Lasiolactols A and B Produced by the Grapevine Fungal Pathogen Lasiodiplodia mediterranea

Chem Biodivers. 2016 Apr;13(4):395-402. doi: 10.1002/cbdv.201500104.

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.

Keywords: Botryosphaeria dieback; Jasmonic acid; Lasiodiplodia mediterranea; Lasiolactols A and B; Phytotoxins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ascomycota / metabolism*
  • Ascomycota / pathogenicity
  • Methanol / analogs & derivatives*
  • Methanol / chemistry
  • Methanol / metabolism
  • Spectrophotometry / methods
  • Vitis / microbiology*

Substances

  • lasiolactol A
  • Methanol

Associated data

  • GENBANK/KJ170150
  • GENBANK/KJ638331
  • GENBANK/KP178596
  • GENBANK/KP178599