Ferulic acid-cyclodextrin covalent coupling compound and its preparation method and application

A technology of covalent coupling and cyclodextrin, which is applied in the fields of medicine and food, can solve the problems of complex properties such as instability, loss, and damage of intermolecular forces, so as to retain antioxidant and biological activity and link stability , The effect of water solubility improvement

Active Publication Date: 2020-07-28
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] At present, studies have published that cyclodextrin-ferulic acid complexes are prepared by using cyclodextrins to entrap ferulic acid, and it has been confirmed that this complex acts through intermolecular forces such as van der Waals forces and hydrophobic interactions. Obtained, but the properties of this kind of complex are unstable. When the external temperature and pH environment change, the intermolecular force will be destroyed, thereby further releasing ferulic acid molecules, and losing the improvement of water solubility and enhanced stability. the goal of

Method used

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  • Ferulic acid-cyclodextrin covalent coupling compound and its preparation method and application
  • Ferulic acid-cyclodextrin covalent coupling compound and its preparation method and application
  • Ferulic acid-cyclodextrin covalent coupling compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1, the synthesis of the ferulic acid-cyclodextrin covalent coupling compound FA-CD-(I) connected by amide bond

[0060] β-cyclodextrin (20g, 17.6mmol) was suspended in 250mL of distilled water, and 10mL of aqueous solution containing NaOH (2.19g, 54.75mmol) was slowly added dropwise to the suspension using a constant pressure dropping funnel, and the whole process was carried out under ice bath conditions. After the solution was clarified after the dropwise addition, p-toluenesulfonyl chloride (5.04 g, 26.46 mmol) was dissolved in 15 mL of acetonitrile, and added dropwise to the above reaction system. After the system was reacted at room temperature for 2 hours, the precipitate was removed by filtration. The filtrate was adjusted to pH 6 with dilute hydrochloric acid, placed in a refrigerator at 4°C overnight, and the precipitate was collected by centrifugation. The precipitate was recrystallized twice in water, and the product mono-6-p-toluenesulfonyl-β-cyc...

Embodiment 2

[0068] Embodiment 2, the synthesis of conjugated product FA-CD (II)

[0069] The preparation method of mono-6-p-toluenesulfonyl-β-cyclodextrin is shown in Example 1.

[0070] Add mono-6-p-toluenesulfonyl-β-cyclodextrin (2.5g, 1.94mmol) into a round-bottomed flask containing 15mL of ethylenediamine, and react at 70°C for 8 hours under nitrogen protection. After the reaction, cool After reaching room temperature, the reaction solution was poured into a large amount of acetone to precipitate a precipitate, which was filtered and dried to obtain the product mono-6-ethylenediamine-β-cyclodextrin.

[0071] To a round bottom flask containing 20 mL of anhydrous DMF was added mono-6-ethylenediamine-β-cyclodextrin (1.177 g, 1 mmol), ferulic acid (0.233 g, 1.2 mmol), EDCI (0.575 g, 3 mmol) and HOBT (0.135g, 1mmol), stirred and reacted under ice bath for half an hour, then warmed up to room temperature, and stirred under nitrogen protection for 36h. After the reaction is complete, pour ...

Embodiment 3

[0075] Embodiment 3, the synthesis of conjugated product FA-CD (Ⅲ)

[0076]Take mono-6-p-toluenesulfonyl-β-cyclodextrin (2.0g, 1.55mmol) into a round-bottomed flask containing 8g of hexamethylenediamine, and react at 80°C for 8 hours under nitrogen protection. After the reaction, cool After reaching room temperature, the reaction solution was poured into a large amount of acetone to precipitate a precipitate, which was filtered and dried to obtain the product mono-6-hexamethylenediamine-β-cyclodextrin.

[0077] To a round bottom flask containing 20 mL of anhydrous DMF was added mono-6-hexanediamine-β-cyclodextrin (1.233 g, 1 mmol), ferulic acid (0.233 g, 1.2 mmol), EDCI (0.575 g, 3 mmol) and HOBT (0.135g, 1mmol), stirred under ice bath for half an hour, then raised to room temperature and stirred for 36h, after the reaction was completed, poured the reaction solution into 300mL acetone, precipitated, filtered, and dissolved the precipitate in a small amount of water and methan...

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Abstract

The invention discloses a ferulic acid-cyclodextrin covalent coupling compound as well as a preparation method and the application thereof. The ferulic acid-cyclodextrin covalent coupling compound hasa structural formula I as shown in the specification, in the formula I, M has a structural formula II as shown in the specification, and X is NH or O; in the formula II, m is an integer of 0-7; n isan integer of 1-8; the sum of m and n is 6, 7 or 8; R1, R2 and R3 are all OH, (CH2)x- or R4(CH2)y2-; at least one or R1, R2 and R3 is (CH2)x- or R4(CH2)y-; R4 is -NH- or x is an integer greater than or equal to 0; y is an integer greater than or equal to 0. The ferulic acid-cyclodextrin covalent coupling compound is applied to the preparation of at least one of anti-cancer drugs, fat-soluble drugcarriers, food additives and cosmetic packing. The ferulic acid-cyclodextrin covalent coupling compound disclosed by the invention is high in water solubility and good in stability, in addition, oxidation resistance of bioactivity of ferulic acid are maintained.

Description

technical field [0001] The invention relates to a ferulic acid-cyclodextrin covalently coupled compound and a preparation method and application thereof, belonging to the fields of medicine and food. Background technique [0002] Ferulic acid (FA for short) is a plant-derived phenolic acid, which has obvious biopharmacological activities such as anti-oxidation, free radical scavenging, anti-inflammatory and antibacterial, and can be used in the fields of medicine, food and cosmetics. However, due to its low water solubility and poor stability, it is easily oxidized after being exposed to air and ultraviolet rays, thus affecting its further use and development. The structural formula of ferulic acid is shown in formula 1. [0003] [0004] Cyclodextrin (CD for short) is a kind of cyclic oligosaccharide obtained by degrading starch under the action of cyclodextrin glycosyltransferase. The keys are formed end to end. According to the number of glucopyranose, it can be div...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/16
CPCC08B37/0012
Inventor 韩笑张国权江昊罗勤贵欧阳韶晖郑建梅
Owner NORTHWEST A & F UNIV
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