CN105949252A - Preparation method of three chemical reference substances chebulinic acid, chebuligic acid and ellagic acid in terminalia chebula medicine - Google Patents
Preparation method of three chemical reference substances chebulinic acid, chebuligic acid and ellagic acid in terminalia chebula medicine Download PDFInfo
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- CN105949252A CN105949252A CN201610063688.7A CN201610063688A CN105949252A CN 105949252 A CN105949252 A CN 105949252A CN 201610063688 A CN201610063688 A CN 201610063688A CN 105949252 A CN105949252 A CN 105949252A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/06—Peri-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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Abstract
The invention relates to a preparation method of three chemical reference substances, chebulinic acid, chebuligic acid and ellagic acid, in terminalia chebula medicine. The method includes the following steps: 1) crushing dried fruits of terminalia chebula and performing ultrasonic extraction to obtain an extract liquid, and performing pressure-reduced concentration and drying to the extract liquid to obtain a crude extract dried powder; 2) with n-hexane/ethyl acetate/methanol/water as a solvent system, separating the crude extract through HSCCC to respectively obtain the chebulinic acid, the chebuligic acid and the ellagic acid, wherein the purities of the chebulinic acid, the chebuligic acid and the ellagic acid are all more than 95% through purity detection by means of high-performance liquid chromatography (HPLC). The method is simple and quick.
Description
Technical field
The present invention relates to the preparation method of a kind of chemical reference substance, particularly relate to chebulinic acid in Fructus Chebulae's medical material,
Chebulagic acid and the preparation method of three kinds of chemical reference substances of ellagic acid.
Background technology
Fructus Chebulae (Terminalia chebula Retz.) is Combretum Racemosum plant, is the main source of Fructus Chebulae's medical material,
Main chemical compositions is Polyphenols, galloyl glucose class, triterpene acids etc., has stronger antioxygen
The multiple actions such as change, anti-inflammation, anticancer, antiallergic, suppression alpha-glucosidase activity, modern pharmacology
Research proves that Polyphenols is main active.But, it is currently used for Fructus Chebulae's medical material and products thereof quality control
The chemical composition of system is gallic acid, is not enough to reflect the quality of Fructus Chebulae comprehensively.Therefore, multiple types is set up
The method of quality control of chemical composition is significant for the comprehensive development and utilization of Fructus Chebulae's medical material, and many
The shortage of phenols chemical reference substance seriously constrains the research of this respect.Especially, obtain high-purity simultaneously
Chebulinic acid, Chebulagic acid and three kinds of chemical reference substances of ellagic acid, have no relevant report.Chebulinic acid, scold
The structural formula of Li Le acid and three kinds of chemical reference substances of ellagic acid is as follows:
High speed adverse current chromatogram (High Speed Counter Current Chromatography, HSCCC) is
The one invented the eighties in last century by Yoichiro doctor Ito of NIH (NIH)
New chromatographic separating and purifying technology based on liquid liquid distribution mechanism, it is not necessary to fixing phase made by solid, does not exist solid
Body to the absorption of sample component, stain, degeneration, inactivate, the phenomenon such as hangover, the highest recovery can be realized
Rate, demonstrates powerful advantage, very in terms of the separation of active ingredient of natural product, purification, preparation
Being suitable for the preparation of chemical reference substance, HSCCC has become an indispensable hands of Tibetan medicine modernization in realization
Section.
Summary of the invention
The technical problem to be solved be to provide chebulinic acid in a kind of simple, fast Fructus Chebulae's medical material,
Chebulagic acid and the preparation method of three kinds of chemical reference substances of ellagic acid.
