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Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens
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, Penicil...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273781/ https://www.ncbi.nlm.nih.gov/pubmed/26907241 http://dx.doi.org/10.3390/molecules21020254 |
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author | Ma, Jimei Li, Yupeng Chen, Hangwei Zeng, Zhen Li, Zi-Long Jiang, Hong |
author_facet | Ma, Jimei Li, Yupeng Chen, Hangwei Zeng, Zhen Li, Zi-Long Jiang, Hong |
author_sort | Ma, Jimei |
collection | PubMed |
description | 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 (IC(50) = 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. |
format | Online Article Text |
id | pubmed-6273781 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62737812018-12-28 Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens Ma, Jimei Li, Yupeng Chen, Hangwei Zeng, Zhen Li, Zi-Long Jiang, Hong Molecules Article 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 (IC(50) = 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. MDPI 2016-02-22 /pmc/articles/PMC6273781/ /pubmed/26907241 http://dx.doi.org/10.3390/molecules21020254 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Ma, Jimei Li, Yupeng Chen, Hangwei Zeng, Zhen Li, Zi-Long Jiang, Hong Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens |
title | Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens |
title_full | Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens |
title_fullStr | Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens |
title_full_unstemmed | Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens |
title_short | Synthesis of Oxylipin Mimics and Their Antifungal Activity against the Citrus Postharvest Pathogens |
title_sort | synthesis of oxylipin mimics and their antifungal activity against the citrus postharvest pathogens |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273781/ https://www.ncbi.nlm.nih.gov/pubmed/26907241 http://dx.doi.org/10.3390/molecules21020254 |
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