Curcumenol glucoside compound and its preparation method and uses

A technology of curcumol and compounds, which is applied in the field of new curcumol glycoside compounds and their preparation and application, can solve the problems of low water solubility and difficult preparation, and achieve high solubility, enhanced water solubility, and improved bioavailability Effect

Inactive Publication Date: 2007-07-11
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The abundant hydroxyl groups on the sugar group can not only solve the problems of low water solubility and difficult preparation of curcumol, but also easily bring curcumol into the water phase to dissolve and transport in the blood. When such derivatives reach the lesion cells, the sugar The base can be hydrolyzed by enzymes on the cell membrane, and the decomposed fat-soluble curcumol can easily pass through the cell membrane and enter the cell to play a role;

Method used

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  • Curcumenol glucoside compound and its preparation method and uses
  • Curcumenol glucoside compound and its preparation method and uses
  • Curcumenol glucoside compound and its preparation method and uses

Examples

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preparation example Construction

[0014] Preparation of Curcumol Glycosides

[0015] Curcuma alcohol is the most abundant component in curcuma oil. After further separation and purification of commercially available curcuma, curcumol with a purity of more than 95% can be obtained, which is used as the raw material for glycosylation modification of curcumol structure in the invention patent. .

[0016] (1). Preparation of curcumitol (hydroxyl on C-6 position) glycoside derivatives

[0017] The 6-hydroxyl group in the curcumitol molecule can be regarded as the product of 6-carbonyl monoketal. Since the 6-carbon is connected with a hydroxyl group and an oxygen bridge, due to the steric effect and the electron-donating effect of the oxygen bridge, its The stability and reactivity are slightly weaker than the general hydroxy compounds, and the reaction conditions should be carefully controlled during the reaction.

[0018] The reaction process is as follows:

[0019] Step 1: Synthesis of Bromoacetylated Sugars ...

Embodiment approach

[0032] When different saccharide compounds are used as reaction raw materials, the proportion of raw materials in the reaction should be adjusted according to the specific situation.

[0033] The following examples are only for further illustrating the present invention, rather than limiting the present invention.

Embodiment 1

[0034] Embodiment 1: the preparation of curcumitol-6-O-β-D-glucopyranoside (II);

[0035]

[0036] ① Add 216 g (200 mL, 2.12 mol) of acetic anhydride to a 500 mL four-neck round-bottomed flask equipped with a mechanical stirrer, a thermometer, and a dropping funnel under ice-bath cooling. After cooling to 0 °C, slowly add 1.2 mL ( 70% to 72%, 0.02mol) perchloric acid. After dripping, the temperature was controlled between 30 and 40° C., and 50 g (0.28 mol) of dry glucose powder was added in batches. After the reaction was completed, it was cooled to 0°C, 15.5 g (0.5 mol) of red phosphorus was added, 90.5 g (29 mL, 1.13 mol) of liquid bromine was added dropwise within 4 h, 150 mL of chloroform was added after the reaction was completed, and the unreacted red phosphorus was removed by filtration , the filtrate was washed three times with 100 mL of ice water, and then washed with saturated sodium bicarbonate until the pH was about 7, and the organic layer was dried with molec...

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Abstract

The invention discloses a new curcumenol glycoside compound and making method and application to treat cancer, bacteria and virus, which is characterized by the following: decorating curcumenol through glycoside; possessing excellent tumour resistant and virus resistant activity.

Description

1. Technical field [0001] The present invention relates to a new compound used for treating cancer, antibacterial and antiviral---Curcitol glycoside compound and its preparation method and application. 2. Technical background [0002] Curcumol, also known as turmeric cyclool and curcuminol, belongs to sesquiterpenoids and is an important component in the volatile oil of Curcuma radix. The volatile oil of Curcuma curcumae (Cucumaria curcumae oil) has been included in the Chinese Pharmacopoeia in 1977 (page 463), and it is mainly used for congestion and amenorrhea, etc. Curcuma alcohol, as one of the main active ingredients in Curcuma curcuma oil, also has pharmacological effects such as anti-tumor, antibacterial, anti-early pregnancy, anti-virus, liver protection, blood circulation and stasis removal. [0003] Curcumol has the molecular formula C 15 H 24 O 2 , [CAS] 4871-97-0, molecular weight 236.134, melting point 141~142℃, colorless needle crystal (absolute ethanol), m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/04A61K31/7048A61P35/00A61P31/12A61P31/04
Inventor 梁广李校堃姚崇舜杨树林
Owner WENZHOU MEDICAL UNIV
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