For solving the problems referred to above, chebulinic acid, Chebulagic acid and ellagic acid in Fructus Chebulae's medical material of the present invention
The preparation method of three kinds of chemical reference substances, comprises the following steps:
(1) extract: after Fructus Chebulae's medicinal material drying fruit is crushed to 40～200 mesh, with 1g:5mL～30mL
Ratio volumetric concentration be 10～95% ethanol under 200～400W, carry out supersound extraction, extraction time
It is 1～3 time, each 30～60min, merge and obtain extracting solution；Described extracting solution is dried through concentrating under reduced pressure
Obtain crude extract dried powder；；
(2) isolated and purified: with n-hexane-ethyl acetate-methanol-water as solvent system, lower as stream
Dynamic phase, is dissolved in the crude extract of described target component in lower phase solution, and injects high-speed counter-current chromatograph and enter
Row separates, and when flowing out chromatographic column mutually wait flowing, collects separator according to chromatographic peak；This separator warp successively
Concentrate, be dried to constant weight, respectively obtain chebulinic acid, Chebulagic acid and ellagic acid；
Further, in described step (1), Fructus Chebulae's medicinal material drying fruit refers to Combretum Racemosum plant Fructus Chebulae
The dry fruit of (Terminalia chebula Retz.).
Further, the normal hexane in described step (2) solvent system, ethyl acetate, methanol, the body of water
Long-pending ratio is 0.5～1.5:5～9:0.3～0.7:1～5.
Further, the separation condition of described step (2) high speed counter-current chromatograph (HSCCC) is stream
Speed 0.5～3.5mL/min, engine speed 700～900rpm, separation temperature 15～35 DEG C, sample size is
50～200mg, the retention rate of fixing phase is 50～71%.
In order to confirm the chebulinic acid prepared by the present invention, Chebulagic acid and the purity of three kinds of chemicals of ellagic acid,
The monomer of described high-speed counter-current chromatograph isolated is utilized respectively high performance liquid chromatography detection purity；?
In purity detecting, high performance liquid chromatography (HPLC) testing conditions refers to use a length of 250mm, a diameter of
4.6mm and the C18 chromatographic column that packing material size is 5 μm, column temperature 25 DEG C, flowing is methanol-0.1% mutually
The mixed solvent of acetic acid, flow velocity is 1mL/min, and detection wavelength is 254nm；Gradient elution program: 0-60
Min, 10-70% methanol；60-70min, 70-90% methanol.Result shows prepared by the inventive method
Chebulinic acid, the purity of Chebulagic acid and three kinds of chemical reference substances of ellagic acid all (sees figure more than 95%
2～5).
In order to confirm chebulinic acid prepared by the present invention, Chebulagic acid and three kinds of chemical reference substance structures of ellagic acid,
Three kinds of chemical reference substances of described high-speed counter-current chromatograph isolated are tested respectively1H-NMR and13C-NMR。
The present invention compared with prior art has the advantage that
1, solvent for use safety non-toxic of the present invention, recoverable, production cost is low.
2, the present invention uses high speed adverse current chromatogram isolated and purified target compound from crude extract, it is not necessary to solid
Make fixing phase, do not exist solid to the absorption of sample component, stain, degeneration, inactivate, the phenomenon such as hangover,
The highest response rate can be realized, be very suitable for the preparation of chemical reference substance.
3, the present invention is simple, convenient, easily be automated control.
4, using the chebulinic acid that the inventive method obtains, Chebulagic acid and ellagic acid all pass through1H-NMR and13C-NMR identifies and meets this compound structure (seeing Fig. 1)；Meanwhile, HPLC is utilized to detect purity
All more than 95%, (see Fig. 2～5).
Accompanying drawing explanation
Fig. 1 is the HSCCC separating spectrum of chebulinic acid of the present invention, Chebulagic acid and ellagic acid；
Fig. 2 is that chebulinic acid HPLC analyzes collection of illustrative plates；
Fig. 3 is that Chebulagic acid HPLC analyzes collection of illustrative plates；
Fig. 4 is that ellagic acid HPLC analyzes collection of illustrative plates；
Fig. 5 is chebulinic acid 1H NMR spectra；
Fig. 6 is chebulinic acid 13C NMR spectra；
Fig. 7 is Chebulagic acid 1H NMR spectra；
Fig. 8 is Chebulagic acid 13C NMR spectra；
Fig. 9 is ellagic acid 1H NMR spectra；
Figure 10 is ellagic acid 13C NMR spectra.
