ROQUEFORTINE C

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H23N5O2
Molecular Weight	389.4503
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@]3(C4=CC=CC=C4N[C@@]3([H])N1C(=O)\C(NC2=O)=C/C5=CNC=N5)C(C)(C)C=C

InChI

InChIKey=SPWSUFUPTSJWNG-JJUKSXGLSA-N

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+/t17-,20-,22+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H23N5O2
Molecular Weight	389.4503
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19286504 | https://www.ncbi.nlm.nih.gov/pubmed/15337583 | https://www.ncbi.nlm.nih.gov/pubmed/2231314 | https://www.ncbi.nlm.nih.gov/pubmed/16019806

Roquefortine C, a cyclopeptide derived from the diketopiperazine cyclo(Trp-dehydroHis), is a secondary metabolite produced by several Penicillium species, especially by Penicillium roqueforti, which is used as starter culture for blue cheese production. Although roquefortine C is frequently detected in the products, it obviously has an insignificant toxicity to humans after ingestion. However, intoxications in dogs and cattle have been reported. Its bacteriostatic activities against Gram-positive bacteria lead to Roquefortine C potential use in antibiotics, but its development as a drug has been stopped due to its neurotoxic effects in mice. Roquefortine C activates P-gp and inhibits P450-3A and other haemoproteins. Roquefortine C can serve as a sensitive biomarker for penitrem A intoxication.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 1A1 31 Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11559041 \| https://www.ncbi.nlm.nih.gov/pubmed/16019806	Inhibitor 8297
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11559041 \| https://www.ncbi.nlm.nih.gov/pubmed/16019806	Inhibitor 8297
P-glycoprotein 1 54 Target ID: CHEMBL4302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16019806	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Penitrem A intoxication 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19286504	Diagnostic		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Acute toxicity studies on roquefortine and PR toxin, metabolites of Penicillium roqueforti, in the mouse.	1978 Aug	711058
Antimicrobial action of roquefortine.	1990 Jan-Apr	2231314
Molecular requirements for inhibition of cytochrome p450 activities by roquefortine.	2001 Sep	11559041
Cytotoxicity of occupationally and environmentally relevant mycotoxins.	2004 Oct 1	15337583
Oxidative metabolism by P450 and function coupling to efflux systems: modulation of mycotoxin toxicity.	2005 Apr	16019806
Using roquefortine C as a biomarker for penitrem A intoxication.	2009 Mar	19286504
The capability of fungi isolated from moldy dwellings to produce toxins.	2016	27518891
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.	2016 Dec	27707355
Modeling Growth and Toxin Production of Toxigenic Fungi Signaled in Cheese under Different Temperature and Water Activity Regimes.	2016 Dec 24	28029129
Production of the Fusarium Mycotoxin Moniliformin by Penicillium melanoconidium.	2016 Jun 8	27195914
OxaD: A Versatile Indolic Nitrone Synthase from the Marine-Derived Fungus Penicillium oxalicum F30.	2016 Sep 7	27505044
Silencing of a second dimethylallyltryptophan synthase of Penicillium roqueforti reveals a novel clavine alkaloid gene cluster.	2017 Aug	28620689
Quinone/hydroquinone meroterpenoids with antitubercular and cytotoxic activities produced by the sponge-derived fungus Gliomastix sp. ZSDS1-F7.	2017 Mar	27417331

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The MIC of roquefortine C for gram-positive organisms were about 80 ug/mL cells on the average. The sensitive bacterium Corynebacterium flaccumfaciens was chosen for characterizing the antimicrobial action of the mycotoxin. Addition of low roquefortine C concentrations at the beginning of bacterial growth resulted in prolongation of both the lag and logarithmic phases. High toxin concentrations (100 ug/mL cells) added to growing cells caused prolongation of logarithmic growth and decreased maximum cell density.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:50:46 UTC 2023` Edited by `admin` on `Fri Dec 15 19:50:46 UTC 2023`
Record UNII	4VW6U94XFK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ROQUEFORTINE C

Common Name

English

ROQUEFORTINE

Common Name

English

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)-

Common Name

English

NSC-292134

Code

English

ROQUEFORTIN

Common Name

English

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)-, (3E,5AS,10BR,11AS)-

Common Name

English

(-)-ROQUEFORTINE C

Common Name

English

ROQUEFORTINE [HSDB]

Common Name

English

Code System Code Type Description

NSC

292134