CN101284022B - Complexation extraction method of plant polyphenols substances - Google Patents
Complexation extraction method of plant polyphenols substances Download PDFInfo
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- CN101284022B CN101284022B CN2007100620428A CN200710062042A CN101284022B CN 101284022 B CN101284022 B CN 101284022B CN 2007100620428 A CN2007100620428 A CN 2007100620428A CN 200710062042 A CN200710062042 A CN 200710062042A CN 101284022 B CN101284022 B CN 101284022B
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Abstract
The invention relates to a method for complexing and extracting plant polyphenol compounds to realizes the extraction of the plant polyphenol compound based on reversible complex reaction. Compared with the conventional physical extraction method, the method has the advantages of high separation efficiency and high purity of plant polyphenols, simple process, easy operation, and low energy consumption.
Description
Technical field
The present invention relates to a kind of extracting process of plant polyphenol.
Background technology
Modern medicine study proves that free radical is the main inducing of human senility and some chronic disease.When free-radical generating too much or removed when slow, various organs are sustained damage, thereby quicken the old and feeble of human body and bring out multiple disease.Because plant polyphenol material; can provide the various reactive oxygen free radical of quencher needed hydrogen; play the effect of removing free radical, inhibited oxidation process, the various organs of protection; therefore become a hot research in recent years and a very fast field of development, have the scholar to be referred to as the 7th class nutrient after dietary fiber.
The physiologically active of polyphenol is its chemically active comprehensive embodiment often.These physiologically actives are except polyphenol and protein (enzyme); alkaloid; beyond the reasons such as compound reaction of biomacromolecule and polysaccharide link; also to have stronger removing free radical and an antioxygenic property closely related with polyphenol. and modern medicine study is verified; it is all relevant with the free radical of surplus that a lot of diseases such as histoorgan are aging etc.; polyphenol is by removing free radical; can the biomacromolecule damage that free radical brings out be played a protective role; keep flowability of cell membranes and proteinic configuration conformation; prevent radiation induced dna break, have tangible mutation (as tea polyphenols); antitumor (as ellagic acid); anticancer disease (peaceful) as Punica granatum L.; suppress hypertension (as the Radix Et Rhizoma Rhei tannin) effect.Polyphenol and proteinic reaction property are called convergence, polyphenol has performances such as good antimicrobial, antiviral, be used for dental caries (inhibition streptococcus growth) as the Semen Arecae tannin, the Rhizoma Osmundae tannin is used for the treatment of flu (suppressing cold virus), be because the protein bound of itself and microorganism, virus etc., thereby make their inactivations.Be subjected to ultraviolet radiation for a long time, can cause people's epidermis cell to be undergone mutation, and then cause pathological changes such as skin carcinoma, polyphenol can absorb the ultraviolet in the daylight effectively, thereby can prevent this class sudden change.Simultaneously, polyphenols can combine with the tyrosine invertase, stops melanic generation, prevents skin darkening or freckle, brown patch etc. occur, is used to preparation of Skin whitening care cosmetics etc. as Radix Hamamelidis Mollis polyphenol and tannin.
Along with the more physiologically active of plant polyphenol is found gradually, researcheres are recognized: physiologically active has strict requirement to the stereochemical structure (configuration and conformation) of polyphenol, its physiologically active of the plant polyphenol that phenolic hydroxyl group is many in the molecule, molecular weight is bigger is higher, and the polyphenol with strong convergence often also has stronger radical scavenging activity simultaneously, thereby also has stronger pharmacologically active.
Plant polyphenol is the mixture of the aldehydes matter of a class complexity, and its molecular weight distribution is very wide, from hundreds of to several ten thousand even can reach hundreds of thousands.A large amount of phenolic hydroxyl groups make it have certain hydrophilic, and are soluble in water, mainly exist with colloidal form in aqueous solution.Plant polyphenol is of a great variety, mainly contains phenolic acid, proanthocyanidin, tannin, flavonoid etc.At present, mainly extract polyphenols both at home and abroad: Folium Camelliae sinensis, Fructus Perillae, Semen Sesami, Semen Vitis viniferae and leaf, codlin, seed of Radix Oenotherae erythrosepalae skin, Pericarpium Citri tangerinae skin, Semen sojae atricolor, eucalyptus leaves, Rhizoma Zingiberis Recens, Folium Mori etc. from following plant component, wherein, grape seed polyphenols proanthocyanidin content has the title of " polyphenol king " up to 90%.
