Chaetoatrosin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00525 |
| CAS | |
| Molecular Weight | 262.26 |
| Molecular Formula | C14H14O5 |
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Description
It is produced by the strain of Chaetomium atrobrunneum F449. Chaetoatrosin inhibits chitin synthase of IC50 of 104 ㎍/mL. Chaetoatrosin has antifungal activity including Pyricularia oryzae, Botrytis cinerea, Cryptococcus neoformans, Trichophyton mentagrophytea and so on.
Specification
| Synonyms | Chaetoatrosin A; chaetoatrosin-a; SCHEMBL12800163 |
| IUPAC Name | 1-(4,5-dihydroxy-7-methoxynaphthalen-2-yl)-2-hydroxypropan-1-one |
| Canonical SMILES | CC(C(=O)C1=CC(=C2C(=C1)C=C(C=C2O)OC)O)O |
| InChI | InChI=1S/C14H14O5/c1-7(15)14(18)9-3-8-4-10(19-2)6-12(17)13(8)11(16)5-9/h3-7,15-17H,1-2H3 |
| InChI Key | XPOXRISVRJOBAH-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | fungi |
| Solubility | Soluble in Methanol |
Reference Reading
1. Fungal endophytes isolated from Protium heptaphyllum and Trattinnickia rhoifolia as antagonists of Fusarium oxysporum
Juan E Fierro-Cruz, Pedro Jiménez, Ericsson Coy-Barrera Rev Argent Microbiol. 2017 Jul-Sep;49(3):255-263. doi: 10.1016/j.ram.2016.12.009. Epub 2017 May 8.
Control of fungal pathogens is mainly addressed by the use of chemically synthesized fungicides which result in environmental pollution, developing resistance after prolonged use. In this context, endophytes have been recognized as potential biocontrollers, and also as a promising source of antifungal metabolites. Therefore, as part of our research on phytopathogen controllers, 355 fungal endophytes were isolated from Protium heptaphyllum and Trattinnickia rhoifolia (Burseraceae), both ethnobotanically important tree species that produce secondary metabolites of agronomic and industrial interest. Endophytes were tested by in vitro dual culture against Fusarium oxysporum, a phytopathogen of agronomic importance. Five endophytes exerted at least 40% inhibition on F. oxysporum growth. Ethyl acetate (EtOAc) extracts were obtained from the most active antagonistic fungi, after growing them in three different liquid media. The extracts were tested against a conidial suspension of F. oxysporum by direct bioautography. Two extracts derived from fungi identified as Chaetomium globosum, F211_UMNG and Meyerozima sp. F281_UMNG showed inhibition of pathogen growth. Isolate C. globosum, F211_UMNG was selected for a chemical analysis by RP-HPLC-DAD-ESI-MS and antifungal molecules such as cladosporin, chaetoatrosin A and chaetoviridin A were annotated and identified based on their MS data.
2. Chaetoatrosin A, a novel chitin synthase II inhibitor produced by Chaetomium atrobrunneum F449
E I Hwang, B S Yun, Y K Kim, B M Kwon, H G Kim, H B Lee, K S Bae, S U Kim J Antibiot (Tokyo). 2000 Mar;53(3):248-55. doi: 10.7164/antibiotics.53.248.
Chaetoatrosin A, a novel chitin synthase II inhibitor, was isolated from the culture broth of fungus F449, which was identified as Chaetomium atrobrunneum F449. Chaetoatrosin A was purified by solvent partition, silica gel, ODS, preparative TLC, and Sephadex LH-20 column chromatographies, consecutively. The structure of chaetoatrosin A was assigned as 1,8-dihydroxy-3(2-hydroxypropionyl)-6-methoxynaphthalene on the basis of various spectroscopic analyses including UV, IR, mass spectral, and NMR. Its molecular weight and formula were found to be 262 and C14H14O5, respectively. ,Chaetoatrosin A inhibited chitin synthase II by 50% at the concentration of 104 microg/ml in an enzyme assay system. This compound showed antifungal activities against Rhizoctonia solani, Pyricularia oryzae, Botrytis cinerea, Cryptococcus neoformans and Trichophyton mentagrophytes.
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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 ╳
