CN103030713A - Preparation method of low-molecular-weight glucan-niacin polymer with hypolipidemic activity - Google Patents
Preparation method of low-molecular-weight glucan-niacin polymer with hypolipidemic activity Download PDFInfo
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- CN103030713A CN103030713A CN2012105609017A CN201210560901A CN103030713A CN 103030713 A CN103030713 A CN 103030713A CN 2012105609017 A CN2012105609017 A CN 2012105609017A CN 201210560901 A CN201210560901 A CN 201210560901A CN 103030713 A CN103030713 A CN 103030713A
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- glucan
- nicotinic acid
- dextran
- niacin
- polymer
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- 229960003512 nicotinic acid Drugs 0.000 title claims abstract description 30
- 239000011664 nicotinic acid Substances 0.000 title claims abstract description 29
- 230000000055 hyoplipidemic effect Effects 0.000 title claims abstract description 6
- 229920000642 polymer Polymers 0.000 title claims abstract 4
- 238000002360 preparation method Methods 0.000 title abstract description 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 235000001968 nicotinic acid Nutrition 0.000 claims abstract description 14
- FYGDTMLNYKFZSV-URKRLVJHSA-N (2s,3r,4s,5s,6r)-2-[(2r,4r,5r,6s)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2r,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1[C@@H](CO)O[C@@H](OC2[C@H](O[C@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-URKRLVJHSA-N 0.000 claims abstract description 13
- 229920002498 Beta-glucan Polymers 0.000 claims abstract description 10
- 210000004369 blood Anatomy 0.000 claims abstract description 10
- 239000008280 blood Substances 0.000 claims abstract description 10
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 125000003700 epoxy group Chemical group 0.000 claims description 7
- 230000004913 activation Effects 0.000 claims description 5
- WKSXRWSOSLGSTN-UHFFFAOYSA-N Methoxypyrazine Chemical compound COC1=CN=CC=N1 WKSXRWSOSLGSTN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000012986 modification Methods 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims description 3
- 229920005654 Sephadex Polymers 0.000 claims description 2
- 239000012507 Sephadex™ Substances 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 229920001503 Glucan Polymers 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- 239000003607 modifier Substances 0.000 claims 1
- 239000002808 molecular sieve Substances 0.000 claims 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims 1
- 238000003912 environmental pollution Methods 0.000 abstract description 3
- 238000002474 experimental method Methods 0.000 abstract description 3
- 239000012190 activator Substances 0.000 abstract 1
- 229920002307 Dextran Polymers 0.000 description 20
- 241000699666 Mus <mouse, genus> Species 0.000 description 14
- 150000002632 lipids Chemical class 0.000 description 12
- 235000013305 food Nutrition 0.000 description 9
- 238000003304 gavage Methods 0.000 description 8
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- -1 niacin compound Chemical class 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 108010023302 HDL Cholesterol Proteins 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 201000005577 familial hyperlipidemia Diseases 0.000 description 3
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229940088594 vitamin Drugs 0.000 description 3
- 235000013343 vitamin Nutrition 0.000 description 3
- 239000011782 vitamin Substances 0.000 description 3
- 229930003231 vitamin Natural products 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000010172 mouse model Methods 0.000 description 2
- 235000005152 nicotinamide Nutrition 0.000 description 2
- 239000011570 nicotinamide Substances 0.000 description 2
- 229960003966 nicotinamide Drugs 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 1
- XJLXINKUBYWONI-NNYOXOHSSA-N NADP zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-NNYOXOHSSA-N 0.000 description 1
- 229930003537 Vitamin B3 Natural products 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000005252 bulbus oculi Anatomy 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000013345 egg yolk Nutrition 0.000 description 1
- 210000002969 egg yolk Anatomy 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 239000003058 plasma substitute Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 235000019160 vitamin B3 Nutrition 0.000 description 1
- 239000011708 vitamin B3 Substances 0.000 description 1
- 229940046001 vitamin b complex Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
一种具有降血脂活性的低分子量葡聚糖-烟酸聚合物的制备方法，属于生物化学领域。本发明通过环氧氯丙烷等活化剂活化β-葡聚糖2000，并将之与烟酸及烟酸衍生物甲氧吡嗪偶联，在小鼠实验中具有显著的降血脂能力。本发明易操作、成本低、环境污染小、适于大规模应用。The invention discloses a preparation method of a low-molecular-weight dextran-niacin polymer with hypolipidemic activity, which belongs to the field of biochemistry. The present invention activates the β-glucan 2000 by an activator such as epichlorohydrin, and couples it with nicotinic acid and nicotinic acid derivative metoxypyrazine, and has remarkable blood lipid-lowering ability in mouse experiments. The invention is easy to operate, low in cost, less in environmental pollution and suitable for large-scale application.
Description
Technical field
The present invention relates to the preparation method of a kind of LMD with hypolipidemic activity-nicotinic acid polymkeric substance, belong to biochemical field.
Background technology
Dextran claims again dextran, is a kind of polysaccharide.It is present in the mucus that certain micro-organisms secretes in process of growth.Dextran can replace a part of whole blood in the blood transfusion process, as the expansion agent (being called plasma substitute) of blood plasma volume.Its applied research at numerous areas such as medicine, food, chemical industry has obtained major progress.For the patient, the effect of dextran reducing blood-fat has research report.
Nicotinic acid is also referred to as vitamin B3, and it is one of 13 kinds of VITAMIN of needed by human, is a kind of water-soluble vitamins, belongs to vitamin B complex.Nicotinic acid is converted into niacinamide in human body, niacinamide is the integral part of cozymase and codehydrogenase Ⅱ, participates in HypercholesterolemicRats, the process that the oxidising process of tissue respiration and carbohydrate anaerobic are decomposed.When its consumption surpasses dosage as the VITAMIN effect, the effect of obvious adjusting blood fat can be arranged.Curative effect and the dosage of nicotinic acid adjusting blood fat are relevant with the front blood lipid level of taking medicine, and blood lipid level is unusually more obvious, and medication dose should be large, and curative effect is also more obvious.In addition, nicotinic acid derivates such as methoxy pyrazine and Vasonicit etc. also are used as blood lipid-lowering medicine widely.
Epoxy chloropropane is a kind of activating reagent commonly used, can act on hydroxyl, amino, carboxylic acid group, sulfydryl isoreactivity group.Use the hydroxyl of Epichlorohydrin activation dextran among the present invention, use epoxy group(ing) and niacin compound serving to carry out crosslinked.
Summary of the invention
The purpose of this invention is to provide the method for preparing small molecules dextran-nicotinic acid polymkeric substance, that the present invention designs is ingenious, mild condition, easy to operate, cost is low, environmental pollution is little, be suitable for large-scale application.
To achieve these goals, technical scheme of the present invention: the preparation method of a kind of LMD with hypolipidemic activity-nicotinic acid polymkeric substance may further comprise the steps:
(1) epoxy chloropropane method activation beta-glucan 2000;
(2) utilize niacin compound serving that the beta-glucan 2000 of activation is modified;
(3) modifying after product uses Sephadex G-50 to carry out sieve chromatography removal unreacting substance; Obtain LMD-nicotinic acid polymkeric substance, products therefrom has significant reducing blood-fat ability in mouse experiment, all has higher reducing blood-fat ability than original unmodified beta-glucan and nicotinic acid class material.
Preferably, in step (1), epoxy chloropropane and dextran hydroxyl molar ratio are 6 ︰ 1.
Preferably, the described reaction of step (1) is carried out in 0.8M NaOH solution, and temperature is 40 ℃.
Preferably, in step (2), niacin compound serving and beta-glucan 2000 epoxy group(ing) molar ratios are 2 ︰ 1.
Preferably, the described pH value in reaction of step (2) maintains 12, and temperature is 50 ℃.
The LMD of described preparation-nicotinic acid polymkeric substance has significant reducing blood-fat ability in mouse experiment, the reducing blood-fat ability all is better than beta-glucan and the niacin compound serving of unmodified.
Beneficial effect of the present invention:
1, the present invention activates its hydroxyl by epoxy chloropropane take natural dextran as matrix;
2, the present invention has optimized the ability of its reducing blood-fat by the modification to dextran.
Embodiment
In order more clearly to understand technology contents of the present invention, describe in detail especially exemplified by following examples.
Embodiment 1 epoxy chloropropane and dextran hydroxyl ratio are on modifying the impact of rear epoxy group(ing) density
:
Beta-glucan 2000 is dissolved in 0.8M NaOH solution, reach 20g/L, add epoxy chloropropane according to dextran and epoxy chloropropane hydroxyl mol ratio (1:1,1:2,1:4,1:6,1:8,1:10), 40 ℃, 50 r/min vibration fixedly 1-4 hour.Mixture adds the ethanol of precooling, centrifugal 5 min of 12000 rpm behind static 10 min, and after the taking-up precipitation, with 3 final vacuum dryings of ethanol cleaning of precooling, the dextran of activation is dissolved with tri-distilled water, measures epoxy group(ing) density, the results are shown in Table 1
Table 1 epoxy chloropropane and dextran hydroxyl molar ratio are on modifying the impact of rear epoxy group(ing) density
| Beta-glucan 2000 and epoxy chloropropane hydroxyl mol ratio | Epoxy group(ing) density (μ mol/g) |
| 1:1 | 0.3 |
| 1:2 | 0.7 |
| 1:4 | 1.1 |
| 1:6 | 1.5 |
| 1:8 | 1.4 |
| 1:10 | 1.3 |
The dextran that embodiment 2 prepares-nicotinic acid polymkeric substance is on the impact of lipid of mice:
Set up the hyperlipidemia mouse model, get 10 of male mice in kunming, high lipid food (the every kg prescription of high lipid food: formed by 840 g basal feeds, the commercially available lard of 100 g, 10 g cholesterol, 50 g egg yolks of feeding and preparing voluntarily, other adds the abundant stirring and evenly mixing of an amount of tap water, granulation shape).Detect respectively on morphology and in the serum after 6 weeks, the result compares with the normal group mouse, and total cholesterol level all obviously raises in model group with hyperlipemia mouse quality and the serum.
