KR101844759B1 - Analytical method and database construction of organic acid profile using gas chromatography in Orostachys japonicus - Google Patents
Analytical method and database construction of organic acid profile using gas chromatography in Orostachys japonicus Download PDFInfo
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Abstract
The present invention relates to a method for distinguishing between wafers using the composition of the organic acid profile, analyzing the profile of the organic acid in the wastes extract using gas chromatographic techniques.
According to the analysis method of the present invention, 12 kinds of organic acid components including malic acid and isocitric acid, which are the major organic acid components of the wastes, are profiled by gas chromatography, and a database on the organic acid composition is constructed Therefore, there is an advantage in that it is possible to discriminate the wastes according to the organic acid profile composition of the wastes.
Description
The present invention relates to a method for differentiating the wastes by analyzing the profiles of organic acids in the wastes extract using gas chromatographic techniques and building a database of the profiles of the organic acids.
Orostachys japonicus is a perennial herbaceous plant with a dicotyledonous rosewood stone crustacean called a rocksol, and it is said that a herbal medicine has a special effect on the anticancer effect, fever, geothermal, hepatitis, eczema, burn and the like. In particular, it is known that it is effective for liver cancer, breast cancer, pancreatic cancer, bone cancer, esophageal cancer, uterine cancer, lymphatic cancer, stomach cancer, colon cancer, diabetes, paralysis, arthritis, gastrointestinal disease, limb pain, limb constipation, vomiting,
As described above, various pharmacological effects have been known for the improvement of immunity, anti-inflammation, antioxidation, antibacterial, anti-hyperlipidemia, antidiabetic, anti-cancer, liver function improvement, atopy and dermatitis treatment. . However, the analysis of Waksong organic acid depends on a small number of target compound analysis, and research on the composition through systematic profile analysis has not been attempted.
Therefore, the present invention has been completed by developing a profile analysis method using gas chromatography as a MO-TBDMS derivative instead of a target analysis for organic acids of the feed, and constructing a database of the organic acid profile of the wastes.
Accordingly, an object of the present invention is to provide a method of distinguishing organic acids by analyzing profiles of organic acids using gas chromatography, establishing a database of profiles, and using the method.
In order to achieve the above object, the present invention provides a method of distinguishing between treatments comprising the step of analyzing the composition of malic acid and isocitric acid in the sample.
In one embodiment of the present invention, the sample is obtained by adding methoxamine hydrochloride to an extract to extract MO (methoxime) derivatization (step 1); Extracting organic acid by adding diethyl ether and ethyl acetate to the reaction solution derivatized with MO (methoxime) (step 2); And TBDMS (tert-butyl dimethyl silyl) derivatization by adding N-methyl-N- (tert-butyldimethylsilyl) trifluoroacetamide to the organic acid extract And a step (step 3).
In one embodiment of the present invention,
In one embodiment of the present invention, the MO (methoxime) derivatized reaction solution of
In one embodiment of the present invention, the composition of the imatinib malic acid and the isocitric acid may be contained in the sample in an amount of 30 to 50% by area of malic acid and 20 to 40% by area of isocitric acid based on 100% by area of the total organic acid profile.
In one embodiment of the present invention, the composition of the malic acid and the isocitric acid may be contained in the sample in a range of 35 to 45 area% malic acid and 25 to 35 area% isocitric acid based on 100 area% of the total organic acid profile.
In one embodiment of the present invention, when the method includes the kind of the organic acid and the composition of the organic acid profile in the following table, it may be judged that the sample is in a feed.
Further, the present invention relates to a method for producing a compound of formula (I), which comprises the step of adding methoxamine hydrochloride to an extract of Wakoshi to derivatize MO (methoxime) (step 1); Extracting organic acid by adding diethyl ether and ethyl acetate to the reaction solution derivatized with MO (methoxime) (step 2); Adding TBDMS (tert-butyldimethylsilyl) derivatization to the organic acid extract by adding N-methyl-N- (tert-butyldimethylsilyl) trifluoroacetamide 3); And analyzing the TBDMS (tert butyl dimethyl silane) derivatized reactant (step 4).
In one embodiment of the present invention,
In one embodiment of the present invention, the MO (methoxime) derivatized reaction solution of
In one embodiment of the present invention, step 4 may be analysis with a gas chromatograph.
According to the method for analyzing the organic acid profile in the feed according to the present invention, a total of 12 kinds of organic acid components including malic acid and isocitric acid, which are major organic acid components of the feed, are profiled using gas chromatography, It is possible to construct a database, so that it is possible to distinguish the wastes according to the organic acid profile composition of the wastes.
FIG. 1 shows the overall process of the method for analyzing the worts extract for analyzing the worts organic acid of the present invention.
2 is a chromatogram showing the peak for the analysis of the organic acid profile in the rocksol analyzed by a gas chromatograph-flame ionization detector connected to the non-polar column of DB-5 in the double capillary column.
FIG. 3 is a chromatogram showing the peak for the analysis of the organic acid profile in the rocksol analyzed by gas chromatograph-flame ionization detector connected to a DB-17 column having an intermediate polarity among the double capillary columns.
Figures 2 and 3 illustrate the chromatogram obtained simultaneously by obtaining a single analysis with a gas chromatograph-flame ionization detector with a double capillary column connected.
Figure 4 is a chromatogram used to identify the structure of the organic acids found in the wastes by analysis with a gas chromatograph-mass spectrometer on the organic acids obtained by analysis with the gas chromatograph-flame ionization detector of Figures 2 and 3 .
The present invention is characterized by providing a method of distinguishing between treatments comprising the step of analyzing the composition of the organic acid profile of malic acid and isocitric acid in a sample.
Further, the present invention relates to a method for producing a compound of formula (I), which comprises the step of adding methoxamine hydrochloride to an extract of Wakoshi to derivatize MO (methoxime) (step 1); Extracting organic acid by adding diethyl ether and ethyl acetate to the reaction solution derivatized with MO (methoxime) (step 2); Adding TBDMS (tert-butyldimethylsilyl) derivatization to the organic acid extract by adding N-methyl-N- (tert-butyldimethylsilyl) trifluoroacetamide 3); And analyzing the TBDMS (tert-butyldimethylsilyl) derivatized reactant (step 4).
In the present invention, " Orostachys japonicus " is a perennial herbaceous plant with a dicotyledonous plant rosewood, which is also called a rocksol, and it is said that a herbal medicine has an anticancer effect, fever, geothermal, hepatitis, have. In particular, it is known that it is effective for liver cancer, breast cancer, pancreatic cancer, bone cancer, esophageal cancer, uterine cancer, lymphatic cancer, stomach cancer, colon cancer, diabetes, paralysis, arthritis, gastrointestinal disease, limb pain, limb constipation, vomiting,
As described above, various pharmacological effects have been known for the improvement of immunity, anti-inflammation, antioxidation, antibacterial, anti-hyperlipidemia, antidiabetic, anti-cancer, liver function improvement, atopy and dermatitis treatment. .
The term " extract " used in the present invention refers to an extract obtained by an extraction treatment of soy sauce, a diluted solution or concentrate of the extract, a dried product obtained by drying the extract, a controlled preparation or a purified product of the extract, Extracts themselves and extracts of all formulations which can be formed using extracts.
In the present invention, the kind of the extraction solvent used for extracting the feed is not particularly limited, and any solvent known in the art can be used. Non-limiting examples of the extraction solvent include water, an alcohol, a mixed solvent thereof, and the like. The saliva extract of the present invention may be a water extract.
In the transdermal extract of the present invention, the method for extracting the above-mentioned transudate is not particularly limited, and may be extracted according to a method commonly used in the art. Nonlimiting examples of the extraction method include room temperature extraction, hot water extraction, cold extraction, reflux cooling extraction, ultrasonic extraction, and steam extraction. These may be performed alone or in combination with two or more methods .
Specifically, in one embodiment of the present invention, the raw wort was pulverized, ultrasonically extracted with water, and then centrifuged to obtain a supernatant liquid.
The above extracts were prepared as samples for the analysis of profiles of organic acids in the wastes by performing MO derivatization, organic acid extraction, volatilization and TBDMS derivatization.
Methoxiamine hydrochloride was used in the MO derivatization step and N-methyl-N- (tert-butyldimethylsilyl) trifluoroacetamide (TBDMS) was used in the TBDMS derivatization step. tert-butyldimethylsilyl) trifluoroacetamide).
The MO derivative converted using the above methoxyamine hydrochloride may have the following structural formula.
The TBDMS derivative converted using the N-methyl-N- (tert-butyldimethylsilyl) trifluoroacetamide (N-methyl-N- (tert-butyldimethylsilyl) trifluoroacetamide) may have the following structural formula.
