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Development and molecular analysis of a novel acetohydroxyacid synthase rapeseed mutant with high resistance to sulfonylurea herbicides

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The Crop Journal 2022年第1期10卷 56-66页

作者： Yue Guo Changle Liu Weihua Long Jianqin Gao Jiefu Zhang Song Chen Huiming Pu Maolong Hu Institute of Industrial Crops Jiangsu Academy of Agricultural Sciences Key Laboratory of Cotton and Rapeseed(Nanjing)Ministry of AgricultureNanjing 210014JiangsuChina Institute of Life Sciences Jiangsu UniversityZhenjiang 212013JiangsuChina School of Food and Biological Engineering Jiangsu UniversityZhenjiang 212013JiangsuChina Provincial Key Laboratory of Agrobiology Jiangsu Academy of Agricultural SciencesNanjing 210014JiangsuChina

With the increasing promotion of simplified rapeseed cultivation in recent years,the development of cultivars with high resistance to herbicides is urgently *** previously developed M342,which shows sulfonylurea herbicide resistance,by targeting acetohydroxyacid synthase(AHAS),a key enzyme in branched-chain amino acid *** the present study,we used a progeny line derived from M342 for an additional round of ethyl methane sulfonate mutagenesis,yielding the novel mutant DS3,which harbored two mutations in AHAS genes and showed high sulfonylurea *** mutation was the substitution Trp574 Leu,as in M342,according to Arabidopsis protein *** other site was a newly recognized substitution,Pro197 Leu.A KASP marker targeting Pro197 Leu was developed and reliably predicted the response to sulfonylurea herbicides in the F2 *** combination of Trp574 Leu and Pro197 Leu in DS3 produced a synergistic effect that greatly increased herbicide *** of the protein structures of AHAS1 and AHAS3 in wild-type and single-gene mutant plants revealed three-dimensional protein conformational changes that could account for differences in herbicide resistance characteristics including toxicity tolerance,AHAS enzyme activity,and AHAS gene expression.

关键词： acetohydroxyacid synthase High-resistance rapeseed Additional round of mutagenesis Sulfonylurea herbicide Synergistic mutations

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Molecular Drug Resistance Prediction for acetohydroxyacid synthase Mutants Against Chlorsulfuron Using MB-QSAR

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Chinese Journal of Chemistry 2013年第9期31卷 1171-1180页

作者： Yinwu He Congwei Niu Xin Wen Zhen Xi State Key Laboratory of Elemento-Organic Chemistry Department of Chemical Biology Nankai University Tianjin 300071 China

Chlorsulfuron is the first commercialized sulfonylurea herbicide, which targets acetohydroxyacid synthase （AHAS）. Mutations in AHAS have caused serious herbicide resistance to chlorsulfuron. Quantitative description of the herbicide resistance in molecular level will benefit the understanding of the resistance mechanism and aid the design of resistance-evading herbicide. We have recently established a MB-QSAR （Mutation-dependent Biomac- romolecular Quantitative Structure-Activity Relationship） method to conduct the 3D-QSAR study in biomacro- molecules. Herein, based on the herbicide resistance data measured for a series of AHAS mutants against chlorsul- furon, we constructed MB-QSAR models to quantitatively predict the herbicide resistance and interpret the struc- ture resistance relationships for AHAS mutants against chlorsulfuron. Quite well correlations between the experi- mental and the predicted pKi values were achieved for MB-QSAR/CoMFA （q^2=0.705, r^2=0.918, r^2pred=0.635） and MB-QSAR/CoMSIA （q^2=0.558, r^2=0.940, r^2pred=0.527） models, and interpretation of the MB-QSAR models gave chemical intuitive information to guide the resistance-evading herbicide design.

