CN111450139A - Eutectic solvent and method for preparing spina gleditsiae total flavonoids by using same - Google Patents
Eutectic solvent and method for preparing spina gleditsiae total flavonoids by using same Download PDFInfo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
- A61K36/483—Gleditsia (locust)
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
Abstract
The invention relates to a eutectic solvent and a method for preparing total flavonoids in spina gleditsiae, belonging to the field of extraction of total flavonoids in spina gleditsiae, and the method comprises the steps of adding spina gleditsiae medicinal material powder into a choline chloride-1, 4-butanediol (1:4) aqueous solution with the eutectic solvent and the water content of 20% for ultrasonic extraction, and performing suction filtration on an extract to obtain the total flavonoids in spina gleditsiae; the solvent used for extraction comprises eutectic solvent and water, wherein the eutectic solvent is prepared by mixing and heating Hydrogen Bond Donor (HBD) and Hydrogen Bond Acceptor (HBA) to obtain uniform solution, and adding a certain amount of water. The invention provides a method for preparing spina gleditsiae total flavonoids by using a green eutectic solvent with high extraction rate, wherein 3,3',5,5', 7-pentahydroxyflavanone with the highest content in the total flavonoids is used as an extraction rate marker, and the extraction rate of the eutectic solvent is increased by 59.1% compared with 75% methanol-water. The method prepares the spina gleditsiae total flavone extract by introducing the environment-friendly eutectic solvent, effectively avoids solvent toxicity caused by organic solvent extraction, and provides a new development idea for extracting spina gleditsiae total flavone.
Description
Technical Field
The invention belongs to the technical field of preparation methods of spina gleditsiae total flavonoids, and particularly relates to a preparation method of spina gleditsiae total flavonoids.
Background
The information in this background section is only for enhancement of understanding of the general background of the invention and is not necessarily to be construed as an admission or any form of suggestion that this information forms the prior art that is already known to a person of ordinary skill in the art.
Spina Gleditsiae Gleditisae Spina is also called as Spina Gleditsiae, Spina Gleditsiae needle, Spina Gleditsiae and the like, is a dry thorn of a Gleditsia Gleditsiae Gleditisia sinensis L am. belonging to the genus Gleditsia (L egumlosae) in the family Leguminosae (Gleditsia L), is a traditional Chinese medicinal material in China, has a long clinical application history and a wide medicinal value, has the effects of pungent taste, warm nature, liver and stomach meridians entering, swelling subsiding and toxin expelling, pus discharging, killing parasites, resisting cancer and the like, is commonly used for treating early carbuncle and non-ulceration of pus clinically, has a good treatment effect on the aspects of improving cardiovascular system, resisting hepatic fibrosis, resisting bacteria, resisting inflammation, improving immunity and the like, has a certain in-vitro cytotoxic activity on various cancer cells such as breast cancer, liver cancer, cervical cancer, rectal cancer and the like, and is also one of the traditional Chinese medicines for treating various cancers.
The chemical components of the spina gleditsiae mainly comprise flavonoid compounds, saponin compounds with low content and the like. The spina gleditsiae flavone is a main active ingredient, has strong anti-tumor activity, and has good clinical application value and development prospect. The traditional extraction solvent of total flavonoids in spina gleditsiae is an organic solvent such as methanol-water, ethanol-water and the like, and the inventor finds that: the common organic solvents have certain toxicity, so that the amplified extraction production of the total flavonoids in the spina gleditsiae has certain disadvantages.
Disclosure of Invention
Aiming at the problems in the prior art, the invention aims to provide a green extraction method of total flavonoids in spina gleditsiae with high extraction rate. Through research on extraction solvents of the spina gleditsiae total flavonoids, an effective eutectic solvent is found for preparing the spina gleditsiae total flavonoids, the 3,3',5,5', 7-pentahydroxyflavanone compound with the highest content is used as an extraction rate marker, and the extraction efficiency of the eutectic solvent is improved by 59.1% compared with 75% methanol. The spina gleditsiae total flavone extract is prepared by introducing the environment-friendly eutectic solvent (DES), has the advantages of greenness, safety and high extraction efficiency, and provides a new development idea for extracting spina gleditsiae total flavone.
