CN109265575A - A kind of 4 oxygen methyl glucose uronic acid class xylans obtained from artemisia seed gum and its application in terms of inhibiting liver tumour - Google Patents
A kind of 4 oxygen methyl glucose uronic acid class xylans obtained from artemisia seed gum and its application in terms of inhibiting liver tumour Download PDFInfo
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- CN109265575A CN109265575A CN201811020812.7A CN201811020812A CN109265575A CN 109265575 A CN109265575 A CN 109265575A CN 201811020812 A CN201811020812 A CN 201811020812A CN 109265575 A CN109265575 A CN 109265575A
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- seed gum
- artemisia
- uronic acid
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- 238000003756 stirring Methods 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
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Abstract
The present invention is handled by the artemisia seed gum (ASKG) to dissolubility difference, obtain a kind of artemisia seed gum polysaccharide of good water solubility, it confirmed that it is a kind of 4 oxygen methyl glucose uronic acid class xylans: using xylose structure unit (1 → 4)-β-Xylf as main chain, and 2 upper ends by 1,2-O- glucosides key connection 4-O-Me- а-GlcAp of every two xylose structure unit (1 → 4)-β-Xylf.Pass through further investigation, it is also expressly that the artemisia seed gum polysaccharide can induce HepG2 apoptosis of human hepatoma cell, so that it is determined that its application in terms of inhibiting liver tumour.
Description
Technical field
The present invention relates to a kind of extraction of artemisia seed gum polysaccharide separation degradation and its applications.
Background technique
Sand sagebrush (Artemisia filifolia), suffruticose plant are distributed in northwest drought desert belt more, and it is a variety of edible that research finds that sand sagebrush (Artemisia filifolia) seed has
Nutriment such as sand sagebrush seed oil, sand sagebrush (Artemisia filifolia) seed albumen and artemisia seed gum etc., are widely used in food additives and feed industry
Etc. industries[1,2].Polysaccharide is one of the important component of sand sagebrush (Artemisia filifolia) seed, is divided into the sand of water-soluble sand sagebrush (Artemisia filifolia) seed polysaccharide and water-insoluble
Wormwood artemisia seed glue.
Water-soluble sand sagebrush (Artemisia filifolia) seed polysaccharide studies relatively broad, Hao Yuqian etc.[3]Glucomannans group is obtained by extraction purification
Point, and its structure is parsed, Qingbin Guo[4]Xylan component is obtained by the ammonium sulfate precipitation method and is finished
Structure parsing.Research finds that water-soluble sand sagebrush (Artemisia filifolia) seed polysaccharide has immunological regulation, anti-oxidant, adjusting glycolipid metabolism, reduction cancer cell living
The multiple biological activities such as power[5,6]。
Artemisia seed gum (ASKG) is attached to the wax-like colloid polysaccharide of sand sagebrush (Artemisia filifolia) seed surface, and molecular weight is big, and content is that water solubility is more
2-3 times of sugar has the multifrequency natures such as high-moisture-retention, thickening property, stability, has in industries such as food, medicine and widely answers
Improve the quality of noodles, also as being applied to increase the elasticity of Flour product in noodles processing industry as food additives with prospect
Carrageenan, guar gum etc. can be replaced to become novel edible-type colloid as the antistaling agent of food, stabilizer[7].In addition, husky
Wormwood artemisia seed glue has multiple biological activities specific to cellulose substances as natural plant glue polysaccharide, as reducing blood sugar and blood lipid,
Prevent cardiovascular and cerebrovascular disease etc..Artemisia seed gum is used as medicine already to treat diabetes by civil Chinese medicine, after etc.[8]To artemisia seed gum
The hypoglycemic effect and mechanism of polysaccharide are studied, and discovery artemisia seed gum can significantly reduce the fasting blood of type-2 diabetes mellitus rat
Sugared content, and glucokinase in liver is increased, promote the conversion of hepatic glycogen.Artemisia seed gum can also dramatically increase sugar
Sick rat liver and SOD in serum enzyme activity are urinated, by improving body polyphenoils enzyme activity, the active oxygen removed in liver is free
Base promotes the secretion of insulin and the synthesis of hepatic glycogen to protect liver and islet cells, to reach the work for adjusting blood glucose
With.
But since artemisia seed gum dissolubility is poor, intermolecular force is strong, its activation plays are caused with certain difficulty,
Research at present, which focuses mostly on, is extracting preparation and direct application aspect, and structure-activity relationship report is relatively fewer.There is research to pass through carboxylic at present
The method of methylation or sulphation modification improves the dissolubility of artemisia seed gum polysaccharide[9], these methods can destroy the former knot of polysaccharide
Structure is modified, and introduces external group, to polysaccharide structures characterization tool have a certain impact, and the performance of active polysaccharide also without
Method determines whether produced by polysaccharide itself.Handling also by alkaline process improves artemisia seed gum dissolubility, but obtained water solubility
Artemisia seed gum polysaccharide molecular weight it is big (more than 500kD), polysaccharide is difficult to enter intracellular performance bioactivity, so also not examining
Activity is inquired into worry.
