Versicolorin A

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 341017

CAS#: 6807-96-1

Description: Versicolorin A is a Potential Indicator of Aflatoxin Contamination in the Granary-Stored Corn.


Price and Availability

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Versicolorin A is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 341017
Name: Versicolorin A
CAS#: 6807-96-1
Chemical Formula: C18H10O7
Exact Mass: 338.0427
Molecular Weight: 338.271
Elemental Analysis: C, 63.91; H, 2.98; O, 33.11


Synonym: Versicolorin A; Versicolorin.

IUPAC/Chemical Name: Anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 3a,12a-dihydro-4,6,8-trihydroxy-, Z-(-)-

InChi Key: SJNDYXPJRUTLNW-ULCDLSAGSA-N

InChi Code: 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

SMILES Code: Oc1cc(O)c2C(=O)c3c(O)c4[C@@H]5C=CO[C@@H]5Oc4cc3C(=O)c2c1


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Liu D, Zhang S, Wang H, Yang M, Yao D, Xie C. Versicolorin A is a Potential Indicator of Aflatoxin Contamination in the Granary-Stored Corn. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2018 Jan 16. doi: 10.1080/19440049.2017.1419579. [Epub ahead of print] PubMed PMID: 29337658.

2: Conradt D, Schätzle MA, Haas J, Townsend CA, Müller M. New Insights into the Conversion of Versicolorin A in the Biosynthesis of Aflatoxin B1. J Am Chem Soc. 2015 Sep 2;137(34):10867-9. doi: 10.1021/jacs.5b06770. Epub 2015 Aug 19. PubMed PMID: 26266881; PubMed Central PMCID: PMC4780671.

3: Wu YZ, Lu FP, Jiang HL, Tan CP, Yao DS, Xie CF, Liu DL. The furofuran-ring selectivity, hydrogen peroxide-production and low Km value are the three elements for highly effective detoxification of aflatoxin oxidase. Food Chem Toxicol. 2015 Feb;76:125-31. doi: 10.1016/j.fct.2014.12.004. Epub 2014 Dec 19. PubMed PMID: 25533793.

4: Chettri P, Ehrlich KC, Cary JW, Collemare J, Cox MP, Griffiths SA, Olson MA, de Wit PJ, Bradshaw RE. Dothistromin genes at multiple separate loci are regulated by AflR. Fungal Genet Biol. 2013 Feb;51:12-20. doi: 10.1016/j.fgb.2012.11.006. Epub 2012 Dec 1. PubMed PMID: 23207690.

5: Jakšić D, Puel O, Canlet C, Kopjar N, Kosalec I, Klarić MŠ. Cytotoxicity and genotoxicity of versicolorins and 5-methoxysterigmatocystin in A549 cells. Arch Toxicol. 2012 Oct;86(10):1583-91. doi: 10.1007/s00204-012-0871-x. Epub 2012 May 31. PubMed PMID: 22648070.

6: Linz JE, Chanda A, Hong SY, Whitten DA, Wilkerson C, Roze LV. Proteomic and biochemical evidence support a role for transport vesicles and endosomes in stress response and secondary metabolism in Aspergillus parasiticus. J Proteome Res. 2012 Feb 3;11(2):767-75. doi: 10.1021/pr2006389. Epub 2011 Dec 5. PubMed PMID: 22103394; PubMed Central PMCID: PMC3272149.

7: Zhang Y, Wu A, Xu X, Yan Y. Geometric dependence of the B3LYP-predicted magnetic shieldings and chemical shifts. J Phys Chem A. 2007 Sep 27;111(38):9431-7. Epub 2007 Aug 14. PubMed PMID: 17696331.

8: Cary JW, OBrian GR, Nielsen DM, Nierman W, Harris-Coward P, Yu J, Bhatnagar D, Cleveland TE, Payne GA, Calvo AM. Elucidation of veA-dependent genes associated with aflatoxin and sclerotial production in Aspergillus flavus by functional genomics. Appl Microbiol Biotechnol. 2007 Oct;76(5):1107-18. Epub 2007 Jul 24. PubMed PMID: 17646985.

