CN1373129A - Process for extracting oligoprotoanthocyanidin from plant - Google Patents
Process for extracting oligoprotoanthocyanidin from plant Download PDFInfo
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- CN1373129A CN1373129A CN01109225A CN01109225A CN1373129A CN 1373129 A CN1373129 A CN 1373129A CN 01109225 A CN01109225 A CN 01109225A CN 01109225 A CN01109225 A CN 01109225A CN 1373129 A CN1373129 A CN 1373129A
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- oligomeric procyanidolics
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Abstract
A process for extracting oligoprotoanthocyanidin from plant includes pulverizing dried raw plant, preparing leach liquid, adding inorganic salt to deposit inpurities, extracting oligoprotoanthocyanidin by polar organic solvent, separating out the oligoprotoanthocyanidin from organic polar solvent by organic non-polar solvent, and purifying. Its advnatages are low cost, less pollution and high purity.
Description
The present invention relates to a kind of method of from plant material, extracting oligomeric procyanidolics.
Pycnogenols with different content and complicated bonding state, comprises the polymkeric substance of the various polymerization degree at nature, and the polymkeric substance from monomer to the phlobaphene type extensively is present among various vegetables, fruit, plant seed benevolence, blade, limb and bark or the like.The intravital this compound of plant is only just presenting Lan Se or redness through after the effect of enzyme.Pycnogenols is catechin, l-Epicatechol or the two phase blended polymkeric substance, and catechin and l-Epicatechol are steric isomer, and their oligopolymer generally is meant the polymkeric substance of the polymerization degree≤15.
Catechin and l-Epicatechol have the molecular structure shown in the following molecular structure 1.When they form polymkeric substance, between the monomer,, or interconnect on the 4th and the 8th position the 4th and the 6th.Because monomer, link position and the polymerization degree is different, oligomeric procyanidolics can have polytype molecule.That has measured structure has dimer A1, an A2 ..., B1, B2 ... B8 and tripolymer C1, C2 ... C8, T1, T2 ... T8 or the like polymkeric substance.Molecular structure 2～molecular structure 4 is procyanidin dimers (B1 and B2), tripolymer (C1) and the polymerization degree smaller or equal to the molecular structural formula of 15 oligomeric procyanidolics.Each molecular structure is as follows:
Molecular structure 1 molecular structure 2
Molecular structure 3 molecular structures 4
By above-mentioned molecular structure as seen, according to their molecular structure, can classify as polyphenol or flavonoids.
When mentioning oligomeric procyanidolics below this paper, indication mainly be these compounds of oligopolymer such as dimer and tripolymer.
Oligomeric procyanidolics is a strongest known natural antioxidants, and its resistance of oxidation far is better than vitamin-E and vitamins C, and has very high bioavailability in human body.In plant materials with the poly-pycnogenols of the height of oligomeric procyanidolics coexistence biologically active not in human body.Oligomeric procyanidolics is ingested behind the human body, as superior antioxidant, can remove free radical effectively, the protection cell exempts from the damage of free radical, thereby reduce the multiple disease that the destruction owing to free radical causes, comprise the incidence probability of the diseases such as retinopathy that cancer, coronary heart disease, diabetes cause; Alleviate symptoms such as allergy, bruise, oedema, inflammation; Improve body immunity; Slow down various preseniles, degenerative disease, for example the process of disease such as presenile dementia, senile cataract; Low density cholesterol level and hematoblastic coherency are reduced, thereby reduce the incidence probability of atherosclerosis and cardiovascular disorder; More since its with collagen protein and elastin between highly avidity is arranged, thereby can play special provide protection to the heart, the cerebrovascular, joint and skin etc.It is worthy of note that especially oligomeric procyanidolics is unique energy provides the anti-oxidation protection effect to brain cell through hemato encephalic barrier a antioxidant.Experiment also confirms in addition, between oligomeric procyanidolics and the vitamins C synergy is arranged, when vitamins C runs into free radical in human body, will be to the free radical donates electrons, make it to become normal molecule, self become simultaneously the not only unhelpful but also harmless weak free radical of human body is excreted.Oligomeric procyanidolics can make deactivated vitamins C repeated regeneration.This synergy has strengthened ascorbic resistance of oxidation significantly, makes the interior a spot of vitamins C of human body can remove relatively large free radical.
