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SML0406

Roquefortine C

Name: Roquefortine C
Brand: SIGMA

≥98% (HPLC), (Penicillium crustosum)

别名:

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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关于此项目

经验公式（希尔记法）:

C₂₂H₂₃N₅O₂

化学文摘社编号:

58735-64-1

分子量:

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.

存储类别

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

法规信息

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Tremorgenic neuromycotoxicosis in 2 dogs ascribed to the ingestion of penitrem A and possibly roquefortine in rice contaminated with Penicillium crustosum.

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

The heterotrimeric Galpha protein pga1 regulates biosynthesis of penicillin, chrysogenin and roquefortine in Penicillium chrysogenum.

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

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)

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全球贸易项目编号

货号	GTIN
SML0406-500UG	04061833222690

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