CN1990494A - Dried rehmannia root oligosaccharide and its preparation method and uses - Google Patents
Dried rehmannia root oligosaccharide and its preparation method and uses Download PDFInfo
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Abstract
The invention relates to rehmanniae radix oligosaccharides, the method for preparing the same, and its application. The method comprises taking rehmanniae radix medicinal materials as raw material, extracting with and getting rehmanniae radix total sugar, separating with silica gel column and getting the oligosaccharides, mainly comprising stachyose, and. The content is more than 60%. It is demonstrated by pharmacodynamics experiment that the oligosaccharides can inhibit rat lung inflammation induced by lipopolysaccharide of coli bacillus, and can be used to prepare drug treating chronic obstructive pulmonary disease.
Description
Technical field
The present invention relates to effective ingredient in Chinese and extraction and separation technology field thereof, be specifically related to a kind of dried rehmannia root oligosaccharide and its production and application.
Background technology
The dried rhizome of rehmannia is conventional Chinese medicine, and nature and flavor are gentle, function clearing heat and cooling blood, nourishing Yin and promoting production of body fluid.The complex chemical composition of Radix Rehmanniae, main component be iridoid glycosides and carbohydrate [cloudy strong chief editor. Chinese medicine modern study and application (second rolls up) [M]. Xueyuan Press, 1752 (1997)].Bibliographical information, [Bi Xiaoli, Zhang Wei, Liaoning Journal of Traditional Chinese Medicine, 26 (3), 110 (1999)], [Bi Xiaoli, Zhang Wei, Liaoning Journal of Traditional Chinese Medicine, 25 (12), 561 (1998)], [Zhang Wei, Bi Xiaoli, practical Chinese materia medica magazine, 16 (3), 3 (2003)], [river is pure beautiful, Bi Xiaoli, Wang Yue, practical Chinese materia medica magazine, 18 (8), 7 (2002)] dried rhizome of rehmannia injection liquid of being made by the single dried rhizome of rehmannia can be observed and improves chronic obstructive pulmonary disease (COPD) patient lung volume, pulmonary ventilation function in clinical application, significantly improves COPD patient CD
4Numerical value and NK cytoactive improve CD
4/ CD
8Ratio improves patient's cellular immune function, and can improve the preceding state of thrombus, reduces blood viscosity and red blood cell hematocrit.But do not carry out the research report of extraction separation at present both at home and abroad as yet with regard to the chemical ingredients that has this respect active function in the dried rhizome of rehmannia.
Summary of the invention
Technical problem to be solved by this invention is dried rhizome of rehmannia active ingredient is carried out extraction separation, obtains the purity height, and drug action is clear and definite, has the reactive site of pharmaceutical use.
Dried rhizome of rehmannia reactive site disclosed by the invention is to be raw material with dried rhizome of rehmannia medicinal material, after carrying, water obtains dried rhizome of rehmannia total reducing sugar, separate the molecular weight ranges obtain at 381～1012 oligose by gel filtration chromatography then, this oligose mainly is made up of stachyose, raffinose and seminose, wherein stachyose content 〉=60%.
Dried rehmannia root oligosaccharide disclosed by the invention is made by following method:
1, with the section of dried dried rhizome of rehmannia medicinal material or pulverize, use water boiling and extraction, extracting solution is through the macroporous adsorbent resin removal of impurities, water elution, the elutriant activated carbon decolorizing, cryoconcentration is dry must dried rhizome of rehmannia total reducing sugar;
2, dried rhizome of rehmannia total reducing sugar is dissolved in water, separate through gel filtration chromatography, and water or rare salts solution wash-out, the thin layer chromatography inspection is known, and collects to merge spot A, B part in the chromatography collection of illustrative plates, and cryoconcentration, lyophilize promptly get the dried rehmannia root oligosaccharide position; Or
The total sugar soln of the dried rhizome of rehmannia is that 1000 nanofiltration membrane and molecular weight cut-off are 200 nanofiltration membrane by molecular weight cut-off successively, collects two intermembranous solution, and lyophilize promptly gets the dried rehmannia root oligosaccharide position.
Dried rhizome of rehmannia medicinal material water boiling and extraction after section of the present invention or the pulverizing, wherein the weight ratio of the dried rhizome of rehmannia and water is preferably the dried rhizome of rehmannia: water=1: 10～17, decocting number of times is 2～4 times.
Described macroporous adsorbent resin is a nonpolar macroporous adsorption resin, is selected from HPD100 and D101.
Extracting solution behind macroporous adsorbent resin removal of impurities, activated carbon decolorizing, the dry dried rhizome of rehmannia total reducing sugar that gets of cryoconcentration, its concentrated mode that adopts is for being lower than 70 ℃ of vacuum concentration.Drying mode adopts lyophilize.
Described dried rhizome of rehmannia total reducing sugar separates the gel that is adopted through gel filtration chromatography: Sephadex G type, Sephacryl S type also can be attempted with Superose type or Superdex type.The separating ranges of selecting for use is 1 * 10
2～1.5 * 10
3Dalton.Preferred Sephadex G-25 or SephadexG-15.
The gel filtration chromatography of dried rhizome of rehmannia total reducing sugar separates used water or rare salts solution wash-out, and described rare salts solution is that concentration is 0.1mol/L NaCl solution.When adopting rare salts solution wash-out, elutriant needs through the SephadexG-10 desalination.
Thin-layer chromatography condition during the used thin layer chromatography inspection of gel filtration chromatography is known is the general thin-layer chromatography condition of oligose, and preferred thin-layer chromatography condition is: thin layer plate: through 0.1mol/LNaH
2PO
4The silica gel G of handling; Developping agent: propyl carbinol-pyridine-water=4: 4: 1; Exhibition distance: 8～10cm; Developer: aniline-pentanoic-phosphoric acid system (phosphoric acid 20ml adds acetone to 200ml for aniline 2ml, pentanoic 2g); 105 ℃ of baking 10～20min.Spot A, B are bigger tetrose position of polarity and trisaccharide position (see figure 1) in the chromatography collection of illustrative plates.
Detect through HPLC and to show that the dried rehmannia root oligosaccharide position mainly forms (see figure 2) by three kinds of oligose.
With the dried rehmannia root oligosaccharide position that the inventive method obtains, analyze its main molecules quasi-molecular ions [M+Na] of demonstration through MS
+Mass-to-charge ratio be m/z689 and m/z527, the ingredient molecular weight ranges is mainly in 1000 following (see figure 3)s.LC-MS analyzes demonstration, and this oligose position mainly is grouped into by three one-tenth; Molecular weight is that 667 stachyose and molecular weight are 504 raffinose and mannotriose (see figure 4).The three has the following formula structure respectively:
A technical problem more to be solved by this invention is to disclose the application of above-mentioned dried rehmannia root oligosaccharide in preparation treatment chronic obstructive pulmonary disease (COPD) medicine.
Studies show that through pharmacodynamic experiment the dried rehmannia root oligosaccharide position that obtains with the inventive method can obviously suppress LPS inductive total white blood cells and the neutrophil leucocyte number raises, the TNF-alpha levels raises, O
2 -Level rising, the rising of MPO level, lung tissue neutrophil infiltration, tracheal mucosa oedema and tissue injury.Has the pulmonary inflammatory effect of obvious inhibition e. coli lipopolysaccharide (LPS) inductive rat.The dried rehmannia root oligosaccharide position that the present invention extracts can be used for preparing the medicine for the treatment of chronic obstructive pulmonary disease.
The invention will be further described below in conjunction with embodiment.
Description of drawings
Fig. 1 dried rhizome of rehmannia total reducing sugar is through gel filtration chromatography separation eluent thin-layer chromatogram
Used condition is: thin layer plate: through 0.1mol/LNaH
2PO
4The silica gel G of handling; Developping agent: propyl carbinol-pyridine-water (4: 4: 1); Exhibition distance: 8～10cm; Developer: aniline-pentanoic-phosphoric acid system (phosphoric acid 20ml adds acetone to 200ml for aniline 2ml, pentanoic 2g); 105 ℃ of baking 10～20min.Wherein spot A is the tetrose position, and spot B is the trisaccharide position, and spot C is the disaccharide position, and spot D is the monose position.
Fig. 2 dried rehmannia root oligosaccharide position HPLC figure
Analytical column is Shodex Asahipak NH
2P-50 (4.6mm * 250mm, 5 μ m); Moving phase: acetonitrile-water (70: 30); Flow velocity 1.0ml/min; The RID detector.Analysis revealed dried rehmannia root oligosaccharide position mainly is made up of three kinds of oligose.
Fig. 3 dried rehmannia root oligosaccharide position MS collection of illustrative plates
Show its main molecules quasi-molecular ions [M+Na]
+Mass-to-charge ratio be m/z689 and m/z527, the ingredient molecular weight ranges is mainly below 1000.
Fig. 4 dried rehmannia root oligosaccharide position LC-MS collection of illustrative plates
Show that three kinds of oligosaccharides molecule amounts that the dried rehmannia root oligosaccharide position mainly contains are respectively 504,504,667.
Embodiment
Embodiment 1
With crude drug dried rhizome of rehmannia 500g clean dry, section, decoct 3 times with 12 times of deionized waters, each 0.5 hour, filter, merging filtrate, centrifugal, supernatant liquor is by the D101 macroporous adsorptive resins, with the water elution of 5 times of resin bed volumes, collect effluent liquid and water elution liquid, 0.1% activated carbon decolorizing 2 times, filter, merging filtrate obtains the total sugar soln of the dried rhizome of rehmannia, is that 1000 nanofiltration membrane and molecular weight cut-off are 200 nanofiltration membrane by molecular weight cut-off successively, collect two intermembranous concentrated solutions, lyophilize obtains dried rehmannia root oligosaccharide position 87g.
Embodiment 2
With crude drug dried rhizome of rehmannia 500g clean dry, section decocts 3 times with 14 times of deionized waters, each 0.5 hour, filter merging filtrate, centrifugal, supernatant liquor is by the HPD100 macroporous adsorptive resins, with the water elution of 5 times of resin bed volumes, collect effluent liquid and water elution liquid, 0.1% activated carbon decolorizing 3 times filters, merging filtrate, 60 ℃ of concentrating under reduced pressure, lyophilize promptly obtains dried rhizome of rehmannia total reducing sugar 210g.Take by weighing dried rhizome of rehmannia total reducing sugar 5g and be dissolved in the 20mL distilled water, filter.Get filtrate and go up Sephadex G-15 gel column, water wash-out, flow velocity are 2mL/min, and every pipe is collected 8-12mL, know with the thin layer chromatography inspection, collect merge contain three, tetrose spot part, 60 ℃ of concentrating under reduced pressure, lyophilize promptly obtains dried rehmannia root oligosaccharide position 2.3g.
Embodiment 3
With crude drug dried rhizome of rehmannia 500g clean dry, it is block to be ground into the 5mm size, decocts 2 times with 12 times of deionized waters, each 1 hour, filter merging filtrate, centrifugal, supernatant liquor is by the HPD100 macroporous adsorptive resins, with the water elution of 5 times of resin bed volumes, collect effluent liquid and water elution liquid, 0.15% activated carbon decolorizing 3 times filters, merging filtrate, 65 ℃ of concentrating under reduced pressure, lyophilize promptly obtains dried rhizome of rehmannia total reducing sugar 225g.Take by weighing dried rhizome of rehmannia total reducing sugar 6g and be dissolved in the 25mL distilled water, filter.Get filtrate and go up Sephadex G-25 gel column, water wash-out, flow velocity are 2mL/min, and every pipe is collected 8-12mL, know with the thin layer chromatography inspection, collect merge contain three, tetrose spot part, 65 ℃ of concentrating under reduced pressure, lyophilize promptly obtains dried rehmannia root oligosaccharide position 2.8g.
Embodiment 4
With crude drug dried rhizome of rehmannia 500g clean dry, it is block to be ground into the 5mm size, decocts 2 times with 12 times of deionized waters, each 1 hour, filter merging filtrate, centrifugal, supernatant liquor is by the HPD100 macroporous adsorptive resins, with the water elution of 5 times of resin bed volumes, collect effluent liquid and water elution liquid, 0.1% activated carbon decolorizing 3 times filters, merging filtrate, 65 ℃ of concentrating under reduced pressure, lyophilize promptly obtains dried rhizome of rehmannia total reducing sugar 225g.Take by weighing dried rhizome of rehmannia total reducing sugar 6g and be dissolved in the 25mL distilled water, filter.Get filtrate and go up Sephadex G-15 post, use the 0.1mol/LNaCl wash-out, flow velocity is 2mL/min, every pipe is collected 8～12mL, knows with the thin layer chromatography inspection, collect merge contain three, tetrose spot part, through the desalination of Sephadex G-10 post, 65 ℃ of concentrating under reduced pressure, lyophilize promptly obtains dried rehmannia root oligosaccharide position 3g.
Embodiment 5 dried rehmannia root oligosaccharide position pharmacological research
The pharmacological evaluation of the pulmonary inflammatory influence of rat is induced at intravenous injection dried rehmannia root oligosaccharide position to LPS:
One, the foundation of pneumonia rat model
After the SD rat was weighed, the chloral hydrate anesthesia rat with 10% was pressed the 3.5ml/kg intraperitoneal injection.Postanesthetic rat immediate surgery exposes tracheae, directly splashes into LPS (3mg/kg) from air flue with microsyringe, puts to death rat after splashing into LPS 6h, collects bronchoalveolar lavage fluid (BALF), gets lung tissue and do pathological section.
Two, experimental design
Random packet, every group of 8～10 rats are divided normal control group, model group, sample sets; Adopt the intravenous administration mode; Be administered twice, deliver medicine to for the first time air flue and splash into 5min before the LPS, after delivering medicine to air flue for the second time and splashing into LPS 3h.
Three, detect index
Total white blood cells and neutrophil leucocyte number in the bronchoalveolar lavage fluid, tumour necrosis factor (TNF-α), superoxide anion (O
2 -), neutrophil leucocyte myeloperoxidase (MPer) content (MPO).
Four, experimental result
1. the inflammatory cell accumulative is influenced
The dried rehmannia root oligosaccharide position can obviously suppress LPS inductive total white blood cells and the neutrophil leucocyte number raises.
To LPS inductive induced lung BALF inflammatory cell accumulative influence (n=8, X ± S)
| Group | Dosage (mg/kg) | Total white blood cells (* 10 7cells) | Neutrophil leucocyte (* 10 7cells) |
| Normal model dried rehmannia root oligosaccharide position | Physiological saline 300 * 2 | 10.3±1.9 95.9±33.1### 25.9±5.7 *** | 0.4±0.2 80.0±30.8### 11.3±4.6 *** |
Compare with model group
* *P＜0.001; Compare ##P＜0.01, ###P＜0.001 with normal group
2. to the influence of TNF-alpha levels
The dried rehmannia root oligosaccharide position can obviously suppress LPS inductive TNF-alpha levels and raise.
To the influence of TNF-alpha levels among the LPS inductive induced lung BALF (n=7～8, X ± S)
| Group | Dosage (mg/kg) | TNF-α(pg/ml) | Inhibiting rate (%) |
| Normal model dried rehmannia root oligosaccharide position | Physiological saline 300 * 2 | 13.1±6.0 770.9±471.3## 193.9±219.4 ** | 74.9 |
Compare with model group
*P＜0.01; Compare ##P＜0.01 with normal group
3. to O
2 -The influence of level
The dried rehmannia root oligosaccharide position can obviously suppress LPS inductive O
2 -Level raises.
