title: Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens.
abstract: 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.
authors.affiliation: Department of Chemistry, College of Sciences, Huazhong Agricultural University, Wuhan 430070, China. majimei@mail.hzau.edu.cn.
authors.forename: Jimei
authors.initials: J
authors.lastname: Ma
authors.affiliation: Department of Chemistry, College of Sciences, Huazhong Agricultural University, Wuhan 430070, China. liyupeng@webmail.hzau.edu.cn.
authors.forename: Yupeng
authors.initials: Y
authors.lastname: Li
authors.affiliation: Department of Chemistry, College of Sciences, Huazhong Agricultural University, Wuhan 430070, China. chw234234@hotmail.com.
authors.forename: Hangwei
authors.initials: H
authors.lastname: Chen
authors.affiliation: Department of Chemistry, College of Sciences, Huazhong Agricultural University, Wuhan 430070, China. zengzhen@mail.hzau.edu.cn.
authors.forename: Zhen
authors.initials: Z
authors.lastname: Zeng
authors.affiliation: Department of Chemistry, College of Sciences, Huazhong Agricultural University, Wuhan 430070, China. lizilong@mail.hzau.edu.cn.
authors.forename: Zi-Long
authors.initials: ZL
authors.lastname: Li
authors.affiliation: Department of Chemistry, College of Sciences, Huazhong Agricultural University, Wuhan 430070, China. Jianghong0066@126.com.
authors.forename: Hong
authors.initials: H
authors.lastname: Jiang
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001234:Aspergillus niger / Q000187:drug effects / Q000472:pathogenicity; D002957:Citrus / Q000382:microbiology*; D005519:Food Preservation; D005638:Fruit / Q000382:microbiology; D008358:Mannose / Q000138:chemical synthesis / Q000737:chemistry; D054883:Oxylipins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010407:Penicillium / Q000187:drug effects / Q000472:pathogenicity
chemical_list: D000935:Antifungal Agents; D054883:Oxylipins; D008358:Mannose
keywords: antifungal activity; citrus; oxylipin; pathogen; synthesis