In addition, by using the MO derivative, it is possible to effectively detect the organic acid component, which is difficult to be analyzed by the decomposition and adsorption of the analyte at the sample inlet, when the MO derivatization is not used. In the case of methoximation of the keto group of keto acid using derivatization, the peak shape and intensities can be increased, so that the linearity within the quantitative range is improved and the analytical sensitivity Improvement.
The MO derivatization can be performed in an extract by reacting with NaOH at a pH of 10 or more in a base condition at 40 to 80 ° C for 20 to 40 minutes, preferably at 60 ° C for 30 minutes, It is not.
The TBDMS derivatization may be performed at 60 ° C for 20-40 minutes to perform an organic acid in the extract, preferably at 60 ° C for 30 minutes, but is not limited thereto.
In general, in order to analyze organic acids using gas chromatography, a process of converting a polar group having an active hydrogen atom of an organic acid into an inactive volatile derivatization is generally required, and when performing a post conversion analysis, a more selective and high It has the advantage of being able to analyze with sensitivity. In the case of organic acids with most keto groups (carbonyl groups), TBDMS only appears as two peaks in keto and enol form. To overcome these drawbacks, the present study has attempted to convert keto groups into MO derivatives in a basic aqueous solution The remaining active hydrogen was converted to TBDMS derivatization. After the derivatization by the method of the present invention and finally the analysis of the organic acid by using the flame ionization detector with MO-TBDMS, especially the detector sensitivity is increased and the characteristic ion peak appears in the mass spectrometry spectrum, There is an advantage to be able to do.
On the other hand, when analyzing samples using a gas chromatograph-flame ionization detector, using DB-5 and DB-17, which are different polarity columns, Can be detected. The DB-5 capillary column is composed of 5% -Phenyl-95% methylpolysiloxane bonded phase and has a column length of 30 m, a diameter of 0.25 mm and a stationary phase thickness of 0.25 μm. The DB-17 capillary columns consist of a fixed phase of 50% -Phenyl-methylpolysiloxane bonded phase, with a capillary length of 30 m, a diameter of 0.25 mm and a fixed bed thickness of 0.25 μm. When used, it provides the advantages of complementary peaks identification of organic acid components in columns of different polarity by a single analysis.
On the other hand, when a sample is analyzed using a gas chromatograph-mass spectrometer, the components are first introduced into the mass spectrometer at a retention time difference between the stationary phase and the mobile phase of the capillary column mounted on the gas chromatograph. The introduced sample is ionized by the ionization apparatus. At this time, the ionization detection method is an electron impact method. The column is Ultra 2, 25 m in length, 0.25 mm in diameter, and 0.11 μm in thickness of the stationary phase.
As the mobile phase gas of the gas chromatograph, nitrogen, hydrogen, or helium gas may be used. Preferably, helium is used, but the present invention is not limited thereto.
Accordingly, the present invention provides a method for analyzing the profile of organic acids in a feed that contains a large amount of useful ingredients.
Also, the present inventors provide a method of using a database for composition in the organic acid profile by analyzing the profile of organic acids in the wastes containing a large amount of useful components as described above, to select the wastes.
The waste differentiation method according to the present invention comprises the step of analyzing the composition for the profile of malic acid and isocitric acid in the sample.
In one embodiment of the present invention, the sample is obtained by adding methoxamine hydrochloride to an extract of Walsh to induce MO (methoxime) derivatization (step 1); Extracting organic acid by adding diethyl ether and ethyl acetate to the reaction solution derivatized with MO (methoxime) (step 2); And tert-butyl dimethylsilyl (TBDMS) derivatization by adding N-methyl-N- (tert-butyldimethylsilyl) trifluoroacetamide to the organic acid extract (Step 3). ≪ / RTI >
In one embodiment of the present invention,
In one embodiment of the present invention, the MO (methoxime) derivatized reaction solution of
In one embodiment of the present invention, the composition of the organic acid profile of malic acid and isocitric acid may be contained in the sample in a range of 30 to 50% by area of malic acid and 20 to 40% by area of isocitric acid based on 100% Preferably 35 to 45% by area of malic acid and 25 to 35% by area of isocitric acid based on 100% by area of total organic acids, but is not limited thereto.
In one embodiment of the present invention, the method may include determining the type of the organic acid and the organic acid profile of the organic acid in the following table.
EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples. However, the following Examples are only the preferred embodiments of the present invention, and the present invention is not limited by the following Examples.
