CN104083556B - 一种从魔芋中提取魔芋神经酰胺的方法 - Google Patents
一种从魔芋中提取魔芋神经酰胺的方法 Download PDFInfo
- Publication number
- CN104083556B CN104083556B CN201410336065.3A CN201410336065A CN104083556B CN 104083556 B CN104083556 B CN 104083556B CN 201410336065 A CN201410336065 A CN 201410336065A CN 104083556 B CN104083556 B CN 104083556B
- Authority
- CN
- China
- Prior art keywords
- extraction
- separating still
- konjaku
- pressure
- temperature
- 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.)
- Active
Links
- 229920002752 Konjac Polymers 0.000 title claims abstract description 59
- 229940106189 ceramide Drugs 0.000 title claims abstract description 35
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 title claims abstract description 34
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 title claims abstract description 34
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 title claims abstract description 34
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 20
- 235000010485 konjac Nutrition 0.000 title claims abstract description 18
- 238000000605 extraction Methods 0.000 claims abstract description 105
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 44
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 22
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 238000003860 storage Methods 0.000 claims abstract description 7
- 238000007664 blowing Methods 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 6
- 230000001351 cycling effect Effects 0.000 claims abstract description 6
- 239000002245 particle Substances 0.000 claims abstract description 6
- 239000000843 powder Substances 0.000 claims abstract description 6
- 239000000284 extract Substances 0.000 description 16
- 238000010992 reflux Methods 0.000 description 15
- 239000000463 material Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 239000000287 crude extract Substances 0.000 description 6
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229940031439 squalene Drugs 0.000 description 6
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 239000000047 product Substances 0.000 description 5
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 4
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 4
- -1 N- acyls sphingosine Chemical class 0.000 description 4
