Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens

Jimei Ma, Yupeng Li, Hangwei Chen, Zhen Zeng, Zi-Long Li, Hong Jiang
2016 Molecules  
Nine oxylipin mimics were designed and synthesized starting from D-mannose. Their antifungal activity against three citrus postharvest pathogens was evaluated by spore germination assay. The results indicated that all the compounds significantly inhibited the growth of Penicillium digitatum, Penicillium italicum and Aspergillus niger. The compound (3Z,6Z,8S,9R,10R)-octadeca-3,6diene-8,9,10-triol (3) exhibited excellent inhibitory effect on both Penicillium digitatum (IC 50 = 34 ppm) and
more » ... 34 ppm) and Penicillium italicum (IC 50 = 94 ppm). Their in vivo antifungal activities against citrus postharvest blue mold were tested with fruit inoculated with the pathogen Penicillium italicum. The compound (3R,4S)-methyl 3,4-dihydroxy-5-octyltetrahydrofuran-2-carboxylate (9) demonstrated significant efficacy by reducing the disease severity to 60%. The antifungal mechanism of these oxylipin mimics was postulated in which both inhibition of pathogenic mycelium and stimuli of the host oxylipin-mediated defense response played important roles. Molecules 2016, 21, 254 2 of 11 paper, a series of oxylipin mimics were designed and synthesized (Scheme 1). Their antifungal effects on P. digitatum, P. italicum and Aspergillus niger in Petri dishes were also investigated.
doi:10.3390/molecules21020254 pmid:26907241 fatcat:fwj3yixrl5ffdnbvsn3zvdsqgi