CN100425605C - Method for extracting persimmon polyphenol from persimmon - Google Patents
Method for extracting persimmon polyphenol from persimmon Download PDFInfo
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- CN100425605C CN100425605C CNB2005100936597A CN200510093659A CN100425605C CN 100425605 C CN100425605 C CN 100425605C CN B2005100936597 A CNB2005100936597 A CN B2005100936597A CN 200510093659 A CN200510093659 A CN 200510093659A CN 100425605 C CN100425605 C CN 100425605C
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Abstract
The present invention discloses a method for extracting persimmon polyphenol from persimmons, which uses persimmons as raw materials and extracts persimmon polyphenol by solvent extraction, condensation, separation and purification, and drying; in the method, water or low-carbon alcohol, such as methanol, alcohol, propyl alcohol, isopropyl alcohol, butanol, etc., is used as solvent; the extracting method adopts heating extraction by the water and the low-carbon alcohol and also adopts ultrasonic extraction or microwave extraction, and the separation and purification can adopt column chromatography. The weight content of the persimmon polyphenol in the extract is more than 70%, and antioxidation performance indexes TEAC and ORAC in the persimmon polyphenol of the extract display that the persimmon polyphenol has very strong antioxidation activity, and overoxidation substances can be effectively removed. The persimmon polyphenol produced by the method of the present invention has the advantages of high polyphenol content, loss avoidance of active components, simplified production technology and shortened production period.
Description
Technical field
The present invention relates to a kind of persimmon preparation method of extract, specifically, relate to a kind of method of from persimmon, extracting the persimmon polyphenol.
Background technology
Persimmon except that taste is good to eat, also has medicinal efficacy, the record of tool Compendium of Material Medica: " edible persimmon can be improved looks and qi-restoratives benefit lung." calyx and receptacle of a persimmon is the good medicine of the contrary vomiting of cough-relieving; Persimmon reveals the detoxifcation of relieving inflammation or internal heat, and treating hematochezia is had special efficacy, and the function of treatment throat, dispute sore pain is arranged again.Persimmon moistens the lung and relieve the cough in addition, the effect of clearing heat and promoting fluid, resolving phlegm and softening hard masses.Bright persimmon is eaten raw, and diseases such as pulmonary tuberculosis cough flaccidity syndrome of the lung due to deficiency-heat, coughing with a lot of sputum, consumptive disease spitting of blood are had good effect.Red soft ripe persimmon can be treated mashed, the disease such as dysphoria with smothery sensation, hot dysentery in the heart of pyreticosis polydipsia, dry lip.
Polyphenol component in the plant has antitumous effect and has obtained proof, and for example, quercetin in the gossypol in catechin monomers ECG in the green tea and EGCG, the cottonseed, the chlorogenic acid in the bark of willow, robur and the Oak Tree and datiscetin etc. all belong to Polyphenols.Germany scientist has had further understanding to the mechanism of polyphenol inhibition growth of tumour cell a few days ago, and finds all to comprise in many plants this natural anti-cancer material.Research group has chosen leukemia cell, lung tumors cell and breast cancer cell as research object in experiment, found that, even have only the polyphenol of trace also can suppress enzyme in the tumour cell, and these enzymes are essential to the generation of triggering tumor cell growth " signal " molecule.In the plant amedica therapy, polyphenol is considered to prevent and suppress the material of tumour.
The persimmon polyphenol not only has antitumous effect, and contains the special polyphenol substance of a class in the persimmon, compares the very big difference of existence with other polyphenols that has now found that such as grape seed polyphenols, Cortex Pini polyphenol, tea-polyphenol etc.Its polyphenols mainly is the macromolecular material of a class that is formed by a plurality of tea-polyphenol topology convergences, the oligomer aldehydes matter of strong anti-oxidation physiologically active will can be obtained having after this type of polyphenol hydrolysis, experiment shows, antioxidant property index TEAC (Trolox Equivalent Antioxidant Capacity) and ORAC (Oxygen RadicalAbsorbance Capacity) show that the persimmon polyphenol has extremely strong anti-oxidant activity, can effectively remove the peroxidation material.
