Application of lipid-modified substance of chlorogenic acid and derivative thereof

A technology of lipid modification and derivatives, which is applied in the field of medicine, can solve the problems of low bioavailability and poor membrane permeability, and achieve the effects of enhancing membrane permeability, improving lipophilicity, and facilitating processing and molding

Inactive Publication Date: 2015-08-12
任静 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The present invention aims at chlorogenic acid and its derivatives due to their good polarity, poor membrane permeability, low bioavailability during administration, and being easily decomposed by various digestive enzymes in the gastrointestinal tract, which limits the development of oral preparations, etc. To solve the problem, pre

Method used

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  • Application of lipid-modified substance of chlorogenic acid and derivative thereof
  • Application of lipid-modified substance of chlorogenic acid and derivative thereof
  • Application of lipid-modified substance of chlorogenic acid and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Get chlorogenic acid and derivatives thereof and lipid equivalent to 0.5 times the weight of chlorogenic acid and derivatives thereof; add an appropriate amount of ethyl acetate, the amount of ethyl acetate used is to make the reaction concentration of chlorogenic acid and derivatives thereof 6mg / ml; reflux at 55°C with constant magnetic stirring for 0.5h to obtain the reaction solution; freeze-dry the reaction solution or dry it under reduced pressure to obtain the crude lipid film of chlorogenic acid and its derivative lipid modification; add diethyl ether to the crude product, Make it fully dispersed to obtain a dispersion liquid; filter the above dispersion liquid, take the filtrate and freeze-dry it again or dry it under reduced pressure to obtain the refined lipid-modified product of chlorogenic acid and its derivatives.

Embodiment 2

[0039] Get chlorogenic acid and derivatives thereof and lipid equivalent to 25 times the weight of chlorogenic acid and derivatives thereof; add appropriate amount of chloroform, the amount of chloroform used is to make the reaction concentration of chlorogenic acid and derivatives thereof be 48mg / ml; Under the condition of 15°C, constant temperature magnetic stirring and reflux for 3.5 hours to obtain the reaction solution; freeze-dry the reaction solution or dry it under reduced pressure to obtain the crude product of chlorogenic acid and its derivative lipid modified lipid film; add ethyl acetate to the crude product to make Fully disperse to obtain a dispersion liquid; filter the above dispersion liquid, and take the filtrate to freeze-dry or dry under reduced pressure again to obtain chlorogenic acid and its derivative lipid modified products.

Embodiment 3

[0041] Take chlorogenic acid and its derivatives and lipid equivalent to 1 times the weight of chlorogenic acid and its derivatives; add an appropriate amount of ethanol, the amount of ethanol used is such that the reaction concentration of chlorogenic acid and its derivatives is 20 mg / ml; Under the condition of 40°C, constant temperature magnetic stirring and reflux for 2.5h to obtain the reaction solution; freeze-dry the reaction solution or dry it under reduced pressure to obtain the crude product of chlorogenic acid and its derivative lipid modified lipid film; add dichloromethane to the crude product to make it Fully disperse to obtain a dispersion liquid; filter the above dispersion liquid, and take the filtrate to freeze-dry or dry under reduced pressure again to obtain chlorogenic acid and its derivative lipid modified products.

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Abstract

The invention provides a lipid-modified substance of chlorogenic acid and a derivative thereof, and a preparation and purification method of the lipid-modified substance, wherein the lipid-modified substance includes the chlorogenic acid or the derivative thereof and phosphoglyceride. A preparation process includes steps of performing constant-temperature magnetic stirring reflux for a certain time to the chlorogenic acid or the derivative thereof and the phosphoglyceride with an aprotic solvent and drying an obtained reaction liquid to obtain a crude product. A purification process includes the steps of re-dissolving the crude product with filtration to obtain a filtrate and then drying the filtrate. The lipid-modified substance of the chlorogenic acid and the derivative thereof is high in composition rate and can significantly improve the fat-solubility of the chlorogenic acid and the derivative thereof, so that a subsequent preparation is convenient to process and shape. The lipid-modified substance can be used as an intermediate for preparing a lipidosome, nano particles, polymer micelles or a dendritic polymer and the like nano drug-delivery systems and micro emulsion, self-micro emulsion and the like micron drug-delivery systems, thereby enhancing in-vivo absorption of the chlorogenic acid and the derivative thereof and further increasing the bioavailability of the medicines in a preparation.

Description

technical field [0001] The invention relates to a lipid modification of chlorogenic acid and its derivatives and a preparation and purification method thereof, belonging to the technical field of medicine. Background technique [0002] Chlorogenic acid (ChA), also known as coffee tannin, is an ester formed by condensation of caffeic acid (CA) and quinic acid (quinic acid, QA), and belongs to polyphenols compounds with a wide range of biological activities. Its sources are mainly the dried flower buds or flowers with early blooming of honeysuckle, honeysuckle, red gland honeysuckle, mountain silver flower or hair style honeysuckle, leaves of Eucommia ulmoides, fruit of Rosaceae hawthorn, and the fruit of Rosaceae Hawthorn. Cauliflower plant, Sapinaceae plant willow, Eurasian water keel root, Verbenaceae plant Pseudomonas root, Brassicaceae plant cabbage stems and leaves, Polygonaceae plant flat-planted whole plant and Rubiaceae plant Pompeo Vegetables and other herbs. [0...

Claims

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Application Information

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IPC IPC(8): A61K47/26A61K31/216A61K9/127A61K9/51A61K9/107A61P31/04A61P31/12A61P37/08A61P7/00A61P1/16A61P35/00A61P9/12A61P3/06A61P39/06A61P25/00A61P9/00
Inventor 任静赖可
Owner 任静
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