CN107789376A - A kind of two-phase depth congruent melting solvent for extracting Active Components of Ginkgo Leaves and preparation method thereof and extracting method - Google Patents
A kind of two-phase depth congruent melting solvent for extracting Active Components of Ginkgo Leaves and preparation method thereof and extracting method Download PDFInfo
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Abstract
The invention discloses a kind of two-phase depth congruent melting solvent for extracting Active Components of Ginkgo Leaves and preparation method thereof and extracting method, the two-phase depth congruent melting solvent is by isometric aqueous favoring and hydrophobic phase composition, aqueous favoring is made up of substance A and substance B, substance A is made up of DES1 and water, and DES1 is prepared by Choline Chloride and levulic acid；Substance B is made up of DES2 and water, and DES2 is prepared by Choline Chloride and malonic acid；Hydrophobic phase is prepared by methyl tricapryl ammonium chloride, octanol and octanoic acid.Two-phase depth congruent melting solvent prepared by the present invention is green solvent, and safety non-pollution, viscosity is small, and hydrogen bond is stable, good fluidity；Hydrophobic active ingredient polyisoamylene alcohol acetic ester and hydrophilic active agents GINKGO BILOBA EXTRACT in ginkgo leaf, terpene lactones and OPC can be extracted simultaneously, and recovery rate is high, safe to use, will not form residual.The preparation method of the deep congruent melting solvent of the present invention is simple and convenient, and cost is low, and biodegradability is high.
Description
Technical field
The present invention relates to the utilization of agricultural living resources, and in particular to a kind of two-phase for extracting Active Components of Ginkgo Leaves is deeply altogether
Molten solvent and preparation method thereof and extracting method.
Background technology
Ginkgo (scientific name：Ginkgo biloba L.), also known as Gong Sunshu, gingko, category gymnosperm, Ginkgoaceae Ginkgo,
Single category single.Ginkgo leaf, fruit etc. have medicinal Development volue, and it is precious living fossil from head to foot to be described as.Ginkgo originates in China, I
State's gingko resource owning amount accounts for more than the 70% of world's total amount.
Mainly include GINKGO BILOBA EXTRACT, terpene lactones, OPC, Polyprenol etc. in Active Components of Ginkgo Leaves.Gingko yellow
The content of letones occupy the first, and total content accounts for 2.5~5.9%, in ginkgo leaf it is separated go out more than 40 kind flavonoids things
Matter.Ginko leaves flavone class compound, which has, to be suppressed platelet aggregation, reduces blood viscosity, improves Brain circlulation, anti-atherogenic
The effect such as hardening, anti-oxidant, promotion adipocyte lipolysis, antitumor, it can be effectively applied to treat coronary heart disease, heart strand
Bitterly, the disease such as cerebral arteriovenous malformation, senile dementia, hypertension.
Ginkgolides is other a kind of important active component in ginkgo leaf, belongs to terpenoid, also known as Ginkgo biloba terpenes
Lactone, mainly include sesquiterpene lactone and diterpenoid-lactone.Bilobalide be in ginkgo leaf it is separated go out only one sequiterpene
Lactone compound.Ginkgolide A. B. C, M, J are diterpene ginkgolide.Ginkolide B is specificity platelet activation
The strong antagonistic of the factor (PAF).Scientists from all over the world carry out pharmacological research discovery, silver to Ginkgolides of Ginkgo Leaf class compound
Apricot lactone is the most medicine of prospect in natural paf receptor antagonistic at present, in protection ischemic brain damage, promotes nerve cord
Cell Differentiating Into Neurons, suppress nerve cell apoptosis, treatment central nervous system degenerative disease and disease of cardiovascular system
Etc. possess good potential applicability in clinical practice.
Polyprenol is a kind of lipids, and structure is mainly by a series of isopentene group units and terminal iso-amylene
Alcohol unit forms.Polyprenol contained by ginkgo leaf belongs to birch polyisoamylene alcohols, mainly exists in the form of acetate
In blade, small part exists in the form of free alcohol.Isopentene group unit number is 14- in ginkgo leaf Polyprenol molecule
24, main component is 17-19 isopentene group unit, accounts for 80% or so of total Polyprenol kind compound content.Poly- isoamyl
It is enols used that there is immunocompetence, can anti HIV-1 virus, it can also be used to treat immune deficiency illness such as septicemia etc., can lure
Apoptosis of tumor cells is led, while also has obvious bioactivity in terms of hepatitis virus resisting and NACT leukaemia, to high blood
The immune function diseases such as pressure, high fat of blood, diabetes, ventilation, lupus erythematosus have therapeutic action.
OPC is a kind of plant polyphenol kind compound with flavan-3-alcohol structure, in ginkgo biloba p.e about
Contain 4~12% content.In addition to well-known antioxidation activity, ginkgo leaf OPC has in cardiovascular system
Anti-hypertension, endothelium-dependent vasodilatation be active, anti-ischemia reperfusion injury, antiatherosclerosis, antiplatelet coagulate
Collection and other effects, also has significant protective effect to acute renal failure.In addition, OPC also has anticancer, immunocompetence
Regulation, capillary permeability, anti-inflammation and other effects are reduced, to diseases such as treatment peripheral vein insufficiency, lymphedemas
There is the effect of fine.
All it is generally at present to be used as Extraction solvent, water by the use of water or organic solvent on Active Components of Ginkgo Leaves extraction
It is poor as Extraction solvent extraction effect, and conventional organic solvents are volatile, easy residual, and environment and human body are damaged, cost
It is high.Further, since GINKGO BILOBA EXTRACT, terpene lactones, OPC have hydrophily, and polyisoamylene alcohol acetic ester has hydrophobicity,
Therefore, conventional Active Components of Ginkgo Leaves extracting method is all by the individually extraction or by hydrophilic composition and hydrophobic of these compositions
Property composition separately extract, so on the one hand cause bioactive ingredients to waste, on the other hand also increase extraction step, raising carries
Take cost.Therefore, seeking a kind of method of green, safe efficient, synchronous extraction ginkgo active component is highly desirable.
