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Regioselective synthesis of plant (iso)flavone glycosides in Escherichia coli

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Abstract

The flavonoids genistein, biochanin A, luteolin, quercetin, and kaempferol are plant natural products with potentially useful pharmacological and nutraceutical activities. These natural products usually exist in plants as glycosides, and their glycosylation has a remarkable influence on their pharmacokinetic properties. The glycosyltransferases UGT71G1 and UGT73C8 from Medicago truncatula are excellent reagents for the regioselective glycosylation of (iso)flavonoids in Escherichia coli grown in Terrific broth. Ten to 20 mg/L of either genistein or biochanin A 7-O-glucoside was produced after feeding genistein or biochanin A to E. coli expressing UGT71G1, and similar levels of luteolin 4’-O- and 7-O-glucosides were produced after feeding luteolin to cultures expressing UGT73C8. For the production of kaempferol 3-O-glucoside or quercetin 3-O-glucoside, the Phe148Val or Tyr202Ala mutants of UGT71G1 were employed. Ten to 16 mg/L of either kaempferol 3-O- or quercetin 3-O-glucosides were produced on feeding kaempferol or quercetin to E. coli expressing these enzymes. More than 90% of the glucoside products were released to the medium, facilitating their isolation.

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Acknowledgements

We thank Dr. L. Modolo for assistance with artwork and Drs Y. Z. Pang and G. J. Peel for critical reading of the manuscript. This work was supported by the Samuel Roberts Noble Foundation.

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Correspondence to Xian-Zhi He.

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Open Access This is an open access article distributed under the terms of the Creative Commons Attribution Noncommercial License (https://creativecommons.org/licenses/by-nc/2.0), which permits any noncommercial use, distribution, and reproduction in any medium, provided the original author(s) and source are credited.

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He, X., Li, W., Blount, J.W. et al. Regioselective synthesis of plant (iso)flavone glycosides in Escherichia coli . Appl Microbiol Biotechnol 80, 253–260 (2008). https://doi.org/10.1007/s00253-008-1554-7

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Keywords

  • Quercetin
  • Genistein
  • Kaempferol
  • Luteolin
  • Flavonoid Glycoside