CN110256206A - A kind of method of high speed adverse current chromatogram separation and Extraction cannabidiol - Google Patents
A kind of method of high speed adverse current chromatogram separation and Extraction cannabidiol Download PDFInfo
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- CN110256206A CN110256206A CN201910590302.1A CN201910590302A CN110256206A CN 110256206 A CN110256206 A CN 110256206A CN 201910590302 A CN201910590302 A CN 201910590302A CN 110256206 A CN110256206 A CN 110256206A
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- petroleum ether
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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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- C—CHEMISTRY; METALLURGY
- 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
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Abstract
The invention discloses a kind of methods of high speed adverse current chromatogram separation and Extraction cannabidiol, belong to industrial hemp and extract field, this method comprises: 1) that industrial hemp floral leaf is dry, crushing；2) cannabidiol is extracted with methanol or ethyl alcohol, obtains cannabidiol alcohol extract；3) petroleum ether phase is obtained with petroleum ether extraction, and removes petroleum ether, obtain extract；4) extract is separated using high-speed countercurrent chromatography, collects eluent；5) eluent concentration, crystallization are obtained into cannabidiol product.
Description
Technical field
The present invention relates to industrial hemp field, a kind of specifically side of high speed adverse current chromatogram separation and Extraction cannabidiol
Method.
Background technique
Hemp (Cannabis sativa L.subsp.sativa) is a kind of annual grass with important medical value
This plant belongs to moraceae plants hemp subfamily Cannabis.There are three types of hemp plant extract main actives (CBD, CBN,
THC), wherein THC is a kind of ingredient being addicting.Hemp plant depends on to people's hallucinogenic action is mainly THC concentration,
The kind of THC < 0.3% does not have psychotropic activity.Therefore EU Committee has formulated unified standard, can plant in hemp dry product
THC content is known as " industrial hemp " not above 0.3%.
The cannboid isolated from hemp at present is more than 80 kinds existing, mainly include cannabidiol CBD, tetrahydro hemp THC,
Cannabinol CBN and cannabigerol CBC etc., research finds that CBD can hinder THC to influence nerve system of human body, and has important
Pharmacological activity.In addition to this, Recent study is found, CBD has tranquilizing soporific, treatment epilepsy, neuroprotection, multiple sclerosis
A series of physiological functions such as disease, rheumatic arthritis, oncotherapy are a kind of in the natural of the great application prospect of medicine and other fields
Active constituent.
Since CBD has a large amount of bioactivity and its medical value, society is to the appearance of CBD product and wanting for quality
Ask higher and higher, since the content of CBD is the primary evaluation index of product quality, price with CBD changes of contents without
Together, therefore, the exploration and optimization of CBD simple substance purification process are inexorable trends.
High speed adverse current chromatogram (high-speed countercurrent chromatography, HSCCC) was 20th century
A kind of liquid luquid partition chromatography isolation technics of the continuous high-efficient to grow up the eighties, it does not have to any solid supporter or
Carrier.It is flat that it sets up a kind of special one-way fluid dynamics using two phase solvent system in high-speed rotating helix tube
Weighing apparatus a, wherein phase, as stationary phase, another phase can retain a large amount of stationary phases during continuous elution as mobile phase.By
In not needing solid support, the separation of substance according to its distribution coefficient in two-phase difference and realize, thus avoid because
Sample loss, inactivation caused by Irreversible Adsorption, denaturation etc., not only enable sample all to recycle, and the sample of recycling more can
Reflect its original characteristic, the separation particularly suitable for natural bioactive ingredients.And since separated object matter and liquid are solid
Determine to come into full contact between phase, so that the preparation amount of sample greatly improves, it is a kind of ideal preparative separation means.
It has applied widely, flexible operation, efficient, quick, preparation relative to traditional solid-liquid Column chromatography techniques
The advantages such as amount is big, expense is low.HSCCC technology is developing into a kind of novel separating and purifying technology being concerned, natural
A kind of effective new separation technology is had been considered as in product industry.
Column chromatography generally is used to isolating and purifying for CBD, as CN201811468947.X discloses one kind from work
The method of separation and Extraction cannabidiol in sparetime university's hemp plant separates CBD using silica gel forward direction column chromatography and C18 reversed-phase column etc.；
CN201810022445 discloses a kind of preparation method of high-purity cannabidiol, using macroporous adsorbent resin column chromatography and polyamides
Amine column chromatography joint technology is purified, and carries out crystal refining using mixed solvent system.
Solvent extraction and recrystallization operation step is more, single treatment amount is less and inefficient.The skills such as HPLC and HPLC-MS
Art, the high requirements on the equipment is cumbersome, instrument it is at high cost, treating capacity is small, is not suitable in industrial production.Column chromatographic purifying
That there are techniques is unreasonable for method, yield is low, agents useful for same or material is complicated or stationary phase is expensive, adsorbent reactivation difficulty with
And solvent was difficult in place of the deficiencies of recycling.
