CN104557836A - Method for extracting alcohol soluble substance from bark of mongolian pine - Google Patents
Method for extracting alcohol soluble substance from bark of mongolian pine Download PDFInfo
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- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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Abstract
A method for extracting an alcohol soluble substance from bark of mongolian pine comprises the following steps: (1), smashing the bark of mongolian pine into particles of 20 to 80 meshes, feeding the particles into n-hexane/chloroform and carrying out ultrasonic treatment to obtain a mixture A; (2). filtering the mixture A to obtain filtrate a and residue, and distilling the filtrate a to distil off n-hexane/chloroform to obtain lipid; (3). feeding the residue into an ethanol solution and carrying out ultrasonic treatment; (4). filtering mixture B to obtain filtrate b, distilling the filtrate b to distil off the ethanol solution to obtain the concentrated solution of the alcohol soluble substance, and drying the concentrated solution to obtain the alcohol soluble substance. The alcohol soluble substance extracted by the method is high in content of flavone, contains sinapic acid, secoisolariciresinol, 7-hydroxy-secoisolariciresinol-9'-p-hydroxy(trans) cinnamate and other effective components, and has anti-oxidation and antimicrobial effects and the like.
Description
Technical field
The invention belongs to effective ingredients in plant extraction process, specifically, relate to the method for natural product in a kind of ultrasonic assistant solvent stage extraction pinus sylvestris var. mongolica bark.
Background technology
Pinus sylvestris var. mongolica is one of China's three northern areas of China Major Fine reproducting tree species, widely distributed, and aboundresources, pinus sylvestris var. mongolica bark is as important forestry by-product, and its resource utilization is lower.
Research shows, containing effective constituents such as polysaccharide, phenolic substance, organic acid, tannin, flavones in the alcohol soluble substance of pinus sylvestris var. mongolica bark extraction using alcohol.Wherein with the natural extract with various health care functions that flavones is generally acknowledged.Fat content in pinus sylvestris var. mongolica is lower, is about the 1%-3% of bark dry weight.
Because in pinus sylvestris var. mongolica bark, fat content is lower, so there is no the attention causing people, in current extraction pinus sylvestris var. mongolica bark, the method for alcohol soluble substance is mainly direct extraction using alcohol, and use the method, in the alcohol soluble natural product of gained, the content of flavones is lower.
Summary of the invention
For in current method, directly extract the defect that the extraction yield of the method existence of the activeconstituents in sample pinus sylvestris var. mongolica bark is low with alcohols material.The invention provides the method for natural product in a kind of stage extraction pinus sylvestris var. mongolica bark.
The method extracting alcohol soluble substance from pinus sylvestris var. mongolica bark of the present invention, comprises the steps:
(1) pinus sylvestris var. mongolica tree bark powder is broken into the particle of 20 ~ 80 order sizes, puts in normal hexane/chloroform, carry out supersound process, the condition of described supersound process is: temperature 30 ~ 60 DEG C, time 15 ~ 60min, frequency 15 ~ 40KHz; , obtain mixture A;
(2) described mixture A is filtered, obtain filtrate a and filter residue; Described filtrate a is distilled, steams normal hexane/chloroform, obtain lipid material;
(3) put in ethanolic soln by described filter residue, carry out supersound process to it, the condition of described supersound process is: temperature 30 ~ 55 DEG C, ultrasonic time 15 ~ 60min, and frequency 10 ~ 35KHz obtains mixture B;
(4) described mixture B is filtered, obtain filtrate b, filtrate b is distilled, steams ethanolic soln, obtain the concentrated solution of alcohol soluble substance, more described concentrated solution is placed in 35 DEG C of oven drying 12-24h, obtain alcohol soluble substance;
Temperature in described step (1) is higher than the temperature in step (3) 5 ~ 15 DEG C, the ultrasonic frequency height 5-10KHz in the frequency ratio step (3) in described step (1).