Bibliography:
[1] Institute of Botany, Chinese Academy of Sciences Chinese Higher plant illustrated handbook first [J] .1990
[2] good characteristic of the black sand sagebrush (Artemisia filifolia) of Zhaoyang and development and utilization [J] China Forest, 2011, (17): 45-.47
[3] property, structure and the immunocompetence research [D] of the pretty Artemisia spharocephala seed glue polysaccharide of Hao Yu；Northwest University, 2009
[4]Guo Q.Physicochemical,Structural and Conformational Properties of
Heteropolysaccharides from Seeds of Artemisia Sphaerocephala Krasch[J]
.Polysaccharides Structure Conformation Artemisia Sphaerocephala Krasch,2013,
(10):40-42
[5] the external hypoglycemic activity of Zhu Yin honor artemisia desertorum polysaccharide and its derivative research [D]；Gansu Agriculture University, 2011
[6]Ren D,Lin D,Alim A,et al.Chemical characterization of a novel
polysaccharide ASKP-1 from Artemisia sphaerocephala Krasch seed and its
macrophage activation via MAPK,PI3k/Akt and NF-κB signaling pathways in
RAW264.7cells[J].Food&Function,2017,8(3):1299
[7] the external hypoglycemic activity of Zhu Yin honor artemisia desertorum polysaccharide and its derivative research [D]；Gansu Agriculture University, 2011
[8]Zhang,J.,Huang,Y.,Hou,T.,&Wang,Y.(2006).Hypoglycaemic effect of
Artemisia sphaerocephala Krasch seed polysaccharide in alloxan-induced
diabetic rats.Swiss Medical Weekly,136(33-34),529
[9]Wang,J.,Wang,Y.,Xu,L.,Wu,Q.,Wang,Q.,Kong,W.,Liang,J.,Yao,J.,&
Zhang,J.(2017).Synthesis and structural features of phosphorylated Artemisia
sphaerocephala polysaccharide.Carbohydrate Polymers,19-26.
Summary of the invention
The present invention is handled by the artemisia seed gum (ASKG) to dissolubility difference, obtains a kind of sand sagebrush (Artemisia filifolia) seed of good water solubility
Glue polysaccharide (AGP-III-C), it is thus identified that it is a kind of 4 oxygen methyl glucose uronic acid class xylans, and furthers investigate and specify this
Artemisia seed gum polysaccharide (AGP-III-C) can induce HepG2 apoptosis of human hepatoma cell, so that it is determined that it is inhibiting liver tumour side
The application in face.
Concrete results are as follows:
The artemisia seed gum polysaccharide is and the every two xylose structure list using xylose structure unit (1 → 4)-β-Xylf as main chain
The upper end by 1,2-O- glucosides key connection 4-O-Me- а-GlcAp of 2 of member (1 → 4)-β-Xylf, as follows:
Above-mentioned artemisia seed gum polysaccharide is that 53kDa or its approximation (such as 52kDa~54kDa) are preferred with molecular weight.
Above-mentioned artemisia seed gum polysaccharide can be induced preparing the purposes in drug for inhibiting liver tumour, the drug
HepG2 apoptosis of human hepatoma cell.The medicine types for the lesion that can especially go directly, such as injection, controlled release preparation (controlled release tablet, control
Release capsule etc.), inhalant etc..
Pharmaceutical composition, it includes above-mentioned artemisia seed gum polysaccharide and pharmaceutical acceptable carriers.
Food, it includes above-mentioned artemisia seed gum polysaccharide.Such as: dairy products, candy, beverage etc..
The invention has the following advantages:
The present invention in the case where not destroying or changing artemisia seed gum polysaccharide structures, by mild alkaline treatment, isolate and purify and
Oxidative degradation (H2O2- Vc oxidative degradation system) method improve the dissolubility of artemisia seed gum polysaccharide, and to the small-molecular-weight of acquisition
Component has carried out active further investigated, clear 4 oxygen methyl glucose uronic acid class xylan component AGP- of wherein small-molecular-weight
III-C can induce HepG2 apoptosis of human hepatoma cell.
Detailed description of the invention
The extraction separation and purification and degradation flow chart of Fig. 1 artemisia seed gum.
Elution profile of Fig. 2 AGP through DEAE- cellulose column.
Influence of Fig. 3 Vc concentration to AGP-III degradable component molecular weight.
The sugared content and glucuronic acid content of Fig. 4 degradation front and back component.
The gas chromatogram of Fig. 5 AGP-III and component AGP-III-A~AGP-III-D after degradation.Monosaccharide standard: 1. mouse
5. mannose (Man) of Lee's sugar (Rha) 2. fucose (Fuc) 3. arabinose (Ara), 4. xylose (Xyl), 6. glucose sugar (Glc) 7.
8. glucuronic acid (GlcA) of galactolipin (Gal), 9. galacturonic acid (GalA) a.4-O- methyl glucose uronic acid.
The influence of Fig. 6 AGP-III and degradable component to HepG2 cell viability.A experimental result is expressed as average value ± standard
Poor (n >=6)；Compared with the control group, * p < 0.05, * * p < 0.01, * * * p < 0.01, B figure are comparative experiments two-by-two as a result, different words
Matrix shows that there is significant difference in P < 0.05.
