Isolation and identification of main constituents in an enzymatically hydrolysed licorice extract sweetener

Food Addit Contam. 2001 Apr;18(4):281-4. doi: 10.1080/02652030116955.

Abstract

Licorice extract including glycyrrhizin as the major component is used as a safe sweetener in many countries. Enzymatically hydrolysed licorice extract (EHLE) is also used as a sweetener in Japan. In the present paper, the constituents of EHLE were investigated as a part of the studies for evaluating its quality and safety as a food additive. Three oleanane-type monoglycosides along with glycyrrhizin (1) eand 3-O-[beta-D-glucuronopyranosyl-(1-->2)-beta-D-glucuronopyranosyl]-18beta-liquiritic acid (2) were isolated from EHLE. The structures of the three compounds have been determined to be 3-O-beta-D-glucuronopyranosyl-24-hydroxy-18beta-glycyrrhetinic acid (3), 3-O-beta-D-glucur-onopyranosyl-18beta-glycyrrhetinic acid (4) and 3-O-beta-D-glucuronopyranosyl-18beta-liquiritic acid (5) based on MS and NMR. Compound 4 was the monoglycosylated derivactive of glycyrrhizin (1). Compounds 3 amd 5 are the monoglycosylated derivatives of the minor constituents in licorice extract. They were first isolated from EHLE, and compound 5 was a new compound.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glucuronidase
  • Glycyrrhizic Acid / chemistry*
  • Humans
  • Hydrolysis
  • Magnetic Resonance Spectroscopy
  • Spectrometry, Mass, Secondary Ion
  • Sweetening Agents / chemistry*

Substances

  • Sweetening Agents
  • Glycyrrhizic Acid
  • Glucuronidase