Compound having tyrosinase inhibitory activity and synthesis method of compound

A tyrosinase, inhibitory activity technology, used in the fields of food, cosmetics and medicine, can solve the problems of low selectivity, strong acid and strong base, too long reaction time, etc.

Inactive Publication Date: 2015-03-25
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have many drawbacks, such as harsh reaction conditions, toxic reagents and metal catalysts, strong acids and bases, oily products, long reaction times, low yields, low selectivities, and cumbersome post-processing procedures
In addition, in most cases, the synthesis of hydroxychalcone derivatives requires protection and deprotection of hydroxyl groups, which not

Method used

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  • Compound having tyrosinase inhibitory activity and synthesis method of compound
  • Compound having tyrosinase inhibitory activity and synthesis method of compound
  • Compound having tyrosinase inhibitory activity and synthesis method of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 Green Synthesis Method of 1,3,5-Tris-(2,4-dihydroxy-phenyl)-pentane-1,5-dione

[0029] Weigh 5g of 2,4-dihydroxybenzaldehyde, 2.5g of 2,4-hydroxyacetophenone, 2.1g of boric acid, 0.5g of ascorbic acid in a 50mL round bottom flask, add 25mL of PEG400 and stir to dissolve, place in a 120°C oil bath Stirred and refluxed for 6h, followed the progress of the reaction by TLC. The reaction solution was extracted three times with ethyl acetate, and the organic phase was concentrated to dryness under reduced pressure; the dried sample was eluted on a silica gel column (particle size 10-40μ) with dichloromethane:methanol=20:1 (v / v), and collected The eluate was concentrated and dried to obtain a dry sample; the dry sample was separated by gel column chromatography (Sephadex LH-20), and eluted with methanol-water (v / v, 1:1); Liquid chromatography (Waters preparative high performance liquid chromatograph, dual-wavelength detector, preparative column is YMC (250mm * 20mm,...

Embodiment 2

[0035] Example 2 Evaluation method for tyrosinase inhibitory activity

[0036] 1,3,5-tris-(2,4-dihydroxy-phenyl)-pentane-1,5-dione was dissolved in DMSO to prepare 50, 10, 5, 2.5, 0.5 μg / mL respectively. The positive control kojic acid was made into solutions with concentrations of 50, 25, 10, 5, and 2.5 μg / mL. Take 300 μL of each of the five concentrations of solutions, use 700 μL of pH 6.8 phosphate buffer solution to make 1 mL, add 0.1 mg / mL tyrosine 1 mL, and then add 1 mL of pH 6.8 phosphate buffer solution. Tyrosinase (400U / mL), incubate at 37°C for 20min, and measure the absorbance at 492nm.

[0037] Enzyme activity inhibition rate=[(A2-A1)-(B2-B1)] / (A2-A1)×100%

[0038] A1 is the absorption value without inhibitor at 0 min; A2 is the absorption value without inhibitor after 20 min;

[0039] B1 is the absorption value of inhibitor added at 0 min; B2 is the absorption value of inhibitor added after 20 min.

Embodiment 3

[0040] Example 3 Evaluation of compound tyrosinase inhibitory activity

[0041] IC of 1,3,5-Tris-(2,4-dihydroxy-phenyl)-pentane-1,5-dione inhibiting tyrosinase 50 The IC of kojic acid is 5.66 μM 50 IC of 67.6 μM, 2,4-dihydroxybenzaldehyde 50 >200 μM, IC of 2,4-dihydroxyacetophenone 50 >300 μM. The tyrosinase inhibitory activity of the compound 1,3,5-tris-(2,4-dihydroxy-phenyl)-pentane-1,5-dione is far greater than that of the positive control kojic acid and the reaction raw material 2,4-hydroxy Acetophenone and 2,4-dihydroxybenzaldehyde.

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Abstract

The invention discloses a compound having a tyrosinase inhibitory activity and a synthesis method of the compound, belonging to the fields of foods, cosmetics and medicines. The synthesis method comprises the following steps: carrying out a reaction between 2,4-dihydroxy benzaldehyde and 2,4-dihydroxy acetophenone under the catalysis of boric acid and vitamin C by taking polyethylene glycol 400 (PEG400) as a solvent for 6h so as to achieve the green synthesis of an efficient tyrosinase inhibiting agent; and carrying out gel column chromatography and high performance liquid chromatography separation so as to prepare a pure product of the efficient tyrosinase inhibiting agent. On the basis of mass spectrum and nuclear magnetism analysis, the substance is determined as 1,3,5-tris-(2,4-dihydroxy-phenyl)-pentane-1,5-dione. The compound disclosed by the invention can be used for effectively inhibiting enzymatic browning of fruits and vegetables, the preparation of whitening cosmetics as well as the preparation of a pharmaceutical preparation for preventing and treating human hyperpigmentation diseases and melanoma caused by excess melanin as well as other requirements to inhibit the activity of the tyrosinase.

Description

technical field [0001] The invention relates to a compound with tyrosinase inhibitory activity and a synthesis method thereof, belonging to the fields of food, cosmetics and medicine. Background technique [0002] Browning and spoilage caused by pathogen infection are two important factors causing postharvest losses of fruits and vegetables. During the processing and storage of fruits and vegetables, enzymatic browning caused by tyrosinase (EC 1.14.18.1) not only affects the color and appearance of products, but also destroys the amino acids of essential products, reduces their nutrition and digestion and absorption, and eventually Seriously affect the nutritional value and market value of the product. Many fruits and vegetables have a short shelf life due to factors such as fungal diseases, mechanical damage and aging. Normally, natural flora often exists in fruit and vegetable products, and may also exist in the process of human consumption. They are generally not toxic ...

Claims

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Application Information

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IPC IPC(8): C07C49/83C07C45/74A23B7/154A61K8/35A61Q19/02A61K31/12A61P17/00A61P35/00
CPCC07C45/74C07C49/83
Inventor 郑宗平陈洁董雪
Owner JIANGNAN UNIV
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