CITRININ

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H14O5
Molecular Weight	250.2473
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1OC=C2C(O)=C(C(O)=O)C(=O)C(C)=C2[C@@H]1C

InChI

InChIKey=CQIUKKVOEOPUDV-IYSWYEEDSA-N

InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m1/s1

HIDE SMILES / InChI

Description
Sources: DOI: 10.2903/j.efsa.2012.2605 | https://www.ncbi.nlm.nih.gov/pubmed/20937400 | https://www.ncbi.nlm.nih.gov/pubmed/29165056 | https://www.ncbi.nlm.nih.gov/pubmed/16183218

Citrinin is a mycotoxin produced by several species of the genera Aspergillus, Penicillium and Monascus. It is often found in food. Citrinin is nephrotoxic agent. Inhibition of RNA (predominantly rRNA) and DNA synthesis by citrinin has been reported in different mammalian cell lines including kidney cells. The induction of oxidative stress has also been proposed to account for citrinin toxicity. Citrinin inhibits immune response – it inhibits lipopolysaccharide/interferon-gamma-induced nitric oxide production in glomerular mesangial cells. Citrinin induced apoptosis in human colon cancer and promyelocytic leukemia cell lines.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29165056 \| https://www.ncbi.nlm.nih.gov/pubmed/16183218 \| https://www.ncbi.nlm.nih.gov/pubmed/18767140 \| https://www.ncbi.nlm.nih.gov/pubmed/17331071	Activator 1430
nitric oxide production involved in inflammatory response 17 Target ID: GO:0002537 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20937400	Inhibitor 8297
Oxidative Stress 160 Target ID: WP408 Sources: DOI: 10.2903/j.efsa.2012.2605	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Transport of ochratoxin A by renal multispecific organic anion transporter 1.	1999 Jun	10336520
The mycotoxins citrinin, gliotoxin, and patulin affect interferon-gamma rather than interleukin-4 production in human blood cells.	2002	12112629
Activation of JNK and PAK2 is essential for citrinin-induced apoptosis in a human osteoblast cell line.	2009 Aug	18767140
Activation of ERK and JNK signaling pathways by mycotoxin citrinin in human cells.	2009 Jun 15	19361540
Citrinin-generated reactive oxygen species cause cell cycle arrest leading to apoptosis via the intrinsic mitochondrial pathway in mouse skin.	2011 Aug	21622943
Mycotoxin citrinin induced cell cycle G2/M arrest and numerical chromosomal aberration associated with disruption of microtubule formation in human cells.	2011 Jan	20929984
Complementary cell-based high-throughput screens identify novel modulators of the unfolded protein response.	2011 Sep	21844328
Evaluation of nephrotoxic effects of mycotoxins, citrinin and patulin, on zebrafish (Danio rerio) embryos.	2012 Dec	22847133
Immune modulatory effects of the foodborne contaminant citrinin in mice.	2012 Oct	22771370
Citrinin reduces testosterone secretion by inducing apoptosis in rat Leydig cells.	2012 Sep	22564900
Cardiotoxicity of mycotoxin citrinin and involvement of microRNA-138 in zebrafish embryos.	2013 Dec	24052562
Cell cycle progression, but not genotoxic activity, mainly contributes to citrinin-induced renal carcinogenesis.	2013 Sep 15	23856526

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 20 ug/kg body weight per day (90 days study)

Route of Administration: Oral

In Vitro Use Guide

10–30 uM citrinin directly induced a ∼7–18-fold increase in the intracellular ROS content of ESC-B5 cells, compared with untreated control cells.

Name

Type

Language

CITRININ

Common Name

English

3H-2-BENZOPYRAN-7-CARBOXYLIC ACID, 4,6-DIHYDRO-8-HYDROXY-3,4,5-TRIMETHYL-6-OXO-, (3R,4S)-

Common Name

English

CITRININ [IARC]

Common Name

English

NSC-186

Code

English

CITRININ [MI]

Common Name

English

CITRININ [HSDB]

Common Name

English

Code System Code Type Description

NSC

186