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Chlorogenic acid acylate capable of improving bioavailability of chlorogenic acid and application thereof

A technology of chlorogenic acid acylate and chlorogenic acid, which is applied in the field of biomedicine, can solve the problems of low bioavailability, unstable polyphenolic compounds, and difficulty in fully exerting the drug effect, so as to improve blood drug concentration, Increased bioavailability, enhanced inhibitory effect

Active Publication Date: 2015-08-05
SICHUAN JIUZHANG BIO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Chlorogenic acid has anti-inflammatory, anti-virus, anti-tumor, and immune-enhancing effects, and is unstable under acid, alkali, light and high temperature conditions. Zhou Honghao, Olthof MR and Gonthier MP and other literature reports indicate that chlorogenic acid is an unstable polyphenolic compound, and is easily affected by factors such as digestive tract flora, and the bioavailability of oral administration is low
Margreet et al. further confirmed in the rat ileostomy experiment that only one-third of the administered dose was absorbed into the blood circulation in the small intestine of rats administered orally. This experimental phenomenon is related to the intestinal flora. Metabolism is closely related; therefore, it is difficult for chlorogenic acid to fully exert its medicinal effect through oral administration

Method used

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  • Chlorogenic acid acylate capable of improving bioavailability of chlorogenic acid and application thereof
  • Chlorogenic acid acylate capable of improving bioavailability of chlorogenic acid and application thereof
  • Chlorogenic acid acylate capable of improving bioavailability of chlorogenic acid and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A chlorogenic acid acylate that improves the bioavailability of chlorogenic acid, characterized in that it has the following structural formula:

[0026]

[0027] where: R 1 , R 2 , R 3 , R 4 , R 5 for RCO + functional group or H + ion, RCO + Functional groups in R 1 , R 2 , R 3 , R 4 , R 5 any one or more of these positions.

[0028] The RCO + R in the functional group is an alkyl group containing 1-6 carbon atoms.

[0029] The chlorogenic acid acylate with such a structure can improve bioavailability and enhance drug efficacy.

[0030] The medicine is an oral preparation prepared by adding chlorogenic acid acylate as an active ingredient and adding one or more pharmaceutically acceptable excipients.

[0031] Wherein, the oral preparations are tablets, capsules, granules, powders, pills, and oral liquids.

[0032] The unit preparation of the oral preparation contains 1-1000 mg of chlorogenic acid acylate, and in the optimized scheme, the unit prepara...

Embodiment 2

[0038] (1) Chlorogenic acid, commercially available; chlorogenic acid acylate: R 1 , R 2 and R 3 for H + ions, where R 4 , R 5 for C 2 h 3 o + , marked as sample 1; R 1 , R 2 and R 3 for C 3 h 5 o + , where R 4 , R 5 for H + ions, labeled as sample 2; R 1 , R 4 and R 5 for H + , where R 2 , R 3 for C 7 h 5 o + ions, labeled as sample 3.

[0039] The preparation method of sample 1 can be: 100ml DMF electromagnetic stirring, add 50g chlorogenic acid, keep the temperature at 10°C, add 0.1ml pyridine dropwise, then add 10ml acetic anhydride to react for 24 hours, vacuum dry at 80°C for 12 hours until dry, add 100ml acetic acid After dissolving in ethyl ester (at room temperature), add 20ml of distilled water to wash three times, separate ethyl acetate and spin dry to obtain chlorogenic acid with acetylated 4 and 5 phenolic hydroxyl groups.

[0040] The preparation methods of samples 2 and 3 may be similar or close to those in sample 1.

[0041] (2) Tes...

Embodiment 3

[0063] (1) Animals BALB / C-nu mice, weighing 18-24 g, were provided by the Experimental Animal Center of Sichuan University.

[0064] (2) Drug Chlorogenic acid, commercially available; Chlorogenic acid acylate: R 1 , R 2 and R 3 for H + ions, where R 4 , R 5 for C 2 h 3 o + , marked as sample 1; R 1 , R 2 and R 3 for C 3 h 5 o + , where R 4 , R 5 for H + ion, labeled as sample 2; R 1 , R 2 , R 4 and R 5 for H + ions, where R 3 for C 7 h 5 o + , labeled as sample 3.

[0065] (3) Cell culture SPCA-1 cell is a human lung adenocarcinoma cell line. The cells were routinely resuscitated and passaged. The second-generation mouse tumor was taken, washed 3 times with Hank's solution, blood stains, fat and necrotic tissue were removed, and the tumor was cut into pieces. 1mm×1mm×1mm fragments, rinsed twice with Hank’s solution, added physiological saline (1g:3ml) in proportion, then ground in a glass homogenizer, filtered through a 80-100 mesh screen to make a si...

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Abstract

The invention especially relates to a chlorogenic acid acylate capable of improving bioavailability of chlorogenic acid and application of the chlorogenic acid acylate with a structural formula as described in the specification in preparation of drugs used for treating tumors, belonging to the field of biological medicine. The chlorogenic acid acylate provided by the invention can improve the in-vivo bioavailability of chlorogenic acid, thereby overcome the problem of low absorptivity of chlorogenic acid in oral administration due to influence of intestinal florae and substantially improving the inhibition effect of chlorogenic acid on tumors.

Description

technical field [0001] The invention belongs to the field of biomedicine, in particular to a chlorogenic acid acylate for improving the bioavailability of chlorogenic acid and its application. Background technique [0002] Chlorogenic acid (English: Chlorogenic acid) is also known as coffee tannin. That is, 3-caffeoylquinic acid, which is a polyphenolic compound, widely exists in higher dicotyledonous plants and ferns, mainly in Lonicera (Lonicera) and Artemisia (Artemisia) plants of Compositae, among which The plants with higher content are mainly eucommia, honeysuckle, sunflower, eucommia, coffee, cocoa and so on. [0003] Chlorogenic acid has anti-inflammatory, anti-virus, anti-tumor, and immune-enhancing effects, and is unstable under acid, alkali, light, and high temperature conditions. According to reports in the literature by Zhou Honghao, Olthof MR, and Gonthier MP, chlorogenic acid is unstable and more Phenolic compounds, and are easily affected by factors such ...

Claims

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Application Information

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IPC IPC(8): A61K31/216A61P35/00
CPCA61K31/216
Inventor 张洁黄望张亮
Owner SICHUAN JIUZHANG BIO TECH CO LTD
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