CN109651322A - The extracting method of Proanthocyanidins from Grape Seeds high polymer cracking and procyanidin B 2 - Google Patents
The extracting method of Proanthocyanidins from Grape Seeds high polymer cracking and procyanidin B 2 Download PDFInfo
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- CN109651322A CN109651322A CN201811561716.3A CN201811561716A CN109651322A CN 109651322 A CN109651322 A CN 109651322A CN 201811561716 A CN201811561716 A CN 201811561716A CN 109651322 A CN109651322 A CN 109651322A
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- Prior art keywords
- procyanidin
- high polymer
- procyanidine
- ethyl acetate
- elution
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- XFZJEEAOWLFHDH-NFJBMHMQSA-N procyanidin B2 Chemical compound C1([C@@H]2[C@H](O)[C@H](C3=C(O)C=C(O)C=C3O2)C=2C(O)=CC(O)=C3C[C@H]([C@H](OC3=2)C=2C=C(O)C(O)=CC=2)O)=CC=C(O)C(O)=C1 XFZJEEAOWLFHDH-NFJBMHMQSA-N 0.000 title claims abstract description 24
- 229920000642 polymer Polymers 0.000 title claims abstract description 18
- 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 15
- 229920002350 Procyanidin B2 Polymers 0.000 title claims abstract description 12
- 238000005336 cracking Methods 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims abstract description 9
- 235000009754 Vitis X bourquina Nutrition 0.000 title description 9
- 235000012333 Vitis X labruscana Nutrition 0.000 title description 9
- 235000014787 Vitis vinifera Nutrition 0.000 title description 9
- 229920002770 condensed tannin Polymers 0.000 title description 7
- 240000006365 Vitis vinifera Species 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 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
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 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
- 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
- 238000007445 Chromatographic isolation Methods 0.000 claims abstract description 5
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 238000001035 drying Methods 0.000 claims description 9
- 238000010828 elution Methods 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 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
- 239000000284 extract Substances 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- 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
- 239000003480 eluent Substances 0.000 claims description 3
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 238000010829 isocratic elution Methods 0.000 claims description 3
- 238000005374 membrane filtration Methods 0.000 claims description 3
- 239000012488 sample solution Substances 0.000 claims description 3
- 238000001514 detection method Methods 0.000 claims description 2
- 238000013517 stratification 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
- 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 8
- 229920000385 Procyanidin B1 Polymers 0.000 description 2
- 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
- XFZJEEAOWLFHDH-UKWJTHFESA-N procyanidin B1 Chemical compound C1([C@@H]2[C@H](O)[C@H](C3=C(O)C=C(O)C=C3O2)C=2C(O)=CC(O)=C3C[C@@H]([C@H](OC3=2)C=2C=C(O)C(O)=CC=2)O)=CC=C(O)C(O)=C1 XFZJEEAOWLFHDH-UKWJTHFESA-N 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
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 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
- 238000007689 inspection Methods 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
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009758 senescence Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Disclosure of the invention is the cracking of procyanidine high polymer and the extracting method of procyanidin B 2, 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, is not only utilized high polymer, and increases the utilization rate of polyphenol, the content of procyanidin B 2 is obtained with chromatographic isolation, product purity is high, reaches 99.1%, procyanidin B 2 yield is 35~42%.
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 B2.
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 Proanthocyanidin B1
Extracting method, which can be cracked into procyanidine oligomer by procyanidine high polymer, increase procyanidine
B2 recovery rate.
The extracting method of procyanidine high polymer cracking and procyanidin B 2, steps are as follows:
(1) commercial glucose seed extract 10g is dissolved in 500ml water, stratification in 4 DEG C of environment, water phase 500ml ethyl acetate
Extraction, separates, three times, water phase extract liquor is concentrated under reduced pressure into drying for water phase coextraction, obtains yellow high polymerization degree component after extraction；
(2) above-mentioned high polymerization degree component is dissolved in ethyl alcohol, adds catechin and hydrochloric acid is added dropwise and reacted, hydrochloric acid is 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
Be 0.1g:5ml with the mass volume ratio of the ethyl alcohol, the mass ratio of the high poly group point and the catechin for 0.1g:0.1~
0.3g；
(3) above-mentioned reaction solution 5ml being prepared into chromatographic isolation with 0.22 μm of membrane filtration, chromatographic column is Welch XB-C18,
21.2 mm × 250 mm, 10 μm, 25 DEG C of column temperature, mobile phase: the acetic acid water of acetonitrile and mass percentage concentration 0.2%, isocratic elution,
Acetonitrile accounts for the 20% of mobile phase volume when 0~25 min is eluted, and acetonitrile accounts for the 45% of mobile phase volume when 25~40 min are eluted, inspection
280 nm of wavelength, each 50 ml of sample solution are surveyed, 27~29 min elution fractions are received；
(4) 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 procyanidin B 2.
