CN106317248B - A kind of new natural products Huang silk granulose CEC-A and its application - Google Patents
A kind of new natural products Huang silk granulose CEC-A and its application Download PDFInfo
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- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
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Abstract
The invention discloses a kind of new natural products Huang silk granulose CEC-A and its application, the heteroglycan that yellow silk granulose CEC-A is made of two monosaccharide, that is β-D-Glucose and α-D-xylose is formed with the ratio of 5:1, average molecular weight is about 61056 D, skeleton with (1-4) β-D-Glucose, one → 1 is connected on 6-O) side chain of-α-D-xylose, the yellow silk granulose CEC-A of doses has significant oxidation resistance and immunoregulatory activities, when concentration is 4.5mg/ml, the Scavenging activity to DPPH free radical is 35.23%；Concentration is 6.4mg/mL, and the Scavenging activity to ABTS free radical is 40.70%.To T, B cell, which has, promotees proliferation activity.
Description
Technical field
The invention belongs to fungi polysaccharide applied technical fields, specifically, it is more to be related to a kind of new natural products Huang silk bacterium
Sugared CEC-A and its application.
Background technique
Polysaccharide (polysaccharides) is also known as polysaccharide, is the generally existing a kind of large biological molecule of organism, not only
The composition of cytoskeleton is participated in, and is the important composition ingredient of a variety of endogenous bioactive molecules.Modern age biochemistry one
Straight grip polysaccharide is regarded as maintaining eucaryotic cell structure (such as cellulose and chitin) in organism and provides energy source (such as starch and sugar
Member) substance, be not given to enough attention.The development of polysaccharide much compared with protein, nucleic acid evening, in addition the complexity of polysaccharide itself
Property and diversity, to polysaccharide structures measurement, characterization identification be proposed huge challenge.Currently, the research level of polysaccharide will be significantly
Lag behind the research of protein and nucleic acid.
In the past 20 years, about polysaccharide bioactivity research report be concentrated mainly on immunological regulation, it is antitumor, antiviral,
Anti-oxidant and hypoglycemic etc., effect is multipath, too many levels, multiple target point.
Yellow silk bacterium (pixie stool, apricot bacterium) Canthar-ellus cibarius Fr. English name: Chanterelle. is real
Body meat, tubaeform, full bacterium apricot, yolk yellow or loquat yellow, cap is 3-9 centimetres wide, initially flat, rear recessed.Have dense
Strongly fragrant almond fruit flavor, it is slightly sweet；It is edible, it gives off a strong fragrance, color is pleasing, and it is tasty, it is full of nutrition, it is bright world's type food
Use bacterium.Rich in there is a variety of mineral nutritions such as carrotene, vitamin A, C and calcium, iron, phosphorus
Currently, the fine structure and antioxidant activity research and its application to yellow silk granulose CEC-A are there is not yet any report
Road.
Summary of the invention
It is an object of the invention to overcome defect existing for above-mentioned technology, a kind of new natural products Huang silk granulose is provided
CEC-A and its application.
Itself the specific technical proposal is:
A kind of new natural products Huang silk granulose CEC-A, the heteroglycan being made of two monosaccharide, i.e. β-D-Glucose and
α-D-xylose is formed with the ratio of 5:1, and average molecular weight is about 61056D, the skeleton with (1-4) β-D-Glucose, on 6-O
Connection one → 1) side chain of-α-D-xylose, the structural formula of yellow silk granulose CEC-A are as follows:
New natural products Huang silk granulose CEC-A of the present invention is in anti-oxidation medicine and immunoregulation medicine preparation mistake
Application in journey.
Compared with prior art, the invention has the benefit that
Yellow silk granulose CEC-A of the invention has significant oxidation resistance, when concentration is 4.5mg/ml, to DPPH
The Scavenging activity of free radical is 35.23%；Concentration is 6.4mg/mL, and the Scavenging activity to ABTS free radical is 40.70%.To T,
B cell, which has, promotees proliferation activity.To T, B cell, which has, promotees proliferation activity.
