Pseurotin A

Specifications / Handling

More Information
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

Product-specific References

Description

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

Novel neuritogenic activities of pseurotin A and penicillic acid: D. Komagata, et al.; J. Antibiot. 49, 958 (1996)
Directed biosynthesis of fluorinated pseurotin A, synerazol and gliotoxin: Y. Igarashi, et al.; J. Antibiot. 57, 748 (2004)
Fumiquinones A and B, nematicidal quinones produced by Aspergillus fumigatus: A. Hayashi, et al.; Biosci. Biotechnol. Biochem. 71, 1697 (2007)
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)
Pseurotin A and its analogues as inhibitors of immunoglobulin E production: M. Ishikawa, et al.; Bioorg. Med. Chem. Lett. 19, 1457 (2009)
Antiparasitic and anticancer constituents of the endophytic fungus Aspergillus sp. strain F1544: S. Martinez-Luis, et al.; Nat. Prod. Commun. 7, 165 (2012)
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)
Angiogenesis Inhibitors and Anti-Inflammatory Agents from Phoma sp. NTOU4195: M.-S. Lee, et al.; J. Nat. Prod. 79, 2983 (2016)
Total syntheses of spirocyclic PKS-NRPS-based fungal metabolites: D. Jo & S. Han; Chem. Comm. 54, 6750 (2018)
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)
Antiglioma pseurotin A from marine Bacillus sp. FS8D regulating tumour metabolic enzymes: K. Anjum, et al.; Nat. Prod. Res. 32, 1353 (2018)
Treatment of epilepsy using pseurotins and azaspirofurans: D. Copmans, et al.; PCT Int. Appl., WO 2019043019 A1 20190307 (2019)
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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