CN102512439A - Ginseng oligosaccharide composition as well as preparation method and application thereof - Google Patents
Ginseng oligosaccharide composition as well as preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a ginseng oligosaccharide composition as well as a preparation method and application thereof. The monosaccharide formation of oligosaccharide contained in the ginseng oligosaccharide composition is glucose; and moreover, the molecular weight of the contained oligosaccharide is distributed within a range of 360 to 2,000. The preparation method of the ginseng oligosaccharide composition comprises the following steps of: (a) pulverizing dried ginseng; (b) extracting by using distilled water under the condition of 70 DEG C, repeating for 3 times under the same condition, merging extract at the three times, decompressing, concentrating, freezing and drying; (c) adding 95 percent of ethanol into powder after freezing and drying in the step (b), soaking, centrifugalizing, repeating the operation on residues and volatilizing the ethanol at normal temperature so as to obtain the residues; and (d) redissolving the residues obtained in the step (c) into the distilled water, dialyzing by using a membrane with the trapping molecular weight of 3,000, freezing and drying so as to obtain the ginseng oligosaccharide composition. The ginseng oligosaccharide composition disclosed by the invention has favorable immune activating action to the lymphocytes and the macrophages of a rat in vitro.
Description
Technical field
The present invention relates to a kind of ginseng oligosaccharide composition and method of making the same and application, said ginseng oligosaccharide compositions has the immune activation effect.
Background technology
Radix Ginseng is the dry root of Araliaceae Radix Ginseng (Panax ginseng C.A.Meyer), is considered to cure food since ancient times with the still good medicinal plants of mending.Have strongly invigorating primordial QI, promote the production of body fluid, the effect of calming the nerves admittedly take off.Big quantity research shows that the Radix Ginseng water extract has good immunoregulatory activity, can induction of lymphocyte propagation and T lymphocyte activity.Except that containing polysaccharide, saponin, protein, also contain a certain amount of ginseng oligosaccharide in the Radix Ginseng water extract.
Oligosaccharide generally is meant the chemical compound that is formed by connecting through glycosidic bond 2-10 monosaccharide molecule, in life entity, mainly participates in vital movement with forms such as glycoprotein, glycolipid and glycopeptides, in the process of performance biological function, plays a decisive role.Deep day by day along with what natural oligosaccharide was studied, its uniqueness also is presented in face of the people gradually.Natural oligosaccharide not only has biological activitys such as anti-inflammatory, anticoagulation, short neovascularity generation, antiviral, immunomodulating, and safety non-toxic.In addition, oligosaccharide has less relatively molecular weight, the accurate mensuration that this will more help its structure, help simultaneously to the oligosaccharide biological activity with and the research of structure activity relationship.Therefore, the research of natural oligosaccharide and become the emerging research field of structural chemistry, molecular biology, medical science and bromatology gradually in the application of health food, field of medicaments.
Summary of the invention
The object of the present invention is to provide a kind of ginseng oligosaccharide composition and method of making the same and application with immunostimulatory activity.
At first, the present invention provides a kind of ginseng oligosaccharide compositions, and the monosaccharide of contained oligosaccharide consists of glucose in this oligosaccharide compositions, and the molecular weight distribution of contained oligosaccharide is in the scope of 360-2000.
And, in ginseng oligosaccharide compositions of the present invention, comprise the oligosaccharide that structural formula is following,
The present invention also provides preparation above-mentioned ginseng oligosaccharide method for compositions, and this method comprises the steps:
A pulverizes Radix Ginseng, gets Radix Ginseng powder;
B carries out water extraction to said Radix Ginseng powder, filters then, must filtrate;
C carries out said filtrating centrifugal, gets supernatant and carries out lyophilization, gets dried powder;
D adds 95% ethanol in said dried powder, centrifugal then, gets residue;
E is soluble in water with said residue, through dialysis or membrane filtration, gets said ginseng oligosaccharide compositions.
Preferably in above-mentioned steps B, at first said Radix Ginseng powder being joined weight is in its 8-15 water doubly, soaks 1-2 hour, extracts 60-120 minute down at 50-70 ℃ then.
Preferably in above-mentioned steps D; In said dried powder, adding volume is its 3-5 95% ethanol doubly, soaks centrifugally after 15-30 minute, obtains said residue; And the adding volume is its 3-5 95% ethanol doubly in the said residue that obtains; Soak centrifugally after 15-30 minute, repeat this operation 5-8 time, at normal temperatures said residue is volatilized ethanol then.
Preferably in above-mentioned steps E, the molecular cut off of said dialysis or membrane filtration is smaller or equal to 3000.Dialysis solution concentrates, lyophilization gets the ginseng oligosaccharide compositions.
The present invention also provides the ginseng oligosaccharide compositions to have the application in the medicine of immunostimulatory activity in preparation.
Said immunostimulatory activity can be for promoting lymphopoiesis.
Said immunostimulatory activity can also be the phagocytic function of enhancing macrophage, and promotes the secretion of macrophage to nitric oxide (NO), tumor necrosis factor-alpha (TNF-α) and active oxygen (ROS).
The ginseng oligosaccharide compositions that the present invention extracts can promote lymphopoiesis, and macrophage is had activation, therefore has the immune activation effect.
The specific embodiment
Based on specific embodiment ginseng oligosaccharide composition and method of making the same of the present invention is described below, but the present invention is not limited to cited embodiment.
Need to prove that the instrument that uses among the present invention is: Aglient RRLC 1200SL chromatograph of liquid, the Voyager-DE STR MALDI TOF mass spectrograph of Applied Biosystems company; The LTQ XL linear ion hydrazine chromatograph of Thermo; Vertex 7.0 infrared spectrometers of Bruker company.
Embodiment 1
Take by weighing Radix Ginseng 1000 grams, be crushed to the 40-60 order, extracted 90 minutes down at 70 ℃ after 1.5 hours with 15 liters of distilled water immersions.Use 5 layers of filtered through gauze then.The residue that filtration obtains repeats to extract twice under the same conditions.Merge three times and extract gained filtrating, with 4000 rev/mins centrifugal 10 minutes, collect supernatant, the gained supernatant utilizes Rotary Evaporators under 60 ℃, to be evaporated to 100mL, lyophilization obtains dried powder (521.3 gram).
Take by weighing above-mentioned dried powder 100 grams, 95% ethanol to wherein adding about 500mL soaked 20 minutes, and is centrifugal, supernatant discarded.In the centrifugal residue that obtains, add 95% ethanol of about 500mL once more, soaked 20 minutes, centrifugal, get residue.Should operate repetition 8 times, volatilize ethanol then at normal temperatures, get dry residue.
Above-mentioned dry residue is dissolved in the distilled water, and solid-to-liquid ratio is 1: 5 (w/w).Utilizing molecular cut off is that 3000 film is dialysed to lysate, dialyses 96 hours.Collect extracellular fluid dialysis, in 60 ℃ of following concentrating under reduced pressure, and lyophilization, get the ginseng oligosaccharide compositions.
The ginseng oligosaccharide compositions that the present invention obtains utilizes HPLC under following condition determination, to analyze through complete acid hydrolysis, gets an eluting peak, and elution time is 24.055 minutes, and hence one can see that, and contained oligosaccharide is made up of glucose in this ginseng oligosaccharide compositions.
The HPLC condition determination is following:
Chromatographic column: DIKMA Inertsil ODS-3 (4.6mm * 150mm)
Detector: UV-VIS DAD
Detect wavelength: 245nm
Mobile phase: PBS (0.1M, pH 7.0): acetonitrile=82: 18 (v/v), pH 7.0
Flow velocity: 1.0mL/min
Sample size: 20 μ L
MALDI-MS analyzes the mass-to-charge ratio (m/z) that occurs in the collection of illustrative plates and is respectively: 365,527,689,851,1013,1175,1337,1499,1661,1823,1985.The result shows, the range of molecular weight distributions 360-2000 of said this ginseng oligosaccharide compositions, and the degree of polymerization is 2-12.
Get exsiccant ginseng oligosaccharide compositions, with the KBr tabletting, at 4000～400cm
-1Scope in carry out IR spectrum scanning, record infrared spectrum diagram data is following: at 3600～3200cm
-1The place is for hydroxyl O-H stretching vibration absworption peak, at 3000～2800cm
-1The place shows the C-H stretching vibration absworption peak of methyl or methine, at 1665～1635cm
-1The place shows the bending vibration absworption peak of hydras hydroxyl.1800～700cm
-1Regional then can reflect the characteristics such as sugar type, substituent group and epimerism that different glucide has.1500～1200cm wherein
-1Show the C-H deformation vibration, enclose at 1150～1060cm
-1The place shows the stretching vibration absworption peak of C-O-C.960～930cm
-1The place shows carbohydrate molecule vibration peak, 930～900cm
-1The place shows the asymmetric ring stretching vibration peak of pyranoid ring, 785～755cm
-1The place shows the symmetrical ring stretching vibration peak of pyranoid ring, 973～961cm
-1The place shows the roll vibration of deoxysaccharide methine, 915～876cm
-1The place shows the C-H angle vibration of pyranose β-anomerism, 855～810cm
-1The place shows the C-H angle vibration of pyranose α-anomerism.
Get 200 milligrams of ginseng oligosaccharide compositionss, be dissolved in the 0.1mL distilled water, the centrifugal 5min of 10000rpm; Getting supernatant is splined on Bio-gel P-2 gel chromatography preparative column (3.0 * 90cm), eluent is a distilled water, flow velocity 0.4mL/ minute; Every pipe is collected 12mL, and phenolsulfuric acid method tracking and monitoring is collected suitable eluting peak respectively; Obtain 4 level parts, be respectively: WGOS-1, WGOS-2, WGOS-3, WGOS-4.
That abundance is the highest in the one-level full scan spectrogram of WGOS-1 is m/z 365, and the result in conjunction with front HPLC analyzes monosaccharide residue can confirm it is Portugal's disaccharide.Its two-stage tandem mass spectrogram analysis gets [Glc
2+ Na]+ion (m/z 365), produce Y through collision induced dissociation
1(m/z 203), B
1(m/z 185),
0,2A
2(m/z 305),
0,3A
2(m/z 275),
0,4A
2(m/z 245) ion.Wherein
0,2A
2(m/z 305),
0,3A
2(m/z275),
0,4A
2(m/z 245) come from parent ion respectively and lose C
2H
4O
2(-60Da), C
3H
6O
3(-90Da), C
4H
8O
4(-120Da) produces, and can judge that WGOS-1 is a dextrinose.That abundance is the highest in the one-level full scan spectrogram of WGOS-2 is m/z 527, explains mainly to contain Portugal's trisaccharide among the WGOS-2.Its two-stage tandem mass spectrum is Y ion and B ion like main fragment ion among the figure.
0,2A
3(m/z 467) and
2,4A
3(m/z 407) explain that the glycosidic bond near reducing end is 1 → 4 type; And
0,2A
2(m/z 305),
0,3A
2(m/z 275),
0,4A
2The existence explanation of (m/z 245) is 1 → 6 type near the glycosidic bond of non-reducing end.That abundance is the highest in the one-level full scan collection of illustrative plates of WGOS-3 is m/z 689, explains mainly to contain Portugal's tetrose among the WGOS-3.Its tandem mass spectrum is analyzed [Glc
4+ Na]+parent ion of (m/z 689) loses 1,2,3 sugar units successively, obtains three Y type daughter ion [Glc respectively
3+ Na]+(m/z 527), [Glc
2+ Na]+(m/z365), [Glc+Na]+(m/z 203), explain that WGOS-3 is a linear chain structure.
0,2A
4(m/z 629) and
2,4A
4The existence explanation of (m/z 569) is 1 → 4 near first glycosidic bond of reducing end;
0,2A (m/z 467,305),
0,3A (m/z 437,275),
0,4A (m/z 407,245) shows that two other glycosidic bond is 1 → 6 type.Mainly there is m/z 851,1013,1175,1337 in the WGOS-4 one-level full scan collection of illustrative plates; 1499,1661,1823,1985; Explain and contain Portugal's oligosaccharide that the degree of polymerization is 8 kinds of degree of polymerization of 5-12 among the WGOS-4, its tandem mass spectrum analysis is drawn similar spectrogram, all only produce
0,2The ion of A series with
2,4The ion of A series, and do not produce
0,3The ion of A series, the glycosidic bond among this explanation WGOS-4 is 1 → 4 type.In addition, successive Y ion and these oligosaccharide of B ion explanation do not have branch, all are linear chain structure.
The test of pesticide effectiveness
The ginseng oligosaccharide compositions of utilizing embodiment 1 to prepare is carried out the immunocompetence experiment
1, the ginseng oligosaccharide compositions stimulates the mouse lymphocyte transformation experiment
The preparation of splenocyte suspension: the ICR male mice (after 20 ± 2g) the disconnected necks execution, dissect mice down and get spleen by aseptic condition; Reject connective tissue with fat and after shredding spleen with shears, add 3mL RPMI1640 culture fluid and process splenocyte liquid, use filtered through gauze, draw D-Hanks liquid flushing gauze with homogenizer grinding spleen tissue.Suspension is collected in the aseptic centrifuge tube, 1500rpm, and centrifugal 5min abandons supernatant, in centrifuge tube, adds the Tris-NH of 0.01mol/L
4The Cl hypotonic medium, centrifugal with splitting erythrocyte 1min, reuse D-Hanks liquid washed cell twice becomes 2 * 10 with RPMI-1640 with cell dilution
6Individual/mL, process single cell suspension.
Above-mentioned cell suspension is added in the 96 porocyte culture plates every hole 100 μ L.With 1,10, the concentration of 50,100,200 μ g/mL adds in 96 orifice plates with the ginseng oligosaccharide compositions, and every hole 10 μ L mend every hole to 200uL with complete medium, and establishes blank and ConA (5 μ g/mL) control wells, and LPS (10 μ g/mL) control wells.Put into 37 ℃ of incubators behind the mixing and cultivated 72 hours, cultivate and finish preceding 4 hours, every hole adds MTT liquid (5mg/mL) 20 μ L, and every hole was inhaled and removed supernatant when cultivation finished, and added dimethyl sulfoxide 150 μ L, detects the 570nm OD of place value (A with ELIASA
570), every group of experimental point established 3 multiple holes.
Table 1 ginseng oligosaccharide compositions is to the influence of mouse lymphocyte propagation
Annotate: compare with matched group:
*P＜0.05,
*P＜0.01;
Compare with the ConA group:
△ △P＜0.01;
Compare with the LPS group:
Can know by table 1, when the ginseng oligosaccharide compositions acts on mouse lymphocyte separately in 10-200 μ g/mL concentration range, can promote lymphopoiesis to some extent.And can promote the propagation of inductive T lymphocyte of ConA and the inductive bone-marrow-derived lymphocyte of LPS.
2, the ginseng oligosaccharide compositions stimulates the Turnover of Mouse Peritoneal Macrophages experiment
(1) the ginseng oligosaccharide compositions stimulates peritoneal macrophage to engulf the dimethyl diaminophenazine chloride experiment:
Peritoneal macrophage preparation: (20 ± 2g) put to death behind the injection 6% soluble starch 2mL ICR male mice in continuous three days.D-Hanks (10mL) cleans the abdominal cavity, and liquid collecting in the abdominal cavity is gone in the centrifuge tube, and 4 ℃ centrifugal, and (1000rpm/min 10min), abandons supernatant, with 1640 complete medium re-suspended cells.The adjustment cell concentration is 2 * 10
6Individual/mL, every hole 100 μ L add in 96 orifice plates.(CO in CO2 gas incubator
2: 5%CO
2, 37 ℃) incubate 3h in advance after, with 37 ℃ in advance the PBS (PH=7.4) of temperature wash 2-3 time, remove not attached cell, promptly obtain the macrophage of purification.