Detailed description of the invention
Fig. 1 Huang silk bacterium holosaccharide CEC-A weight average molecular weight；
The INFRARED SPECTRUM of Fig. 2 Huang silk granulose CEC-A；
The HPLC-UV detection of Fig. 3 Huang silk granulose CEC-A；
The 1H NMR spectra of Fig. 4 Huang silk granulose CEC-A；
The 13C NMR spectra of Fig. 5 Huang silk granulose CEC-A；
The GC-MS map of Fig. 6 Huang silk granulose CEC-A, wherein Fig. 6 a (Isosorbide-5-Nitrae, 6) β-D-Glucose, Fig. 6 b (1-4) β-
D-Glucose, c → 1 Fig. 6)-α-D-xylose side chain；
The structure of Fig. 7 Huang silk granulose CEC-A；
Scavenging effect of Fig. 8 Huang silk granulose CEC-A to DPPH free radical；
Scavenging effect of Fig. 9 Huang silk granulose CEC-A to ABTS free radical；
The influence that Figure 10 Huang silk granulose CEC-A is proliferated T cell；
Influence of Figure 11 Huang silk granulose CEC-A to T cell form, wherein blank group: Figure 11 a；CEC-A experimental group: figure
11b- Figure 11 i, concentration are respectively 0.625,1.25,2.5,5,10,20,40,80 μ g/mL；LPS control group: Figure 11 j concentration is 5 μ
g/mL；
Influence of Figure 12 Huang silk granulose CEC-A to B cell proliferation；
Influence of Figure 13 Huang silk granulose CEC-A to B cell form, wherein blank group: Figure 13 a；CEC-A experimental group: figure
13b- Figure 13 i, concentration are respectively 0.625,1.25,2.5,5,10,20,40,80 μ g/mL；LPS control group: Figure 13 j concentration is 5 μ
g/mL。
Specific embodiment
Technical solution of the present invention is described in more detail in the following with reference to the drawings and specific embodiments.
The separation and Extraction of 1 Huang granulose CEC-A of embodiment
1.1. after hot water extraction, alcohol precipitation, yellow silk granulose CEC-A crude extract is obtained.With DEAE-cellulose
Column and Sephadex G-100column is isolated and purified, and yellow silk granulose CEC-A is obtained.
1.2. the Structural Identification of yellow silk granulose CEC-A
With hydrolysis, methylation analysis, gas-chromatography and mass spectrometric hyphenated technique (GC-MS), scanning electron-microscopy (SEM),
Infrared spectral technology (IR), nuclear magnetic resonance technique (NMR) carry out structure elucidation to yellow silk granulose.
1.2.1 the measurement of molecular weight
3mg Huang silk granulose CEC-A sample is dissolved in 1mlddH2In O, ultrasonic 5min carries out HPGPC analysis, data
Molecular weight 1.1 × 10 is measured with standard curve control with after the analysis of GPC software4D (standard items T-10,20,50,80,130).
1.2.2 the Silylation and methylation analysis of yellow silk granulose CEC-A
Hydrolysate after standard monosaccharide and above-mentioned drying is carried out Silylation, and steps are as follows: the sample dissolution of 1.0mg
In the anhydrous pyridine of 0.2ml, then plus the trim,ethylchlorosilane of the hexamethyldisilazane of 0.2ml and 0.1mg, 50 DEG C of incubations
20min, then 10000rpm is centrifuged 20min, takes upper solution for methylation analysis.
1.2.3 yellow silk granulose CEC-AGC-MS spectrum analysis
GC condition: chromatographic column: the Rtx-5sil MS (μ of 5%phenylmethylsiloxane 30mm × 0.25mm × 0.25
m)；
Sample injector temperature, GC-MS interface temperature, ion source temperature and detector temperature are respectively 250,250,230 and 250
DEG C, temperature program: 80 DEG C of 250 DEG C of (3min) 10 DEG C/min (30min)；Carrier gas: high-purity helium.
1.2.4 the infrared spectrum analysis of yellow silk granulose CEC-A
As yellow silk granulose CEC-A sample 2mg or so, KBr tabletting, infrared spectrophotometer 4000cm-1-400cm-1。
1.2.5 the nuclear magnetic resonance spectroscopy of yellow silk granulose CEC-A
Yellow silk granulose CEC-A sample 10mg or so is taken to be dissolved in 0.5mL heavy water (D2O in), the room temperature in Nuclear Magnetic Resonance
Measurement, 400MHz are surveyed1HNMR spectrum, 400MHz are surveyed13CNMR spectrum.
1.3 result
1.3.1 the fundamental property result of yellow silk granulose CEC-A
Yellow silk bacterium holosaccharide weight average molecular weight is 61056D (see Fig. 1).
1.3.2 the FTIR spectrum analysis of yellow silk granulose CEC-A
As shown in Fig. 2, Huang silk granulose CEC-A shows 3428.78cm in INFRARED SPECTRUM-1Wide absorption peak be appointed as O-H
With N-H stretching vibration peak, there is intramoleculars and intermolecular hydrogen bond.2926.89cm-1It is appointed as-CH2, the flexible vibration of-CH3
Dynamic peak.2127.55cm-1It is appointed as-CH2,-CH3Stretching vibration peak.1651.82cm-1It is appointed as C=O, C=C vibration peak.
