CN104788515A - Method for preparing high-purity water-soluble oleuropein through reduced-pressure ultrasound-assisted extraction - Google Patents
Method for preparing high-purity water-soluble oleuropein through reduced-pressure ultrasound-assisted extraction Download PDFInfo
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- RFWGABANNQMHMZ-UHFFFAOYSA-N 8-acetoxy-7-acetyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline Natural products CC=C1C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(C(=O)OC)=COC1OC1OC(CO)C(O)C(O)C1O RFWGABANNQMHMZ-UHFFFAOYSA-N 0.000 title claims abstract description 60
- HKVGJQVJNQRJPO-UHFFFAOYSA-N Demethyloleuropein Natural products O1C=C(C(O)=O)C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(=CC)C1OC1OC(CO)C(O)C(O)C1O HKVGJQVJNQRJPO-UHFFFAOYSA-N 0.000 title claims abstract description 60
- RFWGABANNQMHMZ-HYYSZPHDSA-N Oleuropein Chemical compound O([C@@H]1OC=C([C@H](C1=CC)CC(=O)OCCC=1C=C(O)C(O)=CC=1)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RFWGABANNQMHMZ-HYYSZPHDSA-N 0.000 title claims abstract description 60
- 235000011576 oleuropein Nutrition 0.000 title claims abstract description 60
- RFWGABANNQMHMZ-CARRXEGNSA-N oleuropein Natural products COC(=O)C1=CO[C@@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)C(=CC)[C@H]1CC(=O)OCCc3ccc(O)c(O)c3 RFWGABANNQMHMZ-CARRXEGNSA-N 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 37
- 238000002137 ultrasound extraction Methods 0.000 title abstract description 11
- 238000000605 extraction Methods 0.000 claims abstract description 23
- 238000005516 engineering process Methods 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000001953 recrystallisation Methods 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 114
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- 239000000284 extract Substances 0.000 claims description 30
- 239000013078 crystal Substances 0.000 claims description 24
- 240000007817 Olea europaea Species 0.000 claims description 23
- 235000002725 Olea europaea Nutrition 0.000 claims description 21
- 238000000967 suction filtration Methods 0.000 claims description 19
- 239000012043 crude product Substances 0.000 claims description 18
- 238000001035 drying Methods 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000000706 filtrate Substances 0.000 claims description 15
- 230000001476 alcoholic effect Effects 0.000 claims description 13
- 230000006837 decompression Effects 0.000 claims description 12
- 239000012535 impurity Substances 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 9
- 238000004090 dissolution Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000001186 cumulative effect Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 238000002203 pretreatment Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 10
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- 239000003814 drug Substances 0.000 abstract description 3
- 238000004042 decolorization Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
- 238000002604 ultrasonography Methods 0.000 abstract 1
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000002131 composite material Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 210000003491 skin Anatomy 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 7
- UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 6
- 239000002024 ethyl acetate extract Substances 0.000 description 6
- 239000012528 membrane Substances 0.000 description 4
- 230000006378 damage Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 210000000630 fibrocyte Anatomy 0.000 description 3
- 229930182470 glycoside Natural products 0.000 description 3
- 150000002338 glycosides Chemical class 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- JUUBCHWRXWPFFH-UHFFFAOYSA-N Hydroxytyrosol Chemical compound OCCC1=CC=C(O)C(O)=C1 JUUBCHWRXWPFFH-UHFFFAOYSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 229930003944 flavone Natural products 0.000 description 2
- 235000011949 flavones Nutrition 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
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- 235000017173 flavonoids Nutrition 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229940114496 olive leaf extract Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 210000004927 skin cell Anatomy 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- UFJORDZSBNSRQT-UHFFFAOYSA-N 3-(4-oxo-2-phenylchromen-3-yl)-2-phenylchromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C(C=2C(C3=CC=CC=C3OC=2C=2C=CC=CC=2)=O)=C1C1=CC=CC=C1 UFJORDZSBNSRQT-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 102000029816 Collagenase Human genes 0.000 description 1
- 108060005980 Collagenase Proteins 0.000 description 1
- 241000207834 Oleaceae Species 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229960000074 biopharmaceutical Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000009084 cardiovascular function Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 208000013507 chronic prostatitis Diseases 0.000 description 1