Ration statistics figure shared by each period after Fig. 7 flow cytomery AGP-III-C processing HepG2 cell.Experiment
As a result it is expressed as mean+SD (n=3)；Compared with the control group, p < 0.01 * p < 0.05, * * p < 0.01, * * *.
Influence of Fig. 8 AGP-III-C to HepG2 cellular morphology.
Influence of Fig. 9 AGP-III-C to HepG2 cell mitochondrial membrane potential and ROS level.HepG2 cell is through different dense
After AGP-III-C (0,1,5,25,50,100 μ g/mL) and 5-FU (20 μ g/mL) processing for 24 hours of degree, dyed with JC-1 and ROS,
And with fluorescence microscope (× 200).Multi-function microplate reader carries out qualitative detection (Fig. 9 A) to JC-1 and carries out to ROS level
Qualitative detection (Fig. 9 B), experimental result are expressed as mean+SD (n=3)；Compared with the control group, * p < 0.05, * * p <
0.01, * p < 0.01 * *.
Influence of Figure 10 AGP-III-C to HepG2 cell MAPK signal path.AGP- of the HepG2 cell through various concentration
After III-C (0,1,5,25,50,100 μ g/mL) and 5-FU (20 μ g/mL) processing for 24 hours, GAP-associated protein GAP in MAPK signal path
Expression quantity.Experimental result is expressed as mean+SD (n=5)；Compared with the control group, * p < 0.05, * * p < 0.01, * * * p <
0.01。
The GC-MS map and ms fragment peak of Figure 11 AGP-III-C and AGP-III-C-R.
Figure 12 AGP-III-C's1H NMR and13C NMR figure.In figure, A:4-O-Me- α-GlcA, B:(1 → 4)-β-Xyl；
C:(1→4)-β‐Xyl-2-O-(4-O-Me-α-GlcA。
The COSY map of Figure 13 AGP-III-C.A, B, C respectively represent three kinds of structural units in AGP-III-C, wherein A:
4-O-Me-α-GlcA；B:(1 → 4)-β-Xyl；C:(1 → 4)-β-Xyl-2-O- (4-O-Me- α-GlcA.
The TCOSY map of Figure 14 AGP-III-C.A, B, C respectively represent three kinds of structural units in AGP-III-C, wherein A:
4-O-Me-α-GlcA；B:(1 → 4)-β-Xyl；C:(1 → 4)-β-Xyl-2-O- (4-O-Me- α-GlcA.
The HSQC map of Figure 15 AGP-III-C.A, B, C respectively represent three kinds of structural units in AGP-III-C, wherein A:
4-O-Me-α-GlcA；B:(1 → 4)-β-Xyl；C:(1 → 4)-β-Xyl-2-O- (4-O-Me- α-GlcA.
The TNNOESY map of Figure 16 AGP-III-C.
The HMBC map of Figure 17 AGP-III-C.
The identification structure of Figure 18 AGP-III-C.
Specific embodiment
The present invention by artemisia seed gum carry out mild alkaline treatment, isolate and purify, then use H2O2- Vc oxidative degradation system pair
One of component after isolating and purifying AGP-III degrades, and the concentration for changing Vc obtains the artemisia seed gum of four small-molecular-weight sections
Polysaccharide A GP-III-A, AGP-III-B, AGP-III-C, AGP-III-D；And tested by cell viability, ability of cell proliferation is surveyed
Signal of interest access in fixed, cell cycle determination, apoptosis status observation, the variation of mitochondrial potential and apoptosis pathway
Correlative protein expression amount is measured in MAPKs, and further investigation artemisia seed gum polysaccharide makees human liver cancer cell HepG2 Apoptosis
Influence.
