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Effective prevention of the pinewood nematode, Bursaphelenchus xylophilus , by enzymatic glycosylation of avermectin
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- URLhttps://db.koreascholar.com/Article/Detail/363296
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. Glycosylation is generally used to enhance the aqueous solubility and biological activity of natural compounds. Uridine diphosphate (UDP)-glycosyltransferase (BLC) from Bacillus licheniformis is involved in the biosynthesis of the bioactive compound by transferring UDP-activated sugar moieties to acceptor molecules. 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 B1a glycosides were produced: avermectin B1a 4’’-β-D-glucoside, avermectin B1a 4’’-β-D-galactoside, avermectin B1a 4’’-β-L-fucoside and avermectin B1a 4’’-β-2-deoxy-D-glucoside. The avermectin B1a glycosides were structurally analyzed based on HR-ESIMS, 1D and 2D nuclear magnetic resonance (NMR) spectra. The solubility of avermectin B1a4’’-β-D-glucoside and avermectin B1a4’’-β-D-galactoside in water are 49 and 21 times higher than that of avermectin B1a. Consistent with the improved water solubility of avermectin glycosides, the anti-nematodal effect of avermectin B1a4’’-β-D-glucoside was found to exhibit the highest activity,which was approximately 32 times greater than that of avermectin B1a, followed by avermectin B1a 4’’-β-2-deoxy-D-glucoside, avermectin B1a 4’’-β-L-fucoside, and avermectin B1a 4’’-β-D-galactoside. These results show that glycosylation of avermectinB1a effectively enhances itsin vitro anti-nematodal activity and that avermectin glycosides can be further applied for treating infestations of the pine wood nematode B. xylophilus.