The content of the invention
Goal of the invention：The problem of existing for prior art, the present invention provide a kind of two-phase depth congruent melting solvent
(TPDESs).Two-phase depth congruent melting solvent provided by the invention safety non-pollution, is repeated and utilized, easily biology as green solvent
Degraded, preparation technology is simple, and cost is low, have steam force down, be non-combustible, dissolubility and excellent conductivity, electrochemical window it is steady
The property such as fixed；Various active composition in ginkgo leaf, including flavones, terpene lactones, former cyanine can be extracted with green safe high efficiency synchronous
Element, polypentenol acetic acid esters.
The present invention also provides the preparation method of the two-phase depth congruent melting solvent and utilizes the two-phase depth congruent melting solvent extraction ginkgo
The method of leaf active component.
Technical scheme：To achieve these goals, a kind of two-phase for extracting Active Components of Ginkgo Leaves as described in the present invention
Deep congruent melting solvent, by isometric aqueous favoring and hydrophobic phase composition, the aqueous favoring is by substance A and substance B 10- by volume
0:0-10 is formed, and the substance A is by DES1 and water in mass ratio 6:3.5-4.5 is formed, and the DES1 is by Choline Chloride and second
Acyl propionic acid is according to mol ratio 1:1.5-2.5 it is prepared；The substance B is by DES2 and water in mass ratio 4.5:5-6 is formed, institute
It is according to mol ratio 1 by Choline Chloride and malonic acid to state DES2:1.5-2.5 it is prepared；The hydrophobic phase is pungent by methyl three
Ammonium chloride, octanol and octanoic acid are according to mol ratio 1:2:The common solvent DES3 of depth that 2.5-3.5 is prepared.
Preferably, the aqueous favoring is by substance A and substance B 7.75-8.75 by volume:2.25-1.25 composition.
Most preferably, in deep congruent melting solvent aqueous favoring by substance A and substance B by volume 8.75:1.25 composition.
Preferably, the substance A is by DES1 and water in mass ratio 6:4-4.5 is formed, and the DES1 is by Choline Chloride
With levulic acid according to mol ratio 1:2-2.5 it is prepared；The substance B is by DES2 and water in mass ratio 4.5:5.5-6 group
Into the DES2 is according to mol ratio 1 by Choline Chloride and malonic acid:1.5-2 it is prepared；The hydrophobic phase is by methyl
Trioctylmethylammonium chloride, octanol and octanoic acid are according to mol ratio 1:2:2.5-3 it is prepared.
Most preferably, the substance A is by DES1 and water in mass ratio 6:4 compositions, the DES1 is by Choline Chloride and second
Acyl propionic acid is according to mol ratio 1:2 are prepared；The substance B is by DES2 and water in mass ratio 4.5:5.5 compositions, the DES2
It is according to mol ratio 1 by Choline Chloride and malonic acid:2 are prepared；The hydrophobic phase DES3 is by methyl trioctylphosphine chlorination
Ammonium, octanol and octanoic acid are according to mol ratio 1:2:3 are prepared.
The preparation method of two-phase depth congruent melting solvent of the present invention, comprises the following steps：
(1) Choline Chloride and levulic acid are weighed in molar ratio and are well mixed, the heating stirring between 80~110 DEG C,
Until forming transparency liquid, it is deep solvent DES1 altogether, DES1 and water is mixed according to mass ratio and produce substance A；
(2) Choline Chloride and malonic acid are weighed in molar ratio and is well mixed, the heating stirring between 80~110 DEG C, directly
To transparency liquid is formed, it is deep solvent DES2 altogether, DES2 and water is mixed according to mass ratio and produce substance B；
(3) substance A and substance B are mixed to the aqueous favoring for producing the deeply common solvent of two-phase by volume；
(4) methyl tricapryl ammonium chloride, octanol and octanoic acid are weighed in molar ratio and is well mixed, between 80~110 DEG C
Heating, until formation transparency liquid, is deeply altogether solvent DES3, the hydrophobic phase as the deeply common solvent of two-phase；
(5) aqueous favoring and hydrophobic equal volume are mixed, are layered after standing, that is, obtain two-phase depth congruent melting solvent.
The method of two-phase depth congruent melting solvent extraction Active Components of Ginkgo Leaves of the present invention, it is characterised in that including such as
Lower step：
(1) first it is placed in and is carried according to the preparation method preparation two-phase depth congruent melting solvent of two-phase depth congruent melting solvent according to solid-liquid ratio
In extracting container, accurately weigh Ginkgo Leaf and add in the deeply common solvent of the two-phase in extraction vessel, be well mixed；
(2) heating extraction after mixing, extraction centrifuge after terminating, two-phase system layering, and upper phase is hydrophobic phase, and lower phase is parent
Aqueous phase.Aqueous favoring detection flavones therein, terpene lactones, procyanidin content are taken, takes hydrophobic phase to detect Polyprenol therein
Acetate content.
Wherein, the mass volume ratio of step (1) Ginkgo Leaf and the deep congruent melting solvent after dilution is 1:15-
25g/mL.It is preferred that the mass volume ratio of Ginkgo Leaf and two-phase depth congruent melting solvent is 1:20-25g/mL.Optimal mass body
Product is than being 1:20g/mL.
Wherein, the heating extraction described in step (2) is vibration heating extraction or agitating and heating extraction.
The rotating speed of the vibration or stirring is 100-300rpm, and temperature is 50-70 DEG C, time 30-60min.
