CN102060693A - Method for enriching and purifying ferulic acid in cimicifugae foetidae - Google Patents
Method for enriching and purifying ferulic acid in cimicifugae foetidae Download PDFInfo
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- CN102060693A CN102060693A CN2010106229389A CN201010622938A CN102060693A CN 102060693 A CN102060693 A CN 102060693A CN 2010106229389 A CN2010106229389 A CN 2010106229389A CN 201010622938 A CN201010622938 A CN 201010622938A CN 102060693 A CN102060693 A CN 102060693A
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- 238000000034 method Methods 0.000 title claims abstract description 47
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 title abstract description 10
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 title abstract description 8
- 235000001785 ferulic acid Nutrition 0.000 title abstract description 8
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 title abstract description 8
- 229940114124 ferulic acid Drugs 0.000 title abstract description 8
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- 238000010828 elution Methods 0.000 claims description 20
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- ATDBDSBKYKMRGZ-ZDUSSCGKSA-N Cimifugin Chemical compound O1C(CO)=CC(=O)C2=C1C=C1O[C@H](C(C)(C)O)CC1=C2OC ATDBDSBKYKMRGZ-ZDUSSCGKSA-N 0.000 description 1
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- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 description 1
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- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 description 1
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- Medicines Containing Plant Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the field of natural organic chemistry and relates to a method for enriching and purifying ferulic acid in cimicifugae foetidae with macroporous adsorption resin. The invention is characterized in that the macroporous adsorption resin technology is adopted to separate and purify ferulic acid, the method has good adsorptive selectivity to ferulic acid, adsorption and desorption can be performed fast, and the adsorption capacity is higher; extraction can be performed conveniently and fast, the raw material is rich in resources, the production cost is low, the separation effect is obvious, the extraction purify is high, the semi-finished ferulic acid product with the content of more than 35% and the finished ferulic acid product with the content of more than 90% can be obtained; and the defects of the conventional extraction method that the extraction rate is lower and the extraction purity is low can be overcome. In the method in the invention, the macroporous adsorption resin with stable physical and chemical properties is selected, the method has the advantages of larger surface area, higher exchange speed, high mechanical strength and high contamination resistance and good thermal stability; ferulic acid can be selectively adsorbed from the solution through physical absorption; and adsorption and desorption can be performed fast and the absorption capacity is higher.
Description
Technical field:
The invention belongs to the natural organic chemistry field, relate to a kind of purification process of forulic acid, particularly relate to a kind of method of utilizing forulic acid in the enriching and purifying macroporous resin rattletop.
Background technology:
Rattletop is big ox card frame, Radix Longan, hole root of the tooth again, is the dry rhizome of the big three leaf rattletops of ranunculaceae plant, Xingan's rattletop or rattletop.Can deliver promoting eruption, clearing heat and detoxicating, the elevate a turnable ladder yang-energy.Be used for headache due to pathogenic wind-heat, dentalgia, aphtha, swelling and pain in the throat, measles without adequate eruption, the sun poison is sent out spot; Prolapse of the anus, uterine prolapse.The rattletop rhizome contains cimicifugine (Cimicifu-gine), Whitfield's ointment (Salicylic acid), tannin (Tannin), resin (Resin), coffic acid (Caffeic acid), forulic acid (Ferulic acid), isoferulic acid (Isoferulic acid), Cimiside (Cimi-cifugo side), Cimigenol xyloside (Cimigenol xyloside) etc.; Xingan's rattletop rhizome contains macrotin (Cimitin), alkaloid (Alkaloid), carbohydrate, resin, glucoside, isoferulic acid, forulic acid and coffic acid; Big three leaf rattletops contain alkaloid, macrotin, Cimiside, Cimigenol xyloside, isoferulic acid etc.
Forulic acid another name 3-methoxyl group-4-hydroxycinnamic acid has platelet aggregation-against, suppresses the thrombocyte serotonin and discharges, and suppresses the generation of the plain A2 of platelet thrombus (TXA2), strengthens the prostaglandin(PG) activity, analgesia, effects such as alleviating vascular spasm.Be to produce the basic raw material that is used for the treatment of disease medicines such as cardiovascular and cerebrovascular diseases and oligoleukocythemia.It can play effect vigorous and graceful and protection skin simultaneously in human body.In recent years, it is found that and contain a large amount of forulic acid in the natural phant rattletop,, therefrom extract forulic acid and obtained encouraging progress because its raw material rattletop source is wider.Name is called and just discloses in the patent application of " rattletop organic acid extracting method and new purposes " rattletop through the technical process of alcohol extracting organic reagent extraction forulic acid.Forulic acid extraction process in the above-mentioned patent documentation mainly is to extract through steps such as the back extractions of directly purifying with alcohol immersion to form, and its separating effect is nothing like macroporous adsorbent resin processing back and is carrying out the isolating effect of silica gel column chromatography.
Summary of the invention:
The objective of the invention is to overcome shortcomings such as the routine techniques extraction yield is relatively low, dna purity is low, a kind of method of utilizing forulic acid in the enriching and purifying macroporous resin rattletop is provided.
For achieving the above object, the technical solution used in the present invention is:
A kind of method of utilizing forulic acid in the enriching and purifying macroporous resin rattletop, its step is as follows:
(1) dried rattletop being pulverized the back extracts with alcohol heating reflux;
(2) will the extracting solution decompression recycling ethanol be got primary extract through the rattletop extracting solution suction filtration of step (1) processing;
(3) obtaining primary extract being added ethyl acetate extraction, is 2.0～2.5 with its pH value of acid accent, leaves standstill, suction filtration and be washed with water to neutrality, and concentrating under reduced pressure gets the forulic acid crude extract;
(4) gained forulic acid crude extract is adsorbed with macroporous adsorbent resin;
(5) with Different concentrations of alcohol macroporous adsorbent resin is carried out wash-out, follow the tracks of with tlc and detect, collect each stepwise elution liquid of forulic acid;
(6) each stepwise elution liquid of forulic acid is concentrated recovery ethanol, get the forulic acid work in-process, its content is more than 35%;
(7) with silica gel column chromatography on the gained forulic acid work in-process, and with acetone, methyl alcohol carries out wash-out with the different volumes ratio, and tlc is followed the tracks of and detected, and collects each stepwise elution liquid of forulic acid;
(8) with collected forulic acid elutriant, adopt activated carbon decolorizing, recrystallization method refining forulic acid, its content is more than 90%.
In the described step (1), cross 40～80 mesh sieves after rattletop is pulverized and carrying out organic solvent extraction.
In the described step (1), extracting used ethanol alcoholic degree is 80%, and extraction time is 2～4 hours, extracts 2～3 times.
In the described step (1), the method for extraction is one or more in infusion method, reflux extraction, percolation, decocting method, the continuous extraction.
In the described step (1), adding the alcoholic acid volume is 5～10 times that rattletop is pulverized volume.
In the described step (3), the amount that adds ethyl acetate is by volume calculated 5～10 times into the extract alcoholic solution, and regulating the used acid of pH value is hydrochloric acid.
Used macroporous adsorbent resin is a kind of in Tianjin Nankai University X-5, the NKA-9, S-8, D 3520, D4006, H103, D4020, AB-8H and the NKA-II type resin that are produced in the described step (4), is adsorbed as Static Adsorption or dynamic adsorption.
Wash-out described in the described step (5) carries out wash-out for the ethanol with 30～90%.
Described in step (5) and (7), the detection method of being taked is tlc and follows the tracks of detection.
The acetone of being taked in the described step (7) and the volume of methyl alcohol are 1～7: 1.
The present invention uses macroporous absorption technology separation and purification forulic acid, and is good to the adsorption selectivity of forulic acid, and the fast parsing of absorption is also fast, and loading capacity is bigger; Extract convenient and swiftly, raw material sources are abundant, low production cost, separating effect is obvious, the dna purity height can obtain forulic acid work in-process and content the forulic acid finished product 90% or more of content more than 35%, has overcome the shortcoming that conventional extraction yield is relatively low, dna purity is low.
The present invention selects that physico-chemical property is stable, surface-area is big, exchange velocity is very fast, physical strength is high, contamination resistance is strong, the macroporous adsorbent resin of Heat stability is good for use, be not dissolved in acid, alkali and organic matchmaker, better to the organism selectivity, the influence that not existed by inorganic salts and strong ion low molecular compound, can from solution, adsorb forulic acid selectively by physical adsorption, absorption is fast, parsing is also fast, and loading capacity is bigger.
Embodiment:
Embodiment 1: a kind of method of utilizing forulic acid in the enriching and purifying macroporous resin rattletop, and its step is as follows:
(1) will be dried rattletop pulverize the back and cross 60 mesh sieves, with the alcohol reflux of long-pending 5 times of rattletop powder 2 times, each 2h;
(2) will the extracting solution decompression recycling ethanol be got primary extract through the rattletop extracting solution suction filtration of step (1) processing;
(3) obtaining primary extract being added volume is that the ethyl acetate of 10 times of extract alcoholic solution volumes extracts, and is 2.0 with its pH value of acid accent then, leaves standstill, suction filtration, decompression and solvent recovery get the forulic acid crude extract;
(4) the gained forulic acid is carried thing with adsorbing on the macroporous adsorption resin chromatography post, used macroporous resin is the NKA-II type resin that Tianjin Nankai University is produced;
(5) in macroporous adsorbent resin layer post, carry out gradient elution successively with 30%, 40%, 50%, 60%, 70%, 80%, 90% ethanol, follow the tracks of with tlc and detect, collect each stepwise elution liquid of forulic acid;
(6) each stepwise elution liquid of forulic acid is concentrated recovery ethanol, obtaining content is 35% forulic acid work in-process;
(7) with silica gel column chromatography on the gained forulic acid work in-process, and use acetone, methyl alcohol carries out gradient elution with 1: 1,2: 1,3: 1,4: 1,5: 1,6: 1,7: 1 volume ratio successively, and tlc is followed the tracks of and detected, and collects each stepwise elution liquid of forulic acid;
(8), adopt activated carbon decolorizing, refining content 90% forulic acid that obtains of recrystallization method with collected forulic acid elutriant.
