CN106045866A - Synthesis and application of sinapine chlorate - Google Patents
Synthesis and application of sinapine chlorate Download PDFInfo
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- CN106045866A CN106045866A CN201610520277.6A CN201610520277A CN106045866A CN 106045866 A CN106045866 A CN 106045866A CN 201610520277 A CN201610520277 A CN 201610520277A CN 106045866 A CN106045866 A CN 106045866A
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- chlorate
- choline ester
- sinapic acid
- acid choline
- sinapine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
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- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention belongs to the field of natural active drugs, and particularly relates to synthesis of sinapine chlorate and application thereof in the aspect of treating inflammation. The synthesis includes that sinapine chlorate is prepared through rapeseed meal; adopting a mouse ear swelling experiment method to verify that sinapine chlorate can be applied in drugs for treating inflammation. The synthesis has the advantages that a sinapine chlorate drug is free of side effect, good in action effect, free of dosage dependence, short in half-life period and supportive of long-time use and can meet needs on treating inflammation.
Description
Technical field
The invention belongs to natural activity drug world, be specifically related to the synthesis of sinapic acid choline ester. chlorate and in treatment inflammation side
Application on face.
Background technology
Inflammation (Inflammation) is the main pathological reaction of numerous disease, is that various damage factors are sent out by body tissue
Raw defence is main reaction.Mainly in the presence of blood vessel, body fluid and cell, there is a series of change in body tissue local
Change, include the reaction beneficially removing pro-inflammatory cytokine, also include that the pathological changes that can cause own cells, tissue or even organ is anti-
Should, so inflammatory reaction is substantially a kind of damage and the process of antibody Monoclonal.
The recovery effects of inflammation is often depending on the comparison of damage and injury-resistance, if inflammatory reaction is relatively more violent,
Pro-inflammatory cytokine fails to be removed in time, and damaged tissues or organ are the most well repaired, and the result of inflammatory reaction is not only
Have a strong impact on the normal learning life of people, even life can be constituted a threat to.The hydrothorax that causes such as pleuritis, pericarditis
The joint deformities that the fiber adhesion that causes, rheumatoid arthritis cause etc. all can constitute serious harm to body health.
In China, inflammation medication is seen everywhere, and almost all of patient suppresses some pain symptoms by eating antibiotic medicine.Life
In conventional NSAID (non-steroidal anti-inflammatory drug) mainly include that some antipyretic analgesic, such as anti-inflammatory agent aspirin have infringement, mouth to gastric mucosa
After taking aspirin, medicine directly contacts gastric mucosa, and it not only can make mucosal epithelial cells layer integrity lose, moreover it is possible to decompose glutinous
Liquid layer, therefore destroys gastric mucosal barrier；Long-term taking ibuprofen, can cause renal failure.Nowadays, inflammation treatment mainly leads to
Cross suppression inflammatory mediator synthesis, play antipyretic, analgesia, the effect of antiinflammatory.Therefore find effective, side effect little, can
The new drug of life-time service is significant.
Summary of the invention
In order to overcome above-mentioned deficiency, it is an object of the invention to provide biological activity sinapic acid choline ester. chlorate in Chinese medicine
Synthesis and its treatment aspect of inflammation on new opplication.
The technical scheme that the present invention takes includes synthesis and its application of sinapic acid choline ester. chlorate.