The volume ratio that the present invention urgees normal hexane and chloroform in described normal hexane/chloroform is 1: 5 ~ 5: 1, because in pinus sylvestris var. mongolica bark, fat content is low, as bad in the extraction effect such as sherwood oil, ether with traditional organic solvent, adopt compound extractant normal hexane/chloroform extraction successful to improve.
The mass volume ratio of particle described in the present invention and normal hexane/chloroform is 1: 10 ~ 1: 30.
The concentration of ethanolic soln described in the present invention is 40% ~ 80%.
The weightmeasurement ratio of particle described in the present invention and ethanolic soln is 1: 10 ~ 1: 50
Extracting method of the present invention comprises following preferred version:
1) pinus sylvestris var. mongolica tree bark powder is broken into the particle of 20 ~ 80 order sizes, puts in normal hexane/chloroform, described normal hexane/chloroform, the volume ratio of normal hexane chloroform is 1: 1 ~ 1: 2, and the mass volume ratio of described particle and normal hexane/chloroform is 1: 15-1: 20; Carry out supersound process, the condition of described supersound process is: temperature 35 ~ 50 DEG C, time 15 ~ 60min, frequency 25 ~ 35KHz; , obtain mixture A;
(2) described mixture A is filtered, obtain filtrate a and filter residue; Filtrate a is distilled, steams normal hexane/chloroform, obtain lipid material;
(3) described filter residue is put in ethanolic soln, the concentration of described ethanolic soln is 50%-80%, the mass volume ratio of described particle and ethanolic soln is 1: 20-1: 25, supersound process is carried out to it, the condition of described supersound process is: temperature 30 ~ 35 DEG C, ultrasonic time 15 ~ 60min, frequency 15 ~ 25KHz, obtain mixture B;
(4) described mixture B is filtered, obtain filtrate b, filtrate b is distilled, steams ethanolic soln, obtain the concentrated solution of alcohol soluble substance, more described concentrated solution is placed in 35 DEG C of oven drying 12-24h, obtain alcohol soluble substance;
Temperature in described step (1) is higher than the temperature in step (3) 5 ~ 15 DEG C, the ultrasonic frequency height 5-10KHz in the frequency ratio step (3) in described step (1).
The method of natural product in a kind of ultrasonic assistant solvent stage extraction pinus sylvestris var. mongolica bark provided by the invention, tool has the following advantages:
(1) method of the stage extraction of the present invention's employing, first extracts lipid and extracts alcohol soluble substance again, effectively reduce the interference of grease in alcohol extract, improve the extraction yield of flavones isoreactivity material in alcohol extract, reduce the difficulty of subsequent purification technique.
(2) the inventive method success extraction and isolation is adopted to go out lipid and alcohol soluble substance two series products, extraction efficiency is high, good separating effect, successfully achieve the utilization that becomes more meticulous modern extraction and separation technology being applied to pinus sylvestris var. mongolica bark, the diversification of pinus sylvestris var. mongolica bark, high-valued, the utilization that becomes more meticulous are had great importance.
Accompanying drawing explanation
Fig. 1: the LC/MS/MS spectrogram of sectioned extracting method gained alcohol soluble substance;
Embodiment
Following examples for illustration of the present invention, but are not used for limiting the scope of the invention.If do not specialize, the conventional means that technique means used in embodiment is well known to those skilled in the art, is raw materials usedly commercial goods.
The pinus sylvestris var. mongolica bark used in following examples gathers from Daxing ' anling, heilongjiang.
Embodiment 1 one kinds extracts the method for alcohol soluble substance from pinus sylvestris var. mongolica bark
Comprise the steps:
(1) 20g pinus sylvestris var. mongolica tree bark powder is broken into the particle of 20 ~ 80 order sizes, and puts in the normal hexane/chloroform of 300mL, the volume ratio of normal hexane and chloroform is 1: 5, ul-trasonic irradiation 30min under 35 DEG C of conditions, and ultrasonic frequency is 25KHz.
(2) while hot vacuum filtration is carried out to the mixture after process, obtain filtrate a and filter residue.Filtrate a is placed in Rotary Evaporators and carries out underpressure distillation, steam normal hexane/chloroform solvent, obtain lipid material.
(3) by step 2) in filter residue drops into 400mL, in 50% ethanolic soln, ul-trasonic irradiation 30min under 30 DEG C of conditions, ultrasonic frequency is 19KHz.
(4) while hot vacuum filtration is carried out to the mixture after process, obtain filtrate b.Filtrate a is placed in Rotary Evaporators and carries out underpressure distillation, steam ethanolic soln, obtain the concentrated solution of alcohol soluble substance, then residuum is placed in 35 DEG C of oven drying 12h.
Lipid material in the pinus sylvestris var. mongolica bark according to said method extracted is 18.60mg/g, and the total amount of alcohol soluble substance is 88.63mg/g.
Detect the flavones in the alcohol soluble substance of gained with nitrous acid aluminium-aluminum nitrate-sodium hydroxide development process (in rutin), wherein flavones content is 23.09mg/g.
Embodiment 2 one kinds extracts the method for alcohol soluble substance from pinus sylvestris var. mongolica bark
(1) 20g pinus sylvestris var. mongolica tree bark powder is broken into the particle of 30 ~ 60 order sizes, and puts in the normal hexane/chloroform of 400mL, the volume ratio of normal hexane and chloroform is 1: 1, ul-trasonic irradiation 60min under 50 DEG C of conditions, and ultrasonic frequency is 30KHz.
(2) while hot vacuum filtration is carried out to the mixture after process, obtain filtrate a and filter residue.Filtrate a is placed in Rotary Evaporators and carries out underpressure distillation, steam normal hexane/chloroform solvent, obtain lipid material.
(3) by step 2) in filter residue drops into 500mL, in 80% ethanolic soln, ul-trasonic irradiation 60min under 35 DEG C of conditions, ultrasonic frequency is 25KHz.
(4) while hot vacuum filtration is carried out to the mixture after process, obtain filtrate b.Filtrate b Rotary Evaporators carries out concentrating under reduced pressure, steams alcohol solvent, obtains the concentrated solution of lipid-soluble substance, concentrated solution is placed in 35 DEG C of oven drying 16h, obtains alcohol soluble substance.
Lipid material in the pinus sylvestris var. mongolica bark according to said method extracted is 24.72mg/g, and the total amount of alcohol soluble substance is 95.24mg/g.
Measure with nitrous acid aluminium-aluminum nitrate-sodium hydroxide development process (in rutin) and detect the flavones in the alcohol soluble substance of gained, wherein flavones content is 26.28mg/g.
Embodiment 3 one kinds extracts the method for alcohol soluble substance from pinus sylvestris var. mongolica bark
(1) 20g pinus sylvestris var. mongolica tree bark powder is broken into the particle of 30-70 order size, and puts in the normal hexane/chloroform of 350mL, the volume ratio of normal hexane and chloroform is 1: 2, ul-trasonic irradiation 50min under 40 DEG C of conditions, and ultrasonic frequency is 35KHz.
(2) while hot vacuum filtration is carried out to the mixture after process, obtain filtrate a and filter residue.Filtrate a is placed in Rotary Evaporators and carries out underpressure distillation, steam normal hexane/chloroform solvent, obtain lipid material.
(3) by step 2) in filter residue drops into 500mL, in 70% ethanolic soln, ul-trasonic irradiation 55min under 30 DEG C of conditions, ultrasonic frequency is 25KHz.
(4) while hot vacuum filtration is carried out to the mixture after process, obtain filtrate b.Filtrate b Rotary Evaporators carries out concentrating under reduced pressure, steams alcohol solvent, obtains the concentrated solution of alcohol soluble substance, concentrated solution is placed in 35 DEG C of oven drying 14h, obtains alcohol soluble substance.
Lipid material in the pinus sylvestris var. mongolica bark according to said method extracted is 24.35mg/g, and the total amount of alcohol soluble substance is 93.52mg/g.
Measure with nitrous acid aluminium-aluminum nitrate-sodium hydroxide development process (in rutin) and detect the flavones in the alcohol soluble substance of gained, wherein flavones content is 25.86mg/g.
Comparative example 1
Compare with embodiment 2, difference is only, the normal hexane/chloroform in step (1) is replaced with ether.Lipid material in the pinus sylvestris var. mongolica bark according to said method extracted is 10.72mg/g, and the total amount of alcohol soluble substance is 100.24mg/g.
Measure with nitrous acid aluminium-aluminum nitrate-sodium hydroxide development process (in rutin) and detect the flavones in the alcohol soluble substance of gained, wherein flavones content is 19.28mg/g.
Comparative example 2
Compare with embodiment 2, its difference is only, the Ultrasonic Conditions in described step (1) and step (2) is: under 35 DEG C of conditions, act on 60min, ultrasonic frequency is 25KHz.
Lipid material in the pinus sylvestris var. mongolica bark according to said method extracted is 15.72mg/g, and the total amount of alcohol soluble substance is 99.52mg/g.
Measure with nitrous acid aluminium-aluminum nitrate-sodium hydroxide development process (in rutin) and detect the flavones in the alcohol soluble substance of gained, wherein flavones content is 21.28mg/g.
Comparative example 3
Compare with embodiment 2, omit the operation of step (1) and (2) extraction grease, other operations are identical.
In the pinus sylvestris var. mongolica bark according to said method extracted, the total amount of alcohol soluble substance is 103.68mg/g.
Measure with nitrous acid aluminium-aluminum nitrate-sodium hydroxide development process (in rutin) and detect the flavones in the alcohol soluble substance of gained, wherein flavones content is 20.15mg/g.
Experimental example 1
Experimental subjects: the alcohol soluble substance that embodiment 2 is extracted.
Experimental technique: utilize the material composition that high performance liquid chromatography is connected in second mass analysis detection alcohol soluble substance.INSTRUMENT MODEL: Thermo Scientific-Q Exactive, data processing software: Xcalibur.UV-detector model: Ultimate 3000, determined wavelength: 280nm.Column type number: Hypersil Gold Dim (mm) 1002.1.Moving phase: A is water, and B is methyl alcohol, flow velocity: 200 μ L/min.Gradient: 0min, 5%B → 10min, 10%B → 30min, 15%B → 45min, 20%B → 60min, 30%B → 70min, 50%B → 100min, 50%B.Ion source: ESI-, m/z sweep limit: 0-1500, spray voltage (-): 2500.00.Sample size 5 μ L.
Experimental result:
The LC/MS/MS spectrogram of embodiment 2 as Fig. 1, to Fig. 1 analyse and compare obtain in the alcohol soluble substance of embodiment 2 composition composition as table 1
Table 1
As can be seen from Table 1, the alcohol soluble substance that embodiment 2 is extracted is separated and obtains 13 chromatographic peaks, analyzed by HPLC-MS-MS, preliminary evaluation goes out wherein 8 kinds of main components, for the flavone component of taxifolin, Hesperitin, Isorhamnetol, tamarack lactone larixinol, and sinapinic acid, the different lariciresinol of open loop, 9 '-to hydroxyl (trans) TRANSCINNAMIC ACID-7-hydroxyl-open loop different larch turpentine alcohol ester 1,9 '-to the different larch turpentine alcohol ester 2 of hydroxyl (trans) TRANSCINNAMIC ACID-7-hydroxyl-open loop.
Experiment conclusion:
The above results shows, sectioned extracting method is taked to extract the alcohol soluble substance in pinus sylvestris var. mongolica bark, the activeconstituents of flavonoid can be obtained, also can obtain the different lariciresinol of open loop, 9 '-to hydroxyl (trans) TRANSCINNAMIC ACID-7-hydroxyl-open loop different larch turpentine alcohol ester isoreactivity composition.Sinapinic acid is one of effective constituent of middle Semen Sinapis Albae, has antimycotic, anti-pyogenic infections effect.9 '-to hydroxyl (trans) TRANSCINNAMIC ACID-7-hydroxyl-open loop different larch turpentine alcohol ester and open loop different tamarack ester be similar in an estrogenic compounds, there is anti-oxidant, antimitotic, antiviral, anticancer, more weak estrogen-like effects, reduce total cholesterol and low density lipoprotein cholesterol.Therefore, this alcohol soluble substance has good functional, can apply further.
