title: Lasiolactols A and B Produced by the Grapevine Fungal Pathogen Lasiodiplodia mediterranea.
abstract: A strain of Lasiodiplodia mediterranea, a fungus associated with grapevine decline in Sicily, produced several metabolites in liquid medium. Two new dimeric γ-lactols, lasiolactols A and B (1 and 2), were characterized as (2S*,3S*,4R*,5R*,2'S*,3'S*,4'R*,5'R*)- and (2R*,3S*,4R*,5R*,2'R*,3'S*,4'R*,5'R*)-(5-(4-hydroxymethyl-3,5-dimethyl-tetrahydro-furan-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.
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte Sant'Angelo, Via Cintia 4, IT-80126, Napoli.
authors.forename: Anna
authors.initials: A
authors.lastname: Andolfi
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte Sant'Angelo, Via Cintia 4, IT-80126, Napoli.
authors.forename: Sara
authors.initials: S
authors.lastname: Basso
authors.affiliation: Dipartimento di Scienze Agrarie e Forestali, Università degli Studi di Palermo, Viale delle Scienze 4, IT-90128, Palermo.
authors.forename: Selene
authors.initials: S
authors.lastname: Giambra
authors.affiliation: Dipartimento di Scienze Agrarie e Forestali, Università degli Studi di Palermo, Viale delle Scienze 4, IT-90128, Palermo.
authors.forename: Gaetano
authors.initials: G
authors.lastname: Conigliaro
authors.affiliation: Dipartimento di Scienze Agrarie e Forestali, Università degli Studi di Palermo, Viale delle Scienze 4, IT-90128, Palermo.
authors.forename: Sandra
authors.initials: S
authors.lastname: Lo Piccolo
authors.affiliation: Departamento de Biologia, CESAM, Universidade de Aveiro, Campus Universitário de Santiago, PT-3810-193, Aveiro.
authors.forename: Artur
authors.initials: A
authors.lastname: Alves
authors.affiliation: Dipartimento di Scienze Agrarie e Forestali, Università degli Studi di Palermo, Viale delle Scienze 4, IT-90128, Palermo.
authors.forename: Santella
authors.initials: S
authors.lastname: Burruano
mesh_terms: D001203:Ascomycota / Q000378:metabolism* / Q000472:pathogenicity; D000432:Methanol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D013053:Spectrophotometry / Q000379:methods; D027843:Vitis / Q000382:microbiology*
chemical_list: C000613354:lasiolactol A; D000432:Methanol
keywords: Botryosphaeria dieback; Jasmonic acid; Lasiodiplodia mediterranea; Lasiolactols A and B; Phytotoxins