Abstract
Twelve candidate uridine diphosphate-dependent glucosyltransferases (UGTs) from Arabidopsis thaliana were screened to identify UGTs that synthesized ferulic acid 4-O-glucoside or feruloyl glucoside, respectively. We used biotransformation using E. coli harboring each UGT. E. coli harboring AtUGT71C1 could synthesize feruloyl glucoside with a conversion rate of 1.8 μM/h. E. coli harboring AtUGT72E2 showed the best conversion rate for converting ferulic acid into ferulic acid glucoside, at 15.8 μM/h. Molecular docking analysis of ferulic acid into the modeled structures of AtUGT71C1 and AtUGT72E2 was used to elucidate the different conversion rates of ferulic acid into corresponding glucoside.
This is a preview of subscription content, log in via an institution to check access.
References
Bowles D, Lim E-K, Poppenberger B, Vaistij FE (2006) Glycosyltransferases of lipophilic small molecules. Annu Rev Plant Biol 57:567–597
Caputi L, Lim E-K, Bowles DJ (2008) Discovery of new biocatalysts for the glycosylation of terpenoid scaffolds. Chem Eur J 14:6656–6662
Han SH, Kim B-G, Yoon JA, Chong Y, Ahn J-H (2014) Synthesis of flavonoid O-pentosides by Escherichia coli through engineering nucleotide sugar synthesis pathway and glycosyltransferase. Appl Environ Microbiol 80:2754–2762
Johnsson P, Peerlkamp N, Kamal-Eldin A, Andersson RE, Andersson R, Lundgren LN, Åmana P (2002) Polymeric fractions containing phenol glucosides in flaxseed. Food Chem 76:207–212
Katsuragi H, Shimoda K, Yamamoto R, Ishihara K, Hiroki H (2011) Glycosylation of capsaicin derivatives and phenylpropanoid derivatives using cultured plant cells. Biochem Insights 4:1–12
Kim HS, Kim B-G, Sung S, Kim M, Mok H, Chong Y, Ahn J-H (2013) Engineering flavonoid glycosyltransferases for enhanced catalytic efficiency and extended sugar donor selectivity. Planta 238:683–693
Kim SY, Lee HR, K-s Park, Kim BG, Ahn J-H (2015) Metabolic engineering of Escherichia coli for the biosynthesis of flavonoid O-glucuronides and flavonoid O-galactoside. Appl Microbiol Biot 99:2233–2242
Kubo A, Arai Y, Nagashima S, Yoshikawa T (2004) Alteration of sugar donor specificities of plant glycosyltransferases by a single point mutation. Arch Biochem Biophys 439:198–203
Lanot A, Hodge D, Jackson RG, George GL, Elias L, Lim EK, Vaistij FE, Bowles DJ (2006) The glucosyltransferase UGT72E2 is responsible for monolignol 4-O-glucoside production in Arabidopsis thaliana. Plant J 48:286–295
Lim E-K, Li Y, Parr A, Jackson R, Ashford DA, Bowles DJ (2001) Identification of glucosyltransferase genes involved in sinapate metabolism and synthesis in Arabidopsis. J Biol Chem 276:4344–4349
Lim EK, Higgins GS, Li Y, Bowles DJ (2003) Regioselectivity of glucosylation of caffeic acid by a UDP-glucose:glucosyltransferase is maintained in planta. Biochem J 373:987–992
Lim E-K, Jackson RG, Bowles DJ (2005) Identification and characterization of Arabidopsis glycosyltransferase capable of glucosylating coniferyl aldehyde and sinapyl aldehyde. FEBS Lett 579:2802–2806
Vogt T, Jones P (2000) Glycosyltransferases in plant natural product synthesis: characterization of a supergene family. Trend Plant Sci 5:380–386
Acknowledgments
This paper was supported by Konkuk University in 2015.
Author information
Authors and Affiliations
Corresponding author
Additional information
Da Ye Han and Hye Rin Lee authors contributed equally to this work.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Han, D.Y., Lee, H.R., Kim, B.G. et al. Biosynthesis of ferulic acid 4-O-glucoside and feruloyl glucoside using Escherichia coli harboring regioselective glucosyltransferases. Appl Biol Chem 59, 481–484 (2016). https://doi.org/10.1007/s13765-016-0186-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13765-016-0186-3