CN1151143C - 原花色素低聚物的提纯方法 - Google Patents
原花色素低聚物的提纯方法 Download PDFInfo
- Publication number
- CN1151143C CN1151143C CNB008089213A CN00808921A CN1151143C CN 1151143 C CN1151143 C CN 1151143C CN B008089213 A CNB008089213 A CN B008089213A CN 00808921 A CN00808921 A CN 00808921A CN 1151143 C CN1151143 C CN 1151143C
- Authority
- CN
- China
- Prior art keywords
- solvent
- proanthocyanidin
- dimerization
- poly
- proanthocyanidin oligomer
- 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 - Lifetime
Links
- 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 claims abstract description 136
- 229920001991 Proanthocyanidin Polymers 0.000 title claims abstract description 134
- 238000000034 method Methods 0.000 title claims abstract description 48
- 239000002904 solvent Substances 0.000 claims abstract description 75
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 68
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims abstract description 66
- 239000002994 raw material Substances 0.000 claims abstract description 42
- 238000000746 purification Methods 0.000 claims abstract description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000012071 phase Substances 0.000 claims abstract description 27
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000012046 mixed solvent Substances 0.000 claims abstract description 17
- 102000004190 Enzymes Human genes 0.000 claims abstract description 15
- 108090000790 Enzymes Proteins 0.000 claims abstract description 15
- 239000000741 silica gel Substances 0.000 claims abstract description 13
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 13
- 239000007791 liquid phase Substances 0.000 claims abstract description 11
- 150000002576 ketones Chemical class 0.000 claims abstract description 9
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 7
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 7
- 230000007062 hydrolysis Effects 0.000 claims abstract description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 75
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- 238000006471 dimerization reaction Methods 0.000 claims description 51
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 49
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 42
- 239000000463 material Substances 0.000 claims description 31
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
- 239000012264 purified product Substances 0.000 claims description 26
- 238000002386 leaching Methods 0.000 claims description 22
- 239000003960 organic solvent Substances 0.000 claims description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 10
- 230000001476 alcoholic effect Effects 0.000 claims description 7
- -1 methyl-formiate Chemical compound 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
- 238000004587 chromatography analysis Methods 0.000 claims description 6
- 239000004210 ether based solvent Substances 0.000 claims description 6
- 238000002203 pretreatment Methods 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 5
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 5
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims 1
- 238000004811 liquid chromatography Methods 0.000 abstract description 6
- QRFZGLTZLZZHCM-NWYMYRDLSA-N Cinnamtannin A3 Chemical compound C1([C@@H]2[C@H](O)[C@H](C3=C(O)C=C(O)C=C3O2)C2=C3O[C@@H]([C@H](O)[C@H](C3=C(O)C=C2O)C2=C3O[C@@H]([C@H](O)[C@H](C3=C(O)C=C2O)C2=C(O)C=C(O)C3=C2O[C@@H]([C@H](O)[C@H]3C=2C(O)=CC(O)=C3C[C@H]([C@H](OC3=2)C=2C=C(O)C(O)=CC=2)O)C=2C=C(O)C(O)=CC=2)C=2C=C(O)C(O)=CC=2)C=2C=C(O)C(O)=CC=2)=CC=C(O)C(O)=C1 QRFZGLTZLZZHCM-NWYMYRDLSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 238000000956 solid--liquid extraction Methods 0.000 abstract 1
- 238000000605 extraction Methods 0.000 description 67
- 239000007788 liquid Substances 0.000 description 32
- 239000000203 mixture Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 15
