CN110041172A - A kind of technique improving cannabidiol recovery rate using microbiological treatment hemp floral leaf - Google Patents
A kind of technique improving cannabidiol recovery rate using microbiological treatment hemp floral leaf Download PDFInfo
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- CN110041172A CN110041172A CN201910484684.XA CN201910484684A CN110041172A CN 110041172 A CN110041172 A CN 110041172A CN 201910484684 A CN201910484684 A CN 201910484684A CN 110041172 A CN110041172 A CN 110041172A
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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
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
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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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
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- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
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Abstract
The invention belongs to field of plant extraction more particularly to a kind of method for utilizing microbiological treatment industrial hemp floral leaf, improving cannabidiol recovery rate, include the following steps: that step 1 separates one or more fungies, culture breeding using industrial hemp plant.Fermentation process is carried out to industrial hemp floral leaf using the fungi, effectively destruction cell wall, to improve the cell permeability of hemp floral leaf.Using the extraction of the organic solvents such as ethyl alcohol, n-hexane, filtering, gained filtrate carries out vacuum-concentrcted, obtains the thick extracted extract containing cannabidiol hemp floral leaf after step 2 fermentation process.Cannabidiol from medicinal extract is isolated and purified out by step 3 using silica gel column chromatography.Cannabidiol is further purified using crystallization means in step 4, obtains the high-purity C BD crystal of liquid content 99.2%.The present invention makes full use of the enzymatic reaction of microorganism, destroys plant cell wall, and the extraction efficiency of object reaches 110-130%, production cost is effectively reduced, and is suitable for industrialized production.
Description
Technical field
The invention belongs to field of plant extraction, and in particular to utilize microbiological treatment industrial hemp floral leaf to a kind of, improve
The technology of cannabidiol recovery rate.
Background technique
Industrial hemp refers to that tetrahydrocannabinol content is lower than the hemp of 0 .3%, and industrial hemp is known as Chinese fiber crops by China
It (hemp), is 1 year raw herbaceous plant of Cannabaceae (Cannabinaceae) Cannabis (Cannabis).At present from cannabis plant
The cannboid (cannabinoids, CBs) isolated is more than 100 kinds existing, mainly includes tetrahydrocannabinol
(tetrahydrocannabinol, THC), cannabidiol (cannabidiol, CBD), cannabinol (cannabinol,
CBN) and cannabigerol (cannabichromene, CBC) etc., wherein THC and CBD content highest.Tetrahydrocannabinol (THC) because
It is unreal additive with causing, limit the development of its medicinal applications value, cannabidiol (CBD) and tetrahydrocannabinol (THC) activity
It acts on completely different, is a kind of non-additive active constituent, does not have neurotoxicity.Research shows that cannabidiol (CBD) has
Important medical value, it is equal in fields such as epilepsy therapy, neuroprotection, multiple sclerosis, rheumatic arthritis, oncotherapies
Good pharmacological activity is shown, there is extraordinary application prospect.
At present to the extraction of industrial hemp, solvent extraction method and supercritical carbon dioxide extraction method are generallyd use, it is subcritical
Also rare report is extracted to refer to.These methods only industrial hemp floral leaf is simply dried, pulverization process, after surpassed
Critical carbon dioxide extracts or the organic solvents soak extractions such as ethyl alcohol, n-hexane.Then it carries out separating by subsequent means pure
Change, obtains CBD crystal.The extract yield of CBD often only has 85-95%.Currently, limited in the introduction of external high-content CBD seed
In the case of, the content of CBD in hemp floral leaf how is improved, is the emphasis of industrial hemp industry common concern.Studies have shown that hemp
Diphenoliac acid (CBDA) at high temperature can decarboxylize be converted to cannabidiol (CBD), improve the yield of CBD.But this conversion has
Limit.So studying other path for transformation to increase CBD recovery rate just and seem particularly important.
Summary of the invention
It is an object of the invention to using a kind of one kind separated from cannabis plants or it is more in fungi, to hemp floral leaf into
Row fermentation process makes full use of microorganism itself enzymatic reaction, decomposes the cell wall of plant cell, to improve hemp floral leaf
The permeability of cell is conducive to the infiltration and dissolution of the Extraction solvent in later period.The present invention relates to the culture of microorganism fungus kind and works
Industry zymotechnique, treated, and hemp floral leaf is extracted, the technologies such as object CBD separation, purifying process.The present invention makes full use of micro-
The enzymatic reaction of biology, destroys plant cell wall, and the extraction efficiency of object reaches 110-130%.
The specific steps of the present invention are as follows:
(1) using the leaf of hemp plant, skin and root tissue as raw material, with 50% ethanol water Rapid Cleaning raw material surface
Spot and bacterium use level-one sterile water wash afterwards.In desinfection chamber, clean plant tissue is placed in PDA plate culture medium,
Sterile culture 24-96 hours.On aseptic operating platform, white hypha body is picked from the plate, test tube slant is placed in, continues to cultivate
48-120 hours, the strain was as level-one provenance.Expand with level-one kind afterwards numerous, so that it may as industrial production strain.Bacterium
Kind and culture medium prescription belong to vital strategic secrets, cannot disclose.
(2) fresh hemp floral leaf is crushed to the particle of 20-200 mesh, strain 0.5-10% described in step (1) is added, mixes
After even, move into fermentation bed and carry out solid fermentation, 25-35 DEG C of fermentation temperature, fermentation time 24-72h, fermentation termination is according to HPLC
The changes of contents situation for detecting object determines.
(3) dry hemp floral leaf is crushed to the particle of 20-200 mesh, the nutrition that the sterile water of 55%-65% is prepared is added
Liquid.The strain progress fermentation process of 10-15% described in access step (1), 25-35 DEG C of fermentation temperature, fermentation time 36-120h,
Fermentation termination is determined according to CBD changes of contents situation in HPLC detection object.
(4) it by the raw material after step (2) or step (3) fermentation process, is directly transferred in extractor, is added 1-6 times
Methanol, ethyl alcohol, ethyl acetate, n-hexane or more than the mixing of several solvents, extract, Extracting temperature is 25-60 DEG C, when extraction
Between 1-3h.Extraction time is 1-3 times.Recycling design is concentrated under reduced pressure in combined extract, obtains industrial hemp and extracts medicinal extract.
(5) by (core technology cannot disclose) after step (4) extraction medicinal extract progress specially treated, with n-hexane extraction medicinal extract
2-3 times, merge organic phase.Vacuum-concentrcted recycles n-hexane, and obtained concentrate is Cannador crude product.
(6) the Cannador crude product of step (5) is added to the n-hexane dissolution of 3 times of amounts, admixes silicon by material ratio 2:1
Glue.After drying, silicagel column in dry method, n-hexane and ethyl acetate 8:1 are eluted, and collect the mobile phase containing CBD.Vacuum decompression is dense
Contracting recycles eluent, obtains cannabidiol semi-finished product.
(7) the cannabidiol semi-finished product of step (6) are dissolved with ethyl alcohol, suitable water is added, stands overnight, vacuum mistake
Filter, obtains CBD crystal, is dried in vacuo to obtain cannabidiol finished product.
The advantages of the method for the present invention and technical effect:
The fungi separated in the present invention is from cannabis plants itself, without artificially adding other fungies and bring hazard residue.
These fungies can decompose the cell wall of cannabis leaf cell, be conducive to the extraction of subsequent plant target substance.It is thin destroying
While cell wall, a series of enzymatic reaction also occurs, is conducive to the generation of target product.Use the processed work of enzymatic reaction
Sparetime university's fried dough twist leaf, the permeability enhancing of cell, solvent readily penetrate through cell wall and enter cell, and extraction time is greatly shortened
70%, solvent usage reduces 50% or more, and extraction cost is greatly reduced.CBD recovery rate is increased to 110%-130%, is significantly increased
Economic benefit.It is effective to remove the impurity such as THC, the very succinct life of use in extract using silica gel column chromatography and recrystallization technology
Production. art obtains the high-purity C BD raw material that content is higher than 99%, can be used for the application of drug, functional food, cosmetics.
Detailed description of the invention
Fig. 1 is standard items CBD liquid phase spectrogram of the invention；
Fig. 2 is finished product CBD liquid phase spectrogram of the invention.
Specific embodiment
In order to make the objectives, technical solutions, and advantages of the present invention clearer, with reference to embodiments, to the present invention
It is further elaborated.
Embodiment 1
1) it pre-processes: taking leaf, skin and the root tissue of the fresh hemp plant to grow fine, the spot on surface is eluted with water.With
50% ethanol-water solution wiping, makes the bacterial death of tissue surface.Level-one sterile water wash is used afterwards, is dried in desinfection chamber standby
With.
It is careful not to be mixed into the plant tissue of lesion, avoids bringing other undesired bacterias into, influence Spawn incubation.50% second
Alcoholic solution wiping, with tissue surface it is wet based on, tissue cannot be immersed in ethanol solution, avoid ethyl alcohol from penetrating into tissue thin
Born of the same parents kill intracellular fungi.
2) Spawn incubation: taking the hemp plant tissue of surface sterile and drying, in desinfection chamber, is placed in PDA plate culture
In base, sterile culture 48h.On aseptic operating platform, white hypha body is picked from the plate, test tube slant is placed in, continues to cultivate
48h hours, the strain was as level-one provenance.Expand with level-one kind afterwards numerous, so that it may as industrial production strain.Strain
Culture is carried out in strict accordance with sterile working, is forbidden to be mixed into other bacteriums, is polluted strain.
3) biofermentation: fresh hemp floral leaf is crushed to 100 mesh, 1% strain is added, stirs evenly, is placed in 25 DEG C
Fermentation bed in, fermentation for 24 hours.
4) solvent extraction: the hemp floral leaf after fermentation is transferred in extractor, and the ethyl alcohol of 4 times of amounts is added, soaks at 50 DEG C
Steep 3h, filtering, 1 times of ethanol washing 2 time measured of filter residue.Merging filtrate and cleaning solution, vacuum-concentrcted at 65 DEG C -75 DEG C,
Ethyl alcohol is recycled, obtains thick extracted extract, CBD recovery rate reaches 115%.
5) column chromatographs: thick extracted extract being added to the n-hexane dissolution of 3 times of amounts, admixes 200 mesh silica gel by material ratio 2:1.It dries
After dry, dry method loading, 200 mesh silica gel load column, n-hexane and ethyl acetate 8:1 elution, collect the mobile phase containing CBD.Very
Sky is concentrated under reduced pressure, and recycles eluent, obtains cannabidiol semi-finished product.
6) crystallize: 90% ethyl alcohol that cannabidiol semi-finished product are measured with 0.8 times dissolves, and stands 12h, rear fast decompression at 0 DEG C
It filters.Filter cake is obtained CBD crystal, is dried in vacuo to obtain cannabidiol finished product with a small amount of cold ethanol washing 2 times, according to external standard curve method,
CBD content 99.25% is calculated.
Embodiment 2
1) it pre-processes: taking leaf, skin and the root tissue of the fresh hemp plant to grow fine, the spot on surface is eluted with water.With
50% ethanol-water solution wiping, makes the bacterial death of tissue surface.Level-one sterile water wash is used afterwards, is dried in desinfection chamber standby
With.It is careful not to be mixed into the plant tissue of lesion, avoids bringing other undesired bacterias into, influence Spawn incubation.50% ethanol solution
Wiping, with tissue surface it is wet based on, tissue cannot be immersed in ethanol solution, ethyl alcohol is avoided to penetrate into histocyte, killed
Intracellular fungi.
2) Spawn incubation: taking the hemp plant tissue of surface sterile and drying, in desinfection chamber, is placed in PDA plate culture
In base, sterile culture 48h.On aseptic operating platform, white hypha body is picked from the plate, test tube slant is placed in, continues to cultivate
48h hours, the strain was as level-one provenance.Expand with level-one kind afterwards numerous, so that it may as industrial production strain.Strain
Culture is carried out in strict accordance with sterile working, is forbidden to be mixed into other bacteriums, is polluted strain.
3) biofermentation: fresh hemp floral leaf is crushed to 100 mesh, 1% strain is added, stirs evenly, is placed in 25 DEG C
Fermentation bed in, ferment 48h.
4) solvent extraction: the hemp floral leaf after fermentation is transferred in extractor, and the ethyl alcohol of 4 times of amounts is added, soaks at 50 DEG C
Steep 3h, filtering, 1 times of ethanol washing 2 time measured of filter residue.Merging filtrate and cleaning solution, vacuum-concentrcted at 65 DEG C -75 DEG C,
Ethyl alcohol is recycled, obtains thick extracted extract, CBD recovery rate reaches 122%.
5) column chromatographs: thick extracted extract being added to the n-hexane dissolution of 3 times of amounts, admixes 200 mesh silica gel by material ratio 2:1.It dries
After dry, dry method loading, 200 mesh silica gel load column, n-hexane and ethyl acetate 8:1 elution, collect the mobile phase containing CBD.Very
Sky is concentrated under reduced pressure, and recycles eluent, obtains cannabidiol semi-finished product.
