CN106913590A - A kind of method that small molecule active composition is extracted from plant endogenesis epiphyte - Google Patents
A kind of method that small molecule active composition is extracted from plant endogenesis epiphyte Download PDFInfo
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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
- A61K36/06—Fungi, e.g. yeasts
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/10—Preparation or pretreatment of starting material
- A61K2236/19—Preparation or pretreatment of starting material involving fermentation using yeast, bacteria or both; enzymatic treatment
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/51—Concentration or drying of the extract, e.g. Lyophilisation, freeze-drying or spray-drying
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/53—Liquid-solid separation, e.g. centrifugation, sedimentation or crystallization
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/55—Liquid-liquid separation; Phase separation
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Abstract
The present invention relates to a kind of method that small molecule active composition is extracted from plant endogenesis epiphyte, including it is characterized in that：(1) plant endogenesis epiphyte thallus suspension liquid is pressurizeed gross porosity filter operation first, mycelium and nutrient solution is carried out into initial gross separation；(2) by the separating obtained quick multigelation of mycelium, pressure filtration, gained nutrient solution filtrate merges through micro porous filtration again, removes big molecular impurity；(3) gained filtrate is concentrated in vacuo, and low temperature ultrasonic extraction is carried out by polarity order addition different organic solvents from low to high；(4) organic solution of gained opposed polarity removes remaining polysaccharide, protein molecule, grease type, pigment impurity, vacuum freeze drying through macroporous resin column chromatography absorption；(4) mixture of gained small molecule active composition is used respectively13C NMR technology means are analyzed.The present invention includes low temperature freeze thawing extraction element and low temperature ultrasonic extraction equipment, it is intended to make up existing general high temperature drying mycelia, the notable defect that plant endogenesis epiphyte small molecule secondary metabolite method is extracted in extraction is crushed again, there is provided a kind of efficient, simple and perfect extracting method.
Description
Technical field
The invention belongs to natural products processed and applied technical field, a kind of carrying for small molecule natural active product is related generally to
Take preparation method.
Background technology
Endogenetic fungus are the quasi-microorganisms for being prevalent in health plant tissue but can't causing plant itself symptom.
Related data shows there is plant endogenesis epiphyte in the plant for there are about more than 50%, and the existing plant endogenesis epiphyte having is conservative to be estimated
Planted in respect of more than 170000.Numerous studies show, the small molecule secondary metabolite that majority of plants endogenetic fungus are produced with post
Main plant natural active product produced in itself has very big similitude.Endogenetic fungus especially in Medicinal Plants study this
Aspect, this characteristic more has commonly used, and the small molecule active composition in Endophytic Fungi of Medicinal Plant secondary metabolite is
It has been increasingly becoming the replacement source that a kind of natural pharmacological component is extracted.Plant endogenesis epiphyte secondary metabolite is extracted now
The correlative study aspect of small molecule active composition is general to use high temperature drying mycelia, then the method for crushing extraction.The method shortcoming
Significantly, three problems of aspect are primarily present：One, the effective active composition contained in mycelia in extraction process may be because
Decomposed for high temperature drying, and simple mechanical is crushed and most of hyphal cell can not be made broken complete, this causes many to have
Effect composition is stranded to be locked in fungal cell, causes extraction efficiency to reduce；Secondly, largely secrete the stimulation generation in fungus culture medium
Thanking to product can not be effectively extracted separation；Thirdly, the filtering that is not added with distinguishing, drying and extraction means cause microbial cell and
The nutrient solution remnants polysaccharide of nutriment, protein molecule, grease type, pigment impurity and small molecule active composition are mingled in one
Rise, organic molecule active component is extracted to separate and causes difficulty with application.So seeking efficiently, simple and perfect extraction
Method is the new problem for being faced for promoting plant endogenesis epiphyte research and linked development.
The content of the invention
It is an object of the invention to provide a kind of method that small molecule active composition is extracted from plant endogenesis epiphyte, it is intended to
Seek to make such extract efficient, simple and perfect technological means.
What the present invention was realized in, one kind extracts small molecule active composition preparation method, institute from plant endogenesis epiphyte
Extraction preparation method is stated to comprise the following steps：
Step one, by fermentation tank or fluid nutrient medium magnify cultivate complete plant endogenesis epiphyte thallus suspension liquid enter
Row pressurization gross porosity filter operation first, and mycelia is repeatedly washed with clean water, mycelium and nutrient solution are carried out into initial gross separation；
Step 2, above-mentioned separating obtained mycelium soak 20min with the 2-3 times of clean water of volume, at -10 DEG C -30 DEG C
Temperature range quick multigelation 4-6 times, gained freeze thawing liquid pressing filtering (0.15MPa maintains 10min), with S101 steps institute
Obtain nutrient solution to merge through the filtering of pore again, remove big molecular impurity；Filtrate is obtained, filter residue is given up；
Step 3, S102 steps gained filtrate is concentrated in vacuo, gained high concentration solution and S101 steps gained
Mycelium mixes, then adds the different organic solvents to carry out low temperature ultrasonic extraction 60-80min, institute by polarity order from low to high
Obtain organic solvent and separate outflow；
Step 4, the organic solution of S103 steps gained opposed polarity remove remaining many through macroporous resin column chromatography absorption
Sugar, protein molecule, grease type, pigment impurity, obtain the organic solution containing small molecule active composition, and vacuum freeze drying is removing
Solvent is removed, small molecule active component substances are obtained；
Step 5, the mixture of S104 steps institute small molecule active composition are used respectively13C-NMR technological means is analyzed,
Distributed area according to its chemical shift come speculate its whether the material containing lateral reactivity structure, to be precisely separated offer reference
Foundation.
Further illustrating the filtering of the gross porosity involved by step one uses the stainless steel of 300-400 mesh numbers slightly to imitate filtering
Net.
The multigelation process involved by step 2 is further illustrated, system should be made to be refrigerated to -10 DEG C of holding 4min, then it is fast
Speed is warming up to 30 DEG C, and heating-up time control keeps constant temperature 10min in 5-10min in 30 DEG C, and the process is repeated again.
The pore filter process involved by step 2 is further illustrated, stainless steel microporous filter screen is used, aperture is about
0.05-0.1mm。
Ultrasonic cryogenic extraction temperature constant temperature involved by step 3 is further illustrated at 25 DEG C, the organic solvent for using should be by
Polarity order extraction from small to large.
Further illustrate the macroreticular resin involved by step 4 and generally use AB-8 type macroreticular resins.
Further illustrate involved by step 513C-NMR technical Analysis gained substance process, Main Basiss chemical shift δ
Appearance region judge, mainly include：
Saturated carbon atom area (δ<100)：If saturated carbon atom is not connected directly with hetero atom (O, S, N, F etc.), its chemical shift
Value is generally less than 55.
Unsaturated carbon atom area (δ 90-160)：Olefinic carbon atoms and aromatic carbon atom are in this region appearance；When its directly and hetero atom
When being connected, chemical displacement value may be big by 160；Then in other region appearances, its chemical displacement value scope is 70- to alkynes carbon atom
100。
Carbonyl Huo Diexi area (δ>150)：The δ values of carbon atom generally higher than 160 in the group in the region.Wherein acid, ester and acid anhydrides
Carbonylic carbon atom in 160-180 appearances, ketone and aldehyde material are in 200 area above appearances.
Another object of the present invention is to provide a kind of low temperature freeze thawing extraction system, setting includes that heating/frozen air is followed
Ring unit, clean water replenishment system, automatic constant-pressure unit, time controlled system and low efficient filter screen；
Heating/frozen air Cycle Unit includes being arranged at air circulation layer and the self-filtering side off the net of freeze thawing kettle outer wall
Temperature sensor, be placed in left side；Automatic constant-pressure unit is arranged at freeze thawing kettle top, is provided with pressure sensor, controls all the time
Pressure is in 0.12-0.15Mpa；Time controlled system is responsible for detecting and controlling the operating time of each small step.
Another object of the present invention is to provide a kind of low temperature ultrasonic extracting system, setting include thermostatted water Cycle Unit,
Condensation cycle guard system, Vltrasonic device, time controlled system and microporous filter screen；
Another object of the present invention is to provide a kind of low temperature ultrasonic extracting system, setting include thermostatted water Cycle Unit,
Condensation cycle guard system, Vltrasonic device, time controlled system and microporous filter screen；
Another object of the present invention is to provide a kind of low temperature ultrasonic extracting system, setting include thermostatted water Cycle Unit,
Condensation cycle guard system, Vltrasonic device, time controlled system and microporous filter screen；
Thermostatted water Cycle Unit should be able to be such that water temperature controls at 0 DEG C -30 DEG C；Condensation cycle guard system is arranged on apparatus main body
Side, for the organic solvent of condensing reflux volatilization.
Thermostatted water Cycle Unit should be able to be such that water temperature controls at 0 DEG C -30 DEG C；Condensation cycle guard system is arranged on apparatus main body
Side, for the organic solvent of condensing reflux volatilization.
