CN109718291B - Method for directionally and rapidly enriching target components in traditional Chinese medicine, particularly fructus evodiae - Google Patents
Method for directionally and rapidly enriching target components in traditional Chinese medicine, particularly fructus evodiae Download PDFInfo
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- CN109718291B CN109718291B CN201811536679.0A CN201811536679A CN109718291B CN 109718291 B CN109718291 B CN 109718291B CN 201811536679 A CN201811536679 A CN 201811536679A CN 109718291 B CN109718291 B CN 109718291B
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Abstract
The invention provides a method for enriching target components of traditional Chinese medicines, which is characterized in that the distribution ratio of the target components in a two-phase solvent system is 0.2-5, the upper phase extraction is carried out for a plurality of times at the lower phase, and then the upper phase extraction is carried out for a plurality of times at the lower phase. More particularly relates to a method for directionally and rapidly enriching target components in fructus evodiae, wherein a sample obtained after crude extraction of the fructus evodiae is subjected to upper phase extraction and lower phase back extraction by adopting a normal hexane-ethyl acetate-methanol-water solvent system, so that the directional and rapid enrichment of the target components is completed. The method can realize the directional rapid enrichment of the target component and the removal of most impurities, is different from the prior liquid-liquid extraction, can realize the large-scale directional rapid enrichment of the target component, greatly reduces the loss of the target component, and removes most impurities.
Description
Technical Field
The invention belongs to the field of plant component extraction, in particular to the field of extraction of target components in traditional Chinese medicines, and particularly relates to a method for enriching target components in fructus evodiae.
Background
Traditional Chinese medicine components are complex, particularly trace components, and in order to further analyze or separate, a sample is usually subjected to further concentration and enrichment treatment so as to improve the content of target components.
At present, the methods for enriching samples are mainly used for solvent extraction, chromatography, solid phase extraction and the like. The solvent extraction method generally adopts organic reagents such as methanol, ethanol, n-butanol, ethyl acetate, petroleum ether, n-hexane and the like for extraction or extraction, the sample processing amount is large, but the target components lack specificity, and the final sample contains a large amount of other impurities, and generally further segmentation and enrichment are carried out by combining with chromatography, so that the efficiency is low and the effect is poor.
The traditional chromatographic enrichment technologies such as macroporous resin, silica gel column chromatography, gel column chromatography and the like generally have the defects of low separation efficiency, long period, poor reproducibility, high solvent consumption, dead sample adsorption, expensive filler, easy loss of small trace components and the like, the sample amount processed by the chromatographic method depends on the capacity of a chromatographic column, the sample amount can reach hundred grams in a laboratory, the final enriched product can reach milligram, and the chromatographic enrichment needs to be carried out for many times in order to obtain more samples, so that the time, labor and reagent cost are extremely high.
The solid phase extraction method is essentially a chromatography, is a relatively new rapid enrichment technology developed in recent years, has the advantages of rapidness, high selectivity, low solvent consumption, high efficiency and the like, is mainly used for enrichment analysis of trace or micro-components such as pesticide residues in biological samples, food and medicines and the like, and has low sample amount of treatment, generally from microgram level to milligram level.
The fructus evodiae is Rutaceae plant fructus evodiaeEuodia rutaecarpa(Juss.) Benth, stone tigerEuodia rutaecarpa (Juss.) Benth. var. officinalis(Dode) Huang or RutaceaeEuodia rutaecarpa (Juss.) Benth. var. bodinieri(Dode) Huang's dried nearly ripe fruit, enter liver, spleen, stomach, kidney channel, have effects of dispelling cold and relieving pain, lowering adverse qi and arresting vomiting, supporting yang and relieving diarrhea. Wu Zhu Yu is the essential herb for warming middle energizer and alleviating pain, since it is listed as a middle-grade herb in Shen nong Ben Cao Jing (Shen nong's herbal Jing). Therefore, the research and development of the enriched fructus evodiae target component for further extracting the effective component have important significance.
Disclosure of Invention
The invention aims to explore a directional processing method which is faster, simpler and more convenient than the prior enrichment method and has larger sample processing amount, and is used for large-scale directional and rapid enrichment of target components in a complex matrix of the traditional Chinese medicine. The target component may be a known component or may be a subject of further study in the future, and the method of the present invention may quantify the target component based on the detected chromatographic peak, and then calculate the distribution ratio based on the peak area, and does not necessarily require that what the specific component is known in advance.
