CN107793314B - Method for preparing 8 monomers from lonicera confusa - Google Patents
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- CN107793314B CN107793314B CN201710984686.6A CN201710984686A CN107793314B CN 107793314 B CN107793314 B CN 107793314B CN 201710984686 A CN201710984686 A CN 201710984686A CN 107793314 B CN107793314 B CN 107793314B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
Abstract
The invention discloses a method for preparing 8 monomers from lonicera confusa, which comprises the following steps: (1) crushing medicinal materials; (2) ultrasonic-assisted extraction; (3) separating and purifying by macroporous resin; (4) filling a dynamic axial compression column; (5) dynamic axial compression column separation. In the invention, 8 monomers including 5-caffeoylquinic acid, tetraacetyl secologanin, chlorogenic acid, swertiamarin, seco-oxide nux vomica, seco-marchantin and 4, 5-dicaffeoylquinic acid are simultaneously prepared in one separation and purification process, and the purity of 8 samples is higher than 95% through high performance liquid chromatography detection. The method has the advantages of simple operation, short production period, small organic solvent consumption, recyclability, high sample purity and high preparation efficiency, and can be used for industrial production.
Description
Technical Field
The invention relates to the technical field of extraction and separation of traditional Chinese medicines, in particular to a method for preparing 8 monomers from lonicera confusa.
Background
Lonicera confusa (Flos Lonicera Confusase) is a dried bud or flower with initial bloom of Lonicera macranthoides, Lonicera hypoglauca, Lonicera confusa or Lonicera fulvescens of Caprifoliaceae. Flos Lonicerae is sweet and slightly bitter, cold in nature, and nontoxic. It enters lung, heart and stomach meridians. The oral administration can cool the intestine, cool blood, remove toxicity, dredge collaterals and promote diuresis. It is used externally to relieve swelling. Can be used for treating common cold, summer heat, constipation, dysentery, hematochezia, coal smoke toxin, rheumatalgia, gingival swelling and pain, cholecystitis, etc.
Chlorogenic acid compounds are main effective components of flos Lonicerae, and chlorogenic acid is used as index of the extract. In the existing research, few reports exist for extracting and separating a plurality of monomers from lonicera confusa. Chinese patent (application No. 201410332285.9) discloses that flos Lonicerae is pulverized and extracted by an extraction tank, the extract is purified by macroporous resin and then separated by industrial chromatography, and finally a sample with chlorogenic acid content of 49.13% is prepared by spray drying technology. Chinese patent (201510379045.9) discloses that honeysuckle is concentrated after extraction, the concentrated solution is extracted by ethyl acetate, and the extract is concentrated and then separated by a dynamic axial compression column to prepare 4 components of neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid and semen strychni Pulveratum, wherein the purity of the 4 components is more than 90%.
Disclosure of Invention
In order to overcome the problems of large organic reagent dosage, low sample purity, less prepared monomer components and the like in the extraction method of the lonicera confusa in the prior art, the invention provides a preparation method for preparing a large amount of various high-purity monomers from the lonicera confusa, and provides a research basis for fully developing and utilizing lonicera confusa plant resources, preparing standard substances and developing new drugs.
The purpose of the invention is realized by the following technical scheme: a method for preparing 8 monomers from lonicera confusa, which comprises the following steps:
step one, crushing medicinal materials: pulverizing flos Lonicerae with pulverizer;
step two, ultrasonic-assisted extraction: adding purified water into flos Lonicerae powder, ultrasonic extracting, and filtering to obtain extractive solution;
step three, separating and purifying by macroporous resin: loading the extract to a macroporous resin column, eluting with water, eluting with an ethanol solution, collecting the eluent, and concentrating the eluent under reduced pressure at 50-70 ℃ to obtain a crude product;
step four, filling the dynamic axial compression column: homogenizing the chromatographic filler with absolute ethyl alcohol, adjusting the filling pressure, pouring the homogenate into a dynamic axial compression column, and compacting the filler after removing the homogenate to finish filling the dynamic axial compression column;
step five, separating the dynamic axial compression column: and (3) after the dynamic axial compression column is filled, balancing by adopting a mobile phase until a chromatographic baseline is stable, dissolving the crude product by using the mobile phase, filtering to obtain a sample solution, separating the sample solution by using industrial preparative chromatography, wherein the detection wavelength is 230nm, collecting target components according to different retention times, and carrying out reduced pressure concentration and freeze drying on the collected solution at 50-70 ℃ to obtain each monomer compound.
Preferably, in the first step, the lonicera confusa medicinal material is crushed into 10-60-mesh powder.
Preferably, in the second step, the ratio of the lonicera confusa medicinal material powder to the purified water is 1: 10-40 (g/ml), and the extraction time is 0.5-2.5 h.
Preferably, in the third step, the macroporous resin is one of D101, HPD-100, AB-8, D301, ADS-7 and JD-1.
Preferably, in the method for preparing 8 monomers from lonicera confusa, the volume fraction of the ethanol solution in the third step is 10-40%.
Preferably, in the fourth step of the method for preparing 8 monomers from lonicera confusa, the packing specification of the dynamic axial compression column is 50mm x 250 mm.
Preferably, in the step five, the industrial preparative chromatographic column packing material is C18-100、UniPS10-300、UniSil NH2 10-120、UniSilC18-100、UniSilC8-100.
Preferably, in the fifth step, the concentration of the sample injection solution is 50-150 mg/ml.
Preferably, in the method for preparing 8 monomers from lonicera confusa, in the fifth step, the mobile phase is methanol with the volume fraction of 10-45%.
Preferably, in the method for preparing 8 monomers from lonicera confusa, the flow rate of the mobile phase in the fifth step is 10ml/min to 40 ml/min.
Compared with the prior art, the invention has the following beneficial effects: the invention adopts a whole set of technology of ultrasonic-assisted extraction, macroporous resin purification and dynamic axial compression column separation as a core to simultaneously extract and separate 5-caffeoylquinic acid, tetraacetyl secologanin, chlorogenic acid, swertiamarin, seco-oxidized nux vomica, seco-loganin and 4, 5-dicaffeoylquinic acid from the lonicera confusa for the first time, and establishes a process route for extracting, purifying and separating 8 monomers from the lonicera confusa, and the process is reasonable and feasible, has simple process, convenient solvent recovery and high purity, can realize large-scale industrial production and has strong practical value.
Drawings
FIG. 1 is a chromatogram of the sample solution from the dynamic axial compression column separation of Lonicera confusa in this example 1;
FIG. 2 is a high performance liquid chromatogram of 5-caffeoylquinic acid monomer in example 1;
FIG. 3 is a high performance liquid chromatogram of tetraacetyl secologanin monomer from example 1;
FIG. 4 is a high performance liquid chromatogram of the split brucine acid monomer in example 1;
FIG. 5 is a high performance liquid chromatogram of chlorogenic acid monomer in example 1;
FIG. 6 is a high performance liquid chromatogram of swertiamarin monomer in this example 1;
FIG. 7 is the high performance liquid chromatogram of the disrupted nux vomica monomer oxide of example 1;
FIG. 8 is a high performance liquid chromatogram of the split ring loganin monomer of example 1;
FIG. 9 is a high performance liquid chromatogram of 4, 5-dicaffeoylquinic acid monomer from example 1.
In the figure: 15-caffeoylquinic acid; 2 tetraacetyl secologanin, 3 secologanin; 4 chlorogenic acid; 5, swertiamarin; 6, breaking oxidized nux vomica; 7 secologanin; 84, 5-dicaffeoylquinic acid.
Detailed Description
In order to better understand the present invention, the technical solutions of the present invention will be clearly and completely described below by way of examples, and it is obvious that the described examples are only a part of the examples of the present invention, not all of the examples. 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
A method for preparing 8 monomers from lonicera confusa, which comprises the following steps:
(1) crushing medicinal materials: taking a lonicera confusa medicinal material, and crushing the lonicera confusa medicinal material into 40 meshes by using a crusher;
(2) ultrasonic-assisted extraction: adding 25 times of purified water (g/ml) into the flos Lonicerae powder, ultrasonic extracting for 1.5h, and filtering to obtain extractive solution after extraction is completed;
(3) separating and purifying by macroporous resin: putting the extracting solution on a pretreated D101 macroporous resin column, eluting with water, then eluting with 20% ethanol solution by volume fraction, collecting the eluent, and concentrating the eluent under reduced pressure at 50-70 ℃ to obtain a crude product;
(4) dynamic axial compression column packing: taking chromatographic packing C18-100400 g, homogenizing with absolute ethyl alcohol, adjusting the filling pressure, pouring the homogenate into a dynamic axial compression column, removing the homogenate, compacting the filler until the filling specification is 50mm multiplied by 250mm, and completing filling of the dynamic axial compression column;
(5) dynamic axial compression column separation: and (2) after the dynamic axial compression column is filled, balancing the dynamic axial compression column by using a mobile phase until a chromatographic baseline is stable, dissolving the crude product by using the mobile phase to prepare 100mg/ml, filtering to obtain a sample solution, separating the sample solution by using industrial preparative chromatography, taking methanol with the volume fraction of 30% as the mobile phase, controlling the flow rate at 25ml/min and the detection wavelength at 230nm, collecting target components according to different retention times, and carrying out reduced pressure concentration and freeze drying on the collected solution at 50-70 ℃ to obtain each monomeric compound.
