Application of four kinds of kaurane diterpene compounds in the preparation of glycosidase inhibitor drugs

A glycosidase inhibitor, a kaurine-type technology is applied to the application field of four kaurane diterpenoid compounds in the preparation of glycosidase inhibitor drugs, achieving the effects of abundant sources, high safety, and easy operation in the preparation process

Active Publication Date: 2016-03-30
SOUTH CHINA BOTANICAL GARDEN CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Compounds 3α-hydroxy-ent-kauran-19-oicacid (1), 3α-tigloyloxy-9β-hydroxy-ent-kaur-16-en-19-oicacid (2), 3α-cinnamoyloxy-ent-kaur-16-en -19-oicacid (3), 3α-cinnamoyloxy-9β-hydroxy-ent-kaur-16-en-19-oicacid (4) are all kaurane diterpene compounds, these compounds have been obtained from the Compositae plant Wedelia trilobata (Wedelia trilobata (L.) Hitchc) (Qiangetal., HelveticaChimicaActa2011,94:817-823; Bohlmannetal., Phytochemistry1981,20:751-756; Maetal., Natural Products and Bioprospecting, 2013,3:107-111), its chemical structure is as follows Formula (I), but so far there is no research report that it has glycosidase inhibitor activity

Method used

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  • Application of four kinds of kaurane diterpene compounds in the preparation of glycosidase inhibitor drugs
  • Application of four kinds of kaurane diterpene compounds in the preparation of glycosidase inhibitor drugs
  • Application of four kinds of kaurane diterpene compounds in the preparation of glycosidase inhibitor drugs

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Example 1: Preparation of four diterpene compounds in Wedelia chinensis

[0018] 1.1 Plant source and identification

[0019] The plant material for extraction, Sphagneticolatrilobata (L.) Pruski plant samples were collected from the South China Botanical Garden in Guangdong Province in September 2009, and were identified by researcher Xing Fuwu, South China Botanical Garden, Chinese Academy of Sciences.

[0020] 1.2 Extraction and separation

[0021] The whole South American Wedelia chrysanthemum plant (dry weight 2kg) is smashed and extracted with 95% ethanol at room temperature for 3 times, 2 days each time, and the extracts are combined; the ethanol in the extract is drained by vacuum concentration and an appropriate amount of water is added to make It became a suspension and was extracted with petroleum ether 4 times; a petroleum ether fraction (45 g) was obtained after concentration under reduced pressure. The obtained petroleum ether extraction part (45g) was subjected ...

Embodiment 2

[0026] Example 2: Detection of α-glycosidase inhibitory activity of the four diterpene compounds

[0027] 2.1 Instruments and reagents

[0028] Experimental instrument: microplate reader Genoismicroplatereader (TecanGENios, Swizerland)

[0029] Reagent samples: α-glucosidase was purchased from Sigma Chemical Co. (Sigma-Aldrich, St. Louis, USA); Acarbose was purchased from Tokyo Chemical Industry Co., Ltd. (Japan); 4-nitrophenol-α- D-glucopyranoside (PNPG) was purchased from Tokyo Chemical Industry Co., Ltd. (Japan); four diterpene compounds α-hydroxy-ent-kauran-19-oicacid (compound 1), 3α-tigloyloxy-9β-hydroxy-ent -kaur-16-en-19-oicacid (compound 2), 3α-cinnamoyloxy-ent-kaur-16-en-19-oicacid (compound 3), 3α-cinnamoyloxy-9β-hydroxy-ent-kaur-16-en -19-oicacid (compound 4) is prepared by the above experimental example 1 or can also refer to the literature Qiangetal., Helvetica Chimica Acta 2011, 94: 817-823; Bohlmannetal., Phytochemistry 1981, 20: 751-756; Maetal., Natural Products a...

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Abstract

The invention provides applications of four kaurane diterpene compounds in preparation of glycosidase inhibitor medicines. The four compounds capable of highly inhibiting alpha-glycosidase activity are natural compounds which are high in safety and capable of rapid natural degradation without residue in the environment. The four compounds are obtained by separation from wedelia trilobata, and other plant materials. The plant materials are rich in source. A preparation process is easy in operation. Monomers of the four compounds are stable and liable to store. The alpha-glucosidase inhibition activity of the four compounds is obviously higher than or equivalent to that of acarbose that is a clinic medicine. The four compounds are extremely likely developed into effective and safe alpha-glucosidase inhibitor medicines used for preventing and treating type II diabetes, and have good prospects.

Description

Technical field [0001] The invention belongs to the field of natural medicinal chemistry, and specifically relates to four kaurane diterpene compounds 3α-hydroxy-ent-kauran-19-oicacid(1), 3α-tigloyloxy-9β-hydroxy-ent-kaur-16-en-19 -oicacid(2), 3α-cinnamoyloxy-ent-kaur-16-en-19-oicacid(3), 3α-cinnamoyloxy-9β-hydroxy-ent-kaur-16-en-19-oicacid(4) or its The use of medicinal salts in the preparation of glycosidase inhibitors or medicines. Background of the invention [0002] Diabetes mellitus is a common clinical endocrine and metabolic disorder. It has an important correlation with the annual high incidence of cardiovascular diseases and cancer, and is an important killer of human health. At present, the incidence of diabetes is increasing on a global scale. In my country, the incidence of diabetes is more than 100 million people, and it is showing an increasing trend year by year. Diabetes is causing more and more losses to the health of our people and the national economy. [000...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/19A61K31/22A61K31/216A61P3/10
Inventor 谭建文任慧周忠玉徐巧林董丽梅
Owner SOUTH CHINA BOTANICAL GARDEN CHINESE ACADEMY OF SCI
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