Ochratoxin B
(Synonyms: 赭曲霉毒素B) 目录号 : GC40870
Ochratoxin B (OTB)是赭曲霉的次级代谢物，是赭曲霉毒素a (OTA)的非氯化类似物，是啮齿类动物中最有效的肾致癌物之一。
Cas No.:4825-86-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
| Cell experiment [1]: | |
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Cell lines |
LLC-PK1 porcine kidney epithelial cells |
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Preparation Method |
Ochratoxin A and Ochratoxin B were freshly dissolved in ethanol and diluted in medium containing 5% FCS. Cells were seeded in 96-well plates at a density of 1×104 cells/well, allowed to grow for 24 h in ochratoxin-free medium and subsequently incubated with Ochratoxin A or Ochratoxin B at concentrations between 0 and 100 µM for 8, 24 and 72 h. |
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Reaction Conditions |
0 and 100 µM for 8, 24 and 72 h |
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Applications |
Cytotoxicity was not observed in LLC-PK1 cells after incubation with Ochratoxin A or Ochratoxin B (up to 100 µM) for 8 h, After 24 h, only minor differences in cytotoxicity were observed between Ochratoxin A and Ochratoxin B. |
| Animal experiment [2]: | |
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Animal models |
Male F344 Fisher rats |
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Preparation Method |
Animals (n = 3/group) were treated with a single dose of Ochratoxin B (10 mg/kg bw) in corn oil by oral gavage or repeatedly administered Ochratoxin B (2 mg/kg bw) for 2 weeks (5 days per week). |
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Dosage form |
10 mg/kg, oral; 2 mg/kg 2 weeks (5 days per week), oral |
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Applications |
After repeated administration of 2 mg/kg bw/day, no lesions indicative of cytotoxicity was observed in renal tubules and the number of mitotic figures in the proximal tubule epithelium. |
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References: [1]: Mally A, Keim-Heusler H, Amberg A, et al. Biotransformation and nephrotoxicity of ochratoxin B in rats[J]. Toxicology and applied pharmacology, 2005, 206(1): 43-53. | |
Ochratoxin B (OTB), a secondary metabolite of Aspergillus ochraceus, is the nonchlorinated analogue of the mycotoxin ochratoxin A (OTA), which is one of the most potent renal carcinogens in rodents [1].
Intracellular concentration of Ochratoxin B following 24-h incubation with a noncytotoxic dose (10 µM) was 2.2 ± 0.25 pmol/ml of cell lysate for Ochratoxin B [1]. Based on fluorescence studies, Ochratoxin B form highly stable complexes with Human serum albumin (HSA) [2].
The rats given ochratoxin B or ochratoxins A and B (4mg/kg) were clinically unaffected, while the rats given ochratoxin A (4mg/kg) reduced food intake by 50%, and they lost ca. 10% of their weight during the experimental period [3]. Both single (10 mg/kg, oral) and repeated (2 mg/kg 2 weeks, oral) administration of ochratoxin B do not induce pronounced adverse effects in rats as indicated by only minor histopathologic changes in the kidney after a single high dose and absence of histopathology in the kidney and the liver after repeated administration [1].
References:
[1]. Mally A, Keim-Heusler H, Amberg A, et al. Biotransformation and nephrotoxicity of ochratoxin B in rats[J]. Toxicology and applied pharmacology, 2005, 206(1): 43-53.
[2]. Faisal Z, VÖrÖs V, FliszÁr-NyÚl E, et al. Probing the interactions of ochratoxin B, ochratoxin C, patulin, deoxynivalenol, and T-2 toxin with human serum albumin[J]. Toxins, 2020, 12(6): 392.
[3]. StØrmer F C, Kolsaker P, Holm H, et al. Metabolism of ochratoxin B and its possible effects upon the metabolism and toxicity of ochratoxin A in rats[J]. Applied and environmental microbiology, 1985, 49(5): 1108-1112.
| Cas No. | 4825-86-9 | SDF | |
| 别名 | 赭曲霉毒素B | ||
| 化学名 | N-[[(3R)-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]-L-phenylalanine | ||
| Canonical SMILES | O=C1O[C@@H](C)CC2=C1C(O)=C(C(N[C@H](C(O)=O)CC3=CC=CC=C3)=O)C=C2 | ||
| 分子式 | C20H19NO6 | 分子量 | 369.4 |
| 溶解度 | 50mg/mL in ethanol, 15mg/mL in DMSO, 10mg/mL in DMF | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.7071 mL | 13.5355 mL | 27.0709 mL |
| 5 mM | 0.5414 mL | 2.7071 mL | 5.4142 mL |
| 10 mM | 0.2707 mL | 1.3535 mL | 2.7071 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Metabolism of Ochratoxin B and its possible effects upon the metabolism and toxicity of ochratoxin A in rats
Appl Environ Microbiol 1985 May;49(5):1108-12.PMID:4004232DOI:10.1128/aem.49.5.1108-1112.1985.
