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Caffeic acid glucoside derivative and preparation method thereof

A technology of caffeic acid and galactoside, which is applied in the field of glycoengineering, can solve problems such as limitations and limitations of glycoside derivatives, and achieve the effects of expanding the application range, increasing water solubility and stability, and broad application prospects

Active Publication Date: 2013-09-18
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although the enzymatic modification of caffeic acid has fewer steps, the process is simple, and it is clean and pollution-free, the natural enzymes that can modify caffeic acid as a substrate for glycosylation are very limited, and the obtained glycoside derivatives are limited to Glucosyl modification
So far, there is no report on enzymatic galactosylation modification of caffeic acid

Method used

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  • Caffeic acid glucoside derivative and preparation method thereof
  • Caffeic acid glucoside derivative and preparation method thereof
  • Caffeic acid glucoside derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Novel caffeic acid galactoside derivatives, the preparation steps are as follows:

[0037] 1. Preparation of β-galactosidase

[0038] Artificially synthesized β-galactosidase gene sequence with GenBank accession number EU734748.1 (encoded protein GenBank accession number is ACE06986.1), ligated it to pET-21b(+) plasmid, and transformed Escherichia coli BL21(DE3) , and then extract the recombinant plasmid, use the plasmid as a template, and introduce a mutation into the enzyme gene sequence by PCR using a mutation kit (Quanjin Easy Mutagenesis System, Beijing);

[0039] The upstream primer is: 5′-CGGGGATGACTCC TTT GGGCAGAAGGTCCA-3'; SEQ ID NO.3

[0040] The downstream primer is: 5′- AAA GGAGTCATCCCCGCCGACCCCCCATCTG-3'; SEQ ID NO.4

[0041] In the primer, TTT encodes phenylalanine, and tryptophan at position 980 is replaced by phenylalanine by PCR;

[0042] PCR amplification conditions were: pre-denaturation at 95°C for 5 minutes; 20 cycles of reaction (denaturatio...

Embodiment 2

[0061] A kind of preparation method of caffeic acid galactoside mixture, following steps are as follows:

[0062] (1) Use phosphate buffer to prepare a reaction system in which the concentration of lactose is 0.2M, the concentration of caffeic acid is 0.05M, and the amino acid sequence is as shown in SEQ ID NO.1, and the amount of β-galactosidase added is 10 μg / mL;

[0063] (2) React the reaction system prepared in step (1) in a water bath at 37°C for 20 minutes, boil to terminate the reaction, centrifuge at 12,000 rpm for 20 minutes, and take the supernatant;

[0064] (3) Separate 2ml of the supernatant obtained in step (2) with a 15mm×100cm Bio-gel P2 chromatographic column, using water as the mobile phase at a flow rate of 0.3mL / min, collect the eluted samples, and thin-layer Analysis and detection, combined products with the same migration distance, freeze-dried and made into powder, namely caffeic acid galactoside.

[0065] TLC detection is as described in Example 1.

...

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Abstract

The invention relates to a caffeic acid glucoside derivative and a preparation method thereof. The caffeic acid galactoside mixture comprises the active ingredients of caffeic acid 3'-O-beta-D-pyran galactoside and caffeic acid 4'-O-beta-D-pyran galactoside, and the mixture has the molecular formula of C15H18O9. The invention also relates to a method for preparing the caffeic acid galactoside mixture. The caffeic acid galactoside is synthesized by employing the mutational beta-galactosidase, and compared with the raw material caffeic acid, the product contains galactosyl, the water solubility and stability are improved, and the application range is widened.

Description

technical field [0001] The invention relates to caffeic acid glycoside derivatives and a preparation method thereof, in particular to a method for synthesizing caffeic acid galactoside by using β-galactosidase mutant enzyme, which belongs to the technical field of sugar engineering. technical background [0002] Caffeic acid (Caffeic acid) belongs to polyhydric phenolic acid compounds, which are widely distributed in plants. Pharmacological effects such as hemostasis and anti-oxidation. Caffeic acid derivatives are hot compounds in the research and development of new drugs in recent years, and have various pharmacological effects such as anti-tumor, anti-oxidation, anti-inflammatory and immune regulation. Most of the currently obtained caffeic acid derivatives are synthesized by chemical methods, and there are only 3 cases of biological enzymatic modification. reaction. [0003] Although the enzymatic modification of caffeic acid has fewer steps, the process is simple, an...

Claims

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Application Information

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IPC IPC(8): C07H15/203C12P19/44
Inventor 卢丽丽肖敏郭玉川
Owner SHANDONG UNIV
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