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Application of flavone diglucuronides in the preparation of cyclooxygenase inhibitors

A technology of cyclooxygenase and compound, applied in application, anti-inflammatory agent, drug combination, etc., can solve the problem of cardiovascular side effects and so on

Active Publication Date: 2021-06-25
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, most cyclooxygenase inhibitors are selective inhibitors, that is, they only inhibit COX-1 or COX-2. However, such selective inhibitors usually have side effects on the gastrointestinal tract and cardiovascular system.

Method used

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  • Application of flavone diglucuronides in the preparation of cyclooxygenase inhibitors
  • Application of flavone diglucuronides in the preparation of cyclooxygenase inhibitors
  • Application of flavone diglucuronides in the preparation of cyclooxygenase inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0121] Example 1 Golden eriodictine-7-O-[β-D-glucuronic acid-(1→2)]-β-D glucuronide, apigenin-7-O-[β-D-glucose uronic acid-(1→2)]-β-D-glucuronide and luteolin-7-O-[β-D-glucuronic acid-(1→2)]-β-D-glucose Preparation of aldoside

[0122] Experimental method one:

[0123] (1) Extraction: get medicinal material Medicago truncatula, pulverize (cross 24 mesh sieves), add 80% methanol aqueous solution and reflux extraction, alcohol consumption is 10 (v / m) times of medicinal material amount, extract 3 times, each time 1 hour, will The extracts were filtered, combined, and dried to obtain the dry extract of Medicago truncatula. The extract was suspended in 4 times the amount of water, and the supernatant was covered with AB-8 macroporous adsorption resin, statically adsorbed for 2 hours, removed with water 3 times the volume of the resin, and then eluted with 20% ethanol, and the eluate was collected. Concentrate under reduced pressure to obtain the total flavonoid glucuronide fract...

Embodiment 2

[0137] Example 2 COX inhibitory activity of flavonoid diglucuronides of the present invention

[0138] 1. Instrument

[0139] Microplate reader Labsystems, wellscan, MK.2

[0140] Centrifuge KA-1000 Shanghai Feige

[0141] Double ultra-clean workbench, Suzhou Purification

[0142] CO 2 Incubator, PHARMA SCIENTIFIC

[0143] Adjustable pipette (Finland, 5-40ul, 40-200ul, 200-1000ul)

[0144] 2. Materials

[0145] Cox Fluorescent Inhibitor Screening Assay Kit (Cayman, USA);

[0146] 96-well black plate (Corning, USA);

[0147] Imported pipette tip (Axygen, USA);

[0148] Indomethacin batch number: 080401Sigma;

[0149] SC-560:

[0150] NS-398:

[0151] Comparative compound 1:

[0152] 3. Method

[0153] 1) Mix buffer (1X), heme, fluorescent substrate ADHP, COX-1 / COX-2, and test compound in sequence in a 200 μl reaction system, and incubate at 25° C. for 5 minutes.

[0154] 2) Adding the cyclooxygenase substrate arachidonic acid.

[0155] 3) Carefully shake th...

Embodiment 3

[0170] Example 3 Pharmacodynamic effects of flavonoid diglucuronide compounds of the present invention on acute inflammation in rats induced by p-carrageenan

[0171] 1 experimental animal

[0172] 1.1 Name: SD rat

[0173] 1.2 Source: Shanghai Sipro-Bikay Experimental Animal Co., Ltd.

[0174] 1.3 Weight: 130-150g

[0175] 1.4 Gender: male

[0176] 1.5 Certificate of Conformity: SCXK (Shanghai) 2008-0016

[0177] 2. Experimental dose design

[0178] Design low and high efficacy dose groups, the doses are respectively: 5mg / kg and 25mg / kg.

[0179] 3 drug preparation

[0180] The low-dose group dissolved 5mg of the drug into 10ml, and the high-dose group dissolved 25mg of the drug into 10ml.

[0181] 4 route of administration and capacity

[0182] 4.1 Route: Oral

[0183] 4.2 Capacity: 100g Rat: 1ml

[0184] 4 positive drugs:

[0185] 4.1 Name: Indomethacin

[0186] 4.2 Provider: Shanghai Xinyi Huanghe Pharmaceutical Co., Ltd.

[0187] 4.3 Batch number: 091201

[...

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Abstract

The invention discloses an application of a flavone diglucuronide compound (compound of formula I) in the preparation of cyclooxygenase inhibitors, specifically, the flavone diglucuronide compound of the invention (compound of formula I) ) has anti-inflammatory activity and cyclooxygenase inhibitory activity, therefore, it can be developed into COX inhibitors and anti-inflammatory drugs, and has great application prospects.

Description

technical field [0001] The invention relates to the field of medicines, in particular to the application of a flavone diglucuronide compound in the preparation of cyclooxygenase inhibitors. Background technique [0002] Flavonoid diglucuronides can be isolated from plants (such as Medicago truncatula), structurally two molecules of glucuronides are connected by 1-2 glycosidic bonds, and then glucuronides are glucuronidated with flavone glycosides. There are very few reports on this type of structural activity, mainly focusing on antioxidant and anti-aging activities. [0003] Cyclooxygenase (cyclooxygenase, COX), also known as prostaglandins (PG) endoperoxidase, is a membrane-bound protein and the rate-limiting enzyme that catalyzes the conversion of arachidonic acid into prostaglandins. Current studies have shown that there are at least two isomers of COX, namely COX-1 and COX-2. COX-1 is structurally expressed in most tissue cells and participates in maintaining physiolo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/7048A61P29/00A61P25/00A61P15/00A61P19/02A61P15/02A23L33/105
CPCA23V2002/00A61K31/7048A23V2200/30
Inventor 胡晓杨义芳许慧牛莉鑫黄春跃刘欣
Owner SHANGHAI INST OF PHARMA IND CO LTD