Cyclopaldic acid
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| Category | Antibiotics |
| Catalog number | BBF-01114 |
| CAS | 477-99-6 |
| Molecular Weight | 238.19 |
| Molecular Formula | C11H10O6 |
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Description
It is produced by the strain of Penicillum cyclopium var. album, Pen. cyclopium 77. Cyclopaldic acid of 2.5 μg/mL can inhibit the spore germination of Garlic botrytis spore 95%-100%.
Specification
| Synonyms | 3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-1,3-dihydro-2-benzofuran-4-carbaldehyde; 1,3-Dihydro-3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-4-isobenzofurancarboxaldehyde; Cyclopaldsaeure |
| IUPAC Name | 3,5-dihydroxy-7-methoxy-6-methyl-1-oxo-3H-2-benzofuran-4-carbaldehyde |
| Canonical SMILES | CC1=C(C(=C2C(OC(=O)C2=C1OC)O)C=O)O |
| InChI | InChI=1S/C11H10O6/c1-4-8(13)5(3-12)6-7(9(4)16-2)11(15)17-10(6)14/h3,10,13-14H,1-2H3 |
| InChI Key | BHVGIMSTMICYNZ-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Boiling Point | 540.9 °C at 760 mmHg |
| Melting Point | 224-225 °C |
| Density | 1.552 g/cm3 |
Reference Reading
1. Cyclopaldic Acid, the Main Phytotoxic Metabolite of Diplodia cupressi, Induces Programmed Cell Death and Autophagy in Arabidopsis thaliana
Simone Samperna, Marco Masi, Maurizio Vurro, Antonio Evidente, Mauro Marra Toxins (Basel). 2022 Jul 11;14(7):474. doi: 10.3390/toxins14070474.
Cyclopaldic acid is one of the main phytotoxic metabolites produced by fungal pathogens of the genus Seiridium, causal agents, among others, of the canker disease of plants of the Cupressaceae family. Previous studies showed that the metabolite can partially reproduce the symptoms of the infection and that it is toxic to different plant species, thereby proving to be a non-specific phytotoxin. Despite the remarkable biological effects of the compound, which revealed also insecticidal, fungicidal and herbicidal properties, information about its mode of action is still lacking. In this study, we investigated the effects of cyclopaldic acid in Arabidopsis thaliana plants and protoplasts, in order to get information about subcellular targets and mechanism of action. Results of biochemical assays showed that cyclopaldic acid induced leaf chlorosis, ion leakage, membrane-lipid peroxidation, hydrogen peroxide production, inhibited root proton extrusion in vivo and plasma membrane H+-ATPase activity in vitro. qRT-PCR experiments demonstrated that the toxin elicited the transcription of key regulators of the immune response to necrotrophic fungi, of hormone biosynthesis, as well as of genes involved in senescence and programmed cell death. Confocal microscopy analysis of protoplasts allowed to address the question of subcellular targets of the toxin. Cyclopaldic acid targeted the plasma membrane H+-ATPase, inducing depolarization of the transmembrane potential, mitochondria, disrupting the mitochondrial network and eliciting overproduction of reactive oxygen species, and vacuole, determining tonoplast disgregation and induction of vacuole-mediated programmed cell death and autophagy.
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. 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.
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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 ╳
