CN107417806A - A kind of preparation method of the gallic acid glucan oligimer with α glucosidase inhibitory actives - Google Patents
A kind of preparation method of the gallic acid glucan oligimer with α glucosidase inhibitory actives Download PDFInfo
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- CN107417806A CN107417806A CN201710595058.9A CN201710595058A CN107417806A CN 107417806 A CN107417806 A CN 107417806A CN 201710595058 A CN201710595058 A CN 201710595058A CN 107417806 A CN107417806 A CN 107417806A
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- 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
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
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Abstract
The invention discloses a kind of preparation method of the gallic acid glucan oligimer with α glucosidase inhibitory actives.This method reacts generation triacetyl gallic acid with gallic acid and acetic anhydride in anhydrous pyridine first, further using dichloromethane as solvent, reacts generation triacetyl nutgall acyl chlorides with thionyl chloride；Again using triacetyl nutgall acyl chlorides as esterifying agent, generation gallic acid glucan oligimer is reacted in anhydrous pyridine with glucan (mean molecule quantity 1,000 5000).The oligomer good water solubility, and can effectively suppress the activity of α glucuroides, there is application prospect in field of functional food.
Description
Technical field
The present invention relates to a kind of preparation side of gallic acid-glucan oligimer with alpha-glucosaccharase enzyme inhibition activity
Method.The preparation technology of the present invention is simple, and gained gallic acid-glucan oligimer can effectively suppress the work of alpha-glucosidase
Property, there is water solubility well, there is application prospect in field of functional food.
Background technology
Diabetes are a kind of diseases characterized by hyperglycaemia and metabolic disorder, and it can not be effectively by the grape in blood
Sugar transportation is to cell.It mainly includes geneogenous 1 patients with type Ⅰ DM, and (type and acquired 2 type, 1 patients with type Ⅰ DM exist
Childhood can is diagnosed, and excreting insulin, diabetes B are not main discoveries caused by insulin resistance in vivo for it
More than 90% belongs to this type in adult, diabetic.It is thin that the alpha-glucosidase of mammal is located at intestinal villi
The surface of born of the same parents, it is the key enzyme that a kind of carbohydrate digestion absorbs, its main function is that oligosaccharides or disaccharides are hydrolyzed into monose
For absorption of human body.Therefore, alpha-glucosidase restrainer can delay the catabolite oligosaccharides or two of carbohydrate in diet
Sugar is hydrolyzed to glucose, so as to reduce intake of the human body to glucose, and then suppresses the elevated effect of postprandial blood sugar.Research
The tanning matter shown from plant has very strong inhibition to alpha-glucosidase, therefore structure has class tannin
The compound of structure, it is a kind of new approach for developing alpha-glucosidase restrainer.The present invention is by short chain glucan（It is flat
Average molecular weight 1000 ~ 5000）Molecular modification, gallic acid-glucan oligimer of synthesizing water-solubility are carried out, the oligomer has
Class tannin structure, has good inhibition to alpha-glucosidase, and it has more wide in field of functional food
Application prospect.
The content of the invention
The main object of the present invention, which is to provide, to be related to a kind of gallic acid-Portugal with alpha-glucosaccharase enzyme inhibition activity and gathers
The preparation method of saccharide oligomers, the technical scheme is that：
A kind of preparation method of gallic acid-glucan oligimer with alpha-glucosaccharase enzyme inhibition activity, including following step
Suddenly：
(1) preparation of triacetyl gallic acid
Gallic acid 10g ~ 20g is weighed, is dried 3 ~ 5 hours under 100 DEG C ~ 120 DEG C baking ovens, by gallic acid, acetic anhydride, anhydrous
Pyridine mol ratio is 1:4:4 order is sequentially added in 250mL beakers, ice bath, reduces temperature to room temperature, magnetic agitation reaction 12
~ 18 hours；5 times of reaction volume distilled water are added into reaction solution, are that 20% ~ 36.5% hydrochloric acid regulation pH value is 1 with mass fraction,
6 ~ 12 hours are stood, is filtered, distills water washing three times with 5mL ~ 15mL, 40 DEG C ~ 50 DEG C are dried under vacuum to constant weight, obtain triacetyl and do not have
Gallate-based.
(2) preparation of triacetyl nutgall acyl chlorides
5g ~ 15g triacetyl gallic acids are taken, sequentially add 25mL ~ 75mL dichloromethane, DMF in order
1.0% ~ 1.5%, thionyl chloride is 1 with gallic acid mol ratio:3；The condensing reflux 2 ~ 4 hours at 60 DEG C ~ 70 DEG C, 40 DEG C ~ 50
DEG C rotary evaporation boils off solvent；Add 25mL ~ 75mL carbon tetrachloride, 60 DEG C ~ 80 DEG C condensing refluxes 1 ~ 2 hour, filter while hot,
Room temperature is naturally cooled to after being recrystallized overnight at 4 DEG C, is filtered, 40 DEG C ~ 50 DEG C are dried under vacuum to constant weight, obtain triacetyl nutgall
Acyl chlorides.
(3) preparation of triacetyl gallic acid-glucan oligimer
Weigh glucan（Mean molecule quantity 1000 ~ 5000）0.5g ~ 1.0g, adds 5mL ~ 10mL anhydrous pyridines, and oil bath stirring rises
Temperature backflow, triacetyl nutgall acyl chlorides obtained by step (2) is added after it is completely dissolved, then to it, glucan does not have with triacetyl
Infanticide acyl chlorides mass ratio is 1:2~1:Reacted 3 ~ 5 hours at 3,120 DEG C；It is cooled to room temperature, adds cold anhydrous of 10 ~ 20 times of volumes
Ethanol, 4 DEG C stand 6 ~ 12 hours, collect solid in reaction system, filter, and 5mL ~ 15mL absolute ethyl alcohols washing filter cake three times, will
Filter cake is quickly collected into glass culture dish, and 40 DEG C ~ 50 DEG C are dried under vacuum to constant weight, and it is few to obtain triacetyl gallic acid-glucan
Polymers.
(4) preparation of gallic acid-glucan oligimer
0.1mol Anhydrous potassium carbonates are dissolved in 20mL absolute methanols, add triacetyl gallic acid-glucan obtained by step (3)
Oligomer；Stir 1 ~ 2 hour, filter at 40 DEG C, three times, 40 DEG C ~ 50 DEG C are dried in vacuo 5mL ~ 15mL absolute methanols washing filter cake
To constant weight, gallic acid-glucan oligimer is obtained.
Advantages of the present invention and effect：
(1) by chemical esterification method to short chain glucan（Mean molecule quantity 1000 ~ 5000）Molecular modification is carried out, synthesis does not have
Gallate-based-glucan oligimer has good inhibition to alpha-glucosidase.
(2) simple production process of the invention, the functional characteristic and bioactivity of former glucan can effectively be improved, and
Organic solvent used can be reclaimed effectively in purification step, save production cost, therefore the present invention has wide city
Field prospect.
Brief description of the drawings
Fig. 1 is the ultraviolet spectra of gallic acid-glucan oligimer of the present invention；
Fig. 2 is gallic acid-glucan oligimer of the present invention1H-NMR spectrum；
Fig. 3 is gallic acid-glucan oligimer of the present invention13C-NMR spectrum；Fig. 4 does not have to be of the present invention
Gallate-based-glucan oligimer suppresses alpha-glucosaccharase enzyme effect；
Embodiment
For the implementation of the present invention is discussed in detail, embodiment is listed below, but protection scope of the present invention is not by following reality
Apply the limitation of example.
Embodiment 1
(1) preparation of triacetyl gallic acid
Dried gallic acid 15g is added in 250mL beakers, adds 35mL acetic anhydrides and 30mL thereto successively in order
Anhydrous pyridine, ice bath, rapid temperature to room temperature, the magnetic agitation that reduce are reacted 12 hours；325mL distillations are added into reaction solution
Water, the concentrated hydrochloric acid that mass fraction is 36.5% is added, regulation pH value is 1, separates out white precipitate, stands 12 hours, filter, uses
10mL distillations water washing three times, is dried under vacuum to constant weight at 40 DEG C, obtains triacetyl gallic acid 14.5g.
(2) preparation of triacetyl nutgall acyl chlorides
Triacetyl gallic acid 10g obtained by weighing step (1), is placed in 250mL round-bottomed flasks, sequentially adds dichloromethane in order
Alkane solvents 50mL, DMF 0.7mL, thionyl chloride 7.5mL, condensing reflux 3 hours at 60 DEG C；50 DEG C of rotations
Turn evaporation and boil off solvent, add 50mL carbon tetrachloride, condensing reflux 2 hours, are filtered while hot at 70 DEG C, naturally cool to room temperature
After being recrystallized overnight at 4 DEG C, filter, filter cake obtains triacetyl nutgall acyl chlorides 6.52g through being dried under vacuum to constant weight at 40 DEG C.
(3) preparation of triacetyl gallic acid-glucan oligimer
Take 0.5g glucans（Mean molecule quantity 1000）It is placed in 250mL round-bottomed flasks, adds 5mL anhydrous pyridine, oil bath is stirred
Temperature rising reflux is mixed, triacetyl nutgall acyl chlorides 1g obtained by step (2) is added after glucan is completely dissolved, then to it, at 120 DEG C
Lower reaction 3 hours；Room temperature is cooled to, adds the cold absolute ethyl alcohols of 50mL, 4 DEG C stand 12 hours, collect solid in reaction system,
Filter, 10mL absolute ethyl alcohols washing filter cake three times, filter cake is quickly collected into glass culture dish, 40 DEG C are dried under vacuum to perseverance
Weight, obtains triacetyl gallic acid-glucan oligimer 0.1964g.
(4) preparation of gallic acid-glucan oligimer
0.0138g Anhydrous potassium carbonates are weighed, are dissolved in 20mL absolute methanols, add triacetyl gallic acid-Portugal obtained by step (3)
Glycan oligomer；Stirring 1 hour, filter at 40 DEG C, three times, 40 DEG C are dried under vacuum to constant weight to 10mL absolute methanols washing filter cake,
Obtain gallic acid-glucan oligimer 0.1675g.
Embodiment 2
(1) preparation of triacetyl gallic acid
Dried gallic acid 10g is added in 250mL beakers, adds 24mL acetic anhydrides and 20mL thereto successively in order
Anhydrous pyridine, ice bath, rapid temperature to room temperature, the magnetic agitation that reduce are reacted 18 hours；220mL distillations are added into reaction solution
Water, the concentrated hydrochloric acid that mass fraction is 30% is added, regulation pH value is 1, separates out white precipitate, stands 10 hours, filter, uses
Three times, 40 DEG C are dried under vacuum to constant weight to 15mL distillations water washing, obtain triacetyl gallic acid 9.6g.
(2) preparation of triacetyl nutgall acyl chlorides
Triacetyl gallic acid 8g obtained by weighing step (1), is placed in 250mL round-bottomed flasks, sequentially adds dichloromethane in order
Alkane solvents 40mL, DMF 0.6mL, thionyl chloride 6mL, condensing reflux 2 hours at 70 DEG C；45 DEG C of rotations
Solvent is boiled off, adds 40mL carbon tetrachloride, condensing reflux 1 hour, is filtered while hot at 80 DEG C, after naturally cooling to room temperature
Recrystallize, filter overnight at 4 DEG C, filter cake obtains triacetyl nutgall acyl chlorides 5.37g through being dried under vacuum to constant weight at 40 DEG C.
(3) preparation of triacetyl gallic acid-glucan oligimer
Take 0.5g（Mean molecule quantity 1000）Glucan is placed in 250mL round-bottomed flasks, adds 5mL anhydrous pyridine, and oil bath is stirred
Temperature rising reflux is mixed, triacetyl nutgall acyl chlorides 1.5g obtained by step (2) is added after glucan is completely dissolved, then to it, 120
Reacted 4 hours at DEG C；Room temperature is cooled to, adds the cold absolute ethyl alcohols of 75mL, 4 DEG C stand 10 hours, collect solid in reaction system
Body, filter, 15mL absolute ethyl alcohols washing filter cake three times, filter cake is quickly collected into glass culture dish, 40 DEG C are dried under vacuum to
Constant weight, obtain triacetyl gallic acid-glucan oligimer 0.4395g.
(4) preparation of gallic acid-glucan oligimer
0.0138g Anhydrous potassium carbonates are weighed, are dissolved in 20mL absolute methanols, add triacetyl gallic acid-Portugal obtained by step (3)
Glycan oligomer；Stirring 2 hours, filter at 40 DEG C, three times, 40 DEG C are dried under vacuum to constant weight to 15mL absolute methanols washing filter cake,
Obtain gallic acid-glucan oligimer 0.2673g.