- 229960002424 collagenase Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002212 flavone derivatives Chemical class 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 235000003248 hydroxytyrosol Nutrition 0.000 description 1
- 229940095066 hydroxytyrosol Drugs 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 201000007094 prostatitis Diseases 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicines Containing Plant Substances (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention discloses a method for preparing high-purity water-soluble oleuropein through reduced-pressure ultrasound-assisted extraction and belongs to the technical field of natural medicine extraction preparation. The method comprises steps as follows: pretreatment of medicinal materials, reduced-pressure ultrasound-assisted extraction, extraction-back extraction, decolorization and crystallization-recrystallization. For characteristics that the oleuropein is low in melting point, easy to decompose and the like, the vacuum degree produced by pressure reduction as well as the cavitation effect and the stirring action produced by ultrasound waves are used, a certain quantity of extracting solution is added, and a new technology for preparing the oleuropein with high purity and good water solubility with a simple separation purification technology is provided. The content of the oleuropein prepared with the technology is higher than 95%; the method has the advantages that the product yield is high, the technology is simple, separation and purification conditions are mild, the toxicity is low, the production cost is low and the like and is applicable to industrial production.
Description
Technical field
The present invention relates to a kind of method that high-purity water dissolubility oleuropein is prepared in extraction, be specifically related to a kind of method that depressurizing ultrasonic assisted extraction prepares oleuropein.
Background technology
Olive leaf is the leaf that Oleaceae wooden slippers olive belongs to olive tree (Olea europaea L), and it is mainly containing secoiridoid and glycosides, flavones and glycosides thereof, biflavone and the composition such as glycosides, low molecule tannin thereof.In Olive leaf P.E, main component is the pained material of iridoids, and that its activity is the highest is oleuropein (Oleuropein).Oleuropein molecular weight is 540.5, No. CAS: 32619-42-4.
Oleuropein is a kind of bimolecular structure phenols and Flavonoid substances, fusing point 87 ~ 89 DEG C, and easy moisture absorption can be decomposed under being exposed to air and sunlight.It has natural anti-oxidant, antitumor, delay senility, strengthen cardiovascular function, treatment chronic prostatitis, strengthening immunity, endocrine regulation system, protect the important nourishing function such as liver, anti-inflammatory, also have reducing blood-fat, hypoglycemic pharmacological action simultaneously, be widely used in the key areas such as food, makeup and bio-pharmaceuticals.
Oleuropein has powerful antibacterium and ntiviral characteristic, can be used for manufacturing caused disease and the treatment flu Dare medicines such as treatment virus, bacterium, protozoa, parasite and blood sucker.Oleuropein can also protect skin cells not by ultraviolet injury; prevent ultraviolet to the decomposition of skin membrane lipid; promote that fibrocyte generates collagen protein; reduce the secretion of fibrocyte collagenase, the anti-glycan reaction of cell membranes in tissue, thus highly protect fibrocyte; naturally resist the skin caused because of oxidation to destroy; more from UV uv damage, effectively maintain the tender and elasticity of skin, reach effect of skin care, tender skin.At present, the oleuropein of water-soluble high-content 90% is mainly used in skin care product, can protect skin cells not by ultraviolet injury, effectively maintains the tender and elasticity of skin, reaches the effect of holding up skin, tender skin.
Openly the extraction separation and purification technology of oleuropein is more at present, general employing alcohol extracting or alkaline extraction extract the effective constituent in olive leaf, then a series of purification procedures such as Column chromatography are carried out, obtain highly purified oleuropein, but traditional technique needs to use resin absorption or filter membrane purifying for improving product content further, power consumption is large, consumptive material is many, length consuming time, the yield of product is low, and industrial pollution is large; And because of characteristics such as its fusing point is low, easy decomposition, general hot formulation is often decomposed in its leaching process, finally causes its yield on the low side.Therefore, more or less there is certain drawback in conventional single extracting method.
