CN104861085A - Chestnut seed alpha-1,6-glucan, preparation method for alpha-1,6-glucan, and application of alpha-1,6-glucan to anticancer drugs - Google Patents
Chestnut seed alpha-1,6-glucan, preparation method for alpha-1,6-glucan, and application of alpha-1,6-glucan to anticancer drugs Download PDFInfo
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Abstract
The invention provides a chestnut seed alpha-1,6-glucan, a preparation method for the chestnut seed alpha-1,6-glucan, and application of the chestnut seed alpha-1,6-glucan to anticancer drugs. The structural formula of the chestnut seed alpha-1,6-glucan is [arrow 6)-alpha-Glcp(1 arrow]n, the weight average molecular weight is in the range of 1600-2400 kDa, and the average molecular weight is 2000 kDa; the chestnut seed alpha-1,6-glucan belongs to homopolysaccharides, and has obvious inhibited activity on proliferation of cervical cancer cells HeLa, breast cancer cells MCF-7 and adriamycin-resistant human breast cancer cell MCF-7 in vitro; chestnut is a rare fruit with the edible Chinese herbal function, and has no serious toxic and side effect; the chestnut seed alpha-1,6-glucan obtained according to the preparation method provided by the invention is high in sugar chain structural integrity, and is expected to be developed into anticancer drugs or assisted anticancer drugs.
Description
Technical field
The present invention relates to a kind of vegetable polysaccharides and preparation method thereof and application, especially relate to a kind of Chinese chestnut kernel α-1,6-dextran and preparation method thereof and the application in antitumor drug.
Background technology
Chinese chestnut is the fruit of Fagaceae Castanea, and taste is sweet, warm in nature, nontoxic, and useful gas tonifying spleen, thick stomach, the strong muscle of kidney tonifying, promoting blood circulation and hemostasis, clearing heat and detoxicating, antidiarrheal control effects such as coughing.Clinically, the diseases such as Chinese chestnut also can be used for treatment gastric disorder causing nausea, has loose bowels, waist leg is weak, spit blood, have blood in stool, metal-inflicted wound.Polysaccharide, as the important composition material of Chinese chestnut kernel, because of many advantages such as its biological function are extensive, toxic side effect is little, is subject to the very big attention of various countries research staff.
Be separated from Zhenan County Chinese chestnut and obtain polysaccharide fraction CPS-a and CPS-b, there are anti-oxidant and antifatigue effect (separation and purification of chestnut polysaccharide, structural analysis and antioxidation in vitro research, Shaanxi Normal University, Master's thesis, 2011; The research of the separation and purification of chestnut polysaccharide, structural analysis and antifatigue effect, food and biotechnology journal, 2013,32,767-772).Polysaccharide in the Chinese chestnut of Luotian is made up of glucose, seminose, wood sugar and pectinose, ratio is 0.58:1.00:0.33:0.18, molecular-weight average is 164.0kDa, there is anti-oxidant, antitumor, anticoagulation and leukocyte increasing isoreactivity, when concentration is 1mg/mL, 32.8% and 12.1% (separation and purification of Luotian chestnut polysaccharide and composition analysis is respectively to the inhibiting rate of human liver cancer cell HepG2 and cervical cancer cell HeLa, Chinese Pharmaceutical Journal, 37 (1), 63-64,2002; The extraction of chestnut polysaccharide, composition analysis and determination of activity, Wuhan University of Technology's journal, 32 (11), 14-16,2010; The separation and purification of chestnut polysaccharide, Structural Identification and activity research thereof, Jiangsu University, Master's thesis, 2013).The restraining effect of swallow dragon chestnut polysaccharide to Human hepatoma cell line Bel-7402, lung carcinoma cell A-549 and uterine cancer cells HCT-8 is more obvious, when polysaccharide concentration is 0.3mg/mL, inhibiting rate is respectively 69.5%, 51.4% and 55.3% (Chinese chestnut different varieties (being) polysaccharide structures and active preliminary study, Hebei Science & Technology Normal College, Master's thesis, 2013).Barbat etc. are from European Chinese chestnut alkaline extraction thing, separation obtains xylan, structure is 4-O-methyl glucose uronic acid xylan and same xylan, wherein 4-O-methyl glucose uronic acid xylan can suppress the hyperplasia of people's epidermal carcinoma cell A431, ability (the Structural Characterization and Cytotoxic Properties of a4-O-Methylglucuronoxylan from Castanea sativa.2.evidence of a structure-activity relationship of migration and invasion, Journal of Natural Product, 71, 1404 – 1409, 2008).