The side-product of ripe, the green fruit and the fruit juice course of processing: marc, peel, seed), fresh and dried feed or other plant material of Fructus Vitis viniferae (comprising: Pericarpium Vitis viniferae, Semen Vitis viniferae), Sorghum vulgare Pers. (comprising: clever shell, seed), Cortex Pini the polyphenols of indication of the present invention is mainly derived from: Fructus Mali pumilae and Prunus humilis (comprising:.
The monomer of indication and polymeric plant polyphenol mainly comprise following seven big classes in this invention:
1. flavonol (Flavonls)
Comprise: isorhamnetin (Isorhamnetin), kaempferol (Kaemopferol), myricetin (Myrincetin), Quercetin (Quercetin).
2. flavone (Flavones)
Comprise: Herba Apii graveolentis aglycon (Apigenin), luteolin (Luteolin)
3. flavanone (Flavanones)
Comprise: eriodictyol (Eriodictyol), Hesperidin (Hesperetin), naringenin (Naringenin),
4, flavan-3-alcohol (Structure of flavan-3-ols)
Comprise: catechin (Catechin), catechin-3-gallate (Catechin-3-gallate), table two theine (Epicatechins), table two theine-3-gallate (Epicatechin-3-gallat), epigallo catechin (Epigallocatechin), epigallo catechin-3-gallate (Epigallocatechin-3-gallate), nutgall catechin (Gallocatechin), nutgall catechin-3-gallate (Gallocatechin-3-gallate),
Flavan-3-ol R1 R2 R3
(+)-Catechin(C) H H OH
(+)-Catechin-3-gallate(CG) H H Gallate
(-)-Epicatechin(EC) H OH H
(-)-Epicatechin-3-gallate(ECG) H Gallate H
(-)-Epigallocatechin(EGC) OH OH H
(-)-Epigallocatechin-3-gallate(EGCG)?OH Gallate H
(+)-Gallocatechin(GC) OH H OH
(+)-Gallocatechin-3-gallate(GCG) OH H Gallate
5, theaflavin (Theaflavins.)
Comprise: theaflavin (theaflavin), theaflavin-3-gallate (theaflavin-3-gallate), theaflavin-3 '-gallate (theaflavin-3 '-gallate), theaflavin-3,3 '-two gallates (theaflavin-3 '-digallate),
6, anthocyanidin (cyanidin)
Comprise: anthocyanidin (cyanidin), delphinidin (delphinidin), diformazan delphinidin (malvidin) pelargonidin (pelargonidin), peonidin (peonidin), petuniaization pigment (petunidin)
7, pass through β C by above-mentioned flavonol monomeric substance
4-C
8, β C
4-C
6With α C
2-O-C
7And C
4-C
8The degree of polymerization that key forms is Polyphenols A, B, the C type polymer of 2-10.
From the key link analyses such as " extraction → separation → purification " that plant polyphenol is produced, general both at home and abroad at present employing water, acid first, ethanol or acetone carry out the lixiviate pretreatment; Then, adopt following method respectively according to dissimilar raw materials and equipment:
(1) organic solvents such as petroleum ether, ether, ethyl acetate carry out physical extraction according to the polarity of different plant polyphenols and the difference of molecular weight, such as Chinese patent 03128215.6 disclosed " extracting method of polyphenol in the Rhizoma Nelumbinis ".Chinese patent 02123883.9 disclosed " extracting the process of tea polyphenols " have all been adopted the organic solvent extracting access method.This theoretical basis of utilizing organic solvent to carry out physical extraction, be based upon the difference of the partition coefficient of plant polyphenol in water and different organic solvents, the efficient of extraction is relatively lower, not enough to the plant polyphenol utilization of having leached, the Recovery of Organic Solvent utilization needs special equipment, and energy resource consumption is higher.