HPLC detection shows that the high performance liquid chromatogram of the monomeric compound is shown in FIG. 1, the purity of 5-caffeoylquinic acid is 96.77%, the purity of tetraacetyl secologanin is 97.38%, the purity of secologanin is 97.55%, the purity of chlorogenic acid is 99.07%, the purity of swertiamarin is 95.82%, the purity of seco-oxide nux vomica is 96.35%, the purity of seco-loganin is 97.47%, the purity of 4, 5-dicaffeoylquinic acid is 98.63%, the purity of each compound is more than 95%, and the high performance liquid chromatogram of each compound is shown in FIGS. 2-9.
Example 2
A method for preparing 8 monomers from lonicera confusa, which comprises the following steps:
(1) crushing medicinal materials: taking a lonicera confusa medicinal material, and crushing the lonicera confusa medicinal material into 10 meshes by using a crusher;
(2) ultrasonic-assisted extraction: adding 10 times of purified water (g/ml) into the flos Lonicerae powder, ultrasonic extracting for 2.5h, and filtering to obtain extractive solution after extraction is completed;
(3) separating and purifying by macroporous resin: putting the extracting solution on a pretreated JD-1 macroporous resin column, eluting with water, then eluting with 10% ethanol solution by volume fraction, collecting eluent, and concentrating the eluent under reduced pressure at 50-70 ℃ to obtain a crude product;
(4) dynamic axial compression column packing: taking chromatographic packing UniSil C8100400 g, homogenizing with absolute ethanol, adjusting filling pressure, pouring the homogenate into a dynamic axial compression column, removing the homogenate, compacting the filler until the filling specification is 50mm × 250mm, and completing filling of the dynamic axial compression column;
(5) dynamic axial compression column separation: and (2) after the dynamic axial compression column is filled, balancing by adopting a mobile phase until a chromatographic baseline is stable, dissolving the crude product by using the mobile phase to prepare 50mg/ml, filtering to obtain a sample solution, separating the sample solution by using industrial preparative chromatography, taking methanol with the volume fraction of 10% as the mobile phase, controlling the flow rate at 40ml/min and the detection wavelength at 230nm, collecting target components according to different retention times, concentrating the collected solution at 50-70 ℃ under reduced pressure, and freeze-drying to obtain each monomeric compound.
HPLC detection shows that the purity of 5-caffeoylquinic acid is 96.13%, the purity of tetraacetyl secologanin is 96.97%, the purity of secologanin is 97.02%, the purity of chlorogenic acid is 98.87%, the purity of swertiamarin is 95.70%, the purity of seco-oxidized nux vomica is 96.13%, the purity of seco-marchantin is 97.15%, the purity of 4, 5-dicaffeoylquinic acid is 98.14%, and the purity of each compound is more than 95%.
Example 3
A method for preparing 8 monomers from lonicera confusa, which comprises the following steps:
(1) crushing medicinal materials: taking a lonicera confusa medicinal material, and crushing the lonicera confusa medicinal material to 60 meshes by using a crusher;
(2) ultrasonic-assisted extraction: adding 40 times of purified water (g/ml) into flos Lonicerae powder, ultrasonic extracting for 0.5h, and filtering to obtain extractive solution;
(3) separating and purifying by macroporous resin: putting the extracting solution on a pretreated HPD-100 macroporous resin column, eluting with water, then eluting with 40% ethanol solution by volume fraction, collecting the eluent, and concentrating the eluent under reduced pressure at 50-70 ℃ to obtain a crude product;
(4) dynamic axial compression column packing: taking chromatographic packing UniSil NH210-120400 g, homogenizing with absolute ethyl alcohol, adjusting filling pressure, pouring the homogenate into a dynamic axial compression column, removing the homogenate, compacting the filler until the filling specification is 50mm multiplied by 250mm, and completing filling of the dynamic axial compression column;
(5) dynamic axial compression column separation: and (2) after the dynamic axial compression column is filled, balancing the dynamic axial compression column by using a mobile phase until a chromatographic baseline is stable, dissolving the crude product by using the mobile phase to prepare 150mg/ml, filtering to obtain a sample solution, separating the sample solution by using industrial preparative chromatography, taking methanol with the volume fraction of 45% as the mobile phase, controlling the flow rate at 10ml/min and the detection wavelength at 230nm, collecting target components according to different retention times, and carrying out reduced pressure concentration and freeze drying on the collected solution at 50-70 ℃ to obtain each monomeric compound.
