Aureobasidine A
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| Category | Antibiotics |
| Catalog number | BBF-00226 |
| CAS | |
| Molecular Weight | 1101.42 |
| Molecular Formula | C60H92N8O11 |
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Description
Aureobasidine A is produced by the strain of Aureobasidium pullulans R106. A has strong activity against candida albicans, Cryptococcus neoformans, budding yeast, histocapsular clinophyte and other pathogenic fungi, and its activity exceeds that of amphotericin B in most cases. The effect on candidiasis is bactericidal, and the therapeutic effect on systemic candidiasis in mice is superior to fluconum and amphotericin B.
Properties
| Appearance | Colorless Fine Rod-like Crystallineline |
| Antibiotic Activity Spectrum | fungi; yeast |
| Melting Point | 155-157 °C |
Reference Reading
1. Inhibitory effects and mechanism of antifungal action of the natural cyclic depsipeptide, aureobasidin A against Cryptococcus neoformans
Mostafa Teymuri, Masoomeh Shams-Ghahfarokhi, Mehdi Razzaghi-Abyaneh Bioorg Med Chem Lett. 2021 Jun 1;41:128013. doi: 10.1016/j.bmcl.2021.128013. Epub 2021 Apr 1.
Cryptococcosis is an opportunistic fungal infection caused mainly by Cryptococcus neoformans. The aim of the present study was to evaluate the inhibitory effect of aureobasidin A on C. neoformans with special focus on its mode of action. The effect of aureobasidin A on cell membrane ergosterol content, cell wall permeability, membrane pumps activities, the total oxidant status (TOS) and melanin production was evaluated. Cytotoxicity and cell hemolysis, and laccase (LacI) and β1,2-xylosyltransferase (Cxt1p) gene expression were also evaluated. Aureobasidin A reduced melanin production and increased extracellular potassium leakage at 0.5 × MIC concentration. This peptide has no effect on fungal cell wall integrity. Cell membrane ergosterol content was decreased by 29.1% and 41.8% at 0.5 × MIC and 1 × MIC concentrations (2 and 4 µL/mL) in aureobasidin A treated samples, respectively. TOS level was significantly increased without activation of antioxidant enzymes. Lac1 gene was over-expressed (11.7-fold), while Cxt1p gene was down regulated (0.2-fold) following treatment with aureobasidin A. Overall, our results indicated that aureobasidin A inhibits C. neoformans growth by targeting different sites in fungal cells and it may be considered as a promising compound to use as an antifungal in treatment of clinical cryptococcosis.
2. Solution cis-Proline Conformation of IPCs Inhibitor Aureobasidin A Elucidated via NMR-Based Conformational Analysis
Qi Gao, Ann E Cleves, Xiao Wang, Yizhou Liu, Sean Bowen, Robert Thomas Williamson, Ajay N Jain, Edward Sherer, Mikhail Reibarkh J Nat Prod. 2022 Jun 24;85(6):1449-1458. doi: 10.1021/acs.jnatprod.1c01071. Epub 2022 May 27.
Aureobasidin A (abA) is a natural depsipeptide that inhibits inositol phosphorylceramide (IPC) synthases with significant broad-spectrum antifungal activity. abA is known to have two distinct conformations in solution corresponding to trans- and cis-proline (Pro) amide bond rotamers. While the trans-Pro conformation has been studied extensively, cis-Pro conformers have remained elusive. Conformational properties of cyclic peptides are known to strongly affect both potency and cell permeability, making a comprehensive characterization of abA conformation highly desirable. Here, we report a high-resolution 3D structure of the cis-Pro conformer of aureobasidin A elucidated for the first time using a recently developed NMR-driven computational approach. This approach utilizes ForceGen's advanced conformational sampling of cyclic peptides augmented by sparse distance and torsion angle constraints derived from NMR data. The obtained 3D conformational structure of cis-Pro abA has been validated using anisotropic residual dipolar coupling measurements. Support for the biological relevance of both the cis-Pro and trans-Pro abA configurations was obtained through molecular similarity experiments, which showed a significant 3D similarity between NMR-restrained abA conformational ensembles and another IPC synthase inhibitor, pleofungin A. Such ligand-based comparisons can further our understanding of the important steric and electrostatic characteristics of abA and can be utilized in the design of future therapeutics.
3. A critical role of farnesol in the modulation of Amphotericin B and Aureobasidin A antifungal drug susceptibility
Venkatramanan Mahendrarajan, Vinay Kumar Bari Mycology. 2022 Oct 28;13(4):305-317. doi: 10.1080/21501203.2022.2138599. eCollection 2022.
Candida albicans and its related species can cause opportunistic infections such as "candidiasis" in immunocompromised individuals with a high morbidity and mortality rate. Several antifungal drugs available in the market are often used to treat infections caused by pathogenic fungi. However, in fungi, the development of resistance against these drugs quickly evolved. Candida is a dimorphic fungus that can switch between yeast to hyphae form, requires an active biosynthesis of membrane constituents. Sphingolipid and ergosterol molecules, are the major fungal plasma membrane components, and their interaction with the antifungal drug can modulate drug susceptibility. A lipophilic compound farnesol acts as a quorum-sensing molecule synthesised by the isoprenoid biosynthesis pathway in the fungal pathogen Candida. Farnesol is secreted in a cell density-dependent manner inhibits hyphae germination and biofilm formation. In this study, we have investigated whether the farnesol molecules affect the drug susceptibility of the antifungal drug Amphotericin B (AmB) which mainly binds with ergosterol, and Aureobasidin A (AbA), a complex sphingolipid biosynthesis inhibitor. Our studies revealed that a non-toxic and low concentration of farnesol can reduce the efficacy of AmB and AbA on yeast cells. This reduction is probably through the alteration in the complex sphingolipid biosynthesis and ATP-binding cassette (ABC) type membrane transport activity. These findings may shed light on a new direction to explore the role of lipid molecules in the antifungal drug resistance mechanisms in pathogenic yeast.
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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 ╳