- 239000000284 extract Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 229920002770 condensed tannin Polymers 0.000 description 14
- 239000000178 monomer Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- 150000008442 polyphenolic compounds Chemical class 0.000 description 12
- 235000013824 polyphenols Nutrition 0.000 description 12
- 239000000523 sample Substances 0.000 description 12
- 239000000539 dimer Substances 0.000 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 description 10
- 229940088598 enzyme Drugs 0.000 description 10
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 10
- 229960001866 silicon dioxide Drugs 0.000 description 10
- 239000012535 impurity Substances 0.000 description 9
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 8
- 235000015203 fruit juice Nutrition 0.000 description 8
- 238000005829 trimerization reaction Methods 0.000 description 8
- 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 7
- 101000925662 Enterobacteria phage PRD1 Endolysin Proteins 0.000 description 7
- 229950001002 cianidanol Drugs 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 6
- 235000005487 catechin Nutrition 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VGEREEWJJVICBM-UHFFFAOYSA-N phloretin Chemical compound C1=CC(O)=CC=C1CCC(=O)C1=C(O)C=C(O)C=C1O VGEREEWJJVICBM-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 238000003953 normal phase liquid chromatography Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000012488 sample solution Substances 0.000 description 5
- 229930013915 (+)-catechin Natural products 0.000 description 4
- 235000007219 (+)-catechin Nutrition 0.000 description 4
- NGSWKAQJJWESNS-ZZXKWVIFSA-M 4-Hydroxycinnamate Natural products OC1=CC=C(\C=C\C([O-])=O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-M 0.000 description 4
- DFYRUELUNQRZTB-UHFFFAOYSA-N Acetovanillone Natural products COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 239000004367 Lipase Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 235000009392 Vitis Nutrition 0.000 description 4
- 241000219095 Vitis Species 0.000 description 4
- 230000004071 biological effect Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- ZWTDXYUDJYDHJR-UHFFFAOYSA-N (E)-1-(2,4-dihydroxyphenyl)-3-(2,4-dihydroxyphenyl)-2-propen-1-one Natural products OC1=CC(O)=CC=C1C=CC(=O)C1=CC=C(O)C=C1O ZWTDXYUDJYDHJR-UHFFFAOYSA-N 0.000 description 3
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 description 3
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 description 3
- 108090001060 Lipase Proteins 0.000 description 3
- 102000004882 Lipase Human genes 0.000 description 3
- 235000011430 Malus pumila Nutrition 0.000 description 3
- 235000015103 Malus silvestris Nutrition 0.000 description 3
- YQHMWTPYORBCMF-UHFFFAOYSA-N Naringenin chalcone Natural products C1=CC(O)=CC=C1C=CC(=O)C1=C(O)C=C(O)C=C1O YQHMWTPYORBCMF-UHFFFAOYSA-N 0.000 description 3
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000299461 Theobroma cacao Species 0.000 description 3
- 235000009470 Theobroma cacao Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000003712 anti-aging effect Effects 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 description 3
- 235000001368 chlorogenic acid Nutrition 0.000 description 3
- 229940074393 chlorogenic acid Drugs 0.000 description 3
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 description 3
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229930003935 flavonoid Natural products 0.000 description 3
- 235000017173 flavonoids Nutrition 0.000 description 3
- 150000002215 flavonoids Chemical class 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 235000019421 lipase Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 235000018192 pine bark supplement Nutrition 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 3
