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Conversion of puerarin into its 7-O-glycoside derivatives by Microbacterium oxydans (CGMCC 1788) to improve its water solubility and pharmacokinetic properties

Abstract

Microbacterium oxydans strain NJ 6 isolated from soil samples converted puerarin into two novel compounds, puerarin-7-O-glucoside and puerarin-7-O-isomaltoside, via an unreported O-glycosylation of the phenolic hydroxyl group at the 7-position of puerarin. Sucrose, maltotriose, and maltose could be used as glucosyl donors for glycosylation of puerarin, but uridine-diphosphate glucose, glucose, fructose, lactose, cyclodextrin, and starch could not. Regardless of the position of B-ring in the (iso)flavonoids core structure, the glycosylation of the phenolic hydroxyl group at the 7-position of (iso)flavonoids was governed by the presence or absence of a glucosyl residue at 8-C. The apparent solubility of puerarin-7-O-glucoside and puerarin-7-O-isomaltoside was approximately 18 and 100 times that of natural puerarin, respectively. Like parent puerarin, puerarin-7-O-glucoside maintained its physiological ability to relax the contractions of isolated rat thoracic aortic rings in vitro induced by phenylephrine. However, puerarin-7-O-glucoside was able to maintain higher plasma concentrations and have a longer mean residence time in the blood than the parent puerarin.

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Acknowledgments

This work was supported financially by Key Basic Research Program of the Jiangsu Higher Education Institutions (06KJA21016), Jiangsu Outstanding Talents Program in Six Areas (06-C-014) and Jiangsu Lianchuang Meditech. Xuansheng Ding and Feng Yu in China Pharmaceutical University, and Shuqing Yu in Nanjing Normal University provided helps for experiments of vasorelaxing effect of puerarin-7-O-glucoside.

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Correspondence to Sheng Yuan or Xiao-dong Cong.

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Jiang, J., Yuan, S., Ding, J. et al. Conversion of puerarin into its 7-O-glycoside derivatives by Microbacterium oxydans (CGMCC 1788) to improve its water solubility and pharmacokinetic properties. Appl Microbiol Biotechnol 81, 647–657 (2008). https://doi.org/10.1007/s00253-008-1683-z

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Keywords

  • Puerarin
  • Glycosylation
  • Microbacterium oxydans
  • Water solubility
  • Vasorelaxing effect