Versicolorin B

Versicolorin B

* Please be kindly noted products are not for therapeutic use. We do not sell to patients.

Versicolorin B
Category Antibiotics
Catalog number BBF-02752
CAS 4331-22-0
Molecular Weight 340.28
Molecular Formula C18H12O7

Online Inquiry

Description

Versicolorin B 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 (3aS,12aR)-4,6,8-trihydroxy-2,3,3a,12a-tetrahydroanthra[2,3-b]furo[3,2-d]furan-5,10-dione; Anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 2,3,3a,12a-tetrahydro-4,6,8-trihydroxy-, cis-(+-)-
IUPAC Name (4S,8R)-2,16,18-trihydroxy-7,9-dioxapentacyclo[10.8.0.03,10.04,8.014,19]icosa-1,3(10),11,14(19),15,17-hexaene-13,20-dione
Canonical SMILES C1COC2C1C3=C(O2)C=C4C(=C3O)C(=O)C5=C(C4=O)C=C(C=C5O)O
InChI InChI=1S/C18H12O7/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/h3-5,7,18-20,23H,1-2H2/t7-,18+/m0/s1
InChI Key BABJNKGTTYCTOO-ULCDLSAGSA-N

Properties

Appearance Orange Yellow Needle Crystal
Antibiotic Activity Spectrum mycobacteria
Boiling Point 396.1°C at 760 mmHg
Melting Point 289°C
Density 1.3361 g/cm3

Reference Reading

1. Biosynthesis of dothistromin
Rosie E Bradshaw, Shuguang Zhang Mycopathologia. 2006 Sep;162(3):201-13. doi: 10.1007/s11046-006-0054-5.
Dothistromin is a mycotoxin that is remarkably similar in structure to versicolorin B, a precursor of both aflatoxin and sterigmatocystin. Dothistromin-producing fungi also produce related compounds, including some aflatoxin precursors as well as alternative forms of dothistromin. Dothistromin is synthesized by pathogenic species of Dothistroma in the red bands of pine needles associated with needle blight, but is also made in culture where it is strongly secreted into the surrounding medium. Orthologs of aflatoxin and sterigmatocystin biosynthetic genes have been found that are required for the biosynthesis of dothistromin, along with others that are speculated to be involved in the same pathway on the basis of their sequence similarity to aflatoxin genes. An epoxide hydrolase gene that has no homolog in the aflatoxin or sterigmatocystin gene clusters is also clustered with the dothistromin genes, and all these genes appear to be located on a minichromosome in Dothistroma septosporum. The dothistromin genes are expressed at an early stage of growth, suggesting a role in the first stages of plant invasion by the fungus. Future studies are expected to reveal more about the role of dothistromin in needle blight and about the genomic organization and expression of dothistromin genes: these studies will provide for interesting comparisons with these aspects of aflatoxin and sterigmatocystin biosynthesis.
2. 4-Hydroxy-7-methyl-3-phenylcoumarin Suppresses Aflatoxin Biosynthesis via Downregulation of aflK Expressing Versicolorin B Synthase in Aspergillus flavus
Young-Sun Moon, Leesun Kim, Hyang Sook Chun, Sung-Eun Lee Molecules. 2017 Apr 29;22(5):712. doi: 10.3390/molecules22050712.
Naturally occurring coumarins possess antibacterial and antifungal properties. In this study, these natural and synthetic coumarins were used to evaluate their antifungal activities against Aspergillus flavus, which produces aflatoxins. In addition to control antifungal activities, antiaflatoxigenic properties were also determined using a high-performance liquid chromatography in conjunction with fluorescence detection. In this study, 38 compounds tested and 4-hydroxy-7-methyl-3-phenyl coumarin showed potent antifungal and antiaflatoxigenic activities against A. flavus. Inhibitory mode of antiaflatoxigenic action by 4-hydroxy-7-methyl-3-phenyl coumarin was based on the downregulation of aflD, aflK, aflQ, and aflR in aflatoxin biosynthesis. In the cases of coumarins, antifungal and aflatoxigenic activities are highly related to the lack of diene moieties in the structures. In structurally related compounds, 2,3-dihydrobenzofuran exhibited antifungal and antiaflatoxigenic activities against A. flavus. The inhibitory mode of antiaflatoxigenic action by 2,3-dihydrobenzofuran was based on the inhibition of the transcription factor (aflS) in the aflatoxin biosynthesis pathway. These potent inhibitions of 2,3-dihydrobenzofuran and 4-hydroxy-7-methyl-3-phenyl coumarin on the Aspergillus growth and production of aflatoxins contribute to the development of new controlling agents to mitigate aflatoxin contamination.
3. Functional analyses of the versicolorin B synthase gene in Aspergillus flavus
Silin Ren, Yuewei Yue, Yu Li, Xiaodong Guo, Shihua Wang Microbiologyopen. 2017 Aug;6(4):e00471. doi: 10.1002/mbo3.471. Epub 2017 Jun 13.
Aflatoxin is a toxic, carcinogenic mycotoxin primarily produced by Aspergillus parasiticus and Aspergillus flavus. Previous studies have predicted the existence of more than 20 genes in the gene cluster involved in aflatoxin biosynthesis. Among these genes, aflK encodes versicolorin B synthase, which converts versiconal to versicolorin B. Past research has investigated aflK in A. parasiticus, but few studies have characterized aflK in the animal, plant, and human pathogen A. flavus. To understand the potential role of aflK in A. flavus, its function was investigated here for the first time using gene replacement and gene complementation strategies. The aflK deletion-mutant ΔaflK exhibited a significant decrease in sclerotial production and aflatoxin biosynthesis compared with wild-type and the complementation strain ΔaflK::aflK. ΔaflK did not affect the ability of A. flavus to infect seeds, but downregulated aflatoxin production after seed infection. This is the first report of a relationship between aflK and sclerotial production in A. flavus, and our findings indicate that aflK regulates aflatoxin formation.

Bio Calculators

Stock concentration: *
Desired final volume: *
Desired concentration: *

L

* 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
g/mol
g

Recently viewed products

Online Inquiry

Verification code
cartIcon
Inquiry Basket