Biocatalysis of Phenolic Glycosides Natural Products in Escherichia coli Strain Using UGT73B6

doi:10.13560/j.cnki.biotech.bull.1985.2017-0363

Abstract

Abstract: The glycosyltransferase UGT73B6 from Rhodiola sachalinensis with substrate flexibility can glycosylate many natural products catalyzed by UDP-glycosyltransferases（UGTs）. To achieve the biosynthesis of phenolic compounds in Escherichia coli,in this study,we utilized the catalytic activity of the glycosyltransferase UGT73B6 and fed 7 different phenolic compounds in Escherichia coli BL21（DE3）. By using biotransformation,we successfully achieved the biocatalysis of 8 glycoside compounds for the first time in Escherichia coli with UGT73B6,and further we explored the substrate flexibility of UGT73B6. On the basis of this study,we provided an effective and economical method to produce phenolic glycosides by microbial transformation,which has a great application value.

Key words: glycosyltransferase UGT73B6, biotransformation, phenolic glycosides, Escherichia coli

HE Qing-lin, BAI Yan-fen, ZHOU Wei, YIN Hua, CHEN Ning, ZHUANG Yi-bin, LIU Tao. Biocatalysis of Phenolic Glycosides Natural Products in Escherichia coli Strain Using UGT73B6[J]. Biotechnology Bulletin, 2017, 33(11): 136-142.

References

[1] Modolo LV, Li L, Pan H, et al. Crystal structures of glycosyltransferase UGT78G1 reveal the molecular basis for glycosylation and deglycosylation of（iso）flavonoids[J]. Journal of Molecular Biology, 2009, 392（5）：1292-1302.
[2] Gachon CM, Langlois-Meurinne M, Saindrenan P. Plant secondary metabolism glycosyltransferases：the emerging functional analysis[J]. Trends in Plant Science, 2005, 10（11）：542-549.
[3] Jones P, Vogt T. Glycosyltransferases in secondary plant metabolism：tranquilizers and stimulant controllers[J]. Planta, 2001, 213（2）：164-174.
[4] Bowles D, Isayenkova J, Lim EK, et al. Glycosyltransferases：managers of small molecules[J]. Current Opinion in Plant Biology, 2005, 8（3）：254-263.
[5] Cheynier V. Phenolic compounds：from plants to foods[J]. Phytochemistry Reviews, 2012, 11（2-3）：153-177.
[6] Lin D, Xiao M, Zhao J, et al. An Overview of plant phenolic compounds and their importance in human nutrition and management of Type 2 diabetes[J]. Molecules, 2016, 21, 1374：1-19.
[7] Woo HJ, Kang HK, Nguyen TT, et al. Synthesis and characterization of ampelopsin glucosides using dextransucrase from Leuconostoc mesenteroides B-1299CB4：glucosylation enhancing physicoche-mical properties[J]. Enzyme and Microbial Technology, 2012, 51（6-7）：311-318.
[8] Raab T, Barron D, Vera FA, et al. Catechin glucosides：occurrence, synthesis, and stability[J]. Journal of Agricultural and Food Chemistry, 2010, 58（4）：2138-2149.
[9] Blanchard S, Thorson JS. Enzymatic tools for engineering natural product glycosylation[J]. Current Opinion in Chemical Biology, 2006, 10（3）：263-271.
[10] Li D, Roh SA, Shim JH, et al. Glycosylation of genistin into soluble inclusion complex form of cyclic glucans by enzymatic modification[J]. Journal of Agricultural and Food Chemistry, 2005, 53（16）：6516-6524.
[11] Leadlay PF. Combinatorial approaches to polyketide biosynthesis [J]. Current Opinion in Chemical Biology, 1997, 1（2）：162-168.
[12] Floss HG. Antibiotic biosynthesis：from natural to unnatural compounds[J]. Journal of Industrial Microbiology & Biotechnology, 2001, 27（3）：183-194.
[13] Mendez C, Salas JA. Altering the glycosylation pattern of bioactive compounds[J]. Trends in Biotechnology, 2001, 19（11）：449-456.
[14] Fu X, Albermann C, Jiang J, et al. Antibiotic optimization via in vitro glycorandomization[J]. Nature Biotechnology, 2003, 21（12）：1467-1469.
[15] Yang J, Hoffmeister D, Liu L, et al. Natural product glycorandomi-zation[J]. Bioorganic & Medicinal Chemistry, 2004, 12（7）：1577-1584.
[16] Rupprath C, Schumacher T, Elling L. Nucleotide deoxysugars：essential tools for the glycosylation engineering of novel bioactive compounds[J]. Current Medicinal Chemistry, 2005, 12（14）：1637-1675.
[17] Melancon CE, 3rd, Thibodeaux CJ, et al. Glyco-stripping and glyco-swapping[J]. ACS Chemical Biology, 2006, 1（8）：499-504.
[18] Ma LQ, Liu BY, Gao DY, et al. Molecular cloning and overexpression of a novel UDP-glucosyltransferase elevating salidroside levels in Rhodiola sachalinensis[J]. Plant Cell Reports, 2007, 26（7）：989-999.
[19] Bai Y, Bi H, Zhuang Y, et al. Production of salidroside in metabolically engineered Escherichia coli[J]. Scientific Reports, 2014, 4：6640.
[20] Zhang Z, Yu B, Schmidt R. Synthesis of mono- and di-O-β-d-glucopyranoside conjugates of（E）-resveratrol[J]. Synthesis, 2006, 2006（8）：1301-1306.
[21] Zhou M, Hamza A, Zhan CG, et al. Assessing the regioselectivity of OleD-catalyzed glycosylation with a diverse set of acceptors[J]. Journal of Natural Products, 2013, 76（2）：279-286.
[22] 田宁, 咸莫, 胡仰栋, 等. 产香叶醇重组大肠杆菌发酵培养基的优化[J]. 林产化学与工业, 2015, 35（4）：131-137.
[23] Gantt RW, Goff RD, Williams GJ, et al. Probing the aglycon promiscuity of an engineered glycosyltransferase[J]. Angewandte Chemie International Edition, 2008, 47：8889-8892.
[24] 刘庆鑫, 李慧梁, 柳润辉, 等. 微生物转化在天然产物研究中的应用[J]. 药学实践杂志, 2012, 30（5）：321-325.