CA2575135C - Method for analyzing oligomeric proanthocyanidin (opc) - Google Patents
Method for analyzing oligomeric proanthocyanidin (opc) Download PDFInfo
- Publication number
- CA2575135C CA2575135C CA2575135A CA2575135A CA2575135C CA 2575135 C CA2575135 C CA 2575135C CA 2575135 A CA2575135 A CA 2575135A CA 2575135 A CA2575135 A CA 2575135A CA 2575135 C CA2575135 C CA 2575135C
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- CA
- Canada
- Prior art keywords
- opc
- analyte
- weight
- polymer
- polymers
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 58
- 229920002770 condensed tannin Polymers 0.000 title claims description 90
- 229920000642 polymer Polymers 0.000 claims abstract description 42
- 229930014669 anthocyanidin Natural products 0.000 claims abstract description 25
- 235000008758 anthocyanidins Nutrition 0.000 claims abstract description 25
- 150000001452 anthocyanidin derivatives Chemical class 0.000 claims abstract description 24
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 22
- 230000007062 hydrolysis Effects 0.000 claims abstract description 21
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 18
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 14
- 235000013305 food Nutrition 0.000 claims abstract description 10
- 239000005445 natural material Substances 0.000 claims abstract description 8
- 235000013361 beverage Nutrition 0.000 claims abstract description 7
- 239000002537 cosmetic Substances 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 239000012491 analyte Substances 0.000 claims description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 24
- 229930182497 flavan-3-ol Natural products 0.000 claims description 20
- OEIJRRGCTVHYTH-UHFFFAOYSA-N Favan-3-ol Chemical compound OC1CC2=CC=CC=C2OC1C1=CC=CC=C1 OEIJRRGCTVHYTH-UHFFFAOYSA-N 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 13
- 238000002835 absorbance Methods 0.000 claims description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 12
- 235000013824 polyphenols Nutrition 0.000 claims description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 238000010521 absorption reaction Methods 0.000 claims description 9
- 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 8
- 235000019253 formic acid Nutrition 0.000 claims description 8
- XFZJEEAOWLFHDH-NFJBMHMQSA-N Epicatechin-(4beta->8)-catechin Natural products 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 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- 235000004298 Tamarindus indica Nutrition 0.000 claims description 7
- 229920002414 procyanidin Polymers 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000005259 measurement Methods 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 229920000385 Procyanidin B1 Polymers 0.000 claims description 5
- 238000000862 absorption spectrum Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- XFZJEEAOWLFHDH-UKWJTHFESA-N procyanidin B1 Chemical group 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 claims description 5
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
- 244000269722 Thea sinensis Species 0.000 claims description 4
- 235000009754 Vitis X bourquina Nutrition 0.000 claims description 4
- 235000012333 Vitis X labruscana Nutrition 0.000 claims description 4
- 235000014787 Vitis vinifera Nutrition 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 235000013616 tea Nutrition 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 244000299461 Theobroma cacao Species 0.000 claims description 2
- 235000009470 Theobroma cacao Nutrition 0.000 claims description 2
- 238000011088 calibration curve Methods 0.000 claims description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 2
- 238000010829 isocratic elution Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 235000010204 pine bark Nutrition 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 240000004584 Tamarindus indica Species 0.000 claims 1
- 240000006365 Vitis vinifera Species 0.000 claims 1
- 235000013334 alcoholic beverage Nutrition 0.000 claims 1
- 239000003480 eluent Substances 0.000 claims 1
- 238000000227 grinding Methods 0.000 claims 1
- 235000014214 soft drink Nutrition 0.000 claims 1
