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Isoflavone derivative, its production and use as antioxidant

A technology of isoflavones and derivatives, applied in the field of new water-soluble antioxidants, can solve the problems of poor water-solubility and fat-solubility, slow absorption, troublesome extraction, etc.

Inactive Publication Date: 2007-06-20
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the existing drugs that can be used as antioxidants are mainly some natural products such as the extracts of Danshen and Angelica. There are some disadvantages in clinical application, such as: the bioavailability is not high, the dosage is large, the tablets or capsules made of it are absorbed slowly in the body, and the limited effect can only be seen in 7 to 14 days. Therefore, it is necessary to look for water-soluble, antioxidant Antioxidants with high capacity and high bioavailability have great practical significance

Method used

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  • Isoflavone derivative, its production and use as antioxidant
  • Isoflavone derivative, its production and use as antioxidant
  • Isoflavone derivative, its production and use as antioxidant

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preparation example Construction

[0018] The preparation method of the novel antioxidant of the present invention comprises sulfonating the general formula (I') and using an alkali metal or alkaline earth metal compound to form a salt, thereby introducing a sulfonate group to obtain an antioxidant with better water solubility:

[0019]

[0020] Wherein X is hydrogen or hydroxyl.

[0021] More specifically, when X in the above general formula (I') is hydrogen, the reaction is as follows:

[0022]

[0023] wherein M is as defined above.

[0024] When X in the above general formula is a hydroxyl group, the reaction is as follows:

[0025]

[0026] wherein M is as defined above.

[0027] Specifically, the preparation of 3'-sulfonic acid group-daidzein metal salt (L3) and 3'-sulfonic acid group-genistein metal salt (L4) can be carried out as follows: make daidzein (L1 ) or genistein (L2) reacts with concentrated sulfuric acid and adds an alkali metal or alkaline earth metal compound to make the sulfo gr...

Embodiment 1

[0031] Synthesis of Antioxidant L3

[0032] Take 2.52g (0.01mol) L1 (supplied by Shaanxi Saide Hi-Tech Biological Co., Ltd.) into 10mL of concentrated sulfuric acid, stir at room temperature for 30 minutes, the solid gradually dissolves, and the solution turns dark yellow. Take a small amount of reaction liquid and drop it in water, if no insoluble matter appears, it means that the reaction is complete. The reaction was slowly and carefully poured into 40 mL of ice water and stirred. Solid NaCl was then added to the filtrate and stirred vigorously until the added NaCl was no longer dissolved. Stand still to form a white flocculent precipitate, filter and wash with saturated saline. Recrystallized with 5% NaCl aqueous solution to obtain 2.6 g of white needle-like crystal daidzein-3'-sulfonic acid sodium salt with a yield of 75%. m.p.349℃, IR(KBr, ν, cm -1 ): 3441.4(-OH), 1635(-CO-), 1193(-SO 3 ); 1 H NMR (D 2 O, 500MHz, δ, ppm): 6.59 (s, 1H, HC-6), 6.64 (s, 1H, HC-8), ...

Embodiment 2

[0034] Synthesis of Antioxidant L4

[0035] Take 2.69g (10mmol) L2 (supplied by Shaanxi Saide Hi-Tech Biological Co., Ltd.) into 10mL concentrated sulfuric acid, stir at room temperature for 30 minutes, the solid gradually dissolves, and the solution turns dark yellow. Take a small amount of reaction liquid and drop it in water, if no insoluble matter appears, it means that the reaction is complete. The reaction was slowly and carefully poured into 40 mL of ice water and stirred. Solid NaCl was then added to the filtrate and stirred vigorously until the added NaCl was no longer dissolved. Stand still to form a white flocculent precipitate, filter and wash with saturated saline. Recrystallized with 5% NaCl aqueous solution to obtain 2.8 g of white needle crystals (L4) (yield 78%). m.p.>260℃(decomposition), IR(KBr, ν, cm -1 ): 3441.4(-OH), 1642.5(-CO-); 1 H NMR (D 2O, 500MHz, δ, ppm): 5.89 or 5.91 (s, 1H, HC-6 or HC-8), 6.90 or 7.02 (d, 1H, HC-5' or HC-6'), 7.59 (s, 1H ...

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Abstract

A soluble antioxidant flavone derivative, its production and use are disclosed. The process is sulfonating for daidzin or genistein and salting. It can remove hydroxyl-free radical or superoxide anion free radical.

Description

field of invention [0001] The present invention relates to novel water-soluble antioxidants, more specifically to isoflavone derivatives, especially daidzein derivatives and genistein derivatives, their preparation methods and their use as antioxidants. Background of the invention [0002] With the continuous development of scientific research, people have gradually realized that free radicals are closely related to diseases (such as inflammation, atherosclerosis, myocardial infarction, shock, poisoning, tumors, mutations, aging, etc.), so the research on free radicals has become increasingly popular. attention. In the normal metabolic process of organisms, oxidation-reduction reactions are the most common reactions. Oxygen is an electron acceptor in organisms. During the reaction process, due to the difference in the number of electrons it obtains, different free radicals can be generated. According to the oxidation Generally, free radicals are divided into two types: oxyg...

Claims

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Application Information

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IPC IPC(8): C07D311/36A61P39/06
Inventor 延玺刘芸马雨伟司书峰
Owner BEIJING NORMAL UNIVERSITY
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