As shown in Figure 1, the extraction separation and purification of the present embodiment progress artemisia seed gum and the process of degradation are specific as follows:
(1) extraction of artemisia seed gum: weighing a certain amount of sand sagebrush (Artemisia filifolia) seed in the water of 40 times of volumes, impregnate 1h at room temperature, in
Constant temperature extracts 5h at 80 DEG C.It is cooled to room temperature, with tissue mashing machine by the broken centrifugation of the blob of viscose of adhesion shape, separates after reaction
Translucent colloid substance out discards supernatant water-soluble sand sagebrush (Artemisia filifolia) seed polysaccharide part and sand sagebrush (Artemisia filifolia) seed shell residue.It is freeze-dried translucent
Colloid substance, be artemisia seed gum ASKG；
(2) preparation of artemisia seed gum polysaccharide: accurately weighing the sample ASKG that step (1) obtains, and it is 1% that solid-liquid ratio, which is made,
Glue suspension stirs 1h and mixes to complete, at room temperature with the NaOH (NaBH containing 0.1mol/L of 1mol/L4) in 70 DEG C of heated at constant temperature
4h, extract acetic acid tune pH to 7,10000r/min are extracted on magnetic stirring apparatus, centrifugation 10min removes insoluble matter, and supernatant is dense
The preferable artemisia seed gum Polysaccharide A SKGP of dissolubility, abbreviation AGP are obtained after contracting, dialysis freeze-drying；
(3) artemisia seed gum polysaccharide isolates and purifies: using DEAE-cellulose column (25cm × 5cm, HCO3-Type) to step
Suddenly (2) obtain AGP and are isolated and purified, and pillar weighs 1g AGP and 20mL distilled water is added after overactivation, after mixing well from
The heart takes supernatant, uniform loading.Successively use distilled water, 0.2mol/L, 0.5mol/L NaHCO3Solution is eluted, pipe detection
Absorbing proteins A280 and sugar absorb A490 (phend-sulphuric acid), make elution curve, collect simple spike, obtain four components, point
Freeze-drying obtains polysaccharide sample, respectively AGP-I, AGP-II, AGP-III, AGP-IV (Fig. 2) yield point after Nong Suo not dialysing
Not Wei 0.10%, 0.034%, 0.27%, 0.17%, the wherein yield highest of component AGP-III；
(4) degradation of AGP-III: since AGP-III molecular weight is greater than 500kDa, molecular weight hardly enters greatly intracellular hair
Its bioactivity is waved, so using H2O2- Vc system degrades to component AGP-III.For the polysaccharide group for obtaining low molecular weight
Point, first by the suitable degradation concentration of study on conditions shown in table 1.Detailed process are as follows: accurately weigh quantitative AGP-III 6
Part, it is made into the suspension that solid-liquid ratio is 0.5% respectively and is placed in 1~No. 6 tool plug bottle, by condition shown in table 1, maintains H2O2It is dense
Degree be 5mmol/L it is constant, change Vc concentration (0.5mmol/L, 1.5mmol/L, 3mmol/L, 5mmol/L, 7mmol/L,
10mmol/L)。
The selection of 1 degradation condition of table
After sealing in 40 DEG C of water-baths isothermal reaction 2h.Reaction is terminated after 2h, product after degradation is concentrated in Rotary Evaporators,
And dialysed three days for 3500 bag filter in 4 DEG C with molecular interception amount, to remove H therein2O2And VC.Finally freeze-drying point
Each degradation sample is not collected.The molecular weight of measurement degradation sample afterwards.The chromatographic column of selection be TSK-gel G 4000PWXL and
TSK-gel G 3000PWXL, when keeping the concentration of polysaccharide to be 0.5%, temperature is 40 DEG C, H2O2Concentration be 5mmol it is constant, VC
Concentration when changing within the scope of 0.5mmol/L~10mmol/L, degradation results are as shown in Figure 3.It was found that working as H2O2One timing of concentration
Change VCConcentration, the molecular weight of AGP-III occurs apparent variation, works as CH2O2/CVCWhen >=1, molecular weight is with VCThe increasing of concentration
It gradually becomes smaller greatly, and the permeability of solution is gradually increased；Work as CH2O2/CVCWhen=1, palliating degradation degree reaches maximum；With VCIt is dense
Degree is gradually increased, and palliating degradation degree declines instead.Excessive Vc inhibits the generation of reaction at this time.Choose wherein four molecular weight
Duan Zufen AGP-III-A:358.9kDa, AGP-III-B:106.7kDa, AGP-III-C:53.1kDa, AGP-III-D:
23.6kDa is largely prepared and follow-up study.
(5) using phend-sulphuric acid to AGP-III and degradable component AGP-III-A, AGP-III-B, AGP-III-C,
The total sugar content of AGP-III-D is measured.Total sugar content is respectively 78.8%, 63.2%, 73.9%, 68.5%, 75.1%.
Using carbazol-sulfuric acid method to AGP-III and AGP-III-A, AGP-III-B, AGP-III-C, AGP-III-D this five components
Glucuronic acid content is measured.Glucuronic acid content is respectively 21.2%, 22.3%, 26.2%, 39.3%, 26.5%.Wherein group
AGP-III-C glucuronic acid content is divided to be significantly higher than other components, (Fig. 4).Monosaccharide composition analysis shows, AGP-III and four group
Dividing AGP-III-A, AGP-III-B, AGP-III-C, AGP-III-D is all the component of acidic xylan type, with degradation journey
The increase of degree can expose more active groups, as the content of acid sugar gradually increases, but can also cause part branch sugared simultaneously
The loss (Fig. 5) of such as glucose.
(6) with mtt assay to four components AGP-III-A, AGP-III-B, AGP-III-C, AGP- after AGP-III and degradation
Influence of the III-D to HepG2 human liver cancer cell vigor, as shown in Figure 6.The HepG2 cell viability when concentration reaches 100 μ g/mL
It is reduced to 83.81%, 67.8%, 65.1%, 59.6%, 64.7% extremely significant compared to the blank group (P < 0.001) respectively.As a result
Show that five kinds of xylan components can reduce human liver cancer cell vigor, and component is big to the inhibition level of cell viability after degradation
In AGP-III, and two-by-two, comparison result shows that component AGP-III-C is significantly stronger than it to the inhibition level of HepG2 cell viability
His component.So the later period selects component AGP-III-C to carry out further activity research.
