CN109734560A - A kind of cannabidiol extract and preparation method thereof - Google Patents
A kind of cannabidiol extract and preparation method thereof Download PDFInfo
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- CN109734560A CN109734560A CN201910148366.6A CN201910148366A CN109734560A CN 109734560 A CN109734560 A CN 109734560A CN 201910148366 A CN201910148366 A CN 201910148366A CN 109734560 A CN109734560 A CN 109734560A
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Abstract
The invention belongs to biomedicine technical fields, more particularly to a kind of cannabidiol extract and preparation method thereof, the weight percentage of cannabidiol is more than or equal to 95% less than 100% in cannabidiol extract of the present invention, and the weight percentage of tetrahydrocannabinol is to be not detected；The technical problem to be solved in the present invention is to provide a kind of new method for preparing cannabidiol using ball-milling method, which can significantly improve the recovery rate that cannabidiol is extracted from industrial hemp, simplify extraction step.
Description
Technical field
The invention belongs to biomedicine technical field, specific a kind of cannabidiol extract and preparation method thereof.
Background technique
Hemp (Cannabis sativa) is a kind of very promising medicinal plant, wherein in cannabinol compounds
The highest compound of medical value is tetrahydrocannabinol and cannabidiol (CBD), research shows that cannabidiol has important face
Bed application prospect, such as kinds cancer, epilepsy, Alzheimer's disease, the specific certain curative effect (Heilungkiang [J] of Huntingdon disease
Science, 2018,1:024).
Ball mill grinding technology is one of micronization technology important composition, be generally used at present material submicron order grinding,
The preparation of mechanical alloy, it can also be used to the biggish medicinal material of thermo-responsive and stickiness and the broken essence of biological cell and mentioning for DNA, RNA
Take ([J] modern medicines and clinical, 2014 (2): 154-157.).Currently, because spreading unchecked for drugs leads to the easily poison processed such as hemp
The supervision of material becomes increasingly strict, therefore to prevent hemp from flowing into illegal channel, current natural drug is extracted in industry more
Tend to extract cannabidiol with industrial hemp.
Industrial hemp is called Chinese fiber crops, refers to the hemp that tetrahydrocannabinol content is lower than 0.3%, does not have drugs exploitation value
Value, same because tetrahydrocannabinol and cannabidiol content are lower, enrichment difficulty is big, and general crude drug extracts industry and generally adopts
Industrialization extraction is carried out with more complicated technique and the method for a large amount of solvent extractions, as CN104277917A discloses one kind
By the extracting method of industrial hemp essential oil, CN106278828A discloses a kind of leach by ethyl alcohol and is prepared into column chromatography
To cannabidiol, but still there is using a large amount of organic solvents to lead to dissolvent residual and polluting environment, extraction process is complicated, mentions
The defects of taking rate inefficiency.
To sum up, study it is a kind of novel, effectively extracted from industrial hemp cannabidiol, reduce organic solvent use and
The extracting method for simplifying processing step extracts commercial value with higher in industry in hemp.
Summary of the invention
For these reasons, applicant is by repeatedly creative test, and the technical problem to be solved in the present invention is to provide one
The new method for preparing cannabidiol using ball-milling method of kind, the preparation method can significantly improve and extract hemp from industrial hemp
The recovery rate of diphenol simplifies extraction step.
Technical scheme is as follows:
A kind of cannabidiol extract, the weight percentage of cannabidiol is to be less than more than or equal to 95% in extract
100%, the weight percentage of tetrahydrocannabinol is to be not detected.
The weight percentage of cannabidiol is more than or equal to 97% less than 100% in preferred extract, tetrahydro hemp
The weight percentage of phenol is to be not detected.
The cannabidiol extract the preparation method comprises the following steps:
(1) it screens and is dehydrated: the industrial hemp dried being put into pulverizer and is crushed, then by the work after pulverizing and sieving
Sparetime university fiber crops are dehydrated, and the industrial hemp crude product (w/w) that moisture content is lower than 10% is prepared；
(2) ball milling: the industrial hemp raw material that step (1) obtains is put into ball mill, cooling by liquid nitrogen, grinding 0.1
Obtain within~5 hours the postindustrial hemp raw material of ball milling；
(3) extract: the raw material that obtains to step (2) is added extraction solvent, soak extraction 1~8 hour under room temperature, obtains just
Extract；
(4) it is centrifuged: the first extract that step (3) obtains being centrifuged, supernatant is taken；
(5) it is concentrated and dry: the supernatant that step (4) obtains is concentrated under reduced pressure, cannabidiol is obtained after drying and is extracted
Object crude product.
The sieve of pulverizer described in step (1) is 30~50 mesh；The temperature of dehydration and drying is selected from 60~80 DEG C.
Ball mill described in step (2) is selected from bead grinding machine, planetary mill, vibration mill, eccentric vibration-type mill
Machine, gravity dependent form ball mill, rod mill and tumbling mill；The abrasive body diameter of the ball mill is selected from 2~15mm.
The range of the D90 of raw material described in step (2) is selected from 500~2000nm；The range of the D50 of the raw material is selected from
1000~2000nm.
Extraction solvent described in step (3) is selected from the alcohols of C1-C4, and preferably methanol, ethyl alcohol, isopropanol or its mixing is molten
Agent.
The plastid ratio of raw material described in step (3) and extraction solvent is selected from 3:1~1:3, preferably 2:1,1:1 or 1:2.
The revolving speed of centrifuge separation described in step (4) is selected from 500~2000 revs/min, preferably 1000~1500 revs/min
Clock.
The preparation method of cannabidiol extract includes:
(1) cannabidiol crude product is dissolved in mixed organic solvents, wherein mixed organic solvents and cannabidiol crude product body
Long-pending and weight ratio is 15-25:1 (ml/g), and cannabidiol crude product solution is prepared；；
(2) under the conditions of 5-10 DEG C, the anti-molten of cannabidiol is added to cannabidiol crude product solution obtained in step (1)
Agent, it filters, it is dry, obtain cannabidiol extract.The saturated alkane class and C1~C3 that the mixed solvent is C5~C10
The mixed solvent of alcohols；The volume ratio of the alcohols of the saturated alkane class and C1~C3 of the C5~C10 is selected from 1:1~1:3；It is described
Anti-solvent is water, and the volume ratio of the water and cannabidiol crude product solution is selected from 1:1~1:5.
The preparation method of cannabidiol extract of the present invention further include: column chromatography method and Xu Ning intermediate processing
Deng
The present invention further provides a kind of cannabidiol highly finished product extracted from industrial hemp by the above method
Purposes in the pharmaceutical composition of preparation treatment neuropsychiatric disease, the neuropsychiatric disease are selected from schizophrenia, suppression
Strongly fragrant disease, anesthesia and mania.
Specific embodiment
Below the technical scheme of the invention is illustrated by a specific example, but the scope of the present invention is not limited thereto.
Content described in this specification embodiment is only enumerating to the way of realization of inventive concept, protection of the invention
Range should not be construed as being limited to the specific forms stated in the embodiments, and protection scope of the present invention is also and in art technology
Personnel conceive according to the present invention it is conceivable that equivalent technologies mean.Although embodiment of the invention below is retouched
It states, but the invention is not limited to above-mentioned specific embodiments and applications field, following specific embodiments is only to show
It is meaning property, guiding, rather than it is restrictive.Those skilled in the art under the enlightenment of this specification and are not taking off
In the case where the range protected from the claims in the present invention, a variety of forms can also be made, these belong to the present invention
The column of protection.
The following tests of the present invention are on the basis of multiple creative test, with the claimed technical solution of the present invention
Based on, the conclusive test of the research staff of summary.
Compared with prior art, technical solution of the present invention has the advantage that
The method provided by the invention for extracting cannabidiol from industrial hemp by ball-milling method is mentioned in the prior art
Method is taken to compare, simple process does not need to extract repeatedly using a large amount of organic solvents；Furthermore it is possible to when greatly shortening extraction
Between and improve recovery rate, have preferable pharmaceuticals industry application value.
Embodiment 1, cannabidiol crude product extract
(1) 10kg industrial hemp cleaned, dried, (bought from the bright food in Nanjing Willie using XL-60C type medicinal herb grinder
Product Machinery Co., Ltd.), 50 meshes are then crossed, the industrial hemp floral leaf after pulverizing and sieving is de- in 75 DEG C in being placed in baking oven
Water is dry, obtains industrial hemp crude product；
(2) industrial hemp crude product the vertical ball mill with liquid nitrogen cooling recirculation system is placed in (to buy from Laizhou City
Long Jun chemical machinery Co., Ltd), it uses diameter to be ground for the spherical steel ball (about 30~50) of 10mm and 8mm, grinds
Time is 1 hour, and temperature setting is -10 DEG C, the partial size for the industrial hemp raw material being prepared (Winner2308 intelligence after measured
The dry-wet integrated laser particle analyzer of energy type), D90 is about 1500~1800nm, and D50 is about 1000~1200nm；
(3) dehydrated alcohol, the matter of dehydrated alcohol and industrial hemp raw material is added to the industrial hemp raw material obtained after ball milling
Volume ratio is 1:1, is impregnated 3 hours under room temperature；
(4) first extract obtained by centrifugation step (3), is centrifuged 15 minutes, takes supernatant by 1000 revs/min of revolving speed；
(5) supernatant obtained by step (4) is concentrated under reduced pressure, is dried at 90 DEG C, cannabidiol crude product is prepared
20.1g。
The purification -1 of embodiment 2, cannabidiol crude product
(1) by 1 gained cannabidiol crude product 10g of embodiment be dissolved in 20ml ethyl alcohol and n-hexane in the mixed solvent (ethyl alcohol with
The volume ratio of n-hexane mixed solvent is 1:1), cannabidiol crude product solution is prepared；
(2) cannabidiol crude product solution temperature obtained by step (1) is reduced to 5 DEG C, pure water (water and big is added into solution
The volume ratio of numb diphenol crude product solution is 1:2), 5~10 DEG C stand overnight, it filters, it is dry, obtain cannabidiol extract
8.16g (cannabidiol content 99.6%, tetrahydrocannabinol is not detected).
The purification -2 of embodiment 3, cannabidiol crude product
(1) by 1 gained cannabidiol crude product 5g of embodiment be dissolved in 10ml ethyl alcohol and normal heptane in the mixed solvent (ethyl alcohol with just
The volume ratio of heptane mixed solvent is 4:1), cannabidiol crude product solution is prepared；
(2) cannabidiol crude product solution temperature obtained by step (1) is reduced to 8 DEG C, pure water (water and big is added into solution
The volume ratio of numb diphenol crude product solution is 1:4), 5~10 DEG C stand overnight, and filter, and it is dry, obtain cannabidiol extract 4.1g
(cannabidiol content 99.5%, tetrahydrocannabinol is not detected).
Test comparison example 4,
Experimental material
Reference substance 1: it is extracted referring to 1 the method for patent CN106278828A embodiment；
Experimental example sample 1: it is prepared referring to 1 the method for embodiment；
Experimental example sample 2: it is prepared referring to 3 the method for embodiment；
Determination method: laboratory apparatus: Hitachi, Japan H itachi L-2300 high performance liquid chromatograph；Japan
Hitachi, Ltd's H itachi L-2400 UV detector；Hitachi, Japan D-2000E lite chromatographic work station；
Sartorius company BP210S electronic balance；
Reagent: ethyl alcohol, tetrahydrofuran are chromatographically pure, are purchased from Shandong YuWang Industry Co., Ltd；Acetic acid is chromatographically pure；It is purchased from
Guangzhou is relied on oneself chromatography tech Co., Ltd；
Test sample: cannabidiol crude product is prepared by 1 the method for embodiment；
Test solution is prepared: taking test solution 1mg, the test solution of 100 μ g/mL is configured to ethyl alcohol constant volume.