The advantage of the invention is that the extracting method of procyanidine high polymer cracking and procyanidin B 2, 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, under acidity
Cracking reaction, procyanidine high polymer are cracked into procyanidine oligomer, and crack reacting condition of the present invention is controllable, not only make high poly-
Body is utilized, and increases the utilization rate of polyphenol, obtains the content of procyanidin B 2 with chromatographic isolation, product purity is high, reaches
To 99.1%, procyanidin B 2 yield is 35~42%.
Specific embodiment
Present invention is further described in detail with reference to embodiments.
Embodiment 1
Commercial glucose seed extract 10g(polyphenol content is higher than 95%, the degree of polymerization 3.7) it is dissolved in 500ml water, it is stood in 4 DEG C of environment
Layering, water phase are extracted with 500ml ethyl acetate, are separated after extraction, three times, water phase is concentrated under reduced pressure into drying for water phase coextraction, obtains
6.2 g(polyphenol content of yellow high polymerization degree component is higher than 95%, the degree of polymerization 5.2).High polymerization degree component is dissolved in ethyl alcohol, is added
The mass volume ratio of catechin and hydrochloric acid, high poly group point and ethyl alcohol is 0.1g:5ml, and high poly group point and the mass ratio of catechin are
0.1g:0.2g, reaction temperature are controlled at 30 DEG C, the reaction time 25 minutes, control hydrochloric acid final concentration 0.02M, reaction solution crosses 0.22 μ
M membrane filtration prepares chromatographic isolation, and chromatographic column is Welch XB-C18,21.2mm × 250mm, 10 μm, 25 DEG C of column temperature, flows
Phase: acetonitrile and 0.2% acetic acid water, isocratic elution, when 0~25 min is eluted, acetonitrile volume accounts for 20%, 25~40 min, elution
When, acetonitrile volume accounts for 45%, and Detection wavelength 280 nm, each 50 ml of sample solution receive 27~29 min elution fractions, depressurizes dense
It is reduced to drying, is mixed with 300~400 mesh silica gel by weight 1:1, the mesh silicagel column of 200-~300 is crossed, ethyl acetate elution subtracts
Pressure concentration ethyl acetate eluent obtains 2.48 g clear crystal procyanidin B 2s to drying.
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 40 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 0.06M, and at 50 DEG C, the reaction time is 10 minutes for reaction temperature control.
Claims (1)
1. the extracting method of procyanidine high polymer cracking and procyanidin B 2, 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, water phase 500ml ethyl acetate
Extraction, separates, three times, water phase extract liquor is concentrated under reduced pressure into drying for water phase coextraction, obtains yellow high polymerization degree component after extraction；
B, above-mentioned high polymerization degree component is dissolved in ethyl alcohol, adds catechin and hydrochloric acid is added dropwise and reacted, hydrochloric acid is 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
Be 0.1g:5ml with the mass volume ratio of the ethyl alcohol, the mass ratio of the high poly group point and the catechin for 0.1g:0.1~
0.3g；
C, by above-mentioned reaction solution 5ml, with 0.22 μm of membrane filtration, chromatographic isolation is prepared, chromatographic column is Welch XB-C18,21.2
Mm × 250 mm, 10 μm, 25 DEG C of column temperature, mobile phase: the acetic acid water of acetonitrile and mass percentage concentration 0.2%, isocratic elution, 0~
Acetonitrile accounts for the 20% of mobile phase volume when 25 min are eluted, and acetonitrile accounts for the 45% of mobile phase volume when 25~40 min are eluted, detection
Wavelength 280 nm, each 50 ml of sample solution receive 27~29 min elution fractions；
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 procyanidin B 2.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811561716.3A CN109651322A (en) | 2018-12-20 | 2018-12-20 | The extracting method of Proanthocyanidins from Grape Seeds high polymer cracking and procyanidin B 2 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811561716.3A CN109651322A (en) | 2018-12-20 | 2018-12-20 | The extracting method of Proanthocyanidins from Grape Seeds high polymer cracking and procyanidin B 2 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109651322A true CN109651322A (en) | 2019-04-19 |
Family
ID=66115896
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|---|---|---|---|
| CN201811561716.3A Pending CN109651322A (en) | 2018-12-20 | 2018-12-20 | The extracting method of Proanthocyanidins from Grape Seeds high polymer cracking and procyanidin B 2 |
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| CN (1) | CN109651322A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114605369A (en) * | 2022-04-07 | 2022-06-10 | 西安天美生物科技股份有限公司 | Procyanidine B2, and purification method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101012216A (en) * | 2007-02-02 | 2007-08-08 | 浙江大学 | Method of preparing oligomeric proanthocyanidins |
| 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 CN201811561716.3A patent/CN109651322A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101012216A (en) * | 2007-02-02 | 2007-08-08 | 浙江大学 | Method of preparing oligomeric proanthocyanidins |
| 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 (1)
| Title |
|---|
| NILS KOHLER等: "New Approach for the Synthesis and Isolation of Dimeric Procyanidins", 《J. AGRIC. FOOD CHEM》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114605369A (en) * | 2022-04-07 | 2022-06-10 | 西安天美生物科技股份有限公司 | Procyanidine B2, and purification method and application thereof |
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