Detailed description of the invention
Embodiment 1
Chebulinic acid, Chebulagic acid and the preparation method of three kinds of chemical reference substances of ellagic acid in Fructus Chebulae's medical material, bag
Include following steps:
(1) extract: after Fructus Chebulae's medicinal material drying fruit is crushed to 40 mesh, takes 500g, use mass concentration
Be 10% ethanol 2.5L under 200W, carry out supersound extraction, extraction time is 1 time, extraction time 30
Min, obtains extracting solution；Extracting solution is at 60 DEG C, and under the conditions of 0.04MPa, concentrating under reduced pressure is dried to obtain extract
Dried powder.
Wherein: Fructus Chebulae's medicinal material drying fruit refers to Combretum Racemosum plant Fructus Chebulae (Terminalia chebula Retz.)
Dry fruit.
(2) isolated and purified: isolated and purified: with n-hexane-ethyl acetate-methanol-water as solvent system, under
Mutually as flowing phase, the crude extract of described target component is dissolved in lower phase solution, and injects high-speed counter-current
Chromatograph separates, and when flowing out chromatographic column mutually wait flowing, collects separator according to chromatographic peak；This separation
Thing is the most concentrated, be dried to constant weight, respectively obtains 3.3mg chebulinic acid, 4.5mg Chebulagic acid and
2.3mg ellagic acid；
Wherein: the normal hexane in solvent system, ethyl acetate, methanol, the volume ratio (L/L) of water are
0.5:5:0.3:1.
The separation condition of high-speed counter-current chromatograph (HSCCC) refers to flow velocity 0.5mL/min, engine speed
700rpm, separation temperature 15 DEG C, sample size is 50mg, and the retention rate of fixing phase is 62%.
Chebulinic acid of the present invention, Chebulagic acid and the HSCCC separating spectrum of three kinds of compounds of ellagic acid
See Fig. 1.
Purity detecting: the monomer of high-speed counter-current chromatograph (HSCCC) isolated is utilized respectively efficiently
Liquid chromatograph (HPLC) detection purity, purity is all more than 95%.Wherein: high performance liquid chromatography (HPLC)
Testing conditions refers to use a length of 250mm, a diameter of 4.6mm and C that packing material size is 5 μm18
Chromatographic column, column temperature 25 DEG C, flowing is the mixed solvent of methanol-water mutually, and flow velocity is 1mL/min, detection
Wavelength is 280nm；Gradient elution program: 0min, 10% methanol；60min, 80% methanol.Fructus Chebulae
Acid, Fig. 2-4 is shown in by the purity analysis collection of illustrative plates of Chebulagic acid and three kinds of chemical reference substances of ellagic acid；
Structural Identification: the monomer of high-speed counter-current chromatograph (HSCCC) isolated is passed through respectively1H-NMR and13C-NMR identifies.Chebulinic acid, Chebulagic acid and three kinds of chemical reference of ellagic acid
1H NMR and the 13C NMR spectra of product are shown in Fig. 5-10.
Embodiment 2
Chebulinic acid, Chebulagic acid and the preparation method of three kinds of chemical reference substances of ellagic acid in Fructus Chebulae's medical material, bag
Include following steps:
(1) extract: after Fructus Chebulae's medicinal material drying fruit is crushed to 200 mesh, take 500g, dense by quality
Degree is that the ethanol 15L of 95% carries out supersound extraction under 400W, and extraction time is 3 times, extraction time
60min, obtains extracting solution；Extracting solution is at 60 DEG C, and under the conditions of 0.04MPa, concentrating under reduced pressure is dried to extract
Thing dried powder.
Wherein: Fructus Chebulae's medicinal material drying fruit refers to Combretum Racemosum plant Fructus Chebulae (Terminalia chebula Retz.)
Dry fruit.
(2) isolated and purified: isolated and purified: with n-hexane-ethyl acetate-methanol-water as solvent system, under
Mutually as flowing phase, the crude extract of described target component is dissolved in lower phase solution, and injects high-speed counter-current
Chromatograph separates, and when flowing out chromatographic column mutually wait flowing, collects separator according to chromatographic peak；This separation
Thing is the most concentrated, be dried to constant weight, respectively obtains 6.3mg chebulinic acid, 9.7mg Chebulagic acid and
5.0mg ellagic acid；
Wherein: the normal hexane in solvent system, ethyl acetate, methanol, the volume ratio (L/L) of water are
1.5:9:0.7:5.The separation condition of high-speed counter-current chromatograph (HSCCC) refers to flow velocity 3.5mL/min,
Engine speed 900rpm, separation temperature 35 DEG C, sample size is 100mg, and the retention rate of fixing phase is
54%.