(2) alkali metal or alkaline-earth metal ions carry out sedimentation method separation; The technological deficiency of precipitation by metallic ion is that metal ion easily and the molecule of plant polyphenol forms stable network and material or make plant polyphenol through oxidation-reduction reaction, causes the biological activity of plant polyphenol molecule to reduce;
(3) use CO
2Surpass and face the separation that extraction carries out plant polyphenol; As Chinese patent 200510048168.0 disclosed " method of supercritical carbon dioxide extracting apple polyphenol from pomace " and Chinese patent 200410013248.8 disclosed " high-purity tea polyphenol extracting method ".All adopt CO
2Supercritical extraction carries out the plant polyphenol separation and Extraction.This method need adopt expensive equipment, and production cost is higher, still is in the experimentation stage at present;
(4) use the large aperture resin adsorption method to carry out the separation and purification of plant polyphenol polyphenol, as Chinese patent 200510060603.1 disclosed " preparation technology of grape seed polyphenols ", adopt water to carry out lixiviate, centrifuge concentrates and macroporous resin adsorption and ethyl acetate extraction technology.Chinese patent 200510129368.9 disclosed " a kind of extracting method of effective portion of polyphenol acid " etc.Adopt the large aperture resin adsorption method to carry out the separation and Extraction of plant polyphenol, have technology characteristics easy, with low cost, still, use the large aperture resin, be subjected to the strictness restriction of relevant industries rules in food production and pharmaceuticals industry field.
Summary of the invention
The present invention is directed to the deficiency that above-mentioned prior art exists, proposed a kind of complex-extracting method of plant polyphenol.
The complex-extracting method of plant polyphenol of the present invention comprises the steps:
(1) pretreatment of raw material: after raw material pulverizing was the 10-20 order, appropriate containers was inserted in weighing, and in 1: the acid pure water that the ratio of 1-7 adds pH value 3-4 soaked 0.5-24 hour, the A sample;
(2) physics extracts: with the A sample that preprocessing process obtains, adopt ultrasound wave or microwave extraction and filter the plant polyphenol filtrate, i.e. B sample;
(3) preparation: with above-mentioned filtrate through centrifugalize or refilter separate the plant polyphenol extracting solution, i.e. C sample;
(4) produce complexing extractant: get tributyl phosphate and/or trioctyl phosphate and/or trioctylphosphine oxygen phosphorus and kerosene under the room temperature respectively, the n-octyl alcohol uniform mixing gets complexing extractant, wherein tributyl phosphate and/or trioctyl phosphate and/or trioctylphosphine oxygen phosphorus content are 300-570ml/1000ml; The content of kerosene is 300-500ml/1000ml; The content of n-octyl alcohol is 100-400ml/1000ml;
(5) extraction process: plant polyphenol extracting solution and complexing extractant that preparation process obtains are inserted appropriate containers by 1: 1 volume ratio, under 15-30 ℃ of temperature conditions, after oscillation extraction 25-40 minute, standing separation 60-120 minute, upper organic phase after the separation is that the extracted species that extractant and plant polyphenol complexation generate is the D sample, and lower floor is a raffinate;
(6) back extraction process: D sample that extraction process is obtained and the alkaline pure water of pH value 10-11 are inserted in the appropriate containers under the 35-45 condition fully vibration 40-60 minute by 1: 1 volume ratio, standing separation got organic facies and water in about 120 minutes then, wherein organic facies is a mixed extractant, and water is the stripping aqueous solution that contains plant polyphenol;
(7) aqueous solution that back extraction process gained is contained plant polyphenol gets the plant polyphenol product through concentrate drying.
The complex-extracting method of described plant polyphenol, physical extracting method wherein are ultrasonic extracting method, preprocessing process gained soak are inserted in the ultrasonic extraction device of 25-80KHZ, extract 40-60 minute under 35-45 ℃ of condition.
The complex-extracting method of described plant polyphenol is characterized in that centrifugal rotational speed 4000-5000 rev/min of described centrifugal separation processes, and disengaging time is 10-20 minute.
The complex-extracting method of described plant polyphenol, wherein the active constituent of chelating agent is one or more the mixture in tributyl phosphate, trioctyl phosphate, the trioctylphosphine oxygen phosphorus, and kerosene is diluent, and n-octyl alcohol is a secondary solvent.
