CN100496504C - Medicinal water-soluble compositions containing 20(R)-ginsenoside (Rg3), and its preparation method - Google Patents
Medicinal water-soluble compositions containing 20(R)-ginsenoside (Rg3), and its preparation method Download PDFInfo
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Abstract
A water-soluble composition of 20(R)-ginsenoside Rg3 for preparing medicine is prepared through preparing the suspension of 20(R)-ginsenoside Rg3, adding it to the aqueous solution of sodium (or magnesium) laurylsulfate, heating to obtain clear aqueous solution, and drying.
Description
Technical field the present invention relates to a kind of ginsenoside's medicinal soluble complex and preparation method thereof.
Background technology ginsenoside Rg3 is a kind of tetracyclic triterpenes saponin compound that is present in the Radix Ginseng, molecular weight is 784.32, it exists with 20 (R)-ginsenoside Rg3s and two kinds of optical isomer forms of 20 (s)-ginsenoside Rg3s again, wherein 20 (R)-ginsenoside Rg3 chemical property are stable, water insoluble, and 20 (s)-ginsenoside Rg3 unstable chemcial properties are soluble in water, and their structural formula is respectively:
20 (R)-ginsenoside Rg3 20 (S)-ginsenoside Rg3s
The molecular structural formula molecular structural formula
It is found that, 20 (R)-ginsenoside Rg3s have stronger inhibition tumor and metastasis effect, but it is again a kind of almost water-fast material, so the bioavailability of its oral formulations is very low, greatly limit the performance of its clinical drug effect, also limited the parenterai administration approach simultaneously.
For making 20 (R)-ginsenoside Rg3s water-soluble, people study this, as on January 29th, 2003 Gazette of Patent for Invention disclosed a kind of＜panaxoside Rg 3 hydroxypropyl-beta-cyclodextrin inclusions and preparation and preparation method (application number 01119929.6) its to the effect that: the hydroxypropyl-beta-cyclodextrin inclusion of panaxoside Rg 3, it is made up of by following weight ratio following raw material, i.e. the ginsenoside: HP-=1:1～200; Its preparation method is that (1) is dissolved in panaxoside Rg 3 in the organic solvent, (2) HP-is soluble in water, (3) under strong agitation, panaxoside Rg 3 solution slowly are added drop-wise in the aqueous solution that contains HP-, all adding the back continues to stir 2～24 hours, use 0.45 μ m filtering with microporous membrane, filtrate is concentrated, eliminate organic solvent, adding injection water dissolves again, cross 0.22 μ m film, the filtrate lyophilization, the white powder that must loosen is ginsenoside's clathrate.
Its weak point is: (1) clathrate is in preparation process, its reactant liquor is recycled to 1/3 o'clock of original volume, still have more organic solvent residual after measured, and lyophilization is invalid to removing residual solvent, thereby this clathrate powder is used to prepare the limit standard that injection is difficult to meet the injection residual solvent.(2) clathrate is in preparation process, because the existence of residual organic solvent, help panaxoside Rg 3 and HP-to form water-soluble clathrate with the ratio of 1:1～200, if residual organic solvent is really eliminated, then in the aforementioned proportion scope, can not form stable clathrate soluble in water, panaxoside Rg 3 can be separated out precipitation very soon from its clathrate aqueous solution, make this clathrate can not be used to prepare injection.(3) panaxoside Rg 3 can not all form clathrate, and utilization rate is 86% only, and the productive rate reduction and the production cost of injection are obviously increased.
Summary of the invention the object of the present invention is to provide 20 (R)-ginseng sapoglycoside Rg 3 medicinal soluble complex and the preparation methoies that a kind of product cost is low, easily be absorbed by the body.
Main material of the present invention (abbreviation major ingredient) is 20 (R)-ginsenoside Rg3s, and auxiliary material (abbreviation adjuvant) is sodium lauryl sulphate (magnesium); The weight ratio of above-mentioned major ingredient and adjuvant is 1:4～50.
The preparation method of 20 (R)-ginseng sapoglycoside Rg 3 medicinal soluble complex:
(1) 20 (R)-ginsenoside Rg3s are soluble in water, make ginsenoside's suspension of 0.01～5%,
(2) sodium lauryl sulphate (magnesium) is soluble in water, make 0.1～5% aqueous solution,
(3) under 1～100 ℃ of condition, stir sodium lauryl sulphate (magnesium) solution and add ginsenoside's suspension, wherein 20 (R)-ginsenoside Rg3s: sodium lauryl sulphate (magnesium)=1:4～50, stirred 1-300 minute,
(4) decompression and solvent recovery is extremely an amount of, drying, and the gained powder is 20 (R)-ginseng sapoglycoside Rg 3 medicinal soluble complex, and 20 (R)-ginsenoside Rg3s' content is 2～20% in this medicinal soluble complex.
The drying means of 20 (R)-ginseng sapoglycoside Rg 3 medicinal soluble complex can be vacuum drying, spray drying and lyophilization.Different drying equipments and drying condition see Table 1.
The different drying equipments of table 1, drying means and drying condition catalog
| Drying equipment | Drying means | Drying condition |
| SZG-4500 type double conic rotary vacuum dryer (Changzhou) | Vacuum drying | 30-60 ℃ of temperature, under 0.01～0.08Mpa pressure, vacuum drying 48 hours. |
| ZLG300 type extractum spray dryer (Changzhou) | Spray drying | Adopt the supersonic jet technology, effluxvelocity 300-990 meter per second is 30～60 ℃ of temperature, under 0.01～0.05Mpa pressure, with the instantaneous drying of hypersonic velocity. |
| FD-1 gland type freezer dryer (Beijing) | Lyophilization | Prior to-45 ℃ of pre-freezes 5 hours, follow procedure intensification lyophilization :-45～-15 ℃ of |
The fusing point test of 20 (R)-ginseng sapoglycoside Rg 3 medicinal soluble complex the results are shown in Table 2.
Table 2 20 (R)-ginsenoside Rg3's raw material and medicinal soluble complex fusing point test result
Saturated solubility test sees Table 3 in the water of 20 (R)-ginseng sapoglycoside Rg 3 medicinal soluble complex.
Maxima solubility measurement result in table 3 20 (R)-ginsenoside Rg3's raw material and the medicinal soluble complex water
| The material title | Dissolubility in the water (g/1000ml) |
| 30% purity 20 (R)-ginsenoside Rg3 | 0.001 |
| The water-soluble compound of 30% purity 20 (R)-ginsenoside Rg3 and |
70 |
| 98% purity 20 (R)- |
0 |
| The water-soluble compound of 98% purity 20 (R)-ginsenoside Rg3 and |
70 |
As seen from table, the saturation solubility of 20 (R)-ginseng sapoglycoside Rg 3 medicinal soluble complex in water is more than 70000 times of its material powder.
The dissolution determination of 20 (R)-ginseng sapoglycoside Rg 3 medicinal soluble complex the results are shown in Table 4.
Dissolution determination result in table 4 20 (R)-ginsenoside Rg3's raw material and the medicinal soluble complex water
| The material title | 5 |
15 |
30 |
45 |
60 minutes |
| 20 (R)- |
0 | 0 | 0 | 0 | 0 |
| The water-soluble compound of 20 (R)-ginsenoside Rg3s and sodium lauryl sulphate | 53.2 | 85.7 | 92.5 | 95.23 | 95.40 |
30 minutes dissolution limit tests of 20 (R)-ginseng sapoglycoside Rg 3 medicinal soluble complex measurement result sees Table 5.
Table 5 20 (R)-ginseng sapoglycoside Rg 3 medicinal soluble complex dissolution limit is measured measurement result
Above-mentioned 20 (R)-ginseng sapoglycoside Rg 3 medicinal soluble complex can be used as preparation antitumor, merging chemicotherapy efficacy enhancing and toxicity reducing, improve immunologic function, antiviral, antithrombotic, resisting fatigue, improvement memory, reducing swelling and alleviating pain, healing of wound and treat the medicaments for coronary disease application, can be made into solid and solution-type oral medicine with it, also can be made into medicine for external use such as aerosol, gel, ointment, patch, suppository.
The present invention has following advantage compared to existing technology:
1. the water-soluble compound that 20 (R)-ginsenoside Rg3s of the present invention and sodium lauryl sulphate (magnesium) form, can be dissolved in the powder of water after drying fully, its saturation solubility in water can reach 70 mg/ml, improves 70000 times than 20 (R)-ginsenoside Rg3 material powders; Maximum dissolution reaches in 95%, 30 minute in the water maximum dissolution greater than 70% in its water, and dissolution is 0 in the water of 20 (R)-ginsenoside Rg3 material powders.Therefore, 20 (R)-ginsenoside Rg3 water-soluble compound utmost points are beneficial to the oral and external absorption of human body.
2. the present invention prepares the process of 20 (R)-ginsenoside Rg3 water-soluble compounds, does not add any organic solvent, so the production process non-environmental-pollution, product does not have dissolvent residual, aspect the environmental protection of production and product, is better than ginsenoside Rg3's clathrate.
3. the water-soluble compound that 20 (R)-ginsenoside Rg3s of the present invention and sodium lauryl sulphate (magnesium) form, the response rate of its main material is 100%, and preparation method operates easily, production cost is starkly lower than ginsenoside Rg3's clathrate.
Description of drawings
Fig. 1 is 20 (R)-ginsenoside Rg3 standard substance qualitative determination high-efficient liquid phase chromatograms.
Fig. 2 is a sodium lauryl sulphate qualitative determination high-efficient liquid phase chromatogram.
Fig. 3 is 20 (R)-ginsenoside Rg3s (30% purity) water-soluble compound assay high-efficient liquid phase chromatogram.
Fig. 4 is that maxima solubility is measured high-efficient liquid phase chromatogram in 20 (R)-ginsenoside Rg3s (30% purity) water-soluble compound water.
Fig. 5 is a dissolution determination high-efficient liquid phase chromatogram in 30 minutes water of 20 (R)-ginsenoside Rg3s (30% purity) water-soluble compound.
Fig. 6 is 20 (R)-ginsenoside Rg3s (98% purity) water-soluble compound assay high-efficient liquid phase chromatogram.
Fig. 7 is a dissolution determination high-efficient liquid phase chromatogram in 30 minutes water of 20 (R)-ginsenoside Rg3s (98% purity) water-soluble compound.
Fig. 8 is 20 (R)-ginsenoside Rg3s (30% purity) fusing point test differential thermal analysis curves.
Fig. 9 is 20 (R)-ginsenoside Rg3s (98% purity) fusing point test differential thermal analysis curves.
Figure 10 is a sodium lauryl sulphate fusing point test differential thermal analysis curve.
Figure 11 is 20 (R)-ginsenoside Rg3s (30% purity) water-soluble compound fusing point test differential thermal analysis curve.
Figure 12 is 20 (R)-ginsenoside Rg3s (98% purity) water-soluble compound fusing point test differential thermal analysis curve.
Figure 13 is 20 (R)-ginsenoside Rg3s (60% purity) water-soluble compound assay high-efficient liquid phase chromatogram.
The specific embodiment
Take by weighing 20 (R)-ginsenoside Rg3s, 5 grams of purity 30%, soluble in water, make ginsenoside's suspension of 0.01%, 70 gram sodium lauryl sulphates are soluble in water, make 5% aqueous solution; Add down ginsenoside's suspension in 1 ℃ of stirring condition, stir and stop to obtain clear and bright aqueous solution after 1 minute; The reclaim under reduced pressure aqueous solution is to original volume 1/5, spray drying, and it is medicinal soluble complex of 2% that the gained powder is 20 (R)-ginsenoside Rg3 content.Get this water-soluble compound 7.15 grams, be dissolved in 10 ml waters, the content of measuring its 20 (R)-ginsenoside Rg3s with high performance liquid chromatograph is 15 mg/ml (see figure 3)s; Other gets this water-soluble compound 33.37 grams, is dissolved in 100 ml waters, and the maximum meltage of measuring its 20 (R)-ginsenoside Rg3 with high performance liquid chromatograph is 70 mg/ml (see figure 4)s, and records that dissolution is 91.46% (see figure 5) in 30 minutes water; Measuring this water-soluble compound fusing point with differential thermal analyzer is 103.38 ℃, 192.16 ℃, 204.27 ℃ and 277.63 ℃ (seeing Figure 11); Measuring 30% purity 20 (R)-ginsenoside Rg3 with differential thermal analyzer is 176.70 ℃, 262.34 ℃ (see figure 8)s; The fusing point of measuring sodium lauryl sulphate with the DSC differential thermal analyzer is 100.74 ℃ of (see figure 10)s.
It is soluble in water to take by weighing 10 milligrams of 20 (R)-ginsenoside Rg3s (purity 98%), makes ginsenoside's suspension of 5%, and 40 milligrams of sodium lauryl sulphates are soluble in water, makes 0.1% aqueous solution; Add down ginsenoside's suspension in 100 ℃ of stirring conditions, stir and stop to obtain clear and bright aqueous solution after 5 hours; The reclaim under reduced pressure aqueous solution is to original volume 1/4, lyophilization, and it is medicinal soluble complex of 20% that the gained powder is 20 (R)-ginsenoside Rg3 content.It all is dissolved in the 100 ml water solution, and the content of measuring its 20 (R)-ginsenoside Rg3s with high performance liquid chromatograph is 0.1 mg/ml (see figure 6), and records that dissolution is 85.33% (see figure 7) in 30 minutes water; Measuring this water-soluble compound fusing point with differential thermal analyzer is 104.16 ℃, 195.27 ℃, 217.25 ℃ and 277.63 ℃ (seeing Figure 12); Measuring 98% purity 20 (R)-ginsenoside Rg3 with differential thermal analyzer is 296.044 ℃ of (see figure 9)s.
Embodiment 3
1 gram 20 (R)-ginsenoside Rg3s (purity 60%) are soluble in water, make ginsenoside's suspension of 2%, 11.4 gram sodium lauryl sulphates are soluble in water, make 3% aqueous solution; Add down ginsenoside's suspension in 20 ℃ of stirring conditions, stir and stop to obtain clear and bright aqueous solution after 0.5 hour; The reclaim under reduced pressure aqueous solution is to 1/10 of original volume, and it is medicinal soluble complex of 4.8% that vacuum drying, gained powder are 20 (R)-ginsenoside Rg3 content.Get these water-soluble compound 8.27 grams and be dissolved in the 10 ml water solution, the content of measuring its 20 (R)-ginsenoside Rg3s with high performance liquid chromatograph is 40 mg/ml (seeing Figure 13).
Repeat the operation of embodiment 1,2,3 respectively, wherein sodium lauryl sulphate replaces with Stepanol MG.
Claims (2)
1 one kind of 20 (R)-ginseng sapoglycoside Rg 3 medicinal soluble complex, it is characterized in that: it is the medicinal soluble complex that is mixed and made into by 1 weight portion 20 (R)-ginsenoside Rg3 and 4～50 weight portion sodium lauryl sulphates, and wherein 20 (R)-ginsenoside Rg3s' content is 2～20%.
