6533b829fe1ef96bd128ae1e
RESEARCH PRODUCT
Lasiolactols A and B Produced by the Grapevine Fungal Pathogen Lasiodiplodia mediterranea
Gaetano ConigliaroSandra Lo PiccoloArtur AlvesAnna AndolfiSelene GiambraSara BassoS. Burruanosubject
0301 basic medicineChemical structureBioengineeringFungusBiochemistryLasiodiplodia mediterranea Botryosphaeria dieback Phytotoxins Lasiolactols A and B Jasmonic acid03 medical and health scienceschemistry.chemical_compoundPhytotoxinAscomycotaBotanyVitisBotryosphaeria diebackMolecular BiologyJasmonic acidbiologyStrain (chemistry)AscomycotaChemistryMethanolJasmonic acidAbsolute configurationSettore AGR/12 - Patologia VegetaleGeneral ChemistryGeneral Medicine030108 mycology & parasitologybiology.organism_classificationHorticultureSpectrophotometryToxicityMolecular MedicinePhytotoxicityLasiodiplodia mediterraneaLasiolactols A and Bdescription
A strain of Lasiodiplodia mediterranea, a fungus associated with grapevine decline in Sicily, produced several metabolites in liquid medium. Two new dimeric c-lactols, lasiolactols A and B (1 and 2), were characterized as (2S*,3S*,4R*,5R*,20S*,30S*,40R*,50R*)-and (2R*,3S*,4R*,5R*,20R*,30S*,40R*,50R*)-(5-(4-hydroxymethyl-3,5-dimethyl-tetrahydrofuran- 2-yloxy)-2,4-dimethyl-tetrahydro-furan-3-yl]-methanols by IR, 1D-and 2D-NMR, and HR-ESI-MS. Other four metabolites were identified as botryosphaeriodiplodin, (5R)-5-hydroxylasiodiplodin, (-)-(1R, 2R)-jasmonic acid, and (-)-(3S, 4R, 5R)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone (3 - 6, resp.). The absolute configuration (R) at hydroxylated secondary C-atom C(7) was also established for compound 3. The compounds 1 - 3, 5, and 6, tested for their phytotoxic activities to grapevine cv. Inzolia leaves at different concentrations (0.125, 0.25, 0.5, and 1 mg/ml) were phytotoxic and compound 5 showed the highest toxicity. All metabolites did not show in vitro antifungal activity against four plant pathogens.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-04-01 |