The complex-extracting method of plant polyphenol of the present invention, different to the physical action of plant polyphenol with organic solvent (ether, ethyl acetate etc.), complexometric extraction is to serve as that the extraction to plant polyphenol is realized on the basis with reversible complex reaction.Compare with traditional physical extraction, have following technical advantage:
The first, complexometric extraction is based on reversible complex reaction, and to the separation efficiency height of plant polyphenol, its separation efficiency quite and more than ten times of physical extraction;
The second, the selectivity of complex reaction is higher, and object purity is higher;
Three, the recyclable recycling of extractant, it is simple and easy to do to have process, and energy resource consumption is low;
Four, all technical process is easy to realize.
Method of the present invention can be extracted plant polyphenol from different tissues such as Fructus Mali pumilae, Prunus humilis, Fructus Vitis viniferae, Sorghum vulgare Pers. and Cortex Pini.With the Fructus Mali pumilae is example, China has come off in fruit and the total output 30% cull fruit full scale of apple cultivation area, per unit area 100---150 kilogram now and calculates, the whole nation has ten thousand tons of 1100---1350 approximately, be used to produce the available resources of apple polyphenol, the whole nation can produce about 250,000 tons of apple polyphenol materials, can count about 2,500,000,000 yuan more than of the output value.If fruit that the orchard produced that will need to eliminate or upgrade and Semen Vitis viniferae, Fructus Crataegi etc. count, the available resources total amount and the potential economic worth that are used to produce plant polyphenol are higher.
The specific embodiment
The complex-extracting method of plant polyphenol of the present invention is different to the physical action of plant polyphenol with organic solvent (ether, ethyl acetate etc.), and complexometric extraction is to serve as that the extraction to plant polyphenol is realized on the basis with reversible complex reaction.According to the broad acid-base theory analysis, plant polyphenol belongs to lewis acid because of containing a plurality of phenolic hydroxyl groups, can combine with lewis base under suitable condition.Complexometric extraction based on reversible complex reaction, it is the method for the polar organic compound extract and separate of professor C.J.King of California, USA university proposition, this kind method has very strong selectivity and high efficiency to the separation of polar organic matter weak solution, and its basic extraction process can be expressed as:
The extracted species that complex reaction forms be in temperature, can decompose again when PH changes, thereby realizes the separation of polar organic compound and the recycling of extractant.
Whole complex extractions processes of plant polyphenol can be represented by flow process shown in Figure 1:
1, preprocessing process: after raw material pulverizing is the 10-20 order, appropriate containers is inserted in weighing, and add the acid pure water of pH value 3-4 by proper proportion, the proper proportion is here mainly seen the kind and the degree of drying of raw material, (wherein: new Cortex Dictamni, leaf class sample are 1: 1-2, seed sample are 1: 1-4, drying sample are 1: 5-7), described acid pure water is allocated by industrial distilled water or industrial pure water and sulphuric acid or hydrochloric acid or other commercial acid and is formed.
Soak time 0.5-24 hour; Soak time is same relevant with the freshness and the degree of drying of raw material.Such as fresh leaf class raw material, then soak time got final product at 0.5-1 hour, and then soak time is longer for exsiccant seed class raw material, can reach 20-24 hour.
2, physics extracts: the better physical extracting method adopts supersonic extracting method, the A sample that preprocessing process is obtained, insert in the ultrasonic extraction device of 25-80KHZ, under 40 ℃ of conditions, extracted 40-60 minute, filter then, collect filtrate, residue under the same conditions, extract operation 2-3 time, collection and merging filtrate obtain the B sample.
As adopt common microwave extraction or other extracting method commonly used can obtain effect same.
3, preparation: the B sample with the ultrasonic extraction process obtains under 4000-5000 rev/min condition, centrifugalize 10-20 minute, obtains the plant polyphenol extracting solution.
This preparation process also can adopt accurate filter paper (plate) filter method, or other physical separation method, can obtain above-mentioned plant polyphenol extracting solution simply and effectively equally.