Through patent retrieval, also not having at present to find with the persimmon is the correlative study report that raw material extracts the persimmon polyphenol.
Summary of the invention
The technical issues that need to address of the present invention be not the defective that raw material extracts the persimmon polyphenol with the persimmon to overcome in the prior art just, a kind of method of extracting the persimmon polyphenol from persimmon is provided, and persimmon polyphenol weight content is more than 70% in the inventive method extract.The persimmon polyphenol content height that the inventive method is produced, avoided activeconstituents loss, simplified production technique, shortened the production cycle.
For addressing the above problem, the present invention adopts following technical scheme:
The present invention extracts the method for persimmon polyphenol from persimmon, it be a kind of be raw material with the persimmon, through the method that extraction solvent extracts, concentrates, the persimmon polyphenol is extracted in separation and purification, persimmon polyphenol weight content is more than 70% in the extract.
The used persimmon of the inventive method can be bright persimmon and/or dried persimmon.
The inventive method can be carried out fragmentation with persimmon earlier before extraction, persimmon helps the abundant stripping of various compositions after fragmentation; Fresh fruit presses broken getting final product with it.
The described extracting method of the inventive method is heating extraction or ultrasonic extraction or microwave extraction.
The described extracting method of the inventive method extracts for heating, extraction time is a key that influences yield and content, and general extraction time is 1～3 time, according to test, take all factors into consideration the utilization ratio of extraction equipment usage space and the working substance content of finished product, extraction time is preferably 2 times; The solvent consumption is 3～12 times, and temperature is 40～100 ℃, and extraction time is solvent boiling back 1～3 hour.
Need to reclaim low-carbon alcohol after persimmon of the present invention extracts and handle, temperature is controlled at below 60 ℃, and vacuum degree control is more than 0.06Mpa, and the soup and the raw material weight ratio that reclaim low-carbon alcohol should be controlled between 1: 2～5.
Extraction solvent described in the inventive method is water or low-carbon alcohol.Described low-carbon alcohol is methyl alcohol, ethanol, propyl alcohol, Virahol or butanols, and the weight concentration of described low-carbon alcohol is 1%～95%.
The described ultrasonic extraction condition of the inventive method is operating frequency 15～80kHz, time 5～120min; The microwave extraction condition is operating frequency 900～2500MHz, time 5～120min.
Separation and purification of the present invention is a column chromatographic isolation and purification.
Column chromatographic isolation and purification of the present invention is:
1) extracting solution is through concentrating (vacuum concentration, temperature is controlled at below 60 degrees centigrade, more than the vacuum tightness 0.08MPa, be concentrated into the 1/4-1/2 of original extracting liquid volume), reclaim low-carbon alcohol, centrifugal (horizontal centrifuge: 4800r/min), directly enter macroporous resin column, flow rate control is about 0.5～1.5BV/hr;
2) it is limpid to effluent liquid to wash post with deionized water, about 2h;
3) wash post to elutriant clarification, transparent with low-carbon alcohol, flow velocity is slightly slower than the speed of absorption;
4) collect effusive clarification from macroporous resin column, transparent, the elutriant of alcohol flavor slightly, about 1～3 times of collecting elutriant and be approximately amount of resin;
5) (vacuum concentration, temperature are controlled at below 60 degrees centigrade pure water elution liquid, and vacuum tightness 0.06-0.1MPa is concentrated into about 10～15 degree Beaume, promptly is concentrated into the 1/4-1/2 of original extracting liquid volume through concentrating.), dry (spraying drying: 160～200 ℃ of intake air temperatures, 80～110 ℃ of air outlet temperature) gets the persimmon polyphenol.
Wherein said low-carbon alcohol is methyl alcohol, ethanol, propyl alcohol, Virahol, butanols or amylalcohol, and the concentration of lower concentration alcohol solution is minimum to be volumetric concentration 30%, and the concentration of high density alcohol solution is up to volumetric concentration 95%; Wherein said macroporous resin is for being the material of skeleton with the polystyrene, and as the DIAION brand, model is: D101, D130, AB-8 or HP-20.
Antioxidant property index TEAC and ORAC show that the persimmon polyphenol has extremely strong anti-oxidant activity, can effectively remove the peroxidation material in the persimmon polyphenol in the extract of the inventive method preparation.
The persimmon polyphenol content height that the inventive method is produced, its weight content is more than 70%, avoided activeconstituents loss, improved production technique, shortened the production cycle.
The test of antioxidant property index TEAC in the persimmon polyphenol (Trolox Equivalent AntioxidantCapacity) and ORAC (Oxygen Radical Absorbance Capacity) anti-oxidant activity:
The antioxidant property of ORAC test in the serum
Reagent is prepared:
1.225mM phosphate buffered saline buffer (pH 7.0): with 39mL 0.45M NaH
2PO
4With 61mL0.45M Na
2HPO
4Mix, regulate pH to 7.0, be diluted to 200mL (room temperature preservation) with deionized water;
2.60nM R-phycoerythrin (PE): with 10mL deionized water dissolving 19.80 μ LR-phycoerythrin (shaking up before the use);
3.18mM AAPH: with 10mL deionized water dissolving 488.1mg AAPH (shaking up before the use)
Method:
The pre-treatment of serum
1. with perchloric acid and the 60 μ L serum mixing in the test tube of 1.5-mL of 20 μ L;
2. then, add 300 μ Ln-butanols, waited for for ten seconds;
With test tube in 12,000rpm centrifugal ten minutes;
4. the last supernatant liquid that pipettes 50L is in the test tube of another 1.5-mL;
5. dry up with purity nitrogen;
6. add 2mL 225mM phosphate buffered saline buffer (pH 7.0)
The ORAC test
1. the serum that 2mL is pretreated and the PE of 2mL mixing in brown test tube;
2.37 ℃ hatched in advance 5 minutes;
3. begin fluorometric analysis (exciting light 540nm by adding 2mLAAPH reagent down at 37 degrees centigrade, radiant light 565nm), after partial reaction solution being transferred to a small test tube in per 3 to 5 minutes, test fluorescence intensity (, stopping test) if fluorescence intensity is reduced to below 20% of original value
Attention:
1.ORAC want lucifuge in the process of the test, close the laboratory luminescent lamp;
2.R-phycoerythrin will in time use after handling;
3.AAPH after the dissolving, must use in ten minutes, because the solution instability;
4.ORAC brown test tube is washed with 1N HCl in the experiment back, removes fluorescin.
The antioxidant property of TEAC test in the serum
Reagent is prepared
(1) 1.25mM trolox solution (standard)
In 10ml 5mM PBS (pH 7.4) lining dissolving 3.13mg Trolox ,-20 ℃ of preservations
(2) 450mM hydrogen peroxide (substratum)
With 0.5ml 30% hydrogen peroxide (H
2O
2) and 9.3ml 5mM PBS mixing, 4 ℃ of preservations (are diluted to 450 μ M H with 5mM PBS during use
2O
2Solution)
(3) 5mM ABTS (DAP) solution (chromogen)
27.43mg ABTS is dissolved among the 10ml 5mM PBS 4 ℃ of brown test tubes keep in Dark Place (being diluted to 500 μ M ABTS solution with 5mM PBS during use)
(4) 70 μ M Met Mb solution (chromogen)
1) purifying Met Mb
68mg myoglobin (Mb) is dissolved in 10ml 5mM PBS (400 μ M Mb)
With 2.44mg of K3[Fe (CN)
6] be dissolved in 10ml 5mM PBS (740 μ MK
3[Fe (CN)
6])
Get 10ml 400 μ M Mb and 10ml 740 μ M K3[Fe (CN)
6] after the mixing, place under the room temperature, activate 15 minutes
With the Sephadex G15-120 post of Met Mb solution by crossing (2.5 φ * 40cm) with 5mM PBS balance
Calculate the elution yield with following formula:
2) calculate purity and concentration
Purity with following little EQUILIBRIUM CALCULATION FOR PROCESS each several part:
[Met?Mb]＝146A490-108A560+2.1A580
[Ferryl?Mb]＝-62A490+242A560-123A580
[MbO2]＝2.8A490-127A560+153A580
(value that deducts the 700nm place is revised background absorption)
When total protein protoheme＞95% is collected Met Mb part, with the concentration in the top formula calculating elutant.