Reference substance: cannabidiol and tetrahydrocannabinol are purchased from Nat'l Pharmaceutical & Biological Products Control Institute
Chromatographic column: chromatographic column is Agilent ZORBAX SB-C18 liquid-phase chromatographic column 880975-902
Mobile phase is prepared: organic phase is ethyl alcohol and tetrahydrofuran mixed solvent (v/v=15:1)；The vinegar that water phase is 0.8%
Acid sodium aqueous solution (w/v)
Mobile phase:
Sodium acetate aqueous solution (with acetic acid tune pH to 2.5)-ethyl alcohol tetrahydrofuran (90:10) of A:0.8%
Sodium acetate aqueous solution (with acetic acid tune pH to 2.5)-ethyl alcohol tetrahydrofuran (60:40) of B:0.8%
Testing conditions: flow velocity 1.0mL/min；Detection wavelength is 220nm；Column temperature is 35 DEG C；Sample volume is 20 μ L
1 gradient condition of table (volume ratio)
| Time (min) | A (%) | B (%) |
| 0 | 80 | 20 |
| 5 | 75 | 25 |
| 15 | 55 | 45 |
| 20 | 45 | 55 |
| 25 | 20 | 80 |
| 30 | 20 | 80 |
Reference substance solution preparation and the determination of equation of linear regression: cannabidiol reference substance (1mg/mL) solution is taken, with second
Alcohol constant volume is prepared into the reference substance mother liquor of 200 μ g/mL cannabidiols, then being configured to concentration gradient is 0.05 μ g/mL, 0.5 μ g/
The cannabidiol reference substance solution of mL, 1 μ g/mL, 5 μ g/mL, 25 μ g/mL, 50 μ g/mL, 100 μ g/mL, 200 μ g/mL；According to big
The identical method of numb diphenol, takes tetrahydrocannabinol reference substance (1mg/mL) solution, it is big to be prepared into 200 μ g/mL with ethyl alcohol constant volume
The reference substance mother liquor of numb diphenol, then being configured to concentration gradient is 0.02 μ g/mL, 0.2 μ g/mL, 0.8 μ g/mL, 4 μ g/mL, 20 μ g/
ML, 40 μ g/mL, 80 μ g/mL, 160 μ/mL tetrahydrocannabinol reference substance solution.
Following equation of linear regression is obtained according to its corresponding peak area:
Cannabidiol: Y=75621X+39051, n=8 (R2=0.9995)
Tetrahydrocannabinol: Y=73973X+36298, n=8 (R2=0.9994)
Above-mentioned reference substance and and experimental example sample CBD content testing result referring to table 2.
The result of 2 each sample CBD content of table
| Title | CBD content | Tetrahydrocannabinol content |
| Standard items | 100% | It is not detected |
| Reference substance | 93.7% | 3.1% |
| Experimental example sample 1 | 90.9% | 4.5% |
| Experimental example sample 2 | 99.5% | It is not detected |
By above-mentioned testing result it is found that method provided by preparation method provided by the present invention and CN106278828A
It compares, simple process, the method for not needing to extract and chromatograph by column repeatedly, recovery rate is up to 90% or more；In addition, purification
Later cannabidiol extract, purity reach 99% or more, tetrahydrocannabinol are not detected, and meet medicinal standard, therefore this hair
Bright preparation and the refining methd of providing is produced suitable for pharmaceuticals industry metaplasia, and the pollution of environment is reduced while reducing production cost.
Claims (11)
1. a kind of cannabidiol extract, it is characterised in that in extract the weight percentage of cannabidiol be more than or equal to
95% less than 100%, and the weight percentage of tetrahydrocannabinol is to be not detected.
2. a kind of cannabidiol extract according to claim 1, it is characterised in that the weight of cannabidiol in extract
Percentage composition is more than or equal to 97% less than 100%, and the weight percentage of tetrahydrocannabinol is to be not detected.