More than extracting the polysaccharide obtained and form by multiple monose in research, is baroque assorted poly-polysaccharide, and it only demonstrates the performance on anti-oxidant, antifatigue and anti-tumor activity.
Summary of the invention
Object of the present invention is just to provide a kind of Chinese chestnut kernel α-1,6-dextran.
Another object of the present invention be to provide a kind of with Qianxi Chinese chestnut kernel for the method for Chinese chestnut kernel α-1,6-dextran prepared by raw material.
Further object of the present invention is to provide Chinese chestnut kernel α-1,6-dextran and is preparing the application on antitumor drug.
It is the pharmaceutical composition of effective constituent with Chinese chestnut kernel α-1,6-dextran that further object of the present invention is to provide a kind of.
The object of the present invention is achieved like this:
A kind of Chinese chestnut kernel α-1,6-dextran, its structural formula is [(1 → 6)-α-Glcp (1 →]
n, wherein n is positive integer, and its weight average molecular weight range is 1600 ~ 2400kDa, and molecular-weight average is 2000kDa.
A kind of with Qianxi Chinese chestnut kernel for the method for described Chinese chestnut kernel α-1,6-dextran prepared by raw material, comprise the following steps:
A. Polyose extraction: Qianxi Chinese chestnut kernel is dry, pulverizing, alcohol degreasing, water extraction is centrifugal, supernatant liquor concentrating under reduced pressure, alcohol precipitation, and lyophilize, obtains Chinese chestnut water extraction Crude polysaccharides;
B. polysaccharide purification: above-mentioned Chinese chestnut water extraction Crude polysaccharides is through Sevag method deproteinated, centrifugal, supernatant liquor is first the dialysis tubing dialysis of 3500 with molecular weight cut-off, then adopts anion-exchange column and gel permeation chromatographic column separation and purification successively, obtains α-1,6-dextran.
Preferably, said method comprising the steps of:
A. Polyose extraction: Qianxi Chinese chestnut kernel is dry, pulverizing, uses 95% alcohol degreasing, drying at room temperature, obtains Chinese chestnut kernel powder; Get Chinese chestnut kernel powder, add water, the mass volume ratio of the two is 1g:10 ~ 30ml, after room temperature leaves standstill 2 ~ 4h, cold water extraction, extracting solution centrifuged deposit repeats extraction 2 ~ 4 times, and concentrating under reduced pressure after gained supernatant liquor merges, adds 95% ethanol of 2 ~ 5 times of volumes, 4 DEG C of hold over night, suction filtration, gained pellet frozen is dry, obtains Chinese chestnut water extraction Crude polysaccharides;
B. polysaccharide purification: Chinese chestnut water extraction Crude polysaccharides is mixed with the aqueous solution, add isopyknic chloroform/propyl carbinol mixed solution, room temperature vigorous stirring 1 ~ 3h, leave standstill separatory, upper strata aqueous phase repeats aforesaid operations 1 ~ 3 time, merge upper strata aqueous phase and concentrate, upper strata aqueous phase molecular weight cut-off after concentrated is that the dialysis tubing of 3500 is to distill water dialysis 3 ~ 5d, to the liquid concentration in dialysis tubing, Q-Sepharose Fast Flow anion-exchange column is adopted to be separated, wash-out is carried out with water, collect water elution component, after concentrated, be dissolved in the ammonium bicarbonate soln of 0.2mol/L, through the separation and purification of Sephacryl S-300 gel permeation chromatographic column after centrifugal, obtain α-1, 6-dextran.
