CN105906676A - Preparation method of isoquercitrin and application of isoquercitrin to aspect of resisting asthma - Google Patents
Preparation method of isoquercitrin and application of isoquercitrin to aspect of resisting asthma Download PDFInfo
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- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
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Abstract
The invention relates to the field of biological medicines and in particular relates to a biological transformation preparation method of isoquercitrin (quercetin-3-O-beta-D-glucopyranoside I). The invention further discloses application of the isoquercitrin to the aspect of resisting asthma. The structural formula is shown in the description.
Description
Technical field
The present invention relates to field of biological medicine, be specifically related to isoquercitrin (Quercetin-3-O-β-D-pyranglucoside, I)
Biotransfer process for preparing, the invention also discloses its purposes in terms of asthma.
Background technology
Asthma is a kind of thin by the inflammatory cells such as eosinophilic granulocyte, T lymphocyte (Th2), mastocyte, airway epithelia
The air flue chronic allergic reaction diseases associated with inflammation that born of the same parents participate in.Asthma is a kind of commonly encountered diseases, frequently-occurring disease, causes human health very
Many adverse effects.Whole world asthmatic patient about 300,000,000 people, China's asthmatic patient about 30,000,000, have nearly 200,000 people to die from every year at present
Asthma, and numerous studies show nearly 20 years in the prevalence of asthma still have the trend being gradually increased.The pathogenesis of asthma is complicated,
The most clearly.In current treating asthma, generally use glucocorticoid to control the chronic inflammatory disease of air flue.So
And, hormone medicine can only mitigation symptoms, it is impossible to the basic reason for asthma is treated, and life-time service side effect is relatively
Greatly.Therefore the exploitation of the small-molecule drug of natural origin and structure of modification, and the research of pharmacological mechanism becomes current new drug
The focus of research and development.Quercetin is the most representational a kind of flavonoid drugs in flavone compound, is distributed in nature
Extensively, there is the multiple biological activitys such as antioxidation, antiinflammatory, protection cardiovascular system.Research shows, Quercetin scalable Th1/Th2
Balance, reduces histamine content and the activity of phospholipase A2, improves eosinophilic granulocyte and neutrophil infiltration, suppresses trachea
Shrink, reach to treat the purpose of asthma.But Quercetin water solublity is relatively low, bioavailability is poor, limits its clinical practice.
Microorganism conversion is the specific biochemical reaction that the specific enzymes exogenous compound utilizing microorganism to produce carries out structural modification.
Microorganism converts the stereochemical structure selectivity with height, can exclusively be catalyzed specific reaction, without loaded down with trivial details protection and remove-insurance
Protect operation, have efficiently, the advantage of environmental protection, be natural active compound a kind of effective ways of carrying out structural modification.Therefore,
We select the mode that microorganism converts, and carry out glycosylation modified to 3 hydroxyls of Quercetin, to improve bioavailability, with
Time keep or increase its activity.
Summary of the invention
The invention discloses the compound of structural formula I:
Named isoquercitrin (Quercetin-3-O-β-D-pyranglucoside).The present invention also includes the compound of structural formula I simultaneously
Solvate.Its13C-NMR (500MHz, DMSO) adds six carbon signals compared with substrate Quercetin, is respectively
δ C100.8, δ C74.0, δ C76.4, δ C69.9, δ C77.5, δ C60.9ppm is consistent this with the chemical displacement value of D-Glucose.1H-NMR (500MHz, DMSO), compared with substrate Quercetin, at chemical shift δ 3.09-δ 5.46, occurs in that D-pyrrole
The hydrogen of glucopyranoside and hydroxyl hydrogen signal: δ 3.09-δ 3.59 (H on 6H, m, glu), δ 5.46 (1H, d, J=7.0Hz,
H-1″)；The chemical shift of anomeric proton is at 5.46, it can be determined that glycosylation site is positioned at 3, and the coupling of anomeric proton is normal
Number is 7.0Hz, shows that the D-Glucose spatial configuration connected is β type.Pharmacological testing shows, the compound of the Formulas I of the present invention
There is antasthmatic activity.
