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SML0406

Sigma-Aldrich

Roquefortine C

≥98% (HPLC), from Penicillium roqueforti

Synonym(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

Empirical Formula (Hill Notation):
C22H23N5O2
CAS Number:
Molecular Weight:
389.45
UNSPSC Code:
12161501
NACRES:
NA.77

biological source

Penicillium roqueforti

Quality Level

Assay

≥98% (HPLC)

solubility

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

storage temp.

−20°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-

InChI key

SPWSUFUPTSJWNG-SXGWCWSVSA-N

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).

Biochem/physiol Actions

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.

Preparation Note

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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C Aninat et al.
Food additives and contaminants, 22(4), 361-368 (2005-07-16)
Man is permanently exposed to exogenous substances, either natural ones (e.g. mycotoxins, plant extracts) or man-made compounds such as pesticides or drugs. In some cases, such foreign compounds can exert either therapeutic (drugs) or toxic effects, or both. In particular
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
M A Mansfield et al.
Phytopathology, 98(3), 330-336 (2008-10-24)
Toxins produced by Penicillium species are reported in maize silage and have been associated with health problems in cattle. Our objectives were to evaluate the prevalence and dynamics of patulin (PAT), mycophenolic acid (MPA), cyclopiazonic acid (CPA), and roquefortine C
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.
Ben Clark et al.
Journal of natural products, 68(11), 1661-1664 (2005-11-29)
The new isoprenylated diketopiperazine roquefortine E (6) has been isolated from an Australian soil isolate of the ascomycete Gymnoascus reessii. The known fungal metabolite roquefortine C (1) was also recovered as the major antibacterial principle, and all structures were assigned

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