JP2016519177A - 青色アントシアニン画分の単離方法 - Google Patents
青色アントシアニン画分の単離方法 Download PDFInfo
- Publication number
- JP2016519177A JP2016519177A JP2016502403A JP2016502403A JP2016519177A JP 2016519177 A JP2016519177 A JP 2016519177A JP 2016502403 A JP2016502403 A JP 2016502403A JP 2016502403 A JP2016502403 A JP 2016502403A JP 2016519177 A JP2016519177 A JP 2016519177A
- Authority
- JP
- Japan
- Prior art keywords
- fraction
- anthocyanin
- anthocyanins
- blue
- solvent
- 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
Links
- 235000010208 anthocyanin Nutrition 0.000 title claims abstract description 231
- 239000004410 anthocyanin Substances 0.000 title claims abstract description 231
- 229930002877 anthocyanin Natural products 0.000 title claims abstract description 231
- 150000004636 anthocyanins Chemical class 0.000 title claims abstract description 229
- 238000002955 isolation Methods 0.000 title description 2
- 239000000284 extract Substances 0.000 claims abstract description 85
- 238000000034 method Methods 0.000 claims abstract description 44
- 235000015203 fruit juice Nutrition 0.000 claims abstract description 39
- 235000015192 vegetable juice Nutrition 0.000 claims abstract description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 71
- 239000007864 aqueous solution Substances 0.000 claims description 56
- 239000002904 solvent Substances 0.000 claims description 53
- 239000000243 solution Substances 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 38
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 claims description 35
- 240000007124 Brassica oleracea Species 0.000 claims description 34
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 claims description 34
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 claims description 34
- 238000005342 ion exchange Methods 0.000 claims description 26
- 238000010521 absorption reaction Methods 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 241000352057 Solanum vernei Species 0.000 claims description 10
- 235000004976 Solanum vernei Nutrition 0.000 claims description 10
- 244000000626 Daucus carota Species 0.000 claims description 9
- 235000002767 Daucus carota Nutrition 0.000 claims description 9
- 239000012156 elution solvent Substances 0.000 claims description 6
- 238000011068 loading method Methods 0.000 claims description 6
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 4
- 238000005341 cation exchange Methods 0.000 claims description 3
- 238000010828 elution Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000003086 colorant Substances 0.000 description 70
- 235000016425 Arthrospira platensis Nutrition 0.000 description 20
- 240000002900 Arthrospira platensis Species 0.000 description 20
- 239000000038 blue colorant Substances 0.000 description 20
- 229940082787 spirulina Drugs 0.000 description 20
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 18
- 235000009508 confectionery Nutrition 0.000 description 13
- 150000001768 cations Chemical group 0.000 description 12
- 235000013399 edible fruits Nutrition 0.000 description 12
- 235000013311 vegetables Nutrition 0.000 description 12
- 230000001747 exhibiting effect Effects 0.000 description 11
- 235000000346 sugar Nutrition 0.000 description 11
- 239000008057 potassium phosphate buffer Substances 0.000 description 10
- 238000012799 strong cation exchange Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 238000011894 semi-preparative HPLC Methods 0.000 description 9
- 235000012745 brilliant blue FCF Nutrition 0.000 description 8
- 239000004161 brilliant blue FCF Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 7
- 238000005194 fractionation Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 230000003595 spectral effect Effects 0.000 description 7
- 230000008859 change Effects 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000008863 intramolecular interaction Effects 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 229930014669 anthocyanidin Natural products 0.000 description 4
