Process for preparing limonin monomer by industrial chromatography method

A technology of limonin and chromatography, applied in the direction of medical preparations containing active ingredients, plant raw materials, plant/algae/fungus/moss components, etc., can solve the problem that the purity is difficult to meet international standards, unfavorable for industrial promotion and application, and cost High cost and other problems, to achieve the effect of improving comprehensive utilization rate, reducing comprehensive cost and simplifying production steps

Inactive Publication Date: 2009-11-18
SHANGHAI XINMA BIOLOGICAL TECH
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AI Technical Summary

Problems solved by technology

However, there has been no technical report on the preparation of limonin monomer by industrial chromatography from the orange stone in the waste residue after production such as squeezed fruit juice as raw material.
In the literature at home and abroad, it is reported that the relevant research is in the laboratory stage, using complex techniques such as preparative high-performance liquid chromatography and flash chromatography, which are costly and are not conducive to industrial promotion and application.
Chinese patent CN1293055 discloses a "process for extracting medicinal active substances from citrus seeds", the main technical feature of which is the comprehensive utilization of citrus seeds by means of extraction and crystallization, but the problem is that the purity is difficult to meet international standards

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  • Process for preparing limonin monomer by industrial chromatography method

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Embodiment 1

[0023] The washed and dried orange cores are cold-pressed to remove fatty acid components, placed in a multifunctional extraction tank and stirred with 70% ethanol at a temperature of 60°C for 20 hours of extraction, and separated by a filter to obtain the filtrate The above-mentioned filtrate is concentrated under reduced pressure to recover ethanol until it has no alcohol taste, and then a concentrated solution containing fatty acids and various limonoid compounds is obtained; the concentrated solution is extracted by chloroform extraction several times, and the combined chloroform layers are concentrated into an extract. Through petroleum ether (manufacturer: Sichuan Honghe Fine Chemical Co., Ltd., specifications: 60-90), reflux extraction at 30°C for 3 hours, degreasing until no fatty acid residues, to obtain an extract containing various limonoid compounds; Add methanol and heat to dissolve, let stand for 1 hour, filter to remove impurities, and obtain crude crystals conta...

Embodiment 2

[0025] The washed and dried orange cores are cold-pressed to remove the fatty acid components, placed in a multi-functional extraction tank and stirred with 90% ethanol at a temperature of 30°C for 15 hours of extraction, and separated by a filter to obtain the filtrate The above-mentioned filtrate is concentrated under reduced pressure to recover ethanol until it has no alcohol taste, and then a concentrated solution containing fatty acids and various limonoid compounds is obtained; the concentrated solution is extracted by chloroform extraction several times, and the combined chloroform layers are concentrated into an extract. Through petroleum ether (manufacturer: Sichuan Honghe Fine Chemical Co., Ltd., specifications: 60-90), reflux extraction at 40°C for 3 hours, degreasing until no fatty acid residues, to obtain an extract containing various limonoid compounds; Add methanol and heat to dissolve, let stand for 1 hour, filter to remove impurities, and obtain crude crystals ...

Embodiment 3

[0027] The washed and dried mandarin stones are mechanically pressed to remove the fatty acid components, placed in a multi-functional extraction tank and stirred with 80% ethanol at a temperature of 50°C for 10 hours of extraction, separated by a filter to obtain Filtrate; the above-mentioned filtrate is concentrated under reduced pressure to recover ethanol until it has no alcohol smell, and a concentrated solution containing fatty acids and various limonoid compounds is obtained; the concentrated solution is extracted by chloroform extraction several times, and the combined chloroform layers are concentrated to form an extract. Through petroleum ether (manufacturer: Sichuan Honghe Fine Chemical Co., Ltd., specification: 60-90), reflux extraction at 35°C for 3 hours, degreasing to no fatty acid residue, and obtaining an extract containing various limonoid compounds; Add methanol and heat to dissolve, let stand for 1 hour, filter to remove impurities, and obtain crude crystals...

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Abstract

The invention provides a process for preparing limonin monomer by an industrial chromatography method. The process comprises the following steps: extracting oil from citrus seeds after being washed and dried by alcohol organic solvent, filtering and separating to obtain filtrate; decompressing and concentrating the filtrate, recycling the alcohol organic solvent, extracting by hydrochloric ether and concentrating to form extract; refluxing and extracting the extract by ether solvent, degreasing the extract, obtaining filtration residues by filtering and washing the filtration residues until no fatty acid exists; adding alcohol solvent into the filtration residues, carrying out recrystallization to obtain coarse crystal containing a plurality of limonin compounds, crystallizing and drying to obtain limonin compound crystal after carrying out the chromatography by an industrial chromatographic column. The process fully utilizes waste citrus seeds and adopts the industrial chromatography method to extract high-purity limonin, improves the comprehensive utilization ratio, has low cost, easy operation and control, repeated solvent utilization and reduced pollution and is suitable for industrialized large-scale production.

Description

technical field [0001] The invention relates to the technical field of limonin preparation, more specifically, to the technical field of limonin monomer preparation, in particular to a process for preparing limonin monomer by industrial chromatography. Background technique [0002] Previous studies and literature have shown that orange stones contain a large number of limonoid compounds with anti-tumor activity, which are a type of natural active substances against cancer. However, there has been no technical report on the preparation of limonin monomer by industrial chromatography from the orange stone in the waste residue after production such as squeezed fruit juice as raw material. In the literature at home and abroad, it is reported that the relevant research is in the laboratory stage, using complex techniques such as preparative high-performance liquid chromatography and flash chromatography, which are costly and are not conducive to industrial promotion and applicati...

Claims

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Application Information

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IPC IPC(8): C07D493/22A61K36/752
Inventor 陈新唐述兵何军
Owner SHANGHAI XINMA BIOLOGICAL TECH
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