CN108114018A - A kind of method for preparing alcohol-soluble licoflavone - Google Patents
A kind of method for preparing alcohol-soluble licoflavone Download PDFInfo
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- CN108114018A CN108114018A CN201810049673.4A CN201810049673A CN108114018A CN 108114018 A CN108114018 A CN 108114018A CN 201810049673 A CN201810049673 A CN 201810049673A CN 108114018 A CN108114018 A CN 108114018A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
- A61K36/484—Glycyrrhiza (licorice)
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/39—Complex extraction schemes, e.g. fractionation or repeated extraction steps
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/53—Liquid-solid separation, e.g. centrifugation, sedimentation or crystallization
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Abstract
This case is related to a kind of method for preparing alcohol-soluble licoflavone, using Radix Glycyrrhizae as raw material, by low-carbon alcohol extracting, concentration, acid concentrate, filtering, precipitation plus low-carbon alcohols dissolving, filtering, alkali tune filtrate, filtering, filtrate concentration, desalination and drying steps is adjusted to obtain alcohol-soluble flavones, the wherein content ＞ 45% of flavones, and the precipitation filtered out after alkali tune can further be comprehensively utilized as glycyrrhizic acid purified feed stock, raw material availability is improved, reduces production cost；Preparation method according to the present invention is simple for process, and treating capacity is big, and the comprehensive utilization ratio of Radix Glycyrrhizae is high, and equipment requirement is low, and Extracting temperature is low, and extraction time is short, and solvent processing is simple, high income etc., suitable for industrial applications.
Description
Technical field
The present invention relates to isolating and purifying for effective components in plants, and in particular to a kind of from Radix Glycyrrhizae or Radix Glycyrrhizae crude extract
In isolate and purify the method for alcohol-soluble general flavone.
Background technology
Radix Glycyrrhizae is a kind of herbaceos perennial, containing the multiple efficacies ingredient such as flavonoids, triterpenes, polysaccharide, therefore
Radix Glycyrrhizae is also the Chinese medicine being worldwide widely used simply.The isolated licoflavone from Radix Glycyrrhizae is because with suppression
The outstanding pharmacological action such as bacterium, antiviral, antitumor, anti-oxidant, liver protection and be increasingly subject to the attention of people, at present from various sweet
Isolated flavone compound is up to more than 100 kinds in grass.
Licoflavone is the general name of a major class active material in Radix Glycyrrhizae, it is made of many heterogeneities, and each into
The pharmacological action divided is again different therefore particularly important to isolating and purifying for licoflavone.Traditional licoflavone separation side
Method complex process, yield are low, of high cost, and make a low multiple use to effective liquorice.In recent years, people are directed to Radix Glycyrrhizae
The separation purifying technique of acid has carried out many researchs, also achieves some achievements, but to the extraction of Flavonoid substances in Radix Glycyrrhizae
Technical study is less, and researches are isolated and purified to alcohol-soluble licoflavone.The separation for the alcohol-soluble licoflavone reported
Purification process includes polyamide partition method, solvent soaking method, supercritical extraction and macroreticular resin partition method etc., these methods are big
All there is complex process, treating capacity is small, Radix Glycyrrhizae is made a low multiple use, equipment requirement is high, Extracting temperature is high, extraction time is long,
The shortcomings such as solvent processing is troublesome, yield is low.
The content of the invention
For shortcoming of the prior art, the object of the present invention is to provide a kind of sides for preparing alcohol-soluble licoflavone
Method.
The present invention provides a kind of methods for preparing alcohol-soluble licoflavone, comprise the following steps：
1) low-carbon alcohol extracting：The low-carbon alcohols of 5-10 times of weight or volume amount are added in into licorice raw material, are carried at 60-90 DEG C
It takes 2-3 times, merges extracting solution, which is concentrated to give concentrate；
2) acid is adjusted：With the pH value of inorganic acid adjusting concentrate in 2-4, precipitation is left and taken in filtering, drying precipitated up to glycyrrhizic acid
Crude product；
3) low-carbon alcohols dissolve：The low-carbon alcohols of 10-20 times of weight or volume amount are added in into glycyrrhizic acid inclusion compound, at 20-60 DEG C
Lower dissolving filters out filter residue, collects lysate；Dissolving 1-2 times is repeated, merges lysate；
4) alkali tune：Lysate pH value is adjusted to 6-8 with aqueous slkali, is separated by filtration filtrate and precipitation, filtrate is concentrated, is taken off
Salt, drying are to get alcohol-soluble flavones.
