CN106349322A - Method for extracting and separating ursolic acid from olive pomace - Google Patents
Method for extracting and separating ursolic acid from olive pomace Download PDFInfo
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- CN106349322A CN106349322A CN201610727808.9A CN201610727808A CN106349322A CN 106349322 A CN106349322 A CN 106349322A CN 201610727808 A CN201610727808 A CN 201610727808A CN 106349322 A CN106349322 A CN 106349322A
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- olive pomace
- ursolic acid
- sodium bicarbonate
- ethanol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
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Abstract
The invention discloses a method for extracting ursolic acid from olive pomace. The method comprises the following steps: 1) extracting olive pomace with a 70-90 vol% ethanol solution, filtering the extracting solution, taking the filtrate, and recovering the ethanol under reduced pressure to obtain a crude extract; 2) adding the crude extract into a 50-65 vol% ethanol solution to be redissolved, thereby obtaining a mixed solution; and 3) passing the mixed solution through an AB-8 macroporous adsorbent resin column, eluting with water to a colorless state, eluting with a 40-50-DEG C 0.1-0.15 mol/L sodium bicarbonate solution, eluting with a 75-78-DEG C 0.6-0.8 mol/L sodium bicarbonate solution, collecting the three eluates, regulating the pH value to 3-5, filtering, taking the filter residue, and drying. The ursolic acid extracted by the method has the advantages of high purity and high yield.
Description
Technical field
The invention belongs to technical field of biological extraction is and in particular to a kind of extract separating ursolic acid from olive pomace
Method.
Background technology
Fructus oleae europaeae (olea europare l.) is world-renowned woody oil tree species, has the cultivation of more than 4000 year to go through
History.Olea europaea fruit produces substantial amounts of marc after squeezing, and major part directly goes out of use, not only serious environment pollution, also result in
The waste of resource.Olive pomace is made up of Fructus oleae europaeae peel, pit and remaining sarcocarp, wherein mainly contains triterpeness, flavone
The effective ingredient such as class, volatile oil, vitamin.Triterpenoid compound is mainly made up of 6 isoprene structures units, most of
It is the terpenoid containing 30 carbon atoms.Olive pomace triterpenes components mainly include oleanolic acid, Crataegolic acid and Folium Vaccinii vitis-idaeae
Acid, and these three structures of matter are similar, generally is carried out separating using Column chromatography techniques, but repeatedly silica gel column chromatography separate and
Recrystallization leads to the sample size finally giving little.Again due to Column chromatography techniques generally existing long processing period, continuous operation property
Not strong, it is difficult to be used for the commercial production process of bioactive substance as separating medium.
Content of the invention
Present invention solves the technical problem that being to provide a kind of method extracting ursolic acid from olive pomace, the method letter
Single, cycle is short, the ursolic acid purity obtaining is high, and yield is big.
The technical scheme that the present invention provides is the method extracting ursolic acid from olive pomace, comprises the following steps:
1) ethanol solution that olive pomace volumetric concentration is 70～90% is extracted, extracting solution is filtered, takes filtrate
Decompression recycling ethanol, obtains crude extract；
2) crude extract addition volumetric concentration is dissolved again for 50～65% ethanol solution, obtain mixed solution；
3) by ab-8 macroporous adsorptive resins on mixed solution, first wash with water to colourless, then adopt 40～50 DEG C,
The sodium bicarbonate solution of 0.1～0.15mol/l carries out eluting, then the sodium bicarbonate solution with 75～78 DEG C, 0.6～0.8mol/l
Carry out eluting, collect third time eluent, adjust ph to 3～5, filter, take filter residue and drying, obtain final product.
In step 1) in, Fructus Canarii albi marc is extracted using the ethanol solution that volumetric concentration is 70～90%, can fully extract olive
Oleanolic acid in olive marc, Crataegolic acid and ursolic acid.Fructus Canarii albi marc is 1g:10～20ml with the solid-liquid ratio of ethanol solution.
Described be extracted as heating and refluxing extraction, extraction time be 1～3 time, each extraction time be 1～3h.
Step 2) in, the ethanol solution dissolving crude extract being 50～65% using volumetric concentration, pole in removable crude extract
The less impurity of property, plays the effect of preliminary purification.Ethanol solution to crude extract concentration is added to be 0.06～0.10g/ml, now
The adsorption effect of upper prop is optimal.
Step 3) in, the macroporous resin of ab-8 model is low pole, and average pore size is 13～14nm, and specific surface area is 480
～520m2/g.Because oleanolic acid, Crataegolic acid, ursolic acid are low pole material, and there is certain hydrophobicity, generate hydrogen
The ability of key is weaker, thus is easily adsorbed by nonpolar and low pole resin.Secondly, during absorption with macroporous adsorbent resin material, quilt
Absorbed component is to be diffused into resin internal surface of hole by the aperture of resin and be adsorbed, when resin aperture is less than effective one-tenth of absorption
During fractionated molecule, effective ingredient molecule can not enter inside resin, can only adsorb in resin outer surface, when resin aperture is more than effectively
During component molecules, effective ingredient can adsorb and also can be adsorbed on inner surface in resin outer surface, to Crataegolic acid, oleanolic acid and
For ursolic acid, its molecular weight is respectively 472,456 and 456, therefore adopts the adsorption effect of ab-8 macroporous resin preferable.Resin
The blade diameter length ratio of post is advisable for 1:3～6, optimal with 1:4.
Oleanolic acid, Crataegolic acid and ursolic acid structure are very much like, and wherein ursolic acid and oleanolic acid are even more isomerism
Body, common column chromatography is difficult to be isolated and comes, but the present invention adopts 40～50 DEG C, the bicarbonate of 0.1～0.15mol/l
Sodium solution can be larger with polarity in resin Fructus Crataegi acid reaction generate soluble sodium salt, and then elute, and polarity be less than normal
Oleanolic acid and the carboxyl of ursolic acid and the polarizability of hydrone poor it is impossible to ionize out h+ it is impossible to enter with sodium bicarbonate
Row reaction generates sodium salt, then stay in resin column.The elution speed of sodium bicarbonate solution be 1～1.5bv/h, its consumption be 1～
During 1.5bv, eluting effect is preferable.
Sodium bicarbonate solution using 75～78 DEG C, 0.6～0.8mol/l carries out eluting, now can with eluting ursolic acid,
And oleanolic acid is not eluted, because oleanolic acid and Crataegolic acid structure are isomerss, therefore, using the speed of eluting faster
Degree 2～2.5bv/h, less amount of eluent is 0.5～1bv, can at utmost eluting ursolic acid, and oleanolic acid is not washed
De-.
The method of the present invention is simple, cycle is short, and the ursolic acid purity of extraction is high, and yield is big.
Specific embodiment
The present invention is further elaborated for specific examples below, but not as a limitation of the invention.
Embodiment 1
1) the ethanol solution ratio mixing for 1g:10ml in solid-liquid ratio being 70% by olive pomace and volumetric concentration,
Heating and refluxing extraction 3h, extracting solution is filtered, and takes decompression filtrate recycling ethanol, obtains crude extract；
2) crude extract being added volumetric concentration is 0.06g/ml for 50% ethanol solution to crude extract concentration, stirs evenly, obtains
Mixed solution；
3) by ab-8 macroporous adsorptive resins on mixed solution, resin column blade diameter length ratio is 1:3, first washes with water to colourless,
Be subsequently adding 40 DEG C, the sodium bicarbonate solution of 0.1mol/l carry out eluting, the elution speed of sodium bicarbonate solution is 1bv/h, its
Consumption is 1bv, then carries out eluting with the sodium bicarbonate solution of 75 DEG C, 0.6mol/l, and elution speed is 2bv/h, and its consumption is
0.5bv, collects third time eluent (i.e. the sodium bicarbonate eluent of 0.6mol/l), adjusts ph to 3, filters, takes filter residue and drying,
Obtain final product.
It is measured according to high performance liquid chromatography, its purity is 99.1%, yield is 90.5%.
Embodiment 2
1) the ethanol solution ratio mixing for 1g:20ml in solid-liquid ratio being 90% by olive pomace and volumetric concentration,
Heating and refluxing extraction 3 times, each extraction time is 3h, extracting solution is filtered, takes decompression filtrate recycling ethanol, obtain crude extract；
2) crude extract being added volumetric concentration is 0.10g/ml for 65% ethanol solution to crude extract concentration, stirs evenly, obtains
Mixed solution；
3) by ab-8 macroporous adsorptive resins on mixed solution, resin column blade diameter length ratio is 1:6, first washes with water to colourless,
Be subsequently adding 50 DEG C, the sodium bicarbonate solution of 0.15mol/l carry out eluting, the elution speed of sodium bicarbonate solution is 1.5bv/h,
Its consumption is 1.5bv, then carries out eluting with the sodium bicarbonate solution of 78 DEG C, 0.8mol/l, and elution speed is 2.5bv/h, its use
Measure as 1bv, collect third time eluent (i.e. the sodium bicarbonate eluent of 0.8mol/l), adjust ph to 5, filter, take filtering residue to do
Dry, obtain final product.
It is measured according to high performance liquid chromatography, its purity is 99.0%, yield is 90.6%.
Embodiment 3
1) the ethanol solution ratio mixing for 1g:20ml in solid-liquid ratio being 90% by olive pomace and volumetric concentration,
Heating and refluxing extraction 2 times, each extraction time is 2h, extracting solution is filtered, takes decompression filtrate recycling ethanol, obtain crude extract；
2) crude extract being added volumetric concentration is 0.08g/ml for 55% ethanol solution to crude extract concentration, stirs evenly, obtains
Mixed solution；
3) by ab-8 macroporous adsorptive resins on mixed solution, resin column blade diameter length ratio is 1:4, first washes with water to colourless,
Be subsequently adding 45 DEG C, the sodium bicarbonate solution of 0.12mol/l carry out eluting, the elution speed of sodium bicarbonate solution is 1.2bv/h,
Its consumption is 1.2bv, then carries out eluting with the sodium bicarbonate solution of 76 DEG C, 0.7mol/l, and elution speed is 2.5bv/h, its use
Measure as 0.5bv, collect third time eluent (the sodium bicarbonate eluent of 0.7mol/l), adjust ph to 4, filter, take filtering residue to do
Dry, obtain final product.