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 description 4
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- XIRNKXNNONJFQO-UHFFFAOYSA-N ethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC XIRNKXNNONJFQO-UHFFFAOYSA-N 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000000638 solvent extraction Methods 0.000 description 4
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 4
- 229940032091 stigmasterol Drugs 0.000 description 4
- 235000016831 stigmasterol Nutrition 0.000 description 4
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 description 4
- WWUZIQQURGPMPG-UHFFFAOYSA-N (-)-D-erythro-Sphingosine Natural products CCCCCCCCCCCCCC=CC(O)C(N)CO WWUZIQQURGPMPG-UHFFFAOYSA-N 0.000 description 3
- LVGKNOAMLMIIKO-VAWYXSNFSA-N 9-Octadecenoic acid, ethyl ester Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-VAWYXSNFSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 3
- NPRJSFWNFTXXQC-QFWQFVLDSA-N N-(hexanoyl)sphing-4-enine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO)NC(=O)CCCCC NPRJSFWNFTXXQC-QFWQFVLDSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 230000017531 blood circulation Effects 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 239000013065 commercial product Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 description 3
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 2
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001278826 Amorphophallus Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 244000205754 Colocasia esculenta Species 0.000 description 2
- 235000006481 Colocasia esculenta Nutrition 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- 229930003427 Vitamin E Natural products 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical group CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 2
- FMMOOAYVCKXGMF-MURFETPASA-N ethyl linoleate Chemical group CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC FMMOOAYVCKXGMF-MURFETPASA-N 0.000 description 2
- 229940031016 ethyl linoleate Drugs 0.000 description 2
- 229940067592 ethyl palmitate Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000035558 fertility Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 150000002617 leukotrienes Chemical class 0.000 description 2
