CN109705080A - The extracting method of Proanthocyanidins from Grape Seeds high polymer cracking and procyanidine B4 - Google Patents
The extracting method of Proanthocyanidins from Grape Seeds high polymer cracking and procyanidine B4 Download PDFInfo
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- CN109705080A CN109705080A CN201811562562.XA CN201811562562A CN109705080A CN 109705080 A CN109705080 A CN 109705080A CN 201811562562 A CN201811562562 A CN 201811562562A CN 109705080 A CN109705080 A CN 109705080A
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- procyanidine
- high polymer
- ethyl acetate
- proanthocyanidins
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- 229920000642 polymer Polymers 0.000 title claims abstract description 19
- XFZJEEAOWLFHDH-UHFFFAOYSA-N (2R,2'R,3R,3'R,4R)-3,3',4',5,7-Pentahydroxyflavan(48)-3,3',4',5,7-pentahydroxyflavan Natural products C=12OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C(O)C=C(O)C=1C(C1=C(O)C=C(O)C=C1O1)C(O)C1C1=CC=C(O)C(O)=C1 XFZJEEAOWLFHDH-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 235000009754 Vitis X bourquina Nutrition 0.000 title claims abstract description 13
- 235000012333 Vitis X labruscana Nutrition 0.000 title claims abstract description 13
- 235000014787 Vitis vinifera Nutrition 0.000 title claims abstract description 13
- 229920002770 condensed tannin Polymers 0.000 title claims abstract description 11
- 238000005336 cracking Methods 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims abstract description 9
- 240000006365 Vitis vinifera Species 0.000 title claims abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000005487 catechin Nutrition 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 229950001002 cianidanol Drugs 0.000 claims abstract description 11
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 claims abstract description 8
- 235000019441 ethanol Nutrition 0.000 claims abstract description 8
- 238000000658 coextraction Methods 0.000 claims abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
- 239000012071 phase Substances 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 238000010828 elution Methods 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000741 silica gel Substances 0.000 claims description 6
- 229910002027 silica gel Inorganic materials 0.000 claims description 6
- 229960001866 silicon dioxide Drugs 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- 239000000284 extract Substances 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 claims description 3
- PFTAWBLQPZVEMU-UHFFFAOYSA-N catechin Chemical compound OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UHFFFAOYSA-N 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 238000001514 detection method Methods 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 238000010829 isocratic elution Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000005374 membrane filtration Methods 0.000 claims description 3
- 238000013517 stratification Methods 0.000 claims description 3
- 239000003480 eluent Substances 0.000 claims description 2
- 239000012488 sample solution Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 abstract description 5
- 235000013824 polyphenols Nutrition 0.000 abstract description 5
- CWEZAWNPTYBADX-UHFFFAOYSA-N Procyanidin Natural products OC1C(OC2C(O)C(Oc3c2c(O)cc(O)c3C4C(O)C(Oc5cc(O)cc(O)c45)c6ccc(O)c(O)c6)c7ccc(O)c(O)c7)c8c(O)cc(O)cc8OC1c9ccc(O)c(O)c9 CWEZAWNPTYBADX-UHFFFAOYSA-N 0.000 abstract description 4
- 229920002414 procyanidin Polymers 0.000 abstract description 4
- 238000007445 Chromatographic isolation Methods 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 238000000354 decomposition reaction Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 241000219095 Vitis Species 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 239000000539 dimer Substances 0.000 description 2
- 229940087603 grape seed extract Drugs 0.000 description 2
- 235000002532 grape seed extract Nutrition 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000001717 vitis vinifera seed extract Substances 0.000 description 2
- PFTAWBLQPZVEMU-ZFWWWQNUSA-N (+)-epicatechin Natural products C1([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-ZFWWWQNUSA-N 0.000 description 1
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 description 1
- 102000004366 Glucosidases Human genes 0.000 description 1
- 108010056771 Glucosidases Proteins 0.000 description 1
- MOJZMWJRUKIQGL-FWCKPOPSSA-N Procyanidin C2 Natural products O[C@@H]1[C@@H](c2cc(O)c(O)cc2)Oc2c([C@H]3[C@H](O)[C@@H](c4cc(O)c(O)cc4)Oc4c3c(O)cc(O)c4)c(O)cc(O)c2[C@@H]1c1c(O)cc(O)c2c1O[C@@H]([C@H](O)C2)c1cc(O)c(O)cc1 MOJZMWJRUKIQGL-FWCKPOPSSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229930014669 anthocyanidin Natural products 0.000 description 1
- 150000001452 anthocyanidin derivatives Chemical class 0.000 description 1
- 235000008758 anthocyanidins Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Natural products Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 description 1
