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
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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.
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)
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