Case study on implementation 2: a kind of method of utilizing forulic acid in the enriching and purifying macroporous resin rattletop, its step is as follows:
(1) will be dried rattletop pulverize the back and cross 40 mesh sieves, with the alcohol reflux of long-pending 8 times of rattletop powder 3 times, each 3h;
(2) will the extracting solution decompression recycling ethanol be got primary extract through the rattletop extracting solution suction filtration of step (1) processing;
(3) obtaining primary extract being added volume is that the ethyl acetate of 8 times of extract alcoholic solution volumes extracts, and is 2.3 with its pH value of acid accent then, leaves standstill, suction filtration, decompression and solvent recovery get the forulic acid crude extract;
(4) gained forulic acid crude extract is adsorbed with macroporous adsorbent resin, used macroporous resin is the D4006 type resin that Tianjin Nankai University is produced;
(5) carry out wash-out with 30%, 50%, 70%, 90% ethanol at macroporous adsorbent resin, follow the tracks of with tlc and detect, collect each stepwise elution liquid of forulic acid;
(6) each stepwise elution liquid of forulic acid is concentrated recovery ethanol, obtain content 37% forulic acid work in-process;
(7) with silica gel column chromatography on the gained forulic acid work in-process, and use acetone, methyl alcohol carries out gradient elution with 1: 1,2: 1,3: 1,4: 1,5: 1,6: 1,7: 1 volume ratio successively, and tlc is followed the tracks of and detected, and collects each stepwise elution liquid of forulic acid;
(8), adopt activated carbon decolorizing, refining content 94% forulic acid that obtains of recrystallization method with collected forulic acid elutriant.
Case study on implementation 3: a kind of method of utilizing forulic acid in the enriching and purifying macroporous resin rattletop, its step is as follows:
(1) dried rattletop is pulverized the back and cross 80 mesh sieves, the ethanol that amasss 10 times with the rattletop powder returns extraction 2 times, each 4h;
(2) will the extracting solution decompression recycling ethanol be got primary extract through the rattletop extracting solution suction filtration of step (1) processing;
(3) obtaining primary extract being added volume is that the ethyl acetate of 5 times of extract alcoholic solution volumes extracts, and is 2.5 with its pH value of acid accent then, leaves standstill, suction filtration, decompression and solvent recovery get the forulic acid crude extract;
(4) with gained forulic acid crude extract with the macroporous adsorption resin chromatography pillar, on adsorb, used macroporous resin is the NKA-9 type resin that Tianjin Nankai University is produced;
(5) in the macroporous adsorption resin chromatography pillar, carry out gradient elution successively with 40%, 60%, 80% ethanol, follow the tracks of with tlc and detect, collect each stepwise elution liquid of forulic acid;
(6) each stepwise elution liquid of forulic acid is concentrated recovery ethanol, obtain content 35% forulic acid work in-process;
(7) with silica gel column chromatography on the gained forulic acid work in-process, and use acetone, methyl alcohol carries out gradient elution with 1: 1,2: 1,3: 1,4: 1,5: 1,6: 1,7: 1 volume ratio successively, and tlc is followed the tracks of and detected, and collects each stepwise elution liquid of forulic acid;
(8), adopt activated carbon decolorizing, refining content 92% forulic acid that obtains of recrystallization method with collected forulic acid elutriant.
Claims (10)
1. a method of utilizing forulic acid in the enriching and purifying macroporous resin rattletop is characterized in that, its step is as follows:
(1) dried rattletop being pulverized the back extracts with alcohol heating reflux;
(2) the rattletop extracting liquid filtering that will handle through (1), filtrate recycling ethanol gets primary extract;
(3) with institute results primary extract with adding ethyl acetate extraction, adjust pH is to 2-2.5, separates, the collecting precipitation thing, and is washed with water to neutrality, obtains the crude extract of forulic acid.
(4) gained forulic acid crude extract is adsorbed with macroporous adsorbent resin;
(5) with the different concentration ethanol aqueous solution macroporous adsorbent resin is carried out wash-out, collect each stepwise elution liquid of forulic acid;
(6) the forulic acid elutriant is concentrated the recovery eluent, get the forulic acid work in-process;
(7) with silica gel column chromatography on the gained forulic acid work in-process, and with methyl alcohol, acetone carries out wash-out with the different volumes ratio, collects each stepwise elution liquid of forulic acid;
(8) with collected that the forulic acid elutriant carries out the purified forulic acid.
2. its speciality of method of forulic acid in the enriching and purifying macroporous resin rattletop of utilizing according to claim 1 is: in the described step (1), cross 40～80 mesh sieves behind the rattletop powder and carry out the alcohol heating reflux extraction again.
3. the method for utilizing forulic acid in the enriching and purifying macroporous resin rattletop according to claim 2 is characterized in that: in affiliated step (1), concentration of ethanol is 80%, can extract each 2～4h 2～3 times.
4. the method for utilizing forulic acid in the enriching and purifying macroporous resin rattletop according to claim 3, it is characterized in that: in the described step (1), the method of extracting is pickling process, reflux extraction, one or more in percolation, decocting method, the continuous extraction.
5. the method for utilizing forulic acid in the enriching and purifying macroporous resin rattletop according to claim 4 is characterized in that; Under step (1) in, add the alcoholic acid volume and be long-pending 5～10 times of rattletop powder.
6. the method for utilizing forulic acid in the enriching and purifying macroporous resin rattletop according to claim 5, it is characterized in that: in described step (3), the amount that adds ethyl acetate is 5～10 times of extract alcoholic solution by volume, and regulating the used acid of pH value is hydrochloric acid.
7. the method for utilizing forulic acid in the enriching and purifying macroporous resin rattletop according to claim 6 is characterized in that: be adsorbed as Static Adsorption or dynamic adsorption described in the step (4): the wash-out described in the step (5) carries out wash-out for the aqueous ethanolic solution with 30～90%.
8. the method for utilizing forulic acid in the enriching and purifying macroporous resin rattletop according to claim 7 is characterized in that: in step (5) and (7), adopt tlc to follow the tracks of in the elution process and detect.
9. the method for utilizing forulic acid in the enriching and purifying macroporous resin rattletop according to claim 8 is characterized in that: in the step (7) the acetone that adopts and methyl alcohol to get volume ratio be 1～7: 1.
10. the method for utilizing forulic acid in the enriching and purifying macroporous resin rattletop according to claim 7 is characterized in that: in step (8), adopt activated carbon decolorizing, recrystallization method to make with extra care.
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Cited By (5)
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| CN103709029A (en) * | 2013-12-13 | 2014-04-09 | 大兴安岭嘉迪欧营养原料有限公司 | Process for extracting and purifying ferulic acid from angelica cartilaginomarginata Nakai |
| CN105497169A (en) * | 2016-01-06 | 2016-04-20 | 南京海源中药饮片有限公司 | Method for extracting phenolic acid effective constituents of rhizome cimicifugae |
| CN107074718A (en) * | 2015-07-23 | 2017-08-18 | 实验室明卡布公司 | Purify forulic acid and/or the method for its salt |
| CN107652179A (en) * | 2017-10-31 | 2018-02-02 | 桂林纽泰生物科技有限公司 | A kind of method that forulic acid is extracted from Desmodium styracifolium |
| CN111705031A (en) * | 2020-07-08 | 2020-09-25 | 四川盈嘉合生科技有限公司 | Genetically engineered bacterium for producing ferulic acid and biosynthesis method of ferulic acid |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103709029A (en) * | 2013-12-13 | 2014-04-09 | 大兴安岭嘉迪欧营养原料有限公司 | Process for extracting and purifying ferulic acid from angelica cartilaginomarginata Nakai |
| CN103709029B (en) * | 2013-12-13 | 2016-06-29 | 大兴安岭嘉迪欧营养原料有限公司 | A kind of technique of extraction purification ferulic acid from Guyuling Capsule |
| CN107074718A (en) * | 2015-07-23 | 2017-08-18 | 实验室明卡布公司 | Purify forulic acid and/or the method for its salt |
| CN105497169A (en) * | 2016-01-06 | 2016-04-20 | 南京海源中药饮片有限公司 | Method for extracting phenolic acid effective constituents of rhizome cimicifugae |
| CN107652179A (en) * | 2017-10-31 | 2018-02-02 | 桂林纽泰生物科技有限公司 | A kind of method that forulic acid is extracted from Desmodium styracifolium |
| CN111705031A (en) * | 2020-07-08 | 2020-09-25 | 四川盈嘉合生科技有限公司 | Genetically engineered bacterium for producing ferulic acid and biosynthesis method of ferulic acid |
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