In order to achieve the technical purpose, the invention adopts the following technical scheme:
in a first aspect of the invention, there is provided a eutectic solvent, the hydrogen bond acceptor is choline chloride and the hydrogen bond donor is a polyol, a sugar or an organic acid.
The extraction efficiency of the eutectic solvent on the total flavonoids in the spina gleditsiae is improved by 59.1 percent compared with 75 percent methanol, and the eutectic solvent has the advantages of greenness, no toxicity and high extraction efficiency, and is expected to be widely applied to the extraction of the total flavonoids in the spina gleditsiae.
In a second aspect of the invention, the invention provides a method for preparing spina gleditsiae total flavonoids by using a eutectic solvent.
The extraction method is simple, efficient, green and nontoxic, and solves the problem that the toxicity of an organic solvent limits the amplification extraction production of the spina gleditsiae total flavonoids.
In a third aspect of the present invention, there is provided a method of obtaining total flavonoids from spina Gleditsiae by any of the above methods.
The method is high in extraction efficiency, green and non-toxic, and is expected to be widely applied to the amplification extraction production of the spina gleditsiae total flavonoids.
The invention has the beneficial effects that:
(1) the invention provides a method for extracting total flavonoids from spina gleditsiae, which is green and high in extraction rate. Through research on extraction solvents of the spina gleditsiae total flavonoids, an effective eutectic solvent is found for preparing the spina gleditsiae total flavonoids, the 3,3',5,5', 7-pentahydroxyflavanone compound with the highest content is used as an extraction rate marker, and the extraction efficiency of the eutectic solvent is improved by 59.1% compared with 75% methanol. The spina gleditsiae total flavone extract is prepared by introducing the environment-friendly eutectic solvent (DES), has the advantages of greenness, safety and high extraction efficiency, and provides a new development idea for extracting spina gleditsiae total flavone.
(2) The method disclosed by the invention is simple, high in extraction rate, strong in practicability and easy to popularize.
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The accompanying drawings, which are incorporated in and constitute a part of this specification, are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification, illustrate exemplary embodiments of the invention and together with the description serve to explain the invention and not to limit the invention.
FIG. 1 is an analytical graph showing HP L C of total flavonoids of spina Gleditsiae obtained from five eutectic solvents (DES-1, DES-2, DES-3, DES-4, DES-5) in example 1 and reference standard methanol-water (75:25, v/v);
FIG. 2 shows the IR spectra of choline chloride (A), 1,4-butanediol (B), choline chloride-1, 4-butanediol (1:2) (C), choline chloride-1, 4-butanediol (1:3) (D), choline chloride-1, 4-butanediol (1:4) (E), choline chloride-1, 4-butanediol (1:5) (F), and choline chloride-1, 4-butanediol (1:6) (G) in example 1.
Detailed Description
It is to be understood that the following detailed description is exemplary and is intended to provide further explanation of the invention as claimed. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of exemplary embodiments according to the invention. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, and it should be understood that when the terms "comprises" and/or "comprising" are used in this specification, they specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof, unless the context clearly indicates otherwise.
The invention provides a method for preparing total flavonoids in spina gleditsiae by using a eutectic solvent, which comprises the following steps: pulverizing spina Gleditsiae, adding spina Gleditsiae powder into eutectic solvent water solution with water content of 20%, ultrasonic extracting at 55 deg.C for 45min at a material-to-liquid ratio of 1:30, and vacuum filtering to obtain filtrate; the solvent used for extraction consists of a eutectic solvent and ultrapure water, wherein the eutectic solvent is prepared by mixing and heating a Hydrogen Bond Donor (HBD) and a Hydrogen Bond Acceptor (HBA) to prepare a uniform solution, and then adding a certain amount of water into the obtained solution to obtain the solvent required for extraction. The Hydrogen Bond Acceptor (HBA) is choline chloride (ChCl), the Hydrogen Bond Donor (HBD) comprises polyalcohol [1, 4-butanediol (1, 4-butandiol), ethylene glycol (ethane diol), Glycerol (Glycerol) ], saccharide [ Glucose (Glucose) ], and organic acid [ Citric acid (Citric acid) ]. The five eutectic solvents are prepared by mixing and heating the hydrogen bond acceptor and the hydrogen bond donor according to different molar ratios, and are shown in table 1.