The compound of formula I of the present invention preferably with microbe transformation method, carries out converting preparation with Quercetin for substrate, and method is as follows:
Be converted into the suitable strain of isoquercitrin for finding Quercetin, the present invention has screened multiple-microorganism, found that preservation
Number for the strain of NRRL 1086, Cortex querci dentatae is have preferable conversion capability (being shown in Table 1).
Fluid medium used by screening is that Compound Potato culture medium (PDA): 200 grams fresh peeled potatoes are cut into fragment,
Adding after distilled water boils 15min in right amount and filter, filtrate adds glucose 20g, KH2PO4 3.0g、MgSO4 0.75g、Vb110.0mg,
Add distilled water and be settled to 1.0L, add NaOH or HCl adjust pH value to 6.0, every bottle of subpackage 30mL liquid of 150mL conical flask
Culture medium, 121 DEG C, 0.15MPa sterilizing 20min.
During strain screening, preserving slant medium used by strain is the agar in aforesaid liquid culture medium addition 1.5%, and 15mL has
Plug test tube often pipe 5mL, 121 DEG C, 0.15MPa sterilizing 20min cooling after make.
The preservation of strain and activation: actication of culture uses two step activation methods, sees: Nair, M.S.R., and
Basile, D.V.Bioconversion of artenium B to artmisinn. natural product magazine (Jounal of Natural Products)
1993,56 (9): 1559.First strain is inoculated in fluid medium, 28 DEG C, after 180r/min rotating and culturing 24-48h, transfer in
Another fluid medium, inoculum concentration 1-5% (V/V), it is loaded with after CMC model 24h.
The preparation of sample and sample-adding: take Quercetin and be dissolved in ethanol, be made into 10mg/mL solution for standby；Every bottle of bacterium through two step activation
Liquid (30mL) adds 0.5mL sample solution, makes every bottle of bacterium solution 5mg Han Quercetin.After CMC model 120h, stopped reaction,
Filtering thalline, the ethyl acetate of fermentation liquid equivalent extracts 3～5 times, combining extraction liquid, recovery ethyl acetate；It is extracted leaching
Cream, thalline ethanol extraction 3 times, united extraction liquid, reclaims ethanol, obtains extracting extractum, merged by two kinds of extractum, add few
Permitted acetic acid ethyl dissolution standby thin layer and identified use.
Blank: blank sets positive control (substrate+culture medium), negative control (culture medium+bacterium), solvent control (training
Support base+bacterium+ethanol), cultivate with extraction conditions ibid.
The thin layer of converted product is identified:
Thin layer condition:
Lamellae: the silica gel G plate that the CMC-Na of 0.7% makes.
Developing solvent: chloroform: methanol: formic acid (85: 15: 0.5) ascending development.
Developer: 5% ferric chloride ethanol solution.
Operation:
Conversion extract and blank extract, respectively at lamellae point sample, take out after being sufficiently spread out, are placed in fume hood and dry,
Spraying 5% ferric chloride chromogenic reagent, conversion results is shown in Table 1.
Table 1 microorganism converts Quercetin the selection result
In terms of the selection result, only NRRL 1086 can convert, and through measuring and calculating, conversion ratio is up to 80%.Therefore, the present invention selects
Bacterial strain NRRL 1086, prepares isoquercitrin with Quercetin for raw material.
The invention discloses the preparation method of a kind of formula I, be that Quercetin is entered by NRRL 1086 bacterial strain with preserving number
Row bioconversion obtains.
Preferred method is: with Quercetin as substrate, utilize preserving number for the bacterial strain of NRRL 1086, by substrate and this bacterial strain
Co-culture 12h in the medium, terminate reaction, extract with organic solvent, concentrated extract, separated i.e. by silica gel column chromatography
?.
Wherein organic solvent one in methanol, ethyl acetate, chloroform, dichloromethane, Ethyl formate, the butyl acetate or
Several.More preferably ethyl acetate.
Silica gel column chromatography separation chloroform and methanol carry out gradient elution.
