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Molecules 2016, 21(2), 254; doi:10.3390/molecules21020254

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

Department of Chemistry, College of Sciences, Huazhong Agricultural University, Wuhan 430070, China
Author to whom correspondence should be addressed.
Academic Editors: Jean Jacques Vanden Eynde and Derek J. McPhee
Received: 29 September 2015 / Revised: 7 January 2016 / Accepted: 13 January 2016 / Published: 22 February 2016
(This article belongs to the Section Bioorganic Chemistry)
View Full-Text   |   Download PDF [628 KB, uploaded 22 February 2016]   |  


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-3,6-diene-8,9,10-triol (3) exhibited excellent inhibitory effect on both Penicillium digitatum (IC50 = 34 ppm) and Penicillium italicum (IC50 = 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. View Full-Text
Keywords: oxylipin; synthesis; antifungal activity; citrus; pathogen oxylipin; synthesis; antifungal activity; citrus; pathogen

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Ma, J.; Li, Y.; Chen, H.; Zeng, Z.; Li, Z.-L.; Jiang, H. Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens. Molecules 2016, 21, 254.

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