Further secondary metabolites produced by the fungus Pyricularia grisea isolated from buffelgrass (Cenchrus ciliaris)
| Autor: | Suzette Clement, Antonio Evidente, Patrizia Scafato, Susan E. Meyer, Ernesto Santoro, Marco Masi, Stefano Superchi |
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| Přispěvatelé: | Masi, Marco, Santoro, Ernesto, Clement, Suzette, Meyer, Susan, Scafato, Patrizia, Superchi, Stefano, Evidente, Antonio |
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Spectrometry
Mass Electrospray Ionization Stereochemistry Electrospray ionization Proton Magnetic Resonance Spectroscopy 010402 general chemistry 01 natural sciences electronic circular dichroism Catalysis Analytical Chemistry Cenchrus ciliaris TDDFT computation Drug Discovery Radicle Carbon-13 Magnetic Resonance Spectroscopy Spectroscopy Pharmacology growth stimulating effect biology Molecular Structure 010405 organic chemistry Chemistry Organic Chemistry Cenchrus Absolute configuration Stereoisomerism biology.organism_classification biopesticide 0104 chemical sciences absolute configuration Coleoptile Epimer Phytotoxicity Biological Assay Weed Pyricularia grisea |
| Popis: | The fungal pathogen Pyricularia grisea has been studied to evaluate its production of phytotoxins for the biocontrol of the buffelgrass (Cenchrus ciliaris L.) weed. A first investigation allowed to isolate several new and known phytotoxic metabolites. However, the further investigation on the organic extract obtained from the fungus liquid culture showed the presence of other metabolites possibly contributing to its phytotoxicity. Thus, four known metabolites were isolated and identified by spectroscopic (nuclear magnetic resonance [NMR] and high-resolution electrospray ionization mass spectrometry [HRESIMS]) methods as dihydropyriculol (1), epi-dihydropyriculol (2), 3-methoxy-6,8-dihydroxy-3-methyl-3,4-dihydroisocoumarin (3), and (R)-mevalonolactone (4). The absolute configuration of 1-3 was determined for the first time by a computational analysis of their electronic circular dichroism (ECD) spectra. When the isolated compounds were bioassayed at a concentration of 5 × 10-3 M in a buffelgrass coleoptile and radicle elongation test no toxicity was detected. On the contrary, compounds 1 and 3 showed a significant stimulating effect of radical elongation. Furthermore, the difference in growth stimulation between 1 and its epimer 2 highlights the tight relationship between absolute configuration and biological activity of these fungal metabolites. |
| Databáze: | OpenAIRE |
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