Patent CN 102532217 A discloses the method for one " from leaf of Fructus oleae europaeae extraction and isolation high-content oleuropein ", and its method comprises: by olive leaf chopping, extract at low temperature, filtration, concentrated or directly chromatography, cryoconcentration, drying, finally obtain the oleuropein product that content is greater than 80%.Its with certain density ethanol or water for Extraction solvent extract at low temperature, utilize resin to connect or second adsorption chromatographic technique, greatly improve the content of product, but need regenerate or recycle because of resin, the more loaded down with trivial details cost adding technique of post-processed, production of cannot magnifying.Patent CN 102702287 A discloses the method for one " from olive leaf extraction purification oleuropein ", its method comprises: be that the alkali lye of 8-10 carries out normal temperature lixiviate to olive leaf by pH value, by gained extracting solution through molecular sieve type macroporous adsorbent resin column chromatography, then post is washed with the ethanol that volumetric concentration is 50-80%, collect the elutriant containing target component, concentrate drying, obtains the oleuropein of low levels; Be the polar solvent dissolving of 3.8-4.2 again by the oleuropein polarity number of low levels, suction filtration, filtrate concentrates, and obtains concentrated solution; In concentrated solution, add organic solvent again regulate polarity, under cold condition, place crystallize out, dry, obtain highly purified oleuropein.This technique is extracted because adopting alkali lye, and oleuropein can be made to be hydrolyzed into Hydroxytyrosol, and extraction time is long, and hydrolysis degree is high, finally causes the yield of product on the low side, is only about 4%.The application of macroporous adsorptive resins, can increase energy consumption, improves production cost.Patent CN 101003557 A discloses the preparation method that one " is rich in the olive leaf extract of high purity Oleuropein ", it comprises the following steps: first extract leaf of Fructus oleae europaeae with polar solvent, alkaline centrifugal settling again, obtain centrifugal clear liquid and throw out, then film integrated separation is carried out, obtain the concentrated solution by nanofiltration membrane, media adsorbs again, wash-out is carried out to adsorption medium and obtains elutriant, vacuum concentration, carry out vacuum lyophilization or spraying dry again, obtain Oleuropein content be greater than 50% be rich in high purity Oleuropein have Olive leaf P.E.This technique saves the energy, clean environment firendly, and step is more loaded down with trivial details, and need use membrane sepn and media adsorbs technology, cost is higher, not easily realizes suitability for industrialized production.Patent CN 102850416 A discloses " a kind of preparation method of olive leaf extract and equipment therefor ", the steps include: leaf of Fructus oleae europaeae first to use mixed solvent, extracts, vacuum filtration, obtain clear liquor through ultrasonic decompression boiling, carry out petroleum ether extraction removing oil-soluble impurities again and collect subnatant, by rotary evaporation to solvent without alcohol taste, redilution, diluent is by after macroporous resin purification, standing for some time makes Oleuropein and Flavonoid substances absorption fully, the ethanol-water mixed solvent re-using proper concn is by Oleuropein wash-out and collect target liquid, by the purifying of the target solution of collection through dextrane gel, ethanol-water solution wash-out is used after leaving standstill, regather the elutriant containing effective constituent, by its rotary evaporation extremely without alcohol taste, finally by extract that is dry or that obtain, wherein the large 85-92% of Oleuropein content and general flavone content reach 25-35%.This technique purification step is more complicated, and consumptive material, power consumption are comparatively large, cannot realize good economic benefit.Patent CN 102228514 A discloses " a kind of method extracting Oleuropein from leaf of Fructus oleae europaeae ", it comprises: after extracting with water or alcohol water mixed solvent, be separated through three steps successively after extracting solution is concentrated: macroporous resin adsorption also uses alcohol water solvent wash-out, decolorizing resin absorption (has the decolorizing resin of favourable absorption effect (Oleuropein to be had to the macroporous adsorbent resin of favourable absorption effect to the pigment in olive extract, wash-out removes other impurity), absorption removing pigment) and organic solvent extraction, progressively separation and purification is carried out to the Oleuropein in the middle of extracting solution, finally obtain the oleuropein extract of high-content, the content of Oleuropein is greater than 40%.This simple process, easy handling, but its product content is lower, directly cannot add in the middle of medicine or makeup, and need further separation and purification.
The present invention be directed to the defect of above-mentioned production technique, solve emphatically the on the low side and labile difficult problem of oleuropein extraction yield, again in conjunction with simple and easy and separation purifying technique effectively, develop rapidly and efficiently to extract and prepare that content is high, the oleuropein novel process of good water solubility, it is with short production cycle, extraction efficiency is high, separation purifying technique is easy, can realize green, environmental protection, reduces production cost, improve yield and the quality of product, be easy to suitability for industrialized production.
Summary of the invention
The present invention proposes first and hyperacoustic cavatition and second-order effect is combined with decompression technology, adopts composite extracting solution, by the separation purifying technique of simple and efficient, and the oleuropein sterling of preparation high purity, good water solubility.This technology effectively can prevent the decomposition of oleuropein, and improves while product yield, also can improve its purity, have simple to operate, high-efficiency environment friendly, with low cost, be easy to the features such as extension production.
For solving the problems of the technologies described above, the present invention by the following technical solutions:
1) raw materials pretreatment: cleaned by olive leaf, dry, pulverize, crosses 80 mesh sieves, obtains olive leaf powder, for subsequent use;
2) depressurizing ultrasonic extracts: olive leaf powder and composite extracting solution are pressed mass volume ratio 1g: 10-15mL and soaks 12-24 hour, at vacuum tightness 0.08-0.1MPa, under the condition of power 200-240W, temperature 35-40 DEG C, depressurizing ultrasonic extracts 30-50 minute, extracts twice; Suction filtration obtains filtrate.
3) extraction and back extraction: by step 2) extracting solution that obtains is evaporated to degree Beaume between 8-10, and be extracted with ethyl acetate 3 to 4 times, combining extraction liquid, be evaporated to without ethyl acetate, then strip through ether, further removal of impurities; By the medicinal extract after reextraction, decompression drying, obtains oleuropein crude product;
4) decolour: by step 3) the certain density alcoholic solution ultrasonic dissolution of oleuropein crude product that obtains, suction filtration, obtains settled solution, then adds proper amount of active carbon and carry out reflux desolventing technology;
5) crystallization-recrystallization: by step 4) solution carries out being evaporated to degree Beaume between 8-10 after the decolouring that obtains, dissolve with certain density alcohol, concentrating under reduced pressure alcoholic solution, to without alcohol taste, is dried, thermosol is carried out again by ethyl acetate, filtered while hot, leaves standstill under low temperature, after crystal is separated out, collecting by filtration crystal, again crystal is used ethyl acetate thermosol, carry out recrystallization by above-mentioned steps, good water solubility, oleuropein sterling that content is high can be prepared.
Particularly, step 2) described in composite extracting solution be 95% ethanol and 95% methyl alcohol by volume 1: 1 mixing solutions.
Particularly, step 2) described in the condition of suction filtration be: vacuum tightness 0.07-0.09MPa.
Particularly, step 3) described in the condition of concentrating under reduced pressure be: vacuum tightness 0.07-0.09MPa, temperature is 40-50 DEG C.
Particularly, step 3) described in concentrated solution be 1: 15-20 with the cumulative volume ratio of ethyl acetate.
Particularly, step 3) described in the mass volume ratio of concentrated extract and ether be 1: 5-10.
Particularly, step 3) described in the condition of decompression drying be: vacuum tightness 0.09-0.1MPa, temperature is 35-40 DEG C.
Particularly, step 3) described in certain density alcoholic solution be: the ethanol of 10-30% or methanol solution.
Particularly, step 4) described in the condition of reflux desolventing technology be: the amount of with the addition of of gac is the 2-3 ‰ of its weight, and temperature is 45-50 DEG C.
Particularly, step 5) described in the condition of concentrating under reduced pressure be: vacuum tightness 0.09-0.1MPa, temperature is 45-50 DEG C.