- 235000012734 epicatechin Nutrition 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 1
- 229940087559 grape seed Drugs 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- HGVVOUNEGQIPMS-UHFFFAOYSA-N procyanidin Chemical compound O1C2=CC(O)=CC(O)=C2C(O)C(O)C1(C=1C=C(O)C(O)=CC=1)OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1 HGVVOUNEGQIPMS-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000009758 senescence Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Disclosure of the invention is the cracking of Proanthocyanidins from Grape Seeds high polymer and the extracting method of procyanidine B4, it is extracted by ethyl acetate, the coextraction of water phase procyanidins high polymer is three times, then using catechin as decomposition agent, ethyl alcohol is solvent, the cracking reaction under acidity, procyanidine high polymer is cracked into procyanidine oligomer, crack reacting condition of the present invention is controllable, not only it is utilized high polymer, and increase the utilization rate of polyphenol, the content of procyanidine B4 is obtained with chromatographic isolation, product purity is high, reach 99.1%, procyanidine B4 yield is 4.2~5.0%.
Description
Technical field
The present invention relates to extract effective ingredient in grape pip, and in particular to the cracking of Proanthocyanidins from Grape Seeds high polymer and original
The extracting method of anthocyanidin B4.
Background technique
Grape seed extract (Grape Seed Extract, GSE) is cannot in a kind of human body extracted from grape seeds
The new and effective Natural Antioxidants of synthesis, it can effectively clear free radical extra in human body, has and delays senescence and increase
The effect of strong immunity.Main active is grape seed polyphenols (Grape Proantho Cyanidins, GPC) in GSE, it
By procyanidine list aggressiveness (catechin, epicatechin, gallate), glucosidase procyanidins (Oligomeric Proantho
Cyanidins, OPC), high poly- procyanidine (Polymers Proantho Cyanidins, PPC) composition.Three classes procyanidine
Condensate antioxidant activity in vitro test result is shown, is improved oxidation resistance with the degree of polymerization and is increased.Oral absorption experimental study
The results show that dimer (Procyanidins B1, B2, B3, B4) bioavilability highest, Dan Ju in procyanidine oligomer
Body bioavilability is lower, and procyanidine high polymer is oral not to be absorbed, and grape pip procyanidin high polymer needs to be cracked into oligomeric
Body can just be utilized by bio-absorbable, if therefore procyanidine high polymer is cracked into dimer in procyanidine oligomer just mentioning
The high utilization rate of grape pip.
Summary of the invention
Technical problem to be solved by the invention is to provide the cracking of Proanthocyanidins from Grape Seeds high polymer and procyanidine B4
Extracting method, which can be cracked into procyanidine oligomer by procyanidine high polymer, increase procyanidine
B4 recovery rate.
The extracting method of Proanthocyanidins from Grape Seeds high polymer cracking and procyanidine B4, its step are as follows:
A, commercial glucose seed extract 10g is dissolved in 500ml water, stratification in 4 DEG C of environment separates organic phase, and water phase is used again
The extraction of 500ml ethyl acetate, separates, three times, last water phase is concentrated under reduced pressure into drying for water phase coextraction, obtains the height of yellow after extraction
Poly group point.It is oligomeric component, i.e. polyphenol and procyanidine oligomer in organic phase, can be utilized with antioxidant；
B, above-mentioned high poly group point is dissolved in ethyl alcohol, adds catechin and hydrochloric acid is added dropwise and is reacted, hydrochloric acid final concentration of 0.02~
0.1M, at 30~50 DEG C, the reaction time is 10~30 minutes for reaction temperature control, obtains reaction solution, the high poly group point with it is described
The mass volume ratio of ethyl alcohol is 0.1g:5ml, and the high poly group is divided and the mass ratio of the catechin is 0.1g:0.1~0.3g；
C, by above-mentioned reaction solution, with 0.22 μm of membrane filtration, liquid chromatogram separation, chromatographic column is Welch XB-C18, specification
For 21.2mm × 250mm, 10 μm, 25 DEG C of column temperature, mobile phase: the acetic acid water of acetonitrile and mass percentage concentration 0.2%, isocratic elution,
When 0~25 min is eluted, acetonitrile volume accounts for 20%, when 25~40 min are eluted in mobile phase, and acetonitrile volume accounts for 45% in mobile phase,
Each sample solution 50ml, 280 nm of Detection wavelength, receive 30~32min elution fraction；
D, by above-mentioned elution fraction, it is concentrated under reduced pressure into drying, is mixed with 300~400 mesh silica gel by weight 1:1, excessively 200~
300 mesh silicagel columns, ethyl acetate elution are concentrated under reduced pressure ethyl acetate eluent to drying, obtain clear crystal procyanidine B4.
The advantage of the invention is that the extracting method of Proanthocyanidins from Grape Seeds high polymer cracking and procyanidine B4, passes through
Ethyl acetate extraction, three times, then using catechin as decomposition agent, ethyl alcohol is solvent to the coextraction of water phase procyanidins high polymer,
The cracking reaction under acidity, procyanidine high polymer are cracked into procyanidine oligomer, and crack reacting condition of the present invention is controllable, no
But it is utilized high polymer, and increases the utilization rate of polyphenol, obtains the content of procyanidine B4 with chromatographic isolation, product is pure
Degree is high, reaches 99.1%, procyanidine B4 yield is 4.2~5.0%.
Specific embodiment
Present invention is further described in detail with reference to embodiments.
Embodiment 1
Commercial glucose seed extract 10g is dissolved in 500ml water, stratification in 4 DEG C of environment, and water phase is extracted with 500ml ethyl acetate
It takes, is separated after extraction, three times, water phase extract liquor is concentrated to dryness for water phase coextraction, obtains the high poly group point of yellow.It is in organic phase
Oligomeric component, i.e. polyphenol and procyanidine oligomer, can be utilized with antioxidant；High polymerization degree component is dissolved in ethyl alcohol,
Add catechin and hydrochloric acid is added dropwise, the mass volume ratio of high poly group point and ethyl alcohol is 0.1g:5ml, matter of the high poly group point with catechin
Amount is than being 0.1g:0.2g, and the final concentration of 0.04M of hydrochloric acid, reaction temperature control is at 35 DEG C, the reaction time 22 minutes, control reaction
Liquid crosses 0.22 μm of membrane filtration, filtrate chromatographic isolation, and chromatographic column is Welch XB-C18, specification be 21.2mm × 250mm,
10 μm, 25 DEG C of column temperature, mobile phase: the mixed liquor of acetonitrile and 0.2% acetic acid water, isocratic elution, when 0~25 min is eluted, mobile phase
Middle acetonitrile volume accounts for 20%, and when 25~40 min are eluted, acetonitrile volume accounts for 45%, 280 nm of Detection wavelength in mobile phase, every time on
50 ml of sample liquid collects 30~32 min elution fractions, merges elution fraction, drying is concentrated under reduced pressure into, with 300~400 mesh silica gel
It is mixed by weight 1:1, crosses 200~300 mesh silicagel columns, ethyl acetate elution is concentrated under reduced pressure ethyl acetate phase to drying, obtains
0.31g clear crystal procyanidine B4.
Embodiment 2
Substantially the same manner as Example 1, the mass ratio of different only high poly group point and catechin is 0.1g:0.1g, and hydrochloric acid is whole
Concentration is 0.1M, and at 30 DEG C, the reaction time is 30 minutes for reaction temperature control.
Embodiment 3
Substantially the same manner as Example 1, the mass ratio of different only high poly group point and catechin is 0.1g:0.3g, and hydrochloric acid is whole
Concentration is 0.02M, and at 50 DEG C, the reaction time is 10 minutes for reaction temperature control.
