CN102464683A - Method for extracting oleuropein from olive leaves - Google Patents
Method for extracting oleuropein from olive leaves Download PDFInfo
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- CN102464683A CN102464683A CN201010549746XA CN201010549746A CN102464683A CN 102464683 A CN102464683 A CN 102464683A CN 201010549746X A CN201010549746X A CN 201010549746XA CN 201010549746 A CN201010549746 A CN 201010549746A CN 102464683 A CN102464683 A CN 102464683A
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Abstract
The invention relates to a method for extracting oleuropein from olive leaves. The method comprises the following steps of: smashing olive leaves; adding saturated lime water in an amount of 8-15 times that of the olive leaves, and heating and extracting for 2-3 times; adjusting an extracting solution to be neutral; adding a filtered extracting solution into a macroporous resin column for adsorbing; gradually eluting with ethanol water; collecting active ingredients; concentrating under reduced pressure; adding water-saturated n-butyl alcohol into a concentrated solution for extracting for 3-5 times; collecting a n-butyl alcohol layer; recovering an organic solvent under reduced pressure to obtain an extract; adding ethanol for refluxing and dissolving; adding active carbon for decoloring for 1-2 hours; filtering the active carbon out; recovering ethanol; and performing freeze drying to obtain the oleuropein product. The method has the advantages of easy operating, no use of toxic reagents in a preparation process, environmental friendliness and high product content, and is suitable for industrial production.
Description
Technical field:
The invention belongs to the Separation of Natural Products field, especially a kind of method of from olive leaf, extracting Oleuropein.
Background technology:
Oleuropein is a kind of phenol secoiridoid glycosides, molecular formula: C
25H
32O
13, molecular weight 540.43 is soluble in hot water, methyl alcohol, ethanol, ETHYLE ACETATE etc., is insoluble to nonpolar organic reagents such as chloroform, sherwood oil.
Oleuropein is a polyphenolic compound, has resistance of oxidation, can alleviate the degree of oxidation of low-density lipoprotein, prevention coronary heart disease, atherosclerotic generation, also can releive vascular smooth muscle with bring high blood pressure down.
Olive leaf is the ripe leaf of Oleaceae olive, and fruit and seed is nutritious, and mostly leaf is waste, but contains a large amount of antioxidant components in the leaf, and Oleuropein is one of its activeconstituents.Along with the modern medicine study development, Olive leaf P.E is widely used in medicines and health protection makeup aspect.
Existing extraction is extracted Oleuropein and is mostly the crude extract that content is low from olive leaf, and cost is higher.
Like Chinese patent " a kind of process for extracting of Olive leaf P.E "; The method that this patent adopts be olive leaf through the clear water rinsing, inject disinfection by chlorine dioxide in the clear water, with the olive leaf warm air drying of handling; Adopt alcohol to extract then for solvent; After vacuum decompression concentrates, in liquid concentrator, add inhibitor---tea-polyphenol (water-soluble), through lyophilize or spraying drying and Olive leaf P.E.
Chinese patent " is rich in the preparation method of the olive leaf extract of high purity Oleuropein " for another example, and this method is disclosed to be leaf of Fructus oleae europaeae to be extracted alkaline again centrifugal settling with polar solvent earlier; Obtain centrifugal clear liquid and throw out; Then carry out the film coupling and separate, obtain liquid concentrator, medium absorption again through nf membrane; Adsorption medium is carried out wash-out obtain elutriant; Vacuum concentration carries out vacuum lyophilization or spraying drying again, obtains Oleuropein content greater than 50% the olive leaf extract that is rich in the high purity Oleuropein.Also having document " technical study of PA membrane on Oleuropein separates " also is to adopt membrane sepn to improve the content of Oleuropein.