- 238000003556 assay Methods 0.000 abstract description 9
- 239000003814 drug Substances 0.000 abstract description 5
- 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 13
- 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 description 13
- 229920001991 Proanthocyanidin Polymers 0.000 description 13
- 239000013638 trimer Substances 0.000 description 13
- 239000000539 dimer Substances 0.000 description 12
- 239000000523 sample Substances 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 10
- VEVZSMAEJFVWIL-UHFFFAOYSA-O cyanidin cation Chemical compound [O+]=1C2=CC(O)=CC(O)=C2C=C(O)C=1C1=CC=C(O)C(O)=C1 VEVZSMAEJFVWIL-UHFFFAOYSA-O 0.000 description 10
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 8
- 235000005487 catechin Nutrition 0.000 description 8
- 229950001002 cianidanol Drugs 0.000 description 8
- 238000004305 normal phase HPLC Methods 0.000 description 7
- 241000596504 Tamarindus Species 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 235000007336 cyanidin Nutrition 0.000 description 5
- FFNDMZIBVDSQFI-UHFFFAOYSA-N delphinidin chloride Chemical compound [Cl-].[O+]=1C2=CC(O)=CC(O)=C2C=C(O)C=1C1=CC(O)=C(O)C(O)=C1 FFNDMZIBVDSQFI-UHFFFAOYSA-N 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- GCPYCNBGGPHOBD-UHFFFAOYSA-N Delphinidin Natural products OC1=Cc2c(O)cc(O)cc2OC1=C3C=C(O)C(=O)C(=C3)O GCPYCNBGGPHOBD-UHFFFAOYSA-N 0.000 description 4
- 235000007242 delphinidin Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- YPVZJXMTXCOTJN-UHFFFAOYSA-N pelargonidin chloride Chemical compound [Cl-].C1=CC(O)=CC=C1C(C(=C1)O)=[O+]C2=C1C(O)=CC(O)=C2 YPVZJXMTXCOTJN-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229930013915 (+)-catechin Natural products 0.000 description 3
- 235000007219 (+)-catechin Nutrition 0.000 description 3
- 241000219095 Vitis Species 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 229940087559 grape seed Drugs 0.000 description 3
- HKUHOPQRJKPJCJ-UHFFFAOYSA-N pelargonidin Natural products OC1=Cc2c(O)cc(O)cc2OC1c1ccc(O)cc1 HKUHOPQRJKPJCJ-UHFFFAOYSA-N 0.000 description 3
- 235000006251 pelargonidin Nutrition 0.000 description 3
- 238000004007 reversed phase HPLC Methods 0.000 description 3
- 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 2
- 229930013783 (-)-epicatechin Natural products 0.000 description 2
- 235000007355 (-)-epicatechin Nutrition 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000002206 flavan-3-ols Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 238000011158 quantitative evaluation Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- CXQWRCVTCMQVQX-LSDHHAIUSA-N (+)-taxifolin Chemical compound C1([C@@H]2[C@H](C(C3=C(O)C=C(O)C=C3O2)=O)O)=CC=C(O)C(O)=C1 CXQWRCVTCMQVQX-LSDHHAIUSA-N 0.000 description 1
- COAWNPJQKJEHPG-UHFFFAOYSA-N 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-1lambda^{4}-chromen-1-ylium chloride Chemical compound [Cl-].[O+]=1C2=CC(O)=CC(O)=C2C=C(O)C=1C1=CC=C(O)C(O)=C1 COAWNPJQKJEHPG-UHFFFAOYSA-N 0.000 description 1
- 102100027324 2-hydroxyacyl-CoA lyase 1 Human genes 0.000 description 1
- 101001009252 Homo sapiens 2-hydroxyacyl-CoA lyase 1 Proteins 0.000 description 1
- 229920002350 Procyanidin B2 Polymers 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
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- CXQWRCVTCMQVQX-UHFFFAOYSA-N cis-dihydroquercetin Natural products O1C2=CC(O)=CC(O)=C2C(=O)C(O)C1C1=CC=C(O)C(O)=C1 CXQWRCVTCMQVQX-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- NWKFECICNXDNOQ-UHFFFAOYSA-N flavylium Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=[O+]1 NWKFECICNXDNOQ-UHFFFAOYSA-N 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 235000009569 green tea Nutrition 0.000 description 1
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003836 peripheral circulation Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000008569 process Effects 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
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/02—Food
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/15—Medicinal preparations ; Physical properties thereof, e.g. dissolubility
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/142222—Hetero-O [e.g., ascorbic acid, etc.]
