ROQUEFORTINE C Chemical Properties

Melting point:

202-205℃

Boiling point:

768.3±60.0 °C(Predicted)

Density 

1.37±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

chloroform: soluble1mg/mL

form 

White to off-white solid.

pka

11.10±0.40(Predicted)

color 

White to off-white

Stability:

Hygroscopic

Safety Information

Hazard Codes 

T

Risk Statements 

23/24/25

Safety Statements 

22-36/37/39-45

RIDADR 

UN 2811 6.1/PG 2

WGK Germany 

3

RTECS 

UQ4730500

HS Code 

2941900000

Hazardous Substances Data

58735-64-1(Hazardous Substances Data)

ROQUEFORTINE C Usage And Synthesis

Description

Roquefortine C is a mycotoxin that was first isolated from a strain of P. roqueforti, a species of Penicillium commercially used to ripen blue-veined cheeses. It has also been isolated from other members of the Penicillium genus found in contaminated food products where it displays neurotoxic properties. It has been shown to both activate a P-glycoprotein transport system involved in the efflux of xenobiotics and to inhibit cytochrome P450 3A detoxification enzymes. It has also been used as a biomarker for penitrem A intoxication.

Description

The third alkaloid isolated from a surface culture of Penicillium roqueforti, roquefortine C is present in only small quantities and the amount obtained is insufficient for the full structure to be established.

Uses

Roquefortine C is a potent tremorgenic mycotoxin originally isolated from Penicillium roqueforti in 1975 in Japan. Parallel research by Scott and colleagues lead to the structure elucidation of roquefortine C as an unusual diketopiperazine formed by coupling a prenylated tryptophan and histidine. Roquefortine C was subsequently found to be produced by a diverse range of fungi, most notably Penicillium species. Roquefortine is an important mycotoxin as low levels can be found in foodstuffs.

Uses

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).

Definition

ChEBI: Roquefortine C is a pyrroloindole.

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.

References

Ohmono et al., Agr. Bioi. Chem., 39, 1333 (1975)

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