Tobacco Research Institute of Chinese Academy of Agricultural Sciences, Qingdao 266101, People's Republic of China.
College of Marine Life Sciences, Ocean University of China, Qingdao 266003, People's Republic of China.
J Agric Food Chem. 2020 Oct 14;68(41):11480-11487. doi: 10.1021/acs.jafc.0c05680. Epub 2020 Oct 2.
Endophytic fungi have proven to be prolific producers of bioactive secondary metabolites with agricultural applications. In this study, bioassay-guided isolation of the endophytic fungus yielded four anthraquinone derivatives (compounds -), including a previously undescribed dimethylated derivative of bipolarin, 6,8-di--methylbipolarin (). Their structures were determined by 1D and 2D nuclear magnetic resonance analysis as well as high-resolution electrospray ionization mass spectrometry data, and the absolute configuration of was established by comparing the calculated and experimental electronic circular dichroism spectra. The insecticidal activity of the isolated compounds against the cotton bollworm was evaluated. The new compound showed the strongest larvicidal activity against the 3rd instar larvae of with an LC value of 0.72 mg/mL. In addition, transcriptome sequencing was performed to evaluate the molecular mechanism of the insecticidal activity. In total, 5732 differentially expressed genes were found, among which 2904 downregulated genes and 2828 upregulated genes were mainly involved in cell autophagy, apoptosis, and DNA mismatch repair and replication. The results presented in this study reveal how exerts its insecticidal effects against via genome-wide differential gene expression analyses. Our findings suggest that anthraquinone derivatives are potential biopesticides for cotton bollworm control.
内生真菌已被证明是生物活性次生代谢产物的丰富生产者,具有农业应用价值。在这项研究中,通过生物测定指导内生真菌的分离,得到了四种蒽醌衍生物(化合物 - ),包括以前未描述的双极性素的二甲基化衍生物,6,8-二--甲基双极性素()。通过 1D 和 2D 核磁共振分析以及高分辨率电喷雾电离质谱数据确定了它们的结构,并通过比较计算和实验电子圆二色谱谱确定了的绝对构型。对分离得到的化合物对棉铃虫的杀虫活性进行了评价。新化合物对 3 龄幼虫的杀虫活性最强,LC 值为 0.72 mg/mL。此外,还进行了转录组测序,以评估杀虫活性的分子机制。共发现 5732 个差异表达基因,其中 2904 个下调基因和 2828 个上调基因主要参与细胞自噬、细胞凋亡和 DNA 错配修复和复制。本研究通过全基因组差异基因表达分析揭示了 对棉铃虫的杀虫作用机制。我们的研究结果表明,蒽醌衍生物是防治棉铃虫的潜在生物农药。