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Use of trisubstituted benzopyranones

A technology of use and extract, applied in the field of tri-substituted benzopyrones, can solve the problems of continuous formation of harmful

Inactive Publication Date: 2007-09-26
DR VILMAR SHVABE GMBKH EHND KO KG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, respiratory bursts are a fundamentally required response in defense against infection, and the increased and continuous formation of ROS is often detrimental because oxidative attack is not limited to invading microorganisms, but the body's own tissues may also be exposed to their toxicity

Method used

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  • Use of trisubstituted benzopyranones
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  • Use of trisubstituted benzopyranones

Examples

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example 1

[0038] Example 1: Preparation of 6,7,8-trihydroxy-2H-1-benzopyran-2-one (compound II)

[0039] At 40 to 50°C, 20g (42.7mmol) of 6,8-bis(sulfoxy)-7-hydroxyl-2H-1-benzopyran-2-one potassium salt was stirred in 480ml of about 2N hydrochloric acid for 20h . After cooling, the precipitated crude product is filtered and recrystallized from water (hot filtration). The crystals were filtered, washed and dried in vacuo at 100°C: 5.9 g (71%), melting point: decomposition started at 260°C; 1 H and 13 CNMR follows the instructions of O. Kayser and H. Kolodziej (Phytochemistry 39, 1181-1135 (1995)).

example 2

[0040] Example 2: Isolation and structure determination of 6,8-bis(sulfoxy)-7-hydroxy-2H-1-benzopyran-2-one potassium salt (potassium salt of compound III)

[0041] 15 kg of ground roots of Pelargonium sidoides were percolated twice with 75 1 and 40 1 of water respectively at room temperature. The aqueous extract was concentrated to about 1 / 3, 7 kg of ammonium sulfate was added thereto and extracted several times with a 3 / 2 mixture of 2-butanone / ethanol. The organic phases were combined and concentrated by evaporation.

[0042] The residue was chromatographed on a HP20 column (eluent: water). The 6,8-bis(sulfoxy)-7-hydroxy-2H-1-chromen-2-one fraction was concentrated, adjusted to pH 8 with potassium hydroxide solution and diluted with ethanol at a ratio of 1 / 1 . The precipitate was filtered and suspended in water. The pH was adjusted to 10.7 with potassium hydroxide solution and diluted with ethanol at a ratio of 1 / 1. The precipitate thus settled was redissolved in hot wa...

example 3

[0049] Example 3: Plant extract with a certain content of 6,8-bis(sulfoxy)-7-hydroxyl-2H-1-benzopyran-2-one (compound III)

[0050] 500 g of ground roots of Pelargonium sidoides were extracted with 3 kg of water over 4 h at room temperature. The extracted plant material was filtered and extracted once more with 2 kg of water and filtered as above. The filtrates were combined, concentrated at about 35°C and lyophilized: 58.7 g (11.7%) of dry extracts, of which the content of compound III was 1.54%.

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Abstract

The invention relates to the use of trisubstituted benzopyranones in the treatment or prophylaxis of pathological conditions that are related to oxidative stress and / or inflammatory reactions, to novel trisubstituted benzopyranones and to the physiologically acceptable salts thereof. The invention also relates to plant extracts, drugs, dietetic food and pharmaceutical preparations containing said compounds.

Description

technical field [0001] The present invention relates to the use of trisubstituted benzopyrone for the treatment or prevention of pathological conditions associated with oxidative stress and / or inflammatory responses, and to novel trisubstituted benzopyrone and its physiologically acceptable Salt. The invention further relates to plant extracts, medicaments, therapeutic foods and pharmaceutical preparations. Background technique [0002] Free radicals are atoms or molecules that have unpaired electrons in their outer orbitals. For biological processes, the most important free radical is molecular oxygen, which can be reduced to form different metabolites. Such metabolites are generally summarized under the collective term "reactive oxygen species" (ROS). Examples of ROS include peroxide anion, hydroxyl radical, hydrogen peroxide, peroxide anion, singlet oxygen, hypochlorite, nitrogen oxide, and peroxynitrite. [0003] ROS are naturally formed by various biological process...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/18A61K31/352A23L33/00
CPCC07D311/18C07D311/14A61K31/352C07D311/16A23L1/3002A23L33/105A61P1/04A61P1/16A61P11/06A61P17/06A61P19/02A61P25/00A61P25/16A61P25/28A61P27/12A61P29/00A61P3/10A61P31/00A61P31/04A61P31/16A61P31/18A61P33/00A61P35/00A61P39/06A61P43/00A61P9/10C07D311/08
Inventor 斯得凡·桔门荷尔曼·休格伊哥·酷克卡尔·斯哥芝
Owner DR VILMAR SHVABE GMBKH EHND KO KG
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