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Novel derivative of conjugate polyenoic fatty acid polyol ester, macrogol ester and sugar ester and application thereof

A technology of conjugated polyene fatty acid and polyethylene glycol ester, which can be used in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of poor oxidative stability, inapplicability, loss of anticancer activity, etc. Effects of improved oxidative stability, improved stability, and strong anticancer activity

Inactive Publication Date: 2012-07-18
HENAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the huge disadvantage of this method is that the anti-cancer activity of antioxidants is almost lost while improving their stability[4]
[0004] However, none of these existing methods are suitable for the above-mentioned conjugated polyene fatty acids with extremely poor oxidation stability, so it is necessary to develop new methods to improve stability while retaining their strong anticancer activity

Method used

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  • Novel derivative of conjugate polyenoic fatty acid polyol ester, macrogol ester and sugar ester and application thereof
  • Novel derivative of conjugate polyenoic fatty acid polyol ester, macrogol ester and sugar ester and application thereof
  • Novel derivative of conjugate polyenoic fatty acid polyol ester, macrogol ester and sugar ester and application thereof

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Experimental program
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Effect test

Embodiment 1

[0029] Embodiment 1: glyceryl punicate

[0030] Dissolve punicic acid (1 mol) and glycerol (2 mol) in dichloromethane, add dicyclohexylcarbodiimide (0.5 mol) and pyridine (1 mL), fill with N2 and seal, then stir and react at 15°C for 24 hours. After the reaction, the filtrate was collected, washed 5 times with 1.0 mol / L dilute sulfuric acid aqueous solution, and the upper dichloromethane phase was collected. After concentrated by rotary evaporation, the product glyceryl punicate was separated by TLC thin plate (n-hexane:chloroform=10:1). The infrared spectrum and hydrogen nuclear magnetic resonance spectrum of the derivative are as follows: figure 1 , as shown in 2. The oxidation stability curves of free punicic acid and glyceryl punicate derivatives in air at 50°C are as follows: image 3 The results received show that the stability of glyceryl punicate derivatives is greatly improved compared to free punicic acid. Glyceryl punicate was added to RPMI1640 cell culture medi...

Embodiment 2

[0031] Embodiment 2: β-cartoic acid macrogol 400 ester

[0032] Dissolve β-carboric acid (2mol) and polyethylene glycol 400 (1mol) in ethyl acetate, add 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (1.5mol) and dimethylamine (0.5 mL), filled with N2 and sealed, then stirred and reacted at 35° C. for 18 hours. After the reaction, the filtrate was collected, washed 5 times with 1.5 mol / L dilute sulfuric acid aqueous solution, and the upper ethyl acetate phase was collected. After concentrated by rotary evaporation, the product was separated by TLC thin plate (n-hexane:chloroform=8:2.1) to obtain the product β-caryoic acid polyethylene glycol 400 ester. The infrared spectrum and hydrogen nuclear magnetic resonance spectrum of the derivative are as follows: Figure 5 , as shown in 6. The oxidation stability curves of free β-caryoic acid and β-cartoic acid polyethylene glycol 400 ester derivatives in air at 50°C are as follows: Figure 7 The results received show that the β-c...

Embodiment 3

[0033] Embodiment 3: cis-PnA sucrose ester

[0034] Dissolve cis-PnA (5 mol) and sucrose (1 mol) in DMF, add diisopropylcarbodiimide (3.2 mol) and triethylamine (1 mL), fill with N2 and seal, then stir the reaction at 45°C for 48 Hour. After the reaction, the filtrate was collected and washed 5 times with 1.5 mol / L dilute sulfuric acid aqueous solution. The crude product was extracted by adding dichloromethane, concentrated by rotary evaporation, and separated by TLC thin plate (n-hexane: chloroform = 6: 2.9) to obtain the product cis-PnA sucrose ester. The infrared spectrum and hydrogen nuclear magnetic resonance spectrum of the derivative are as follows: Figure 9 , as shown in 10. The oxidation stability curves of free cis-PnA and cis-PnA sucrose ester derivatives in air at 50°C are as follows Figure 11 The results received show that the stability of cis-PnA sucrose ester derivatives is greatly improved compared to free punicic acid. Add cis-PnA sucrose ester to RPMI1...

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Abstract

The invention relates to a novel derivative of conjugate polyenoic fatty acid polyol ester, macrogol ester and sugar ester and an application thereof. A plurality of conjugate polyenoic fatty acids have biological activities of cancer resistance, blood fat reduction, blood sugar reduction and the like, so that the conjugate polyenoic fatty acids receive much concern. However, the extremely easy oxidation characteristics of the polyenoic fatty acids are extremely unbeneficial to the applications of the polyenoic fatty acids. The novel derivative provided by the invention is an ester derivative which is synthesized by treating a plurality of conjugate polyenoic fatty acids, polylol, polyethyleneglycol and sugar molecules serving as raw materials with a catalytic dehydration method and has high oxidation stability and high anticancer activity. Compared with free conjugate polyenoic fatty acids, the novel ester derivative provided by the invention has the advantages that: the oxidation stability of the novel ester derivative is enhanced greatly, the novel ester derivative can be taken as a food additive and a nutrition enhancer, and the shelf life of a conjugate polyenoic fatty acid product is prolonged. More importantly, high anticancer activity of the derivative is kept while the oxidation stability is enhanced, and the derivative can be taken as a novel anticancer medicament and has a wide application prospect.

Description

technical field [0001] The invention relates to novel conjugated polyene fatty acid polyol esters, polyethylene glycol esters, sugar ester derivatives and uses thereof. Background technique [0002] A variety of conjugated polyene fatty acids, such as conjugated octadecatrienoic acid (also known as conjugated linolenic acid, Conjugated linolenic acid, CLnA), conjugated octadecatetraenoic acid (also known as Parilla oleic acid, Parinaric acid, PnA), conjugated docosahexenoic acid (Conjugated Docosahexenoic Acid; CDHA), conjugated eicosapentaenoic acid (Conjugated Eicosapentemacnioc Acid, CEPA), etc. For example, they have a strong preventive and therapeutic effect on malignant tumors such as breast cancer, liver cancer, gastric cancer, and neuroma, which has caused a research boom [1]. However, the above-mentioned conjugated polyene fatty acids are extremely easy to be oxidized. For example, our research group found that in the air at 50°C, it only takes 20 hours for the co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/587C07C67/08C08G65/48C07H13/06C07H1/00A61K31/7024A61K31/25A61K31/22A61P35/00
Inventor 王华杰余学红和明莉曹莹曹翠张延华杨林
Owner HENAN NORMAL UNIV
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