Flavanol-menthane heterozygote as well as pharmaceutical composition, preparation method and application thereof

A flavanol and menthane technology, applied in the field of flavanol-menthane hybrids, can solve the problem of no compound

Active Publication Date: 2020-09-25
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there are no reports of A–H (amomutsaokins A–H, 1~8) in the prior art, and no reports of compounds 1~8 and their pharmaceutical com

Method used

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  • Flavanol-menthane heterozygote as well as pharmaceutical composition, preparation method and application thereof
  • Flavanol-menthane heterozygote as well as pharmaceutical composition, preparation method and application thereof
  • Flavanol-menthane heterozygote as well as pharmaceutical composition, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of Compounds 1-8:

[0030] The dried fruit of Cao Guo was crushed and extracted three times with 50% ethanol under reflux for 2 hours each time. The ethanol extracts were combined, and the ethanol was recovered under reduced pressure to obtain the extract. The extract was dispersed in water and extracted with ethyl acetate, then concentrated to the ethyl acetate extract. Then the ethyl acetate fraction (Fr.A) was subjected to silica gel column chromatography, eluting with methanol-chloroform (0:100, 5:95, 10:90, 20:80 and 40:60, v / v) Seven fractions of Fr.A-1~Fr.A-7 were obtained by gradient elution of reagents. Fraction Fr.A-6 was subjected to MCI CHP 20P gel column chromatography (methanol-water, 40:60, 60:40, 80:20 and 100:0) to obtain four subfractions Fr.A-6-1~Fr.A-6-4. Fr.A-6-2 was subjected to silica gel column chromatography (MeOH-CHCl 3 , 2:98) to obtain three subfractions Fr.A-6-2-1 ~ Fr.A-6-2-2. Fr.A-6-2-2 (2.2g) was purified by Sephadex LH-20...

Embodiment 2

[0127] PTP1B and α-glucosidase inhibitory activity

[0128] 1 Materials and methods

[0129] 1.1 Materials

[0130] α-glucosidase (Sigma Aldrich, St.Louis, MO, USA); phosphate buffer (≥99%, Meilun Bio, Dalian); p-nitrophenyl-α-D-glucopyranose (≥99%) %, Yuanye Biology, Shanghai); acarbose (≥98%, Bayer Pharmaceuticals, Beijing); PTP1B (protein tyrosine phosphatase) was purchased from Sino Biological (Wayne, PA, USA); suramin sodium was purchased from From ACROS (New Jersey USA)

[0131] 1.2 Instruments

[0132] Flex Station 3 desktop multifunctional microplate reader (Bio-RAD 680, USA); analytical balance (AG135, Metler Toledo, China); thermostat box (DHP-9082, Shanghai).

[0133] 1.3 Experimental process

[0134] PTP1B inhibitory activity was performed according to the inventors' previous studies. Briefly, the working buffer (workingbuffer, WB) was composed of 3-(N-morpholino)propanesulfonic acid (MOPS, 722.02mg), dithiothreitol (DTT, 30mg), EDTA (25.7mg), It is prepared...

preparation Embodiment 1～8

[0146] In the following preparation examples, conventional reagents are selected, and preparations are prepared according to existing conventional methods. This example only reflects that at least one of the compounds 1 to 8 of the present invention can be prepared into different preparations. Specific reagents and The operation is not specifically limited:

[0147] 1. After dissolving at least one of the compounds 1 to 8 prepared in Example 1 with DMSO, add water for injection according to a conventional method, fine filter, potting and sterilizing to make an injection, and the concentration of the injection is 0.5 ~5 mg / mL.

[0148] 2. After dissolving at least one of the compounds 1 to 8 prepared in Example 1 with DMSO, dissolve it in sterile water for injection, stir to dissolve it, filter it with a sterile suction filter funnel, and then sterilize it. filtered, divided into ampoules, freeze-dried at low temperature and sealed aseptically to obtain a powder injection.

...

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Abstract

The invention provides eight new flavanol-menthane polymers shown as a structural formula (I), namely amomutsaokins A-H (compounds 1-8), a preparation method, a pharmaceutical composition and application thereof, and relates to the technical field of medicines. The provided compounds have obvious inhibitory activity on PTP1B and alpha-glucosidase, can form a pharmaceutical composition with a medicinal carrier or excipient, and can be used for preparing PTP1B and alpha-glucosidase inhibitor drugs, hypoglycemic drugs or health foods.

Description

Technical field: [0001] The invention belongs to the technical field of medicines. Specifically, it involves 8 new flavanol-menthane hybrids, amomutsaokins A-H (amomutsaokins A-H, 1-8), their preparation methods and applications, pharmaceutical compositions and their applications. Background technique: [0002] Type 2 diabetes is a chronic metabolic disease whose prevalence increases with age worldwide and is characterized by hyperglycemia, insulin resistance, and relative insulin deficiency. The etiology of type 2 diabetes is complex but is generally thought to be related to genetics and lifestyle-related factors such as obesity, physical activity, diet and stress. Postprandial hyperglycemia, as one of the two indicators of chronic hyperglycemia in the diagnosis of type 2 diabetes, is the main factor leading to the onset and development of type 2 diabetes. The occurrence of postprandial hyperglycemia is mainly due to the rapid absorption of glucose in the intestine, and α...

Claims

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Application Information

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IPC IPC(8): C07D493/18C07D493/08A61K31/352A61P3/10A23L33/105
CPCC07D493/18C07D493/08A61P3/10A23L33/105C07B2200/07A23V2002/00A23V2200/328A23V2250/2132
Inventor 耿长安何小凤陈纪军胡敬李天泽黄晓燕马云保张雪梅
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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