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Cyclic polyhydroxy compound quinic acid is a common metabolite synthesized in plant tissues, including sweet potato tubers, showing weak antifungal properties. Although several\n                      <jats:italic>O<\/jats:italic>\n                      \u2010acylated quinic acid derivatives have been synthesized and found in nature and their antifungal properties have been explored, derivatives based on modification of the carboxylic acid have never been evaluated.\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>RESULTS<\/jats:title>\n                    <jats:p>\n                      In this study, amide derivatives were synthesized\n                      <jats:italic>via<\/jats:italic>\n                      linkage of amines with the carboxylic acid moiety of quinic acid. Derivatives with high dipolar moments and a low number of rotatable bonds showed greater antifungal activities toward\n                      <jats:italic>C. fimbriata in vitro<\/jats:italic>\n                      than quinic and chlorogenic acids. Derivative\n                      <jats:bold>5b<\/jats:bold>\n                      , which was synthesized by coupling\n                      <jats:italic>p<\/jats:italic>\n                      \u2010aminobenzoic acid (\n                      <jats:italic>p<\/jats:italic>\n                      ABA) with quinic acid, had the greatest antifungal activity.\n                      <jats:bold>5b<\/jats:bold>\n                      showed iron(II)\u2010chelating properties and reduced ergosterol content in\n                      <jats:italic>C. fimbriata<\/jats:italic>\n                      cells, causing irregularities in the fungal cell wall and inhibiting conidia agglutination. Application of 3\u2009m\n                      <jats:sc>m<\/jats:sc>\n                      <jats:bold>5b<\/jats:bold>\n                      reduced black rot symptoms in sweet potatoes by 70.1%.\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>CONCLUSIONS<\/jats:title>\n                    <jats:p>\n                      Collectively, derivatization of the carboxylic acid from quinic acid was demonstrated to be a suitable strategy to improve the antifungal properties of this compound. This study reveals a new efficient strategy for management of the sweet potato pathogen\n                      <jats:italic>C. fimbriata<\/jats:italic>\n                      . \u00a9 2024 Society of Chemical Industry.\n                    <\/jats:p>\n                  <\/jats:sec>","DOI":"10.1002\/ps.8527","type":"journal-article","created":{"date-parts":[[2024,11,6]],"date-time":"2024-11-06T03:24:35Z","timestamp":1730863475000},"page":"1286-1298","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Synthesis and antifungal activity of novel amide derivatives from quinic acid against the sweet potato pathogen\n                    <scp>\n                      <i>Ceratocystis fimbriata<\/i>\n                    <\/scp>"],"prefix":"10.1002","volume":"81","author":[{"given":"Yong\u2010Hui","family":"Jiang","sequence":"first","affiliation":[{"name":"School of Life Sciences Nantong University  Nantong P. R. 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