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Novel tyrosinase inhibitor and use thereof

A technology of tyrosinase and inhibitors, applied in the field of biphenyl glycoside compounds, can solve problems such as difficult to maintain stable product quality, achieve good skin pigmentation, improve melanin production inhibition effect and whitening effect, and prevent skin pigmentation Effect

Inactive Publication Date: 2006-09-06
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these extracts often show different effects due to differences in production areas, and it is difficult to maintain stable product quality

Method used

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  • Novel tyrosinase inhibitor and use thereof
  • Novel tyrosinase inhibitor and use thereof
  • Novel tyrosinase inhibitor and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1, the preparation of the biphenyl glycoside derivative represented by the following formula I

[0028]

[0029] Take the dried fruit of Pyracantha fortuneana in Qinling Mountains, Shaanxi, use 5 times the amount of 60% ethanol solution, heat reflux to extract three times, each time for 2 hours, combine the extracts, filter to remove insoluble matter, and concentrate the filtrate under reduced pressure to dry. The compound was dispersed in an equal volume of water and extracted with chloroform and n-butanol successively. The n-butanol extraction part was dried under reduced pressure in vacuum to obtain the n-butanol extract. Subsequently, carry out chromatography with macroporous adsorbent resin open column, be respectively 10, 30, 50, 70, 95% ethanol aqueous solution gradient elution with concentration; Get 30% ethanol aqueous solution elution part and carry out silica gel open column chromatography, The chloroform:methanol was 20:1, 10:1, 4:1, 2:1, 1:1 ...

Embodiment 2

[0048] Example 2: Determination of Tyrosinase Inhibitory Activity

[0049] Test samples: Compounds 1-4 prepared in Example 1 were taken, and tyrosinase was purchased from Sigma Company and extracted from mushrooms.

[0050] Reference substance: arbutin

[0051] Test method: firstly, the substrate L-tyrosine was dissolved in a phosphate buffer solution (25 mM, pH 6.8) to reach a concentration of 0.1 mg / mL. Into a 96-well plate, 40 μL of the above substrate solution, 80 μL of phosphate buffer (25 mM, pH 6.8), and 40 μL of formula (I) dissolved in 20% methanol-water were added. Add 40 μL of 20% methanol-water to the blank control air. Add 40 μL of tyrosinase in phosphate buffer solution (100 U / mL, 25 mM, pH 6.8) to start the reaction, and incubate at 37° C. for 30 minutes. The absorbance of each well was measured at 492 nm before and after incubation.

[0052] According to the absorbance at 492nm, the inhibitory rate (%) of compound (I) to tyrosinase is calculated, and the co...

Embodiment 3

[0061] Example 3: Whitening Cream

[0062] Prescription: compound 3 0.1g cysteine ​​0.1g

[0063] Stearic acid 10.0g Cetyl alcohol 4.5g

[0064] Lanolin 1.0g Propylene Glycol 15.0g

[0065] Triethanolamine 0.7g Sodium Lauryl Sulfate 0.5g

[0066] Ethyl p-hydroxybenzoate 0.1g Distilled water 68.ml

[0067] Preparation method: mix stearic acid, cetyl alcohol, and lanolin; mix another compound, propylene glycol, triethanolamine, sodium lauryl sulfate, ethyl p-hydroxybenzoate, and distilled water, and heat them in a beaker until melted Or dissolve, store at about 70°C, add the oil phase to the water phase with stirring, and stir until condensed to obtain

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PUM

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Abstract

The invention relates to a new tyrosinase inhibitor and its usage. The inventive content is that it provides biphenylglycosidicderivatives which can be used in the spheres of medicine and daily-use chemistry as melanin inhibiting agents or brightening agents, speaking in detail, it provides biphenylglycosidicderivatives represented by the above general formula (I), in which R1 stands for hydrogen, hydroxy,oxomethyl or gluconic group, R2 stands for hydrogen, hydroxyl or gluconic group, and R3 and R4 stand for hydrogen or gluconic group; and provides compositions with the said tyrosinase inhibitors. The new tyrosinase inhibitors and the compositions with the new compounds can be used as cosmetics to restrain melanin or brighten, medicines, externally used skin-care agent and so on.

Description

technical field [0001] The invention relates to a biphenyl glycoside compound, which is a new tyrosinase inhibitor and is used in the fields of medicine, food and daily chemical industry as a melanin inhibitor or whitening agent. Background technique [0002] Skin pigmentation caused by sun exposure and other reasons has become a big worry for young and middle-aged people, especially young women. With the improvement of material living standards, people's requirements for healthy and whitening skin are increasing day by day, and the consumer market is also expanding. [0003] Recent studies have proved that hyperpigmentation is caused by the activation of melanin-producing enzymes in melanocytes in the epidermis by ultraviolet rays to produce pigments. In the process of melanin production, tyrosinase converts tyrosine into dopa and dopaquinone, and polymerizes into macromolecular melanin through non-enzymatic oxidation (Li Shaoyong et al., "Journal ...

Claims

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Application Information

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IPC IPC(8): C07H15/20A61K31/70A61K8/60A61Q19/02
Inventor 姚新生栗原博戴毅
Owner JINAN UNIVERSITY
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