CN110746470B - Method for extracting phenylethanoid glycosides from cistanche tubulosa by ionic liquid aqueous two-phase extraction - Google Patents

Method for extracting phenylethanoid glycosides from cistanche tubulosa by ionic liquid aqueous two-phase extraction Download PDF

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CN110746470B
CN110746470B CN201911230059.9A CN201911230059A CN110746470B CN 110746470 B CN110746470 B CN 110746470B CN 201911230059 A CN201911230059 A CN 201911230059A CN 110746470 B CN110746470 B CN 110746470B
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李雪琴
徐鹤林
张金利
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Shihezi University
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Abstract

The invention discloses a method for extracting phenylethanoid glycosides from cistanche tubulosa by ionic liquid aqueous two-phase extraction, which comprises the following steps: s1, adding an ionic liquid solution into the cistanche tubulosa crude extract, uniformly mixing, adding an inorganic salt, and uniformly mixing to form a suspension; s2, performing ultrasonic extraction on the suspension, and standing after extraction to obtain a two-aqueous-phase system, wherein the upper layer of the two-aqueous-phase system is an aqueous phase in which inorganic salt is dissolved, and the lower layer of the two-aqueous-phase system is an ionic liquid phase containing phenylethanoid glycoside; s3, separating the aqueous two-phase system to obtain a phenylethanoid glycoside concentrated solution; s4, separating the ionic liquid in the concentrated solution to obtain the extract rich in the phenylethanoid glycosides. The method for extracting phenylethanoid glycosides from cistanche tubulosa by using the ionic liquid aqueous two-phase extraction method disclosed by the embodiment of the invention is environment-friendly, simple to operate, high in extraction efficiency and low in energy consumption, and provides a new method for efficiently separating phenylethanoid glycosides compounds from active ingredients of natural products.

Description

Method for extracting phenylethanoid glycosides from cistanche tubulosa by ionic liquid aqueous two-phase extraction
Technical Field
The invention belongs to the technical field of material extraction, and particularly relates to a method for extracting phenylethanoid glycosides from cistanche tubulosa with ionic liquid in a two-aqueous phase manner.
Background
Cistanche tubulosa is a parasitic plant of the family Orobanchaceae, commonly called tamarix rupestris, parasitic on the roots of tamarix plants, and mainly distributed in the northern regions of Xinjiang and around Takrama desert in the southern regions of Xinjiang in China. Meanwhile, cistanche tubulosa is a precious nourishing Chinese herbal medicine, is known as 'desert ginseng', and has the functions of nourishing kidney, resisting aging, enhancing blood essence, moistening large intestine and smoothing stool. Studies show that phenylethanoid glycosides, iridoids and polysaccharides are the main chemical components of cistanche tubulosa. Phenylethanoid glycosides are the main active ingredients of cistanche tubulosa, and have neuroprotective, immunoregulatory, antiinflammatory, hepatoprotective, and antioxidant effects. Phenylethanoid glycosides are a group of water-soluble natural products, are a common structure consisting of cinnamic acid and hydroxyphenyl ethyl, are connected with beta-glucopyranose through ester and glycosidic bonds, and mainly comprise echinacoside and verbascoside. The natural product system is a complex system, which comprises thousands of molecules, and the contents of the molecules are very different, and a plurality of components have similar structures, so that the separation difficulty is high. The purity requirement of active substances of natural products makes the selective separation of single substances more and more important, and the existing separation and purification method of active ingredients of natural products mainly comprises the following steps: aqueous two-phase extraction, macroporous resin, membrane separation, etc. The aqueous two-phase extraction is a novel separation technology which can obtain high yield and purity by using simple equipment and performing simple operation under mild conditions, and is one of ideal methods for separating effective components of natural products.
At present, patent document No. CN104189100a discloses a method for aqueous two-phase extraction of desert cistanche phenylethanoid glycosides, wherein although a method for aqueous two-phase extraction of desert cistanche phenylethanoid glycosides is also disclosed, the method is only applicable to desert cistanche raw material powder, and the operation process is complex, the phenylethanoid glycoside extraction efficiency is low, the energy consumption is high, and the method is not suitable for popularization and use.
