Hydrolyzed Fumonisin B1
(Synonyms: Aminopentol) 目录号 : GC36270
Hydrolyzed Fumonisin B1 (Aminopentol) 是真菌毒素 fumonisin B1 (FB1) 的主要水解产物，具有较弱的抑制神经酰胺合成酶的作用。
Cas No.:145040-09-1
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
Hydrolyzed Fumonisin B1 (Aminopentol) is the backbone and main hydrolysis product of the mycotoxin fumonisin B1 (FB1), can weakly inhibit ceramide synthase[1].
[1]. Collins TF, et al. Effects of aminopentol on in utero development in rats. Food Chem Toxicol. 2006 Feb;44(2):161-9. [2]. Humpf HU, et al. Acylation of naturally occurring and synthetic 1-deoxysphinganines by ceramide synthase. Formation of N-palmitoyl-aminopentol produces a toxic metabolite of hydrolyzed fumonisin, AP1, and a new category of ceramide synthase inhibitor. J Biol Chem. 1998 Jul 24;273(30):19060-4. [3]. Schmelz EM, et al. Induction of apoptosis by fumonisin B1 in HT29 cells is mediated by the accumulation of endogenous free sphingoid bases. Toxicol Appl Pharmacol. 1998 Feb;148(2):252-60.
| Cas No. | 145040-09-1 | SDF | |
| 别名 | Aminopentol | ||
| Canonical SMILES | C[C@H](N)[C@@H](O)C[C@H](O)CCCC[C@@H](O)C[C@H](C)C[C@H](O)[C@H](O)[C@H](C)CCCC | ||
| 分子式 | C22H47NO5 | 分子量 | 405.61 |
| 溶解度 | Soluble in DMSO | 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 | 2.4654 mL | 12.3271 mL | 24.6542 mL |
| 5 mM | 0.4931 mL | 2.4654 mL | 4.9308 mL |
| 10 mM | 0.2465 mL | 1.2327 mL | 2.4654 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。
Mechanisms of Fumonisin B1 Toxicity: A Computational Perspective beyond the Ceramide Synthases Inhibition
Chem Res Toxicol 2018 Nov 19;31(11):1203-1212.PMID:30346146DOI:10.1021/acs.chemrestox.8b00188.
Fumonisins are mycotoxins produced by Fusarium fujikuroi species complex that may contaminate food and feed threatening human and animal health. Among the fumonisins group, fumonisin B1 is the most widespread and best characterized in terms of toxicity, while additional toxicological data on its congeners, such as N-acylated and hydrolyzed forms, need to be collected to support the group-based risk assessment. The inhibition of ceramide synthase has been identified as the key molecular mechanism of fumonisins toxicity resulting in modifications of sphingolipids rheostat. However, the existence of ancillary mechanisms and biological targets are likely to occur given the growing number of evidence reporting the multitarget mechanisms of mycotoxins toxicity. Therefore, in the framework of the early warning analysis of multitarget toxicity of fumonisins group, the present study aimed at searching potential targets for future hazard characterization studies of fumonisin B1 and its hydrolyzed and N-acetylated forms. In particular, on the basis of structural analogies with known inhibitors, the molecular interaction between N-acylated and hydrolyzed forms of fumonisin B1 and either ceramide transfer protein or sphingosine kinase I was assessed with a molecular modeling study. Our results pointed out that the molecular features of N-acylated Hydrolyzed Fumonisin B1 and Hydrolyzed Fumonisin B1 may allow the interaction with the ceramide transfer protein and with the sphingosine kinase I enzyme, respectively. Overall, our results identified such proteins as relevant targets that might take part in fumonisins group toxicity, adding plausible mechanistic insights to better understand fumonisins toxicity. Moreover, possible divergences in the mechanisms of action of fumonisin B1 and its modified forms were identified pointing out the need to assess their relevance with high priority to enhance the understanding of group toxicity.
Reduction of fumonisin B1 in corn grits by single-screw extrusion
J Agric Food Chem 2008 Apr 9;56(7):2400-5.PMID:18327966DOI:10.1021/jf0729513.
This study was designed to determine the efficacy of extrusion in reducing fumonisin B1 in corn flaking grits in the presence and absence of glucose. In addition, degradation products of fumonisin B1 during extrusion were identified and quantitated with a mass balance approach. Uncontaminated clean corn grits, grits spiked with 30 microg/g fumonisin B1, and grits fermented with Fusarium verticillioides M-2552 (40-50 microg/g fumonisin B1) were extruded in the presence and absence of glucose (10%, w/w) using a single-screw extruder. Extrusion decreased fumonisin B1 by 21-37%, whereas the same process with added glucose further decreased fumonisin B1 by 77-87%. LC-fluorescence and LC-MS showed that most fumonisin in the extruded samples without added glucose was the fumonisin B1 form, whereas the main degradation product in grits extruded with glucose was N-(deoxy- d-fructos-1-yl)fumonisin B1. The formation of Hydrolyzed Fumonisin B1 was not significant during extrusion. Results suggest that extrusion in the presence of glucose may reduce fumonisin B1 in corn grits significantly.
Fumonisin B1 and Hydrolyzed Fumonisin B1 (AP1) in tortillas and nixtamalized corn (Zea mays L.) from two different geographic locations in Guatemala
J Food Prot 1999 Oct;62(10):1218-22.PMID:10528731DOI:10.4315/0362-028x-62.10.1218.
