CN104208122A - Preparation method of chlorogenic acid extract - Google Patents
Preparation method of chlorogenic acid extract Download PDFInfo
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- CN104208122A CN104208122A CN201410257405.3A CN201410257405A CN104208122A CN 104208122 A CN104208122 A CN 104208122A CN 201410257405 A CN201410257405 A CN 201410257405A CN 104208122 A CN104208122 A CN 104208122A
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Abstract
A preparation method of a chlorogenic acid extract comprises the following steps: carrying out adsorbing separation on an aqueous solution containing chlorogenic acid by a first macroporous resin adsorption unit until the concentration of chlorogenic acid in the discharged aqueous solution is not less than the concentration of chlorogenic acid in the aqueous solution which is not adsorbed or separated, washing by water with the pH value of 2-8, collecting, mixing the water eluate containing chlorogenic acid and flowing out of the first macroporous resin adsorption unit with the above obtained water flushing liquid, adjusting the pH value to 2-4, adsorbing by a second macroporous resin adsorption unit, washing by using water with the pH value of 2-4 to remove impurities, eluting by using an ethanol-water solution with the ethanol volume content of 30-95%, collecting the obtained eluate, and removing solvent to obtain the chlorogenic acid extract. The preparation method can substantially improve the content of chlorogenic acid, and has practical application values.
Description
Technical field
The preparation method, particularly origin that the present invention relates to a kind of chlorogenic acid extract come from the method that the product containing chlorogenic acid that various method obtains prepares its purified extract.
Background technology
Chlorogenic acid be plant in aerobic respiration process through a kind of Phenylpropanoid Glycosides class material synthesized by the intermediate product of phosphopentose pathway, chlorogenic acid is mainly present in Caprifoliaceae Lonicera, Compositae artemisia and Eucommiaceae Cortex Eucommiae platymiscium.The former content of sunflower seed medium green is 1.5 ~ 3.3%, and the former content of Flos Lonicerae medium green is 0.2 ~ 11.2%, and the green former content of Folium Eucommiae is 1 ~ 5%.Chlorogenic acid has function of gallbladder promoting, antibacterial, antiviral, blood pressure lowering, the multiple pharmacological effect such as leukocyte increasing and stimulating central nervous system system, chlorogenic acid is the natural specificity inhibitor of hyaluronidase (HAase) and Gle-6-p displacement enzyme, also be the scavenger of selectivity hydroxyl radical free radical and peroxy radical, can be used as the important source material of the industry such as health product, food, medicine, cosmetics.The common methods of separation and purification chlorogenic acid, has the modes such as precipitate with ethanol, inorganic salt precipitation, solvent extraction, ion exchange resin separation, gel chromatography separation, high performance liquid chromatography separation and macroporous adsorbent resin separation.From the viewpoint of the safety, production efficiency etc. of product, macroporous adsorbent resin separation and purification is the main development direction of suitability for industrialized production chlorogenic acid.As lijin to fly etc. to report research (the West China pharmaceutical journal of NKA-9 type resin to chlorogenic acid adsorption separation performance, 2004,19 (1): 1-4), Wang Fang etc. report the research (Strait Pharmaceutical Journal of macroporous adsorbent resin to Adsorption of Chlorogenic Acid, 2006,18 (1): 97-99), Chinese patent CN 102285885A etc. also disclose the method for macroporous adsorbent resin separation and purification chlorogenic acid.The conventional method preparing chlorogenic acid by macroporous adsorbent resin of current bibliographical information is: will containing the aqueous solution of chlorogenic acid or aqueous extract, after upper macroporous adsorptive resins, first wash remove impurity with water, use ethanol elution (parsing) again, collect ethanol elution, except desolventizing, namely chlorogenic acid extract is obtained, wherein the pH value of upper prop liquid and slurry is 1 ~ 8, and preferred pH value is 1 ~ 4, and eluting concentration of alcohol is 20 ~ 95%.Applicant studies discovery, and the content of the chlorogenic acid extract that this kind of conventional macroporous resin method reported at present prepares is all lower.