A metabolic product was formed from Ochratoxin B by rat liver microsomal fractions in the presence of NADPH. It was isolated from the incubation mixture by extraction, thin-layer chromatography, high-pressure liquid chromatography, and crystallization. On the basis of mass and nuclear magnetic resonance spectroscopy, the structure is suggested to be 4-hydroxyochratoxin B. The Km for the formation of 4-hydroxyochratoxin B was determined, and the hydroxylation of ochratoxin A was not altered by the presence of Ochratoxin B. Rats were given ochratoxin A or B, or a mixture of both intraperitoneally. The ratios of the three metabolites, ochratoxin A, (4R)-4-hydroxyochratoxin A, and ochratoxin alpha, excreted in the urine did not change in the presence of Ochratoxin B. Ochratoxin B was metabolized to 4-hydroxyochratoxin B and ochratoxin beta, but in a different ratio than for the ochratoxin A metabolites. When given intraperitoneally, ochratoxin beta was excreted within 24 h. In rats treated with ochratoxin A alone, the food intake was reduced by 50%, and histologically severe lesions, degeneration, and necrosis were observed in the proximal tubules. When ochratoxin A and B given in combination, the animals were clinically unaffected and histologically there was only slight damage of proximal tubules. These observations indicate that Ochratoxin B considerably reduces the toxic effects of ochratoxin A.
Determination of Ochratoxin A and Ochratoxin B in Archived Tokaj Wines (Vintage 1959-2017) Using On-Line Solid Phase Extraction Coupled to Liquid Chromatography
Toxins (Basel) 2020 Nov 24;12(12):739.PMID:33255273DOI:10.3390/toxins12120739.
According to the EU legislation, ochratoxin A contamination is controlled in wines. Tokaj wine is a special type of sweet wine produced from botrytized grapes infected by "noble rot" Botrytis cinerea. Although a high contamination was reported in sweet wines and noble rot grapes could be susceptible to coinfection with other fungi, including ochratoxigenic species, no screening of Tokaj wines for mycotoxin contamination has been carried out so far. Therefore, we developed an analytical method for the determination of ochratoxin A (OTA) and Ochratoxin B (OTB) involving online SPE coupled to HPLC-FD using column switching to achieve the fast and sensitive control of mycotoxin contamination. The method was validated with recoveries ranging from 91.6% to 99.1% with an RSD less than 2%. The limits of quantification were 0.1 and 0.2 µg L-1 for OTA and OTB, respectively. The total analysis time of the online SPE-HPLC-FD method was a mere 6 min. This high throughput enables routine analysis. Finally, we carried out an extensive investigation of the ochratoxin contamination in 59 Slovak Tokaj wines of 1959-2017 vintage. Only a few positives were detected. The OTA content in most of the checked wines did not exceed the EU maximum tolerable limit of 2 µg L-1, indicating a good quality of winegrowing and storing.
Synthesis of 14C-ochratoxin A and 14C-ochratoxin B and a comparative study of their distribution in rats using whole body autoradiography
Pharmacol Toxicol 1992 Apr;70(4):255-61.PMID:1608909DOI:10.1111/j.1600-0773.1992.tb00467.x.
Methods for preparation of labelled ochratoxin A and B are described. The method for preparation of labelled Ochratoxin B involves the synthesis of the azide of ochratoxin beta via the mixed anhydride and subsequent conjugation to labelled phenylalanine to yield 14C-ochratoxin B. The labelled ochratoxins were injected into male Wistar rats and after different survival times they were sacrificed and subjected to whole body autoradiography. The distribution pattern of ochratoxin A in the rat did not differ from that earlier registered for mouse. The previously known, high susceptibility of rats (and not mice) to ochratoxin A-induced cancer could thus not be explained by an accumulation of the toxin in specific cells or organs. The distribution patterns of ochratoxin A and B were almost congruent--the only apparent difference being a much longer retention of the labelled ochratoxin A in the blood compared to Ochratoxin B, which was much faster excreted. When analyzing tissue extracts for labelled metabolites only the extracts from the rats injected with Ochratoxin B were found to contain easily detectable concentrations, while no metabolites of ochratoxin A were seen.
Probing the Interactions of Ochratoxin B, Ochratoxin C, Patulin, Deoxynivalenol, and T-2 Toxin with Human Serum Albumin
Toxins (Basel) 2020 Jun 13;12(6):392.PMID:32545742DOI: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.
The individual and combined effects of ochratoxin A with citrinin and their metabolites (Ochratoxin B, ochratoxin C, and dihydrocitrinone) on 2D/3D cell cultures, and zebrafish embryo models
Food Chem Toxicol 2021 Dec;158:112674.PMID:34800554DOI:10.1016/j.fct.2021.112674.
Ochratoxin A and citrinin are nephrotoxic mycotoxins produced by Aspergillus, Penicillium, and/or Monascus species. The combined effects of ochratoxin A and citrinin have been examined in more studies; however, only limited data are available regarding the co-exposure to their metabolites. In this investigation, the individual toxic effects of ochratoxin A, Ochratoxin B, ochratoxin C, citrinin, and dihydrocitrinone were tested as well as the combinations of ochratoxin A with the latter mycotoxins were examined on 2D and 3D cell cultures, and on zebrafish embryos. Our results demonstrate that even subtoxic concentrations of certain mycotoxins can increase the toxic impact of ochratoxin A. In addition, typically additive effects or synergism were observed as the combined effects of mycotoxins tested. These observations highlight that different cell lines (e.g. MDBK vs. MDCK), cell cultures (e.g. 2D vs. 3D), and models (e.g. in vitro vs. in vivo) can show different (sometimes opposite) impacts. Mycotoxin combinations considerably increased miR-731 levels in zebrafish embryos, which is an early marker of the toxicity on kidney development. These results underline that the co-exposure to mycotoxins (and/or mycotoxin metabolites) should be seriously considered, since even the barely toxic mycotoxins (or metabolites) in combinations can cause significant toxicity.