Radicinin
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| Category | Antibiotics |
| Catalog number | BBF-02172 |
| CAS | 10088-95-6 |
| Molecular Weight | 236.22 |
| Molecular Formula | C12H12O5 |
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Description
Radicinin is produced by the strain of Curvularia lunata IAM-18010. It has anti-bacterial effect, but its activity is weak.
Specification
| Synonyms | Stemphylone; NSC 118343; 2,3-Dihydro-3-alpha-hydroxy-2-beta-methyl-7-propenyl-4H,5H-pyrano(4,3-b)pyran-4,5-dione |
| IUPAC Name | (2S,3S)-3-hydroxy-2-methyl-7-[(E)-prop-1-enyl]-2,3-dihydropyrano[3,2-c]pyran-4,5-dione |
| Canonical SMILES | CC=CC1=CC2=C(C(=O)C(C(O2)C)O)C(=O)O1 |
| InChI | InChI=1S/C12H12O5/c1-3-4-7-5-8-9(12(15)17-7)11(14)10(13)6(2)16-8/h3-6,10,13H,1-2H3/b4-3+/t6-,10-/m0/s1 |
| InChI Key | SDKXGAICTNHFCN-DCJAWTJCSA-N |
Properties
| Appearance | Colorless Long Acicular Crystal |
| Boiling Point | 430.8°C at 760 mmHg |
| Melting Point | 238-240°C |
| Density | 1.35 g/cm3 |
Reference Reading
1. In Vitro Effects of Fungal Phytotoxins on Cancer Cell Viability: First Insight into Structure Activity Relationship of a Potent Metabolite of Cochliobolus australiensis Radicinin
Veronique Mathieu, Stefano Superchi, Marco Masi, Patrizia Scafato, Alexander Kornienko, Antonio Evidente Toxins (Basel). 2022 Jul 29;14(8):517. doi: 10.3390/toxins14080517.
Natural compounds have always represented an important source for new drugs. Although fungi represent one such viable source, to date, no fungal metabolite has been marketed as an anticancer drug. Based on our work with phytotoxins as potential chemical scaffolds and our recent findings involving three phytopathogenic fungi, i.e., Cochliobolus australiensis, Kalmusia variispora and Hymenoscyphus fraxineus, herein, we evaluate the in vitro anti-cancer activity of the metabolites of these fungi by MTT assays on three cancer cell models harboring various resistance levels to chemotherapeutic drugs. Radicinin, a phytotoxic dihydropyranopyran-4,5-dione produced by Cochliobolus australiensis, with great potential for the biocontrol of the invasive weed buffelgrass (Cenchrus ciliaris), showed significant anticancer activity in the micromolar range. Furthermore, a SAR study was carried out using radicinin, some natural analogues and hemisynthetic derivatives prepared by synthetic methods developed as part of work aimed at the potential application of these molecules as bioherbicides. This investigation opens new avenues for the design and synthesis of novel radicinin analogues as potential anticancer agents.
2. Radicinin, a Fungal Phytotoxin as a Target-Specific Bioherbicide for Invasive Buffelgrass ( Cenchrus ciliaris) Control
Marco Masi, Fabrizio Freda, Felicia Sangermano, Viola Calabrò, Alessio Cimmino, Massimo Cristofaro, Susan Meyer, Antonio Evidente Molecules. 2019 Mar 19;24(6):1086. doi: 10.3390/molecules24061086.
The fungal pathogens Cochliobolus australiensis and Pyricularia grisea have recently been isolated from diseased leaves of buffelgrass (Cenchrus ciliaris) in its North American range, and their ability to produce phytotoxic metabolites that could potentially be used as natural herbicides against this invasive weed was investigated. Fourteen secondary metabolites obtained from in vitro cultures of these two pathogens were tested by leaf puncture assay on the host plant at different concentrations. Radicinin and (10S, 11S)-epi-pyriculol proved to be the most promising compounds. Thus, their phytotoxic activity was also evaluated on non-host indigenous plants. Radicinin demonstrated high target-specific toxicity on buffelgrass, low toxicity to native plants, and no teratogenic, sub-lethal, or lethal effects on zebrafish (Brachydanio rerio) embryos. It is now under consideration for the development of a target-specific bioherbicide to be used against buffelgrass in natural systems where synthetic herbicides cause excessive damage to native plants.
3. Effect of cultural conditions on the production of radicinin, a specific fungal phytotoxin for buffelgrass ( Cenchrus ciliaris) biocontrol, by different Cochlioboulus australiensis strains
Marco Masi, Susan Meyer, Suzette Clement, Alessio Cimmino, Antonio Evidente Nat Prod Res. 2021 Jan;35(1):99-107. doi: 10.1080/14786419.2019.1614583. Epub 2019 Jun 5.
Radicinin is a phytotoxic fungal dihydropyranopyran-4,5-dione under evaluation for the development of a target-specific bioherbicide for invasive buffelgrass (Cenchrus ciliaris) control. It has already demonstrated high toxicity on host plants, low toxicity to native plants and no negative effects on zebrafish embryos. To continue these studies at the whole-plant level there is a need to obtain much larger quantities of radicinin, either by optimizing its large-scale production by fungal fermentation or through its total stereoselective synthesis. A rapid and sensitive HPLC method for quantification of radicinin in complex mixtures has been developed in order to evaluate its production by different Cochliobolus australiensis strains and in different cultural conditions. The analysis proved that radicinin is not produced by all the strains tested and its synthesis is strongly affected by cultural conditions. The HPLC method could be useful in selecting the best fungal source for the production of this promising potential bioherbicide.
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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 ╳