The method preparing sinapic acid choline ester. chlorate comprises the steps:
1) first water was not had completely the Semen Brassicae campestris dregs of rice, wherein: Semen Brassicae campestris dregs of rice kg: tap water L=1:4～1:10, soak 2～
6 hours, it is then placed within electric heating cover heating, uses voltage-regulation instrument regulation voltage so that it is remain at micro-boiling
State, stirring 5 per minute～6 times, extract 3～4 times, each 3～5 hours, extracting institute's water requirement ratio was 5:4:4:3, with 6 layers
Filtered through gauze, concentrates filtrate with Rotary Evaporators, obtains extractum, with extractum: the ratio ethanol of ethanol=1:10～1:20
Gained extractum is extracted, extracts 3～4 times, each 3～4 hours；Extraction gained solution is carried out sucking filtration, and the beds of precipitation abandon,
Ethanol sucking filtration layer Rotary Evaporators carries out being concentrated into without alcohol taste；
2) being diluted being concentrated into the extractum distilled water without alcohol taste, ratio is water milliliter: extractum gram=10:1～30:
1, the solution sucking filtration of dilution, add 20% appropriate potassium thiocyanate, potassium rhodanate solution is sufficiently mixed with diluent, is placed in
In 4 DEG C of refrigerators cool down 48～72 hours, after the beds of precipitation are leached, the beds of precipitation are gained Sinapine Thiocyanate, filter precipitation
After, continuing to be placed in 4 DEG C of refrigerators crystallisation by cooling 12～24 hours, take out and filter, such repeated crystallization, by sinapic acid choline ester. Hydrogen thiocyanate
Salt dissolves with the methanol of 40 DEG C～50 DEG C, Sinapine Thiocyanate gram: methanol milliliter=1:100～1:200, mistake while hot after dissolving
Filter, filtrate layers at room temperature stands 6～8 hours, has gray crystals produce raw, crystallization is scraped, and is placed in drying under reduced pressure case dry
Dry 24～48h, just obtain the powder of Sinapine Thiocyanate, the beds of precipitation dissolve with 40 DEG C～50 DEG C of methanol again, are partly dissolved,
According to top-operation 3～5 times, obtain the purity Sinapine Thiocyanate more than 90%.
3) preparation of sinapic acid choline ester. chlorate: weigh Sinapine Thiocyanate 1 gram, is dissolved in 800-1000 milliliter water, adds
717 anion exchange resin 150-160 gram that Shanghai traditional Chinese medicines produce, detects with ferric chloride solution after 30 minutes, sinapic acid choline ester.
Rhodanate is met ferric chloride solution and is become blood red, with sinapic acid choline ester. chlorate invariant color.Resin treatment method with 2% sodium hydroxide
400-500 milliliter soaks 1.5-2 hour, with the punching of about 1800-2000 milliliter distilled water to neutral, then with 2% soak with hydrochloric acid 1.5-2
Hour, with the punching of 1800-2000 milliliter distilled water to neutral, stand-by.
Sinapic acid choline ester. chlorate can be applicable to treat on the medicine of aspect of inflammation.
The invention has the beneficial effects as follows that sinapic acid choline ester. chlorate medicine has no side effect on antiinflammatory, action effect is strong, without dosage
Dependency, half-life be short, can the advantage such as life-time service, it is possible to meet the requirement for the treatment of inflammation.
Accompanying drawing explanation
Fig. 1 is swelling average figure；
Fig. 2 is swelling rate average figure.
Detailed description of the invention
Below in conjunction with Fig. 1, Fig. 2 and embodiment the present invention will be further described the present invention.
The method preparing sinapic acid choline ester. chlorate comprises the steps:
1) first water was not had completely the Semen Brassicae campestris dregs of rice, wherein: Semen Brassicae campestris dregs of rice kg: tap water L=1:4～1:10, soak 2～
6 hours, it is then placed within electric heating cover heating, uses voltage-regulation instrument regulation voltage so that it is remain at micro-boiling
State, stirring 5 per minute～6 times, extract 3～4 times, each 3～5 hours, extracting institute's water requirement ratio was 5:4:4:3, with 6 layers
Filtered through gauze, concentrates filtrate with Rotary Evaporators, obtains extractum, with extractum: the ratio ethanol of ethanol=1:10～1:20
Gained extractum is extracted, extracts 3～4 times, each 3～4 hours；Extraction gained solution is carried out sucking filtration, and the beds of precipitation abandon,
Ethanol sucking filtration layer Rotary Evaporators carries out being concentrated into without alcohol taste；
2) being diluted being concentrated into the extractum distilled water without alcohol taste, ratio is water milliliter: extractum gram=10:1～30:
1, the solution sucking filtration of dilution, add 20% appropriate potassium thiocyanate, potassium rhodanate solution is sufficiently mixed with diluent, is placed in
In 4 DEG C of refrigerators cool down 48～72 hours, after the beds of precipitation are leached, the beds of precipitation are gained Sinapine Thiocyanate, filter precipitation
After, continuing to be placed in 4 DEG C of refrigerators crystallisation by cooling 12～24 hours, take out and filter, such repeated crystallization, by sinapic acid choline ester. Hydrogen thiocyanate
Salt dissolves with the methanol of 40 DEG C～50 DEG C, Sinapine Thiocyanate gram: methanol milliliter=1:100～1:200, mistake while hot after dissolving
Filter, filtrate layers at room temperature stands 6～8 hours, has gray crystals produce raw, crystallization is scraped, and is placed in drying under reduced pressure case dry
Dry 24～48h, just obtain the powder of Sinapine Thiocyanate, the beds of precipitation dissolve with 40 DEG C～50 DEG C of methanol again, are partly dissolved,
According to top-operation 3～5 times, obtain the purity Sinapine Thiocyanate more than 90%.
