Versicolorin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02751 |
| CAS | 6807-96-1 |
| Molecular Weight | 338.27 |
| Molecular Formula | C18H10O7 |
| Purity | 98% |
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Description
Versicolorin A is a quinone antibiotic produced by the strain of Asp. versicolor. It has the effect of anti-tuberculosis Mycobacterium H37RV and other mycobacteria.
Specification
| Synonyms | Z-(-)-4,6,8-Trihydroxy-3a,12a-dihydroanthra(2,3-b)furo(3,2-d)furan-5,10-dione; NSC 274542; (3aS,12aR)-4,6,8-trihydroxy-3a,12a-dihydroanthra[2,3-b]furo[3,2-d]furan-5,10-dione |
| IUPAC Name | (4S,8R)-2,16,18-trihydroxy-7,9-dioxapentacyclo[10.8.0.03,10.04,8.014,19]icosa-1,3(10),5,11,14(19),15,17-heptaene-13,20-dione |
| Canonical SMILES | C1=COC2C1C3=C(O2)C=C4C(=C3O)C(=O)C5=C(C4=O)C=C(C=C5O)O |
| InChI | InChI=1S/C18H10O7/c19-6-3-8-12(10(20)4-6)16(22)14-9(15(8)21)5-11-13(17(14)23)7-1-2-24-18(7)25-11/h1-5,7,18-20,23H/t7-,18+/m0/s1 |
| InChI Key | SJNDYXPJRUTLNW-ULCDLSAGSA-N |
Properties
| Appearance | Orange Yellow Needle Crystal |
| Antibiotic Activity Spectrum | mycobacteria |
| Boiling Point | 434.43°C at 760 mmHg |
| Melting Point | 289°C |
| Density | 1.3994 g/cm3 |
Reference Reading
1. Near-infrared reflectance spectroscopy-based fast versicolorin A detection in maize for early aflatoxin warning and safety sorting
Shao-Yan Zheng, Ze-Shun Wei, Shuang Li, Shi-Jia Zhang, Chun-Fang Xie, Dong-Sheng Yao, Da-Ling Liu Food Chem. 2020 Dec 1;332:127419. doi: 10.1016/j.foodchem.2020.127419. Epub 2020 Jun 27.
Aflatoxins (AFs) are potent carcinogens present in numerous crops. Access to accurate methods for evaluating contamination is a critical factor in aflatoxin risk assessment. Versicolorin A (Ver A), a precursor of aflatoxin B1 (AFB1), can be used as an indicator for the presence of AFB1, even when the AF is not yet detectable. Currently employed Ver A detection methods are expensive, time consuming, and difficult to apply to numerous samples. Herein, Ver A was detected via near-infrared spectroscopy. Both quantitative and two-grade sorting methods were set-up using the extreme gradient boosting algorithm coupled with a support vector machine. This two-tiered method obtained a root-mean-square error of prediction value of 3.57 μg/kg for the quantitative model, and an accuracy rate of 90.32% for the sorting approach. This novel method is rapid, accurate, solvent free, requires no sample pretreatment, and detects Ver A in maize, making it convenient for practical use.
2. Versicolorin A enhances the genotoxicity of aflatoxin B1 in human liver cells by inducing the transactivation of the Ah-receptor
Clémence Budin, Hai-Yen Man, Carine Al-Ayoubi, Sylvie Puel, Barbara M A van Vugt-Lussenburg, Abraham Brouwer, Isabelle P Oswald, Bart van der Burg, Laura Soler Food Chem Toxicol. 2021 Jul;153:112258. doi: 10.1016/j.fct.2021.112258. Epub 2021 May 10.
Aflatoxins are a group of mycotoxins that have major adverse effects on human health. Aflatoxin B1 (AFB1) is the most important aflatoxin and a potent carcinogen once converted into a DNA-reactive form by cytochrome P450 enzymes (CYP450). AFB1 biosynthesis involves the formation of Versicolorin A (VerA) which shares structural similarities with AFB1 and can be found in contaminated commodities, often co-occurring with AFB1. This study investigated and compared the toxicity of VerA and AFB1, alone or in combination, in HepG2 human liver cells. Our results show that both toxins have similar cytotoxic effects and are genotoxic although, unlike AFB1, the main genotoxic mechanism of VerA does not involve the formation of DNA double-strand breaks. Additionally, we show that VerA activates the aryl hydrocarbon receptor (AhR) and significantly induce the expression of the CYP450-1A1 (CYP1A1) while AFB1 did not induce AhR-dependent CYP1A1 activation. Combination of VerA with AFB1 resulted in enhanced genotoxic effects, suggesting that AhR-activation by VerA influences AFB1 genotoxicity by promoting its bioactivation by CYP450s to a highly DNA-reactive metabolite. Our results emphasize the need for expanding the toxicological knowledge regarding mycotoxin biosynthetic precursors to identify those who may pose, directly or indirectly, a threat to human health.
3. Metabolism of versicolorin A, a genotoxic precursor of aflatoxin B1: Characterization of metabolites using in vitro production of standards
Carine Al-Ayoubi, Justin Oules, Elodie Person, Sandrine Bruel, Alyssa Bouville, Philippe Pinton, Isabelle P Oswald, Emilien L Jamin, Olivier Puel, Laura Soler Food Chem Toxicol. 2022 Sep;167:113272. doi: 10.1016/j.fct.2022.113272. Epub 2022 Jul 6.
The toxicity of mycotoxins containing bisfuranoid structures such as aflatoxin B1 (AFB1) depends largely on biotransformation processes. While the genotoxicity and mutagenicity of several bisfuranoid mycotoxins including AFB1 and sterigmatocystin have been linked to in vivo bioactivation of these molecules into reactive epoxide forms, the metabolites of genotoxic and mutagenic AFB1 precursor versicolorin A (VerA) have not yet been characterized. Because this molecule is not available commercially, our strategy was to produce a library of metabolites derived from the biotransformation of in-house purified VerA, following incubation with human liver S9 fractions, in presence of appropriate cofactors. The resulting chromatographic and mass-spectrometric data were used to identify VerA metabolites produced by intestinal cell lines as well as intestinal and liver tissues exposed ex vivo. In this way, we obtained a panel of metabolites suggesting the involvement of phase I (M + O) and phase II (glucuronide and sulfate metabolites) enzymes, the latter of which is implicated in the detoxification process. This first qualitative description of the metabolization products of VerA suggests bioactivation of the molecule into an epoxide form and provides qualitative analytic data to further conduct a precise metabolism study of VerA required for the risk assessment of this emerging mycotoxin.
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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 ╳