Disclosure of Invention
The present invention is directed to solving at least one of the problems of the prior art.
Therefore, the invention provides a method for extracting phenylethanoid glycosides from cistanche tubulosa with ionic liquid in two aqueous phases, which has the advantages of high extraction efficiency, simple operation and low energy consumption.
The method for extracting phenylethanoid glycosides from cistanche tubulosa by using the ionic liquid through the aqueous two-phase extraction method comprises the following steps of: s1, adding an ionic liquid solution into the cistanche tubulosa crude extract, uniformly mixing, adding an inorganic salt, and uniformly mixing to form a suspension; s2, performing ultrasonic extraction on the suspension, and standing after extraction to obtain a two-aqueous-phase system, wherein the upper layer of the two-aqueous-phase system is an aqueous phase in which inorganic salt is dissolved, and the lower layer of the two-aqueous-phase system is an ionic liquid phase containing phenylethanoid glycoside; s3, separating the aqueous two-phase system to obtain a concentrated solution of phenylethanoid glycosides; s4, separating the ionic liquid in the concentrated solution to obtain the extract rich in the phenylethanoid glycosides.
The method for extracting phenylethanoid glycosides from cistanche tubulosa by using the ionic liquid through the aqueous two-phase extraction method disclosed by the embodiment of the invention is environment-friendly, simple to operate, high in extraction efficiency and low in energy consumption, and provides a new method for efficiently separating phenylethanoid glycosides compounds in active ingredients of natural products.
According to an embodiment of the present invention, in step S1, the concentration of the phenylethanoid glycosides in the cistanche tubulosa crude extract is 0.5mg/mL to 3mg/mL.
According to one embodiment of the invention, in step S1, the ionic liquid is 1-butyl-3-methylimidazolium tetrafluoroborate.
According to one embodiment of the invention, the concentration of the 1-butyl-3-methylimidazolium tetrafluoroborate solution is between 0.25mg/mL and 2.3mg/mL.
According to an embodiment of the present invention, in step S1, the inorganic salt is at least one selected from the group consisting of sodium carbonate, ammonium sulfate, sodium dihydrogen phosphate, dipotassium hydrogen phosphate and potassium phosphate.
According to one embodiment of the invention, the inorganic salt is ammonium sulfate, and the concentration of ammonium sulfate in the ionic liquid solution is 0.05 mg/mL-0.25 mg/mL.
According to an embodiment of the invention, in the step S2, the ultrasonic extraction time is 5min to 10min, the ultrasonic power is 100W to 300W, and the standing time is 25min to 35min.
According to one embodiment of the invention, step S4 comprises: s41, adding ethyl acetate into the concentrated solution of the phenylethanoid glycosides, uniformly mixing, standing and layering to obtain an ethyl acetate phase and an ionic liquid phase; s42, removing ethyl acetate from the obtained ethyl acetate phase, and then drying in vacuum to obtain the extract rich in phenylethanoid glycosides.
According to an embodiment of the invention, step S4 further comprises: s43, carrying out vacuum drying on the obtained ionic liquid phase to obtain an ionic liquid recovery liquid.
According to one embodiment of the invention, the phenylethanoid glycosides are verbascosides.
Additional aspects and advantages of the invention will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the invention.
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The above and/or additional aspects and advantages of the present invention will become apparent and readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawings of which:
fig. 1 is a flow chart of a method for extracting phenylethanoid glycosides from cistanche tubulosa by using ionic liquid and aqueous two-phase, according to an embodiment of the invention.
Detailed Description
Reference will now be made in detail to embodiments of the present invention, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to the same or similar elements or elements having the same or similar functions throughout. The embodiments described below with reference to the accompanying drawings are illustrative only for the purpose of explaining the present invention, and are not to be construed as limiting the present invention.
The following description first refers to the accompanying drawings to describe a method for extracting phenylethanoid glycosides from cistanche tubulosa by ionic liquid aqueous two-phase extraction according to an embodiment of the present invention.
