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Merck
CN

SML0406

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

Key Documents

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SMILES string

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-

InChI key

SPWSUFUPTSJWNG-SXGWCWSVSA-N

biological source

Penicillium roqueforti

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

Quality Level

200

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.
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

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

hcodes

H301,H373

Hazard Classifications

Acute Tox. 3 Oral - STOT RE 2

target_organs

Nervous system

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000524189
0000524189
019M4132V
14171013
126M4168V

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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
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
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.
Katarina Kosalková et al.
Biochimie, 91(2), 214-225 (2008-10-28)
The biosynthesis of the beta-lactam antibiotic penicillin is an excellent model for the study of secondary metabolites produced by filamentous fungi due to the good background knowledge on the biochemistry and molecular genetics of the beta-lactam producing microorganisms. The three
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