关键词： MB-QSAR QSAR drug resistance prediction acetohydroxyacid synthase chlorsulfuron

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Experimental and computational correlation and prediction on herbicide resistance for acetohydroxyacid synthase mutants to Bispyribac

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Science China Chemistry 2013年第3期56卷 286-405页

作者： HE YinWu NIU CongWei LI Hank WEN Xin XI Zhen State Key Laboratory of Elemento-Organic Chemistry

Bispyribac is a widely used herbicide that targets the acetohydroxyacid synthase(AHAS) *** in AHAS have caused serious herbicide resistance that threatened the continued use of the *** far,a unified model to decipher herbicide resistance in molecular level with good prediction is still *** this paper,we have established a new QSAR method to construct a prediction model for AHAS mutation resistance to herbicide Bispyribac.A series of AHAS mutants concerned with the herbicide resistance were constructed,and the inhibitory properties of Bispyribac against these mutants were *** 3D-QSAR method has been transformed to process the AHAS mutants and proposed as mutation-dependent biomacromolecular QSAR(MB-QSAR).The excellent correlation between experimental and computational data gave the MB-QSAR/CoMFA model(q2=0.615,r2=0.921,r2 pred=0.598) and the MB-QSAR/CoMSIA model(q2=0.446,r2=0.929,r2 pred=0.612),which showed good prediction for the inhibition properties of Bispyribac against AHAS *** MB-QSAR models,containing the three-dimensional molecular interaction diagram,not only disclose to us for the first time the detailed three-dimensional information about the structure-resistance relationships,but may also provide further guidance to resistance mutation ***,the molecular interaction diagram derived from MB-QSAR models may aid the resistance-evading herbicide design.

关键词： MB-QSAR resistance prediction herbicide resistance Bispyribac-sodium acetohydroxyacid synthase

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Inheritance and molecular characterization of a novel acetohydroxyacid synthase(AHAS)gene responsible for resistance to AHAS herbicides in rapeseed(Brassica napus L.)

Inheritance and molecular characterization of a novel acetoh...

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中国作物学会油料作物专业委员会第八次会员代表大会暨学术...

作者： HUANG Qian-xin Lyn Jin-yang SUN Yan-yan WANG Hong-mei GUO Yuan QU Gao-ping HU Sheng-wu State Key Laboratory of Crop Stress Biology in Arid Areas College of AgronomyNorthwest A&F University

Utilization of post-emergence herbicides is an effective and economical way to control weeds in rapeseed ***,the availability of selective herbicides for oilseed rape is quite limited due to the shortage of herbicide-resistant cultivars in *** point mutation in acetohydroxyacid synthase(AHAS) gene could be achieved by non-GMO(non-genetically modified organism) way and lead to AHAS-inhibition herbicides-resistance in many *** present study,a tribennuron-methyl(TBM) resistant mutant K5 was screened from ethyl methyl sulfonate mutagenic rapeseed(Brassica napus L.) cultivar Zhongshuang 9(ZS9).The inheritance analysis indicated that TBM resistance was controlled by one dominant nuclear *** sequences analysis revealed that a novel substitution of C with T at position 544 from the translation start site in BnAHAS1 were identified mutant K5,which leading to the alteration of Pro with Ser at position 197 in BnAHAS1(refer to Arabidopsis thaliala sequence).Herbicides-spraying experiments revealed that ZS9 was killed with the treatment of 2.0 mg/L TBM whereas TBM resistance of K5 was almost 100 times than that of control ZS9,and K5 also showed a certain cross-resistance to bensulfuron-methyl and ***1 transgenic Arabidopsis plants exhibited a much higher TBM resistance than its wild-type at 5-6 leaf stage,which confirmed that the single point substitution in BnAHASl was responsible for herbicides-resistance of K5.A CAPS(cleaved amplified polymorphic sequence) marker,which can quickly distinguish both heterozygous and homozygous mutated alleles in BnAHAS1,was developed based on restriction sites of endonuclease Ava ***,a fast way to screen novel TBM-resistant plants in candidate library at their cotyledon stage by treated with 0.5 mg/L TBM in greenhouse was *** general,our research lay a foundation for developing herbicide-resistance rapeseed cultivars with independent intellectual property rights,and confi

关键词： rapeseed(Brassica napus L.) herbicide resistance tribennuron-methyl acetohydroxyacid synthase inheritance molecular characterization

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Unexpected strucuture of free plant acetohydroxyacid synthase

Unexpected strucuture of free plant acetohydroxyacid synthas...