As shown in fig. 1, the method for extracting phenylethanoid glycosides from cistanche tubulosa by using ionic liquid and aqueous two-phase extraction according to the embodiment of the invention comprises the following steps:
s1, adding an ionic liquid solution into the cistanche tubulosa crude extract, uniformly mixing, adding an inorganic salt into a system, and fully mixing to form a uniform suspension.
And S2, carrying out ultrasonic extraction on the suspension, and standing after extraction to obtain a two-aqueous-phase system, wherein the upper layer of the two-aqueous-phase system is an aqueous phase in which inorganic salt is dissolved, and the lower layer of the two-aqueous-phase system is an ionic liquid phase containing phenylethanoid glycoside.
And S3, separating the aqueous two-phase system to obtain a lower-layer solution, namely a phenylethanoid glycoside concentrated solution.
And S4, separating the ionic liquid in the concentrated solution rich in phenylethanoid glycosides to obtain an extract rich in phenylethanoid glycosides.
According to an embodiment of the present invention, in step S1, the concentration of the phenylethanoid glycosides in the cistanche tubulosa crude extract is 0.5mg/mL to 3mg/mL.
Alternatively, in step S1, the ionic liquid is 1-butyl-3-methylimidazolium tetrafluoroborate (C4 mimBF 4), and the concentration of the 1-butyl-3-methylimidazolium tetrafluoroborate solution is 0.25mg/mL to 2.3mg/mL, and preferably may be 2.2mg/mL.
In some embodiments of the present invention, in step S1, the inorganic salt is at least one selected from the group consisting of sodium carbonate, ammonium sulfate, sodium dihydrogen phosphate, dipotassium hydrogen phosphate and potassium phosphate. Optionally, the inorganic salt is ammonium sulfate, and the concentration of ammonium sulfate in the ionic liquid solution is 0.05mg/mL to 0.25mg/mL, and preferably can be 0.1mg/mL.
According to one embodiment of the invention, in the step S2, the ultrasonic extraction time is 5 min-10 min, the ultrasonic power is 100W-300W, and the standing time is 25 min-35 min.
In some embodiments of the invention, step S4 comprises:
s41, adding ethyl acetate into the concentrated solution of the phenylethanoid glycosides, uniformly mixing, standing and layering to obtain an ethyl acetate phase and an ionic liquid phase;
s42, removing ethyl acetate from the obtained ethyl acetate phase, and then drying in vacuum to obtain the extract rich in the phenylethanoid glycosides.
Further, step S4 further includes:
s43, carrying out vacuum drying on the obtained ionic liquid phase to obtain an ionic liquid recovery liquid.
It should be noted that, in the present invention, the phenylethanoid glycosides may be verbascoside.
Therefore, the method for extracting phenylethanoid glycosides from cistanche tubulosa by using the ionic liquid through the aqueous two-phase extraction method disclosed by the embodiment of the invention is environment-friendly, simple to operate, high in extraction efficiency and low in energy consumption, and provides a new method for efficiently separating phenylethanoid glycosides compounds in active ingredients of natural products.
The following describes the method for extracting phenylethanoid glycosides from cistanche tubulosa with ionic liquid in aqueous two-phase mode with reference to specific examples.
Example 1
(1) 4.5g of [ C4mim ] was added to the test tube]BF4 solution, 0.8g of (NH) 4 ) 2 SO 4 3mL of distilled water is added, and then 1mL of the pre-prepared phenylethanoid glycoside solution with the mass concentration of 2.0mg/mL is added.
For accuracy of the test data, three parallel runs were made for each sample.
(2) After the ionic liquid aqueous two-phase system is prepared, fully shaking for 5min to ensure that the whole system is uniformly mixed, and then standing for 1h at room temperature. And after phase splitting is finished, respectively taking the upper phase solution and the lower phase solution to measure the concentration of the phenylethanoid glycoside.
(3) In this example, the phenylethanoid glycoside concentration is determined by HPLC, and the UV absorption wavelength of 330nm is selected.
Wherein, blank samples are: 1mL of the phenylethanoid glycoside solution with the mass concentration of 2.0mg/mL in the step (1) is replaced by 1mL of distilled water, and the rest is unchanged.
