Ochratoxin C
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| Category | Mycotoxins |
| Catalog number | BBF-04439 |
| CAS | 4865-85-4 |
| Molecular Weight | 431.87 |
| Molecular Formula | C22H22ClNO6 |
| Purity | >95% by HPLC |
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Description
A minor component of the ochratoxin complex produced by Aspergillus orchraceus and penicillium sp. It is a mycotoxin associated with food spoilage. It is the ethyl ester of ochratoxin A and represents a different hazard to the acidic major components ochratoxins A and B.
Specification
| Synonyms | Ochratoxin A ethyl ester; ethyl ((R)-5-chloro-8-hydroxy-3-methyl-1-oxoisochromane-7-carbonyl)-L-phenylalaninate; L-Phenylalanine, N-((5-chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl)-, ethyl ester, (R)-; N-[[(3R)-5-chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]-L-phenylalanine, ethyl ester |
| Storage | Store at -20°C |
| IUPAC Name | ethyl (2S)-2-[[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl]amino]-3-phenylpropanoate |
| Canonical SMILES | CCOC(=O)C(CC1=CC=CC=C1)NC(=O)C2=CC(=C3CC(OC(=O)C3=C2O)C)Cl |
| InChI | InChI=1S/C22H22ClNO6/c1-3-29-21(27)17(10-13-7-5-4-6-8-13)24-20(26)15-11-16(23)14-9-12(2)30-22(28)18(14)19(15)25/h4-8,11-12,17,25H,3,9-10H2,1-2H3,(H,24,26)/t12-,17+/m1/s1 |
| InChI Key | BPZZWRPHVVDAPT-PXAZEXFGSA-N |
| Source | Aspergillus sp. |
Properties
| Appearance | Off-white Solid |
| Boiling Point | 612.6±55.0°C (Predicted) |
| Density | 1.328±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Ochratoxin A, a metabolite of Ochratoxin C, has been shown to be weakly mutagenic, possibly by induction of oxidative DNA damage. The nephrotoxin ochratoxin A (OTA) causes a reduction of glomerular filtration rate (GFR) and of para-aminohippuric acid (PAH) clearance. It is a nephrotoxin which blocks plasma membrane anion conductance in Madin-Darby canine kidney (MDCK) cells. |
Reference Reading
1. Lipid peroxidation as a possible cause of ochratoxin A toxicity
V Bussacchini-Griot, A D Rahimtula, H Bartsch, J C Béréziat Biochem Pharmacol . 1988 Dec 1;37(23):4469-77. doi: 10.1016/0006-2952(88)90662-4.
Addition of the mycotoxin ochratoxin A (OA), a nephrotoxic carcinogen, to rat liver microsomes greatly enhanced the rate of NADPH or ascorbate-dependent lipid peroxidation as measured by malondialdehyde formation. NADPH-dependent lipid peroxidation in kidney microsomes was similarly enhanced by OA. The process required the presence of trace amounts of iron but cytochrome P-450 and free active oxygen species appeared not to be involved. The efficiency of several ochratoxins (ochratoxins A, B, C, alpha and O-methyl-ochratoxin C) to enhance lipid peroxidation was related to the presence and reactivity of the phenolic hydroxyl group. Furthermore, the ability of these ochratoxins to enhance lipid peroxidation in microsomes correlated precisely with their known toxicities in chicks. Administration of ochratoxin A to rats also resulted in enhanced lipid peroxidation in vivo as evidenced by a seven-fold increase in the rate of ethane exhalation. These results suggest that lipid peroxidation may play a role in the observed toxicity of ochratoxin A in animals; a mechanism is proposed. (Formula: see text). Ochratoxin A: X = Cl; R1 = R2 = R3 = R4 = H Ochratoxin B: X = H; R1 = R2 = R3 = R4 = H Ochratoxin C: X = Cl; R1 = R2 = R3 = H; = R4 = CH3 O-Methyl-ochratoxin C: X = Cl; R2 = R3 = H; R1 = R4 = CH3 (4R)-4-hydroxyochratoxin A: X = Cl; R1 = R3 = R4 = H; R2 = OH (4S)-4-hydroxyochratoxin A: X = Cl; R1 = R2 = R4 = H; R3 = OH Fig. 1. Chemical structures of the various ochratoxins.
2. Probing the Interactions of Ochratoxin B, Ochratoxin C, Patulin, Deoxynivalenol, and T-2 Toxin with Human Serum Albumin
Virág Vörös, Ferenc Zsila, Zelma Faisal, Beáta Lemli, Tamás Kőszegi, Miklós Poór, Rita Csepregi, Sándor Kunsági-Máté, Eszter Fliszár-Nyúl Toxins (Basel) . 2020 Jun 13;12(6):392. doi: 10.3390/toxins12060392.
Ochratoxins, patulin, deoxynivalenol, and T-2 toxin are mycotoxins, and common contaminants in food and drinks. Human serum albumin (HSA) forms complexes with certain mycotoxins. Since HSA can affect the toxicokinetics of bound ligand molecules, the potential interactions of ochratoxin B (OTB), ochratoxin C (OTC), patulin, deoxynivalenol, and T-2 toxin with HSA were examined, employing spectroscopic (fluorescence, UV, and circular dichroism) and ultrafiltration techniques. Furthermore, the influence of albumin on the cytotoxicity of these xenobiotics was also evaluated in cell experiments. Fluorescence studies showed the formation of highly stable OTB-HSA and OTC-HSA complexes. Furthermore, fluorescence quenching and circular dichroism measurements suggest weak or no interaction of patulin, deoxynivalenol, and T-2 toxin with HSA. In ultrafiltration studies, OTB and OTC strongly displaced the Sudlow's site I ligand warfarin, while other mycotoxins tested did not affect either the albumin binding of warfarin or naproxen. The presence of HSA significantly decreased or even abolished the OTB- and OTC-induced cytotoxicity in cell experiments; however, the toxic impacts of patulin, deoxynivalenol, and T-2 toxin were not affected by HSA. In summary, the complex formation of OTB and OTC with albumin is relevant, whereas the interactions of patulin, deoxynivalenol, and T-2 toxin with HSA may have low toxicological importance.
3. Nuclease-aided target recycling signal amplification strategy for ochratoxin A monitoring
Zhijun Guo, Yangyang Zhao, Lei Lv, Donghao Li, Chengbi Cui Biosens Bioelectron . 2017 Jan 15;87:136-141. doi: 10.1016/j.bios.2016.08.024.
Ochratoxin A (OTA), a toxin produced by Aspergillus ochraceus and Penicillium verrucosum, is one of the most abundant food-contaminating mycotoxins worldwide. OTA mainly exerts nephrotoxicity, immunotoxicity, mutagenicity, carcinogenicity, teratogenicity, and neurotoxicity. This paper describes a simple and sensitive aptamer/single-walled carbon nanohorn (SWCNH)-based assay for OTA detection. SWCNHs can protect DNA from DNase I cleavage. However, aptamers can be detached from the surface of SWCNHs through specific target binding, exposing them to enzymatic cleavage and releases the target for a new cycle. Cycling of targets leads to significant signal amplification and low limit of detection (LOD), resulting in a nearly 20-fold reduction in LOD for OTA assay compared with non-target recycling under the same experimental parameters. This technique responded specifically to OTA without interference from other analogues (Ochratoxin B, Ochratoxin C, warfarin, and N-acetyl-l-phenylalanine). Moreover, the application of this technique in real sample has been verified using red wine samples spiked with a series of OTA concentrations. This aptasensor offers a great practical importance in food safety and can be widely extended for detection of other toxins by replacing the sequence of the recognition aptamer.
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