To O among the LPS inductive induced lung BALF
2 -The influence of level (n=7～8, X ± S)
| Group | Dosage (mg/kg) | O 2 -(u/L) | Inhibiting rate (%) |
| Normal model dried rehmannia root oligosaccharide position | Physiological saline 300 * 2 | 48.5±34.0 130.0±31.3## 71.1±18.0 *** | 45.3 |
Compare with model group
* *P＜0.001; Compare ##P＜0.01 with normal group
4. to the influence of MPO level
The dried rehmannia root oligosaccharide position can obviously suppress LPS inductive MPO level and raise.
To the influence of MPO level among the LPS inductive induced lung BALF (n=7～8, X ± S)
| Group | Dosage (mg/kg) | MPO(u/L) | Inhibiting rate (%) |
| Normal model dried rehmannia root oligosaccharide position | Physiological saline 300 * 2 | 222.0±73.4 389.2±165.8# 216.8±56.0 ** | 44.3 |
Compare with model group
*P＜0.01; Compare #P＜0.05 with normal group
5. pathological examination results
The dried rehmannia root oligosaccharide position can obviously suppress LPS inductive lung tissue neutrophil infiltration, tracheal mucosa oedema and tissue injury.
To the influence of LPS inductive induced lung inflammation pathological change (n=8, X ± S)
| Group | Dosage (mg/kg) | The neutrophil infiltration integration | The mucosa edema integration | Lung tissue damage integration |
| Normal model dried rehmannia root oligosaccharide position | Physiological saline 300 * 2 | 0.19±0.37 3.34±0.61### 1.43±0.14 *** | 0.36±0.37 4.14±0.26### 2.03±0.17 *** | 0.25±0.46 4.50±0.58### 2.85±0.30 *** |
Compare with model group
* *P＜0.001; Compare ###P＜0.001 with normal group
Five, conclusion
Intravenous injection dried rehmannia root oligosaccharide position can significantly suppress the rising of lung tissue of rats total white blood cells, neutrophil accumulation that LPS induces generation, to TNF-α, MPO and O among the lung BALF
2 -Level raises and variations such as lung tissue inflammatory cell infiltration, air flue mucosa edema and damage have obvious restraining effect, prompting dried rehmannia root oligosaccharide position is the efficient part of dried rhizome of rehmannia treatment COPD, the effect of anti-inflammatory, inhibition release of cytokines, the release of inflammation-inhibiting medium and anti-oxidant aspect is one of mechanism of Radix Rehmanniae and oligose position (RGOS) thereof treatment COPD.
Claims (10)
1, a kind of dried rehmannia root oligosaccharide, it is characterized in that this oligose is is raw material with dried rhizome of rehmannia medicinal material, after carrying, water obtains dried rhizome of rehmannia total reducing sugar, separate by gel filtration chromatography then and get, molecular weight ranges is 381～1012, mainly form, wherein stachyose content 〉=60% by stachyose, raffinose and seminose.
2, a kind of preparation method of dried rehmannia root oligosaccharide according to claim 1 is characterized in that this preparation method is:
1) with the section of dried dried rhizome of rehmannia medicinal material or pulverize, use water boiling and extraction, extracting solution is through the macroporous adsorbent resin removal of impurities, water elution, the elutriant activated carbon decolorizing, cryoconcentration is dry must dried rhizome of rehmannia total reducing sugar;
2) dried rhizome of rehmannia total reducing sugar is dissolved in water, separate through gel filtration chromatography, and water or rare salts solution wash-out, the thin layer chromatography inspection is known, and collects to merge spot A, B part in the chromatography collection of illustrative plates, and cryoconcentration, lyophilize promptly get the dried rehmannia root oligosaccharide position; Or
The total sugar soln of the dried rhizome of rehmannia is that 1000 nanofiltration membrane and molecular weight cut-off are 200 nanofiltration membrane by molecular weight cut-off successively, collects two intermembranous solution, and lyophilize promptly gets the dried rehmannia root oligosaccharide position.
3, the preparation method of dried rehmannia root oligosaccharide according to claim 2, the weight ratio of the dried rhizome of rehmannia and water is the dried rhizome of rehmannia when it is characterized in that wherein said dried rhizome of rehmannia medicinal material with water boiling and extraction: water=1: 10～17, decocting number of times is 2～4 times.