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Pathology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004-222255 | 2004-07-29 | ||
| JP2004222255A JP4659407B2 (ja) | 2004-07-29 | 2004-07-29 | オリゴメリックプロアントシアニジン（ｏｐｃ）の分析方法 |
| PCT/JP2005/014153 WO2006011640A1 (en) | 2004-07-29 | 2005-07-27 | Method for analyzing oligomeric proanthocyanidin (opc) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2575135A1 CA2575135A1 (en) | 2006-02-02 |
| CA2575135C true CA2575135C (en) | 2014-01-21 |
Family
ID=35448015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2575135A Expired - Fee Related CA2575135C (en) | 2004-07-29 | 2005-07-27 | Method for analyzing oligomeric proanthocyanidin (opc) |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8383413B2 (enExample) |
| EP (1) | EP1774319B1 (enExample) |
| JP (1) | JP4659407B2 (enExample) |
| KR (1) | KR101166393B1 (enExample) |
| CN (2) | CN102818865A (enExample) |
| CA (1) | CA2575135C (enExample) |
| SG (1) | SG145718A1 (enExample) |
| TW (1) | TWI355490B (enExample) |
| WO (1) | WO2006011640A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4942953B2 (ja) * | 2005-06-30 | 2012-05-30 | サントリーホールディングス株式会社 | プロシアニジンの分析方法 |
| JP2007306872A (ja) | 2006-05-19 | 2007-11-29 | Suntory Ltd | プロアントシアニジン含有茶飲料 |
| WO2008038726A1 (fr) * | 2006-09-29 | 2008-04-03 | Arysta Lifescience Corporation | Procédé de détermination de procyanidine oligomérique (opc) |
| KR100897519B1 (ko) * | 2007-08-31 | 2009-05-15 | (주)아모레퍼시픽 | 자외선차단 성분의 동시분석법 |
| JP2010236905A (ja) * | 2009-03-30 | 2010-10-21 | Meiji Seika Kaisha Ltd | アントシアニンの分析方法 |
| JP5337574B2 (ja) * | 2009-05-08 | 2013-11-06 | フジッコ株式会社 | プロアントシアニジンの分離精製方法 |
| CN102141519B (zh) * | 2010-12-30 | 2013-03-13 | 浙江现代中药与天然药物研究院有限公司 | 一种检测原花青素含量的方法 |
| US8877275B2 (en) | 2011-03-31 | 2014-11-04 | Suntory Holdings Limited | Proanthocyanidin-rich plant extract and method for preparing same |
| CN102323378A (zh) * | 2011-08-29 | 2012-01-18 | 湖南科技大学 | 一种快速检测植物中含原花色素的方法 |
| KR101877780B1 (ko) * | 2011-09-08 | 2018-07-13 | (주)바이오메디앙 | 유럽종 포도 추출물의 분석방법 |
| CN102924422B (zh) * | 2012-09-10 | 2015-03-11 | 华南理工大学 | 脉冲电场强化降解制备低聚原花青素的方法 |
| US20150237906A1 (en) | 2012-09-28 | 2015-08-27 | Suntory Holdings Limited | Monomeric proanthocyanidin-removed plant extract |
| JP5437537B1 (ja) * | 2012-10-05 | 2014-03-12 | フジッコ株式会社 | 低重合度プロアントシアニジンの製法 |
| WO2015020138A1 (ja) | 2013-08-09 | 2015-02-12 | サントリーホールディングス株式会社 | ヒドロキシチロソール及びその誘導体の体内吸収促進剤及びその利用 |
| CN103954700A (zh) * | 2014-04-12 | 2014-07-30 | 陕西衡道检测技术有限公司 | 一种测定原花青素含量及鉴别的方法 |
| CN105424947B (zh) * | 2015-12-28 | 2016-08-24 | 青岛古高生物科技有限公司 | 原花青素的应用及含原花青素的凝血酶时间测定试剂 |
| CN107247029B (zh) * | 2017-06-06 | 2020-01-21 | 桂林理工大学 | 一种快速检测有机半导体溴化反应产物组成的紫外可见吸收光谱分析法 |
| WO2019066031A1 (ja) | 2017-09-29 | 2019-04-04 | サントリーホールディングス株式会社 | アクアポリン３発現促進用組成物及びその使用 |
| CN109705080A (zh) * | 2018-12-20 | 2019-05-03 | 宁波天鼎生物科技有限公司 | 葡萄籽中原花青素高聚体裂解与原花青素b4的提取方法 |
| CN110988237B (zh) * | 2019-12-07 | 2022-07-01 | 四川汇宇制药股份有限公司 | 混合液中多成分检测方法 |
| FR3114814B1 (fr) | 2020-10-07 | 2023-10-27 | M&M Braun GmbH | Extrait de pépins de raisin à efficacité biologique positive accrue, son procédé de fabrication et ses utilisations |
| CN113156036B (zh) * | 2021-05-25 | 2022-08-05 | 浙江大学 | 亲水作用和反相液相色谱联用分析原花色素结构的方法 |
| CN114910578B (zh) * | 2022-04-11 | 2024-08-02 | 汤臣倍健股份有限公司 | 一种葡萄籽提取物中原花青素c1的测定方法 |
| CN117285498B (zh) * | 2023-09-26 | 2025-07-22 | 汤臣倍健股份有限公司 | 一种原花青素c1的制备方法 |
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| US191131A (en) * | 1877-05-22 | Improvement in filtering apparatus | ||