- FMMOOAYVCKXGMF-UHFFFAOYSA-N linoleic acid ethyl ester Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCC FMMOOAYVCKXGMF-UHFFFAOYSA-N 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 210000005229 liver cell Anatomy 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 238000000194 supercritical-fluid extraction Methods 0.000 description 2
- 235000019165 vitamin E Nutrition 0.000 description 2
- 239000011709 vitamin E Substances 0.000 description 2
- 229940046009 vitamin E Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HITROERJXNWVOI-SOFGYWHQSA-N (5e)-octa-1,5-diene Chemical compound CC\C=C\CCC=C HITROERJXNWVOI-SOFGYWHQSA-N 0.000 description 1
- YWHWYTRNKBGSRE-HKQCOZBKSA-N (8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 YWHWYTRNKBGSRE-HKQCOZBKSA-N 0.000 description 1
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 244000247812 Amorphophallus rivieri Species 0.000 description 1
- 235000001206 Amorphophallus rivieri Nutrition 0.000 description 1
- 241000209524 Araceae Species 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 241000238370 Sepia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010067868 Skin mass Diseases 0.000 description 1
- 102000011971 Sphingomyelin Phosphodiesterase Human genes 0.000 description 1
- 108010061312 Sphingomyelin Phosphodiesterase Proteins 0.000 description 1
- 102000019197 Superoxide Dismutase Human genes 0.000 description 1
- 108010012715 Superoxide dismutase Proteins 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 206010000269 abscess Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 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
- 230000036772 blood pressure Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 150000001783 ceramides Chemical class 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
- 229960003964 deoxycholic acid Drugs 0.000 description 1
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 235000014103 egg white Nutrition 0.000 description 1
- 210000000969 egg white Anatomy 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003163 gonadal steroid hormone Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000252 konjac Substances 0.000 description 1
- 208000006443 lactic acidosis Diseases 0.000 description 1