The technical principle of the invention is provided by the inventor through research and analysis. Assume that three components (each component consisting of one or more compounds) are present in a sample: the amount of the impurity 1, the target component a,impurity 2, which has a retention time in reverse phase chromatography as shown in FIG. 1, and a partition coefficient in a two-phase system ofK 1 、K A 、K 2 Then, the polarities of the three components are in descending order: impurity 1>Target component A>Impurity 2, three componentsKThe value size order is:K 1 <K A <K 2。
distribution coefficient
（1）
（VOn the upper part、VLower partAre respectively the volume of the upper phase and the lower phase, COn the upper part、CLower partRespectively the concentration of the components in the upper phase and the lower phase)
When the volumes of the upper phase and the lower phase are the same, the following are provided:
K=Con the upper part/CLower part (2)
When the lower phase is extracted for multiple times by using the equal volume of the upper phase, for the compound A, the enrichment ratio of the upper phase A is as follows when the upper phase and the lower phase are distributed:
MA=（Con the upper part/（COn the upper part+CLower part））×100%
Substituting into formula (2) to obtain
MA=(1/(1+1/K A))×100% （3）
At this time, the process of the present invention,K A the larger the value, the higher the enrichment of A, but at the same time impurity 2 is also extracted to the upper phase.
When the upper phase is extracted for multiple times by using the equal volume of the lower phase, for the compound A, the enrichment ratio of the upper phase A is as follows when the upper phase and the lower phase are distributed:
MA=（Clower part/（COn the upper part+CLower part））×100%
Substituting into formula (2) to obtain
MA=(1/(1+K A)) ×100% （4）
At this time, the process of the present invention,K A the smaller the value, the higher the enrichment of A, but at the same time impurity 1 is also extracted toThe lower phase.
As can be inferred from the formulas (3) and (4), in order to realize the enrichment of the target component A, while the impurities 1 and 2 are as small as possible,K A the value needs a reasonable interval, andK1、K2andK A the difference of (a) is sufficiently large. Under the premise of meeting the requirement, the lower phase can be enriched into the upper phase by the extraction of the upper phase, and the lower phase can be simultaneously removedKImpurity 1 with smaller value is then enriched in the upper phase by extraction of the lower phase into the lower phase and simultaneously removedKImpurity 2 with a larger value.
Enrichment ratio during upper phase extraction and lower phaseKThe relationship between the number of extractions is:
the function curve of equation (5) is:
as can be seen from fig. 2, when the upper phase is extracted from the lower phase,Kif the extraction times n =5 and 0.2, the enrichment rate can reach 60 percent, and if the extraction times n =5, the enrichment rate can reach 60 percentK>At 0.2, the enrichment ratio is higher for the same extraction times. The extraction times can be increased or increased for higher enrichmentKThe value is obtained.
Enrichment ratio during lower phase extraction and upper phase extractionKThe relationship between the number of extractions m is:
the function curve of equation (6) is:
as can be seen from fig. 2, when the upper phase is extracted from the lower phase,Kwhen the extraction times n =5 is =0.2, the enrichment ratio can reach 59.8 percent, and when the extraction times n =0.2, the enrichment ratio is higher than the threshold valueK>When the concentration is 0.2, the enrichment ratio is higher for the same extraction timesHigh. The extraction times can be increased or increased for higher enrichmentKThe value is obtained.
As can be seen from fig. 3, when the upper phase extracts the lower phase,K=5, when the extraction times m =5, the enrichment ratio can reach 59.8 percent, and when the extraction times m =5, the enrichment ratio is higher thanK<5When the enrichment ratio is higher for the same extraction times, the extraction times can be increased or decreased properly for higher enrichment ratioKThe value is obtained.
This gives an enrichment for a group of compounds of which the constituent compounds areKThe value distribution is more reasonable to be 0.2<K<5, the extraction times are 5 times, and the enrichment rate can reach 59.8 percent. The actual situation can be combined with the figure 2 and the figure 3 according toKAnd determining the extraction times n and m respectively according to the actual condition of the value distribution.
