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SML0406

Sigma-Aldrich

Roquefortine C

≥98% (HPLC), from Penicillium roqueforti

同義詞:

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

經驗公式(希爾表示法):
C22H23N5O2
CAS號碼:
分子量::
389.45
分類程式碼代碼:
12161501
NACRES:
NA.77

生物源

Penicillium roqueforti

品質等級

化驗

≥98% (HPLC)

溶解度

chloroform: 1 mg/mL
ethyl acetate: 1 mg/mL
DMSO: 10 mg/mL
methanol: 10 mg/mL

儲存溫度

−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 密鑰

SPWSUFUPTSJWNG-SXGWCWSVSA-N

應用

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).

生化/生理作用

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.

準備報告

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.

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


分析證明 (COA)

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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
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.
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
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

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