roquefortine
Identification
| Name | roquefortine |
| CAS Number | 58735-64-1 |
| FDA UNII | 4VW6U94XFK |
| Molecular Formula | C22 H23 N5 O2 |
| Molecular Weight | 389.45871000 |
| Beilstein | 1231991 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 205.3 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for roquefortine usage levels up to | not for fragrance use. |
| Recommendation for roquefortine flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
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)-
roquefortine C
PubMed:
Effect of Penicillium roqueforti mycotoxins on Caco-2 cells: Acute and chronic exposure.
PubMed:
Role of
sfk1
Gene in the Filamentous Fungus
Penicillium roqueforti
PubMed:
Silencing of a second dimethylallyltryptophan synthase of Penicillium roqueforti reveals a novel clavine alkaloid gene cluster.
PubMed:
Modeling Growth and Toxin Production of Toxigenic Fungi Signaled in Cheese under Different Temperature and Water Activity Regimes.
PubMed:
Validation and application of a liquid chromatography-tandem mass spectrometry based method for the assessment of the co-occurrence of mycotoxins in maize silages from dairy farms in NW Spain.
PubMed:
Biosynthetic gene clusters for relevant secondary metabolites produced by Penicillium roqueforti in blue cheeses.
PubMed:
The capability of fungi isolated from moldy dwellings to produce toxins.
PubMed:
OxaD: A Versatile Indolic Nitrone Synthase from the Marine-Derived Fungus Penicillium oxalicum F30.
PubMed:
[Exometabolites of the Fungal Isolates (Genus Penicillium, Section Chrysogena) from Low-Temperature Ecotopes].
PubMed:
Quinone/hydroquinone meroterpenoids with antitubercular and cytotoxic activities produced by the sponge-derived fungus Gliomastix sp. ZSDS1-F7.
PubMed:
Production of the Fusarium Mycotoxin Moniliformin by Penicillium melanoconidium.
PubMed:
Genome sequencing and secondary metabolism of the postharvest pathogen Penicillium griseofulvum.
PubMed:
The indole alkaloid meleagrin, from the olive tree endophytic fungus Penicillium chrysogenum, as a novel lead for the control of c-Met-dependent breast cancer proliferation, migration and invasion.
PubMed:
Evolutionary formation of gene clusters by reorganization: the meleagrin/roquefortine paradigm in different fungi.
PubMed:
Incorporating Fermentation into Undergraduate Laboratory Courses.
PubMed:
Influence of intraspecific variability and abiotic factors on mycotoxin production in Penicillium roqueforti.
PubMed:
A natural short pathway synthesizes roquefortine C but not meleagrin in three different Penicillium roqueforti strains.
PubMed:
A mutasynthesis approach with a Penicillium chrysogenum ÎroqA strain yields new roquefortine D analogues.
PubMed:
Mycotoxin production capability of Penicillium roqueforti in strains isolated from mould-ripened traditional Turkish civil cheese.
PubMed:
Secondary Metabolites from
Penicillium roqueforti
, A Starter for the Production of Gorgonzola Cheese.
PubMed:
Penicillium strains isolated from Slovak grape berries taxonomy assessment by secondary metabolite profile.
PubMed:
Antimicrobial and allelopathic metabolites produced by Penicillium brasilianum.
PubMed:
A comprehensive study to explore differences in mycotoxin patterns from agro-ecological regions through maize, peanut, and cassava products: a case study, Cameroon.
PubMed:
Novel key metabolites reveal further branching of the roquefortine/meleagrin biosynthetic pathway.
PubMed:
Exo-metabolites of mycelial fungi isolated in production premises of cheese-making and meat-processing plants.
PubMed:
Penicillium decumbens BrlA extensively regulates secondary metabolism and functionally associates with the expression of cellulase genes.
PubMed:
Pigment production by filamentous fungi on agro-industrial byproducts: an eco-friendly alternative.
PubMed:
A branched biosynthetic pathway is involved in production of roquefortine and related compounds in Penicillium chrysogenum.
PubMed:
Morphological, molecular, and mycotoxigenic identification of dominant filamentous fungi from moldy civil cheese.
PubMed:
Could cheese be the missing piece in the French paradox puzzle?
PubMed:
A single cluster of coregulated genes encodes the biosynthesis of the mycotoxins roquefortine C and meleagrin in Penicillium chrysogenum.
PubMed:
Ultrahigh-performance liquid chromatographic-tandem mass spectrometric multimycotoxin method for quantitating 26 mycotoxins in maize silage.
PubMed:
Isolation and structure elucidation of secopenitrem D, an indole alkaloid from Penicillium crustosum Thom.
PubMed:
Sex in Penicillium series Roqueforti.
PubMed:
Growth and mycotoxin production by fungi in atmospheres containing 80% carbon dioxide and 20% oxygen.
PubMed:
In vitro cytotoxicity of fungi spoiling maize silage.
PubMed:
Multi-mycotoxin analysis of maize silage by LC-MS/MS.
PubMed:
Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities.
PubMed:
Total Synthesis of Isoroquefortine E and Phenylahistin.
PubMed:
Occurrence of mycotoxins in feed as analyzed by a multi-mycotoxin LC-MS/MS method.
PubMed:
Poisoning of dogs with tremorgenic Penicillium toxins.
PubMed:
Proteolytic activity, mycotoxins and andrastin A in Penicillium roqueforti strains isolated from Cabrales, Valdeón and Bejes-Tresviso local varieties of blue-veined cheeses.
PubMed:
JEM Spotlight: Fungi, mycotoxins and microbial volatile organic compounds in mouldy interiors from water-damaged buildings.
PubMed:
Effect of a heterotrimeric G protein alpha subunit on conidia germination, stress response, and roquefortine C production in Penicillium roqueforti.
PubMed:
Growth and mycotoxin production by food spoilage fungi under high carbon dioxide and low oxygen atmospheres.
PubMed:
Using roquefortine C as a biomarker for penitrem A intoxication.
PubMed:
Intramolecular hydrogen bonding as a determinant of the inhibitory potency of N-unsubstituted imidazole derivatives towards mammalian hemoproteins.
PubMed:
The heterotrimeric Galpha protein pga1 regulates biosynthesis of penicillin, chrysogenin and roquefortine in Penicillium chrysogenum.
PubMed:
The global regulator LaeA controls penicillin biosynthesis, pigmentation and sporulation, but not roquefortine C synthesis in Penicillium chrysogenum.
PubMed:
Occurrence of mycotoxins in feedstuffs of dairy cows and estimation of total dietary intakes.
PubMed:
Contamination of fresh and ensiled maize by multiple penicillium mycotoxins.
PubMed:
Post-translational enzyme modification by the phosphopantetheinyl transferase is required for lysine and penicillin biosynthesis but not for roquefortine or fatty acid formation in Penicillium chrysogenum.
PubMed:
Rapid analysis of fungal cultures and dried figs for secondary metabolites by LC/TOF-MS.
PubMed:
The total synthesis of roquefortine C and a rationale for the thermodynamic stability of isoroquefortine C over roquefortine C.
PubMed:
Toxins from strains of Penicillium chrysogenum isolated from buildings and other sources.
PubMed:
Mycotoxins and other secondary metabolites produced in vitro by Penicillium paneum Frisvad and Penicillium roqueforti Thom isolated from baled grass silage in Ireland.
PubMed:
LC-MS/MS screen for penitrem A and roquefortine C in serum and urine samples.
PubMed:
Comparison of secondary metabolite production by Penicillium crustosum strains, isolated from Arctic and other various ecological niches.
PubMed:
Roquefortine E, a diketopiperazine from an Australian isolate of Gymnoascus reessii.
PubMed:
Roquefortine/oxaline biosynthesis pathway metabolites in Penicillium ser. Corymbifera: in planta production and implications for competitive fitness.