New technology HSCCC is also largely used to during the isolating and purifying of natural products, as CN201811587229 is disclosed
A method of there is the Chinese medical extract of antitumor action using high-speed countercurrent chromatography preparation, this method is to Chinese medicine fourth
Last of the ten Heavenly stems grass, alcohol extracting extract to obtain acetic acid ethyl ester extract；Acetic acid ethyl ester extract is separated using high-speed countercurrent chromatography, is obtained
The Chinese medical extract.CN201811514536 discloses a kind of utilization one step purifying purple sweet potato alkali of high performance countercurrent chromatography technology
The method of soluble polysaccharide, this method purify through high performance countercurrent chromatography and obtain purple sweetpotato alkali-soluble polysaccharide；It is dialysed, is freeze-dried,
Purifying, obtains purple sweetpotato alkali-soluble polysaccharide fine work etc..
The parameter and solvent selection of high speed adverse current chromatogram are always that it can not be applied to what some active ingredients of plants extracted
Major reason, such as in extracting traditional Chinese medicine ingredients, different raw materials needs different materials and parameter, and basis is needed specifically to mention
Object is taken to select specific materials and parameter, and the selection of materials and parameter needs to do a large amount of experiment.Such as CBD extraction in if
Parameter and materials selection are incorrect, can not separating effect, or the CBD purity isolated is high.
There is presently no preferable technological parameters, enable high speed adverse current chromatogram to the cannabidiol in industrial hemp
(CBD) it is purified, formulates the cannabidiol of high-purity, especially to stationary phase, mobile phase and ultraviolet detection wavelength, collection
The selection at position, slightly changing for selection will will have a direct impact on the purity of separating effect and product.
Summary of the invention
It is an object of the invention to: the problem of working as the prior art, discloses a kind of high speed adverse current chromatogram point
Easy to operate, high-efficient, price is low from the method for extracting cannabidiol, purity is high, preparation amount is big, is suitable for industrialized production.
This method comprises:
1) industrial hemp floral leaf is dry, crushing；
2) cannabidiol is extracted with methanol or ethyl alcohol, obtains cannabidiol alcohol extract；
3) petroleum ether phase is obtained with petroleum ether extraction, and removes petroleum ether, obtain extract；
4) extract is separated using high-speed countercurrent chromatography, collects eluent；
5) eluent concentration, crystallization are obtained into cannabidiol product.
In some preferred embodiments, the solvent that high-speed countercurrent chromatography uses is chloroform, methanol and water；Wherein
The volume ratio of chloroform, methanol and water is (1-4): (2-3): (1-2), high speed adverse current chromatogram host rotate clockwise, and revolving speed is
700~1000rpm；Stationary phase retention are as follows: 60%~80%, the flow velocity of mobile phase is 1~2ml/min；Separation temperature is 15
~30 DEG C；Ultraviolet detection wavelength is 190~254nm；The elution position of 25~33min is collected after sample introduction.
Above-mentioned high-speed countercurrent chromatography is this experimenter lower selection after using multiple solvents and process conditions
Optimal condition, according to the lower cannabidiol of the high-speed countercurrent chromatography of above-mentioned parameter and materials purification with good separating effect,
The cannabidiol impurity of preparation is small, and purity is high can reach 98% or more.
In some preferred embodiments, the drying is that industrial hemp floral leaf is first dried in the shade, then is dried.?
In some preferred embodiments, drying is that the industrial hemp floral leaf that will be dried in the shade dries 0.4-5h at 100-140 DEG C.
In some preferred embodiments, with the following method with petroleum ether extraction: successively using n-butanol, ethyl acetate
It is extracted respectively with petroleum ether 1~3 time, takes petroleum ether extraction position, concentration removal petroleum ether solvent obtains petroleum ether extract.?
It in some preferred embodiments, is successively extracted respectively 2 times with n-butanol, ethyl acetate, petroleum ether, takes 2 times and be obtained by extraction
Petroleum ether extraction position merge, concentration removal petroleum ether solvent, obtain petroleum ether extract.Work as in some preferred embodiments
In, the volumetric usage ratio of n-butanol, the volumetric usage of ethyl acetate and petroleum ether and water is 1:1 in each extraction process.
In some preferred embodiments, ethyl alcohol is used in step 2, the solid-liquid ratio of ethyl alcohol and industrial hemp floral leaf is
30:1。
The present invention provides a kind of preparation method of completely new cannabidiol using industrial hemp floral leaf as raw material；This method
Using Separation of Natural Products state-of-the-art technology, hemp two is prepared from industrial hemp using high-speed countercurrent chromatography for the first time
Phenol.Simultaneously using high speed adverse current chromatogram can also be similar with extraction purification cannabinoid, including but not limited to CBDV, CBN,
CBG, CBC, CBL, CBE etc..