Although above the present invention is described in detail with a general description of the specific embodiments, on basis of the present invention, can make some modifications or improvements it, this will be apparent to those skilled in the art.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, all belong to the scope of protection of present invention.
Claims (8)
1. from pinus sylvestris var. mongolica bark, extract a method for alcohol soluble substance, comprise the steps:
(1) pinus sylvestris var. mongolica tree bark powder is broken into the particle of 20 ~ 80 order sizes, puts in normal hexane/chloroform, carry out supersound process, the condition of described supersound process is: temperature 30 ~ 60 DEG C, and time 15 ~ 60min, frequency 15 ~ 40KHz, obtain mixture A;
(2) described mixture A is filtered, obtain filtrate a and filter residue; Described filtrate a is distilled, steams normal hexane/chloroform, obtain lipid material;
(3) put in ethanolic soln by described filter residue, carry out supersound process to it, the condition of described supersound process is: temperature 30 ~ 55 DEG C, time 15 ~ 60min, and frequency 10 ~ 35KHz obtains mixture B;
(4) described mixture B is filtered, obtain filtrate b, filtrate b is distilled, steams ethanolic soln, obtain the concentrated solution of alcohol soluble substance, more described concentrated solution is placed in 35 DEG C of oven drying 12-24h, obtain alcohol soluble substance.
2. according to the method described in claim 1, it is characterized in that, in described normal hexane/chloroform, the volume ratio of normal hexane and chloroform is 1:5 ~ 5:1.
3. according to the method described in claim 1, it is characterized in that, the mass volume ratio of described particle and normal hexane/chloroform is 1:10 ~ 1:30.
4. according to the method described in claim 1, it is characterized in that, the concentration of described ethanolic soln is 40% ~ 80%.
5. according to described in claim 1 method, it is characterized in that, the mass volume ratio of described particle and ethanolic soln is 1:10 ~ 1:50.
6. according to the method described in claim 1, it is characterized in that, the temperature in described step (1) is higher than the temperature in step (3) 5 ~ 15 DEG C, the frequency height 5-10KHz in frequency ratio step (3).
7. the method according to any one of claim 1-6, it is characterized in that, comprise the steps: 1) pinus sylvestris var. mongolica tree bark powder is broken into the particle of 20 ~ 80 order sizes, put in normal hexane/chloroform, described normal hexane/chloroform, the volume ratio of normal hexane chloroform is 1:1 ~ 1:2, and the mass volume ratio of described particle and normal hexane/chloroform is 1:15-1:20; Carry out supersound process, the condition of described supersound process is: temperature 35 ~ 50 DEG C, time 15 ~ 60min, frequency 25 ~ 35KHz; , obtain mixture A;
(2) described mixture A is filtered, obtain filtrate a and filter residue; Filtrate a is distilled, steams normal hexane/chloroform, obtain lipid material;
(3) described filter residue is put in ethanolic soln, the concentration of described ethanolic soln is 50%-80%, the mass volume ratio of described particle and ethanolic soln is 1:20-1:25, supersound process is carried out to it, the condition of described supersound process is: temperature 30 ~ 35 DEG C, ultrasonic time 15 ~ 60min, frequency 15 ~ 25KHz, obtain mixture B;
(4) described mixture B is filtered, obtain filtrate b, filtrate b is distilled, steams ethanolic soln, obtain the concentrated solution of alcohol soluble substance, more described concentrated solution is placed in 35 DEG C of oven drying 12-24h, obtain alcohol soluble substance.
