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A bibenzyl derivative in dendrobium officinale leaves and its preparation method and application

A bibenzyl and compound technology, applied in the field of medicine, can solve problems such as waste of biological resources, and achieve the effects of extending the value chain, novel structure, and significant respiratory burst activity of PMNs

Active Publication Date: 2020-06-09
JIANGXI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The medicinal part of Dendrobium officinale is its stem, so when harvesting, a large number of leaves are directly discarded as agricultural by-products, resulting in a certain waste of biological resources

Method used

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  • A bibenzyl derivative in dendrobium officinale leaves and its preparation method and application
  • A bibenzyl derivative in dendrobium officinale leaves and its preparation method and application
  • A bibenzyl derivative in dendrobium officinale leaves and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Preparation of bibenzyl compound denofficin in Dendrobium officinale leaves

[0030] Take 30 kg of shade-dried Dendrobium officinale leaves, crush them, and extract them twice with 150 L of 95% ethanol at room temperature for 20 days each time, filter the extract, recover the solvent under reduced pressure, and obtain 1.7 kg of black extract. Take 1.5 kg of extract, disperse it with 3 L of 10% ethanol hot solution, put it on HP-20 macroporous adsorption resin column (50 × 15 cm), and then wash it with water, 10% ethanol, 20% ethanol, 30% ethanol, 40% ethanol , 50% ethanol, 60% ethanol, 70% ethanol, 80% ethanol, and 90% ethanol for gradient elution, and each gradient eluted with 5 column volumes to obtain 10 fractions frs. H0-H9.

[0031] Fraction fr. H7 (76.2 g) eluted with 70% ethanol was chromatographed on MCI CHP-20P resin column and eluted with ethanol-water solvent system (20:80~90:10) gradient to obtain 8 fractions frs. H7M1 -H7M8. The fraction fr. H7M...

Embodiment 2

[0033] Example 2 Structural identification of 3 bibenzyl compounds isolated from Dendrobium officinale leaves

[0034] Compound 1 is a white amorphous powder. HR-ESI-MS gives quasi-molecular ion peaks m / z 629.2388 ([M-H] - , Calculated value: 629.2392), determine its molecular formula as C 36 h 38 o 10 . The IR spectrum of Denofficin shows the hydroxyl group (3519, 3445 cm -1 ), methoxy (2936, 2852 cm -1 ), carbonyl (1733 cm -1 ) and aromatic rings (1606, 1516,1454 cm -1 ) characteristic absorption. That 1H NMR spectrum (600 MHz, CDCl 3 ) shows 12 proton signals from four aromatic ring systems. Among them, 8 are from two independent A 2 B 2 Type aromatic ring spin coupling system signal: δ H 7.10 (2 H, d, J = 8.5 Hz, H-2′, 6′), 6.83 (2 H, d, J = 8.5 Hz, 3′, 5′), 7.04(2 H, d, J = 8.3 Hz, H-2′′′, 6′′′), 6.70 (2 H, d, J = 8.3 Hz, 3′′′, 5′′′); 2 signals from a set of 1,3,4,5-symmetric tetrasubstituted aromatic ring protons: δ H 6.55 (2 H, s, H-2′′, 6′′)...

Embodiment 3

[0039] Example 3 The cytotoxicity evaluation experiment of the three bibenzyl compounds isolated on rat PMNs

[0040] Rat PMNs were isolated and purified using the following experimental procedures. Take clean-grade SD rats (Jiangxi University of Traditional Chinese Medicine Experimental Animal Center, animal license number: SCXK (Gan) 2018-0003), take 9 mL of blood from the orbit, drop vertically into the glass that has been anticoagulated with 1 mL of 1% heparin sodium in a centrifuge tube. 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 t...

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Abstract

Dendrobium officinale is a rare medicinal plant, stem is the medicinal part of dendrobium officinale, leaves of dendrobium officinale are directly discarded as agricultural byproducts, and certain biological resource waste is caused. The invention relates to a bibenzyl compound extracted from dendrobium officinale leaves, a preparation method of the bibenzyl compound and application of the bibenzyl compound in preparation of medicines for treating inflammatory diseases. The bibenzyl compound is a new compound, is named as denofficin, and has a structure shown in the invention specification. Itis shown by activity test results that denofficin has strong inhibitory activity on rat neutrophil respiratory outbreak, the half inhibitory concentration is 0.22 + / -0.09 [mu]M respectively, and denofficin can be further used for preparing drugs for treating inflammatory diseases. The invention provides a theoretical basis for preparing medicines for treating inflammatory diseases by comprehensively utilizing waste biological resources in dendrobium officinale production process.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a bibenzyl compound in the leaves of dendrobium officinale, a preparation method thereof, and an application in preparation of medicines for treating inflammatory diseases. Background technique [0002] Respiratory burst of neutrophils (PMNs) refers to the process by which activated neutrophils consume large amounts of oxygen to generate reactive oxygen species (ROS). ROS has high reactivity and can undergo redox reactions with cell membranes, nucleic acid molecules, and proteins, causing damage and death to biological cells. Therefore, when foreign pathogens invade, PMNs are activated as the host's first line of defense against the invasion of foreign pathogens, and then release ROS through respiratory burst to play a bactericidal function. However, the activation of PMNs is a double-edged sword. Normally, it can eliminate exogenous pathogens, remove necrotic tissue, and pro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D319/20A61P29/00A61P19/02
CPCA61P19/02A61P29/00C07D319/20
Inventor 任刚陈云龙吴春花肖川云叶金宝周家林
Owner JIANGXI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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