- 235000008758 anthocyanidins Nutrition 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 239000000976 ink Substances 0.000 description 4
- 230000009878 intermolecular interaction Effects 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- -1 methoxyl groups Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 235000017647 Brassica oleracea var italica Nutrition 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 244000088415 Raphanus sativus Species 0.000 description 3
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000078534 Vaccinium myrtillus Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- NWKFECICNXDNOQ-UHFFFAOYSA-N flavylium Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=[O+]1 NWKFECICNXDNOQ-UHFFFAOYSA-N 0.000 description 3
- 235000012055 fruits and vegetables Nutrition 0.000 description 3
- KHLVKKOJDHCJMG-QDBORUFSSA-L indigo carmine Chemical compound [Na+].[Na+].N/1C2=CC=C(S([O-])(=O)=O)C=C2C(=O)C\1=C1/NC2=CC=C(S(=O)(=O)[O-])C=C2C1=O KHLVKKOJDHCJMG-QDBORUFSSA-L 0.000 description 3
- 235000012738 indigotine Nutrition 0.000 description 3
- 239000004179 indigotine Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 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
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 2
- 240000003259 Brassica oleracea var. botrytis Species 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 235000017537 Vaccinium myrtillus Nutrition 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000005349 anion exchange Methods 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 235000013365 dairy product Nutrition 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012500 ion exchange media Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 150000007965 phenolic acids Chemical class 0.000 description 2
- 235000009048 phenolic acids Nutrition 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000020374 simple syrup Nutrition 0.000 description 2
- 235000011888 snacks Nutrition 0.000 description 2
- 235000014347 soups Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 description 2
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical group C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 239000013598 vector Substances 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RMZNXRYIFGTWPF-UHFFFAOYSA-N 2-nitrosoacetic acid Chemical group OC(=O)CN=O RMZNXRYIFGTWPF-UHFFFAOYSA-N 0.000 description 1
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 1
- 241001499808 Allium atrorubens Species 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 244000178937 Brassica oleracea var. capitata Species 0.000 description 1
- 244000308180 Brassica oleracea var. italica Species 0.000 description 1
- 241001107116 Castanospermum australe Species 0.000 description 1
- 235000005976 Citrus sinensis Nutrition 0.000 description 1
- 240000002319 Citrus sinensis Species 0.000 description 1
- 241000371652 Curvularia clavata Species 0.000 description 1
- 241000192700 Cyanobacteria Species 0.000 description 1
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 244000207620 Euterpe oleracea Species 0.000 description 1
- 235000012601 Euterpe oleracea Nutrition 0.000 description 1
- 244000307700 Fragaria vesca Species 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 1
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241000220225 Malus Species 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 235000016357 Mirtillo rosso Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000006029 Prunus persica var nucipersica Nutrition 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 244000017714 Prunus persica var. nucipersica Species 0.000 description 1
- 235000002357 Ribes grossularia Nutrition 0.000 description 1
- 244000171263 Ribes grossularia Species 0.000 description 1
- 240000001890 Ribes hudsonianum Species 0.000 description 1
- 235000016954 Ribes hudsonianum Nutrition 0.000 description 1
