SMB01003

Cyclopenin

≥90% (LC/MS-ELSD)

• Synonym(s): (-)-Cyclopenin, (-)-Cyclopenine, 4-methyl-3′-phenylspiro[1H-1,4-benzodiazepine-3,2′-oxirane]-2,5-dione
• Empirical Formula (Hill Notation): C₁₇H₁₄N₂O₃
• CAS Number: 20007-87-8
• Molecular Weight: 294.30
• UNSPSC Code: 12352205
• NACRES: NA.25

Properties

• biological source: plant
• assay: ≥90% (LC/MS-ELSD)
• form: solid
• mol wt: 294.3
• solubility: water: slightly soluble
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• storage temp.: −20°C
• InChI: 1S/C17H14N2O3/c1-19-15(20)12-9-5-6-10-13(12)18-16(21)17(19)14(22-17)11-7-3-2-4-8-11/h2-10,14H,1H3,(H,18,21)
• InChI key: APLKWZASYUZSBL-UHFFFAOYSA-N

Description

General description

Cyclopenin, a benzodiazepine alkaloid, is a natural product commonly available from strains of Penicillum cyclopium, Penicillium aurantiogriseum and Penicillum corymbiferum. Existing research suggests that this Penicillium metabolite exerts various biological activities, including antibacterial, antiviral, antitumor, anti-inflammatory, and neuroprotective properties.

Application

It is a natural product derived from plant source that finds application in compound screening libraries, metabolomics, phytochemical, and pharmaceutical research.

Biochem/physiol Actions

According to existing research, Cyclopenin displays selective inhibition against acetylcholinesterase (AChE). Furthermore, it demonstrates anti-inflammatory properties by inhibiting nitric oxide production, NF-κB activation, and the expression of inflammatory factors such as IL-1β, IL-6, and iNOS in brain macrophages. In an Alzheimer′s disease model, Cyclopenin exhibited the ability to rescue learning deficits induced by amyloid-β42 overexpression in flies, indicating its potential as an anti-inflammatory agent for neurodegenerative diseases. Isolated from Penicillium polonicum MCCC3A00951, Cyclopenin displayed potent inhibition of influenza neuraminidase (NA) with an IC50 value of 5.02μM, suggesting its potential as a candidate for anti-influenza NA therapy. Cyclopenin, identified in the fungus Penicillium auratiogriseum Sp-19, demonstrated cytotoxicity against the tsFT210 cell line at a concentration of 3 μg/mL-1, implying its potential as an antitumor agent.(3)Cyclopenin, isolated from Penicillium polonicum MCCC3A00951, exhibited strong inhibition of influenza neuraminidase (NA) with an IC50 value of 5.02μM. This suggests that Cyclopenin has the potential to be developed as an anti-influenza NA candidate.

Features and Benefits

• High quality compound suitable for multiple research applications
• Compatible with HPLC and mass spectrometry techniques

Other Notes

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Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable