CN110330409A - A kind of preparation method of industrial hemp extract - Google Patents
A kind of preparation method of industrial hemp extract Download PDFInfo
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- CN110330409A CN110330409A CN201910670464.6A CN201910670464A CN110330409A CN 110330409 A CN110330409 A CN 110330409A CN 201910670464 A CN201910670464 A CN 201910670464A CN 110330409 A CN110330409 A CN 110330409A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
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- 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)
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- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/60—Moraceae (Mulberry family), e.g. breadfruit or fig
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
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- A61P25/00—Drugs for disorders of the nervous system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/004—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from plant material or from animal material
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Abstract
The invention discloses a kind of preparation methods of industrial hemp extract, it is enriched with cannabinol compounds by the way of adding salt and centrifugation, one step is completely removed water-solubility impurity, it avoids sinking technique using conventional water or removes the toluene introduced when water-solubility impurity, dimethylbenzene equal solvent residual using macroreticular resin, production cost and quality control cost are dramatically saved, and psychoactive compositions THC can be excluded completely.The very low three classes organic reagent of purified water and toxicity is only used in the above method, reagent environmental protection, technological operation is simple, and instrument and equipment is easy to get, and can reduce cost, reduces pollution, is conducive to industrialized production.Industrial hemp extract obtained by the above method is rich in cannabinol compounds CBDV, CBG and CBD etc., wherein the total content of above-mentioned cannabinol compounds may be up to 80% or more, the rate of transform may be up to 99% or more.
Description
Technical field
The present invention relates to extractive technique fields, and in particular to a kind of industrial hemp extract rich in cannabinol compounds
Preparation method.
Background technique
Hemp (scientific name: Cannabis sativa L.) is Cannabaceae, Cannabis plant, is commonly called as Chinese fiber crops, hemp, fire fiber crops,
Plant it is with a long history, have important agricultural and medical value, be mainly distributed on the ground such as Yunnan, Guizhou, Sichuan, Guangxi, Anhui,
Ancient times are mainly used for making clothes, papermaking material, rope and grease etc..Contain a kind of toxic component tetrahydrocannabinol in hemp
(THC) it can make one to cause unreal habituation, easily be used to refine drugs, harm society, once by multiple countries when considerably long by criminal
It forbids cultivating in phase.
Since the economy of hemp, medical value are high, in the 1980s, there is European countries' research to cultivate low toxicity greatly
Numb kind and the plantation that puts it over.In the 1990s, height of the European Union according to THC content in hemp floral leaf, hemp is divided into
Medicinal (THC > 0.5%), osculant (0.3% < THC < 0.5%) and fibroid (THC < 0.3%).Wherein fibroid poison
Property is low, specializes in industrial use, referred to as " industrial hemp ", the THC content in growth period hemp floral leaf is less than 3/1000ths, no
Have drugs utility value, it can legal progress large-scale planting and industrialized developing utilization.It is higher in view of the value of industrial hemp,
China gradually releases the limitation to industrial hemp in multiple provinces, and under multidisciplinary common supervision, and plantation, exploitation industry are big
Fiber crops.
Industrial hemp is treasured from head to foot, and wherein cannabinol compounds have high medical value.Currently, people are from big
More than 80 cannabinol compounds are isolated in numb plant.Cannabinol compounds are a kind of terpenes phenolic compounds, wherein
Mainly there are cannabidiol (CBD), cannabidivarin (CBDV), cannabinol (CBN), cannabigerol (CBG), cannabichromene
(CBC)、THC、Δ9Tetrahydro time cannabinol (THCV) etc..These cannabinol compounds have been shown to have very strong pharmacology
Activity, e.g., CBD do not have neurotoxicity, can hinder influence of the THC to nerve system of human body, and have apparent anti-convulsion
The pharmacological activity such as contraction, resisting rheumatoid arthritis, antianxiety have huge industry development value；CBD and THCV can influence lipid and
Glycometabolism is likely to become new selection of control type 2 diabetic patient's blood glucose etc., and CBDV has preferable antiepileptic activity, simultaneously
Some researches show that CBDV can reduce nausea, helps to treat gastrointestinal problems, and the joint of these cannabinol compounds
Application effect is stronger.
In cannabinol compounds, CBD, CBDV, CBG, CBDA etc. are non-spiritual active component, and CBN, THC etc. are essence
Refreshing active constituent.
Currently, the research for extracting preparation to non-psychotropic activity cannabinol compounds is relatively fewer, and non-psychotropic activity
Ingredient is similar to psychoactive compositions structure, it is difficult to remove.The prior art is to extract cannabidiol monomer in industrial hemp mostly,
Other cannabinol compounds are not comprehensively considered.Patent application CN106860492A and CN109568389A disclose cannabinoids
The extraction preparation method of compound, but its technique is cumbersome, and agents useful for same is two class reagents, there is certain toxic, can be to experiment people
Member and environmental pollution.
Summary of the invention
In order to overcome the deficiencies of the prior art, the present invention provides a kind of rich in cannabinol compounds CBDV, CBG and CBD
The preparation method of industrial hemp extract.
Above-mentioned preparation method includes the following steps:
(1) hemp medicinal powder is extracted using water-organic reagent mixed solvent I, obtains extracting solution, be concentrated, leaching must be concentrated
Cream；
(2) purified water is added in medicinal extract obtained by step (1), insulated and stirred dissolution is molten by the way that salt is added after being cooled to room temperature
Solution is then allowed to stand layering or by centrifugation layering, separates supernatant liquor, obtains crude extract；
(3) crude extract obtained by step (2) is dissolved, is decolourized, filtering obtains de-inking solution, is concentrated, obtains concentrated extract；
(4) medicinal extract obtained by step (3) is dissolved, carries out column chromatography, eluted with water-organic reagent mixed solvent II, collected
The eluent of cannabinol compounds ingredient.
Optionally, (5) eluent obtained by step (4) is concentrated, and obtains concentrated extract.
Further, above-mentioned cannabinol compounds include CBDV, CBG and CBD etc..
Further, above-mentioned cannabinol compounds further include THCV.
Further, above-mentioned hemp is industrial hemp.
Further, in step (1), hemp medicinal material is selected from: marihuana, cannabis, cannabis root, hemp stalk core and hempseed
The combination of one or more of dregs of rice arbitrary proportion；Preferably, which is cannabis and/or marihuana；Into one
Preferably, the cannabis and/or marihuana use the cannabis and/or marihuana of full-bloom stage to step.
Further, in step (1), the granularity of hemp medicinal powder is that hemp medicinal material is smashed it through to powder obtained by No. 1 sieve
End；Further, the granularity of hemp medicinal powder is that hemp medicinal material is smashed it through to powder obtained by No. 3 sieves.
Further, in step (1), hemp medicinal powder is the hemp medicinal powder after baking.
Still further, above-mentioned baking temperature is 100-200 DEG C.
Still further, above-mentioned baking time is 60-200min.
Further, in step (1), the organic solvent in water-organic solvent mixed solvent I is selected from: methanol, ethyl alcohol and third
The combination of one or more of ketone arbitrary proportion；In one embodiment of the invention, which is ethyl alcohol.
Further, in step (1), the concentration of organic solvent is 70%-99% (tool in water-organic solvent mixed solvent I
Body such as 70%, 80%, 85%, 90%, 95%, 99%).
In one embodiment of the invention, mixed solvent used is water-soluble for the ethyl alcohol of concentration 90-99% in step (1)
Liquid.
Further, in step (1), hemp medicinal powder and water-organic reagent mixed solvent I solid-liquid ratio are 1:5-
1:15 (specific such as 1:5,1:8,1:10,1:12,1:15, w/v).
Further, the extracting method in step (1) is selected from: cold-maceration, ultrasonic extraction, reflux extraction and leaching are filtered method
One or more of combination；In one embodiment of the invention, which is cold-maceration.
Further, in step (1), extraction time is 1-5 times, and each extraction time can be 0.5-2 hours.
Further, it in step (1), is concentrated to be concentrated under reduced pressure, concentration pressure is -0.08~-0.09Mpa.
Further, in step (1), thickening temperature is 55-75 DEG C (specific such as 55,60,65,70,75 DEG C).
In an embodiment of the invention, step (1) includes: to crush hemp medicinal material, and water-is added in baking
Organic reagent mixed solvent, stirring extract, obtain extracting solution, by the extracting solution centrifugal filtration, obtain filtrate, which are carried out dense
Contracting, obtains concentrated extract.
Further, in step (2), the dosage of purified water is 1-3 times of equivalent of hemp medicinal powder.
Further, in step (2), holding temperature be 55-95 DEG C (it is specific such as 55,60,65,70,75,80,85,90,
95℃)。
Further, in step (2), the insulated and stirred time is 0.5-3h (specific such as 0.5,1,2,3h).
Further, in step (2), salt is highly basic salt, strong base ion such as Li+、Na+, K+, Ca2+Such as Deng, acid ion:
Carbonate, bicarbonate radical, sulfate radical, bisulfate ion, citric acid radical, tartrate anion, malate, Vitamin C acid group, methanesulfonic acid
Root, oxalate, halogen ion etc.；Specifically, which can be selected from: sodium carbonate, sodium bicarbonate, sodium sulphate, sodium bisulfate, citric acid
Sodium, sodium tartrate, natrium malicum, sodium ascorbate, methanesulfonic sodium, sodium oxalate, potassium carbonate, saleratus, potassium sulfate, hydrogen sulfate
Potassium, potassium citrate, potassium tartrate, potassium malate, potassium ascorbate, methanesulfonic acid potassium, potassium oxalate, lithium chloride, lithium bromide, iodate
The combination of one or more of lithium, sodium chloride, sodium bromide, sodium iodide, potassium chloride, potassium bromide, potassium iodide.
Further, in step (2), adding time of repose after salt is 2-6h (specific such as 2,3,4,5,6h).
Further, in step (2), the mode of centrifugation is selected from: one or both series connection makes in butterfly centrifugal, tubular type centrifugation
With.
It further, is that water-organic solvent mixing is molten by the dissolution solvent for use of crude extract obtained by step (2) in step (3)
Agent III, wherein organic solvent is selected from: the combination of one or more of methanol, ethyl alcohol and acetone arbitrary proportion；In this hair
In bright one embodiment, which is ethyl alcohol.
Still further, the concentration of organic solvent is 70%-95% (specific in above-mentioned water-organic solvent mixed solvent III
Such as 70%, 75%, 80%, 85%, 90%, 95%).
It in one embodiment of the invention, is that 95% ethyl alcohol is water-soluble by the dissolution solvent for use of crude extract obtained by step (2)
Liquid.
Further, in step (3), the dosage of above-mentioned solvent be hemp medicinal powder equivalent 1-5 times (specific such as 1,
2,3,4,5 times).
Further, in step (3), the decolorising agent used that decolourizes is selected from: active carbon, diatomite, atlapulgite, decoloration sand,
A combination of one or more in talcum powder and paper pulp.
Further, in step (3), the quality for the decolorising agent used that decolourizes is 0.01-0.10 times of hemp medicinal powder
(specific such as 0.01,0.02,0.04,0.05,0.06,0.08,0.10).
Further, in step (3), the temperature of decoloration is 5-60 DEG C (specific such as 5,10,20,25,30,40,50,60
℃)；In one embodiment of the invention, bleaching temperature is room temperature.
Further, in step (3), the time of decoloration is 30-60min (specific such as 30,40,50,60min).
It further, is water-organic solvent mixed solvent by the dissolution solvent for use of medicinal extract obtained by step (3) in step (4)
IV, wherein organic solvent is selected from: the combination of one or more of methanol, ethyl alcohol and acetone arbitrary proportion；In the present invention
One embodiment in, the organic solvent be ethyl alcohol.
Still further, the concentration of organic solvent is 70%-95% (specific in above-mentioned water-organic solvent mixed solvent IV
Such as 70%, 75%, 80%, 85%, 90%, 95%).
It in one embodiment of the invention, is that 95% ethyl alcohol is water-soluble by the dissolution solvent for use of crude extract obtained by step (3)
Liquid.
Further, in step (4), the dosage of above-mentioned solvent is that 0.05-0.20 times of hemp medicinal powder equivalent is (specific
Such as 0.05,0.08,0.10,0.15,0.20 times).
Further, in step (4), column chromatographs filler used and is selected from: bonded silica gel (such as octadecylsilane bonded silica
Glue, octyl silane group silica gel), the combination of polymerization filling, one or more of silica gel；In an implementation of the invention
In example, which is octadecylsilane chemically bonded silica.
Further, in step (4), column chromatograph the partial size of filler used be 10-100 μm (it is specific such as 10,20,30,40,
50、60、70、75、80、90、100μm)。
Further, in step (4), the diameter height that column chromatographs chromatographic column used compares for 3:2-3:12.
Further, in step (4), the organic solvent in water-organic solvent mixed solvent II is selected from: methanol, ethyl alcohol and
The combination of one or more of acetone arbitrary proportion；In one embodiment of the invention, which is ethyl alcohol.
Further, in step (4), the concentration of the organic solvent in water-organic solvent mixed solvent II is 70%-95%
(specific such as 70%, 75%, 80%, 85%, 90%, 95%).
In one embodiment of the invention, above-mentioned water-organic solvent mixed solvent II is the ethyl alcohol that concentration is 70-95%
Aqueous solution.
Further, in step (4), elution flow rate is 2-5BV/h (specific such as 2,3,4,5BV/h).
Further, it in step (5), is concentrated to be concentrated under reduced pressure.
The present invention also provides the industrial hemp extract prepared by the above method, rich in cannabinol compounds CBDV,
CBG and CBD, especially wherein the total content of above-mentioned cannabinol compounds may be up to 80% or more, and the rate of transform may be up to 99%
More than.
The present invention also provides above-mentioned industrial hemp extracts and preparation method thereof to prepare drug, medical and beauty treatment product and change
Application in cosmetic.
The present invention also provides a kind of drug, medical and beauty treatment product and makeups comprising the above-mentioned industrial hemp extract of the present invention
Product.
The present invention is enriched with cannabinol compounds by the way of adding salt and centrifugation, and a step is completely removed water-soluble miscellaneous
Matter avoids sinking technique using conventional water or removes the toluene introduced when water-solubility impurity, dimethylbenzene equal solvent using macroreticular resin
Residual, dramatically saves production cost and quality control cost, and can exclude psychoactive compositions THC completely, in technique only
The very low three classes organic reagent of purified water and toxicity is used, reagent environmental protection, technological operation is simple, and instrument and equipment is easy to get, and can drop
Low cost reduces pollution, is conducive to industrialized production.Industrial hemp extract prepared by the present invention is rich in cannabinol compounds
The total content of CBDV, CBG and CBD, especially above-mentioned cannabinol compounds may be up to 80% or more, and the rate of transform may be up to
99% or more.
Detailed description of the invention
Fig. 1 show the liquid chromatogram of blank control (95% ethyl alcohol).
Fig. 2 show the liquid chromatogram of cannabinol compounds (CBDV, CBG, CBD, THCV, THC) reference substance.
Fig. 3 show the liquid phase color of cannabinol compounds (CBDV, CBG, CBD, THCV, THC) in 1 sample solution of embodiment
Spectrogram.
Fig. 4 show cannabinol compounds in the Cannador that embodiment 1 obtains (CBDV, CBG, CBD, THCV,
THC liquid chromatogram).
Fig. 5 show the liquid phase color of cannabinol compounds (CBDV, CBG, CBD, THCV, THC) in 2 sample solution of embodiment
Spectrogram.
Fig. 6 show cannabinol compounds in the Cannador that embodiment 2 obtains (CBDV, CBG, CBD, THCV,
THC liquid chromatogram).
Specific embodiment
Unless otherwise defined, the present invention used in all scientific and technical terms have with the present invention relates to technologies to lead
The normally understood identical meaning of the technical staff in domain.
Heretofore described " Cannador " refers to from the raw material of hemp extract part (such as cannabis and/or leaf)
Obtained product is extracted, can be liquid or solid form, wherein including at least one cannabinol compounds, it is preferable that packet
Containing CBD, CBDV, CBG and THCV, particularly, THC is free of.
Unless stated otherwise, heretofore described " content " is generally mass content, for example, the CBDV in extract
Content be x%, refer to: in extract, the quality of CBDV accounts for the x% of extract gross mass.
The description such as heretofore described " x times of medicinal material equivalent ", refers to solvent such as purified water, ethanol solution of use etc.
Volume is x times of quality of medicinal material, and specifically, such as " 1 times of medicinal material equivalent ", if quality of medicinal material is 1g, the dosage of solvent for use is
1mL。
To make the object, technical solutions and advantages of the present invention clearer, below in conjunction with the embodiment of the present invention to this hair
Bright technical solution, which is done, to be further fully described by.The described embodiment is only a part of the embodiment of the present invention, does not constitute pair
The restriction of the scope of the present invention, it is obtained by those of ordinary skill in the art without making creative efforts all
Other embodiments shall fall within the protection scope of the present invention.
Sample detection analysis uses high performance liquid chromatography in following example and comparative example, and the specific method is as follows:
Chromatographic condition and system suitability: using octadecylsilane chemically bonded silica as filler；With 0.1% formic acid water
Solution is mobile phase A, using 0.1% formic acid acetonitrile as Mobile phase B, is eluted by the elution program of table 1；Detection wavelength is 220nm.Reason
5000 should be not less than by calculating by plate number by the peak CBD.
1 elution program of table
| Time/min | A (0.1% aqueous formic acid) | B (0.1% formic acid acetonitrile) |
| 0 | 30% | 70% |
| 6 | 30% | 70% |
| 12 | 23% | 77% |
| 22 | 23% | 77% |
| 22.2 | 30% | 70% |
| 26 | 30% | 70% |
The preparation of reference substance solution: precision weighs CBD reference substance, adds methanol that the reference substance solution of 0.15mg/mL is made, i.e.,
?；Precision weighs CBDV reference substance, add methanol be made the reference substance solution of 0.01mg/mL to get；Precision weighs THCV control
Product, add methanol be made the reference substance solution of 0.01mg/mL to get；Precision weighs CBG reference substance, adds methanol that 0.01mg/mL is made
Reference substance solution to get；Precision weighs tetrahydrocannabinol reference substance, adds methanol that the reference substance solution of 0.01mg/mL is made, i.e.,
?.
The preparation of test solution: taking sample solution 1.1mL, adds methanol constant volume to 25mL, with miillpore filter (0.45 μm)
Filtration, take subsequent filtrate to get.
Measuring method: accurate absorption reference substance solution and each 10 μ L of test solution respectively, injection liquid chromatograph, measurement,
To obtain the final product.
Fig. 1 show blank control (95% ethyl alcohol) liquid chromatogram, Fig. 2 show cannabinol compounds (CBDV,
CBG, CBD, THCV, THC) reference substance liquid chromatogram, wherein the retention time of each cannabinol compounds is respectively as follows:
CBDV:5.680min；CBG:9.055min；CBD:9.590min；THCV:10.363min；THC:16.976min.
Embodiment 1
(1) industrial hemp floral leaf medicinal material is crushed, crosses No. 1 sieve, 100 DEG C of baking 200min, after taking a certain amount of baking
Hemp floral leaf medicinal material, by solid-liquid ratio 1:8 (w/v) be added 95% ethyl alcohol, be stirred at room temperature extraction twice, 1 hour every time, filtering,
Combined extract, centrifugal filtration, centrifugal filtration liquid are concentrated under reduced pressure (65 DEG C, -0.08~-0.09Mpa) to medicinal extract, medicinal material are added
The purified water that 3 times of equivalent, insulated and stirred 30 minutes at 75 DEG C, sets in liquid separation tank and is cooled to room temperature, and it is molten that sodium carbonate stirring is added
Xie Hou is stored at room temperature 3h, separates upper layer to get hemp crude extract.
(2) medicinal material equivalent is added in the 95% ethyl alcohol stirring and dissolving for measuring gained hemp crude extract with 3 times of medicinal material equivalent
0.05 times of active carbon is stirred at room temperature 40 minutes, then filters, and filtrate is concentrated into medicinal extract after mixing, and 0.1 times of medicinal material equivalent is added
95% ethyl alcohol dissolved, obtain sample solution, analyzed it by high performance liquid chromatography, chromatogram is as shown in Figure 3.On
Sample carries out column chromatography, and chromatographic stuffing is octadecylsilane chemically bonded silica, and it is mobile phase with 75% ethyl alcohol that partial size, which is 30 μm, stream
Speed is that 4BV/h is eluted, and collects the 1st to the 2.5th times of column volume fraction, is concentrated under reduced pressure into thick paste to get rich in cannabinoids
The extract of compound, is analyzed it by high performance liquid chromatography, and chromatogram is as shown in Figure 4.Wherein, cannabinoids
Closing object total content is 80.6%, wherein CBDV content is 10.99%, CBG content is 1.42%, CBD content is 66.38%,
THCV content is that 1.81%, THC is not detected.
Embodiment 2
(1) industrial hemp floral leaf medicinal material is crushed, crosses No. 3 sieves, 200 DEG C of baking 60min, after taking a certain amount of baking
Hemp floral leaf medicinal material is added 90% ethyl alcohol by solid-liquid ratio 1:10 (w/v), extraction is stirred at room temperature twice, and 1 hour every time, filtering,
Combined extract, centrifugal filtration, centrifugal filtration liquid are concentrated under reduced pressure (65 DEG C, -0.08~-0.09Mpa) to medicinal extract, medicinal material are added
2 times of amount purified waters of equivalent, heat preservation rotation 30 minutes at 70 DEG C, will turn solution and carry out butterfly centrifugal layering, revolving speed 5000
Rev/min, upper layer is separated to get hemp crude extract.
(2) medicinal material equivalent is added in the 95% ethyl alcohol stirring and dissolving for measuring gained hemp crude extract with 3 times of medicinal material equivalent
0.05 times of diatomite is stirred at room temperature 30 minutes, then filters, and filtrate is concentrated into medicinal extract after mixing, and the 0.08 of medicinal material equivalent is added
95% ethyl alcohol again is dissolved, and is obtained sample solution, is analyzed it by high performance liquid chromatography, chromatogram is as shown in Figure 5.
Loading carries out column chromatography, and chromatographic stuffing is octadecylsilane chemically bonded silica, and it is mobile phase with 70% ethyl alcohol that partial size, which is 75 μm,
Flow velocity is that 3BV/h carries out isocratic elution, collects the 0.5th to the 2nd times of column volume fraction, is concentrated under reduced pressure into thick paste to get rich in big
The extract of numb phenolic compound, is analyzed it by high performance liquid chromatography, and chromatogram is as shown in Figure 6.Wherein, hemp
Phenolic compound total content is 76.8%, and wherein CBDV content is 10.47%, CBG content is 1.28%, CBD content is
63.34%, THCV content is that 1.71%, THC is not detected.
Comparative example 1
Referring to extraction, concentration step and the parameter in 1 step of embodiment (1), mentioned by the hemp floral leaf of identical weight
Take, be concentrated, by medicinal extract be added 6 times of medicinal material equivalent amount purified waters, stirring be suspended, in 12 DEG C or less stratification 8 hours, receive
Collect lower sediment to get hemp crude extract.
Comparative example 2
Referring to extraction, concentration step and the parameter in 2 step of embodiment (1), mentioned by the hemp floral leaf of identical weight
It takes, be concentrated, medicinal extract is added to the purified water of 4 times of medicinal material equivalent amounts, be suspended, through macroporous resin purification, first removed with purifying water elution
Water-solubility impurity is removed, then with 90% ethanol elution, to get hemp crude extract after concentration.
Detect prepared by embodiment 1-2 and comparative example 1-2 respectively in crude extract the total content of cannabinol compounds and
The rate of transform.Testing result is as shown in table 2.
The different crude separation method Contrast on effect of table 2
| Serial number | Crude separation temperature | The crude separation time (h) | Total content | The rate of transform |
| Embodiment 1 | Room temperature | 3 | 23.25% | 99.87% |
| Embodiment 2 | Room temperature | 0.5 | 23.89% | 99.56% |
| Comparative example 1 | 12 DEG C of < | 8 | 18.56% | 87.17% |
| Comparative example 2 | Room temperature | 6 | 23.12% | 88.45% |
Comparative example 3
Referring to decoloration, concentration, dissolution and the column chromatography steps and parameter in 1 step of embodiment (2), by the big of identical weight
Fried dough twist Leave extract (1 step of embodiment (1) preparation), through decolorization, concentration, medicinal extract is dissolved with 95% ethyl alcohol, obtains sample solution,
Column chromatography is carried out, chromatographic stuffing is octadecylsilane chemically bonded silica, is eluted with 65% methanol aqueous solution, is collected in addition to THC
The fraction of other cannabinol compounds merges, and is concentrated to get Cannador finished product.
Comparative example 4
Referring to decoloration, concentration, dissolution and the column chromatography steps and parameter in 2 step of embodiment (2), by the big of identical weight
Fried dough twist Leave extract (2 step of embodiment (1) preparation), through decolorization, concentration, medicinal extract is dissolved with 95% ethyl alcohol, obtains sample solution,
Column chromatography is carried out, chromatographic stuffing is octadecylsilane chemically bonded silica, is eluted with 55% acetonitrile solution, is collected in addition to THC
The fraction of other cannabinol compounds merges, and is concentrated to get Cannador finished product.
Detect prepared by embodiment 1-2 and comparative example 3-4 respectively in extract the total content of cannabinol compounds and
The rate of transform.Testing result is as shown in table 2.
The different isolation and purification method Contrast on effect of table 3
| Serial number | Column chromatographic stuffing and eluant, eluent | Total content | The rate of transform | THC content |
| Embodiment 1 | Octadecylsilane chemically bonded silica；75% ethyl alcohol | 80.60% | 92.54% | It is not detected |
| Embodiment 2 | Octadecylsilane chemically bonded silica；70% ethyl alcohol | 76.80% | 88.18% | It is not detected |
| Comparative example 3 | Octadecylsilane chemically bonded silica；65% methanol | 69.44% | 85.70% | It is not detected |
| Comparative example 4 | Octadecylsilane chemically bonded silica；55% acetonitrile | 68.32% | 84.47% | It is not detected |
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Within mind and principle, made any modification, equivalent replacement etc. be should all be included in the protection scope of the present invention.
Claims (14)
1. a kind of preparation method of industrial hemp extract comprising following steps:
(1) industrial hemp medicinal powder is extracted using water-organic reagent mixed solvent I, obtains extracting solution, be concentrated, leaching must be concentrated
Cream；
(2) purified water is added in medicinal extract obtained by step (1), insulated and stirred dissolution is right by the way that salt dissolution is added after being cooled to room temperature
Afterwards stratification or by centrifugation layering, separate supernatant liquor, obtain crude extract；
(3) crude extract obtained by step (2) is dissolved, is decolourized, filtering obtains de-inking solution, is concentrated, obtains concentrated extract；
(4) medicinal extract obtained by step (3) is dissolved, carries out column chromatography, eluted with water-organic reagent mixed solvent II, collect hemp
The eluent of phenolic compound ingredient；
Preferably, the cannabinol compounds include cannabidivarin, cannabigerol and cannabidiol.
2. preparation method as claimed in claim 1, which is characterized in that in step (1), the industrial hemp medicinal material is selected from: marihuana,
The combination of one or more of cannabis, cannabis root, hemp stalk core and hemp seed meal arbitrary proportion；Preferably, described
Industrial hemp medicinal material is cannabis and/or marihuana；
The industrial hemp medicinal powder is the gained powder after baking by industrial hemp pulverizing medicinal materials；
The baking temperature is 100-200 DEG C, baking time 60-200min.
3. preparation method as claimed in claim 1, which is characterized in that in step (1), in the water-organic solvent mixed solvent I,
The organic solvent is selected from: the combination of one or more of methanol, ethyl alcohol and acetone arbitrary proportion；The water-is organic
The concentration of organic solvent is 70%-99% in solvent mixed solvent I；
Preferably, the water-organic solvent mixed solvent I is the ethanol water of concentration 90-99%.
4. preparation method as claimed in claim 1, which is characterized in that industrial hemp medicinal powder described in step (1) and water-are organic
The solid-liquid ratio of reagent mixed solvent I is 1:5-1:15；
The dosage of purified water described in step (2) is 1-3 times of equivalent of industrial hemp medicinal powder.
5. preparation method as claimed in claim 1, which is characterized in that in step (2), the holding temperature is 55-95 DEG C；Heat preservation is stirred
Mixing the time is 0.5-3h.
6. preparation method as claimed in claim 1, which is characterized in that salt described in step (2) is highly basic salt；Preferably, the salt
It is selected from: sodium carbonate, sodium bicarbonate, sodium sulphate, sodium bisulfate, sodium citrate, sodium tartrate, natrium malicum, sodium ascorbate, first
It is sodium sulfonate, sodium oxalate, potassium carbonate, saleratus, potassium sulfate, potassium acid sulfate, potassium citrate, potassium tartrate, potassium malate, anti-bad
Hematic acid potassium, methanesulfonic acid potassium, potassium oxalate, lithium chloride, lithium bromide, lithium iodide, sodium chloride, sodium bromide, sodium iodide, potassium chloride, bromination
The combination of one or more of potassium, potassium iodide；
The time of repose is 2-6h.
7. preparation method as claimed in claim 1, which is characterized in that be centrifuged and be selected from described in step (2): butterfly centrifugal, tubular type from
One or both is used in series in the heart.
8. preparation method as claimed in claim 1, which is characterized in that, will be used in the dissolution of crude extract obtained by step (2) in step (3)
Solvent is water-organic solvent mixed solvent III；
Wherein the organic solvent is selected from: the combination of one or more of methanol, ethyl alcohol and acetone arbitrary proportion；It is described
The concentration of organic solvent is 70%-95% in water-organic solvent mixed solvent III；
The water-organic solvent mixed solvent III dosage is 1-5 times of industrial hemp medicinal powder equivalent.
9. preparation method as claimed in claim 1, which is characterized in that in step (3), the decolorising agent used that decolourizes is selected from: active carbon, silicon
A combination of one or more in diatomaceous earth, atlapulgite, decoloration sand, talcum powder and paper pulp；
The quality of decolorising agent used in decolourizing is 0.01-0.10 times of hemp medicinal powder；
The temperature of decoloration is 5-60 DEG C；
The time of decoloration is 30-60min.
10. preparation method as claimed in claim 1, which is characterized in that in step (4), the dissolution of medicinal extract obtained by step (3) is used molten
Agent is water-organic solvent mixed solvent IV；
Wherein the organic solvent is selected from: the combination of one or more of methanol, ethyl alcohol and acetone arbitrary proportion；It is described
The concentration of organic solvent is 70%-95% in water-organic solvent mixed solvent IV；
The water-organic solvent mixed solvent IV dosage is 0.05-0.20 times of industrial hemp medicinal powder equivalent.
11. preparation method as claimed in claim 1, which is characterized in that the column chromatographs filler used and is selected from: bonded silica gel, polymerization
The combination of one or more of filler, silica gel；Preferably octadecylsilane chemically bonded silica；
The partial size that the column chromatographs filler used is 10-100 μm；
The diameter height that the column chromatographs chromatographic column used compares for 3:2-3:12；
The elution flow rate is 2-5BV/h.
12. such as the described in any item preparation methods of claim 1-11, which is characterized in that water-organic solvent described in step (4)
Organic solvent in mixed solvent II is selected from: the combination of one or more of methanol, ethyl alcohol and acetone arbitrary proportion；Institute
The concentration for stating organic solvent in water-organic solvent mixed solvent II is 70%-95%；
Preferably, the water-organic solvent mixed solvent II is the ethanol water that concentration is 70-95%.
13. a kind of industrial hemp extract of any one of claim 1-12 the method preparation.
14. industrial hemp extract as claimed in claim 13 is preparing answering in drug, medical and beauty treatment product and cosmetics
With.
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