SMB01003
Cyclopenin
≥90% (LC/MS-ELSD)
Synonym(s):
(-)-Cyclopenin, (-)-Cyclopenine, 4-methyl-3′-phenylspiro[1H-1,4-benzodiazepine-3,2′-oxirane]-2,5-dione
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About This Item
Empirical Formula (Hill Notation):
C17H14N2O3
CAS Number:
Molecular Weight:
294.30
UNSPSC Code:
12352205
NACRES:
NA.25
SMILES string
N1(C3(OC3c4ccccc4)C(=O)Nc2c(cccc2)C1=O)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
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
Related Categories
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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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Bioactive compounds derived from the marine-derived fungus MCCC3A00951 and their influenza neuraminidase inhibition activity in vitro and in silico
Liu S Z, et al.
Natural product research, 35, 5621-5628 (2021)
Liyan Wang et al.
The Journal of antibiotics, 73(9), 622-629 (2020-03-27)
In the course of screening lipopolysaccharide (LPS)-induced nitric oxide (NO) production inhibitors, two related benzodiazepine derivatives, cyclopenol and cyclopenin, were isolated from the extract of a deep marine-derived fungal strain, Aspergillus sp. SCSIOW2. Cyclopenol and cyclopenin inhibited the LPS-induced formation
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