The macrophage phagocytic dimethyl diaminophenazine chloride: macrophage is through behind the purification, and adding concentration is 1,10,50,100; 200 μ g/mL ginseng oligosaccharide compositionss (100 μ L/ hole) continue to cultivate 24h, inhale and go supernatant, every hole to add 100 μ L; Concentration is 0.075% neutral red solution, continues to cultivate 1h, after the remaining dimethyl diaminophenazine chloride of PBS (PH=7.4) flush away, adds the cell pyrolysis liquid (ethanol: acetic acid=1: 1 of 100 μ L; V/v), cracking 24h detects with ELIASA, and wavelength is 550nm.
(2) the ginseng oligosaccharide compositions stimulates peritoneal macrophage secretion NO experiment:
The peritoneal macrophage for preparing purification according to the method described above, and with 1,10,50,100,200 μ g/mL (200 μ l/ hole) ginseng oligosaccharide compositions stimulates macrophage after 24 hours, obtains macrophage culture fluid supernatant.Draw 100 μ L cell culture fluid supernatants and add in another 96 well culture plate, and add isopyknic Griess reagent, detect with ELIASA behind the 10min, the detection wavelength is 540nm, and according to the NaNO that is drawn
2The solution standard curve calculates the output of NO behind the variable concentrations sample stimulus macrophage.
(3) the ginseng oligosaccharide compositions stimulates peritoneal macrophage TNF secretion-α experiment:
The peritoneal macrophage for preparing purification according to the method described above, and with 1,10,50,100,200 μ g/mL (200 μ l/ hole) ginseng oligosaccharide compositions stimulates macrophage after 24 hours, obtains macrophage culture fluid supernatant.With the L929 cell with 3 * 10
6The concentration of individual/mL adds in 96 orifice plates, 200 μ l/ holes.After treating cell attachment, discard cell culture fluid, add above-mentioned gained macrophage culture fluid supernatant (100 μ l/ hole), continue to cultivate 18 hours.After cultivate finishing, with PBS cells washed 2 times, every hole adds MTT liquid (5mg/mL, 20 μ L), cultivates to finish the back and inhale and go supernatant, every hole to add 150 μ L dimethyl sulfoxide, detects the 570nm OD of place value with ELIASA, and every experimental point is established 3 holes again.Calculate the L929 cell viability, its cell viability has reflected the TNF-alpha levels indirectly.
Cytotoxicity (%)=(negative control OD value-sample OD value)/negative control OD value * 100
With cell toxicant 50% is an active unit
(4) the ginseng oligosaccharide compositions stimulates peritoneal macrophage secretion ROS experiment:
Adopt the fluorescent probe of DCFH-DA as ROS level in the indicator cells, research ginseng oligosaccharide compositions is to the influence of mouse macrophage ROS burst size.Itself does not fluoresce DCFH-DA, and fat-soluble DCFH-DA is sent fluorescence after the intracellular ROS oxidation after getting into cell, thus the ROS level in the indicator cells.The peritoneal macrophage for preparing purification according to the method described above, with 1,10,50,100,200 μ g/mL ginseng oligosaccharide compositionss stimulate macrophage, and 200 μ l/ holes acted on after 24 hours, discarded the cell culture fluid supernatant.Every hole adds the serum-free RPMI1640 culture fluid that contains DCFH-DA (10 μ mol/L) probe and continues to cultivate 30min.Supernatant discarded does not get into the probe of cell with the PBS flush away, and every Kong Zhongzai adds 200 μ L PBS, on ELIASA, reads fluorescent value (excitation wavelength 488nm, emission wavelength 525nm).
