CN102949440A - Licoflavone phospholipid complex and preparation method and application thereof - Google Patents
Licoflavone phospholipid complex and preparation method and application thereof Download PDFInfo
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- CN102949440A CN102949440A CN2012105174104A CN201210517410A CN102949440A CN 102949440 A CN102949440 A CN 102949440A CN 2012105174104 A CN2012105174104 A CN 2012105174104A CN 201210517410 A CN201210517410 A CN 201210517410A CN 102949440 A CN102949440 A CN 102949440A
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Abstract
The invention relates to a preparation method of a complex, in particular to a licoflavone phospholipid complex and a preparation method and the application of the licoflavone phospholipid complex; the licoflavone phospholipid complex comprises licoflavone and phospholipid by mass ratio of 1: 0.1-10; and the method comprises the steps of: according to the proportion, adding the licoflavone and the phospholipid into organic solvent, controlling the temperature to be within the range of 10-90 DEG C and carrying out reaction for 20min-8h until the reaction liquid is clear; carrying out pressure reduction or freeze drying to remove the organic solvent; after that, adding inert solvent to separate free drug which is not compounded; and removing the inert solvent and drying to obtain the licoflavone phospholipid complex. The invention is simple in preparation technology and good in reproducibility, and can improves the physicochemical properties including hydrophilic property and oleophylic property of the licoflavone by embedding the licoflavone by the phospholipid, so that the dissolving property of the licoflavone can be improved, the bioavailability of the licoflavone is increased, the problem that the licoflavone is not easily absorbed can be solved, the oxidation resistance of the licoflavone in different environments can be maintained or enhanced.
Description
Technical field
The present invention relates to a kind of preparation method of complex, especially relate to a kind of licoflavone phosphatide complexes and its preparation method and application.
Background technology
Radix Glycyrrhizae is a kind of broad-spectrum Chinese herbal medicine, can coordinating the actions of various ingredients in a prescription, again can QI invigorating and in, eliminating fire and detoxication, strong muscles and bones; Cure mainly the diseases such as weakness of the spleen and stomach, many, the pharyngalgia of cough, carbuncle and painful swelling, infantile carbuncle, can also play antiulcer, anti-inflammatory, blood pressure lowering, blood fat reducing, maincenter inhibition even antineoplastic action, be called as " state is old " in the Chinese medicine, praise and be " king in the medicine ".
Mainly contain triterpenes, flavonoid and polysaccharide compound in the Radix Glycyrrhizae, since the sixties in 20th century, it is found that the flavone compound in the glycyrrhiza genus has the effects such as antiinflammatory, antiviral, heart tonifying, calmness and analgesia.After find that again they have the effects such as antioxidation, defying age, antitumor.Especially in recent years find also that the flavonoid composition has very strong inhibition proliferation function to HIV (human immunodeficiency virus) (HIV) in the Radix Glycyrrhizae, to the research of liquorice flavonoids compound with use and become gradually focus.
Antitumor action: Radix Glycyrrhizae total flavones can suppress generation and the development of mouse interior tumor, can significantly improve the increase in life span of H22 ascites tumor mice, and can increase the thymus index of sarcoma mice, reduces the spleen index of S180 murine sarcoma.Radix Glycyrrhizae total flavones can suppress tumor growth in vivo, and its tumor suppression mechanism may be to realize by the immune system that improves mice.Antioxidation: take peroxide value (POV) as index, adopt Schaal Oven Method research Radix Glycyrrhizae total flavones to the antioxygenic property of oils and fats.The result shows that Radix Glycyrrhizae total flavones all has good antioxidant effect to 4 kinds of edible oil and fat.Anti-aging effects: the SOD enzyme activity raises in the administration group mice serum, and the MDA amount descends, and the mice anti-stress ability strengthens, and weight of mice is also faster than matched group.Show that licoflavone has anti-aging effects.Antiarrhythmic effect: Radix Glycyrrhizae total flavones can prolong the mice arrhythmia incubation period of Aconitine Induced, the mice ventricular fibrillation positive rate that the minimizing chloroform brings out; Can increase ouabain and bring out that ventricular premature contraction, chamber speed appears in Cavia porcellus, quiver in the chamber and the used dosage of asystole, shows that Radix Glycyrrhizae total flavones has antiarrhythmic effect.Anti HIV-1 virus effect Japanese scholars resulting phenol sexual element from Radix Glycyrrhizae tannin active ingredient research comprises that the flavonoid composition strengthened HIV (human immunodeficiency virus) (HIV) derives from adult T-cell leukemia patient's cell strain to ATL-IK antagonism.Wherein demonstrate the inhibitory action to HIV propagation during two kinds of new liquorice chalcone low concentrations.The pharmaceutical compositions that crosses the treatment acquired immune deficiency syndrome (AIDS) of limit and the invention such as great mainly contains licoflavone class such as glycyrrhizin, isoliquiritigenin, liquirtin, isoliquiritin, its HIV (human immunodeficiency virus)-resistant activity is 15～100 times of glycyrrhizic acid, and proved that the existence of glycyrrhizic acid does not affect the pharmacological effect of flavone, caused the extensive attention of Chinese scholars.
But because licoflavone dissolubility in water is very little, had a strong impact on its absorption in vivo, bioavailability is low, and this has affected the performance of its curative effect to a certain extent.Therefore being made into the higher phosphatide complexes of oral administration biaavailability will more have the application future than general oral formulations.But current position does not also pass through the phospholipid embedding of licoflavone, to improve the physicochemical property of licoflavone hydrophilic and oleophilic, and keep or strengthen its non-oxidizability in varying environment, improve licoflavone phosphatide complexes of its bioavailability and preparation method thereof.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art, provide that a kind of preparation technology is simple, favorable reproducibility, the phospholipid embedding by licoflavone, to improve the physicochemical property of licoflavone hydrophilic and oleophilic, improve the solubility property of licoflavone, improve its bioavailability, can effectively solve the problem that it is difficult for absorption, and keep or strengthen the preparation method and application of a kind of licoflavone phosphatide complexes of its non-oxidizability in varying environment.
The present invention realizes in the following way:
A kind of licoflavone phosphatide complexes is characterized in that: this licoflavone phosphatide complexes be licoflavone and phospholipid with the complex of mass ratio 1: 0.1-10, described phospholipid is natural phospholipid or synthetic phospholipid;
The method is according to described proportional quantity, licoflavone and phospholipid are joined in the organic solvent, 10 ℃-90 ℃ of temperature, reaction 20min-8h clarifies to reactant liquor, and organic solvent is removed in decompression or lyophilization, add again atent solvent and separate not compound free drug, remove atent solvent, drying namely gets the licoflavone phosphatide complexes;
The consumption of described organic solvent is as the criterion can dissolve licoflavone and phospholipid and to clarify, described organic solvent is any one in ethyl acetate, oxolane, dichloromethane, chloroform, normal hexane, cyclohexane extraction, methanol, ethanol, isopropyl alcohol, n-butyl alcohol or the acetone, its consumption is for to be not less than 1mg medicine/ml solvent in licoflavone, and the optimum medicine concentration after the optimization is 5-25mg medicine/ml solvent;
Described atent solvent is any one or any two kinds mixture in dichloromethane, chloroform or the ethyl acetate, also can be above-mentioned three kinds of mixture;
Described natural phospholipid is soybean lecithin or Ovum Gallus domesticus Flavus lecithin, or the combination of soybean lecithin and Ovum Gallus domesticus Flavus lecithin; Described synthetic phospholipid is two hard ester phosphatidyl cholines, two hard ester acyl phosphatidyl glycerols, dipalmitoyl phosphatidyl choline, DOPC or DPPE, also can be above arbitrarily combination;
The active component that described licoflavone phosphatide complexes can be used as pharmaceutical composition or pharmaceutical preparation is made tablet, slow releasing tablet, capsule, suppository, freeze-dried powder, injection, compound tablet, gel, Emulsion etc.
The present invention has following effect:
1) simple, the favorable reproducibility of preparation technology: licoflavone phosphatide complexes provided by the invention be licoflavone and phospholipid with the complex of mass ratio 1: 0.1-10, described phospholipid is natural phospholipid or synthetic phospholipid; The preparation method of this licoflavone phosphatide complexes, for according to described proportional quantity, licoflavone and phospholipid are joined in the organic solvent, 10 ℃-90 ℃ of room temperatures, reaction 20min-8h clarifies to reactant liquor, decompression or lyophilization, remove organic solvent, add again atent solvent and separate not compound free drug, remove atent solvent, drying namely gets the licoflavone phosphatide complexes.
2) be fit to suitability for industrialized production: it is raw material that the present invention adopts licoflavone, makes the licoflavone phosphatide complexes with phospholipid with suitable preparation method; Or make the dosage forms such as tablet, capsule behind the adding sorptive material.The present invention is by forming phosphatide complexes with licoflavone and a certain amount of phospholipid in suitable solvent, thereby changes the physicochemical property of licoflavone, strengthens its dissolubility and stability, thereby improves its bioavailability.
3) of many uses: the active component that licoflavone phosphatide complexes provided by the invention can be used as pharmaceutical composition or pharmaceutical preparation is made tablet, slow releasing tablet, capsule, suppository, freeze-dried powder, injection, compound tablet, gel, Emulsion etc.
4) experimental results show that the phospholipid embedding by licoflavone of the present invention below by solubility experiment, animal organism availability, to improve the physicochemical property of licoflavone hydrophilic and oleophilic, and keep or strengthen its non-oxidizability in varying environment, improve its bioavailability, and improved the solubility property of licoflavone, can effectively solve it and be difficult for the problem that absorbs.
Licoflavone and the test of phosphatide complexes apparent solubility thereof
Take by weighing respectively the mixture of the licoflavone of excessive licoflavone, licoflavone phosphatide complexes, preparation ratio and phospholipid in 20mL water, stirring at room 24h.Get respectively each sample of 5mL, the centrifugal 10min of 12000rmin-1, after accurate absorption supernatant 1ml diluted with methanol, UV measured.
The apparent solubility measurement result of the mixture of licoflavone, licoflavone phosphatide complexes, licoflavone and phospholipid in water sees Table 1.By data in the table 1 as can be known, the apparent solubility in water of physical mixture and phosphatide complexes is all high than licoflavone crude drug, the apparent solubility of physical mixture in water is 2.45 times of licoflavone crude drug, and the apparent solubility of phosphatide complexes in water is 10.70 times of the licoflavone crude drug, explanation is prepared into phosphatide complexes with licoflavone and has increased its dissolubility in water, and this solubilizing effect has benefited from the formation of this dosage form of phosphatide complexes, and is not only the solubilization of phospholipid.
The mixture of table 1 licoflavone, licoflavone phosphatide complexes, licoflavone and phospholipid
At 20 ℃ apparent solubilities (n=3)
(2) licoflavone, licoflavone phosphatide complexes bioavailability in rats are investigated
Healthy male SD rat, body weight 180-200g, test fasting in front 24 hours and can't help water, every group 8, gavage gives licoflavone and licoflavone phosphatide complexes suspension respectively, take the licoflavone dosage as 500mg/kg, and the tail venous blood sampling, the blood drug level of licoflavone calculates under the plasma concentration curve and meets personally AUC and relative availability behind the mensuration administration different time.The AUC0-∞ that rat oral gavage gives behind licoflavone and the licoflavone phosphatide complexes suspension is respectively 2.96 ± 0.75 μ gmL-1h and 11.18 ± 4.05 μ gmL-1h.The result shows, makes the bioavailability that can significantly improve licoflavone behind the phosphatide complexes, and its relative bioavailability is 377.7%.
The specific embodiment
Embodiment 1
Licoflavone phosphatide complexes (medicine: fat=6: 1)
Take by weighing licoflavone 800mg and soybean phospholipid 200mg, place conical flask, add ethanol 80ml, in 30 ℃ of stirred in water bath 3h, form transparent dark brown yellow solution, the decompressing and extracting organic solvent adds an amount of chloroform, makes the solution clarification, shake well, remove by filter precipitation, filtrate is dry, namely gets the licoflavone phosphatide complexes.
Embodiment 2
The licoflavone phosphatide complexes
Take by weighing licoflavone 600mg and soybean phospholipid 400mg, place conical flask, add ethanol 60ml, in 30 ℃ of stirred in water bath 4h, form transparent dark brown yellow solution, the decompressing and extracting organic solvent adds an amount of chloroform, makes the solution clarification, shake well, remove by filter precipitation, filtrate is dry, namely gets the licoflavone phosphatide complexes.
Embodiment 3
The licoflavone phosphatide complexes
Take by weighing licoflavone 400mg and soybean phospholipid 600mg, place conical flask, add ethanol 40ml, in 30 ℃ of stirred in water bath 1.5h, form transparent brown yellow solution, the decompressing and extracting organic solvent, add an amount of ethyl acetate, shake well removes by filter precipitation, filtrate is dry, namely gets the licoflavone phosphatide complexes.
Embodiment 4
The licoflavone phosphatide complexes
Take by weighing licoflavone 245mg and soybean phospholipid 755mg, place conical flask, add methanol 25ml, in 40 ℃ of stirred in water bath 2h, form transparent brown yellow solution, the decompressing and extracting organic solvent adds an amount of ethyl acetate, makes the solution clarification, shake well, remove by filter precipitation, filtrate is dry, namely gets the licoflavone phosphatide complexes.
Embodiment 5
The licoflavone phosphatide complexes
Take by weighing licoflavone 200mg and soybean phospholipid 800mg, place conical flask, add oxolane 40ml, in 30 ℃ of stirred in water bath 3h, form transparent brown yellow solution, the decompressing and extracting organic solvent adds an amount of chloroform, makes the solution clarification, shake well, remove by filter precipitation, filtrate is dry, namely gets the licoflavone phosphatide complexes.
Embodiment 6
The licoflavone phosphatide complexes
Take by weighing licoflavone 400mg and egg yolk lecithin 600mg, place conical flask, add oxolane 40ml, in 30 ℃ of stirred in water bath 2h, form transparent brown yellow solution, the decompressing and extracting organic solvent adds an amount of chloroform, makes the solution clarification, shake well, remove by filter precipitation, filtrate is dry, namely gets the licoflavone phosphatide complexes.
Embodiment 7
The licoflavone phosphatide complexes
Take by weighing licoflavone 400mg and hydrogenated phospholipid 600mg, place conical flask, add ethanol 40ml, in 30 ℃ of stirred in water bath 1.5h, form transparent brown yellow solution, the decompressing and extracting organic solvent adds an amount of chloroform, makes the solution clarification, shake well, remove by filter precipitation, filtrate is dry, namely gets the licoflavone phosphatide complexes.
Embodiment 8
Licoflavone phosphatide complexes tablet
With licoflavone phosphatide complexes 5g, mix the micropowder silica gel of 0.1-5.0%, place mortar, porphyrize is crossed 80 eye mesh screens; The powder of obtaining adds 0.5% magnesium stearate, tabletting, and get final product.
Embodiment 9
Licoflavone phosphatide complexes capsule
With licoflavone phosphatide complexes 5g, mix the starch of 2%-50%, place mortar, porphyrize is crossed 80 eye mesh screens; Granulate drying; The granule of obtaining incapsulates, and get final product.
Embodiment 10
Licoflavone phosphatide complexes capsule
The licoflavone phosphatide complexes is mixed a certain amount of dextrin, place mortar, porphyrize is crossed 80 eye mesh screens; Granulate drying; The granule of obtaining incapsulates, and get final product.
Embodiment 11
Licoflavone phosphatide complexes capsule
With licoflavone phosphatide complexes 5g, mix the sodium carboxymethyl cellulose of 0.5-5%, place mortar, porphyrize is crossed 80 eye mesh screens; The powder of obtaining incapsulates, and get final product.
The active component that above-mentioned licoflavone phosphatide complexes can be used as pharmaceutical composition or pharmaceutical preparation is made tablet, slow releasing tablet, capsule, suppository, freeze-dried powder, injection, compound tablet, gel, Emulsion etc.
Claims (6)
1. licoflavone phosphatide complexes is characterized in that: this licoflavone phosphatide complexes be licoflavone and phospholipid with the complex of mass ratio 1:0.1-10, described phospholipid is natural phospholipid or synthetic phospholipid.
2. the preparation method of a kind of licoflavone phosphatide complexes as claimed in claim 1, it is characterized in that: the method is according to described proportional quantity, licoflavone and phospholipid are joined in the organic solvent, 10 ℃-90 ℃ of temperature, reaction 20min-8h clarifies to reactant liquor, decompression or lyophilization, remove organic solvent, add again atent solvent and separate not compound free drug, remove atent solvent, drying namely gets the licoflavone phosphatide complexes.
3. the preparation method of a kind of licoflavone phosphatide complexes as claimed in claim 2, it is characterized in that: the consumption of described organic solvent is as the criterion can dissolve licoflavone and phospholipid and to clarify, described organic solvent is any one in ethyl acetate, oxolane, dichloromethane, chloroform, normal hexane, cyclohexane extraction, methanol, ethanol, isopropyl alcohol, n-butyl alcohol or the acetone, its consumption is for to be not less than 1mg medicine/ml solvent in licoflavone, and the optimum medicine concentration after the optimization is 5-25 mg medicine/ml solvent.
4. the preparation method of a kind of licoflavone phosphatide complexes as claimed in claim 2, it is characterized in that: described atent solvent is any one or any two kinds mixture in dichloromethane, chloroform or the ethyl acetate, also can be above-mentioned three kinds of mixture.
5. a kind of licoflavone phosphatide complexes as claimed in claim 1, it is characterized in that: described natural phospholipid is soybean lecithin or Ovum Gallus domesticus Flavus lecithin, or the combination of soybean lecithin and Ovum Gallus domesticus Flavus lecithin; Described synthetic phospholipid is two hard ester phosphatidyl cholines, two hard ester acyl phosphatidyl glycerols, dipalmitoyl phosphatidyl choline, DOPC or DPPE, also can be above arbitrarily combination.
6. the purposes of a kind of licoflavone phosphatide complexes as claimed in claim 1, it is characterized in that: the active component that described licoflavone phosphatide complexes can be used as pharmaceutical composition or pharmaceutical preparation is made tablet, slow releasing tablet, capsule, suppository, freeze-dried powder, injection, compound tablet, gel, Emulsion etc.
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Cited By (6)
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| CN104644503A (en) * | 2015-02-06 | 2015-05-27 | 深圳唯美度生物科技有限公司 | Massage cream capable of deeply retaining water and moisturizing and resisting long-wavelength ultraviolet rays |
| CN104644459A (en) * | 2015-02-06 | 2015-05-27 | 深圳唯美度生物科技有限公司 | Freckle-removing and beautifying cream suitable for all kinds of skin |
| CN105012289A (en) * | 2014-04-29 | 2015-11-04 | 上海鑫昊生物科技有限公司 | Anti-AIDS application of licoricone or derivative of licoricone |
| CN105833288A (en) * | 2016-05-10 | 2016-08-10 | 吉林大学 | Gallic acid phospholipid complex and preparing method and application thereof |
| CN111803393A (en) * | 2020-08-03 | 2020-10-23 | 上海奥利实业有限公司 | Transparent aqueous solution of water-oil insoluble licoflavone, and preparation method and application thereof |
| CN112544972A (en) * | 2019-09-26 | 2021-03-26 | 泰州医药城国科化物生物医药科技有限公司 | Spina date seed flavone phospholipid complex and preparation method and application thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105012289A (en) * | 2014-04-29 | 2015-11-04 | 上海鑫昊生物科技有限公司 | Anti-AIDS application of licoricone or derivative of licoricone |
| CN104644503A (en) * | 2015-02-06 | 2015-05-27 | 深圳唯美度生物科技有限公司 | Massage cream capable of deeply retaining water and moisturizing and resisting long-wavelength ultraviolet rays |
| CN104644459A (en) * | 2015-02-06 | 2015-05-27 | 深圳唯美度生物科技有限公司 | Freckle-removing and beautifying cream suitable for all kinds of skin |
| CN105833288A (en) * | 2016-05-10 | 2016-08-10 | 吉林大学 | Gallic acid phospholipid complex and preparing method and application thereof |
| CN112544972A (en) * | 2019-09-26 | 2021-03-26 | 泰州医药城国科化物生物医药科技有限公司 | Spina date seed flavone phospholipid complex and preparation method and application thereof |
| WO2021056805A1 (en) * | 2019-09-26 | 2021-04-01 | 泰州医药城国科化物生物医药科技有限公司 | Wild jujube seed flavone and phospholipid composite as well as preparation method therefor and application thereof |
| CN111803393A (en) * | 2020-08-03 | 2020-10-23 | 上海奥利实业有限公司 | Transparent aqueous solution of water-oil insoluble licoflavone, and preparation method and application thereof |
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Application publication date: 20130306 |