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Mol. Cells 2013; 36(4): 362-367

Published online October 22, 2013

https://doi.org/10.1007/s10059-013-0181-z

© The Korean Society for Molecular and Cellular Biology

Enzymatic Synthesis of Apigenin Glucosides by Glucosyltransferase (YjiC) from Bacillus licheniformis DSM 13

Rit Bahadur Gurung, Eun-Hee Kim, Tae-Jin Oh, and Jae Kyung Sohng

Department of Pharmaceutical Engineering, Institute of Biomolecule Reconstruction, Sun Moon University, Asan 336-708, Korea, 1Division of Magnetic Resonance, Korea Basic Science Institute, Ochang 363-883, Korea

Received: June 17, 2013; Revised: July 28, 2013; Accepted: August 26, 2013

Abstract

Apigenin, a member of the flavone subclass of flavono-ids, has long been considered to have various biological activities. Its glucosides, in particular, have been reported to have higher water solubility, increased chemical stability, and enhanced biological activities. Here, the synthesis of apigenin glucosides by the in vitro glucosylation reaction was successfully performed using a UDP-glucosyltrans-ferase YjiC, from Bacillus licheniformis DSM 13. The glucosylation has been confirmed at the phenolic groups of C-4′ and C-7 positions ensuing apigenin 4′-O-glucoside, apigenin 7-O-glucoside and apigenin 4′,7-O-diglucoside as the products leaving the C-5 position unglucosylated. The position of glucosylation and the chemical structures of glucosides were elucidated by liquid chromatography/ mass spectroscopy and nuclear magnetic resonance spec- troscopy. The parameters such as pH, UDP glucose concentration and time of incubation were also analyzed during this study.

Keywords apigenin, enzymatic synthesis, glucosides, UDP-glucosyltransferase, YjiC

Article

Research Article

Mol. Cells 2013; 36(4): 362-367

Published online October 31, 2013 https://doi.org/10.1007/s10059-013-0181-z

Copyright © The Korean Society for Molecular and Cellular Biology.

Enzymatic Synthesis of Apigenin Glucosides by Glucosyltransferase (YjiC) from Bacillus licheniformis DSM 13

Rit Bahadur Gurung, Eun-Hee Kim, Tae-Jin Oh, and Jae Kyung Sohng

Department of Pharmaceutical Engineering, Institute of Biomolecule Reconstruction, Sun Moon University, Asan 336-708, Korea, 1Division of Magnetic Resonance, Korea Basic Science Institute, Ochang 363-883, Korea

Received: June 17, 2013; Revised: July 28, 2013; Accepted: August 26, 2013

Abstract

Apigenin, a member of the flavone subclass of flavono-ids, has long been considered to have various biological activities. Its glucosides, in particular, have been reported to have higher water solubility, increased chemical stability, and enhanced biological activities. Here, the synthesis of apigenin glucosides by the in vitro glucosylation reaction was successfully performed using a UDP-glucosyltrans-ferase YjiC, from Bacillus licheniformis DSM 13. The glucosylation has been confirmed at the phenolic groups of C-4′ and C-7 positions ensuing apigenin 4′-O-glucoside, apigenin 7-O-glucoside and apigenin 4′,7-O-diglucoside as the products leaving the C-5 position unglucosylated. The position of glucosylation and the chemical structures of glucosides were elucidated by liquid chromatography/ mass spectroscopy and nuclear magnetic resonance spec- troscopy. The parameters such as pH, UDP glucose concentration and time of incubation were also analyzed during this study.

Keywords: apigenin, enzymatic synthesis, glucosides, UDP-glucosyltransferase, YjiC

Mol. Cells
Nov 30, 2023 Vol.46 No.11, pp. 655~725
COVER PICTURE
Kim et al. (pp. 710-724) demonstrated that a pathogen-derived Ralstonia pseudosolanacearum type III effector RipL delays flowering time and enhances susceptibility to bacterial infection in Arabidopsis thaliana. Shown is the RipL-expressing Arabidopsis plant, which displays general dampening of the transcriptional program during pathogen infection, grown in long-day conditions.

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