摘要
α-红没药醇的抗胶孢炭疽菌活性及相关构效关系尚未明确,本研究以α-红没药醇为母体,通过酯化反应在羟基位点引入不同脂肪族含氟酰基或芳香族酰基,设计合成10种结构新颖的酯类衍生物(A-J)。采用核磁共振氢谱(^(1)H NMR)、碳谱(^(13)C NMR)对目标化合物结构进行确证,并以菌丝生长速率法(浓度为0.5 mg·mL^(-1))评价其对胶孢炭疽菌的体外抑菌活性。结果表明,目标化合物的抑菌活性与酯基结构密切相关:芳香族酯类衍生物(C-J)的抑菌活性整体优于脂肪族含氟酯类(A、B,抑菌率<1.5%);苯环通过亚甲基与酯基连接的化合物C(α-红没药醇-2,5-二甲基苯乙酸酯)表现出最强的抑菌活性,抑菌率最高达到(22.32±1.26)%;未取代的苯甲酸酯衍生物D抑菌率较低为(7.82±0.34)%,其活性显著高于多数苯环取代衍生物(E-J),提示苯环取代基可能通过空间位阻或电子效应降低活性。本研究明确了α-红没药醇衍生物抗胶孢炭疽菌的构效关系,筛选出较高活性化合物C,为新型绿色抗油茶炭疽病药剂的研发提供了重要理论依据。
Since the antifungal activity ofα-bisabolol against Colletotrichum gloeosporioides and its associated structure-activity relationship(SAR)remained unclear,this study designed and synthesized ten novel ester derivatives(A-J)based on its structure.The derivatives were achieved via esterification at the hydroxyl group through introducing various aliphatic fluorine containing or aromatic acyl moieties.Their structures were confirmed by ^(1)H NMR and ^(13)C NMR,and the antifungal activity against C.gloeosporioides in vitro was evaluated using the mycelial growth rate method at a final concentration of 0.5 mg·mL^(-1).The results indicated that the antifungal activity was closely related to the ester structure.The aromatic ester derivatives(C-J)generally exhibited superior activity compared to the aliphatic fluorine-containing esters(A and B,inhibition rates<1.5%).Notably,compound C(α-bisabolol-2,5-dimethylphenylacetate),which features a phenyl group connected to the ester carbonyl via a methylene bridge,demonstrated the strongest activity with an inhibition rate of(22.32±1.26)%.Furthermore,the unsubstituted benzoate derivative D(inhibition rate of(7.82±0.34)%)was significantly more active than most substituted benzoate derivatives(E-J),suggesting that substituents on the phenyl ring might reduce the activity due to the steric hindrance or electronic effects.This study clarifies the SAR ofα-bisabolol derivatives against C.gloeosporioides,identifies a highly active lead compound(C),and provides a crucial theoretical foundation for developing new green agents to control C.oleifera anthracnose.
作者
张学斌
胡文杰
罗辉
黄小流
李娇楠
周升团
戴彩华
ZHANG Xuebin;HU Wenjie;LUO Hui;HUAN Xiaoliu;Li Jiaonan;ZHOU Shengtuan;DAI Caihua(School of Life Sciences,Jinggangshan University,Ji’an,Jiangxi 343009,China;School of Basic Medicine,Jinggangshan University,Ji’an,Jiangxi 343009,China)
出处
《井冈山大学学报(自然科学版)》
2026年第2期39-45,共7页
Journal of Jinggangshan University (Natural Science Edition)
基金
国家自然科学基金项目(32160089)
江西省自然科学基金面上项目(20232BAB205044,20181BAB204014,20252BAC240486)
江西省教育厅科技研究重点项目(GJJ2201609)。
关键词
α-红没药醇
设计合成
胶孢炭疽菌
抑菌活性
α-bisabolol
design and synthesis
Colletotrichumgloeosporioides
antifungal activity