The blank control is used for measuring the absorbance value of the sample, the content of the phenylethanoid glycosides is calculated according to the standard curve, the extraction rate is calculated, the extraction rate is 87.45 percent, the distribution coefficient is 19.1, and the selectivity is 70.67.
Example 2
(1) 4.5g of [ C4mim ] was added to the test tube]BF4 solution, 1.0g of (NH) 4 ) 2 SO 4 3mL of distilled water is added, and then 1mL of the pre-prepared phenylethanoid glycoside solution with the mass concentration of 2.0mg/mL is added.
For accuracy of the test data, three sets of parallel tests were run for each sample.
(2) After the ionic liquid aqueous two-phase system is prepared, fully shaking for 5min to ensure that the whole system is uniformly mixed, and then standing for 1h at room temperature. And after phase separation is finished, taking the upper phase solution and the lower phase solution respectively to measure the concentration of the phenylethanoid glycosides.
(3) In this example, the phenylethanoid glycoside concentration is determined by HPLC, and the UV absorption wavelength of 330nm is selected.
Wherein, blank samples are: 1mL of the phenylethanoid glycoside solution with the mass concentration of 2.0mg/mL in the step (1) is replaced by 1mL of distilled water, and the rest is unchanged.
The blank control is used for measuring the absorbance value of the sample, the content of the phenylethanoid glycosides is calculated according to the standard curve, the extraction rate is calculated, the extraction rate is 93.15%, the distribution coefficient is 28.46, and the selectivity is 158.11.
Example 3
(1) Adding into a test tube4.5g of [ C4mim]BF4 solution, 1.0g of (NH) 4 ) 2 SO 4 3mL of distilled water is added, and then 1mL of the pre-prepared phenylethanoid glycoside solution with the mass concentration of 2.0mg/mL is added.
For accuracy of the test data, three sets of parallel tests were run for each sample.
(2) After the ionic liquid aqueous two-phase system is prepared, fully shaking for 5min to ensure that the whole system is uniformly mixed, and then standing for 1h at 15 ℃. And after phase separation is finished, taking the upper phase solution and the lower phase solution respectively to measure the concentration of the phenylethanoid glycosides.
(3) In this example, the phenylethanoid glycoside concentration is determined by HPLC, and the UV absorption wavelength of 330nm is selected.
Wherein, blank sample is: 1mL of the phenylethanoid glycoside solution with the mass concentration of 2.0mg/mL in the step (1) is replaced by 1mL of distilled water, and the rest is unchanged.
And (3) measuring the absorbance value of the sample by using a blank control, calculating the content of the phenylethanoid glycosides according to a standard curve, and calculating the extraction rate, wherein the extraction rate is 94.00%, the distribution coefficient is 25.8, and the selectivity is 103.2.
Example 4
(1) 4.5g of [ C4mim ] was added to the test tube]BF4 solution, 1.0g of (NH) 4 ) 2 SO 4 3mL of distilled water was added, and then 1mL of a pre-prepared phenylethanoid glycoside solution with a mass concentration of 2.0mg/mL was added, and the pH was adjusted =6.
For accuracy of the test data, three sets of parallel tests were run for each sample.
(2) After the ionic liquid aqueous two-phase system is prepared, fully shaking for 5min to ensure that the whole system is uniformly mixed, and then standing for 1h at room temperature. And after phase separation is finished, taking the upper phase solution and the lower phase solution respectively to measure the concentration of the phenylethanoid glycosides.
(3) In this example, the phenylethanoid glycoside concentration is determined by HPLC, and the UV absorption wavelength of 330nm is selected.
Wherein, blank sample is: 1mL of the phenylethanoid glycoside solution with the mass concentration of 2.0mg/mL in the step (1) is replaced by 1mL of distilled water, and the rest is unchanged.
The blank control is used for measuring the absorbance value of the sample, the content of the phenylethanoid glycosides is calculated according to the standard curve, the extraction rate is calculated, the extraction rate is 99.78%, the distribution coefficient is 33.82, and the selectivity is 230.5.