Culture medium is containing 10～the Rhizoma Solani tuber osi decoction liquor of 30%, KH2PO4、MgSO4, vitamin B1 and selected from glucose, sucrose,
One or more carbon sources in maltose, xylose, starch, medium pH=5.0～7.0.Wherein by 20% Rhizoma Solani tuber osi decoction liquor 100
Milliliter meter, in culture medium, the preferred content of each component is KH2PO4Containing 0.1～0.5 gram；MgSO4Containing 0.05～0.5 gram；Fructus Vitis viniferae
Sugar or sucrose 0.5-2.5 gram.
Highly preferred preparation method is: by bacterial strain that preserving number is G.deliquescens NRRL 1086 by inclined plane inoculating to liquid
In body culture medium, put 28 DEG C, rotating speed be 180r/m shaking table in cultivate within 24 hours, become seed liquor, seed liquor be forwarded to fermentation
Continue after liquid to cultivate 24 hours, add conversion of substrate；Terminate catalytic reaction after continuing to cultivate 12 hours, filter thalline, fermentation
The ethyl acetate of liquid equivalent extracts 5 times, combining extraction liquid, recovery ethyl acetate, is extracted extractum, and extractum is mixed through silica gel
Column chromatography for separation after sample；With chloroform-methanol as elution system.Converted product, through recrystallizing methanol, obtains the conversion of yellow powder
Product.
Pharmacological testing proves, the Compounds of structural formula I of the present invention has significant asthma effect, the following is test method and result:
The research of isoquercitrin antiasthmatic activity
1, the preclinical impact of Experimental Asthma In Guinea-pigs that acetylcholine and histamine are caused by isoquercitrin
Choose Holland healthy, male and plant Cavia porcellus, body weight 300 ± 20g.Cavia porcellus is positioned over the glass of 20cm × 20cm × 50cm
In case, preparing 2% acetylcholine and 0.2% histamine phosphate mixed liquor, ultrasonic atomizatio sprays into 15s, filters out asthmatic latent period and is less than
The Cavia porcellus of 120s.Next day, Cavia porcellus is randomly divided into 6 groups, often group 10, i.e. blank group (normal saline, 10ml/kg),
Model control group (normal saline, 10ml/kg), positive controls (dexamethasone, 5mg/kg) and isoquercitrin low dosage
Group (20mg/kg), middle dosage group (40mg/kg), high dose group (80mg/kg), gastric infusion 1 time.After being administered 1h,
Ultrasonic atomizatio sprays with 2% acetylcholine and 0.2% histamine phosphate mixed liquor, continues 15s.Measure asthmatic latent period (i.e. to open from spraying
Begin to asthma attack, dyspnea, until twitching the time fallen down to the ground).
Table 2 isoquercitrin on the impact of Cavia porcellus asthmatic latent period (, n=10)
Note:*P ＜ 0.05,**P ＜ 0.01
As shown in Table 2, isoquercitrin basic, normal, high dosage group compares model control group, and the asthmatic latent period of Cavia porcellus the most substantially prolongs
Long, wherein the asthmatic latent period of high dose group is the longest, and antiasthmatic effect is best, and is better than positive drug group.Show isoquercitrin
Asthma effect.
2, the isoquercitrin effect to guinea pig in vitro pulmonary branches tracheal smooth muscle tension force
Choose Holland healthy, male and plant Cavia porcellus, body weight 300 ± 20g.Cavia porcellus is randomly divided into 6 groups, often group 10, i.e. model
Matched group, positive controls (isoproterenol, 300mg/l) and isoquercitrin low dose group (100mg/l), middle dose
Amount group (200mg/l), high dose group (400mg/l).Be prepared in advance lung airway perfusion device, is full of oxygen-containing in storage stream bottle
Le Shi nutritional solution.Taking Cavia porcellus, mallet shoots dead, carotid artery blood-letting, opens rapidly thoracic cavity, exposes heart, lung, cuts one section
Trachea takes out outside thoracic cavity together with heart and pulmo, is immersed by lung in the culture dish of 37 DEG C of oxygen-containing Le Shi nutritional solutions, squeezes lung gently
For several times, to get rid of the gas in lung, then trachea line is tied on the sleeve pipe of perfusion device, with locke solution perfusion, at lung table
Face can use syringe needle to be dispersed in and wears 7～9 holes, and regulation perfusion rate is 50/min.After perfusion flow is constant, can be by 0.5ml medicine
In the rubber tube on thing sprue bushing top.After observing and comparing administration, in 3min, liquid flows out and drips number and discharge.