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第十届全国化学生物学学术会议

作者： Jian-Guo Wang Luke William Guddat State-Key Laboratory and Research Institute of Elemento-Organic Chemistry National Pesticide Engineering Research Center College of Chemistry Nankai University School of Chemistry and Molecular Biosciences the University of Queensland

acetohydroxyacid synthase（AHAS,E.C.2.***.1.6）is the first enzyme in the branched chain amino acid biosynthesis *** of the most widely used commercial herbicides（*** and imidazolinones et al.）target this *** have determined the crystal structure of a plant AHAS in the absence of any inhibitor and it shows that the herbicide-binding site adopts a foldedwhich was shown in the previous plant AHAS structures inhibited byThis is unexpected because the equivalent regions for herbicide binding in uninhibited Saccharomyces cerevisiae AHAS are either disordered,or adopt a different fold when the herbicide is not *** addition,the structure provides an explanation as to why some herbicides are more potent inhibitors of Arabidopsis thaliana AHAS compared to AHASs from other species（*** cerevisiae）.The elucidation of the native structure of plant AHAS provides a new platform for future rational structure-based herbicide design efforts.

关键词： acetohydroxyacid synthase binding site Arabidopsis thaliana

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Synthesis and Characterization of Novel-4-Methyl-3-isoxazolidinone Derivatives

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Chemical Research in Chinese Universities 2006年第6期22卷 717-720页

作者： GAO Fei-fei ZHANG Guang-liang ZHENG Liang-yu LI Yao-xian ZHANG Suo-qin College of Chemistry Ministry of Education Jilin University Changchun 130021 P. R. China Key Lab for Molecular Enzymology and Engineering Ministry of Education Jilin University Changchun 130021 P. R. China

A novel type of aeetohydrexyacid synthase inhibitors, 4-methyl-3-isoxazolidinone derivatives of sulfonylurea, was designed and synthesized. The structures of these compounds were confirmed by using MS, NMR, and elemen... 详细信息

关键词： 4-Methyl-3-isoxazolidinone Sulfonylureas acetohydroxyacid synthase Herbicidal activity

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Synthesis and Evaluation of Novel N-（4＇-Arylpyrimidin-2＇-yl） Sulfonylurea Derivatives as Potential Antifungal Agents

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Chemical Research in Chinese Universities 2015年第2期31卷 218-223页

作者： CHEN Wei LI Yuxin SHI Yanxia WEI Wei CHEN Youwei LI Yonghong LIU Jingbo LI Baoju LI Zhengmmg State Key Laboratory of Elemento-Organie Chemistry Collaborative Innovation Center of Chemical Science and Engineering(Tianjin) Nankai University Tianjin 300071 P. R. China Institute of Vegetables and Flowers Chinese Academy of Agricultural Sciences Beijing 100081 P. R. China

Sulfonylureas（SUs） are potent and selective inhibitors of acetohydroxyacid synthase and has been used as herbicides. Some SUs also displayed other biological activities. In order to discuss the antifungal activity of SUs, a series of novel SUs containing aryl-substituted pyrimidine moieties was designed and synthesized. The preliminary bioassay showed that the title compounds exhibited moderate to favorable fungicidal activities in vivo. Especially, compound 9b exhibited more efficacy than the controls against five fungi at 25 mg/L. These promising results indicate that an aryl group on pyrimidine ring is favorable for antifungal activity and SUs are potential inhibitors for some phytopathogenic fungi.

关键词： acetohydroxyacid synthase Sulfonylurea Fungicidal activity Substituted pyrimidine

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Design, Syntheses and Biological Activities of Novel Sulfonylureas Containing an Oxime Ether Moiety

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Chemical Research in Chinese Universities 2016年第2期32卷 195-201页

作者： WEI Wei CHENG Dandan CHEN Wei LIU Jingbo WAN Yingying LI Yuxin LI Yonghong YU Shujing LI Zhengming State Key Laboratory of Elemento-organic Chemistry Institute of Elemento-organic Chemistry Collaborative Innovation Center of Chemical Science and Engineering(Tianjin) Nankai University Tianjin 300071 P. R. China

Since sulfonylurea is one of the most potent acetohydroxyacid synthase（AHAS） inhibitors, a series of novel sulfonylureas containing an oxime ether moiety was designed and synthesized and their chemical structures were determined by means of 1H nuclear magnetic resonance（NMR）, 13C NMR and high-resolution mass spectrometry（HRMS）. In the herbicidal bioassay, several compounds showed moderate to good herbicidal activities against dicotyledons, but their activities against monocotyledons decreased. The in vitro antifungal activity was tested at a dosage of 50 mg/L. And the results show that compounds 71, 7m and 7n exhibit promising antifungal activities against six common plant pathogenic fungi. Further investigations on molecular modification are in progress.

关键词： acetohydroxyacid synthase Sulfonylurea Oxime ether

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Synthesis and Herbicidal Activity of Novel Phenoxysulfonylureas Derivatives

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Chemical Research in Chinese Universities 2009年第5期25卷 648-652页

作者： ZHANG Xin-min ZHENG Liang-yu GAO Jun-long LIU Qing-wen SUN Guo-dong QIN Lin ZHANG Suo-qin College of Chemistry Jilin University Changchun 130021 P. R. China Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education Jilin University Changchun 130021 P. R. China

Thirteen novel phenoxysulfonylureas derivatives were synthesized, and their structures were confirmed by MS, NMR and element analysis. The herbicidal activity and structure-activity relationship were also investigated... 详细信息

关键词： Phenoxysulfonylurea acetohydroxyacid synthase Herbicidal activity

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抗除草剂假单胞菌的分离及其AHAS基因ilvIH的克隆

抗除草剂假单胞菌的分离及其AHAS基因ilvIH的克隆

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第四次全国土壤生物和生物化学学术研讨会

作者：孙笑非黄星李顺鹏何健南京农业大学生命科学学院微生物学系农业部农业环境微生物工程重点开放实验室

乙酰乳酸合酶(也称乙酰羟酸合酶 acetohydroxyacid synthase,AHAS)是植物、真菌和细菌细胞内支链氨基酸 Val、Leu、Ile 生物合成过程中关键酶。本文从长期受甲磺隆污染的土壤中分离,纯化出1株甲磺隆的抗性菌 Lm10。经形态、生理生化特... 详细信息

乙酰乳酸合酶(也称乙酰羟酸合酶 acetohydroxyacid synthase,AHAS)是植物、真菌和细菌细胞内支链氨基酸 Val、Leu、Ile 生物合成过程中关键酶。本文从长期受甲磺隆污染的土壤中分离,纯化出1株甲磺隆的抗性菌 Lm10。经形态、生理生化特性测定、16S rDNA 序列同源性比较和系统进化树的分析将甲磺隆抗性菌 Lm10鉴定为假单孢菌(***)。菌株 Lm10对甲磺隆的最高耐受浓度达到13.75nmol/L,且对各种乙酰乳酸合酶抑制剂类除草剂具有交叉抗性。利用 PCR 技术从 Lm10总 DNA 中克隆到 AHAS 大小亚基基因 ilvIH,氨基酸比对结果表明菌株 Lm10与标准菌株 kt2440的 IlvI 的5个位点有差异,而小亚基则与标准菌株 kt2440的 ilvH 完全相同。为阐明抗性产生机制和通过基因工程获得性能更优良的乙酰乳酸合酶基因提供了重要的理论基础和应用价值。

关键词： ALS inhibitors herbicides herbicides-resistant bacterium acetohydroxyacid synthase ilvIH

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