Table 1 kinds of eutectic solvents.
Extracting total flavonoids from spina Gleditsiae with methanol-water (75:25, v/v) as reference standard, treating with 5 eutectic solvents (DES-1, DES-2, DES-3, DES-4, DES-5) in Table 1 to remove components in the eutectic solvent, separating with AB-8 macroporous resin column, analyzing with HP L C, comparing with methanol-water (75:25, v/v) extract HP L C liquid phase diagram, determining that the obtained liquid phase diagrams of extracts of polyalcohol eutectic solvents DES-1 and DES-2 are consistent with the reference standard, and further determining DES-1[ choline chloride-1, 4-butanediol (Ch-But) ] as optimal extraction solvent according to the content ratio of 5 index components in the extract.
Firstly, optimizing the molar ratio of choline chloride and 1,4-butanediol in DES-1, and comparing infrared spectrograms of eutectic solvents with 5 different molar compositions (1:2, 1:3, 1:4, 1:5, 1:6) to find that the characteristic absorption peak of the hydroxyl group of the choline chloride-1, 4-butanediol (1:4) is widest, which indicates that the contained hydroxyl group is the largest, namely the number of flavones complexed through hydrogen bonds is the largest, and further, the extraction rate of the choline chloride-1, 4-butanediol (1:4) is the highest by taking a 3,3',5,5', 7-pentahydrofluorone compound with the highest content in total flavones of spina gleditsiae as an extraction rate marker, so that the optimal molar ratio of the choline chloride to the 1,4-butanediol is finally determined to be 1: 4.
Secondly, the extraction temperature is optimized, 4 different extraction temperatures (45 ℃, 55 ℃, 65 ℃ and 75 ℃) are set, and through taking the 3,3',5,5', 7-pentahydroxyflavone compound (peak 3 in figure 1) with the highest content in the spina gleditsiae total flavonoids as an extraction rate marker, the extraction rate of 55 ℃ increased to 65 ℃ is not changed greatly, so that the 55 ℃ is finally determined as the optimal extraction temperature.
Thirdly, the water content of the eutectic solvent is optimized, 4 different water contents (0, 20%, 40% and 60%) are set, and the extraction rate is the highest when the water content is 20% by using the 3,3',5,5', 7-pentahydroflavone compound with the highest content in the spina gleditsiae total flavonoids as an extraction rate marker, so that the optimal water content is finally determined to be 20%.
Fourthly, optimizing the material-liquid ratio of the medicinal materials to the solvent, setting 4 different material-liquid ratios (1:10, 1:20, 1:30 and 1:40mg/m L), and finally determining the optimal material-liquid ratio to be 1:30mg/m L by using the 3,3',5,5', 7-pentahydroxyflavone compound with the highest content in the total flavonoids of the spina gleditsiae as an extraction rate marker and finding that the extraction rate is the highest when the material-liquid ratio is 1:30mg/m L.
And finally, optimizing the extraction time, setting 4 different extraction times (15, 30, 45 and 60min), and finding that the extraction rate is not changed greatly in the process of changing the extraction time from 45min to 60min by using the 3,3',5,5', 7-pentahydroxyflavone compound with the highest content in the spina gleditsiae total flavonoids as an extraction rate marker, so that the optimal extraction time is finally determined to be 45 min.
In conclusion, the choline chloride-1, 4-butanediol (1: 4)/20% aqueous solution is the eutectic solvent with the highest extraction rate, wherein the optimized extraction temperature is 55 ℃, the feed-liquid ratio is 1:30mg/m L, and the extraction time is 45 min.
The present invention is described in further detail below with reference to specific examples, which are intended to be illustrative of the invention and not limiting.