4, the preparation method of dried rehmannia root oligosaccharide according to claim 2 is characterized in that wherein said macroporous adsorbent resin is HPD100 and D101.
5, the preparation method of dried rehmannia root oligosaccharide according to claim 2 is characterized in that cryoconcentration is meant in the wherein said cryoconcentration drying and is lower than 70 ℃ of vacuum concentration; Drying mode is lyophilize.
6, the preparation method of dried rehmannia root oligosaccharide according to claim 2, it is characterized in that wherein said gel filtration chromatography separates the gel that is adopted and is: Sephadex G type, Sephacryl S type, separating ranges are 1 * 10
2～1.5 * 10
3Dalton.
7, the preparation method of dried rehmannia root oligosaccharide according to claim 2 is characterized in that wherein said rare salts solution is that concentration is the NaCl solution of 0.1mol/L.
8, the preparation method of dried rehmannia root oligosaccharide according to claim 2, when it is characterized in that wherein said gel filtration chromatography separates with rare salts solution wash-out, the elutriant need are through the SephadexG-10 desalination.
9, the preparation method of dried rehmannia root oligosaccharide according to claim 2 is characterized in that wherein said gel filtration chromatography knows with thin layer chromatography inspection, and its thin-layer chromatography condition is: thin layer plate: through 0.1mol/LNaH
2PO
4The silica gel G of handling; Developping agent: propyl carbinol: pyridine: water=4: 4: 1; Exhibition distance: 8～10cm; The developer proportioning: aniline 2ml, pentanoic 2g, phosphoric acid 20ml adds acetone to 200ml; 105 ℃ of baking 10～20min.
10, the application of the described dried rehmannia root oligosaccharide of claim 1 in preparation treatment chronic obstructive pulmonary disease medicine.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101633676B (en) * | 2009-06-04 | 2011-06-08 | 中国食品发酵工业研究院 | Method for preparing high-purity stachyose by using plant chromatographic separation technology |
| CN102875607A (en) * | 2012-09-28 | 2013-01-16 | 浙江大学 | Separation and purification method of raffinose |
| CN102028801B (en) * | 2009-09-30 | 2013-03-20 | 上海中医药大学附属曙光医院 | Radix Rehmanniae oligosaccharide pulmonary delivery traditional Chinese medicinal preparation as well as preparation method and application thereof |
| CN103265583A (en) * | 2013-03-05 | 2013-08-28 | 中国食品发酵工业研究院 | Method for preparing stachyose crystal |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1093544C (en) * | 1999-12-23 | 2002-10-30 | 中国食品发酵工业研究所 | Stachyose and its preparing process |
| CN100354290C (en) * | 2005-05-23 | 2007-12-12 | 青岛国风药业股份有限公司 | Raffinoses oligosaccharide with stachyose as main materials and method for preparing same |
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2005
- 2005-12-30 CN CNB2005101124248A patent/CN100537583C/en active Active
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101633676B (en) * | 2009-06-04 | 2011-06-08 | 中国食品发酵工业研究院 | Method for preparing high-purity stachyose by using plant chromatographic separation technology |
| CN102028801B (en) * | 2009-09-30 | 2013-03-20 | 上海中医药大学附属曙光医院 | Radix Rehmanniae oligosaccharide pulmonary delivery traditional Chinese medicinal preparation as well as preparation method and application thereof |
| CN102875607A (en) * | 2012-09-28 | 2013-01-16 | 浙江大学 | Separation and purification method of raffinose |
| CN102875607B (en) * | 2012-09-28 | 2015-03-04 | 浙江大学 | Separation and purification method of raffinose |
| CN103265583A (en) * | 2013-03-05 | 2013-08-28 | 中国食品发酵工业研究院 | Method for preparing stachyose crystal |
| CN103265583B (en) * | 2013-03-05 | 2016-01-13 | 中国食品发酵工业研究院 | A kind of preparation method of stachyose crystal |
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