Epoformin
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| Category | Antibiotics |
| Catalog number | BBF-00847 |
| CAS | 52146-62-0 |
| Molecular Weight | 140.14 |
| Molecular Formula | C7H8O3 |
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Description
Epoformin is an antibiotic produced by Penicillum claviforme. It has only weak antibacterial activity, but it has a strong effect on PS cells and a poor effect on sarcoma L-1210.
Specification
| Synonyms | Antibiotic 417-A |
| IUPAC Name | (1R,5R,6R)-5-hydroxy-3-methyl-7-oxabicyclo[4.1.0]hept-3-en-2-one |
| Canonical SMILES | CC1=CC(C2C(C1=O)O2)O |
| InChI | InChI=1S/C7H8O3/c1-3-2-4(8)6-7(10-6)5(3)9/h2,4,6-8H,1H3/t4-,6-,7+/m1/s1 |
| InChI Key | WCZPXJJNPSYRIV-QXRNQMCJSA-N |
Properties
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 89-91°C |
| Solubility | Soluble in Methanol, Water, butanol |
Reference Reading
1. Fungal Metabolites with Antagonistic Activity against Fungi of Lithic Substrata
Marco Masi, Mariagioia Petraretti, Antonino De Natale, Antonino Pollio, Antonio Evidente Biomolecules. 2021 Feb 16;11(2):295. doi: 10.3390/biom11020295.
Fungi are among the biotic agents that can cause deterioration of building stones and cultural heritage. The most common methods used to control fungal spread and growth are based on chemical pesticides. However, the massive use of these synthetic chemicals produces heavy environmental pollution and risk to human and animal health. Furthermore, their use is time dependent and relies on the repetition of treatments, which increases the possibility of altering building stones and culture heritage through environmental contamination. One alternative is the use of natural products with high antifungal activity, which can result in reduced toxicity and deterioration of archeological remains. Recently, three fungal strains, namely Aspergillus niger, Alternaria alternata and Fusarium oxysporum, were isolated as damaging agents from the external tuff wall of the Roman remains "Villa of Poppea" in Oplontis, Naples, Italy. In this manuscript, three selected fungal metabolites, namely cyclopaldic acid, cavoxin and epi-epoformin, produced by fungi pathogenic for forest plants, were evaluated as potential antifungal compounds against the above fungi. Cavoxin and epi-epoformin showed antifungal activity against Asperigillus niger and Fusarium oxysporum, while cyclopaldic acid showed no activity when tested on the three fungi. The same antifungal activity was observed in vitro experiments on infected stones of the Neapolitan yellow tuff (NYT), a volcanic lithotype widely diffused in the archeological sites of Campania, Italy. This study represents a first step in the use of these two fungal metabolites to allow better preservation of artworks and to guarantee the conditions suitable for their conservation.
2. In Vitro and In Vivo Toxicity Evaluation of Natural Products with Potential Applications as Biopesticides
Felicia Sangermano, Marco Masi, Amrish Kumar, Ravindra Peravali, Angela Tuzi, Alessio Cimmino, Daniela Vallone, Giuliana Giamundo, Ivan Conte, Antonio Evidente, Viola Calabrò Toxins (Basel). 2021 Nov 15;13(11):805. doi: 10.3390/toxins13110805.
The use of natural products in agriculture as pesticides has been strongly advocated. However, it is necessary to assess their toxicity to ensure their safe use. In the present study, mammalian cell lines and fish models of the zebrafish (Danio rerio) and medaka (Oryzias latipes) have been used to investigate the toxic effects of ten natural products which have potential applications as biopesticides. The fungal metabolites cavoxin, epi-epoformin, papyracillic acid, seiridin and sphaeropsidone, together with the plant compounds inuloxins A and C and ungeremine, showed no toxic effects in mammalian cells and zebrafish embryos. Conversely, cyclopaldic and α-costic acids, produced by Seiridium cupressi and Dittrichia viscosa, respectively, caused significant mortality in zebrafish and medaka embryos as a result of yolk coagulation. However, both compounds showed little effect in zebrafish or mammalian cell lines in culture, thus highlighting the importance of the fish embryotoxicity test in the assessment of environmental impact. Given the embryotoxicity of α-costic acid and cyclopaldic acid, their use as biopesticides is not recommended. Further ecotoxicological studies are needed to evaluate the potential applications of the other compounds.
3. An Ecotoxicological Evaluation of Four Fungal Metabolites with Potential Application as Biocides for the Conservation of Cultural Heritage
Mariagioia Petraretti, Antonietta Siciliano, Federica Carraturo, Alessio Cimmino, Antonino De Natale, Marco Guida, Antonino Pollio, Antonio Evidente, Marco Masi Toxins (Basel). 2022 Jun 14;14(6):407. doi: 10.3390/toxins14060407.
Biocides based on chemical synthetic compounds have been commonly used to counteract damages caused by microorganisms on stone cultural heritage. However, in the last few years, the use of commercial and traditional biocides has been banned and/or limited due to their dangerous profile for the environment, as well as human and animal health. Natural products could be used as suitable alternatives for cultural heritage purposes, as they have low toxicity and stability compared with synthetic pesticides. Even if most of the investigated solutions have already shown promising results, their efficiency, ecotoxicological, and chemical features are poorly investigated. In this manuscript, we aimed to evaluate the ecotoxicological profile of four fungal metabolites-namely, cavoxin, epi-epoformin, seiridin, and sphaeropsidone-with potential antimicrobial properties for monumental artworks. A battery of ecotoxicological tests using Aliivibrio fischeri (bacterium), Raphidocelis subcapitata (alga), Raphanus sativus L. (macrophyte), Daphnia magna (crustacean), and Caenorhabditis elegans (nematode) revealed a relative lower toxicity of these compounds, especially when compared with Preventol® and Rocima®, commercial biocides mainly used for the conservation of cultural heritage.
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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 ╳
