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Method for synthesizing tilianin from naringin as raw material

A technology of naringin and terizin, which is applied in chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., can solve the problems of unreported synthesis methods and low cytotoxicity of terizin.

Inactive Publication Date: 2018-11-02
INNER MONGOLIA MEDICAL UNIV
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Problems solved by technology

[0004] In recent years, studies have shown that stinariside has low cytotoxicity, good safety, and has a certain inhibitory effect on tumors. However, at present, this monomer is mostly obtained by separation and purification, and its synthesis method has not been reported in the literature.

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  • Method for synthesizing tilianin from naringin as raw material

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Embodiment Construction

[0018] In order to make the objects and advantages of the present invention clearer, the present invention will be further described in detail below in conjunction with the examples. It should be understood that the specific embodiments described here are only used to explain the present invention, not to limit the present invention.

[0019] like figure 1 As shown, the embodiment of the present invention provides a method for synthesizing stellin by using naringin as a raw material, comprising the following steps:

[0020] S1, the synthesis of Rhodorin

[0021] Naringin (10.02g, 17.25mmol) was dissolved in 100mL of pyridine, under argon protection, iodine (4.45g, 17.05mmol) was added, and heated to 95°C for 2h. The reaction solution was cooled to room temperature, and a pale yellow solid was precipitated. After suction filtration, the crude product was recrystallized with acetone to obtain 8.14 g of the product, with a yield of 82.83%, m.p.236-238°C.

[0022] Synthesis of ...

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Abstract

The invention discloses a method for synthesizing tilianin from naringin as a raw material. The method comprises the following steps: S1, synthesizing rhoifolin; S2, synthesizing a compound, namely 5,7-dyhydroxy-2-(4-methoxy-phenyl)-4H-chromene-4-ketone; S3, synthesizing acetoxyl methyl)-6-((5-hydroxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromene-7-yl) alkoxy) tetrahydro-2H-pyran-3,4,5-triester triacetate; S4, synthesizing a compound, namely 5-hydroxy-2-(4-methoxy-phenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yl-yl) alkoxy)-4H-benzopyran-4-ketone. By adopting the method, the naringin is adopted as the raw material to synthesize the tilianin through reactions such as oxidation, methylation and hydrolysis.

Description

technical field [0001] The invention relates to the field of compound preparation, in particular to a method for synthesizing scinnabin with naringin as a raw material. Background technique [0002] Xiangqinglan is a traditional medicinal material of Uygur and Mongolian. It has hundreds of years of medicinal history. It is mainly used for the treatment of diseases such as hypertension, hyperlipidemia and asthma. It has the function of inhibiting platelet activation and stabilizing platelets. Various chemical components such as triterpenoids, flavonoids and polysaccharides have been isolated from it. Among them, the total flavonoids of Xiangqinglan are the effective parts of the flavonoids extracted and purified from Xiangqinglan. A variety of flavonoids such as abibiscidin and kaempferol have good anti-oxidation, anti-asthma, sedative and hypnotic effects, and protect the brain from transient ischemia. They can regulate lipid metabolism disorders and dilate blood vessels. Th...

Claims

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Application Information

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IPC IPC(8): C07H17/07C07H1/00
CPCC07H1/00C07H17/07
Inventor 张振涛曲丽丽樊丽雅马宇衡刘宏
Owner INNER MONGOLIA MEDICAL UNIV
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