Document " leaf of Fructus oleae europaeae polyphenoils effective constituent and the research of content rule thereof ", the document has been optimized the industrial manufacture process condition of olive leaf extract.Adopt water-bath heat to put forward mode, extraction conditions is: extract with 80% alcohol-water, and extraction time 3.5h, temperature: 70 ℃, solid-to-liquid ratio 1: 10.Adopt the macroporous resin adsorption separation and purification, through the absorption of contrast different resins to Oleuropein, filter out the good AB-8 resin of selective adsorption, adsorptive capacity is the 32.1mg/g wet resin.The top condition of AB-8 resin purification is: appearance concentration is 2mg/mL on the sample, and flow velocity is 3mL/min, and 70% alcohol-water wash-out, elutriant consumption are 3BV.The olive leaf extract of preparation, Oleuropein content is 47.9%.
And patent " a kind of preparation method of Olive leaf P.E " disclosed method is with polar solvent olive leaf to be extracted earlier; With the flocculation agent deposition, obtain centrifugal clear liquid and throw out again, centrifugal clear liquid extracts; Ethyl acetate extraction further separates with the preparative high performance liquid chromatography post mutually; Differential refraction detector carries out online detection, and targeted is collected the Oleuropein product section, preparation liquid concentrating under reduced pressure; Carry out vacuum-drying or spraying drying again, obtain Oleuropein content greater than 90% Olive leaf P.E.This method adopts preparation liquid phase purifying, is difficult to industriallization.
The extraction process of simultaneously traditional Oleuropein is extraction from daphne lilac, and operational path is: daphne lilac-alcohol reflux-diafiltration concentrates-SX-propyl carbinol medicinal extract-column chromatography branch-Oleuropein.This technology consumption of organic solvent is big, and cost is high.
Summary of the invention:
The technical problem that the present invention will solve provides a kind of industrial extraction method of Oleuropein cheaply, and the Oleuropein content that this method obtains is higher.
The present invention adopts following technical scheme to realize:
A kind of method of from olive leaf, extracting Oleuropein is characterized in that comprising following steps:
1) extract: olive leaf is pulverized, and adds 8-15 amount times saturated limewater heating and extracting 2-3 time, and extracting solution is regulated neutrality, filter extracting solution;
2) macroporous resin adsorption: add macroporous resin column absorption to said extracted liquid, ethanol water gradient elution is collected effective constituent, and concentrating under reduced pressure gets liquid concentrator;
3) extraction: above-mentioned liquid concentrator is added water-saturated n-butanol extraction 3-5 time, collect n-butanol layer reclaim under reduced pressure propyl carbinol, obtain medicinal extract;
4) decolouring: above-mentioned medicinal extract added activated carbon decolorizing 1-2 hour after adding the alcohol reflux dissolving again, and the filtering gac reclaims ethanol, and spraying drying gets product.
Heating temperature is 40-60 ℃ in the said step 1), extraction time 2-3 hour.
Said step 2) a kind of among the optional AB-8 of macroporous resin model, LSA-8, SPD-700 and the LSA-10 in, ethanol water gradient is 4-8BV water → 3-6BV20-30% ethanol → 5-6BV50-70% ethanol.
Ethanol in the said step 4) adds to concentration 70-90%, and gac is a medical injection class gac, and add-on is the 0.5-1% of amount of liquid.
In sum, positively effect of the present invention is: the saturated limewater extraction of heating, and lower than organic reagent extraction cost; And need not to concentrate directly upper prop, cutting down the consumption of energy, present method adopts and extracts with macroporous resin adsorption earlier again; Reduced the consumption of propyl carbinol, the resin isolation cost is low again than simple extraction or first macroporous resin, follow-up activated carbon decolorizing; Than membrane separating effect,, be difficult for causing effective constituent to lose in a large number through molecular film because the molecular structure of Oleuropein is a wire; This technology is for to use toxic reagent, and products obtained therefrom can directly be used for medicine and protective foods production.
To combine embodiment to further specify the present invention below, but the scope that the present invention requires to protect is not limited to following embodiment.