- 230000003859 lipid peroxidation Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 201000007227 lymph node tuberculosis Diseases 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000012372 quality testing Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 230000019100 sperm motility Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000002137 ultrasound extraction Methods 0.000 description 1
- 238000009777 vacuum freeze-drying Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 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 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Medicines Containing Plant Substances (AREA)
- Extraction Or Liquid Replacement (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明公开了一种从魔芋中提取魔芋神经酰胺的方法,步骤如下:(1)将魔芋粉碎成细粉,然后加入乙醇,料液比为1.5:500‑1200Kg/ml,然后制粒;(2)将步骤(1)制备的魔芋颗粒加入超临界CO2萃取设备的萃取釜中,对萃取釜、分离釜Ⅰ、分离釜Ⅱ进行加热,并对冷机及储罐制冷,当萃取釜温度为30‑70℃,分离釜Ⅰ温度为40‑65℃,分离釜Ⅱ温度为30‑60℃时,开启二氧化碳气瓶,通过高压泵对萃取釜、分离釜进行加压,当萃取釜压力为20‑40MPa,分离釜Ⅰ压力为6‑18MPa,分离釜Ⅱ压力为4‑7MPa时,关闭二氧化碳,开启循环阀,进行萃取循环,每循环30min,分别从分离釜Ⅰ、Ⅱ放料,循环萃取1‑2h。本发明的方法提取的C6‑神经酰胺的收率高,且萃取产物品质较好。
Description
技术领域
本发明涉及提取分离技术领域,尤其涉及一种从魔芋中提取魔芋神经酰胺的方法。
背景技术
魔芋(konjac)属于天南星科(Araceae)魔芋属(Amorphophallus B1.ex Decne.)草本植物的块茎,又名磨芋、鬼芋、鬼头、花莲杆、蛇六谷等,主要产于东半球热带、亚热带,在我国有较广泛的分布。魔芋性寒、辛,有毒;可活血化瘀,解毒消肿,宽肠通便,化痰软坚;主治降血压、降血糖、瘰疬痰核、损伤瘀肿、便秘腹痛、咽喉肿痛、牙龈肿痛等症。
神经酰胺类化合物(Ceramide),即N-脂酰神经鞘氨醇,是由神经鞘氨醇(sphingosine)和长链脂肪酸缩合而成的一类化合物,是鞘脂类化合物中最重要的一种。神经酰胺是最近几年新兴的一种活性成分,魔芋中含有比较丰富的神经酰胺,其神经酰胺的含量高达0.15~0.2%,是目前所采用的原料如米糠、大豆、小麦等原料的10倍。
提取神经酰胺最常用的是有机溶剂提取,通常采用异丙醇、乙酸乙酯或氯仿提取。刘仁萍等在探索回流提取法提取魔芋神经酰胺时,发现在相同条件下中等极性溶剂乙酸乙酯的提取效果最理想。但是,在相同提取条件下,用95%乙醇提取后经石油醚萃取的效果与乙酸乙酯的提取效果相差不大,并且乙酸乙酯价格较高,提取过程中挥发较大,因此,采用95%乙醇作为提取溶剂。作者通过正交试验确定提取的最佳工艺为95%乙醇、提取温度80℃、提取时间8h、料液比1:10,最高提取量达到4.34mg/g。
催韶晖等,采用95%乙醇,料液比1:7.5,水浴温度80℃~90℃,提取时间8h~10h,用去离子水调提取液乙醇溶度至70%,石油醚萃取,旋转蒸发仪浓缩。浓缩液以石油醚:丙酮(7:3)200ml进行硅胶柱层析2次分离纯化,流速为1d/s,洗脱液用旋转蒸发仪浓缩,浓缩液进行真空冷冻干燥得到白色粗品,粗品用丙酮重结晶进行纯化,得到白色纯化的神经酰胺样品。
魏静等对不同提取方法进行分析测定,结果表明在相似的条件下溶剂浸提法测定的含量为1.93%,而超声波法测得的含量为2.24%,后者提取效果明显优于前者。作者采用单因素实验法对影响神经酰胺提取率的主要因素进行了分析,利用正交实验优化了提取神经酰胺的最佳工艺条件。研究表明,超声提取魔芋神经酰胺的最佳条件为:乙醇浓度95%,料液质量比为1:4,提取温度60℃,提取时间35min。在该条件下神经酰胺粗提物的提取率为2.89%。
超临界萃取技术在魔芋提取神经酰胺中的应用虽尚未见报道,但李佳在研究微生物发酵米糠制备神经酰胺中应用了该技术,预示着超临界萃取技术将在魔芋提取神经酰胺得到应用。李佳利用鞘磷脂酶使米糠中游离的神经酰胺的含量提高3倍以上,并以萃取压力为30MPa,萃取温度32℃~35℃,分离釜压力为7MPa~8MPa,温度35℃~38℃的条件进行超临界萃取获得最佳萃取效果。
