CN101036643A - Pharmaceutical composition containing arctigenin and preparation method - Google Patents
Pharmaceutical composition containing arctigenin and preparation method Download PDFInfo
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- CN101036643A CN101036643A CNA2007101356460A CN200710135646A CN101036643A CN 101036643 A CN101036643 A CN 101036643A CN A2007101356460 A CNA2007101356460 A CN A2007101356460A CN 200710135646 A CN200710135646 A CN 200710135646A CN 101036643 A CN101036643 A CN 101036643A
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Abstract
A composition for medicine having arctigenin and a method for preparing the same. The composition includes arctigeni, oil, emulsifier and water which is capable of producing emulsion for oral taking and intravenous.
Description
Technical field
The present invention relates to the Pharmaceutical composition of arctigenin, be specially the Pharmaceutical composition and the preparation method of arctigenin, as Emulsion and preparation thereof.
Background technology
Fructus Arctii ArctiumlappaL. is Compositae (Compositae) burdock, and its seed, root, Ye Junke are used as medicine.The medicinal part that Fructus Arctii is commonly used is its fruit, claims Fructus Arctii.Its acrid in the mouth hardship, cold.The effect of tool dispelling wind and heat pathogens, lung qi dispersing rash, subduing swelling and detoxicating is used for saturating, the diseases such as rubella is had an itch, carbuncle sore tumefacting virus of anemopyretic cold, cough with copious phlegm, laryngopharynx swelling and pain, macule.Mainly contain lignanoid and glycoside thereof in the Fructus Arctii.The kind of the lignanoid that occurring in nature has been found has a lot, and the physiology and the pharmacologically active of the lignanoid that studies show that different types of structure in recent years are not quite similar.Lignan component in the Fructus Arctii mainly contains arctiin and arctigenin (arctigenin).Arctigenin molecular formula: C
21H
24O
6Molecular weight: 372; Structural formula is as follows:
The molecular structure of arctigenin
It is reported that the high-load composition arctiin in the oral Fructus Arctii of rat (Arctium lappa) seed is converted into the metabolite arctigenin through the rat intestinal microbial population, show that arctiin is an aglycon active precursor material.The active report of arctigenin mainly contains following several respects: 1) antiviral and antiinflammatory; 2) immunoregulation effect; 3) hypoglycemic activity; 4) antitumor action.
Because arctigenin is fat-soluble compound, its preparation uses especially that drug administration by injection is restricted, and finds relevant report as yet.The present invention has solved the arctigenin solubility problem by experimental study, has enlarged the range of application of arctigenin.
Summary of the invention
The technical problem to be solved in the present invention is prescription of arctigenin Emulsion pharmaceutical composition and preparation method thereof, and wherein Emulsion comprises Orally taken emulsion and vein emulsion.For addressing the above problem, the invention provides following technical scheme:
A kind of pharmaceutical composition of arctigenin contains the arctigenin for the treatment of effective dose, and described pharmaceutical composition can contain the adjuvant of pharmaceutically said oral or intravenously administrable emulsion preparations.
Pharmaceutical composition of the present invention is more preferably formed: contain by weight/weight meter content is arctigenin, pharmaceutically can be used as oil, emulsifying agent and the water of carrier; Its proportioning is arctigenin 0.05~2.0g, oil 5~20g, emulsifying agent 0.5~5.0g, oleic acid 0.02-0.2g, adds water to 100ml;
Preferred compositions proportioning is to contain arctigenin 0.05~1.0g, oil 5~15g, emulsifying agent 1.0~3.0g in every 100ml compositions, oleic acid 0.02-0.08g, isoosmotic adjusting agent by weight/water of weight meter 2.0~3.0% and surplus.
Most preferred compositions proportioning is to contain arctigenin 0.3~0.6g, oil 10~15g, emulsifying agent 1.0~2.0g in every 100ml compositions, oleic acid 0.04-0.07g, isoosmotic adjusting agent by weight/water of weight meter 2.0~3.0% and surplus.
Described preparation of drug combination method is: arctigenin is mixed with oil, be heated to 60~80 ℃, stir, make to be dissolved as clear and bright solution, add oleic acid and emulsifying agent, stir, make to be dissolved as clear and bright solution, get oil phase; With isotonic agent formation water soluble in water, be heated to 60-80 ℃; Under high-speed stirred, oil phase is added to aqueous phase and forms colostrum, after the gained colostrum adds the water standardize solution,, obtain Emulsion through high pressure homogenizer emulsifying.