The preferable rotating speed for vibrating or stirring is 150-160rpm, and temperature is 60-65 DEG C, time 40-45min.
Optimal vibration or the rotating speed of stirring are 150rpm, and temperature is 60 DEG C, time 40min.
The constituent of two-phase depth congruent melting solvent (TPDESs) property and each phase depth congruent melting solvent (DESs) of the present invention,
Constitutive molar ratio and water content have important relationship, and trickle component difference can cause DESs properties greatly to change, can be with
Property is carried out to DESs using this characteristic and is adapted to different application demands.The TPDESs of the present invention, can be the same as the moment
It is interior that several active components in ginkgo leaf are efficiently extracted, because the hydrophobicity of polyprenols is larger,
Differed greatly with material polarity such as flavones, terpene lactones, single solvent progress combined highly effective extraction feasibility is little, and the present invention is set
Two-phase system depth congruent melting solvent has been counted out, stable two-phase system can have been formed, upper phase is hydrophobic phase, and lower phase is aqueous favoring.Stir
Two-phase can also be divided into rapidly after mixing extraction, as shown in Figure 1.
Beneficial effect：Compared with prior art, the invention has the advantages that：
(1) two-phase depth congruent melting solvent prepared by the present invention is green solvent, safety non-pollution, repeats and utilizes, easily biology
Degraded, there is steam to force down, be non-combustible, the property such as dissolubility and excellent conductivity, electrochemical window are stable；The present invention simultaneously
TPDESs viscosity it is small, hydrogen bond is stable, good fluidity；It can be extracted simultaneously using the TPDESs of the present invention more in ginkgo leaf
Kind active component, and residual will not be formed, harm will not be produced to environment and human body.
(2) preparation method of the deep congruent melting solvent of the present invention is simple and convenient, and raw material sources are wide, and cost is low, and raw degradability is high.
(3) it is easy to operate using the method for two-phase depth congruent melting solvent extraction Active Components of Ginkgo Leaves of the present invention, extraction effect
Rate is high, safe to use, will not cause the wasting of resources.
Brief description of the drawings
Fig. 1 is the schematic diagram of two-phase system and two-phase system after extraction before DESs extractions；
Fig. 2 is the influence graph of a relation that different Extracting temperatures extract Active Components of Ginkgo Leaves recovery rate to DESs；
Fig. 3 is the influence graph of a relation for different extraction times Active Components of Ginkgo Leaves recovery rate being extracted to DESs.
Embodiment
Below in conjunction with drawings and examples, the present invention will be further described.
Experimental raw：
The raw material ginkgo leaf of experiment comes from Pizhou City Tie Fu towns ginkgo leaf production base, and ginkgo leaf plucking time is 5
Month.
Standard items rutin is purchased from Shanghai Yuan Ye bio tech ltd, and standard items ginkalide A is given birth to from Chinese medicine
Tetramune examines and determine institute, and isopropanol, methanol, n-hexane are chromatographically pure, and other medicines used are that analysis is pure.
P1201 high performance liquid chromatographs and UV1201 detectors, Dalian Yilite Analytical Instrument Co., Ltd；
UV-1200 type ultraviolet-uisible spectrophotometers, Shanghai Mei Puda Instrument Ltd.；
JY-2 constant temperature stirs oil bath pan, Tian Jing laboratory apparatus factory of Jintan City；
Constant temperature culture oscillator ZWYR-2112B, Shanghai Zhi Cheng analytical instrument Manufacturing Co., Ltd；
TG16A-WS table model high speed centrifuges, Shanghai Lu Xiang instrument centrifuges Instrument Ltd..
Other raw materials are all commercially available, by raw material Choline Chloride, levulic acid, malonic acid, methyl trioctylphosphine chlorination
Ammonium, octanol and octanoic acid dry water removal in vacuum drying chamber.
Embodiment 1
(1) example 1 in molar ratio:2 weigh Choline Chloride and levulic acid and are well mixed, and are heated between 80~110 DEG C
Stirring, it is deep solvent DES1 altogether, by DES1 and water according to mass ratio 6 until forming transparency liquid:4 mix and produce material
A；
(2) in molar ratio 1:2 weigh Choline Chloride and malonic acid and are well mixed, and heat and stir between 80~110 DEG C
Mix, be deep solvent DES2 altogether, by DES2 and water according to mass ratio 4.5 until forming transparency liquid:5.5 mix and produce thing
Matter B；
(3) by substance A and substance B by volume 8.75:1.25 mix the aqueous favoring for producing the deeply common solvent of two-phase；
(4) in molar ratio 1:2:3 weigh methyl tricapryl ammonium chloride, octanol and octanoic acid and are well mixed, 80~110
Heated between DEG C, until formation transparency liquid, is deeply altogether solvent DES3, the hydrophobic phase as the deeply common solvent of two-phase；
(5) by aqueous favoring and hydrophobic phase by volume 1:1 mixes, and is layered after standing, that is, obtains two-phase depth congruent melting solvent.
Embodiment 2
(1) example 1 in molar ratio:2.5 weigh Choline Chloride and levulic acid and are well mixed, and add between 80~110 DEG C
Thermal agitation, it is deep solvent DES1 altogether, by DES1 and water according to mass ratio 6 until forming transparency liquid:4.5 mix and produce
Substance A；
(2) in molar ratio 1:2.5 weigh Choline Chloride and malonic acid and are well mixed, and heat and stir between 80~110 DEG C
Mix, be deep solvent DES2 altogether, by DES2 and water according to mass ratio 4.5 until forming transparency liquid:6 mix and produce material
B；
(3) by substance A and substance B by volume 7.75:2.25 mix the aqueous favoring for producing the deeply common solvent of two-phase；
(4) in molar ratio 1:2:3.5 weigh methyl tricapryl ammonium chloride, octanol and octanoic acid and are well mixed, 80~
Heated between 110 DEG C, until formation transparency liquid, is deep solvent DES3 altogether, as the hydrophobic of the deeply common solvent of two-phase
Phase；
(5) by aqueous favoring and hydrophobic phase by volume 1:1 mixes, and is layered after standing, that is, obtains two-phase depth congruent melting solvent.