魔芋神经酰胺为植物源神经酰胺,安全性高于动物源神经酰胺和合成神经酰胺,含量也高于其他植物来源。从已有文献来看,对魔芋神经酰胺的研究主要集中在其药理活性方面,而其提取分离及质量分析方面较少,且提取分离方法传统繁琐、分析方法不够系统全面,也未见其神经酰胺的超临界CO2萃取工艺研究。
发明内容
本发明提供了一种从魔芋中提取魔芋神经酰胺的方法。
本发明采用如下技术方案:
本发明的从魔芋中提取魔芋神经酰胺的方法的具体步骤如下:
(1)将魔芋粉碎成细粉,然后加入乙醇,料液比为1.5:500-1200Kg/ml,然后制粒;
(2)将步骤(1)制备的魔芋颗粒加入超临界CO2萃取设备的萃取釜中,对萃取釜、分离釜Ⅰ、分离釜Ⅱ进行加热,并对冷机及储罐制冷,当萃取釜温度为30-70℃,分离釜Ⅰ温度为40-65℃,分离釜Ⅱ温度为30-60℃时,开启二氧化碳气瓶,通过高压泵对萃取釜、分离釜进行加压,当萃取釜压力为20-40MPa,分离釜Ⅰ压力为6-18MPa,分离釜Ⅱ压力为4-7MPa时,关闭二氧化碳,开启循环阀,进行萃取循环,每循环30min,分别从分离釜Ⅰ、Ⅱ放料,循环萃取1-2h。
步骤(1)中,乙醇的浓度为95%,料液比优选为1.5:1000Kg/ml。
步骤(2)中,优选萃取釜温度为60℃,压力为35MPa。
步骤(2)中,优选分离釜Ⅰ温度为50℃,压力为15MPa。
步骤(2)中,优选分离釜Ⅱ温度为45℃,压力为6MPa。
步骤(2)中,优选萃取时间为1.5h。
本发明的技术效果:
本发明的从魔芋中提取魔芋神经酰胺的方法与溶剂回流提取法相比较,超临界CO2萃取较回流提取的C6-神经酰胺的收率高约20%,且超临界CO2萃取产物品质较好,在外观、C6-神经酰胺含量等方面都优于溶剂回流提取法,同时萃取工艺简单、效率高,解决了传统回流提取法溶剂用量大、易燃易爆等问题。
附图说明
图1是本发明的超临界CO2萃取设备流程示意图。
图中:1-萃取釜、2-分离釜Ⅰ、3-分离釜Ⅱ、4-分离柱、5-换热器、6-高压泵、7-CO2气瓶、8-冷机储罐、9-流量计。
具体实施方式
下面的实施例是对本发明的进一步详细描述。
实施例1
(1)将魔芋粉碎成细粉,然后加入乙醇,料液比为1.5:500Kg/ml,然后制粒;
(2)将步骤(1)制备的魔芋颗粒加入超临界CO2萃取设备的萃取釜中,对萃取釜、分离釜Ⅰ、分离釜Ⅱ进行加热,并对冷机及储罐制冷,当萃取釜温度为30℃,分离釜Ⅰ温度为40℃,分离釜Ⅱ温度为30℃时,开启二氧化碳气瓶,通过高压泵对萃取釜、分离釜进行加压,当萃取釜压力为20MPa,分离釜Ⅰ压力为6MPa,分离釜Ⅱ压力为4MPa时,关闭二氧化碳,开启循环阀,进行萃取循环,每循环30min,分别从分离釜Ⅰ、Ⅱ放料,循环萃取2h。
步骤(1)中,乙醇的浓度为95%。
实施例2
(1)将魔芋粉碎成细粉,然后加入乙醇,料液比为1.5:1200Kg/ml,然后制粒;
(2)将步骤(1)制备的魔芋颗粒加入超临界CO2萃取设备的萃取釜中,对萃取釜、分离釜Ⅰ、分离釜Ⅱ进行加热,并对冷机及储罐制冷,当萃取釜温度为70℃,分离釜Ⅰ温度为65℃,分离釜Ⅱ温度为60℃时,开启二氧化碳气瓶,通过高压泵对萃取釜、分离釜进行加压,当萃取釜压力为40MPa,分离釜Ⅰ压力为18MPa,分离釜Ⅱ压力为7MPa时,关闭二氧化碳,开启循环阀,进行萃取循环,每循环30min,分别从分离釜Ⅰ、Ⅱ放料,循环萃取1h。
步骤(1)中,乙醇的浓度为95%。
实施例3
(1)将魔芋粉碎成细粉,然后加入乙醇,料液比为1.5:1000Kg/ml,然后制粒;
(2)将步骤(1)制备的魔芋颗粒加入超临界CO2萃取设备的萃取釜中,对萃取釜、分离釜Ⅰ、分离釜Ⅱ进行加热,并对冷机及储罐制冷,当萃取釜温度为60℃,分离釜Ⅰ温度为50℃,分离釜Ⅱ温度为45℃时,开启二氧化碳气瓶,通过高压泵对萃取釜、分离釜进行加压,当萃取釜压力为35MPa,分离釜Ⅰ压力为15MPa,分离釜Ⅱ压力为6MPa时,关闭二氧化碳,开启循环阀,进行萃取循环,每循环30min,分别从分离釜Ⅰ、Ⅱ放料,循环萃取1.5h。
步骤(1)中,乙醇的浓度为95%。
对比例(传统溶剂提取)
称取魔芋粉,放入圆底烧瓶,加入95%乙醇,80℃水浴回流提取2次,每次2h(第一次加入960ml95%乙醇,第二次加入720ml95%乙醇),过滤,合并提取液,50℃旋蒸浓缩至无水,得棕褐色油状提取物,称重并计算收率。
收率的计算
收率是评价萃取效果的重要指标,收率的计算公式如下:
粗提物收率=药材粗提物质量÷药材投料量×100%
C6-Cer收率=药材粗提物质量×粗提物中C6-Cer百分含量%÷药材投料量×100%。
实施例1-3的收率如表1所示:
表1
以实施例3为例对比超临界CO2萃取法与传统溶剂提取的优劣,结果如表2所示:
表2 超临界CO2萃取法与传统回流提取法的比较
由表2可以看出:超临界CO2萃取魔芋神经酰胺粗提物收率比回流提取法低,而C6-Cer收率较高,可能由于溶剂提取的产物含较多极性大的杂质。与传统的乙醇回流提取法相比,超临界萃取物在色泽、神经酰胺含量和收率等方面都优于传统回流提取法。因此,采用超临界CO2萃取魔芋神经酰胺,优于常规提取方法。
与传统溶剂回流提取法相比较,本发明的魔芋神经酰胺的超临界CO2萃取工艺具有以下特点:
(1)萃取能力强,萃取效率高,收率比回流提取法高约20%;
