TWI466709B - From the original berry Wolfberry a liquid - liquid freezing method for separation of high purity theaflavins palmitate Maize - Google Patents
From the original berry Wolfberry a liquid - liquid freezing method for separation of high purity theaflavins palmitate Maize Download PDFInfo
- Publication number
- TWI466709B TWI466709B TW100125694A TW100125694A TWI466709B TW I466709 B TWI466709 B TW I466709B TW 100125694 A TW100125694 A TW 100125694A TW 100125694 A TW100125694 A TW 100125694A TW I466709 B TWI466709 B TW I466709B
- Authority
- TW
- Taiwan
- Prior art keywords
- liquid
- zeaxanthin
- tetrahydrofuran
- palmitate
- solvent
- Prior art date
Links
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 title claims description 22
- 230000008014 freezing Effects 0.000 title claims description 19
- 238000007710 freezing Methods 0.000 title claims description 19
- 239000007788 liquid Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 11
- 235000002017 Zea mays subsp mays Nutrition 0.000 title description 3
- 238000000926 separation method Methods 0.000 title description 2
- 244000241838 Lycium barbarum Species 0.000 title 1
- 235000015459 Lycium barbarum Nutrition 0.000 title 1
- 235000015468 Lycium chinense Nutrition 0.000 title 1
- 240000008042 Zea mays Species 0.000 title 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 title 1
- 235000021028 berry Nutrition 0.000 title 1
- 235000009973 maize Nutrition 0.000 title 1
- 235000014620 theaflavin Nutrition 0.000 title 1
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 claims description 49
- JKQXZKUSFCKOGQ-LQFQNGICSA-N Z-zeaxanthin Natural products C([C@H](O)CC=1C)C(C)(C)C=1C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-LQFQNGICSA-N 0.000 claims description 46
- QOPRSMDTRDMBNK-RNUUUQFGSA-N Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCC(O)C1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C QOPRSMDTRDMBNK-RNUUUQFGSA-N 0.000 claims description 46
- JKQXZKUSFCKOGQ-LOFNIBRQSA-N all-trans-Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C JKQXZKUSFCKOGQ-LOFNIBRQSA-N 0.000 claims description 46
- 235000010930 zeaxanthin Nutrition 0.000 claims description 46
- 229940043269 zeaxanthin Drugs 0.000 claims description 46
- 239000001775 zeaxanthin Substances 0.000 claims description 45
- JKQXZKUSFCKOGQ-JLGXGRJMSA-N (3R,3'R)-beta,beta-carotene-3,3'-diol Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-JLGXGRJMSA-N 0.000 claims description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 29
- 239000000284 extract Substances 0.000 claims description 16