Since early 1950s is found the special protection and therapeutic action of oligomeric procyanidolics to human body; in Europe,, decades had been used before this afterwards in the North America; and, have no precedent the report of any toxic side effect through experimentation on animals widely and clinical and experimental study.So the cut-and-try work of Pasteur Institut and German cytology research and other international well-known research institution confirms that oligomeric procyanidolics is without any anxious, slow toxicity, and is not carcinogenic, unlikely monster, mutagenesis does not cause allergy, and its security and vitamins C are equal to.Can say for certain: pycnogenols is a kind of totally nontoxic, fool proof and to safeguarding that HUMAN HEALTH has the very material of high value.
In a word, oligomeric procyanidolics has very important health care and medical value, at aspects such as healthcare products, food, skin cosmetic and medicine industries wide direct application and secondary development future is arranged.
The purpose of this invention is to provide a kind of method of from plant material, extracting oligomeric procyanidolics, using this method to extract main component from natural plant raw material is dimer and trimerical oligomeric procyanidolics, easy and simple to handle, be easy to realize, and oligomeric procyanidolics content is higher in the product.
For achieving the above object, the present invention has adopted following technical scheme:
This method of extracting oligomeric procyanidolics from plant material may further comprise the steps:
A, the plant material that exsiccant is contained pycnogenols are crushed to suitable granularity;
The leach liquor that the solvent preparation contains pycnogenols is leached in b, adding;
C, in the leach liquor of gained, add inorganic salt and make contamination precipitation;
D, with polar organic solvent extraction oligomeric procyanidolics;
E, oligomeric procyanidolics is separated out from polar organic solvent with non-polar organic solvent;
F, the product of separating out is made purification process.
The plant material that can be used for extracting oligomeric procyanidolics is a lot of, the composition of polyphenol or flavonoids is different with content in the various raw materials, and wherein oligomeric procyanidolics content is higher, the source is wide, lower the having of price: leaf, cone or bark of fruit, Testa arachidis hypogaeae and podocarpus falcatus, Araucaria bidwilli, Ramulus et folium taxi cuspidatae, Japanese red pine and maritime pine etc. or the like are planted in trester (mixture of Pericarpium Vitis viniferae and Semen Vitis viniferae), mountain.Trester is meant that grape fruit through pressing extracting juice, is used to make grape juice beverage or by product vinous.
Different and different because of plant variety and growing environment condition of the content of oligomeric procyanidolics and extraction yield in the various raw materials, raw material stores or through long-distance transport, extraction yield greatly reduced as long-time in high temperature, moist environment.Therefore, after obtaining raw material, should as far as possible in time carry out the non high temperature drying treatment on the spot or nearby, and then deposit and wait until extraction.
The best plant material that contains pycnogenols described in the inventive method step is mainly leaf, cone or the bark etc. of trester, Fructus Crataegi, Testa arachidis hypogaeae or aforementioned kind pine, China fir.
Method of the present invention is based on following principle:
Contain a plurality of hydroxyls in the oligomeric procyanidolics molecule, therefore soluble in water, methyl alcohol, ethanol, propyl alcohol, acetone, ethyl acetate isopolarity solvent or the mixture of several solvents wherein; Be not soluble in non-polar solvent or their mixtures such as ether, methylene dichloride, chloroform.These solvents all are operable solvents in food and medicine processing and preparation.Utilize the above-mentioned character of oligomeric procyanidolics dexterously, it can be separated with a large amount of impurity in the raw material.
The present invention is the oligomeric procyanidolics goods that obtain high density with the method for organic solvent extraction and selective precipitation.Concrete grammar is as follows:
One, the preparation of raw material:
To be crushed to through the plant material that the non high temperature exsiccant contains pycnogenols suitable granularity (raw material is without pulverizing, though or excessive through pulverizing granularity, leaching yield will be reduced).
Two, leaching and initial gross separation:
According to the difference of raw material, add the water of capacity or the mixed solution of water and alcohol or acetone, at degree centigrade following dipping of room temperature to 100, constantly fully stir to promote leaching.
Above-mentioned solidliquid mixture is left standstill, treat undissolved solid settlement after, inclining drains supernatant liquor, perhaps by centrifugal or filter and to carry out solid-liquid separation.Flood filter residue 2-3 time repeatedly with homogeneous solvent.Merge each time gained solution.
In the solution that merges, add inorganic salt to saturation concentration, make contamination precipitation.It can be ammonium sulfate, ammonium chloride, sodium sulfate, sodium-chlor or calcium chloride that institute adds inorganic salt.Through centrifugal or filter to remove precipitation.
Three, extraction and phase-splitting:
With appropriate amount of organic above-mentioned solution is extracted.Enough place for a long time by centrifugal or process, isolate water, organic phase and colloid layer.Used organic solvent should be water-fast polar organic solvent, or the mixture of several polar organic solvents.Re-extract 2～5 times.Merge each time gained organic phase and colloid layer respectively.
