CN110128565B - Ganoderma beta-glucan sulfate and synthesis method and application thereof - Google Patents
Ganoderma beta-glucan sulfate and synthesis method and application thereof Download PDFInfo
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- CN110128565B CN110128565B CN201910372145.7A CN201910372145A CN110128565B CN 110128565 B CN110128565 B CN 110128565B CN 201910372145 A CN201910372145 A CN 201910372145A CN 110128565 B CN110128565 B CN 110128565B
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
Abstract
The invention discloses ganoderma lucidum beta-glucan sulfate with a structural formula (I). The invention provides the following structural formula(I) The compound has strong in-vitro anticoagulant activity, and can be used as an anticoagulant in the pharmaceutical industry.
Description
Technical Field
The invention relates to the field of biological macromolecules, in particular to ganoderma lucidum beta-glucan sulfate and a synthesis method and application thereof.
Background
Glucans are a class of high molecular polysaccharides polymerized from glucose monomers and can be classified into alpha-type and beta-type. Common alpha-glucan mainly comprises starch, dextrin, glycogen and the like, and the biological activity of the alpha-glucan is considered to be low or no biological activity by pharmacological research at present; beta-glucan is a major component of the fungal cell wall and is a typical "biological response modifier" (BRM). Research results show that the fungus beta-glucan not only can activate B, T immune cells such as lymphocytes and macrophages, but also can promote the generation of cytokines, activate a complement system, promote the generation of antibodies and play a multi-aspect regulating role on the immune system, and the anti-tumor effect of the fungus beta-glucan is also considered to be related to the activation of the immune system of the body (Int J Biol Macromol,2015,72, 588-598). Because the fungus beta-glucan has multiple effects of immunoregulation, tumor resistance and the like, the fungus beta-glucan has wide development and application prospects in the fields of food, medicine, biological materials and the like.
Ganoderma beta-glucan is one of the main active components in Ganoderma (Ganoderma lucidum), and can exert its corresponding biological activity by affecting immune cells such as hematopoietic stem cells, macrophages and lymphocytes, etc., to enhance and activate the body's immune function. Patent ZL 201510727866.7 discloses a ganoderma lucidum beta-glucan and a preparation method thereof, and provides the application of the ganoderma lucidum beta-glucan in the aspects of immune regulation and tumor resistance. However, the molecular weight of ganoderma lucidum beta-glucan is up to three million, and the ganoderma lucidum beta-glucan has extremely poor solubility in cold water, so that the ganoderma lucidum beta-glucan is limited in application.
Disclosure of Invention
The invention aims to provide ganoderma lucidum beta-glucan sulfate which is a compound with the following structural formula (I):
wherein R is1、R2、R3、R1’、R2’、R3’、R4' is H or SO respectively3H；
One preferred way is: r1、R2、R3、R1’、R2’、R3’、R4Are both SO3H；
Another preferred embodiment is: r1、R2、R1’、R2’、R4' is H, R3、R3Is' SO3H；
Another preferred embodiment is: r1、R2、R1’、R2’、R4Is' SO3H，R3、R3' is H;
specifically, the ganoderma lucidum beta-glucan sulfate provided by the invention is a compound with the following structural formula (II):
or a compound of the following structural formula (III):
or a compound of the following structural formula (IV):
the invention also provides a synthesis method of the ganoderma lucidum beta-glucan sulfate, and the reaction route is as follows:
the raw material is beta- (1 → 3) -glucan, 1 glucose branch chain is connected with every 2 residues beta- (1 → 6), and the beta-glucan is directly sulfated and modified, or is sulfated and modified on the 6 position, the 2 position or the 4 position of the glucan through a group protection strategy to respectively generate ganoderma lucidum beta-glucan sulfate with full substitution, 6-position substitution and 2, 4-position substitution.
