CN102304158A - Acylated flavonoid glycoside compounds and application thereof in preparation of complement inhibitor medicines - Google Patents
Acylated flavonoid glycoside compounds and application thereof in preparation of complement inhibitor medicines Download PDFInfo
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Abstract
The invention discloses acylated flavonoid glycoside compounds shown as a formula I and application thereof in preparation of complement inhibitor medicines. Acylated flavonoid glycosides extracted and separated from cudweed herb are proved to inhibit hemolysis caused by activation of a complement system in a classical pathway through in vitro experiments, and have complement inhibition effect; the activity of each monomericcompound is higher than that of a total extract of cudweed herb; and the acylated flavonoid glycoside compounds are good complement inhibitors and have low effective concentration, can serve as active ingredients to prepare novel complement inhibitor medicines for treating various diseases caused by abnormal activation of complements, are low in toxicity, safe in administration and rich in raw material sources and have great clinical application value. The structure of the formula I is shown as the specifications, wherein R1 and R2 are same or different, and respectively H, OH or OCH3; and R3 and R4 are respectively H or groups shown in the specifications.
Description
Technical field
The present invention relates to the complement inhibitor medicine, be specifically related to acidylate flavonoid glycoside compound and the application in the preparation anticomplement medicament thereof.
Background technology
Complement system is one of immune defense system of wanting of body weight for humans.Under normal physiological condition, the function of complement mainly is to attack external cause of disease and remove immunocomplex, and keeps organism balance.Yet the improper activation of complement system can cause human immune system's overreaction, causes the damage and the inflammatory reaction of human body self healthy tissues, is the important medium of autoimmune inflammation reaction.More and more evidences shows, the generation of inflammatory disease, development are relevant with the activation of complement.Therefore, how to disturb and suppress the damage of complement activation generation, become one of focus of pharmaceutical research.
Prove that at present all the excessive activation with complement is relevant for multiple diseases such as rheumatoid arthritis, apoplexy, ephritis, systemic lupus erythematous, senile dementia, ischemic damage and reperfusion, acute myocardial infarction, acute respiratory distress syndrome.Multiple complement inhibitor is applied to clinically just under study for action in the monoclonal antibody of existing complement receptor (CR) of the U.S. and anti-C5a, obtain curative effect preferably.Though but these systemic complement inhibitors have improved inflammatory reaction,, produce the general complement simultaneously and suppress because complement system has important defense reaction in body; Therefore; Prolonged application can reduce the defence capability of body, produces multiple complications, also causes infection to wait the potential spinoff.In order to give full play to the curative effect of complement inhibitor, reduce untoward reaction, people are trying to explore the novel complement inhibitor of high-efficiency low-toxicity in the natural product.
The progress of ACA composition in the natural product in recent years; Be not difficult to find out the ACA composition of from natural product, having told multiple structure type, mainly contain flavones, polysaccharide and terpenoid, wherein the acidylate flavonoid glycoside has significant inhibitory effect to complement system; And in natural phant, distribute extensively; Feverfew Baikal life everlasting (Gnaphalium uliginosum) (Phytochemistry Letters, 2010,3:45-47), polygonaceae plant pale persicaria (Persicaria lapathifolia) (Chem.Pharm.Bull.1999; 47 (10): 1484-1486), Magnoliacea plant Flos Magnoliae (Magnolia fargesii) (Biol.Pharm.Bull.1998; 21 (10): 1077-1078), leguminous plants donkey food grass (Onobrychis viciifolia) (Phytochemistry, 2011,72:423-429) with Kent basic note Chinese scholartree (Cladrastis kentukea) (Phytochemistry; 2011; 72:372-384) and pinaceae plant newveitch spruce (Picea neoveitchii) (Phytochemistry, 2011,72:490-494) wait in the plant distribution all arranged.Pharmacological actions such as that this compounds has is antimycotic, cell toxicant, but do not see so far Flavone aglycone-4 '-sugar-aromatic ring structure or the acidylate flavonoid glycoside anticomplement of Flavone aglycone-7-sugar-aromatic ring structure and the report of preparation complement suppressive drug thereof.
The inventor once studied and had reported that the life everlasting extract was used for pharmacy (one Chinese patent application number: 201110059384.0); Discover that further the monomer new compound acidylate flavonoid glycoside that separation obtains from life everlasting has significant ACA, and the activity of each monomeric compound all is better than the activity of life everlasting total extract at present.