Particularly, step 3) described in certain density alcoholic solution be: the ethanol of 95% or methanol solution.
Particularly, step 5) described in the condition of ethyl acetate thermosol be: the mass volume ratio of oleuropein crude product and ethyl acetate is 1g: 8-10mL, and thermosol temperature is 45-50 DEG C.
Particularly, step 5) described in the condition of stand at low temperature be: cryogenic temperature is 0 to 5 DEG C, and the time left standstill is 12-24 hour.
Specific implementation method
[embodiment 1]
Get olive leaf 1kg, clean, dry, pulverized 80 mesh sieves, add composite extracting solution (95% ethanol and 95% methyl alcohol by volume 1: 1) 10L, soak 12h.Use depressurizing ultrasonic extraction equipment, at vacuum tightness 0.08MPa, power 200W, under the condition that temperature is 35 DEG C, depressurizing ultrasonic extracts 30 minutes, extract twice, and suction filtration merges twice filtrate under vacuum tightness 0.07MPa.At vacuum tightness 0.07MPa, temperature is that under the condition of 40 DEG C, concentrating under reduced pressure filtrate to degree Beaume is 8.The ethyl acetate of getting 3L is divided and is extracted concentrated solutions three times, collects acetic acid ethyl acetate extract, is evaporated to without ethyl acetate, then divides with the ether of 0.3L and carry out reextraction removal of impurities three times, and recovery extracted with diethyl ether phase, extracting phase carries out decompression drying, obtains oleuropein crude product.By the crude product after drying, with the ethanolic soln ultrasonic dissolution of 0.15L 10%, suction filtration, obtains settled solution, then adds 0.8g gac and carry out reflux desolventing technology.After decolouring, solution carries out being evaporated to degree Beaume is 8, dissolves with 0.1L 95% ethanol, and concentrating under reduced pressure alcoholic solution is extremely without alcohol taste, dry, then carry out 45 DEG C of thermosols by 0.1L ethyl acetate, filtered while hot, leave standstill under low temperature, after crystal is separated out, collecting by filtration crystal, then by crystal 0.07L ethyl acetate 45 DEG C of thermosols, recrystallization is carried out by above-mentioned steps, can prepare good water solubility, oleuropein sterling that content is high, its purity can reach 95.06%, and yield is 6.86%.
[embodiment 2]
Get olive leaf 5kg, clean, dry, pulverized 80 mesh sieves, add composite extracting solution 60L, soak 15h.Use depressurizing ultrasonic extraction equipment, at vacuum tightness 0.08MPa, power 220W, under the condition that temperature is 40 DEG C, depressurizing ultrasonic extracts 40 minutes, extract twice, and suction filtration merges twice filtrate under vacuum tightness 0.07MPa.At vacuum tightness 0.07MPa, temperature is that under the condition of 40 DEG C, concentrating under reduced pressure filtrate to degree Beaume is 8.The ethyl acetate of getting 15L divides three extraction concentrated solutions, and collect acetic acid ethyl acetate extract, be evaporated to without ethyl acetate, divide carry out reextraction removal of impurities three times with the ether of 1L, reclaim extracted with diethyl ether phase, extracting phase carries out decompression drying, obtains oleuropein crude product.By the crude product after drying, with the ethanolic soln ultrasonic dissolution of 0.8L 10%, suction filtration, obtains settled solution, then adds 5g gac and carry out reflux desolventing technology.After decolouring, solution carries out being evaporated to degree Beaume is 8, dissolves with 0.5L 95% ethanol, and concentrating under reduced pressure alcoholic solution is extremely without alcohol taste, dry, then carry out 45 DEG C of thermosols by 0.5L ethyl acetate, filtered while hot, leave standstill under low temperature, after crystal is separated out, collecting by filtration crystal, then by crystal 0.35L ethyl acetate 45 DEG C of thermosols, recrystallization is carried out by above-mentioned steps, can prepare good water solubility, oleuropein sterling that content is high, its purity can reach 95.34%, and yield is 7.03%.
