518-75-2 Usage
Description
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.
Chemical Properties
Different sources of media describe the Chemical Properties of 518-75-2 differently. You can refer to the following data:
1. yellow crystalline powder or flakes
2. Antimycin (A3C26H36N2O9) and (Antimycin
A1) C28H40N2O9 are crystalline solids.
Uses
Different sources of media describe the Uses of 518-75-2 differently. You can refer to the following data:
1. Antibiotic substance produced by a white spore aspergilus which has been placed under the species name Aspergillus niveus. Also produced in small quantities by Penicillium citrinum.
2. antibacterial
3. Citrinin is a quinonemethine mycotoxin produced by diverse fungi including Aspergillus and Penicillium. Citrinin has been extensively investigate, and is a potent nephrotoxin with hepatoxic and teratogenic activity. Citrinin is the causative agent of Balkan nephropathy and yellow rice fever in humans. At the molecular level, citrinin exhibits a range of effects including free radical damage to DNA and disruption of mitochondrial membrane-bound enzymic activities and structural integrity. Specifically, citrinin is an inhibitor of NADH dehydrogenase in the mitochondrial electron transport chain and this action is responsible for recent reports of citrinin's apoptotic activity.
General Description
Citrinin is a hepato-nephrotoxic mycotoxin. It can be produced by several filamentous fungi genera of Monauscus, Aspergillus, and Penicillium, which is commonly found as a contaminant in stored grains, foods, feedstuffs and also in biological fluids.
Potential Exposure
Specific uses for antimycin A were
not found, however, antimycin A1, and antimycin A3 are
reported to be antibiotic substances produced by streptomyces
for use as a fungicide, possible insecticide and miticide.
Registered as a pesticide in the U.S.
in vitro
previous study found that exposure of hek293 cells to citrinin led to an arrest of cell cycle g2/m in a concentration-dependent increase. citrinin treatment could also elevate the expression levels of p53 and p21 proteins, yet attenuate the signals of phosphorylated cell division cycle 2. moreover, treating hek293 with citrinin could increase both the value of mitotic index and the population of cells, indicating that arrest of citrinin -induced cell cycle occurred mainly during the mitotic phase [1].
in vivo
previous study showed that citrinin acted as a nephrotoxin in all tested animal species, but its acute toxicity varied in different species. the 50% lethal dose for ducks is 57 mg/kg; for chickens it is 95 mg/kg; and for rabbits it is 134 mg/kg. in murine kidneys, citrinin could also synergistically act with ochratoxin a to depress rna synthesis [2].
Shipping
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required.
references
[1] chang ch, yu fy, wu ts, wang lt, liu bh. mycotoxin citrinin induced cell cycle g2/m arrest and numerical chromosomal aberration associated with disruption of microtubule formation in human cells. toxicol sci. 2011 jan;119(1):84-92. [2] j. w. bennett and m. klich. mycotoxins. clin.microbiol.rev. 16(3), 497-516 (2003).
Check Digit Verification of cas no
The CAS Registry Mumber 518-75-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 8 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 518-75:
(5*5)+(4*1)+(3*8)+(2*7)+(1*5)=72
72 % 10 = 2
So 518-75-2 is a valid CAS Registry Number.
InChI:InChI=1/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
518-75-2Relevant articles and documents
Carbon-13 NMR of citrinin in the solid state and in solutions
Poupko,Luz,Destro
, p. 5097 - 5102 (1997)
Carbon-13 NMR is used to study the tautomeric equilibrium of citrinin in the solid state. The results confirm earlier X-ray diffraction studies, which indicated that the compound crystallizes in a disordered structure, with the p-quinone and o-quinone forms in a dynamic equilibrium. Analysis of the NMR data yields the equilibrium constant K(T) = [o]/[p] = exp(4.2/R) exp(-1610/RT) (where R is in cal mol-1 K-1), which is essentially identical to that determined by X-ray. The tautomerism is extremely fast on the NMR time scale (> 106 s-1). In methylene chloride solution citrinin also exists as a fast interconverting mixture of the two isomers with an equilibrium constant K ～ 0.7 at room temperature. However, the temperature dependence of the carbon-13 and oxygen-17 chemical shifts gave conflicting results, thus preventing a reliable determination of the thermodynamic parameters of K. In methanol and methanol/methylene chloride mixtures, citrinin undergoes a nucleophilic, Michael type, addition. The reaction is reversible, and the equilibrium shifts toward the normal cirtrinin form upon increasing temperature and in methanol/methylene chloride mixtures with increasing methylene chloride fraction. Only normal citrinin is obtained on crystallization, even from neat methanol.
Enantioselective Synthesis of the Polyketide Antibiotic (3R,4S)-(-)-Citrinin
Roedel, Thomas,Gerlach, Hans
, p. 885 - 888 (2007/10/02)
The fungal metabolite (-)-citrinin (1) was synthesized for the first time.Reaction of the Grignard reagent of 2,4-bis(benzyloxy)-6-bromotoluene (3) with (2S)-trans-(-)-2,3-dimethyloxirane (6) in the presence of 1,5-cyclooctadienecopper(I) chloride as catalyst leads to the formation of (2S,3S)-(-)-7 with erythro configuration.Compound (-)-7 could be transformed into (2R,3S)-(-)-9 with threo configuration via the formate (1R,2S)-(+)-8 by a Mitsunobu reaction.Reaction of the Grignard reagent of 3 with the achiral cis-2,3-dimethyl-oxirane yielded directly (+/-)-9.The starting material 3 was readily available from 1,3-bis(benzyloxy)-5-bromobenzene (4).Formylation of 4 furnished the aldehyde 5 which could be reduced to 3 with borane.Hydrogenolysis of the benzyl ether groups in (-)-9 gave (-)-2 with threo configuration.The remaining steps to produce citrinin from (-)-2 required carboxylation to 11, formylation and in situ ring closure with ethyl orthoformate to produce the required quinomethide structure.Application of the same reactions to (+/-)-9 and (+/-)-2 afforded (+/-)-citrinin in 40percent overall yield. - Key Words: Citrinin, (3R,4S)-(-)- / 2,3-Dimethyloxirane, trans-(-)- and cis- / Synthesis of erythro- and threo-3-arylbutan-2-ols