It is measured according to high performance liquid chromatography, its purity is 99.5%, yield is 93.5%.
Embodiment 4
1) the ethanol solution ratio mixing for 1g:20ml in solid-liquid ratio being 70% by olive pomace and volumetric concentration,
Heating and refluxing extraction 3 times, each extraction time is 1h, extracting solution is filtered, takes decompression filtrate recycling ethanol, obtain crude extract；
2) crude extract being added volumetric concentration is 0.06g/ml for 65% ethanol solution to crude extract concentration, stirs evenly, obtains
Mixed solution；
3) by ab-8 macroporous adsorptive resins on mixed solution, resin column blade diameter length ratio is 1:3, first washes with water to colourless,
Be subsequently adding 50 DEG C, the sodium bicarbonate solution of 0.1mol/l carry out eluting, the elution speed of sodium bicarbonate solution is 1.5bv/h,
Its consumption is 1bv, then carries out eluting with the sodium bicarbonate solution of 75 DEG C, 0.8mol/l, and elution speed is 2bv/h, and its consumption is
1bv, collects third time eluent (i.e. the sodium bicarbonate eluent of 0.8mol/l), adjusts ph to 3～5, filters, and takes filtering residue to do
Dry, obtain final product.
It is measured according to high performance liquid chromatography, its purity is 99.0%, yield is 91.2%.
Claims (6)
1. from olive pomace extract ursolic acid method it is characterised in that: comprise the following steps:
1) ethanol solution that olive pomace volumetric concentration is 70～90% is extracted, extracting solution is filtered, takes filtrate decompression
Reclaim ethanol, obtain crude extract；
2) crude extract addition volumetric concentration is dissolved again for 50～65% ethanol solution, obtain mixed solution；
3) by ab-8 macroporous adsorptive resins on mixed solution, first wash with water to colourless, then adopt 40～50 DEG C, 0.1～
The sodium bicarbonate solution of 0.15mol/l carries out eluting, then is carried out with the sodium bicarbonate solution of 75～78 DEG C, 0.6～0.8mol/l
Eluting, collects third time eluent, adjusts ph to 3～5, filters, takes filter residue and drying, obtain final product.
2. according to claim 1 from olive pomace extract ursolic acid method it is characterised in that: step 1) in,
Olive pomace is 1g:10～20ml with the solid-liquid ratio of ethanol solution.
3. according to claim 1 from olive pomace extract ursolic acid method it is characterised in that: step 1) in,
Described extraction time 1～3 time, each extraction time is 1～3h.
4. according to claim 1 from olive pomace extract ursolic acid method it is characterised in that: step 2) in,
Ethanol solution to crude extract concentration is added to be 0.06～0.10g/ml.
5. according to claim 1 from olive pomace extract ursolic acid method it is characterised in that: step 3) in,
Concentration is the elution speed of the sodium bicarbonate solution of 0.1～0.15mol/l is 1～1.5bv/h, and its consumption is 1～1.5bv.
6. according to claim 1 from olive pomace extract ursolic acid method it is characterised in that: step 3) in,
Concentration is the elution speed of the sodium bicarbonate solution of 0.6～0.8mol/l is 2～2.5bv/h, and its consumption is 0.5～1bv.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102370713A (en) * | 2010-08-26 | 2012-03-14 | 苏州宝泽堂医药科技有限公司 | Preparation method for momordin |
| CN103169771A (en) * | 2011-12-23 | 2013-06-26 | 中国科学院兰州化学物理研究所 | Method for extracting maslinic acid and oleanolic acid containing mixture from olea europaea L. pomace |
| CN104876998A (en) * | 2015-05-28 | 2015-09-02 | 天津大学 | Method for adopting pH gradient elution method to synchronously separate triterpenoid saponins and licorice flavonoid |
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2016
- 2016-08-25 CN CN201610727808.9A patent/CN106349322B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102370713A (en) * | 2010-08-26 | 2012-03-14 | 苏州宝泽堂医药科技有限公司 | Preparation method for momordin |
| CN103169771A (en) * | 2011-12-23 | 2013-06-26 | 中国科学院兰州化学物理研究所 | Method for extracting maslinic acid and oleanolic acid containing mixture from olea europaea L. pomace |
| CN104876998A (en) * | 2015-05-28 | 2015-09-02 | 天津大学 | Method for adopting pH gradient elution method to synchronously separate triterpenoid saponins and licorice flavonoid |
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