Preferably, in described step a, the mass volume ratio of Chinese chestnut kernel powder and water is 1g:20ml.
Preferably, in the alcohol precipitation operation of described step a the add-on of 95% ethanol be concentrated after 3 times of supernatant volume.
On the other hand, the invention provides described Chinese chestnut kernel α-1,6-dextran and preparing the application in antitumor drug, specifically, described tumour is cervical cancer, mammary cancer or resistance mammary cancer, especially adriamycin-resistant mammary cancer.
Again on the one hand, the invention provides pharmaceutical composition, it comprises Chinese chestnut kernel α-1,6-dextran of the present invention as effective ingredient, and one or more pharmaceutically acceptable auxiliary materials.
Pharmaceutical composition provided by the invention, containing the carrier that Chinese chestnut kernel α-1,6-dextran, pharmacopedics are permitted or with the combination that mix with pharmaceutical excipient or thinner of Chinese chestnut kernel α-1,6-dextran as activeconstituents.
The carrier that the pharmacopedics of described pharmaceutical composition is permitted refers to the pharmaceutical carrier of pharmaceutical field routine, such as: thinner is as water etc., vehicle is as starch, sucrose etc., tackiness agent is as derivatived cellulose, alginate, gelatin etc., and wetting agent is as glycerine etc., and disintegrating agent is as agar, calcium carbonate, Calcium hydrogen carbonate etc., absorption agent is as quaternary ammonium compound etc., tensio-active agent is as cetyl alcohol etc., and absorption carrier is as kaolin etc., and lubricant is as talcum powder, calcium stearate, Magnesium Stearate etc.Other assistant agent can also be added in addition in the composition as flavouring agent, sweeting agent etc.
Pharmaceutical composition provided by the invention can by oral, snuffing enters, the mode of rectum or administered parenterally is applied to the patient needing this treatment.For time oral, conventional solid preparation can be made into as tablet, pulvis, granula, capsule etc., make liquid preparation if water or oil-suspending agent or other liquid preparations are as syrup, tincture etc.; During for administered parenterally, can be made into the solution of injection, water or oleaginous suspension etc., preferred form is tablet, capsule and injection.
The various formulations of pharmaceutical composition provided by the invention can be prepared according to the conventional production process of pharmaceutical field, such as, make activeconstituents mix with one or more carriers, be then made into required formulation.
Chinese chestnut kernel α-1,6-dextran provided by the invention is homopolymerization polysaccharide, and Chinese chestnut kernel α-1, the 6-dextran obtained by preparation method provided by the invention, the structural integrity of sugar chain is good.It has significant inhibit activities except external to cervical cancer cell HeLa, breast cancer cell MCF-7, also has more excellent inhibit activities to the propagation of adriamycin-resistant breast cancer cell MCF-7/ADR.
Accompanying drawing explanation
Fig. 1 is the Purity figure of α-1,6-dextran.
Fig. 2 is α-1,6-dextran
13c NMR (DEPT) spectrogram.
Embodiment
Below in an example, the various process do not described in detail and method are ordinary methods as known in the art, agents useful for same do not indicate source, specification be commercially available analytical pure or chemical pure.
Embodiment 1
Qianxi Chinese chestnut kernel (place of production is Qianxi County, Hebei province) is dry, pulverizing, gained powder 95% alcohol degreasing 2 days, after drying at room temperature, the Chinese chestnut kernel powder getting 100g adds the water of 2000mL, after room temperature leaves standstill 2h, cold water stirs and extracts 2h, and centrifugal, residue repeats extraction 2 times again with the same terms, merge supernatant liquor, be evaporated to 150mL, under agitation add 95% ethanol of 3 times of volumes, 4 DEG C of hold over night, suction filtration, dehydrated alcohol dewaters, and gained pellet frozen is dry, obtains Chinese chestnut water extraction Crude polysaccharides 9.6g.
