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SML0406

Roquefortine C

Name: Roquefortine C
Brand: SIGMA

≥98% (HPLC), (Penicillium crustosum)

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

Assay:

≥98% (HPLC)

Quality level:

200

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Quality Level

200

biological source

(Penicillium crustosum)

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

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

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

GHS06,GHS08

signalword

Danger

hcodes

H301,H373

pcodes

P260 - P264 - P301 + P310 - P314 - P405 - P501

Hazard Classifications

Acute Tox. 3 Oral - STOT RE 2

target_organs

Nervous system

Regulatory Information

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Effect of a heterotrimeric G protein alpha subunit on conidia germination, stress response, and roquefortine C production in Penicillium roqueforti.

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

Synthetic studies of roquefortine C: synthesis of isoroquefortine C and a heterocycle.

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.

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)

Roquefortine E, a diketopiperazine from an Australian isolate of Gymnoascus reessii.

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

The global regulator LaeA controls penicillin biosynthesis, pigmentation and sporulation, but not roquefortine C synthesis in Penicillium chrysogenum.

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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Global Trade Item Number

SKU	GTIN
SML0406-500UG	04061833222690

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