Preferably, in the step 1), the licorice raw material exists for licorice root particles of the grain size more than 10mm or thickness
The Radix Glycyrrhizae section of 2-4mm, the low-carbon alcohols are methanol solution or ethanol solution of the mass fraction in 40%-70%.
Preferably, inorganic acid is selected from hydrochloric acid or sulfuric acid in the step 2).
Preferably, low-carbon alcohols are molten for methanol solution or ethyl alcohol of the mass fraction in 90%-100% in the step 3)
Liquid.
Preferably, the species of alkali is ammonium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, carbonic acid in the step 4)
One kind in sodium, sodium acid carbonate, the precipitation can be used as glycyrrhizic acid purified feed stock.
Preferably, contain to help in the low-carbon alcohols of the step 3) and carry composition；This helps extract composition to contain 30-35 weights
Measure part chitosan oligosaccharide, 20-25 parts by weight lactic acid and 10-15 parts by weight dihydroxyacetone (DHA)s.
Preferably, the mass fraction for carrying composition is helped in the low-carbon alcohols of the step 3) in 0-0.5%.
Elaboration to the present invention and its advantage：Using Radix Glycyrrhizae as raw material in the present invention, by low-carbon alcohol extracting, concentration,
Acid adjusts pH value to 2-4, precipitation is dry, adds low-carbon alcohols dissolving, filtering, filtrate adjusting PH with base value to 6-8, filtering, filtrate concentration, desalination
And drying steps have obtained the content ＞ 45% of alcohol-soluble flavones, wherein flavones, and the precipitation filtered out after alkali tune can
It is further comprehensively utilized as glycyrrhizic acid purified feed stock, improves raw material availability, reduce production cost；It is made in the present invention
Standby alcohol-soluble licoflavone meets《Chinese Pharmacopoeia》Dissolving requirement under note on the use item, i.e., solute 1g (mL) can be in 10-30mL (no
Including 30mL) it dissolves in ethyl alcohol.
Inventor is accumulated based on the research isolated and purified to licoflavone, discovery passes through low-carbon alcohol extracting, acid sinks, alcohol is molten,
Add alkali removal of impurities, washing, drying that can obtain the alcohol-soluble flavones of high-content；Further, inventor is had found in extraction or molten
Solution carries composition with being added in low carbon alcohol solution by helping of forming of chitosan oligosaccharide, lactic acid and dihydroxyacetone (DHA) on a small quantity, molten by alcohol
Synergistic effect between property flavones and three, can be effectively increased the solubility of alcohol-soluble flavones, improve its recovery rate, and help
Carrying composition can be completely removed in subsequent alkali tune and during being concentrated and dried, and the alcohol-soluble flavones of preparation will not be produced
Raw any negative effect；Using the content of alcohol-soluble flavones made from method in this case is high, preparation process is simple, the rate of transform
Good, at low cost, the suitable scale industrial production of height, alcohol-soluble, has a extensive future.
Description of the drawings
Fig. 1 is the liquid chromatogram peak calibration maps of alcohol-soluble licoflavone；
Wherein, S1-S4 is respectively that the standard sample chromatography of alcohol-soluble licoflavone class chemical composition of Chinese materia medica goes out peak figure；
The chromatography that S5-S9 is followed successively by the alcohol-soluble glycyrrhiza total flavonoid prepared by embodiment 2-6 goes out peak figure.
Specific embodiment
With reference to embodiment, the present invention is described in further detail, to make those skilled in the art with reference to specification
Word can be implemented according to this.The present invention provides a kind of method for preparing alcohol-soluble licoflavone, the following examples can be helped
Help those skilled in the art that the present invention, but do not limit the invention in any way is more fully understood.
Embodiment 1
1) extracting liquorice medicinal material 100g (20mm particles) adds in 70% ethanol water of 1000mL, is extracted back at 90 DEG C
1h is flowed, obtains an extract；70% ethanol water of 800mL is continuously added into the dregs of a decoction, extraction reflux 1h, obtains two and carry at 90 DEG C
Liquid；Merge extracting solution twice, and with sock filtration, collection filtered fluid；Filtered fluid is concentrated into no alcohol taste, while recycles ethyl alcohol；
2) 50% sulfuric acid solution (v is added in into concentrate again:V), it is 2 to adjust pH value, and filtering is left and taken precipitation, and washed
PH value is precipitated to 4 or so, dry glycyrrhizic acid inclusion compound 15.4g will be precipitated；
3) 300mL95% ethyl alcohol is added in into glycyrrhizic acid inclusion compound, dissolves to obtain lysate at 20 DEG C, and it is wherein heavy to filter removal
It forms sediment；
4) using concentrated ammonia liquor adjusting lysate pH value to 7.5, filtrate and precipitation is separated by filtration, concentrates the filtrate to paste,
Add the water washing paste, desalination, drying are simultaneously crushed up to alcohol-soluble glycyrrhiza total flavonoid 5.9g (content 51.2%).
Embodiment 2
1) extracting liquorice medicinal material 100g (section) adds in 50% ethanol water of 600mL, the extraction reflux 1h at 80 DEG C,
Obtain an extract；50% ethanol water of 400mL is continuously added into the dregs of a decoction, extraction reflux 1h, obtains two extracts at 90 DEG C；To
50% ethanol water of 400mL is continuously added in the dregs of a decoction, extraction reflux 1h, obtains three extracts at 90 DEG C；Merging is extracted three times
Liquid, and with sock filtration, collect filtered fluid；Filtered fluid is concentrated into no alcohol taste, while recycles ethyl alcohol；
2) 50% sulfuric acid solution (v is added in into concentrate again:V), it is 3 to adjust pH value, and filtering is left and taken precipitation, and washed
PH value is precipitated to 4 or so, dry glycyrrhizic acid inclusion compound 16.3g will be precipitated；
3) 200mL95% ethyl alcohol is added in into glycyrrhizic acid inclusion compound, dissolves to obtain lysate at 40 DEG C；It filters out residual in lysate
Slag is continued to extract residue with 95% ethyl alcohol, filters extracting solution, and merge with lysate；
4) the lysate pH value after merging is adjusted to 8 using concentrated ammonia liquor, be separated by filtration filtrate and precipitation, concentrate the filtrate to
Paste, adds the water washing paste, and desalination, drying are simultaneously crushed up to alcohol-soluble glycyrrhiza total flavonoid 6.8g (content 49.8%).
Embodiment 3
1) extracting liquorice medicinal material 100g (20mm particles) adds in 40% ethanol water of 800mL, and reflux is extracted at 90 DEG C
1h obtains an extract；40% ethanol water of 600mL is continuously added into the dregs of a decoction, extraction reflux 1h, obtains two and carry at 90 DEG C
Liquid；Merge extracting solution twice, and with sock filtration, collection filtered fluid；Filtered fluid is concentrated into no alcohol taste, while recycles ethyl alcohol；
2) 50% sulfuric acid solution (v is added in into concentrate again:V), it is 2 to adjust pH value, and filtering is left and taken precipitation, and washed
PH value is precipitated to 4 or so, dry glycyrrhizic acid inclusion compound 15.8g will be precipitated；
3) 180mL95% ethyl alcohol is added in into glycyrrhizic acid inclusion compound, dissolves to obtain lysate at 60 DEG C；It filters out residual in lysate
Slag is continued to extract residue with 95% ethyl alcohol, filters extracting solution, and merge with lysate；
4) the lysate pH value after merging is adjusted to 6 using concentrated ammonia liquor, be separated by filtration filtrate and precipitation, concentrate the filtrate to
Paste, adds the water washing paste, and desalination, drying are simultaneously crushed up to alcohol-soluble glycyrrhiza total flavonoid 7.2g (content 47.8%).
Embodiment 4
1) extracting liquorice medicinal material 100g (20mm particles) adds in 40% ethanol water of 800mL, and reflux is extracted at 90 DEG C
1h obtains an extract；40% ethanol water of 600mL is continuously added into the dregs of a decoction, extraction reflux 1h, obtains two and carry at 90 DEG C
Liquid；Merge extracting solution twice, and with sock filtration, collection filtered fluid；Filtered fluid is concentrated into no alcohol taste, while recycles ethyl alcohol；
2) 50% sulfuric acid solution (v is added in into concentrate again:V), it is 2 to adjust pH value, and filtering is left and taken precipitation, and washed
PH value is precipitated to 4 or so, dry glycyrrhizic acid inclusion compound 15.8g will be precipitated；
3) 180mL95% ethyl alcohol is added in into glycyrrhizic acid inclusion compound, dissolves to obtain lysate at 60 DEG C；It filters out residual in lysate
Slag is continued to extract residue with 95% ethyl alcohol, filters extracting solution, and merge with lysate；Wherein, in 95% ethyl alcohol contain by
0.30g chitosan oligosaccharides, 0.22g lactic acid and helping for 0.13g dihydroxyacetone (DHA)s composition carry composition；
4) the lysate pH value after merging is adjusted to 6 using concentrated ammonia liquor, be separated by filtration filtrate and precipitation, concentrate the filtrate to
Paste, adds the water washing paste, and desalination, drying are simultaneously crushed up to alcohol-soluble glycyrrhiza total flavonoid 7.6g (content 57.6%).
