CN106397529B - The method of extraction separation crataegolic acid from olive pomace - Google Patents
The method of extraction separation crataegolic acid from olive pomace Download PDFInfo
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- CN106397529B CN106397529B CN201610728762.2A CN201610728762A CN106397529B CN 106397529 B CN106397529 B CN 106397529B CN 201610728762 A CN201610728762 A CN 201610728762A CN 106397529 B CN106397529 B CN 106397529B
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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
Abstract
The invention discloses a kind of method that crataegolic acid is extracted from olive pomace, comprise the following steps：1) ethanol solution that olive pomace volumetric concentration is 70~90% is extracted, extract solution is filtered, takes decompression filtrate recycling ethanol, obtains crude extract；2) it is that 50~65% ethanol solutions dissolve again crude extract to be added into volumetric concentration, obtains mixed solution；3) by the large pore resin absorption columns of AB on mixed solution 8, first it is eluted with water to colourless, then adds 40~50 DEG C, 0.1~0.15mol/L sodium bicarbonate solution eluted, sodium acid carbonate eluent is collected, adjusts pH to 3~5, filtering, filter residue and drying is taken, is produced.The crataegolic acid purity that the present invention extracts is high, and yield is big.
Description
Technical field
The invention belongs to technical field of biological extraction, and in particular to a kind of extraction separation crataegolic acid from olive pomace
Method.
Background technology
Olive (Olea europare L.) is world-renowned woody oil tree species, and the cultivation for having more than 4000 years is gone through
History.Olea europaea fruit produces substantial amounts of pomace after squeezing, most of directly to go out of use, and not only seriously pollutes environment, also result in
The waste of resource.Olive pomace is made up of olive pericarp, fruit stone and remaining pulp, wherein mainly containing triterpenes, flavones
The active ingredients such as class, volatile oil, vitamin.Triterpene compound is mainly made up of 6 isoprene structures units, most of
For the terpenoid containing 30 carbon atoms.Olive pomace triterpenes components mainly include oleanolic acid, crataegolic acid and black bearberry
Acid, and these three structures of matter are similar, generally use Column chromatography techniques are separated, but repeatedly silica gel column chromatography separation and
Recrystallization causes the sample size that finally gives seldom.Again due to Column chromatography techniques generally existing long processing period, continuous operation property
It is not strong, it is not easy the industrial production process for being used for bioactive substance as separating medium.
The content of the invention
Present invention solves the technical problem that it is to provide a kind of method that crataegolic acid is extracted from olive pomace, this method letter
Single, the cycle is short, and obtained crataegolic acid purity is high, and yield is big.
Technical scheme provided by the invention is the method that crataegolic acid is extracted from olive pomace, is comprised the following steps：
1) ethanol solution that olive pomace volumetric concentration is 70~90% is extracted, extract solution is filtered, takes filtrate
Ethanol is recovered under reduced pressure, obtains crude extract；
2) it is that 50~65% ethanol solutions dissolve again crude extract to be added into volumetric concentration, obtains mixed solution；
3) by AB-8 large pore resin absorption columns on mixed solution, be first eluted with water to colourless, then add 40~50 DEG C,
0.1~0.15mol/L sodium bicarbonate solution is eluted, and collects sodium acid carbonate eluent, is adjusted pH to 3~5, filtering, is taken
Filter residue and drying, produce.
In step 1), use volumetric concentration to extract olive pomace for 70~90% ethanol solution, can fully extract
Oleanolic acid, crataegolic acid and ursolic acid in olive pomace.The solid-liquid ratio of olive pomace and ethanol solution is 1g：10~
20ml.Described to be extracted as heating and refluxing extraction, extraction time is 1~3 time, and each extraction time is 1~3h.
In step 2), use volumetric concentration to dissolve crude extract for 50~65% ethanol solution, can remove pole in crude extract
The less impurity of property, play the effect of preliminary purification.It is 0.06~0.10g/ml to add ethanol solution to crude extract concentration, now
The adsorption effect of upper prop is optimal.
In step 3), the macroreticular resins of AB-8 models is low pole, and average pore size is 13~14nm, specific surface area 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 macroporous absorbent resin adsorbent, quilt
Absorbed component is to be diffused into resin internal surface of hole by the aperture of resin and adsorbed, when resin aperture be less than absorption it is effective into
During fractionated molecule, active ingredient molecule can not enter inside resin, can only adsorb in resin outer surface, when resin aperture is more than effectively
During component molecules, active ingredient can be adsorbed 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 preferable using the adsorption effect of AB-8 macroreticular resins.Resin
The blade diameter length ratio of post is 1:3~6 are advisable, with 1:4 is optimal.
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 are difficult to be isolated to come, but the present invention uses 40~50 DEG C, 0.1~0.15mol/L bicarbonate
Sodium solution can be larger with polarity in resin hawthorn acid reaction generation soluble sodium salt, and then elute, and polarity is less than normal
Oleanolic acid and the carboxyl of ursolic acid and the polarizability of hydrone it is poor, it is impossible to ionize out H+, can not enter with sodium acid carbonate
Row reaction generation sodium salt, then stay in resin column.
Method of the invention is simple, the cycle is short, and the crataegolic acid purity of extraction is high, and yield is big.
Embodiment
The present invention is further elaborated for specific examples below, but not as a limitation of the invention.