Final enrichment ratio of target component andKthe relationship of the values is:
substituting formula (2):
when n = m =5, the function curve is:
from enrichment rate-KThe function curve shows whenKWhen the value is 1, that is, the concentrations of the target component A in the upper phase and the lower phase are the same, the extraction rate is the highest, and when the concentration is 1K<1, because the phase efficiency is reduced due to the upper phase extraction,K>1, the final enrichment rate is reduced due to the reduced efficiency of the lower phase extraction and the upper phase. Thus, it is possible to provideKIs the theoretical optimal balance point of the invention when =1K=1, when the extraction times is 5, the high enrichment of the target component can be realized, and the content of the impurity 1 can reach 93.85 percentKSmall valueThe efficiency is lower when the upper phase is extracted to the lower phase, and the impurity 2 isKThe larger value, the lower phase extraction phase ratio is lower, so that impurities 1 and 2 can be mostly removed.
Calculated, 0.2<K<5 reasonable enrichment of target componentKValue ranges which allow an enrichment rate of 59.8% to be achieved, and which are referred to when enriching multiple targets, and which are recommended when enriching a single compoundKValues close to 1 are most effective.
Wherein the two-phase solvent system used differs for different target components, such as solvent ratio and/or solvent composition. Known literature on countercurrent chromatographic separation reports on two-phase solvent systems for which different components are suitable. However, these documents are intended for separation and are not directed to the directed enrichment performed by the present invention. I.e. the two are essentially different, but the two-phase system used can be adapted to the process of the invention itself. Therefore, the gist of the present invention is: when the distribution ratio of the target component in the two-phase solvent system is adjusted within a suitable range, the two-phase system used may have no direct relationship with the solvent, and specifically, the distribution ratio of the target component in the two-phase system may be set to 0.2 to 5, preferably 0.3 to 5. The solvent system can realize the directional rapid enrichment of target components and the removal of most impurities through multiple extractions, and the method is different from the prior liquid-liquid extraction, can realize the large-scale directional rapid enrichment of the target components, and greatly reduces the loss of the target components. A method for enriching target components of traditional Chinese medicine is characterized in that the distribution ratio of the target components in a two-phase solvent system is 0.2-5, preferably 0.3-5, and the upper phase extraction is performed for a plurality of times at the lower phase, and then the upper phase extraction is performed for a plurality of times at the lower phase, or the upper phase extraction is performed for a plurality of times at the upper phase, and then the upper phase extraction is performed for a plurality of times at the lower phase. The above extraction sequence is suitable for different Chinese medicinal materials, but can be preferably selected according to different Chinese medicinal materials.
In the present invention, it is preferable that the partition ratio of the objective component in the two-phase solvent system is in the range of 0.2 to 5, and the upper phase is extracted first from the lower phase and then from the upper phase. For example, a method for enriching target components of fructus evodiae is characterized in that the distribution ratio of the target components in a two-phase solvent system is 0.2-5, preferably 0.3-5, and the upper phase is extracted for a plurality of times by the lower phase, and then the lower phase is extracted for a plurality of times by the upper phase. Wherein preferably one or more of said times is 3 to 8 times, preferably 4 to 6 times, most preferably 5 times. Wherein, for the evodia rutaecarpa, an upper phase is extracted to form a lower phase, water-soluble impurities such as polysaccharide and the like are removed from a middle sample, the efficiency is high when the solvent is recovered, and a large amount of foams generated during reduced pressure distillation due to high concentration of the sample can be avoided. Although the upper phase can also be enriched with the target component by first performing a lower phase extraction.
Further, most of the current liquid-liquid extraction is a two-phase solvent system composed of binary solvents, generally water and an organic phase immiscible with water, the organic phase is generally reagents such as n-hexane, petroleum ether, chloroform, diethyl ether, ethyl acetate, n-butanol and the like, the selection range is narrow, and the distribution coefficient cannot be directionally adjusted according to the properties of the target compound. The invention adopts a quaternary solvent system, selects and inspects the quaternary solvent system according to the physicochemical properties of the target compound by adjusting the type and the proportion of the quaternary solvent system, and establishes a rapid directional enrichment method suitable for the target component in the fructus evodiae.
