| Identification | Back Directory | [Name]
ROQUEFORTINE C | [CAS]
58735-64-1 | [Synonyms]
Nsc292134
Aids031208
Aids-031208
ROQUEFORTIN
RORIFONE95%
ROQUEFORTINE
ROQUEFORTINE C
ISOROQUEFORTINE C
PYRAZINO1215PYRROLO23BINDOLE143H5AH
roquefortine from penicillium*roqueforti
1-dimethyl-2-propenyl)-3-(1h-imidazol-4-ylmethylene)-rahydro-10b-(
2h-pyrazino(1’,2’:1,5)pyrrolo(2,3-b)indole-1,4-(3h,5ah)-dione,6,10b,11,11a-tet
10B-(1,1-DIMETHYL-2-PROPENYL)-6,10B,11,11A-TETRAHYDRO-3-(1H-IMIDAZOL-4-YLMETHYLENE)-2H-PYRAZINO(1',2':1,5)PYRROLO(2,3-B)INDOLE-1,4(3H,5AH)-DIONE
2H-Pyrazino[1',2':1,5]pyrrolo[2,3-B]indole-1,4(3H,5ah)-dione, 10B-(1,1-dimethyl-2-propenyl)-6,10B,11,11A-tetrahydro-3-(1H-imidazol-4-ylmethylene)-, (3Z)-
(3E,5aS,5aβ)-10bβ-(1,1-Dimethyl-2-propenyl)-3-(1H-imidazol-4-yl)methylene-6,10b,11,11aα-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione
(5aS)-3-[(E)-(1H-Imidazole-4-yl)methylene]-10bβ-(1,1-dimethyl-2-propenyl)-1,3,4,5aβ,6,10b,11,11aα-octahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione
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)-
10b-(1,1-dimethyl-2-propenyl)-6,10b,11,11a-tetrahydro-3-(1H-imidazol-4-ylmethylene)-2H-pyrazino(1,2:1,5)pyrrolo(2,3-b)indole-1,4(3H,5aH)-dione, Isoroquefortine C, Roquefortin, Roquefortine C | [Molecular Formula]
C22H23N5O2 | [MDL Number]
MFCD00133802 | [MOL File]
58735-64-1.mol | [Molecular Weight]
389.45 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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. | [Definition]
ChEBI: Roquefortine C is a pyrroloindole. | [Biological Activity]
Potent neurotoxin produced by a diverse range of fungi, most notably Penicillium species. Inhibits growth of Gram-positive bacteria. Inhibits cytochrome p450. | [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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