Ochratoxin B
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| Category | Mycotoxins |
| Catalog number | BBF-04064 |
| CAS | 4825-86-9 |
| Molecular Weight | 369.37 |
| Molecular Formula | C20H19NO6 |
| Purity | >99% by HPLC |
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Description
Ochratoxin B is an analogue of Ochratoxin A. Ochratoxins are mycotoxins produced by Aspergillus and Penicillium.
Specification
| Storage | Store at -20°C |
| IUPAC Name | (2S)-2-[[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl]amino]-3-phenylpropanoic acid |
| Canonical SMILES | CC1CC2=C(C(=C(C=C2)C(=O)NC(CC3=CC=CC=C3)C(=O)O)O)C(=O)O1 |
| InChI | InChI=1S/C20H19NO6/c1-11-9-13-7-8-14(17(22)16(13)20(26)27-11)18(23)21-15(19(24)25)10-12-5-3-2-4-6-12/h2-8,11,15,22H,9-10H2,1H3,(H,21,23)(H,24,25)/t11-,15+/m1/s1 |
| InChI Key | DAEYIVCTQUFNTM-ABAIWWIYSA-N |
| Source | Aspergillus ochraceus |
Properties
| Appearance | Pale Yellow Solid |
| Boiling Point | 632.4°C at 760 mmHg |
| Melting Point | 221°C |
| Density | 1.361 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Ochratoxin B is thought to inhibit the accumulation of cartilage proteoglycans and general protein synthesis in a concentration-related manner. |
Reference Reading
1.Characterization of oligosorbents and application to the purification of ochratoxin A from wheat extracts.
Ali WH1, Pichon V. Anal Bioanal Chem. 2014 Feb;406(4):1233-40. doi: 10.1007/s00216-013-7509-6. Epub 2013 Dec 6.
The aim of this work was to optimize the preparation of an anti-ochratoxin A (OTA) oligosorbent (OS), a solid-phase extraction sorbent based on OTA aptamers covalently immobilized on sepharose. Different syntheses were carried out by modifying the side of the oligonucleotide chain bound to the sepharose, the length of the spacer arm between the aptamer and the sepharose and the amount of the aptamers introduced during the covalent grafting. Indeed, the capacity of OSs prepared using 3'- or 5'-amino-modified sequences with a C6 or a C12 was studied. In the best conditions, the concentration of aptamers sequence used during their grafting was increased and a capacity close to 40 nmol g(-1) of OS was reached. The potential of the resulting OSs was also studied in pure media. For this, their selectivity was checked by comparing them to a control sorbent prepared without immobilizing aptamers. Extraction recoveries close to 100% were obtained on all OSs, while no retention was observed on the control sorbent.
2.Natural co-occurrence of ochratoxin A, ochratoxin B and aflatoxins in Sicilian red wines.
Di Stefano V1, Avellone G, Pitonzo R, Capocchiano VG, Mazza A, Cicero N, Dugo G. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2015;32(8):1343-51. doi: 10.1080/19440049.2015.1055521. Epub 2015 Jul 9.
The natural occurrence of ochratoxin A, ochratoxin B, aflatoxin B1, aflatoxin B2, aflatoxin G1 and aflatoxin G2 (OTA, OTB, AFB1, AFB2, AFG1, AFG2) in red wines was investigated by HPLC/FLD after immunoaffinity column clean-up in 57 market samples produced in Sicily (Italy). The results showed a very low incidence of these mycotoxins in analysed samples, confirming the high degree of quality and safety of Sicilian red wines. The results indicated 71.9% and 64.9% positive samples for OTA and OTB respectively, with an average level of 0.13 μg l(-1), well below the European maximum permitted levels (MLs). The aflatoxin most frequently detected in the samples was AFG1, present in 57.9% of samples, while the other aflatoxins were rarely present. Recovery experiments were carried out on eight mycotoxin-free red wines spiked with OTA, OTB, AFB1, AFB2, AFG1 and AFG2 at two different levels. The limits of detection (LODs) in wines were 0.02 µg l(-1) for OTA, 0.
3.Miniaturized DNA aptamer-based monolithic sorbent for selective extraction of a target analyte coupled on-line to nanoLC.
Brothier F1, Pichon V. Anal Bioanal Chem. 2014 Dec;406(30):7875-86. doi: 10.1007/s00216-014-8256-z. Epub 2014 Oct 22.
A complete characterization of a novel target-specific DNA aptamer-based miniaturized solid phase extraction (SPE)-sorbent coupled on-line to nanoLC is presented. A miniaturized oligosorbent (mOS) was prepared via the in situ sol-gel synthesis of a hybrid organic-inorganic monolith in 100 μm i.d. capillary columns using tetraethoxysilane and 3-aminopropyltriethoxysilane as precursors, followed by covalent binding of a 5'-amino-modified DNA aptamer with a C12 spacer arm specific for a molecule of small molecular weight. Ochratoxin A (OTA), one of the most abundant naturally occurring mycotoxins, was chosen as model analyte to demonstrate the principle of such an approach. The mOS was coupled on-line to RP-nanoLC-LIF. Selective extraction of OTA on several mOSs was demonstrated with an average extraction recovery above 80 % when percolating spiked binding buffer and a low recovery on control monoliths grafted with a non-specific aptamer. Reproducibility of mOSs preparation was highlighted by comparing extraction yields.
4.Impedimetric aptasensor for ochratoxin A determination based on Au nanoparticles stabilized with hyper-branched polymer.
Evtugyn G1, Porfireva A, Stepanova V, Kutyreva M, Gataulina A, Ulakhovich N, Evtugyn V, Hianik T. Sensors (Basel). 2013 Nov 26;13(12):16129-45. doi: 10.3390/s131216129.
An impedimetric aptasensor for ochratoxin A (OTA) detection has been developed on the base of a gold electrode covered with a new modifier consisting of electropolymerized Neutral Red and a mixture of Au nanoparticles suspended in the dendrimeric polymer Botlorn H30®. Thiolated aptamer specific to OTA was covalently attached to Au nanoparticles via Au-S bonding. The interaction of the aptamer with OTA induced the conformational switch of the aptamer from linear to guanine quadruplex form followed by consolidation of the surface layer and an increase of the charge transfer resistance. The aptasensor makes it possible to detect from 0.1 to 100 nM of OTA (limit of detection: 0.02 nM) in the presence of at least 50 fold excess of ochratoxin B. The applicability of the aptasensor for real sample assay was confirmed by testing spiked beer samples. The recovery of 2 nM OTA was found to be 70% for light beer and 78% for dark beer.
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
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