- 235000001466 Ribes nigrum Nutrition 0.000 description 1
- 235000016911 Ribes sativum Nutrition 0.000 description 1
- 235000002355 Ribes spicatum Nutrition 0.000 description 1
- 244000281209 Ribes triste Species 0.000 description 1
- 235000016897 Ribes triste Nutrition 0.000 description 1
- OVVGHDNPYGTYIT-VHBGUFLRSA-N Robinobiose Natural products O(C[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](C)O1 OVVGHDNPYGTYIT-VHBGUFLRSA-N 0.000 description 1
- 240000007651 Rubus glaucus Species 0.000 description 1
- 235000011034 Rubus glaucus Nutrition 0.000 description 1
- 235000009122 Rubus idaeus Nutrition 0.000 description 1
- BUEBVQCTEJTADB-UHFFFAOYSA-N Sambubiose Natural products OC1C(O)C(CO)OC(O)C1OC1C(O)C(O)C(O)CO1 BUEBVQCTEJTADB-UHFFFAOYSA-N 0.000 description 1
- 244000151637 Sambucus canadensis Species 0.000 description 1
- 235000018735 Sambucus canadensis Nutrition 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- HIWPGCMGAMJNRG-ACCAVRKYSA-N Sophorose Natural products O([C@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HIWPGCMGAMJNRG-ACCAVRKYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 235000003095 Vaccinium corymbosum Nutrition 0.000 description 1
- 240000001717 Vaccinium macrocarpon Species 0.000 description 1
- 235000012545 Vaccinium macrocarpon Nutrition 0.000 description 1
- 235000002118 Vaccinium oxycoccus Nutrition 0.000 description 1
- 235000017606 Vaccinium vitis idaea Nutrition 0.000 description 1
- 244000077923 Vaccinium vitis idaea Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 241000219095 Vitis Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 241001593968 Vitis palmata Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 235000003650 acai Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000001453 anthocyanidins Chemical group 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 235000015173 baked goods and baking mixes Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- HIWPGCMGAMJNRG-UHFFFAOYSA-N beta-sophorose Natural products OC1C(O)C(CO)OC(O)C1OC1C(O)C(O)C(O)C(CO)O1 HIWPGCMGAMJNRG-UHFFFAOYSA-N 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 235000021279 black bean Nutrition 0.000 description 1
- 235000007123 blue elder Nutrition 0.000 description 1
- 235000021014 blueberries Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 235000004883 caffeic acid Nutrition 0.000 description 1
- 229940074360 caffeic acid Drugs 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 235000012182 cereal bars Nutrition 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 239000007910 chewable tablet Substances 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 235000012495 crackers Nutrition 0.000 description 1
- 235000004634 cranberry Nutrition 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 235000021185 dessert Nutrition 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000007124 elderberry Nutrition 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000008995 european elder Nutrition 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 1
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 1
- 235000001785 ferulic acid Nutrition 0.000 description 1
- 229940114124 ferulic acid Drugs 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 210000003918 fraction a Anatomy 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 125000003147 glycosyl group Chemical group 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000013178 mathematical model Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 235000013606 potato chips Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000012434 pretzels Nutrition 0.000 description 1
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- OVVGHDNPYGTYIT-BNXXONSGSA-N rutinose Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1 OVVGHDNPYGTYIT-BNXXONSGSA-N 0.000 description 1