The preparation method that small molecule active composition is extracted from plant endogenesis epiphyte that the present invention is provided, first will in the present invention
The plant endogenesis epiphyte thallus suspension liquid that cultivation of being magnified in fermentation tank or fluid nutrient medium is completed carries out the behaviour of gross porosity filtering first
Make, mycelium and nutrient solution are carried out into initial gross separation, nutriment is remaining during this pressurized raw effect filtering can avoid nutrient solution
Cell, impurity component particle and mycelium are mixed in together, and subsequent extracted is interfered；
Separating obtained mycelium soaks 20min with the 2-3 times of clean water of volume, quick in -10 DEG C of -30 DEG C of temperature ranges
Multigelation 4-6 times, gained freeze thawing liquid merges through the filtering of pore again with preceding step gained nutrient solution, removes macromolecular miscellaneous
Matter；To mycelial drying when the method need not be crushed routinely, fresh plant endogenesis epiphyte mycelium take repeatedly water suction,
Freezing expansion ruptures, and repressurization leaches somatic cells liquid；By the material of such treatment, fungal cell can be sufficiently discharged
Interior active component, reduces decomposition and derivative of the active component in original general high temperature working processes, significantly improves
Recovery rate in extraction.
Above-mentioned steps gained filtrate is concentrated in vacuo, gained mycelium after the completion of gained high concentration solution and freeze thawing
Mix, then add different organic solvents to carry out low temperature ultrasonic by polarity order from low to high and extract 60-80min, gained is organic
Solvent separates outflow；On the one hand to be different from general dry in the past molten added with machine for the low temperature ultrasonic extracting system used by the operation
Agent extracting method.It does not require to be completely dried extracting substance, cost-effective；And it is possible to prevente effectively from solvent volatilization institute
The loss for causing and potential safety hazard, and ultrasound can make extraction organic phase be mixed with water conjunction completely, and solute substance is fully exchanged,
The ascending organic solvent extraction of another aspect polarity can be such that the small-molecule active substance of opposed polarity is dissolved accordingly
Wherein, the method can carry out preferably peeling off layer by layer to its original mixed extract.
13C-NMR technical Analysis gained substance process changes in the past general mass spectrum and goes to analyze doing compared with pure natural components
Method, for it is with respect to mass spectral analysis prediction, is more beneficial for researcher from molecular structure of compounds and naturally produces inferring to extract
The potential value and molecule pharmacological activity of thing.
Brief description of the drawings
Fig. 1 is the preparation flow figure of extraction small molecule active composition in plant endogenesis epiphyte provided in an embodiment of the present invention.
Fig. 2 is low temperature freeze thawing extraction element structural representation provided in an embodiment of the present invention.
Fig. 3 is low temperature ultrasonic extraction equipment structural representation provided in an embodiment of the present invention.
Specific embodiment
With reference to embodiments, in order to make the purpose , technical scheme and advantage of the present invention be clearer, to the present invention
It is further elaborated.It is to be understood that the specific embodiments described herein are merely illustrative of the present invention, not
For limiting the present invention.
Below in conjunction with the accompanying drawings and specific embodiment is further described to application principle of the invention.
As shown in the figure, the extraction preparation method of the natural products of the embodiment of the present invention is comprised the following steps：
S101, by fermentation tank or fluid nutrient medium magnify cultivate complete plant endogenesis epiphyte thallus suspension liquid carry out
Pressurization gross porosity filter operation first simultaneously repeatedly washs mycelia with clean water, and mycelium and nutrient solution are carried out into initial gross separation.
S102, above-mentioned separating obtained mycelium soak 20min with the 2-3 times of clean water of volume, in -10 DEG C of -30 DEG C of temperature
Degree interval quick multigelation 4-6 times, gained freeze thawing liquid, repressurization filtering (0.15MPa maintains 10min) and S101 steps
Gained nutrient solution merges through the filtering of pore again, removes big molecular impurity；Filtrate is obtained, filter residue is given up.
S103, S102 steps gained filtrate is concentrated in vacuo, gained high concentration solution and S101 steps gained bacterium
Filament mixes, then adds the different organic solvents to carry out low temperature ultrasonic extraction 60-80min, gained by polarity order from low to high
Organic solvent separates outflow.
S104, the organic solution of S103 steps gained opposed polarity is removed through macroporous resin column chromatography absorption it is remaining many
Sugar, protein molecule, grease type, pigment impurity, obtain the organic solution containing small molecule active composition, and vacuum freeze drying is removing
Solvent is removed, small molecule active component substances are obtained.