(7) proliferation of HepG2 human liver cancer cell can be inhibited to inquire into AGP-III-C, this research selects Colony forming real
It tests to be observed, AGP-III-C and 5-FU (the 20 μ g/ of HepG2 cell various concentration (0,1,5,25,50,100 μ g/mL)
ML it) handles, experiment number n >=6.Crystal violet is a kind of basic dyeing liquid, can dye bluish violet in conjunction with core DNA.Experiment knot
Fruit: bluish violet is presented in Normal group cell, illustrate 7 days inner cells of culture can normal growth, and sample group cell is given, with giving
The increase of sample concentration, bluish violet lighter illustrate that cell quantity is few or insufficient.The experimental results showed that HepG2 people after sample
There is Proliferation Ability phenomenon and concentration dependent are presented in liver cancer cells.When concentration reaches 50 μ g/mL since sample inhibits
There is phenomena such as cell detachment in the proliferation of cell, occurs substantially without bluish violet, and degree is similar with positive control 5-FU.
(8) this experiment detects influence of the AGP-III-C to the HepG2 cell cycle by the analysis means of flow cytometry.
As shown in fig. 7, compared to blank group, when AGP-III-C concentration is greater than 1 μ g/mL, with the increase of AGP-III-C concentration,
Relative percentage shared by G0/G1, which is gradually increased from 59.50%, increases to 75.85%.Relative percentage shared by S phase and G2-M phase
It reduces, there is significant statistical significance.Show AGP-III-C by inducing HepG2 cell-cycle arrest in G0/G1 phase
Apoptosis.
(9) to inquire into influence of the AGP-III-C to HepG2 human liver cancer cell form, as shown in Figure 8.Blank control group is thin
Born of the same parents are uniformly bright, spindle shape are presented, cellular morphology is complete, and cell contact is complete.And AGP-III-C processing group cell, cell
Chromatin pyknosis in core, shape change, and cell rounding becomes smaller, and cell contact disappears, and edge is roughening, and cell number is reduced.
And concentration, when being gradually increased, the change of cellular morphology is further obvious, and cell gradually appears the state to fall off.5-FU processing group is sun
Property control, it can be observed that cellular morphology when cancer cell-apoptosis changes.Further to inquire into whether AGP-III-C induces
HepG2 apoptosis of human hepatoma cell, the method that AO-EB bis- fluorescent stainings and DAPI fluorescent staining are selected in this research observe AGP-
The modal variation of HepG2 apoptosis of human hepatoma cell after III-C processing.AO can through the complete cell of film enter nucleus with
Double-stranded DNA, which combines, issues green fluorescence.And EB is only capable of the cell being damaged through film, insertion core DNA issues Chinese red fluorescence.Such as figure
Shown in 8B, cellular control unit, cell membrane form is complete, and uniform green fluorescence is presented, and low concentration processing group cell is thin
After birth permeability increases, and gradually has EB to enter intracellular, dyes together with AO, and orange fluorescence is presented, and with to sample concentration
Be continuously increased, discovery enter intracellular EB amount gradually increase, illustrate cell membrane integrality reduce so that red fluorescence
Amount increase.From the increase that can be seen that with AGP-III-C concentration in figure, red fluorescence gradually increases, and illustrates AGP-
III-C can induce HepG2 apoptosis of human hepatoma cell.Likewise, DAPI fluorescent dye meeting syncaryon DNA in normal cell is in
Now uniform blue-fluorescence, when there is apoptotic state in cell, cell membrane integrity destroy, into intracellular DAPI dyestuff by
It is cumulative more, so that cell is it is observed that rear be presented bright blue-fluorescence.As shown in Figure 8 C, the cell of blank control group culture solution,
Membrane structure is complete, uniform into intracellular DAPI fluorescent dyeing.Uniform blue-fluorescence is presented, and it is thin to sample group
Born of the same parents' form changes, nuclear chromatin condensation, and cell membrane integrity reduces, and increases into intracellular DAPI, causes dyeing not
Uniformly, bright blue-fluorescence is presented after cell observation.Illustrate AGP-III-C can induce HepG2 apoptosis of human hepatoma cell and
In concentration dependent.
(10) influence of the AGP-III-C to HepG2 human liver cancer cell mitochondrial potential
Using the variation of JC-1 specific fluorescence dye measurement mitochondrial membrane potential.There are two types of existence forms by JC-1, normally
In cell, the JC-1 of multimeric forms, which is gathered in the matrix of mitochondria, there is red fluorescence, and mitochondrial membrane potential is higher at this time.
When the membrane potential of mitochondria reduces, permeability changes, JC-1 cannot form polymer, exist with monomeric form, and it is glimmering green occur
Light.Red fluorescence is presented in the cell of control group, illustrates that JC-1 exists in the form of polymer, mitochondrial function is normal.And with
The increase of AGP-III-C concentration, green fluorescence significantly increase, and red fluorescence gradually decreases, and green fluorescence and red fluorescence
The ratio of intensity significantly increases, and as shown in Figure 9 A, illustrates that AGP-III-C being capable of the reduction of inducing cell mitochondrial membrane potential.Into one
It walks the ROS level intracellular to HepG after AGP-III-C processing to be measured, as shown in Figure 9 B.Compared with blank control group, 1 μ
G/mL, 5 μ g/mL, 25 μ g/mL, 50 μ g/mL, 100 μ g/mL AGP-III-C processing for 24 hours after, HepG2 human liver cancer cell ROS contains
Amount has increased separately 0.078 ± 0.0086%, 0.29 ± 0.0051%, 0.75 ± 0.056%, 1.18 ± 0.068% and 2.79
± 0.011%.It the result shows that AGP-III-C is capable of the raising of significant (P < 0.001) promotion intracellular ROS level, and is in concentration
Dependence.