3) preparation 70 μ M Met Mb solution
With the Met Mb solution behind the 5mM PBS dilution purifying, 4 ℃ of preservations
Experimental technique:
(1) 36 μ l70 μ M Met Mb is in the sample tube of 1.5-ml;
(2) in test tube, add 300 μ l500 μ M ABTS and 487 μ l 5mM PBS
(3) add 10 μ l serum or 1.25mM trolox solution
(4) slowly behind the mixing, test tube is stored 5 minutes in 0 ℃
(5) add 167 μ l, 450 μ M H then
2O
2, mixing placed for ten seconds
(6) in (20-25 ℃) accurate period under the room temperature, reacted 5 minutes
(7) use ultraviolet spectrophotometer in the 734nm specimen
Trolox?equivalent?antioxidant?capacity(TEAC)
(1) calculates the light absorption ratio of serum sample with reference to per unit 1.25mM trolox solution
(2) calculate the value of TEAC in the serum sample (mM) with reference to 1.00mM trolox
Embodiment
Embodiment 1
1) pre-treatment: press the persimmon fresh fruit broken.
2) extract: with raw material and deionized water by 1: 3 mixed extractor of packing into, be heated to the boiling back and kept temperature 2 hours, collect and extract feed liquid for the first time, extract the deionized water that adds 3 times of amounts more for the second time, ebuillition of heated insulation 2 hours is collected and is extracted feed liquid for the second time.
3) concentrating under reduced pressure: extracting solution imported carry out concentrating under reduced pressure in the thickener, temperature is controlled at below 60 degrees centigrade, and vacuum degree control is more than 0.06MPa.
4) centrifugal: the extracting solution after will concentrating is centrifugal by whizzer.
5) concentrate, the extracting solution after centrifugal directly advances macroporous resin column;
6) it is limpid to effluent liquid to wash post with water;
7) it is tasteless to effluent liquid to wash post with ethanol;
8) effluent liquid of collection from macroporous resin column;
9) elutriant carries out concentrating under reduced pressure, is concentrated into 10 degree Beaume;
10) spraying drying, sterilising packaging
Embodiment 2
1) pre-treatment: will choose, reject persimmon dry fruit and fresh fruit fragmentation behind the impurity;
2) extract: qualified raw material is put in the clean extractor, add 5 times of amount 65% (v/v) ethanol, refluxing extraction 3h for the first time, from solvent boiling timing, 80 ℃ of controlled temperature, insulation then extrude soup, the alcohol reflux 2h that adds for the second time 3 times of amount 65% (v/v) again, merging filtrate;
3) reclaim ethanol: will carry out concentrating under reduced pressure in the soup suction concentration tank that extract, reclaim ethanol, temperature be controlled at below 60 ℃, and vacuum degree control is more than 0.06Mpa.After being recycled to nothing alcohol flavor, soup is pressed into container for storing liquid;
4) add water, leave standstill, cooling: reclaim alcoholic acid soup and raw material ratio and should be controlled at about 1: 4, then add water inadequately, leave standstill, cooling;
5) centrifugal: the refrigerative soup is centrifugal with whizzer, and soup should be no any throw out;
6) post absorption: the soup after centrifugal is advanced the D101 resin column;
7) washing: after absorption finishes, wash, wash about about 2h with deionized water.
8) wash-out: carry out wash-out with 70% (v/v) ethanol, collect slightly alcohol flavor, and the elutriant clarification, transparent, the collection elutriant is about 3 times of amount of resin approximately;
9) concentrate: elutriant carries out concentrating under reduced pressure, and temperature is controlled at below 60 ℃, and vacuum tightness should be controlled at more than the 0.06MPa, is concentrated into about 15 degree Beaume.
10) spraying drying, sterilising packaging.
