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Preparation method of 2,3-cis-silybin B

A silibinin and semi-preparative chromatographic technology, applied in the field of preparation of 2,3-cis-silibinin B, can solve the problems of low content, inability to prepare high-purity compounds, and no separation to obtain high-purity compounds. Achieving shortened process, reduced sample and solvent consumption, fast and efficient method

Inactive Publication Date: 2015-06-17
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0005] The content of this compound in plants is low, and it is interfered by other isomeric compounds during the separation process. Conventional chemical separation methods cannot produce high-purity compounds. It is only proved by chromatography-mass spectrometry that it exists in milk thistle, and has not been isolated so far. high purity compound

Method used

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  • Preparation method of 2,3-cis-silybin B
  • Preparation method of 2,3-cis-silybin B

Examples

Experimental program
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Effect test

Embodiment 1

[0028] 10g silybin mixture (for analysis see figure 1 A) Mix with 5g Na2CO3 and dissolve in 40% methanol, heat to reflux for 12 hours, cool, neutralize the reaction solution to pH7 with HCl, filter to obtain 2,3-cis-silibinin B conversion with a purity of 3% (Analysis see figure 1 B). The transformed product was separated by an industrial chromatographic column (190×80mm, 15um) and eluted with 55% methanol. The fractions containing the target compound were collected and concentrated under reduced pressure to obtain 2,3-cis-silibinin B-rich with a purity of 70%. Collection (analysis see figure 1 C), the enrichment was separated by a semi-preparative chromatographic column (250×20mm, 5um), eluted with 60% methanol, and the fraction containing the target compound was collected and concentrated under reduced pressure to obtain 2,3-cis with a purity of 98.4%. - silybin B product (analysis see figure 1 D).

Embodiment 2

[0030] 10g silybin mixture and 100g NaHCO3 were mixed and dissolved in 100% methanol, heated to reflux for 16 hours, cooled, neutralized with HCl to pH7, filtered to obtain 2,3-cis-silymarin with a purity of 3% Bin B transformants. The transformed product was separated by an industrial chromatographic column (190×80mm, 15um) and eluted with 55% methanol. The fractions containing the target compound were collected and concentrated under reduced pressure to obtain 2,3-cis-silibinin B-rich with a purity of 30%. The enriched material was separated by a semi-preparative chromatographic column (250×20mm, 10um) and eluted with 60% methanol. The fraction containing the target compound was collected and concentrated under reduced pressure to obtain 2,3-cis with a purity of 95.5%. - a silybin B product.

Embodiment 3

[0032] Mix 0.1g of silybin B monomer compound with 0.5ml of ammonia water and dissolve in 40% ethanol, heat to reflux for 24 hours, cool, neutralize the reaction solution with HCl to pH7, and filter to obtain 2,3- Cis-silibinin B transformant. The transformed product was separated by an industrial chromatographic column (240×100mm, 45um) and eluted with 55% methanol. The fractions containing the target compound were collected and concentrated under reduced pressure to obtain 2,3-cis-silibinin B-rich with a purity of 50%. The enriched material was separated by a semi-preparative chromatographic column (250×10mm, 5um) and eluted with 55% methanol. The fraction containing the target compound was collected and concentrated under reduced pressure to obtain 2,3-cis with a purity of 97.3%. - a silybin B product.

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Abstract

The invention relates to a preparation method of 2,3-cis-silybin B. With silybin B as a raw material, and under an alkaline condition, silybin B is subjected to catalytic conversion into low-content 2,3-cis-silybin B, industrial chromatography enrichment is adopted and combined with semi-preparative chromatographic purification and separation, and thus high-purity 2,3-cis-silybin B is obtained. The 2,3-cis-silybin B is a flavone lignin compound which naturally exists but has low content, a conventional chemical separation method is unable to prepare the high-purity compound, and the method can be used for effective separation to obtain the high-purity 2,3-cis-silybin B.

Description

technical field [0001] The invention relates to a method for preparing 2,3-cis-silibinin B. Background technique [0002] Milk thistle is the seed of milk thistle, a medicinal plant of Compositae. It has a history of more than 2,000 years in the treatment of liver and gallbladder diseases. It can prevent damage to the liver caused by chemical toxins, food toxins and drugs, and promote the regeneration and repair of liver cells. It is known as It is a "natural liver protection drug"; in addition, as a strong antioxidant, milk thistle can remove free radicals in the human body and delay aging. In recent years, its anticancer and tumor prevention effects have shown good development potential. [0003] Silymarin (Silybin) is a class of flavonoid lignans extracted from the seed coat of milk thistle seeds. It is the main active ingredient of milk thistle, including silybin (Silybin), isosilibin ( Isosilybin), silychristin (Silychristin) and silydianin (Silydianin) and other 10 i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D407/04
CPCC07D407/04
Inventor 肖红斌高明哲赵楠邹晓伟
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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