CN108524865A - A kind of extraction of turmeric and enrichment method - Google Patents
A kind of extraction of turmeric and enrichment method Download PDFInfo
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- CN108524865A CN108524865A CN201810126179.3A CN201810126179A CN108524865A CN 108524865 A CN108524865 A CN 108524865A CN 201810126179 A CN201810126179 A CN 201810126179A CN 108524865 A CN108524865 A CN 108524865A
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- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/906—Zingiberaceae (Ginger family)
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- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/331—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using water, e.g. cold water, infusion, tea, steam distillation, decoction
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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
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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
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Abstract
The invention discloses a kind of extraction of turmeric and enrichment methods, belong to Natural Medicine Chemistry extractive technique neighborhood.The extraction of turmeric and enrichment method, include the following steps：1. the preparation of chitin nanometer；2. the crushing of medicinal material；3. the preparation of ionic liquid and chitin nanometer solution：Ionic liquid, 3 methylimidazole of bromination dodecyl, 200mM.Chitin nanometer, 200 μ g/mL；4. ionic liquid ultrasonic extraction：0.2g Turmeric Roots are added in 10mL ionic liquids in Ultrasound Instrument, the ultrasonic extraction 30min at 40 DEG C；5. chitin nanometer is enriched with：The turmeric ionic liquid extract liquid of 1.0mg/mL is enriched with 0.6 μ g/mL chitin nanometers；6. eluting solvent：Acetone.The method significantly reduce the use of organic solvent, the pollution and harm in extraction process are significantly reduced, extraction effect and extraction efficiency is improved, and this method is simple, has wide range of applications, easy to use, concentration effect is notable.
Description
Technical field
The invention belongs to natural drugs to extract preparation field.It is related to a kind of traditional Chinese medicine extraction enrichment method, specifically, it
It is related to by ionic liquid as Extraction solvent and chitin nanometer as adsorbent, extraction is enriched with having in Turmeric
Imitate ingredient.I.e. the present invention provides a kind of new method, this method is by the ingenious combination of the property of ionic liquid and chitin nanometer
Get up, the active ingredient that can be fast and effeciently enriched in natural products.
Background technology
Natural products is the biologically active compound of the non-synthetic containing abundant source, has unique pharmacological action
With reliable therapeutic efficiency.They be mainly derived from plant, animal, marine organisms, insect, microorganism and fungi chemistry at
Point, also form the basis of important synthesis or semi-synthetic compound.The analysis of natural extracts is one attractive
Research field, caused the extensive concern of domestic and international researcher in recent years.Although in terms of extractive technique obtain it is important into
Exhibition, but for the analysis and research of natural extracts, for solid sample, extract multifarious target compound
It is still a difficult task.Recent research indicate that liquid-solid extraction technology, as ultrasound on extracting, Soxhlet extraction, immersion carry
It takes, refluxing extraction, supercritical fluid extraction, can be used for the extraction of natural products.However, these extraction process often take
, and consume a large amount of organic solvent.Therefore, a kind of green, efficient pre-concentration extracting method are developed for natural products,
Especially solid sample is necessary.
Chitosan is a kind of linear cationic polysaccharide that nature is widely present, and is acted on by deacetylated by chitin
It arrives, chemical name is Chitosan (1-4) -2- amino-beta-D glucose.Since 1859, the natural goods of this nonhazardous
Matter is due to its abundant natural source, biocompatibility, broad spectrum antibacterial, microbic resolvability, non-toxic, strong adsorptivity and easily
In excellent performances such as chemical modifications, it is considered as a kind of bioabsorbable polymer material with unique potential.In recent years, chitosan nano
Particle shows great application prospect in terms of biology, medicine and food.In the various sides for preparing chitin nanometer
In method, Ionic gelation method is since its process is nontoxic, conveniently and has controllably attracted wide public concern.Currently, chitosan nano
Son has been applied to therapeutic protein, polypeptide, the transmission of pDNA, siRNA and Medicine small molecule.However, as far as we know, shell is poly-
Research of the sugared nano-particle in terms of Natural Product Samples extraction has not been reported.
In nature, pigment is by extraction in animal and plant tissue and microorganism (culture) and biosynthesis not phase
The multifarious compound closed, there are one common features for tool：Their electronic structure often contains chromophore, is responsible for these changes
Close the characteristic color of object.Currently, the natural pigment in plant is used in the industrial circles such as food, cosmetics, medicine, feed stripped
Make additive or nutritional supplement.Turmeric is famous one of natural plant pigment, and being commonly used for fragrance, (curry is its feature perfume
The main component of taste), the pigment and dyestuff of textile, food color and traditional Chinese medicine.Curcumin, mainly from turmeric rhizome
In isolated xanthein, be made of three polyphenol compounds：Curcumin, Demethoxycurcumin and double de-methoxies
Curcumin.Curcumin chemical compounds have extensive bioactivity and pharmacological action, including antitumor, anti-inflammatory, antiviral, anti-
Oxidation, anti-senile dementia, anti-liver poison, AIDS virus resisting and cardiovascular protection.Currently, the extraction of turmeric mainly uses tradition
Method, such as subcritical and fluid under pressure extraction, microwave―assisted extraction, water bath reflux method, ultrasonic extraction, Solid Phase Extraction
Method.However, the extracting method of this quasi-tradition exists, time-consuming, solvent toxicity is big, amount of samples is more, environmental pollution is serious and cannot be rich
The shortcomings of collection.Therefore, analysis of a kind of environmentally protective enrichment extracting method of exploitation for curcumin chemical compounds is very must
It wants.
Invention content
It is a kind of compared to the previous enrichment method more rapidly and efficiently technology of convenient nonhazardous it is an object of the invention to seek,
For the active constituent in Extraction and enrichment natural products.Invention is characterized by chitin nanometer enrichment and ionic liquid extraction
The ingenious combination of the two, is naturally produced at the advantages of having given full play to both Extraction and enrichment modes with this combination technique Extraction and enrichment
Active ingredient in object can obtain effect that is unprecedented, getting instant result.
The present invention specifically provides a kind of using ionic liquid as Extraction solvent and chitin nanometer as adsorbent
Beneficiation technologies, the curcumin chemical compounds ingredient for being enriched in turmeric.It specifically includes：With reference to pharmacopeia, replaced with ionic liquid
Organic solvent extracts the active ingredient in raw medicinal material turmeric, is prepared into the dilution of turmeric extract, and chitosan nano is added
Rice corpuscles dispersion liquid is enriched with, and dissolving step is volatilized using elution, and last sample introduction is analyzed.
