{"title":"新型齐墩果酸28-哌嗪磺胺类抗菌药物的设计、合成及体外评价","authors":"Fengwei Ma (Conceptualization Investigation Writing – original draft Writing – review & editing) , Yihao Lu (Investigation Methodology Writing – original draft) , Buyan Zhang (Investigation Methodology) , Zhenghong Jia (Data curation Investigation) , Haijiang Chen (Resources Software) , Qiang Fei (Formal analysis Methodology) , Su Xu (Funding acquisition Software) , Wenneng Wu (Conceptualization Funding acquisition Project administration)","doi":"10.1080/10426507.2025.2553641","DOIUrl":null,"url":null,"abstract":"<div><div>A series of novel oleanolic acid (OA) derivatives were designed and synthesized, and their structures were characterized through <sup>1</sup>H NMR, <sup>13</sup>C NMR spectroscopy, and HRMS. The antimicrobial activities were evaluated against nine phytopathogenic fungi and three phytopathogenic bacteria, respectively. Results showed that all these title compounds exhibited moderate or good fungicidal activities compared to the commercial agents. Compounds <strong>5d</strong>, <strong>5f</strong>, <strong>5g</strong> and <strong>5l</strong> exhibited antifungal activity better than commercial agent azoxystrobin at the concentration of 50 µg/mL. Among them, compound <strong>5d</strong> demonstrated the optimal antifungal activity against <em>Botrytis cinerea</em> in strawberry, <em>Botrytis cinerea</em> in blueberry, and <em>Botrytis cinerea</em> in tobacco with the half-maximal effective concentration (EC<sub>50</sub>) value of 6.91 µg/mL, 9.16 µg/mL and 11.58 µg/mL, respectively. The antibacterial results showed the synthesized compounds exhibited moderate-to-good activities and in which compounds <strong>5e</strong> and <strong>5j</strong> exhibited relative broad-spectrum activities. Compound <strong>5e</strong> demonstrated the optimal antibacterial activity against <em>Xanthomonas axonopodis</em> pv. <em>citri</em> (XAC) with the EC<sub>50</sub> value of 31.40 µg/mL. Compound <strong>5i</strong> exhibited best antibacterial activities against <em>Xanthomonas oryzae</em> pv. <em>oryzicola</em> (XOO) and <em>Pseudomonas syringae</em> pv. <em>actinidiae</em> (PSA) with the EC<sub>50</sub> values of 67.64 µg/mL and 77.15 µg/mL, respectively. These results indicated that natural product derivatives like oleanolic acid bearing sulfanilic amide moieties were promising antimicrobial candidates for pesticides development.</div></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"200 11","pages":"Pages 897-904"},"PeriodicalIF":1.6000,"publicationDate":"2025-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Design, synthesis and in vitro evaluation of novel oleanolic acid (OA) 28-piperazine sulfonamide derivatives as potential antimicrobial agents\",\"authors\":\"Fengwei Ma (Conceptualization Investigation Writing – original draft Writing – review & editing) , Yihao Lu (Investigation Methodology Writing – original draft) , Buyan Zhang (Investigation Methodology) , Zhenghong Jia (Data curation Investigation) , Haijiang Chen (Resources Software) , Qiang Fei (Formal analysis Methodology) , Su Xu (Funding acquisition Software) , Wenneng Wu (Conceptualization Funding acquisition Project administration)\",\"doi\":\"10.1080/10426507.2025.2553641\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A series of novel oleanolic acid (OA) derivatives were designed and synthesized, and their structures were characterized through <sup>1</sup>H NMR, <sup>13</sup>C NMR spectroscopy, and HRMS. The antimicrobial activities were evaluated against nine phytopathogenic fungi and three phytopathogenic bacteria, respectively. Results showed that all these title compounds exhibited moderate or good fungicidal activities compared to the commercial agents. Compounds <strong>5d</strong>, <strong>5f</strong>, <strong>5g</strong> and <strong>5l</strong> exhibited antifungal activity better than commercial agent azoxystrobin at the concentration of 50 µg/mL. Among them, compound <strong>5d</strong> demonstrated the optimal antifungal activity against <em>Botrytis cinerea</em> in strawberry, <em>Botrytis cinerea</em> in blueberry, and <em>Botrytis cinerea</em> in tobacco with the half-maximal effective concentration (EC<sub>50</sub>) value of 6.91 µg/mL, 9.16 µg/mL and 11.58 µg/mL, respectively. The antibacterial results showed the synthesized compounds exhibited moderate-to-good activities and in which compounds <strong>5e</strong> and <strong>5j</strong> exhibited relative broad-spectrum activities. Compound <strong>5e</strong> demonstrated the optimal antibacterial activity against <em>Xanthomonas axonopodis</em> pv. <em>citri</em> (XAC) with the EC<sub>50</sub> value of 31.40 µg/mL. Compound <strong>5i</strong> exhibited best antibacterial activities against <em>Xanthomonas oryzae</em> pv. <em>oryzicola</em> (XOO) and <em>Pseudomonas syringae</em> pv. <em>actinidiae</em> (PSA) with the EC<sub>50</sub> values of 67.64 µg/mL and 77.15 µg/mL, respectively. These results indicated that natural product derivatives like oleanolic acid bearing sulfanilic amide moieties were promising antimicrobial candidates for pesticides development.</div></div>\",\"PeriodicalId\":20056,\"journal\":{\"name\":\"Phosphorus, Sulfur, and Silicon and the Related Elements\",\"volume\":\"200 11\",\"pages\":\"Pages 897-904\"},\"PeriodicalIF\":1.6000,\"publicationDate\":\"2025-08-26\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Phosphorus, Sulfur, and Silicon and the Related Elements\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1042650725000851\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, INORGANIC & NUCLEAR\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phosphorus, Sulfur, and Silicon and the Related Elements","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1042650725000851","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
Design, synthesis and in vitro evaluation of novel oleanolic acid (OA) 28-piperazine sulfonamide derivatives as potential antimicrobial agents
A series of novel oleanolic acid (OA) derivatives were designed and synthesized, and their structures were characterized through 1H NMR, 13C NMR spectroscopy, and HRMS. The antimicrobial activities were evaluated against nine phytopathogenic fungi and three phytopathogenic bacteria, respectively. Results showed that all these title compounds exhibited moderate or good fungicidal activities compared to the commercial agents. Compounds 5d, 5f, 5g and 5l exhibited antifungal activity better than commercial agent azoxystrobin at the concentration of 50 µg/mL. Among them, compound 5d demonstrated the optimal antifungal activity against Botrytis cinerea in strawberry, Botrytis cinerea in blueberry, and Botrytis cinerea in tobacco with the half-maximal effective concentration (EC50) value of 6.91 µg/mL, 9.16 µg/mL and 11.58 µg/mL, respectively. The antibacterial results showed the synthesized compounds exhibited moderate-to-good activities and in which compounds 5e and 5j exhibited relative broad-spectrum activities. Compound 5e demonstrated the optimal antibacterial activity against Xanthomonas axonopodis pv. citri (XAC) with the EC50 value of 31.40 µg/mL. Compound 5i exhibited best antibacterial activities against Xanthomonas oryzae pv. oryzicola (XOO) and Pseudomonas syringae pv. actinidiae (PSA) with the EC50 values of 67.64 µg/mL and 77.15 µg/mL, respectively. These results indicated that natural product derivatives like oleanolic acid bearing sulfanilic amide moieties were promising antimicrobial candidates for pesticides development.
期刊介绍:
Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.