Get the aqueous solution (W/V, mass body volume concentrations) that Chinese chestnut water extraction Crude polysaccharides 1g is mixed with 1%, adopt Sevag method deproteinated, add isopyknic chloroform/propyl carbinol mixed solution (chloroform: propyl carbinol=4:1; V/V, volume ratio), room temperature vigorous stirring 2h, leaves standstill separatory, and upper strata aqueous phase repeats deproteinated step 2 time, merges upper strata aqueous phase and concentrates.Upper strata aqueous phase molecular weight cut-off after concentrated is that the dialysis tubing of 3500 is to distill water dialysis 3d, to the liquid concentration in dialysis tubing, Q-Sepharose Fast Flow anion-exchange column is adopted to be separated polysaccharide, with deionized water wash-out, sulfuric acid-phynol detects, collect deionized water wash-out polysaccharide fraction, after concentrated frozen drying, obtain polysaccharide CP0.Polysaccharide CP0 is dissolved in 0.2mol/L ammonium bicarbonate soln, and be separated through Sephacryl S-300 gel chromatographic columns after centrifugal, flow velocity is 0.35mL/min, and Phenol-sulphate acid method detects, and collects polysaccharide fraction, obtains polysaccharide CP 0.45g.
Polysaccharide structures is resolved:
High productivity computing method (HPGPC) is adopted to measure relative molecular mass and the purity of product, Purity result as shown in Figure 1, for single symmetrical elution peak, illustrate that gained polysaccharide is the homogeneous polysaccharide of structure, the relative weight average molecular weight of product is 2000kDa.Instrument is Agilent 1260 high performance liquid chromatograph, and moving phase is 0.1mol/L sodium sulfate, and chromatographic column is ShodexOhpak SB-804, and flow velocity is 0.5ml/min, and column temperature is 35 DEG C.
Monosaccharide composition analysis shows that polysaccharide CP is made up of glucose.
The specific rotatory power measuring product through polarimeter is [α]
20 d=+203 ° of (c 1.0H
2o), wherein test condition is: temperature 20 DEG C, and concentration is 0.1g/100mL, and water is solvent.
The mode of connection of methylation analysis polysaccharide CP, result shows that polysaccharide CP is the glucose that 1,6-connects.
Figure 2 shows that polysaccharide CP's
13c NMR (DEPT) spectrogram, the carbon signal being positioned at δ 98.5ppm in figure is the C-1 signal of alpha-glucan, other carbon signals are followed successively by C-2 (δ 72.2ppm), C-3 (δ 74.2ppm), C-4 (δ 70.3ppm), C-5 (δ 71.0ppm) and C-6 (δ 66.4ppm).
Above result shows that the structure of polysaccharide CP is:
[→6)-α-Glcp(1→]
n
Wherein n is positive integer.
Embodiment 2
Anticancer proliferation experiment
1. test materials
Given the test agent: α-1, the 6-dextran of preparation in embodiment 1.
Negative controls: physiological saline.
Blank product: PBS.
Cell strain: human cervical carcinoma cell HeLa, breast cancer cell MCF-7, adriamycin-resistant breast cancer cell MCF-7/ADR (all purchased from Chinese Academy of Sciences's cell bank).
Reagent and instrument: 0.25% trypsin Invitrogen company), MTT (5mg/mL, Sigma company); Microplate reader (Bio-Rad 3550, the U.S.).
2. test method
2.1 drug treating metering and compound methods
α-1, the 6-dextran of preparation in embodiment 1 is dissolved in PBS, is mixed with concentration and is respectively 250 μ g/mL, 500 μ g/mL, 1000 μ g/mL, 2000 μ g/mL, the serial solution of 4000 μ g/mL.
