An effective way to biosynthesize α-glucosyl eugenol with a high yield by Xanthomonas maltophilia

Pharm Biol. 2012 Jun;50(6):727-31. doi: 10.3109/13880209.2011.624104. Epub 2011 Nov 9.

Abstract

Context: Eugenol is known for its analgesic, local anesthetic, anti-inflammatory, antibacterial, and hair growing effects, the application of which, however, is limited by its low solubility, liability of sublimating, and its pungent smell. Compared to eugenol, its glycosylated derivate [eugenol α-glucoside (α-EG)] has more advantages in application.

Objective: The biosynthesis of α-EG by Xanthomonas maltophilia Hugh (Xanthomonadaceae) BT-112 and the optimum conditions for α-EG production are investigated here.

Materials and methods: The α-EG was obtained by fermentation using Xanthomonas maltophilia BT-112 and purified by macroporous absorption resin. The identity of α-EG is confirmed by high performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR).

Results: The maximum yield of α-EG reached 10.62 g/L broth when the suspension of Xanthomonas maltophilia strain was incubated at 30°C with 70 mM eugenol and 1.0 M maltose.

Discussion and conclusion: Bio-fermentation was applied in this work to get α-EG with a high mole conversion, which is a potentially efficient and highly promising approach to modify phenolic compounds into glucosides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anesthetics, Local / chemistry
  • Anesthetics, Local / isolation & purification
  • Anesthetics, Local / metabolism
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / metabolism
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
  • Anti-Inflammatory Agents, Non-Steroidal / metabolism*
  • Biocatalysis
  • Chemistry, Pharmaceutical
  • Eugenol / analogs & derivatives*
  • Eugenol / chemistry
  • Eugenol / isolation & purification
  • Eugenol / metabolism
  • Fermentation
  • Glucosides / chemistry
  • Glucosides / isolation & purification
  • Glucosides / metabolism*
  • Kinetics
  • Maltose / metabolism
  • Odorants
  • Solubility
  • Stenotrophomonas maltophilia / growth & development
  • Stenotrophomonas maltophilia / metabolism*
  • Stereoisomerism
  • Volatilization

Substances

  • Anesthetics, Local
  • Anti-Bacterial Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Glucosides
  • Eugenol
  • Maltose