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Herbicidal Sorbicillinoid Analogs Cause Lignin Accumulation in Aspergillus aculeatus TE-65L
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-09-13 , DOI: 10.1021/acs.jafc.4c06809 Xin-Rong Huang 1, 2 , Chao-Nan Jiang 1 , Hai-Su Wang 1 , Gan Gu 1 , Mei Wang 1 , Xiao-Na Sui 1 , Tong Si 2 , Zhong-Feng Zhang 1 , Peng Zhang 1 , Dong-Lin Zhao 1
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-09-13 , DOI: 10.1021/acs.jafc.4c06809 Xin-Rong Huang 1, 2 , Chao-Nan Jiang 1 , Hai-Su Wang 1 , Gan Gu 1 , Mei Wang 1 , Xiao-Na Sui 1 , Tong Si 2 , Zhong-Feng Zhang 1 , Peng Zhang 1 , Dong-Lin Zhao 1
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Five new sorbicillinoid derivatives, including (±)-aspersorbicillin A [(±)-1], a pair of enantiomers at C-9, and aspersorbicillins B–D (2–4), together with two known analogs (5 and 6) were isolated from the endophytic fungus Aspergillus aculeatus TE-65L. Their structures including absolute configurations were determined by detailed spectroscopic analyses and electronic circular dichroism calculations. The herbicidal activity of sorbicillinoids on the germ and radicle elongation of various weed types was reported for the first time. Compound 1 displayed significant herbicidal activity against Eleusine indica germ elongation (IC50 = 28.8 μg/mL), while compound 6 inhibited radicle elongation (IC50 = 25.6 μg/mL). Both were stronger than those of glyphosate (66.2 and 30.9 μg/mL, respectively). Further transcriptomic and LC-MS/MS metabolomic analysis indicated that 6 induced the transcriptional expressions of genes related to the lignin biosynthetic pathway, resulting in lignin accumulation. Transmission electron microscopy confirmed the cell wall thickening of seeds treated with 6, suggesting weed growth inhibition. This study reveals new lead compounds for fabricating natural herbicides and expands the agricultural use of sorbicillinoid analogs.
中文翻译：
除草山梨西林类似物导致棘孢曲霉 TE-65L 中木质素积累
五种新的山梨西林衍生物，包括 (±)-阿帕山西林 A [(±)- 1 ]、一对 C-9 对映体、阿帕山西林 B–D ( 2 – 4 )，以及两种已知的类似物 ( 5和6 )从内生真菌Aspergillus aculeatus TE-65L 中分离出来。它们的结构（包括绝对构型）是通过详细的光谱分析和电子圆二色性计算确定的。首次报道了山梨西林类化合物对各种杂草的胚芽和胚根伸长的除草活性。化合物1对牛筋草胚芽伸长表现出显着的除草活性 (IC 50 = 28.8 μg/mL)，而化合物6则抑制胚根伸长 (IC 50 = 25.6 μg/mL)。两者均强于草甘膦（分别为 66.2 和 30.9 μg/mL）。进一步的转录组学和LC-MS/MS代谢组学分析表明， 6诱导木质素生物合成途径相关基因的转录表达，导致木质素积累。透射电子显微镜证实用6处理的种子细胞壁增厚，表明杂草生长受到抑制。这项研究揭示了用于制造天然除草剂的新先导化合物，并扩大了山梨西林类似物的农业用途。
更新日期：2024-09-13
中文翻译：
除草山梨西林类似物导致棘孢曲霉 TE-65L 中木质素积累
五种新的山梨西林衍生物，包括 (±)-阿帕山西林 A [(±)- 1 ]、一对 C-9 对映体、阿帕山西林 B–D ( 2 – 4 )，以及两种已知的类似物 ( 5和6 )从内生真菌Aspergillus aculeatus TE-65L 中分离出来。它们的结构（包括绝对构型）是通过详细的光谱分析和电子圆二色性计算确定的。首次报道了山梨西林类化合物对各种杂草的胚芽和胚根伸长的除草活性。化合物1对牛筋草胚芽伸长表现出显着的除草活性 (IC 50 = 28.8 μg/mL)，而化合物6则抑制胚根伸长 (IC 50 = 25.6 μg/mL)。两者均强于草甘膦（分别为 66.2 和 30.9 μg/mL）。进一步的转录组学和LC-MS/MS代谢组学分析表明， 6诱导木质素生物合成途径相关基因的转录表达，导致木质素积累。透射电子显微镜证实用6处理的种子细胞壁增厚，表明杂草生长受到抑制。这项研究揭示了用于制造天然除草剂的新先导化合物，并扩大了山梨西林类似物的农业用途。
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