The invention specifically relates to a technical scheme of fructus evodiae, which comprises the following steps: a method for directionally and rapidly enriching target components in fructus evodiae is characterized by comprising the following steps:
and (2) adding an upper phase dissolved extract of a crude extracted sample of fructus evodiae into a lower phase with the same volume, standing, taking out an upper phase, adding the upper phase into the lower phase for extraction, preferably extracting for 3 to 8 times, preferably for 4 to 6 times, most preferably for 5 times, combining the upper phases, evaporating to dryness, adding the upper phase for dissolution, adding the lower phase, mixing, standing, taking out the lower phase, preferably extracting for 3 to 8 times, preferably for 4 to 6 times, most preferably for 5 times, combining the lower phases, and evaporating to dryness to obtain the enriched target component.
Preferably, the fructus evodiae crude extract can be prepared by conventional methods such as ultrasonic extraction method, heating reflux extraction method, etc., wherein ultrasonic extraction is preferably adopted, for example, fructus evodiae is pulverized, sieved by a No. 3 sieve, added with methanol 40 kHz, ultrasonically extracted for 30min, extracted for 3 times, filtrates in each time are combined, and further evaporated to dryness to obtain an extract for later use.
Preferably, the solvent system is n-hexane-ethyl acetate-methanol-water in a volume ratio of 1: 2: 2.3-2.5: 2, preferably 1: 2: 2.3: 2.
the invention belongs to liquid-liquid extraction method, improves specificity and selectivity compared with the traditional method, and can complete directional rapid enrichment of target components by adjusting the solvent composition of a two-phase solvent system to ensure that the distribution ratio of the target components in the two-phase system is 0.2-5, preferably 0.3-5, namely, by multiple times of upper-phase extraction and lower-phase back extraction. The method has the characteristics of orientation and rapidness, is suitable for enriching target components in traditional Chinese medicines and natural medicines, has high enrichment efficiency and large sample handling capacity, can perform oriented adjustment according to the physicochemical properties of target compounds, is simple and convenient to operate, and does not need expensive reagents and equipment. Particularly, the solvent system screened according to the invention has very obvious effect on the enrichment of the target component in the fructus evodiae, and experiments show that the content of the target component in the enriched sample reaches 69.71%, more specifically, the content is improved by 900.65% compared with the content of the original sample, and most of impurity components are removed.
Drawings
FIG. 1 principle sample reverse chromatogram
Enrichment ratio during upper phase extraction and lower phase extraction in FIG. 2KThe relationship between the number of extractions n
FIG. 3 enrichment ratio during lower phase extraction and upper phase extractionKThe relationship between the number of extractions m
Final enrichment ratio at n = m =5 in fig. 4-KCurve of function
FIG. 5 chromatogram of the initial sample
FIG. 65 lower phase extraction by lower phase and lower phase
FIG. 75 time upper phase extraction lower phase and upper phase
FIG. 85 time lower phase extraction upper phase
FIG. 95 lower phase extraction upper phase and lower phase (final enriched product)
Detailed Description
The invention is further illustrated by the following examples.
Example 1
1 sample extraction method
Pulverizing 300 g fructus evodiae, sieving with No. 3 sieve, adding 500 mL methanol 40 kHz, ultrasonic extracting for 30min, extracting for 3 times, filtering, mixing filtrates, and evaporating to obtain fructus evodiae methanol extract 13.13 g.
2. Chromatographic analysis conditions
By Agilent SB-C18(250 mm. times.4.6 mm, 5 μm) chromatography column; the detection wavelength is 210 nm; flow rate 1.0 mL/min-1(ii) a The column temperature is 30 ℃; the sample size is 10 μ L, the mobile phase is water (a) -acetonitrile (B) gradient elution, the phase B proportion varies with time: 0-10 min, 10% -45%; 45 percent in 10-30 min; 45-100% of the total amount of the mixture for 30-35 min; 35-45 min, 100%.
