced mainly in eastern Turkey. This cheese is produced with Civil cheese and whey curd cheese (Lor). Civil cheese has had a geographical presence since 2009 and is manufactured with skim milk.
Long Wang et al.
Antonie van Leeuwenhoek, 86(2), 173-179 (2004-07-29)
A unique Penicillium isolate from Chinese soil with terverticillate penicilli and ellipsoidal to cylindrical smooth-walled conidia, produces, in addition to the common metabolite ergosterol, copious amounts of an unknown peach-red pigment and the following secondary metabolites: griseofulvin, dechlorogriseofulvin, lichexanthone, roquefortine
A natural short pathway synthesizes roquefortine C but not meleagrin in three different Penicillium roqueforti strains
Kosalkova K, et al.
Applied Microbiology and Biotechnology, 99(18), 7601-7612 (2015)
Ramón O García-Rico et al.
International microbiology : the official journal of the Spanish Society for Microbiology, 12(2), 123-129 (2009-09-29)
Heterotrimeric G protein signaling regulates many processes in fungi, such as development, pathogenicity, and secondary metabolite biosynthesis. For example, the Galpha subunit Pga1 from Penicillium chrysogenum regulates conidiation and secondary metabolite production in this fungus. The dominant activating allele, pga1G42R
David J Richard et al.
Proceedings of the National Academy of Sciences of the United States of America, 101(33), 11971-11976 (2004-05-14)
The syntheses of isoroquefortine C and a related heterocycle were achieved by implementation of both intra- and intermolecular vinyl amidation reactions. These accomplishments represent a significant advance in the use of these strategies in the generation of complex molecules.

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