Preparation method of the reference substance of cyanidin-3-coumaroyl-diglucose-5-glucoside

A technology of glucoside and coumaroyl, applied in the field of preparation of bluebonnet-3-coumaroyl-diglucose-5-glucoside, can solve the problem of unmentioned, inability to obtain high-purity products, and inability to provide flower colors Glycosides and other problems, to achieve the effect of simple and easy method

Active Publication Date: 2021-03-05
上海诗丹德标准技术服务有限公司
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  • Claims
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Problems solved by technology

But there is no mention of cyanidin-3-coumaroyl-diglucose-5-glucoside, and the scheme it provides can only obtain anthocyanins with a purity of 92.4-94.3%, and cannot provide anthocyanins with a purity of more than 98%. Anthocyanins
The inventors of the present invention used the scheme described in it to separate and prepare cyanidin-3-coumaroyl-diglucose-5-glucoside from purple cabbage, and found that countercurrent chromatography is effective for cyanidin-3-coumaroyl-diglucose The separation effect of -5-glucoside is very poor, and high-purity products cannot be obtained at all

Method used

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  • Preparation method of the reference substance of cyanidin-3-coumaroyl-diglucose-5-glucoside
  • Preparation method of the reference substance of cyanidin-3-coumaroyl-diglucose-5-glucoside
  • Preparation method of the reference substance of cyanidin-3-coumaroyl-diglucose-5-glucoside

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preparation example Construction

[0036] After extensive and in-depth research, the inventors first developed a method for preparing a high-purity cyanidin-3-coumaroyl-diglucose-5-glucoside reference substance. Separation method of the present invention comprises the following steps: comprises the following steps successively:

[0037] In the high-pressure reverse-phase chromatography column separation process, the crude product containing cyanidin-3-coumaroyl-diglucose-5-glucoside is loaded onto the high-pressure reverse-phase chromatography column, and the pressure is 5-15.0Mpa to contain 0.05-1 % formic acid and 15%-20% acetonitrile in water to obtain a solution of the target object.

[0038] In the solidification process, the solution of the target substance obtained in the reverse phase chromatography column preparation process is concentrated until the concentration of cyanidin-3-coumaroyl-diglucose-5-glucoside is 5% to 50%, and the concentrated solution is frozen After drying, a solid powder of the forma...

Embodiment 1

[0060] A. Raw material extraction: Add 0.5kg cabbage red powder to 5L methanol solution containing 0.05% hydrochloric acid, ultrasonically extract 3 times, 1 hour each time, cool to room temperature, filter with suction, combine the filtrates, concentrate at 45 degrees until there is no alcohol smell, 500mL;

[0061] B. Macroporous resin enrichment: Weigh 8Kg AB-8 macroporous adsorption resin and load it into a column, use the concentrated solution of step A to dynamically adsorb and load the sample with macroporous resin, then use 20L of water to elute impurities, and then use 30L of 0.05 % hydrochloric acid methanol solution to elute the target substance, collect the eluate, and concentrate to 1L;

[0062] C. Medium-pressure preparation: A medium-pressure column is loaded with a concentrated solution of a crude product with a solid content of about 100g, and the target content is about 10g, and 4 columns are loaded in parallel.

[0063] Medium-pressure preparative column: D...

Embodiment 2

[0071] Except that in the step of E. high pressure preparation, gradient elution was carried out using the eluent of 15%-20% acetonitrile (containing 0.1% formic acid), the rest were performed in the same manner as in Example 1 to obtain cyanidin-3 with a purity of 98.4%. - Coumaroyl-diglucose-5-glucoside about 0.55 g. The HPLC spectrum of the liquid before the solid product recovery process, and the HPLC spectrum of the solid after freeze-drying can refer to figure 2 , can stably provide high-purity formate of the target product.

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Abstract

The present invention provides a method for preparing a reference substance of cyanidin-3-coumaryl-diglucose-5-glucoside with a purity of more than 98%, comprising enrichment and concentration process, chromatographic column purification process and solidification process, The solution of the target substance obtained in the chromatographic column preparation process is concentrated to a concentration of cyanidin-3-coumaroyl-diglucose-5-glucoside of 5% to 30%, and the concentrated solution is freeze-dried to obtain cyanidin The solid powder of ‑3‑coumaroyl‑diglucose‑5‑glucoside, the stability of cyanidin‑3‑coumaroyl‑diglucose‑5‑glucoside was verified, and it was found that its formate could exist stably , It is also found that the current anthocyanin standard substance has obtained a solid powder reference substance, which is very beneficial to the storage and distribution of the reference substance.

Description

technical field [0001] The present invention relates to a preparation method of cyanidin-3-coumaroyl-diglucose-5-glucoside, in particular to high-purity cyanidin-3-coumaroyl-diglucose-5-glucoside from purple cabbage Preparation method of solid reference substance of glucoside. Background technique [0002] cyanidin-3-coumaroyl-diglucose-5-glucoside is a kind of anthocyanin, the structure is as shown in the following formula 1, it was first reported structure by Ole-P. Johansen et al. (Phytochemistry, 1991, 30 , 4137-4141). [0003] Formula 1 [0004] The researchers also found it in purple cabbage. Purple cabbage is a common vegetable, also known as purple cabbage, red cabbage, purple cabbage, and red cabbage. Varieties, which originated in the Mediterranean Sea and western and southern Europe, are currently grown and eaten all over the world, and have always been a research hotspot for medicinal and edible homologous products. In recent years, there have been many re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/065C07H1/08
CPCC07H1/08C07H17/065
Inventor 舒亚平孙马蔷黄建东钱勇谢天培
Owner 上海诗丹德标准技术服务有限公司
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