2.2 cell cultures
The DMEM of human cervical carcinoma cell HeLa containing 10% foetal calf serum cultivates based on 5%CO
2incubator 37 DEG C cultivation, changes liquid for 2-3 days 1 time.After cell attachment covers with, after 0.25% tryptic digestion, with 2 × 10
4individual/mL cell is inoculated into 96 porocyte culture plates, and every pore volume 90 μ L, 37 DEG C of cultivations make cell attachment.
Breast cancer cell MCF-7 and adriamycin-resistant breast cancer cell MCF-7/ADR cultivates based on 5%CO with containing 1640 of 10% foetal calf serum respectively
2incubator 37 DEG C cultivation, changes liquid for 2-3 days 1 time.After cell attachment covers with, after 0.25% tryptic digestion, with 2 × 10
4individual/mL cell is inoculated into 96 porocyte culture plates, and every pore volume 90 μ L, 37 DEG C of cultivations make cell attachment.
2.3 α-1,6-dextran are to the restraining effect of growth of cancer cells
Series concentration (250 μ g/mL are added respectively in Tissue Culture Plate, 500 μ g/mL, 1000 μ g/mL, 2000 μ g/mL, 4000 μ g/mL) α-1,6-dextran solution 10 μ L makes its final concentration be respectively 25 μ g/mL, 50 μ g/mL, 100 μ g/mL, 200 μ g/mL, 400 μ g/mL, blank group is isopyknic PBS, and negative control is isopyknic physiological saline.Application of sample group and control group all establish 3 compound plates, plate are all established 3 multiple holes, cell temperature 37 DEG C, 5%CO
2incubator in, the compound plate of application of sample group and control group measures OD value respectively after hatching 24h, 48h and 72h, to calculate the given the test agent of different concns at the inhibiting rate of different time to three kinds of cancer cells.Measuring method is: add MTT, 10 μ L/ holes, after continuing to cultivate 4h, adds DMSO 100 μ L/ hole, places after spending the night, measure the OD value in each hole respectively by microplate reader under 570nm wavelength.
Data processing: cell survival rate (%)=[OD
dosing group-OD
blank]/[OD
negative control group-OD
blank];
Cell inhibitory rate (%)=100%-cell survival rate (%);
Test-results is as shown in table 1, table 2.
Table 1 α-1,6-dextran is to human cervical carcinoma cell HeLa proliferation inhibition rate
Table 2 α-1,6-dextran is to human breast cancer cell line Bcap-37 and multidrug resistance MCF-7/ADR proliferation inhibition rate
Claims (9)
1. Chinese chestnut kernel α-1, a 6-dextran, its structural formula is:
[(1→6)-α-Glc
p(1→]
n，
Wherein n is positive integer, and its weight average molecular weight range is 1600 ~ 2400 kDa, and molecular-weight average is 2000 kDa.
2. one kind with Qianxi Chinese chestnut kernel for the method for Chinese chestnut kernel α-1,6-dextran as claimed in claim 1 prepared by raw material, it is characterized in that, comprise the following steps:
A. Polyose extraction: Qianxi Chinese chestnut kernel is dry, pulverizing, alcohol degreasing, water extraction is centrifugal, supernatant liquor concentrating under reduced pressure, alcohol precipitation, and lyophilize, obtains Chinese chestnut water extraction Crude polysaccharides;
B. polysaccharide purification: above-mentioned Chinese chestnut water extraction Crude polysaccharides is through Sevag method deproteinated, centrifugal, supernatant liquor is first the dialysis tubing dialysis of 3500 with molecular weight cut-off, then adopts anion-exchange column and gel permeation chromatographic column separation and purification successively, obtains α-1,6-dextran.