The monomer of high-speed counter-current chromatograph (HSCCC) isolated is utilized respectively high performance liquid chromatography
(HPLC) detection purity, purity is all more than 95%.
Wherein: high performance liquid chromatography (HPLC) testing conditions is with embodiment 1.
The monomer of high-speed counter-current chromatograph (HSCCC) isolated is passed through respectively1H-NMR and13C-NMR identifies.
Embodiment 3
Chebulinic acid, Chebulagic acid and the preparation method of three kinds of chemical reference substances of ellagic acid in Fructus Chebulae's medical material, bag
Include following steps:
(1) extract: after Fructus Chebulae's medicinal material drying fruit is crushed to 80 mesh, takes 500g, use mass concentration
Be 70% ethanol 5L under 350W, carry out supersound extraction, extraction time is 3 times, extraction time 40min,
Obtain extracting solution；Extracting solution is at 60 DEG C, and under the conditions of 0.04MPa, concentrating under reduced pressure is dried to obtain extract xeraphium
End.
Wherein: Fructus Chebulae's medicinal material drying fruit refers to Combretum Racemosum plant Fructus Chebulae (Terminalia chebula Retz.)
Dry fruit.
(2) isolated and purified: isolated and purified: with n-hexane-ethyl acetate-methanol-water as solvent system, under
Mutually as flowing phase, the crude extract of described target component is dissolved in lower phase solution, and injects high-speed counter-current
Chromatograph separates, and when flowing out chromatographic column mutually wait flowing, collects separator according to chromatographic peak；This separation
Thing is the most concentrated, be dried to constant weight, respectively obtains 13mg chebulinic acid, 18mg Chebulagic acid and 9
Mg ellagic acid；
Wherein: the normal hexane in solvent system, ethyl acetate, methanol, the volume ratio (L/L) of water are 1:
8:0.5:4.The separation condition of high-speed counter-current chromatograph (HSCCC) refers to flow velocity 1.5mL/min, main
Machine rotating speed 900rpm, separation temperature 30 DEG C, sample size is 200mg, and the retention rate of fixing phase is 65%.
The monomer of high-speed counter-current chromatograph (HSCCC) isolated is utilized respectively high performance liquid chromatography
(HPLC) detection purity, purity is all more than 95%.
Wherein: high performance liquid chromatography (HPLC) testing conditions is with embodiment 1.
The monomer of high-speed counter-current chromatograph (HSCCC) isolated is passed through respectively1H-NMR and13C-NMR identifies.
Embodiment 4
Chebulinic acid, Chebulagic acid and the preparation method of three kinds of chemical reference substances of ellagic acid in Fructus Chebulae's medical material, bag
Include following steps:
(1) extract: after Fructus Chebulae's medicinal material drying fruit is crushed to 100 mesh, take 500g, dense by quality
Degree is that the ethanol 7.5L of 50% carries out supersound extraction under 300W, and extraction time is 3 times, extraction time
40min, obtains extracting solution；Extracting solution is at 70 DEG C, and under the conditions of 0.064MPa, concentrating under reduced pressure is dried to carry
Take thing dried powder.
Wherein: Fructus Chebulae's medicinal material drying fruit refers to Combretum Racemosum plant Fructus Chebulae (Terminalia chebula Retz.)
Dry fruit.
(2) isolated and purified: isolated and purified: with n-hexane-ethyl acetate-methanol-water as solvent system, under
Mutually as flowing phase, the crude extract of described target component is dissolved in lower phase solution, and injects high-speed counter-current
Chromatograph separates, and when flowing out chromatographic column mutually wait flowing, collects separator according to chromatographic peak；This separation
Thing is the most concentrated, be dried to constant weight, respectively obtains 6.3mg chebulinic acid, 9.7mg Chebulagic acid and
5.0mg ellagic acid；
Wherein: the normal hexane in solvent system, ethyl acetate, methanol, the volume ratio (L/L) of water are 1:
7:0.5:3.The separation condition of high-speed counter-current chromatograph (HSCCC) refers to flow velocity 2mL/min, main
Machine rotating speed 800rpm, separation temperature 30 DEG C, sample size is 100mg, and the retention rate of fixing phase is 62%.