Example 1:
a method for preparing spina gleditsiae total flavonoids by using a eutectic solvent comprises the following steps:
(1) the optimization of the eutectic solvent is that after the spina gleditsiae medicinal materials are crushed, 1.0g of spina gleditsiae medicinal material powder is added into eutectic solvent water solution (v/v) DES-1 with the water content of 20% for ultrasonic extraction (the power is 40Khz), the extraction temperature is 55 ℃, the material-liquid ratio is 1:30, the extraction time is 45 minutes, after the extraction is finished, the extract is filtered to obtain filtrate, the eutectic solvent extract filtrate is added into a glass column (50cm × 3cm) filled with AB-8 macroporous resin filler, firstly 5L water is used for elution, the eutectic solvent components are eluted, then 1L 90% ethanol (v/v) is used for elution, the eluent is collected, the concentrated and recovered solvent is combined to obtain an HP total flavonoid eutectic solvent extract, then HP L C analysis is carried out, and then DES-2, DES-3, DES-4 and DES-5 are used for extraction of total flavonoid of spina according to the method, four types of total flavonoid extracts are obtained in sequence, and the eutectic solvent extract is L C analysis is carried out.
(2) The extraction method of spina gleditsiae total flavone reference standard substance comprises the steps of crushing spina gleditsiae medicinal materials, adding 1.0g of spina gleditsiae medicinal material powder into methanol-water (75:25, v/v) for ultrasonic extraction, carrying out ultrasonic extraction at 55 ℃, wherein the material-liquid ratio is 1:30, the extraction time is 45 minutes, carrying out suction filtration on the extract after the extraction is finished to obtain filtrate, namely spina gleditsiae total flavone reference standard substance, carrying out HP L C analysis on the obtained reference substance, comparing the obtained reference substance with HP L C spectrums of DES-1, DES-2, DES-3, DES-4 and DES-5 in the step (1), and finding that DES-1 and DES-2 are consistent with HP L C spectrums of the reference standard, comparing the contents of 5 index flavone components in the extract by taking the index as an index, and finally determining DES-1[ choline chloride-1, 4-butanediol (Ch-But) ] as an optimal extraction solvent as shown in a result in a.
Table 2 DES-1 and DES-2 are compared with 5 index flavonoid contents in HP L C profile of reference standard.
(3) Optimization of molar composition ratio of choline chloride and 1,4-butanediol in DES-1: the molar ratio of choline chloride and 1,4-butanediol in DES-1 is optimized, and by comparing infrared spectrograms of eutectic solvents with 5 different molar compositions (1:2, 1:3, 1:4, 1:5, 1:6) (shown in figure 2), the characteristic absorption peak of the hydroxyl group of choline chloride-1, 4-butanediol (1:4) is the widest, which indicates that the contained hydroxyl group is the largest, namely the number of flavonoids complexed through hydrogen bonds is the largest, and further by the peak 3 with the highest content in total flavonoids of spina gleditsiae: 3,3',5,5', 7-pentahydroxyflavanone compound is used as an extraction rate marker, the extraction rate of choline chloride-1, 4-butanediol (1:4) is found to be the highest, and the result is shown in Table 3, so that the optimal molar ratio of the choline chloride to the 1,4-butanediol is finally determined to be 1: 4.
Table 3 molar composition of choline chloride and 1,4-butanediol in DES-1 vs peak 3: influence of extraction rate of 3,3',5,5', 7-pentahydroxyflavanone.
(4) Optimization of extraction temperature: the extraction temperature is optimized, 4 different extraction temperatures (45 ℃, 55 ℃, 65 ℃ and 75 ℃) are set, and Ch-But (1:4) is adopted to extract the saponin through the peak 3 with the highest content in the total flavonoids of the spina gleditsiae: 3,3',5,5', 7-pentahydroflavone compound is used as an extraction rate marker, and the extraction rate of 55 ℃ raised to 65 ℃ is not changed greatly, and the result is shown in table 4, so that 55 ℃ is finally determined as the optimal extraction temperature.
Table 4 Ch-But (1:4) extraction temperature vs peak 3: influence of extraction rate of 3,3',5,5', 7-pentahydroxyflavanone.
(5) Optimization of the water content in the Ch-But (1:4) eutectic solvent: the water content of Ch-But (1:4) eutectic solvent is optimized, 4 different water contents (0, 20%, 40%, 60%) are set, and the peak 3 with the highest content in spina gleditsiae total flavonoids is determined: the 3,3',5,5', 7-pentahydroflavonone compound was used as an extraction rate marker, and the extraction rate was found to be the highest when the water content was 20%, and the results are shown in table 5, so that the optimum water content was finally determined to be 20%.
TABLE 5 water content in Ch-But (1:4) vs Peak 3: influence of extraction rate of 3,3',5,5', 7-pentahydroxyflavanone.
(6) Optimization of material-liquid ratio, namely, optimizing the material-liquid ratio of the spina gleditsiae and the eutectic solvent, setting 4 different material-liquid ratios (1:10, 1:20, 1:30 and 1:40mg/m L), and finding that the extraction rate is highest when the material-liquid ratio is 1:30mg/m L by using a peak 3: 3,3',5,5', 7-pentahydroxyflavanone compound with the highest content in total flavonoids of the spina gleditsiae as an extraction rate marker, wherein the result is shown in table 6, so that the optimal material-liquid ratio is finally determined to be 1:30mg/m L.
Table 6 feed-liquid ratio peak 3: influence of extraction rate of 3,3',5,5', 7-pentahydroxyflavanone.
(7) Optimization of extraction time: the extraction time is optimized, 4 different extraction times (15, 30, 45 and 60min) are set, the 3,3',5,5', 7-pentahydroxyflavone compound with the highest content in the total flavonoids of the spina gleditsiae is used as an extraction rate marker, the extraction rate change is not large in the process that the extraction time is changed from 45min to 60min, and the result is shown in table 7, so that the optimal extraction time is finally determined to be 45 min.
Table 7 extraction time vs peak 3: influence of extraction rate of 3,3',5,5', 7-pentahydroxyflavanone.
In conclusion, the choline chloride-1, 4-butanediol (1: 4)/20% aqueous solution is the eutectic solvent with the highest extraction rate, wherein the optimized extraction temperature is 55 ℃, the feed-liquid ratio is 1:30mg/m L, and the extraction time is 45 min.
It should be noted that the above-mentioned embodiments are only preferred embodiments of the present invention, and the present invention is not limited thereto, and although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that modifications and equivalents can be made in the technical solutions described in the foregoing embodiments, or equivalents thereof. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention. Although the present invention has been described with reference to the specific embodiments, it should be understood by those skilled in the art that various changes and modifications may be made without departing from the spirit and scope of the invention.
Claims (10)
1. The eutectic solvent is characterized in that a hydrogen bond acceptor is choline chloride, and a hydrogen bond donor is polyalcohol, sugar or organic acid.
2. The eutectic solvent according to claim 1, wherein the polyol is 1,4-butanediol, ethylene glycol, or glycerol.
3. The eutectic solvent according to claim 1, wherein the sugar is glucose.
4. The eutectic solvent according to claim 1, wherein the organic acid is citric acid.
5. The eutectic solvent according to claim 1, wherein a molar ratio of the hydrogen bond acceptor to the hydrogen bond donor is 1:2 to 6.
6. A method for preparing spina gleditsiae total flavonoids by using a eutectic solvent is characterized in that spina gleditsiae medicinal materials are crushed, dispersed in an aqueous solution of the eutectic solvent, subjected to ultrasonic extraction and separated to obtain spina gleditsiae total flavonoids extracts.
7. The method for preparing total flavonoids of spina gleditsiae according to claim 6, characterized in that the water content of the aqueous solution of the eutectic solvent is 10-60%.
8. The method for preparing total flavonoids of spina gleditsiae by using the eutectic solvent as claimed in claim 6, wherein the ratio of the raw materials to the liquid is 1: 10-40.
9. The method for preparing total flavonoids of spina gleditsiae by using the eutectic solvent as claimed in claim 6, wherein the extraction temperature is 45-75 ℃ and the extraction time is 15-60 min.
10. The method of any one of claims 6-9 to obtain total flavonoids from spina Gleditsiae.
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