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A kind of isopentenyl stilbene and its application in the preparation of medicine for treating inflammatory diseases

A technology of isopentenyl stilbene and inflammatory diseases, which is applied in the field of medicine and can solve problems such as tissue damage, microcirculation blockage, damage to vascular endothelial cells and extravascular tissue cells

Active Publication Date: 2019-11-15
JIANGXI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, while ROS kills invading bacteria, it can also cause damage to surrounding normal tissues, causing obstruction of microcirculation, damage to vascular endothelial cells and extravascular tissue cells, release and promote the release of inflammatory mediators, and become a "destroyer".

Method used

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  • A kind of isopentenyl stilbene and its application in the preparation of medicine for treating inflammatory diseases
  • A kind of isopentenyl stilbene and its application in the preparation of medicine for treating inflammatory diseases
  • A kind of isopentenyl stilbene and its application in the preparation of medicine for treating inflammatory diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Preparation of isopentenyl stilbene (±)-dichroma phenol A in dichroma jackfruit:

[0024] Take 13.9 Kg of jackfruit root, extract by leakage with 95% ethanol, and concentrate the extract under reduced pressure to obtain 1.3 Kg of extract. The extract was suspended in 1 L of water, extracted successively with petroleum ether, chloroform, ethyl acetate and n-butanol (volume ratio 2:1), and concentrated to dryness respectively. Take 118.9 g of the extract from the chloroform extraction part, mix the sample with HP-20 macroporous adsorption resin (weight ratio 1:1), put it on HP-20 type macroporous adsorption resin column (column specification: 10*45 cm), and mix with ethanol-water (0~95%) gradient elution to obtain 6 fractions Frs. H1-H6. 50% ethanol eluted fraction Fr. H4 (44.8 g) was subjected to ODS column chromatography (column size: 4*22 cm), MeOH -H 2 O (volume ratio 6:4, 7:3, 8:2, 9:1, 10:0) gradient elution to obtain 15 fractions Frs. H4O1-H4O15. Fraction Fr.H4O...

Embodiment 2

[0026] Structural identification of isopentenyl stilbene (±)-dichromophenol A in jackfruit dichroma:

[0027] (±)-Dichroic pirophenol A, a yellow amorphous powder (acetone). HR-ESI-MS gives quasi-molecular ion peaks m / z 379.1906 ([M-H] - , Calculated value: 379.1915), determine its molecular formula as C 24 h 28 o 4 . Its UV spectrum shows the characteristic absorption of non-conjugated aromatic rings ( lambda max 211 and 285 nm), suggesting that (±)-dichromophorol A may be a dihydrostilbene derivative. (±)-Dichroic pirophenol A 1 H NMR spectrum (600 MHz, acetone- d 6 ) shows the following proton signals: a pair of meta-coupled aromatic ring protons δ H 6.23 (1 H, d, J = 2.3 Hz, H-2) and 6.07 (1 H, d, J= 2.3 Hz, H-4); two aromatic ring protons appear as a singlet δ H 6.98 (1 H, s, H-7) and 6.37 (1H, s, H-10); a 1,1-dimethylallyl-type isoprene substituent δ H 6.24 (1 H, dd, J = 17.5,10.6 Hz, H-23), 4.97 (1 H, dd, J = 17.5, 1.6 Hz, H α -24), 4.9...

Embodiment 3

[0031] Cytotoxicity evaluation experiment of (±)-dichrome pirophenol A on rat PMNs:

[0032] Rat PMNs were isolated and purified using the following experimental procedures. Take clean SD rats (Jiangxi University of Traditional Chinese Medicine Experimental Animal Center, animal qualification certificate number: JZDW2011304), take 9 mL of blood from the orbit, and drop it vertically into a glass centrifuge tube that has been anticoagulated with 1 mL of 1% heparin sodium. Add 4.5% dextran T-500 saline solution at a ratio of 5:1, mix well, and let stand at 4°C for about 1 hour. Take the supernatant, add it to the centrifuge tube pre-filled with lymphocyte separation medium at a ratio of 3:1, 800 rpm (275 g ) Centrifuge for 15 minutes, take out the centrifuge tube, the tube is divided into three layers, the upper layer is light yellow serum, the middle white misty area is monocytes and lymphocytes, and the lower layer is PMNs that settle to the bottom of the tube. Discard the s...

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Abstract

The invention relates to isopentenyl toluylene and application thereof in preparing medicine for treating inflammatory diseases. The isopentenyl toluylene is a new compound separated from Artocarpus styracifolius Pierre which is a plant of moraceae artocarpus, the compound is named as (+ / -)-styracifolius phenol A, and the structure is shown in the description. The compound has strong inhibitory activity on respiratory burst of rat PMNs, the IC50 of the compound is 2.62+ / -0.35 muM, and the compound can be further used for preparing the medicine for treating the inflammatory diseases, and used for clinical treatment of various kinds of oxidative damages such as rheumatoid arthritis, compensatory anti-inflammatory response syndrome, and systemic inflammatory response syndrome caused by excessive activation of the PMNs.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to the application of a prenyl stilbene compound in jackfruit dicolor to the preparation of medicines for treating inflammatory diseases. Background technique [0002] Neutrophils (PMNs) are the body's first line of defense against the invasion of foreign pathogens. When PMNs recognize the small peptide secreted by the receptor or the complex formed by the bacteria and the antibody in the serum, the cell is activated through the mediation of the receptor on the membrane, and a large amount of superoxide anion (O 2 •- ). o 2 •- Under the catalysis of superoxide dismutase and myeloperoxidase, a series of free radical chain reactions occurred, producing various reactive oxygen species (ROS), including hydroxyl radical (HO ), hydrogen peroxide (H 2 o 2 ) and hypochlorous acid (HOCl). These ROS can efficiently eliminate invading pathogenic microorganisms, a phenomenon called re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/23A61K31/05A61P29/00
CPCA61P29/00C07C39/23C07C2602/10
Inventor 任刚李文艳袁金斌易文芳林沁华叶金宝
Owner JIANGXI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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