Summary of the invention
Technical problem to be solved by this invention is to overcome above-mentioned weak point, and the acidylate flavonoid glycoside that research and design is new prepares the complement suppressive drug.
The invention provides the application of a kind of acidylate flavonoid glycoside compound in the preparation anticomplement medicament.
Said acidylate flavonoid glycoside compound has the chemical structure of formula I:
Formula I
R wherein
1, R
2Can be identical or different, can be respectively H, OH or OCH
3
R
3, R
4Difference can be respectively H or be following groups:
Acidylate flavonoid glycoside compound preferred for this invention comprises following compounds:
Apigenin-4 '-O-β-D-(6 " the E-coffee acyl)-glucoside 1;
Luteolin-4 '-O-β-D-(6 " the E-coffee acyl)-glucoside 2;
Quercetin-4 '-O-β-D-(6 " the E-coffee acyl)-glucoside 3;
Apigenin-7-O-beta-D-(6 " the E-coffee acyl)-glucose 4.
Wherein compound 1,2, and 3 for separating the new compound that obtains from life everlasting.
Above-claimed cpd through HR-ESI-MS, IR,
1H-NMR (DMSO-d
6, 600MHz),
13C-NMR (DMSO-d
6, 150MHz) wait detection, proved conclusively their structure.
Acidylate flavonoid glycoside compound of the present invention, through in vitro tests, confirmation can suppress classical pathway of complement and activate the cell haemolysis that causes; Significant ACA is arranged; The activity of each monomeric compound all is better than the activity of life everlasting total extract, thereby, can be used for preparing anticomplement medicament.
Above-claimed cpd of the present invention separates from life everlasting and obtains, through following method preparation:
Life everlasting herb 25kg pulverizes, and 80% alcohol heat reflux extracts 3 times, stepwise solvent extraction behind the medicinal extract, obtain sherwood oil, ETHYLE ACETATE, propyl carbinol and four parts of water liquid.Ethyl acetate extract is through silica gel (100～200 order) column chromatography, with methylene dichloride: methyl alcohol (70: 1,50: 1; 30: 1,20: 1,10: 1; 5: 1,3: 1,1: 1) gradient elution; Collect methylene dichloride: methyl alcohol (10: 1) wash-out stream part is carried out repeatedly silica gel column chromatography, reversed-phase column chromatography purifying, separates obtaining compound 1,2,3,4.
The life everlasting that the present invention uses obtains through commercially available.
The pharmaceutical composition that medicine of the present invention is made up of as activeconstituents and pharmaceutical carrier formula I compound.
Medicine of the present invention by apigenin-4 '-pharmaceutical composition that O-β-D-(6 " E-coffee acyl)-glucoside 1 is formed as activeconstituents and pharmaceutical carrier.
Medicine of the present invention by luteolin-4 '-pharmaceutical composition that O-β-D-(6 " E-coffee acyl)-glucoside 2 is formed as activeconstituents and pharmaceutical carrier.
Medicine of the present invention by Quercetin-4 '-pharmaceutical composition that O-β-D-(6 " E-coffee acyl)-glucoside 3 is formed as activeconstituents and pharmaceutical carrier.
The pharmaceutical composition that medicine of the present invention is made up of as activeconstituents and pharmaceutical carrier apigenin-7-O-beta-D-(6 " E-coffee acyl)-glucose 4.
Pharmaceutical composition of the present invention has significant ACA, can be used for the various diseases that the improper activation of complement causes.
Acidylate flavonoid glycoside of the present invention has significant ACA, and the activity of each monomeric compound all is better than the activity of life everlasting total extract; Be one type of good complement inhibitor, can be used for the various diseases that the improper activation of complement causes, and effective concentration be low; Toxicity is low; Drug safety, raw material sources are abundant, and bigger clinical value is arranged.
Embodiment
With indefiniteness embodiment the present invention is further specified below.