In the present invention, the ionic liquid is selected from 1- ethyl-3-methylimidazoles-Pfansteihl salt, 1- hexyl pyridinium tetrafluoroborates
Salt, bromination 1- dodecyl -3- methylimidazoles, chlorination 1- dodecyl -3- methylimidazoles, 1- dodecyl -3- methylimidazoles
Any one in mesylate, 1- dodecyl -3- methylimidazolium nitrates.Preferred ionic liquid is bromination 1- dodecanes
Base -3- methylimidazoles.
Specifically, Chinese medicine pre-treating method of the present invention is realized by following technical measures：
A. the pretreatment of raw medicinal material is sieved through sieve through being ground into powdery granule, and by No.1；
B. with reference to pharmacopeia, turmeric raw medicinal material is pre-processed, ionic liquid is used to prepare turmeric medicine as Extraction solvent
Material extracting solution mother liquor；
C. it weighs chitin nanometer and nano dispersion fluid is made；
D. by optimal enrichment strategy, sample mixed liquor is enriched with；
E. pregnant solution is filtered, and through eluting link, volatilizing link, dissolving link, rear sample introduction is analyzed and characterized its concentration effect.
The enrichment mixed liquor, it is characterised in that including turmeric medicinal material dilution, chitin nanometer dispersion liquid, and
The volume ratio of the two is V (turmeric medicinal material dilution)：V (chitin nanometer dispersion liquid)=997：3
The turmeric medicinal material dilution, it is characterised in that mixed liquor includes Radix Et Rhizoma Rhei extract mother liquor and water, and the two
Volume ratio be V (turmeric extract mother liquor)：V (water)=50：947
The water, it is characterised in that the pH=6.5 of water
The chitin nanometer dispersion liquid, it is characterised in that mass concentration is the aqueous solution of 200 μ g/mL, and every
The addition volume range of chitin nanometer is in 10-50 μ L in 1000 μ L mixed liquors.
The bromination 1- dodecyl -3- methylimidazole aqueous solutions, it is characterised in that mass concentration is the water-soluble of 200mM
Liquid.
The elution link, it is characterised in that eluted 3 times with containing 100 μ L of acetone.Described volatilizes link, feature
It is that 80 DEG C of normal pressure water-baths volatilize.The dissolving link, it is characterised in that 100 μ L acetone ultrasounds 2min are added.
The concentration effect measures the content of active ingredient in turmeric to characterize this by Agilent 1290UHPLC
The validity of enrichment method.
Specific operation process is：
1. the preparation process of turmeric extract mother liquor：
By turmeric pulverizing medicinal materials, powder (crossing No. four sieves) about 0.2g is taken, it is accurately weighed, it sets in conical flask with cover, precision adds
People 200mM bromination 1- dodecyl -3- methyl imidazole solutions 10mL, weighed weight are heated to reflux 30 minutes, let cool, then weighed
Weight is supplied the weight of less loss with 200mM bromination 1- dodecyl -3- methyl imidazole solutions, is shaken up, and filtration takes subsequent filtrate, i.e.,
.
2. enrichment process operating procedure：
2.1 take 1 clean 30mL specifications tool plug wide-mouth bottle, and chitin nanometer dispersion liquid (200 μ g/mL) 30 is added
μ L, 9470 μ L of water of pH=6.5,500 μ L of turmeric herbal extract.
Wide-mouth bottle is placed in oscillation convolution 60s on cyclotron oscillation instrument by 2.2.
2.3 take specification for the miillpore filter of the syringe and 0.22 μm of specification of 10mL, use 1mL methanol and pure water to filter respectively
Film is activated, and draws mixed liquor, enrichment filtering is carried out to mixed liquor using the filter membrane after activation.
2.4 elute three times the chitin nanometer particle in filter membrane with acetone, every time 100 μ L.It is another take 1 it is clean
Centrifuge tube is packed into the eluent of merging, which is placed in 80 DEG C of water-baths and is volatilized.
2.5 volatilize after residual solids 100 μ L dissolving of acetone, ultrasonic 2min is placed in 13000rpm centrifuges and centrifuges
5min takes supernatant liquor to fill sample, and with UHPLC, sample introduction is analyzed.
The advantage of the invention is that：
1. the method for the present invention is enriched with, link intention is novel, and thinking is ingenious.Use chitin nanometer as absorption for the first time
Technology of the agent for enrichment, and apply and be enriched with field in natural product extraction.Used novel green extraction system-from
Sub- liquid surfactant system, in particular by ling-chain ion liquid-bromination 1- dodecyl -3- methylimidazoles as extractant
When for separation and concentration turmeric effective ingredient, extraction effect is suitable with methanol.The extraction system has a series of excellent outstanding
Characteristic：It is nontoxic to human body, free from environmental pollution；Thermal stability and chemical stability are good, nonflammable, and safe operating environment is reliable.
2 after enrichment method processing, and the sensitivity of instrument greatly improves, each curcumin ingredient in turmeric medicinal material
Detection limit than conventional method reduce at least 50 times or so so that curcumin, de-methoxy ginger in measuring turmeric medicinal material
Flavine, Bisdemethoxycurcumin three classes curcumin ingredient are more accurate effective.And the enrichment times of the technology of the present invention are high
Up to 79~169 times.
3. this method has wide range of applications, either the raw medicinal material of turmeric or other medicinal materials, as rheum officinale can use this
Inventive method carries out separation and concentration.And the application of the present invention for measuring turmeric medicinal material and rhubarb medicinal material these two aspects also falls within head
Example.
4. ionic liquid and chitin nanometer material that the present invention uses, not only cheap and easy to get, but also they are
Have a series of excellent physicochemical properties outstanding：Chemical stability and good thermal stability are nontoxic to human body, do not pollute
Environment, it is nonflammable.
5. experiment concentration effect provided by the invention is efficiently notable, and safe operating environment, operating procedure are concise.
That is the present invention provides a new technique, the technology adsorb ionic liquid extract technology and chitin nanometer
Characteristic is ingenious to be combined, can curcumin active ingredient of the convenient and efficient ground in separation and concentration natural products.
Description of the drawings
Fig. 1 is the process flow chart of enrichment method of the present invention.
Fig. 2 is scanning and the projection electron microscope of chitosan and chitin nanometer.
Fig. 3 is (-) Q-TOF (the ESI)/MS chromatographies and cracking rule figure of Curcumins in Curcuma longa L.It is alphabetical in figure
A, B, C respectively represent active ingredient different in turmeric, respectively：A, Bisdemethoxycurcumin；B, Demethoxycurcumin；
C, curcumin.
Fig. 4 A are the concentration effect block diagram for investigating different ions liquid type.In figure, 1,2,3 respectively represent difference in turmeric
Active ingredient, respectively：1, Bisdemethoxycurcumin；2, Demethoxycurcumin；3, curcumin.In figure, A, B, C, D,
E, F respectively represents different ionic liquid types, respectively：A, 1- ethyl-3-methylimidazole-Pfansteihl salt；B, 1- dodecyl-
3- methylimidazole mesylates；C, 1- hexyl pyridinium tetrafluoroborate salt；D, chlorination 1- dodecyl -3- methylimidazoles；E, 1- ten
Dialkyl group -3- methylimidazolium nitrates；F, bromination 1- dodecyl -3- methylimidazoles.
Fig. 4 B are the concentration effect line chart for investigating different ions liquid concentration.In figure, 1,2,3 respectively represent difference in turmeric
Active ingredient, respectively：1, Bisdemethoxycurcumin；2, Demethoxycurcumin；3, curcumin.
Fig. 4 C are the concentration effect line chart for investigating different chitin nanometer concentration.In figure, 1,2,3 respectively represent ginger
Different active ingredient in Huang, respectively：1, Bisdemethoxycurcumin；2, Demethoxycurcumin；3, curcumin.
Fig. 4 D are the concentration effect block diagram for investigating different eluting solvent types.In figure, 1,2,3 respectively represent in turmeric not
Same active ingredient, respectively：1, Bisdemethoxycurcumin；2, Demethoxycurcumin；3, curcumin.
Fig. 4 E are the concentration effect line chart for investigating different duration of oscillation.In figure, 1,2,3 respectively represent it is different in turmeric
Active ingredient, respectively：1, Bisdemethoxycurcumin；2, Demethoxycurcumin；3, curcumin.
Fig. 4 F are the concentration effect line chart investigated under different pH.In figure, 1,2,3 respectively represent it is different effective in turmeric
Ingredient, respectively：1, Bisdemethoxycurcumin；2, Demethoxycurcumin；3, curcumin.
Fig. 5 A are the liquid chromatogram of turmeric extract.In figure, 1,2,3 respectively represent active ingredient different in turmeric,
Respectively：1, Bisdemethoxycurcumin；2, Demethoxycurcumin；3, curcumin.Letter a, b, c respectively represent difference in figure
Sample, respectively：A, organic solvent extracting solution；B, ionic liquid extracting solution；C, the chitin nanometer of ionic liquid extracting solution
Pregnant solution.
Fig. 5 B are that the TIC/EIC of turmeric extract schemes.In figure, 1,2,3 respectively represent active ingredient different in turmeric, point
It is not：1, Bisdemethoxycurcumin；2, Demethoxycurcumin；3, curcumin.Letter a, b, c are respectively represented different in figure
Sample, respectively：A, organic solvent extracting solution；B, ionic liquid extracting solution；The chitin nanometer of c, ionic liquid extracting solution are rich
Liquid collecting.
Specific implementation mode
Beneficiation technologies provided by the present invention are described in more detail by following instance.Since it applies model
It encloses extensively, therefore specific embodiment is also more, the discussion below in conjunction with several examples is further elaborated present disclosure.
Chitin nanometer in the embodiment of the present invention is made by the following method：
2.0g chitosans (containing 0.1% acetic acid) are added in 98.0g deionized waters and vibrate 60min at room temperature.Again thereto by
It is added dropwise to 100mL sodium tripolyphosphate solutions (1.0mg/mL).Mixture is continuously stirred at room temperature for 24 hours, it is outstanding to obtain milky
Turbid.Milky suspension 30min under 4000 turns obtained by centrifugation removes supernatant liquor, is cleaned with deionized water, and freezing is dry
It is dry to get chitin nanometer.
1- ethyl-3-methylimidazoles-Pfansteihl salt, 1- hexyl pyridinium tetrafluoroborates salt, bromination 1- dodecyl -3- methyl
Imidazoles, chlorination 1- dodecyl -3- methylimidazoles, 1- dodecyl -3- methylimidazoles mesylate, 1- dodecyl -3- first
Base imidazole nitrate
Embodiment 1. investigates influence of the ionic liquid type to concentration effect
1.1 take 6 clean 30mL tools plug wide-mouth bottles, number 1,2,3,4,5,6 that 20mg/mL turmeric ionic liquids are added and carry
Take liquid 0.5mL, 200 μ g/mL chitin nanometers 0.02mL and deionized water 9.48mL.The turmeric ionic liquid of No. 1 addition carries
It is that 1- ethyl-3-methylimidazoles-Pfansteihl salt carries to take liquid, and the turmeric ionic liquid extracting solution of No. 2 additions is 1- dodecyls -3-
Methylimidazole mesylate carries, and the turmeric ionic liquid extracting solution of No. 3 additions is that 1- hexyl pyridinium tetrafluoroborate salt carries, No. 4
The turmeric ionic liquid extracting solution of addition is that chlorination 1- dodecyl -3- methylimidazoles carry, the turmeric ionic liquid extraction of No. 5 additions
Liquid is that 1- dodecyl -3- methylimidazolium nitrates carry, and the turmeric ionic liquid extracting solution of No. 6 additions is bromination 1- dodecanes
Base -3- methylimidazoles carry.
1.2. the wide-mouth bottle equipped with mixed liquor is put into cyclotron oscillation device, vibrates 60s.It is drawn with 10mL disposable syringes
Solution in wide-mouth bottle.
1.3 remove syringe needle, load onto 0.22 μm of filtering head, syringe is placed on solid-phase extracting instrument and is filtered, until nothing
Until water droplet, filtering head is removed.
1.4 take 6 1.5mL specification centrifuge tubes, and number 1-6, three times with 100 μ L methanol elution filtering head, cleaning solution is collected
In in 1.5mL specification centrifuge tubes, vortex 5s.Cleaning solution is volatilized, is redissolved with 100 μ L methanol.
Centrifuge tube is placed in centrifuge by 1.5, and 5min is centrifuged under 13000rpmin, sample is filled, with UHPLC analysis results.
UHPLC chromatographic conditions are：
Chromatographic column：Agilent SB-C18 (1.8 μm, 50mm × 4.6mm i.d.), Detection wavelength：430nm, column temperature：25
DEG C, sample size：1.0 μ L, flow velocity 0.4mL/min, mobile phase：A：4% glacial acetic acid, B：Acetonitrile.Gradient elution：0~4min, 46%
~46%B；4~5min, 46%~48%B；5~7min, 48%~48%B；7~8min, 48%~50%B；8~
8.5min, 50%~70%B；8.5~9min, 70%~100%B.
Experimental result such as the following table 1, the data in table 1 are peak area.
Table 1
Fig. 4 A show the concentration effect block diagram of different ions liquid type.In figure, 1,2,3 respectively represent difference in turmeric
Active ingredient, respectively：1, Bisdemethoxycurcumin；2, Demethoxycurcumin；3, curcumin.
From above-mentioned data it can be found that the extraction efficiency of ling-chain ion liquid is significantly greater than short chain ionic liquid.Possible cause is,
The hydrophobicity of the growth of ionic liquid alkyl chain therewith, ionic liquid also enhances, and the active constituent in turmeric is slightly soluble in water, according to
The similar principle that mixes, ionic liquid enhance the extraction efficiency of target analytes with the increase of long alkyl chains.Different sun
Extraction efficiency from molecular ling-chain ion liquid is also different, and the concentration effect for the ionic liquid being made of bromide ion is best, so
Select bromination 1- dodecyl -3- methylimidazoles.
Embodiment 2. investigates influence of the ionic liquid concentration to concentration effect
2.1 take 5 clean 30mL tools plug wide-mouth bottles, number 1,2,3,4,5 that the extraction of 20mg/mL turmeric ionic liquids is added
Liquid 0.5mL, 200 μ g/mL chitin nanometers 0.02mL and deionized water 9.48mL.The turmeric ionic liquid extraction of No. 1 addition
Liquid is that 100mM bromination 1- dodecyl -3- methylimidazoles carry, and the turmeric ionic liquid extracting solution of No. 2 additions is 150mM brominations 1-
Dodecyl -3- methylimidazoles carry, and the turmeric ionic liquid extracting solution of No. 3 additions is 200mM bromination 1- dodecyl -3- methyl
What imidazoles carried, the turmeric ionic liquid extracting solution of No. 4 additions is that 250mM bromination 1- dodecyl -3- methylimidazoles carry, and No. 5 add
The turmeric ionic liquid extracting solution entered is that 300mM bromination 1- dodecyl -3- methylimidazoles carry.
Wide-mouth bottle equipped with mixed liquor is put into cyclotron oscillation device by 2.2, vibrates 60s.It is drawn with 10mL disposable syringes
Solution in wide-mouth bottle.
2.3 remove syringe needle, load onto 0.22 μm of filtering head, syringe is placed on solid-phase extracting instrument and is filtered, until nothing
Until water droplet, filtering head is removed.
2.4 take 5 1.5mL specification centrifuge tubes, and number 1-5, three times with 100 μ L methanol elution filtering head, cleaning solution is collected
In in 1.5mL specification centrifuge tubes, vortex 5s.Cleaning solution is volatilized, is redissolved with 100 μ L methanol.
Centrifuge tube is placed in centrifuge by 2.5, and 5min is centrifuged under 13000rpmin, sample is filled, with UHPLC analysis results.
UHPLC chromatographic conditions are：
Chromatographic column：Agilent SB-C18 (1.8 μm, 50mm × 4.6mm i.d.), Detection wavelength：430nm, column temperature：25
DEG C, sample size：1.0 μ L, flow velocity 0.4mL/min, mobile phase：A：4% glacial acetic acid, B：Acetonitrile.Gradient elution：0~4min, 46%
~46%B；4~5min, 46%~48%B；5~7min, 48%~48%B；7~8min, 48%~50%B；8~
8.5min, 50%~70%B；8.5~9min, 70%~100%B.
Experimental result such as the following table 2, the data in table 2 are peak area.
Table 2.
Fig. 4 B show the concentration effect line chart under different ions liquid concentration.In figure, 1,2,3 respectively represent in turmeric not
Same active ingredient, respectively：1, Bisdemethoxycurcumin；2, Demethoxycurcumin；3, curcumin.
From above-mentioned data it is found that with bromination 1- dodecyl -3- methylimidazole concentration increase, concentration effect present on
The trend of liter, and reach maximum value in 200mM, then it is further added by the concentration of bromination 1- dodecyl -3- methylimidazoles, turmeric
The extraction efficiency of middle active ingredient is in reduction trend.Possible reason, bromination 1- dodecyl -3- methylimidazoles have good
The ability (cellulose is the constituent of cell wall) for dissolving cellulose, with bromination 1- dodecyl -3- methylimidazole concentration
Increase, more active constituents are extracted, but concentration is further added by therewith, and the viscosity of Extraction solvent increases so that object
The mass transfer of matter is hindered, and extraction efficiency reduces, so the concentration of bromination 1- dodecyl -3- methylimidazoles is finally selected as
200mM。
Embodiment 3. investigates influence of the chitin nanometer concentration to concentration effect
3.1 take 6 clean 30mL tools plug wide-mouth bottles, number 1,2,3,4,5,6 that 20mg/mL turmeric ionic liquids are added and carry
Take liquid 0.5mL, the 0 μ L of chitin nanometer dispersion liquid and deionized water 9.5mL, No. 2 200 μ of addition of No. 1 200 μ g/mL of addition
The 10 μ L of chitin nanometer dispersion liquid and deionized water 9.49mL of g/mL, the chitosan nano of No. 3 200 μ g/mL of addition
The 30 μ L of chitin nanometer dispersion liquid of 20 μ L of sub- dispersion liquid and deionized water 9.48mL, No. 4 200 μ g/mL of addition and go from
Sub- water 9.47mL, the 40 μ L of chitin nanometer dispersion liquid and deionized water 9.46mL of No. 5 200 μ g/mL of addition, No. 6 additions
The chitin nanometer dispersion liquid 50 μ L and deionized water 9.45mL of 200 μ g/mL so that chitosan in 1-6 mixed liquors
Concentration is followed successively by：0.0μg/mL、0.2μg/mL、0.4μg/mL、0.6μg/mL、0.8μg/mL、1.0μg/mL.