Specific embodiment
The present invention is described in detail below.
Embodiment 1:
Step 1: industrial hemp floral leaf is taken, is dried in the shade；The industrial hemp floral leaf dried in the shade is dried into 0.4h at 140 DEG C, sufficiently
Remove the moisture in floral leaf, be crushed to 40 mesh or more later, with 95% alcohol at normal temperature seepage pressure effects, wherein industrial hemp floral leaf with
The solid-liquid ratio of 95% ethyl alcohol is 1:30, later rotary evaporation, recycles extraction solvent, obtains the alcohol extract of industrial hemp floral leaf；
Step 2: adding water to be suspended the alcohol extract of industrial hemp floral leaf, then successively uses n-butanol, ethyl acetate, petroleum
Ether extracts 2 times respectively, and 2 petroleum ether extraction positions being obtained by extraction is taken to merge, and concentration removal petroleum ether solvent obtains petroleum ether extraction
Take object；Wherein the amount ratio of cannabis alcohol extracts from the leaves and water is 1:20；N-butanol, ethyl acetate and petroleum in each extraction process
The volumetric usage of ether and the volumetric usage ratio of water are 1:1；
Step 3: petroleum ether extract is separated using high-speed countercurrent chromatography, specifically, by chloroform, methanol with
And water is 2:(2.5 by volume): (1.5) mixing, stratification obtains upper and lower phase solution after shake well mixes after mixing, and
After will mutually separate above and below and after ultrasonic degassing 30min, take phase solution as mobile phase, lower phase solution is stationary phase, open into
Stationary phase is pumped under the maximum flow rate of equipment and full of current chromatographic column by sample pump, be then turned on high speed adverse current chromatogram host and
Detector, chromatographic work station are pumped into mobile phase under conditions of revolving speed 855rpm, flow velocity 1.5ml/min；
Step 4: it takes petroleum ether extract to be dissolved in lower phase solution and obtains sample solution, be then charged into sample introduction test tube；Wherein
The amount ratio of petroleum ether extract and lower phase solution is 2:1；
Step 5: being put into sample introduction filter in test tube, and sample solution is pumped into adverse current chromatogram pipe with the flow velocity of 1.5ml/min
Road, sample solution is into continuing after complete with the flow pump of 1.5ml/min to collect the elution portion of 25-33min after sample introduction into mobile phase
Position is to get the cannabidiol product；High speed adverse current chromatogram host rotates clockwise, and stationary phase retention is 76%, detection
Wavelength is 235nm；Separation temperature is 25 DEG C.
The present embodiment prepares cannabidiol product using high-speed countercurrent chromatography from industrial hemp, obtained function
Ingredient purity is high, can reach 98% or more.The cannabidiol of high-purity is conducive to other productions of the further manufacture to cannabidiol
Product and research.The separation of the present embodiment, method of purification are simple, reproducible, can be used for a large amount of preparations of compound.
Those skilled in the art will be without departing substantially from the broad range of the disclosure, can be to above-described embodiment
Carry out a variety of variations and/or modification.Therefore, the embodiment of the present invention is regarded as illustrative and non-limiting in all respects
's.The step of separately or cooperatively being pointed out in disclosed herein or the description of the present application, feature, entirety, composition and/or chemical combination
Any and all combinations of object and two or more described steps or feature.Described herein and/or reference all Shens
It please be hereby incorporated herein by reference.Document, operation, material, device, article for having included in the description of the invention etc.
Any discussion be used only for providing context of the invention.Should not be construed as having recognised any or all these item by
Before the priority date that it comes across each claim of the present invention, and thinks any or all these item and constitute existing skill
The a part on art basis or the common sense of relevant art.
Claims (9)
1. a kind of method of high speed adverse current chromatogram separation and Extraction cannabidiol, which is characterized in that this method comprises:
1) industrial hemp floral leaf is dry, crushing；
2) cannabidiol is extracted with methanol or ethyl alcohol, obtains cannabidiol alcohol extract；
3) petroleum ether phase is obtained with petroleum ether extraction, and removes petroleum ether, obtain extract；
4) extract is separated using high-speed countercurrent chromatography, collects eluent；
5) eluent concentration, crystallization are obtained into cannabidiol product.
2. the method for high speed adverse current chromatogram separation and Extraction cannabidiol according to claim 1, it is characterised in that inverse at a high speed
The solvent that flow chromatography uses is made of chloroform, methanol and water；Wherein the volume ratio of chloroform, methanol and water is (1~4):
(2~3): (1~2).