Summary of the invention
For above-mentioned situation, the invention provides a kind of preparation method of chlorogenic acid extract, particularly the method that the product containing chlorogenic acid that various method obtains prepares its purified extract is come to origin.
The preparation method of chlorogenic acid extract of the present invention, make the first macroporous resin adsorption unit of the aqueous solution containing chlorogenic acid carry out adsorbing separation, to the concentration >=upper prop flowing out aqueous solution Content of Chlorogenic Acid aqueous solution Content of Chlorogenic Acid concentration after, with the water washing of pH value 2 ~ 8, collect, merge the described aqueous effluent containing chlorogenic acid by flowing out after the first macroporous resin adsorption unit and water lotion and after adjust ph 2 ~ 4, adsorb with the second macroporous resin adsorption unit, then after using the water washing remove impurity of pH value 2 ~ 4, be the ethanol-water solution eluting of 30 ~ 95% again with alcohol volume content, desolventizing is removed after collecting eluent, obtain chlorogenic acid extract.
As the aqueous solution containing chlorogenic acid described in raw materials in said method, the various raw material containing chlorogenic acid composition can be derived from, as, both the processed goods of medical material containing chlorogenic acid or corresponding medical material can have been comprised, as Flos Lonicerae, Flos Lonicerae, river Flos Lonicerae, Folium Eucommiae, Caulis Lonicerae, sunflower seed dregs; The stem branch of Flos Lonicerae, Flos Lonicerae, river Flos Lonicerae and/or leaf, and containing the aqueous extract that other medicinal plants of chlorogenic acid, medical material and decoction pieces etc. obtain, also can be the aqueous solution of the corresponding converted products prepared further by the extract of the medical material containing chlorogenic acid or corresponding processing of crude drugs product.
Deep research experiment display, macroporous resin is to chlorogenic acid and commonly in its extract all have absorbability as the impurity such as flavone, saponin composition, but compares, and the absorption affinity (intensity) of macroporous resin to chlorogenic acid is more weak.Therefore, after macroporous resin adsorption is saturated, chlorogenic acid flows out at first, other composition such as flavone, saponin then still can by continuation absorption, and along with the described aqueous solution containing chlorogenic acid continue enter, by competitive adsorption effect, formerly on resin, also can be departed from macroporous resin by the stronger component permutation (or substituting) of the absorption affinity such as flavone, saponin by the chlorogenic acid that adsorbs and go out with water liquid stream.The present invention utilizes this characteristic just, first with first macropore resin unit absorption saturated after chlorogenic acid is flowed out, to the concentration >=upper prop of aqueous effluent Content of Chlorogenic Acid aqueous solution Content of Chlorogenic Acid concentration after, wash with water again, substantially can washing the former chlorogenic acid composition adsorbed on most macroporous resin, continuing to be adsorbed that be deposited in macroporous resin is then the impurity composition for removing such as a large amount of flavone, saponin etc. that are separated with chlorogenic acid.By collect merged by the aqueous effluent containing chlorogenic acid after the first macroporous resin adsorption unit remove impurity and water lotion after, again according to a conventional method with second largest macroporous adsorbent resin unit absorption, then after the further remove impurity of water washing, use alcohol desorbing eluting again, eluent, except after desolventizing, namely obtains the chlorogenic acid extract of high-load.
Macroporous resin adsorption unit described in said method of the present invention, can adopt and the most conventional be filled with the forms such as the adsorption column of macroporous adsorbent resin.The first and second described macroporous resin adsorption unit, according to practical situation, separate two macroporous resin adsorption unit (can be made up of single and/or many resin absorbing columns respectively) can be adopted, also can adopting by the alternate operation in an alternating manner of same macroporous resin adsorption unit, making for realizing respectively as the first and second resin absorption unit.For adopting the first and second macroporous adsorbent resin unit of separate setting, can also adopt by it suitably and connect and/or the compound mode operation such as series winding, to meet the needs of specific treatment scale and actual production.