The colloid layer that merges is placed through centrifugal or long period again.Further isolated clarification organic solution and above-mentioned organic phase merge.
Four, processed:
Add siccative in the organic solvent extraction liquid that merges, for example anhydrous sodium sulphate or Calcium Chloride Powder Anhydrous etc. are to remove wherein contained moisture.Extraction liquid is carried out processed can improve the following rate of recovery of separating out in the step.
Five, concentrate organic phase and recovery organic solvent:
The above-mentioned organic extract liquid of underpressure distillation makes it to be concentrated into 1/5 to 1/10 of original volume, reclaims organic solvent simultaneously, waits until recycling.
Six, separate out:
Above-mentioned spissated organic solution is progressively added in the non-polar solvent that is several times as much as its volume, constantly stir the latter simultaneously, oligomeric procyanidolics will be separated out this moment.Used non-polar solvent can be a kind of or wherein several mixture in the aforementioned non-polar solvent (ether, methylene dichloride, chloroform etc.).
Precipitate 2-3 time with a small amount of non-polar solvent washing gained of the same race.
The exhausted non-polar solvent after underpressure distillation, can recycle.
Seven, purifying:
With the precipitation of an amount of above-mentioned polar organic solvent dissolving, remove the insoluble substance that may occur through washing.Again gained organic solution is progressively added in the non-polar solvent that is several times as much as its volume, repeat the above-mentioned step of separating out.
Repeat this purification step several times, can obtain the purified product.
The oligomeric procyanidolics that obtains with aforesaid method extraction, separation and purifying is the oldlace amorphous powder, and nothing is smelt, and is water-soluble entirely.Dry product is at room temperature stable, can preserve indefinitely in dry environment.
Method of the present invention is owing to adopt technique scheme, and have the following advantages: raw material obtains easily, and cheap; Agents useful for same is common agents, and can re-use after recovery to reduce production costs, and reduces and pollutes; Operational condition is fairly simple, is easy to realize; Procyanidin content is higher in the products obtained therefrom; Residue behind the extraction pycnogenols also can be used as high-quality feed or fertilizer, has significant commercial advantage.
The invention will be further described below in conjunction with embodiment.
Embodiment: from trester (or Fructus Crataegi), extract oligomeric procyanidolics.
1, with exsiccant trester (or Fructus Crataegi) raw material pulverizing to 18～100 order.
2, in through the raw material of pulverizing, add 8-15 doubly to the water of its quality or the mixed solution of water and acetone (water is 1:(0～0.5 with the ratio of acetone)), in degree centigrade down dipping and fully stirring 1～4 hour of room temperature to 50.
3, through standing sedimentation, filter or the centrifugal dregs of removing, keep leach liquor.
4, the mixed solution of water or water and acetone floods above-mentioned dregs 2-5 time repeatedly, and the gained leach liquor all merges with above-mentioned leach liquor.
5, in above-mentioned amalgamation liquid, add ammonium sulfate or sodium-chlor to its saturation concentration.Centrifugal or filter with disgorging, keep solution.
6, with ethyl acetate above-mentioned solution is extracted, the volume ratio of ethyl acetate and above-mentioned solution is 1: (2～10).
7, extraction liquid is left standstill 4～100 hours, perhaps centrifugal to improve the branch interval velocity.Water phase separated, organic phase and colloid layer.
8, with ethyl acetate above-mentioned water is extracted 1～4 time again.With the same method water phase separated, organic phase and colloid layer.The organic phase and the colloid layer that merge each time extraction gained respectively.
9, the colloid layer that merges was left standstill 24～48 hours, treat its further layering, perhaps centrifugal to improve its stratified speed.Organic phase in isolated organic phase and the step 7 merges.
10, in the organic phase that merges, add siccative such as anhydrous sodium sulphate or Calcium Chloride Powder Anhydrous, to remove wherein residual moisture.By centrifugal or filtering separation organic solution and siccative.Siccative is waited until after reclaiming dehydration and is recycled.
11, dried organic solution is under reduced pressure distilled, make it to be concentrated into about 1/10 of original volume, reclaim organic solvent simultaneously, wait until recycling.
12, above-mentioned concentrated organic solution is progressively added 1～4 times in the chloroform of its volume, constantly stir chloroform simultaneously, oligomeric procyanidolics is separated out.Filtration or centrifugal to isolate precipitation, collecting precipitation.
13, wash isolated precipitation with minimum of chloroform.Merge the used chloroform of each time, after distillation is reclaimed, wait until recycling.
