Screening of Secondary Metabolites Produced by Nigrospora sphaerica Associated with the Invasive Weed Cenchrus ciliaris 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 has been evaluated to control b...

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Published in:Molecules (Basel, Switzerland) Switzerland), 2024-01, Vol.29 (2), p.438
Main Authors: Salvatore, Maria Michela, Russo, Maria Teresa, Meyer, Susan, Tuzi, Angela, Della Greca, Marina, Masi, Marco, Andolfi, Anna
Format: Article
Language:English
Subjects:
Agricultural production
Ascomycota
Bioassays
bioherbicide
buffelgrass
Cenchrus
Crystallography, X-Ray
Herbicides
Metabolites
metabolomics
Microorganisms
Pathogens
Pesticides
phytopathogen
Plant Weeds
specialized metabolites
Toxicity
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Summary: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 has been evaluated to control buffelgrass ( ). 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 ,4 ,5 )-nigrosphaerilactone, previously reported as (3 ,4 ,5 )-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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules29020438