Embodiment 3
(1) example 1 in molar ratio:1.5 weigh Choline Chloride and levulic acid and are well mixed, and add between 80~110 DEG C
Thermal agitation, it is deep solvent DES1 altogether, by DES1 and water according to mass ratio 6 until forming transparency liquid:3.5 mix and produce
Substance A；
(2) in molar ratio 1:1.5 weigh Choline Chloride and malonic acid and are well mixed, and heat and stir between 80~110 DEG C
Mix, be deep solvent DES2 altogether, by DES2 and water according to mass ratio 4.5 until forming transparency liquid:5 mix and produce material
B；
(3) by substance A and substance B by volume 8.75:1.25 mix the aqueous favoring for producing the deeply common solvent of two-phase；
(4) in molar ratio 1:2:2.5 weigh methyl tricapryl ammonium chloride, octanol and octanoic acid and are well mixed, 80~
Heated between 110 DEG C, until formation transparency liquid, is deep solvent DES3 altogether, as the hydrophobic of the deeply common solvent of two-phase
Phase；
(5) by aqueous favoring and hydrophobic phase by volume 1:1 mixes, and is layered after standing, that is, obtains two-phase depth congruent melting solvent.
Embodiment 4
The difference identical with the preparation method of embodiment 1 of embodiment 4 is：By the aqueous favoring for comprising only substance A and dredge
Aqueous phase by volume 1:1 mixes, and is layered after standing, that is, obtains two-phase depth congruent melting solvent.
Embodiment 5
The difference identical with the preparation method of embodiment 1 of embodiment 5 is：Substance B aqueous favoring and hydrophobic will be comprised only
Mutually by volume 1:1 mixes, and is layered after standing, that is, obtains two-phase depth congruent melting solvent.
Embodiment 6
(1) any one the two-phase depth congruent melting solvent 4mL for preparing embodiment 1-5 is added in 20mL tool plug vials, essence
Really weigh the mesh Ginkgo Leafs of 0.2g 40 to add in the two-phase depth congruent melting solvent in tool plug vial, be vortexed and mix；
(2) at 60 DEG C after mixing, 150rpm magnetic agitations extraction 40min, extraction centrifuges after terminating under 10000rpm
10min, aqueous favoring is taken after centrifugation, detect flavones therein, terpene lactones, procyanidin content, take hydrophobic phase detection therein poly-
Pentenol acetate content.
Embodiment 7
(1) any one the two-phase depth congruent melting solvent 3mL for preparing embodiment 1-5 is added in 20mL tool plug vials, essence
Really weigh the mesh Ginkgo Leafs of 0.2g 40 to add in the two-phase depth congruent melting solvent in tool plug vial, be vortexed and mix；
(2) at 50 DEG C after mixing, 160rpm magnetic agitations extraction 45min, extraction centrifuges after terminating under 10000rpm
10min, aqueous favoring is taken after centrifugation, detect flavones therein, terpene lactones, procyanidin content, take hydrophobic phase detection therein poly-
Pentenol acetate content.
Embodiment 8
(1) any one the two-phase depth congruent melting solvent 5mL for preparing embodiment 1-5 is added in 20mL tool plug vials, essence
Really weigh in the two-phase depth congruent melting solvent during the mesh Ginkgo Leafs of 0.2g 40 add in tool plug vial, be vortexed and mix；
(2) at 70 DEG C after mixing, 100rpm magnetic agitations extraction 60min, extraction centrifuges after terminating under 10000rpm
10min, aqueous favoring is taken after centrifugation, detect flavones therein, terpene lactones, procyanidin content, take hydrophobic phase detection therein poly-
Pentenol acetate content.
Embodiment 9
(1) any one the two-phase depth congruent melting solvent 4mL for preparing embodiment 1-5 is added in 20mL tool plug vials, essence
Really weigh the mesh Ginkgo Leafs of 0.2g 40 to add in the two-phase depth congruent melting solvent in tool plug vial, be vortexed and mix；
(2) at 65 DEG C after mixing, 300rpm vibration stirring extraction 30min, extraction centrifuges after terminating under 10000rpm
10min, aqueous favoring is taken after centrifugation, detect flavones therein, terpene lactones, procyanidin content, take hydrophobic phase detection therein poly-
Pentenol acetate content.
Embodiment 10
(1) any one the two-phase depth congruent melting solvent 4mL for preparing embodiment 1-5 is added in 20mL tool plug vials, essence
Really weigh the mesh Ginkgo Leafs of 0.2g 40 to add in the two-phase depth congruent melting solvent in tool plug vial, be vortexed and mix；
(2) at 50 DEG C after mixing, 300rpm magnetic agitations extraction 30min, extraction centrifuges after terminating under 10000rpm
10min, aqueous favoring is taken after centrifugation, detect flavones therein, terpene lactones, procyanidin content, take hydrophobic phase detection therein poly-
Pentenol acetate content.
The detection method of the active component of embodiment 11
(1) ginko leaves flavone content detection
Flavones detection uses ultraviolet specrophotometer rutin method.0.5mL testing samples are taken, add 0.3mL5% natrium nitrosums
Solution, 6min is placed, add 10% aluminum nitrate solution 0.3mL, place 6min, add 4% sodium hydroxide solution 4mL, 70% second
Alcohol 4.5mL, 20min is placed after well mixed, is detected under 510nm.
Be made into titer with rutin standard items and be diluted to corresponding multiple, concentration gradient is respectively 0.008,0.016,
0.024th, 0.032,0.04,0.048,0.056,0.064,0.072mg/mL, is detected, and draw standard curve after colour developing.
The flavones standard curve detected using rutin method is y=6.1786x -0.0689, R2=0.9989, detection range
0-0.072mg/mL。
(2) Ginkgolides of Ginkgo Leaf content detection
Ring-opening reaction can occur terpene lactones for (pH ＞ 7.5) in the basic conditions, and different hydroxyl oxime fat is generated in the presence of azanol
Acid, then same FeCl3Reaction generation colored complex, can be standard specimen with ginkalide A based on the reaction mechanism, using point
Total terpene lactones content in light Spectrophotometric Determination of Silver apricot leaf.
Formulate standard curve process be：Accurate preparation 1.42mg/mL ginkalide A standard liquid 10mL, absorption 0.0,
0.2nd, 0.4,0.6,0.8,1.0mL is respectively placed in 6 20mL colorimetric cylinders, and respectively plus 70% ethanol solution is to 1.0mL, Ran Houjia
Enter 0.4mL alkalescence hydroxylamine solution (the 13.9% hydroxylamine hydrochloride aqueous solution+3.5mol/LNaOH solution (1:2) mix, it is current existing
With), add 3mol/L HCI solution 0.4mL, 6%FeCl after reacting 5min3Solution 0.2mL, it is well mixed, adds 70%
Ethanol solution 5mL, determined after shaking up at wavelength 517mn and draw standard curve.
The standard curve of terpene lactones is y=1.2243x-0.00154, R2=0.9992, detection range 0-1mg/mL.
(3) assay of ginkgo leaf OPC
Procyanidin content measure selects 4- dimethyl cinnamic acid (DMAC) AAS, and specific detection method is：Essence
12.5mL concentrated hydrochloric acids, 12.5mL water really are measured, being settled to 100mL with absolute ethyl alcohol is made acidic ethanol, and acidic ethanol need to now match somebody with somebody
It is current.50mg DMAC are settled to 50mL with acidic ethanol and are configured to developer.1mL sample liquids add 3mL developers, in room temperature
Lower placement 10min carries out chromogenic reaction, is detected after reaction at 644nm.
Titer is made into ginkgo leaf OPC standard items and is diluted to corresponding multiple, and concentration gradient is respectively
0.0129th, 0.0258,0.0387,0.0516,0.0645,0.0774,0.0903,0.1032,0.1161,0.129mg/mL, shows
Detected after color, and draw standard curve.
According to 10 groups of standard liquids after dilution, with the light absorption value that detection obtains with procyanidin concentration in Excel charts
Standard curve is drawn in instrument, draws up corresponding linear governing equation, the calibration curve equation of obtained OPC is：
Y=8.8157x+0.0114 (0<x<0.129)
R2=0.9994, illustrate that OPC lienar in 0~0.129mg/mL concentration ranges is good, this method can
For the quantitative analysis of OPC.
(4) detection method of content of Polyprenols From Ginkgo Biloba L acetic acid esters
Analyze the determination of chromatographic condition
Detection is analyzed polypentenol acetate compounds using HPLC high performance liquid chromatography, in different flowings
Sample introduction under the conditions of phase, column temperature, Detection wavelength, it is determined that most suitable testing conditions.
The foundation of polypentenol acetate standard curve
14.7mg polypentenol acetate standard product accurately are weighed, is dissolved in 6mL n-hexanes, is prepared into polypentenol second
Acid esters titer.Titer is diluted to the solution of 11 groups of various concentrations, is respectively：0.0613、 0.0245、0.49、0.735、
0.98th, 1.225,1.47,1.715,1.96,2.205,2.45 (unit：Mg/mL), the peak face under each group concentration is detected with HPLC
Product, according to peak area and the relation of concentration, draws out standard curve.
According to 11 groups of standard liquids after dilution, existed with the peak area that detection obtains and polypentenol Acetate concentration
Coordinate diagram is drawn in Excel graph tools, draws up corresponding linear governing equation, the standard of obtained polypentenol acetic acid esters
Curve：Y=1179.4x+12.746 (0<x<1.96), R2=0.9991, illustrate polypentenol acetic acid esters in 0~1.96mg/mL
Lienar for is good in concentration range, and this method can be used for the quantitative analysis of polypentenol acetic acid esters.
Test example 1
TPDESs is studied the active component recovery rate in ginkgo leaf, as a result as shown in table 1.
Embodiment 1-3 TPDESs is wherein used, and using the extracting method of embodiment 6, investigates TPDESs of the invention
And extracting method is to the recovery rate of the active component in ginkgo leaf；
Comparative example 1 is that Extraction solvent is water, and using the extracting method of embodiment 4.
Comparative example 2 is that Extraction solvent is 70% ethanol, and using the extracting method of embodiment 4.