4, produce complexing extractant: get tributyl phosphate and/or trioctyl phosphate and/or trioctylphosphine oxygen phosphorus and kerosene under the room temperature respectively, the n-octyl alcohol uniform mixing gets complexing extractant, wherein tributyl phosphate, trioctyl phosphate, trioctylphosphine oxygen phosphorus are the active ingredients of chelating agent, get they one or more mixture and diluent kerosene and secondary solvent n-octyl alcohol at normal temperatures mix homogeneously get final product.
The content of each composition is as follows: the content of tributyl phosphate and/or trioctyl phosphate and/or trioctylphosphine oxygen phosphorus is 300-570ml/1000ml; The content of kerosene is 300-500ml/1000ml; The content of n-octyl alcohol is 100-400ml/1000ml;
5, extraction process: will prepare the plant polyphenol extracting solution that leaching process obtains, insert suitable container with mixed extractant by 1: 1 volume ratio, abundant mixing, under 15-30 ℃ of temperature conditions, carry out the oscillation extraction operation after 25-40 minute, standing separation 60-120 minute then, upper organic phase after the separation is the extracted species that extractant and plant polyphenol complexation generate, lower floor is a raffinate, and with isolating raffinate repetitive operation 2-3 time, and the gained organic facies is merged promptly is whole extracted specieses.
6, back extraction process: extracted species that extraction process is obtained and the alkaline pure water of pH value 10-11 are inserted in the proper container by 1: 1 volume ratio, carry out the back extraction operation under 35-50 ℃ of condition, after fully vibrating 40-60 minute, and about 120 minutes of standing separation; Organic facies after the separation is a mixed extractant, and water is the stripping aqueous solution that contains plant polyphenol, and isolated organic facies is repeated back extraction operation 2-3 time, with next step concentrate drying of stripping aqueous solution mixing carrying out of back extraction gained.
Described alkaline pure water is formed by industrial distilled water or industrial pure water and sodium hydroxide or the allotment of other industrial soda.
7, concentrate drying: with the 1/3-1/10 of stripping aqueous solution simmer down to original volume under 40-60 ℃ of condition, and dry under the same conditions, obtain the plant polyphenol product.
Product can carry out the mensuration of plant polyphenol total amount according to Folin-phenol method, and flavonol is measured with the vanillin method, and proanthocyanidin is measured with the n-butyl alcohol method, and also available liquid chromatography is distinguished quantitative analysis to one-component and measured.
Embodiment-1: the complexometric extraction of Fructus Mali pumilae and Prunus humilis polyphenol
1. preprocessing process:
(wherein: the Fructus Mali pumilae fruit is cut into the cutting about 0.5 centimetre to take by weighing marc, peel, the fruit of Fructus Mali pumilae or Prunus humilis respectively, the Prunus humilis fruit shreds after removing kernel) raw material 500 grams, insert in the proper container, acid pure water with pH value 3-4 soaked 30 minutes for 1000 milliliters, pulverize about 30 seconds with pulverizer, make raw meal particle size reach the 10-20 order, supersound process is 40 minutes under ultrasonic frequency 40KHZ, power 200W, 40 ℃ of conditions of temperature, get filtrate after filtration, residue can repeat to extract processing 2-3 time and the gained filtrate is merged under the same conditions; Under 4000-4500 rev/min of condition, centrifugalize 10 minutes discards residue with above-mentioned whole filtrate, gets extracting solution;
2. extraction process:
With pipette, extract tributyl phosphate 31ml, n-octyl alcohol 22ml, kerosene 47ml, fully mix homogeneously is mixed with complexing extractant to room temperature down;
Measure 250 milliliters of extracting solution, 250 milliliters of extractants with graduated cylinder, place 1000 milliliters of separatory funnels, separatory funnel is placed on the temperature control shaking table, vibration is after 25 minutes under the condition of temperature 25-30 ℃, rotating speed 200-250 rev/min, separated in static 60 minutes, lower floor after the separation is a raffinate, and the upper strata is the organic facies that contains extracted species; Lower floor's raffinate is repeated this operation 2-3 time, and will each isolatingly contain the organic facies merging of extracted species;
3. back extraction process:
Organic facies that contains extracted species and alkaline pure water (pH=11), measure 250ml respectively, by volume ratio according to 1: 1, insert in 1000 milliliters of separatory funnels, place on the temperature control shaking table, under the condition of temperature 35---45 ℃, rotating speed 200-250 rev/min, vibrated 40 minutes, separate after static 120 minutes; Lower floor is the strip liquor that contains plant polyphenol, and the upper strata is the organic facies that contains extracted species; Upper organic phase is repeated this operation 2---3 time, and the upper organic phase after the separation can be reused in extracting operation; And the strip liquor that will each isolatingly contain plant polyphenol merges;
4. concentrated, dry run:
The strip liquor that contains apple polyphenol, under 35-45 ℃ of temperature conditions, after the employing concentrator is concentrated into the 1/3---1/5 of original volume, under the uniform temp condition, carry out dried, can obtain Fructus Mali pumilae or Prunus humilis polyphenol product.
Embodiment-2: the complexometric extraction of Semen Vitis viniferae, Fructus Mali pumilae seed polyphenol
1, preprocessing process:
Take by weighing exsiccant Semen Vitis viniferae, Fructus Mali pumilae seed 500 grams respectively, broken, insert in the proper container, acid pure water with pH value 3-4 soaked 24 hours for 2000 milliliters, supersound process 50 minutes and filtration under ultrasonic frequency 80KHZ, power 200W, 40 ℃ of conditions of temperature, residue repeats to extract under the same conditions handles merging filtrate 2--3 time; Above-mentioned filtrate under 4000---4500 rev/min condition, centrifugalize 10-20 minute, is got extracting solution;
2, extraction process:
With pipette, extract trioctyl phosphate 48ml, n-octyl alcohol 13ml, kerosene 39ml, fully mix homogeneously is mixed with extractant;
Measure 250 milliliters of extracting solution, 250 milliliters of extractants with graduated cylinder, place 1000 milliliters of separatory funnels, separatory funnel is placed on the temperature control shaking table, under the condition of temperature 25-30 ℃, rotating speed 200-250 rev/min, vibrate after 45 minutes, static 120 minutes, the lower floor after the separation was a raffinate, and the upper strata is the organic facies that contains extracted species; Lower floor's raffinate is repeated this operating process 2-3 time, and will each isolatingly contain the organic facies merging of extracted species;
3, back extraction process:
Organic facies that contains extracted species and alkaline pure water (pH value 11), measure 250ml respectively, by volume ratio according to 1: 1, insert in 1000 milliliters of separatory funnels, place on the temperature control shaking table, under the condition of temperature 35-45 ℃, rotating speed 200-250 rev/min, vibrated 40-45 minute, separate after static 100-120 minute; Lower floor is the strip liquor that contains plant polyphenol, and the upper strata is the organic facies that contains extracted species; Upper organic phase is repeated this operation 2-3 time, and the upper organic phase after the separation can be reused in extracting operation; And the strip liquor that will each isolatingly contain plant polyphenol merges;
4. concentrated, dry run:
The strip liquor that contains grape polyphenols, under 35---45 ℃ of temperature conditions, after the employing concentrator is concentrated into the 1/3---1/5 of original volume with strip liquor, under the uniform temp condition, carry out dried, can obtain Semen Vitis viniferae, Fructus Mali pumilae seed polyphenol product.