PubMed:
Determination of selected mycotoxins in mould cheeses with liquid chromatography coupled to tandem with mass spectrometry.
PubMed:
Oxidative metabolism by P450 and function coupling to efflux systems: modulation of mycotoxin toxicity.
PubMed:
Isolation and metabolite production by Penicillium roqueforti, P. paneum and P. crustosum isolated in Canada.
PubMed:
Inflammatory and cytotoxic responses in mouse lungs exposed to purified toxins from building isolated Penicillium brevicompactum Dierckx and P. chrysogenum Thom.
PubMed:
The effect of substrate on mycotoxin production of selected Penicillium strains.
PubMed:
The effects of the Penicillium mycotoxins citrinin, cyclopiazonic acid, ochratoxin A, patulin, penicillic acid, and roquefortine C on in vitro proliferation of porcine lymphocytes.
PubMed:
Combined effects of selected Penicillium mycotoxins on in vitro proliferation of porcine lymphocytes.
PubMed:
Cytotoxicity of occupationally and environmentally relevant mycotoxins.
PubMed:
Penicillium persicinum, a new griseofulvin, chrysogine and roquefortine C producing species from Qinghai Province, China.
PubMed:
Liquid chromatography method for the quantitation of the breast cancer resistance protein ABCG2 inhibitor fumitremorgin C and its chemical analogues in mouse plasma and tissues.
PubMed:
Penitrem and thomitrem formation by Penicillium crustosum.
PubMed:
Synthetic studies of roquefortine C: synthesis of isoroquefortine C and a heterocycle.
PubMed:
Penicillium expansum: consistent production of patulin, chaetoglobosins, and other secondary metabolites in culture and their natural occurrence in fruit products.
PubMed:
Mycotoxin-forming ability of two Penicillium roqueforti strains in blue moldy tulum cheese ripened at various temperatures.
PubMed:
The presence of Penicillium and Penicillium mycotoxins in food wastes.
PubMed:
[Formation of alkaloids from Penicillium species fungi during growth on wheat kernels].
PubMed:
[Isolation of Penicillium DIERCKX 1901--a producer of diketopiperazine alkaloids rokefortin and 3,12-dihydrokefortin--from permafrost].
PubMed:
Isolation of moulds capable of producing mycotoxins from blue mouldy Tulum cheeses produced in Turkey.
PubMed:
Tremorgenic neuromycotoxicosis in 2 dogs ascribed to the ingestion of penitrem A and possibly roquefortine in rice contaminated with Penicillium crustosum.
PubMed:
[Analysis of secondary metabolites of microscopic fungi of the genus Penicillium by chromatographic techniques].
PubMed:
Thin layer chromatography convulsant screen extended by gas chromatography-mass spectrometry.
PubMed:
[The biosynthesis of low-molecular-weight nitrogen-containing secondary metabolite-alkaloids by the resident strains of Penicillium chrysogenum and Penicillium expansum isolated on the board of the Mir space station ].
PubMed:
Tremorgenic mycotoxin intoxication with penitrem A and roquefortine in two dogs.
PubMed:
Tremorgenic mycotoxicosis in four dogs from a single household.
PubMed:
Cell cytotoxicity and mycotoxin and secondary metabolite production by common penicillia on cheese agar.
PubMed:
Determination of Penicillium mycotoxins in foods and feeds using liquid chromatography-mass spectrometry.
PubMed:
[Optimization of the medium and cultivation conditions of Penicillium roquefortii f39 producing the diketopiperazine alkaloid roquefortine].
PubMed:
Mycotoxins.
PubMed:
Acute penitrem A and roquefortine poisoning in a dog.
PubMed:
Total synthesis of isoroquefortine C.
PubMed:
[Factors contributing to roquefortine yield variability during cultivation of penicillium roquefortii].
PubMed:
Inhibitory effects of roquefortine on hepatic cytochromes P450.
PubMed:
Molecular requirements for inhibition of cytochrome p450 activities by roquefortine.