Embodiment:
Embodiment 1:
Olive leaf is pulverized, and gets 1kg, adds the 8kg saturated limewater and is heated to 50 ℃, soaking and extracting 3 hours; Leach liquid, add the 8kg saturated limewater again and extracted 2 hours, merge extracted twice liquid, it is neutral that hydrochloric acid is regulated pH; Filter, add the absorption of 1LAB-8 macroporous resin column, absorption finishes, and uses 5L water → 5L30% ethanol → 6L60% ethanolic soln wash-out successively; Collect 60% ethanol eluate and be evaporated to density 1.07, change in the beaker and to add the 100ml water-saturated n-butanol and stir, pour the separating funnel layering into after, collect propyl carbinol after; Extract again 4 times, merge n-butanol layer reclaim under reduced pressure propyl carbinol, obtain medicinal extract.After the adding alcohol reflux is dissolved to determining alcohol 70% in the medicinal extract, added 5g medical injection class activated carbon decolorizing again 2 hours, the filtering gac reclaims ethanol, and the liquid concentrator spraying drying gets off-white color Oleuropein 10.5g, through high phase Liquid Detection content 84.6%.
Embodiment 2:
Olive leaf is pulverized, and gets 1kg, adds the 10kg saturated limewater and is heated to 40 ℃, soaking and extracting 2 hours; Leach liquid, add the 8kg saturated limewater again and extracted 2 hours, merge extracted twice liquid, it is neutral that sulfuric acid is regulated pH; Filter, add the absorption of 1L LSA-8 macroporous resin column, absorption finishes, and uses 8L water → 5L30% ethanol → 6L50% ethanolic soln wash-out successively; Collect 50% ethanol eluate and be evaporated to density 1.05, change in the beaker and to add the 200ml water-saturated n-butanol and stir, pour the separating funnel layering into after, collect propyl carbinol after; Extract again 3 times, merge n-butanol layer reclaim under reduced pressure propyl carbinol, obtain medicinal extract.After the adding alcohol reflux is dissolved to determining alcohol 80% in the medicinal extract, added 7g medical injection class activated carbon decolorizing again 1 hour, the filtering gac reclaims ethanol, and the liquid concentrator spraying drying gets off-white color Oleuropein 9.2g, through high phase Liquid Detection content 87.5%.
Embodiment 3:
Olive leaf is pulverized, and gets 1kg, adds the 8kg saturated limewater and is heated to 60 ℃, soaking and extracting 3 hours; Leach liquid, add the 8kg saturated limewater again and extracted 2 hours, merge extracted twice liquid, it is neutral that hydrochloric acid is regulated pH; Filter, add the absorption of 1L SPD-700 macroporous resin column, absorption finishes, and uses 6L water → 6L20% ethanol → 5L70% ethanolic soln wash-out successively; Collect 70% ethanol eluate and be evaporated to density 1.04, change in the beaker and to add the 200ml water-saturated n-butanol and stir, pour the separating funnel layering into after, collect propyl carbinol after; Extract again 3 times, merge n-butanol layer reclaim under reduced pressure propyl carbinol, obtain medicinal extract.After the adding alcohol reflux is dissolved to determining alcohol 90% in the medicinal extract, added 10g medical injection class activated carbon decolorizing again 1 hour, the filtering gac reclaims ethanol, and the liquid concentrator spraying drying gets off-white color Oleuropein 8.5g, through high phase Liquid Detection content 88.6%.
Embodiment 4:
Olive leaf is pulverized, and gets 10kg, adds the 80kg saturated limewater and is heated to 50 ℃, soaking and extracting 2 hours; Leach liquid, add the 80kg saturated limewater again and extracted 2 hours, merge extracted twice liquid, it is neutral that hydrochloric acid is regulated pH; Filter, add the absorption of 10L LSA-10 macroporous resin column, absorption finishes, and uses 70L water → 50L30% ethanol → 60L60% ethanolic soln wash-out successively; Collect 60% ethanol eluate and be evaporated to density 1.05, change in the beaker and to add the 1.5L water-saturated n-butanol and stir, pour the separating funnel layering into after, collect propyl carbinol after; Extract again 3 times, merge n-butanol layer reclaim under reduced pressure propyl carbinol, obtain medicinal extract.After the adding alcohol reflux is dissolved to determining alcohol 80% in the medicinal extract, added 70g medical injection class activated carbon decolorizing again 2 hours, the filtering gac reclaims ethanol, and the liquid concentrator spraying drying gets off-white color Oleuropein 92.3g, through high phase Liquid Detection content 86.6%.