Table 3 isoquercitrin to the effect of guinea pig in vitro pulmonary branches tracheal smooth muscle tension force (, n=10)
Note:*P ＜ 0.05,**P ＜ 0.01
Table 3 shows, isoquercitrin acts on the isolated bronchia smooth muscle of Cavia porcellus, can increase perfusion number of drops and liquid outflow amount,
Prompting isoquercitrin has certain diastole effect to bronchial smooth muscle.
3, leukotriene B4, the impact of D4 in the Asthmatic Rat Lung that antigen is caused by isoquercitrin
Take health, cleaning grade SD rat, body weight 200 ± 20g, male and female half and half.It is randomly divided into 6 groups, often group 10, i.e. empty
White matched group (normal saline, 10ml/kg), model control group (normal saline, 10ml/kg), positive controls (fill in rice
Pine, 5mg/kg) and isoquercitrin low dose group (20mg/kg), middle dosage group (40mg/kg), high dose group (80mg/kg).
Use antigen ovalbumin sensitization model, prepare every milliliter of (OH) Han ovalbumin 10mg, Al3The normal saline of dry powder 100mg
Suspension, in addition to blank group, by other 5 treated animal respectively at the 1st, 2,3 days lumbar injection sensitization liquid 1ml, the 8th
It repeats sensitization 1 time.From the beginning of the 15th day, this 5 treated animal ultrasonic atomizatio 1% ovalbumin is excited, every day 1
Secondary, each 30min.Until rat occurs that asthma sample shows effect, totally 4 weeks.See during atomization rat occur dysphoria, sneeze,
Gatism, grab the symptom such as ear, cyanosis, show modeling success.From the 5th week, by packet requirement gastric infusion respectively,
Every day 1 time, continue 30 days.Last be administered after 1h, with 2% pentobarbital sodium (40mg/kg) intraperitoneal injection of anesthesia rat,
Taking right lung and make 10% tissue homogenate, the homogenate prepared is put into 3500r/min in centrifuge and is centrifuged 10min, extracts supernatant,
First measure protein concentration in lung homogenate with dihomocinchonine acid albumin quantification kit, use ELISA method, say by test kit
Bright book measures leukotriene B4 (LTB in homogenate4)、D4(LTD4) content, measurement result contains with albumen in every milliliter of homogenate
Amount (pg/mgprot) is corrected.
Table 4 isoquercitrin is to LTB in Asthmatic Rat Lung4、LTD4Content impact (, n=10, pg/mgprot)
Note:*P ＜ 0.05,**P ＜ 0.01
As shown in table 4, relative to blank group, LTB in model group4、LTD4Content significantly raises, and shows that modeling is the most successful.
Compare model group, LTB in basic, normal, high three the dosage groups of isoquercitrin4、LTD4Content significantly reduces, and shows isoquercitrin
The inflammatory factor leukotriene B4 in Rat Asthma Model, the expression of D4 can be reduced.
To sum up, isoquercitrin can significantly extend asthma attack incubation period, expansion bronchus smooth muscle, thus plays antiasthmatic effect.
Meanwhile, experiments prove that isoquercitrin can reduce the content of inflammatory factor leukotriene B4, D4 in lung tissue, thus it is speculated that it is put down
The effect of breathing heavily may be relevant with antiinflammatory.
The isoquercitrin of the present invention can mix with pharmaceutically acceptable carrier, is used for preparing medicine for treatment compositions.Can be prepared as
Dosage form general on pharmaceutics, such as gastrointestinal administrations such as capsule, tablet, pill, oral liquid, granule, tincture, slow releasing agents
The parenteral dosage forms such as dosage form and injection, transdermal patch, external preparation.