- XMOCLSLCDHWDHP-SWLSCSKDSA-N (+)-Epigallocatechin Natural products C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-SWLSCSKDSA-N 0.000 description 2
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 2
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- FZXRXKLUIMKDEL-UHFFFAOYSA-N 2-Methylpropyl propanoate Chemical compound CCC(=O)OCC(C)C FZXRXKLUIMKDEL-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 2
- 108010001682 Dextranase Proteins 0.000 description 2
- 244000236655 Diospyros kaki Species 0.000 description 2
- 108090000371 Esterases Proteins 0.000 description 2
- 240000008620 Fagopyrum esculentum Species 0.000 description 2
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229940126902 Phlorizin Drugs 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 2
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 240000001417 Vigna umbellata Species 0.000 description 2
- 235000011453 Vigna umbellata Nutrition 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 229920005601 base polymer Polymers 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 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 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- XMOCLSLCDHWDHP-IUODEOHRSA-N epi-Gallocatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-IUODEOHRSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- RGFNRWTWDWVHDD-UHFFFAOYSA-N isobutyl butyrate Chemical compound CCCC(=O)OCC(C)C RGFNRWTWDWVHDD-UHFFFAOYSA-N 0.000 description 2
- 238000000622 liquid--liquid extraction Methods 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- LQERIDTXQFOHKA-UHFFFAOYSA-N nonadecane Chemical compound CCCCCCCCCCCCCCCCCCC LQERIDTXQFOHKA-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- IOUVKUPGCMBWBT-UHFFFAOYSA-N phloridzosid Natural products OC1C(O)C(O)C(CO)OC1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 IOUVKUPGCMBWBT-UHFFFAOYSA-N 0.000 description 2
- IOUVKUPGCMBWBT-GHRYLNIYSA-N phlorizin Chemical compound O[C@@H]1[C@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 IOUVKUPGCMBWBT-GHRYLNIYSA-N 0.000 description 2
- 235000019139 phlorizin Nutrition 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 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 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229930013884 (+)-gallocatechin Natural products 0.000 description 1
- 235000007243 (+)-gallocatechin Nutrition 0.000 description 1
- 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 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 1
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 1
- AVMSWPWPYJVYKY-UHFFFAOYSA-N 2-Methylpropyl formate Chemical compound CC(C)COC=O AVMSWPWPYJVYKY-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
- 108010013043 Acetylesterase Proteins 0.000 description 1
- 239000004382 Amylase Substances 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- 108010053652 Butyrylcholinesterase Proteins 0.000 description 1
- 108010051152 Carboxylesterase Proteins 0.000 description 1
- 102000013392 Carboxylesterase Human genes 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- 244000060020 Chamaerops excelsa Species 0.000 description 1
- 235000013164 Chamaerops excelsa Nutrition 0.000 description 1
- 108010022172 Chitinases Proteins 0.000 description 1
- 102000012286 Chitinases Human genes 0.000 description 1
- 102100032404 Cholinesterase Human genes 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 101000874334 Dalbergia nigrescens Isoflavonoid 7-O-beta-apiosyl-glucoside beta-glycosidase Proteins 0.000 description 1
- HRNMOJZLZGYPOJ-UHFFFAOYSA-N Delphisine Natural products CC(=O)OC1C2C3C4(C5C6OC)C(O)CCC5(COC)CN(CC)C4C6C2(OC(C)=O)CC(OC)C1C3 HRNMOJZLZGYPOJ-UHFFFAOYSA-N 0.000 description 1
- 235000011511 Diospyros Nutrition 0.000 description 1
- 235000008597 Diospyros kaki Nutrition 0.000 description 1