3) preparation of sinapic acid choline ester. chlorate: weigh Sinapine Thiocyanate 1 gram, is dissolved in 800-1000 milliliter water, adds
717 anion exchange resin 150-160 gram that Shanghai traditional Chinese medicines produce, detects with ferric chloride solution after 30 minutes, sinapic acid choline ester.
Rhodanate is met ferric chloride solution and is become blood red, with sinapic acid choline ester. chlorate invariant color.Resin treatment method with 2% sodium hydroxide
400-500 milliliter soaks 1.5-2 hour, with the punching of about 1800-2000 milliliter distilled water to neutral, then with 2% soak with hydrochloric acid 1.5-2
Hour, with the punching of 1800-2000 milliliter distilled water to neutral, stand-by.
The antiinflammatory action of sinapic acid choline ester. chlorate.
1. method: use mouse ear swelling test method.
2. material: synthesized sinapic acid choline ester. chlorate, mice by University Of Dalian's experimental animal feeding center provide, dimethylbenzene by
Tianjin Kermel Chemical Reagent Co., Ltd. provides, and dexamethasone phosphoric acid injection is carried by Guangzhou Kanghe Pharmaceutical Co., Ltd.
Confession, remaining reagent is commercially available AR level.
Instrument and equipment: electronic balance, card Teller-torr benefit instrument (Shanghai) Co., Ltd., model is AL104.
3. experimentation
The preparation of 3.1 experimental drugs: Concentraton gradient dilution method configuration 15.0mg/ml sinapic acid choline ester. chlorate solution and 7.5mg/
Ml sinapic acid choline ester. chlorate solution, normal saline, dexamethasone phosphoric acid injection.
3.2 experiment mice packets: taking Kunming mouse 92, male and female half and half, be randomly divided into four groups, sinapic acid choline ester. chlorate is low
Dosage group, sinapic acid choline ester. chlorate high dose group, normal saline group (blank group), positive controls (shine rice pine group).
3.3 experiment mices are administered: use intraperitoneal injection.Every mice of normal saline group is to normal saline 0.2ml, mustard
Sub-alkali every mice of chlorate low dose group is to 7.5mg/ml sinapic acid choline ester. chlorate 0.2ml, and sinapic acid choline ester. chlorate high dose group is every
Mice is to 15.0mg/ml sinapic acid choline ester. chlorate 0.2ml, and Dexamethasone group every mice is to dexamethasone liquid 0.2ml.
3.4 experiment mices cause inflammation: after every mice is administered 30 minutes, take dimethylbenzene 50 microlitre uniform application at the left ear of mice
Both sides front and back.
3.5 put to death mice, take auricle: after every mice causes scorching one hour, and de-neck puts to death mice, cuts respectively with medical scissors
Go out mice left and right ear, then at the ear symmetric position of left and right, lay auricle along ear edge with 7 millimeters of card punch.
3.6 experimental results process: will obtain auricle, and weigh by precision electronic balance immediately, record its quality, calculate swelling
Degree and swelling rate.
Swelling=left ear quality-auris dextra quality；
Swelling rate=(left ear quality-auris dextra quality)/auris dextra quality * 100%.