PubMed:
Surface mycoflora of a Spanish fermented meat sausage and toxigenicity of Penicillium isolates.
PubMed:
Characterization of Penicillium roqueforti strains used as cheese starter cultures by RAPD typing.
PubMed:
[Not Available].
PubMed:
[Minor alkaloids from the fungus Penicillium roquefortii Thom 1906].
PubMed:
Roquefortine C occurrence in blue cheese.
PubMed:
[Taxonomic position and nitrogen-containing secondary metabolites of the fungus Penicillium vitale Pidoplichko Et Bilai Apud Bilai].
PubMed:
[Diketopiperazine alkaloids from the fungus Penicillium piscarium Westling].
PubMed:
[Mycotoxins from the fungi Penicillium vulpinum (Cooke & Massee) Seifert & Samson].
PubMed:
Determination of roquefortine C in blue cheese using on-line column-switching liquid chromatography.
PubMed:
Determination of roquefortine C in blue cheese using on-line column-switching liquid chromatography.
PubMed:
A rapid bioassay to detect mycotoxins using a melanin precursor overproducer mutant of the ciliate Tetrahymena thermophila.
PubMed:
Toxin-producing species of Penicillium and the development of mycotoxins in must and homemade wine.
PubMed:
MS/MS screen for the tremorgenic mycotoxins roquefortine and penitrem A.
PubMed:
Mycotoxins in two Spanish cheese varieties.
PubMed:
Study of the alkaloid composition of the food-infecting penicilles.
PubMed:
[Nitrogen-containing mycotoxins of fungi of Aspergillus and Penicillium species infesting grain and its products].
PubMed:
Roquefortine in the stomach contents of dogs suspected of strychnine poisoning in Alberta.
PubMed:
Alberta. Roquefortine identified as a major differential diagnosis in suspected strychnine poisoning in dogs.
PubMed:
Isolation of roquefortine C from feed grain.
PubMed:
Synthesis and metabolism of roquefortine in Penicillium species.
PubMed:
Antimicrobial action of roquefortine.
PubMed:
Roquefortine toxicity in a dog.
PubMed:
Investigation of Penicillium chrysogenum Isolates for their Suitability as Starter Cultures.
PubMed:
Elimination of roquefortine in the rat.
PubMed:
Thin-layer chromatography of mycotoxins.
PubMed:
Genetics of ergoline alkaloid formation in Penicillium roquefortii.
PubMed:
[Mutagenicity testing of commercially used strains of P. camemberti and P. roqueforti].
PubMed:
Classification of terverticillate penicillia based on profiles of mycotoxins and other secondary metabolites.
PubMed:
Biosynthesis of penitrems and roquefortine by Penicillium crustosum.
PubMed:
Simple screening method for molds producing intracellular mycotoxins in pure cultures.
PubMed:
[Role of tryptophan and histidine in alkaloid biosynthesis by Penicillium roqueforti].
PubMed:
Novel metabolites from Penicillium crustosum, including penitrem E, a tremorgenic mycotoxin.
PubMed:
Determination of roquefortine in blue cheese and blue cheese dressing by high pressure liquid chromatography with ultraviolet and electrochemical detectors.
PubMed:
Penitrem A and Roquefortine Production by Penicillium commune.
PubMed:
[Intracellular and extracellular alkaloids of Penicillium roqueforti].
PubMed:
[UV-densitometric analysis of roquefortin and PR toxin].
PubMed:
Acute toxicity studies on roquefortine and PR toxin, metabolites of Penicillium roqueforti, in the mouse.
PubMed:
[Harmlessness to human health of the mold cultures used in cheesemaking].
PubMed:
Study of conditions of production of roquefortine and other metabolites of Penicillin roqueforti.
PubMed:
Roquefortine and isofumigaclavine A, alkaloids from Penicillium roqueforti.
PubMed:
Analysis of blue cheese for roquefortine and other alkaloids from Penicillium roqueforti.