- 101000757733 Enterococcus faecalis (strain ATCC 700802 / V583) Autolysin Proteins 0.000 description 1
- 235000011201 Ginkgo Nutrition 0.000 description 1
- 244000194101 Ginkgo biloba Species 0.000 description 1
- 235000008100 Ginkgo biloba Nutrition 0.000 description 1
- 108010000540 Hexosaminidases Proteins 0.000 description 1
- 102000002268 Hexosaminidases Human genes 0.000 description 1
- 102000004157 Hydrolases Human genes 0.000 description 1
- 108090000604 Hydrolases Proteins 0.000 description 1
- RMOUBSOVHSONPZ-UHFFFAOYSA-N Isopropyl formate Chemical compound CC(C)OC=O RMOUBSOVHSONPZ-UHFFFAOYSA-N 0.000 description 1
- IJMWOMHMDSDKGK-UHFFFAOYSA-N Isopropyl propionate Chemical compound CCC(=O)OC(C)C IJMWOMHMDSDKGK-UHFFFAOYSA-N 0.000 description 1
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 1
- XMOCLSLCDHWDHP-UHFFFAOYSA-N L-Epigallocatechin Natural products OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-UHFFFAOYSA-N 0.000 description 1
- 241000220225 Malus Species 0.000 description 1
- 108010054377 Mannosidases Proteins 0.000 description 1
- 102000001696 Mannosidases Human genes 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- 241000581835 Monodora junodii Species 0.000 description 1
- 101000757734 Mycolicibacterium phlei 38 kDa autolysin Proteins 0.000 description 1
- 239000010022 Myron Substances 0.000 description 1
- 241001439614 Myron Species 0.000 description 1
- 108010064696 N,O-diacetylmuramidase Proteins 0.000 description 1
- 108010006232 Neuraminidase Proteins 0.000 description 1
- 102000005348 Neuraminidase Human genes 0.000 description 1
- 241000219050 Polygonaceae Species 0.000 description 1
- 229920002350 Procyanidin B2 Polymers 0.000 description 1
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 1
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 101000693619 Starmerella bombicola Lactone esterase Proteins 0.000 description 1
- 108010055297 Sterol Esterase Proteins 0.000 description 1
- 102000000019 Sterol Esterase Human genes 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 102100029677 Trehalase Human genes 0.000 description 1
- 108010087472 Trehalase Proteins 0.000 description 1
- 240000000851 Vaccinium corymbosum Species 0.000 description 1
- 235000003095 Vaccinium corymbosum Nutrition 0.000 description 1
- 235000017537 Vaccinium myrtillus Nutrition 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 108010045649 agarase Proteins 0.000 description 1
- 108010061314 alpha-L-Fucosidase Proteins 0.000 description 1
- 102000012086 alpha-L-Fucosidase Human genes 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 108010009043 arylesterase Proteins 0.000 description 1
- 102000028848 arylesterase Human genes 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 235000021014 blueberries Nutrition 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001765 catechin Chemical class 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000007336 cyanidin Nutrition 0.000 description 1
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- HRNMOJZLZGYPOJ-PQJDTJHCSA-N delphisine Chemical compound CC(=O)O[C@@H]1[C@H]2[C@@H]3[C@@]4([C@@H]5[C@H]6OC)[C@@H](O)CC[C@@]5(COC)CN(CC)C4[C@H]6[C@@]2(OC(C)=O)C[C@H](OC)[C@H]1C3 HRNMOJZLZGYPOJ-PQJDTJHCSA-N 0.000 description 1
- YTJJRAWFHJBAMT-UHFFFAOYSA-N depside Natural products OC(=O)CC1=C(O)C=C(O)C=C1OC(=O)C1=CC=C(O)C(O)=C1 YTJJRAWFHJBAMT-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- DZYNKLUGCOSVKS-UHFFFAOYSA-N epigallocatechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3cc(O)c(O)c(O)c3 DZYNKLUGCOSVKS-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 229940087559 grape seed Drugs 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229930005346 hydroxycinnamic acid Natural products 0.000 description 1
- 235000010359 hydroxycinnamic acids Nutrition 0.000 description 1
- 108010090785 inulinase Proteins 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- JSLCOZYBKYHZNL-UHFFFAOYSA-N isobutyric acid butyl ester Natural products CCCCOC(=O)C(C)C JSLCOZYBKYHZNL-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 238000010829 isocratic elution Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- HKUHOPQRJKPJCJ-UHFFFAOYSA-N pelargonidin Natural products OC1=Cc2c(O)cc(O)cc2OC1c1ccc(O)cc1 HKUHOPQRJKPJCJ-UHFFFAOYSA-N 0.000 description 1
- 235000006251 pelargonidin Nutrition 0.000 description 1
- XVFMGWDSJLBXDZ-UHFFFAOYSA-O pelargonidin Chemical compound C1=CC(O)=CC=C1C(C(=C1)O)=[O+]C2=C1C(O)=CC(O)=C2 XVFMGWDSJLBXDZ-UHFFFAOYSA-O 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 108010038851 tannase Proteins 0.000 description 1
- 229960002203 tilactase Drugs 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
Images
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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
产量(g) | 固含量收率(%) | PB1 | PB2 | PC1 | PB1+PB2+PC1 | ||||||
含量(g) | 收率(%) | 含量(g) | 收率(%) | 含量(g) | 收率(%) | 含量(g) | 收率(%) | 纯度(%) | |||
萃取前样品 | (30.0) | (1.22) | (4.34) | (1.96) | (7.52) | (25.1) | |||||
乙酸甲酯萃取物 | 17.5 | 58.3 | 1.16 | 95.1 | 4.03 | 92.8 | 1.65 | 84.2 | 6.84 | 91.0 | 39.1 |
乙酸甲酯萃取后的非萃取物 | 12.5 | 41.7 | 0.06 | 4.9 | 0.31 | 7.2 | 0.31 | 15.8 | 0.68 | 9.0 | 5.4 |
萃取用的溶剂 | 固含量收率(%) | PB1(mg) | PB2(mg) | PC1(mg) | PB1+PB2+PC1 | ||
萃取量(mg) | 收率(%) | 纯度(%) | |||||
未用萃取溶剂处理 | (100) | 36.4 | 136.1 | 63.0 | 235.5 | (100) | 23.6 |
乙酸乙酯(对比实施例) | 9.9 | 6.2 | 24.3 | 7.0 | 37.5 | 15.1 | 38.3 |
100%乙酸甲酯 | 39.9 | 25.9 | 87.7 | 31.1 | 144.7 | 61.5 | 36.3 |
乙酸甲酯/甲醇(9/1) | 82.8 | 39.5 | 137.1 | 62.7 | 239.3 | 101.6 | 28.9 |
乙酸甲酯/乙醇(9/1) | 80.5 | 39.8 | 140.1 | 64.6 | 244.4 | 103.8 | 30.4 |
乙酸甲酯/丙醇(9/1) | 77.2 | 38.9 | 134.0 | 62.4 | 235.3 | 99.9 | 30.5 |
乙酸甲酯/丁醇(9/1) | 79.0 | 38.4 | 136.6 | 62.7 | 237.7 | 100.9 | 30.1 |
乙酸甲酯/甲酸乙酯(9/1) | 40.0 | 26.3 | 89.9 | 31.1 | 147.3 | 62.5 | 36.8 |
乙酸甲酯/乙酸乙酯(9/1) | 39.6 | 25.4 | 86.6 | 30.1 | 142.1 | 60.3 | 35.9 |
乙酸甲酯/丙酮(9/1) | 56.1 | 33.5 | 120.7 | 50.2 | 204.4 | 86.8 | 36.5 |
乙酸甲酯/乙腈(9/1) | 59.3 | 35.8 | 123.2 | 51.3 | 210.4 | 89.3 | 35.5 |
乙酸甲酯/四氢呋喃(9/1) | 83.7 | 34.4 | 120.1 | 51.3 | 205.8 | 87.4 | 24.6 |
乙酸甲酯/乙酸(9/1) | 70.5 | 38.3 | 131.1 | 56.5 | 225.9 | 95.9 | 32.1 |
乙酸甲酯/己烷(95/5) | 15.7 | 10.7 | 41.0 | 9.9 | 61.6 | 24.8 | 39.2 |
萃取用的溶剂 | 固含量收率(%) | PB1(mg)(%) | PB2(mg)(%) | PC1(mg)(%) | PB1+PB2+PC1 | ||
萃取量(mg) | 收率(%) | 纯度(%) | |||||
未用萃取溶剂处理 | 100 | 39.9(100) | 153.4(100) | 66.9(100) | 260.2 | 100 | 26 |
乙酸乙酯(对比实施例) | 34.9 | 23.0(57.6) | 90.4(58.9) | 28.7(42.9) | 142.1 | 54.6 | 40.7 |
乙酸乙酯/乙酸甲酯(9/1) | 39.2 | 25.8(64.7) | 100.9(65.8) | 32.3(48.3) | 159 | 61.1 | 40.6 |
乙酸乙酯/乙酸甲酯(7/3) | 42.5 | 28.6(71.7) | 110.2(71.8) | 35.5(53.1) | 174.3 | 67 | 41 |
乙酸乙酯/乙酸甲酯(5/5) | 46.5 | 31.0(77.7) | 121.0(78.9) | 39.9(59.6) | 191.9 | 73.8 | 41.3 |
乙酸乙酯/乙酸甲酯(3/7) | 51 | 33.8(84.7) | 130.1(84.8) | 44.5(66.5) | 208.4 | 80.1 | 40.9 |
乙酸乙酯/乙酸甲酯(1/9) | 51.6 | 33.0(82.7) | 127.7(83.2) | 45.4(67.9) | 206.1 | 79.2 | 39.9 |
乙酸乙酯/乙酸甲酯(1/10) | 52.4 | 33.3(83.5) | 128.9(84.0) | 47.1(70.4) | 209.3 | 80.4 | 39.9 |
Claims (6)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP116380/1999 | 1999-04-23 | ||
JP11638099 | 1999-04-23 | ||
JP116380/99 | 1999-04-23 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2003101047596A Division CN1238350C (zh) | 1999-04-23 | 2000-03-03 | 原花色素低聚物的提纯方法 |
CNB2003101047581A Division CN1276088C (zh) | 1999-04-23 | 2000-03-03 | 原花色素低聚物的提纯方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1356994A CN1356994A (zh) | 2002-07-03 |
CN1151143C true CN1151143C (zh) | 2004-05-26 |
Family
ID=14685579
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2003101047596A Expired - Lifetime CN1238350C (zh) | 1999-04-23 | 2000-03-03 | 原花色素低聚物的提纯方法 |
CNB2003101047581A Expired - Fee Related CN1276088C (zh) | 1999-04-23 | 2000-03-03 | 原花色素低聚物的提纯方法 |
CNB008089213A Expired - Lifetime CN1151143C (zh) | 1999-04-23 | 2000-03-03 | 原花色素低聚物的提纯方法 |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2003101047596A Expired - Lifetime CN1238350C (zh) | 1999-04-23 | 2000-03-03 | 原花色素低聚物的提纯方法 |
CNB2003101047581A Expired - Fee Related CN1276088C (zh) | 1999-04-23 | 2000-03-03 | 原花色素低聚物的提纯方法 |
Country Status (13)
Country | Link |
---|---|
US (1) | US6800433B1 (zh) |
EP (3) | EP1666476B1 (zh) |
JP (2) | JP4582917B2 (zh) |
KR (1) | KR100478296B1 (zh) |
CN (3) | CN1238350C (zh) |
AT (3) | ATE337310T1 (zh) |
AU (1) | AU774390B2 (zh) |
CA (1) | CA2370238A1 (zh) |
DE (3) | DE60037838T2 (zh) |
ES (3) | ES2296046T3 (zh) |
HK (1) | HK1043361A1 (zh) |
NZ (1) | NZ515078A (zh) |
WO (1) | WO2000064883A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102086187A (zh) * | 2011-01-28 | 2011-06-08 | 云南瑞升烟草技术(集团)有限公司 | 一种提取分离云南松树皮中低聚原花青素的方法 |
Families Citing this family (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2002311198A1 (en) * | 2002-04-24 | 2003-11-10 | Toyo Shinyaku Co., Ltd. | Process for producing proanthocyanidine-rich material |
WO2004080993A1 (ja) * | 2003-03-11 | 2004-09-23 | Toyo Shinyaku Co., Ltd. | プロアントシアニジン高含有物の製造方法 |
US20060216248A1 (en) * | 2003-04-30 | 2006-09-28 | Asahi Breweries, Ltd. | Material for inhibiting enamel decalcification |
JP2005082497A (ja) * | 2003-09-05 | 2005-03-31 | Asahi Breweries Ltd | 植物由来ポリフェノール成分を有効成分として含むことを特徴とする免疫調節剤 |
CN1303165C (zh) * | 2004-01-12 | 2007-03-07 | 四川大学 | 原花红色素的提取、分离及其衍生物的制备方法 |
JPWO2005070443A1 (ja) * | 2004-01-21 | 2007-12-27 | 株式会社東洋新薬 | 樹皮抽出物 |
JP4659407B2 (ja) * | 2004-07-29 | 2011-03-30 | サントリーホールディングス株式会社 | オリゴメリックプロアントシアニジン(opc)の分析方法 |
JP2006104181A (ja) * | 2004-09-13 | 2006-04-20 | Takahiro Tsujita | ブナ科植物由来の糖質分解酵素阻害物質、及びその用途 |
CN100566723C (zh) * | 2004-09-13 | 2009-12-09 | 辻田隆广 | 衍生自壳斗植物的糖酶抑制剂及其应用 |
JP2006096693A (ja) * | 2004-09-29 | 2006-04-13 | Tohoku Univ | 抗アレルギー剤 |
JP2006096694A (ja) * | 2004-09-29 | 2006-04-13 | Asahi Breweries Ltd | 食物アレルギー予防剤 |
AU2006216182A1 (en) | 2005-02-25 | 2006-08-31 | Amino Up Chemical Co., Ltd. | Method of producing proanthocyanidin oligomer |
WO2007003068A1 (fr) * | 2005-06-30 | 2007-01-11 | Hangzhou Lixin Biotechnology Co. Ltd. | Additif pour nourriture, procédé de préparation de celui-ci et application de celui-ci |
JP4798607B2 (ja) * | 2005-08-11 | 2011-10-19 | クラシエフーズ株式会社 | アンジオテンシン変換酵素阻害剤及びそれを用いた飲食品 |
US20080096825A1 (en) * | 2006-04-21 | 2008-04-24 | Ehrenkranz Joel R L | Preparation and Use of Phlorizin Compositions |
US7993687B2 (en) * | 2006-07-12 | 2011-08-09 | Julianne Marie Kawa | Compositions and methods for management of diabetes |
US20100040713A1 (en) * | 2006-08-11 | 2010-02-18 | Kracie Foods, Ltd. | Fat absorption inhibitor and food and drink using the same |
JP2008156265A (ja) * | 2006-12-22 | 2008-07-10 | Yamagata Prefecture | A型プロアントシアニジンオリゴマー画分及びその製造方法 |
WO2009080778A2 (de) * | 2007-12-21 | 2009-07-02 | Finzelberg Gmbh & Co. Kg | Zubereitungen mit hagebuttenextrakten sowie verfahren zur herstellung von hagebuttenextrakten |
JP5352258B2 (ja) * | 2008-01-31 | 2013-11-27 | 株式会社スギヨ | 栗皮の処理方法 |
FR2929853B1 (fr) * | 2008-04-09 | 2010-10-08 | Diana Naturals | Extrait de canneberge d'amerique et son utilisation |
CA2659498A1 (fr) * | 2008-04-09 | 2009-10-09 | Diana Naturals | Extrait de canneberge d'amerique et son utilisation |
US9173912B2 (en) | 2008-05-06 | 2015-11-03 | Finzelberg Gmbh & Co. Kg | Cistus extract containing enriched secondary plant ingredients |
JP4892690B2 (ja) | 2008-09-03 | 2012-03-07 | 財団法人宮崎県産業支援財団 | C型肝炎ウイルス産生抑制剤 |
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 |
CA2829907C (en) | 2011-03-31 | 2019-01-29 | Suntory Holdings Limited | Proanthocyanidin-rich plant extract |
CN102362876A (zh) * | 2011-10-24 | 2012-02-29 | 浙江省医学科学院 | 一种水杉皮提取物及其制备方法和用途 |
TWI574954B (zh) * | 2011-12-28 | 2017-03-21 | 三得利控股股份有限公司 | 寡聚原花青素之製造方法、聚合度之調整方法以及透明質酸酶抑制劑與膠原酶抑制劑 |
