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自然C-9-甲基替代的10个成员乳及其半合成衍生物的结构-活性关系

Anatoly Fedorov¹, Vsevolod Dubovik¹, Sergey Smirnov²

¹All-Russian Institute of Plant Protection, Podbelskogo Street, 3, Pushkin, St. Petersburg 196608, Russian Federation.

Journal of natural products

|April 8, 2024

概括

的10个成员乳显示出作为天然除草剂的潜力. 结构-活性分析揭示了具有植物毒性和昆虫毒性作用的特定化合物,指导了未来除草剂的开发.

科学领域:

自然产品化学自然产品化学
农业化学研究农业化学研究
菌类学菌类学是指菌类学.

背景情况:

的10个成员乳 (TMLs) 是一种化合物的类别,具有作为自然衍生的除草剂的潜在应用.
之前的研究已经确定了几个具有有前途的生物活性的TML,但需要全面了解它们的结构-活性关系 (SAR).

研究的目的:

使用多目标生物试验方法研究C-9-甲基替代TML的SAR.
识别具有有用生物活性 (植物毒性,昆虫毒性,抗菌性) 和不良生物活性 (细胞毒性) 的TML.
引导基于TML的新型除草剂的合理设计.

主要方法:

从真菌培养物 (Stagonospora cirsii) 中分离和净化新的和已知的TMLs.
TML衍生物的半合成.
多目标生物测试以评估植物毒性,昆虫毒性,抗微生物活性和细胞毒性.
对所选化合物的绝对配置进行修订.

主要成果:

确定了一种新的TML,斯塔戈诺利德L (1),以及已知的化合物 (2-6).
制备了五种半合成衍生物 (7-11).
化合物4表现出植物毒性,而化合物5a,b表现出昆虫毒性.
化合物6表现出非选择性毒性,支持α,β不和碳基基组在一般毒性的作用.
发现化合物4中的环氧化物对其植物毒性至关重要.

结论:

阐明了C-9-甲基替代TML的SAR模式.
α,β-不和碳基组与TML中高的一般毒性有关.
化合物4中的4,5-环氧基对植物毒性很重要,这表明它在设计新的除草剂 (如curvulide A类似物) 中具有实用性.

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