Embodiment-3: the complexometric extraction of Sorghum vulgare Pers. polyphenol
1. preprocessing process:
The sorghum husk of 10 mesh sieves will be crossed after exsiccant Sorghum vulgare Pers. seed or dry and the pulverizing, take by weighing 500 grams, insert in the proper container, after soaking 24 hours with 3000 milliliters of the acid pure water of pH=3-4, supersound process is 40 minutes under ultrasonic frequency 40KHZ, power 200W, 40 ℃ of conditions of temperature, filters, and gets filtrate, residue can repeat under the same conditions to extract and handle 2-3 time, merges filtrate; Under 4000---4500 rev/min of condition, centrifugalize 10 minutes gets extracting solution with filtrate;
2, extraction process:
With pipette, extract trioctyl phosphate 31ml, n-octyl alcohol 39ml, kerosene 30ml, fully mix homogeneously is mixed with extractant;
Measure 250 milliliters of extracting solution, 250 milliliters of extractants with graduated cylinder, place 1000 milliliters of separatory funnels, separatory funnel is placed on the temperature control shaking table, vibration static 90 minutes, separated after 25 minutes under the condition of temperature 25-30 ℃, rotating speed 200-250 rev/min; Lower floor after the separation is a raffinate, and the upper strata is the organic facies that contains extracted species; Lower floor's raffinate is repeated this operation 2---3 time, and will each isolatingly contain the organic facies merging of extracted species;
3. back extraction process:
Organic facies that contains extracted species and pure water (pH11), measure 250ml respectively, by volume ratio according to 1: 1, insert in 1000 milliliters of separatory funnels, place on the temperature control shaking table, under the condition of temperature 35---45 ℃, rotating speed 200-250 rev/min, vibrated 40 minutes, and separated after static 120 minutes; Lower floor is the strip liquor that contains plant polyphenol, and the upper strata is the organic facies that contains extracted species; Upper organic phase is repeated this operation 2---3 time, and the upper organic phase after the separation can be reused in extracting operation; And the strip liquor that will each isolatingly contain plant polyphenol merges;
4. concentrated, dry run:
The strip liquor that contains the Sorghum vulgare Pers. polyphenol, under 35---45 ℃ of temperature conditions, be concentrated into the 1/3---1/5 of original volume after, under the uniform temp condition, carry out dried, can obtain Sorghum vulgare Pers. polyphenol product.
Embodiment-4: the complexometric extraction of Cortex Pini polyphenol
1. preprocessing process: exsiccant Cortex Pini sample is pulverized, cross 10 mesh sieves, claim sample 500 grams, after soaking 24 hours with 3500 milliliters of the acid pure water of pH=3-4, supersound process is 40 minutes under ultrasonic frequency 40KHZ, power 200W, 40 ℃ of conditions of temperature, filters, and gets extracting solution, residue can repeat to extract under the same conditions handles merge extractive liquid, 23 times; Extracting solution is under 4000---4500 rev/min of condition, and centrifugalize 10 minutes discards residue, and extracting solution extracts;
2. extraction process: draw tributyl phosphate 10ml, trioctylphosphine oxygen phosphorus 20ml, trioctyl phosphate 27ml respectively with pipet, n-octyl alcohol 12ml, kerosene 31ml with the abundant mix homogeneously of above-mentioned composition, are mixed with extractant;
Measure 250 milliliters of extracting solution, 250 milliliters of extractants with graduated cylinder, place 1000 milliliters of separatory funnels, separatory funnel is placed on the temperature control shaking table, vibration static 120 minutes, separated after 25 minutes under the condition of temperature 25-30 ℃, rotating speed 200-250 rev/min; Lower floor after the separation is a raffinate, and the upper strata is the organic facies that contains extracted species; Lower floor's raffinate is repeated this operation 2---3 time, and will each isolatingly contain the organic facies merging of extracted species;
3. back extraction process: organic facies that contains extracted species and pure water (pH10), measure 250ml respectively, by volume ratio according to 1: 1, insert in 1000 milliliters of separatory funnels, place on the temperature control shaking table, under the condition of temperature 35---45 ℃, rotating speed 200-250 rev/min, vibrated 40 minutes, separate after static 90---120 minute; Lower floor is the strip liquor that contains plant polyphenol, and the upper strata is the organic facies that contains extracted species; Upper organic phase is repeated this operation 2---3 time, and the upper organic phase after the separation can be reused in extracting operation; And the strip liquor that will each isolatingly contain plant polyphenol merges;
4. concentrate, dry run: the strip liquor that contains Pine Procyanidins, under 35---45 ℃ of temperature conditions, be concentrated into the 1/3---1/5 of original volume after, under the uniform temp condition, carry out dried, can obtain the Pine Procyanidins product.