WO2014050840A1 (ja) * | 2012-09-28 | 2014-04-03 | サントリーホールディングス株式会社 | 単量体プロアントシアニジン除去植物抽出物 |
CN104837824B (zh) * | 2012-12-14 | 2017-10-20 | 株式会社明治 | 饮食品、补品和医药品等使用的特定多酚及其制造方法 |
CN103265519B (zh) * | 2013-05-15 | 2015-09-09 | 浙江大学 | 一种分离制备杨梅叶原花色素的方法 |
KR101756123B1 (ko) * | 2016-01-27 | 2017-07-17 | 주식회사 키토라이프 | 아스퍼질러스 속 균 유래의 조효소를 이용하는 안토시아닌 올리고머의 제조 방법 |
TW201733605A (zh) * | 2016-02-29 | 2017-10-01 | 明治股份有限公司 | 可可水萃物、含它之飲食品、可可萃取物之製造方法、及多酚之萃取方法 |
JP2019131536A (ja) | 2018-01-30 | 2019-08-08 | 学校法人北里研究所 | 麻黄エキス、又はエフェドリンアルカロイド除去麻黄エキスより得られた高分子縮合型タンニンを含有する抽出分画物とその製法及び用途 |
CN108164491B (zh) * | 2018-03-05 | 2019-10-25 | 湖北大学 | 具有抗炎作用的5,8-对醌式黄烷类化合物及其提取分离方法和应用 |
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 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6116982A (ja) * | 1984-07-03 | 1986-01-24 | Kikkoman Corp | 抗酸化剤 |
US4698360B1 (en) | 1985-04-09 | 1997-11-04 | D Investigations Pharmacologiq | Plant extract with a proanthocyanidins content as therapeutic agent having radical scavenger effect and use thereof |
US5484594A (en) | 1988-06-28 | 1996-01-16 | Tecnofarmaci S.P.A. | Process for preparing grapeseed extracts enriched in procyanidol oligomers |
JP2694748B2 (ja) | 1989-12-28 | 1997-12-24 | キッコーマン株式会社 | プロアントシアニジンの製造法 |
JP3200781B2 (ja) | 1993-02-12 | 2001-08-20 | 大成建設株式会社 | 地下水の還元方法 |
JPH0762014A (ja) | 1993-08-27 | 1995-03-07 | Tosoh Corp | 立体規則性ポリ−α−オレフィンの製造方法 |
FR2722498B1 (fr) * | 1994-07-12 | 1996-10-11 | Berkem Sa | Procede de preparation d'extraits contenant des composes polyphenoliques oligomeres de type catechique a partir de xources vegetales et extraits obtenus |
US5554645A (en) * | 1994-10-03 | 1996-09-10 | Mars, Incorporated | Antineoplastic cocoa extracts and methods for making and using the same |
FR2725447B1 (fr) | 1994-10-11 | 1996-12-27 | Sanofi Sa | Procede d'obtention d'oligomeres procyanidoliques |
JPH08283257A (ja) | 1995-02-15 | 1996-10-29 | Kikkoman Corp | プロアントシアニジンの品質改良法及び品質の改良されたプロアントシアニジンの製造法 |
JPH09221484A (ja) * | 1996-02-14 | 1997-08-26 | Kikkoman Corp | プロアントシアニジンの製造法 |
WO1997039632A1 (en) | 1996-04-22 | 1997-10-30 | Henkel Corporation | Natural antioxidant composition |
WO1997044407A1 (en) | 1996-05-23 | 1997-11-27 | Ian Alexander Gilmour | Process for extraction of proanthocyanidins from botanical material |
US6015913A (en) * | 1996-09-06 | 2000-01-18 | Mars, Incorporated | Method for producing fat and/or solids from cocoa beans |
JPH10218769A (ja) | 1997-02-06 | 1998-08-18 | Kikkoman Corp | 抗潰瘍剤 |
-
2000
- 2000-03-03 DE DE60037838T patent/DE60037838T2/de not_active Expired - Lifetime
- 2000-03-03 ES ES05024213T patent/ES2296046T3/es not_active Expired - Lifetime
- 2000-03-03 DE DE60030276T patent/DE60030276T2/de not_active Expired - Lifetime
- 2000-03-03 CN CNB2003101047596A patent/CN1238350C/zh not_active Expired - Lifetime
- 2000-03-03 EP EP05024213A patent/EP1666476B1/en not_active Expired - Lifetime
- 2000-03-03 EP EP00906694A patent/EP1180516B1/en not_active Expired - Lifetime
- 2000-03-03 KR KR10-2001-7013444A patent/KR100478296B1/ko not_active IP Right Cessation
- 2000-03-03 JP JP2000614235A patent/JP4582917B2/ja not_active Expired - Lifetime
- 2000-03-03 AT AT00906694T patent/ATE337310T1/de not_active IP Right Cessation
- 2000-03-03 ES ES05024212T patent/ES2305981T3/es not_active Expired - Lifetime
- 2000-03-03 AT AT05024212T patent/ATE396983T1/de not_active IP Right Cessation
- 2000-03-03 EP EP05024212A patent/EP1632486B1/en not_active Expired - Lifetime
- 2000-03-03 AT AT05024213T patent/ATE384056T1/de not_active IP Right Cessation
- 2000-03-03 AU AU28287/00A patent/AU774390B2/en not_active Ceased
- 2000-03-03 DE DE60039080T patent/DE60039080D1/de not_active Expired - Fee Related
- 2000-03-03 CA CA002370238A patent/CA2370238A1/en not_active Abandoned
- 2000-03-03 US US09/959,274 patent/US6800433B1/en not_active Expired - Fee Related