Influences of the table 1TPDESss to active component recovery rate in ginkgo leaf
| OPC (mg/g) | Flavones (mg/g) | Terpene lactones (mg/g) | Polypentenol acetic acid esters (mg/g) | |
| Embodiment 1 | 21.284±0.9169 | 2.2165±0.0458 | 22.9552±0.0578 | 74.2829±1.9386 |
| Embodiment 2 | 21.145±0.9124 | 2.2127±0.0567 | 22.8436±0.0479 | 74.1857±1.9367 |
| Embodiment 3 | 21.168±0.9135 | 2.2089±0.0538 | 22.8735±0.0597 | 74.1753±1.8769 |
| Comparative example 1 | 11.2574±0.2537 | 1.0537±0.0236 | 12.3582±0.0247 | Do not measure |
| Comparative example 2 | 18.4372±0.2742 | 1.6832±0.5218 | 19.3527±0.6831 | Do not detect |
As seen from the results in Table 1, using the two-phase depth congruent melting solvent and extracting method of the present invention, it compared for traditional extraction
The recovery rate of aqueous solvent and 70% ethanol, embodiments of the invention recovery rate are substantially higher, and can reach recovery rate
22.0956±0.7129mg/g.This can illustrate that TPDESs of the invention can apply to synchronously carrying for Active Components of Ginkgo Leaves
Take, extraction efficiency is better than conventional solvent, its procyanidins 21.284 ± 0.9169mg/g of recovery rate, extracting flavonoids rate
2.2165 ± 0.0458mg/g, terpene lactones recovery rate are 22.9552 ± 0.0578mg/g, and polypentenol acetic acid esters recovery rate is
74.2829 ± 1.9386mg/g, OPC, flavones, terpene lactones, an extraction efficiency of polypentenol acetic acid esters are respectively
86.07%, 77.72%, 93.29% and 94.63%.Therefore, TPDESs of the invention efficiently can be extracted synchronously in ginkgo leaf
Multiple active components.And TPDESs of the present invention is a kind of efficient green solvent, will not be produced relative to conventional organic solvents
Any pollution, and it is safe to use.
Test example 2
Influence of the DESs component ratios to active component recovery rate in ginkgo leaf.
Using embodiment 1-3 TPDESs, and using the extracting method of embodiment 6；Investigate the depth of the embodiment of the present invention 1
Congruent melting solvent is to the recovery rate to the active component in ginkgo leaf；As a result it is as shown in table 2.
Wherein comparative example 3 is identical with the deep congruent melting solvent materials and preparation method of embodiment 1, difference component chlorination
The mol ratio of choline and malonic acid is 1:1, the mol ratio of Choline Chloride and levulic acid is 1:1, methyl tricapryl ammonium chloride,
Octanol and sad mol ratio are 1:1:4, and use identical extracting method.
Wherein comparative example 4 is identical with the deep congruent melting solvent materials and preparation method of embodiment 1, difference component chlorination
The mol ratio of choline and malonic acid is 1:3, the mol ratio of Choline Chloride and levulic acid is 1:3, methyl tricapryl ammonium chloride,
Octanol and sad mol ratio are 1:3:2, and use identical extracting method.
Table 2TPDESs components different mol ratio influences on Active Components of Ginkgo Leaves recovery rate
As seen from the results in Table 2, using two-phase depth congruent melting solvent and comparative example phase obtained by the mol ratio of the embodiment of the present invention
Than being substantially higher for the recovery rate of active component in ginkgo leaf.Wherein the mol ratio of comparative example 4 can not form stabilization
Two-phase system, therefore can not be extracted.Component molar has a significant impact than the formation for DESs and property.DESs component
Mol ratio influences whether the properties such as DESs viscosity, surface tension, can also influence between DESs components, between DESs and extract
Hydrogen bond action, Van der Waals force, hydrophobic forces equimolecular intermolecular forces, and then influence recovery rate.
Embodiment 3
Different hydrophilic phase and hydrophobic phase prepare influences of the TPDESs of gained to active component recovery rate in ginkgo leaf.
Using the two-phase depth congruent melting solvent (TPDESs) of embodiment 1, embodiment 4 and embodiment 5, ginkgo leaf and TPDESs
Mass volume ratio 1:20 (g/ml, solid-liquid ratios), magnetic agitation 150rpm, 50 DEG C of Extracting temperature, extraction time 30min.
Choose substance A and substance B volume ratio 8.75:Extraction solvents of the TPDESs of 1.25 compositions as combined extracting, it is former
Anthocyanidin recovery rate is 17.5974 ± 0.8514mg/g, higher than the single substance A/ hydrophobic phase two-phase system recovery rates of embodiment 4
10.71%, it is higher by 9.02% than the single substance B/ hydrophobic phase two-phase system recovery rates of embodiment 5；Extracting flavonoids rate be 2.1815 ±
0.0168mg/g, it is higher by 6.98% than single substance A/ hydrophobic phase two-phase system recovery rates, than single substance B/ hydrophobic phase two-phase mixtures
It is that recovery rate is high by 15.91%；Terpene lactones recovery rate is 17.7957 ± 0.8657mg/g, than single substance A/ hydrophobic phase two-phase mixtures
It is that recovery rate is high by 24.83%, but it is higher by 2.47% than single substance B/ hydrophobic phase two-phase system recovery rates；Polyprenol second
Acid esters recovery rate is 75.7373 ± 2.0148mg/g, identical with single substance A/ hydrophobic phase two-phase system recovery rates, than single
Substance B/hydrophobic phase two-phase system recovery rate is high by 78.53%, significant effect.
Test example 4
Influence of the TPDESs extracting methods to Active Components of Ginkgo Leaves recovery rate.
Using the TPDESs of embodiment 1, while substance A in embodiment 1 and the ratio of substance B will be substituted for 8.25:
1.75；Respectively using extraction conditions magnetic agitation (150rpm), ultrasonic extraction (150w) and shaking table concussion (150rpm) as to be selected
Extracting method, remaining condition are：The mass volume ratio 1 of ginkgo leaf and TPDESs:20 (g/mL), aqueous favoring with it is hydrophobic equal
Volume mixture, 50 DEG C of Extracting temperature, extraction time 30min.It is as shown in table 3 to extract result.
The Different Extraction Method of table 3 extracts the influence of Active Components of Ginkgo Leaves to TPDESs
| OPC (mg/g) | Flavones (mg/g) | Terpene lactones (mg/g) | Polypentenol acetic acid esters (mg/g) | |
| 8.75:1.25 stirring | 17.5974±0.8514 | 2.1815±0.0168 | 17.7957±0.8657 | 75.7373±2.0148 |
| 8.75:It is 1.25 ultrasonic | 12.1337±0.9780 | 1.8766±0.0531 | 13.0311±0.5659 | 47.8669±1.1068 |
| 8.75:1.25 vibration | 14.1188±0.9098 | 1.7998±0.0515 | 12.5002±0.0578 | 57.8056±1.7012 |
| 8.25:1.75 stirring | 16.3307±1.1017 | 2.0493±0.0910 | 18.3675±0.3683 | 74.4370±1.5761 |
| 8.25:It is 1.75 ultrasonic | 10.6401±0.9625 | 1.6743±0.0343 | 15.5223±0.0578 | 46.6246±1.8307 |
| 8.25:1.75 vibration | 14.4401±0.4813 | 1.7957±0.0584 | 14.4469±0.6238 | 51.1173±1.7426 |
| 7.75:2.25 stirring | 17.0113±0.9169 | 2.0196±0.0168 | 20.0828±0.4991 | 74.8909±1.5994 |
| 7.75:It is 2.25 ultrasonic | 8.7495±0.8589 | 1.3210±0.0474 | 15.9171±0.3401 | 43.6770±0.6890 |
| 7.75:2.25 vibration | 14.7048±0.4723 | 1.6689±0.0327 | 15.0731±0.231 | 44.3698±1.0139 |
As seen from the results in Table 3, for same Extraction solvent, recovery rate of three kinds of extracting methods to four kinds of active components
It is：Magnetic agitation ＞ shaking tables extract ＞ ultrasonic extractions.In magnetic agitation method, as substance B ratio raises, polypentenol
Acetic acid esters and OPC recovery rate are substantially similar, and all in error range, extracting flavonoids rate declines, on terpene lactones recovery rate
Rise；In ultrasonic extracting method, as substance B ratio raises, terpene lactones recovery rate rises, under its excess-three index extraction rate
Drop；In shaking table mechanical shaking extraction method, OPC recovery rate is held essentially constant, flavones and the extraction of polypentenol acetic acid esters
Rate somewhat declines, and terpene lactones recovery rate rises.The extractability that comprehensive diphasic system is shown in three extracting methods, can
To be inferred to, with the rise of DES1 contents, TPDESs two-phase systems extraction OPC ability is substantially similar, extracts flavones
Decline with polypentenol acetic acid esters ability, extraction terpene lactones ability rises.So optimal magnetic agitation 150rpm, simultaneously
Substance A and the volume ratio of substance B are 8.75:When 1.25, extraction effect is best.
Test example 5
Shadow of ginkgo leaf and the TPDESs mass volume ratio (g/mL) (i.e. solid-liquid ratio) to Active Components of Ginkgo Leaves recovery rate
Ring.
Extraction conditions are：Magnetic agitation 150rpm, 50 DEG C of Extracting temperature, extraction time 30min；Investigate ginkgo leaf and this
Influence of the mass volume ratios (g/mL) different the TPDESs of inventive embodiments 1 to Active Components of Ginkgo Leaves recovery rate, selection
Feed liquid ratio is respectively 1:5、1:10、1:15、1:20、1:25、1:30 (g/mL) situation, as a result as shown in table 4；
The influence that the solid-liquid ratio of table 4 extracts to Active Components of Ginkgo Leaves
As seen from the results in Table 4, it is 1 to extract solid-liquid ratio:15-25 active component recovery rates are preferable.With TPDESs increasing
Add, recovery rate is gradually increasing, until 1:20 reach balance, now, are further added by TPDESs volumes, and recovery rate no longer rises, to 1:
Decline when 30 obvious.Through analysis, when solid-liquid ratio is 1:When 20, recovery rate is higher.For TPDESs, aqueous favoring/hydrophobic phase
=1:1 (v/v), if reducing hydrophilic Phase Proportion, aqueous favoring solid-liquid ratio reduces, and hydrophilic composition recovery rate reduces, hydrophobic phase feed liquid
Than increase, but lyophobic dust recovery rate does not raise, and therefore, it is optimal that hydrophilic DESs is mixed in equal volume with hydrophobic DESs
Mixed proportion.
Test example 6
Different temperatures extracts the influence of Active Components of Ginkgo Leaves recovery rate to TPDESs.
Extraction conditions are：Magnetic agitation 150rpm, ginkgo leaf and TPDESs mass volume ratio 1:20 (g/mL), extraction
Time 30min；The TPDESs of the embodiment of the present invention 1 is investigated at different temperature to the recovery rate of Active Components of Ginkgo Leaves, choosing
The temperature taken is 45,50,55,60,65,70 DEG C and active component is extracted；As a result it is as shown in Figure 2.
As shown in Figure 2, polypentenol acetic acid esters reaches equilibrium valve at 50 DEG C, and flavones reaches extraction balance, original flower at 55 DEG C
Blue or green element and terpene lactones just reach extraction balance at 60 DEG C.In order to consider the recovery rate of four materials, Extracting temperature selection
50-70℃；It is preferred that 60-65 DEG C, optimum temperature is 60 DEG C.
Test example 7
Different extraction times extract the influence of Active Components of Ginkgo Leaves recovery rate to TPDESs.
Extraction conditions are：Magnetic agitation 150rpm, ginkgo leaf and TPDESs mass volume ratio 1:20 (g/mL), extraction
Time 30min, 60 DEG C of Extracting temperature；The TPDESs for investigating the embodiment of the present invention 1 lives under different extraction times to ginkgo leaf
The recovery rate of property composition, access time 25,30,35,40,45,50,55,60,65min extract to active component；Knot
Fruit is as shown in Figure 3.
