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Preparation method and application of hydroxyl cinnamyl ester type catechin

A technology of cinnamoyl ester type and catechin, applied in the field of natural medicinal chemistry, can solve the problems of inability to meet the reaction requirements, unable to complete the preparation, complex synthesis method and the like, and achieve the effects of easy implementation, low cost and simple preparation method

Active Publication Date: 2020-06-05
ANHUI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis method of this type of catechin disclosed in the prior art is complex and the reaction conditions are harsh, and the general laboratory conditions cannot meet the reaction requirements, and the preparation cannot be completed

Method used

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  • Preparation method and application of hydroxyl cinnamyl ester type catechin
  • Preparation method and application of hydroxyl cinnamyl ester type catechin
  • Preparation method and application of hydroxyl cinnamyl ester type catechin

Examples

Experimental program
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Effect test

Embodiment 1

[0066] Epigallocatechin transcoumarate, epicatechin transcaffeate, epigallocatechin transcoumarate and epigallocatechin transcaffeate hydroxycinnamoyl ester type The preparation of tea;

[0067] 1.1 Instruments and reagents

[0068] 1 H nuclear magnetic resonance spectrum adopts Agilent DD2600 MHz nuclear magnetic resonance instrument; mass spectrum adopts Agilent6465UPLC-Q-TOF-MS.

[0069] Epicatechin (EC) and epigallocatechin (EGC) were purchased from Chengdu Biopharmaceutical Co., Ltd. and Hubei Jusheng Technology Co., Ltd.; caffeic acid and p-coumaric acid were purchased from Anaiji Chemical; other reagents were Domestic analytically pure.

[0070] 1.2 Epicatechin trans-coumarate, epicatechin trans-caffeate, epigallocatechin trans-coumarate and epicatechin trans-caffeate hydroxycinnamoyl esters The synthesis route of tea is as follows figure 1 shown;

[0071] 1.3 Specific implementation methods:

[0072] Synthesis of compound 1a:

[0073] Weigh 1.16g (4.0mmol) of e...

Embodiment 2

[0113]The epicatechin trans-coumarate, epicatechin trans-caffeate, epigallocatechin trans-coumarate and epigallocatechin trans-caffeate prepared in Example 1 Four hydroxycinnamoyl catechins were tested for their inhibition of α-glucosidase activity in vitro.

[0114] 2.1 Experimental materials and reagents

[0115] Acarbose, potassium phosphate buffer (PPBS, 10mM, pH 6.9), α-glucosidase (0.1U·mL -1 ), 4-nitrophenyl-α-D-glucopyranoside (pNPG, 2.5mM), dimethylsulfoxide (DMSO)

[0116] 2.2 Experimental methods and results

[0117] Add 60 μL of α-glucosidase solution to a 96-well plate, add 60 μL of four hydroxycinnamoyl ester catechins with different concentration gradients, and pre-incubate at 37°C for 10 minutes, add 60 μL of pNPG solution respectively, and continue to After incubating at 37°C for 20 minutes, place it in a microplate reader (25°C), and record the A value of the reaction solution under visible light with a wavelength of 405nm. All samples were repeated 3 tim...

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Abstract

The invention relates to a preparation method and application of hydroxyl cinnamyl ester type catechins. The hydroxyl cinnamyl ester type catechins comprise four catechins which are respectively namedas epicatechin trans-coumarate, epicatechin trans-caffeic acid ester, epigallocatechin trans-coumarate and epigallocatechin trans-caffeic acid ester. The hydroxyl cinnamyl ester type catechins are prepared by the following steps: carrying out four steps of full acetylation on epicatechin and epigallocatechin, removal of acetyl on phenolic hydroxyl, silanizing of phenolic hydroxyl and removal of 3-acetyl, then respectively esterifying with acetylated caffeic acid or coumaric acid acyl chloride, and removing a protecting group. The preparation method of the four catechins is simple and mild inconditions, and can be completed under general experimental conditions. The four hydroxycinnamyl ester type catechins have a certain inhibition effect on the activity of alpha-glucosidase, can be usedfor hypoglycemic drugs, and have important significance in the fields of agriculture and medicine.

Description

technical field [0001] The invention belongs to the technical field of natural medicinal chemistry, and specifically relates to four kinds of drugs named respectively epicatechin trans coumarate, epicatechin trans caffeate, epigallocatechin trans coumarate and epigallocatechin trans coumarate and epigallocatechin The preparation method and application of the hydroxycinnamoyl ester type catechin of gallocatechin trans-caffeate. Background technique [0002] Tea is rich in tea polyphenols, accounting for 18%-36% of the dry matter of tea. Among them, most of them are catechins (flavanols), accounting for 12%-24% of the dry matter of tea leaves. Studies have shown that catechin is an important taste substance in tea. Moreover, catechins also have pharmacological functions such as anti-inflammatory, anti-oxidation, anti-cancer, cardiovascular and neuroprotective effects. [0003] Chemical synthesis experiments usually require special reaction conditions, and the pharmaceutical...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/62A61P3/10A61K31/353
CPCC07D311/62A61P3/10C07B2200/07Y02P20/55
Inventor 鲍官虎王威
Owner ANHUI AGRICULTURAL UNIVERSITY
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