CN114113409A - High performance liquid chromatography detection method for berberine intermediate - Google Patents
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- 238000001514 detection method Methods 0.000 title claims abstract description 32
- 229940093265 berberine Drugs 0.000 title claims abstract description 31
- QISXPYZVZJBNDM-UHFFFAOYSA-N berberine Natural products COc1ccc2C=C3N(Cc2c1OC)C=Cc4cc5OCOc5cc34 QISXPYZVZJBNDM-UHFFFAOYSA-N 0.000 title claims abstract description 31
- YBHILYKTIRIUTE-UHFFFAOYSA-N berberine Chemical compound C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 YBHILYKTIRIUTE-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000004128 high performance liquid chromatography Methods 0.000 title claims abstract description 25
- 239000012085 test solution Substances 0.000 claims abstract description 18
- RRIRDPSOCUCGBV-UHFFFAOYSA-N methylenedioxyphenethylamine Chemical compound NCCC1=CC=C2OCOC2=C1 RRIRDPSOCUCGBV-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000012088 reference solution Substances 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 8
- 238000010812 external standard method Methods 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000012086 standard solution Substances 0.000 claims description 10
- 238000010828 elution Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000003643 water by type Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 230000035945 sensitivity Effects 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 15
- 238000003908 quality control method Methods 0.000 description 3
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 241000224489 Amoeba Species 0.000 description 1
- 208000004429 Bacillary Dysentery Diseases 0.000 description 1
- VKJGBAJNNALVAV-UHFFFAOYSA-M Berberine chloride (TN) Chemical compound [Cl-].C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 VKJGBAJNNALVAV-UHFFFAOYSA-M 0.000 description 1
- 241001083847 Berberis Species 0.000 description 1
- 241001407408 Berberis fortunei Species 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 244000247747 Coptis groenlandica Species 0.000 description 1
- 235000002991 Coptis groenlandica Nutrition 0.000 description 1
- 208000005577 Gastroenteritis Diseases 0.000 description 1
- 206010017915 Gastroenteritis shigella Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000588653 Neisseria Species 0.000 description 1
- 206010057249 Phagocytosis Diseases 0.000 description 1
- 241000972672 Phellodendron Species 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- 206010039587 Scarlet Fever Diseases 0.000 description 1
- 241000607768 Shigella Species 0.000 description 1
- 241000607762 Shigella flexneri Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 206010001093 acute tonsillitis Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000003836 berberines Chemical group 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008782 phagocytosis Effects 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 208000008128 pulmonary tuberculosis Diseases 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 201000005113 shigellosis Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- G—PHYSICS
- G01—MEASURING; TESTING
- 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
- G01N30/02—Column chromatography
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention belongs to the field of medical intermediate detection, and particularly discloses a high performance liquid chromatography detection method of a berberine intermediate, wherein the intermediate is piperonylethylamine and has the chemical name of 3, 4-methylenedioxyphenylethylamine, the detection method comprises the steps of determining chromatographic conditions, preparing a test solution, preparing a reference solution, preparing a standard substance and calculating a standard curve; respectively and precisely measuring a test solution and a reference solution, injecting the test solution and the reference solution into a liquid chromatograph, recording a chromatogram, and calculating the content according to the peak area by an external standard method. The detection method disclosed by the invention has the advantages of good specificity, high sensitivity, high separation degree, durability, linearity and the like, and can meet the requirements.
Description
Technical Field
The invention belongs to the field of detection of medical intermediates, and particularly discloses a high performance liquid chromatography detection method of a berberine intermediate.
Background
Berberine, also known as berberine, is an important antibiotic, has antibacterial effects on hemolytic streptococcus, Staphylococcus aureus, gonococcus, Shigella flexneri and Shigella shigella, has phagocytosis enhancing effect on leucocytes, has inhibitory effects on tubercle bacillus and plague bacillus to different degrees, and has inhibitory effect on rat amoeba. The hydrochloride of berberine (commonly called berberine hydrochloride) has been widely used for treating gastroenteritis, bacillary dysentery, etc., and also has certain curative effect on pulmonary tuberculosis, scarlet fever, acute tonsillitis and respiratory tract infection. In traditional Chinese medicine, coptis, phellodendron, barberry root, Chinese mahonia and the like are commonly used as heat-clearing and detoxifying drugs, wherein the main effective component is berberine.