Male mice in kunming is divided into 4 groups at random, is respectively normal group: mouse feeds with basal feed, and gavage 9 g/L NaCl solution; Model group with hyperlipemia: mouse feeds the high lipid food of preparing with voluntarily, and gavage 9 g/ L NaCl solution; The nicotinic acid control group: mouse feeds with high lipid food, and gavage 15 g/ L nicotinic acid aquas; Methoxy pyrazine control group: mouse feeds with high lipid food, and gavage 15 g/ L methoxy pyrazine aquas; The dextran control group: mouse feeds with high lipid food, and gavage 20 g/ L dextran aquas; Dextran-nicotinic acid group: mouse feeds with high lipid food, and gavage 15 g/ L dextran-nicotinic acid aquas; Dextran-methoxy pyrazine group: mouse feeds with high lipid food, and gavage 15 g/ L dextran-methoxy pyrazine aqua; Every group of 10 mouse, each organizes the equal ad lib of mouse, and aqua and NaCl solution gavage amount are 0.4 mL/ (d is only), continue to raise for 6 weeks.After each was organized mouse and raises 6 fasting at weekend, 12 h, eyeball was got blood, isolates serum, measured and respectively organized total cholesterol in the mice serum (T C), high density lipoprotein cholesterol fat (HDL-C) the results are shown in Table 2.
Table 2 dextran-nicotinic acid polymkeric substance is on the impact of lipid of mice
| Group | TC/（mmol/L） | HDL-C/（mmol/L） |
| Normal group | 3.25±0.19 | 2.09±0.14 |
| Model group with hyperlipemia | 6.32±0.22 | 2.67±0.17 |
| The nicotinic acid control group | 5.74±0.25 | 2.51±0.15 |
| The dextran control group | 5.87±0.16 | 2.59±0.13 |
| Dextran-nicotinic acid group | 4.43±0.21 | 2.32±0.24 |
| Dextran-methoxy pyrazine group | 4.51±0.18 | 2.39±0.19 |
As can be seen from the above embodiments, adopt dextran and the nicotinic acid class material of the reducing blood-fat ability contrast unmodified of method dextran of the present invention-nicotinic acid polymkeric substance in mouse model, be significantly improved.TC(mmol/L) be down to about 4.5 from 6.32.Therefore, employing the present invention can significantly put forward the reducing blood-fat ability of dextran, and further using for this its provides solid basis.
To sum up, ingenious, the mild condition of dextran of the present invention-nicotinic acid polymkeric substance method design, easy to operate, cost is low, environmental pollution is little, be suitable for large-scale application.
In this specification sheets, the present invention is described with reference to its specific embodiment.But, still can make various modifications and conversion obviously and not deviate from the spirit and scope of the present invention.Therefore, specification sheets is regarded in an illustrative, rather than a restrictive.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2012105609017A CN103030713A (en) | 2012-12-21 | 2012-12-21 | Preparation method of low-molecular-weight glucan-niacin polymer with hypolipidemic activity |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106084083A (en) * | 2016-07-05 | 2016-11-09 | 潍坊医学院 | A kind of marine algae polysaccharide derivant and preparation method thereof |
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|---|---|---|---|---|
| WO1998008603A1 (en) * | 1996-08-30 | 1998-03-05 | Upfront Chromatography A/S | Isolation of immunoglobulins |
| CN1342170A (en) * | 1999-02-05 | 2002-03-27 | 维特罗莱夫英国有限公司 | Process for cross-linking hyaluronic acid to polymers |
| US6365186B1 (en) * | 1997-11-05 | 2002-04-02 | Geltex Pharmaceuticals, Inc. | Combination therapy for treating hypercholesterolemia |
| CN101095964A (en) * | 2006-06-26 | 2008-01-02 | 房新雨 | Method for preparing glucosan gel rubber embolism microsphere suspending liquid |
-
2012
- 2012-12-21 CN CN2012105609017A patent/CN103030713A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998008603A1 (en) * | 1996-08-30 | 1998-03-05 | Upfront Chromatography A/S | Isolation of immunoglobulins |
| US6365186B1 (en) * | 1997-11-05 | 2002-04-02 | Geltex Pharmaceuticals, Inc. | Combination therapy for treating hypercholesterolemia |
| CN1342170A (en) * | 1999-02-05 | 2002-03-27 | 维特罗莱夫英国有限公司 | Process for cross-linking hyaluronic acid to polymers |
| CN101095964A (en) * | 2006-06-26 | 2008-01-02 | 房新雨 | Method for preparing glucosan gel rubber embolism microsphere suspending liquid |
Non-Patent Citations (2)
| Title |
|---|
| CHUAN-XIN ZHANG, ZE-MEI GE, TIE-MING CHENG AND RUN-TAO LI: "Synthesis and analgesic activity of secondary amine analogues of pyridylmethylamine and positional isomeric analogues of ABT-594", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》, no. 16, 31 December 2006 (2006-12-31), pages 2013 - 2015 * |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106084083A (en) * | 2016-07-05 | 2016-11-09 | 潍坊医学院 | A kind of marine algae polysaccharide derivant and preparation method thereof |
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