CN110849999B - Liquid chromatography method for separating 8-epiloganin and loganin - Google Patents
Liquid chromatography method for separating 8-epiloganin and loganin Download PDFInfo
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Abstract
The invention discloses a liquid chromatography method for separating 8-epiloganin and loganin. As known to those skilled in the art, chiral compounds often need to be separated by means of a chiral chromatographic column, but the chiral chromatographic column has high cost, short service life and poor repeatability as compared with a conventional C18 chromatographic column, and in this case, a chiral mobile phase analysis method based on the conventional C18 chromatographic column is not lost as an option, low cost and stable analysis performance. The invention realizes the chromatographic separation of secoisolaricoside hemiacetal lactone and 8-epiloglycoside and loglycoside by using a chiral mobile phase analysis method based on a conventional C18 chromatographic column, and the method can be used for detecting whether the compound samples are single products or mixed products.
Description
Technical Field
The invention belongs to the field of pharmaceutical analysis, relates to separation and detection of optical isomers, and particularly relates to a liquid chromatography method for separating 8-epiloglycoside and loglycoside.
Background
The epiloganin hemiacetal lactone and the secologanin hemiacetal lactone, and the 8-epiloganin and the loganin are two pairs of isomers respectively, are chiral isomers, and have the following chemical structural formulas.
The secoisolaricoside hemiacetal lactone and secoisolaricoside hemiacetal lactone, and the 8-epistrychnine and the strychnine are chiral compounds, so that the epistrychnine and the strychnine are extremely difficult to separate on a conventional C18 chromatographic column. In this case, the secoisolaricoside hemiacetal lactone and the secoisolaricoside hemiacetal lactone may be mixed with each other, or the 8-epiloglycoside and the strychnine may be mixed with each other, and it is not possible to determine whether the compound sample is a monomer or a mixture, which affects the reliability of the pharmacodynamic test result.
Disclosure of Invention
The invention provides a liquid chromatography method for separating 8-epiloganin and loganin in order to overcome the defects of the prior art.
The technical scheme of the invention is as follows:
a liquid chromatography method for separating secoisolaricoside hemiacetal lactone and secoisolaricoside hemiacetal lactone comprises the following steps:
preparation of a mobile phase: accurately weighing a proper amount of D-cycloserine and blue copperas, dissolving with deionized water to prepare aqueous solutions of D-cycloserine and copper ion concentrations of 4mM and 1mM respectively, mixing the aqueous solutions with methanol and acetonitrile according to a volume ratio of 5.
Setting chromatographic parameters and analyzing sample injection: the chromatographic column is a C18 chromatographic column, the column temperature is set to be 30 ℃, the flow rate is 1.0mL/min, the detection wavelength is 240nm, the sample injection amount is 10 mu L, and the elution is carried out at the same degree by the mobile phase, and the sample injection and collection are carried out.
In a specific embodiment, the HPLC is an LC-20AT HPLC.
In a specific embodiment, the chromatography column is a Kromasil100-5C18 chromatography column.
In a specific embodiment, the column size is 250mm × 4.6mm,5 μm.
A liquid chromatography method for separating 8-epiloglycoside and loglycoside comprises the following steps:
preparation of a mobile phase: accurately weighing a proper amount of D-cycloserine and blue copperas, dissolving with deionized water to prepare aqueous solutions of D-cycloserine and copper ion concentrations of 4.5mM and 1.5mM respectively, mixing the aqueous solutions with methanol and acetonitrile according to a volume ratio of 5.
Setting chromatographic parameters and analyzing sample injection: the chromatographic column is a C18 chromatographic column, the column temperature is set to be 30 ℃, the flow rate is 1.0mL/min, the detection wavelength is 240nm, the sample injection amount is 10 mu L, and the elution is carried out at the same degree by the mobile phase, and the sample injection and collection are carried out.
In a specific embodiment, the HPLC is an LC-20AT HPLC.
In a specific embodiment, the chromatography column is a Kromasil100-5C18 chromatography column.
In a specific embodiment, the column size is 250mm × 4.6mm,5 μm.
The beneficial technical effects are as follows:
as known to those skilled in the art, chiral compounds often need to be separated by means of a chiral chromatographic column, but the chiral chromatographic column has high cost, short service life and poor repeatability as compared with a conventional C18 chromatographic column, and in this case, a chiral mobile phase analysis method based on the conventional C18 chromatographic column is not lost as an option, low cost and stable analysis performance. The invention realizes the chromatographic separation of secoisolaricoside hemiacetal lactone and 8-epiloglycoside and loglycoside by using a chiral mobile phase analysis method based on a conventional C18 chromatographic column, and the method can be used for detecting whether the compound samples are single products or mixed products.
Drawings
FIG. 1 is a chromatogram obtained by separating secoisolaricoside hemiacetal lactone from secoisolaricoside hemiacetal lactone, wherein the mobile phase is as follows: accurately weighing a proper amount of D-cycloserine and blue vitriod, dissolving with deionized water to prepare aqueous solutions of D-cycloserine and copper ion concentrations of 4mM and 1mM respectively, mixing the aqueous solutions with methanol and acetonitrile according to a volume ratio of 5; baseline separation of secoisolaricoside hemiacetal lactone from secoisolaricoside hemiacetal lactone under the chromatographic conditions is achieved;
FIG. 2 is a chromatogram obtained by separating secoisolaricoside hemiacetal lactone from secoisolaricoside hemiacetal lactone, with the mobile phase being: accurately weighing a proper amount of D-cycloserine, dissolving the D-cycloserine in deionized water to prepare an aqueous solution with the concentration of 4mM of D-cycloserine, mixing the aqueous solution with methanol and acetonitrile according to a volume ratio of 5; coelution semiacetal lactone and secoisolaricoside semiacetal lactone are co-eluted under the chromatographic conditions and cannot be separated;
FIG. 3 is a separation chromatogram of epiloglycoside hemiacetal lactone and secologlycoside hemiacetal lactone, and the mobile phase is: accurately weighing a proper amount of blue vitriol, dissolving with deionized water to prepare an aqueous solution with copper ion concentration of 1mM, mixing the aqueous solution with methanol and acetonitrile according to a volume ratio of 5; coelution semiacetal lactone and secoisolaricoside semiacetal lactone are co-eluted under the chromatographic conditions and cannot be separated;
FIG. 4 is a separation chromatogram of 8-epiloganin and loganin, and the mobile phase is: accurately weighing a proper amount of D-cycloserine and blue vitriod, dissolving the D-cycloserine and the blue vitriod by deionized water to prepare aqueous solutions with the concentrations of D-cycloserine and copper ions of 4.5mM and 1.5mM respectively, mixing the aqueous solutions with methanol and acetonitrile according to a volume ratio of 5; 8-epiloglycoside is separated from loglycoside at baseline under the chromatographic conditions;
FIG. 5 is a chromatogram for separating loganin from loganin, wherein the mobile phase is: accurately weighing a proper amount of D-cycloserine, dissolving the D-cycloserine with deionized water to prepare an aqueous solution with the concentration of the D-cycloserine of 4.5mM, mixing the aqueous solution with methanol and acetonitrile according to a volume ratio of 5; co-eluting 8-epiloganin and loganin under the chromatographic condition, and separating;
FIG. 6 is a chromatogram for separating loganin from loganin, wherein the mobile phase is: firstly, precisely weighing a proper amount of blue vitriol, dissolving the blue vitriol with deionized water to prepare an aqueous solution with copper ion concentration of 1.5mM, mixing the aqueous solution with methanol and acetonitrile according to a volume ratio of 5; the 8-epiloganin and the loganin are eluted together under the chromatographic conditions and cannot be separated.
Detailed Description
The following detailed description of the invention refers to the accompanying drawings, which are included to provide a further understanding of the invention, and are incorporated by reference into the accompanying drawings.
Example 1: separation of epiloganin hemiacetal lactone and secologanin hemiacetal lactone
1. Materials and methods
(1) Preparation of independent reference substance solution: firstly, precisely weighing a proper amount of secoisolaricoside hemiacetal lactone (the purity is more than or equal to 98 percent, the same below) or a proper amount of secoisolaricoside hemiacetal lactone (the purity is more than or equal to 98 percent, the same below) standard substance, and dissolving the mixture by using a water-methanol-acetonitrile mixed solvent with the volume ratio of 5;
(2) Preparing a mixed reference substance solution: firstly, precisely weighing a proper amount of secoisolaricoside hemiacetal lactone and a proper amount of secoisolaricoside hemiacetal lactone standard substance, and then dissolving the two standard substances by using a water-methanol-acetonitrile mixed solvent with the volume ratio of 5;
(3) Preparation of a mobile phase: precisely weighing a proper amount of D-cycloserine (the purity is more than or equal to 98 percent, the same below) and blue vitriol (the purity is more than or equal to 99 percent, the same below), dissolving with deionized water to prepare aqueous solution of D-cycloserine and copper ion concentration of 4mM and 1mM respectively, mixing the aqueous solution with methanol and acetonitrile according to a volume ratio of 5;
(4) Preparation of comparative mobile phase 1: accurately weighing a proper amount of D-cycloserine, dissolving the D-cycloserine with deionized water to prepare an aqueous solution with the concentration of 4mM of D-cycloserine, mixing the aqueous solution with methanol and acetonitrile according to a volume ratio of 5;
(5) Preparation of comparative mobile phase 2: accurately weighing a proper amount of blue vitriol, dissolving with deionized water to prepare an aqueous solution with copper ion concentration of 1mM, mixing the aqueous solution with methanol and acetonitrile according to a volume ratio of 5;
(6) Setting chromatographic parameters and analyzing sample injection:
the HPLC is LC-20AT HPLC, the chromatography column is Kromasil100-5C18 chromatography column (250 mm × 4.6mm,5 μm), the column temperature is set AT 30 deg.C, the flow rate is 1.0mL/min, the detection wavelength is 240nm, the sample injection amount is 10 μ L, and the mobile phases prepared in the above (3), (4) and (5) are eluted AT equal time, and sample injection and collection are carried out.
2. Analysis results
Fig. 1, fig. 2, and fig. 3 are chromatograms of the independent control solution and/or the mixed control solution, respectively, through the mobile phase separation prepared in (3), (4), and (5), and it can be seen that the secoisolaricoside hemiacetal lactone and the secoisolaricoside hemiacetal lactone can be effectively separated only when D-cycloserine and copper ions are used as a common chiral additive, which may be a result of differentiating the difference of acting forces of the secoisolaricoside hemiacetal lactone and the secoisolaricoside hemiacetal lactone after the D-cycloserine and the copper ions form a complex.
Example 2: 8-Epilonux vomica glycoside and nux vomica glycoside separation
1. Materials and methods
(1) Preparation of independent reference substance solution: accurately weighing a proper amount of 8-epiloglycoside (the purity is more than or equal to 98 percent and the same below) or loglycoside (the purity is more than or equal to 98 percent and the same below) standard substance, and dissolving the standard substance by using a water-methanol-acetonitrile mixed solvent with the volume ratio of 5;
(2) Preparing a mixed reference substance solution: accurately weighing a proper amount of 8-epiloglycoside and loglycoside standard substances, and dissolving by using a water-methanol-acetonitrile mixed solvent with a volume ratio of 5;
(3) Preparation of a mobile phase: precisely weighing a proper amount of D-cycloserine (the purity is more than or equal to 98 percent, the same below) and blue vitriol (the purity is more than or equal to 99 percent, the same below), dissolving with deionized water to prepare aqueous solution of D-cycloserine and copper ion concentration of 4.5mM and 1.5mM respectively, mixing the aqueous solution with methanol and acetonitrile according to a volume ratio of 5;
(4) Preparation of comparative mobile phase 1: accurately weighing a proper amount of D-cycloserine, dissolving the D-cycloserine with deionized water to prepare an aqueous solution with the concentration of the D-cycloserine being 4.5mM, mixing the aqueous solution with methanol and acetonitrile according to a volume ratio of 5;
(5) Formulation of comparative mobile phase 2: firstly, precisely weighing a proper amount of blue vitriol, dissolving the blue vitriol with deionized water to prepare an aqueous solution with copper ion concentration of 1.5mM, mixing the aqueous solution with methanol and acetonitrile according to a volume ratio of 5;
(6) Setting chromatographic parameters and analyzing sample injection:
the HPLC is LC-20AT HPLC, the column is Kromasil100-5C18 column (250 mm × 4.6mm,5 μm), the column temperature is set AT 30 deg.C, the flow rate is 1.0mL/min, the detection wavelength is 240nm, the sample injection amount is 10 μ L, and the mobile phases prepared in the above (3), (4) and (5) are eluted AT equal intervals, and the sample is injected and collected.
2. Analysis results
Fig. 4, fig. 5, and fig. 6 are chromatograms of the independent control solution and/or the mixed control solution, respectively, through the mobile phase separation prepared in (3), (4), and (5), and it can be seen that 8-epiloglycoside and loganin can be effectively separated only when D-cycloserine and copper ion are used as the common chiral additive, which may be the result of the difference of acting force of 8-epiloglycoside and loganin after D-cycloserine and copper ion form a complex.
As known to those skilled in the art, chiral compounds often need to be separated by means of a chiral chromatographic column, but the chiral chromatographic column has high cost, short service life and poor repeatability as compared with a conventional C18 chromatographic column, and in this case, a chiral mobile phase analysis method based on the conventional C18 chromatographic column is not lost as an option, low cost and stable analysis performance. The invention realizes the chromatographic separation of secoisolaricoside hemiacetal lactone and 8-epiloglycoside and loglycoside by using a chiral mobile phase analysis method based on a conventional C18 chromatographic column, and the method can be used for detecting whether the compound samples are single products or mixed products.
The above embodiments are intended to specifically describe the substance of the present invention, but those skilled in the art should understand that the scope of the present invention should not be limited to the above embodiments.
Claims (1)
1. A liquid chromatography method for separating 8-epiloglycoside and loglycoside is characterized by comprising the following steps and parameters:
preparation of a mobile phase: accurately weighing a proper amount of D-cycloserine and blue vitriod, dissolving the D-cycloserine and the blue vitriod by deionized water to prepare aqueous solutions with the concentrations of D-cycloserine and copper ions of 4.5mM and 1.5mM respectively, mixing the aqueous solutions with methanol and acetonitrile according to a volume ratio of 5;
setting chromatographic parameters and analyzing sample injection: the HPLC is LC-20AT HPLC, the column is Kromasil100-5C18 column, the specification is 250mm × 4.6mm,5 μm, the column temperature is set AT 30 deg.C, the flow rate is 1.0mL/min, the detection wavelength is 240nm, the sample injection amount is 10 μ L, and the mobile phase is used for isocratic elution, sample injection and collection.
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