Wide-mouth bottle equipped with mixed liquor is put into cyclotron oscillation device by 3.2, vibrates 60s.It is drawn with 10mL disposable syringes
Solution in wide-mouth bottle.
3.3 remove syringe needle, load onto 0.22 μm of filtering head, syringe is placed on solid-phase extracting instrument and is filtered, until nothing
Until water droplet, filtering head is removed.
3.4 take 6 1.5mL specification centrifuge tubes, and number 1-6, three times with 100 μ L methanol elution filtering head, cleaning solution is collected
In in 1.5mL specification centrifuge tubes, vortex 5s.Cleaning solution is volatilized, is redissolved with 100 μ L methanol.
Centrifuge tube is placed in centrifuge by 3.5, and 5min is centrifuged under 13000rpmin, sample is filled, with UHPLC analysis results.
UHPLC chromatographic conditions are：
Chromatographic column：Agilent SB-C18 (1.8 μm, 50mm × 4.6mm i.d.), Detection wavelength：430nm, column temperature：25
DEG C, sample size：1.0 μ L, flow velocity 0.4mL/min, mobile phase：A：4% glacial acetic acid, B：Acetonitrile.Gradient elution：0~4min, 46%
~46%B；4~5min, 46%~48%B；5~7min, 48%~48%B；7~8min, 48%~50%B；8~
8.5min, 50%~70%B；8.5~9min, 70%~100%B.
Experimental result such as the following table 3, the data in table 3 are peak area.
Table 3.
Fig. 4 C show the concentration effect line chart under different chitin nanometer dispersion liquid concentrations.In figure, 1,2,3 point
Active ingredient different in turmeric is not represented, respectively：1, Bisdemethoxycurcumin；2, Demethoxycurcumin；3, turmeric
Element.
From above-mentioned data it is found that with chitin nanometer dispersion liquid concentration increase, chitin nanometer and object
The effect that matter combines is increasing.It is excessive due to interacting after the concentration of chitin nanometer reaches certain value, elution
Agent cannot be eluted well, so as to cause substance peak area with the increase that chitin nanometer concentration is added
And there is the phenomenon that being reduced after changing from small to big, so the chitosan of selection 0.6ug/mL.
Embodiment 4. investigates influence of the eluant, eluent type to concentration effect
4.1 take 6 clean 30mL tools plug wide-mouth bottles, number 1,2,3,4,5,6 that 20mg/mL turmeric ionic liquids are added and carry
Take the chitin nanometer dispersion liquid 30 μ L and deionized water 9.47mL of liquid 0.5mL, 200 μ g/mL.
Wide-mouth bottle equipped with mixed liquor is put into cyclotron oscillation device by 4.2, vibrates 60s.It is drawn with 10mL disposable syringes
Solution in wide-mouth bottle.
4.3 remove syringe needle, load onto 0.22 μm of filtering head, syringe is placed on solid-phase extracting instrument and is filtered, until nothing
Until water droplet, filtering head is removed.
4.4 take 6 1.5mL specification centrifuge tubes, and number 1-6, No. 1 elutes filtering head three times with 100 μ L80% methanol, washing
Liquid is collected in 1.5mL specification centrifuge tubes, and vortex 5s volatilizes cleaning solution, is redissolved with 100 μ L80% methanol.No. 2 with 100 μ L first
Alcohol elutes filtering head three times, and cleaning solution is collected in 1.5mL specification centrifuge tubes, and vortex 5s volatilizes cleaning solution, with 100 μ L methanol
It redissolves.No. 3 with 100 μ L ethanol elutions filtering heads three times, cleaning solution is collected in 1.5mL specification centrifuge tubes, and vortex 5s is volatilized and washed
Liquid is washed, is redissolved with 100 μ L ethyl alcohol.No. 4 elute filtering head three times with 100 μ L acetone, and cleaning solution is collected in 1.5mL specification centrifuge tubes
Interior, vortex 5s volatilizes cleaning solution, is redissolved with 100 μ L acetone.No. 5 elute filtering head three times with 100 μ L acetonitriles, and cleaning solution is collected
In in 1.5mL specification centrifuge tubes, vortex 5s volatilizes cleaning solution, is redissolved with 100 μ L acetonitriles.No. 6 are eluted with 100 μ L chloroforms
Three times, cleaning solution is collected in 1.5mL specification centrifuge tubes filtering head, and vortex 5s volatilizes cleaning solution, multiple with 100 μ L chloroforms
It is molten.
Centrifuge tube is placed in centrifuge by 4.5, and 5min is centrifuged under 13000rpmin, sample is filled, with UHPLC analysis results.
UHPLC chromatographic conditions are：
Chromatographic column：Agilent SB-C18 (1.8 μm, 50mm × 4.6mm i.d.), Detection wavelength：430nm, column temperature：25
DEG C, sample size：1.0 μ L, flow velocity 0.4mL/min, mobile phase：A：4% glacial acetic acid, B：Acetonitrile.Gradient elution：0~4min, 46%
~46%B；4~5min, 46%~48%B；5~7min, 48%~48%B；7~8min, 48%~50%B；8~
8.5min, 50%~70%B；8.5~9min, 70%~100%B.
Experimental result such as the following table 4, the data in table 4 are peak area.
Table 4.
Fig. 4 D show the concentration effect block diagram under different eluting solvents.In figure, 1,2,3 respectively represent difference in turmeric
Active ingredient, respectively：1, Bisdemethoxycurcumin；2, Demethoxycurcumin；3, curcumin.
Above-mentioned data explanation, different eluting solvents lead to different concentration effects, and the elution effect of acetone is best, first
Alcohol, ethyl alcohol, the elution effect of acetonitrile are suitable.Curcumin chemical compounds are polar substances, are had in intensive polar solvent better
Dissolubility.When selecting intensive polar solvent as eluting solvent, since the solubility of target compound in a solvent causes
Substance is transferred to the difficulty in eluting solvent, so acetone is optimal eluting solvent.
Embodiment 5. investigates influence of the duration of oscillation to concentration effect
5.1 take 5 clean 30mL tools plug wide-mouth bottles, number 1,2,3,4,5 that the extraction of 20mg/mL turmeric ionic liquids is added
The chitin nanometer dispersion liquid 30 μ L and deionized water 9.47mL of liquid 0.5mL, 200 μ g/mL.