Embodiment 5:
Olive leaf is pulverized, and gets 20kg, adds the 200kg saturated limewater and is heated to 50 ℃, soaking and extracting 2 hours; Leach liquid, add the 160kg saturated limewater again and extracted 2 hours, merge extracted twice liquid, it is neutral that hydrochloric acid is regulated pH; Filter, add the absorption of 20L SPD-700 macroporous resin column, absorption finishes, and uses 120L water → 100L30% ethanol → 120L60% ethanolic soln wash-out successively; Collect 60% ethanol eluate and be evaporated to density 1.05, change in the beaker and to add the 4L water-saturated n-butanol and stir, pour the separating funnel layering into after, collect propyl carbinol after; Extract again 3 times, merge n-butanol layer reclaim under reduced pressure propyl carbinol, obtain medicinal extract.After the adding alcohol reflux is dissolved to determining alcohol 85% in the medicinal extract, added 150g medical injection class activated carbon decolorizing again 1 hour, the filtering gac reclaims ethanol, and the liquid concentrator spraying drying gets off-white color Oleuropein 191.5g, through high phase Liquid Detection content 84.8%.
Embodiment 6:
Olive leaf is pulverized, and gets 50kg, adds the 500kg saturated limewater and is heated to 50 ℃, soaking and extracting 2 hours; Leach liquid, add the 400kg saturated limewater again and extracted 2 hours, merge extracted twice liquid, it is neutral that hydrochloric acid is regulated pH; Filter, add the absorption of 50L LSA-8 macroporous resin column, absorption finishes, and uses 300L water → 200L30% ethanol → 300L50% ethanolic soln wash-out successively; Collect 50% ethanol eluate and be evaporated to density 1.05, change in a mixing bowl and to add the 8L water-saturated n-butanol and stir, pour in the separator after the layering, collect propyl carbinol after; Extract again 4 times, merge n-butanol layer reclaim under reduced pressure propyl carbinol, obtain medicinal extract.After the adding alcohol reflux is dissolved to determining alcohol 80% in the medicinal extract, added 300g medical injection class activated carbon decolorizing again 2 hours, the filtering gac reclaims ethanol, and the liquid concentrator spraying drying gets off-white color Oleuropein 480.4g, through high phase Liquid Detection content 85.6%.
Claims (4)
1. method of from olive leaf, extracting Oleuropein is characterized in that comprising following steps:
1) extract: olive leaf is pulverized, and adds 8-15 and doubly measures the saturated limewater heating and extracting 2-3 time, and extracting solution is regulated neutrality, filter extracting solution;
2) macroporous resin adsorption: add macroporous resin column absorption to said extracted liquid, ethanol water gradient elution is collected effective constituent, and concentrating under reduced pressure gets liquid concentrator;
3) extraction: above-mentioned liquid concentrator is added water-saturated n-butanol extraction 3-5 time, collect n-butanol layer reclaim under reduced pressure propyl carbinol, obtain medicinal extract;
4) decolouring: above-mentioned medicinal extract added activated carbon decolorizing 1-2 hour after adding the alcohol reflux dissolving again, and the filtering gac reclaims ethanol, and spraying drying gets product.
2. the method for from olive leaf, extracting Oleuropein as claimed in claim 1 is characterized in that Heating temperature is 40-60 ℃ in the said step 1), extraction time 2-3 hour.
3. the method for from olive leaf, extracting Oleuropein as claimed in claim 1; It is characterized in that said step 2) in the optional AB-8 of macroporous resin model, LSA-8, SPD-700 and LSA-10 in a kind of, ethanol water gradient is 4-8BV water → 3-6BV20-30% ethanol → 5-6BV50-70% ethanol.
4. the method for from olive leaf, extracting Oleuropein as claimed in claim 1 is characterized in that the ethanol in the said step 4) adds to concentration 70-90%, and gac is a medical injection class gac, and add-on is the 0.5-1% of amount of liquid.