9: Cary JW, Ehrlich KC, Bland JM, Montalbano BG. The aflatoxin biosynthesis cluster gene, aflX, encodes an oxidoreductase involved in conversion of versicolorin A to demethylsterigmatocystin. Appl Environ Microbiol. 2006 Feb;72(2):1096-101. PubMed PMID: 16461654; PubMed Central PMCID: PMC1392920.

10: Ehrlich KC, Montalbano B, Boué SM, Bhatnagar D. An aflatoxin biosynthesis cluster gene encodes a novel oxidase required for conversion of versicolorin a to sterigmatocystin. Appl Environ Microbiol. 2005 Dec;71(12):8963-5. PubMed PMID: 16332900; PubMed Central PMCID: PMC1317430.

11: Shier WT, Lao Y, Steele TW, Abbas HK. Yellow pigments used in rapid identification of aflatoxin-producing Aspergillus strains are anthraquinones associated with the aflatoxin biosynthetic pathway. Bioorg Chem. 2005 Dec;33(6):426-38. Epub 2005 Nov 2. PubMed PMID: 16260026.

12: Henry KM, Townsend CA. Ordering the reductive and cytochrome P450 oxidative steps in demethylsterigmatocystin formation yields general insights into the biosynthesis of aflatoxin and related fungal metabolites. J Am Chem Soc. 2005 Mar 23;127(11):3724-33. PubMed PMID: 15771506.

13: Henry KM, Townsend CA. Synthesis and fate of o-carboxybenzophenones in the biosynthesis of aflatoxin. J Am Chem Soc. 2005 Mar 16;127(10):3300-9. PubMed PMID: 15755146.

14: Wilkinson HH, Ramaswamy A, Sim SC, Keller NP. Increased conidiation associated with progression along the sterigmatocystin biosynthetic pathway. Mycologia. 2004 Nov-Dec;96(6):1190-8. PubMed PMID: 21148941.

15: Calvo AM, Bok J, Brooks W, Keller NP. veA is required for toxin and sclerotial production in Aspergillus parasiticus. Appl Environ Microbiol. 2004 Aug;70(8):4733-9. PubMed PMID: 15294809; PubMed Central PMCID: PMC492383.

16: Chang PK, Yabe K, Yu J. The Aspergillus parasiticus estA-encoded esterase converts versiconal hemiacetal acetate to versiconal and versiconol acetate to versiconol in aflatoxin biosynthesis. Appl Environ Microbiol. 2004 Jun;70(6):3593-9. PubMed PMID: 15184162; PubMed Central PMCID: PMC427728.

17: Yabe K, Chihaya N, Hamamatsu S, Sakuno E, Hamasaki T, Nakajima H, Bennett JW. Enzymatic conversion of averufin to hydroxyversicolorone and elucidation of a novel metabolic grid involved in aflatoxin biosynthesis. Appl Environ Microbiol. 2003 Jan;69(1):66-73. PubMed PMID: 12513978; PubMed Central PMCID: PMC152417.

18: Takahashi T, Chang PK, Matsushima K, Yu J, Abe K, Bhatnagar D, Cleveland TE, Koyama Y. Nonfunctionality of Aspergillus sojae aflR in a strain of Aspergillus parasiticus with a disrupted aflR gene. Appl Environ Microbiol. 2002 Aug;68(8):3737-43. PubMed PMID: 12147467; PubMed Central PMCID: PMC124037.

19: Bradshaw RE, Bhatnagar D, Ganley RJ, Gillman CJ, Monahan BJ, Seconi JM. Dothistroma pini, a forest pathogen, contains homologs of aflatoxin biosynthetic pathway genes. Appl Environ Microbiol. 2002 Jun;68(6):2885-92. PubMed PMID: 12039746; PubMed Central PMCID: PMC123981.

20: Chen RS, Tsay JG, Huang YF, Chiou RY. Polymerase chain reaction-mediated characterization of molds belonging to the Aspergillus flavus group and detection of Aspergillus parasiticus in peanut kernels by a multiplex polymerase chain reaction. J Food Prot. 2002 May;65(5):840-4. PubMed PMID: 12030297.