- BUEBVQCTEJTADB-IGQSMMPPSA-N sambubiose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)CO1 BUEBVQCTEJTADB-IGQSMMPPSA-N 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- PCMORTLOPMLEFB-ONEGZZNKSA-N sinapic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-ONEGZZNKSA-N 0.000 description 1
- PCMORTLOPMLEFB-UHFFFAOYSA-N sinapinic acid Natural products COC1=CC(C=CC(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-UHFFFAOYSA-N 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- PZDOWFGHCNHPQD-VNNZMYODSA-N sophorose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](C=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PZDOWFGHCNHPQD-VNNZMYODSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 210000003934 vacuole Anatomy 0.000 description 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008256 whipped cream Substances 0.000 description 1
- 239000001060 yellow colorant Substances 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation containing fruit or vegetable juices
- A23L2/04—Extraction of juices
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/58—Colouring agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/70—Clarifying or fining of non-alcoholic beverages; Removing unwanted matter
- A23L2/78—Clarifying or fining of non-alcoholic beverages; Removing unwanted matter by ion-exchange
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
- A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction
- B01D15/361—Ion-exchange
- B01D15/362—Cation-exchange
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/42—Selective adsorption, e.g. chromatography characterised by the development mode, e.g. by displacement or by elution
- B01D15/424—Elution mode
- B01D15/426—Specific type of solvent
-
- 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Cosmetics (AREA)
Abstract
Description
R5は、H、OH、またはOCH3であり、
R6は、HまたはOHであり、
R7は、OHまたはOCH3であり、
R3’は、H、OH、またはOCH3であり、
R4’は、OHまたはOCH3であり、
R5’は、H、OH、またはOCH3である)。
500〜1000ppmの間の濃度においては(0<t<1):
L*=10.49+13.58*t
a*=15.82+−6.02*t
b*=−44.99+−13.19*t
100〜500ppmの間の濃度においては(0<t<1):
L*=24.07+28.36*t
a*=9.80+−39.37*t
b*=−58.18+0.80*t
50〜100ppmの間の濃度においては(0<t<1):
L*=52.43+11.21*t
a*=−29.57+−14.14*t
b*=−57.38+9.07*t
10〜50ppmの間の濃度においては(0<t<1):
L*=63.64+20.61*t
a*=−43.71+6.48*t
b*=−48.31+24.89*t
5〜10ppmの間の濃度においては(0<t<1):
L*=84.25+6.40*t
a*=−37.23+12.83*t
b*=−23.42+9.14*t
1〜5ppmの間の濃度においては(0<t<1):
L*=90.65+7.04*t
a*=−24.40+17.97*t
b*=−14.28+10.71*t
図1に、L*a*b*空間におけるFD&C Blue No.1の線分モデルを示す。
X0=(69.97,−29.69,−43.56)
である。Spirulina Blueを206mg/L含む溶液のL*a*b*色空間におけるX0は:
X0=(80.3,−23.97,−29.39)
である。
X1=(63.64,−43.71,−48.31)
X2=(84.25,−37.23,−23.24)
式5から求められるdminは、404.8mg/LのSpirulina Blue溶液については12.4であり、206mg/LのSpirulina Blue溶液については14.4である。したがって、FD&C Blue No.1を10ppmおよび50ppmを含む水溶液のL*a*b*値により定められる線分に対し測定を行った場合、Spirulina Blue溶液の呈する色は、FD&C Blue No.1の水溶液が呈する色と比較してΔEが12以下にはならない。
強陽イオン交換カートリッジを用いた紫キャベツ抽出物の分画
Phenomenex(登録商標)(Torrance,CA)からのSCX(強陽イオン交換)固相抽出カートリッジを純粋なメタノールを用いて活性化した。このカートリッジを酸性化した水(0.01%v/v)を用いて洗浄した。紫キャベツ抽出物の水溶液をカートリッジに投入し、酸性化した水(0.01%v/v)で洗浄した。カートリッジにpH8のリン酸カリウム緩衝液(0.1M)を通過させた。画分1をpH8のメタノール溶液(25%v/v)で溶出し、回収した。画分2をpH8のメタノール溶液(70%v/v)で溶出し、回収した。
L*a*b*色空間におけるpH7.6の画分2のX0:
X0=(91.62,−4.17,−5.68)
L*a*b*色空間におけるpH8.0の画分2のX0は:
X0=(91.56,−5.80,−5.81)
X1およびX2は、FD&C Blue No.1モデルからの2点である:
X1=(90.65,−24.40,−14.28)
X2=(97.69,−6.43,−3.57)
dminすなわちΔE値の計算値は、pH7.6の画分2が6.7であり、pH8.0の画分2が6.0である。
強陽イオン交換カートリッジおよび異なる高pH値の溶媒を用いた紫キャベツ抽出物の分画
Phenomenex(登録商標)(Torrance,CA)からのSCX(強陽イオン交換)固相抽出カートリッジを使用した。酸性化水(0.01%v/v)(10〜15ml)で希釈した紫キャベツ抽出物をカートリッジに投入し、酸性化水(0.01%v/v)で洗浄した。カートリッジにpH6のリン酸カリウム緩衝液(0.1M)を通過させた。pH6のメタノール溶液(25%v/v)を用いて画分1を溶出し、回収した。カートリッジにpH7のリン酸カリウム緩衝液(0.1M)を通過させた。画分2をpH7のメタノール溶液(25%v/v)を用いて溶出し、回収した。カートリッジにpH8のリン酸カリウム緩衝液(0.1M)を通過させた。画分3をpH8のメタノール溶液(25%v/v)を用いて溶出し、回収した。画分4をpH8のメタノール溶液(70%v/v)を用いて溶出し、回収した。
L*a*b*色空間におけるpH8.0の画分4のX0:
X0=(90.08,−7.87,−7.20)
X1およびX2はFD&C Blue No.1モデルからの2点である:
X1=(90.65,−24.40,−14.28)
X2=(97.69,−6.43,−3.57)
dminすなわちΔE値の計算値は、pH8.0の画分4が6.7である。
セミ分取HPLCを用いた紫キャベツ抽出物ピーク群の分離