6) crystallize: 90% ethyl alcohol that cannabidiol semi-finished product are measured with 0.8 times dissolves, and stands 12h, rear fast decompression at 0 DEG C
It filters.Filter cake is obtained CBD crystal, is dried in vacuo to obtain cannabidiol finished product with a small amount of cold ethanol washing 2 times.According to external standard curve method,
CBD content 99.33% is calculated.
Embodiment 3
1) it pre-processes: taking leaf, skin and the root tissue of the fresh hemp plant to grow fine, the spot on surface is eluted with water.With
50% ethanol-water solution wiping, makes the bacterial death of tissue surface.Level-one sterile water wash is used afterwards, is dried in desinfection chamber standby
With.
It is careful not to be mixed into the plant tissue of lesion, avoids bringing other undesired bacterias into, influence Spawn incubation.50% second
Alcoholic solution wiping, with tissue surface it is wet based on, tissue cannot be immersed in ethanol solution, avoid ethyl alcohol from penetrating into tissue thin
Born of the same parents kill intracellular fungi.
2) Spawn incubation: taking the hemp plant tissue of surface sterile and drying, in desinfection chamber, is placed in PDA plate culture
In base, sterile culture 48h.On aseptic operating platform, white hypha body is picked from the plate, test tube slant is placed in, continues to cultivate
48h hours, the strain was as level-one provenance.Expand with level-one kind afterwards numerous, so that it may as industrial production strain.Strain
Culture is carried out in strict accordance with sterile working, is forbidden to be mixed into other bacteriums, is polluted strain.
3) biofermentation: fresh hemp floral leaf is crushed to 50 mesh, 2% strain is added, stirs evenly, is placed in 35 DEG C
Fermentation bed in, ferment 48h.
4) solvent extraction: the hemp floral leaf after fermentation is transferred in extractor, and the ethyl alcohol of 4 times of amounts is added, soaks at 50 DEG C
Steep 3h, filtering, 1 times of ethanol washing 2 time measured of filter residue.Merging filtrate and cleaning solution, vacuum-concentrcted at 65 DEG C -75 DEG C,
Ethyl alcohol is recycled, obtains thick extracted extract, CBD recovery rate reaches 130%.
5) column chromatographs: thick extracted extract being added to the n-hexane dissolution of 3 times of amounts, admixes 200 mesh silica gel by material ratio 2:1.It dries
After dry, dry method loading, 200 mesh silica gel load column, n-hexane and ethyl acetate 8:1 elution, collect the mobile phase containing CBD.Very
Sky is concentrated under reduced pressure, and recycles eluent, obtains cannabidiol semi-finished product.
6) crystallize: 90% ethyl alcohol that cannabidiol semi-finished product are measured with 0.8 times dissolves, and stands 12h, rear fast decompression at 0 DEG C
It filters.Filter cake is obtained CBD crystal, is dried in vacuo to obtain cannabidiol finished product with a small amount of cold ethanol washing 2 times, according to external standard curve method,
CBD content 99.28% is calculated.
1. usual vehicle extraction method of table and the comparison of biological fermentation process CBD recovery rate
A series of embodiments explanation listed above, only for illustrating for feasible embodiment of the invention,
And to apply any restrictions to protection scope of the present invention, it is all without departing from same embodiment made by the technology of the present invention spirit or
It changes within the scope of the present invention.
It is obvious to a person skilled in the art that invention is not limited to the details of the above exemplary embodiments, Er Qie
In the case where without departing substantially from spirit or essential attributes of the invention, the present invention can be realized in other specific forms.Therefore, no matter
From the point of view of which point, the present embodiments are to be considered as illustrative and not restrictive, and the scope of the present invention is by appended power
Benefit requires rather than above description limits, it is intended that all by what is fallen within the meaning and scope of the equivalent elements of the claims
Variation is included within the present invention.