3. the method for high speed adverse current chromatogram separation and Extraction cannabidiol according to claim 2, which is characterized in that inverse at a high speed
Flow chromatography host rotates clockwise, and revolving speed is 700~1000rpm；Stationary phase retention are as follows: 60%~80%, the stream of mobile phase
Speed is 1~2ml/min；Separation temperature is 15~30 DEG C；Ultraviolet detection wavelength is 190~254nm；After sample introduction collect 25~
The elution position of 33min.
4. the method for high speed adverse current chromatogram separation and Extraction cannabidiol according to claim 3, which is characterized in that described
Drying is that industrial hemp floral leaf is first dried in the shade, then is dried.
5. the method for high speed adverse current chromatogram separation and Extraction cannabidiol according to claim 4, which is characterized in that described
Drying is that the industrial hemp floral leaf that will be dried in the shade dries 0.4-5h at 100~140 DEG C.
6. the method for high speed adverse current chromatogram separation and Extraction cannabidiol according to claim 5, which is characterized in that use petroleum
Ether extracts with the following method: successively being extracted 1~3 time with n-butanol, ethyl acetate and petroleum ether respectively, takes petroleum ether extraction portion
Position, concentration removal petroleum ether solvent, obtains petroleum ether extract.
7. the method for high speed adverse current chromatogram separation and Extraction cannabidiol according to claim 6, which is characterized in that successively use
N-butanol, ethyl acetate, petroleum ether extract 2 times respectively, take 2 petroleum ether extraction positions being obtained by extraction to merge, concentration removal
Petroleum ether solvent obtains petroleum ether extract.
8. the method for high speed adverse current chromatogram separation and Extraction cannabidiol according to claim 7, which is characterized in that extraction every time
The volumetric usage ratio of n-butanol, the volumetric usage of ethyl acetate and petroleum ether and water is 1:1 during taking.
9. the method for high speed adverse current chromatogram separation and Extraction cannabidiol according to claim 6, which is characterized in that step 2
Middle to use ethyl alcohol, the solid-liquid ratio of ethyl alcohol and industrial hemp floral leaf is 30:1.
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Cited By (7)
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| CN110746275A (en) * | 2019-11-08 | 2020-02-04 | 河南汉麻生物科技有限公司 | Method for separating cannabidiol by using continuous chromatographic system |
| CN111960929A (en) * | 2020-08-11 | 2020-11-20 | 江苏哈工药机科技股份有限公司 | Method for extracting CBD full-spectrum oil from industrial cannabis sativa leaves |
| CN111960928A (en) * | 2020-08-11 | 2020-11-20 | 江苏哈工药机科技股份有限公司 | Method for extracting CBD full spectrum oil |
| CN112939745A (en) * | 2021-03-29 | 2021-06-11 | 天津信汇制药股份有限公司 | Separation system and separation method of cannabidiol |
| CN112979488A (en) * | 2021-04-02 | 2021-06-18 | 黑龙江展延自动化科技有限公司 | Cannabinoid production method based on axial dynamic extraction two-fluid separation technology |
| CN113135885A (en) * | 2021-04-07 | 2021-07-20 | 上海同田生物技术有限公司 | Method for separating and purifying tetrahydrocannabinol by high-speed counter-current chromatography |
| CN113956228A (en) * | 2021-11-05 | 2022-01-21 | 中国农业科学院麻类研究所 | Extraction and separation method of cannabinol |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110746275A (en) * | 2019-11-08 | 2020-02-04 | 河南汉麻生物科技有限公司 | Method for separating cannabidiol by using continuous chromatographic system |
| CN111960929A (en) * | 2020-08-11 | 2020-11-20 | 江苏哈工药机科技股份有限公司 | Method for extracting CBD full-spectrum oil from industrial cannabis sativa leaves |
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| CN111960929B (en) * | 2020-08-11 | 2022-07-22 | 江苏哈工药机科技股份有限公司 | Method for extracting CBD full-spectrum oil from industrial cannabis sativa leaves |
| CN112939745A (en) * | 2021-03-29 | 2021-06-11 | 天津信汇制药股份有限公司 | Separation system and separation method of cannabidiol |
| CN112979488A (en) * | 2021-04-02 | 2021-06-18 | 黑龙江展延自动化科技有限公司 | Cannabinoid production method based on axial dynamic extraction two-fluid separation technology |
| CN113135885A (en) * | 2021-04-07 | 2021-07-20 | 上海同田生物技术有限公司 | Method for separating and purifying tetrahydrocannabinol by high-speed counter-current chromatography |
| CN113956228A (en) * | 2021-11-05 | 2022-01-21 | 中国农业科学院麻类研究所 | Extraction and separation method of cannabinol |
| CN113956228B (en) * | 2021-11-05 | 2023-07-07 | 中国农业科学院麻类研究所 | Extraction and separation method of cannabinol |
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Application publication date: 20190920 |