Specifically, the invention also provides a synthesis method of the compounds with structural formulas (II), (III) and (IV), which comprises the following steps:
1. synthesis of compound of structural formula (ii) (fully substituted ganoderma β -glucan sulfate, SGLP): adding ganoderma beta-glucan (purity 95%) into a reaction bottle containing N, N-Dimethylformamide (DMF), stirring at room temperature for 0.5 h, adding a sulfonation reagent sulfur trioxide pyridine complex, stirring at 60 ℃ for reaction for 2h, cooling to room temperature, neutralizing with dilute alkali liquor, precipitating with 80% ethanol, dissolving the precipitate in distilled water again, dialyzing with a dialysis bag, and freeze-drying the dialysate to obtain SGLP.
2. Compound of structural formula (III) (6-substituted ganoderma beta-glucan sulfate, S)6-OGLP) synthesis: adding Ganoderma beta-glucan (purity 95%) into a reaction bottle containing dichloromethane, adding a group protection reagent hexamethyldisilazane and a catalyst trifluoromethanesulfonic trimethyl silicone grease, stirring at 30 ℃ for reaction for 2h, removing dichloromethane solvent, obtaining a sulfation intermediate product according to the sulfation reaction step of SGLP, adding 80% acetic acid solution, reacting at room temperature for 4h, removing protection groups, precipitating with ethanol, dialyzing with distilled water, and freeze-drying to obtain S6-OGLP。
3. Compound of structural formula (IV) (2, 4-substituted ganoderma lucidum beta-dextran sulfate, S)2,4-OGLP) synthesis: adding Ganoderma beta-glucan (purity 95%) into a reaction bottle containing N, N-dimethylformamide, adding protective group 4,4' -dimethoxy triphenylchloromethane and catalyst pyridine, stirring at 80 deg.C for reaction for 12h, adding ethanol for precipitation, ultrasonically washing the precipitate with ethanol, drying the precipitate to obtain 6-position protected sulfated derivative, performing full sulfation reaction to obtain sulfated intermediate product, adding 80% acetic acid solution, reacting at room temperature for 4h, removing the protective group, precipitating with ethanol, dialyzing with distilled water, and freeze-drying to obtain S2,4-OGLP。
In vitro anticoagulant activity experiments show that the ganoderma lucidum beta-glucan sulfate with the structural formula (I) provided by the invention has strong in vitro anticoagulant activity, has an anticoagulant mechanism different from that of heparin sodium, and can be used as an anticoagulant in the pharmaceutical industry.
Therefore, the invention also provides the application of the ganoderma lucidum beta-glucan sulfate shown in the structural formula (I) as an anticoagulant.
According to the ganoderma lucidum beta-glucan sulfate with the structural formula (I), provided by the invention, the primary hydroxyl, non-primary hydroxyl or all hydroxyl of the ganoderma lucidum beta-glucan is subjected to sulfation modification through stereoselectivity modification on the ganoderma lucidum beta-glucan, so that the solubility of the ganoderma lucidum beta-glucan is enhanced, and the biological activity of the ganoderma lucidum beta-glucan is enhanced or expanded; in vitro anticoagulant activity experiments show that the ganoderma lucidum beta-glucan sulfate has remarkable anticoagulant activity, and the ganoderma lucidum beta-glucan sulfate with 6-substituted position has the strongest anticoagulant activity and can be used as an anticoagulant.
Compared with the prior art, the invention has the following advantages:
1. the invention utilizes a new group protection technology, and the stereoselectively synthesized 6-substituted ganoderma lucidum beta-glucan sulfate has high substitution degree and strongest in vitro anticoagulation activity; meanwhile, the original group protection technology is improved, and the stereoselectively synthesized 2, 4-substituted ganoderma lucidum beta-glucan sulfate has higher substitution degree and stronger in-vitro anticoagulation activity than full substitution; these facilitate the use of ganoderma beta-glucan as a natural active polysaccharide.
2. The substitution degree and the molecular weight of the ganoderma lucidum beta-glucan sulfate prepared by the invention can be adjusted and optimized through the proportion of a sulfonation reagent, the reaction temperature and the reaction time so as to meet the application requirements of different fields.
3. The invention does not need special equipment, has simple preparation process, low cost and controllable product and is suitable for popularization and application.