Further, be 2 ~ 8 with the pH value of the described aqueous solution containing chlorogenic acid of the first macroporous resin adsorption unit absorption described in said method; The described pH value of water solution containing chlorogenic acid of preferred use first macroporous resin adsorption unit absorption is 2 ~ 4.To the adjustment of pH value, except preferred with except hydrochloric acid that is the most conventional in commercial production and that be easy to get, also can use other acid ingredients such as comprising phosphoric acid, the acid ingredient that particularly can allow and accept in pharmacy carries out acidify adjustment.
Chlorogenic acid is faintly acid composition, unstable under alkali condition, therefore generally should at absorption or eluting under about neutral or acid condition, therefore, the absorption of the present invention first macroporous resin adsorption unit and the pH value of water elution are 2 ~ 8, mainly keep chlorogenic acid stable, because chlorogenic acid is more easily adsorbed and resin absorption capacity is larger in acid condition, therefore the pH value that the pH value of preferred resin absorption is the 2 ~ 4, second macroporous resin adsorption unit water elution is also preferably 2 ~ 4.Alcohol-water mixed solution all complete chlorogenic acid compositions of energy eluting of 30 ~ 95%, but consider from reduction production cost, preferred eluant ethanol concentration can be 30 ~ 50%.
Experiment display, state on the invention in method and in the first and second macroporous resin adsorption unit, allow the macroporous adsorbent resin used can have comparatively more options, such as, two macroporous resin adsorption unit can separately be selected from but be not limited at least one in the macroporous adsorbent resin of the models such as HPD100, HPD300, D101, D100, NKA-2, NKA-9, S-8, LS-600, HZ806 or AB-8.
Experimental result shows, compared with current conventional method, the preparation method of aforesaid way of the present invention, can significantly improve the content of chlorogenic acid extract.
Detailed description of the invention is by the following examples described in further detail foregoing of the present invention again.But this should be interpreted as that the scope of the above-mentioned theme of the present invention is only limitted to following example.Without departing from the idea case in the present invention described above, the various replacement made according to ordinary skill knowledge and customary means or change, all should comprise within the scope of the invention.
Detailed description of the invention
embodiment 1
(pH value is about 5 to the aqueous extract of river Flos Lonicerae, chlorogenic acid content is 2.5mg/ml), a upper HPD100 macroporous adsorptive resins, collect aqueous effluent, HPLC detects the content of chlorogenic acid, content to aqueous effluent Content of Chlorogenic Acid is 3.0mg/ml, stop loading, use the water elution of bed volume 2 ~ 6 times instead, collect water lotion, merge the aqueous effluent containing chlorogenic acid and water lotion, adjust ph 2 ~ 4, go up the 2nd HPD100 macroporous adsorptive resins again, after pH value 2 ~ 4 acid rinsing, be the ethanol-water solution eluting of 30 ~ 50% again with alcohol volume content, collect ethanol elution, except desolventizing, dry, obtain described chlorogenic acid extract.
embodiment 2
(adjust pH is 2 to the aqueous extract of Flos Lonicerae, chlorogenic acid content is 2.1mg/ml), a upper D101 macroporous adsorptive resins, collect aqueous effluent, HPLC detects the content of chlorogenic acid, content to aqueous effluent Content of Chlorogenic Acid is 2.4mg/ml, stop loading, use the water elution of bed volume 4 times instead, collect water lotion, merge the aqueous effluent containing chlorogenic acid and water lotion, adjust ph is 4, go up the 2nd HPD101 macroporous adsorptive resins again, after the acid rinsing of pH=4, be the ethanol-water solution eluting of 70% again with alcohol volume content, collect ethanol elution, except desolventizing, dry, obtain described chlorogenic acid extract.
embodiment 3
(adjust pH is 3 to the aqueous extract of Flos Lonicerae, chlorogenic acid content is 1.2mg/ml), a upper NKA-2 macroporous adsorptive resins, collect aqueous effluent, HPLC detects the content of chlorogenic acid, content to aqueous effluent Content of Chlorogenic Acid is 1.2mg/ml, stop loading, use the water elution of bed volume 5 times instead, collect water lotion, merge the aqueous effluent containing chlorogenic acid and water lotion, adjust ph is 3, go up the 2nd NKA-2 macroporous adsorptive resins again, after the acid rinsing of pH=3, be the ethanol-water solution eluting of 40% again with alcohol volume content, collect ethanol elution, except desolventizing, dry, obtain described chlorogenic acid extract.
embodiment 4
The aqueous extract (pH value is about 6) of Folium Eucommiae, a upper S-8 macroporous adsorptive resins, collect aqueous effluent, detect the content of chlorogenic acid, the concentration of aqueous solution Content of Chlorogenic Acid to the concentration >=upper prop of aqueous effluent Content of Chlorogenic Acid, stop loading, use the water elution of bed volume 3 times instead, collect water lotion, merge the aqueous effluent containing chlorogenic acid and water lotion, adjust ph is 2, go up the 2nd S-8 macroporous adsorptive resins again, after the acid rinsing of pH=4, be the ethanol-water solution eluting of 30% again with alcohol volume content, collect ethanol elution, except desolventizing, dry, obtain described chlorogenic acid extract.
embodiment 5
The aqueous extract (adjust pH is 8) of sunflower seed dregs, a upper AB-8 macroporous adsorptive resins, collect aqueous effluent, detect the content of chlorogenic acid, the concentration of aqueous solution Content of Chlorogenic Acid to the concentration >=upper prop of aqueous effluent Content of Chlorogenic Acid, stop loading, use bed volume 2 times instead, the water elution of pH=8, collect water lotion, merge the aqueous effluent containing chlorogenic acid and water lotion, adjust ph is 2, go up the 2nd AB-8 macroporous adsorptive resins again, after the acid rinsing of pH=4, be the ethanol-water solution eluting of 95% again with alcohol volume content, collect ethanol elution, except desolventizing, dry, obtain described chlorogenic acid extract.
embodiment 6
The aqueous extract of river Flos Lonicerae stem branch and leaf, a upper HZ806 macroporous adsorptive resins, collect aqueous effluent, detect the content of chlorogenic acid, the concentration of aqueous solution Content of Chlorogenic Acid to the concentration >=upper prop of aqueous effluent Content of Chlorogenic Acid, stop loading, use the water elution of bed volume 3 times instead, collect water lotion, merge the aqueous effluent containing chlorogenic acid and water lotion, adjust ph is 4, go up the 2nd LS-600 macroporous adsorptive resins again, after the acid rinsing of pH=4, be the ethanol-water solution eluting of 50% again with alcohol volume content, collect ethanol elution, except desolventizing, dry, obtain described chlorogenic acid extract.
embodiment 7
The aqueous solution (pH value is about 5) of Lonicera confusa extract, a upper S-8 macroporous adsorptive resins, collect aqueous effluent, detect the content of chlorogenic acid, the concentration of aqueous solution Content of Chlorogenic Acid to the concentration >=upper prop of aqueous effluent Content of Chlorogenic Acid, stop loading, use bed volume 4 times instead, the water elution of pH=5, collect water lotion, merge the aqueous effluent containing chlorogenic acid and water lotion, adjust ph is 3, go up the 2nd NKA-9 macroporous adsorptive resins again, after the acid rinsing of pH=3, be the ethanol-water solution eluting of 60% again with alcohol volume content, collect ethanol elution, except desolventizing, dry, obtain described chlorogenic acid extract.
embodiment 8
The aqueous solution (adjust pH is 3) of river Flos Lonicerae extract, a upper D-100 macroporous adsorptive resins, collect aqueous effluent, detect the content of chlorogenic acid, the concentration of aqueous solution Content of Chlorogenic Acid to the concentration >=upper prop of aqueous effluent Content of Chlorogenic Acid, stop loading, use the water elution of bed volume 6 times instead, collect water lotion, merge the aqueous effluent containing chlorogenic acid and water lotion, adjust ph is 3, go up the 2nd HPD300 macroporous adsorptive resins again, after the acid rinsing of pH=2, be the ethanol-water solution eluting of 30% again with alcohol volume content, collect ethanol elution, except desolventizing, dry, obtain described chlorogenic acid extract.
embodiment 9
(adjust pH is 4 to the aqueous extract of river, south Flos Lonicerae, chlorogenic acid content is 2.3mg/ml), a upper HPD100 macroporous adsorptive resins, collect aqueous effluent, detect the content of chlorogenic acid, content to aqueous effluent Content of Chlorogenic Acid is 2.6mg/ml, stop loading, use bed volume 5 times instead, the sour water eluting of pH=4, collect water lotion, aqueous effluent containing chlorogenic acid and water lotion are passed through the 2nd HPD300 macroporous adsorptive resins successively, be the ethanol-water solution eluting of 40% again with alcohol volume content, collect ethanol elution, except desolventizing, dry, obtain described chlorogenic acid extract.
embodiment 10
70% ethanol extract of Lonicera fulvotnetosa Hsu et S. C. Cheng. Ms, recovery eliminates ethanol, thin up, adjust pH is 3, filter, the upper D101 macroporous adsorptive resins of filtrate, detect the content of chlorogenic acid, the concentration of aqueous solution Content of Chlorogenic Acid to the concentration >=upper prop of aqueous effluent Content of Chlorogenic Acid, stop loading, use bed volume 4 times instead, the sour water eluting of pH=3, collect water lotion, aqueous effluent containing chlorogenic acid and water lotion are passed through the 2nd NKA-2 macroporous adsorptive resins successively, be the ethanol-water solution eluting of 50% again with alcohol volume content, collect ethanol elution, except desolventizing, dry, obtain described chlorogenic acid extract.
embodiment 11
The aqueous solution (adjust pH is 2) of Folium Eucommiae extract, a upper NKA-9 macroporous adsorptive resins, detect the content of chlorogenic acid, the concentration of aqueous solution Content of Chlorogenic Acid to the concentration >=upper prop of aqueous effluent Content of Chlorogenic Acid, stop loading, use the sour water eluting of bed volume 5 times, pH=2 instead, collect water lotion, aqueous effluent containing chlorogenic acid and water lotion are passed through the 2nd NKA-9 macroporous adsorptive resins successively, be the ethanol-water solution eluting of 30% again with alcohol volume content, collect ethanol elution, except desolventizing, drying, obtains described chlorogenic acid extract.
Below by way of being evaluation index to the content of chlorogenic acid extract, further illustrate the beneficial effect of preparation method of the present invention.
Determination of chlorogenic acid: measure by the determination of chlorogenic acid method under 2010 editions Chinese Pharmacopoeias Flos Lonicerae item.
Embodiment 1 to embodiment 11 is containing the medical material of chlorogenic acid and the aqueous extract of processed goods thereof, or the aqueous solution of the extract containing chlorogenic acid, after adsorbing with the macroporous adsorptive resins corresponding to each embodiment respectively according to a conventional method, first wash with water, again by the ethanol elution described in each embodiment, except desolventizing, dry, obtain chlorogenic acid extract prepared by conventional method.
The chlorogenic acid extract that the embodiment of the present invention 1 to embodiment 11 obtains and the chlorogenic acid extract prepared according to a conventional method, carry out the assay of active ingredient chlorogenic acid, the results are shown in Table 1 by official method.
Contrasted from table 1, the chlorogenic acid extract Content of Chlorogenic Acid height about about 50% that the chlorogenic acid extract that preparation method of the present invention obtains is prepared than conventional method, significantly improve the content of effective ingredient, and the extraction rate of transform of two kinds of preparation method Content of Chlorogenic Acids is suitable, (what show the first macroporous adsorbent resin unit of the inventive method removes miscellaneous operation to no significant difference, substantially only impurity is removed, can't impact the recovery of chlorogenic acid composition), be about 90%.In addition, the beyond thought effect that the inventive method also has further is, the amount of alcohol of eluting can reduce about half, thus greatly reduces production cost, improves production efficiency.And the resin model described in conventional macroporous resin preparation method of existing bibliographical information/use at present, eluting concentration of alcohol, containing the aqueous extract of chlorogenic acid or aqueous solution etc., all be applicable to the inventive method, the meaning and value of wide popularization and application that made it have more.
The comparison of the extract Content of Chlorogenic Acid that the different preparation method of table 1 obtains
| Embodiment | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 |
| Preparation method of the present invention each embodiment content % | 61.5 | 57.8 | 46.3 | 47.1 | 52.6 | 36.7 | 67.2 | 75.4 | 58.7 | 43.2 | 66.0 |
| Customary preparation methods corresponding comparative example content % | 40.1 | 38.2 | 29.4 | 30.7 | 33.5 | 25.3 | 45.6 | 49.5 | 39.0 | 35.4 | 43.6 |
Claims (5)
1. the preparation method of chlorogenic acid extract, it is characterized in that making the first macroporous resin adsorption unit of the aqueous solution containing chlorogenic acid carry out adsorbing separation, to the concentration >=upper prop flowing out aqueous solution Content of Chlorogenic Acid aqueous solution Content of Chlorogenic Acid concentration after, with the water washing of pH value 2 ~ 8, collect, merge the described aqueous effluent containing chlorogenic acid by flowing out after the first macroporous resin adsorption unit and water lotion and after adjust ph 2 ~ 4, adsorb with the second macroporous resin adsorption unit, then after using the water washing remove impurity of pH value 2 ~ 4, be the ethanol-water solution eluting of 30 ~ 95% again with alcohol volume content, desolventizing is removed after collecting eluent, obtain chlorogenic acid extract.
2. preparation method as claimed in claim 1, it is characterized in that the described aqueous solution containing chlorogenic acid carrying out adsorbing separation with the first macroporous resin adsorption unit, for the direct aqueous extract of the medical material containing chlorogenic acid or processing of crude drugs product, or the aqueous solution obtained by the extract of the medical material containing chlorogenic acid or processing of crude drugs product.
3. preparation method as claimed in claim 1, is characterized in that the pH value 2 ~ 8 of the described aqueous solution containing chlorogenic acid with the first macroporous resin adsorption unit absorption.
4. preparation method as claimed in claim 3, is characterized in that the pH value 2 ~ 4 of the described aqueous solution containing chlorogenic acid with the first macroporous resin adsorption unit absorption.
5. the preparation method as described in one of Claims 1-4, is characterized in that the adsorbent resin of described each macroporous resin adsorption unit is separately selected from least one in HPD100, HPD300, D101, D100, NKA-2, NKA-9, S-8, LS-600, HZ806 or AB-8 type macroporous adsorbent resin.
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Cited By (1)
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| CN113413392A (en) * | 2021-07-07 | 2021-09-21 | 江西普正制药股份有限公司 | Eucommia ulmoides extract composition and preparation method and application thereof |
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| CN101314568A (en) * | 2008-06-24 | 2008-12-03 | 南京工业大学 | Novel method for adsorption separation of high purity chlorogenic acid |
| CN103830306A (en) * | 2014-02-20 | 2014-06-04 | 鲁南制药集团股份有限公司 | Preparation method of honey suckle leaf effective extract product |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101314568A (en) * | 2008-06-24 | 2008-12-03 | 南京工业大学 | Novel method for adsorption separation of high purity chlorogenic acid |
| CN103830306A (en) * | 2014-02-20 | 2014-06-04 | 鲁南制药集团股份有限公司 | Preparation method of honey suckle leaf effective extract product |
Non-Patent Citations (1)
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| 卢琪等: "杜仲绿原酸的分离纯化及结构鉴定", 《食品科学》 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113413392A (en) * | 2021-07-07 | 2021-09-21 | 江西普正制药股份有限公司 | Eucommia ulmoides extract composition and preparation method and application thereof |
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