HPLC detection shows that the purity of 5-caffeoylquinic acid is 96.25%, the purity of tetraacetyl secologanin is 97.03%, the purity of secologanin is 96.95%, the purity of chlorogenic acid is 98.95%, the purity of swertiamarin is 95.56%, the purity of seco-oxidized nux vomica is 95.99%, the purity of seco-marchantin is 97.20%, the purity of 4, 5-dicaffeoylquinic acid is 97.95%, and the purity of each compound is more than 95%.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. A method for preparing 8 monomers from lonicera confusa, which is characterized by comprising the following steps:
step one, crushing medicinal materials: pulverizing flos Lonicerae with pulverizer;
step two, ultrasonic-assisted extraction: adding purified water into flos Lonicerae powder, ultrasonic extracting, and filtering to obtain extractive solution;
step three, separating and purifying by macroporous resin: loading the extract to a macroporous resin column, eluting with water, eluting with an ethanol solution, collecting the eluent, and concentrating the eluent under reduced pressure at 50-70 ℃ to obtain a crude product;
step four, filling the dynamic axial compression column: homogenizing the chromatographic filler with absolute ethyl alcohol, adjusting the filling pressure, pouring the homogenate into a dynamic axial compression column, and compacting the filler after removing the homogenate to finish filling the dynamic axial compression column;
step five, separating the dynamic axial compression column: after the dynamic axial compression column is filled, adopting a mobile phase to balance until a chromatographic baseline is stable, dissolving a crude product by using the mobile phase and then filtering to obtain a sample solution, separating the sample solution by using industrial preparative chromatography, wherein the detection wavelength is 230nm, collecting target components according to different retention times, and carrying out reduced pressure concentration and freeze drying on the collected solution at 50-70 ℃ to obtain each monomer compound;
each monomeric compound is: 5-caffeoylquinic acid, tetraacetyl secologanin, secologenin, chlorogenic acid, swertiamarin, secoisolariciresinol diglucoside, secologenin and 4, 5-dicaffeoylquinic acid.
2. The method for preparing 8 monomers from lonicera confusa according to claim 1, wherein the method comprises the following steps: in the first step, the lonicera confusa medicinal material is crushed into 10-60 meshes of powder.
3. The method for preparing 8 monomers from lonicera confusa according to claim 1, wherein the method comprises the following steps: in the second step, the material-liquid ratio of the lonicera confusa medicinal material powder to the purified water is 1: 10-40 (g/ml), and the extraction time is 0.5-2.5 h.
4. The method for preparing 8 monomers from lonicera confusa according to claim 1, wherein the method comprises the following steps: in the third step, the macroporous resin is one of D101, HPD-100, AB-8, D301, ADS-7 and JD-1.
5. The method for preparing 8 monomers from lonicera confusa according to claim 1, wherein the method comprises the following steps: in the third step, the volume fraction of the ethanol solution is 10-40%.
6. The method for preparing 8 monomers from lonicera confusa according to claim 1, wherein the method comprises the following steps: in the fourth step, the packing specification of the dynamic axial compression column is 50mm multiplied by 250 mm.
7. The method for preparing 8 monomers from lonicera confusa according to claim 1, wherein the method comprises the following steps: in the fifth step, the industrial preparation chromatographic column filler is C18-100、UniPS10-300、UniSilNH210-120、UniSilC18-100、UniSilC8-100.
8. The method for preparing 8 monomers from lonicera confusa according to claim 1, wherein the method comprises the following steps: in the fifth step, the concentration of the sample injection liquid is 50-150 mg/ml.
9. The method for preparing 8 monomers from lonicera confusa according to claim 1, wherein the method comprises the following steps: in the fifth step, the mobile phase is methanol with the volume fraction of 10-45%.
10. The method for preparing 8 monomers from lonicera confusa according to claim 1, wherein the method comprises the following steps: in the fifth step, the flow rate of the mobile phase is 10 ml/min-40 ml/min.
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| CN101085795A (en) * | 2006-06-07 | 2007-12-12 | 石家庄汉康生化药品有限公司 | Honeysuckle extract and its preparation method and application |
| CN104086424A (en) * | 2014-07-11 | 2014-10-08 | 广州中大南沙科技创新产业园有限公司 | Method for extracting and separating chlorogenic acid from honeysuckle flower |
| CN106317141A (en) * | 2015-07-01 | 2017-01-11 | 沈阳药科大学 | Method for preparing lonicerae flos monomer with dynamic axial compression column |
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2017
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101085795A (en) * | 2006-06-07 | 2007-12-12 | 石家庄汉康生化药品有限公司 | Honeysuckle extract and its preparation method and application |
| CN104086424A (en) * | 2014-07-11 | 2014-10-08 | 广州中大南沙科技创新产业园有限公司 | Method for extracting and separating chlorogenic acid from honeysuckle flower |
| CN106317141A (en) * | 2015-07-01 | 2017-01-11 | 沈阳药科大学 | Method for preparing lonicerae flos monomer with dynamic axial compression column |
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