Comparative example 1
4.5g of [ C4mim ] was added to the test tube]Cl solution, 1.0g of K was added 2 HPO 4 Adding 3mL of distilled water, then adding 1mL of prepared phenylethanoid glycoside solution with the mass concentration of 2.0mg/mL, adjusting the pH =6, fully shaking for 5min to ensure that the whole system is uniformly mixed, and then standing for 1h at room temperature. And after phase separation is finished, taking the upper phase solution and the lower phase solution respectively to measure the concentration of the phenylethanoid glycosides. The extraction rate was calculated to be 30.20%, the partition coefficient was 1.56, and the selectivity was 0.85.
Comparative example 2
Adding 4.5g of [ C4mim ] BF4 solution into a test tube, adding 1.0g of NaCl, adding 3mL of distilled water, then adding 1mL of prepared phenylethanoid glycoside solution with the mass concentration of 2.0mg/mL, adjusting the pH to be =6, fully shaking for 5min, ensuring that the whole system is uniformly mixed, and then standing for 1h at room temperature. And after phase separation is finished, taking the upper phase solution and the lower phase solution respectively to measure the concentration of the phenylethanoid glycosides. The extraction rate was calculated to be 68.80%, the partition coefficient was 10.54, and the selectivity was 61.38.
The embodiment and the comparative example show that the method for extracting phenylethanoid glycosides from cistanche tubulosa by using the ionic liquid through the aqueous two-phase method is environment-friendly, simple to operate, high in extraction efficiency and low in energy consumption, and provides a new method for efficiently separating phenylethanoid glycosides compounds from active ingredients of natural products.
In the description herein, references to the description of the term "one embodiment," "some embodiments," "an illustrative embodiment," "an example," "a specific example," or "some examples" or the like mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
While embodiments of the invention have been shown and described, it will be understood by those of ordinary skill in the art that: various changes, modifications, substitutions and alterations can be made to the embodiments without departing from the principles and spirit of the invention, the scope of which is defined by the claims and their equivalents.

Claims (6)

1. A method for extracting phenylethanoid glycosides from cistanche tubulosa by ionic liquid aqueous two-phase extraction is characterized by comprising the following steps: the method comprises the following steps:
s1, adding an ionic liquid solution into the cistanche tubulosa crude extract, uniformly mixing, adding inorganic salt, and uniformly mixing to form a suspension, wherein the inorganic salt is ammonium sulfate, and the concentration of the ammonium sulfate in the ionic liquid solution is 0.05 mg/mL-0.25 mg/mL;
s2, performing ultrasonic extraction on the suspension, and standing after extraction to obtain a double-aqueous-phase system, wherein the upper layer of the double-aqueous-phase system is an aqueous phase in which inorganic salt is dissolved, and the lower layer of the double-aqueous-phase system is an ionic liquid phase containing phenylethanoid glycoside;
s3, separating the aqueous two-phase system to obtain a concentrated solution of phenylethanoid glycosides;
s4, separating the ionic liquid in the concentrated solution to obtain an extract rich in phenylethanoid glycosides,
in step S1, the ionic liquid is 1-butyl-3-methylimidazole tetrafluoroborate, and the concentration of the 1-butyl-3-methylimidazole tetrafluoroborate solution is 0.25-mg/mL-2.3 mg/mL.
2. The method according to claim 1, wherein in step S1, the concentration of phenylethanoid glycosides in the cistanche tubulosa crude extract is 0.5 mg/mL-3 mg/mL.
3. The method of claim 1, wherein in step S2, the time of ultrasonic extraction is 5min to 10min, the ultrasonic power is 100W to 300W, and the standing time is 25min to 35min.
4. The method according to claim 1, wherein step S4 comprises:
s41, adding ethyl acetate into the concentrated solution of the phenylethanoid glycosides, uniformly mixing, standing and layering to obtain an ethyl acetate phase and an ionic liquid phase;
s42, removing ethyl acetate from the obtained ethyl acetate phase, and then drying in vacuum to obtain the extract rich in phenylethanoid glycosides.
5. The method of claim 4, wherein step S4 further comprises:
s43, carrying out vacuum drying on the obtained ionic liquid phase to obtain an ionic liquid recovery liquid.
6. The method according to any one of claims 1 to 5, wherein the phenylethanoid glycoside is verbascoside.
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