Drawings
FIG. 1 shows the infrared absorption spectrum of fully substituted Ganoderma beta-glucan sulfate
FIG. 2 nuclear magnetic resonance carbon spectrum of fully substituted ganoderma lucidum beta-dextran sulfate
FIG. 3, infrared absorption spectrum of 6-substituted Ganoderma beta-dextran sulfate
FIG. 4 nuclear magnetic resonance carbon spectrum of 6-substituted ganoderma lucidum beta-glucan sulfate
FIG. 5 is an infrared absorption spectrum of 2, 4-substituted Ganoderma beta-glucan sulfate
FIG. 6 nuclear magnetic resonance carbon spectrum of 2, 4-substituted Ganoderma beta-dextran sulfate
FIG. 7, APTT diagram of Ganoderma lucidum beta-glucan and its sulfate.
FIG. 8, PT diagram of Ganoderma lucidum beta-glucan and its sulfate.
FIG. 9, TT diagram of Ganoderma lucidum beta-glucan and its sulfate.
WhereinIn FIGS. 7-9: heparin sodium: heparin sodium; GLP: ganoderma lucidum beta-glucan; SGLP: fully substituted beta-glucan sulfate of ganoderma lucidum; s2,4-OGLP: 2, 4-substituted ganoderma beta-glucan sulfate; s6-OGLP: 6-substituted ganoderma beta-glucan sulfate
The specific implementation mode is as follows:
material sources are as follows:
the preparation method of Ganoderma beta-glucan is disclosed in patent CN 105175575A;
the sulfur trioxide pyridine complex and dialysis bag were purchased from SIGMA-ALDRICH.
Example 1: preparation of fully substituted ganoderma beta-dextran sulfate (reaction route I)
Adding ganoderma beta-glucan (1g) into a two-mouth reaction bottle with a reflux condenser tube, adding 50mL of DMF, stirring at room temperature for 0.5 hour, adding sulfur trioxide pyridine complex (4g) under the protection of nitrogen, stirring at 60 ℃ for 2 hours, cooling to room temperature, adding 50mL of distilled water, adjusting the pH to 7-8 with 3mol/mL of NaOH solution, adding 400mL of ethanol for precipitation, centrifuging the precipitate with a centrifuge at 8000rpm for 20 minutes, taking the precipitate, dissolving the precipitate in 200mL of distilled water, centrifuging with the centrifuge at 8000rpm for 20 minutes again, taking the supernatant, dialyzing with a dialysis bag (molecular weight cut-off of 3500g/mol) for 72 hours, and freeze-drying the dialysate to obtain the fully-substituted ganoderma beta-glucan sulfate. The infrared absorption spectrum and nuclear magnetic resonance carbon spectrum of the fully-substituted ganoderma lucidum beta-dextran sulfate are respectively shown in figure 1 and figure 2.
EXAMPLE 2 preparation of 6-substituted Ganoderma beta-Glucan sulfate (scheme II)
Adding ganoderma beta-glucan (1g) into a two-mouth reaction bottle with a reflux condenser tube, adding 30mL of dichloromethane, adding 4.6mL of hexamethyldisilazane and 0.2mL of trimethylsilyl trifluoromethanesulfonate under the protection of nitrogen, stirring at 30 ℃ for 2h for reaction, removing dichloromethane after the reaction is finished, obtaining a sulfated intermediate product according to the sulfation reaction step of fully-substituted ganoderma beta-glucan sulfate, adding 100mL of 80% acetic acid solution, reacting at room temperature for 4h, adding 100mL of 80% ethanol for precipitation, dissolving the precipitate in 200mL of distilled water, centrifuging at 8000rpm by using a centrifuge for 20min, taking the supernatant, dialyzing by using a dialysis bag (molecular weight cut-off is 3500g/mol) for 72 h, and freeze-drying the dialysate to obtain 6-position-substituted ganoderma beta-glucan sulfate. The infrared absorption spectrum and nuclear magnetic resonance carbon spectrum of the 6-substituted Ganoderma beta-dextran sulfate are respectively shown in figure 3 and figure 4.