Fumonisin B1 (FB1) is a common contaminant of corn worldwide and is responsible for several diseases of animals. In the preparation of tortillas, corn is treated with lime (producing nixtamal) that when heated hydrolyzes at least a portion of the FB1 to the aminopentol backbone (AP1), another known toxin. This study analyzed the amounts of FB1 and AP1 in tortillas and nixtamal from two communities in the central highlands of Guatemala where corn is a major dietary staple (Santa Maria de Jesus, Sacatepequez, and Patzicia, Chimaltenango). The amounts of FB1 and AP1 in tortillas from Santa Maria de Jesus were, respectively, 0.85 +/- 2.0 and 26.1 +/- 38.5 microg/g dry weight (mean +/- SD), and from Patzicia were 2.2 +/- 3.6 and 5.7 +/- 9.4 microg/g dry weight. Less than 6% of the tortillas from both locations contained > or = 10 microg FB1/g dry weight; whereas, 66% of the samples from Santa Maria de Jesus and 29% from Patzicia contained > or = 10 microg AP1/g dry weight. The highest amount of AP1 (185 microg/g dry weight) was found in tortillas from Santa Maria de Jesus. The highest amounts of FB1 were 6.5 and 11.6 microg/g dry weight in tortillas from Santa Maria de Jesus and Patzicia, respectively. The mean concentration of FB1 in nixtamal was significantly higher in Santa Maria de Jesus compared to Patzicia. Surprisingly, AP1 was not detected in any of the nixtamal samples. The human impact of exposure to these amounts of fumonisins is not known. However, based on findings with other animals, where corn is a dietary staple, long-term consumption of FB1 and AP1 (especially at > or = 10 microg/g of the diet) may pose a risk to human health.
Colorimetric determination of fumonisin B1 based on the aggregation of cysteamine-functionalized gold nanoparticles induced by a product of its hydrolysis
Mikrochim Acta 2019 Aug 28;186(9):655.PMID:31463772DOI:10.1007/s00604-019-3778-x.
A colorimetric method was developed for the determination of the mold toxin fumonisin B1 (FB1). It is based on the aggregation of cysteamine-capped gold nanoparticles (Cys-AuNPs). The assay involves alkaline hydrolysis of FB1 to obtain Hydrolyzed Fumonisin B1 (HFB1). The latter induces the aggregation of Cys-AuNPs which results in a color change from wine-red to blue-gray, best at a pH value of 9.0. A plot of absorbance ratio at 645/520 nm versus FB1 concentration is linear in the 2-8 μg kg-1 FB1 concentration range, and the detection limit is 0.90 μg kg-1. Inter-day and intra-day precisions are <6.2%, and recoveries from spiked samples ranged from 93 to 99%. The assay was successfully applied to the determination of FB1 in corn samples. It has a high selectivity over other competitive mycotoxins including aflatoxin, zearalenone, citrinin and patulin. The method is more selective than the detection of FB1 directly which may lead to false-positive errors. Graphical abstract Schematic representation of colorimetric assay of fumonisin B1 (FB1). FB1 was alkali-hydrolyzed and its product (Hydrolyzed Fumonisin B1) induces cysteamine-capped gold nanoparticles (Cys-AuNPs) via hydrogen bondings. The aggregation of Cys-AuNPs causes changes in color from wine-red to blue-gray.
Identification of fumonisin B1 as an inhibitor of argininosuccinate synthetase using fumonisin affinity chromatography and in vitro kinetic studies
J Biochem Mol Toxicol 2000;14(6):320-8.PMID:11083085DOI:10.1002/1099-0461(2000)14:6<320::AID-JBT4>3.0.CO;2-9.
Fumonisin B1, a fungal mycotoxin that grows on corn and other agricultural products, alters sphingolipid metabolism by inhibiting ceramide synthase. The precise mechanism of fumonisin B1 toxicity has not been completely elucidated; however, a central feature in the cytotoxicity is alteration of sphingolipid metabolism through interruption of de novo ceramide synthesis. An affinity column consisting of fumonisin B1 covalently bound to an HPLC column matrix was used to isolate a rat liver protein that consistently bound to the column. The protein was identified as argininosuccinate synthetase by protein sequencing. The enzyme-catalyzed formation of argininosuccinic acid from citrulline and aspartate by recombinant human and rat liver argininosuccinate synthetase was inhibited by fumonisin B1. Fumonisin B1 showed mixed inhibition against citrulline, aspartate, and ATP to the enzyme. Fumonisin B1 had a Ki' of approximately 6 mM with the recombinant human argininosuccinate synthase and a Ki' of 35 mM with a crude preparation of enzyme prepared from rat liver. Neither tricarballylic acid nor Hydrolyzed Fumonisin B1 inhibited recombinant human argininosuccinate synthetase. This is the first demonstration of fumonisin B1 inhibition of argininosuccinate synthethase, a urea cycle enzyme, which adds to the list of enzymes that are inhibited in vitro by fumonisin B1 (ceramide synthase, protein serine/threonine phosphatase). The extent of the inhibition of argininosuccinate synthetase in cells, and the possible role of this enzyme inhibition in the cellular toxicity of FB1, remains to be established.