Wide-mouth bottle equipped with mixed liquor is put into cyclotron oscillation device by 5.2, and No. 1 oscillation 20s, No. 2 oscillation 40s, No. 3 vibrate
60s, No. 4 oscillations 80s, No. 5 oscillation 100s.The solution in wide-mouth bottle is drawn with 10mL disposable syringes.
5.3 remove syringe needle, load onto 0.22 μm of filtering head, syringe is placed on solid-phase extracting instrument and is filtered, until nothing
Until water droplet, filtering head is removed.
5.4 take 5 1.5mL specification centrifuge tubes, and number 1-5, three times with 100 μ L acetone elution filtering head, cleaning solution is collected
In in 1.5mL specification centrifuge tubes, vortex 5s.Cleaning solution is volatilized, is redissolved with 100 μ L acetone.
Centrifuge tube is placed in centrifuge by 5.5, and 5min is centrifuged under 13000rpmin, sample is filled, with UHPLC analysis results.
UHPLC chromatographic conditions are：
Chromatographic column：Agilent SB-C18 (1.8 μm, 50mm × 4.6mm i.d.), Detection wavelength：430nm, column temperature：25
DEG C, sample size：1.0 μ L, flow velocity 0.4mL/min, mobile phase：A：4% glacial acetic acid, B：Acetonitrile.Gradient elution：0~4min, 46%
~46%B；4~5min, 46%~48%B；5~7min, 48%~48%B；7~8min, 48%~50%B；8~
8.5min, 50%~70%B；8.5~9min, 70%~100%B.
Experimental result such as the following table 5, the data in table 5 are peak area.
Table 5.
Fig. 4 E show the concentration effect line chart under different duration of oscillation.In figure, 1,2,3 respectively represent difference in turmeric
Active ingredient, respectively：1, Bisdemethoxycurcumin；2, Demethoxycurcumin；3, curcumin.
It is above-mentioned statistics indicate that, with the increase of extraction time, concentration effect gradually promotes and reaches at 60s saturation, past
Afterwards after extraction time increase, enrichment times are not promoted, and it is between substance and adsorbent to have downward trend, possible cause instead
Effect enhances with the increase of duration of oscillation, adsorption and desorption balance has been reached in 60s, the substance when being further added by the time
Desorption is more than suction-operated, and so as to cause the reduction of active material enrichment times, therefore optimal conditions is 60s.
Embodiment 6. investigates the concentration effect of different pH
6.1 take 10 clean 30mL tools plug wide-mouth bottles, number 1-10 that 20mg/mL turmeric ionic liquid extracting solutions are added
The 30 μ L of chitin nanometer dispersion liquid of 0.5mL and 200 μ g/mL, No. 1 is added 1200 μ L of 1M acetic acid solutions and deionized water
8.27mL, No. 2 are added 800 μ L of 1M acetic acid solutions and deionized water 8.67mL, and No. 3 are added 400 μ L of 1M acetic acid solutions and deionization
Water 9.07mL, No. 4 are added 200 μ L of 1M acetic acid solutions and deionized water 9.27mL, and No. 5 are added deionized water 9.47mL, No. 6 additions
5 μ L of 0.1M sodium hydroxides and deionized water 9.465mL, No. 7 are added 35 μ L of 0.1M sodium hydroxides and deionized water 9.435mL, No. 8
50 μ L of 0.1M sodium hydroxides and deionized water 9.42mL is added, No. 9 are added 5 μ L and deionized water 9.465mL of 1.0M sodium hydroxides,
No. 10 are added 20 μ L and deionized water 9.45mL of 1.0M sodium hydroxides so that the pH value of 1-10 mixed liquors is followed successively by：4.5、
5.0、5.5、6.0、6.5、7.0、7.5、8.0、8.5、9.0。
Wide-mouth bottle equipped with mixed liquor is put into cyclotron oscillation device by 6.2, vibrates 60s.It is drawn with 10mL disposable syringes
Solution in wide-mouth bottle.
6.3 remove syringe needle, load onto 0.22 μm of filtering head, syringe is placed on solid-phase extracting instrument and is filtered, until nothing
Until water droplet, filtering head is removed.
6.4 take 10 1.5mL specification centrifuge tubes, and number 1-10, three times with 100 μ L acetone elution filtering head, cleaning solution is received
It combines in 1.5mL specification centrifuge tubes, vortex 5s.Cleaning solution is volatilized, is redissolved with 100 μ L acetone.
Centrifuge tube is placed in centrifuge by 6.5, and 5min is centrifuged under 13000rpmin, sample is filled, with UHPLC analysis results.
UHPLC chromatographic conditions are：
Chromatographic column：Agilent SB-C18 (1.8 μm, 50mm × 4.6mm i.d.), Detection wavelength：430nm, column temperature：25
DEG C, sample size：1.0 μ L, flow velocity 0.4mL/min, mobile phase：A：4% glacial acetic acid, B：Acetonitrile.Gradient elution：0~4min, 46%
~46%B；4~5min, 46%~48%B；5~7min, 48%~48%B；7~8min, 48%~50%B；8~
8.5min, 50%~70%B；8.5~9min, 70%~100%B.
Experimental result such as the following table 6, the data in table 6 are peak area.
Table 6.
Fig. 4 F show the concentration effect line chart under different pH.In figure, 1,2,3 respectively represent it is different effective in turmeric
Ingredient, respectively：1, Bisdemethoxycurcumin；2, Demethoxycurcumin；3, curcumin.
It is above-mentioned statistics indicate that, in acid condition, more chitin nanometers be in cationic structural, the effect with substance
Increasingly stronger, substance is difficult to elute, and concentration effect continuously decreases；Under strongly alkaline conditions, the sun on chitin nanometer surface
Ion causes substance to be difficult to adsorb by alkali neutralization, and to be unable to reach concentration effect, therefore optimal conditions is pH=6.5.
Embodiment 7. measures the active component content in turmeric medicinal material
7.1, by the turmeric pulverizing medicinal materials in two different sources (Anhui and Guangdong), take powder (crossing No. four sieves) about 0.2g, essence
It is close weighed, it sets in 2 conical flask with cover, number A (Anhui), B (Guangdong), accurate plus people's 200mM bromination 1- dodecyls -3-
Methyl imidazole solution 10mL, weighed weight are heated to reflux 30 minutes, let cool, then weighed weight, with 200mM bromination 1- dodecanes
Base -3- methyl imidazole solutions supply the weight of less loss, shake up, and filtration takes subsequent filtrate to get turmeric ionic liquid extracting solution.
7.2 take 2 clean 30mL tools plug wide-mouth bottles, number 1,2, No. 1 addition 20mg/mL turmeric ionic liquid extracting solution
The 30 μ L of chitin nanometer dispersion liquid and deionized water 9.47mL of A0.5mL, 200 μ g/mL, No. 2 addition 20mg/mL turmerics
The chitin nanometer dispersion liquid 30 μ L and deionized water 9.47mL of ionic liquid extracting solution B 0.5mL, 200 μ g/mL.
Wide-mouth bottle equipped with mixed liquor is put into cyclotron oscillation device by 7.3, vibrates 60s.It is drawn with 10mL disposable syringes
Solution in wide-mouth bottle.
7.4 take 2 1.5mL specification centrifuge tubes, and number 1,2, three times with 100 μ L acetone elution filtering head, cleaning solution is received
It combines in 1.5mL specification centrifuge tubes, vortex 5s.Cleaning solution is volatilized, is redissolved with 100 μ L acetone.
Centrifuge tube is placed in centrifuge by 7.5, and 5min is centrifuged under 13000rpmin, sample is filled, with UHPLC analysis results.
UHPLC chromatographic conditions are：
Chromatographic column：Agilent SB-C18 (1.8 μm, 50mm × 4.6mm i.d.), Detection wavelength：430nm, column temperature：25
DEG C, sample size：1.0 μ L, flow velocity 0.4mL/min, mobile phase：A：4% glacial acetic acid, B：Acetonitrile.Gradient elution：0~4min, 46%
~46%B；4~5min, 46%~48%B；5~7min, 48%~48%B；7~8min, 48%~50%B；8~
8.5min, 50%~70%B；8.5~9min, 70%~100%B.
After measured, the content of curcumin is 282.1mg/g, the content of Demethoxycurcumin in the turmeric medicinal material of Anhui production
Content for 391.5mg/g, Bisdemethoxycurcumin is 52.1mg/g.
After measured, the content of curcumin is 4638.1mg/g in the turmeric medicinal material of Guangdong production, and Demethoxycurcumin contains
Amount is 2858.5mg/g, and the content of Bisdemethoxycurcumin is 5045.7mg/g.
In order to further verify the feasibility of this method, the investigation for having carried out methodology includes withinday precision, every other day essence
Density, repeatability and sample recovery rate.
Withinday precision
1 takes 1 clean 30mL tools plug wide-mouth bottle, and 20mg/mL turmeric ionic liquid extracting solution 0.5mL are added, 200 μ g/mL's
Chitin nanometer dispersion liquid 30 μ L and deionized water 9.47mL.
Wide-mouth bottle equipped with mixed liquor is put into cyclotron oscillation device by 2, vibrates 60s.It is drawn with 10mL disposable syringes wide
Solution in mouth bottle.
3 remove syringe needle, load onto 0.22 μm of filtering head, syringe is placed on solid-phase extracting instrument and is filtered, until anhydrous
Until drop, filtering head is removed.
4 take 1 1.5mL specification centrifuge tube, and three times with 100 μ L acetone elution filtering head, cleaning solution is collected in 1.5mL specifications
In centrifuge tube, vortex 5s.Cleaning solution is volatilized, is redissolved with 100 μ L acetone.
Centrifuge tube is placed in centrifuge by 5, and 5min is centrifuged under 13000rpmin, sample is filled, with UHPLC analysis results.
Sample introduction is analyzed, the different period sample introduction 6 times on the same day.
Day to day precision
1 takes 1 clean 30mL tools plug wide-mouth bottle, and 20mg/mL turmeric ionic liquid extracting solution 0.5mL are added, 200 μ g/mL's
Chitin nanometer dispersion liquid 30 μ L and deionized water 9.47mL.
Wide-mouth bottle equipped with mixed liquor is put into cyclotron oscillation device by 2, vibrates 60s.It is drawn with 10mL disposable syringes wide
Solution in mouth bottle.
3 remove syringe needle, load onto 0.22 μm of filtering head, syringe is placed on solid-phase extracting instrument and is filtered, until anhydrous
Until drop, filtering head is removed.
4 take 1 1.5mL specification centrifuge tube, and three times with 100 μ L acetone elution filtering head, cleaning solution is collected in 1.5mL specifications
In centrifuge tube, vortex 5s.Cleaning solution is volatilized, is redissolved with 100 μ L acetone.
Centrifuge tube is placed in centrifuge by 5, and 5min is centrifuged under 13000rpmin, sample is filled, with UHPLC analysis results.
Sample introduction is analyzed, the identical time point sample introduction in three days, daily into 2 times.
Repeatability
It is parallel to do 3 groups with reference to following experiments step, as investigation
1 takes 1 clean 30mL tools plug wide-mouth bottle, and 20mg/mL turmeric ionic liquid extracting solution 0.5mL are added, 200 μ g/mL's
Chitin nanometer dispersion liquid 30 μ L and deionized water 9.47mL.
Wide-mouth bottle equipped with mixed liquor is put into cyclotron oscillation device by 2, vibrates 60s.It is drawn with 10mL disposable syringes wide
Solution in mouth bottle.
3 remove syringe needle, load onto 0.22 μm of filtering head, syringe is placed on solid-phase extracting instrument and is filtered, until anhydrous
Until drop, filtering head is removed.
4 take 1 1.5mL specification centrifuge tube, and three times with 100 μ L acetone elution filtering head, cleaning solution is collected in 1.5mL specifications
In centrifuge tube, vortex 5s.Cleaning solution is volatilized, is redissolved with 100 μ L acetone.
Centrifuge tube is placed in centrifuge by 5, and 5min is centrifuged under 13000rpmin, sample is filled, with UHPLC analysis results.