4, result:
Table 1 experimental data average result
Note: sinapic acid choline ester. chlorate group compared with normal saline group,*P<0.05；Sinapic acid choline ester. chlorate group and dexamethasone
Group compares,#P<0.05。
SPSS data processing software one factor analysis of variance is utilized to obtain, its swelling (P=0.026 < 0.05) significance
Substantially.Inspection after this again, multiple comparisons, find normal saline group and sinapic acid choline ester. chlorate 15mg/ml (P=0.005 < 0.05)
Having significance, sinapic acid choline ester. chlorate 7.5mg/ml and sinapic acid choline ester. chlorate 15mg/ml (P=0.015 < 0.05) has significantly
Property.Its swelling rate (P=0.019 < 0.05) significance is obvious.Inspection after this again, multiple comparisons, find normal saline group and mustard
Sub-alkali chlorate 15mg/ml (P=0.008 < 0.05) has significance, Dexamethasone group and sinapic acid choline ester. chlorate 15mg/ml (P
=0.028 < 0.05) there is significance, sinapic acid choline ester. chlorate 7.5mg/ml and sinapic acid choline ester. chlorate 15mg/ml (P=0.006 <
0.05) there is significance.In conjunction with Fig. 1 and Fig. 2 analysis, the low high dose group of sinapic acid choline ester. chlorate, Dexamethasone group and normal saline
Group compares, and sinapic acid choline ester. chlorate and dexamethasone all have antiinflammatory action, and sinapic acid choline ester. chlorate concentration to mice caused by dimethylbenzene xylene inflammation
When 7.5mg/ml, its antiphlogistic effects is compared with Dexamethasone group, and dexamethasone antiphlogistic effects is more preferable, and sinapic acid choline ester. chlorate is dense
Degree compares with Dexamethasone group for its antiphlogistic effects during 15.0mg/ml, and sinapic acid choline ester. chlorate 15.0mg/ml group antiphlogistic effects is obvious
Higher than Dexamethasone group.
Experiments indicate that: mouse ear caused by sinapic acid choline ester. chlorate xylol has antiinflammatory action after causing inflammation,
Its antiinflammatory action is strong and weak compared with positive controls, and sinapic acid choline ester. chlorate antiinflammatory action when high dose is better than dexamethasone
Group, antiinflammatory action is less than Dexamethasone group when low dosage for sinapic acid choline ester. chlorate, and the low high dose group of sinapic acid choline ester. chlorate compares,
Find that antiinflammatory action strengthens along with sinapic acid choline ester. chlorate concentration raises.Early-stage Study finds that sinapic acid choline ester. chlorate also has suppression one
Nitrogen oxide effect, provides help in conjunction with this research for sinapic acid choline ester. chlorate treatment related inflammation.
The above, the only detailed description of the invention of the present invention, but protection scope of the present invention is not limited thereto, and any
Those familiar with the art is in the range of the technology of the present invention discloses, according to technical scheme and invention thereof
Conceive equivalent or change in addition, all should contain with protection scope of the present invention within.
Claims (2)
1. the synthesis of sinapic acid choline ester. chlorate and application thereof, it is characterised in that sinapic acid choline ester. chlorate can be applicable to treat aspect of inflammation
Medicine on.
The synthesis of sinapic acid choline ester. chlorate the most according to claim 1, it is characterised in that comprise the steps:
1) first water was not had completely the Semen Brassicae campestris dregs of rice, wherein: Semen Brassicae campestris dregs of rice kg: tap water L=1:4～1:10, soaked 2～6
Hour, it is then placed within electric heating cover heating, uses voltage-regulation instrument regulation voltage so that it is remain at micro-boiling-like
State, stirring 5 per minute～6 times, extract 3～4 times, each 3～5 hours, extracting institute's water requirement ratio was 5:4:4:3, with 6 layers of yarn
Cloth filters, and filtrate is concentrated with Rotary Evaporators, obtains extractum, with extractum: the ratio ethanol pair of ethanol=1:10～1:20
Gained extractum extracts, and extracts 3～4 times, each 3～4 hours；Extraction gained solution is carried out sucking filtration, and the beds of precipitation abandon, second
