CN113358808A - Method for qualitatively identifying polar compounds by using reversed-phase chromatographic retention index - Google Patents
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- 238000000034 method Methods 0.000 title claims abstract description 35
- 238000013178 mathematical model Methods 0.000 claims abstract description 15
- 238000004366 reverse phase liquid chromatography Methods 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 9
- 238000004007 reversed phase HPLC Methods 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000004458 analytical method Methods 0.000 claims description 8
- 238000004090 dissolution Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
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- 230000005526 G1 to G0 transition Effects 0.000 claims description 4
- 230000001419 dependent effect Effects 0.000 claims description 4
- 238000012417 linear regression Methods 0.000 claims description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 235000010288 sodium nitrite Nutrition 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims 1
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 238000004364 calculation method Methods 0.000 description 12
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- 229930003935 flavonoid Natural products 0.000 description 8
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- 238000002790 cross-validation Methods 0.000 description 6
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- 238000001514 detection method Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000003775 Density Functional Theory Methods 0.000 description 2
- 238000013051 Liquid chromatography–high-resolution mass spectrometry Methods 0.000 description 2
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- 238000010276 construction Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
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- 229930014626 natural product Natural products 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 238000005220 pharmaceutical analysis Methods 0.000 description 1
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- 238000001228 spectrum Methods 0.000 description 1
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- 238000004809 thin layer chromatography Methods 0.000 description 1
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- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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- G—PHYSICS
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
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Abstract
本发明公开了一种利用反相色谱保留指数对极性化合物辅助定性鉴别的方法，包括：将亚硝酸钠，配制成10μg/ml的溶液，进行反相高效液相色谱分析，测定不同配比流动相中出峰时间t0；将15种具有类似化学结构的化合物标准品，配制成10μg/ml的溶液，进行反相高效液相色谱分析，测定不同配比流动相中的保留时间tR；计算上述15种化合物的容量因子k′；计算上述15种化合物的色谱保留值参数c；计算上述15种化合物的分子描述符VM、EB、XB；构建上述15种化合物的QSRR数学模型；QSRR数学模型的验证；以QSRR数学模型对极性化合物定性。The invention discloses a method for assisting qualitative identification of polar compounds by using reversed-phase chromatography retention index. The peak appearance time t 0 in the mobile phase; 15 kinds of standard compounds with similar chemical structures were prepared into a solution of 10 μg/ml, and analyzed by reversed-phase high performance liquid chromatography to determine the retention time t R in the mobile phase with different ratios ; Calculate the capacity factor k' of the above-mentioned 15 kinds of compounds; Calculate the chromatographic retention value parameter c of the above-mentioned 15 kinds of compounds; Calculate the molecular descriptors VM, E B and X B of the above - mentioned 15 kinds of compounds; Construct the QSRR mathematics of the above-mentioned 15 kinds of compounds Model; Validation of QSRR mathematical model; Qualification of polar compounds with QSRR mathematical model.
Description
Technical Field
The invention relates to the technical field of pharmaceutical analysis, in particular to a method for qualitatively identifying a polar compound by using a reversed-phase chromatographic retention index.
Background
The existing compound characterization method mainly comprises the following steps: a spectrum analysis method, an ultraviolet spectrum method, a thin layer chromatography, a high performance liquid chromatography, an ultra high performance liquid chromatography-mass spectrometry, a UHPLC-MS combined database method, a UHPLC-MS combined mass spectrum cracking rule method and the like. The spectrum analysis method is a gold standard for identifying unknown compounds, but the method requires obtaining the pure products of the unknown compounds, and has the disadvantages of complicated extraction, separation and purification processes, long period and high cost; ultraviolet spectroscopy, poor specificity; the thin layer method has low sensitivity and low separation efficiency; high performance liquid chromatography and ultra high performance liquid chromatography, although improving the identification sensitivity, specificity and analysis speed of polar compounds, require the use of standard substances and are prone to false positive due to the existence of overlapping peaks. Due to the characteristics of high sensitivity, high selectivity and high flux, the continuous perfection of a mass spectrum database and the clear mass spectrum cracking rule, the liquid chromatography-mass spectrometry technology, especially the ultra-high performance liquid chromatography-high resolution mass spectrometry technology, provides an effective analysis means for the qualitative analysis of polar natural products. An ultra-high performance liquid chromatography high-resolution mass spectrometry combined technology (UHPLC-HRMS) is a modern analysis technology integrating the high separation effect of chromatography and the accurate and sensitive qualitative and quantitative analysis capability of mass spectrometry. This technique has several major irreplaceable advantages: high efficiency and high separation speed; the sensitivity is high, and the detection of trace compounds can be dealt with; high separation degree, and can simplify complex components; high selectivity, and can obtain accurate molecular weight and molecular formula of the compound to be detected; high information acquisition speed and can realize high-flux qualitative analysis of multiple components. By means of the high resolution capability and isotope peak shape distribution determination capability of the high resolution mass spectrum, accurate qualitative and unknown substance screening is carried out through full scanning, and then the compound is further confirmed through a secondary mass spectrum combined with a spectrum library retrieval, ion fragment analysis and the like, so that accurate identification and analysis of complex matrix multi-component are realized.