S105, the mixture of S104 steps institute small molecule active composition is used respectively13C-NMR technological means is analyzed,
Distributed area according to its chemical shift come speculate its whether the material containing lateral reactivity structure, to be precisely separated offer reference
Foundation.
The appearance region of Main Basiss chemical shift δ judges, mainly includes：
Saturated carbon atom area (δ<100)：If saturated carbon atom is not connected directly with hetero atom (O, S, N, F etc.), its chemical shift
Value is generally less than 55.
Unsaturated carbon atom area (δ 90-160)：Olefinic carbon atoms and aromatic carbon atom are in this region appearance；When its directly and hetero atom
When being connected, chemical displacement value may be big by 160；Then in other region appearances, its chemical displacement value scope is 70- to alkynes carbon atom
100。
Carbonyl Huo Diexi area (δ>150)：The δ values of carbon atom generally higher than 160 in the group in the region.Wherein acid, ester and acid anhydrides
Carbonylic carbon atom in 160-180 appearances, ketone and aldehyde material are in 200 area above appearances.
When processing refined extraction product by macroreticular resin column method, if larger residual absorption occurs in product, second can be used
Alcohol is rinsed；Or the macroreticular resin of corresponding polarity model can be selected.
The capital equipment used in the present invention has low temperature freeze thawing extraction system and low temperature ultrasonic extracting system.
As shown in Fig. 2 the capital equipment of low temperature freeze thawing extraction system includes in the present invention：Heating/frozen air circulator
Group 10, low efficient filter screen 20, temperature sensing controller 30, automatic constant-pressure unit 40 and clean water replenishment system 50 and time control
System processed.Wherein heating/frozen air Cycle Unit adjusts circulation air by the Monitoring Data that temperature sensor is reversely passed back
Temperature；Automatic constant-pressure unit carries out constant voltage operation by pressure sensor, and the instruction of binding time control system is carried out
The time control of different pressures level.
Low temperature ultrasonic extracting system：Using industrialization low temperature ultrasonic extraction equipment by the active material of rough gained in low temperature
Under the conditions of layer by layer stripping type extract, extraction rate reached to more than 90% and realize initial gross separation.
As shown in figure 3, the capital equipment that low temperature ultrasonic extracting system is used in the present invention includes：Thermostatted water Cycle Unit
60th, Vltrasonic device 70, microporous filter screen 80, temperature sensing controller 90, condensation cycle guard system 100 and time control system
System.
Low temperature ultrasonic extracting system general ultrasonic extraction system different from the past, it does not require that extracted material belongs to
Solid state, this requires to dry the cost of the aqueous solution in greatling save conventional natural product extraction method, and in the present invention
Make two-phase mixtures fully using ultrasonic wave, substantially increase the extraction efficiency that machinery in the past stands extraction.
Thermostatted water Cycle Unit, maintains for the low temperature in extraction process, and extraction temperature is set as 20 DEG C -24 DEG C, it is to avoid
The temperature that ultrasound is caused is raised；Condensation cycle guard system is radiated using screw type pipeline and condensed, and is caused for elimination solvent volatilization
Potential safety hazard, and solvent can be recycled, reduce loss.
Presently preferred embodiments of the present invention is the foregoing is only, is not intended to limit the invention, it is all in essence of the invention
Any modification, equivalent and improvement made within god and principle etc., should be included within the scope of the present invention.
Claims (5)
1. it is a kind of from plant endogenesis epiphyte extract small molecule active composition method, it is characterised in that, the small molecule is natural
The extraction preparation method of activated product is comprised the following steps:
Step one, by fermentation tank or fluid nutrient medium magnify cultivate complete plant endogenesis epiphyte thallus suspension liquid carry out head
Secondary pressurization gross porosity filter operation, and mycelia is repeatedly washed with clean water, mycelium and nutrient solution are carried out into initial gross separation；
Step 2, above-mentioned separating obtained mycelium soak 20min with the 2-3 times of clean water of volume, in -10 DEG C of -30 DEG C of temperature
Interval quick multigelation 4-6 times, gained freeze thawing liquid pressing filtering (0.15MPa maintains 10min), trains with S101 steps gained
Nutrient solution merges through micro porous filtration again, removes big molecular impurity；Filtrate is obtained, filter residue is given up；
Step 3, S102 steps gained filtrate is concentrated in vacuo, gained high concentration solution and S101 steps gained mycelia
Body mixes, then adds the different organic solvents to carry out low temperature ultrasonic extraction 60-80min, extraction temperature by polarity order from low to high
Degree is set as 20 DEG C -24 DEG C, and gained organic solvent separates outflow；
Step 4, the organic solution of S103 steps gained opposed polarity remove remaining polysaccharide, egg through macroporous resin column chromatography absorption
White matter molecule, grease type, pigment impurity, obtain the organic solution containing small molecule active composition, and vacuum freeze drying is molten to remove
Agent, obtains small molecule active component substances；
Step 5, the mixture of S104 steps institute small molecule active composition are used respectively13C-NMR technological means is analyzed, according to
The distributed area of its chemical shift come speculate its whether the material containing lateral reactivity structure, for be precisely separated provide with reference to according to
According to.
