数字农科院2.0

Designed biosynthesis of 25-methyl and 25-ethyl ivermectin with enhanced insecticidal activity by domain swap of avermectin polyketide synthase

文献类型： 外文期刊

作者： Yan, Yi-Jun;An, Jing;Wang, Xiang-Jing;Xiang, Wen-Sheng;Xiang, Wen-Sheng;Yan, Yi-Jun;Huang, Sheng-Xiong

作者机构：

关键词： 25-Ethyl ivermectin;25-Methyl ivermectin;Domain swap;Insecticidal activity

期刊名称： MICROBIAL CELL FACTORIES

ISSN： 1475-2859

年卷期： 2015 年 14 卷

页码：

收录情况： SCI

摘要： Background: Avermectin and milbemycin are important 16-membered macrolides that have been widely used as pesticides in agriculture. However, the wide use of these pesticides inevitably causes serious drug resistance, it is therefore imperative to develop new avermectin and milbemycin analogs. The biosynthetic gene clusters of avermectin and milbemycin have been identified and the biosynthetic pathways have been elucidated. Combinatorial biosynthesis by domain swap provides an efficient strategy to generate chemical diversity according to the module polyketide synthase (PKS) assembly line. Results: The substitution of aveDH2-KR2 located in avermectin biosynthetic gene cluster in the industrial avermectin-producing strain Streptomyces avermitilis NA-108 with the DNA regions milDH2-ER2-KR2 located in milbemycin biosynthetic gene cluster in Streptomyces bingchenggensis led to S. avermitilis AVE-T27, which produced ivermectin B1a with high yield of 3450 +/- 65 mu g/ml. The subsequent replacement of aveLAT-ACP encoding the loading module of avermectin PKS with milLAT-ACP encoding the loading module of milbemycin PKS led to strain S. avermitilis AVE-H39, which produced two new avermectin derivatives 25-ethyl and 25-methyl ivermectin (1 and 2) with yields of 951 +/- 46 and 2093 +/- 61 mu g/ml, respectively. Compared to commercial insecticide ivermectin, the mixture of 25-methyl and 25-ethyl ivermectin (2:1 = 3:7) exhibited 4.6-fold increase in insecticidal activity against Caenorhabditis elegans. Moreover, the insecticidal activity of the mixture of 25-methyl and 25-ethyl ivermectin was 2.5-fold and 5.7-fold higher than that of milbemycin A3/A4 against C. elegans and the second-instar larva of Mythimna separate, respectively. Conclusions: Two new avermectin derivatives 25-methyl and 25-ethyl ivermectin were generated by the domain swap of avermectin PKS. The enhanced insecticidal activity of 25-methyl and 25-ethyl ivermectin implied the potential use as insecticide in agriculture. Furthermore, the high yield and genetic stability of the engineered strains S. avermitilis AVE-T27 and AVE-H39 suggested the enormous potential in industrial production of the commercial insecticide ivermectin and 25-methyl/25-ethyl ivermectins, respectively.

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[1]MOESM15 of Designed biosynthesis of 25-methyl and 25-ethyl ivermectin with enhanced insecticidal activity by domain swap of avermectin polyketide synthase. Yan, Yi-Jun,Sheng-Xiong Huang,Zhang, Ji,Xiang, Wen-Sheng,Xiang-Jing Wang,An, Jing

[2]MOESM9 of Designed biosynthesis of 25-methyl and 25-ethyl ivermectin with enhanced insecticidal activity by domain swap of avermectin polyketide synthase. Xiang, Wen-Sheng,Sheng-Xiong Huang,Yan, Yi-Jun,Zhang, Ji,An, Jing,Xiang-Jing Wang

[3]MOESM12 of Designed biosynthesis of 25-methyl and 25-ethyl ivermectin with enhanced insecticidal activity by domain swap of avermectin polyketide synthase. Zhang, Ji,Sheng-Xiong Huang,Xiang-Jing Wang,Xiang, Wen-Sheng,An, Jing,Yan, Yi-Jun

[4]MOESM13 of Designed biosynthesis of 25-methyl and 25-ethyl ivermectin with enhanced insecticidal activity by domain swap of avermectin polyketide synthase. An, Jing,Zhang, Ji,Xiang, Wen-Sheng,Sheng-Xiong Huang,Yan, Yi-Jun,Xiang-Jing Wang

[5]MOESM11 of Designed biosynthesis of 25-methyl and 25-ethyl ivermectin with enhanced insecticidal activity by domain swap of avermectin polyketide synthase. Zhang, Ji,Yan, Yi-Jun,Xiang, Wen-Sheng,Sheng-Xiong Huang,An, Jing,Xiang-Jing Wang

[6]MOESM5 of Designed biosynthesis of 25-methyl and 25-ethyl ivermectin with enhanced insecticidal activity by domain swap of avermectin polyketide synthase. Zhang, Ji,An, Jing,Sheng-Xiong Huang,Xiang-Jing Wang,Xiang, Wen-Sheng,Yan, Yi-Jun

[7]MOESM1 of Designed biosynthesis of 25-methyl and 25-ethyl ivermectin with enhanced insecticidal activity by domain swap of avermectin polyketide synthase. Yan, Yi-Jun,Sheng-Xiong Huang,Xiang, Wen-Sheng,Xiang-Jing Wang,Zhang, Ji,An, Jing

[8]MOESM14 of Designed biosynthesis of 25-methyl and 25-ethyl ivermectin with enhanced insecticidal activity by domain swap of avermectin polyketide synthase. Xiang-Jing Wang,Yan, Yi-Jun,Sheng-Xiong Huang,Zhang, Ji,Xiang, Wen-Sheng,An, Jing

[9]MOESM3 of Designed biosynthesis of 25-methyl and 25-ethyl ivermectin with enhanced insecticidal activity by domain swap of avermectin polyketide synthase. Zhang, Ji,Xiang, Wen-Sheng,Sheng-Xiong Huang,An, Jing,Yan, Yi-Jun,Xiang-Jing Wang

[10]MOESM2 of Designed biosynthesis of 25-methyl and 25-ethyl ivermectin with enhanced insecticidal activity by domain swap of avermectin polyketide synthase. Xiang, Wen-Sheng,Yan, Yi-Jun,Zhang, Ji,Sheng-Xiong Huang,An, Jing,Xiang-Jing Wang

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