Sample recovery rate
With reference to following experiments step, each concentration is parallel to do 3 groups
1. taking the tool plug wide-mouth bottle of 4 30mL specifications, number 1-4, No. 1 10mL are enriched with production turmeric ionic liquid in Anhui in mother liquor
Extracting solution 1mg/mL, 0.6 μ g/mL of chitin nanometer, curcumin standard items 141mg/g, Demethoxycurcumin 196mg/
G, Bisdemethoxycurcumin 26mg/g, No. 2 10mL are enriched with Anhui production turmeric ionic liquid extracting solution 1mg/mL, chitosan in mother liquors
0.6 μ g/mL of nano-particle, curcumin standard items 423mg/g, Demethoxycurcumin 588mg/g, Bisdemethoxycurcumin
Guangdong production turmeric ionic liquid extracting solution 1mg/mL in 78mg/g, No. 3 10mL enrichment mother liquors, 0.6 μ g/mL of chitin nanometer,
Curcumin standard items 2319mg/g, Demethoxycurcumin 1429mg/g, Bisdemethoxycurcumin 2523mg/g, No. 4 10mL
It is enriched with Guangdong production turmeric ionic liquid extracting solution 1mg/mL, 0.6 μ g/mL of chitin nanometer, curcumin standard items in mother liquor
6957mg/g, Demethoxycurcumin 4288mg/g, Bisdemethoxycurcumin 7568mg/g.
2. the wide-mouth bottle equipped with mixed liquor is put into cyclotron oscillation device, 60s is vibrated.It is drawn with 10mL disposable syringes wide
Solution in mouth bottle.
3. removing syringe needle, 0.22 μm of filtering head is loaded onto, syringe is placed on solid-phase extracting instrument and is filtered, until anhydrous
Until drop, filtering head is removed.
4. taking 4 1.5mL specification centrifuge tubes, number 1-4, three times with 100 μ L acetone elution filtering head, cleaning solution is collected
In in 1.5mL specification centrifuge tubes, vortex 5s.Cleaning solution is volatilized, is redissolved with 100 μ L acetone.
5. centrifuge tube is placed in centrifuge, 5min is centrifuged under 13000rpmin, sample is filled, with UHPLC analysis results.
Experimental result is summarized as follows table 7 and table 8：
Table 7.
Table 8.
The result shows that the repeatability of the method for the present invention is good, the rate of recovery is high, and detection accuracy is high.
Claims (10)
1. extraction and the enrichment method of a kind of turmeric, turmeric effective constituents are curcumin, de-methoxy turmeric in the turmeric
Element and Bisdemethoxycurcumin, it is characterised in that the described method comprises the following steps：The pretreatment of raw medicinal material, through being ground into
Powdery granule, and it is sieved through sieve by No.1；With reference to pharmacopeia, turmeric raw medicinal material is pre-processed, use ionic liquid as
Extraction solvent prepares turmeric herbal extract mother liquor；It weighs chitin nanometer and nano dispersion fluid is made；Pass through optimal richness
Collection scheme is enriched with sample mixed liquor；Pregnant solution is filtered, and through eluting link, volatilizing link, dissolving link, rear sample introduction
It is analyzed and characterized its concentration effect.
2. turmeric ionic liquid extracting solution as described in claim 1, it is characterised in that be made by the following method：
By turmeric pulverizing medicinal materials, powder (crossing No. four sieves) about 0.2g is taken, it is accurately weighed, it sets in conical flask with cover, precision plus people
200mM bromination 1- dodecyl -3- methyl imidazole solutions 10mL, weighed weight are heated to reflux 30 minutes, let cool, then weighed heavy
Amount, the weight of less loss is supplied with 200mM bromination 1- dodecyl -3- methyl imidazole solutions, is shaken up, and is filtered, is taken subsequent filtrate, i.e.,
.
3. chitin nanometer as described in claim 1, it is characterised in that the nano material is made by the following method：
2.0g chitosans (containing 0.1% acetic acid) are added in 98.0g deionized waters and vibrate 60min at room temperature.Add dropwise thereto again
Enter 100mL sodium tripolyphosphate solutions (1.0mg/mL).Mixture is continuously stirred at room temperature for 24 hours, milky suspension is obtained.
Milky suspension 30min under 4000 turns obtained by centrifugation removes supernatant liquor, is cleaned with deionized water, is freeze-dried, i.e.,
Obtain chitin nanometer.
4. ionic liquid as described in claim 1 is selected from 1- ethyl-3-methylimidazoles-Pfansteihl salt, 1- hexyl pyridinium tetrafluoroborates
Salt, bromination 1- dodecyl -3- methylimidazoles, chlorination 1- dodecyl -3- methylimidazoles, 1- dodecyl -3- methylimidazoles
Mesylate, 1- dodecyl -3- methylimidazolium nitrates.
5. a concentration of 100~300mM of ionic liquid as described in claim 1, preferably 200mM.
6. chitin nanometer dispersion liquid concentration as described in claim 1 is 0.0~1.0 μ g/mL, preferably 0.6 μ g/mL.
7. duration of oscillation as described in claim 1 is 20~100s, preferably 60s.
8. elution process as described in claim 1 eluting solvent elutes 3 times, every time 100 μ L, after gained eluent volatilizes, then
It is redissolved with 100 μ L eluting solvents.
9. the preferred eluting solvent of elution process as described in claim 1 is acetone.
10. enrichment process as described in claim 1, the pH value for being enriched with mother liquor is 6.5.
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| CN109535116A (en) * | 2018-11-21 | 2019-03-29 | 南京师范大学镇江创新发展研究院 | Method based on eutectic solvent mechanochemistry extraction natural active matter |
| CN109608428A (en) * | 2018-12-29 | 2019-04-12 | 杭州师范大学 | Micro- extracting method of phenolic compound in a kind of propolis |
| CN109557222A (en) * | 2019-01-28 | 2019-04-02 | 浙江工业大学 | A kind of Extraction and enrichment method of Sesquiterpene Polyesterss in RADIX CURCUMAE |
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| CN111777499A (en) * | 2020-08-11 | 2020-10-16 | 福州福德恩生物科技有限公司 | Curcumin extraction and purification method |
| CN113209666A (en) * | 2021-06-17 | 2021-08-06 | 浙江大学 | Preparation method and application of ionic liquid solution containing nano bubbles |
| CN116868996A (en) * | 2023-09-04 | 2023-10-13 | 成都绿金高新技术股份有限公司 | Pyrethrin emulsion with high stability and preparation method thereof |
| CN116868996B (en) * | 2023-09-04 | 2024-01-02 | 成都绿金高新技术股份有限公司 | Pyrethrin emulsion with high stability and preparation method thereof |
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