3. a kind of cannabidiol extract according to claim 1 or 2, it is characterised in that: the cannabidiol extract
The preparation method comprises the following steps:
(1) it screens and is dehydrated: the industrial hemp dried being put into pulverizer and is crushed, then the industry after pulverizing and sieving is big
Fiber crops are dehydrated, and the industrial hemp crude product (w/w) that moisture content is lower than 10% is prepared；
(2) ball milling: the industrial hemp raw material that step (1) obtains is put into ball mill, cooling by liquid nitrogen, and grinding 0.1~5 is small
When obtain the postindustrial hemp raw material of ball milling；
(3) extract: the raw material that obtains to step (2) is added extraction solvent, soak extraction 1~8 hour under room temperature, obtains just mentioning
Liquid；
(4) it is centrifuged: the first extract that step (3) obtains being centrifuged, supernatant is taken；
(5) it is concentrated and dry: the supernatant that step (4) obtains is concentrated under reduced pressure, it is thick that cannabidiol extract is obtained after drying
Product.
4. a kind of cannabidiol extract according to claim 3, which is characterized in that pulverizer described in step (1)
Sieve is 30~50 mesh；The temperature of dehydration and drying is selected from 60~80 DEG C.
5. a kind of cannabidiol extract according to claim 3, which is characterized in that ball mill described in step (2)
Selected from bead grinding machine, planetary mill, vibration mill, eccentric vibration-type grinding machine, gravity dependent form ball mill, rod mill and rolling
Grinding machine；The abrasive body diameter of the ball mill is selected from 2~15mm.
6. a kind of cannabidiol extract according to claim 3, which is characterized in that raw material described in step (2)
The range of D90 is selected from 500~2000nm；The range of the D50 of the raw material is selected from 1000~2000nm.
7. a kind of cannabidiol extract according to claim 3, which is characterized in that extraction described in step (3) is molten
Agent is selected from the alcohols of C1-C4, preferably methanol, ethyl alcohol, isopropanol or its mixed solvent.
8. a kind of cannabidiol extract according to claim 3, which is characterized in that raw material described in step (3) and leaching
The plastid ratio of extraction solvent is selected from 3:1~1:3, preferably 2:1,1:1 or 1:2.
9. a kind of cannabidiol extract according to claim 3, which is characterized in that be centrifugated described in step (4)
Revolving speed be selected from 500~2000 revs/min, preferably 1000~1500 revs/min.
10. a kind of cannabidiol extract as described in any one of claims 1 to 9, it is characterised in that cannabidiol extract
Preparation method include:
(1) cannabidiol crude product is dissolved in mixed organic solvents, wherein mixed organic solvents and cannabidiol crude product volume with
Weight ratio is 15-25:1, and cannabidiol crude product solution is prepared；
Under the conditions of (2) 5 DEG C -10 DEG C, the anti-solvent of cannabidiol is added to cannabidiol crude product solution obtained in step (1),
Filtering, it is dry, obtain cannabidiol extract.
11. a kind of cannabidiol extract as claimed in claim 10, which is characterized in that the mixed solvent is C5~C10
Saturated alkane class and C1~C3 alcohols mixed solvent；The alcohols of the saturated alkane class and C1~C3 of the C5~C10
Volume ratio is selected from 1:1~1:3；The anti-solvent is water, and the volume ratio of the water and cannabidiol crude product solution is selected from 1:1~1:
5。
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110279812A (en) * | 2019-05-27 | 2019-09-27 | 大兴安岭林格贝寒带生物科技股份有限公司 | A method of the traditional Chinese medicine composition for treating epileptics containing cannabidiol |
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| CN106278828A (en) * | 2016-08-16 | 2017-01-04 | 云南汉素生物科技有限公司 | A kind of method extracting cannabidiol from industrial hemp floral leaf |
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2019
- 2019-02-28 CN CN201910148366.6A patent/CN109734560A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106278828A (en) * | 2016-08-16 | 2017-01-04 | 云南汉素生物科技有限公司 | A kind of method extracting cannabidiol from industrial hemp floral leaf |
| CN107227198A (en) * | 2017-07-28 | 2017-10-03 | 云南汉木森生物科技有限责任公司 | The cannabis leaf oil extracting method and its cannabis leaf oil of high extraction |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110279812A (en) * | 2019-05-27 | 2019-09-27 | 大兴安岭林格贝寒带生物科技股份有限公司 | A method of the traditional Chinese medicine composition for treating epileptics containing cannabidiol |
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