≪ Example 1 >
Manufacture of Wassong Extract
Orostachys japonicus , 419-4 Yongdang-dong, Suncheon-si, Jeollanam-do) The leaves (25-30g) were weighed and washed in running water for 2 ~ 3 minutes. The mixture was milled using a blender, and 0.1g (250-300 mL), sonicated for 30 min, and centrifuged at 3500 rpm for 5 min. The supernatant was used.
≪ Example 2 >
Mathoxime derivatization reaction
To 0.2 mL of the extract at 0.1 g / mL concentration obtained in Example 1, 0.8 mL of distilled water was added to dilute to 1 mL, and then 0.1 mL of methoxiamine hydrochloride (10 μg / μL) solution and 5 mL of 5 M NaOH 0.1 mL, the pH was adjusted to 12 or higher and the reaction was carried out at 60 ° C for 30 minutes to convert the keto group of the keto acid into the methoxime derivative in the extract (see FIG. 1).
≪ Example 3 >
Extraction and concentration
0.8 g of NaCl was added to the reacted Methoxime derivatization reaction solution in Example 2 to adjust the pH to 2 or less by adding 0.2 mL of 10% sulfuric acid, followed by the addition of 3 mL of diethyl ether and 2 mL of ethyl acetate The organic acids including keto acid were extracted and 5 μL of triethylamine was added to the flask and completely volatilized and dried under a nitrogen stream. Then, 0.1 mL of methylene chloride was added to completely remove moisture, followed by further volatilization-drying under a nitrogen stream.
<Example 4>
TBDMS derivatization reaction
10 μL of N-methyl-N- (tert-butyldimethylsilyl) trifluoroacetamide and 20 μL of toluene were placed in the volatile dried residue obtained in Example 3, and the remaining active hydrogen was converted into TBDMS derivative by reacting at 60 ° C. for 30 minutes 1).
≪ Example 5 >
Analysis of organic acids as MO-TBDMS derivatives
<5-1> Dual Capillary Column Gas Chromatography - Flame Ionization Detection
(Nonpolar column: length 30 m, inner diameter 0.25 mm, film thickness 0.25 μm) and DB-17 (intermediate polar column: length 30 m, inner diameter: 0.25 mm, film thickness 0.25 um) was used as the Agilent 7890N gas chromatograph of Agilent. Helium was used as the mobile phase gas, the flow rate was 1 mL / min, and the sample injection method was splitless mode (purge delay time: 0.7 min). The temperature of the column was initially maintained at 60 캜 for 2 minutes, and then the temperature was raised to 290 캜 at a rate of 5 캜 / min. Finally, it was allowed to stand at 290 ° C for 10 minutes. The temperature of the sample inlet was 260 ° C and the temperature of the flame ionization detector was 290 ° C.
As a result of the analysis of the MO-TBDMS derivative of Wassong extract as a double capillary column gas-chromatograph-flame ionization detector, as shown in FIGS. 2 and 3, 12 kinds of organic acids were found (1 = lactic acid; 2 = glycolic acid 4 = 3-hydroxypropionic acid; 5 = malonic acid; 6 = succinic acid; 7 = fumaric acid; 8 = 2-ketoglutaric acid a ; 8 '= 2-ketoglutaric acid b = 9 malic acid; 10 = 4-hydroxycinnamic acid; 11 = citric acid; 12 = isocitric acid) and 12 kinds of organic acids.
The results of profile analysis of organic acids with double capillary column gas chromatograph-flame ionization detector of different polarity DB-5 (nonpolar column) and DB-17 (intermediate polar column) It was confirmed that they exhibit different but almost similar peak heights and areas, which were useful for complementary peak identification (see FIGS. 2 and 3).
<5-2> Gas Chromatography - Mass Spectrometry
Agilent 7890N Gas Chromatography-5975C mass spectrometer from Agilent was used for structural analysis of organic acids found in Wassong. The ionization method was an electron impact method and the temperature of the ion source was 230 ° C. The column used was Ultra 2 (length 25 m, 0.25 mm ID, film thickness 0.11 μm), mobile phase gas was helium and flow rate was 0.5 mL / min. The sample was injected in a split mode (10: 1 split ratio). The column temperature was initially maintained at 100 占 폚 for 2 minutes, then heated to 250 占 폚 at a rate of 5 占 폚 / min, and finally heated to 300 占 폚 at 20 占 폚 / min for 5 minutes. The temperature of the sample inlet was 260 ° C and the temperature of the connecting device was 300 ° C.
As shown in FIG. 4, a total of 12 organic acids were found ((1 = lactic acid; 2 = glycolic acid; 3 = oxalic acid; = 3-hydroxypropionic acid; 5 = malonic acid; 6 = succinic acid; 7 = fumaric acid; 8 = 2-ketoglutaric acid a; 8 '= 2-ketoglutaric acid b; 9 = malic acid; 10 = 4-hydroxycinnamic acid; 11 = citric acid, 12 = isocitric acid) and 12 kinds of organic acids.
<5-3> Analysis of composition of organic acid profile
The total area was calculated by summing the areas for each of the 12 organic acids found in the wastes after the analysis by a double capillary column gas chromatograph-flame ionization detector. Then, the area for each organic acid was divided by the total area to calculate the area percent (%) and the composition was shown (see Table 1).
As a result of the analysis of the composition of the organic acid profile of wasong, it was confirmed that malic acid and isocitric acid were contained in an excess amount, and oxalic acid which was reported as an organic acid component of wastes was contained Lactic acid, glycolic acid, 3-hydroxypropionic acid, malonic acid, succinic acid, and fumaric acid as a new organic acid in Wassong. , 2-ketoglutaric acid, malic acid, 4-hydroxycinnamic acid, citric acid and isocitric acid to find organic acid profile The database of the composition was newly constructed.
In summary, the present invention establishes a method for the analysis of organic acid profiles using a dual capillary column gas-chromatographic-flame ionization detector and a gas chromatograph-mass spectrometer as MO-TBDMS derivatives of watson extract, A total of 12 kinds of organic acids were identified.
On the other hand, lactic acid, succinic acid; malic acid and citric acid are contained in the feed of the present invention, and an excessive amount of malic acid, which can be used as an antibacterial biomarker due to its antibacterial activity, can be distinguished by the method of the present invention.
The present invention has been described with reference to the preferred embodiments. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims. Therefore, the disclosed embodiments should be considered in an illustrative rather than a restrictive sense. The scope of the present invention is indicated by the appended claims rather than by the foregoing description, and all differences within the scope of equivalents thereof should be construed as being included in the present invention.
Claims (11)
The sample is obtained by adding methoxamine hydrochloride to the Wako extract to conduct MO (methoxime) derivatization (step 1);
Extracting organic acid by adding diethyl ether and ethyl acetate to the reaction solution derivatized with MO (methoxime) (step 2); And
A step of subjecting an organic acid extract to TBDMS (tert-butyldimethylsilyl) derivatization by adding N-methyl-N- (tert-butyldimethylsilyl) trifluoroacetamide Wherein the sample is a sample obtained by a method including the step (3).
Wherein the step 1 is carried out at a pH of 10 or more.
Wherein the MO (methoxime) derivatized reaction solution of step 2 is saturated with sodium chloride (NaCl) at a pH of 2 or less.
Wherein the organic acid profile composition of the malic acid and the isocitric acid is contained in the sample in an amount of 30 to 50% by area of malic acid and 20 to 40% by area of isocitric acid based on 100% by area of the total organic acid profile.
Wherein the composition of the organic acid profile of the malic acid and the isocitric acid is contained in the sample in an amount of 35 to 45% by area of malic acid and 25 to 35% by area of isocitric acid based on 100% by area of the total organic acid profile.
Wherein the method comprises determining the type of the organic acid and the composition of the organic acid profile in the table below.
Extracting organic acid by adding diethyl ether and ethyl acetate to the reaction solution derivatized with MO (methoxime) (step 2);
(Tert-butyldimethylsilyl) trifluoroacetamide to N-methyl-N- (tert-butyldimethylsilyl) trifluoroacetamide to the organic acid extract to make TBDMS (tert-butyldimethylsilyl) 3); And
And analyzing the TBDMS (tert-butyldimethylsilyl) derivatized reactant (step 4).
Wherein the step 1 is carried out at a pH of 10 or more.
Wherein the MO (methoxime) derivatized reaction solution of step 2 is saturated with sodium chloride (NaCl) at a pH of 2 or less.
Wherein the step 4 is carried out with a gas chromatograph.
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| Korean J. Microscopy 39(4), 333-340(2009) |
| Mass Spectrometry Letters Vol. 3, No. 3, 2012 |
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