図7のクロマトグラムに示す2つの特定のピーク群に付随する画分を、セミ分取HPLCを用いて紫キャベツ抽出物溶液から分離し、回収することができる。紫キャベツ抽出物溶液をC18セミ分取HPLCカートリッジに投入し、2つの画分すなわち520nm画分(λmax=524nm)および530nm画分(λmax=532nm)を酸性アセトニトリルおよび水のグラジエント溶出によって溶出した。ロータリーエバポレータを用いて各画分から残留アセトニトリルを蒸発させた。
L*a*b*色空間におけるpH7.6の530nm画分のX0:
X0=(87.67,−5.44,−9.90)
L*a*b*色空間におけるpH8.0の530nm画分のX0:
X0=(86.39,−11.79,−11.98)
X1およびX2はFD&C Blue No.1モデルからの2点である:
X1=(84.25,−37.23,−23.42)
X2=(90.65,−24.40,−14.28)
dminすなわちΔE値の計算値は、pH7.6の530nm画分が12.1、pH8.0の530nm画分が9.9である。
国際公開第2004/012526号の実施例に開示されている幾つかの異なる濃度の紫キャベツアントシアニン溶液をpH8.0で調製した。分離されたアントシアニン含有着色料を分離および回収するための分画は行われていなかった。結果として得られた溶液の極大吸収は610nmであった。この色は、FD&C Blue No.1との整合性という観点では、許容されるものとは見なされなかった。
Claims (18)
- アントシアニンを含有する野菜または果物の汁もしくは抽出物またはこれらの組合せからアントシアニンの画分を単離する方法において:
a)アントシアニンを含有する野菜または果物の汁もしくは抽出物またはこれらの組合せをイオン交換カラムに投入するステップと、
b)前記イオン交換カラム上で、前記アントシアニン分子の電荷および極性の差に基づき、選択されたpHを有する溶媒を用いて、アントシアニンを選択的に分離するステップと、
c)分離されたアントシアニンを含む1つの画分または画分の組合せを選択するステップであって、前記1つの画分または前記画分の組合せ中に含まれる前記分離されたアントシアニンの水溶液のpH8.0における吸収極大が615nm〜635nmとなるように、選択するステップと
を含むことを特徴とする、方法。 - 前記1つの画分または前記画分の組合せ中に含まれる前記分離されたアントシアニンを少なくとも1つの濃度で含む水溶液がpH8.0において呈する色特性が、FD&C Blue No.1を5ppmおよび10ppmで含む水溶液のL*a*b*値により定められる線分により定められる色特性と比較して、ΔE値が12以下であることを特徴とする、請求項1に記載の方法。
- 前記アントシアニンを含有する野菜または果物の汁または抽出物の供給源が、紫キャベツ、紫イモ、紫ジャガイモ、黒ニンジン、紫ニンジンおよびこれらの組合せからなる群から選択されることを特徴とする、請求項1に記載の方法。
- 前記アントシアニンを含有する野菜または果物の汁または抽出物の前記供給源が、紫キャベツであることを特徴とする、請求項3に記載の方法。
- 前記選択されたアントシアニン含有画分が、前記アントシアニンを含有する野菜または果物の汁もしくは抽出物またはこれらの組合せから、約4〜約9の選択されたpHを有する溶媒を用いて分離されることを特徴とする、請求項1に記載の方法。
- 前記選択されたアントシアニン含有画分が、前記アントシアニンを含有する野菜または果物の汁もしくは抽出物またはこれらの組合せから、約4〜約9の選択されたpHを有する溶媒を用いて分離されることを特徴とする、請求項5に記載の方法。
- 第1アントシアニン含有画分が、pH8のメタノール溶液(25%v/v)で溶出し、前記1つの画分である後続アントシアニン含有画分または前記画分の組合せである複数の後続画分が、pH8のメタノール溶液(70%v/v)で溶出することを特徴とする、請求項6に記載の方法。
- 前記1つの画分または前記画分の組合せを精製するステップをさらに含むことを特徴とする、請求項7に記載の方法。
- 前記1つの画分または前記画分の組合せの前記分離されたアントシアニンを少なくとも1つの濃度で含む水溶液がpH8.0において呈する色特性が、FD&C Blue No.1を5ppmおよび10ppmで含む水溶液のL*a*b*値により定められる線分により定められる色特性と比較して、ΔE値が12以下であることを特徴とする、請求項8に記載の方法。
- 前記イオン交換カラムが陽イオン交換カラムであることを特徴とする、請求項1に記載の方法。
- 前記アントシアニン分子の電荷および極性の差に基づき前記イオン交換カラム上でアントシアニンを選択的に分離する前記ステップが、(i)最初に、第1画分を得るために選択されたpHを有する前記溶媒を使用するステップと、(ii)前記1つの画分である後続画分を得るため、または前記画分の組合せである複数の後続画分の組合せを得るために、第2の選択されたpHを有する第2溶媒を使用するステップであって、前記第2溶媒の前記pH値は前記第1溶媒の前記pH値とは異なる、ステップと、を含み、前記1つの画分または画分の組合せ中に含まれる前記分離されたアントシアニンを少なくとも1つの濃度で含む水溶液がpH8.0において呈する色特性は、FD&C Blue No.1を5ppmおよび10ppmで含む水溶液のL*a*b*値により定められる線分により定められる色特性と比較して、ΔE値が12以下であることを特徴とする、請求項1に記載の方法。
- d)分離されたアントシアニンを含む前記選択された1つの画分または画分の組合せをイオン交換カラムに投入するステップと、
e)ステップd)において前記イオン交換カラムに投入された前記アントシアニンを、前記アントシアニン分子の電荷および極性の差に基づき、選択されたpHを有する溶媒を用いて、選択的に分離するステップと、
f)ステップe)において分離された、分離されたアントシアニンを含む1つの画分または画分の組合せを選択するステップであって、ステップf)において選択された前記分離されたアントシアニンの水溶液のpH8.0における吸収極大が620nm〜635nmとなるように、選択する、ステップをさらに含むことを特徴とする、請求項1に記載の方法。 - ステップf)において選択された前記分離されたアントシアニンを少なくとも1つの濃度で含む水溶液がpH8.0において呈する色特性が、FD&C Blue No.1を5ppmおよび10ppmで含む水溶液のL*a*b*値により定められる線分により定められる色特性と比較して、ΔE値が12以下であることを特徴とする、請求項12に記載の方法。
- アントシアニンを前記アントシアニン分子の電荷および極性の差に基づき前記イオン交換カラム上で選択的に分離する前記ステップが、(i)最初に、第1画分を得るために、第1溶出溶媒である選択されたpHを有する前記溶媒を使用するステップと、(ii)前記1つの画分または画分の組合せを得るために、選択されたpHを有する1つまたは複数の後続溶出溶媒を使用するステップとを含み、各溶出溶媒は異なっており、その差は、pH、溶媒の構成またはこれらの組合せの群から独立に選択することができることを特徴とする、請求項1に記載の方法。
- 前記1つの画分または前記画分の組合せに含まれる前記分離されたアントシアニンを少なくとも1つの濃度で含む水溶液のpH8.0における色特性が、FD&C Blue No.1を5ppmおよび10ppmで含む水溶液のL*a*b*値により定められる線分で定められる色特性と比較して、ΔE値が12以下であることを特徴とする、請求項14に記載の方法。
- 前記第1溶出溶媒が、第1濃度の有機溶媒と水との混合物であり、後続溶出溶媒は、第2濃度の有機溶媒と水との第2混合物が使用され、前記第1濃度は前記第2濃度とは異なることを特徴とする、請求項15に記載の方法。
- 前記第1溶出溶媒の選択されたpHが、前記後続溶出溶媒の選択されたpHとは異なることを特徴とする、請求項14に記載の方法。
- 前記第1溶出溶媒の前記選択されたpHが、前記後続溶出溶媒の前記選択されたpHよりも低いことを特徴とする、請求項17に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201361790842P | 2013-03-15 | 2013-03-15 | |
US61/790,842 | 2013-03-15 | ||
PCT/US2014/027319 WO2014152417A2 (en) | 2013-03-15 | 2014-03-14 | Method of isolating blue anthocyanin fractions |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2016519177A true JP2016519177A (ja) | 2016-06-30 |
JP5981675B2 JP5981675B2 (ja) | 2016-08-31 |
Family
ID=50733323
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016502403A Active JP5981675B2 (ja) | 2013-03-15 | 2014-03-14 | 青色アントシアニン画分の単離方法 |
Country Status (12)
Country | Link |
---|---|
US (2) | US9598581B2 (ja) |
EP (1) | EP2986675B1 (ja) |
JP (1) | JP5981675B2 (ja) |
CN (1) | CN105229084B (ja) |
AU (1) | AU2014239875B2 (ja) |
BR (1) | BR112015021402B1 (ja) |
CA (1) | CA2904650C (ja) |
GB (1) | GB2527453B (ja) |
HK (1) | HK1215040A1 (ja) |
MX (1) | MX362026B (ja) |
RU (1) | RU2629257C2 (ja) |
WO (1) | WO2014152417A2 (ja) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105229084B (zh) | 2013-03-15 | 2017-09-01 | 马斯公司 | 分离蓝色的花青素苷级分的方法 |
CN104961783B (zh) * | 2015-04-17 | 2018-07-10 | 浙江惠松制药有限公司 | 一种有效提取花青素和花色苷的方法 |
AU2016288697B2 (en) * | 2015-06-30 | 2020-11-26 | Mars, Incorporated | Acylated anthocyanin based colourant composition and methods of use thereof |
CA3048457C (en) | 2016-12-29 | 2023-03-07 | Mars, Incorporated | Edible ink formulations including calcium carbonate |
CN112351687A (zh) | 2018-06-28 | 2021-02-09 | 马斯公司 | 含碳酸钙的改进可食用油墨配制剂 |
WO2020047276A1 (en) | 2018-08-31 | 2020-03-05 | Mars, Incorporated | Anthocyanin-based colorant compositions and methods of use thereof |
WO2021067627A1 (en) | 2019-10-01 | 2021-04-08 | Mars, Incorporated | Enzymatic treatment of anthocyanins |
EP3939437A1 (en) * | 2020-07-17 | 2022-01-19 | GNT Group B.V. | A composition comprising spirulina extract |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003064538A1 (fr) * | 2002-02-01 | 2003-08-07 | San-Ei Gen F.F.I., Inc. | Couleur de mais rouge purifiee et procede de preparation de celle-ci |
WO2005007088A2 (en) * | 2003-07-03 | 2005-01-27 | Unibar Corporation | Stabilized anthocyanin extract from garcinia indica |
WO2008111589A1 (ja) * | 2007-03-12 | 2008-09-18 | National University Corporation Kagawa University | 精製アントシアニンの製造方法 |
WO2009100165A2 (en) * | 2008-02-06 | 2009-08-13 | The Ohio State University Research Foundation | High-purity fractionation of anthocyanins from fruits and vegetables |
WO2010114568A1 (en) * | 2009-04-03 | 2010-10-07 | Dianaplantsciences, Inc. | Methods for creating color variation in anthocyanins produced by cell culture |
WO2010131049A2 (en) * | 2009-05-15 | 2010-11-18 | University Of Leeds | Natural hair dyes |
WO2012172429A2 (en) * | 2011-06-13 | 2012-12-20 | E.P.C. (Beijing) Plant Pharmaceutical Technology Co., Ltd. | Anthocyanin based colorant compositions |
Family Cites Families (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3361631A (en) | 1963-09-30 | 1968-01-02 | Sandoz Ag | Method of sugar coating pharmaceutical tablets |
DE1482489A1 (de) | 1965-01-13 | 1970-03-12 | Boehringer Mannheim Gmbh | Vollautomatisches Dragierverfahren |
NL6601426A (ja) | 1965-02-12 | 1966-08-15 | ||
US4172902A (en) | 1978-05-26 | 1979-10-30 | The United States Of America As Represented By The Secretary Of Agriculture | Stable foods and beverages containing the anthocyanin, peonidin 3-(dicaffeylsophoroside)-5-glucoside |
JPS6025181B2 (ja) | 1982-10-04 | 1985-06-17 | フロイント産業株式会社 | パンコ−チング装置 |
US4681766A (en) | 1986-01-07 | 1987-07-21 | Warner-Lambert Company | Coatings for chewing gums containing gum arabic and a soluble calcium salt |
JPH083047B2 (ja) | 1986-06-21 | 1996-01-17 | サントリー株式会社 | 天然青色系色素組成物及びそれを用いた着色剤 |
CA2170497C (en) | 1993-09-15 | 1999-07-13 | Michael A. Reed | Hard coated chewing gum with improved shelf life, with mixed polyol coatings |
JPH07188572A (ja) | 1993-12-27 | 1995-07-25 | Kyodo Nyugyo Kk | マロ−由来の天然色素 |
WO1997026802A1 (en) | 1996-01-22 | 1997-07-31 | Chr. Hansen A/S | Water dispersible compositions containing natural hydrophobic pigment, method of preparing same and their use |
US6541048B2 (en) | 1999-09-02 | 2003-04-01 | Wm. Wrigley Jr. Company | Coated chewing gum products containing an acid blocker and process of preparing |
WO2001067894A1 (en) | 2000-03-16 | 2001-09-20 | San-Ei Gen F.F.I., Inc. | Fading inhibitors |
WO2001090254A1 (fr) | 2000-05-26 | 2001-11-29 | San-Ei Gen F.F.I., Inc. | Colorant desodorise de brassicaceae |
US6572900B1 (en) | 2000-06-09 | 2003-06-03 | Wm. Wrigley, Jr. Company | Method for making coated chewing gum products including a high-intensity sweetener |
US6881430B2 (en) | 2001-07-26 | 2005-04-19 | Chr. Hansen A/S | Food coloring substances and method for their preparation |
ATE323744T1 (de) | 2001-07-26 | 2006-05-15 | Hansens Lab | Lebensmittelfärbende substanzen auf anthocyaninbasis |
JP4590034B2 (ja) | 2002-01-31 | 2010-12-01 | 三菱商事フードテック株式会社 | 硬質糖衣製剤、糖衣液及び硬質糖衣製剤の製造方法 |
DE10227151B4 (de) | 2002-06-18 | 2007-03-15 | Wild Flavors Berlin Gmbh & Co. Kg | Extrakt aus Nebenprodukten der Nussverarbeitung, Verfahren zu dessen Herstellung und dessen Verwendung |
FR2842993B1 (fr) * | 2002-07-31 | 2006-02-17 | Mars Inc | Nouvelle composition de confiserie |
US7378118B2 (en) | 2002-08-14 | 2008-05-27 | Wm. Wrigley Jr. Company | Methods for manufacturing coated confectionary products |
US20040105919A1 (en) | 2002-12-02 | 2004-06-03 | Mars, Incorporated | Processing system having a process injection apparatus |
US7279189B2 (en) | 2004-07-02 | 2007-10-09 | Colormaker, Inc. | Stabilized natural blue and green colorants |
EP2484773A3 (en) | 2004-07-10 | 2015-01-21 | The Research Foundation of State University of New York | Process for producing anthocyanins |
CN102864195B (zh) | 2004-10-29 | 2014-11-12 | 三得利控股株式会社 | 利用编码花色苷3′位芳香族酰基转移酶的基因的花色苷色素稳定化和蓝化方法 |
JP2008524266A (ja) | 2004-12-22 | 2008-07-10 | コラローム インコーポレイティド | 天然の水−不溶性カプセル化組成物及びその製造法 |
RU2302423C2 (ru) * | 2005-06-10 | 2007-07-10 | Закрытое акционерное общество "Научно-производственное объединение "ТЕХКОН" | Способ выделения биологически активных антоцианов |
FR2914311B1 (fr) | 2007-03-28 | 2011-02-11 | Diana Naturals | Modification de la nuance colorante d'anthocyanes pour l'obtention de substances colorantes |
EP2070422A1 (en) | 2007-12-05 | 2009-06-17 | Südzucker Aktiengesellschaft Mannheim/Ochsenfurt | Confectionery products promoting dental health |
US8575334B2 (en) | 2008-02-06 | 2013-11-05 | The Ohio State University Research Foundation | High-purity fractionation of anthocyanins from fruits and vegetables |
US8557319B2 (en) | 2008-03-28 | 2013-10-15 | Wild Flavors, Inc. | Stable natural color process, products and use thereof |
FR2930557B1 (fr) | 2008-04-29 | 2013-08-30 | Lvmh Rech | Matieres colorantes d'origine vegetale et leur utilisation pour colorer des compositions, en particulier des compositions cosmetiques |
US20090298952A1 (en) | 2008-05-07 | 2009-12-03 | Brimmer Karen S | Platable soluble dyes |
BRPI0922484A2 (pt) | 2008-12-18 | 2015-08-11 | Dianaplantsciences Inc | Cultura de célula de planta para produção de produtos naturais com contaminação de glucosinolato reduzida |
US8765180B2 (en) | 2009-01-07 | 2014-07-01 | Chr. Hansen A/S | Composition comprising calcium carbonate as a white pigment |
CA2781256C (en) | 2009-11-25 | 2017-11-07 | Sensient Colors Inc. | Natural blue-shade colorants and methods of making and using same |
JP2012067241A (ja) * | 2010-09-27 | 2012-04-05 | Riken Vitamin Co Ltd | クチナシ青色素の製造方法 |
EA023010B1 (ru) | 2010-11-05 | 2016-04-29 | Кр. Хансен Нэйчурал Колорс А/С | Многофазные эмульсии для красителей |
EP2545787B1 (de) | 2011-07-11 | 2016-04-13 | RUDOLF WILD GmbH & CO. KG | Anthocyanhaltige Zusammensetzung |
MX2014000460A (es) | 2011-07-15 | 2014-02-20 | Nestec Sa | Encapsulado azul de grado alimetario y proceso para su produccion. |
WO2013106179A1 (en) | 2011-12-19 | 2013-07-18 | Sensient Colors Llc | Color compositions and methods of making color compositions comprising starch as a matrix |
US20130184359A1 (en) | 2012-01-13 | 2013-07-18 | Karim Nafisi-Movaghar | Processes for Extracting Colors from Hibiscus Plants |
WO2014023712A1 (en) | 2012-08-09 | 2014-02-13 | Nestec S.A. | Anthocyanin colouring composition |
MX359096B (es) | 2013-03-15 | 2018-09-14 | Mars Inc | Estabilizacion de colorantes que contienen antocianina natural de color azul y productos elaborados. |
RU2641830C2 (ru) | 2013-03-15 | 2018-01-22 | Марс, Инкорпорейтед | Натуральные синие антоцианин-содержащие красители |
