A fungal secondary metabolite
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Pseurotin A

Item No. 14441

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5S)-8S-benzoyl-2-[1S,2S-dihydroxy-3Z-hexen-1-yl]-9R-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
CAS Number
58523-30-1
Synonyms
  • NSC 348694
Molecular Formula
C22H25NO8
Formula Weight
431.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
O=C1N[C@](C(C2=CC=CC=C2)=O)(OC)[C@H](O)[C@@]31C(C(C)=C([C@@H](O)[C@@H](O)/C=C\CC)O3)=O
InChi Code
InChI=1S/C22H25NO8/c1-4-5-11-14(24)15(25)16-12(2)17(26)21(31-16)19(28)22(30-3,23-20(21)29)18(27)13-9-7-6-8-10-13/h5-11,14-15,19,24-25,28H,4H2,1-3H3,(H,23,29)/b11-5-/t14-,15-,19+,21+,22+/m0/s1
InChi Key
SLYDIPAXCVVRNY-UOWMTANKSA-N
Origin
Fungus/Aspergillus fumigatus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Its expression is induced in response to hypoxia.1 Pseurotin A has been shown to inhibit IgE production by mouse B cells in culture (IC50 = 3.6 μM) and dose-dependently (0.4-25 μg/ml) stimulate neuritogenic activity in rat pheochromocytoma PC12 cells.2,3 It also demonstrates nematicidal activity at 300 μg/ml.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Vödisch, M., Scherlach, K., Winkler, R., et al. Analysis of the Aspergillus fumigatus proteome reveals metabolic changes and the activation of the pseurotin A biosynthesis gene cluster in response to hypoxia. J. Proteome Res. 10(5), 2508-2524 (2011).

    2. Ishikawa, M., Ninomiya, T., Akabane, H., et al. Pseurotin A and its analogues as inhibitors of immunoglobulin E production. Bioorg. Med. Chem. Lett. 19(5), 1457-1460 (2009).

    3. Komagata, D., Fujita, S., Yamashita, N., et al. Novel neuritogenic activities of pseurotin A and penicillic acid. J. Antibiot. (Tokyo) 49(9), 958-959 (1996).

    4. Hayashi, A., Fujioka, S., Nukina, M., et al. Fumiquinones A and B, nematicidal quinones produced by Aspergillus fumigatus. Biosci. Biotechnol. Biochem. 71(7), 1697-1702 (2007).