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Caffeoyl hydroquinone ester and preparation method and application of caffeoyl hydroquinone ester in preparation of tyrosinase inhibitor

A technology of tyrosinase and inhibitors, applied in the field of a new natural compound of caffeoyl p-hydroxyphenol ester, which can solve pigmentation, dark spots, age spots, reduce storage period, nutritional value and market value, pigmentation Diseases and other problems, to achieve the effect of wide application potential and rich material sources

Active Publication Date: 2015-05-13
SOUTH CHINA BOTANICAL GARDEN CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] As a key enzyme in melanin synthesis, its abnormal overexpression can lead to pigmentation diseases in the human body, causing serious health and beauty problems, such as pigmentation, dark spots, age spots, etc.; It plays an important role in synthesis, wound healing, ossification, etc., and is related to tanning in the process of insect molting. It is an important enzyme that insects depend on for survival; in fruit and vegetable and food processing, tyrosinase is the cause of Major enzymes for browning, which catalyze reactions that cause browning of fresh fruits, vegetables and beverages, reducing their shelf life, nutritional value and market value

Method used

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  • Caffeoyl hydroquinone ester and preparation method and application of caffeoyl hydroquinone ester in preparation of tyrosinase inhibitor
  • Caffeoyl hydroquinone ester and preparation method and application of caffeoyl hydroquinone ester in preparation of tyrosinase inhibitor
  • Caffeoyl hydroquinone ester and preparation method and application of caffeoyl hydroquinone ester in preparation of tyrosinase inhibitor

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Experimental program
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Effect test

Embodiment 1

[0028] Example 1: Preparation of caffeoyl p-hydroxyphenol ester p-hydroxyphenyl caffeate in Wedelia chinensis

[0029] 1.1 Instruments and reagents

[0030] The decompression concentration adopts N-1000 rotary evaporator, CCA-1110 circulating cooling box and SB-1000 electric heating constant temperature water bath from Tokyo Physical and Chemical Company of Japan; instrument and C18 reverse-phase chromatographic column (particle size 50 μm, YMC Co. Ltd., Kyoto, Japan, 400 mm × 25 mm); electrospray mass spectrometry (ESIMS) using MDS SCIEX API 2000 LC / MS / MS instrument from Applied Biosystems, USA, with Methanol is used as a solvent for direct sampling determination; 1 H NMR spectrum and 13 C NMR spectrum was determined by Bruker AVANCE 600 nuclear magnetic resonance instrument, and tetramethylsilane was used as internal standard. The color development method is treated with 10% sulfuric acid ethanol solution and then heated for color development.

[0031] 1.2 Plant source a...

Embodiment 2

[0042] Example 2: Detection of tyrosinase inhibitory activity of compound p-hydroxyphenyl caffeate

[0043] 2.1 Reagents and instruments

[0044] Reagents: Tyrosinase was purchased from Sigma Chemical Co. (Sigma-Aldrich, St.Louis, USA), levodopa (L-DOPA) and kojic acid were purchased from Aladdin Industrial Corporation (USA), Na 2 HPO 4 , NaH 2 PO 4 , the compound to be tested was prepared for phytochemical analysis experiments;

[0045] Experimental equipment: microplate reader (Genois microplate reader, Tecan GENios, Switzerland).

[0046] 2.2 Test method

[0047] a) Preparation of drug solution: the compound to be tested, p-hydroxyphenyl caffeate, and kojic acid were formulated with dimethyl sulfoxide (DMSO) to form a 10 mg / ml solution, 67 mmol of phosphate buffer (prepared with ultrapure water), 46 U / ml Tyrosinase solution (prepared with phosphate buffer), 2.5mM L-DOPA (prepared with phosphate buffer).

[0048] b) Using a colorimetric method to complete the determin...

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Abstract

The invention discloses caffeoyl hydroquinone ester, a preparation method of caffeoyl hydroquinone ester and application of caffeoyl hydroquinone ester in preparation of a tyrosinase inhibitor. According to the preparation method, a strong tyrosinase inhibitor compound (p-hydroxyphenyl caffeate) is extracted and separated from sphagneticola trilobata; the plant raw material source is rich; the preparation method is high in economical benefit, and environmentally friendly; the pharmacology experiment shows that the compound p-hydroxyphenyl caffeate has the tyrosinase inhibiting activity superior to that of kojic acid and is expected to be further developed to be a novel synergist of whitening cosmetics, a medicine for treating chromatodermatosis, an insect control agent and even a food preservative, and has good prospect.

Description

Technical field: [0001] The invention belongs to natural medicinal chemistry and relates to the fields of medicine and cosmetics, in particular to a new natural compound of caffeoyl p-hydroxyphenol ester, i.e. p-hydroxyphenyl caffeate, a method for extracting, separating and preparing the new compound from the plant Wedelia chinensis and the Application of compound or pharmaceutically acceptable salt thereof in preparation of tyrosinase inhibitor or related medicine. Background technique: [0002] Tyrosinase, also known as phenol oxidase and polyphenol oxidase, widely exists in microorganisms, plants and mammals, and is a key enzyme that regulates the synthesis of melanin in organisms. Tyrosinase catalyzes the oxidation of monophenolic hydroxyl groups to o-diphenols, and then the o-diphenols are further oxidized to o-diquinones under its catalysis, and then undergoes a series of complex non-enzymatic reaction processes to finally generate melanin , in this process, tyrosina...

Claims

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Application Information

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IPC IPC(8): C07C67/48C07C67/56C07C69/732A61K31/216A61P17/00A01N37/38A01P7/04A61K8/37A61Q19/02A23L3/3517
CPCA23L3/3517A23V2002/00A61K8/37A61Q19/02C07C67/48C07C67/56C07C69/732A23V2200/10
Inventor 谭建文任慧周忠玉徐巧林
Owner SOUTH CHINA BOTANICAL GARDEN CHINESE ACADEMY OF SCI
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