58523-30-1

Basic information

• Product Name: pseurotin
• Synonyms: pseurotin;(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;PB-1;NSC 348694
• CAS NO: 58523-30-1
• Molecular Formula: C₂₂H₂₅NO₈
• Molecular Weight: 431.439
• Mol File: 58523-30-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 126.0-126.9℃
• Boiling Point: 751.5°C at 760 mmHg
• Flash Point: 408.3°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 1E-23mmHg at 25°C
• Refractive Index: 1.626
• Storage Temp.: -20°C
• Solubility: Soluble in DMSO (10 mg/ml)
• PKA: 14.76±0.20(Predicted)
• 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.
• CAS DataBase Reference: pseurotin(CAS DataBase Reference)
• NIST Chemistry Reference: pseurotin(58523-30-1)
• EPA Substance Registry System: pseurotin(58523-30-1)

Safety Data

• Hazardous Substances Data: 58523-30-1(Hazardous Substances Data)

Usage

Description

Pseurotin A, a fungal metabolite with a unique hetero-spirocyclic ring system, is known for its potent neuritogenic activity in PC12 cells. It induces multipolar and branching neurites, similar to those produced by β-NGF, an endogenous neurotrophic factor. Pseurotin A also exhibits immunosuppressive activity by inhibiting immunoglobulin E production, antiproliferative effects on glioma cell lines, chitinase inhibition, and acts synergistically with azole antifungal agents.

Uses

1. Used in Anticancer Applications:
Pseurotin A is used as an anticancer agent for its antiproliferative effects on four glioma cell lines by regulating tumor metabolic enzymes.
2. Used in Immunosuppressive Applications:
Pseurotin A is used as an immunosuppressive agent for its ability to inhibit immunoglobulin E production in vitro.
3. Used in Neuronal Differentiation:
Pseurotin A is used as a neuritogenic agent in PC12 phaechromocytoma cells, a useful model for adrenergic neuronal differentiation, as it induces multipolar and branching neurites comparable to β-NGF.
4. Used in Antifungal Applications:
Pseurotin A is used as an antifungal agent, exhibiting chitinase inhibition and acting synergistically with azole antifungal agents.
5. Used in Bone Health Applications:
Pseurotin A is used to inhibit osteoclastogenesis and prevent ovariectomized-induced bone loss by suppressing reactive oxygen species (ROS).

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

InChI:InChI=1/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

Upstream product

• 67-56-1 methanol 
• 149883-42-1 (5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexenyl]-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione 
• 562858-39-3 (5S,8S,9R)-8-benzoyl-2-((2S,4S,5S)-(Z)-5-(but-1-enyl)-2-methyl-[1,3]dioxolan-4-yl)-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione 
• 16749-42-1 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 
• 127941-81-5 (+)-synerazol 
• 58546-67-1 (12S,13S)-12,13-dibromo-12,13-dihydropseurotin A 
• 499120-97-7 (2S,3R,4R)-4-benzyloxy-2,3-isopropylidenedioxy-3-vinyl-hexan-1-ol 
• 660842-21-7 (5S,9S)-2-((Z)-(1S,2S)-1,2-Bis-methoxymethoxy-hex-3-enyl)-9-methoxymethoxy-3-methyl-8-[1-phenyl-meth-(Z)-ylidene]-1-oxa-7-aza-spiro[4.4]non-2-ene-4,6-dione 
• 660842-22-8 (5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-bis(methoxymethoxy)-3-hexenyl]-8-hydroxy-9-methoxymethoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione 
• 660842-20-6 (5S,8R,9R)-8-benzyl-2-[(1S,2S,3Z)-1,2-bis(methoxymethoxy)-3-hexenyl]-8-hydroxy-9-methoxymethoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione 
• 660842-19-3 (S)-5-((Z)-(1S,2S)-1,2-Bis-methoxymethoxy-hex-3-enyl)-2-((R)-1-methoxymethoxy-2-oxo-3-phenyl-propyl)-4-methyl-3-oxo-2,3-dihydro-furan-2-carboxylic acid amide 
• 660842-18-2 (5S,8R,9S)-8-benzyl-2-[(1S,2S,3Z)-1,2-bis(methoxymethoxy)-3-hexenyl]-9-methoxymethoxy-3-methyl-1,7-dioxaspiro[4.4]non-2-ene-4,6-dione 
• 499121-02-7 (3S,4S,5R)-5-Benzyl-3-((Z)-(4R,5S)-3-hydroxy-4,5-bis-methoxymethoxy-2-methyl-non-6-enoyl)-3,4-bis-triethylsilanyloxy-dihydro-furan-2-one 
• 499121-03-8 (3S,4S,5R)-5-Benzyl-3-hydroxy-3-((Z)-(4R,5S)-3-hydroxy-4,5-bis-methoxymethoxy-2-methyl-non-6-enoyl)-4-triethylsilanyloxy-dihydro-furan-2-one 