Claims (7)
1. a kind of technique for improving cannabidiol recovery rate using microbiological treatment hemp floral leaf, which is characterized in that including as follows
Step:
Step 1, one or more fungies are separated using industrial hemp plant, carries out culture breeding；It is big to industry using the fungi
Fried dough twist leaf carries out biofermentation processing, effectively destruction cell wall, to improve the cell permeability of hemp floral leaf；
Step 2, the hemp floral leaf after fermentation process is extracted, is enriched with the thick extracted extract containing cannabidiol；
Step 3, cannabidiol is isolated and purified out from medicinal extract using silica gel column chromatography；
Step 4, cannabidiol is further purified using crystallization means, is dried in vacuo, obtains high-purity C BD crystal.
2. a kind of technique that cannabidiol recovery rate is improved using microbiological treatment hemp floral leaf according to claim 1,
It is characterized in that, the step 1 fungal culture breeding specifically includes: the fungi is the leaf, skin and root with hemp plant
It organizes to be raw material, sterile culture 24-96 hours in PDA plate culture medium, on aseptic operating platform, picks from the plate white
Mycelium is placed in test tube slant, continues culture 48-120 hours, hemp floral leaf is crushed to 10-200 mesh.
3. a kind of technique that cannabidiol recovery rate is improved using microbiological treatment hemp floral leaf according to claim 1,
It is characterized in that, step 1 biofermentation specifically includes: fungi accounts for the 0.5-10% of floral leaf weight, after mixing evenly, moves into
Fermentation bed carries out solid fermentation, and 20-55 DEG C of fermentation temperature, fermentation time 24-96h, fermentation termination detects target according to HPLC
The changes of contents situation of object determines.
4. a kind of technique that cannabidiol recovery rate is improved using microbiological treatment hemp floral leaf according to claim 1,
It is characterized in that, the step 2 specifically includes: extraction method includes solvent extraction, supercritical carbon dioxide extraction, sub-critical extraction
Method.
5. a kind of technique that cannabidiol recovery rate is improved using microbiological treatment hemp floral leaf according to claim 1,
It is characterized in that, the step 3 specifically includes: silica gel mesh number 60-400 mesh, mobile phase can using n-hexane-ethyl acetate,
Petroleum ether-ethyl acetate, n-hexane-methylene chloride, petroleum ether-methylene chloride or in which several solvents mixed solvent, chromatography
Mode can use normal pressure or pressurization, and type of elution can use isocratic elution or gradient elution, eluent segmentation concentration, concentration
35-60 DEG C of temperature, pressure 10-100KPa；
Further, n-hexane: ethyl acetate volume ratio 10:1-2:1, pressure limit is in normal pressure between 7bar.
6. a kind of technique that cannabidiol recovery rate is improved using microbiological treatment hemp floral leaf according to claim 1,
It is characterized in that, the step 4 specifically includes: recrystallisation solvent has methanol, ethyl alcohol, acetone, n-hexane, normal heptane, water, or in which
The mixed solvent of several solvents, solvent are 0.5-2 times of crude product quality ratio to be crystallized, and crystallization mode has room temperature supersaturation crystallization
And -35 DEG C of -2 DEG C of low temperature crystallizations.
7. a kind of technique that cannabidiol recovery rate is improved using microbiological treatment hemp floral leaf according to claim 4,
It is characterized in that, the extraction method specifically includes: solvent extraction method, Extraction solvent include methanol, ethyl alcohol, ethyl acetate, just oneself
Alkane, petroleum ether or more than mixed solvent composed by several solvents, 1-6 times of solvent usage amount, extraction time 1-3 times extracts
Time 1-3h, 25-60 DEG C of Extracting temperature；Supercritical carbon dioxide extracts: extraction kettle pressure 15-30MPa, extraction temperature 35-
60 DEG C, extraction time be 0.5-3 hours；Extraction-container temperature is 35-50 DEG C, parsing pressure is 1-15MPa.
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| CN110423187A (en) * | 2019-08-22 | 2019-11-08 | 哈尔滨工业大学 | A kind of tunnel ultrasound and thermo-circulation distillation combination extraction cannabidiol (CBD) method |
| CN110467521A (en) * | 2019-08-22 | 2019-11-19 | 哈尔滨工业大学 | It is a kind of using industrial hemp as cannabidiol (CBD) isolation and purification method of raw material |
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| CN115504864A (en) * | 2021-06-07 | 2022-12-23 | 南通新世元生物科技有限公司 | Method for obtaining high-purity cannabidiol from industrial cannabis sativa |
| CN115850031A (en) * | 2022-11-24 | 2023-03-28 | 齐齐哈尔大学 | Method for preparing cannabidiol from industrial cannabis sativa suspension cells |
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