Lasiolactols A and B Produced by the Grapevine Fungal Pathogen Lasiodiplodia mediterranea |
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Authors: | Anna Andolfi Sara Basso Selene Giambra Gaetano Conigliaro Sandra Lo Piccolo Artur Alves Santella Burruano |
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Affiliation: | 1. Dipartimento di Scienze Chimiche, Università di Napoli Federico II, Napoli;2. Dipartimento di Scienze Agrarie e Forestali, Università degli Studi di Palermo, Palermo;3. Departamento de Biologia, CESAM, Universidade de Aveiro, Aveiro |
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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. |
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Keywords: |
Lasiodiplodia mediterranea
Botryosphaeria dieback Phytotoxins Lasiolactols A and B Jasmonic acid |
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