Alcohol sucking filtration layer Rotary Evaporators carries out being concentrated into without alcohol taste；
2) being diluted being concentrated into the extractum distilled water without alcohol taste, ratio is water milliliter: extractum gram=10:1～30:1,
The solution sucking filtration of dilution, adds 20% appropriate potassium thiocyanate, is sufficiently mixed with diluent by potassium rhodanate solution, be placed in 4 DEG C
In refrigerator cool down 48～72 hours, after the beds of precipitation are leached, the beds of precipitation are gained Sinapine Thiocyanate, after filtering precipitation,
Continuing to be placed in 4 DEG C of refrigerators crystallisation by cooling 12～24 hours, take out and filter, such repeated crystallization, by Sinapine Thiocyanate
Dissolve with the methanol of 40 DEG C～50 DEG C, Sinapine Thiocyanate gram: methanol milliliter=1:100～1:200, mistake while hot after dissolving
Filter, filtrate layers at room temperature stands 6～8 hours, has gray crystals produce raw, crystallization is scraped, and is placed in drying under reduced pressure case dry
Dry 24～48h, just obtain the powder of Sinapine Thiocyanate, the beds of precipitation dissolve with 40 DEG C～50 DEG C of methanol again, are partly dissolved,
According to top-operation 3～5 times, obtain the purity Sinapine Thiocyanate more than 90%；
3) preparation of sinapic acid choline ester. chlorate: weigh Sinapine Thiocyanate 1 gram, is dissolved in 800-1000 milliliter water, add cloudy from
Sub-exchange resin 150-160 gram, detected with ferric chloride solution after 30 minutes, and Sinapine Thiocyanate is met ferric chloride solution and become
Blood red, with sinapic acid choline ester. chlorate invariant color, it is little that resin treatment method soaks 1.5-2 with the sodium hydroxide 400-500 milliliter of 2%
Time, with the punching of about 1800-2000 milliliter distilled water to neutral, then with 2% soak with hydrochloric acid 1.5-2 hour, steam with 1800-2000 milliliter
Distilled water punching is to neutral, stand-by.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610520277.6A CN106045866A (en) | 2016-07-05 | 2016-07-05 | Synthesis and application of sinapine chlorate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201610520277.6A CN106045866A (en) | 2016-07-05 | 2016-07-05 | Synthesis and application of sinapine chlorate |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1615829A (en) * | 2004-09-20 | 2005-05-18 | 中国药科大学 | Use of sinapine in preparing medicine for preventing and curing senile dementia |
| CN102146045A (en) * | 2010-02-08 | 2011-08-10 | 大连大学 | Method for preparing sinapine |
| CN103083677A (en) * | 2012-11-30 | 2013-05-08 | 甘肃中医学院 | Permeation accelerator and application thereof to permeation acceleration |
| CN103804207A (en) * | 2012-11-06 | 2014-05-21 | 大连大学 | Sinapine chloride preparation method and medicine application thereof |
-
2016
- 2016-07-05 CN CN201610520277.6A patent/CN106045866A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1615829A (en) * | 2004-09-20 | 2005-05-18 | 中国药科大学 | Use of sinapine in preparing medicine for preventing and curing senile dementia |
| CN102146045A (en) * | 2010-02-08 | 2011-08-10 | 大连大学 | Method for preparing sinapine |
| CN103804207A (en) * | 2012-11-06 | 2014-05-21 | 大连大学 | Sinapine chloride preparation method and medicine application thereof |
| CN103083677A (en) * | 2012-11-30 | 2013-05-08 | 甘肃中医学院 | Permeation accelerator and application thereof to permeation acceleration |
Non-Patent Citations (6)
| Title |
|---|
| KHATTAB, RABIE Y.等: "Production of Canolol from Canola Meal Phenolics via Hydrolysis and Microwave-Induced Decarboxylation", 《JOURNAL OF THE AMERICAN OIL CHEMISTS" SOCIETY》 * |
| NICIFOROVIC, NEDA等: "Sinapic Acid and Its Derivatives: Natural Sources and Bioactivity", 《COMPREHENSIVE REVIEWS IN FOOD SCIENCE AND FOOD SAFETY》 * |
| SONG, FANGMING等: "Eriodictyol Inhibits RANKL-Induced Osteoclast Formation and Function Via Inhibition of NFATc1 Activity", 《JOURNAL OF CELLULAR PHYSIOLOGY》 * |
| VUORELA, SATU等: "Effect of Plant Phenolics on Protein and Lipid Oxidation in Cooked Pork Meat Patties", 《JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY》 * |
| 丁韵等: "芥子碱氯化盐的制备及其对自发性高血压大鼠的降压作用", 《沈阳药科大学学报》 * |
| 张明发等: "芥子碱的抗炎和抗腹泻作用", 《中药药理与临床》 * |
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