| US402738A (en) * | 1889-05-07 | Valve mechanism for washing filter-beds | ||
| US2066479A (en) * | 1931-06-08 | 1937-01-05 | Vernon W Macisaac | Fluid straining method and apparatus |
| US3357566A (en) * | 1964-06-22 | 1967-12-12 | Zurn Ind Inc | Dual element filter assembly with backwash arms |
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| JPS5325344B2 (enExample) * | 1974-03-28 | 1978-07-26 | ||
| IL47305A (en) * | 1975-05-14 | 1978-07-31 | Filtomat Water Filters For Agr | Method and apparatus for effecting the cleaning of a fluid filter |
| DE2645948C2 (de) * | 1976-10-12 | 1987-01-08 | Honeywell-Braukmann GmbH, 6950 Mosbach | Rückspülbare Filtereinrichtung |
| JPH0615672B2 (ja) * | 1984-10-03 | 1994-03-02 | 英一 井高 | アントシアニンの分析及び分取方法 |
| IL74527A0 (en) * | 1985-03-07 | 1985-06-30 | Amiad Sinon Vehashkaya | Fluid filtering device |
| US5236126A (en) * | 1989-02-23 | 1993-08-17 | Anzen Motor Co., Ltd. | Rotating nozzle apparatus with magnetic braking |
| IL94630A (en) | 1990-06-06 | 1993-08-18 | Filtration Ltd Herzliya And Yt | Self-cleaning filter |
| US5824229A (en) * | 1996-04-19 | 1998-10-20 | Larkey; James G. | Filtration of rolling solutions |
| US7015338B1 (en) | 1999-04-15 | 2006-03-21 | Mars Incorporated | Synthetic methods for preparing procyanidin oligomers |
| HK1043361A1 (en) * | 1999-04-23 | 2002-09-13 | Kyowa Hakko Kogyo Co., Ltd. | Methods for purifying proanthocyanidin oligomers |
| US6267879B1 (en) * | 1999-08-11 | 2001-07-31 | Odis Irrigation Equipment Ltd. | Continuous liquid filtering apparatus with multi-layer sintered filtering element |
| ITMI991896A1 (it) * | 1999-09-09 | 2001-03-09 | Carlo Ghisalberti | Melanine e pigmenti vegetali |
| RU2286778C2 (ru) * | 2000-03-22 | 2006-11-10 | Марс, Инк. | Применение процианидинов какао в сочетании с ацетилсалициловой кислотой как противотромбоцитного терапевтического средства |
| WO2008038726A1 (fr) * | 2006-09-29 | 2008-04-03 | Arysta Lifescience Corporation | Procédé de détermination de procyanidine oligomérique (opc) |
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- 2004-07-29 JP JP2004222255A patent/JP4659407B2/ja not_active Expired - Lifetime
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- 2005-07-27 EP EP05768820.2A patent/EP1774319B1/en not_active Expired - Lifetime
- 2005-07-27 CN CN2012102496110A patent/CN102818865A/zh active Pending
- 2005-07-27 CN CNA200580025187XA patent/CN1989407A/zh active Pending
- 2005-07-27 KR KR1020077002928A patent/KR101166393B1/ko not_active Expired - Fee Related
- 2005-07-27 WO PCT/JP2005/014153 patent/WO2006011640A1/en not_active Ceased
- 2005-07-27 SG SG200805839-8A patent/SG145718A1/en unknown
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- 2005-07-27 US US11/658,311 patent/US8383413B2/en not_active Expired - Fee Related
- 2005-07-28 TW TW094125641A patent/TWI355490B/zh not_active IP Right Cessation
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| US8383413B2 (en) | 2013-02-26 |
| KR20070039585A (ko) | 2007-04-12 |
| JP4659407B2 (ja) | 2011-03-30 |
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| CA2575135A1 (en) | 2006-02-02 |
| TW200617386A (en) | 2006-06-01 |
| EP1774319A1 (en) | 2007-04-18 |
| CN1989407A (zh) | 2007-06-27 |
| CN102818865A (zh) | 2012-12-12 |
| TWI355490B (en) | 2012-01-01 |
| WO2006011640A8 (en) | 2006-04-13 |
| US20080311662A1 (en) | 2008-12-18 |
| SG145718A1 (en) | 2008-09-29 |
| EP1774319B1 (en) | 2015-09-09 |
| JP2006038763A (ja) | 2006-02-09 |
| KR101166393B1 (ko) | 2012-07-23 |
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