(2)萃取温度低,有效保护热敏有效成分;
(3)能选择性萃取和分离成分,萃取过程的同时可分离杂质;
(4)生产工艺简单,不需过滤等工艺;
(5)萃取在高压惰性条件下进行,几乎可完全杀灭好氧微生物,有效保证和提高产品的质量
(6)避免有机溶剂的使用,降低乙醇的用量。
魔芋超临界CO2萃取物挥发性成分分析
对实施例3制备的及溶剂法制备的魔芋神经酰胺提取物的挥发性成分进行气质色谱分析对比:
气相色谱条件:色谱柱为TR-1MS型100%二甲基聚硅烷弹性石英毛细管柱(30m×0.25mm×0.25μm);进样口温度250℃,不分流,载气为氦气,流速1ml/min,进样量:1μL。质谱条件:传输管温度280℃;离子源温度230℃;EI离子源,电子能量70ev;全扫描,扫描范围:40-450。
分别对实施例3、市售产品和对比例的产品进行成分分析,结果如表3所示:
表3 3种不同产品挥发性成分对比表
根据表3分析结果可知,三种样品中的成分种类以及数目存在较大差异,魔芋超临界CO2萃取物主要成分为亚油酸乙酯、棕榈酸乙酯、豆甾-4-烯-3-酮、亚麻酸、反油酸乙酯等物质;魔芋市售产品主要成分为亚油酸甲酯、穿贝海绵甾醇、豆甾醇、维生素E等物质;魔芋回流提取物主要成分为邻苯二甲酸二异丁酯、穿贝海绵甾醇、豆甾醇、2,6-二甲基-1,6-二醇-2,7-辛二烯等物质。
魔芋超临界CO2萃取物中脂肪酸(酯)类物质主要为亚麻酸、亚油酸乙酯、棕榈酸乙酯、反油酸乙酯等成分,总相对含量达到71.68%;魔芋回流提取物质则几乎没有此类物质;市售魔芋提取物主要含有亚油酸甲酯、棕榈酸乙酯、反油酸乙酯等成分,相对含量为31.61%。
魔芋超临界CO2萃取物中主要的甾醇为豆甾-4-烯-3-酮、豆固酮、4-胆甾烯-3-酮等物质,总相对含量达到12.93%;魔芋回流提取物主要甾醇为穿贝海绵甾醇、豆甾醇和甘油脱氧胆酸,相对含量为18.21%;市售魔芋提取物主要含穿贝海绵甾醇和豆甾醇,相对含量为14.31%。
角鲨烯是一种脂质不皂化物。在三种魔芋提取物中均含有角鲨烯,在超临界CO2萃取物中的相对含量为1.71%,在回流提取物中为1.84%,在市售提取物中为3.39%。角鲨烯能促进肝细胞的再生并保护肝细胞,从而改善肝脏的功能;角鲨烯能促使体内超氧化酶与乳酸脱氢酶显著升高,促进乳酸分解,使体内能量代谢旺盛,体力快速恢复,及时消除疲劳;角鲨烯能促进血液循环,降低胆固醇和甘油三酯的含量,抑制血清中胆固醇浓度,降低脂蛋白浓度,并加速胆固醇的排出,可延缓动脉粥样硬化的形成,预防心脑血管疾病的发生。除此之外,角鲨烯还具有抗衰老、抗肿瘤等作用。
维生素E是一种脂溶性维生素,又称生育酚,是最主要的抗氧化剂之一。在魔芋超临界萃取物中的相对含量为0.63%,市售产品中为6.00%,而回流提取物中则物检测出。维生素E具有广泛的生理功能,其能通过自身被氧化成生育醌,将活泼的ROO﹣转变成不活泼的ROOH,从而中断脂类过氧化的连锁反应,抑制脂类的过氧化作用,保护细胞免受伤害;促进性激素分泌,使男子精子活力和数量增加,提高生育能力;维持毛细血管的通透性,增加血流量,增强抵御寒冷的能力,并修复血管壁损伤后的疤痕,抑制血小板的聚集,防止血栓的形成。魔芋的醇溶性成分大部分具有生理活性作用,与魔芋的部分功效相同或相近,可以推断魔芋的部分功效可能与其醇溶性成分有关。为魔芋的进一步开发与利用提供科学的依据。
尽管已经示出和描述了本发明的实施例,对于本领域的普通技术人员而言,可以理解在不脱离本发明的原理和精神的情况下可以对这些实施例进行多种变化、修改、替换和变型,本发明的范围由所附权利要求及其等同物限定。
Claims (3)
1.一种从魔芋中提取魔芋神经酰胺的方法,其特征在于:所述方法的具体步骤如下:
(1)将魔芋粉碎成细粉,然后加入95%乙醇,料液比为1.5:1000Kg/ml,然后制粒;
(2)将步骤(1)制备的魔芋颗粒加入超临界CO2萃取设备的萃取釜中,对萃取釜、分离釜Ⅰ、分离釜Ⅱ进行加热,并对冷机及储罐制冷,当萃取釜温度为30-70℃,分离釜Ⅰ温度为50℃,分离釜Ⅱ温度为45℃时,开启二氧化碳气瓶,通过高压泵对萃取釜、分离釜进行加压,当萃取釜压力为20-40MPa,分离釜Ⅰ压力为15MPa,分离釜Ⅱ压力为6MPa时,关闭二氧化碳,开启循环阀,进行萃取循环,每循环30min,分别从分离釜Ⅰ、Ⅱ放料,循环萃取1-2h。
2.如权利要求1所述的从魔芋中提取魔芋神经酰胺的方法,其特征在于:步骤(2)中,萃取釜温度为60℃,压力为35MPa。
3.如权利要求1所述的从魔芋中提取魔芋神经酰胺的方法,其特征在于:步骤(2)中,萃取时间为1.5h。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410336065.3A CN104083556B (zh) | 2014-07-15 | 2014-07-15 | 一种从魔芋中提取魔芋神经酰胺的方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410336065.3A CN104083556B (zh) | 2014-07-15 | 2014-07-15 | 一种从魔芋中提取魔芋神经酰胺的方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104083556A CN104083556A (zh) | 2014-10-08 |
CN104083556B true CN104083556B (zh) | 2018-04-17 |
Family
ID=51631384
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410336065.3A Active CN104083556B (zh) | 2014-07-15 | 2014-07-15 | 一种从魔芋中提取魔芋神经酰胺的方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104083556B (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105403633B (zh) * | 2015-10-28 | 2018-05-11 | 广州中大南沙科技创新产业园有限公司 | 魔芋中神经酰胺含量测定方法 |
CN107721871B (zh) * | 2017-10-20 | 2020-10-27 | 中山大学 | 一种分子蒸馏分离纯化魔芋神经酰胺的方法 |
CN113413632B (zh) * | 2021-07-08 | 2022-06-03 | 宁夏大学 | 一种银柴胡脂类提取物及其制备方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103755583A (zh) * | 2014-01-27 | 2014-04-30 | 广州市娇兰化妆品有限公司 | 魔芋飞粉中神经酰胺的提取分离方法 |
-
2014
- 2014-07-15 CN CN201410336065.3A patent/CN104083556B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103755583A (zh) * | 2014-01-27 | 2014-04-30 | 广州市娇兰化妆品有限公司 | 魔芋飞粉中神经酰胺的提取分离方法 |
Non-Patent Citations (1)
Title |
---|
微生物发酵米糠制备神经酰胺;李佳等;《化学研究与应用》;20070630;第19卷(第6期);第652-656页 * |
Also Published As
Publication number | Publication date |
---|---|
CN104083556A (zh) | 2014-10-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN103351941B (zh) | 一种采用超临界co2变温变压萃取灵芝孢子油的方法 | |
CN102100260B (zh) | 酵母油脂及其制备方法和应用 | |
CN103450808B (zh) | 一种采用亚临界流体丁烷提取生姜油树脂的方法 | |
CN104073344A (zh) | 一种灵芝孢子油的提取方法 | |
CN105602719B (zh) | 一种茶油的超临界提取方法 | |
CN102234563B (zh) | 超声波辅助超临界co2萃取枸杞籽油的方法 | |
CN106187977A (zh) | 一种提取山竹壳中原花青素的方法 | |
CN105623842A (zh) | 亚临界萃取辣木籽油的方法及其甘油三酯位置分布测定的方法 | |
CN104083556B (zh) | 一种从魔芋中提取魔芋神经酰胺的方法 | |
CN103087818A (zh) | 超声波辅助超临界co2萃取葵花籽油的方法 | |
CN101891580A (zh) | 二氧化碳超临界萃取西瓜番茄红素的方法 | |
CN101863764B (zh) | 超临界co2分步提取及分离薏苡仁酯和薏苡仁油的方法 | |
CN108424816A (zh) | 一种百里香精油的提取工艺 | |
CN101982191A (zh) | 一种提取荷叶降脂复方功能性物质的方法 | |
CN105878323A (zh) | 一种超声辅助超临界萃取精馏纯化朝鲜蓟中洋蓟素的方法 | |
CN104591993B (zh) | 一种发酵菌体中辅酶q10的提取方法 | |
CN109054992A (zh) | 一种提取沙棘籽油的方法 | |
CN106187976A (zh) | 一种提取紫薯中原花青素的方法 | |
CN104073355A (zh) | 一种广藿香挥发油的提取方法 | |
CN101390975A (zh) | 柑橘活性成分的萃取方法 | |
CN106187978A (zh) | 一种提取火龙果皮中原花青素的方法 | |
CN107033045A (zh) | 一种高纯度天然大蒜阿霍烯的制备方法 | |
CN102260587A (zh) | 一种提取葡萄籽油和原花青素的方法 | |
CN106083797A (zh) | 一种提取怀枝果皮中原花青素的方法 | |
CN104547204A (zh) | 一种从荔枝果皮提取多酚物质的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |