CN102443619A - Method for extracting chlorogenic acid and hederagenin from honeysuckle flower - Google Patents

Method for extracting chlorogenic acid and hederagenin from honeysuckle flower Download PDF

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Publication number
CN102443619A
CN102443619A CN2010105001623A CN201010500162A CN102443619A CN 102443619 A CN102443619 A CN 102443619A CN 2010105001623 A CN2010105001623 A CN 2010105001623A CN 201010500162 A CN201010500162 A CN 201010500162A CN 102443619 A CN102443619 A CN 102443619A
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Prior art keywords
hederagenin
adds
extracting
chlorogenicacid
chlorogenic acid
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CN2010105001623A
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李法庆
杨成东
刘东锋
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Suzhou Baozetang Medical Technology Co Ltd
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Suzhou Baozetang Medical Technology Co Ltd
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Abstract

The invention relates to a method for extracting chlorogenic acid and hederagenin from honeysuckle flower. The method is characterized by comprising the following steps of: smashing the honeysuckle flower; extracting with a 70-90 percent ethanol solution; recovering ethanol from an extracting solution under reduced pressure; adding water into a concentrated solution for dispersing; adding into a macroporous resin column for adsorbing; eluting with a 40-70 percent of ethanol solution; recovering ethanol from an eluent and adding n-butyl alcohol for extracting; recovering n-butyl alcohol; adjusting the pH of the concentrated solution to 4-7, and adding a biological enzyme for performing enzymolysis; concentrating a hydrolysate; and filtering to obtain a solid and a filtrate; and purifying the solid and the filtrate respectively to obtain a hederagenin product and a chlorogenic acid production. The method has simple process operation and high raw material utilization ratio, and is suitable for industrial production.

Description

The method of chlorogenic acid extracting and hederagenin from Japanese Honeysuckle
Technical field:
The invention belongs to the Separation of Natural Products technical field, especially relate to a kind of from Japanese Honeysuckle the method for chlorogenic acid extracting and hederagenin.
Background technology:
Chlorogenicacid, molecular formula are C 16H 18O 9, 3-caffetannic acid, semihydrate are needle crystal (water), 110 ℃ become anhydrous compound.Soluble in water, ethanol and acetone, the atomic vinyl acetic monomer that is dissolved in.
Hederagenin, molecular formula are C 30H 48O 4, (3beta, 4alpha)-3, the acid of 23-dihydroxyl olean-12-alkene-28-is dissolved in ethanol, methyl alcohol, acetate, oxyhydroxide alkaline solution, water insoluble, ether, benzene, chloroform and sherwood oil.
Japanese Honeysuckle is the caprifoliaceae plant dry flower of honeysuckle, have clearing heat and detoxicating, the effect of wind-heat dissipating.Be used for the swollen furunculosis of carbuncle, larynx numbness erysipelas, the heat poison, bloody flux, common cold due to wind-heat, the seasonal febrile diseases heating is one of clinical Chinese medicinal materials commonly used.The Japanese Honeysuckle chemical constitution study shows that it contains organic acid, triterpene saponin etc.Chlorogenicacid is the main effective constituent of organic acid, and triterpenoid saponin is main with Hederagenin.That chlorogenicacid has is anti-oxidant, remove radical, anti-microbial activity, also has flavouring and colour-preserving function simultaneously, can be used for the preservation and antisepsis of food and fruit.Aspect anti-oxidant, chlorogenicacid increases resistance of oxidation with concentration and strengthens, and high purity is better than the chlorogenicacid of low-purity.Aspect the removing radical, chlorogenicacid has stronger removing ability, has selectivity, and the different removing abilities of purity differ bigger.Aspect anti-microbial activity, chlorogenicacid all has stronger restraining effect to intestinal bacteria and streptococcus aureus.Hederagenin belongs to the pentacyclic triterpene constituents, has cholagogic, protects the liver, antitumor action.
The chlorogenicacid source is mainly the Japanese Honeysuckle and the bark of eucommia at present, and (application number: 200910115669.4) " method that a kind of chlorogenicacid extracts ", this patent disclosed method are from Japanese Honeysuckle, Folium Eucommiae, Cortex Eucommiae, to extract and the preparation chlorogenicacid like patent; Existing process for extracting is mainly water extraction, supercritical fluid extraction, membrane separation process, lead salt precipitation and macroporous resin column adsorption method; Like patent (application number: 03129007.8) " compsn of chlorogenicacid, isochlorogenic acid and its medical usage "; This patent disclosed method be from Japanese Honeysuckle through decocting twice, decocting liquid is evaporated to certain volume, rare milk of lime suspension liquid transfers pH to alkalescence; Spinning; Throw out and 2 times of ethanol grind well to stir and add diluted acid accent pH to 3, and centrifugal, supernatant adds the alkali crystallization and promptly gets chlorogenicacid.It is not high that water is put forward milk of lime precipitator method chlorogenicacid yield, and purity is low; The supercritical fluid extraction expense is higher, is unfavorable for suitability for industrialized production; Membrane separation process has certain restriction to pore size; The lead salt deposition has been used deleterious heavy metal, and chlorogenicacid is had pollution.And the hederagenin multi-source is in girald acanthopanax bark leaf, Japanese Honeysuckle and dimension medicine nigella glandulifera Freyn seed; The main macroporous resin adsorption again that adopts after the acid hydrolysis; (application number: 200710146725.1) " hederagenin ", this patent disclosed method are the hederagenins that from dimension medicine nigella glandulifera Freyn seed, adopts the method extraction of degreasing, extraction and macroporous resin adsorption like patent.And from Japanese Honeysuckle simultaneously extraction separation obtain chlorogenicacid and two kinds of materials of hederagenin method seldom.
Summary of the invention:
The present invention want the technical solution problem provide a kind of from Japanese Honeysuckle the method for chlorogenic acid extracting and hederagenin.
In order to address the above problem, the present invention adopts following technical scheme to realize:
A kind of from Japanese Honeysuckle the method for chlorogenic acid extracting and hederagenin, it is characterized in that comprising following steps:
1) preparation:, add 10-15 and doubly measure 70-90% ethanolic soln heating and extracting 2-3 time, extracting solution decompression recycling ethanol solution raw material pulverizing; Liquid concentrator adds water-dispersion, adds macroporous resin column absorption again, washes sugared reaction negative; Doubly measure 60-80% ethanolic soln wash-out with 5-7 again, decompression recycling ethanol, liquid concentrator add water-saturated n-butanol extraction 3-5 time; Reclaim propyl carbinol, get liquid concentrator;
2) separate: above-mentioned liquid concentrator adds water-dispersion adjusting pH4-6 and adds the enzyme enzymolysis, concentrates enzymolysis solution and filters, and solids is the hederagenin crude extract, and mother liquor is a chlorogenicacid liquid;
3) hederagenin purifying: above-mentioned hederagenin crude extract is refluxed dissolving crystallized 2-3 time with absolute ethyl alcohol, and vacuum-drying promptly gets the hederagenin product;
4) chlorogenicacid purifying: above-mentioned mother liquor is added ethyl acetate extraction 3-5 time, and acetic acid ethyl acetate extract adds activated carbon decolorizing, filters and is concentrated into 1/6-1/15, adds an amount of ether, crystallization 1-2 time, and the vacuum-drying crystallisate gets the chlorogenicacid product.
Extract 50-70 ℃ of temperature in the said step 1), a kind of among the optional AB-8 of macroporous resin model, SPD-100, LSA-21 and the HZ806.
Said step 2) one or more in the optional glycase of enzyme, cellulase and the beta-glucan glycosides enzyme, hydrolysis temperature 40-55 ℃, enzymolysis time is no less than 24 hours, regulates sour optional organic acid or the mineral acid of pH.
Advantage of the present invention in sum is:
1) the present invention's while chlorogenic acid extracting and two kinds of active substances of hederagenin from Japanese Honeysuckle have improved utilization ratio of raw materials, have reduced cost.
2) the present invention adopts enzymolysis, and mild condition can not destroyed the aglycon structure, and yield is high, also is beneficial to the chlorogenicacid purifying simultaneously.
Embodiment:
Embodiment 1:
Pulverize Japanese Honeysuckle, get 1kg, drop into extractor, add the 15kg90% ethanolic soln and be heated to 55 ℃ of extractions 2 hours; Suction filtration liquid adds the 10kg90% ethanolic soln again and extracts 1 time, obtains liquid concentrator behind the extracting solution decompression recycling ethanol solution, and liquid concentrator adds the 4L water-dispersion; Add the absorption of 1L SPD-100 macroporous resin column, flow velocity 1L/h, absorption is washed sugared reaction negative after finishing; Use 7L60% ethanolic soln wash-out again, collect the elutriant decompression recycling ethanol, add 1L water-saturated n-butanol extraction 5 times, reclaim propyl carbinol; Liquid concentrator adds suitable quantity of water and regulates pH4 with hydrochloric acid, add the 5g cellulase, enzymolysis 30h under 55 ℃ the temperature; Concentrate enzymolysis solution and filter, solids refluxes to dissolve with the 500ml absolute ethyl alcohol and filters, and places crystallization; Crystallisate refluxes dissolving crystallized 2 times with absolute ethyl alcohol again, leaches crystallization vacuum-drying and promptly gets hederagenin product 4.1g, content 99.1%; The enzymolysis mother liquor adds the 600ml ethyl acetate extraction 3 times, and acetic acid ethyl acetate extract adds 10g gac reflux decolour, filters and is concentrated into 1/6 of original volume; Add the 25ml ether; Place crystallization, repeat 2 vacuum-drying crystallisates of crystallization and get chlorogenicacid product 7.2g, content 94.7%.
Embodiment 2:
Pulverize Japanese Honeysuckle, get 1kg, drop into extractor, add the 15kg70% ethanolic soln and be heated to 70 ℃ of extractions 1 hour; Suction filtration liquid adds the 15kg70% ethanolic soln again and extracts 2 times, obtains liquid concentrator behind the extracting solution decompression recycling ethanol solution, and liquid concentrator adds the 1L water-dispersion; Add the absorption of 1L AB-8 macroporous resin column, flow velocity 2kg/h, absorption is washed sugared reaction negative after finishing; Use 5L80% ethanolic soln wash-out again, collect the elutriant decompression recycling ethanol, add 4L water-saturated n-butanol extraction 4 times; Reclaim propyl carbinol, liquid concentrator adds the suitable quantity of water Hydrocerol A and regulates pH5, enzymolysis 24h under the temperature that adding 5g cellulase is 40 ℃; Concentrate enzymolysis solution and filter, solids refluxes with the 600ml absolute ethyl alcohol and dissolves, and filters and places crystallization; Crystallisate refluxes dissolving crystallized again with absolute ethyl alcohol, leach crystallization vacuum-drying and promptly get hederagenin product 4.5g, content 97%; Above-mentioned enzymolysis mother liquor adds the 300ml ethyl acetate extraction 5 times, and acetic acid ethyl acetate extract adds the 15g activated carbon decolorizing, filters and is concentrated into 1/10 of original volume, adds the 15ml ether, places crystallization, and the vacuum-drying crystallisate gets chlorogenicacid product 8.7g, content 91%.
Embodiment 3:
Pulverize Japanese Honeysuckle, get 1kg, drop into extractor, add the 12kg80% ethanolic soln and be heated to 60 ℃ of extractions 1 hour; Suction filtration liquid adds the 15kg80% ethanolic soln again and extracts 2 times, obtains liquid concentrator behind the extracting solution decompression recycling ethanol solution, and liquid concentrator adds the 2L water-dispersion; Add the absorption of 1L LSA-21 macroporous resin column, flow velocity 1kg/h, absorption is washed sugared reaction negative after finishing; Use 6L70% ethanolic soln wash-out again, collect the elutriant decompression recycling ethanol, add 5L water-saturated n-butanol extraction 3 times; Reclaim propyl carbinol, add suitable quantity of water and regulate pH4, enzymolysis 48h under the temperature that adding 2g beta-glucan glycosides enzyme is 50 ℃ with sulfuric acid; Concentrate enzymolysis solution and filter, solids refluxes with the 500ml absolute ethyl alcohol and dissolves, and places crystallization; Crystallisate refluxes dissolving crystallized again with absolute ethyl alcohol, leach crystallization vacuum-drying and promptly get hederagenin product 5g, content 98.2%; Above-mentioned enzymolysis mother liquor adds the 200ml ethyl acetate extraction 5 times, and acetic acid ethyl acetate extract adds the 30g activated carbon decolorizing, filters and is concentrated into 1/12 of original volume, adds the 10ml ether, places crystallization, and the vacuum-drying crystallisate gets chlorogenicacid product 8.9g, content 94.2%.
Embodiment 4:
Pulverize Japanese Honeysuckle, get 1kg, drop into extractor, add the 12kg80% ethanolic soln and be heated to 60 ℃ of extractions 1 hour; Suction filtration liquid adds the 10kg80% ethanolic soln again and extracts 2 times, obtains liquid concentrator behind the extracting solution decompression recycling ethanol solution, and liquid concentrator adds the 2L water-dispersion; Add the absorption of 1L HZ806 macroporous resin column, flow velocity 1.5kg/h, absorption is washed sugared reaction negative after finishing; Use 6L70% ethanolic soln wash-out again, collect the elutriant decompression recycling ethanol, add 3L water-saturated n-butanol extraction 5 times, reclaim propyl carbinol; Liquid concentrator adds suitable quantity of water and regulates pH5 with Hydrocerol A, adds 5g beta-glucan glycosides enzyme and cellulase, enzymolysis 30h under 50 ℃ the temperature; Concentrate enzymolysis solution and filter, solids refluxes with the 500ml absolute ethyl alcohol and dissolves, and places crystallization; Crystallisate refluxes dissolving crystallized again with absolute ethyl alcohol, leach crystallization vacuum-drying and promptly get hederagenin product 5g, content 98.2%; Above-mentioned enzymolysis mother liquor adds the 200ml ethyl acetate extraction 5 times, and acetic acid ethyl acetate extract adds the 15g activated carbon decolorizing, filters and is concentrated into 1/12 of original volume, adds the crystallization of 10ml ether, crystallization 2 times, and the vacuum-drying crystallisate gets chlorogenicacid product 6.5g, content 97%.
Embodiment 5:
Pulverize Japanese Honeysuckle, get 10kg, drop into extractor, add the 100kg80% ethanolic soln and be heated to 60 ℃ of extractions 1 hour; Suction filtration liquid adds the 100kg80% ethanolic soln again and extracts 2 times, obtains liquid concentrator behind the extracting solution decompression recycling ethanol solution, and liquid concentrator adds the 20L water-dispersion; Add the absorption of 10L LSA-21 macroporous resin column, flow velocity 13kg/h, absorption is washed sugared reaction negative after finishing; Use 60L70% ethanolic soln wash-out again, collect the elutriant decompression recycling ethanol, add 40L water-saturated n-butanol extraction 4 times, reclaim propyl carbinol; Liquid concentrator adds suitable quantity of water hydrochloric acid and regulates pH4, adds 50g beta-glucan glycosides enzyme and glycase, enzymolysis 36h under 50 ℃ the temperature; Concentrate enzymolysis solution and filter, solids refluxes with the 5L absolute ethyl alcohol and dissolves, and places crystallization; Crystallisate refluxes dissolving crystallized 2 times with absolute ethyl alcohol again, leaches crystallization vacuum-drying and promptly gets hederagenin product 49g, content 98.5%; Above-mentioned enzymolysis mother liquor adds the 4L ethyl acetate extraction 3 times, and acetic acid ethyl acetate extract adds the 200g activated carbon decolorizing, filters and is concentrated into 1/15 of original volume, adds the 100ml ether, crystallization 2 times, and the vacuum-drying crystallisate gets chlorogenicacid product 70g, content 96%.

Claims (3)

1. the method for chlorogenic acid extracting and hederagenin from Japanese Honeysuckle is characterized in that comprising following steps:
1) preparation:, add 10-15 and doubly measure 70-90% ethanolic soln heating and extracting 2-3 time, extracting solution decompression recycling ethanol solution raw material pulverizing; Liquid concentrator adds water-dispersion, adds macroporous resin column absorption again, washes sugared reaction negative; Doubly measure 60-80% ethanolic soln wash-out with 5-7 again, decompression recycling ethanol, liquid concentrator add water-saturated n-butanol extraction 3-5 time; Reclaim propyl carbinol, get liquid concentrator;
2) separate: above-mentioned liquid concentrator adds water-dispersion adjusting pH4-6 and adds the enzyme enzymolysis, concentrates enzymolysis solution and filters, and solids is the hederagenin crude extract, and mother liquor is a chlorogenicacid liquid;
3) hederagenin purifying: above-mentioned hederagenin crude extract is refluxed dissolving crystallized 2-3 time with absolute ethyl alcohol, and vacuum-drying promptly gets the hederagenin product;
4) chlorogenicacid purifying: above-mentioned mother liquor is added ethyl acetate extraction 3-5 time, and acetic acid ethyl acetate extract adds activated carbon decolorizing, filters and is concentrated into 1/6-1/15, adds an amount of ether, crystallization 1-2 time, and the vacuum-drying crystallisate gets the chlorogenicacid product.
2. the method for chlorogenic acid extracting and hederagenin simultaneously from Japanese Honeysuckle according to claim 1 is characterized in that in the said step 1) 50-70 ℃ of extraction temperature, a kind of among the optional AB-8 of macroporous resin model, SPD-100, LSA-21 and the HZ806.
3. the method for chlorogenic acid extracting and hederagenin simultaneously from Japanese Honeysuckle according to claim 1; It is characterized in that said step 2) in the optional glycase of enzyme, cellulase and the beta-glucan glycosides enzyme one or more; Hydrolysis temperature 40-55 ℃; Enzymolysis time is no less than 24 hours, regulates sour optional organic acid or the mineral acid of pH.
CN2010105001623A 2010-10-09 2010-10-09 Method for extracting chlorogenic acid and hederagenin from honeysuckle flower Pending CN102443619A (en)

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Cited By (7)

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Publication number Priority date Publication date Assignee Title
CN103860622A (en) * 2012-12-07 2014-06-18 廉吉芳 Method for extracting saponin compounds from honeysuckle
CN104387273A (en) * 2014-10-20 2015-03-04 湖北大别山药业有限公司 Method for extracting chlorogenic acid from honeysuckle
CN104523698A (en) * 2013-09-28 2015-04-22 杨小林 Application of hederagenin to preparation of drug for resisting to HEC-1 tumors of endometrial carcinoma cells
CN107879937A (en) * 2017-10-24 2018-04-06 四川九章生物科技有限公司 A kind of new crystal of chlorogenic acid and preparation method thereof
CN111533658A (en) * 2020-04-20 2020-08-14 湖南鸿利药业股份有限公司 Method for extracting high-purity chlorogenic acid from honeysuckle
CN114085778A (en) * 2021-11-04 2022-02-25 浙江工业大学 Rhizopus oryzae JYH-4-23 and application thereof in extraction of chlorogenic acid in honeysuckle
CN115108914A (en) * 2022-07-13 2022-09-27 湖南凯耀生物科技有限公司 Preparation method and device for industrially extracting chlorogenic acid based on honeysuckle

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103860622A (en) * 2012-12-07 2014-06-18 廉吉芳 Method for extracting saponin compounds from honeysuckle
CN104523698A (en) * 2013-09-28 2015-04-22 杨小林 Application of hederagenin to preparation of drug for resisting to HEC-1 tumors of endometrial carcinoma cells
CN104523698B (en) * 2013-09-28 2019-09-13 杨小林 Application of the hederagenin in preparation anti-endometrial cancer cell HEC-1 tumour medicine
CN104387273A (en) * 2014-10-20 2015-03-04 湖北大别山药业有限公司 Method for extracting chlorogenic acid from honeysuckle
CN107879937A (en) * 2017-10-24 2018-04-06 四川九章生物科技有限公司 A kind of new crystal of chlorogenic acid and preparation method thereof
CN111533658A (en) * 2020-04-20 2020-08-14 湖南鸿利药业股份有限公司 Method for extracting high-purity chlorogenic acid from honeysuckle
CN114085778A (en) * 2021-11-04 2022-02-25 浙江工业大学 Rhizopus oryzae JYH-4-23 and application thereof in extraction of chlorogenic acid in honeysuckle
CN114085778B (en) * 2021-11-04 2023-09-15 浙江工业大学 Rhizopus oryzae JYH-4-23 and application thereof in extraction of chlorogenic acid in honeysuckle
CN115108914A (en) * 2022-07-13 2022-09-27 湖南凯耀生物科技有限公司 Preparation method and device for industrially extracting chlorogenic acid based on honeysuckle

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