3. method according to claim 2, is characterized in that, comprises the following steps:
A. Polyose extraction: Qianxi Chinese chestnut kernel is dry, pulverizing, uses 95% alcohol degreasing, drying at room temperature, obtains Chinese chestnut kernel powder; Get Chinese chestnut kernel powder, add water, the mass volume ratio of the two is 1g:10 ~ 30ml, and after room temperature leaves standstill 2 ~ 4h, cold water extraction, extracting solution centrifuged deposit repeats extraction 2 ~ 4 times, and concentrating under reduced pressure after gained supernatant liquor merges, adds 95% ethanol of 2 ~ 5 times of volumes, 4
oc hold over night, suction filtration, gained pellet frozen is dry, obtains Chinese chestnut water extraction Crude polysaccharides;
B. polysaccharide purification: Chinese chestnut water extraction Crude polysaccharides is mixed with the aqueous solution, add isopyknic chloroform/propyl carbinol mixed solution, room temperature vigorous stirring 1 ~ 3h, leave standstill separatory, upper strata aqueous phase repeats aforesaid operations 1 ~ 3 time, merge upper strata aqueous phase and concentrate, be that the dialysis tubing of 3500 is to distill water dialysis 3 ~ 5 d with molecular weight cut-off, to the liquid concentration in dialysis tubing, Q-Sepharose Fast Flow anion-exchange column is adopted to be separated, wash-out is carried out with water, collect water elution component, after concentrated, be dissolved in the ammonium bicarbonate soln of 0.2 mol/L, through the separation and purification of Sephacryl S-300 gel permeation chromatographic column after centrifugal, obtain α-1, 6-dextran.
4. preparation method according to claim 3, is characterized in that, in described step a, the mass volume ratio of Chinese chestnut kernel powder and water is 1g:20ml.
5. preparation method according to claim 3, is characterized in that, in the alcohol precipitation operation of described step a, the add-on of 95% ethanol is 3 times of concentrated rear supernatant volume.
6. Chinese chestnut kernel α-1,6-dextran according to claim 1 is preparing the application in antitumor drug.
7. application according to claim 6, is characterized in that, described tumour is cervical cancer, mammary cancer or resistance mammary cancer.
8. application according to claim 7, is characterized in that, described tumour adriamycin-resistant mammary cancer.
9. pharmaceutical composition, is characterized in that, wherein containing Chinese chestnut kernel α-1,6-dextran described in claim 1 as effective ingredient, and one or more pharmaceutically acceptable auxiliary materials.
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Cited By (4)
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| WO2017190396A1 (en) * | 2016-05-04 | 2017-11-09 | 中国科学院华南植物园 | Method for preparing α-1,6-glucan |
| CN107880147A (en) * | 2017-12-26 | 2018-04-06 | 河北科技师范学院 | Chinese chestnut active anticancer polysaccharide and its isolation and purification method |
| CN107982276A (en) * | 2017-12-26 | 2018-05-04 | 河北科技师范学院 | Purposes of the chestnut polysaccharide in the medicine for suppressing growth of cancer cells is prepared |
| CN108079010A (en) * | 2017-12-26 | 2018-05-29 | 河北科技师范学院 | Chestnut polysaccharide pharmaceutical composition with antitumaous effect and preparation method thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017190396A1 (en) * | 2016-05-04 | 2017-11-09 | 中国科学院华南植物园 | Method for preparing α-1,6-glucan |
| US10233264B2 (en) | 2016-05-04 | 2019-03-19 | South China Botanical Garden, Chinese Academy Of Sciences | Process for preparing (1→6)-α-D-glucan |
| CN107880147A (en) * | 2017-12-26 | 2018-04-06 | 河北科技师范学院 | Chinese chestnut active anticancer polysaccharide and its isolation and purification method |
| CN107982276A (en) * | 2017-12-26 | 2018-05-04 | 河北科技师范学院 | Purposes of the chestnut polysaccharide in the medicine for suppressing growth of cancer cells is prepared |
| CN108079010A (en) * | 2017-12-26 | 2018-05-29 | 河北科技师范学院 | Chestnut polysaccharide pharmaceutical composition with antitumaous effect and preparation method thereof |
| CN108079010B (en) * | 2017-12-26 | 2020-04-07 | 河北科技师范学院 | Chinese chestnut polysaccharide pharmaceutical composition with anticancer effect and preparation method thereof |
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