A kind of method utilizing lipase to catalyze the synthesis of dihydromyricetin monoester compound

A lipase-catalyzed dihydro and dihydromyricetin single technology, which is applied in fermentation and other fields, can solve the problems of seldom reported hydroxyl esterification on flavonoid aglycones, poor oil solubility of dihydromyricetin molecules, and difficulties in hydroxyl esterification reactions, etc. problem, to achieve the effect of reducing production cost, retaining antioxidant activity, and easy continuous production

Inactive Publication Date: 2018-07-03
HUBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Dihydromyricetin molecule has poor oil solubility, which limits its dispersion in the oil phase, which is not conducive to its antioxidant effect
At present, most of the reports on the enzymatic esterification of flavonoids are aimed at the hydroxyl groups on the flavonoid glycosides, and there are few reports on the esterification of the hydroxyl groups on the flavone aglycones.
Most of the dihydromyricetin hydroxyl groups are directly connected to the benzene ring. Due to the electron-withdrawing effect of the benzene ring, the electron cloud density of the oxygen atom of the hydroxyl group decreases, making the hydroxyl esterification reaction difficult.
There is no report on the enzymatic esterification of dihydromyricetin

Method used

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  • A kind of method utilizing lipase to catalyze the synthesis of dihydromyricetin monoester compound
  • A kind of method utilizing lipase to catalyze the synthesis of dihydromyricetin monoester compound
  • A kind of method utilizing lipase to catalyze the synthesis of dihydromyricetin monoester compound

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Experimental program
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Effect test

Embodiment 1

[0029] (1) Dissolve dihydromyricetin in 2 mL of organic solvent, and then add vinyl acetate (the initial concentrations of dihydromyricetin and vinyl acetate are 20 and 500 mmol / L, respectively), and then add 500 U of immobilized Aspergillus niger HGD0823 lipase was reacted for 24 hours at a temperature of 35°C and a shaker speed of 200r / min.

[0030] (2) After the reaction, the reaction solution is centrifuged, the supernatant is taken, the solvent is recovered, and the obtained solid is the product containing dihydromyricetin monoester.

[0031] The organic solvents used in this example are acetonitrile, acetone, tetrahydrofuran, tert-butanol, and dimethyl sulfoxide, respectively. In different organic solvents, the conversion rate (measured by HPLC) of dihydromyricetin under the catalysis of immobilized Aspergillus niger HGD0823 lipase is shown in Table 1.

[0032] Table 1. The conversion rate of dihydromyricetin in different organic solvents

[0033]

Embodiment 2

[0035] (1) Dissolve dihydromyricetin in 2 mL of acetonitrile, and then add vinyl acetate after all the dissolution (the initial concentrations of dihydromyricetin and vinyl acetate are 20 and 500 mmol / L, respectively), and then add 500 U of lipase, The reaction was carried out for 24 hours under the conditions of a temperature of 35° C. and a shaker rotation speed of 200 r / min.

[0036] (2) After the reaction, the reaction solution is centrifuged, the supernatant is taken, the solvent is recovered, and the obtained solid is the product containing dihydromyricetin monoester.

[0037] The lipases used in the present embodiment are free lipases respectively: Penicillium salmonella casei lipase (LPC), Rhizopus sinensis lipase (Lipase RC), Pseudomonas cepacia lipase (PCL), porcine pancreatic lipase (PPL), Rhizopus niger lipase (Lipase RN), Penicillium extensa lipase (PEL), Aspergillus niger HGD0823 lipase; immobilized lipase: Lipozyme IM TL, Lipozyme IM RM, Novozym435, immobiliz...

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Abstract

The invention discloses a method for catalyzing and synthesizing dihydromyricetin monoester by using lipase, which belongs to the field of biocatalysis. The method of the present invention comprises the following steps: dissolving dihydromyricetin and acyl donor in an organic solvent, adding free or immobilized lipase, and reacting on a shaking table at 30-40°C and 200-300r / min for 1-2 days; After the reaction, the reaction solution is centrifuged, the supernatant is taken, the solvent is evaporated, and the obtained solid is dihydromyricetin monoester. The present invention catalyzes the synthesis of dihydromyricetin monoester by free or immobilized lipase for the first time, and the esterification position of the product is at the 3-hydroxyl group with the lowest antioxidant activity, which maximizes the antioxidant activity of dihydromyricetin It improves its oil solubility and makes it more practical. The method has the advantages of low catalyst price, mild reaction conditions, high reaction specificity, high selectivity, repeated use of lipase, low production cost and the like.

Description

technical field [0001] The invention belongs to the field of biocatalysis, and relates to a method for catalyzing and synthesizing dihydromyricetin monoester by using lipase. Background technique [0002] Dihydromyricetin is a flavonoid aglycone compound, chemically named 3,5,7,3',4',5'-hexahydroxy-2,3-dihydroflavonol (dihydromyricetin, DMY), also known as bis Hydromyricetin, dihydromyricetin, staphylophyllin. The mass fraction of dihydromyricetin in the dried stems and leaves of S. chinensis can be as high as more than 30%. Dihydromyricetin has a variety of pharmacological activities, such as anti-inflammatory, analgesic, cough-relieving, expectorant, anti-hypertensive, liver-protecting and anti-alcoholic, fat-reducing, hypoglycemic, enhancing immunity, anti-oxidation and antibacterial effects, etc. , It is expected to be developed into food antioxidants, health food, cosmetics, pharmaceuticals, etc. [0003] Dihydromyricetin molecule has poor oil solubility, which limit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P17/06
Inventor 李卫吴欢李斌万端极
Owner HUBEI UNIV OF TECH
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