The monomer of high-speed counter-current chromatograph (HSCCC) isolated is utilized respectively high performance liquid chromatography
(HPLC) detection purity, purity is all more than 95%.
Wherein: high performance liquid chromatography (HPLC) testing conditions is with embodiment 1.
The monomer of high-speed counter-current chromatograph (HSCCC) isolated is passed through respectively1H-NMR and13C-NMR identifies.
Embodiment 5
Chebulinic acid, Chebulagic acid and the preparation method of three kinds of chemical reference substances of ellagic acid in Fructus Chebulae's medical material, bag
Include following steps:
(1) extract: after Fructus Chebulae's medicinal material drying fruit is crushed to 160 mesh, take 500g, dense by quality
Degree is that the ethanol 10L of 60% carries out supersound extraction under 250W, and extraction time is 2 times, extraction time
40min, obtains extracting solution；Extracting solution is at 70 DEG C, and under the conditions of 0.064MPa, concentrating under reduced pressure is dried to carry
Take thing dried powder.
Wherein: Fructus Chebulae's medicinal material drying fruit refers to Combretum Racemosum plant Fructus Chebulae (Terminalia chebula Retz.)
Dry fruit.
(2) isolated and purified: isolated and purified: with n-hexane-ethyl acetate-methanol-water as solvent system, under
Mutually as flowing phase, the crude extract of described target component is dissolved in lower phase solution, and injects high-speed counter-current
Chromatograph separates, and when flowing out chromatographic column mutually wait flowing, collects separator according to chromatographic peak；This separation
Thing is the most concentrated, be dried to constant weight, respectively obtains 6.6mg chebulinic acid, 9.2mg Chebulagic acid and
4.8mg ellagic acid；
Wherein: the normal hexane in solvent system, ethyl acetate, methanol, the volume ratio (L/L) of water are 1:
7:0.5:3.The separation condition of high-speed counter-current chromatograph (HSCCC) refers to flow velocity 2mL/min, main
Machine rotating speed 800rpm, separation temperature 25 DEG C, sample size is 100mg, and the retention rate of fixing phase is 61%.
The monomer of high-speed counter-current chromatograph (HSCCC) isolated is utilized respectively high performance liquid chromatography
(HPLC) detection purity, purity is all more than 95%.
Wherein: high performance liquid chromatography (HPLC) testing conditions is with embodiment 1.
The monomer of high-speed counter-current chromatograph (HSCCC) isolated is passed through respectively1H-NMR and13C-NMR identifies.
The effect of above-described embodiment indicates that the essentiality content of the present invention, but does not limit this with this
Bright protection domain.It will be understood by those within the art that, can be to technical scheme
Modify or equivalent, without deviating from essence and the protection domain of technical solution of the present invention.
Claims (4)
1. chebulinic acid, Chebulagic acid and the preparation method of three kinds of chemical reference substances of ellagic acid in Fructus Chebulae's medical material,
It is characterized in that, comprise the following steps:
(1) extract: after Fructus Chebulae's medicinal material drying fruit is crushed to 40～200 mesh, with 1g:5mL～30mL
Ratio volumetric concentration be 10～95% ethanol under 200～400W, carry out supersound extraction, extraction time
It is 1～3 time, each 30～60min, merge and obtain extracting solution；Described extracting solution is dried through concentrating under reduced pressure
Crude extract dried powder；
(2) isolated and purified: with n-hexane-ethyl acetate-methanol-water as solvent system, lower as flowing
Phase, is dissolved in the crude extract of described target component in lower phase solution, and injects high-speed counter-current chromatograph and carry out
Separate, when flowing out chromatographic column mutually wait flowing, collect separator according to chromatographic peak；This separator is successively through dense
Contract, be dried to constant weight, respectively obtain chebulinic acid, Chebulagic acid and ellagic acid.