Embodiment 3
1) pre-treatment: will choose, reject the persimmon dry fruit fragmentation behind the impurity;
2) extract: with qualified raw material and weight concentration be 60% ethanol by 1: 10 mixed, carry out ultrasonic extraction, extraction conditions is operating frequency 80kHz, time 120min extracts 2 times;
3) reclaim ethanol: will carry out concentrating under reduced pressure in the soup suction concentration tank that extract, reclaim ethanol, temperature be controlled at below 60 ℃, and vacuum degree control is more than 0.06Mpa.After being recycled to nothing alcohol flavor, soup is pressed into container for storing liquid;
4) add water, leave standstill, cooling: reclaim alcoholic acid soup and raw material ratio and should be controlled at about 1: 4, then add water inadequately, leave standstill, cooling;
5) centrifugal: the refrigerative soup is centrifugal with whizzer, and soup should be no any throw out;
6) post absorption: the soup after centrifugal is advanced the D101 resin column;
7) washing: after absorption finishes, wash, wash about about 2h with deionized water.
8) wash-out: carry out wash-out with 70% (v/v) ethanol, collect slightly alcohol flavor, and the elutriant clarification, transparent, the collection elutriant is about 3 times of amount of resin approximately;
9) concentrate: elutriant carries out concentrating under reduced pressure, and temperature is controlled at below 60 ℃, and vacuum tightness should be controlled at more than the 0.06MPa, is concentrated into about 15 degree Beaume.
10) spraying drying, sterilising packaging.
Embodiment 4
1) pre-treatment: will choose, reject the persimmon dry fruit fragmentation behind the impurity;
2) extract: qualified raw material is put in the clean extractor, is added 10 times of amount 85% (v/v) methyl alcohol, refluxing extraction 3h for the first time,, add 8 times of methanol eddies extraction 2h that measure 85% (v/v) for the second time again, merging filtrate;
3) reclaim methyl alcohol: will carry out concentrating under reduced pressure in the soup suction concentration tank that extract, reclaim methyl alcohol, temperature be controlled at below 60 ℃, and vacuum degree control is more than 0.06Mpa.After being recycled to nothing alcohol flavor, soup is pressed into container for storing liquid;
4) add water, leave standstill, cooling: the soup and the raw material ratio that reclaim methyl alcohol should be controlled at about 1: 3, then add water inadequately, leave standstill cooling;
5) centrifugal: the refrigerative soup is centrifugal with whizzer, and soup should be no any throw out;
6) post absorption: the soup after centrifugal is advanced the HP20 resin column;
7) washing: after absorption finishes, wash, wash about about 2h with deionized water.
8) wash-out: carry out wash-out with 90% (v/v) methyl alcohol, collect slightly alcohol flavor, and the elutriant clarification, transparent, the collection elutriant is about 3 times of amount of resin approximately;
9) concentrate: elutriant carries out concentrating under reduced pressure, and temperature is controlled at below 60 ℃, and vacuum tightness should be controlled at more than the 0.06MPa, is concentrated into about 15 degree Beaume.
10) spraying drying, sterilising packaging.
Claims (8)
1, a kind of method of from persimmon, extracting the persimmon polyphenol, it is characterized in that it be a kind of be raw material with the persimmon, through the method that extraction solvent extracts, concentrates, the persimmon polyphenol is extracted in separation and purification, persimmon polyphenol weight content is more than 70% in the extract; Described extraction solvent is that water or volumetric concentration are 65% ethanol, and described separation and purification is a column chromatographic isolation and purification.
2, extract the method for persimmon polyphenol according to claim 1 from persimmon, it is characterized in that: described persimmon is bright persimmon and/or dried persimmon.
3, extract the method for persimmon polyphenol according to claim 1 from persimmon, it is characterized in that: described extracting method is heating extraction or ultrasonic extraction or microwave extraction.
4, as extract the method for persimmon polyphenol as described in the claim 3 from persimmon, it is characterized in that: it is 1～3 time that extraction time is extracted in described heating, and the solvent consumption is 3～12 times of amounts of raw material weight; Temperature is 40～100 ℃, and extraction time is solvent boiling back 1～3 hour; Need to reclaim alcohol after described persimmon extracts and handle, temperature is controlled at below 60 ℃, and vacuum degree control is more than 0.06Mpa, and the soup and the raw material weight ratio that reclaim alcohol are controlled between 1: 2～5.