EXAMPLE 3 preparation of 2, 4-substituted Ganoderma beta-Glucan sulfate (scheme III)
Adding Ganoderma beta-dextran (1g) into a two-mouth reaction flask with reflux condenser, adding 50mL DMF, adding 1mL pyridine under nitrogen protection, stirring at room temperature for 0.5 hr, adding 4,4' -dimethoxytriphenylchloromethane (2.8g), stirring at 80 deg.C for reaction for 12 hr, stopping reaction, cooling, adding 200mL anhydrous ethanol for precipitation, washing the precipitate with anhydrous ethanol, drying the precipitate to obtain 6-position protected sulfated derivative, performing full sulfation reaction to obtain sulfated intermediate product, adding 100mL 80% acetic acid solution, reacting at room temperature for 6 hr, adding 400mL ethanol for precipitation, washing the precipitate with anhydrous ethanol, dissolving in 200mL distilled water, centrifuging at 8000rpm for 20min, collecting supernatant, dialyzing with dialysis bag (molecular weight cut-off of 3500g/mol) for 72 hr, the dialyzate is frozen and dried to obtain the 2, 4-substituted ganoderma lucidum beta-glucan sulfate. The infrared absorption spectrum of 2, 4-substituted Ganoderma beta-dextran sulfate is shown in figure 5, and the nuclear magnetic resonance carbon spectrum is shown in figure 6.
Example 4 structural characterization analysis of Ganoderma beta-Glucan sulfate
Separating by high performance GEL chromatography (waters 2695 pump separation system) with TSK-GEL series G6000PWXL and G4000PWXL chromatographic columns (7.8mm × 300mm, TOSOH, Japan) in series at octagonal degreeThe results of the analyses performed by the laser light scattering detector (MALLS, Wyatt Co.) and the Waters 2414 differential detector (RI) revealed that the weight average molecular weights of the fully substituted ganoderma lucidum β -glucan sulfate, the 6-substituted ganoderma lucidum β -glucan sulfate and the 2, 4-substituted ganoderma lucidum β -glucan sulfate of examples 1 to 3 were 1.71X 10, respectively4g/mol，6.27×104g/mol and 5.68X 104g/mol, the weight average molecular weight thereof can be adjusted depending on the reaction conditions.
The S content was measured by an elemental analyzer (Vario EL Cube, Elementar, Germany), and the degrees of substitution of the three types of Ganoderma β -glucan sulfates of examples 1-3 were calculated to be 1.72, 1.24 and 1.47, respectively, using the formula, and the degrees of substitution could be adjusted according to the reaction conditions.
The infrared absorption spectrum and the nuclear magnetic resonance carbon spectrum show that most of hydroxyl, 6-hydroxyl and 2, 4-hydroxyl of the ganoderma lucidum beta-glucan are respectively subjected to sulfation reaction to generate fully substituted, 6-substituted and 2, 4-substituted ganoderma lucidum beta-glucan sulfate.
Example 5: in vitro anticoagulant activity test of ganoderma lucidum beta-dextran sulfate
The three items of coagulation include Activated Partial Thromboplastin Time (APTT), Prothrombin Time (PT), and Thrombin Time (TT). APTT is used to evaluate the role of coagulation factors VIII, IX, XI and prekallikrein in the intrinsic coagulation pathway. PT was used to characterize the extrinsic coagulation factor. TT is used as an index of the blood coagulation state and reflects the time for converting fibrinogen into fibrin.
In vitro anticoagulant activity test of ganoderma lucidum beta-glucan sulfate, heparin sodium is used as a positive control, and APTT, PT and TT values are measured according to a classical in vitro coagulation test method (Carbohydrate Polymer,2012,87(3),2052-2057) to evaluate the in vitro anticoagulant activity of the ganoderma lucidum beta-glucan sulfate.
The full-automatic coagulation analyzer RAC030 and the APTT, PT and TT reagents are purchased from Shenzhen Redu Life sciences GmbH, and the normal human plasma sample is purchased from Chengdu-collaborating Biotech GmbH.
The specific clotting assay is as follows:
1. preparation of samples
Precisely weighing about 10mg of ganoderma lucidum beta-dextran sulfate sample, adding quantitative distilled water to fully dissolve the ganoderma lucidum beta-dextran sulfate sample, centrifuging for 30min at 18000g, diluting the supernatant, and preparing into sample solutions of 2.5, 5, 10, 25, 50, 80 and 100 mu g/mL for later use.
