Actiphenol
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| Category | Antibiotics |
| Catalog number | BBF-00028 |
| CAS | 526-02-3 |
| Molecular Weight | 275.30 |
| Molecular Formula | C15H17NO4 |
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Description
Actiphenol is a glutarimide antibiotic isolated from Streptomyces sp. ETH 7796. Actiphenol has an inhibitory effect on yeast.
Specification
| Synonyms | 3-(2-Hydroxy-3,5-dimethylphenacyl)glutarimide |
| Storage | Store at -20°C |
| IUPAC Name | 4-[2-(2-hydroxy-3,5-dimethylphenyl)-2-oxoethyl]piperidine-2,6-dione |
| Canonical SMILES | CC1=CC(=C(C(=C1)C(=O)CC2CC(=O)NC(=O)C2)O)C |
| InChI | InChI=1S/C15H17NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h3-4,10,20H,5-7H2,1-2H3,(H,16,18,19) |
| InChI Key | YTLMIHBTPWTPEV-UHFFFAOYSA-N |
Properties
| Appearance | white needle Crystal |
| Antibiotic Activity Spectrum | yeast |
| Boiling Point | 498.7°C at 760 mmHg |
| Melting Point | 199-200°C |
| Density | 1.232 g/cm3 |
Reference Reading
1. Polyenic Antibiotics and Other Antifungal Compounds Produced by Hemolytic Streptomyces Species
Jan Bobek, Eliška Filipová, Natalie Bergman, Matouš Čihák, Miroslav Petříček, Ana Catalina Lara, Vaclav Kristufek, Melinda Megyes, Theresa Wurzer, Alica Chroňáková, Kateřina Petříčková Int J Mol Sci. 2022 Nov 30;23(23):15045. doi: 10.3390/ijms232315045.
Streptomyces are of great interest in the pharmaceutical industry as they produce a plethora of secondary metabolites that act as antibacterial and antifungal agents. They may thrive on their own in the soil, or associate with other organisms, such as plants or invertebrates. Some soil-derived strains exhibit hemolytic properties when cultivated on blood agar, raising the question of whether hemolysis could be a virulence factor of the bacteria. In this work we examined hemolytic compound production in 23 β-hemolytic Streptomyces isolates; of these 12 were soil-derived, 10 were arthropod-associated, and 1 was plant-associated. An additional human-associated S. sp. TR1341 served as a control. Mass spectrometry analysis suggested synthesis of polyene molecules responsible for the hemolysis: candicidins, filipins, strevertene A, tetrafungin, and tetrin A, as well as four novel polyene compounds (denoted here as polyene A, B, C, and D) in individual liquid cultures or paired co-cultures. The non-polyene antifungal compounds actiphenol and surugamide A were also identified. The findings indicate that the ability of Streptomyces to produce cytolytic compounds (here manifested by hemolysis on blood agar) is an intrinsic feature of the bacteria in the soil environment and could even serve as a virulence factor when colonizing available host organisms. Additionally, a literature review of polyenes and non-polyene hemolytic metabolites produced by Streptomyces is presented.
2. Antimicrobial investigation of selected soil actinomycetes isolated from unexplored regions of Kashmir Himalayas, India
Aabid Manzoor Shah, Shakeel-U-Rehman, Aehtesham Hussain, Saleem Mushtaq, Muzafar Ahmad Rather, Aiyatullah Shah, Zahoor Ahmad, Inshad Ali Khan, Khursheed Ahmad Bhat, Qazi Parvaiz Hassan Microb Pathog. 2017 Sep;110:93-99. doi: 10.1016/j.micpath.2017.06.017. Epub 2017 Jun 22.
The aim of the present study was to isolate and evaluate the antimicrobial potential of soil actinomycetes of Kashmir Himalayas. The secondary metabolites of actinomycetes are the prominent source of antibiotics. A total of 121 morphologically different actinomycete strains were isolated and screened for antimicrobial activity against various human pathogens. The ethyl acetate extract of fermented broth an actinomycete strain, identified as Streptomyces pratensis exhibited significant antimicrobial activity against Staphylococcus aureus ATCC 29213 with MIC 0.25 μg/ml and Mycobacterium tuberculosis Strain H37Rv with MIC 0.062 μg/ml. The strain S. pratensis IIIM06 was grown on large scale and their broth was extracted with ethyl acetate. The extract was subjected to various chromatography techniques which led to the isolation of four compounds whose structures were established as actinomycin C1, actinomycin C2, actinomycin C3 and actiphenol on the basis of spectral data analysis. Actinomycin C1, C2 and C3 exhibited potent antimicrobial activity against S. aureus as well as M. tuberculosis. The isolated indigenous actinomycetes exhibited good antibacterial activity and the study reveals that IIIM06 is a promising strain and could be of great potential for industrial applications.
3. Discovery and Biosynthesis of Glycosylated Cycloheximide from a Millipede-Associated Actinomycete
Jia-Qi Hu, Ai Zhang, Han Wang, Luo Niu, Qing-Xia Wang, Le-Le Zhu, Yue-Zhong Li, Changsheng Wu J Nat Prod. 2023 Feb 24;86(2):340-345. doi: 10.1021/acs.jnatprod.2c00951. Epub 2023 Jan 24.
Chemical redundancy of microbial natural products (NPs) underscores the importance to exploit new resources of microorganisms. Insect-associated microbes are prolific but largely underexplored sources of diverse NPs. Herein, we discovered the new compound α-l-rhamnosyl-actiphenol (1) from a millipede-associated Streptomyces sp. ML6, which is the first glycosylated cycloheximide-class natural product. Interestingly, bioinformatics analysis of the ML6 genome revealed that the biosynthesis of 1 involves a cooperation between two gene clusters (chx and rml) located distantly on the genome of ML6. We also carried out in vitro enzymatic glycosylation of cycloheximide using an exotic promiscuous glycosyltransferase BsGT-1, which resulted in the production of an additional cycloheximide glycoside cycloheximide 7-O-β-d-glucoside (5). Although the antifungal and cytotoxic activities of the new compounds 1 and 5 were attenuated relative to those of cycloheximide, our work not only enriches the chemical repertoire of the cycloheximide family but also provides new insights into the structure-activity relationship optimization and ecological roles of cycloheximide.
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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 ╳
