CN1603320A - Method for preparing high content proanthocyanidin - Google Patents
Method for preparing high content proanthocyanidin Download PDFInfo
- Publication number
- CN1603320A CN1603320A CN 200410053240 CN200410053240A CN1603320A CN 1603320 A CN1603320 A CN 1603320A CN 200410053240 CN200410053240 CN 200410053240 CN 200410053240 A CN200410053240 A CN 200410053240A CN 1603320 A CN1603320 A CN 1603320A
- Authority
- CN
- China
- Prior art keywords
- pycnogenols
- solvent
- column chromatography
- bed volume
- chromatography
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 238000000034 method Methods 0.000 title claims abstract description 16
- JPFCOVZKLAXXOE-XBNSMERZSA-N (3r)-2-(3,5-dihydroxy-4-methoxyphenyl)-8-[(2r,3r,4r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-chromen-4-yl]-3,4-dihydro-2h-chromene-3,5,7-triol Chemical compound C1=C(O)C(OC)=C(O)C=C1C1[C@H](O)CC(C(O)=CC(O)=C2[C@H]3C4=C(O)C=C(O)C=C4O[C@@H]([C@@H]3O)C=3C=CC(O)=CC=3)=C2O1 JPFCOVZKLAXXOE-XBNSMERZSA-N 0.000 title 1
- 229920001991 Proanthocyanidin Polymers 0.000 title 1
- 239000002904 solvent Substances 0.000 claims abstract description 27
- 238000004440 column chromatography Methods 0.000 claims abstract description 22
- 239000003463 adsorbent Substances 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 238000003556 assay Methods 0.000 claims abstract description 10
- 238000000926 separation method Methods 0.000 claims abstract description 8
- 238000000638 solvent extraction Methods 0.000 claims abstract description 7
- 239000000287 crude extract Substances 0.000 claims abstract description 5
- 229920002770 condensed tannin Polymers 0.000 claims description 31
- 235000018192 pine bark supplement Nutrition 0.000 claims description 31
- 238000004587 chromatography analysis Methods 0.000 claims description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 14
- 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 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 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 claims description 13
- 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 claims description 13
- 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 claims description 13
- 229920002414 procyanidin Polymers 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 11
- 238000000605 extraction Methods 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 7
- 235000009392 Vitis Nutrition 0.000 claims description 7
- 241000219095 Vitis Species 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- 210000000582 semen Anatomy 0.000 claims description 7
- 239000012141 concentrate Substances 0.000 claims description 6
- 239000000284 extract Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000008367 deionised water Substances 0.000 claims description 5
- 229910021641 deionized water Inorganic materials 0.000 claims description 5
- 230000008021 deposition Effects 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 238000005137 deposition process Methods 0.000 claims description 4
- 238000005119 centrifugation Methods 0.000 claims description 3
- 238000002203 pretreatment Methods 0.000 claims description 3
- 238000002086 displacement chromatography Methods 0.000 claims description 2
- 238000011010 flushing procedure Methods 0.000 claims description 2
- 150000004676 glycans Chemical class 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims description 2
- 229920001282 polysaccharide Polymers 0.000 claims description 2
- 239000005017 polysaccharide Substances 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 238000001556 precipitation Methods 0.000 abstract 2
- 229940087559 grape seed Drugs 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000011148 porous material Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 10
- 239000000945 filler Substances 0.000 description 5
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000011049 filling Methods 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 229930003427 Vitamin E Natural products 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 235000019165 vitamin E Nutrition 0.000 description 2
- 229940046009 vitamin E Drugs 0.000 description 2
- 239000011709 vitamin E Substances 0.000 description 2
- 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 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