1124.92cm-1, 1082.90cm-1In 1200-1000cm-1C-O-H stretching vibration and the pyrans being appointed as in range in-COOH
Ehter bond C-O-C stretching vibration in ring.791.10cm-1Instruction Huang silk granulose CEC-A has α type pyranoid ring.
1.3.3 the high-efficient liquid phase analysis result of yellow silk granulose CEC-A
Yellow silk granulose CEC-A is made of two kinds of sugar of alpha-D-glucose and alpha-D-xylose, and ratio is 5:1 (Fig. 3)
1.3.4 the H NMR spectroscopy analysis of yellow silk granulose CEC-A
There is (see Fig. 4) in anomer hydrogen signal δ 4.865, δ 4.854 instruction α type anomer hydrogen in yellow silk granulose CEC-A, and
It is both shown with INFRARED SPECTRUM consistent.In carbon spectrum13The resonance signal peak in 95 region -105ppm C NMR (400MHz) belongs to
In the carbonaceous subsignal of β-D-Glucose and α-D- galactolipin (see Fig. 5, table 1).
1 Huang granulose CEC-A's of table13Chemical shift in C NMR figure
1.3.5 the GC-MS spectrum analysis result of yellow silk granulose CEC-A
The heteroglycan being made of two monosaccharide an of structure novel is obtained from yellow silk bacterium, i.e., β-D-Glucose is (see figure
6a, Fig. 6 b) and α-D- galactolipin (Fig. 6 c), it is formed with the ratio of 2:1, average molecular weight is about 9279D, has (1-4) β-D-
The skeleton of glucose connects one → 3 on 6-O) side chain (table 2) of-α-D- galactolipin, it to sum up can tentatively infer yellow silk granulose
The structure of CEC-A (see Fig. 7).
The methylation GC-MS data of 2 Huang granulose CEC-A of table
The antioxidant activity research of 2. Huang granulose CEC-A of embodiment
The antioxidant activity of two kinds of chemical gauging oronge bacterium holosaccharides, including DPPH- freedom are used in vitro
The removing of base, ABTS+Radical cation is removed.
2.1 reagent
1,1- diphenyl -2- picryl hydrazine (DPPH-)；30%H2O2；Vitamin C (Vc)；2,6- di-t-butyl -4- methylbenzene
Phenol (BHT)；ABTS
2.2 instrument
721 type spectrophotometers (Shanghai third analysis instrument factory)；
2.3 method
2.3.1DPPH free radical scavenging ability measures
The measurement of DPPH free radical scavenging ability referring to Braca method, sample extracting solution be configured to suitable concentration (1,2,3,4,
5,6mg/mL).1mL solution to be measured is taken, is added 2.0mL 0.2mM DPPH- solution (being prepared with dehydrated alcohol), is placed after shaking up
30min.Ethyl alcohol returns to zero, and the light absorption value of A sample is measured at 517nm.1.0mL sample solution is measured simultaneously to mix with 2.0mL ethyl alcohol
Liquid, the absorbance at 517nm are compareed as A.Using Vc and BHT as positive control.DPPH Scavenging activity=(1-A sample/A
Control) × 100%.
2.3.2ABTS+The measurement of radical cation Scavenging activity
7mmol/LABTS aqueous solution and 2.45mmol/L potassium peroxydisulfate are protected from light reduction 12-16h, ABTS solution PBS
(pH7.4) being diluted to 630nm measured value is 0.50 ± 0.05.10 μ L sample, 90 μ LABTS solution hybrid reaction is taken, dark place is placed in
3min.Use sample P BS solution as color sample blank reference, PBS solution is blank control, in microplate reader at 734nm
Detection.According to following equation calculating clearance rate: ABTS clearance rate (%)=[A blank-(A sample-A control)]/A blank ×
100%
The immunoregulatory activities of 3. Huang granulose CEC-A of embodiment are studied
Proliferation function of the 3.1CEC-A to T, B cell
It is real with proliferation of Cell counting Kit CCK-8 (cell counting kit) the method measurement CEC-A to T, B cell
Cell number in testing.With culture solution dissolve CEC-A polysaccharide, stored for future use with 0.22 μm of filter degerming, the used time with culture solution step by step
Dilution.T, B cell and the RAW264.7 cell of logarithmic growth phase, replace fresh culture solution, and 2 are diluted to culture solution ×
The surrounding of 96 orifice plates is added in PBS buffer solution by 10 5 cells/mL, keeps sterile water environment, then 100 μ are added in remaining hole
L cell diluent.After cultivating 24 hours in 37 DEG C, the incubator of 5%CO2,100 μ L cell culture fluid (blank are sequentially added
Control), the CEC-A solution of LPS (whole 10 μ g/mL of mass concentration, positive control) and various concentration, in 37 DEG C, 5%CO2
It is cultivated 24 hours in incubator.Every hole is added 5 μ L of CCK-8 solution and continues culture 3 hours, measures light absorption value under 450nm, record knot
Fruit.It draws using concentration as abscissa, light absorption value is the curve of ordinate, and takes pictures.