3. Research on enrichment method
3.1 investigation of solvent systems
When solvent systems such as n-butanol-water, ethyl acetate-methanol-water, methyl tert-butyl ether-methanol-water, chloroform-water, n-hexane-ethyl acetate-methanol-water and the like are considered, the target component in the fructus evodiae has a reasonable distribution ratio in the n-hexane-ethyl acetate-methanol-water system (the ratio is: (KValue), therefore, the ratio of the n-hexane-ethyl acetate-methanol-water solvent system was investigated, and the target components in each ratio system wereKThe values are shown in Table 1. When the ratio is 1: 2: 2.3: 2, target componentKThe values are distributed in a reasonable interval, so that the final selection system is n-hexane-ethyl acetate-methanol-water (1: 2: 2.3: 2).
TABLE 1 of the target component in the respective solvent systemsKValue of
3.2 optimal solvent System extraction method
Preparing a proper amount of n-hexane-ethyl acetate-methanol-water (1: 2: 2.3: 2) solvent system, taking 200 mL of each of the upper phase and the lower phase, dissolving the evodia rutaecarpa methanol extract, shaking, standing for layering, collecting the upper phase, continuously extracting the lower phase with the new upper phase for 5 times, combining the upper phases, and recovering the solvent to obtain a middle enriched product of 3.54 g. And (3) dissolving the intermediate product in 200 mL of each of the upper phase and the lower phase, shaking, standing for layering, collecting the lower phase, continuously extracting the upper phase with the new lower phase for 5 times, combining the lower phases, and recovering the solvent to obtain 1.41 g of the final enriched product.
Chromatograms of the initial sample 3.3, the lower phase after the upper phase extraction, the upper phase after the lower phase extraction, the upper phase after the upper phase extraction, the 5 lower phase after the upper phase extraction, and the lower phase after the upper phase extraction (final enriched product) of the 5 lower phase are respectively shown in fig. 5-9, and the target component is peak 1-6. The target component is a characteristic component in the fingerprint of the fructus evodiae, and the mass numbers of No. 1-6 chromatographic peaks in a negative mode are respectively found by analyzing a sample through liquid chromatography-mass spectrometry, wherein the mass numbers of the No. 1 chromatographic peaks are as follows: 485.2 and 258.0; peak No. 2: 469.3, respectively; peak No. 3: 483.2, respectively; peak No. 4: 467.3; peak No. 5: 302.2; peak No. 6: 292.1. according to the nitrogen rule, 258.0, 5 and 6 peaks in the No. 1 peak are alkaloid components, and the rest components may be saponin or flavonoid glycoside components, and all the components may be effective components in the fructus evodiae, so that the enrichment method is favorable for subsequent further research.
The percentage content of the target component in the initial sample is 7.74 percent through the area normalization method, the percentage content of the target component in the enriched sample is 69.71 percent, the content of the enriched target component is improved by 900.65 percent, and most impurity components are removed.
Claims (5)
1. A method for enriching target components of fructus evodiae is characterized in that the distribution ratio of the target components in a two-phase solvent system is 0.2-5, a sample obtained after coarse extraction of the fructus evodiae adopts an upper phase dissolving extract of a normal hexane-ethyl acetate-methanol-water solvent system, a lower phase with the same volume is added and mixed uniformly, standing is carried out, an upper phase is taken out, then an upper phase is added into the lower phase for extraction, repeated extraction is carried out for 3-8 times, the upper phase is combined, an equal volume of the lower phase and the upper phase are added for dissolution after evaporation, mixing is carried out, standing is carried out, the lower phase is taken out, repeated extraction is carried out for 3-8 times, the lower phase is combined, and evaporation is carried out to obtain the enriched target components;
wherein the solvent system ratio of the n-hexane-ethyl acetate-methanol-water is 1: 2: 2.3: 2.
2. the method of claim 1, wherein: the times of the upper phase extraction and the lower phase extraction are respectively 4-6 times.
3. The method of claim 2, wherein: the times of the upper phase extraction and the lower phase extraction are respectively 5 times.
4. The method of claim 1, wherein: the fructus evodiae crude extract can be prepared by ultrasonic extraction method or heating reflux extraction method.
5. The method of claim 4, wherein: the ultrasonic extraction is to pulverize fructus evodiae, screen with No. 3 sieve, add methanol 40 kHz, and perform ultrasonic extraction for 30min for 3 times.
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| RapidandpreparativeseparationoftraditionalChinesemedicine;YanbinLu 等;《JournalofChromatographyA》;20091231;第4140-4146页 * |
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