Embodiment 1 preparation acidylate flavonoid glycoside compound
Dry herb (purchasing in medicinal material market, Bozhou, the Chinese Anhui) 25kg of life everlasting pulverizes, and 80% alcohol heat reflux extracts three times (200L * 3), and united extraction liquid reclaims ethanol; 60 ℃ are evaporated to dried; Life everlasting total extract medicinal extract 2.9kg, get total extract 2.5kg water (15L) suspendible, use isopyknic sherwood oil, ETHYLE ACETATE, n-butanol extraction successively 3 times; The combined ethyl acetate extraction liquid concentrates 60 ℃ and is decompressed to driedly, promptly gets acetic acid ethyl ester extract 450g.Get acetic acid ethyl ester extract 400g through silicagel column (chromatogram of 10cm * 100cm) is with methylene dichloride for 4kg, 100～200 orders: methyl alcohol (70: 1,50: 1,30: 1,20: 1; 10: 1,5: 1,3: 1,1: 1) gradient elution, each gradient elution 20L collects methylene dichloride: methyl alcohol (10: 1) wash-out stream part 20L; 60 ℃ be evaporated to dried, 80g medicinal extract, again through silicagel column (1kg, 200～300 orders, the chromatography of 10cm * 60cm); With methylene dichloride: methyl alcohol (30: 1,20: 1,15: 1,10: 1,5: 1; 3: 1,1: 1,0: 1) wash-out, each gradient elution 10L obtains 8 stream part (Fr
1-Fr
8).Stream part Fr
7(23.3g) through the reverse phase silica gel post (125g, the methanol of 5cm * 20cm) (1: 4,1: 2,1: 1; 3: 2,4: 1, pure methyl alcohol) gradient elution, each gradient elution 2L; I-VI6 stream part, wherein stream part III (4.5g) again through the reverse phase silica gel post (100g, the methanol (2: 3) of 5cm * 15cm) is purifying 2 times repeatedly, purifying eluting solvent amount is 1.5L at every turn; 60 ℃ of decompression and solvent recoveries get compound 1 (118.1mg), and stream part IV (6.4g) is through silicagel column (70g; The methylene dichloride of 5cm * 20cm): methyl alcohol (10: 1) is purifying 3 times repeatedly, and each purifying eluting solvent amount is 1.5L, 60 ℃ of decompression decompression and solvent recoveries; Compound 2 (315.6mg), stream part V (5.7g) and stream part VI (1.6g) respectively through the reverse phase silica gel post (100g, the methanol (2: 3) of 5cm * 15cm) is purifying 3 times repeatedly; Each purifying eluting solvent amount is 1.5L, and 60 ℃ of decompression and solvent recoveries get compound 3 (245.3mg) and 4 (29.4mg).
The detected result of the compound 1,2,3,4 that obtains is following:
Apigenin-4 '-O-β-D-(6 " the E-coffee acyl)-glucoside compound 1, C
30H
26O
13, yellow powder.HR-ESI-MS(m/z?594.1450[M+H]
+).IR：3356，1701，1654，1606，1506。
1H-NMR(DMSO-d
6，600MHz)δppm：6.77(1H，s，H-3)，6.20(1H，d，J＝1.8Hz，H-6)，6.46(1H，d，J＝1.8Hz，H-8)，7.98(2H，d，J＝8.4Hz，H-2′，H-6′)，7.20(2H，d，J＝8.4Hz，H-3′，H-5′)，5.16(1H，d，J＝7.2Hz，H-1″)，7.03(1H，d，J＝1.8Hz，H-2″′)，6.73(1H，d，J＝8.4Hz，H-5″′)，6.99(1H，dd，J＝8.4，1.8Hz，H-6″′)，7.46(1H，d，J＝15.6Hz，H-7″′)，6.27(1H，d，J＝15.6Hz?H-8″′).