Piperonylethylamine, chemical name 3, 4-methylenedioxyphenethylamine, is a pharmaceutical intermediate, and the structural formula is shown in figure 1. 3, 4-methylenedioxyphenethylamine is a key intermediate in the berberine synthesis reaction process, the content of the 3, 4-methylenedioxyphenethylamine directly affects the content and yield of a berberine finished product, but a rapid detection method for the content of the berberine has not been reported in related documents.
High Performance Liquid Chromatography (HPLC) has been rapidly developed in the 70 th 20 th century to become a conventional high performance separation and analysis technique, which is one of the most widely used fields in various chromatographic modes at present, and about 80% of compounds can be separated and analyzed by HPLC in different modes. Since the 80 s, HPLC has become the fastest branch of the international analytical chemistry community and has been widely used in many disciplines.
Therefore, the research and development of a high performance liquid chromatography method for detecting the content of the 3, 4-methylenedioxyphenylethylamine is a new problem to be solved urgently, and has important significance on the production and quality control of berberine products.
Disclosure of Invention
Aiming at the situation, the invention discloses a high performance liquid chromatography detection method of a berberine intermediate, which has the characteristics of good specificity, high sensitivity, durability, linearity and the like which can meet the requirements, and is very suitable for controlling the quality of the content of the berberine key intermediate 3, 4-methylenedioxyphenylethylamine.
The technical scheme of the invention is as follows:
a high performance liquid chromatography detection method of a berberine intermediate comprises the following steps:
1) determination of chromatographic conditions:
a chromatographic column: c18;
a detector: an ultraviolet detector;
mobile phase: acetonitrile + sodium dodecyl sulfate water solution is used as a mobile phase;
the detection wavelength of the detector is 200-210 nm;
the volume ratio of acetonitrile to sodium dodecyl sulfate aqueous solution in the mobile phase is 50: 50;
the column temperature is 30-50 ℃;
the flow rate is 0.5-1.5 mL/min;
the sample injection volume is 5-15 uL;
and (3) an elution mode: eluting at equal concentration;
2) preparing a test solution;
3) preparation of control solutions:
4) the determination method comprises the following steps:
a. preparing a standard substance and calculating a standard curve;
b. respectively and precisely measuring a test solution and a reference solution, injecting the test solution and the reference solution into a liquid chromatograph, recording a chromatogram, and calculating the content according to the peak area by an external standard method;
preferably, the chromatographic column is SunFieTM C18250x4.6mm 5 μm.
Preferably, the ultraviolet detector is a Waters 2489 UV/ViS detector.
Preferably, the column temperature is 40 ℃.
Preferably, the flow rate is 1 mL/min.
Preferably, the sample injection volume is 10 uL.
Preferably, the standard solution is 0.02, 0.04, 0.06, 0.08, 0.1mg/mL of 3, 4-methylenedioxyphenylethylamine standard solution.
Preferably, the standard curve is Y =2 × 102X+233，R2=0.9966。
Preferably, the detection limit of the above method is 20. mu.g/mL.
Preferably, the method for detecting the berberine intermediate by high performance liquid chromatography is applied to preparing the berberine.
Compared with the prior art, the invention has the following beneficial effects:
the invention discloses a high performance liquid chromatography detection method of a berberine intermediate, which has the characteristics of good specificity, high sensitivity, durability, linearity and the like which can meet the requirements, and is very suitable for performing quality control on the content of a key berberine intermediate 3, 4-methylenedioxyphenylethylamine.
Drawings
FIG. 1 shows the structural formula of a berberine intermediate 3, 4-methylenedioxyphenethylamine.
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.
The reagents or instruments used in the examples of the present invention are not indicated by manufacturers, and are all conventional reagent products available from commercial sources.
Example 1
A high performance liquid chromatography detection method of a berberine intermediate comprises the following steps:
1) determination of chromatographic conditions:
a chromatographic column: c18;
a detector: an ultraviolet detector;
mobile phase: acetonitrile + sodium dodecyl sulfate water solution is used as a mobile phase;
the detection wavelength of the detector is 200 nm;
the volume ratio of acetonitrile to sodium dodecyl sulfate aqueous solution in the mobile phase is 50: 50;
the column temperature is 30 ℃;
the flow rate is 0.5 mL/min;
sample introduction volume is 5 uL;
and (3) an elution mode: eluting at equal concentration;
2) preparing a test solution;
3) preparation of control solutions:
4) the determination method comprises the following steps:
a. preparing a standard substance and calculating a standard curve;
b. respectively and precisely measuring a test solution and a reference solution, injecting the test solution and the reference solution into a liquid chromatograph, recording a chromatogram, and calculating the content according to the peak area by an external standard method.
The column was SunFieTM C18250x4.6mm 5 μm.
The ultraviolet detector is a Waters 2489 UV/Vis detector.
The standard solution is 0.02, 0.04, 0.06, 0.08 and 0.1mg/mL of 3, 4-methylenedioxyphenylethylamine standard solution.
The concentration of the sodium dodecyl sulfate aqueous solution is 0.01 mol/L.
Example 2
A high performance liquid chromatography detection method of a berberine intermediate comprises the following steps:
1) determination of chromatographic conditions:
a chromatographic column: c18;
a detector: an ultraviolet detector;
mobile phase: acetonitrile + sodium dodecyl sulfate water solution is used as a mobile phase;
the detection wavelength of the detector is 205 nm;
the volume ratio of acetonitrile to sodium dodecyl sulfate aqueous solution in the mobile phase is 50: 50;
the column temperature was 40 ℃;
the flow rate is 1 mL/min;
sample introduction volume is 10 uL;
and (3) an elution mode: eluting at equal concentration;
2) preparing a test solution;
3) preparation of control solutions:
4) the determination method comprises the following steps:
a. preparing a standard substance and calculating a standard curve;
b. respectively and precisely measuring a test solution and a reference solution, injecting the test solution and the reference solution into a liquid chromatograph, recording a chromatogram, and calculating the content according to the peak area by an external standard method.
The column was SunFieTM C18250x4.6mm 5 μm.
The ultraviolet detector is a Waters 2489 UV/Vis detector.
The standard solution is 0.02, 0.04, 0.06, 0.08 and 0.1mg/mL of 3, 4-methylenedioxyphenylethylamine standard solution.
The concentration of the sodium dodecyl sulfate aqueous solution is 0.02 mol/L.
Example 3
A high performance liquid chromatography detection method of a berberine intermediate comprises the following steps:
1) determination of chromatographic conditions:
a chromatographic column: c18;
a detector: an ultraviolet detector;
mobile phase: acetonitrile + sodium dodecyl sulfate water solution is used as a mobile phase;
the detection wavelength of the detector is 210 nm;
the volume ratio of acetonitrile to sodium dodecyl sulfate aqueous solution in the mobile phase is 50: 50;
the column temperature is 50 ℃;
the flow rate is 1.5 mL/min;
sample introduction volume is 15 uL;
and (3) an elution mode: eluting at equal concentration;
2) preparing a test solution;
3) preparation of control solutions:
4) the determination method comprises the following steps:
a. preparing a standard substance and calculating a standard curve;
b. respectively and precisely measuring a test solution and a reference solution, injecting the test solution and the reference solution into a liquid chromatograph, recording a chromatogram, and calculating the content according to the peak area by an external standard method.
The column was SunFieTM C18250x4.6mm 5 μm.
The ultraviolet detector is a Waters 2489 UV/Vis detector.
The standard solution is 0.02, 0.04, 0.06, 0.08 and 0.1mg/mL of 3, 4-methylenedioxyphenylethylamine standard solution.
The concentration of the sodium dodecyl sulfate aqueous solution is 0.03 mol/L.
Test example
From the above examples 1-3, it can be determined that the optimum chromatographic conditions are as follows:
a chromatographic column: SunFeire C18250x4.6mm 5 μm;
a detector: waters 2489 UV/Vis detector;
mobile phase: acetonitrile + sodium dodecyl sulfate aqueous solution (0.02 mol) is adopted as a mobile phase;
the detection wavelength of the detector is 205 nm;
the volume ratio of acetonitrile to sodium dodecyl sulfate aqueous solution in the mobile phase is 50: 50;
the column temperature was 40 ℃;
the flow rate is 1.0 mL/min;
sample introduction volume is 10 uL;
and (3) an elution mode: and (4) eluting at equal concentration.
By using the chromatographic condition and actual test, the detection limit is as low as 20 mug/mL, so that the method has the characteristics of good specificity, high sensitivity, durability, linearity and the like which can meet the requirements, and is very suitable for quality control of the content of the key berberine intermediate 3, 4-methylenedioxyphenylethylamine.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should integrate the description, and the embodiments may be combined as appropriate to form other embodiments understood by those skilled in the art.
Claims (10)
1. A high performance liquid chromatography detection method of a berberine intermediate is characterized by comprising the following steps:
1) determination of chromatographic conditions:
a chromatographic column: c18;
a detector: an ultraviolet detector;
mobile phase: acetonitrile + sodium dodecyl sulfate water solution is used as a mobile phase;
the detection wavelength of the detector is 200-210 nm;
the volume ratio of acetonitrile to sodium dodecyl sulfate aqueous solution in the mobile phase is 50: 50;
the column temperature is 30-50 ℃;
the flow rate is 0.5-1.5 mL/min;
the sample injection volume is 5-15 uL;
and (3) an elution mode: eluting at equal concentration;
2) preparing a test solution;
3) preparation of control solutions:
4) the determination method comprises the following steps:
a. preparing a standard substance and calculating a standard curve;
b. respectively and precisely measuring a test solution and a reference solution, injecting the test solution and the reference solution into a liquid chromatograph, recording a chromatogram, and calculating the content according to the peak area by an external standard method.
2. The method for detecting the berberine intermediate by high performance liquid chromatography as claimed in claim 1, wherein the chromatographic column is SunFieTM C18250x4.6mm 5 μm.
3. The HPLC detection method of a berberine intermediate as claimed in claim 1, wherein said UV detector is a Waters 2489 UV/Vis detector.
4. The high performance liquid chromatography detection method of a berberine intermediate according to claim 1,
the column temperature was 40 ℃.
5. The HPLC detection method of a berberine intermediate as claimed in claim 1, wherein said flow rate is 1 mL/min.
6. The HPLC detection method of claim 1, wherein the sample injection volume is 10 uL.
7. The HPLC detection method of claim 1, wherein the standard solution is 0.02, 0.04, 0.06, 0.08, 0.1mg/mL of 3, 4-methylenedioxyphenylethylamine standard solution.
8. The HPLC detection method of claim 1, wherein the standard curve is Y = 2X 102X+233，R2=0.9966。
9. The HPLC detection method of claim 1, wherein the detection limit is 20 μ g/mL.
10. Use of the method for detecting berberine intermediate according to any one of claims 1-9 by high performance liquid chromatography in the preparation of berberine.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114839294A (en) * | 2022-05-06 | 2022-08-02 | 宿迁市振兴化工有限公司 | Method for measuring content of hindered amine light stabilizer intermediate |
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|---|---|---|---|---|
| CN1396160A (en) * | 2002-07-24 | 2003-02-12 | 广州市众为生物技术有限公司 | Process for preparing N-methyl piperethanamine salt |
| CN109001342A (en) * | 2018-09-30 | 2018-12-14 | 东北制药集团股份有限公司 | A kind of efficient liquid phase method detecting N-2,3- veratryl homopiperony lamine and its salt content |
| CN114544798A (en) * | 2022-01-05 | 2022-05-27 | 湖南恒生制药股份有限公司 | Method for detecting dopamine hydrochloride intermediate 1, 3-benzodioxole |
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2021
- 2021-12-06 CN CN202111529931.7A patent/CN114113409A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1396160A (en) * | 2002-07-24 | 2003-02-12 | 广州市众为生物技术有限公司 | Process for preparing N-methyl piperethanamine salt |
| CN109001342A (en) * | 2018-09-30 | 2018-12-14 | 东北制药集团股份有限公司 | A kind of efficient liquid phase method detecting N-2,3- veratryl homopiperony lamine and its salt content |
| CN114544798A (en) * | 2022-01-05 | 2022-05-27 | 湖南恒生制药股份有限公司 | Method for detecting dopamine hydrochloride intermediate 1, 3-benzodioxole |
Non-Patent Citations (1)
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