Embodiment 5
1) extracting liquorice medicinal material 1kg (20mm particles) adds in 50% ethanol water of 8L, the extraction reflux 1h at 90 DEG C,
Obtain an extract；50% ethanol water of 6L is continuously added into the dregs of a decoction, extraction reflux 1h, obtains two extracts at 90 DEG C；Merge
Extracting solution twice, and with sock filtration, collect filtered fluid；Filtered fluid is concentrated into no alcohol taste, while recycles ethyl alcohol；
2) 50% sulfuric acid solution (v is added in into concentrate again:V), it is 2 to adjust pH value, and filtering is left and taken precipitation, and washed
PH value is precipitated to 4 or so, dry glycyrrhizic acid inclusion compound 149g will be precipitated；
3) 1.5L95% ethyl alcohol is added in into glycyrrhizic acid inclusion compound, dissolves to obtain lysate at 60 DEG C, and it is wherein heavy to filter removal
It forms sediment；
4) using concentrated ammonia liquor adjusting lysate pH value to 6.5, filtrate and precipitation is separated by filtration, concentrates the filtrate to paste,
Add the water washing paste, desalination, drying are simultaneously crushed up to alcohol-soluble glycyrrhiza total flavonoid 63g (content 52.8%).
Embodiment 6
1) extracting liquorice medicinal material 1kg (20mm particles) adds in 50% ethanol water of 8L, the extraction reflux 1h at 90 DEG C,
Obtain an extract；50% ethanol water of 6L is continuously added into the dregs of a decoction, extraction reflux 1h, obtains two extracts at 90 DEG C；Merge
Extracting solution twice, and with sock filtration, collect filtered fluid；Filtered fluid is concentrated into no alcohol taste, while recycles ethyl alcohol；
2) 50% sulfuric acid solution (v is added in into concentrate again:V), it is 2 to adjust pH value, and filtering is left and taken precipitation, and washed
PH value is precipitated to 4 or so, dry glycyrrhizic acid inclusion compound 149g will be precipitated；
3) 1.5L95% ethyl alcohol is added in into glycyrrhizic acid inclusion compound, dissolves to obtain lysate at 60 DEG C, and it is wherein heavy to filter removal
It forms sediment；Wherein, contain in 95% ethyl alcohol and composition is carried by helping of forming of 2.8g chitosan oligosaccharides, 1.9g lactic acid and 1.0g dihydroxyacetone (DHA)s；
4) using concentrated ammonia liquor adjusting lysate pH value to 6.5, filtrate and precipitation is separated by filtration, concentrates the filtrate to paste,
Add the water washing paste, desalination, drying are simultaneously crushed up to alcohol-soluble glycyrrhiza total flavonoid 72g (content 59.2%).
Ultraviolet-visible spectrophotometry is used to the detection of the alcohol-soluble glycyrrhiza total flavonoid prepared by embodiment 1-6, use is sweet
Careless glycosides is colour reagent as reference substance, 10% potassium hydroxide solution, and pure water is as sample treatment solvent；According to embodiment 1-
The content of flavones is all higher than 47%, especially embodiment 4 and embodiment 6 in the alcohol-soluble licoflavone that in 6 prepared by method, respectively
A small amount of helping is added when alcohol is molten on the basis of embodiment 3 and embodiment 5 and carry composition, effectively increase alcohol-soluble Radix Glycyrrhizae
The flavones rate of transform and wherein flavones content make the content of its flavones reach more than 57%.
It is first for the component and content of prepared alcohol-soluble glycyrrhiza total flavonoid in the further qualitative and quantitative detection present invention
First, inventor has demarcated the chemical composition of Chinese materia medica standard sample of alcohol-soluble licoflavone class using liquid chromatogram respectively, including celery
Sugared liquiritin 1, liquiritin 2, isoliquiritin 3, Radix Glycyrrhizae are looked into and ketone B4, glycyrrhizin 5, isoliquiritigenin 6, licochalcone A 7, are obtained
Their appearance time and content and the relation of peak area, i.e. S1-S4 in Fig. 1；Then, under identical testing conditions,
Alcohol-soluble licoflavone separated in embodiment 2-6 is subjected to liquid chromatogram test respectively, and obtains corresponding chromatography appearance
Scheme, i.e. S5-S9 in Fig. 1.
It is easily analyzed according to Fig. 1, impurity content is few in prepared alcohol-soluble licoflavone in embodiment 2-6, effectively
Licoflavone class chemical composition of Chinese materia medica content it is more, product purity is high；And each active ingredient peak area in comparison S6 and S7, S7
The peak area for being all higher than licochalcone A 7 in S6, especially S7 is about twice of S6, i.e., licochalcone A 7 in embodiment 3
Content is about twice of licochalcone A 7 in S6, this illustrates to add in help in low-carbon alcohols in preparation process to carry composition, can
The purification efficiency of effective alcohol-soluble licoflavone class is significantly improved, improves the utilization rate of raw material, production cost is reduced, passes through Fig. 1
The comparison of middle S8 and S9 can be led to the same conclusion；By in the present invention method prepare alcohol-soluble glycyrrhiza total flavonoid cost it is low,
Simple for process, more existing alcohol-soluble licoflavone preparation method advantageously, is also more suitable for industrialized production.
Although the embodiments of the present invention have been disclosed as above, but its be not restricted in specification and embodiment it is listed
With it can be fully applied to various fields suitable for the present invention, for those skilled in the art, can be easily
Realize other modification, therefore without departing from the general concept defined in the claims and the equivalent scope, it is of the invention and unlimited
In specific details.
Claims (7)
- A kind of 1. method for preparing alcohol-soluble licoflavone, which is characterized in that comprise the following steps：1) low-carbon alcohol extracting：The low-carbon alcohols of 5-10 times of weight or volume amount are added in into licorice raw material, 2- is extracted at 60-90 DEG C 3 times, merge extracting solution, which is concentrated to give concentrate；2) acid is adjusted：With the pH value of inorganic acid adjusting concentrate in 2-4, precipitation is left and taken in filtering, drying precipitated thick up to glycyrrhizic acid Product；3) low-carbon alcohols dissolve：The low-carbon alcohols of 10-20 times of weight or volume amount are added in into glycyrrhizic acid inclusion compound, it is molten at 20-60 DEG C Solution, filtering removal filter residue, collects lysate；Dissolving 1-2 times is repeated, merges lysate；4) alkali tune：Lysate pH value is adjusted to 6-8 with aqueous slkali, is separated by filtration filtrate and precipitation, and filtrate is concentrated, is desalination, dry It is dry to get alcohol-soluble flavones.
- 2. according to the method described in claim 1, it is characterized in that, in the step 1), the licorice raw material is more than for grain size Radix Glycyrrhizae of the licorice root particles or thickness of 10mm in 2-4mm is cut into slices, and the low-carbon alcohols are methanol of the mass fraction in 40%-70% Solution or ethanol solution.
- 3. according to the method described in claim 1, it is characterized in that, inorganic acid is selected from hydrochloric acid or sulfuric acid in the step 2).
- 4. according to the method described in claim 1, it is characterized in that, low-carbon alcohols are mass fraction in 90%- in the step 3) 100% methanol solution or ethanol solution.
- 5. according to the method described in claim 1, it is characterized in that, in the step 4) alkali species for ammonium hydroxide, sodium hydroxide, One kind in potassium hydroxide, calcium hydroxide, sodium carbonate, sodium acid carbonate, the precipitation are used as glycyrrhizic acid purified feed stock.
- 6. according to the method described in claim 1, carry composition it is characterized in that, containing to help in the low-carbon alcohols of the step 3)； This helps extract composition to contain 30-35 parts by weight chitosan oligosaccharide, 20-25 parts by weight lactic acid and 10-15 parts by weight dihydroxyacetone (DHA)s.
- 7. according to the method described in claim 6, it is characterized in that, the quality that carries composition is helped in the low-carbon alcohols of the step 3) Fraction is in 0-0.5%.
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| CN117018060A (en) * | 2023-09-19 | 2023-11-10 | 新疆维吾尔自治区药物研究所 | Total flavone extract of new tower flower and its prepn |
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| CN113694096A (en) * | 2021-08-06 | 2021-11-26 | 中国农业科学院兰州畜牧与兽药研究所 | Licorice extract and preparation method and application thereof |
| CN113694096B (en) * | 2021-08-06 | 2023-09-22 | 中国农业科学院兰州畜牧与兽药研究所 | Licorice extract and preparation method and application thereof |
| CN115368729A (en) * | 2022-08-02 | 2022-11-22 | 百草边大生物科技(青岛)有限公司 | Preparation method of macrobiological functional agent containing liquorice active substance |
| CN117018060A (en) * | 2023-09-19 | 2023-11-10 | 新疆维吾尔自治区药物研究所 | Total flavone extract of new tower flower and its prepn |
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