Citrinin

Citrinin is a mycotoxin that has been found in Monascus and has diverse biological activities. It is active against S. aureus, methicillin-resistant S. aureus (MRSA), rifampicin-resistant S. aureus, and vancomycin-resistant E. faecium (MICs = 1.95, 3.9, 0.97, and 7.81 µg/ml, respectively), as well as the pathogenic yeast C. neoformans (MIC = 3.9 µg/ml). It is cytotoxic to a variety of cells in vitro, including bovine kidney cells and mice embryonic stem cells. Citrinin (30 µM) induces reactive oxygen species (ROS) production, mitochondrial membrane potential loss, and apoptosis in HepG2 cells, effects that can be blocked by the antioxidant resveratrol. In contrast, citrinin reduces glutamate-induced excitotoxicity in primary rat cortical neurons at concentrations ranging from 0.1 to 1,000 nM and inhibits LPS-induced production of nitric oxide (NO) in RAW 264.7 cells at 0.625 to 40 µM. It is toxic to brine shrimp larvae (LD50 = 96 µg/ml), as well as to rats and mice with oral LD50 values of 50 and 87-105 mg/kg, respectively. It induces reproductive abnormalities in male mice and toxic effects in the liver, kidney, heart, and gastrointestinal tracts of various animals. Citrinin has been found in stored cereal grains, as well as beans, fruit, and herbs.Formal Name: (3R,4S)-4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid. CAS Number: 518-75-2. Synonyms: NSC 186, (-)-Citrinin, CTN. Molecular Formula: C13H14O5. Formula Weight: 250.3. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 30 mg/ml, DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml, DMSO: 20 mg/ml, Ethanol: 2 mg/ml. lambdamax: 223, 251, 330 nm. SMILES: O=C1C(C)=C2[C@@H](C)[C@H](C)OC=C2C(O)=C1C(O)=O. InChi Code: 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-/m0/s1. InChi Key: CQIUKKVOEOPUDV-FSPLSTOPSA-N. Origin: Fungus/Penicillium citrinum.