Claims (1)
1. the extracting method of Proanthocyanidins from Grape Seeds high polymer cracking and procyanidine B4, it is characterised in that steps are as follows:
A, commercial glucose seed extract 10g is dissolved in 500ml water, stratification in 4 DEG C of environment separates organic phase, and water phase is used again
The extraction of 500ml ethyl acetate, separates, three times, last water phase is concentrated under reduced pressure into drying for water phase coextraction, obtains the height of yellow after extraction
Poly group point；
B, above-mentioned high poly group point is dissolved in ethyl alcohol, adds catechin and hydrochloric acid is added dropwise and is reacted, hydrochloric acid final concentration of 0.02~
0.1M, at 30~50 DEG C, the reaction time is 10~30 minutes for reaction temperature control, obtains reaction solution, the high poly group point with it is described
The mass volume ratio of ethyl alcohol is 0.1g:5ml, and the high poly group is divided and the mass ratio of the catechin is 0.1g:0.1~0.3g；
C, by above-mentioned reaction solution, with 0.22 μm of membrane filtration, liquid chromatogram separation, chromatographic column is Welch XB-C18, specification
For 21.2mm × 250mm, 10 μm, 25 DEG C of column temperature, mobile phase: the acetic acid water of acetonitrile and mass percentage concentration 0.2%, isocratic elution,
When 0~25 min is eluted, acetonitrile volume accounts for 20%, when 25~40 min are eluted in mobile phase, and acetonitrile volume accounts for 45% in mobile phase,
Each sample solution 50ml, 280 nm of Detection wavelength, receive 30~32min elution fraction；
D, by above-mentioned elution fraction, it is concentrated under reduced pressure into drying, is mixed with 300~400 mesh silica gel by weight 1:1, excessively 200~
300 mesh silicagel columns, ethyl acetate elution are concentrated under reduced pressure ethyl acetate eluent to drying, obtain clear crystal procyanidine B4.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811562562.XA CN109705080A (en) | 2018-12-20 | 2018-12-20 | The extracting method of Proanthocyanidins from Grape Seeds high polymer cracking and procyanidine B4 |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811562562.XA CN109705080A (en) | 2018-12-20 | 2018-12-20 | The extracting method of Proanthocyanidins from Grape Seeds high polymer cracking and procyanidine B4 |
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| Publication Number | Publication Date |
|---|---|
| CN109705080A true CN109705080A (en) | 2019-05-03 |
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|---|---|---|---|
| CN201811562562.XA Pending CN109705080A (en) | 2018-12-20 | 2018-12-20 | The extracting method of Proanthocyanidins from Grape Seeds high polymer cracking and procyanidine B4 |
Country Status (1)
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5484594A (en) * | 1988-06-28 | 1996-01-16 | Tecnofarmaci S.P.A. | Process for preparing grapeseed extracts enriched in procyanidol oligomers |
| US20080311662A1 (en) * | 2004-07-29 | 2008-12-18 | Yuko Fukui | Method for Analyzing Oligomeric Proanthocyanidin (Opc) |
| CN101565414A (en) * | 2009-06-03 | 2009-10-28 | 中国科学院山西煤炭化学研究所 | Method for extracting and separating procyanidine |
| CN106381319A (en) * | 2016-08-31 | 2017-02-08 | 山东省葡萄研究院 | High-efficiency extraction and separation method of grape seed proanthocyanidin oligomer |
-
2018
- 2018-12-20 CN CN201811562562.XA patent/CN109705080A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5484594A (en) * | 1988-06-28 | 1996-01-16 | Tecnofarmaci S.P.A. | Process for preparing grapeseed extracts enriched in procyanidol oligomers |
| US20080311662A1 (en) * | 2004-07-29 | 2008-12-18 | Yuko Fukui | Method for Analyzing Oligomeric Proanthocyanidin (Opc) |
| CN101565414A (en) * | 2009-06-03 | 2009-10-28 | 中国科学院山西煤炭化学研究所 | Method for extracting and separating procyanidine |
| CN106381319A (en) * | 2016-08-31 | 2017-02-08 | 山东省葡萄研究院 | High-efficiency extraction and separation method of grape seed proanthocyanidin oligomer |
Non-Patent Citations (3)
| Title |
|---|
| LANXIN LUOA,ET.: ""An approach for degradation of grape seed and skin proanthocyanidin polymers into oligomers by sulphurous acid"", 《FOOD CHEMISTRY》 * |
| NILS KOHLER,ET.: ""New Approach for the Synthesis and Isolation of Dimeric Procyanidins"", 《J. AGRIC. FOOD CHEM》 * |
| 刘俊英: ""原花青素低聚体制备"", 《万方学位论文》 * |
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Inventor after: Wang Jing Inventor after: Wang Qiang Inventor after: Wen Kuishan Inventor after: Qian Jinjin Inventor before: Wang Qiang Inventor before: Wang Jing Inventor before: Wen Kuishan Inventor before: Qian Jinjin |
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Application publication date: 20190503 |