13C-NMR(DMSO-d
6，150MHz)δppm：162.9(C-2)，103.7(C-3)，181.6(C-4)，161.3(C-5)，98.8(C-6)，164.2(C-7)，93.9(C-8)，157.2(C-9)，103.7(C-10)，124.0(C-1′)，128.0(C-2′)，116.5(C-3′)，159.9(C-4′)，116.5(C-5′)，128.0(C-6′)，99.6(C-1″)，73.0(C-2″)，73.7(C-3″)，69.7(C-4″)，76.2(C-5″)，63.1(C-6″)，125.3(C-1″′)，114.8(C-2″′)，145.5(C-3″′)，148.4(C-4″′)，115.7(C-5″′)，121.1(C-6″′)，145.3(C-7″′)，113.6(C-8″′)，166.3(C-9″′)。
Luteolin-4 '-O-β-D-(6 " the E-coffee acyl)-glucoside compound 2, C
30H
26O
14, yellow powder.HR-ESI-MS(m/z?611.1382[M+H]
+).IR：3394，1657，1625，1509。
1H-NMR(DMSO-d
6，600MHz)δppm：6.69(1H，s，H-3)，6.20(1H，d，J＝2.4Hz，H-6)，6.44(1H，d，J＝1.8Hz，H-8)，7.49(1H，d，J＝2.4Hz，H-2′)，7.22(1H，d，J＝8.4Hz，H-5′)，7.42(1H，dd，J＝8.4，2.4Hz，H-6′)，4.99(1H，d，J＝7.2Hz，H-1″)，7.05(1H，d，J＝1.8Hz，H-2″′)，6.75(1H，d，J＝8.4Hz，H-5″′)，7.02(1H，dd，J＝8.4，1.8Hz，H-6″′)，7.50(1H，d，J＝15.6Hz，H-7″′)，6.29(1H，d，J＝15.6Hz?H-8″′)。
13C-NMR(DMSO-d
6，150MHz)δppm：163.0(C-2)，103.7(C-3)，181.6(C-4)，161.7(C-5)，98.9(C-6)，164.2(C-7)，93.9(C-8)，157.3(C-9)，103.9(C-10)，124.8(C-1′)，113.6(C-2′)，146.9(C-3′)，148.2(C-4′)，115.8(C-5′)，118.3(C-6′)，100.8(C-1″)，73.1(C-2″)，75.7(C-3″)，69.8(C-4″)，73.9(C-5″)，63.1(C-6″)，125.4(C-1″′)，114.9(C-2″′)，145.5(C-3″′)，148.4(C-4″′)，115.8(C-5″′)，121.2(C-6″′)，145.3(C-7″′)，113.7(C-8″′)，166.3(C-9″′)。
Quercetin-4 '-O-β-D-(6 " the E-coffee acyl)-glucoside compound 3, C
30H
26O
15, yellow powder.HR-ESI-MS (m/z?627.1350[M+H]
+).IR：3405，1686，1599，1506。
1H-NMR(DMSO-d
6，600MHz)δppm：6.20(1H，d，J＝2.4Hz，H-6)，6.39(1H，d，J＝1.8Hz，H-8)，7.71(1H，d，J＝1.8Hz，H-2′)，7.23(1H，d，J＝9.0Hz，H-5′)，7.59(1H，dd，J＝9.0，2.4Hz，H-6′)，4.96(1H，d，J＝7.2Hz，H-1″)，6.73(1H，d，J＝8.4Hz，H-5″′)，7.00(1H，dd，J＝8.4，1.8Hz，H-6″′)，7.49(1H，d，J＝15.6Hz，H-7″′)，6.29(1H，d，J＝15.6Hz?H-8″′)。
13C-NMR(DMSO-d
6，150MHz)δppm：145.8(C-2)，136.4(C-3)，176.0(C-4)，160.7(C-5)，98.2(C-6)，164.0(C-7)，93.5(C-8)，156.2(C-9)，103.1(C-10)，125.2(C-1′)，115.3(C-2′)，146.3(C-3′)，146.5(C-4′)，115.6(C-5′)，119.4(C-6′)，101.1(C-1″)，73.2(C-2″)，75.7(C-3″)，69.8(C-4″)，73.9(C-5″)，63.2(C-6″)，125.4(C-1″′)，114.9(C-2″′)，145.5(C-3″′)，148.4(C-4″′)，115.8(C-5″′)，121.2(C-6″′)，145.3(C-7″′)，113.7(C-8″′)，166.4(C-9″′)。
Apigenin-7-O-beta-D-(6 " the E-coffee acyl)-glucoside compound 4, C
30H
26O
13, yellow powder.