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| CN201010549746XA CN102464683A (en) | 2010-11-19 | 2010-11-19 | Method for extracting oleuropein from olive leaves |
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| CN201010549746XA CN102464683A (en) | 2010-11-19 | 2010-11-19 | Method for extracting oleuropein from olive leaves |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102701914A (en) * | 2012-06-21 | 2012-10-03 | 桂林三宝药业有限公司 | Method for extracting hydroxytyrosol from olive leaves |
| 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 |
| CN103333213A (en) * | 2013-07-24 | 2013-10-02 | 桂林茗兴生物科技有限公司 | Method for extracting oleuropein from olive leaves |
| CN104610398A (en) * | 2015-02-03 | 2015-05-13 | 黑龙江省科学院自然与生态研究所 | Method for extracting oleuropein from syringa reticulata |
| CN110327266A (en) * | 2019-08-09 | 2019-10-15 | 肇庆市凯捷科技有限公司 | A kind of amino acid shampoo with bacterio static itching-relieving and hair care repair function |
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| JP2002128678A (en) * | 2000-10-17 | 2002-05-09 | Tama Seikagaku Kk | Method for producing extract composition containing oleuropein |
| EP1795201A1 (en) * | 2005-12-09 | 2007-06-13 | Mediterrenean Agronomic Institute of Chania (MAICH) | Isolation of oleuropein from the leaves of olive tree |
| CN101003557A (en) * | 2006-12-12 | 2007-07-25 | 中国林业科学研究院林产化学工业研究所 | Method for preparing extractive of olive leaves rich in oleuropein in high purity |
| CN101781344A (en) * | 2009-12-13 | 2010-07-21 | 成都普思生物科技有限公司 | Method for preparing olive leaf extract |
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2010
- 2010-11-19 CN CN201010549746XA patent/CN102464683A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002128678A (en) * | 2000-10-17 | 2002-05-09 | Tama Seikagaku Kk | Method for producing extract composition containing oleuropein |
| EP1795201A1 (en) * | 2005-12-09 | 2007-06-13 | Mediterrenean Agronomic Institute of Chania (MAICH) | Isolation of oleuropein from the leaves of olive tree |
| CN101003557A (en) * | 2006-12-12 | 2007-07-25 | 中国林业科学研究院林产化学工业研究所 | Method for preparing extractive of olive leaves rich in oleuropein in high purity |
| CN101781344A (en) * | 2009-12-13 | 2010-07-21 | 成都普思生物科技有限公司 | Method for preparing olive leaf extract |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102701914A (en) * | 2012-06-21 | 2012-10-03 | 桂林三宝药业有限公司 | Method for extracting hydroxytyrosol from olive leaves |
| 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 |
| CN102701914B (en) * | 2012-06-21 | 2014-04-23 | 桂林三宝药业有限公司 | Method for extracting hydroxytyrosol from olive leaves |
| CN103333213A (en) * | 2013-07-24 | 2013-10-02 | 桂林茗兴生物科技有限公司 | Method for extracting oleuropein from olive leaves |
| CN103333213B (en) * | 2013-07-24 | 2015-10-07 | 桂林茗兴生物科技有限公司 | The method of oleuropein is extracted from leaf of Fructus oleae europaeae |
| CN104610398A (en) * | 2015-02-03 | 2015-05-13 | 黑龙江省科学院自然与生态研究所 | Method for extracting oleuropein from syringa reticulata |
| CN104610398B (en) * | 2015-02-03 | 2017-03-22 | 黑龙江省科学院自然与生态研究所 | Method for extracting oleuropein from syringa reticulata |
| CN110327266A (en) * | 2019-08-09 | 2019-10-15 | 肇庆市凯捷科技有限公司 | A kind of amino acid shampoo with bacterio static itching-relieving and hair care repair function |
| CN110327266B (en) * | 2019-08-09 | 2022-05-24 | 肇庆市凯捷科技有限公司 | Amino acid shampoo with functions of inhibiting bacteria, relieving itching and protecting hair and repairing |
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Application publication date: 20120523 |