Pseurotin A

CHF 115.00
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BVT-0003-M0011 mgCHF 115.00
BVT-0003-M0055 mgCHF 345.00
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Product Details
Synonyms (5S,8S,9R)-8-Benzoyl-2-((1S,2S,Z)-1,2-dihydroxyhex-3-en-1-yl)-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
Product Type Chemical
Properties
Formula

C22H25NO8

MW 431.4
CAS 58523-30-1
Source/Host Chemicals Isolated from Aspergillus fumigatus.
Purity Chemicals ≥98% (HPLC)
Appearance White to off-white powder.
Solubility Soluble in methanol or ethyl acetate; poorly soluble in water.
Identity Determined by 1H-NMR.
Declaration Manufactured by BioViotica.
InChi Key SLYDIPAXCVVRNY-UOWMTANKSA-N
Smiles CC1=C([C@@H](O)[C@@H](O)/C=C\CC)O[C@@]2([C@@H](O)[C@](OC)(C(C3=CC=CC=C3)=O)NC2=O)C1=O
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Use/Stability Stable for at least 1 year after receipt when stored at -20°C.
After reconstitution protect from light at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • Antibiotic.
  • Chitin synthase, monoamine oxidase and IgE production inhibitor.
  • Cytotoxic.
  • Shows nematicidal and antileishmanial activity.
  • Antiproliferative against four different glioma cells. Downregulates the expression of tumour glycolytic enzymes pyruvate kinase M2 (PKM2) and lactate dehydrogenase 5 (LDH5) and upregulates the expression of pyruvate dehydrogenase beta (PDHB), adenosine triphosphate synthase beta (ATPB) and cytochrome C, important regulators for tricarboxylic acid cycle and oxidative phosphorylation.
  • Inhibits activation of B-cells and differentiation into the plasma cells
Product References
  1. Novel neuritogenic activities of pseurotin A and penicillic acid: D. Komagata, et al.; J. Antibiot. 49, 958 (1996)
  2. Directed biosynthesis of fluorinated pseurotin A, synerazol and gliotoxin: Y. Igarashi, et al.; J. Antibiot. 57, 748 (2004)
  3. Fumiquinones A and B, nematicidal quinones produced by Aspergillus fumigatus: A. Hayashi, et al.; Biosci. Biotechnol. Biochem. 71, 1697 (2007)
  4. Identification of a hybrid PKS/NRPS required for Pseurotin A biosynthesis in the human pathogen Aspergillus fumigatus: S. Maiya, et al.; ChemBioChem 8, 1736 (2007)
  5. Pseurotin A and its analogues as inhibitors of immunoglobulin E production: M. Ishikawa, et al.; Bioorg. Med. Chem. Lett. 19, 1457 (2009)
  6. Antiparasitic and anticancer constituents of the endophytic fungus Aspergillus sp. strain F1544: S. Martinez-Luis, et al.; Nat. Prod. Commun. 7, 165 (2012)
  7. Elucidation of Pseurotin Biosynthetic Pathway Points to Trans-Acting C-Methyltransferase: Generation of Chemical Diversity: Y. Tsunematsu, et al.; Angew. Chem. Int. Ed. 53, 8475 (2014)
  8. Angiogenesis Inhibitors and Anti-Inflammatory Agents from Phoma sp. NTOU4195: M.-S. Lee, et al.; J. Nat. Prod. 79, 2983 (2016)
  9. Total syntheses of spirocyclic PKS-NRPS-based fungal metabolites: D. Jo & S. Han; Chem. Comm. 54, 6750 (2018)
  10. Zebrafish-Based Discovery of Antiseizure Compounds from the Red Sea: Pseurotin A2 and Azaspirofuran A: D. Copmans, et al.; ACS Chem. Neurosci. 9, 1652 (2018)
  11. Antiglioma pseurotin A from marine Bacillus sp. FS8D regulating tumour metabolic enzymes: K. Anjum, et al.; Nat. Prod. Res. 32, 1353 (2018)
  12. Treatment of epilepsy using pseurotins and azaspirofurans: D. Copmans, et al.; PCT Int. Appl., WO 2019043019 A1 20190307 (2019)
  13. Natural pseurotins and analogs thereof inhibit activation of B-cells and differentiation into the plasma cells: O. Vasicek, et al.; Phytomedicine in press (2020)
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