14, the content of pycnogenols is not less than 60% in the gained precipitation, and other is the residual less phenolic compound of pectin, carbohydrate, protein and molecular weight.Gained is precipitated water-soluble, extract with ethyl acetate again, in chloroform, precipitate then.Repeat this operation 1～3 time, can further improve the wherein content of oligomeric procyanidolics with purifying products to required purity.
The said products is removed residual organic solvent simultaneously through vacuum-drying or low-temperature reduced-pressure drying, incapsulates, is pressed into tablet or make electuary behind adding batching and the auxiliary material, for oral.Also can be used as the raw material of secondary development, be used to produce protective foods, beverage or skin cosmetic.
Is that the product that raw material obtains is pure oldlace with the trester, with the Fructus Crataegi be the product that obtains of raw material then slightly redly, behind purifying repeatedly, redness will be subdued.No matter be to use wherein which kind of raw material, all stable with the product chemical property that obtains behind aforesaid method extraction and the purifying, but under room temperature and exsiccant condition, all store indefinitely.
Claims (10)
1, a kind of method of extracting oligomeric procyanidolics from plant material, this method comprises the steps:
A, the plant material that exsiccant is contained pycnogenols are crushed to suitable granularity;
The leach liquor that the solvent preparation contains pycnogenols is leached in b, adding;
C, in the leach liquor of gained, add inorganic salt and make contamination precipitation;
D, with polar organic solvent extraction oligomeric procyanidolics;
E, oligomeric procyanidolics is separated out from polar organic solvent with non-polar organic solvent;
F, the product of separating out is made purification process.
2, the method for extracting oligomeric procyanidolics from plant material according to claim 1, it is characterized in that: the described plant material that contains pycnogenols is leaf, cone or the bark of trester, Fructus Crataegi, Testa arachidis hypogaeae and podocarpus falcatus, Araucaria bidwilli, Ramulus et folium taxi cuspidatae, Japanese red pine and maritime pine etc.
3, the method for extracting oligomeric procyanidolics from plant material according to claim 1, it is characterized in that: described leaching solvent is the mixed solution of water and water and alcohol or acetone.
4, the method for extracting oligomeric procyanidolics from plant material according to claim 1 is characterized in that: described to make the inorganic salt of mixed solution contamination precipitation can be ammonium sulfate, ammonium chloride, sodium sulfate, sodium-chlor or calcium chloride.
5, the method for extracting oligomeric procyanidolics from plant material according to claim 1 is characterized in that: described polar organic solvent can be ethanol, propyl alcohol, butanols, acetone, ethyl acetate or the mixture of several solvents wherein.
6, the method for extracting oligomeric procyanidolics from plant material according to claim 1, it is characterized in that: described non-polar organic solvent can be ether, methylene dichloride, chloroform or their mixture.
7, the method for extracting oligomeric procyanidolics from plant material according to claim 1, it is characterized in that: described steps d can repeat 2～5 times.
8, the method for from plant material, extracting oligomeric procyanidolics according to claim 1, it is characterized in that: the described concrete grammar that oligomeric procyanidolics is separated out with non-polar organic solvent from polar organic solvent is by the concentrated solution of oligomeric procyanidolics in polar organic solvent joined in the relatively large non-polar organic solvent, makes oligomeric procyanidolics separate out and separate with impurity.
9, the method for extracting oligomeric procyanidolics from plant material according to claim 1 is characterized in that: separating out that product can repeatedly dissolve again and separate out and carry out purifying described in the step f.
10, the method for extracting oligomeric procyanidolics from plant material according to claim 1 is characterized in that: reclaim various polarity, non-polar organic solvent among implementation step d, the e simultaneously, for recycling.
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| CN01109225A CN1373129A (en) | 2001-02-28 | 2001-02-28 | Process for extracting oligoprotoanthocyanidin from plant |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101845036A (en) * | 2010-06-01 | 2010-09-29 | 新疆海瑞盛生物工程股份有限公司 | Method for extracting procyanidin from wine lees |
| CN102086187A (en) * | 2011-01-28 | 2011-06-08 | 云南瑞升烟草技术（集团）有限公司 | Method for extracting and separating out oligomeric proanthocyanidins from Yunnan pine barks |
| CN102585543A (en) * | 2011-12-16 | 2012-07-18 | 青岛春明调味品有限公司 | Ingredient for preparing peanut red skin pigment and preparation method |
| CN102911150A (en) * | 2012-11-15 | 2013-02-06 | 山东沂蒙山花生油股份有限公司 | Process for preparing oligomeric proantho cyanidins by peanut skin |
| CN103833718A (en) * | 2013-04-24 | 2014-06-04 | 新乡医学院 | Preparation method and application of proanthocyanidin derivative |
| CN105770213A (en) * | 2016-04-14 | 2016-07-20 | 天津药物研究院有限公司 | Grape-seed specific mean-degree-of-polymerization procyanidin extract and preparing method and application thereof |
| CN106083799A (en) * | 2016-07-31 | 2016-11-09 | 江南大学 | A kind of method preparing different purity and the procyanidin without aflatoxin |
| CN107951964A (en) * | 2017-12-12 | 2018-04-24 | 山东金胜粮油集团有限公司 | A kind of peanut red coat extract and grape seed extract compounding capsule and its production method |
| CN109054434A (en) * | 2018-08-31 | 2018-12-21 | 浙江理工大学 | The preparation method and applications of Chinese fir leaf natural dye |
| CN109096236A (en) * | 2018-08-13 | 2018-12-28 | 安徽兆龙生物科技有限公司 | Blueberry procyanidine biological extraction process |
| CN112159382A (en) * | 2020-09-14 | 2021-01-01 | 华南农业大学 | Method for efficiently preparing active oligomeric proanthocyanidins from physiological fruit drop of litchi |
| CN113956679A (en) * | 2021-11-19 | 2022-01-21 | 长江师范学院 | Method for rapidly extracting carmine radish anthocyanin |
-
2001
- 2001-02-28 CN CN01109225A patent/CN1373129A/en active Pending
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101845036A (en) * | 2010-06-01 | 2010-09-29 | 新疆海瑞盛生物工程股份有限公司 | Method for extracting procyanidin from wine lees |
| CN102086187A (en) * | 2011-01-28 | 2011-06-08 | 云南瑞升烟草技术（集团）有限公司 | Method for extracting and separating out oligomeric proanthocyanidins from Yunnan pine barks |
| CN102086187B (en) * | 2011-01-28 | 2012-05-23 | 云南瑞升烟草技术（集团）有限公司 | Method for extracting and separating out oligomeric proanthocyanidins from Yunnan pine barks |
| CN102585543A (en) * | 2011-12-16 | 2012-07-18 | 青岛春明调味品有限公司 | Ingredient for preparing peanut red skin pigment and preparation method |
| CN102911150A (en) * | 2012-11-15 | 2013-02-06 | 山东沂蒙山花生油股份有限公司 | Process for preparing oligomeric proantho cyanidins by peanut skin |
| CN102911150B (en) * | 2012-11-15 | 2014-07-09 | 山东沂蒙山花生油股份有限公司 | Process for preparing oligomeric proantho cyanidins by peanut skin |
| CN103833718A (en) * | 2013-04-24 | 2014-06-04 | 新乡医学院 | Preparation method and application of proanthocyanidin derivative |
| CN105770213A (en) * | 2016-04-14 | 2016-07-20 | 天津药物研究院有限公司 | Grape-seed specific mean-degree-of-polymerization procyanidin extract and preparing method and application thereof |
| CN106083799A (en) * | 2016-07-31 | 2016-11-09 | 江南大学 | A kind of method preparing different purity and the procyanidin without aflatoxin |
| CN106083799B (en) * | 2016-07-31 | 2018-08-14 | 江南大学 | A method of preparing different purity and the procyanidine without aflatoxin |
| CN107951964A (en) * | 2017-12-12 | 2018-04-24 | 山东金胜粮油集团有限公司 | A kind of peanut red coat extract and grape seed extract compounding capsule and its production method |
| CN107951964B (en) * | 2017-12-12 | 2021-02-09 | 山东金胜粮油集团有限公司 | Peanut skin extract and grape seed extract compound capsule and production method thereof |
| CN109096236A (en) * | 2018-08-13 | 2018-12-28 | 安徽兆龙生物科技有限公司 | Blueberry procyanidine biological extraction process |
| CN109054434A (en) * | 2018-08-31 | 2018-12-21 | 浙江理工大学 | The preparation method and applications of Chinese fir leaf natural dye |
| CN112159382A (en) * | 2020-09-14 | 2021-01-01 | 华南农业大学 | Method for efficiently preparing active oligomeric proanthocyanidins from physiological fruit drop of litchi |
| CN112159382B (en) * | 2020-09-14 | 2023-02-28 | 华南农业大学 | Method for efficiently preparing active oligomeric proanthocyanidins from physiological fruit drop of litchi |
| CN113956679A (en) * | 2021-11-19 | 2022-01-21 | 长江师范学院 | Method for rapidly extracting carmine radish anthocyanin |
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