However, when UHPLC-HRMS technology is combined with a database to rapidly identify chemical components of a traditional Chinese medicine, problems mainly arise, namely, a problem that a compound loaded in the database is not complete and matching rates are different even if the compound is loaded, and a problem that an extracted chromatogram with the same mass-to-charge ratio has a plurality of chromatographic peaks, that is, isomers composed of the same elements, and when a database is used for matching, the plurality of chromatographic peaks are often matched with the same compound. A research paper on the correlation of retention indices and connectivity indices of alcohols and methyl esters with complex cyclic structures, Kaliszan r, opened the direction of research using quantitative relationships between descriptors of molecular structures of compounds to be analyzed and chromatographic retention behavior, i.e., now referred to as the chromatographic Quantitative Structure Retention Relationship (QSRR) method. With the development of quantum computational chemistry, chromatographic techniques and statistics, QSRR methods have been widely used in a variety of scientific fields, such as predicting retention time of compounds, identifying unknown compounds, studying chromatographic separation mechanisms under given conditions, quantitatively comparing separation performance of various chromatographic columns, evaluating lipophilicity and dissociation constants of analytes, evaluating biological activity of drugs and characteristics of chemical materials.
However, when a mathematical model between the analyte retention parameter and the molecular description is constructed, the problems of using a large number of molecular descriptors, or using semi-empirical molecular descriptors, and not sufficiently considering the reproducibility of the retention parameter determination also exist, so that the method still has a large gap from practical application.
Therefore, how to use the chromatographic retention value of an analyte, the accurate molecular weight of a mass spectrum, the element composition and chemical formula information of the mass spectrum, the secondary mass spectrum fragment of a high-resolution mass spectrum and the structural information provided by a compound database provided by the UHPLC-HRMS technology, obtain as few molecular descriptors with physical significance as possible and as few standards as possible through quantum chemical calculation, construct a transformable mathematical model based on the quantitative molecular structure descriptors and the chromatographic retention parameters, and identify polar compound isomers and unknown compounds are problems that need to be solved urgently by those skilled in the art.
Disclosure of Invention
In view of the above, the present invention provides a method for qualitative identification of polar compounds using reversed phase chromatography retention index.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for qualitative identification of polar compounds using reversed phase chromatographic retention index comprising the steps of:
1) preparing sodium nitrite into 10 mu g/ml solution, carrying out reversed phase high performance liquid chromatography analysis, and measuring the peak emergence time t in mobile phases with different proportions0。
2) Preparing 15 compound standards with similar chemical structures into 10 mu g/ml solution, performing reversed phase high performance liquid chromatography, and measuring retention time t in mobile phases with different ratiosR；
3) Calculating the capacity factor k' of the 15 compounds;
4) calculating the chromatographic retention parameter c of the 15 compounds;
5) calculating the molecular descriptors V of the above 15 compoundsM、EB、XB；
6) Building QSRR mathematical models of the 15 compounds;
7) verifying a QSRR mathematical model;
8) the polar compounds were characterized by QSRR mathematical models.
The method adopts an isocratic elution mode to determine the volume factor k' and the chromatographic retention value parameter c of the modeling compound and the compound to be identified under different proportions of mobile phases (methanol: water or acetonitrile: water), has simple and convenient operation, obtains comprehensive information, and can verify whether the logarithm of the volume factor of the compound is in a linear relation with the concentration of a strong solvent of the mobile phase.
As a preferred technical solution of the present invention, in step 1) and step 2), the mobile phase with different mixture ratios is methanol to water, wherein the ratio of methanol to water is 90:10, 80:20, 70:30, 60:40, 50:50, 40:60, 30:70, 20:80 and 10: 90; or acetonitrile, water 90:10, 80:20, 70:30, 60:40, 50:50, 40:60, 30:70, 20:80, and 10: 90.
As a preferred technical scheme of the invention, in the step 2), the stationary phase is C18The column is filled with octadecylsilane chemically bonded silica, the particle size is 1.7-5 μm, the column length is 100-250mm, and the column diameter is 3-4.6 mm.
As a preferable technical scheme of the invention, in the step 2), the concentration of the standard substance is 1-10 mu g/ml of water or alcohol solution.
As a preferred embodiment of the present invention, in step 3), k ═ (t) according to the formulaR-t0) And/t 0, calculating the capacity factor k' of the 15 compounds in the mobile phase with different proportions.
As a preferred embodiment of the present invention, in step 4), the chromatographic retention parameter c of 15 compounds in different proportions of mobile phase is calculated according to the formula ln (k') ═ a + c × CB.
As a preferable technical scheme of the invention, in the step 5), 15 compounds are structurally optimized by using quantum chemical calculation software, and the molecular volume V of each compound is calculated on the basis of the optimized structure with the lowest energyMFree energy of dissolution in a strong solvent EBAnd hydrogen bonding energy XB。
As a preferred technical scheme of the invention, in the step 6), the chromatographic retention value parameter c is taken as a dependent variable, and V isMAnd EB and XB are independent variables to perform multiple linear regression, and a qualitative identification QSRR mathematical model of the compound is constructed.
As a preferred technical scheme of the invention, in the step 7), 3 to 5 compounds of the same type are taken, and the steps 1) to 6) are repeated to obtain VM、EB、XBSubstituting the value into a QSRR mathematical model to obtain a theoretical chromatogram retention value c value; and comparing the calculated value with a c value obtained by a high performance liquid chromatography-high resolution mass spectrometry combined technology, calculating whether the relative error is less than 10%, and verifying the feasibility of the model.
As a preferable technical scheme, in the step 8), the compound is additionally taken, the retention value c value of the theoretical chromatogram is calculated, a c value library is established, and the aim of auxiliary identification of the compound based on the reversed-phase high performance liquid chromatography is fulfilled.
In conclusion, the invention uses a small amount of standard products of the same kind of compounds to construct a mathematical model, can realize the auxiliary qualitative analysis of the compounds, has simple and convenient method and high accuracy, and is particularly suitable for determining the compounds as a certain kind of compounds by a liquid chromatography-mass spectrometry technology, but is difficult to determine the compounds as the specific compounds for the auxiliary qualitative identification analysis.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1 construction of reverse phase chromatography QSRR model for benzene and benzene ring substituents
(I) obtaining the experimental value of the quantitative parameter c
Using a C18 chromatographic column as a stationary phase, methanol-water (A: B) as a mobile phase, under the conditions of A: B of 70:30, 60:40, 50:50 and 40:60 isocratic respectively, using 240nm as a detection wavelength, injecting 10 mu l of benzene and methanol solution (20 shown in table 1) of benzene ring substitutes with the concentration of 5 mu g/ml, carrying out chromatographic analysis to obtain the retention time and the adjustment retention time of each compound under different mobile phase elution conditions, and obtaining the retention time according to the formula lnk ═ a + C C ═ C-BAnd calculating to obtain quantitative parameter c value experimental values of the benzene and the benzene ring substituent, which are shown in table 1.
Calculation of the (two) molecular descriptors
Calculating the single-point energy E of benzene and its homologous compounds by adopting the density functional theory (DFT-B3lyp 6-31G) calculation method in quantum chemical software0Calculating the volume V for the optimized gaseous resultsM. By using (m)062 x-6-31G) calculation method, the energy calculation of a recessive solvent model is carried out on the optimized result, and the single-point energy E of solute dissolved in methanol is obtainedB0Calculating the free energy of dissolution EBCalculation of intermolecular Hydrogen bonding energy X according to literature methodsB. The results are shown in Table 1. According to c ═ m + nESolution-x V+y XAHWith molecular descriptors (E)Solution，V，XAH) The experimental c value is a dependent variable, and multiple linear regression is carried out to obtain a regression method with the equation c being-0.723296 +0.0676ESolution-0.0426V+0.0839XAHAccording to the equation, the calculated c value and the absolute value of the experiment c are obtainedThe results of the error and the relative error are shown in the table 1, which shows that the method can be used for identifying benzene and benzene ring substitutes.
TABLE 1 retention parameter c of benzene and its homologues in methanol and results of molecular descriptor calculation
(III) building QSRR model of quantitative parameter c value and cross validation
The molecular volume V of the obtained benzene and benzene ring substituentMFree energy of dissolution EBAnd intermolecular hydrogen bonding energy XBAnd correlating with the value of the chromatographic retention value parameter c to obtain a QSRR model of the parameter c.
The QSRR model with the constructed quantitative parameter c value is verified, the QSRR model with the constructed quantitative parameter c value is constructed after two compounds are cancelled each time, and the quantitative relation of the QSRR model in a methanol solution is shown in a table 2. The QSRR model cross validation error values of benzene and benzene substitutes in methanol are both less than 12%.
TABLE 2 QSRR model of benzene and benzene ring substituents in methanol and cross-validation results
Example 2 construction of reverse phase chromatography QSRR model for flavonoids
(I) obtaining the experimental value of the quantitative parameter c
Using C18 chromatographic column as stationary phase, methanol-water (A: B) as mobile phase, under the conditions of A: B of 70:30, 60:40, 50:50, 40:60 isocratic respectively, using 254nm as detection wavelength, injecting 10 μ l of methanol solution (16 shown in Table 3) of flavonoid compound control with concentration of 5 μ g/ml, and performing chromatographic analysis to obtain retention time and elution condition of each compound under different mobile phasesAdjusting the retention time according to the formula lnk ═ a + C ═ CBAnd calculating to obtain quantitative parameter c value experimental values of the benzene and the benzene ring substituent, which are shown in table 3.
Calculation of the (two) molecular descriptors
Calculating single-point energy E of the flavonoid compound by adopting a density functional theory (DFT-B3lyp 6-31G) calculation method in quantum chemistry software0Calculating the volume V for the optimized gaseous resultsM. By using (m)062 x-6-31G) calculation method, the energy calculation of a recessive solvent model is carried out on the optimized result, and the single-point energy E of solute dissolved in methanol is obtainedB0Calculating the free energy of dissolution EBCalculation of intermolecular Hydrogen bonding energy X according to literature methodsB. As shown in table 3. According to c ═ m + nESolution-x V+y XAHWith molecular descriptors (E)Solution，V，XAH) The independent variable and the dependent variable are used as experimental c values, and multiple linear regression is carried out to obtain a regression method with the equation c being-5.12784 +0.19ESolution-0.0054V+0.0358XAHThe calculated c value and the absolute error and the relative error of the calculated c value and the experiment c are obtained according to the equation, and the result is shown in table 3, which indicates that the method can be used for identifying the flavonoid compounds.
TABLE 3 Retention value parameter c value and molecular descriptor calculation results of flavonoids in methanol
(III) building QSRR model of quantitative parameter c value and cross validation
The molecular volume V of the obtained flavonoid compoundMFree energy of dissolution EBAnd intermolecular hydrogen bonding energy XBAnd correlating with the value of the chromatographic retention value parameter c to obtain a QSRR model of the parameter c.
The QSRR model with the constructed quantitative parameter c value is verified in the research, the QSRR model is constructed after 1 compound is cancelled each time, and the quantitative relation of the QSRR model in the methanol solution is shown in a table 4. The QSRR model cross validation error values of the flavonoids compounds in methanol are all less than 7%.
TABLE 4 QSRR model of flavonoids in methanol and cross-validation results
The embodiments in the present description are described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
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| CN114280199A (en) * | 2021-12-30 | 2022-04-05 | 中国计量科学研究院 | Transplantation of Retention Index for Reversed-Phase Liquid Chromatography |
| CN114724637A (en) * | 2022-03-09 | 2022-07-08 | 华南理工大学 | Method for determining vinyl ether ozonization monomolecular reaction product based on high-level quantum chemical calculation method combined with experiment |
| CN115963207A (en) * | 2023-01-10 | 2023-04-14 | 佳木斯大学 | Reversed phase chromatography qualitative identification method by utilizing dissolving energy of polar compound |
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