Led to by the expression quantity of the total protein and phosphorylated protein that detect ERK1/2, JNK and p38 to have inquired into MAPK signal
Whether road takes part in the HepG2 apoptosis of human hepatoma cell of AGP-III-C induction.As shown in Figure 10, AGP-III-C can significantly increase
Add the expression of p38, ERK, JNK phosphorylated protein, and is in concentration dependent.Show that AGP-III-C passes through in activation HepG2 cell
MAPK approach come participate in regulation AGP-III-C induction apoptosis process.
Establishing AGP-III-C above is optimum activity component, therefore carries out structural characterization to it.Derivatization is used below
Method is analyzed by GC-MS and NMR spectra, obtains the structural information of AGP-III-C.
The reduction of uronic acid in 1.AGP-III-C
Since uronic acid is easy to lose with the neutral sugar being connected acidic polysaccharose in acid hydrolysis, and spread out in methylation
During life, sugar chain is easy to happen β-elimination to detect to it under the alkaline condition in reaction.So to acid
Property sugar carry out structure elucidation when needs first uronic acid is restored.
Uronic acid is restored using the method for Taylor and Conrad, weighs the AGP-III-C sample of 10mg or so,
The distilled water of 1.5mL or so is added, concussion shakes up, and is slowly added to 30mg CMC, and keep pH on 4 left sides with 0.01mol/L HCl
The right side is persistently stirred to react 2h, then proceedes to that 1mL 100mg/mL NaBH is slowly added dropwise into reaction4, keeping body in reaction process
The pH of system is 7, the reaction was continued 1h, and the glacial acetic acid tune pH to 5 diluted is slowly added to after reaction was completed, is dialysed 3 days, and freezing is dry
It is dry.It repeats the above steps 5 times and is restored completely to uronic acid, products therefrom is named as AGP-III-C-R.
The methylation analysis of 2.AGP-III-C and AGP-III-C-R
Methylation analysis is carried out to AGP-III-C and AGP-III-C-R using Needs method, by the AGP- of 10mg or so
III-C and AGP-III-C-R are dissolved in the DMSO of 1.5mL, ultrasonic dissolution 1h, and 50 DEG C are stirred overnight and dissolve polysaccharide sufficiently, are added
Enter to grind the NaOH powder 100mg or so, ultrasonic reaction 1h of drying in advance.Room temperature is protected from light lower addition 2mL iodomethane, ultrasonic reaction
2h.Water quenching is added to go out, reaction was completed.It dialyses 3 days to water, freeze-drying.It repeats the above steps 4 times, until methylation is completely, it is rear to carry out
Acetolysis, the complete sample that will methylate is separately added into 3mL formic acid and goes down to polymerize hydrolysis 3h at 100 DEG C, after rotation is evaporated
Formic acid is removed, the rear TFA that 2mol/L is added hydrolyzes 2h at 121 DEG C.15% NaBH is added in decompressing and extracting after neutralization4It carries out
It restores, glacial acetic acid is added dropwise after 2h and neutralizes, methanol extraction is added after decompressing and extracting into sample and removes borate for several times.After be added
The pyridine of 1mL and the acetic anhydride reaction overnight of 1mL.CH is dissolved in after decompressing and extracting2Cl2, distilled water extracted several times are added.It prepares
Sample carry out GC-MS analysis and GC quantitative analysis.
GC-MS program chromatographic column is rtx-5ms column (30m × 0.25mm × 0.25 μm), and temperature programming condition is at 140 DEG C
3min is kept, 250 DEG C is warming up to the speed of 2 DEG C/min and keeps 20min with this condition；Helium is carrier gas, and flow velocity is
0.6mL/min；Mass ion source is EI+Source, temperature are 210 DEG C.
GC program chromatographic column is rtx-5ms column (30m × 0.25mm × 0.25 μm), and temperature programming condition is 140 DEG C of holdings
3min is warming up to 250 DEG C with the speed of 2 DEG C/min and keeps 20min with this condition；Helium is carrier gas, flow velocity 0.6mL/
min；
3.AGP-III-C's1H and13C analysis
50mg or so AGP-III-C is weighed, 1mL heavy water is dissolved in, after dissolution fullys shake, centrifuging and taking supernatant, freeze-drying,
It repeats aforesaid operations 3 times.Nmr analysis is carried out with being transferred in nuclear magnetic tube after the heavy water sample dissolution of 400 μ L.
Nmr analysis condition is carried out in Varian 600MHz Nuclear Magnetic Resonance under the conditions of 30 DEG C1H and13C map and two
Tie up the acquisition of map.