- MJVXHGRPDSIPMQ-UHFFFAOYSA-N hydrazine;oxolane Chemical compound NN.C1CCOC1 MJVXHGRPDSIPMQ-UHFFFAOYSA-N 0.000 claims description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 238000000746 purification Methods 0.000 claims description 9
- 239000012296 anti-solvent Substances 0.000 claims description 8
- 239000008187 granular material Substances 0.000 claims description 8
- -1 zeaxanthin ester Chemical class 0.000 claims description 8
- 238000011084 recovery Methods 0.000 claims description 7
- 238000001953 recrystallisation Methods 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 6
- 238000004090 dissolution Methods 0.000 claims description 5
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000013019 agitation Methods 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 239000002775 capsule Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 241000209149 Zea Species 0.000 description 4
- 235000021466 carotenoid Nutrition 0.000 description 4
- 150000001747 carotenoids Chemical class 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000000287 crude extract Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000001656 lutein Substances 0.000 description 3
- 235000012680 lutein Nutrition 0.000 description 3
- KBPHJBAIARWVSC-RGZFRNHPSA-N lutein Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C KBPHJBAIARWVSC-RGZFRNHPSA-N 0.000 description 3
- 229960005375 lutein Drugs 0.000 description 3
- ORAKUVXRZWMARG-WZLJTJAWSA-N lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C ORAKUVXRZWMARG-WZLJTJAWSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 206010025421 Macule Diseases 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 206010064930 age-related macular degeneration Diseases 0.000 description 2
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 235000013734 beta-carotene Nutrition 0.000 description 2
- 239000011648 beta-carotene Substances 0.000 description 2
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 2
- 229960002747 betacarotene Drugs 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000004438 eyesight Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 208000002780 macular degeneration Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 238000002137 ultrasound extraction Methods 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 241000195649 Chlorella <Chlorellales> Species 0.000 description 1
- 241000195651 Chlorella sp. Species 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000723382 Corylus Species 0.000 description 1
- 235000007466 Corylus avellana Nutrition 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- 230000002292 Radical scavenging effect Effects 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- MGJZITXUQXWAKY-UHFFFAOYSA-N diphenyl-(2,4,6-trinitrophenyl)iminoazanium Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1N=[N+](C=1C=CC=CC=1)C1=CC=CC=C1 MGJZITXUQXWAKY-UHFFFAOYSA-N 0.000 description 1
- 235000011869 dried fruits Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 241001233061 earthworms Species 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- DVBDWJXHMORLMQ-UHFFFAOYSA-N hexadecanoic acid;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCCCCC(O)=O DVBDWJXHMORLMQ-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002398 materia medica Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 230000009978 visual deterioration Effects 0.000 description 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
本發明係關於從原枸杞果粒中提取玉米黃素棕櫚酸酯之方法。
老年性黃斑部病變(AMD)是導致65歲以上老年人視力退化的主要原因。生物物理學家伯恩(Bone)博士表示，藍色光線對位於視網膜中心的黃斑部有害，而黃斑部中含有高量的黃體素和玉米黃素，這兩種色素有過濾出藍色光線的功效。
從古代文獻(本草剛目)至現今許多研究報告均指出食用枸杞可達到「明目」之效。分析枸杞的營養成份，它包含有生物活性物質(枸杞紅素、枸杞多糖、玉米黃質、葉黃素、β胡蘿蔔素、類胡蘿蔔素、核黃素、甜菜鹼、牛磺酸)、不飽和脂肪酸(油酸、亞麻油酸、次亞麻油酸、花生四烯酸)、微量元素(氟、錳、鉻、鎂、鋅、銅、硒、鉬、鎳、鈣、磷、鋰、鈉、鍺、鈷、鐵、矽、釩、鉀等)。其中類蘿蔔素、玉米黃素、β-胡蘿蔔素為所有蔬果中含量最高者，而玉米黃素、葉黃素已被證實有助於增強視網膜黃斑組織。經實驗及研究證明服用枸杞中所含有的玉米黃素棕櫚酸酯化物，可使血液中的玉米黃素含量增加，其作用機轉在於玉米黃素棕櫚酸酯化物在人體內會被皂化成玉米黃素。基於此，除了玉米黃素可做為明目藥食材之外，玉米黃素棕欄酸酯也可以做為玉米黃素的替代來源。
關於從食物或植物中提取玉米黃素的文獻，如文獻(1)中華民國發明專利公開第201114466號「超臨界流體抗溶結晶微藻類胡蘿蔔素及純化玉米黃素程序」、文獻(2)中華民國國科會計劃編號NSC 98-2815-C-005-039-E「高含量擬球藻玉米黃素抗氧化保健原料製備方法」、文獻(3)中華民國發明專利申請案「具有生物活性的玉米黃素棕櫚酸酯的結晶純化方法」文獻(4)中華民國發明專利申請案「以可再生吸附劑產製高回收率之藻類玉米黃素保眼原料」。其中：
文獻(1)主要技術係利用抗溶結晶技術自索氏二氯甲烷萃取物中獲得含有高濃度之類葫蘿蔔素沉澱物，並分離純化出高純度玉米黃素。
文獻(2)揭露以各種分離程序，對擬球藻萃取物進行純化實驗，所得之產物藉由1,1-二苯基-2-苦味肼基團自由基(1,1-diphenyl-2-picrylhydrazyl,DPPH)測試其清除DPPH自由基能力，並求出相對應半效濃度(EC50
)值，並以維生素E(α-tocopherol)當作正面控制組。結果顯示，控制組的EC50
為0.06 mg/mL，索氏二氯甲烷粗萃物經管柱純化40%玉米黃素(zea)與29%zea樣品，其EC50
值分別為0.389 mg/mL、0.563 mg/mL；索氏二氯甲烷粗萃物(含玉米黃素20.1mg/gext
)EC50
為1.103mg/mL，超臨界流體粗萃物(含玉米黃素13.17mg/gext
)EC50
為1.612 mg/mL。樣品清除DPPH自由基能力，隨著玉米黃素濃度之增加而增加。
文獻(3)是利用超音波攪拌溶劑，從除醣的枸杞乾燥果粒中提取玉米黃素棕櫚酸酯，再以管柱層析純化程序產製富含玉米黃素棕櫚酸酯分劃層；最後再以液-液抗溶結晶純化程序，得到純品98.3%的玉米黃素棕櫚酸酯。
文獻(4)是以丙酮(或95%藥用乙醇)為溶劑進行超音波攪拌萃取，再經減壓濃縮後所得之超音波微藻萃取物；最後，再進行微藻超音波萃取，然後經過以PS100樹脂為吸附劑之管柱純化後，最後得到80%以上的回收率且純度在300 mg/g至400 mg/g之玉米黃素固態產物。
本發明之目的係在提出一種從原枸杞果粒提析出高純度玉米黃素棕櫚酸酯之方法，本發明採用了不同於上述各文獻的技術方案，從一單位重量的原枸杞果粒中回收酯化物，且回收值高達76%，並可產製純度至少為81.1%的王米黃素棕櫚酸酯。
本發明從原枸杞果粒以液-液冷凍析出高純度玉米黃素棕櫚酸酯之方法，包含以下步驟：
(a)將原枸杞果粒研磨成枸杞粉粒；
(b)將該枸杞粉粒浸於四氫呋喃(THF)溶劑中得一枸杞四氫呋喃混合物，並進行超音波攪拌；
(c)將經超音波攪拌之枸杞四氫呋喃混合物進行去除溶劑之步驟，獲得固態之枸杞四氫呋喃萃出物；
(d)將上述枸杞四氫呋喃萃出物於四氫呋喃溶劑中進行溶解，獲得枸杞四氫呋喃提出液；
(e)將抗溶劑乙醇加入該枸杞四氫呋喃提出液中，於一冷凍溫度下進行低溫冷凍抗溶再結晶，獲得玉米黃素酯化物；
(f)將該玉米黃素酯化物於一冷凍溫度下進行分離純化，沈澱析出玉米黃素棕櫚酸酯。
本發明之實驗材料為原枸杞果粒，實驗溶劑為四氫呋喃(tetrahydrofuran,THF)，抗溶劑為乙醇。
本發明是以萃取原枸杞果粒步驟、抗溶再結晶純化步驟製得純度至少為76%，回收率至少為81.1%的玉米黃素棕櫚酸酯粉粒。
取3克經冷凍的原枸杞果粒，磨碎成3000至4000微米之枸杞粉粒，將該枸杞粉粒浸入240毫升的四氫呋喃((Tetrahydrofuran，THF)溶劑中，製得一枸杞四氫呋喃混合物。
將該枸杞四氫呋喃混合物進行超音波攪拌，條件為溫度為303K，頻率40KHz，功率300W，萃取時間30分鐘。
再以過濾步驟去除溶劑，獲得固態之枸杞四氫呋喃萃出物0.102克。將該萃出物保存於-10℃。以便後續進行HPLC，分析萃出物之成份及含量。
取113毫克之枸杞四氫呋喃萃出物，溶解於5.0mL的四氫呋喃溶劑中，製得枸杞四氫呋喃提出液；再以50mL 99%乙醇為抗溶劑，加入上述枸杞四氫呋喃提出液中，於一冷凍溫度下進行低溫冷凍抗溶再結晶；所述之冷凍溫度為-5℃～-10℃，最佳為-10℃；冷凍時間為至少24小時。經該低溫冷凍抗溶再結晶可獲得玉米黃素酯化物；之後，將該玉米黃素酯化物於一冷凍溫度下進行離心純化，所述之冷凍溫度為-5℃～-10℃，最佳為-5℃；離心純化係為一離心機中進行，離心轉速為8000rpm，時間為5分鐘，沈澱析出玉米黃素棕櫚酸酯。將該玉米黃素棕櫚酸酯進行乾燥，即得玉米黃素棕櫚酸酯固態粉末。
以HPLC(High Pressure Liquid Chromatography,高壓液相層析儀)對上述枸杞四氫呋喃萃出物以及玉米黃素棕櫚酸酯固態粉末進行定性和定量分析。
本發明之HPLC係採用Hitachi 2130泵，配有2400 UV系統，分析管柱為YMC C-30(5μm,250mm×4.6mm i.d.)每次樣品注入體積為20μL，波長為450nm，採用梯度沖提，沖提劑為甲醇及甲基第三丁基醚之混合液；流速控制在1 mL/min。梯度沖提條件為0~5min：70% A及30% B；5~20min：40% A，60% B；20~26min：20% A，80% B；26~30min：20% A，80% B。(A：甲醇；B：甲基第三丁基醚)。
以上述HPLC之條件對所獲得之定性及定量分析結果，從枸杞四氫呋喃萃出物經液-液抗溶再結晶步驟，可得之玉米黃素酯化物回收率高達76%；再經離心析出沈澱而得之玉米黃素棕櫚酸酯之純度更高達81.1%。
本發明方法開發了高收回率及高純度玉米黃素棕櫚酯，做為玉米黃素的替代來源。所獲得之玉米黃素棕櫚酸酯固態粉末可被添加於保健產品中，使該保健產品產生保護眼睛黃斑部的效果。
Claims (4)
- 一種從原枸杞果粒以液-液冷凍析出高純度玉米黃素棕櫚酸酯之方法，包含以下步驟：(a)將原枸杞果粒研磨成枸杞粉粒；(b)將該枸杞粉粒浸於四氫呋喃(THF)溶劑中得一枸杞四氫呋喃混合物，並進行超音波攪拌；(c)將經超音波攪拌之枸杞四氫呋喃混合物進行去除溶劑之步驟，獲得固態之枸杞四氫呋喃萃出物；(d)將上述枸杞四氫呋喃萃出物於四氫呋喃溶劑中進行溶解，獲得枸杞四氫呋喃提出液；(e)將抗溶劑乙醇加入該枸杞四氫呋喃提出液中，於一冷凍溫度下進行低溫冷凍液-液抗溶再結晶，獲得玉米黃素酯化物；溶劑與抗溶劑之容積比為1：1至1：10；冷凍溫度為-5℃至-10℃，冷凍時間至少24小時；(f)將該玉米黃素酯化物於一冷凍溫度下進行離心純化，沈澱析出玉米黃素棕櫚酸酯；冷凍溫度為-5℃至-10℃；所獲得之玉米黃素酯化物之回收率至少76%；所獲得之玉米黃素棕櫚酸酯之純度至少為81.1%。
- 如申請專利範圍第1項所述之方法，其中，溶劑與抗溶劑之最佳容積比為1：10。
- 如申請專利範圍第1項所述之方法，其中，步驟(e)之最佳冷凍溫度為-10℃。
- 如申請專利範圍第1項所述之方法，其中，步驟(f)之最佳冷凍溫度為-5℃。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW100125694A TWI466709B (zh) | 2011-07-20 | 2011-07-20 | From the original berry Wolfberry a liquid - liquid freezing method for separation of high purity theaflavins palmitate Maize |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW100125694A TWI466709B (zh) | 2011-07-20 | 2011-07-20 | From the original berry Wolfberry a liquid - liquid freezing method for separation of high purity theaflavins palmitate Maize |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201304846A TW201304846A (zh) | 2013-02-01 |
| TWI466709B true TWI466709B (zh) | 2015-01-01 |
Family
ID=48168911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW100125694A TWI466709B (zh) | 2011-07-20 | 2011-07-20 | From the original berry Wolfberry a liquid - liquid freezing method for separation of high purity theaflavins palmitate Maize |
Country Status (1)
| Country | Link |
|---|---|
| TW (1) | TWI466709B (zh) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999020587A1 (en) * | 1997-10-21 | 1999-04-29 | Office Of Technology Liaison | Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants |
| TW200500095A (en) * | 2003-04-29 | 2005-01-01 | Akzo Nobel Nv | Antisolvent solidification process |
| TW201114466A (en) * | 2009-10-30 | 2011-05-01 | Nat Univ Chung Hsing | tion procedure |
-
2011
- 2011-07-20 TW TW100125694A patent/TWI466709B/zh not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999020587A1 (en) * | 1997-10-21 | 1999-04-29 | Office Of Technology Liaison | Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants |
| TW200500095A (en) * | 2003-04-29 | 2005-01-01 | Akzo Nobel Nv | Antisolvent solidification process |
| TW201114466A (en) * | 2009-10-30 | 2011-05-01 | Nat Univ Chung Hsing | tion procedure |
Also Published As
| Publication number | Publication date |
|---|---|
| TW201304846A (zh) | 2013-02-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2656834B1 (en) | Carotenoid oil suspension with high bioavailability and preparation method thereof | |
| JP3547741B2 (ja) | 高シス−β−カロチン組成物 | |
| JP6245170B2 (ja) | フコキサンチン含有組成物の製造方法 | |
| US7109361B2 (en) | Isolation of lutein from alfalfa | |
| EP2882841B1 (fr) | Procédé d'obtention d'une composition riche en lutéine produite par des microalgues | |
| AU2010200636B2 (en) | A process for isolation of carotenoids from plant sources | |
| CN101505615A (zh) | 基于生物番茄红素的食品补充剂和获得生物番茄红素的方法 | |
| US8034983B2 (en) | Process for the preparation of xanthophyll crystals | |
| CN103936643B (zh) | 一种提取分离万寿菊中叶黄素和黄酮的方法 | |
| JP6202270B2 (ja) | コウオウソウ属種−マリーゴールド花粗粉からの単段式ルテインエステル抽出 | |
| CA2857368C (en) | Method for extracting anthocyanin derivatives from a plant source | |
| CN1493622A (zh) | 番茄红素的制备方法 | |
| WO2013097056A1 (zh) | 一种制备叶黄素晶体的方法 | |
| WO2004094350A1 (en) | Method for extracting lutein from green plant materials | |
| WO2007056701A2 (en) | Nutrient extracts derived from green plant materials | |
| CN101985440B (zh) | 一种胡椒碱的生产方法 | |
| CN104694244A (zh) | 一种双溶剂提取高酯化虾青素高磷脂的磷虾油制备方法 | |
| TWI466709B (zh) | From the original berry Wolfberry a liquid - liquid freezing method for separation of high purity theaflavins palmitate Maize | |
| CN113876754A (zh) | 黑果枸杞花青素提取物及冻干粉的制备方法和在防治糖尿病性白内障产品中的应用 | |
| WO2015109657A1 (zh) | 一种原位富集制备天然玉米黄素的方法 | |
| CN111264861A (zh) | 一种天然虾青素的微胶囊及其制备方法 | |
| CN109097190B (zh) | 一种从磷虾油中富集磷脂的方法 | |
| CN1325485C (zh) | 一种从海藻中分离岩藻黄素的方法 | |
| CN114920797A (zh) | 一种从亚麻籽粕饼制备高纯度亚麻籽环肽的方法 | |
| JP5471824B2 (ja) | カロテノイド組成物の製造方法、高濃度カロテノイド組成物の製造方法、高純度遊離型カロテノイド組成物の製造方法、カロテノイド組成物、高濃度カロテノイド組成物、及び高純度遊離型カロテノイド組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |