| Identification | Back Directory | [Name]
pseurotin | [CAS]
58523-30-1 | [Synonyms]
PB-1
pseurotin
NSC 348694
(5S,8S,9R)-8-Benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexenyl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
1-Oxa-7-azaspiro[4.4]non-2-ene-4,6-dione, 8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexen-1-yl]-9-hydroxy-8-methoxy-3-methyl-, (5S,8S,9R)- | [Molecular Formula]
C22H25NO8 | [MOL File]
58523-30-1.mol | [Molecular Weight]
431.44 |
| Chemical Properties | Back Directory | [Melting point ]
126.0-126.9℃ | [Boiling point ]
751.5±60.0 °C(Predicted) | [density ]
1.41±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
Soluble in DMSO (10 mg/ml) | [form ]
White to off-white powder. | [pka]
14.76±0.20(Predicted) | [color ]
White | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. |
| Hazard Information | Back Directory | [Description]
Pseurotin A (58523-30-1) is a fungal metabolite with novel structure. Displays potent neuritogenic activity in PC12 cells. Induces multipolar and branching neurites comparable to that produced by β-NGF.1 Displays immunosuppressive activity via inhibition of immunoglobulin E production in vitro.2 Displays antiproliferative effects on four glioma cell lines by regulating tumor metabolic enzymes.3 Inhibits osteoclastogenesis and prevents ovariectomized-induced bone loss by suppression of ROS.4 | [Uses]
Pseurotin A is a fungal metabolite with an unusual hetero-spirocyclic ring system. It has potent neuritogenic activity in PC12 phaechromocytoma cells, a useful model for adrenergic neuronal differentiation. Pseurotin A induces multipolar and branching neurites comparable to β-NGF, an endogenous neurotrophic factor. Pseurotin A also exhibits chitinase inhibition and acts synergistically with azole antifungal agents. | [Uses]
Pseurotin A shows antiparasitic and anticancer activity. It exhibits inhibition towards IgE (immunoglobin E) production. | [Definition]
ChEBI: A spirocyclic that is 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione bearing 1,2-dihydroxyhex-3-en-1-yl, methyl, methoxy, benzoyl and hydroxy substituents at positions 2, 3, 8, 8 and 9 respectively. | [storage]
+4°C | [References]
1) Komagata et al. (1996), Novel neuritogenic activities of pseurotin A and penicillic acid; J. Antibiot., 49 958
2) Ishikawa et al. (2009), Pseurotin A and its analogues as inhibitors of immunoglobulin E? production; Bioorg, Med. Chem. Lett., 19 1457
3) Anjum et al. (2018), Antiglioma pseurotin A from marine Bacillus sp. FS8D regulating tumour metabolic enzymes; Nat. Prod. Res., 32 1353
4) Chen et al. (2019), Pseurotin A Inhibits Osteoclastogenesis and Prevents Ovariectomized-Induced Bone Loss by Suppressing Reactive Oxygen Species; Theranostics, 9 1634 |
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