5, extract the method for persimmon polyphenol according to claim 1 from persimmon, it is characterized in that: the ultrasonic extraction condition is operating frequency 15～80kHz, time 5～120min.
6, extract the method for persimmon polyphenol according to claim 1 from persimmon, it is characterized in that: the microwave extraction condition is operating frequency 900～2500MHz, time 5～120min.
7, extract the method for persimmon polyphenol according to claim 1 from persimmon, it is characterized in that: described column chromatographic isolation and purification step is:
The A extracting solution through concentrate, reclaim alcohol, centrifugal after, directly enter macroporous resin column, flow velocity is 0.5～1.5BV/hr; Described simmer down to vacuum concentration, thickening temperature are controlled at below 60 ℃, and vacuum tightness is more than the 0.08MPa, is concentrated into the 1/4-1/2 of original extracting liquid volume; Centrifugal employing horizontal centrifuge, rotating speed are 4800r/min;
It is limpid to effluent liquid that B washes post with deionized water, and the time is 2h;
The C volumetric concentration is that 70% ethanol is washed post to elutriant clarification, transparent, and flow velocity is slightly slower than the speed of absorption;
D collects effusive clarification from macroporous resin column, transparent, the elutriant of alcohol flavor slightly, 1～3 times of collecting elutriant and be amount of resin;
E alcohol water elution liquid is concentrated, dry, described simmer down to vacuum concentration, and temperature is controlled at below 60 ℃, and vacuum tightness 0.06-0.1MPa is concentrated into 10～15 degree Beaume; Drying is a spraying drying: 160～200 ℃ of intake air temperatures, 80～110 ℃ of air outlet temperature.
8, as extract the method for persimmon polyphenol as described in the claim 7 from persimmon, it is characterized in that: described macroporous resin is for being the material of skeleton with the polystyrene, and model is D101, D130, AB-8 or HP-20.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11464247B2 (en) | 2006-09-07 | 2022-10-11 | Guilin Gfs Monk Fruit Corp. | Sweetening compositions and processes for preparing them |
| US11576412B2 (en) | 2016-10-24 | 2023-02-14 | Guilin Gfs Monk Fruit Corporation | Extracts from fruits of the Cucurbitaceae family, and methods of preparing thereof |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101294048B (en) * | 2008-06-19 | 2010-06-23 | 晋城市柿宝科技发展有限公司 | Method for preparing persimmon tannin extract |
| CN102269702A (en) * | 2011-05-05 | 2011-12-07 | 江苏省农业科学院 | Detection kit for determining small berry ORAC (oxygen radical absorbance capacity) and detection method thereof |
| CN103141786A (en) * | 2013-04-03 | 2013-06-12 | 石林绿汀甜柿产品开发有限公司 | Persimmon buccal tablet candy |
| CN104666392B (en) * | 2015-03-31 | 2018-08-21 | 桂林得坤生物科技股份有限公司 | A method of preparing persimmon polyphenol from persimmon |
| CN108524586A (en) * | 2018-06-20 | 2018-09-14 | 罗国球 | A method of extracting persimmon polyphenol from persimmon |
| CN109511704A (en) * | 2018-11-23 | 2019-03-26 | 桂林莱茵生物科技股份有限公司 | A kind of preparation method and applications of the persimmon polyphenol of no bitter taste |
| CN109575635A (en) * | 2019-01-23 | 2019-04-05 | 西北农林科技大学 | The extraction separation method of persimmon natural pigment |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11464247B2 (en) | 2006-09-07 | 2022-10-11 | Guilin Gfs Monk Fruit Corp. | Sweetening compositions and processes for preparing them |
| US11576412B2 (en) | 2016-10-24 | 2023-02-14 | Guilin Gfs Monk Fruit Corporation | Extracts from fruits of the Cucurbitaceae family, and methods of preparing thereof |
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