1H-NMR(DMSO-d
6，600MHz)δppm：6.80(1H，s，H-3)，6.49(1H，d，J＝1.8Hz，H-6)，6.80(1H，d，J＝1.8Hz，H-8)，7.92(2H，d，J＝8.4Hz，H-2′，H-6′)，6.91(2H，d，J＝8.4Hz，H-3′，H-5′)，5.16(1H，d，J＝7.2Hz，H-1″)，6.96(1H，d，J＝1.2Hz，H-2″′)，6.65(1H，d，J＝8.4Hz，H-5″′)，6.84(1H，dd，J＝8.4，1.8Hz，H-6″′)，7.43(1H，d，J＝15.6Hz，H-7″′)，6.23(1H，d，J＝15.6Hz?H-8″′)。
13C-NMR(DMSO-d
6，150MHz)δppm：164.2(C-2)，103.0(C-3)，181.8(C-4)，161.1(C-5)，99.3(C-6)，162.6(C-7)，94.7(C-8)，156.8(C-9)，105.3(C-10)，120.8(C-1′)，128.4(C-2′)，115.9(C-3′)，161.2(C-4′)，115.9(C-5′)，128.4(C-6′)，99.5(C-1″)，72.9(C-2″)，76.2(C-3″)，69.8(C-4″)，73.8(C-5″)，63.2(C-6″)，125.3(C-1″′)，114.9(C-2″′)，145.4(C-3″′，148.2(C-4″′)，115.6(C-5″′)，120.9(C-6″′)，145.2(C-7″′)，113.5(C-8″′)，166.3(C-9″′)(Phytochemistry，1995，47：865-874)。
Embodiment 2 classical pathway complement inhibition tests
1 instrument and reagent
Low-temperature and high-speed whizzer (Jouan MR22i), ELIASA (Thermo Labsystems, Well scanMK3), sheep red blood cell (SRBC), anti-sheep red blood cell (SRBC) antibody (sigma company), human serum, veronal-Veronal sodium buffering salt (BBS
2+, pH=7.4 contains 0.5mM Mg
2+With 0.15mM Ca
2+), tri-distilled water, heparin sodium, thermostat water bath.
2 trial drugs
The life everlasting general extractive of embodiment 1 preparation with therefrom separate the acidylate flavonoid glycoside compound that obtains
3 experimental techniques
Get human serum, with VBS
2+(barbitol buffer solution, pH=7.4 contain 0.5mM Mg to damping fluid
2+With 0.15mM Ca
2+) dilution is 1: 10, as " complement " of classical pathway source.With the antibody of anti-sheep red blood cell with VBS
2+Damping fluid dilution be 1: 1000 as hemolysin; Sheep red blood cell (SRBC) is used VBS
2+Damping fluid is configured to 2% sheep red blood cell (SRBC).Acidylate flavonoid glycoside compound 1～4 sample 2mg of precision weighing embodiment 1 preparation adds VBS respectively
2+Damping fluid 1ml dissolves (the methyl-sulphoxide hydrotropy of adding 1%), is made into the sample solution of 2mg/ml, uses VBS then
2+The damping fluid two-fold dilution becomes 1mg/ml, 0.5mg/ml, 0.25mg/ml, 0.125mg/ml, 0.0625mg/ml, 0.03125mg/ml, 0.015625mg/ml, 8 different concns of 0.0078125mg/ml." complement " 0.2ml of the sample solution 0.2ml of different concns and 1: 10 is behind 37 ℃ of preincubate 10min; Add anti-sheep red blood cell antibody of 0.1ml (1: 1000) and 0.1ml 2% sheep red blood cell (SRBC) successively;, 37 ℃ of water-baths put into the low-temperature and high-speed whizzer after hatching 30min; At 5000rpm, centrifugal 10min under 4 ℃ of conditions.Get every pipe supernatant 0.2ml respectively on enzyme plate, measure absorbancy down at ELIASA (Thermo Labsystems, Well scan MK3) 405nm.Experiment is provided with the sample control group simultaneously, and (sample solution of 0.2ml respective concentration adds 0.4ml VBS
2+Damping fluid), the complement control group is (with 0.2ml VBS
2+Damping fluid replaces sample solution) and full haemolysis group (0.1ml 2% sheep red blood cell (SRBC) is dissolved in three distillatory water of 0.5ml).Calculate the haemolysis inhibiting rate behind the sample sets absorbance deduction respective sample control group absorbance with each concentration.As the X axle, the haemolysis inhibiting rate is as the mapping of Y axle, the fitting a straight line calculation of half inhibitory concentration IC that obtains with the logarithm of sample concentration
50Value.
4 experimental results
As positive control drug, the result shows that the acidylate flavonoid glycoside 1～4 of above embodiment preparation can suppress classical pathway of complement and activate the cell haemolysis that is caused, and has significant ACA with heparin sodium.The result sees table 1
Table 1 compound 1-4 is to the restraining effect
of complement system classical pathway
5 experiment brief summaries
Acidylate flavonoid glycoside 1～4 has identical configuration: Flavone aglycone-sugar-aromatic ring side chain, and can suppress classical pathway of complement and activate the cell haemolysis that is caused, have significant ACA; The activity of each monomeric compound all is better than the activity of life everlasting total extract, and visible this compounds is one type of good complement inhibitor, can be used for the various diseases that the improper activation of complement causes; And effective concentration is low, and toxicity is low, drug safety; Wide material sources, and compound 1～3 is a new compound; The acidylate flavonoid glycoside can directly be digested and assimilated by body as the part of medicinal plant, and the complement inhibitor of from natural product, developing also has the low advantage of cost, is indicating that this compounds has a good application prospect.
