Flavane compound, preparation method thereof and hypoglycemic activity

A compound and flavan technology, applied in the field of medicine, can solve the problems of immature research, complex structure, and difficult purification of monomer compounds.

Active Publication Date: 2015-11-25
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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Problems solved by technology

[0004] Flavans and their polymers are a class of chemical components that widely exist in traditional medicinal plants. The results of pharmacological activity studies show that flavans have hypoglycemic, neuroprotective, antioxidant, antibacterial, antiviral, and anti-inflammatory properties. However, although the activity of flavan polymers has been reported in recent years, its research is not yet mature, and its structure is complex, and monomer compounds are not easy to purify
It has been reported in the literature that flavan polymers can be degraded by thiolysis to obtain flavan derivatives that are thiolated at the 4-position. However, due to the complexity of the product, it is not easy to separate and purify. Less derivatives substituted by heteroatoms
[0005] On the basis of the previous research of this project, it was found that the polymerization unit of the flavan polymer in Rhodiola rosea is relatively simple, and the 3-position of its flavan is acylated by gall, and the product after thiolysis is relatively simple, which is easy to separate and purify. The pharmacological activity of such flavan derivatives has been reported, so this kind of polymer was further derivatized and synthesized to obtain a series of thio derivatives with flavan as the core, and their antidiabetic activity was tested Evaluation, pharmacological results show that these derivatives have good α-glucosidase inhibitory activity, in terms of the impact on the oral sucrose tolerance of mice, similar to the effect of acarbose, flavan derivatives JP-3, JP -7, JP-12, JP-16, JP-22, JP-47 can significantly reduce the blood sugar rise after sucrose loading in normal mice, and significantly reduce the AUC value of the area under the blood sugar-time curve

Method used

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  • Flavane compound, preparation method thereof and hypoglycemic activity
  • Flavane compound, preparation method thereof and hypoglycemic activity
  • Flavane compound, preparation method thereof and hypoglycemic activity

Examples

Experimental program
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Effect test

preparation example 1

[0103] The extraction of preparation example 1 flavan polymer part

[0104] The extracting of this part refers to the Chinese patent before, and the application number is the extraction method of the effective part of Rhodiola rosea of ​​201010587820.7, collect each 20kg of Rhodiola rosea and Rhodiola angustifolia, concentrate after 3 times of 80% ethanol extraction, obtain extract, and then Add distilled water with a mass ratio of 10 times the amount to the extract and let it stand for 96 hours at about 10°C. After the supernatant is concentrated, the macroporous resin is separated through four gradients of water, 5% ethanol, 50% ethanol, and 95% ethanol in sequence. The 50% water-ethanol fraction was concentrated and freeze-dried to obtain two fractions rich in different types of flavan polymers.

preparation example 2

[0105] The preparation of preparation example 2 flavan derivatives

[0106] Take a certain amount of flavan polymer parts of Dahua or Rhodiola angustifolia, dissolve it in anhydrous methanol according to the mass ratio of 1:30, and add the corresponding thio reagent according to the mass ratio of 1:0.5, and the mass ratio of 1 Add 48% HBr aqueous solution at a ratio of 0.5, react at 60°C for 4h, suspend the reaction solution with distilled water with a mass ratio of 5:1 to the reaction solution, extract 3 times with ethyl acetate, combine the organic layers, and organic After the layer was dried and concentrated under reduced pressure, the 200-300 mesh silica gel column separation and LH-20 column chromatography separation were carried out in sequence, and the methanol aqueous solution with a mass fraction of 30-70% was used to efficiently prepare the liquid phase to obtain the 4-position thio-substituted flavan derivative At present, a total of 51 new compounds are obtained, ...

Embodiment 14

[0116] Example 14- Preparation of (S)-(2,4-dichlorobenzylthio)-epicatechin gallate (JP-1)

[0117] The preparation method is the same as that of Preparation Example 2, the flavan polymer raw material used is 50% part of Rhodiola rosea, and the 2,4-dichlorobenzylthiol used as the thio reagent is used to efficiently prepare 70% of the liquid phase (MeOH / H 2 (2 volume ratio) to obtain compound JP-1, light red powder, yield 32.1%. The NMR data of the compound are as follows:

[0118] (c0.1MeOH); HR-ESI-MS (m / z633.0386[M+H] + ,calcd,633.0383); 1 HNMR (500MHz, DMSO-d 6 )δ: 7.65 (1H, s, 3″’-H), 7.62 (1H, dd, J=8.0, 1.5, 5″’-H), 7.41 (1H, d, J=8.0, 6″’-H ),6.87(1H,d,J=1.5,2′-H),6.82(2H,s,2″,6″-H),6.72(1H,dd,J=8.0,1.5,6′-H) ,6.68(1H,d,J=8.0,5′-H),5.91(1H,d,J=2.0,8-H),5.83(1H,d,J=2.0,6-H),5.44(1H ,s,3-H),5.27(1H,s,2-H),4.12(1H,s,4-H),4.10(2H,s,S-C-H); 13 CNMR (125MHz, DMSO-d 6 )δ: 165.2(O-C-O), 158.1(C-5), 157.2(C-7), 155.4(C-9), 145.4(C-3″,5″), 144.9(C-3′,4′) ,138.9(C-4″),13...

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Abstract

The invention discloses a flavane compound shown in a formula I, a preparation method thereof and an application of medicine and health product for treating and/or preventing obesity and diabetes and abnormal glucose tolerance. The flavane compound is obtained from a flavane polymer (taking ECG as a polymerization unit) in rhodiola crenulata and the flavane polymer (taking EGCG as the polymerization unit) in rhodiola kirilowii through derivatization of a thiolysis reagent connected to different functional groups. The pharmacological result displays the flavane compound has good pharmacological effect on the hypoglycemic aspect.

Description

technical field [0001] The invention relates to the technical field of medicine, a class of flavan compounds, a preparation method thereof and its use in anti-diabetic drugs and health care products. Background technique [0002] Diabetes is a common endocrine and metabolic disorder. Diabetes and its complications are major diseases that threaten human health. The mortality rate is second only to tumors and cardiovascular diseases. At present, the pathogenesis of diabetic vascular disease has not been fully determined, and the main theories include non-enzymatic glycochemistry theory, oxidative stress theory and Xinhao conduction theory. The hypoglycemic drugs currently on the market are mainly divided into the following types: α-glucosidase inhibitors, thiazolidinones, biguanides, sulfonylureas, repaglinides, dipeptidyl peptidase-4 inhibitors They all show different toxic and side effects, and the more typical pioglitazone is the thiazolidinone class, which is currently ba...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/32C07D311/40C07D405/12C07D407/12A61K31/353A61K31/506A61P3/10A61P3/04A23L1/29A23L33/00
Inventor 张培成叶菲杨桠楠田金英贠菊平张晓琳冯子明黄立伟姜建双李莫涵安亚文唐冉琪
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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