2. chebulinic acid, Chebulagic acid and three kinds of chemistry of ellagic acid in Fructus Chebulae's medical material as claimed in claim 1
The preparation method of reference substance, it is characterised in that: described step (1) middle Fructus Chebulae's medicinal material drying fruit is to instigate monarch
The dry fruit of scarabaeidae plant Fructus Chebulae.
3. chebulinic acid, Chebulagic acid and three kinds of chemistry of ellagic acid in Fructus Chebulae's medical material as claimed in claim 1
The preparation method of reference substance, it is characterised in that: the normal hexane in described step (2) solvent system, acetic acid
Ethyl ester, methanol, the volume ratio of water are 0.5～1.5:5～9:0.3～0.7:1～5.
4. chebulinic acid, Chebulagic acid and three kinds of chemistry of ellagic acid in Fructus Chebulae's medical material as claimed in claim 1
The preparation method of reference substance, it is characterised in that: the lightning strip of described step (2) high speed counter-current chromatograph
Part refers to flow velocity 0.5～3.5mL/min, engine speed 700～900rpm, separation temperature 15～35 DEG C, enters
Sample amount is 50～200mg, and the retention rate of fixing phase is 50～71%.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108467417A (en) * | 2018-04-23 | 2018-08-31 | 中国科学院成都生物研究所 | FRUCTUS TERMINALIAE IMMATURUS extract, FRUCTUS TERMINALIAE IMMATURUS extract monomeric compound and its application in inhibiting monoamine oxidase B activity |
| CN109966328A (en) * | 2019-04-29 | 2019-07-05 | 白吉日木吐 | Ellagic acid and the extracting method of chebulinic acid and combinations thereof in a kind of myrobalan |
| CN111272904A (en) * | 2020-03-23 | 2020-06-12 | 广东一方制药有限公司 | Construction method and application of characteristic spectrum of medicine terminalia chebula and fructus chebulae tomentosa |
| CN114414701A (en) * | 2022-01-28 | 2022-04-29 | 辽宁中医药大学 | Preparation method and content determination method of myrobalamin acid in myrobalan meat |
| CN114965751A (en) * | 2022-05-05 | 2022-08-30 | 天津中医药大学 | Method for measuring chemical component content in myrobalan |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108467417A (en) * | 2018-04-23 | 2018-08-31 | 中国科学院成都生物研究所 | FRUCTUS TERMINALIAE IMMATURUS extract, FRUCTUS TERMINALIAE IMMATURUS extract monomeric compound and its application in inhibiting monoamine oxidase B activity |
| CN108467417B (en) * | 2018-04-23 | 2021-07-06 | 中国科学院成都生物研究所 | Fructus chebulae immaturus extract, fructus chebulae immaturus extract monomer compound and application of fructus chebulae immaturus extract monomer compound in inhibition of monoamine oxidase B activity |
| CN109966328A (en) * | 2019-04-29 | 2019-07-05 | 白吉日木吐 | Ellagic acid and the extracting method of chebulinic acid and combinations thereof in a kind of myrobalan |
| CN109966328B (en) * | 2019-04-29 | 2022-05-10 | 内蒙古阿尔善药业有限公司 | Method for extracting ellagic acid and myrobalan acid from myrobalan and composition thereof |
| CN111272904A (en) * | 2020-03-23 | 2020-06-12 | 广东一方制药有限公司 | Construction method and application of characteristic spectrum of medicine terminalia chebula and fructus chebulae tomentosa |
| CN111272904B (en) * | 2020-03-23 | 2022-04-05 | 广东一方制药有限公司 | Construction method and application of characteristic spectrum of medicine terminalia chebula and fructus chebulae tomentosa |
| CN114414701A (en) * | 2022-01-28 | 2022-04-29 | 辽宁中医药大学 | Preparation method and content determination method of myrobalamin acid in myrobalan meat |
| CN114965751A (en) * | 2022-05-05 | 2022-08-30 | 天津中医药大学 | Method for measuring chemical component content in myrobalan |
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