Table 2. ginseng oligosaccharide compositions is tested the macrophage activation effect
*The expression experimental group is compared p＜0.01 with negative control group
The result is as shown in table 2, and the ginseng oligosaccharide compositions can significantly strengthen the phagocytic function of Turnover of Mouse Peritoneal Macrophages at 1-200 μ g/mL, increases the secretion level of NO, TNF-α and ROS, and the amount effect relationship, when effect concentration is 50 μ g/mL, acts on the most remarkable.Prompting ginseng oligosaccharide compositions has significant immunostimulatory activity to macrophage.
Claims (9)
1. a ginseng oligosaccharide compositions is characterized in that, the monosaccharide of contained oligosaccharide consists of glucose, and the molecular weight distribution of contained oligosaccharide is in the scope of 360-2000.
2. ginseng oligosaccharide compositions according to claim 1 is characterized in that, comprises the oligosaccharide that structural formula is following in the said oligosaccharide compositions,
3. preparation claim 1 or 2 described ginseng oligosaccharide method for compositions is characterized in that this method comprises the steps:
A pulverizes Radix Ginseng, gets Radix Ginseng powder;
B carries out water extraction to said Radix Ginseng powder, filters then, must filtrate;
C carries out said filtrating centrifugal, gets supernatant and carries out lyophilization, gets dried powder;
D adds 95% ethanol in said dried powder, centrifugal then, gets residue;
E is soluble in water with said residue, through dialysis or membrane filtration, gets said ginseng oligosaccharide compositions.
4. method according to claim 3 is characterized in that, said step B carries out as follows:
At first said Radix Ginseng powder being joined weight is to soak 1-2 hour in its 8-15 water doubly, extracts 60-120 minute down at 50-70 ℃ then.
5. method according to claim 3 is characterized in that, said step D carries out as follows:
In said dried powder, add volume and be behind doubly 95% soak with ethanol 15-30 minute of its 3-5 centrifugal, obtain said residue; And the said residue that will obtain repeats this operation 5-8 time, at normal temperatures said residue volatilized ethanol then.
6. method according to claim 3 is characterized in that, the said dialysis in the step e or the molecular cut off of membrane filtration are smaller or equal to 3000.
7. the described ginseng oligosaccharide compositions of claim 1 has the application in the medicine of immunostimulatory activity in preparation.
8. application according to claim 7 is characterized in that, said immunostimulatory activity is for promoting lymphopoiesis.
9. application according to claim 7 is characterized in that, said immunostimulatory activity is the phagocytic function of enhancing macrophage, and promotes the secretion of macrophage to nitric oxide, tumor necrosis factor-alpha and active oxygen.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102872178A (en) * | 2012-09-15 | 2013-01-16 | 吉林农业大学 | Preparation method of ginseng oligosaccharide extract and application of ginseng oligosaccharide extract |
| CN103385888A (en) * | 2013-07-24 | 2013-11-13 | 刘淑莹 | Application of ginseng oligosaccharide composition in preparation of anti-oxidation medicine or health-care food |
| CN105699478A (en) * | 2016-03-21 | 2016-06-22 | 长春中医药大学 | Method for quickly identifying sugar |
-
2011
- 2011-10-28 CN CN2011103330156A patent/CN102512439A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| 刘杨: "《人参寡糖的分析》", 8 October 2008 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102872178A (en) * | 2012-09-15 | 2013-01-16 | 吉林农业大学 | Preparation method of ginseng oligosaccharide extract and application of ginseng oligosaccharide extract |
| CN103385888A (en) * | 2013-07-24 | 2013-11-13 | 刘淑莹 | Application of ginseng oligosaccharide composition in preparation of anti-oxidation medicine or health-care food |
| CN105699478A (en) * | 2016-03-21 | 2016-06-22 | 长春中医药大学 | Method for quickly identifying sugar |
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Application publication date: 20120627 |