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Compound isoglycyrdeuteroside and preparation and usage thereof

A technology of glycyrrhetin and crude glycyrrhetin, which is applied in the direction of steroidal compounds, food preparation, application, etc.

Inactive Publication Date: 2008-01-30
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there is no report about the production method of isoglycyrrhetin

Method used

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  • Compound isoglycyrdeuteroside and preparation and usage thereof
  • Compound isoglycyrdeuteroside and preparation and usage thereof
  • Compound isoglycyrdeuteroside and preparation and usage thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In a 50mL conical flask with a stopper, add 10mL of 20g / L 18α-glycyrrhizic acid solution (pH 6.0), then add 0.2g of pig liver enzyme powder (containing β-glucuronidase), and cover the grinding mouth tightly. Bottle stopper, react for 24h on a water bath shaker at 50°C and 120r / min. After the reaction was completed, the pH of the reaction solution was adjusted to 2-3, extracted with n-butanol for 2-3 times, the extracts were combined, and the organic solvent was removed by rotary evaporation to obtain 0.16 g of crude isoglycyrrhizin with a purity of 72% as determined by HPLC.

Embodiment 2

[0022] The crude isoliquiritiside prepared according to Example 1 was recrystallized 3-5 times with 85% glacial acetic acid to obtain 0.12 g of isoliquiritiside, the sweetness of which was about 900 times that of sucrose. That 1 H-NMR and 13 Assignment of C-NMR signals (DMSO-d 6 , internal standard TMS, 303K) as follows:

[0023] No.

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PUM

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Abstract

The invention discloses pentacyclic triterpenoid compound - iso-glycyrrhizin and the preparation method and the application thereof, with a chemical name 18Alpha-hydro -20Beta-carboxy -11-oxy -oleanane -12-en-3Beta-yl -2-O-Beta-D- pyranyl glucuronic acid. The preparation method is that: enzyme preparation is added into the solution of 18Alpha-glycyrhizic acid in a certain concentration and PH value, then iso-glycyrrhizin is produced in the suitable condition. After the reaction, iso-glycyrrhizin is produced through butanol extraction, macroporous absorption resin separation and purification, recrystalization. The iso-glycyrrhizin disclosed by the invention is a novel compound with obvious sweet performance.

Description

technical field [0001] The present invention relates to the structure, preparation and application of a new compound isoliquiritiside. Background technique [0002] Glycyrrhizic acid is the main component of traditional Chinese medicine licorice, which has anti-inflammatory, anti-viral, anti-allergic and other effects. Glycyrrhizic acid can be hydrolyzed to lose a glucuronic acid group under the action of enzymes to obtain glycyrrhizin, which has higher sweetness performance and bioavailability. Natural glycyrrhizic acid is mainly β body, which can be transformed into α body 18α-glycyrrhizic acid under certain conditions. Conformational analysis showed that 18α-H was not in the same plane as the carboxyl group on C30, while 18β-H was in the same plane. Due to the steric hindrance effect, the former is more lipophilic than the latter, and is easy to bind to receptor proteins in vivo. The D / E ring in the α body structure is in a trans configuration, similar to prednisolone, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A23L1/236A23L27/30
Inventor 卢定强肖洁瑾李晖欧阳平凯
Owner NANJING UNIV OF TECH
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