As shown in Fig. 3 results, polypentenol acetic acid esters reaches extraction balance in 30min, and flavones and terpene lactones are in 35min
Reach extraction balance, and the equilibration time of OPC is 40min.So far, the selection and withdrawal time is 30-60min, preferably 40-
45min, optimal is 40min.
In summary, the deep congruent melting solvent that prepared by the present invention, in speed of agitator 150rpm, 60 DEG C of Extracting temperature, solid-liquid ratio
1:20, time 40min.OPC 21.284 ± 0.9169mg/g of recovery rate, extracting flavonoids rate 2.2165 ±
0.0458mg/g, terpene lactones recovery rate are 22.9552 ± 0.0578mg/g, polypentenol acetic acid esters recovery rate is 74.2829 ±
1.9386mg/g, OPC, flavones, terpene lactones, an extraction efficiency of polypentenol acetic acid esters are respectively 86.07%,
77.72%, 93.29% and 94.63%.Therefore, the two-phase system depth congruent melting solvent that prepared by the present invention, can be simultaneously efficient
Multiple active components in combined extracting ginkgo leaf.
Claims (10)
1. a kind of two-phase depth congruent melting solvent for extracting Active Components of Ginkgo Leaves, it is characterised in that by isometric aqueous favoring and dredge
Aqueous phase forms, and the aqueous favoring is by substance A and substance B 10-0 by volume:0-10 is formed, and the substance A is pressed by DES1 and water
Mass ratio 6:3.5-4.5 is formed, and the DES1 is according to mol ratio 1 by Choline Chloride and levulic acid:1.5-2.5 prepare and
Into；The substance B is by DES2 and water in mass ratio 4.5:5-6 is formed, and the DES2 is according to rubbing by Choline Chloride and malonic acid
That ratio 1:1.5-2.5 it is prepared；The hydrophobic phase DES3 is according to mol ratio by methyl tricapryl ammonium chloride, octanol and octanoic acid
1:2:2.5-3.5 it is prepared.
2. two-phase depth congruent melting solvent according to claim 1, it is characterised in that the aqueous favoring is pressed by substance A and substance B
Volume ratio 7.75-8.75:2.25-1.25 composition.
3. two-phase depth congruent melting solvent according to claim 1, it is characterised in that the substance A presses quality by DES1 and water
Than 6:4-5 is formed, and the DES1 is according to mol ratio 1 by Choline Chloride and levulic acid:2-2.5 it is prepared；The substance B
By DES2 and water in mass ratio 4.5:5.5-6 is formed, and the DES2 is according to mol ratio 1 by Choline Chloride and malonic acid:1.5-
2.5 it is prepared；The hydrophobic phase DES3 is according to mol ratio 1 by methyl tricapryl ammonium chloride, octanol and octanoic acid:2:2.5-3
It is prepared.
4. the preparation method of the two-phase depth congruent melting solvent described in a kind of claim 1, it is characterised in that comprise the following steps：
(1) Choline Chloride and levulic acid are weighed in molar ratio and are well mixed, the heating stirring between 80~110 DEG C, until
Transparency liquid is formed, as deep congruent melting solvent DES1, DES1 and water is mixed according to mass ratio and produce substance A；
(2) Choline Chloride and malonic acid are weighed in molar ratio and is well mixed, the heating stirring between 80~110 DEG C, until shape
Into transparency liquid, it is deep solvent DES2 altogether, DES2 and water is mixed according to mass ratio and produce substance B；
(3) substance A and substance B are mixed to the aqueous favoring for producing the deeply common solvent of two-phase by volume；
(4) methyl tricapryl ammonium chloride, octanol and octanoic acid are weighed in molar ratio and is well mixed, and are heated between 80~110 DEG C,
Until formation transparency liquid, is deeply altogether solvent DES3, the hydrophobic phase as the deeply common solvent of two-phase；
(5) aqueous favoring and hydrophobic equal volume are mixed, are layered after standing, that is, obtain two-phase depth congruent melting solvent.
5. a kind of method of two-phase depth congruent melting solvent extraction Active Components of Ginkgo Leaves using described in claim 1, its feature exist
In comprising the following steps：
(1) two-phase depth congruent melting solvent is placed in extraction vessel, accurately weighs the two-phase that Ginkgo Leaf is added in extraction vessel
In deep solvent altogether, it is well mixed；
(2) heating extraction after mixing, extraction centrifuge after terminating, and two-phase system layering, upper phase is hydrophobic phase, and lower phase is aqueous favoring；
Aqueous favoring detection flavones therein, terpene lactones, procyanidin content are taken, takes hydrophobic phase to detect polyisoamylene alcohol acetic ester therein
Content.
6. the method for the extraction Active Components of Ginkgo Leaves according to right wants 5, it is characterised in that step (1) described ginkgo leaf
The mass volume ratio of powder and two-phase depth congruent melting solvent is 1:15-25g/mL.
7. the method for extraction Active Components of Ginkgo Leaves according to claim 6, it is characterised in that step (1) described ginkgo
The mass volume ratio of leaf powder and two-phase depth congruent melting solvent is 1:20-25g/mL.
8. the method for extraction Active Components of Ginkgo Leaves according to claim 5, it is characterised in that adding described in step (2)
Heat is extracted as vibrating heating extraction or agitating and heating extraction.
9. the method for extraction Active Components of Ginkgo Leaves according to claim 5, it is characterised in that the vibration or stirring
Rotating speed is 100-300rpm, and temperature is 50-70 DEG C, time 30-60min.
10. the method for extraction Active Components of Ginkgo Leaves according to claim 9, it is characterised in that the vibration or stirring
Rotating speed be 150-160rpm, temperature is 60-65 DEG C, time 40-45min.
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