Embodiment 3
(1) preparation of triacetyl gallic acid
Dry gallic acid 15g is added in 250mL beakers, add thereto successively in order 42mL acetic anhydrides and 36mL without
Water pyridine, ice bath, rapid temperature to room temperature, the magnetic agitation that reduce are reacted 12 hours；390mL distilled water is added into reaction solution,
The concentrated hydrochloric acid that mass fraction is 36.5% is added, regulation pH value is 1, separates out white precipitate, stands 12 hours, filters, use 10mL
Distill water washing three times, 50 DEG C are dried under vacuum to constant weight, obtain triacetyl gallic acid 14.8g.
(2) preparation of triacetyl nutgall acyl chlorides
Triacetyl gallic acid 15g obtained by weighing step (1), is placed in 250mL round-bottomed flasks, sequentially adds dichloromethane in order
Alkane solvents 75mL, DMF 1.0mL, thionyl chloride 11.3mL, condensing reflux 3 hours at 60 DEG C；50 DEG C of rotations
Turn evaporation and boil off solvent, add 75mL carbon tetrachloride, condensing reflux 2 hours, are filtered while hot at 70 DEG C, naturally cool to room temperature
After being recrystallized overnight at 4 DEG C, filter, filter cake obtains triacetyl nutgall acyl chlorides 10.68g through being dried under vacuum to constant weight at 50 DEG C.
(3) preparation of triacetyl gallic acid-glucan oligimer
Take 1g glucans（Mean molecule quantity 5000）It is placed in 250mL round-bottomed flasks, adds 10mL anhydrous pyridine, oil bath stirring
Temperature rising reflux, triacetyl nutgall acyl chlorides 2g obtained by step (2) is added at 120 DEG C after glucan is completely dissolved, then to it
Reaction 4 hours；Room temperature is cooled to, adds the cold absolute ethyl alcohols of 150mL, 4 DEG C stand 12 hours, collect solid in reaction system,
Filter, 10mL absolute ethyl alcohols washing filter cake three times, filter cake is quickly collected into glass culture dish, 50 DEG C are dried under vacuum to perseverance
Weight, obtains triacetyl gallic acid-glucan oligimer 0.6987g.
(4) preparation of gallic acid-glucan oligimer
0.0138g Anhydrous potassium carbonates are weighed, are dissolved in 20mL absolute methanols, add triacetyl gallic acid-Portugal obtained by step (3)
Glycan oligomer；Stirring 2 hours, filter at 40 DEG C, three times, 50 DEG C are dried under vacuum to constant weight to 10mL absolute methanols washing filter cake,
Obtain gallic acid-glucan oligimer 0.5212g.
Claims (5)
1. a kind of preparation method of gallic acid-glucan oligimer with alpha-glucosaccharase enzyme inhibition activity, including it is following
Step：
(1) preparation of triacetyl gallic acid
Take gallic acid after drying to be placed in beaker, sequentially add acetic anhydride and anhydrous pyridine in order, ice bath, reduce temperature extremely
Room temperature, magnetic agitation reaction a period of time；Distilled water is added into reaction solution, is 1 with salt acid for adjusting pH value, separates out precipitation, it is quiet
Put, filter, distill water washing, vacuum drying, obtain triacetyl gallic acid；
(2) preparation of triacetyl nutgall acyl chlorides
Take triacetyl gallic acid obtained by step (1) to be placed in round-bottomed flask, sequentially add dichloromethane, N, N- diformazans in order
Base formamide, thionyl chloride, condensing reflux reaction a period of time；Solvent is boiled off, carbon tetrachloride recrystallization, is filtered, vacuum drying,
Obtain triacetyl nutgall acyl chlorides；
(3) preparation of triacetyl gallic acid-glucan oligimer
Glucan is placed in round-bottomed flask, adds anhydrous pyridine, temperature rising reflux is stirred in oil bath, after it is completely dissolved, then to
It adds triacetyl nutgall acyl chlorides obtained by step (2), reaction a period of time, is cooled to room temperature；Added into reaction system big
Cold absolute ethyl alcohol is measured, is stood, collects solid in reaction system, is filtered, absolute ethyl alcohol washing, filter cake is quickly collected to glass
In culture dish, vacuum drying, triacetyl gallic acid-glucan oligimer is obtained；
(4) preparation of gallic acid-glucan oligimer
Anhydrous potassium carbonate is dissolved in absolute methanol, adds triacetyl gallic acid-glucan oligimer obtained by step (3),
Stirring reaction for a period of time, filters, and vacuum drying, obtains gallic acid-glucan oligimer.
2. as weigh profit require 1 as described in method, it is characterised in that：Taken in step (1) gallic acid 10g ~ 20g 100 DEG C ~
Dried 3 ~ 5 hours under 120 DEG C of baking ovens；Gallic acid, acetic anhydride, the mol ratio of anhydrous pyridine are 1:4:4；Magnetic agitation reaction 12
~ 18 hours；5 times of reaction volume distilled water are added, hydrochloric acid mass fraction is 20% ~ 36.5%；6 ~ 12 hours are stood, filters, uses 5mL
Three times, 40 DEG C ~ 50 DEG C are dried under vacuum to constant weight to ~ 15mL distillations water washing.
3. method as claimed in claim 2, it is characterised in that：5g ~ 15g triacetyl gallic acids are taken in step (2), add two
Chloromethane alkane solvents 25mL ~ 75mL, DMF 1.0% ~ 1.5%, thionyl chloride are 1 with gallic acid mol ratio:3；
The condensing reflux 2 ~ 4 hours at 60 DEG C ~ 70 DEG C, 40 DEG C ~ 50 DEG C rotary evaporations boil off solvent；Add the chlorinations of 25mL ~ 75mL tetra-
Carbon, 60 DEG C ~ 80 DEG C condensing refluxes 1 ~ 2 hour, is filtered while hot, is naturally cooled to room temperature after being recrystallized overnight at 4 DEG C, is filtered,
40 DEG C ~ 50 DEG C are dried under vacuum to constant weight.
4. method as claimed in claim 3, it is characterised in that：Step takes glucan (mean molecule quantity 1000-5000) in (3)
0.5g ~ 1.0g, adds 5mL ~ 10mL anhydrous pyridines, and glucan is 1 with triacetyl nutgall acyl chlorides mass ratio：2~1：3,120 DEG C
Lower reaction 3 ~ 5 hours；The cold absolute ethyl alcohol of 10 ~ 20 times of volumes is added, 4 DEG C stand 6 ~ 12 hours；Filter, the anhydrous second of 5mL ~ 15mL
Three times, 40 DEG C ~ 50 DEG C are dried under vacuum to constant weight to alcohol washing filter cake.
5. method as claimed in claim 4, it is characterised in that：In step (4) by 0.1mol Anhydrous potassium carbonates be dissolved in 20mL without
Water methanol；Stir 1 ~ 2 hour, filter, 40 DEG C ~ 50 DEG C are dried under vacuum to constant weight at 40 DEG C.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102627701A (en) * | 2012-04-11 | 2012-08-08 | 承德医学院中药研究所 | Preparation method of galloyl konjac glucomannan |
| CN102936296A (en) * | 2012-12-06 | 2013-02-20 | 承德天创生物制品有限公司 | Preparation method for galloyl konjac glucomannan |
| CN103435589A (en) * | 2013-09-17 | 2013-12-11 | 北京林业大学 | Treatment method for enhancing stability of blueberry cyanidin |
| CN104530263A (en) * | 2014-12-17 | 2015-04-22 | 桂林理工大学 | Preparation method of gallic acid-bagasse xylan ester |
-
2017
- 2017-07-20 CN CN201710595058.9A patent/CN107417806A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102627701A (en) * | 2012-04-11 | 2012-08-08 | 承德医学院中药研究所 | Preparation method of galloyl konjac glucomannan |
| CN102936296A (en) * | 2012-12-06 | 2013-02-20 | 承德天创生物制品有限公司 | Preparation method for galloyl konjac glucomannan |
| CN103435589A (en) * | 2013-09-17 | 2013-12-11 | 北京林业大学 | Treatment method for enhancing stability of blueberry cyanidin |
| CN104530263A (en) * | 2014-12-17 | 2015-04-22 | 桂林理工大学 | Preparation method of gallic acid-bagasse xylan ester |
Non-Patent Citations (2)
| Title |
|---|
| 张海凤等: "没食子酸对α-葡萄糖苷酶的抑制作用及其降糖机制研究", 《中国药业》 * |
| 李金凤等: "多糖-酚酸缀合物的合成及特性研究进展", 《食品与发酵工业》 * |
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Application publication date: 20171201 |