2. In vitro anticoagulation experiment
mu.L of normal human plasma samples and 50. mu.L of sample solutions at concentrations of 2.5, 5, 10, 25, 50, 80 and 100. mu.g/mL, respectively, were incubated at 37 ℃ for 60s, then 50. mu.L of pre-warmed APTT-analyzing reagent was added, and incubated at 37 ℃ for 180 s, followed by 0.25M calcium chloride (50. mu.L), and the clotting time, i.e., APTT value, was determined. Mixing normal human plasma (30 μ L) with 20 μ L polysaccharide solution, incubating at 37 deg.C for 150s, adding 100 μ L PT reagent pre-incubated at 37 deg.C, and determining coagulation time, i.e. PT value. mu.L of normal human plasma was mixed with 20. mu.L of polysaccharide solution, incubated at 37 ℃ for 90s, 100. mu.L of TT reagent pre-incubated at 37 ℃ was added, and the clotting time, i.e., TT value, was recorded. All clotting assays were performed 3 times. Results are expressed as mean ± Standard Deviation (SD).
3. Analysis of results
FIG. 7, FIG. 8 and FIG. 9 show the in vitro anticoagulant activity of Ganoderma lucidum beta-glucan and its sulfate. The APTT diagram of figure 7 reflects the role of coagulation factors VIII, IX, XI and prekallikrein in the intrinsic coagulation pathway. It can be seen from FIG. 7 that the 6-substituted ganoderma beta-glucan sulfate has the strongest in vitro anticoagulant activity at concentrations above 25. mu.g/mL, and is stronger than heparin sodium and other derivatives. When the concentration exceeds 50 mu g/mL, the in vitro anticoagulant activity of the 2, 4-substituted ganoderma lucidum beta-glucan sulfate is equivalent to that of heparin sodium and is stronger than that of the fully substituted ganoderma lucidum beta-glucan sulfate. The Ganoderma beta-glucan as raw material has no anticoagulant activity.
The PT plot of figure 8 reflects the role of extrinsic coagulation factors in the coagulation pathway. It can be seen from FIG. 8 that the 6-substituted beta-glucan sulfate has the strongest in vitro anticoagulant activity at concentrations above 50. mu.g/mL, and is stronger than heparin sodium and other derivatives. When the concentration exceeds 80 mug/mL, the in vitro anticoagulant activity of the fully substituted, 2, 4-substituted ganoderma lucidum beta-glucan sulfate and the heparin sodium is equivalent to that of the heparin sodium, but the activity is weaker. The Ganoderma beta-glucan as raw material has no anticoagulant activity.
The TT plot of fig. 9 reflects the time to convert fibrinogen to fibrin. As can be seen from FIG. 9, the 6-substituted beta-glucan sulfate of Ganoderma lucidum has the strongest in vitro anticoagulant activity at concentrations above 50. mu.g/mL, and is stronger than heparin sodium and other derivatives. When the concentration exceeds 80 mug/mL, the in vitro anticoagulant activity of the fully substituted, 2, 4-substituted ganoderma lucidum beta-glucan sulfate and the heparin sodium is equivalent to that of the heparin sodium, but the activity is weaker. The Ganoderma beta-glucan as raw material has no anticoagulant activity.
The in vitro anticoagulant activity experiments show that sulfate groups in the ganoderma lucidum beta-glucan derivatives play a determining role in the in vitro anticoagulant activity, the 6-substituted ganoderma lucidum beta-glucan sulfate has the strongest in vitro anticoagulant activity, and the anticoagulant mechanism is different from that of heparin sodium, so that the ganoderma lucidum beta-glucan derivatives can be used as potential anticoagulants in the pharmaceutical industry.
Claims (2)
1. A ganoderma beta-glucan sulfate is a compound with the following structural formula (I):
（Ⅰ）
wherein
R1、R2、R1’、R2’、 R4' is H, R3、R3Is' SO3H；
Or R1、R2、R1’、R2’、 R4Is' SO3H，R3、R3' is H.
2. The use of ganoderma lucidum beta-glucan sulphate as claimed in claim 1 in the preparation of an anticoagulant.
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