The preparation method of 2 20 (R)-ginseng sapoglycoside Rg 3 medicinal soluble complex according to claim 1 is characterized in that:
(1) 20 (R)-ginsenoside Rg3s are soluble in water, make ginsenoside's suspension of 0.01～5%,
(2) sodium lauryl sulphate is soluble in water, make 0.1～5% aqueous solution,
(3) under 1～100 ℃ of condition, stir sodium dodecyl sulfate solution and add ginsenoside's suspension, and 20 (R)-ginsenoside Rg3: sodium lauryl sulphate=1:4～50, stirred 1～300 minute,
(4) decompression and solvent recovery is extremely an amount of, drying, and the gained powder is 20 (R)-ginseng sapoglycoside Rg 3 medicinal soluble complex.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3295950B1 (en) * | 2015-05-15 | 2020-11-18 | Fu, Li | Use of ginseng extract, ginsenoside and ginsenoside derivative in the preparation of medicine or health care product for treating cytomegalovirus infection disorders |
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| CN101530389B (en) * | 2008-03-11 | 2012-02-15 | 沈阳市万嘉生物技术研究所 | Ginsenoside Rg 3 and phospholipid complex and preparing method thereof |
| CN103845280B (en) * | 2012-11-30 | 2017-04-12 | 富力 | 20(R)-ginsenoside Rg3 preparation for external use, preparing method thereof and applications thereof |
| CN103845349A (en) * | 2012-11-30 | 2014-06-11 | 富力 | Application of 20(R)-ginsenoside Rg3 in preparation of medicines for treating leucoderma |
| CN103845348B (en) * | 2012-11-30 | 2016-07-13 | 富力 | 20 (R)-ginsenoside Rg3s application in preparation dysmenorrhea medicine |
| CN104622877A (en) * | 2013-11-14 | 2015-05-20 | 富力 | Application of 20(R)-ginsenoside Rg3 in preparation of medicine for treating hyperlipidemia |
| CN104644651A (en) * | 2013-11-18 | 2015-05-27 | 富力 | Applications of 20(R)-ginsenoside Rg3 in preparation of anti-aging drugs |
| CN104644655A (en) * | 2013-11-20 | 2015-05-27 | 富力 | Applications of 20(R)-ginsenoside Rg3 in preparation of drugs for releasing or/and treating insomnia, and drugs for releasing or/and treating insomnia |
| CN104644661A (en) * | 2013-11-21 | 2015-05-27 | 富力 | Application of 20(R)-ginsenoside Rg3 in preparation of medicament for relieving or/and treating hepatitis B and medicament |
| CN104644653A (en) * | 2013-11-22 | 2015-05-27 | 富力 | Application of 20(R)-ginsenoside Rg3 in preparation of drug for treating anxiety disorder and the drug |
| CN104644652A (en) * | 2013-11-22 | 2015-05-27 | 富力 | Application of 20(R)-ginsenoside Rg3 in preparation of drug for treating depression and the drug |
| CN104644659B (en) * | 2013-11-22 | 2018-02-09 | 富力 | 20 (R) ginseng sapoglycoside Rg 3s are preparing the application in alleviating and/or treating pharyngitis medicine |
| CN105816469B (en) * | 2015-01-06 | 2020-06-26 | 富力 | Application of 20(R) -ginsenoside Rg3 in preparation of medicine or health product for treating osteoporosis and medicine |
| CN105853450A (en) * | 2015-01-20 | 2016-08-17 | 富力 | Application of 20(R)-ginsenoside Rg3 in preparation of medicine or health product for alleviating or/and treating impotence as well as medicine thereof |
| CN109912677A (en) * | 2017-12-12 | 2019-06-21 | 中国科学院大连化学物理研究所 | An ABPP-based molecular probe for ginsenoside Rg3 activity and its synthesis and application |
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| 人参皂苷Rg3的研究进展. 张南生等.医药导报，第25卷第7期. 2006 |
| 人参皂苷Rg3的研究进展. 张南生等.医药导报，第25卷第7期. 2006 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3295950B1 (en) * | 2015-05-15 | 2020-11-18 | Fu, Li | Use of ginseng extract, ginsenoside and ginsenoside derivative in the preparation of medicine or health care product for treating cytomegalovirus infection disorders |
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