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N-unsaturated fatty acid acylated chitosan oligosaccharide and preparation and application thereof

A technique for acylating chitosan oligosaccharide and unsaturated fatty acid with fatty acid, which is applied in the field of N-unsaturated fatty acid acylating chitooligosaccharide and its preparation, and can solve the problems of troublesome use and storage, insufficient stability of unsaturated fatty acid, insufficient activity, etc., To achieve the effect of mild conditions, simple operation process and shortened reaction time

Active Publication Date: 2014-11-26
DALIAN GLYCOBIO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there are many foods and health products about unsaturated fatty acids, but there are still some problems, such as the activity is not high enough; in addition, unsaturated fatty acids are generally not stable enough, and it is troublesome to use and store

Method used

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  • N-unsaturated fatty acid acylated chitosan oligosaccharide and preparation and application thereof
  • N-unsaturated fatty acid acylated chitosan oligosaccharide and preparation and application thereof
  • N-unsaturated fatty acid acylated chitosan oligosaccharide and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: the preparation of N-linoleic acid acylated chitosan oligosaccharide (ammonolysis method):

[0032] Dissolve 2.8g of linoleic acid in N,N-dimethylformamide (DMF), add 2.7g of p-nitrophenol, stir, add 0.1g of dimethylaminopyridine, dropwise add 2.06g of dicyclohexylcarbodiene Dissolve the imine in 5mL of DMF, react under heating conditions at 60-70°C for 2-6 hours after dripping, filter, pour the filtrate into ice water, precipitate white crystals, filter, and recrystallize with absolute ethanol to obtain linoleic acid p-Nitrophenyl ester 2.0g, aminolysis of ester:

[0033] Get 1.28g (3.2mmol) of p-nitrophenyl linoleate and dissolve it in 30mL of anhydrous dimethyl sulfoxide, and add 0.6g (3.1mmol) of chitosan oligosaccharide with a degree of polymerization of 2-8 (the mole of ester and oligosaccharide The ratio is 1-2:1 (calculated according to the glucosamine residue in chitosan oligosaccharide), react at 60-70°C for 4 hours, add ether / acetone solution 5...

Embodiment 2

[0036] Embodiment 2: the preparation of N-linoleic acid acylated chitosan oligosaccharide (one-step method)

[0037] Take 1.62g of chitosan oligosaccharide with a degree of polymerization of 2-15 and dissolve it in 30mL of N,N-dimethylformamide, then add 0.1g of dimethylaminopyridine, add 4mL of methanol; take 3.0g of linoleic acid and dissolve it in Add N,N-dimethylformamide to the above solution; after reacting at 60°C for 4 hours, add 5 times the volume of ethanol to the reaction solution to produce a large amount of yellow precipitate, suction filter, and filter the cake with anhydrous Wash with acetone for 3 times to obtain a yellow powder, which is vacuum-dried to obtain N-linoleic acid acylated chitosan oligosaccharide powder as a solid. The infrared data are identical or substantially identical to Example 1. The degree of substitution was determined to be 71% by nuclear magnetic resonance.

Embodiment 3

[0038] Embodiment 3: the preparation of N-eicosapentaenoic acid acylated chitosan oligosaccharide (one-step method)

[0039]Take 1.62g chitosan oligosaccharide and dissolve it in 30mL of N,N-dimethylformamide, then add 0.1g of dimethylaminopyridine, add 4mL of methanol; take 3.5g of linoleic acid and dissolve it in N,N-dimethylformamide Formamide was added to the above solution; after reacting at 60°C for 4 hours, 5 times the volume of ethanol was added to the reaction solution to produce a large amount of light yellow precipitate, which was filtered by suction, and the filter cake was washed 3 times with anhydrous acetone to obtain Yellow powder, vacuum-dried to obtain N-eicosapentaenoic acid acylated chitosan oligosaccharide powder solid. Infrared spectrum (KBr) main absorption peak (IRu, cm -1 ): 3580~3390 (OH, NH); 3095 (HC=CH) 2939; 2860 (CH+CH 2 ); 1705 (C=C); 1685 (amide-I band); 1650 (amide-II band); 1116, 1054, 1033 (C-O); 891 (β, C-H). Same; The degree of substitu...

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Abstract

The invention relates to N-unsaturated fatty acid acylated chitosan oligosaccharide and preparation and application thereof, which is a mixing component with the molecular weight of 800-15000Da. Degree of deacetylation of the mixing component is 50%-100%, degree of substitution of the N-unsaturated fatty acid acylated is 30-100%, the structure of the composition is shown in the description, wherein R is the N-unsaturated fatty acid acylated acyl group, hydrogen or CH3CO- with the carbon chain length of 12-22, and n is an integral between 0 and 30. The first glass N-unsaturated fatty acid acylated chitosan oligosaccharide can resist oxidant, delay senility, restrain tumour, resist inflammatory, reduce blood press, avoid thrombopoiesis, improve diabetes mellitus, regulate blood sugar level, resist atherosclerosis, promote plant grow and induce activity such as plant antiviral, and the first glass N-unsaturated fatty acid acylated chitosan oligosaccharide can serve as important raw materials of medicaments, health foods, cosmetics and biopesticide.

Description

technical field [0001] The invention relates to N-unsaturated fatty acid acylated chitosan oligosaccharide, specifically N-unsaturated fatty acid acylated chitosan oligosaccharide and its preparation method and application. Background technique [0002] Chitooligosaccharide, its structure is β-(1,4)-2-deoxy-2-glucosamine oligosaccharide. It is a rare alkaline oligosaccharide with special physical and chemical properties and excellent biological activity. Oligochitosan has the effects of lowering blood sugar, blood lipid, cholesterol, enhancing immune function, inhibiting tumors, anti-fatigue, delaying aging, antibacterial, antiviral, etc. It has been used in medicine, health food, cosmetics, agriculture, etc. . [0003] Unsaturated fatty acids are divided into monounsaturated fatty acids and polyunsaturated fatty acids according to the number of double bonds. Monounsaturated fatty acids refer to fatty acids with one double bond in the carbon chain. Polyunsaturated fatty ac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H5/06A61K31/722A61P9/12A61P3/10A61P35/00A61P9/10A01N43/16A01P21/00A01P1/00A23L1/09
Inventor 杜昱光刘启顺乔莹张红艳白雪芳崔刚
Owner DALIAN GLYCOBIO
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