8. the alcohols material of any one of claim 1-7 method extraction.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410820123.XA CN104557836B (en) | 2014-12-23 | 2014-12-23 | A kind of method extracting alcohol-soluble material from Pinus sylvestnis var. mongolica Litv. bark |
| PCT/CN2015/000921 WO2016101335A1 (en) | 2014-12-23 | 2015-12-22 | Method for extracting alcohol-soluble substance from bark of pinus sylvestris |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201410820123.XA CN104557836B (en) | 2014-12-23 | 2014-12-23 | A kind of method extracting alcohol-soluble material from Pinus sylvestnis var. mongolica Litv. bark |
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| CN104557836A true CN104557836A (en) | 2015-04-29 |
| CN104557836B CN104557836B (en) | 2016-07-06 |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016101335A1 (en) * | 2014-12-23 | 2016-06-30 | 孙昊东 | Method for extracting alcohol-soluble substance from bark of pinus sylvestris |
| CN108673677A (en) * | 2018-04-21 | 2018-10-19 | 阜南县金威工艺品有限公司 | A kind of preparation method of the hand-weaving product stalk of stable structure |
| CN108789727A (en) * | 2018-04-21 | 2018-11-13 | 阜南县金威工艺品有限公司 | A kind of batch manufacturing method of high stability rice straw for braiding |
| WO2020127890A1 (en) * | 2018-12-21 | 2020-06-25 | Rampf Holding Gmbh & Co. Kg | Method for producing a mixture comprising at least one compound having at least two hydroxy and/or amino groups and use thereof for producing a polymer |
| CN113101690A (en) * | 2021-04-14 | 2021-07-13 | 云南省粮油科学研究院（云南省粮油产品质量监督检验测试中心） | Extraction method and application of antioxidant in juglans sigillata peel |
| CN113100375A (en) * | 2021-04-14 | 2021-07-13 | 云南省粮油科学研究院（云南省粮油产品质量监督检验测试中心） | Extraction method and application of antioxidant in green tangerine peels of tea seeds |
| CN114481658A (en) * | 2022-02-09 | 2022-05-13 | 北京航空航天大学 | Controllable preparation method of nano-cellulose by taking bagasse as raw material |
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| CN113413845A (en) * | 2021-05-28 | 2021-09-21 | 漳州职业技术学院 | Preparation method of zinc-iron bimetallic complex of cortex magnoliae officinalis extract |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016101335A1 (en) * | 2014-12-23 | 2016-06-30 | 孙昊东 | Method for extracting alcohol-soluble substance from bark of pinus sylvestris |
| CN108673677A (en) * | 2018-04-21 | 2018-10-19 | 阜南县金威工艺品有限公司 | A kind of preparation method of the hand-weaving product stalk of stable structure |
| CN108789727A (en) * | 2018-04-21 | 2018-11-13 | 阜南县金威工艺品有限公司 | A kind of batch manufacturing method of high stability rice straw for braiding |
| WO2020127890A1 (en) * | 2018-12-21 | 2020-06-25 | Rampf Holding Gmbh & Co. Kg | Method for producing a mixture comprising at least one compound having at least two hydroxy and/or amino groups and use thereof for producing a polymer |
| CN113101690A (en) * | 2021-04-14 | 2021-07-13 | 云南省粮油科学研究院（云南省粮油产品质量监督检验测试中心） | Extraction method and application of antioxidant in juglans sigillata peel |
| CN113100375A (en) * | 2021-04-14 | 2021-07-13 | 云南省粮油科学研究院（云南省粮油产品质量监督检验测试中心） | Extraction method and application of antioxidant in green tangerine peels of tea seeds |
| CN114481658A (en) * | 2022-02-09 | 2022-05-13 | 北京航空航天大学 | Controllable preparation method of nano-cellulose by taking bagasse as raw material |
| CN114481658B (en) * | 2022-02-09 | 2023-01-20 | 北京航空航天大学 | Controllable preparation method of nano-cellulose by taking bagasse as raw material |
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| WO2016101335A1 (en) | 2016-06-30 |
| CN104557836B (en) | 2016-07-06 |
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