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Method of catalytically synthesizing alpha-monolinolenin by using immobilization lipase

A technology for immobilizing lipase and linolenic acid monoglyceride, which is applied in the direction of being fixed on/in an organic carrier, can solve the problem of hindering the wide application of α-linolenic acid monoglyceride, excessive organic solvent residues in medicine, extraction It can solve the problems of difficult purification and other problems, so as to achieve the effect of easy continuous production, large-scale industrial production and low cost.

Inactive Publication Date: 2010-07-28
JILIN UNIV
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  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the traditional method has many disadvantages: (1) the price of the raw material coix seed is relatively high, and the content of α-linolenic acid monoglyceride in the coix seed itself is very small (about 1.31%); (2) the extraction process is very Complex, difficult to purify the extract, and high cost; (3) A large amount of organic solvents are used in the preparation process, resulting in excessive organic solvent residues in the drug
Therefore, the traditional preparation method has seriously hindered the wide application of α-linolenic acid monoglyceride as a raw material for anticancer drugs.

Method used

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  • Method of catalytically synthesizing alpha-monolinolenin by using immobilization lipase
  • Method of catalytically synthesizing alpha-monolinolenin by using immobilization lipase
  • Method of catalytically synthesizing alpha-monolinolenin by using immobilization lipase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 Pore expansion modification and characterization of mesoporous material SBA-15

[0028] Dissolve 0.8 g of the triblock copolymer compound P123 (Pluronic P123) in deionized water, add it into hydrochloric acid after the P123 is completely dissolved, and stir to dissolve. The mixture was stirred at a constant temperature of 50° C. to 60° C. for 30 to 45 minutes, then 3 ml of ethanol was added, stirred, put into a reaction kettle, and placed in an oven at 100° C. for 48 hours. The product was filtered, washed and dried. Then burn at 500°C-550°C for 6-8 hours to completely remove the surfactant. The product name is: SBA-15 / 80.

[0029] The mesoporous material SBA-15 / 80 was dissolved in deionized water with a mass:volume ratio of 1g:30ml, heated to reflux for 3.5h, the mixture was cooled and centrifuged to remove water, and the white solid was dried in air for 6 days. Take the hydrated mesoporous material and add 130ml of toluene and 15ml of APTES successively, ...

Embodiment 2

[0036] The assembly of embodiment 2 immobilized lipase and determination of its optimum conditions

[0037] Get the mesoporous material NH that embodiment 1 makes 2 -SBA-15 / 80 and glutaraldehyde, mass:volume ratio 1g:30ml, reacted for 3h under stirring, then washed with phosphate buffer to remove unreacted glutaraldehyde. Add 30ml Candida lipase solution to the mesoporous material and react for 5 hours, finally wash with PBS and centrifuge (5000rpm, 13min) until no protein can be detected in the solution.

[0038] In this example, the Candida lipase was replaced by Pseudomonas aeruginosa lipase, the usage is the same, and the effect of the two is also the same.

[0039] For the optimum temperature of immobilized lipase, the optimum pH, the determination of the Michaelis constant (Km) and the thermal stability, see the attached Figure 5-8 .

[0040] Figure 5 It shows the change of optimum temperature before and after lipase immobilization, that is, after the enzyme is imm...

Embodiment 3

[0045] Example 3 Synthesis of α-linolenic acid monoglyceride in organic phase by immobilized enzyme

[0046] Take 1 g of the immobilized enzyme synthesized in Example 2, add the organic solvent n-hexane, and stir evenly. Add linolenic acid and glycerin (20ml each), and the initial concentrations are 25mmol / ml and 30.0mmol / ml respectively. The mixture was incubated in a constant temperature water bath shaker at 20-50°C for a certain period of time. Finally, the reaction mixture was filtered to remove the immobilized enzyme, and n-hexane was evaporated under reduced pressure. The residue is the product alpha-linolenic acid monoglyceride, a coixenolide. Qualitatively and quantitatively determined by high-performance liquid chromatography, the yield is 75-80%.

[0047] In this embodiment, the organic solvent n-hexane can be replaced by ethyl acetate.

[0048] In this example, there is a slight increase or decrease in the amount of each raw material (as within the scope of the ...

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Abstract

The invention discloses a method of catalyzing and synthesizing alpha-glyceryl linolenate with immobilized lipolytic enzyme in the manufacturing method field of a anti-cancer drug material, which comprises the following steps: making immobilized enzyme carrier including hole enlarge of dielectric hole material and the amido modification; making immobilized lipolytic enzyme, synthesizing alpha-glyceryl linolenate with immobilized enzyme in organic medium. The invention provides a good steady, and SBA-15 still shows regular hexagonal structure after modification, a uniform pore path, a big aperture and meets the need of synthesizing alpha-glyceryl linolenate; improvement of the lipase proper temperature improves the productivity; the product is provided with a light yellow color, a good quality, a good curative effect, enhancing heat stability.

Description

technical field [0001] The invention belongs to the technical field of synthesis methods of anticancer drug raw materials, in particular to a method for catalytically synthesizing anticancer drug raw material α-linolenic acid monoglyceride by immobilized lipase method. Background technique [0002] α-linolenic acid monoglyceride is mainly found in the traditional Chinese medicine coicis. As a non-cytotoxic anti-cancer substance, α-linolenic acid monoglyceride can inhibit tumor growth and regulate the immune function of the body. Its role is mainly to induce cell apoptosis, and can reverse drug-resistant tumor cells, and has a synergistic effect with chemotherapy. Clinically, coix seed is mainly used for the treatment of nasopharyngeal carcinoma. [0003] The traditional preparation method of α-linolenic acid monoglyceride is to extract from the raw material coix seed through an organic solvent, and the prior art similar to the present invention is a paper titled "Preparati...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P7/64C12N11/08
Inventor 高波滕利荣孟庆繁王博
Owner JILIN UNIV
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