2. the preparation method that small molecule active composition is extracted from plant endogenesis epiphyte as described in right 1 is required, its feature exists
In the method for using is that slightly effect filtering makes mycelium and nutrient solution crush fungal cell using multigelation after separating；
Mycelium soaks 20min with the clean water of 2-3 times of volume, in -10 DEG C of -30 DEG C of temperature ranges quick multigelation 4-6 times, gained
Freeze thawing liquid pressing filtering (0.15MPa maintains 10min).
3. low temperature ultrasonic extracting process is used as described in right 1 is required, by vacuum concentration after containing the water-soluble of active component
Liquid mix with gained mycelium after the completion of freeze thawing, then to add different organic solvents to carry out low temperature by polarity order from low to high super
Sound extracts 60-80min, and extraction temperature is set as 20 DEG C -24 DEG C.
4. the extraction preparation method from plant endogenesis epiphyte small molecular active component as described in right 1-3 any one, its
It is characterised by, the capital equipment of the low temperature freeze thawing extraction system for using includes：Heating/frozen air Cycle Unit, thick effect filtering
Net, temperature sensing controller, automatic constant-pressure unit and clean water replenishment system and time controlled system.Wherein heating/freezing
Air circulation unit adjusts the temperature of circulation air by the Monitoring Data that temperature sensor is reversely passed back；Automatic constant-pressure unit leads to
Over-pressed force snesor carries out constant voltage operation, and the time for instructing to carry out different pressures level of binding time control system is controlled
System.
5. the capital equipment that the low temperature ultrasonic extracting system as described in right 1-3 any one is used includes：Thermostatted water circulator
Group, Vltrasonic device, microporous filter screen, temperature sensing controller, condensation cycle guard system and time controlled system.
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Cited By (3)
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| CN107879905A (en) * | 2017-11-15 | 2018-04-06 | 中南大学 | The extracting method of the trichloroanisole of intracellular 2,4,6 and 2,4,6 trichlorophenol, 2,4,6,-Ts in fungi methylation reaction |
| CN109486685A (en) * | 2018-12-04 | 2019-03-19 | 海南师范大学 | A kind of mangrove cusp sea lotus endogenetic fungus and its application in preparation anti-insect activity terpene crystalline compounds |
| CN117919150A (en) * | 2024-03-19 | 2024-04-26 | 昆明康尔迅生物工程有限公司 | Preparation method and application of small molecular plant water base |
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| CN102464634A (en) * | 2010-11-11 | 2012-05-23 | 阅微生物技术（上海）有限公司 | New compound in secondary metabolites of cephalotaxus fortunei endophytic fungi, and preparation method and application thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107879905A (en) * | 2017-11-15 | 2018-04-06 | 中南大学 | The extracting method of the trichloroanisole of intracellular 2,4,6 and 2,4,6 trichlorophenol, 2,4,6,-Ts in fungi methylation reaction |
| CN107879905B (en) * | 2017-11-15 | 2021-04-02 | 中南大学 | Method for extracting intracellular 2,4,6-trichloroanisole and 2,4,6-trichlorophenol in fungus methylation reaction |
| CN109486685A (en) * | 2018-12-04 | 2019-03-19 | 海南师范大学 | A kind of mangrove cusp sea lotus endogenetic fungus and its application in preparation anti-insect activity terpene crystalline compounds |
| CN109486685B (en) * | 2018-12-04 | 2020-10-30 | 海南师范大学 | Mangrove cuspid and sea lotus endophytic fungus and application thereof in preparation of anti-insect active terpenoid crystal compound |
| CN117919150A (en) * | 2024-03-19 | 2024-04-26 | 昆明康尔迅生物工程有限公司 | Preparation method and application of small molecular plant water base |
| CN117919150B (en) * | 2024-03-19 | 2024-06-04 | 昆明康尔迅生物工程有限公司 | Preparation method and application of small molecular plant water base |
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Application publication date: 20170704 |