BioBioPha
China
Product Name: Pseurotin A
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Purity: 98.0%
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Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: 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)-
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Purity: 98.0%
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58523-30-1

58523-30-1 structure

58523-30-1 structure

Name: pseurotin A
Chemical Name: pseurotin A
CAS Number: 58523-30-1
Molecular Formula: C₂₂H₂₅NO₈
Molecular Weight: 431.436
Catalog: Natural product Alkaloid
Create Date: 2017-11-28 22:20:01
Modify Date: 2024-01-04 09:24:10
Pseurotin A, a secondary metabolite of Aspergillus and other fungi, is a competitive inhibitor of chitin synthase and a neuritogenic agent. Pseurotin A inhibits IgE production (IC50=3.6 μM). Antitumor activity[1][2][3].

Name	pseurotin A
Synonyms	(5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-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 (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 pseurotin A PB-1 (5S,8S,9R)-8-Benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexen-1-yl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione pseurotin-A pseurotin 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)- (5S)-8c-benzoyl-9t-hydroxy-2-((1S,2S)-1,2-dihydroxy-hex-3c-enyl)-8t-methoxy-3-methyl-(5rO)-1-oxa-7-aza-spiro[4.4]non-2-ene-4,6-dione

Description	Pseurotin A, a secondary metabolite of Aspergillus and other fungi, is a competitive inhibitor of chitin synthase and a neuritogenic agent. Pseurotin A inhibits IgE production (IC50=3.6 μM). Antitumor activity[1][2][3].
Related Catalog	Research Areas >> Cancer Signaling Pathways >> Others >> Others
In Vitro	Pseurotin A inhibits the expression of PCSK9 in HepG2 cells, with an IC50 value of 1.2 μM. Pseurotin A (25-100 μM; 72 hours) significantly suppressed the PCSK9 level in a dose dependent manner in BT-474 and T47D BC cell lines. Pseurotin A (25-100 μM; 72 hours) significantly increases LDLR level in a dose dependent manner[3]. Pseurotin A (40-200 μM; 24-72 hours) shows anti-proliferative activity in the hormone-dependent BC cells[3]. Cell Viability Assay[3] Cell Line: BT-474 cells, T47D cells Concentration: 40-200 μM Incubation Time: 24-72 hours Result: Showed weak but time and dose-dependent inhibition of the growth of BT-474 and T47D BC cells, with gradual decrease of the IC50 values over time (260.83-93.64 μM and 267.84-113.08 μM, respectively).
In Vivo	Pseurotin A (10 mg/kg; p.o.; 7X/week, 30 days) shows anti-tumor activity[3]. Animal Model: HFD-fed orthotopic athymic mice (bearing BT-474 tumor cells xenograft mode)[1] Dosage: 10 mg/kg Administration: P.o.; 7X/week, 30 days Result: Significantly suppressed the growth of BT474 tumors.
References	[1]. Ishikawa M, et al. Pseurotin A and its analogues as inhibitors of immunoglobulin E [correction of immunoglobuline E] production. Bioorg Med Chem Lett. 2009;19(5):1457-1460. [2]. Maiya S, Grundmann A, Li X, Li SM, Turner G. Identification of a hybrid PKS/NRPS required for pseurotin A biosynthesis in the human pathogen Aspergillus fumigatus. Chembiochem. 2007;8(14):1736-1743. [3]. Abdelwahed KS, et al. Pseurotin A as a novel suppressor of hormone dependent breast cancer progression and recurrence by inhibiting PCSK9 secretion and interaction with LDL receptor. Pharmacol Res. 2020;158:104847.

Density	1.4±0.1 g/cm3
Boiling Point	751.5±60.0 °C at 760 mmHg
Melting Point	126.0-126.9℃
Molecular Formula	C₂₂H₂₅NO₈
Molecular Weight	431.436
Flash Point	408.3±32.9 °C
Exact Mass	431.158020
PSA	142.39000
LogP	3.23
Vapour Pressure	0.0±2.6 mmHg at 25°C
Index of Refraction	1.626

Hazard Codes	Xi

Precursor 2
67-56-1 64638-65-9
DownStream 0