000150484 001__ 150484
000150484 005__ 20250214141230.0
000150484 0247_ $$2doi$$a10.1002/ps.8527
000150484 0248_ $$2sideral$$a142688
000150484 037__ $$aART-2024-142688
000150484 041__ $$aeng
000150484 100__ $$aJiang, Yong-Hui
000150484 245__ $$aSynthesis and antifungal activity of novel amide derivatives from quinic acid against the sweet potato pathogen <scp><i>Ceratocystis fimbriata</i></scp>
000150484 260__ $$c2024
000150484 5203_ $$aBACKGROUND: Ceratocystis fimbriata is a fungal pathogen that infects sweet potato roots, producing enormous economic losses. Cyclic polyhydroxy compound quinic acid is a common metabolite synthesized in plant tissues, including sweet potato tubers, showing weak antifungal properties. Although several O‐acylated 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. RESULTS: In this study, amide derivatives were synthesized via 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 C. fimbriata in vitro than quinic and chlorogenic acids. Derivative 5b, which was synthesized by coupling p‐aminobenzoic acid (pABA) with quinic acid, had the greatest antifungal activity. 5b showed iron(II)‐chelating properties and reduced ergosterol content in C. fimbriata cells, causing irregularities in the fungal cell wall and inhibiting conidia agglutination. Application of 3 mm 5b reduced black rot symptoms in sweet potatoes by 70.1%. CONCLUSIONS: 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 C. fimbriata. © 2024 Society of Chemical Industry.
000150484 540__ $$9info:eu-repo/semantics/closedAccess$$aAll rights reserved$$uhttp://www.europeana.eu/rights/rr-f/
000150484 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000150484 700__ $$aShi, Xin-Chi
000150484 700__ $$aWu, Ting
000150484 700__ $$aDu, Hao
000150484 700__ $$aPang, Yi-Bo
000150484 700__ $$aZhou, Rong
000150484 700__ $$aYin, Hong-Ping
000150484 700__ $$aHerrera-Balandrano, Daniela D
000150484 700__ $$aYang, Dong-Jing
000150484 700__ $$aLu, Ai-Min
000150484 700__ $$aLaborda, Pedro
000150484 700__ $$0(orcid)0000-0001-5823-7965$$aPolo, Victor$$uUniversidad de Zaragoza
000150484 700__ $$aWang, Su-Yan
000150484 7102_ $$12012$$2755$$aUniversidad de Zaragoza$$bDpto. Química Física$$cÁrea Química Física
000150484 773__ $$g81, 3 (2024), 1286-1298$$pPest manag. sci.$$tPEST MANAGEMENT SCIENCE$$x1526-498X
000150484 8564_ $$s1971202$$uhttps://zaguan.unizar.es/record/150484/files/texto_completo.pdf$$yVersión publicada$$zinfo:eu-repo/date/embargoEnd/2025-11-06
000150484 8564_ $$s2699747$$uhttps://zaguan.unizar.es/record/150484/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada$$zinfo:eu-repo/date/embargoEnd/2025-11-06
000150484 909CO $$ooai:zaguan.unizar.es:150484$$particulos$$pdriver
000150484 951__ $$a2025-02-14-14:11:33
000150484 980__ $$aARTICLE