Superbacteria Research Center, Korea Research Institute of Bioscience and Biotechnology, Yusong, Daejeon, 305-806, Republic of Korea.
Department of Bio-Molecular Science, KRIBB School of Bioscience, Korea University of Science and Technology (UST), Yusong, Daejeon, 305-806, Republic of Korea.
Appl Microbiol Biotechnol. 2018 Mar;102(5):2155-2165. doi: 10.1007/s00253-018-8764-4. Epub 2018 Jan 25.
Avermectin produced by Streptomyces avermitilis is an anti-nematodal agent against the pine wood nematode Bursaphelenchus xylophilus. However, its potential usage is limited by its poor water solubility. For this reason, continuous efforts are underway to produce new derivatives that are more water soluble. Here, the enzymatic glycosylation of avermectin was catalyzed by uridine diphosphate (UDP)-glycosyltransferase from Bacillus licheniformis with various UDP sugars. As a result, the following four avermectin B glycosides were produced: avermectin B 4″-β-D-glucoside, avermectin B 4″-β-D-galactoside, avermectin B 4″-β-L-fucoside, and avermectin B 4″-β-2-deoxy-D-glucoside. The avermectin B glycosides were structurally analyzed based on HR-ESI MS and 1D and 2D nuclear magnetic resonance spectra, and the anti-nematodal effect of avermectin B 4″-β-D-glucoside was found to exhibit the highest activity (IC = 0.23 μM), which was approximately 32 times greater than that of avermectin B (IC = 7.30 μM), followed by avermectin B 4″-β-2-deoxy-D-glucoside (IC = 0.69 μM), avermectin B 4″-β-L-fucoside (IC = 0.89 μM), and avermectin B 4″-β-D-galactoside (IC = 1.07 μM). These results show that glycosylation of avermectin B effectively enhances its in vitro anti-nematodal activity and that avermectin glycosides can be further applied for treating infestations of the pine wood nematode B. xylophilus.
阿维菌素是由阿维链霉菌产生的一种抗线虫剂，可用于防治松材线虫。然而，其水溶性差限制了其应用。因此，人们一直在努力生产水溶性更好的新衍生物。在这里，通过来自地衣芽孢杆菌的尿苷二磷酸（UDP）-糖基转移酶，用各种 UDP 糖对阿维菌素进行了酶促糖基化。结果生成了以下四种阿维菌素 B 糖苷：阿维菌素 B 4″-β-D-葡萄糖苷、阿维菌素 B 4″-β-D-半乳糖苷、阿维菌素 B 4″-β-L-岩藻糖苷和阿维菌素 B 4″-β-2-脱氧-D-葡萄糖苷。根据高分辨电喷雾质谱（HR-ESI MS）和一维及二维核磁共振谱对阿维菌素 B 糖苷进行了结构分析，并发现阿维菌素 B 4″-β-D-葡萄糖苷的抗线虫活性最高（IC=0.23 μM），约为阿维菌素 B 的 32 倍（IC=7.30 μM），其次是阿维菌素 B 4″-β-2-脱氧-D-葡萄糖苷（IC=0.69 μM）、阿维菌素 B 4″-β-L-岩藻糖苷（IC=0.89 μM）和阿维菌素 B 4″-β-D-半乳糖苷（IC=1.07 μM）。这些结果表明，阿维菌素 B 的糖基化可有效提高其体外抗线虫活性，且阿维菌素糖苷可进一步用于防治松材线虫的侵害。