Preferred manufacturing procedure is: will contain treatment effective dose arctigenin, soybean phospholipid and/or egg yolk lecithin, midchain oil mixes with long-chain oil, is heated to 70~80 ℃, adding oleic acid makes to be dissolved as clear and bright solution, must oil phase; With glycerol formation water soluble in water, be heated to 70-80 ℃; The oil phase that contains arctigenin is added to aqueous phase forms colostrum, after the gained colostrum adds the water standardize solution,, make Emulsion through high pressure homogenizer emulsifying under the condition of pressure 100Mpa with high-speed stirred.
Arctigenin of the present invention extracts by ethanol lixiviate of Fructus Arctii medical material or CO2 supercritical fluid extraction and obtains, and through column chromatography purification acquisition arctiin, arctiin obtains the white crystals arctigenin through column chromatography purification behind acid hydrolysis or enzymolysis, it is 98.2% that the HPLC method records purity.
Arctigenin is the active ingredient in the pharmaceutical composition of the present invention.
Described oil is meant biological acceptable material, refers generally to vegetable oil, animal oil, midchain oil or its mixture.Vegetable oil can be among a kind of or several in soybean oil, Semen Maydis oil, Oleum Arachidis hypogaeae semen, olive oil, Oleum Ricini, Petiolus Trachycarpi oil, Oleum Cocois, Oleum Brassicae campestris, Oleum sesami or the Oleum Gossypii semen; Be preferably the oil that soybean oil, Semen Sesami wet goods are rich in triglyceride.Also can be selected from Fructus Schisandrae oil, Oleum Hippophae, peach kernel oil, almond oil, safflower oil, Oleum Camelliae, Radix Oenotherae erythrosepalae oil, Semen Tritici aestivi germ oil, perilla oil, litsea cubeba oil, Oleum Fructus Bruceae or the Oleum Curcumae one or more; Perhaps be selected from linoleic acid, conjugated linoleic acid, ethyl oleate, castor oil hydrogenated, hydrogenated groundnut, hydrogenated cottonseed oil, Ethyl linoleate, conjugated linoleic acid ethyl ester, self-emulsifying monostearate, suffering/caprin or the glycerol triethyl one or more.Animal oil is selected from: derive from Animal fat usually, comprise fish oil, oleic acid, Whale wax oil etc.Midchain oil (middle-chain triglycerides (MCT)) is a median chain triglyceride oil, and promptly hot capric acid glyceride is semisynthetic natural function oils and fats, carbon chain lengths C
8-10, derive from Oleum Cocois.
Emulsifying agent of the present invention can be one or more in anion surfactant, cationic surface agent, amphoteric surfactant or the non-ionic surface active agent.Wherein anion surfactant is selected from one or more in salt, sulfated oil and the high fatty alcohol sulfuric acid ester of higher fatty acids, as enuatrol, potassium oleate, 12 (14,16,18) alkyl sodium sulfate etc.Cationic surfactant is selected from azochlorosulfonate acid compound, as in octyl sulphuric acid (sulfonic acid) sodium, dioctyl sodium sulfosuccinate, the dodecylbenzene sodium sulfonate one or more; Amphoteric surfactant is selected from one or more in fabaceous lecithin, egg yolk lecithin, phosphatidylcholine, PHOSPHATIDYL ETHANOLAMINE, serinephosphatide, lipositol, phosphatidic acid, cephalin or the hydrogenated phospholipid; Non-ionic surface active agent is selected from one or more in sucrose-fatty esters (as sucrose ester), spans, Tweens, polyoxyethylene fatty acid ester class (as Myrij Myrij), polyoxyethylene aliphatic alcohol ether class (as Bian Ze Brij), Cetomacrogol class, Cremophore EL class or the poloxamer class (as poloxamer).In the preferred soybean phospholipid of emulsifying agent of the present invention, egg yolk lecithin, the hydrogenated phospholipid etc. one or more, more preferably soybean phospholipid and/or egg yolk lecithin.
The isoosmotic adjusting agent of arctigenin Emulsion of the present invention is conventional adjuvant, conventional amount used, oozes purpose as long as reach etc., and isoosmotic adjusting agent is a glycerol as described.
Arctigenin compositions antiinflammatory weight range is everyone 125-500mg every day, and usage can intravenous injection, also can be oral.Because this dosage is to calculate according to animal pharmacological test to get that in view of the diversity of animals and human beings body, the clinical consumption in historical facts or anecdotes border can allow to adjust to some extent.
The specific embodiment
Midchain oil, refined soybean oil, refining Oleum sesami, fish oil, Semen Maydis oil all adopt the commercially available product that Tieling Beiya Medical Oil Co., Ltd. produces to be provided among the embodiment.The commercially available product that fabaceous lecithin, egg yolk lecithin, hydrogenated phospholipid, oleic acid all adopt Shanghai Dong Shang Industrial Co., Ltd. to provide.
Preparation example 1: preparation arctiin
Fructus Arctii is worn into coarse powder, through petroleum ether, ethyl acetate and 80% ethanol reflux, extract, successively, reclaims solvent respectively, gets the ethanol extract part.This extract water is transferred to certain volume, use n-butanol extraction, reclaim n-butyl alcohol, get n-butyl alcohol extract, get the dried cream of above-mentioned n-butyl alcohol extract, carry out macroporous adsorbent resin column chromatography (ratio of dried cream and resin is 1: 30).Wash with water to eluent colourlessly earlier, it is colourless to its liquid to use 30% ethanol elution then instead, reclaims to concentrate behind the ethanol to leave standstill, and occurs the pale powder granule then.Pale powder is by the silica gel H post (dry column-packing) that reduces pressure, with chloroform-methanol (9: 1) eluting, reclaim solvent after, the pure white crystallization be arctiin, it is 98.3% that the HPLC method records purity.
Preparation example 2: preparation arctigenin
Get in the preparation example 1 arctiin and add heating for dissolving in the sterilized water, put coldly, add an amount of Snailase, 37 ℃ of constant temperature shaking tables were cultivated 36 hours, added ethanol and ended enzyme digestion reaction, with the enzymolysis solution evaporated under reduced pressure, residue adds the chloroform dissolving, get chloroform solution, reclaim solvent and get degradation product, with the gained degradation product by the silica gel H post (dry column-packing) that reduces pressure, with the chloroform-methanol gradient elution, after reclaiming solvent, get the pure white crystallization and be arctigenin, it is 98.2% that the HPLC method records purity.
Preparation example 3: the preparation of blank Emulsion
With egg yolk lecithin 1.2g, join in the miscella of refined soybean oil 10g, add oleic acid 0.1g, be heated to 60~80 ℃, stir to make and be dissolved as clear and bright solution, oil phase; Glycerol 2.25g is dissolved in the 60ml water forms water, be heated to 60-80 ℃; Oil phase is added to aqueous phase is emulsified into colostrum with high-speed stirred, after the gained colostrum added water and is settled to 100ml, after emulsifying under the condition of pressure 100Mpa, 121 ℃ of sterilizations were 15 minutes after the packing, make Emulsion through high pressure homogenizer.Gained Emulsion is homogeneous latex emulsion, mean diameter 168nm.
Embodiment 1: the preparation of arctigenin Emulsion
With arctigenin 0.05g, fabaceous lecithin 0.5g, join among the soybean oil 5.0g, add oleic acid 0.02g, be heated to 60~80 ℃, stir to make and be dissolved as clear and bright solution, oil phase; 80ml water is heated to 60-80 ℃; The oil phase that contains arctigenin is added to aqueous phase is emulsified into colostrum with high-speed stirred, after the gained colostrum added water and is settled to 100ml, after emulsifying under the condition of pressure 100Mpa, 121 ℃ of sterilizations were 15 minutes after the packing, make Emulsion through high pressure homogenizer.Gained Emulsion is uniform emulsion, mean diameter 366nm.
Embodiment 2: the preparation of arctigenin Emulsion
With arctigenin 2.0g, egg yolk lecithin 5.0g, join in the miscella of refining Oleum sesami 5g and midchain oil 15g, add oleic acid 0.2g, be heated to 60~80 ℃, stir to make and be dissolved as clear and bright solution, oil phase; 60ml water is heated to 60-80 ℃; The oil phase that contains arctigenin is added to aqueous phase is emulsified into colostrum with high-speed stirred, after the gained colostrum added water and is settled to 100ml, after emulsifying under the condition of pressure 100Mpa, 121 ℃ of sterilizations were 15 minutes after the packing, make Emulsion through high pressure homogenizer.Gained Emulsion is homogeneous latex emulsion, mean diameter 368nm.
Embodiment 3: the preparation of arctigenin Emulsion
With arctigenin 1.0g, egg yolk lecithin 3.0g, join among the midchain oil 15g, add oleic acid 0.08g, be heated to 60~80 ℃, stir to make and be dissolved as clear and bright solution, oil phase; Glycerol 3.0g is dissolved in the 60ml water forms water, be heated to 60-80 ℃; The oil phase that contains arctigenin is added to aqueous phase is emulsified into colostrum with high-speed stirred, after the gained colostrum added water and is settled to 100ml, after emulsifying under the condition of pressure 100Mpa, 121 ℃ of sterilizations were 15 minutes after the packing, make Emulsion through high pressure homogenizer.Gained Emulsion is uniform emulsion, mean diameter 265nm.
Embodiment 4: the preparation of arctigenin Emulsion
With arctigenin 0.05g, egg yolk lecithin 1.0g, join among the fish oil 5.0g, add oleic acid 0.02g, nitrogen protection is heated to 50~70 ℃, stir to make to be dissolved as clear and bright solution, oil phase; Glycerol 2.0g is dissolved in the 40ml water forms water, be heated to 70-80 ℃; The oil phase that contains arctigenin is added to aqueous phase is emulsified into colostrum with high-speed stirred, after the gained colostrum added water and is settled to 100ml, after emulsifying under the condition of pressure 100Mpa, 121 ℃ of sterilizations were 15 minutes after the packing, make Emulsion through high pressure homogenizer.Gained Emulsion is uniform emulsion, mean diameter 274nm.
Embodiment 5: the preparation of arctigenin Emulsion
With arctigenin 0.3g, egg yolk lecithin 1.0g, join in the miscella of soybean oil 6.0g and midchain oil 4.0g, add oleic acid 0.04g, be heated to 70~80 ℃, stir to make and be dissolved as clear and bright solution, oil phase; Glycerol 2.0g is dissolved in the 30ml water forms water, be heated to 70-80 ℃; The oil phase that contains arctigenin is added to aqueous phase is emulsified into colostrum with high-speed stirred, after the gained colostrum added water and is settled to 100ml, after emulsifying under the condition of pressure 100Mpa, 121 ℃ of sterilizations were 15 minutes after the packing, make Emulsion through high pressure homogenizer.Gained Emulsion is uniform emulsion, mean diameter 204nm.
Embodiment 6: the preparation of arctigenin Emulsion
With arctigenin 0.6g, hydrogenated phospholipid 2.0g, join in the miscella of midchain oil 5.0g and Semen Maydis oil 10.0g, add oleic acid 0.07g, be heated to 60~80 ℃, stir to make and be dissolved as clear and bright solution, oil phase; Glycerol 3.0g is dissolved in the 50ml water forms water, be heated to 60-80 ℃; The oil phase that contains arctigenin is added to aqueous phase is emulsified into colostrum with high-speed stirred, after the gained colostrum added water and is settled to 100ml, after emulsifying under the condition of pressure 100Mpa, 121 ℃ of sterilizations were 15 minutes after the packing, make Emulsion through high pressure homogenizer.Gained Emulsion is uniform emulsion, mean diameter 198nm.
Embodiment 7: the preparation of arctigenin Emulsion
With arctigenin 0.5g, egg yolk lecithin 1.4g, join in the miscella of midchain oil 8.0g and soybean oil 7.0g, add oleic acid 0.06g, be heated to 60~80 ℃, stir to make and be dissolved as clear and bright solution, oil phase; Glycerol 2.5g is dissolved in the 60ml water forms water, be heated to 60-80 ℃; The oil phase that contains arctigenin is added to aqueous phase is emulsified into colostrum with high-speed stirred, after the gained colostrum added water and is settled to 100ml, after emulsifying under the condition of pressure 100Mpa, 121 ℃ of sterilizations were 15 minutes after the packing, make Emulsion through high pressure homogenizer.Gained Emulsion is uniform emulsion, mean diameter 155nm.
Embodiment 7: the preparation of arctigenin Emulsion
With arctigenin 0.2g, lecithin 1.4g, join among the soybean oil 10.0g, add oleic acid 0.06g, be heated to 60~80 ℃, stir to make and be dissolved as clear and bright solution, oil phase; Glycerol 2.5g is dissolved in the 80ml water forms water, be heated to 60-80 ℃; The oil phase that contains arctigenin is added to aqueous phase is emulsified into colostrum with high-speed stirred, after the gained colostrum added water and is settled to 100ml, after emulsifying under the condition of pressure 100Mpa, 121 ℃ of sterilizations were 15 minutes after the packing, make Emulsion through high pressure homogenizer.Gained Emulsion is uniform emulsion, mean diameter 175nm.
The influence of test example 1 arctigenin Emulsion xylol induced mice auricle edema
1. material and animal
Arctigenin Emulsion: press embodiment 3 preparations.
Blank Emulsion: by preparation example 3 preparations.
Dexamethasone: lot number 0601146, Zhengzhou Lingrui Pharmaceutical Co., Ltd. produces.
Dimethylbenzene: Hangzhou Zhong Shan chemistry company limited production.
Kunming mouse, unming Medical College's Experimental Animal Center provides.
2. divide into groups and method
Get 80 of Kunming kind white mice, be divided into 8 groups at random.Model group (blank Emulsion), arctigenin Emulsion high dose group (iv, 100mg/kg), middle dosage group (iv, 50mg/kg), low dose group (iv, 25mg/kg), arctigenin Emulsion high dose group (ig, 100mg/kg), middle dosage group (ig, 50mg/kg), low dose group (ig, 25mg/kg), the dexamethasone positive controls (iv, 2mg/kg).40min after the administration is applied to the wide two sides of mouse right ear with 50 μ l dimethylbenzene and causes inflammation, and left ear in contrast, cause the disconnected neck of scorching back 1h and put to death power, cut two ears, lay auricle at same position respectively with the card punch of diameter 9mm along the auricle baseline, immediately weigh, calculate and respectively organize swelling degree and suppression ratio.
Heavy (the mg)-auris dextra auricle of swelling degree (mg)=left ear auricle heavy (mg)
Suppression ratio (%)=(the average auricle of the average auricle weight-administration of model group group is heavy)/average auricle of model group heavy * 100%
3. result
No matter oral still intravenous injection all can significantly suppress the auricle edema that dimethylbenzene causes to arctigenin Emulsion (25mg/kg, 50mg/kg, 100mg/kg), but the injection effect is better than oral.See table 1 for details.
Table 1 arctigenin clathrate xylol cause mice auricle swelling influence (x ± s, n=10)
Group | Dosage (mg/kg) | Swelling degree (mg) | Suppression ratio (%) |
Model group Dexamethasone group arctigenin emulsion (ig) arctigenin emulsion (iv) | - - 25 50 100 25 50 100 | 22.14±2.45 4.15±2.55 *** 13.05±2.24 * 10.16±2.65 ** 8.29±2.10 *** 11.37±2.75 * 7.66±2.41 ** 5.18±1.39 *** | - 81.3 41.1 54.1 62.6 48.6 65.4 76.6 |
Annotate: compare with model group
*P<0.05,
*P<0.01,
* *P<0.001.
Claims (8)
1, a kind of pharmaceutical composition that contains arctigenin, it consists of, and contains in every 100ml compositions:
Arctigenin 0.05~2.0g, oil 5~20g, emulsifying agent 0.5~5.0g, oleic acid 0.02-0.2g, the water of surplus.
2, pharmaceutical composition as claimed in claim 1 is characterized in that, described oil is pharmaceutically as the oil of carrier.
3, pharmaceutical composition as claimed in claim 1, it is characterized in that, described oil is a kind of or its mixture in vegetable oil, animal oil or the midchain oil, and described vegetable oil is soybean oil, Semen Maydis oil, Oleum Arachidis hypogaeae semen, olive oil, Oleum Ricini, Petiolus Trachycarpi oil, Oleum Cocois, Oleum Brassicae campestris, Oleum sesami, Oleum Gossypii semen or their mixture; Described animal oil is fish oil, oleic acid, Whale wax oil or their mixture; Described midchain oil is a decanoyl/octanoyl glycerides, is semisynthetic natural function oils and fats, carbon chain lengths C
8-C
10
4, pharmaceutical composition as claimed in claim 1, it is characterized in that described emulsifying agent is soybean phospholipid, egg yolk lecithin, hydrogenated phospholipid, phosphatidylcholine, PHOSPHATIDYL ETHANOLAMINE, serinephosphatide, lipositol, phosphatidic acid, cephalin or their mixture.
5, pharmaceutical composition as claimed in claim 1, it is characterized in that, contain arctigenin 0.05~1.0g, oil 5~15g, emulsifying agent 1.0~3.0g in every 100ml compositions, oleic acid 0.02-0.08g, isoosmotic adjusting agent by weight/water of weight meter 2.0~3.0% and surplus.
6, pharmaceutical composition as claimed in claim 1, it is characterized in that, contain arctigenin 0.3~0.6g, oil 10~15g, emulsifying agent 1.0~2.0g in every 100ml compositions, oleic acid 0.04-0.07g, isoosmotic adjusting agent by weight/water of weight meter 2.0~3.0% and surplus.
7, pharmaceutical composition according to claim 1 is characterized in that described compositions is Orally taken emulsion or vein emulsion.
8, the described arbitrary preparation of compositions method of claim 1-7 is characterized in that, arctigenin and emulsifying agent are mixed with oil, and heating is stirred, and makes to be dissolved as clear and bright solution, gets oil phase; With isotonic agent formation water soluble in water; Under high-speed stirred, oil phase is added to aqueous phase and forms colostrum, after the gained colostrum adds the water standardize solution,, obtain Emulsion through high pressure homogenizer emulsifying.
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