Antifungal application of pine derived products for sustainable forest resource exploitation
Antifungal application of pine derived products for sustainable forest resource exploitation
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DOI：
10.1016/j.indcrop.2019.111892
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发表时间：
2020
影响因子：
5.9
通讯作者：
Chengyu Wu;Pan Tao;Jian Li;Yanqing Gao;Shibin Shang;Zhan‐qian Song
中科院分区：
文献类型：
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作者：
Chengyu Wu;Pan Tao;Jian Li;Yanqing Gao;Shibin Shang;Zhan‐qian Song
为了研究噻吩杂环基团对其抗真菌活性的影响，设计并合成了两个系列的松香基衍生物。评估了对黄瓜炭疽菌、灰葡萄孢、苹果腐烂病菌和核盘菌的抗真菌作用。含有噻吩杂环基团的脱氢枞基酰基硫脲化合物对V具有轻度至强的抗真菌作用。马里。在这些分子中，化合物5e对V表现出更优异的效果。 50%最大作用浓度（EC50）为0.184mg/L，低于多菌灵。化合物 5e 对 V 也有效。与对照组相比，马里体内的细胞形态显着改变，细胞膜通透性升高，果胶酶活性降低。接下来，四个参数将 V 的结构特征和抗真菌作用联系起来。进行了检查，包括 S 原子的最大净原子电荷 (qSmax)、原子单位中最高占据分子轨道与最低未占据轨道之间的能隙 (HOMO-LUMO)、分子表面积的对数 (logMS) 和偶极矩 (DM)，并用于构建定量构效关系 (QSAR) 模型 (R2= 0.9660）。初步构效关系（SAR）和QSAR评估表明电子和空间效应，不同化合物的能量差异对抗真菌性能有显着影响。这些结果为松香基噻吩杂环衍生物的抗真菌特性背后的机制提供了新的见解。在这项研究的指导下，一些潜在的替代品目前可以用于杀菌剂，并可以引导一些新的抗真菌药物的开发。
In order to investigate the effect of thiophene heterocyclic group on antifungal activity, two series of rosin-based derivatives were designed and synthesized. The antifungal effects onThanatephorus cucumeris,Botrytis cinerea,Valsa mali, andSclerotinia sclerotiorumwere assessed. The dehydroabietyl acyl-thiourea compounds containing a thiophene heterocyclic group had mild to strong antifungal effects onV. mali. Among these molecules, compound 5e showed more excellent effects onV. maliwith concentration for 50% of maximal effect (EC50) of 0.184 mg/L, which was lower than carbendazim. Compound 5e was also efficient againstV. mali in vivo, with remarkably altered morphology, elevated cell membrane permeability, and decreased pectinase activity compared with the control group. Next, four parameters linking structural features and antifungal effects onV. maliwere examined, including max net atomic charge for a S atom (qSmax), energy gap between the highest occupied molecular orbit and the lowest unoccupied orbit in atomic units (HOMO-LUMO), the logarithm of molecular surface area (logMS), and dipole moment (DM), and used for building a quantitative structure-activity relationship (QSAR) model (R2= 0.9660). Preliminary structure-activity relationship (SAR) and QSAR evaluations indicated electronic and steric effects, and energy differences of different compounds had remarkable influences on antifungal properties. These results provided new insights into the mechanisms behind the antifungal properties of rosin-based with thiophene heterocyclic group derivatives. Guided by this study, some potential substitutes can be currently used in fungicides and some new antifungals can be led for developing.