Statistics and analysis
All data use mean ± SD to indicate, the conspicuousness of difference is examined with t-test, significantly use * with control group comparison
It indicates, P < 0.05 is extremely significant to be indicated with * *, P < 0.001.
As a result
1) Huang silk granulose CEC-A is to DPPH- free radical scavenging activity
Fig. 8 illustrates that the yellow more DPPH free radicals of silk granulose CEC-A sample of purifying have good scavenging capacity, and concentration is
When 4.5mg/ml, the Scavenging activity to DPPH free radical is 35.23%.
2) activity that Huang silk granulose CEC-A removes ABTS+ radical cation
ABTS+ radical cation is removed using measurement Huang silk granulose CEC-A of the spectrophotometer at 734nm
Activity.The result shows that (Fig. 9), concentration 6.4mg/mL, the Scavenging activity to ABTS free radical are 40.70%.
3) influence that .CEC-A is proliferated T lymphocyte
T cultivation effect is as shown in Figure 10, and control group is the LPS that concentration is 5 μ g/mL.CEC-A is 0.625-20 μ g/mL's
In concentration range, it is positively correlated with T cell cultivation effect；When CEC-A concentration is 0.625-2.5 μ g/mL, T cell cultivation effect
Significantly (P < 0.05), when concentration is 5-20 μ g/mL, T cell cultivation effect is extremely significant (P < 0.001)；When CEC-A concentration
Reach maximum value (P < 0.001) in 5 μ g/mL, continues to increase concentration, cell, which is affected by the ambient, causes cell to increase
Effect is grown to decline instead.
The proliferation form of T cell is as shown in Figure 11 a-11j.With the increase of CEC-A concentration, accelerated cell division becomes larger
It is agglomerating.When being stimulated with the CEC-A concentration of 5 μ g/mL, cell is agglomerating at most and maximum.
4) influence of the .CEC-A to B lymphocyte proliferation
As a result as shown in figure 12, control group is the LPS of 5 μ g/mL.CEC-A increases when concentration is 0.625-80 μ g/mL
It grows effect and reaches extremely significant (P < 0.001)；It is also best in the concentration cultivation effect of 20 μ g/mL.From the perspective of morphology, B cell is in
Regular circle, it will be apparent that cluster growth.For B cell proliferation form of the invention as shown in Figure 13 a-13j, B cell is suspended in training
It supports in hole, growth conditions are good, and after CEC-A stimulation, the group of being polymerized to after cell volume becomes larger, proliferative capacity is vigorous.
The foregoing is only a preferred embodiment of the present invention, the scope of protection of the present invention is not limited to this, it is any ripe
It knows those skilled in the art within the technical scope of the present disclosure, the simple of technical solution can be become apparent to
Variation or equivalence replacement are fallen within the protection scope of the present invention.
Claims (2)
1. a kind of natural products Huang silk granulose CEC-A, which is characterized in that the heteroglycan being made of two monosaccharide, the i.e. Portugal β-D-
Grape sugar and α-D-xylose are formed with the ratio of 5:1, average molecular weight 61056D, the skeleton with (1-4) β-D-Glucose, 6-
One → 1 is connected on O) side chain of-α-D-xylose, the structural formula of yellow silk granulose CEC-A are as follows:
2. natural products Huang silk granulose CEC-A described in claim 1 is in anti-oxidation medicine and immunoregulation medicine preparation process
In application.
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| CN1472226A (en) * | 2003-06-20 | 2004-02-04 | 宁波泰康红豆杉生物工程有限公司 | Extractive in Taxus chinensis branches and leaves and extracting method thereof |
| CN103554285A (en) * | 2013-10-15 | 2014-02-05 | 甘肃省商业科技研究所 | Extraction method of chanterelle mycelium polysaccharide |
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| CN1472226A (en) * | 2003-06-20 | 2004-02-04 | 宁波泰康红豆杉生物工程有限公司 | Extractive in Taxus chinensis branches and leaves and extracting method thereof |
| CN103554285A (en) * | 2013-10-15 | 2014-02-05 | 甘肃省商业科技研究所 | Extraction method of chanterelle mycelium polysaccharide |
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