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Merck

SML0406

Roquefortine C

≥98% (HPLC), from Penicillium roqueforti

동의어(들):

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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제품정보 (DICE 배송 시 비용 별도)

실험식(Hill 표기법):
C22H23N5O2
CAS 번호:
Molecular Weight:
389.45
UNSPSC Code:
12161501
NACRES:
NA.77
Assay:
≥98% (HPLC)
Quality level:
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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

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.

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral - STOT RE 2

target_organs

Nervous system

저장 등급

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


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문서 라이브러리에서 최근에 구매한 제품에 대한 문서를 찾아보세요.

문서 라이브러리 방문

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)
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
C Aninat et al.
Food additives and contaminants, 22(4), 361-368 (2005-07-16)
Man is permanently exposed to exogenous substances, either natural ones (e.g. mycotoxins, plant extracts) or man-made compounds such as pesticides or drugs. In some cases, such foreign compounds can exert either therapeutic (drugs) or toxic effects, or both. In particular
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
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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