Andolfi, Anna and Maddau, Lucia and Cimmino, Alessio and Linaldeddu, Benedetto Teodoro and Basso, Sara and Deidda, Antonio and Serra, Salvatorica and Evidente, Antonio (2014) Lasiojasmonates A—C, three jasmonic acid esters produced by Lasiodiplodia sp., a grapevine pathogen. Phytochemistry, Vol. 103 , p. 145-153. ISSN 0031-9422. Article.
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In this study, a strain (BL 101) of a species of Lasiodiplodia, not yet formally described, which was isolated from declining grapevine plants showing wedge-shaped cankers, was investigated for its ability to produce in vitro bioactive secondary metabolites. From culture filtrates of this strain three jasmonic acid esters, named lasiojasmonates A—C and 16-O-acetylbotryosphaerilactones A and C were isolated together with (1R,2R)-jasmonic acid, its methyl ester, botryosphaerilactone A, (3S,4R,5R)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone and (3R,4S)-botryodiplodin. The structures of lasiojasmonates A–C were established by spectroscopic methods as (1R∗,2R∗,3′S∗,4′R∗,5′R∗)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone, (1R∗,2R∗,3′S∗,4′R∗,5′R∗,10′R∗,12′R∗,13′R∗,14′S∗) and (1R∗,2R∗,3′S∗,4′R∗,5′R∗,10′S∗,12′R∗,13′R∗,14′S∗)-4-(4-hydroxymethyl-3,5-dimethyltetrahydro-furan-2-yloxymethyl)-3,5-dimethyldihydro-2-furanones jasmonates (1, 4 and 5). The structures of 16-O-acetylbotryosphaerilactones A and C were determined by comparison of their spectral data with those of the corresponding acetyl derivatives obtained by acetylation of botryosphaerilactone A. The metabolites isolated, except 4 and 5, were tested at 1 mg/mL on leaves of grapevine cv. Cannonau and cork oak using the leaf puncture assay. They were also tested on detached grapevine leaves at 0.5 mg/mL and tomato cuttings at 0.1 mg/mL. In all phytotoxic assays only jasmonic acid was found to be active. All metabolites were inactive in the zootoxic assay at 50 μg/mL.
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