isoroquefortine C

Names

[ Name ]:
isoroquefortine C

[Synonym ]:
isoroquefortine C
roquefortine from penicillium*roqueforti
10b-(1,1-dimethyl-allyl)-3-(1(3)H-imidazol-4-ylmethylene)-2,3,6,10b,11,11a-hexahydro-5aH-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)-, (3Z,5aS,10bR,11aS)-
(3Z,5aS,10bR,11aS)-3-(1H-Imidazol-5-ylmethylene)-10b-(2-methyl-3-buten-2-yl)-6,10b,11,11a-tetrahydro-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
isoroquefortine
Roquefortin
PYRAZINO1215PYRROLO23BINDOLE143H5AH
RORIFONE
ROQUEFORTINE

Biological Activity

[Description]:

Roquefortine C, a fungal cyclopeptide isolated from Penicillium roquefortii, activates P-gp and also inhibits P450-3A and other haemoproteins. Roquefortine C has bacteriostatic activities against Gram-positive bacteria[1].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

Signaling Pathways >> Membrane Transporter/Ion Channel >> P-glycoprotein

Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. García-Rico RO, et al. Effect of a heterotrimeric G protein alpha subunit on conidia germination, stress response, and roquefortine C production in Penicillium roqueforti. Food Addit Contam. 2005 Apr;22(4):361-8.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
768.3±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₂H₂₃N₅O₂

[ Molecular Weight ]:
389.450

[ Flash Point ]:
418.4±32.9 °C

[ Exact Mass ]:
389.185181

[ PSA ]:
90.12000

[ LogP ]:
1.40

[ Vapour Pressure ]:
0.0±2.6 mmHg at 25°C

[ Index of Refraction ]:
1.687

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UQ4730500

CAS REGISTRY NUMBER :: 58735-64-1

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C22-H23-N5-O2

MOLECULAR WEIGHT :: 389.50

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 15 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 32,140,1976

Safety Information

[ Risk Phrases ]:
23/24/25

[ Safety Phrases ]:
22-36/37/39-45

[ RIDADR ]:
UN 2811 6.1/PG 2

[ HS Code ]:
2933990090

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Novel key metabolites reveal further branching of the roquefortine/meleagrin biosynthetic pathway.

J. Biol. Chem. 288(52) , 37289-95, (2013)

Metabolic profiling and structural elucidation of novel secondary metabolites obtained from derived deletion strains of the filamentous fungus Penicillium chrysogenum were used to reassign various pre...

Determination of selected mycotoxins in mould cheeses with liquid chromatography coupled to tandem with mass spectrometry.

Food Addit. Contam. 22(5) , 449-56, (2005)

A simple and feasible method is described for analysing nine mycotoxins in cheese matrix. The method involves liquid extraction followed by high performance liquid chromatographic separation and mass ...

A single cluster of coregulated genes encodes the biosynthesis of the mycotoxins roquefortine C and meleagrin in Penicillium chrysogenum.

Chem. Biol. 18(11) , 1499-512, (2011)

A single gene cluster of Penicillium chrysogenum contains genes involved in the biosynthesis and secretion of the mycotoxins roquefortine C and meleagrin. Five of these genes have been silenced by RNA...