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Five ent-atisane type diterpenoid compounds derived from euphorbia antiquorum and preparation method and application of ent-atisane type diterpenoid compounds

A compound, the technology of Huoyele, which is applied in the field of diterpenoids and its preparation, can solve the problems of surrounding tissue and cell damage

Active Publication Date: 2020-07-28
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The cytotoxicity of excess NO is non-specific, not only targeting microorganisms, but also causing damage to surrounding tissues and cells

Method used

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  • Five ent-atisane type diterpenoid compounds derived from euphorbia antiquorum and preparation method and application of ent-atisane type diterpenoid compounds
  • Five ent-atisane type diterpenoid compounds derived from euphorbia antiquorum and preparation method and application of ent-atisane type diterpenoid compounds
  • Five ent-atisane type diterpenoid compounds derived from euphorbia antiquorum and preparation method and application of ent-atisane type diterpenoid compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] (1) 11.5 kg of Huoyele stems were extracted with methanol three times (amount of 3 × 60 L), and the extract was recovered under reduced pressure to obtain a crude extract;

[0046] (2) Add water to the methanol extract obtained in step (1) to make a suspension, and extract with ethyl acetate and petroleum ether respectively to obtain ethyl acetate and petroleum ether extracts;

[0047] (3) Step (2) The petroleum ether extract was separated by silica gel column chromatography, followed by petroleum ether: acetone 100:0, 100:2, 100:4, 100:6, 100:8, 100:11, 100:16, 100:23, 100:30 elution;

[0048] (3) The petroleum ether:acetone 100:2~100:23 fraction obtained in the above step (2) is separated by medium pressure liquid chromatography (MPLC), using methanol / water 6:4~9:1 as the mobile phase gradient Elution;

[0049] (4) The methanol / water (6:4) and (8:2) fractions obtained in the above step (3) were separated by HPLC-RI and eluted with methanol / water 60:40-90:10 as the m...

Embodiment 2

[0067] (1) 8.0 kg of Huoyele whole herb was extracted 3 times with ethanol (amount of 3×48 L), and the extract was recovered under reduced pressure to obtain a crude extract;

[0068] (2) The ethanol extract obtained in step (1) is added with water to make a suspension, and extracted with ethyl acetate to obtain the ethyl acetate extract;

[0069] (3) Step (2) is separated by silica gel column chromatography, and eluted with petroleum ether: acetone 100:4, 100:6, 100:8, 100:11, 100:16, 100:23, 100:30 in sequence;

[0070] (3) Petroleum ether obtained in the above step (2): ethyl acetate 100:2~100:23 fractions are separated by medium pressure liquid chromatography (MPLC), using methanol / water 7:3~9:1 as the flow Phase gradient elution;

[0071] (4) The methanol / water (8:2) fraction obtained in the above step (3) was separated by HPLC-RI, and the new compound 1 was obtained by eluting with methanol / water 70:30~90:10 as mobile phase (yield 0.001 %), 2 (0.002% yield), 3 (0.003% ...

Embodiment 3

[0074] (1) 8.0 kg of Huoyele whole herb was extracted 3 times with acetone (amount of 3 × 48 L), and the extract was recovered under reduced pressure to obtain a crude extract;

[0075] (2) Add water to the acetone extract obtained in step (1) to make a suspension, and extract with dichloromethane to obtain a dichloromethane extract;

[0076] (3) Step (2) is separated by silica gel column chromatography, and eluted with petroleum ether: acetone 100:4, 100:6, 100:8, 100:11, 100:16, 100:23, 100:30 in sequence;

[0077] (3) The petroleum ether:acetone 100:2~100:23 fraction obtained in the above step (2) is separated by medium pressure liquid chromatography (MPLC), using methanol / water 7:3~9:1 as the mobile phase gradient Elution;

[0078] (4) The methanol / water (8:2) fraction obtained in the above step (3) was separated by HPLC-RI and eluted with acetonitrile / water 70:30-90:10 as the mobile phase to obtain the new compound 1 (yield 0.001 %), 2 (0.001% yield), 3 (0.003% yield), ...

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Abstract

The invention relates to structures of five new ent-atisane diterpenoid compounds (1-5), a preparation method and application of the five new ent-atisane diterpenoid compounds (1-5) in anti-inflammatory and neurodegenerative disease treatment drugs. The new compounds (1-5) have the following structures as shown in the specification. The five new compounds provided by the invention have NO inhibition and nerve axon growth promotion activity, and can be used for development and application of anti-inflammatory and neurodegenerative disease treatment drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a new diterpenoid compound in Huoyele and its preparation method and application. Background technique [0002] NO (Nitric oxide) is an important messenger molecule, which plays a key role in various physiological and biochemical processes and has a miraculous physiological regulation function. In many tissues, although the real release amount is still difficult to detect, different concentrations of NO have been clearly released, and the change of the concentration is closely related to the physiological function of the body. Many diseases, including inflammation, neurodegenerative diseases, cancer, etc., may be caused by abnormal release or regulation of NO. [0003] During an inflammatory response, inflammatory mediators or inflammatory substances can induce or increase the synthesis and release of local NO, and the release of NO can induce the production of pro-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/145C07C69/16C07C69/24C07C69/533C07C67/48C07C67/56C07C67/58C07C49/743C07C45/78C07C45/79C07C45/80A61P29/00A61P25/28A61K31/22A61K31/122
CPCC07C69/145C07C69/16C07C69/24C07C69/533C07C67/48C07C67/56C07C67/58C07C49/743C07C45/78C07C45/79C07C45/80A61P29/00A61P25/28C07C2603/86C07B2200/07
Inventor 郭远强许婧梁月石照宇安莉君
Owner NANKAI UNIV
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