CN105229084B (zh) | 2013-03-15 | 2017-09-01 | 马斯公司 | 分离蓝色的花青素苷级分的方法 |
-
2014
- 2014-03-14 CN CN201480013986.4A patent/CN105229084B/zh active Active
- 2014-03-14 US US14/773,103 patent/US9598581B2/en active Active
- 2014-03-14 CA CA2904650A patent/CA2904650C/en active Active
- 2014-03-14 GB GB1517443.6A patent/GB2527453B/en not_active Expired - Fee Related
- 2014-03-14 JP JP2016502403A patent/JP5981675B2/ja active Active
- 2014-03-14 AU AU2014239875A patent/AU2014239875B2/en active Active
- 2014-03-14 RU RU2015144064A patent/RU2629257C2/ru active
- 2014-03-14 BR BR112015021402-9A patent/BR112015021402B1/pt active IP Right Grant
- 2014-03-14 WO PCT/US2014/027319 patent/WO2014152417A2/en active Application Filing
- 2014-03-14 EP EP14724849.6A patent/EP2986675B1/en active Active
- 2014-03-14 MX MX2015011349A patent/MX362026B/es active IP Right Grant
-
2016
- 2016-03-14 HK HK16102887.4A patent/HK1215040A1/zh unknown
-
2017
- 2017-02-07 US US15/426,559 patent/US10119029B2/en active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003064538A1 (fr) * | 2002-02-01 | 2003-08-07 | San-Ei Gen F.F.I., Inc. | Couleur de mais rouge purifiee et procede de preparation de celle-ci |
WO2005007088A2 (en) * | 2003-07-03 | 2005-01-27 | Unibar Corporation | Stabilized anthocyanin extract from garcinia indica |
WO2008111589A1 (ja) * | 2007-03-12 | 2008-09-18 | National University Corporation Kagawa University | 精製アントシアニンの製造方法 |
WO2009100165A2 (en) * | 2008-02-06 | 2009-08-13 | The Ohio State University Research Foundation | High-purity fractionation of anthocyanins from fruits and vegetables |
WO2010114568A1 (en) * | 2009-04-03 | 2010-10-07 | Dianaplantsciences, Inc. | Methods for creating color variation in anthocyanins produced by cell culture |
WO2010131049A2 (en) * | 2009-05-15 | 2010-11-18 | University Of Leeds | Natural hair dyes |
WO2012172429A2 (en) * | 2011-06-13 | 2012-12-20 | E.P.C. (Beijing) Plant Pharmaceutical Technology Co., Ltd. | Anthocyanin based colorant compositions |
Also Published As
Publication number | Publication date |
---|---|
US9598581B2 (en) | 2017-03-21 |
HK1215040A1 (zh) | 2016-08-12 |
US20160017150A1 (en) | 2016-01-21 |
JP5981675B2 (ja) | 2016-08-31 |
BR112015021402A2 (ja) | 2017-08-22 |
GB2527453B (en) | 2017-03-15 |
CA2904650A1 (en) | 2014-09-25 |
US10119029B2 (en) | 2018-11-06 |
RU2629257C2 (ru) | 2017-08-28 |
CN105229084A (zh) | 2016-01-06 |
US20170204269A1 (en) | 2017-07-20 |
CA2904650C (en) | 2016-07-12 |
EP2986675B1 (en) | 2016-10-05 |
BR112015021402A8 (pt) | 2021-09-08 |
WO2014152417A3 (en) | 2014-11-20 |
EP2986675A2 (en) | 2016-02-24 |
AU2014239875B2 (en) | 2016-02-04 |
BR112015021402B1 (pt) | 2021-11-03 |
AU2014239875A1 (en) | 2015-11-05 |
GB2527453A (en) | 2015-12-23 |
MX362026B (es) | 2019-01-04 |
MX2015011349A (es) | 2016-06-06 |
GB201517443D0 (en) | 2015-11-18 |
CN105229084B (zh) | 2017-09-01 |
WO2014152417A2 (en) | 2014-09-25 |
RU2015144064A (ru) | 2017-04-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5981675B2 (ja) | 青色アントシアニン画分の単離方法 | |
JP5981676B2 (ja) | 天然の青色アントシアニンを含有する着色料 | |
Pazmiño-Durán et al. | Anthocyanins from banana bracts (Musa X paradisiaca) as potential food colorants | |
AU2016288697B2 (en) | Acylated anthocyanin based colourant composition and methods of use thereof | |
JP6334671B2 (ja) | 天然青色アントシアニン含有着色料およびそれにより製造された製品の安定化 | |
WO2020047276A1 (en) | Anthocyanin-based colorant compositions and methods of use thereof | |
Giusti Hundskopf | Structure and conformation of red radish (Raphanus sativus L.) anthocyanins and their effect on color and pigment stability | |
Oliveira et al. | Pigments in Fruit and Vegetables |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160530 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20160628 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160728 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5981675 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |