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Cyclopenin Sale

(Synonyms: (-)-Cyclopenine) 目录号 : GC40569

An AChE inhibitor

Cyclopenin Chemical Structure

Cas No.:20007-87-8

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5mg
¥4,025.00
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25mg
¥14,099.00
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产品描述

Cyclopenin is an inhibitor of acetylcholinesterase (AChE; IC50 = 2.04 μM for human recombinant AChE) that is produced by Penicillium. It exhibits greater than 2,000-fold selectivity over recombinant equine butyrylcholinesterase with an IC50 value greater than 4,080 μM. Cyclopenin also has antibacterial activity against E. coli and M. pyogenes.

Chemical Properties

Cas No. 20007-87-8 SDF
别名 (-)-Cyclopenine
Canonical SMILES O=C(C1=CC=CC=C1N2)N(C)[C@]3([C@@](O3)([H])C4=CC=CC=C4)C2=O
分子式 C17H14N2O3 分子量 294.3
溶解度 Soluble in DMSO 储存条件 Store at -20°C
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1 mM 3.3979 mL 16.9895 mL 33.9789 mL
5 mM 0.6796 mL 3.3979 mL 6.7958 mL
10 mM 0.3398 mL 1.6989 mL 3.3979 mL
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Research Update

Bioguided Isolation of Cyclopenin Analogues as Potential SARS-CoV-2 Mpro Inhibitors from Penicillium citrinum TDPEF34

Biomolecules 2021 Sep 15;11(9):1366.PMID:34572579DOI:10.3390/biom11091366.

SARS-CoV-2 virus mutations might increase its virulence, and thus the severity and duration of the ongoing pandemic. Global drug discovery campaigns have successfully developed several vaccines to reduce the number of infections by the virus. However, finding a small molecule pharmaceutical that is effective in inhibiting SARS-CoV-2 remains a challenge. Natural products are the origin of many currently used pharmaceuticals and, for this reason, a library of in-house fungal extracts were screened to assess their potential to inhibit the main viral protease Mpro in vitro. The extract of Penicillium citrinum, TDPEF34, showed potential inhibition and was further analysed to identify potential Mpro inhibitors. Following bio-guided isolation, a series of benzodiazepine alkaloids cyclopenins with good-to-moderate activity against SARS-CoV-2 Mpro were identified. The mode of enzyme inhibition of these compounds was predicted by docking and molecular dynamic simulation. Compounds 1 (isolated as two conformers of S- and R-isomers), 2, and 4 were found to have promising in vitro inhibitory activity towards Mpro, with an IC50 values range of 0.36-0.89 µM comparable to the positive control GC376. The in silico investigation revealed compounds to achieve stable binding with the enzyme active site through multiple H-bonding and hydrophobic interactions. Additionally, the isolated compounds showed very good drug-likeness and ADMET properties. Our findings could be utilized in further in vitro and in vivo investigations to produce anti-SARS-CoV-2 drug candidates. These findings also provide critical structural information that could be used in the future for designing potent Mpro inhibitors.

Inhibition of cellular inflammatory mediator production and amelioration of learning deficit in flies by deep sea Aspergillus-derived Cyclopenin

J Antibiot (Tokyo) 2020 Sep;73(9):622-629.PMID:32210361DOI: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.

Nuclear inheritance of the biosynthesis of Cyclopenin and cyclopenol in Penicillium cyclopium

Z Allg Mikrobiol 1984;24(9):615-8.PMID:6151759DOI:10.1002/jobm.3630240908.

Balanced heterokarions were grown from Penicillium cyclopium aux-glu 1, a glutamic acid auxotroph producing benzodiazepine alkaloids of the cyclopenin-cyclopenol group, and P. viridicatum aux-met 1, a methionine auxotroph forming these alkaloids in traces only. In contrast to the hyphae of the parent strains, the hyphae of the heterokarions were dark orange-brown and grew well on media without the auxotrophic factors. In surface cultures they synthesized the benzodiazepine alkaloids Cyclopenin and cyclopenol in amounts similar to those formed by the hyphae of P. cyclopium aux-glu 1. From the monokariotic conidiospores of the heterokarions homokariotic daughter strains were obtained which were similar to the parent strains in every respect. Hence no exchange of features of cyclopenin-cyclopenol biosynthesis took place between the parent strains at the stage of the heterokarion. This result indicates that the formation of Cyclopenin and cyclopenol in P. cyclopium aux-glu 1 and the nearly complete lack of biosynthesis of these compounds in P. viridicatum aux-met 1 is encoded within the nucleus and is not influenced by plasmic genetic material.

New compounds from a hydrothermal vent crab-associated fungus Aspergillus versicolor XZ-4

Org Biomol Chem 2017 Feb 1;15(5):1155-1163.PMID:28074949DOI: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.

Effect of different storage conditions on the stability and safety of almonds

J Food Sci 2023 Feb;88(2):848-859.PMID:36633227DOI:10.1111/1750-3841.16453.

Almond production in Portugal is of great importance for the economy of their main producing areas. However, the contamination of these nut fruits with fungi and mycotoxins poses a significant risk to food safety and security. This work intended to evaluate the influence of storage conditions on the microbial and mycotoxin stability and safety of almonds throughout long-term storage. Two almond varieties-Lauranne and Guara-were submitted to three different storage conditions, namely, 4°C with noncontrolled relative humidity (RH), 60% RH at 25°C, and 70% RH at 25°C, for a storage period of 9 months. Samples were collected after 0, 3, 6, and 9 months of storage and analyzed for microbial loads (aerobic mesophiles, yeasts, and molds), mold incidence and diversity, and mycotoxin contamination. In total, 26 species were identified belonging to 6 genera: Aspergillus, Cladosporium, Fusarium, Penicillium, Paecilomyces, and Talaromyces. For the variety Guara, mycotoxins related to Aspergillus sect. Flavi, such as aflatoxins, averufin, versicolorin C, and norsolorinic acid, were detected only after 9 months of storage at 70% and 60% RH. Penicillium mycotoxins, such as quinolactacin A and roquefortine C, were also detected. For the variety Lauranne, Penicillium mycotoxins were detected, such as citrinin, quinolactacins A and B, roquefortines C and D, Cyclopenin, cyclopenol, penitrem A, viridicatin, and viridicatol. Mycotoxins related to Aspergillus, such as aspulvinone E, flavoglaucin, paspalin, asperglaucide, asperphenamate, cyclo(L-Pro-L-Tyr), and cyclo(L-Pro-L-Val), were also detected. PRACTICAL APPLICATION: (Optional, for JFS Research Articles ONLY) The quality of almonds depends on the storage period and the RH and temperature at which they are stored. Storage of almonds at 60% RH at 25°C is a good storage condition to maintain the stability and safety of nuts in terms of microbial and mycotoxin contaminations.