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Method for preparing hyaluronan oligosaccharide chain modified flavonoid compound carrying glucuronic acid on terminal

A technology of hyaluronic acid oligosaccharides and glucuronic acid, which is applied in the direction of fermentation, etc., to achieve the effect of simple process, easy operation and stable activity

Inactive Publication Date: 2015-03-04
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, after searching, the flavonoid compound with glucuronic acid at the end is the leader, and under the catalysis of hyaluronic acid synthase, the hyaluronic acid oligosaccharide chain is extended on the terminal glucuronic acid group of the flavonoid compound. , the preparation of flavonoids modified by the hyaluronic acid oligosaccharide chain has not been reported in the patent or literature

Method used

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  • Method for preparing hyaluronan oligosaccharide chain modified flavonoid compound carrying glucuronic acid on terminal
  • Method for preparing hyaluronan oligosaccharide chain modified flavonoid compound carrying glucuronic acid on terminal
  • Method for preparing hyaluronan oligosaccharide chain modified flavonoid compound carrying glucuronic acid on terminal

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Effect test

Embodiment 1

[0061] Example 1 A preparation method of hyaluronic acid oligosaccharide chain modified flavonoid glycoside compound

[0062] A method for modifying flavonoids with glucuronic acid at the end of a hyaluronic acid oligosaccharide chain, the steps are as follows:

[0063] 1. Preparation of Hyaluronan Synthase

[0064] According to the GenBank accession number AF036004, the hyaluronan synthase gene was obtained by gene synthesis. The target gene was obtained by PCR and constructed into the pET-15b vector, and the recombinant vector obtained by the construction was transformed into the expression strain Escherichiacoli BL21 (DE3), and isopropylthiogalactoside (IPTG) induced the expression of hyaluronic acid synthase; The hyaluronic acid synthase is obtained by ultrasonically disrupting the bacteria, purifying by Ni-NTA affinity chromatography, and concentrating by ultrafiltration. The molecular weight and purity of the target protein were tested by sodium dodecyl sulfate polyacr...

Embodiment 2

[0082] Example 2 A preparation method of a flavonoid compound whose hyaluronic acid oligosaccharide chain modification end is glucuronic acid

[0083] A kind of hyaluronic acid oligosaccharide chain modified end is the preparation method of the flavonoid compound of glucuronic acid as described in embodiment 1, difference is:

[0084] The final molar concentration ratio of the reaction solution of UDP-GlcNAc, UDP-GlcA and hyaluronic acid trisaccharide-modified flavonoids is 100:100:1.

[0085] The product electrophoresis detection results were as follows: Figure 7 Strip 1 is shown.

Embodiment 3

[0086] Example 3 A preparation method of flavonoids whose hyaluronic acid oligosaccharide chains are modified with glucuronic acid at the end

[0087] A kind of hyaluronic acid oligosaccharide chain modified end is the preparation method of the flavonoid compound of glucuronic acid as described in embodiment 1, difference is:

[0088] The final molar concentration ratio of the reaction solution of UDP-GlcNAc, UDP-GlcA and hyaluronic acid trisaccharide-modified flavonoids is 1000:1000:1.

[0089] The product electrophoresis detection results were as follows: Figure 7 Shown in strip 3.

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Abstract

The invention discloses a method for preparing a hyaluronan oligosaccharide chain modified flavonoid compound carrying glucuronic acid on the terminal, and belongs to the technical field of biological pharmacy. According to the method, a flavonoid compound carrying glucuronic acid on the terminal is selected as a start, and a difunctional hyaluronic synthase with beta(1->4) O-linked N-acetylgtucosamine activity and beta (1->3) glucuronyl transferase activity is utilized to synthesize a hyaluronan oligosaccharide chain based on glucuronic acid on the terminal, so that the hyaluronan oligosaccharide chain modified flavonoid compound is prepared. The method can be used for avoiding frequent protecting and de-protecting steps of chemical synthesis, has the advantages of economy, environmental friendliness, high efficiency and the like, is capable of enlarging derivation of flavonoid compounds, preparing novel flavonoid medicines with a drug delivery target label and opening a novel means for researches and development of novel target anti-cancer medicines, and has potential clinical application prospects.

Description

technical field [0001] The invention belongs to the technical field of biopharmaceuticals. The invention relates to a method for modifying a flavonoid compound with glucuronic acid at the end by a hyaluronic acid oligosaccharide chain. Background technique [0002] Flavonoids (Flavonoids) are an important class of polyphenolic compounds that widely exist in nature. With 2-phenylchromone (2-phenylchromone) as the core, two benzene rings (A and B rings) pass through the central three A series of compounds formed by interconnecting carbon chains. Flavonoids are widely distributed in the plant kingdom and are the products of plant secondary metabolism, mostly present in higher plants and ferns. Flavonoids extracted directly from natural plants generally exist in the form of free or glycosides, and the molecules contain multiple phenolic hydroxyl groups. [0003] [0004] The research on the anticancer activity of flavonoids has become a hotspot in the research of tumor pre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P19/60
Inventor 房俊强王鹏付玄薛梦阳
Owner SHANDONG UNIV
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