- 2000-03-03 WO PCT/JP2000/001307 patent/WO2000064883A1/ja active IP Right Grant
- 2000-03-03 ES ES00906694T patent/ES2269104T3/es not_active Expired - Lifetime
- 2000-03-03 NZ NZ515078A patent/NZ515078A/en unknown
- 2000-03-03 CN CNB2003101047581A patent/CN1276088C/zh not_active Expired - Fee Related
- 2000-03-03 CN CNB008089213A patent/CN1151143C/zh not_active Expired - Lifetime
-
2002
- 2002-05-31 HK HK02104157.9A patent/HK1043361A1/zh unknown
-
2010
- 2010-07-26 JP JP2010167536A patent/JP5094927B2/ja not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102086187A (zh) * | 2011-01-28 | 2011-06-08 | 云南瑞升烟草技术(集团)有限公司 | 一种提取分离云南松树皮中低聚原花青素的方法 |
CN102086187B (zh) * | 2011-01-28 | 2012-05-23 | 云南瑞升烟草技术(集团)有限公司 | 一种提取分离云南松树皮中低聚原花青素的方法 |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1151143C (zh) | 原花色素低聚物的提纯方法 | |
CN105037300B (zh) | 一种从马尾藻中综合提取岩藻黄素和褐藻多酚的方法 | |
CN1121924A (zh) | 水果多酚及其生产方法以及其用途 | |
CN100387588C (zh) | 从植物中提取杨梅树皮素的方法 | |
CN1159447C (zh) | 微生物发酵法生产香料苯乙醇的工艺 | |
CN106226426B (zh) | 一种高效液相色谱拆分卡格列净五元环杂质对映体的方法 | |
CN1197972C (zh) | 一种生产番茄红素的方法 | |
KR100659945B1 (ko) | 천연용매를 추출매체로 하는 소나무류 수피 유래 항산화성물질 추출방법 및 이에 의한 항산화성 추출물 | |
CN1246316C (zh) | 大豆异黄酮主要单体组分的分离方法 | |
CN101608193B (zh) | 无溶剂体系酶促合成防晒油阿魏酸辛酸甘油酯的方法 | |
NZ525540A (en) | A process for purification of dimeric to pentameric proanthocyanidin oligomers with uniform polymerization degree | |
AU2004200132A1 (en) | Methods for purifying proanthocyanidin oligomers | |
JP2004026760A (ja) | 癌細胞のアポトーシス誘導剤、その製造方法、それを有効成分とする抗癌剤、食品製剤及び化粧品 | |
CN1166675C (zh) | 生产高活性银杏叶提取物的萃取剂及其提取与分析方法 | |
Altiok et al. | Recovery of proanthocyanidin from waste of Turkish traditional product, Pekmez (molasses) | |
CN112159382A (zh) | 一种从荔枝生理落果中高效制备活性低聚原花青素的方法 | |
CN1780816A (zh) | 2"-羟基烟草胺及其制造方法,及血管紧张素转换酶抑制剂、降压剂及健康食品 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C06 | Publication | ||
PB01 | Publication | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: KYOWA HAKKO KOGYO CO., LTD.; ASAHI CO., LTD. Free format text: FORMER OWNER: KYOWA HAKKO KOGYO CO., LTD.; THE NIKKA WHISKY DISTILLING CO., LTD. Effective date: 20080704 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20080704 Address after: Tokyo, Japan Co-patentee after: Asahi Breweries, Ltd. Patentee after: kyowa hakko Address before: Tokyo, Japan Co-patentee before: NIKKA WHISKY DISTILLING Co., Ltd. Patentee before: kyowa hakko |
|
ASS | Succession or assignment of patent right |
Owner name: XIEHE FERMENTATION BIOCHEMICAL CO., LTD. Free format text: FORMER OWNER: KYOWA HAKKO KOGYO CO., LTD. Effective date: 20100122 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20100122 Address after: Tokyo, Japan Co-patentee after: Asahi Breweries, Ltd. Patentee after: Concorde fermentation Biochemical Co., Ltd. Address before: Tokyo, Japan Co-patentee before: Asahi Breweries, Ltd. Patentee before: kyowa hakko |
|
C56 | Change in the name or address of the patentee | ||
CP01 | Change in the name or title of a patent holder |
Address after: Tokyo, Japan, Japan Co-patentee after: Asahi Group Holdings Ltd. Patentee after: Kyowa Hakko Bio Co., Ltd. Address before: Tokyo, Japan, Japan Co-patentee before: Asahi Breweries, Ltd. Patentee before: Kyowa Hakko Bio Co., Ltd. |
|
ASS | Succession or assignment of patent right |
Free format text: FORMER OWNER: ASAHI GROUP HOLDINGS, LTD. Effective date: 20120608 Owner name: ASAHI GROUP HOLDINGS, LTD. Free format text: FORMER OWNER: KYOWA HAKKO KOGYO KK Effective date: 20120608 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20120608 Address after: Tokyo, Japan, Japan Patentee after: Asahi Group Holdings Ltd. Address before: Tokyo, Japan, Japan Co-patentee before: Asahi Group Holdings Ltd. Patentee before: Kyowa Hakko Bio Co., Ltd. |
|
CX01 | Expiry of patent term |
Granted publication date: 20040526 |
|
CX01 | Expiry of patent term |