Embodiment 1
1) it is 1g by solid-liquid ratio by ethanol solution that olive pomace and volumetric concentration are 70%：10ml ratio mixing,
Heating and refluxing extraction 3h, extract solution is filtered, and takes decompression filtrate recycling ethanol, obtains crude extract；
2) it is that 50% ethanol solution to crude extract concentration is 0.06g/ml by crude extract addition volumetric concentration, stirs evenly, obtain
Mixed solution；
3) by AB-8 large pore resin absorption columns on mixed solution, resin column blade diameter length ratio is 1:3, first it is eluted with water to colourless,
Then 40 DEG C of addition, 0.1mol/L sodium bicarbonate solution are eluted, and the elution speed of sodium bicarbonate solution is 1BV/h, its
Dosage is 1BV, collects sodium acid carbonate eluent, adjusts pH to 3, filtering, takes filter residue and drying, produce.According to high performance liquid chromatography
Method is measured, and its purity is 99.1%, yield 95.3%.
Embodiment 2
1) it is 1g by solid-liquid ratio by ethanol solution that olive pomace and volumetric concentration are 90%：20ml ratio mixing,
Heating and refluxing extraction 3 times, each extraction time are 3h, and extract solution is filtered, takes decompression filtrate recycling ethanol, obtains crude extract；
2) it is that 65% ethanol solution to crude extract concentration is 0.10g/ml by crude extract addition volumetric concentration, stirs evenly, obtain
Mixed solution；
3) by AB-8 large pore resin absorption columns on mixed solution, resin column blade diameter length ratio is 1:6, first it is eluted with water to colourless,
Then 50 DEG C of addition, 0.15mol/L sodium bicarbonate solution are eluted, and the elution speed of sodium bicarbonate solution is 1.5BV/h,
Its dosage is 1.5BV, collects sodium acid carbonate eluent, adjusts pH to 5, filtering, takes filter residue and drying, produce.According to efficient liquid phase
Chromatography is measured, and its purity is 99.0%, yield 95.1%.
Embodiment 3
1) it is 1g by solid-liquid ratio by ethanol solution that olive pomace and volumetric concentration are 90%：20ml ratio mixing,
Heating and refluxing extraction 2 times, each extraction time are 2h, and extract solution is filtered, takes decompression filtrate recycling ethanol, obtains crude extract；
2) it is that 55% ethanol solution to crude extract concentration is 0.08g/ml by crude extract addition volumetric concentration, stirs evenly, obtain
Mixed solution；
3) by AB-8 large pore resin absorption columns on mixed solution, resin column blade diameter length ratio is 1:4, first it is eluted with water to colourless,
Then 45 DEG C of addition, 0.12mol/L sodium bicarbonate solution are eluted, and the elution speed of sodium bicarbonate solution is 1.2BV/h,
Its dosage is 1.2BV, collects sodium acid carbonate eluent, adjusts pH to 4, filtering, takes filter residue and drying, produce.According to efficient liquid phase
Chromatography is measured, and its purity is 99.5%, yield 96.8%.
Embodiment 4
1) it is 1g by solid-liquid ratio by ethanol solution that olive pomace and volumetric concentration are 70%：20ml ratio mixing,
Heating and refluxing extraction 3 times, each extraction time are 1h, and extract solution is filtered, takes decompression filtrate recycling ethanol, obtains crude extract；
2) it is that 65% ethanol solution to crude extract concentration is 0.06g/ml by crude extract addition volumetric concentration, stirs evenly, obtain
Mixed solution；
3) by AB-8 large pore resin absorption columns on mixed solution, resin column blade diameter length ratio is 1:3, first it is eluted with water to colourless,
Then 50 DEG C of addition, 0.1mol/L sodium bicarbonate solution are eluted, and the elution speed of sodium bicarbonate solution is 1.5BV/h,
Its dosage is 1BV, collects sodium acid carbonate eluent, adjusts pH to 5, filtering, takes filter residue and drying, produce.According to high-efficient liquid phase color
Spectrometry is measured, and its purity is 99.0%, yield 95.4%.
Claims (5)
1. the method for crataegolic acid is extracted from olive pomace, it is characterised in that：Comprise the following steps：
1) ethanol solution that olive pomace volumetric concentration is 70~90% is extracted, extract solution is filtered, takes filtrate decompression
Ethanol is reclaimed, obtains crude extract；
2) it is that 50~65% ethanol solutions dissolve again crude extract to be added into volumetric concentration, obtains mixed solution；
3) by AB-8 large pore resin absorption columns on mixed solution, be first eluted with water to colourless, then add 40~50 DEG C, 0.1~
0.15mol/L sodium bicarbonate solution is eluted, and collects sodium acid carbonate eluent, is adjusted pH to 3~5, filtering, is taken filter residue to do
It is dry, produce.
2. the method according to claim 1 that crataegolic acid is extracted from olive pomace, it is characterised in that：In step 1),
The solid-liquid ratio of olive pomace and ethanol solution is 1g：10~20ml.
3. the method according to claim 1 that crataegolic acid is extracted from olive pomace, it is characterised in that：In step 1),
The extraction time 1~3 time, each extraction time is 1~3h.
4. the method according to claim 1 that crataegolic acid is extracted from olive pomace, it is characterised in that：In step 2),
It is 0.06~0.10g/ml to add ethanol solution to crude extract concentration.
5. the method according to claim 1 that crataegolic acid is extracted from olive pomace, it is characterised in that：In step 3),
The elution speed of sodium bicarbonate solution is 1~1.5BV/h, and its dosage is 1~1.5BV.
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| CN111303236B (en) * | 2020-03-02 | 2022-10-04 | 陕西富恒生物科技有限公司 | Method for simultaneously extracting and separating maslinic acid, oleuropein and oleanolic acid from olive leaves |
| CN115583983B (en) * | 2022-10-27 | 2024-04-09 | 中国科学院兰州化学物理研究所 | Method for preparing high-purity crataegolic acid through separation |
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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- 2016-08-25 CN CN201610728762.2A patent/CN106397529B/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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