CN114099570A - Preparation method of low-loss fructus cannabis small molecule extract - Google Patents

Preparation method of low-loss fructus cannabis small molecule extract Download PDF

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CN114099570A
CN114099570A CN202111463915.2A CN202111463915A CN114099570A CN 114099570 A CN114099570 A CN 114099570A CN 202111463915 A CN202111463915 A CN 202111463915A CN 114099570 A CN114099570 A CN 114099570A
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extraction
extract
fructus cannabis
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water
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张边江
唐宁
陈全战
杨平
王立科
钱保俐
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Nanjing Xiaozhuang University
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Nanjing Xiaozhuang University
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Abstract

The invention provides a preparation method of a fructus cannabis micromolecule extract, which adopts the main technical scheme that: the fructus cannabis meal after oil extraction is degreased, extracted by adopting secondary water extraction combined with primary alcohol extraction, extracted by a micelle medium of a specific system, recovered by organic layer micromolecules, and purified and distilled by combining rapid molecular distillation. The method of the invention can obviously improve the extraction efficiency and purity of the product and effectively reduce the product loss by means of the magnetic microsphere mediated organic layer micromolecule recovery method with specific surface structure and proper molecular distillation, and the magnetic microsphere material used for separation can be recycled, the process is simple and efficient, and the method has the characteristics of low loss, simple process, no need of chromatographic operation, suitability for industrial mass production and the like.

Description

Preparation method of low-loss fructus cannabis small molecule extract
Technical Field
The invention belongs to the field of medicinal extracts, and relates to a low-loss preparation process of an extract mainly containing small molecule components of fructus cannabis which basically does not contain grease and protein.
Background
Fructus Cannabis is dry mature seed of Cannabis sativa L.of Moraceae, and is rich in protein and oil. Wherein the sum of the contents of the oil and the protein exceeds 75 percent, and the total content of the fat, the protein and the carbohydrate (containing water-soluble polysaccharide) is about 90 percent; the rest is mainly small molecule active substance such as alkaloid, ketone, phenol, etc., specifically including lecithin, glucuronic acid, sterol, calcium, magnesium, vitamin B1, B2, cannabinol, etc., and also contains other water soluble or alcohol soluble vitamin components of wide variety.
Because of rich oil and protein contents of fructus cannabis, extraction research on fructus cannabis in the prior art mainly focuses on oil and protein, while other small molecular substances also have corresponding activities in the aspects of blood pressure reduction, blood fat reduction, oxidation resistance, aging resistance, memory improvement, health preservation and health care and other effects, for example, small molecular substances including phytosterol and the like have the effects of oxidation resistance, free radical removal, aging resistance, inflammation resistance, blood fat reduction, prostate disease prevention and treatment and the like, and are widely applied to foods, medicines and cosmetics.
In the prior art, the technical field of extraction of Chinese medicines CN 111973655A discloses a preparation method of a fructus cannabis extract, which comprises the following steps: preparing fructus cannabis decoction pieces into coarsest powder, putting the coarse powder and water with the weight 6-12 times of that of the fructus cannabis decoction pieces into an extraction tank, adding a beta-cyclodextrin solution prepared by dissolving beta-cyclodextrin with the weight 2-10% of that of the fructus cannabis coarsest powder in water with the weight 5-20 times of that of the fructus cannabis decoction pieces, dynamically stirring, keeping boiling for 0.5-3 hours, and filtering to obtain a first extracting solution and dregs; putting the medicine residues and water with the weight 5-12 times of the coarsest powder of fructus cannabis into an extraction tank, dynamically stirring, keeping boiling for 0.5-3 h, and filtering to obtain a second extracting solution; mixing the two extractive solutions, and centrifuging to obtain centrifugate; concentrating the centrifugate at low temperature under reduced pressure to obtain fructus Cannabis extract.
Although the application can effectively extract the water-soluble substances of the fructus cannabis, the extraction efficiency of the fat-soluble ingredients is low due to the adoption of a water decoction mode; the extraction target of the application is fructus cannabis decoction pieces, the main components extracted by the fructus cannabis decoction pieces are protein and grease with abundant contents, and the extraction improvement of small molecular substance components is not emphasized.
CN 110777183A discloses a method for preparing fructus cannabis oligopeptide by using fructus cannabis protein powder as a raw material and utilizing a biological enzymolysis technology. The method comprises the following steps: screening raw materials, dynamically extracting slurry to obtain an extracting solution, carrying out enzymolysis step by step to obtain an enzymolysis solution, purifying the enzymolysis solution, and then carrying out powder processing to obtain fructus cannabis oligopeptide powder. The application focuses on the preparation of fructus cannabis oligopeptide powder, belongs to the extraction range of protein, and does not relate to the extraction of small molecular substances.
At present, the utilization of the fructus cannabis in the prior art is generally oil extraction (a small amount of protein is researched by the prior art), the residual residues are discarded or used as feed, so that the waste of small molecular nutrient components is caused, and the waste nutrient components have application values in the fields of food processing, beauty cosmetics and medicine. Therefore, the extraction and separation of small molecular components from fructus cannabis meal are of great necessity for application or research, but no report is available on the total extraction method of fructus cannabis small molecular active substances at present, and the total extract of the small molecular beneficial substances can be obtained efficiently, so that the method has a remarkable application prospect both for direct application (as a natural food or health product additive) and for the research of further separation and individual component.
Disclosure of Invention
Aiming at the problems in the prior art, the invention aims at providing a preparation method of a fructus cannabis small molecule extract mainly containing water-soluble components. The preparation method can not only efficiently extract high-purity fructus Cannabis water-soluble substances (including a small amount of polysaccharide components), but also retain part of effective small molecule alcohol-soluble active ingredients (including flavonoids, sterols, etc.) except fatty acid.
The preparation method of the invention also aims to effectively improve the yield and purity of the fructus cannabis small molecule extract and reduce the loss in the extraction process. In addition, the preparation method has the characteristics of low loss, simple process, no need of chromatographic operation, suitability for industrial mass production and the like.
The invention adopts the main technical scheme that: the method is characterized in that after the hemp seed meal subjected to oil extraction is subjected to degreasing treatment, secondary water extraction and primary alcohol extraction are adopted for extraction, micelle medium extraction and organic layer small molecule recovery of a specific system are combined, and a means of combining rapid molecular distillation purification and distillation is combined, particularly by means of a magnetic microsphere mediated organic layer small molecule recovery method with a specific surface structure and proper molecular distillation, the extraction efficiency and purity of a product can be remarkably improved, the product loss is effectively reduced, the magnetic microsphere material used for separation can be recycled, and the process is efficient and simple.
Specifically, the technical scheme of the invention is as follows.
In a first aspect, the present invention provides a method for preparing a high-purity fructus cannabis small molecule extract based on fructus cannabis meal, comprising the following steps S1-S6:
step S1: carrying out degreasing pretreatment on the fructus cannabis meal after oil separation:
1) drying the fructus cannabis cake or solid residue (including oil separation by mechanical squeezing or extraction method) after oil separation, crushing and sieving with a 100-mesh and 200-mesh sieve to obtain fructus cannabis cake powder.
2) Degreasing with petroleum ether at room temperature for 0.5-2h for 2-3 times at a ratio of 1 g/2-5 ml, preferably controlling the content of residual oil below 2%; degreasing, filtering, washing filter residue with ethanol, and drying to obtain degreased fructus cannabis powder.
The degreasing in this step can remove not only most of the remaining fat and oil but also an undesirable part of the alkaloids (although a trace amount of the hemp seed alkaloids is toxic, they are likely to cause side effects such as diarrhea).
Degreasing means are known in the art, and degreasing can be performed, for example, using conventional extraction degreasing or subcritical extraction methods.
Step S2: water extraction-alcohol extraction combined method
1) Carrying out water extraction for the first time: adding distilled water into the degreased fructus cannabis powder according to the weight ratio of 1:8-15 of the feed liquid, and grinding for 5-10min in a colloid mill to obtain a mixed liquid; adding the mixed solution into an extraction tank, extracting at 40-60 deg.C (preferably at a rotation speed of not more than 120 rpm) under stirring for 3-5h, and filtering while hot to obtain water extract A and residue A;
2) secondary water extraction: adding distilled water into the residue A according to the weight ratio of 1:5-10, carrying out ultrasonic extraction for 0.5-1h in an extraction tank, and filtering while the solution is hot to obtain a water extract B and residue B; and (3) combining the water extract A, B to obtain the fructus cannabis water extract.
3) Alcohol extraction: drying the filter residue after the secondary water extraction, adding 75-80% ethanol according to the weight ratio of 1g to 5-10ml of the feed liquid, soaking at 40-50 ℃ for 6-12h, and performing Soxhlet extraction in a Soxhlet extractor for 0.5-2 h; the alcohol extract is obtained and concentrated under reduced pressure to less than half of the original volume.
Step S3: primary deproteinization:
1) concentrating fructus Cannabis water extractive solution under reduced pressure to 5-50% of the original volume (preferably to about equal weight 1-2 times of fructus Cannabis meal), and mixing with the above concentrated ethanol extractive solution to obtain concentrated total extractive solution 1;
mixing 100 volume parts of concentrated total extract 1 with 20-25 volume parts of Sevage reagent (composed of chloroform and n-butanol, the volume ratio of chloroform to n-butanol is 3-4:1), shaking for 15-30min, centrifuging, layering, collecting aqueous solution to obtain primary deproteinized total extract 1, and separating the protein layer for later use.
Wherein, the concentration under reduced pressure is preferably carried out in a vacuum concentrator at low temperature, such as 50-80 deg.C, and vacuum degree of-0.08-0.09 Mpa to relative density of about 1.1.
2) Synchronously removing residual protein and pigment by a micelle medium extraction method:
firstly, dissolving a proper amount of biosurfactant (preferably sophorolipid) in a mixed organic solvent of hexane and butanol (the volume ratio of the butanol to the hexane is preferably 1:2-3), and uniformly mixing to obtain a micelle medium extract (the concentration of the biosurfactant is preferably 2-5 wt%) for later use;
secondly, according to the extraction liquid of the micelle medium: adding the micelle medium extraction liquid into the primary deproteinized total extraction liquid 1 according to the mass ratio of 1:4-5, adding NaCl to 2-4 wt%, violently shaking for extraction for 10-15min (preferably vortex shaking), then centrifuging at high speed for layering, and taking the lower-layer aqueous solution to obtain the extraction liquid simultaneously removing residual protein and pigment impurities, wherein in the step, the total pigment removal rate is greater than 80%, and the total protein removal rate after twice deproteinization is greater than 85%.
Compared with activated carbon decolorization, the loss rate of active components can be greatly reduced by extracting and decolorizing the pigment with the micelle medium, because the activated carbon has stronger adsorption capacity and can adsorb a large amount of small-molecule active components together, thereby causing larger loss.
Step S4: recovering small molecule active species from the organic layer:
combining the organic layer obtained in the preliminary deproteinization treatment step and the organic layer obtained in the micelle medium extraction step, adding magnetic microspheres to 3-15 wt% (preferably 5-10 wt%), shaking at room temperature for 0.5-1h, then performing solid-liquid separation under the action of a magnetic field, and collecting the magnetic microspheres; washing the microspheres with distilled water, placing the microspheres in a proper amount of 95% ethanol or absolute ethanol, performing ultrasonic oscillation for 5-10min for desorption, magnetically separating the microspheres, concentrating the obtained mother liquor under reduced pressure until the organic solvent is removed by drying, dissolving the obtained solid in the absolute ethanol again, and merging the solid into the deproteinized and pigment impurity-removed extracting solution obtained in the step S3 to obtain the total extracting solution 2.
In this step, the shaking treatment was performed on a shaker at a frequency of 100-.
In the step, the adsorption capacity of the magnetic microspheres to the small molecular substances is stronger than that of the high molecular substances, so that most of the small molecular substances in the organic layer can be recovered.
Optionally, the magnetic microspheres can be subjected to column chromatography separation, the magnetic microspheres are loaded into a column and then eluted by ethanol with different concentrations, and the detected eluent is collected until the eluent basically does not contain small molecular components.
The magnetic microspheres are magnetic microspheres with functional groups, preferably polyvinyl alcohol magnetic microspheres or polystyrene magnetic microspheres with amino or carboxyl modified surfaces. Which may be commercially available or prepared according to methods known in the art.
The preferable magnetic microsphere is polyvinyl alcohol magnetic microsphere, and the preparation method comprises the following steps:
dissolving polyvinyl alcohol and magnetic ferroferric oxide (the preferred mass ratio is 3-8:1) nanoparticles (50-500nm) in deionized water, heating and slowly stirring for 0.5-1h, cooling, adding liquid paraffin and span activator, continuously stirring for 0.5-1h, then adding dilute hydrochloric acid solution and a proper amount of cross-linking agent, continuously heating to stir and react for 0.5-1h, cooling, performing magnetic absorption separation to obtain microspheres, sequentially washing with petroleum ether and deionized water, and then performing vacuum drying to obtain powdery solid. Adding magnetic solid powder into ethylenediamine, adding sodium hydroxide and a surfactant, stirring in a water bath at 90 ℃ for 5-10h, filtering distilled water after the reaction is finished, cleaning with petroleum ether, and drying in vacuum to obtain the magnetic polyvinyl alcohol microspheres with aminated surfaces. Further, a secondary magnetization treatment may be performed to enhance both the homogenization and the magnetic properties.
Step S5: and (3) purification treatment:
concentrating the total extractive solution 2 under reduced pressure to remove organic solvent (preferably to below 40 vol%), preheating in preheater of molecular distiller, molecular distilling, and collecting small molecular distillation component flowing out along condensation column to obtain composite extract containing small molecular substance as main component.
Specifically, the distillation parameters were: the vacuum degree is 10-20Pa, the distillation temperature is 100-120 ℃, the feeding speed is 3-5ml/min, the condensation temperature is 5-10 ℃, and the preferred film scraping rotation speed is 150-300 r/min.
The molecular distillation step can effectively remove a small amount of protein, nucleic acid and other high molecular impurities attached when the magnetic microspheres adsorb small molecular active substances in the organic layer, and reagents and impurities added subsequently such as sodium chloride and the like; the content of high molecular impurities such as oil, protein and the like in the solution obtained after distillation is determined to be less than 10 percent (including a small amount of polysaccharide).
After the separation, a large amount of grease, protein, nucleic acid and the like of the fructus cannabis are separated, so that an extract product (containing partial polysaccharide) mainly containing small molecular substances with higher purity (about 90%) is obtained through purification.
Step S6: embedding treatment to prepare finished preparation
Dissolving the distilled compound extract with appropriate amount of 30-70% volume fraction ethanol solution completely, adding into 40-50 deg.C 30-50 wt% cyclodextrin solution under rapid stirring, continuously stirring for 10-15min to substantially uniform, and cooling; homogenizing the mixed solution in a homogenizer for 2-3 times, and then spray drying the homogenized solution in a high-speed centrifugal spray dryer to obtain the fructus cannabis extract powder preparation finished product.
Wherein, the mass dosage of the cyclodextrin solution is preferably more than 10 times of that of the compound solution.
Wherein the air inlet temperature of the spray drying is 110-130 ℃, and the air outlet temperature is 70-90 ℃.
Because the small molecular extract contains more easily-oxidized components, the fructus cannabis extract is embedded to prepare the solid preparation, so that the active components are not easily oxidized, and the oxidation resistance and the storage stability of the product are improved.
In a second aspect of the invention, a finished product of fructus cannabis extract or powder preparation prepared by the method is provided.
In a third aspect of the present invention, there is provided the use of the above-mentioned fructus cannabis extract or preparation in the fields of medicine and food.
Compared with the prior art, the technical scheme of the invention also has at least the following beneficial effects:
1) the method can effectively improve the yield (containing partial alcohol-soluble components) of the extract (containing no main components such as grease, protein and the like) mainly containing water-soluble micromolecule components in the fructus cannabis meal, and effectively improve the purity of the extract; compared with a pure water extraction method, the yield can be improved by more than 30%, the total content of the small molecular extract can reach about 90%, and the yield and the purity of the extract are obviously improved on the premise of no chromatographic purification.
2) The method provided by the invention can be used for micronizing fructus cannabis meal and carrying out colloid mill treatment, so that the influence of seed coat structure on extraction is avoided; the method combining the water extraction and the alcohol extraction twice is adopted, so that the dissolution of water-soluble components can be maximized, and alcohol-soluble micromolecular components in the water-soluble components are extracted.
3) The invention removes residual protein and pigment synchronously by conventional protein removing and micelle medium extracting, and basically removes protein/nucleic acid macromolecules by molecular distillation and purification means; the secondary recovery of the alcohol-soluble components from the organic layer is combined, so that the loss of the alcohol-soluble components is effectively avoided, the yield and the purity of the extract mainly containing the small molecular components are ensured, and the process is effective and simple and feasible.
4) Although polymer embedding is a common embedding means in the field, the invention adopts a method of firstly purifying and then embedding cyclodextrin, so that various extract small molecular substances are easier to embed into cyclodextrin holes; due to the excessive existence of cyclodextrin, the embedding rate of small molecules is extremely high, even a trace amount of water-soluble polysaccharide components contained in the extract can be effectively embedded, and thus the stability of the extract is effectively improved.
Detailed Description
The present invention will be described in detail with reference to specific examples, but the scope of the present invention is not limited to these examples in any way.
Preparation example
Preparation of magnetic polyvinyl alcohol microspheres
1) Dissolving 20g of polyvinyl alcohol and 4g of magnetic ferroferric oxide nanoparticles (average particle size of 100-.
2) And then, soaking 3g of the obtained magnetic solid powder in 12 wt% diluted hydrochloric acid for 30min for acidification treatment, washing and drying with deionized water, then adding the magnetic solid powder into 76mL of ethylenediamine, then adding 6g of sodium hydroxide and 2g of surfactant tetrabutylammonium chloride, stirring in a water bath at 90 ℃ for 5h, filtering with distilled water after the reaction is finished, washing with petroleum ether, and drying in vacuum to obtain the magnetic polyvinyl alcohol microspheres with the moderately aminated and modified surfaces.
Example 1
A preparation method of fructus Cannabis small molecule extract comprises the following steps S1-S6:
step S1: degreasing pretreatment is carried out on the hemp seed meal after oil separation
1) And (3) fully drying about 100g of the hemp seed meal (about 4% of the residual oil component) after oil separation, crushing and sieving by a 200-mesh sieve to obtain the hemp seed meal powder.
2) According to the ratio of material to liquid of 1g to 3ml, refluxing and degreasing for 2 times by using petroleum ether at normal temperature, wherein the degreasing time is 1h each time; degreasing, filtering, washing filter residue with ethanol, and drying to obtain degreased fructus cannabis powder.
Step S2: water extraction-alcohol extraction combined method
1) Carrying out water extraction for the first time: adding distilled water into the degreased fructus cannabis powder according to the weight ratio of 1:10 of the feed liquid, and grinding for 5min in a colloid mill to obtain a mixed liquid; putting the mixed solution into an extraction tank, stirring for 3h at 50 ℃ for extraction, and filtering while the solution is hot to obtain a water extract A and a residue A;
2) secondary water extraction: adding distilled water into residue A (without drying, directly used) at a weight ratio of 1:5, ultrasonic extracting at 50 deg.C for 0.5 hr with ultrasonic power of 120W, and filtering while hot after ultrasonic extraction to obtain water extract B and residue B; and (3) combining the water extract A, B to obtain the fructus cannabis water extract.
3) Alcohol extraction: drying the filter residue B after the secondary water extraction, adding 75% ethanol by volume according to the weight ratio of 1g to 8ml of the feed liquid, soaking for 6h at 45 ℃, and performing Soxhlet extraction for 0.5h in a Soxhlet extractor; the resulting alcoholic extract was concentrated under reduced pressure to about 86 ml.
Step S3: primary deproteinization:
1) decompressing and concentrating the fructus cannabis water extract to about 220ml, and combining the concentrated fructus cannabis water extract with the concentrated alcohol extract to obtain a concentrated total extract 1; wherein the vacuum concentration is carried out in a vacuum concentrator at 55 deg.C and-0.09 Mpa. Mixing the concentrated total extract with 65ml Sevage reagent (the volume ratio of chloroform to n-butanol is 3:1), shaking for 20min, centrifuging, and collecting aqueous solution to obtain the total extract subjected to primary deproteinization treatment.
2) Synchronously removing residual protein and pigment by a micelle medium extraction method:
firstly, mixing a proper amount of biosurfactant sophorolipid with a hexane/butanol mixed solvent (the volume ratio of butanol to hexane is 1:2), fully shaking and uniformly mixing to obtain micelle medium extract (the concentration of the biosurfactant is 3wt percent) for later use;
and then, adding 52g of the micelle medium extraction liquid into the total extraction liquid subjected to primary deproteinization, adding 8g of NaCl, performing vortex oscillation extraction for 12min, performing high-speed centrifugation for layering, and taking the lower-layer aqueous solution to obtain the extraction liquid simultaneously removing residual protein and pigment impurities, wherein in the step, the total pigment removal rate is about 82%, and the total protein removal rate after twice deproteinization is about 88%.
Step S4: recovery of small molecule active species from organic layers
Combining the Sevage organic layer obtained in the preliminary deproteinization step S3 with the organic layer obtained in the micelle medium extraction step, adding the magnetic microspheres prepared in the preparation example to about 8 wt%, shaking at room temperature for 1h, performing solid-liquid separation under the action of a magnetic field, and collecting the magnetic microspheres; washing the microspheres with distilled water, placing the microspheres in absolute ethyl alcohol, performing ultrasonic oscillation for 5-6min for desorption, magnetically separating the microspheres, concentrating the obtained mother liquor under reduced pressure, evaporating to remove the solvent, dissolving with a proper amount of absolute ethyl alcohol, and combining the dissolved mother liquor with the deproteinized pigment impurity-removed extracting solution obtained in the step S3 to obtain a total extracting solution 2.
Step S5: concentrating the total extractive solution 2 to 80ml under reduced pressure, preheating in preheater of molecular distiller, molecular distilling, collecting small molecular distillation components flowing out along condensing column, and evaporating solvent under reduced pressure to obtain composite extract containing no oil, protein and pigment about 7.8g, wherein the content of residual components of high molecular such as protein is less than 8%. Wherein the distillation parameters are as follows: the vacuum degree is 10-15Pa, the distillation temperature is 110 ℃, the feeding speed is 3ml/min, and the condensation temperature is 5 ℃.
Step S6: embedding treatment to prepare finished preparation
Dissolving the above distilled compound extract with 40% volume fraction ethanol at room temperature, adding into 40 deg.C 32 wt% alpha-cyclodextrin solution (360g) under rapid stirring, stirring for 10min until it is substantially uniform, and cooling; homogenizing the mixed solution in a homogenizer for 2 times, and then spray drying the homogenized solution in a high-speed centrifugal spray dryer to obtain the finished product of the fructus cannabis extract powder preparation basically free of grease, protein and pigment. Wherein the air inlet temperature of the spray drying is 110 ℃, and the air outlet temperature is 90 ℃.
Example 2
Step S1: degreasing pretreatment
1) And (3) fully drying about 100g of the hemp seed meal after the oil is separated, crushing and sieving by a 200-mesh sieve to obtain the hemp seed meal powder.
2) According to the ratio of material to liquid of 1g to 4ml, refluxing and degreasing for 2 times by using petroleum ether at normal temperature; degreasing, filtering, washing filter residue with ethanol, and drying to obtain degreased fructus cannabis powder.
Step S2: water extraction-alcohol extraction combined method
1) Carrying out water extraction for the first time: adding distilled water into the degreased fructus cannabis powder according to the weight ratio of the material liquid to the material liquid of 1:15, and grinding for 10min in a colloid mill to obtain a mixed liquid; putting the mixed solution into an extraction tank, stirring for 4h at 50 ℃ for extraction, and filtering while the solution is hot to obtain a water extract A and a residue A;
2) secondary water extraction: adding distilled water into residue A (without drying, directly used) at a weight ratio of 1:6, ultrasonic extracting at 50 deg.C for 0.5h with ultrasonic power of 150W, and filtering while hot after ultrasonic extraction to obtain water extract B and residue B; and (3) combining the water extract A, B to obtain the fructus cannabis water extract.
3) Alcohol extraction: drying the filter residue B after the secondary water extraction, adding 75% ethanol by volume according to the weight ratio of 1g to 10ml of the feed liquid, soaking for 8 hours at 45 ℃, and then performing Soxhlet extraction for 1 hour in a Soxhlet extractor; the resulting alcoholic extract was concentrated under reduced pressure to about 80 ml.
Step S3: primary deproteinization:
1) decompressing and concentrating the fructus cannabis water extract to about 250ml, and combining the concentrated fructus cannabis water extract with the concentrated alcohol extract to obtain a concentrated total extract 1; wherein the vacuum concentration is carried out in a vacuum concentrator at 60 deg.C under-0.09 MPa. Mixing the concentrated total extract with 78ml Sevage reagent (volume ratio of chloroform to n-butanol is 4:1), shaking for 30min, centrifuging, and collecting aqueous solution to obtain total extract for primary deproteinization treatment.
2) Synchronously removing residual protein and pigment by a micelle medium extraction method:
firstly, mixing a proper amount of biosurfactant sophorolipid with a hexane/butanol mixed solvent (butanol: hexane volume ratio is 1:3), fully shaking and uniformly mixing to obtain micelle medium extract (biosurfactant concentration is 4 wt%) for later use;
and then, adding about 60g of the micelle medium extraction liquid and 8.5g of NaCl into the total extraction liquid subjected to primary deproteinization treatment, performing vortex oscillation extraction for 12min, performing high-speed centrifugation for layering, and taking the lower-layer aqueous solution to obtain the extraction liquid with residual protein and pigment impurities removed simultaneously.
Step S4: recovery of small molecule active species from organic layers
Combining the Sevage organic layer obtained in the preliminary deproteinization step S3 with the organic layer obtained in the micelle medium extraction step, adding the magnetic microspheres prepared in the preparation example to about 10 wt%, shaking at room temperature for 1h, performing solid-liquid separation under the action of a magnetic field, and collecting the magnetic microspheres; washing the microspheres with distilled water, placing the microspheres in absolute ethyl alcohol, performing ultrasonic oscillation for 5-6min, performing desorption, magnetically separating the microspheres, concentrating mother liquor obtained after separating the microspheres under reduced pressure, evaporating to remove the solvent, dissolving with a proper amount of absolute ethyl alcohol, and combining the mother liquor with the deproteinized and pigment impurity-removed extracting solution obtained in the step S3 to obtain a total extracting solution 2.
Step S5: concentrating the total extractive solution 2 to about 85ml under reduced pressure, preheating in a preheater of a molecular distiller, performing molecular distillation, collecting small molecular distillation components flowing out along a condensation column, and evaporating solvent under reduced pressure to obtain about 8.2g of compound extract containing substantially no oil, protein and pigment. The distillation parameters were the same as in example 1.
Step S6: embedding treatment to prepare finished preparation
Dissolving the above distilled compound extract with 50% volume fraction ethanol at room temperature, adding into 35 wt% beta-cyclodextrin solution (380g) at 50 deg.C under rapid stirring, stirring for 15min until it is substantially uniform, and cooling; homogenizing the mixed solution in a homogenizer for 2 times, and then spray drying the homogenized solution in a high-speed centrifugal spray dryer to obtain the fructus cannabis extract powder preparation finished product. Wherein the air inlet temperature of the spray drying is 120 ℃, and the air outlet temperature is 90 ℃.
Comparative example
1) About 100g of the hemp seed meal after the oil separation in the same manner as in example 1 was taken, sufficiently dried, crushed and sieved with a 200-mesh sieve to obtain hemp seed meal powder.
2) According to the ratio of material to liquid of 1g to 3ml, refluxing and degreasing for 2 times by using petroleum ether at normal temperature; degreasing, filtering, washing filter residue with ethanol, and drying to obtain degreased fructus cannabis powder.
3) Adding distilled water into the degreased fructus cannabis powder according to the weight ratio of 1:10 of the feed liquid to obtain a mixed liquid; putting the mixed solution into an extraction tank, stirring for 6h at 50 ℃ for extraction, and filtering while the solution is hot to obtain a water extract A and a residue A; adding distilled water into the residue (without drying, directly used) at a weight ratio of 1:5, extracting at 50 deg.C under stirring for 0.5h, and filtering while hot to obtain water extractive solution B and residue B; and (3) combining the water extract A, B to obtain the fructus cannabis water extract.
4) Drying the residue B, adding 75% ethanol according to the weight ratio of 1g to 10ml of the material liquid, soaking at 45 ℃ for 6h, and performing reflux extraction for 1 h; obtaining an alcohol extract, and concentrating under reduced pressure.
5) Decompressing and concentrating the fructus cannabis water extract to about 250ml, and combining the concentrated fructus cannabis water extract with the concentrated alcohol extract to obtain a concentrated total extract 1; mixing the concentrated total extract with 70ml Sevage reagent (the volume ratio of chloroform to n-butanol is 3:1), shaking for 30min, centrifuging, and collecting aqueous solution to obtain deproteinized total extract.
6) The obtained extract was concentrated under reduced pressure and then vacuum-dried to obtain about 6.4g of a hemp seed extract in which the residual protein content was about 18% (while still containing a pigment component), and the obtained extract was poor in color due to the presence of the pigment.
Examples 1-2 compared to the comparative examples, it can be seen that the total extraction yield and total relative purity (relative to macromolecular components such as proteins) of the small molecule complex extract substantially free of lipids, proteins and pigments according to the present invention are significantly increased, which is mainly due to the fact that the extraction of small molecule substances is more thorough and efficient by virtue of the specific multiple extraction separation and the recovery of the effective components lost in the organic layer of the extraction step.
The above embodiments do not limit the technical solutions of the present invention, and a person skilled in the art may modify the technical solutions described in the above embodiments without departing from the scope of the technical solutions of the present invention.

Claims (9)

1. A preparation method of a fructus cannabis small molecule extract is characterized by comprising the following steps:
step S1: degreasing fructus Cannabis dregs for separating oil
1-1) drying the fructus cannabis cake after oil separation, crushing and sieving with a 100-mesh and 200-mesh sieve to obtain fructus cannabis cake powder;
1-2) degreasing the fructus cannabis meal with petroleum ether for 2-3 times at normal temperature according to the ratio of 1g to 2-5ml, wherein the degreasing time is 0.5-2h each time; filtering after degreasing treatment, washing and drying filter residues by using ethanol to obtain degreased fructus cannabis powder;
step S2: water extraction-alcohol extraction combined method
1) Carrying out water extraction for the first time: adding distilled water into the degreased fructus cannabis powder according to the weight ratio of 1:8-15 of the feed liquid, and grinding for 5-10min in a colloid mill to obtain a mixed liquid; putting the mixed solution into an extraction tank, stirring for 3-5h at 40-60 ℃ for extraction, and filtering while hot to obtain a water extract A and a residue A;
2) secondary water extraction: adding distilled water into the residue A according to the weight ratio of 1:5-10, carrying out ultrasonic extraction for 0.5-1h in an extraction tank, and filtering while the solution is hot to obtain a water extract B and residue B; combining the aqueous extracts A, B to obtain an aqueous extract of fructus Cannabis;
3) alcohol extraction: drying the filter residue after the secondary water extraction, adding 75-80% ethanol according to the weight ratio of 1g to 5-10ml of the feed liquid, soaking at 40-50 ℃ for 6-12h, and performing Soxhlet extraction in a Soxhlet extractor for 0.5-2 h; obtaining alcohol extract, and concentrating under reduced pressure;
step S3: preliminary deproteinization
1) Decompressing and concentrating the fructus cannabis water extract to 5-50% of the original volume, and combining the concentrated alcohol extract to obtain a concentrated total extract 1; mixing 100 parts by volume of the concentrated total extract 1 with 20-25 parts by volume of Sevage reagent, shaking for 15-30min, centrifuging, layering, and taking aqueous solution to obtain a primary deproteinized total extract 1;
2) micellar medium extraction method for synchronously removing residual protein and pigment
Firstly, dissolving a proper amount of biosurfactant in a mixed organic solvent of hexane and butanol, and uniformly mixing to obtain micelle medium extract;
secondly, according to the extraction liquid of the micelle medium: adding the micelle medium extraction liquid into the primary deproteinized total extraction liquid 1, adding NaCl to 2-4 wt%, violently shaking for extraction for 10-15min, centrifuging at high speed for layering, and taking the lower-layer aqueous solution to obtain an extraction liquid with residual protein and pigment impurities removed simultaneously;
step S4: recovery of small molecule active species from organic layers
Combining the organic layer obtained in the preliminary deproteinization treatment step with the organic layer obtained in the micelle medium extraction step, adding magnetic microspheres to 3-15 wt%, shaking at room temperature for 0.5-1h, then performing solid-liquid separation under the action of a magnetic field, and collecting the magnetic microspheres; washing the microspheres with distilled water, placing the microspheres in a proper amount of 95% ethanol or absolute ethanol, performing ultrasonic oscillation for 5-10min for desorption, magnetically separating the microspheres, concentrating the obtained mother liquor under reduced pressure until the organic solvent is removed by drying, dissolving the obtained solid in the absolute ethanol again, and merging the solid into the deproteinized and pigment impurity-removed extracting solution obtained in the step S3 to obtain a total extracting solution 2;
wherein the magnetic microspheres are polyvinyl alcohol magnetic microspheres or polystyrene magnetic microspheres;
step S5: purification treatment
Concentrating the total extractive solution 2 under reduced pressure to remove organic solvent, preheating in preheater of molecular distiller, performing molecular distillation, and collecting small molecular distillation components to obtain composite extract containing small molecular substance as main component;
preferably, the following step S6 is further included:
step S6: embedding process
Dissolving the distilled compound extract with 30-70% volume fraction ethanol solution completely, adding into 40-50 deg.C 30-50 wt% cyclodextrin solution under rapid stirring, stirring for 10-15min, and cooling; homogenizing the mixed solution in a homogenizer for 2-3 times, and then spray drying the homogenized solution in a high-speed centrifugal spray dryer to obtain fructus Cannabis extract granule.
2. The method according to claim 1, wherein in step S3, the Sevage reagent consists of chloroform and n-butanol, and the volume ratio of chloroform to n-butanol is 3-4: 1; vacuum concentrating at 50-80 deg.C in a vacuum concentrator.
3. The method according to claim 1, wherein in step S3, the biosurfactant is sophorolipid, and the volume ratio of butanol to hexane in the hexane-butanol mixed organic solvent is 1: 2-3.
4. The method of claim 1, wherein in step S4, the magnetic microspheres are polyvinyl alcohol magnetic microspheres, and are prepared by the following method:
dissolving polyvinyl alcohol and magnetic ferroferric oxide nanoparticles in a mass ratio of 3-8:1 in deionized water, heating and slowly stirring for 0.5-1h, cooling, adding liquid paraffin and span active agent, continuously stirring for 0.5-1h, then adding dilute hydrochloric acid solution and a proper amount of cross-linking agent, continuously heating until stirring and reacting for 0.5-1h, cooling, performing magnetic separation to obtain microspheres, sequentially washing with petroleum ether and deionized water, and then performing vacuum drying to obtain powdery solid; adding magnetic solid powder into ethylenediamine, adding sodium hydroxide and surfactant, stirring in 90 deg.C water bath for 5-10h, filtering with distilled water after reaction, cleaning with petroleum ether, and vacuum drying to obtain magnetic polyvinyl alcohol microsphere.
5. The method of claim 1, wherein in step S5, the distillation parameters are: the vacuum degree is 10-20Pa, the distillation temperature is 100-120 ℃, the feeding speed is 3-5ml/min, and the condensation temperature is 5-10 ℃.
6. The method according to claim 1, wherein in step S6, the cyclodextrin solution is used in an amount of 10 times or more by mass as much as the complex solution.
7. The method according to claim 1, wherein in step S6, the inlet air temperature for spray drying is 110-130 ℃ and the outlet air temperature is 70-90 ℃.
8. A hemp seed extract or preparation produced according to the method of any one of claims 1 to 7.
9. Use of the hemp seed extract or preparation according to claim 8 in the fields of medicine and food.
CN202111463915.2A 2021-12-03 2021-12-03 Preparation method of low-loss fructus cannabis small molecule extract Pending CN114099570A (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107793492A (en) * 2017-11-17 2018-03-13 浙江海洋大学 A kind of extracting method of fructus cannabis polysaccharide
CN111973655A (en) * 2020-09-10 2020-11-24 广州市香雪制药股份有限公司 Preparation method of fructus cannabis extract

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107793492A (en) * 2017-11-17 2018-03-13 浙江海洋大学 A kind of extracting method of fructus cannabis polysaccharide
CN111973655A (en) * 2020-09-10 2020-11-24 广州市香雪制药股份有限公司 Preparation method of fructus cannabis extract

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