Experimental result
The reduction of 1 uronic acid
It obtains restoring complete sample AGP-III-C-R after uronic acid reduction, GC analysis, comparison reduction front and back is carried out to it
GC map, uronic acid disappear, and the glucuronic acid content of colorimetric method for determining be 5.2%, illustrate that uronic acid restores completely substantially.
2 AGP-III-C and AGP-III-C-R exhaustive methylation are analyzed
After AGP-III-C and AGP-III-C-R carry out exhaustive methylation analysis, using being obtained after reduction and acetylation
The sugar alcohol acetonyl ester derivatization sample of partial methylation.The map obtained after GC-MS analysis and corresponding fragment peak are carried out as schemed
Shown in 11, there are 2 peaks on the GC-MS map of AGP-III-C derivative, and has on the GC-MS map of AGP-III-C-R derivative
3 peaks belong to each peak according to the retention time of chromatographic peak and the fragments characteristic of mass spectra peak, infer that their sugar is residual
Base type.Wherein 2,3-Me2- Xyl and 3-Me-Xyl is shared peak, and new peak 2 is added in AGP-III-C-R, 3,
4,6‐Me4- Glc, the peak newly increased is from the 4-O-Me-GlcA and GlcA being reduced.In AGP-III-C-R after derivatization
Three kinds of saccharide residue 2,3-Me2- Xyl, 3-Me-Xyl and 2,3,4,6-Me4- Glc represents three kinds of connection types i.e. -4) Xylf (1-, -
2,4)Xylf(4-,4‐O‐Me‐GlcAp(1-.The analysis result ownership of methylation is as shown in table 2 below:
The methylation analysis of table 2 GP-III-C and AGP-III-C-R
The relative mole ratios of each saccharide residue are calculated according to the peak area of GC map and response factor, three in AGP-III-C-R
Kind saccharide residue -4) ((molar ratio of 1- is 1:1.34:1.23 to Xylf (1-, -2,4) Xylf by 4-, 4-O-Me-GlcAp.Wherein branch
Glycosyl -2,4) (1- number is equal with terminal saccharide number-GlcA, illustrates that methylation is complete by Xylf.
3 AGP-III-C's1H and13C analysis
The glycosidic bond configuration of AGP-III-C, the sugar chain structures information such as connection type are divided by nuclear magnetic resonance (NMR)
Analysis, as a result as shown in figure 12.Related chemistry displacement is belonged in conjunction with GC-MS saccharide residue ownership and nuclear magnetic spectrum analysis.
AGP-III-C's1In H spectrum, there are three types of the displacement of anomeric proton, respectively δ 5.15,4.32,4.49 is respectively designated as A, B, C.
The chemical shift of A belongs to α type anomeric proton between δ 5.1~5.4, and without peak is split, which is generated by 4-O-Me-GlcA.δ
4.49 and δ 4.32 has the chemical shift for splitting peak and saccharide ring proton to belong to β type glycosidic bond between δ 4.5- δ 5.0ppm, respectively represents
Saccharide residue -4) Xylf (1- and -2,4) Xylf (signal caused by 4-.1The integrated peak areas molar ratio B of Xyl and GlcA in H spectrum
+ C:A=1.53:1.0.This is close with main chain in methylation with the molar ratio 1.90:1 of side chain.13The different head of saccharide residue in C spectrum
Carbon chemical shifts are generally concentrated between δ 90-110, AGP-III-C's13The chemical shift point of the anomeric carbon of A, B, C in C spectrum
Not Wei Yu δ 100.98, δ 104.51, δ 104.01ppm, in addition the signal peak at δ 62.83ppm shows there is methoxy in AGP-III-C
Base group.
It is all1H and13The chemical shift of C signal passes through same core correlation spectrum (COSY) respectively, total correlation spectrum (TOCSY),
TNNOESY spectrum and heteronuclear multiple key correlation spectrum (HMBC) are belonged to.
Since the chemical shift of the non-anomeric proton of saccharide ring is generally overlapped, therefore need to be displaced by proton in each saccharide residue related
Map is analyzed.The COSY spectrum and TOCSY spectrum of AGP-III-C is as shown in Figure 13 and Figure 14.It can be found from COSY spectrum
Direct-coupling relevant peaks between adjacent protons, such as the different head signal H1 of saccharide residue unit B (δ 4.33ppm) and H2 (δ 3.15ppm) phase
It closes, H2 (δ 3.15ppm) is related to H3 (δ 3.44ppm), and H3 (δ 3.44ppm) is related to H4 (δ 3.64ppm), H4 (δ 3.64ppm)
It is again related to H5 (δ 4.02ppm), so that the chemistry to proton each in residue B uniquely belongs to.Similarly to residue A and C also into
Row ownership.In addition the relevant peaks in anomeric proton and saccharide ring between remaining proton are belonged to by TOCSY spectrum.It is noticeable
It is in TOCSY spectrogram, and to observe that chemical shift of proton is that 3.34ppm intersecting in the relevant peaks of residue A anomeric proton
Peak.The peak belongs to the proton of methoxyl group,13Chemical shift in C is 62.51ppm.In addition, observing friendship in HMBC map
Pitch peak e:A4C(δ84.90)/AH O‐Me(δ 3.34) and f:A4H(δ3.34)/AC O‐Me(δ 62.83) shows that O-Me is connected to residue A
The position O-4.This is consistent with methylation analysis results, it was demonstrated that saccharide residue A is 4-O- methylglucuronic acid end.Remaining each proton
Chemical shift ownership be shown in Table 3.
