Cyclopenin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01747 |
| CAS | 20007-87-8 |
| Molecular Weight | 294.30 |
| Molecular Formula | C17H14N2O3 |
| Purity | ≥99% |
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Description
It is produced by the strain of Penicillum cyclopium and Pen. corymbiferum. Cyclopenin can inhibit the growth of plants. Cyclopenin acts as an inhibitor of acetylcholinesterase (AChE). Cyclopenin also has antibacterial activity against E. coli and M. pyogenes.
Specification
| Related CAS | 19553-26-5 (R-isomer) |
| Synonyms | (-)-Cyclopenine; (-)-Cyclopenin; Cyclopenine; (3S,3'R)-4-Methyl-3'-phenylspiro[3H-1,4-benzodiazepine-3,2'-oxirane]-2,5(1H,4H)-dione; Spiro(3H-1,4-benzodiazepine-3,2'-oxirane)-2,5(1H,4H)-dione, 4-methyl-3'-phenyl-, cis-(-)-(9CI)- |
| IUPAC Name | (3S,3'R)-4-methyl-3'-phenylspiro[1H-1,4-benzodiazepine-3,2'-oxirane]-2,5-dione |
| Canonical SMILES | CN1C(=O)C2=CC=CC=C2NC(=O)C13C(O3)C4=CC=CC=C4 |
| InChI | 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)/t14-,17+/m1/s1 |
| InChI Key | APLKWZASYUZSBL-PBHICJAKSA-N |
Properties
| Appearance | Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Boiling Point | 572.5 °C at 760 mmHg |
| Melting Point | 183-184 °C |
| Density | 1.40 g/cm3 |
| Solubility | Soluble in Methanol, Ethanol |
Reference Reading
1. Inhibition of cellular inflammatory mediator production and amelioration of learning deficit in flies by deep sea Aspergillus-derived cyclopenin
Jianhua Ju, Hiromi Suzuki, Mengjie Li, Liyan Wang, Yinzhi Lin, Kazuo Umezawa, Zhenyu Liu, Shuwen Du, Makoto Sawada J Antibiot (Tokyo) . 2020 Sep;73(9):622-629. doi: 10.1038/s41429-020-0302-9.
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 of NO and secretion of IL-6 in RAW264.7 cells at nontoxic concentrations. In terms of the mechanism underlying these effects, cyclopenol and cyclopenin were found to inhibit the upstream signal of NF-κB activation. These compounds also inhibited the expression of IL-1β, IL-6, and inducible nitric oxide synthase (iNOS) in mouse microglia cells, macrophages in the brain. In relation to the cause of Alzheimer's disease, amyloid-β-peptide is known to induce inflammation in the brain. Therefore, the present study investigated the ameliorative effects of these inhibitors on an in vivo Alzheimer's model using flies. Learning deficits were induced by the overexpression of amyloid-β42 in flies, and cyclopenin but not cyclopenol was found to rescue learning impairment. Therefore, novel anti-inflammatory activities of cyclopenin were identified, which may be useful as a candidate of anti-inflammatory agents for neurodegenerative diseases.
2. Enzymatic one-step ring contraction for quinolone biosynthesis
Hiroshi Hashimoto, Yi Tang, Pier Alexandre Champagne, Kodai Hara, Shinji Kishimoto, Yuichiro Hirayama, Kendall N Houk, Kenji Watanabe Nat Commun . 2018 Jul 19;9(1):2826. doi: 10.1038/s41467-018-05221-5.
The 6,6-quinolone scaffolds on which viridicatin-type fungal alkaloids are built are frequently found in metabolites that display useful biological activities. Here we report in vitro and computational analyses leading to the discovery of a hemocyanin-like protein AsqI from the Aspergillus nidulans aspoquinolone biosynthetic pathway that forms viridicatins via a conversion of the cyclopenin-type 6,7-bicyclic system into the viridicatin-type 6,6-bicyclic core through elimination of carbon dioxide and methylamine through methyl isocyanate.
3. New compounds from a hydrothermal vent crab-associated fungus Aspergillus versicolor XZ-4
Bin Wu, Xuegang Chen, Chen-Tung Arthur Chen, Xinyi Tao, Chengqian Pan, Yutong Shi Org Biomol Chem . 2017 Feb 1;15(5):1155-1163. doi: 10.1039/c6ob02374f.
Three new quinazoline derivatives (1-3), one new oxepin-containing natural product (4) and four new cyclopenin derivatives (5-7 and 9) have been isolated from an EtOAc extract of the Taiwan Kueishantao hydrothermal vent crab-associated fungus Aspergillus versicolor XZ-4. Their planar structures were established by HRMS, 1D and 2D NMR spectroscopic data analyses. The absolute configurations for compounds 1 and 4 were determined by chiral phase HPLC analysis of their hydrolysis products. The absolute configurations of 2, 3 and 7 were defined mainly by comparison of the quantum chemical TDDFT calculated and the experimental ECD spectra, and the absolute configuration of 5 was deduced from comparison of the optical rotation values reported in the literature. The presence of two atropisomers of 5 was established by NOE analyses. The Ile & Val units in compounds 1-3 allowed the assignment of a new quinazoline skeleton and it's the first time the configuration of isoleucine in the quinazoline skeleton was defined. A series of 7-methoxy cyclopenin derivatives were reported for the first time in this study. The bioevaluation of compounds 5, 7, 8 and 9 revealed inhibitory activities against E. coli at MIC values around 32 μg mL-1.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