[embodiment 3]
Get olive leaf 10kg, clean, dry, pulverized 80 mesh sieves, add composite extracting solution 130L, soak 18h.Use depressurizing ultrasonic extraction equipment, at vacuum tightness 0.08MPa, power 240W, under the condition that temperature is 40 DEG C, depressurizing ultrasonic extracts 50 minutes, extract twice, and suction filtration merges twice filtrate under vacuum tightness 0.07MPa.At vacuum tightness 0.07MPa, temperature is that under the condition of 40 DEG C, concentrating under reduced pressure filtrate to degree Beaume is 8.The ethyl acetate of getting 30L divides three extraction concentrated solutions, and collect acetic acid ethyl acetate extract, be evaporated to without ethyl acetate, divide carry out reextraction removal of impurities three times with the ether of 2L, reclaim extracted with diethyl ether phase, extracting phase carries out decompression drying, obtains oleuropein crude product.By the crude product after drying, with the ethanolic soln ultrasonic dissolution of 1.6L 10%, suction filtration, obtains settled solution, then adds 11g gac and carry out reflux desolventing technology.After decolouring, solution carries out being evaporated to degree Beaume is 8, dissolves with 0.5L 95% ethanol, and concentrating under reduced pressure alcoholic solution is extremely without alcohol taste, dry, then carry out 45 DEG C of thermosols by 0.8L ethyl acetate, filtered while hot, leave standstill under low temperature, after crystal is separated out, collecting by filtration crystal, then by crystal 0.7L ethyl acetate 45 DEG C of thermosols, recrystallization is carried out by above-mentioned steps, can prepare good water solubility, oleuropein sterling that content is high, its purity can reach 95.62%, and yield is 7.41%.
[embodiment 4]
Get olive leaf 100kg, clean, dry, pulverized 80 mesh sieves, add composite extracting solution 1500L, soak 20h.Use depressurizing ultrasonic extraction equipment, at vacuum tightness 0.08MPa, power 240W, under the condition that temperature is 40 DEG C, depressurizing ultrasonic extracts 50 minutes, and extract twice, under vacuum tightness 0.07MPa, suction filtration merges twice filtrate, at vacuum tightness 0.07MPa, temperature is that under the condition of 40 DEG C, concentrating under reduced pressure filtrate to degree Beaume is 8.The ethyl acetate of getting 300L divides three extraction concentrated solutions, and collect acetic acid ethyl acetate extract, be evaporated to without ethyl acetate, divide carry out reextraction removal of impurities three times with the ether of 21L, reclaim extracted with diethyl ether phase, extracting phase carries out decompression drying, obtains oleuropein crude product.By the crude product after drying, with the ethanolic soln ultrasonic dissolution of 17L 10%, suction filtration, obtains settled solution, then adds 120g gac and carry out reflux desolventing technology.After decolouring, solution carries out being evaporated to degree Beaume is 8, dissolves with 5L 95% ethanol, and concentrating under reduced pressure alcoholic solution is extremely without alcohol taste, dry, then carry out 45 DEG C of thermosols by 9L ethyl acetate, filtered while hot, leave standstill under low temperature, after crystal is separated out, collecting by filtration crystal, then by crystal 8L ethyl acetate 45 DEG C of thermosols, recrystallization is carried out by above-mentioned steps, can prepare good water solubility, oleuropein sterling that content is high, its purity can reach 95.83%, and yield is 7.49%.
[embodiment 5]
Get olive leaf 300kg, clean, dry, pulverized 80 mesh sieves, add composite extracting solution 4500L, soak 24h.Use depressurizing ultrasonic extraction equipment, at vacuum tightness 0.08MPa, power 240W, under the condition that temperature is 40 DEG C, depressurizing ultrasonic extracts 50 minutes, extract twice, and suction filtration merges twice filtrate under vacuum tightness 0.07MPa.At vacuum tightness 0.07MPa, temperature is that under the condition of 40 DEG C, concentrating under reduced pressure filtrate to degree Beaume is 8.The ethyl acetate of getting 900L divides three extraction concentrated solutions, and collect acetic acid ethyl acetate extract, be evaporated to without ethyl acetate, divide carry out reextraction removal of impurities three times with the ether of 60L, reclaim extracted with diethyl ether phase, extracting phase carries out decompression drying, obtains oleuropein crude product.By the crude product after drying, with the ethanolic soln ultrasonic dissolution of 50L 10%, suction filtration, obtains settled solution, then adds 360g gac and carry out reflux desolventing technology.After decolouring, solution carries out being evaporated to degree Beaume is 8, dissolves with 15L 95% ethanol, and concentrating under reduced pressure alcoholic solution is extremely without alcohol taste, dry, then carry out 45 DEG C of thermosols by 27L ethyl acetate, filtered while hot, leave standstill under low temperature, after crystal is separated out, collecting by filtration crystal, then by crystal 25L ethyl acetate 45 DEG C of thermosols, recrystallization is carried out by above-mentioned steps, can prepare good water solubility, oleuropein sterling that content is high, its purity can reach 95.90%, and yield is 7.51%.
[embodiment 6]
Get olive leaf 500kg, clean, dry, pulverized 80 mesh sieves, add composite extracting solution 7500L, soak 24h.Use depressurizing ultrasonic extraction equipment, at vacuum tightness 0.08MPa, power 240W, under the condition that temperature is 40 DEG C, depressurizing ultrasonic extracts 50 minutes, extract twice, and suction filtration merges twice filtrate under vacuum tightness 0.07MPa.At vacuum tightness 0.07MPa, temperature is that under the condition of 40 DEG C, concentrating under reduced pressure filtrate to degree Beaume is 8.The ethyl acetate of getting 1500L is divided and is carried out reextraction concentrated solution three times, and collect acetic acid ethyl acetate extract, be evaporated to without ethyl acetate, divide three abstraction impurity removals with the ether of 102L, recovery extracted with diethyl ether phase, extracting phase carries out decompression drying, obtains oleuropein crude product.By the crude product after drying, with the ethanolic soln ultrasonic dissolution of 75L 10%, suction filtration, obtains settled solution, then adds 600g gac and carry out reflux desolventing technology.After decolouring, solution carries out being evaporated to degree Beaume is 8, dissolves with 25L 95% ethanol, and concentrating under reduced pressure alcoholic solution is extremely without alcohol taste, dry, then carry out 45 DEG C of thermosols by 44L ethyl acetate, filtered while hot, leave standstill under low temperature, after crystal is separated out, collecting by filtration crystal, then by crystal 41L ethyl acetate 45 DEG C of thermosols, recrystallization is carried out by above-mentioned steps, can prepare good water solubility, oleuropein sterling that content is high, its purity can reach 95.98%, and yield is 7.50%.
Claims (11)
1. the method preparing high purity oleuropein is extracted in depressurizing ultrasonic coupling, it is characterized in that, comprises the steps:
1) medicinal material pre-treatment: cleaned by olive leaf, dry, pulverize, crosses 80 mesh sieves, obtains olive leaf powder, for subsequent use;
2) depressurizing ultrasonic extracts: olive leaf powder and extracting solution are pressed mass volume ratio 1g: 10-15mL and soak 12-24 hour, at vacuum tightness 0.08-0.1MPa, under the condition of power 200-240W, temperature 35-40 DEG C, depressurizing ultrasonic extracts 30-50 minute, extracts twice; Suction filtration obtains filtrate.
3) extraction and back extraction: by step 2) extracting solution that obtains is evaporated to degree Beaume between 8-10, and be extracted with ethyl acetate 3 to 4 times, combining extraction liquid, be evaporated to without ethyl acetate, then strip through ether, further removal of impurities; By the medicinal extract after reextraction, decompression drying, obtains oleuropein crude product;
4) decolour: by step 3) the certain density alcoholic solution ultrasonic dissolution of oleuropein crude product that obtains, suction filtration, obtains settled solution, then adds proper amount of active carbon and carry out reflux desolventing technology;
5) crystallization-recrystallization: by step 4) solution carries out being evaporated to degree Beaume between 8-10 after the decolouring that obtains, dissolve with certain density alcoholic solution, concentrating under reduced pressure alcoholic solution, to without alcohol taste, is dried, thermosol is carried out again by ethyl acetate, filtered while hot, leaves standstill under low temperature, after crystal is separated out, collecting by filtration crystal, again crystal is used ethyl acetate thermosol, carry out recrystallization by above-mentioned steps, good water solubility, oleuropein fine work that content is high can be prepared.
2. method according to claim 1, is characterized in that, step 2) described in exclusive extraction agent be industrial alcohol and industrial methanol by volume 1: 1 combination solution.
3. method according to claim 1, is characterized in that, step 2) described in the condition of suction filtration be: vacuum tightness 0.07-0.09MPa.
4. method according to claim 1, is characterized in that, step 3) described in the condition of concentrating under reduced pressure be: vacuum tightness 0.07-0.09MPa, temperature is 40-50 DEG C.
5. method according to claim 1, is characterized in that, step 3) described in concentrated solution be 1: 15-20 with the cumulative volume ratio of ethyl acetate.
6. method according to claim 1, is characterized in that, step 3) described in the mass volume ratio of concentrated extract and ether be 1: 5-10.
7. method according to claim 1, is characterized in that, step 3) described in the condition of decompression drying be: vacuum tightness 0.09-0.1MPa, temperature is 35-40 DEG C.
8. method according to claim 1, is characterized in that, step 4) described in the condition of reflux desolventing technology be: the amount of with the addition of of gac is the 2-3 ‰ of its weight, and temperature is 45-50 DEG C.
9. method according to claim 1, is characterized in that, step 5) described in the condition of concentrating under reduced pressure be: vacuum tightness 0.09-0.1MPa, temperature is 45-50 DEG C.
10. method according to claim 1, is characterized in that, step 5) described in the condition of ethyl acetate thermosol be: the mass volume ratio of oleuropein crude product and ethyl acetate is 1g: 8-10mL, and thermosol temperature is 45-50 DEG C.
11. methods according to claim 1, is characterized in that, step 5) described in the condition of stand at low temperature be: cryogenic temperature is 0 to 5 DEG C, and the time left standstill is 12-24 hour.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106046078A (en) * | 2016-06-28 | 2016-10-26 | 郭舒洋 | Method for extracting oleuropein from olea europaea leaves |
| CN107652336A (en) * | 2017-11-01 | 2018-02-02 | 安徽龙津生物科技有限公司 | It is a kind of in high yield, the extracting method of high-purity oleuropein |
| CN109125182A (en) * | 2018-10-16 | 2019-01-04 | 阿谷巴科技（唐山）有限公司 | A kind of Cleupin cold cream and preparation method thereof with bacteriostasis |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102702287A (en) * | 2012-06-21 | 2012-10-03 | 桂林三宝药业有限公司 | Method for extracting purified oleuropein from olive leaves |
| CN102850416A (en) * | 2012-09-07 | 2013-01-02 | 中国林业科学研究院林产化学工业研究所 | Method and apparatus used for preparing olive leaf extract |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102702287A (en) * | 2012-06-21 | 2012-10-03 | 桂林三宝药业有限公司 | Method for extracting purified oleuropein from olive leaves |
| CN102850416A (en) * | 2012-09-07 | 2013-01-02 | 中国林业科学研究院林产化学工业研究所 | Method and apparatus used for preparing olive leaf extract |
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| 谢普军等: "橄榄苦苷提取工艺的研究进展", 《生物质化学工程》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106046078A (en) * | 2016-06-28 | 2016-10-26 | 郭舒洋 | Method for extracting oleuropein from olea europaea leaves |
| CN107652336A (en) * | 2017-11-01 | 2018-02-02 | 安徽龙津生物科技有限公司 | It is a kind of in high yield, the extracting method of high-purity oleuropein |
| CN109125182A (en) * | 2018-10-16 | 2019-01-04 | 阿谷巴科技（唐山）有限公司 | A kind of Cleupin cold cream and preparation method thereof with bacteriostasis |
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