CN1977855A - Medicinal composition containing mangiferin and its preparing method - Google Patents
Medicinal composition containing mangiferin and its preparing method Download PDFInfo
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- CN1977855A CN1977855A CN 200610166842 CN200610166842A CN1977855A CN 1977855 A CN1977855 A CN 1977855A CN 200610166842 CN200610166842 CN 200610166842 CN 200610166842 A CN200610166842 A CN 200610166842A CN 1977855 A CN1977855 A CN 1977855A
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- chimonin
- cyclodextrin
- cyclodextrin derivative
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Abstract
The present invention relates to a medicine composition containing mangiferin and its preparation method. It is characterized by that the mangiferin is contained in the cyclodextrin derivative, and the mixing ratio of both them is as follows: mangiferin 1g and cyclodextrin derivative 3g-30g. It can effectively raise solubility and bioavailability of mangiferin.
Description
Technical field:
The present invention relates to a kind of Pharmaceutical composition that contains chimonin and preparation method thereof.
Background technology:
Chimonin (mangiferin) has another name called mangiferin, Chinonin, is the natural polyphenol compounds that extracts from plants such as the Anacardiaceae plant Folium mangiferae or the liliaceous plant Rhizoma Anemarrhenae, molecular formula: C
19H
18O
11, molecular weight: 422.Its chemical constitution is as follows:
The pharmacological research of chimonin shows that it has multiple biological activity, as antioxidation, antitumor, antibiotic, antiviral, blood sugar lowering, antiinflammatory, function of gallbladder promoting, immunomodulating or the like.But water-soluble hardly, poorly soluble because of this product, bioavailability is low, and has limited its research and development as new drug to a certain extent.
For this reason, we have invented a kind of Pharmaceutical composition that contains chimonin by a large amount of research, said composition can increase the dissolubility of chimonin effectively, improve bioavailability, and can be made into various dosage forms such as injection, thereby make this chemical compound performance drug effect better.
Summary of the invention:
The purpose of this invention is to provide a kind of Pharmaceutical composition that contains chimonin and preparation method thereof, under the prerequisite that does not change the chimonin structure, increase the chimonin water solublity, overcome the poorly soluble defective of chimonin, and increase its bioavailability.It is characterized in that: select cyclodextrin derivative as the enclose material, chimonin is made clathrate, increase the dissolubility of chimonin in water with this.The ratio of cyclodextrin and chimonin can be 3g-30g: any ratio of 1g scope.Said cyclodextrin derivative comprises: various substituent alpha-cyclodextrin derivants, beta-cyclodextrin derivative, hydroxypropyl-gamma-cyclodextrin derivant and sulfobutyl ether-beta-cyclodextrin derivant etc.
Technical solution of the present invention is that chimonin is added the appropriate amount of organic dissolving, under stirring state, is added drop-wise in the water-soluble cyclodextrin derivative solution, continues to mix solution, makes cyclodextrin derivative that the chimonin enclose is complete.Preparation has better water miscible preparation thus.
Concrete technology is as follows:
Get the chimonin of 1 weight portion, with about 150 weight portions, 60% ethanol heating for dissolving; Get the cyclodextrin derivative of 3-30 weight portion, add the water stirring and dissolving of twice cyclodextrin derivative amount, be thick to cyclodextrin derivative solution.
Two parts of solution are put into water-bath, under the high-speed stirred situation, the chimonin drips of solution is added in the cyclodextrin derivative solution.Continue agitating solution, until being thick.Obtain the chimonin cyclodextrin mixt.
Mangiferin clathrate provided by the invention is 15-30mg/ day as the rat effective dosage ranges of chemotherapeutic sensitivity medicine, and folding to human body according to dosage reduction formula between various animals is 150-300mg/ day/people.Route of administration is oral, every day 3 times.Because of the difference between the animals and human beings body, so allow practical clinical dosage to adjust to some extent.Also can adopt other route of administration.
Pharmaceutical composition provided by the invention adds one or more pharmaceutic adjuvants and makes dosage form on any pharmaceutics.
The specific embodiment:
The following example is intended to further describe for example the present invention, rather than limit the present invention by any way, under the prerequisite that does not deviate from the spirit and principles in the present invention, any change that those of ordinary skills that the present invention did are realized easily all will fall within the claim scope that awaits the reply of the present invention.
Preparation example 1
Folium mangiferae 95% ethanol percolate extraction, decompression recycling ethanol, thick paste are used petroleum ether, ethyl acetate extraction successively, reclaim solvent and obtain Petroleum ether extraction portion, ethyl acetate extraction portion, water layer precipitate.Wherein the water layer precipitate is proposed cooling with 55% ethanol heat and is obtained yellow acicular crystal, obtains chimonin through purification process repeatedly.It is 90% that HPLC measures chimonin content.
Preparation example 2
Rhizoma Anemarrhenae decoction pieces decocting boils twice, and each 1 hour, decocting liquid concentrated, and 80% ethanol precipitation is got supernatant, decompression recycling ethanol, and last absorption with macroporous adsorbent resin is washed to clearly, and 30% ethanol elution is collected eluent, decompression recycling ethanol, drying under reduced pressure, promptly.It is 88% that HPLC measures chimonin content.
Embodiment 1:
Get chimonin 100mg, make it dissolving with the about 15mL heating of 60% ethanol; Take by weighing HP-3.0g, add stirring and dissolving under the water 5mL room temperature.Drip chimonin solution.Add solution, continue to stir, be thick until solution, drying under reduced pressure, promptly.
Embodiment 2:
Get chimonin 100mg, make it dissolving with the about 15mL heating of 70% ethanol; Take by weighing HP-0.3g, add stirring and dissolving under the water 15mL room temperature.Drip chimonin solution.Add solution, continue to stir, be thick until solution, drying under reduced pressure, promptly.
Embodiment 3:
Get chimonin 100mg, make it dissolving with the about 15mL heating of 65% ethanol; Take by weighing alpha-cyclodextrin 1.0g, add stirring and dissolving under the water 10mL room temperature.Drip chimonin solution.Add solution, continue to stir, be thick until solution, drying under reduced pressure, promptly.
Embodiment 4:
Get chimonin 100mg, make it dissolving with the about 5mL heating of acetone; Take by weighing beta-schardinger dextrin-1.0g, add stirring and dissolving under the water 5mL room temperature.Drip chimonin solution.Add solution, continue to stir, be thick until solution, drying under reduced pressure, promptly.
Embodiment 5:
Get chimonin 100mg, make it dissolving with the about 15mL heating of dehydrated alcohol; Take by weighing hydroxypropyl-gamma-cyclodextrin 1.0g, add stirring and dissolving under the water 5mL room temperature.Drip chimonin solution.Add solution, continue to stir, be thick until solution, drying under reduced pressure, promptly.
Embodiment 6:
Get chimonin 100mg, make it dissolving with the about 15mL heating of methanol; Take by weighing sulfobutyl ether-beta-cyclodextrin 1.0g, add stirring and dissolving under the water 20mL room temperature.Drip chimonin solution.Add solution, continue to stir, be thick until solution, drying under reduced pressure, promptly.
The preparation of formulation preparation example 1 chimonin cyclodextrin inclusion compound composition injection
Get chimonin hydroxypropyl-beta-cyclodextrin inclusion 10g, add in the 1000ml double distilled water, the 0.22um filter membrane is crossed in dissolving, 120 ℃ of sterilization 15min, promptly.
The capsular preparation of formulation preparation example 2 chimonin hydroxypropyl-beta-cyclodextrin inclusions
Chimonin hydroxypropyl-beta-cyclodextrin inclusion 200g crosses 80 mesh sieves, adds microcrystalline Cellulose 100 grams as the diluent compositing formula, mixing, and encapsulated, that is, content of dispersion is the 100mg/ grain.
The 1 chimonin cyclodextrin clathrate solubility test of test example
Precision takes by weighing and is ground into fine powder chimonin 5mg and chimonin hydroxypropyl-beta-cyclodextrin inclusion 500mg respectively, places 25 ± 2 ℃ of 50ml distilled water, 30 seconds of powerful jolting every 5 minutes; Observe the dissolving situation in 30 minutes.Chimonin still has visible particles of solute, and its water solubility belongs to almost insoluble matter of water less than 0.1mg/ml; The chimonin HP-is dissolving fully then.In addition precision takes by weighing and is ground into fine powder chimonin hydroxypropyl-beta-cyclodextrin inclusion 1000mg, places 25 ℃ ± 2 ℃ 30ml distilled water, 30 seconds of powerful jolting every 5 minutes; Observe the dissolving situation in 30 minutes, the chimonin HP-has a small amount of visible particles of solute.Therefore chimonin HP-water solubility belongs to the slightly molten material of water greater than 10mg/ml.
Test example 2 chimonin hydroxypropyl-beta-cyclodextrin inclusions and chimonin oral administration biaavailability are relatively.
1. medicinal liquid preparation
It is an amount of to take by weighing the chimonin hydroxypropyl-beta-cyclodextrin inclusion, adds deionized water dissolving, and being made into concentration is 5mg/mL solution, is sample A; It is an amount of to take by weighing chimonin, adds 1% carboxymethylcellulose sodium solution suspendible, makes the 5mg/mL suspension, is sample B.
2. gastric infusion scheme rat fasting 16h freely drinks water, difference gastric infusion sample A and sample B, and dosage is respectively 50mg/kg.Respectively at 15min, 30min after 5min before the administration and the administration, 45min, 60min, 90min, 120min, 180min, 240min, 300min,, 360min, 480min get blood, separation of serum.
3. sample treatment
The accurate just sample 0.2mL of blood plasma that draws of the processing of plasma sample, accurate 10% trichloroacetic acid, the 40 μ L that add cold preservation, vortex 3min, the centrifugal 10min of 12000r/min draws the about 120 μ L of supernatant and places point end sample introduction bottle, HPLC auto injection.
The mensuration of 4 samples
4.1 instrument
1100 series of high efficiency chromatograph of liquid (U.S. Agilent company); Comprise the G1312A binary pump, the G1313A automatic sampler,
4.2 the chromatographic condition chromatographic column that plasma sample is measured: Tianjin, island Shim packCLC ODS post (150mm * 6mm, 5 μ m); Mobile phase: methanol acetonitrile 1.2%KH2PO4 aqueous solution (24: 2: 74); Flow velocity 0.8mL/min detects wavelength: the 254nm column temperature: 40 ℃.
4.3 result
The bioavailability of table 1 mangiferin clathrate and chimonin relatively
| Parameter | Chimonin | Mangiferin clathrate |
| Tmax/h | 0.75 | 2.0 |
| Cmax/μg/ml | 5.2 | 38.7 |
| T 1/2/h | 1.5 | 3.0 |
| AUC 0-∞/μg.h/ml | 171.34 | 1294.57 |
The above results shows: oral chimonin hydroxypropyl-beta-cyclodextrin inclusion blood drug level (Cmax) shows that far above oral chimonin blood drug level (Cmax) the mangiferin clathrate bioavailability improves a lot.Test example 3 mangiferin clathrate tumor potentiations research
1. medicine
Mangiferin clathrate according to 2 preparations of formulation preparation example.Cisplatin is produced by Dezhou, Shandong Province pharmaceutical factory.
2. animal
The Wistar rat, SPF level, male and female half and half, 150～180g, 18～25 ℃ of room temperatures, humidity 40～60%.Provide by unming Medical College's Experimental Animal Center.Feedstuff is provided by medical animal experiment center, Guangdong Province, freely ingests and drinks water, and changes the drinking-water bottle every day once.
3. experimental technique:
3.1 modeling: Walker256 cell line is drawn the pharmacological room from Shanghai Institute of Pharmaceutical Industry, cell line is cultivated in 1640 culture medium, cell concentration furnishing about 1 * 10
6, aseptic down with the 0.5ml injection cell in weanling Wistar rat abdominal cavity, grew up to ascites tumor in 6-8 days.Again the ascites tumor Mus is put to death, collect ascites in sterile vials, get 0.5ml cell row behind sterilization skin and be subcutaneously injected into the weaning rat oxter and make solid tumor, 8-10 days with sacrifice of animal, aseptic getting tumor tissue places the plate that fills 1640 culture medium down, and tumor is cut into 1mm
3The tumor piece of size is standby.Other gets rat, and male and female are regardless of, sub-model group, cisplatin group, mangiferin clathrate senior middle school low dose group, mangiferin clathrate senior middle school low dose group and cisplatin combination group, totally 8 groups.Animal is cut the abdominal cavity down in the sodium intravenous anesthesia of 2% pentobarbital, expose liver, on liver, make a call to a tunnel gently, the tumor piece is implanted with ophthalmic forceps, hemostasis by compression, pass abdomen posterior vein injection 1ml normal saline is put back in the cage and is raised.
3.2 grouping: the hepatocarcinoma rat is divided into 8 groups at random by body weight, 10 every group.Be respectively model group, cisplatin group, mangiferin clathrate senior middle school low dose group, mangiferin clathrate senior middle school low dose group and cisplatin combination group.Be administered once successive administration 14 days every day by dosage shown in the table 2 and administering mode.
4. detection index: the last administration was put to death after 24 hours, got blood, stripped tumor tissue.
5.1 tumor is heavy and tumour inhibiting rate: tumour inhibiting rate %=(the average tumor of the average tumor weight/model group of 1-administration group is heavy) * 100%
According to each group tumour inhibiting rate, by the Burgi correction formula drug combination group is carried out curative effect and judge.That is: Q=drug combination group tumour inhibiting rate/(cisplatin group tumour inhibiting rate+chimonin group tumour inhibiting rate-cisplatin group tumour inhibiting rate * chimonin group tumour inhibiting rate)
If q value is 0.85～1.15 for simple addition, q＞1.15 are enhancing, and q＜0.85 is an antagonism.
5. result: chimonin solution presses down the potentiation of tumor to cisplatin
Table 2 chimonin is to the influence of hepatocarcinoma rat tumour inhibiting rate
| Group | Administering mode | Dosage (mg/kg) | Tumor heavy (g) | Tumour inhibiting rate (%) | Q-value |
| Model mangiferin clathrate mangiferin clathrate mangiferin clathrate cis-platinum mangiferin clathrate+cis-platinum mangiferin clathrate+cis-platinum mangiferin clathrate+cis-platinum | —— i.g i.g i.g i.p i.g i.g i.g | —— 30 15 5 0.5 30+0.5 15+0.5 5+0.5 | 4.30±0.76 3.29±0.56 * 3.47±0.88 * 3.84±0.72 3.26±0.69 * 1.07±0.36 **##△ 1.95±0.32 **#△ 3.07±0.26 ** | —— 23.4 19.3 10.6 24.3 75.2 54.7 28.5 | 1.79 1.41 0.88 |
Compare with model group:
*, P＜0.05;
*, P＜0.01.Compare with corresponding chemotherapeutic group:
#, P＜0.05;
##, P＜0.01.Compare with same dose chimonin solution group:
△, P＜0.05;
△ △, P＜0.01.
The result shows, lower than the antitumor activity of cisplatin (0.5mg/kg) hepatocarcinoma of low dosage, tumour inhibiting rate only reaches 24.3%.Mangiferin clathrate only shows significantly antitumor activity under 30mg/kg dosage, tumour inhibiting rate is 23.4%.When mangiferin clathrate and cisplatin combined application, antitumor activity obviously improves, and each group relatively has significant difference with model group.The q value was 1.41 and 1.79 when mangiferin clathrate 15mg/kg and 30mg/kg and cisplatin share, and greater than 1.15, showed that mangiferin clathrate has certain potentiation to the tumor that presses down of cisplatin.
7 conclusions
Mangiferin clathrate and cisplatin coupling can obviously strengthen the antitumor activity of cisplatin.
Claims (6)
1, a kind of pharmaceutical composition that contains chimonin and cyclodextrin derivative is characterized in that chimonin is comprised in the cyclodextrin derivative, and the two proportioning is: chimonin 1g, cyclodextrin derivative 3g-30g.
2, the described pharmaceutical composition of claim 1 is characterized in that chimonin is comprised in the cyclodextrin derivative, and the two proportioning is: chimonin 1g, cyclodextrin derivative 3g-10g.
3, the described pharmaceutical composition of claim 1, it is characterized in that: cyclodextrin derivative can be selected from: various substituent alpha-cyclodextrin derivants, beta-cyclodextrin derivative, hydroxypropyl-gamma-cyclodextrin derivant and sulfobutyl ether-beta-cyclodextrin derivant etc.
4, the described pharmaceutical composition of claim 1, it is characterized in that: cyclodextrin derivative is preferably HP-.
5, the preparation of drug combination method of claim 1 is characterized in that: get chimonin, dissolve with appropriate solvent; Get cyclodextrin derivative, add an amount of water stirring and dissolving, under the high-speed stirred situation, the chimonin drips of solution is added in the cyclodextrin derivative solution.Continue agitating solution, until being thick.Obtain the chimonin cyclodextrin mixt.
6, the Pharmaceutical composition of claim 1 adds one or more pharmaceutic adjuvants and makes dosage form on any pharmaceutics.
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| Application Number | Priority Date | Filing Date | Title |
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| CN 200610166842 CN1977855A (en) | 2005-12-09 | 2006-12-07 | Medicinal composition containing mangiferin and its preparing method |
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| CN101810591A (en) * | 2010-03-31 | 2010-08-25 | 昆明制药集团股份有限公司 | Mangiferin dispersible tablets and preparation method thereof |
| CN102161657A (en) * | 2010-02-24 | 2011-08-24 | 昆明制药集团股份有限公司 | Mangiferin crystal I and preparation method thereof |
| CN101647794B (en) * | 2009-09-11 | 2012-09-19 | 天津中医药大学 | Diffractive ring mangiferin in mango leaf and new application of mango leaf extract containing diffractive ring mangiferin |
| CN103110660A (en) * | 2013-03-15 | 2013-05-22 | 广西中医药大学 | Mangiferin-cis-platinum composition and use thereof for treating cancer |
| JP2017031146A (en) * | 2015-07-30 | 2017-02-09 | 学校法人近畿大学 | NIK inhibitor |
| WO2019150087A1 (en) * | 2018-01-30 | 2019-08-08 | Olusola Clement Idowu | Mangiferin as a protective agent against mitochondrial dna damage and skin-care compositions comprising same |
| GB2576301A (en) * | 2018-07-06 | 2020-02-19 | Clement Idowu Olusola | Mangiferin-containing skin-care compositions and methods |
| US10624830B2 (en) | 2017-11-30 | 2020-04-21 | L'oreal | Aqueous compositions with mangiferin for cosmetic applications |
| CN111194908A (en) * | 2020-01-16 | 2020-05-26 | 河南科技学院 | Preparation method of Pickering high internal phase emulsion gel based on mangiferin/gamma-cyclodextrin compound |
| CN111803421A (en) * | 2020-08-13 | 2020-10-23 | 苏格格 | Moisturizing, whitening and skin-care cream |
| US10898420B2 (en) | 2016-10-31 | 2021-01-26 | L'oreal | Compositions containing phenolic compounds having synergistic antioxidant benefits |
| CN115737624A (en) * | 2021-12-31 | 2023-03-07 | 山东省妇幼保健院 | Application of natural medicine in preparation of anti-acinetobacter baumannii medicine |
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2006
- 2006-12-07 CN CN 200610166842 patent/CN1977855A/en active Pending
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101647794B (en) * | 2009-09-11 | 2012-09-19 | 天津中医药大学 | Diffractive ring mangiferin in mango leaf and new application of mango leaf extract containing diffractive ring mangiferin |
| CN102161657A (en) * | 2010-02-24 | 2011-08-24 | 昆明制药集团股份有限公司 | Mangiferin crystal I and preparation method thereof |
| CN102161657B (en) * | 2010-02-24 | 2013-12-11 | 昆明制药集团股份有限公司 | Mangiferin crystal I and preparation method thereof |
| CN101810591A (en) * | 2010-03-31 | 2010-08-25 | 昆明制药集团股份有限公司 | Mangiferin dispersible tablets and preparation method thereof |
| CN103110660A (en) * | 2013-03-15 | 2013-05-22 | 广西中医药大学 | Mangiferin-cis-platinum composition and use thereof for treating cancer |
| JP2017031146A (en) * | 2015-07-30 | 2017-02-09 | 学校法人近畿大学 | NIK inhibitor |
| US10898420B2 (en) | 2016-10-31 | 2021-01-26 | L'oreal | Compositions containing phenolic compounds having synergistic antioxidant benefits |
| US10624830B2 (en) | 2017-11-30 | 2020-04-21 | L'oreal | Aqueous compositions with mangiferin for cosmetic applications |
| WO2019150087A1 (en) * | 2018-01-30 | 2019-08-08 | Olusola Clement Idowu | Mangiferin as a protective agent against mitochondrial dna damage and skin-care compositions comprising same |
| GB2576301A (en) * | 2018-07-06 | 2020-02-19 | Clement Idowu Olusola | Mangiferin-containing skin-care compositions and methods |
| CN111194908A (en) * | 2020-01-16 | 2020-05-26 | 河南科技学院 | Preparation method of Pickering high internal phase emulsion gel based on mangiferin/gamma-cyclodextrin compound |
| CN111194908B (en) * | 2020-01-16 | 2022-06-17 | 河南科技学院 | Preparation method of Pickering high internal phase emulsion gel based on mangiferin/gamma-cyclodextrin compound |
| CN111803421A (en) * | 2020-08-13 | 2020-10-23 | 苏格格 | Moisturizing, whitening and skin-care cream |
| CN115737624A (en) * | 2021-12-31 | 2023-03-07 | 山东省妇幼保健院 | Application of natural medicine in preparation of anti-acinetobacter baumannii medicine |
| CN115737624B (en) * | 2021-12-31 | 2024-03-12 | 山东省妇幼保健院 | Application of natural medicine in preparation of anti-Acinetobacter baumannii medicine |
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