Hydrocarbon coherent signal can be detected by hsqc spectrum, as shown in figure 15, sugar unit A is in δ 5.15ppm and δ
The strong different head signal of 100.98ppm；Strong different head signal of the sugar unit B in δ 4.32ppm and δ 104.51ppm；Sugar unit C exists
The strong different head signal of δ 4.49ppm and δ 104.01ppm.Thus further demonstrate in AGP-III-C three kinds be mainly crosslinked it is residual
Base unit.Non- anomeric carbon chemical shift can also be belonged to by HSQC simultaneously, at H4 in sugar unit A and 84.90ppm
C4 signal is related, and H5 is related to C5 signal at 73.35ppm.Other carbon chemical shifts can similarly be belonged to.
Connection type between the glycosidic bond of AGP-III-C is by TNNOESY and HMBC spectrum determination, as shown in Figure 16 and Figure 17.
It is observed in TNNOESY spectrum and intersects peak b':B1H (δ 4.49)/C4H (δ 3.64) and c':C1H(δ4.33)/B4H(δ 3.65),
It is observed in HMBC spectrum and intersects peak a:C1H(δ4.49)/B4C(δ78.81)；B:B1H(δ4.32)/C4C(δ79.46)；C:B4H(δ
3.64)/C1C(δ 104.10) signal is related.
These results prove that AGP-III-C is using -4) (1- is the primary structure repetitive unit of sugar chain to Xylf.And TNNOESY
Intersect in spectrum and intersects peak d:C2H (δ 3.27)/A in peak a ': A1H (δ 5.15)/C2H (δ 3.28) and HMBC1C(δ 100.87) shows
End -4-O-Me-GlcA is by 1,2-O- glucosides key connection -2,4) Xylf is (on 2 of 1- saccharide residue.It is formed in conjunction with monosaccharide,
The analysis of methylation analysis and nuclear magnetic resonance map is as a result, the structure of presumption AGP-III-C is as shown in figure 18.
3 GP-III-C's of table1H NMR and13The displacement of C nmr chemical
In order to illustrate the primary structure of AGP-III-C, by monosaccharide composition analysis, infrared spectrum measurement, uronic acid is restored,
The analysis means such as methylation analysis and 2D nuclear magnetic resonance spectroscopy technology to single group at type, the type of saccharide residue, glycosidic bond
Configuration, order of connection of saccharide residue etc. carry out analysis detection.Recently as the maturation of NMR spectrum technology, to polysaccharide
The parsing of structure is more and more accurate, and sample does not need to perform the derivatization processing, directly by detection to the structural information of polysaccharide into
Row is intuitive to be detected, can the accurate structural information for showing AGP-III-C in nuclear magnetic spectrum.From AGP-III-C's1H map
It can be seen that residue A 4-O-Me- а-GlcAp content highest, illustrate that acid sugar proportion is big, but be less than linear xylan
Molal quantity, as a result cross and be not much different with methylation result, and known between saccharide residue by TNNOESY spectrum and HMBC spectrum
The end of connection type, branch 4-O-Me- а-GlcAp is connected to two neighboring -4) Xylf is (on 1- backbone structure unit.Pass through
The structure of AGP-III-C is parsed, typical 4 oxygen methyl glucose uronic acid xylan type is found to be.Studies have reported that
The degree of polymerization of xylan, uronic acid can all influence the performance of bioactivity relative to the distributing position of xylose and than column.
Expert's conclusion: the structural information of AGP-III-C after purification is: using (1 → 4)-β-Xylf as main chain, and every two
The upper end by 1,2-O- glucosides key connection 4-O-Me- а-GlcAp of 2 of xylose structure unit.
Claims (5)
1. a kind of 4 oxygen methyl glucose uronic acid class xylans obtained from artemisia seed gum, it is characterised in that: with xylose structure list
Member (1 → 4)-β-Xylf is main chain, and 2 of every two xylose structure unit (1 → 4)-β-Xylf are upper by 1,2-O- glucosides
It is keyed the end of 4-O-Me- а-GlcAp, as follows:
2. 4 oxygen methyl glucose uronic acid class xylan according to claim 1, it is characterised in that: molecular weight be 53kDa or
Its approximation.
3. 4 oxygen methyl glucose uronic acid class xylan of any of claims 1 or 2 is in preparing the drug for inhibiting liver tumour
Purposes, which can induce HepG2 apoptosis of human hepatoma cell.
4. pharmaceutical composition, it includes 4 oxygen methyl glucose uronic acid class xylan of any of claims 1 or 2 and medicinal connect
By carrier.
5. food, it includes 4 oxygen methyl glucose uronic acid class xylans of any of claims 1 or 2.
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