Screening of Secondary Metabolites Produced by <i>Nigrospora sphaerica</i> Associated with the Invasive Weed <i>Cenchrus ciliaris</i> Reveals Two New Structurally Related Compounds
In the search for new alternative biocontrol strategies, phytopathogenic fungi could represent a new frontier for weed management. In this respect, as part of our ongoing work aiming at using fungal pathogens as an alternative to common herbicides, the foliar pathogen <i>Nigrospora sphaerica&l...
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| Format: | Article |
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MDPI AG
2024-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/29/2/438 |
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| author | Maria Michela Salvatore Maria Teresa Russo Susan Meyer Angela Tuzi Marina Della Greca Marco Masi Anna Andolfi |
| author_facet | Maria Michela Salvatore Maria Teresa Russo Susan Meyer Angela Tuzi Marina Della Greca Marco Masi Anna Andolfi |
| author_sort | Maria Michela Salvatore |
| collection | DOAJ |
| description | In the search for new alternative biocontrol strategies, phytopathogenic fungi could represent a new frontier for weed management. In this respect, as part of our ongoing work aiming at using fungal pathogens as an alternative to common herbicides, the foliar pathogen <i>Nigrospora sphaerica</i> has been evaluated to control buffelgrass (<i>Cenchrus ciliaris</i>). In particular, in this work, the isolation and structural elucidation of two new biosynthetically related metabolites, named nigrosphaeritriol (3-(hydroxymethyl)-2-methylpentane-1,4-diol) and nigrosphaerilactol (3-(1-hydroxyethyl)-4-methyltetrahydrofuran-2-ol), from the phytotoxic culture filtrate extract were described, along with the identification of several known metabolites. Moreover, the absolute stereochemistry of (3<i>R</i>,4<i>S</i>,5<i>S</i>)-nigrosphaerilactone, previously reported as (3<i>S</i>,4<i>R</i>,5<i>R</i>)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone, was determined for the first time by X-ray diffraction analysis. Considering their structural relationship, the determination of the absolute stereochemistry of nigrosphaerilactone allowed us to hypothesize the absolute stereochemistry of nigrosphaeritriol and nigrosphaerilactol. |
| first_indexed | 2024-03-08T09:50:11Z |
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| id | doaj.art-d24d436ab07048e3aeb9baa5b59bd8f5 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-08T09:50:11Z |
| publishDate | 2024-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-d24d436ab07048e3aeb9baa5b59bd8f52024-01-29T14:08:37ZengMDPI AGMolecules1420-30492024-01-0129243810.3390/molecules29020438Screening of Secondary Metabolites Produced by <i>Nigrospora sphaerica</i> Associated with the Invasive Weed <i>Cenchrus ciliaris</i> Reveals Two New Structurally Related CompoundsMaria Michela Salvatore0Maria Teresa Russo1Susan Meyer2Angela Tuzi3Marina Della Greca4Marco Masi5Anna Andolfi6Department of Chemical Sciences, University of Naples Federico II, 80126 Naples, ItalyDepartment of Chemical Sciences, University of Naples Federico II, 80126 Naples, ItalyDepartment of Geosciences, Southern Utah University, Cedar City, UT 84721, USADepartment of Chemical Sciences, University of Naples Federico II, 80126 Naples, ItalyDepartment of Chemical Sciences, University of Naples Federico II, 80126 Naples, ItalyDepartment of Chemical Sciences, University of Naples Federico II, 80126 Naples, ItalyDepartment of Chemical Sciences, University of Naples Federico II, 80126 Naples, ItalyIn the search for new alternative biocontrol strategies, phytopathogenic fungi could represent a new frontier for weed management. In this respect, as part of our ongoing work aiming at using fungal pathogens as an alternative to common herbicides, the foliar pathogen <i>Nigrospora sphaerica</i> has been evaluated to control buffelgrass (<i>Cenchrus ciliaris</i>). In particular, in this work, the isolation and structural elucidation of two new biosynthetically related metabolites, named nigrosphaeritriol (3-(hydroxymethyl)-2-methylpentane-1,4-diol) and nigrosphaerilactol (3-(1-hydroxyethyl)-4-methyltetrahydrofuran-2-ol), from the phytotoxic culture filtrate extract were described, along with the identification of several known metabolites. Moreover, the absolute stereochemistry of (3<i>R</i>,4<i>S</i>,5<i>S</i>)-nigrosphaerilactone, previously reported as (3<i>S</i>,4<i>R</i>,5<i>R</i>)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone, was determined for the first time by X-ray diffraction analysis. Considering their structural relationship, the determination of the absolute stereochemistry of nigrosphaerilactone allowed us to hypothesize the absolute stereochemistry of nigrosphaeritriol and nigrosphaerilactol.https://www.mdpi.com/1420-3049/29/2/438specialized metabolitesbuffelgrassphytopathogenbioherbicidemetabolomics |
| spellingShingle | Maria Michela Salvatore Maria Teresa Russo Susan Meyer Angela Tuzi Marina Della Greca Marco Masi Anna Andolfi Screening of Secondary Metabolites Produced by <i>Nigrospora sphaerica</i> Associated with the Invasive Weed <i>Cenchrus ciliaris</i> Reveals Two New Structurally Related Compounds Molecules specialized metabolites buffelgrass phytopathogen bioherbicide metabolomics |
| title | Screening of Secondary Metabolites Produced by <i>Nigrospora sphaerica</i> Associated with the Invasive Weed <i>Cenchrus ciliaris</i> Reveals Two New Structurally Related Compounds |
| title_full | Screening of Secondary Metabolites Produced by <i>Nigrospora sphaerica</i> Associated with the Invasive Weed <i>Cenchrus ciliaris</i> Reveals Two New Structurally Related Compounds |
| title_fullStr | Screening of Secondary Metabolites Produced by <i>Nigrospora sphaerica</i> Associated with the Invasive Weed <i>Cenchrus ciliaris</i> Reveals Two New Structurally Related Compounds |
| title_full_unstemmed | Screening of Secondary Metabolites Produced by <i>Nigrospora sphaerica</i> Associated with the Invasive Weed <i>Cenchrus ciliaris</i> Reveals Two New Structurally Related Compounds |
| title_short | Screening of Secondary Metabolites Produced by <i>Nigrospora sphaerica</i> Associated with the Invasive Weed <i>Cenchrus ciliaris</i> Reveals Two New Structurally Related Compounds |
| title_sort | screening of secondary metabolites produced by i nigrospora sphaerica i associated with the invasive weed i cenchrus ciliaris i reveals two new structurally related compounds |
| topic | specialized metabolites buffelgrass phytopathogen bioherbicide metabolomics |
| url | https://www.mdpi.com/1420-3049/29/2/438 |
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