Claims (10)
1. acidylate flavonoid glycoside compound is characterized in that, compound has the structure of formula I:
Formula I
R wherein
1, R
2For identical or different, they are respectively H, OH or OCH
3
R
3, R
4Be respectively H or be following groups:
2. acidylate flavonoid glycoside compound according to claim 1 is characterized in that, said compound be apigenin-4 '-O-β-D-(6 " E-coffee acyl)-glucoside 1, following structural formula:
3. acidylate flavonoid glycoside compound according to claim 1 is characterized in that, said compound be luteolin-4 '-O-β-D-(6 " E-coffee acyl)-glucoside 2, following structural formula:
4. acidylate flavonoid glycoside compound according to claim 1 is characterized in that, said compound be Quercetin-4 '-O-β-D-(6 " E-coffee acyl)-glucoside 3, following structural formula:
5. acidylate flavonoid glycoside compound according to claim 1 is characterized in that, said compound is apigenin-7-O-beta-D-(6 " E-coffee acyl)-glucose 4, following structural formula:
6. the application of acidylate flavonoid glycoside compound in the preparation anticomplement medicament according to claim 1.
7. application according to claim 6 is characterized in that, the pharmaceutical composition that described medicine is made up of as activeconstituents and pharmaceutical carrier formula I compound.
8. according to the application of claim 7, it is characterized in that, described medicine by apigenin-4 '-pharmaceutical composition that O-β-D-(6 " E-coffee acyl)-glucoside 1 is formed as activeconstituents and pharmaceutical carrier.
9. according to the application of claim 7, it is characterized in that, described medicine by luteolin-4 '-pharmaceutical composition that O-β-D-(6 " E-coffee acyl)-glucoside 2 is formed as activeconstituents and pharmaceutical carrier.
10. according to the application of claim 7; It is characterized in that, described medicine by Quercetin-4 '-pharmaceutical composition that O-β-D-(6 " E-coffee acyl)-glucoside 3 or apigenin-7-O-beta-D-(6 "-E-coffee acyl)-glucose 4 is formed as activeconstituents and pharmaceutical carrier.
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| CN108129437A (en) * | 2018-01-26 | 2018-06-08 | 扬州工业职业技术学院 | A kind of chromocor compound and preparation method and application |
| CN108239059A (en) * | 2018-01-29 | 2018-07-03 | 扬州工业职业技术学院 | It is a kind of using Simulation moving bed from ginkgo biloba p.e separating flavone class compound method |
| CN108250258A (en) * | 2018-04-10 | 2018-07-06 | 扬州工业职业技术学院 | A kind of neoflavone glucosides prepared using fermentation with ultrasonic wave extraction |
| CN109897030A (en) * | 2019-03-26 | 2019-06-18 | 吉林大学 | A kind of 6 "-oxygen-coffee acyl orientin preparation methods |
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| CN104592331A (en) * | 2015-02-03 | 2015-05-06 | 天津科技大学 | Quercetin derivative as well as preparation process and application thereof |
| CN104592331B (en) * | 2015-02-03 | 2017-03-29 | 天津科技大学 | A kind of quercetin derivative and its preparation technology and application |
| CN108129437A (en) * | 2018-01-26 | 2018-06-08 | 扬州工业职业技术学院 | A kind of chromocor compound and preparation method and application |
| CN108239059A (en) * | 2018-01-29 | 2018-07-03 | 扬州工业职业技术学院 | It is a kind of using Simulation moving bed from ginkgo biloba p.e separating flavone class compound method |
| CN108250258A (en) * | 2018-04-10 | 2018-07-06 | 扬州工业职业技术学院 | A kind of neoflavone glucosides prepared using fermentation with ultrasonic wave extraction |
| CN109897030A (en) * | 2019-03-26 | 2019-06-18 | 吉林大学 | A kind of 6 "-oxygen-coffee acyl orientin preparation methods |
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