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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:
58735-64-1
Molecular Weight:
389.45
UNSPSC Code:
12161501
NACRES:
NA.77

biological source

Penicillium roqueforti

Quality Level

200

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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T W Naudé et al.
Journal of the South African Veterinary Association, 73(4), 211-215 (2003-04-01)
Two dogs developed alarming tremorgenic nervous stimulation shortly after ingesting discarded rice that had been forgotten in a refrigerator for an undetermined period and that was covered with a grey-green mould. Both dogs exhibited vomition followed by slight salivation, tremors
Ramón O García-Rico et al.
Microbiology (Reading, England), 154(Pt 11), 3567-3578 (2008-10-30)
We have studied the role of the pga1 gene of Penicillium chrysogenum, encoding the alpha subunit of a heterotrimeric G protein, in secondary metabolite production. The dominant activating pga1(G42R) mutation caused an increase in the production of the three secondary
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)
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.
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
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