- 229920002307 Dextran Polymers 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229940123457 Free radical scavenger Drugs 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229940126707 lipid peroxidation inhibitor Drugs 0.000 description 1
- 230000004089 microcirculation Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Medicines Containing Plant Substances (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Abstract
Description
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200410053240 CN1253446C (en) | 2004-07-23 | 2004-07-23 | Method for preparing high content proanthocyanidin |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200410053240 CN1253446C (en) | 2004-07-23 | 2004-07-23 | Method for preparing high content proanthocyanidin |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1603320A true CN1603320A (en) | 2005-04-06 |
CN1253446C CN1253446C (en) | 2006-04-26 |
Family
ID=34666092
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 200410053240 Expired - Fee Related CN1253446C (en) | 2004-07-23 | 2004-07-23 | Method for preparing high content proanthocyanidin |
Country Status (1)
Country | Link |
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CN (1) | CN1253446C (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1313460C (en) * | 2004-11-15 | 2007-05-02 | 西安皓天生物工程技术有限责任公司 | Method for extracting anthocyanidin |
CN101781279A (en) * | 2010-01-29 | 2010-07-21 | 青岛大学 | Preparation method of grape seed procyanidin |
CN102093328A (en) * | 2010-12-20 | 2011-06-15 | 大兴安岭林格贝有机食品有限责任公司 | Method for enriching and purifying procyanidin in pine bark |
CN101239962B (en) * | 2007-02-07 | 2011-12-07 | 上海华珠生物科技有限公司 | Method for extracting proanthocyanidins from cranberry |
CN103405583A (en) * | 2013-08-13 | 2013-11-27 | 新疆西部牧业股份有限公司 | Method for purifying grape seed polyphenol substance |
CN104496957A (en) * | 2014-12-01 | 2015-04-08 | 成都红柿子科技有限公司 | Method for extracting procyanidine from grape skins |
CN105925005A (en) * | 2016-04-22 | 2016-09-07 | 江苏省农业科学院 | Preparation method of highly pure anthocyanin pigment powder |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104447944A (en) * | 2014-12-26 | 2015-03-25 | 青岛海隆达生物科技有限公司 | Extracting method of grape seed protein |
-
2004
- 2004-07-23 CN CN 200410053240 patent/CN1253446C/en not_active Expired - Fee Related
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1313460C (en) * | 2004-11-15 | 2007-05-02 | 西安皓天生物工程技术有限责任公司 | Method for extracting anthocyanidin |
CN101239962B (en) * | 2007-02-07 | 2011-12-07 | 上海华珠生物科技有限公司 | Method for extracting proanthocyanidins from cranberry |
CN101781279A (en) * | 2010-01-29 | 2010-07-21 | 青岛大学 | Preparation method of grape seed procyanidin |
CN101781279B (en) * | 2010-01-29 | 2013-10-09 | 青岛大学 | Preparation method of grape seed procyanidin |
CN102093328A (en) * | 2010-12-20 | 2011-06-15 | 大兴安岭林格贝有机食品有限责任公司 | Method for enriching and purifying procyanidin in pine bark |
CN103405583A (en) * | 2013-08-13 | 2013-11-27 | 新疆西部牧业股份有限公司 | Method for purifying grape seed polyphenol substance |
CN104496957A (en) * | 2014-12-01 | 2015-04-08 | 成都红柿子科技有限公司 | Method for extracting procyanidine from grape skins |
CN105925005A (en) * | 2016-04-22 | 2016-09-07 | 江苏省农业科学院 | Preparation method of highly pure anthocyanin pigment powder |
Also Published As
Publication number | Publication date |
---|---|
CN1253446C (en) | 2006-04-26 |
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C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract |
Assignee: HANGZHOU XIASHA BIOCHEMICAL TECH Co.,Ltd. Assignor: Zhejiang University Contract fulfillment period: 2008.9.1 to 2013.8.31 Contract record no.: 2008330002497 Denomination of invention: Method for preparing high content proanthocyanidin Granted publication date: 20060426 License type: Exclusive license Record date: 20081201 |
|
LIC | Patent licence contract for exploitation submitted for record |
Free format text: EXCLUSIVE LICENSE; TIME LIMIT OF IMPLEMENTING CONTACT: 2008.9.1 TO 2013.8.31; CHANGE OF CONTRACT Name of requester: HANGZHOU XIASHA BIOTECHNOLOGY CO., LTD. Effective date: 20081201 |
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CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20060426 Termination date: 20210723 |
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CF01 | Termination of patent right due to non-payment of annual fee |