Detailed description of the invention
Embodiment 1
The preparation of isoquercitrin
Strain NRRL 1086 is seeded to liquid PDA culture medium by the solid slope of 4 DEG C, and (culture medium is by 100 milliliter of 20% Ma Ling
Containing KH in potato decoction liquor2PO40.3 gram；MgSO40.75 gram；Glucose 10 grams；VitaminB10 .01 gram preparation, liquid is trained
Support base subpackage to the triangular flask of 150mL, every bottled liquid 30mL), to shaking table, cultivate 24 hours (28 DEG C, 180r/m), i.e.
For seed liquor；Seed liquor is aseptically transferred in liquid PDA culture medium (culture medium composition is the same), in shaking table
Continue to cultivate 24 hours.Every bottle adds 1ml Quercetin ethanol solution (20mg/ml), cotransformation 200mg, after cultivating 12 hours
Terminate reaction.The ethyl acetate of fermentation liquid equivalent extracts 5 times, combining extraction liquid, recovery ethyl acetate；It is extracted extractum
321mg, weighs 100-200 mesh silica gel 0.8g and uniformly mixes sample, column chromatography 200～300 mesh 20g dry column-packing, chloroform with residue
-methanol elution gradient, in chloroform-methanol=95: in the eluting fraction of 5, can obtain targeted transformation product isoquercitrin, through methanol weight
Crystallization, obtains yellow powder 267mg.
Its carbon spectrum is as mentioned above
Embodiment 2
Tablet
The isoquercitrin 100g that Example 1 prepares mixes with starch 50g, dextrin 50g, makees wetting agent with appropriate 30% ethanol,
Making soft material, conventional method is pelletized, and adds the mixing of appropriate magnesium stearate, makes tablet.
Claims (9)
1. the compound of structural formula I or its pharmaceutically acceptable solvate:
2. the compound of claim 1 or the preparation method of its pharmaceutically acceptable solvate, is characterized in that: with protecting
Tibetan number carries out bioconversion acquisition for NRRL 1086 bacterial strain to Quercetin.
3. the preparation method of claim 2, wherein bioconversion method is as follows: with Quercetin as substrate, utilizes preserving number
For the bacterial strain of NRRL 1086, substrate and this bacterial strain are cultivated 12h in the medium, terminate reaction, fermentation liquid
Extract with organic solvent, concentrated extract, obtain extractum, by silica gel column chromatography isolated target compound.
4. the preparation method of claim 3, wherein organic solvent includes: ethyl acetate, chloroform, dichloromethane, formic acid
Ethyl ester, butyl acetate, toluene, hexane, n-butyl alcohol etc..
5. the preparation method of claim 3, culture medium is containing 10～the Rhizoma Solani tuber osi decoction liquor of 30%, KH2PO4、MgSO4、
Vitamin B1With the carbon source of one or more in glucose, sucrose, maltose, xylose, starch, cultivate
Base pH=5.0～7.0.
6. the preparation method of claim 3, wherein based on 20% Rhizoma Solani tuber osi decoction liquor 100 milliliters, KH2PO40.1～0.5
Gram；MgSO40.05～0.5 gram；Glucose 0.5-2.5 gram (or sucrose 0.5-2.5 gram).
7. the preparation method of claim 2, wherein strain first activates before cultivation, soak time 20～30h.
8. a pharmaceutical composition, wherein contain the compound of claim 1 or its pharmaceutically acceptable solvate and
Pharmaceutically acceptable carrier.
9. compound or its pharmaceutically acceptable solvate of claim 1 is used for preparing the purposes of suppressing panting calming medicine.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2648451C1 (en) * | 2017-07-05 | 2018-03-26 | Федеральное государственное бюджетное научное учреждение "Томский национальный исследовательский медицинский центр Российский академии наук" (Томский НИМЦ) | Cerebroprotective agent |
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| RU2648451C1 (en) * | 2017-07-05 | 2018-03-26 | Федеральное государственное бюджетное научное учреждение "Томский национальный исследовательский медицинский центр Российский академии наук" (Томский НИМЦ) | Cerebroprotective agent |
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Application publication date: 20160831 |