Claims (4)
1. the complex-extracting method of a plant polyphenol comprises the steps:
(1) pretreatment of raw material: after raw material pulverizing was the 10-20 order, appropriate containers was inserted in weighing, and in 1: the acid pure water that the ratio of 1-7 adds pH value 3-4 soaked 0.5-24 hour, the A sample;
(2) physics extracts: with the A sample that preprocessing process obtains, adopt ultrasound wave or microwave extraction and filter the plant polyphenol filtrate, i.e. B sample;
(3) preparation: with above-mentioned filtrate through centrifugalize or refilter separate the plant polyphenol extracting solution, i.e. C sample;
(4) produce complexing extractant: get tributyl phosphate and/or trioctyl phosphate and/or trioctylphosphine oxygen phosphorus and kerosene under the room temperature respectively, the n-octyl alcohol uniform mixing gets complexing extractant, wherein tributyl phosphate and/or trioctyl phosphate and/or trioctylphosphine oxygen phosphorus content are 300-570ml/1000ml; The content of kerosene is 300-500ml/1000ml; The content of n-octyl alcohol is 100-400ml/1000ml;
(5) extraction process: plant polyphenol extracting solution and complexing extractant that preparation process obtains are inserted appropriate containers by 1: 1 volume ratio, under 15-30 ℃ of temperature conditions, after oscillation extraction 25-40 minute, standing separation 60-120 minute, upper organic phase after the separation is that the extracted species that extractant and plant polyphenol complexation generate is the D sample, and lower floor is a raffinate;
(6) back extraction process: D sample that extraction process is obtained and the alkaline pure water of pH value 10-11 are inserted in the appropriate containers under 35-45 ℃ of condition fully vibration 40-60 minute by 1: 1 volume ratio, standing separation got organic facies and water in about 120 minutes then, wherein organic facies is a mixed extractant, and water is the stripping aqueous solution that contains plant polyphenol;
(7) aqueous solution that back extraction process gained is contained plant polyphenol gets the plant polyphenol product through concentrate drying.
2. according to the complex-extracting method of the plant polyphenol of claim 1, it is characterized in that the described physical extracting method of step (2) is a ultrasonic extracting method, preprocessing process gained soak is inserted in the ultrasonic extraction device of 25-80KHZ, under 35-45 ℃ of condition, extracted 40-60 minute.
3. according to the complex-extracting method of the plant polyphenol of claim 1, it is characterized in that centrifugal rotational speed 4000-5000 rev/min of the described centrifugal separation processes of step (3), disengaging time is 10-20 minute.
4. according to the complex-extracting method of the plant polyphenol of claim 1, it is characterized in that the active constituent of chelating agent in the step (4) is one or more the mixture in tributyl phosphate, trioctyl phosphate, the trioctylphosphine oxygen phosphorus, kerosene is diluent, and n-octyl alcohol is a secondary solvent.
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| CN101428069B (en) * | 2008-12-08 | 2011-07-20 | 广东省农业科学院蚕业与农产品加工研究所 | Process for producing mulberry leaf polyphenol, microcapsule and uses thereof |
| CN101849977A (en) * | 2010-05-27 | 2010-10-06 | 东北林业大学 | Method for extracting polyphenol from Mongolian oak leaves |
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| CN102823919B (en) * | 2012-09-19 | 2013-08-28 | 昆明理工大学 | Method for extracting insoluble polyphenol in plant dross |
| CN103468755B (en) * | 2013-09-02 | 2015-05-20 | 江苏科技大学 | Method for enzymatic synthesis of phenethyl caffeate in complexation extraction agent/ionic liquid system |
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| CN105250356B (en) * | 2015-09-10 | 2020-01-14 | 黑龙江八一农垦大学 | Method for extracting mung bean polyphenol by microwave and ultrasonic wave synergistic auxiliary solvent |
| CN105558927A (en) * | 2015-12-30 | 2016-05-11 | 湖北文理学院 | Apple seed oxidation preventing additive and preparation method thereof |
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| CN110819745A (en) * | 2019-11-29 | 2020-02-21 | 明新旭腾新材料股份有限公司 | Method for improving smell of leather product by using natural tea leaves |
| CN112316009B (en) * | 2020-12-02 | 2022-04-08 | 宁夏医科大学 | Application of cerasus humilis extract in preparation of antibacterial product |
| CN114377537A (en) * | 2022-01-14 | 2022-04-22 | 浙江工商大学 | Natural plant deodorant and preparation method and application thereof |
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