Downstream Products

• 77353-57-2 (9-O),(10-O),(11-O)-triacetylpseurotin A 
• 77353-58-3 7,(9-O),(10-O),(11-O)-tetraacetylpseurotin A 
• 1576-87-0 trans-2-pentenal 
• 1145685-16-0 C₂₄H₂₉NO₈ 
• 1145685-15-9 C₂₁H₂₃NO₈ 
• 1145685-14-8 C₂₂H₂₅NO₈ 
• 1145685-30-8 12,13-cyclopropylpseurotin A 
• 1145685-18-2 C₂₈H₂₉NO₈ 
• 956904-34-0 11-O-methylpseurotin A 
• 1145685-28-4 12,13-epoxypseurotin A 
• 1145685-13-7 8-ethoxypseurotin A 
• 1145685-17-1 C₂₂H₂₃NO₁₀ 
• 1145685-19-3 C₂₅H₂₉NO₈ 
• 1145685-34-2 C₂₉H₂₉NO₉S 

Relevant articles and documents

Elucidation of pseurotin biosynthetic pathway points to trans-acting C-methyltransferase: Generation of chemical diversity

Pseurotins comprise a family of structurally related Aspergillal natural products having interesting bioactivity. However, little is known about the biosynthetic steps involved in the formation of their complex chemical features. Systematic deletion of the pseurotin biosynthetic genes in A. fumigatus and invivo and invitro characterization of the tailoring enzymes to determine the biosynthetic intermediates, and the gene products responsible for the formation of each intermediate, are described. Thus, the main biosynthetic steps leading to the formation of pseurotinA from the predominant precursor, azaspirene, were elucidated. The study revealed the combinatorial nature of the biosynthesis of the pseurotin family of compounds and the intermediates. Most interestingly, we report the first identification of an epoxidase C-methyltransferase bifunctional fusion protein PsoF which appears to methylate the nascent polyketide backbone carbon atom in trans. A maze: Pseurotins are a family of structurally related bioactive natural products from Aspergilli. Through genetic and biochemical studies, the biosynthetic pathway for the formation of azaspirene, synerazol, and pseurotin A/D have been elucidated, and reveal the combinatorial nature of their biosyntheses. PsoF was identified as bifunctional epoxidase methyltransferase enzyme, thus providing the first example of a trans-acting polyketide C-methyltransferase.

Total syntheses of natural pseurotins A and F2 and azaspirene

Total syntheses of natural pseurotins A (1) and F2 (8-O-demethylpseurotin A) (2) and structurally related azaspirene (3), each possessing a novel heterospirocyclic system, i.e., 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione skeleton, have been accom

Asymmetric total synthesis of pseurotin A

(Matrix presented) The asymmetric total syntheses of pseurotin A and 8-O-demethylpseurotin A have been accomplished. Key reactions are a NaH-promoted intramolecular cyclization of an alkynylamide to form a γ-lactam, an aldol reaction of a benzylidene-subs