CN106366152B - 从积雪草中提取积雪草苷的方法 - Google Patents
从积雪草中提取积雪草苷的方法 Download PDFInfo
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- CN106366152B CN106366152B CN201610726900.3A CN201610726900A CN106366152B CN 106366152 B CN106366152 B CN 106366152B CN 201610726900 A CN201610726900 A CN 201610726900A CN 106366152 B CN106366152 B CN 106366152B
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- Prior art keywords
- centella
- asiaticosid
- ethanol
- extracted
- crude extract
- Prior art date
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- WYQVAPGDARQUBT-FGWHUCSPSA-N Madecassol Chemical compound O([C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)OC[C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)OC(=O)[C@]12CC[C@H]([C@@H]([C@H]1C=1[C@@]([C@@]3(CC[C@H]4[C@](C)(CO)[C@@H](O)[C@H](O)C[C@]4(C)[C@H]3CC=1)C)(C)CC2)C)C)[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O WYQVAPGDARQUBT-FGWHUCSPSA-N 0.000 title claims abstract description 37
- WYQVAPGDARQUBT-XCWYDTOWSA-N asiaticoside Natural products O=C(O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]2[C@H](O)[C@H](O)[C@H](O[C@H]3[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O3)[C@@H](CO)O2)O1)[C@@]12[C@@H]([C@@H](C)[C@H](C)CC1)C=1[C@](C)([C@@]3(C)[C@@H]([C@@]4(C)[C@H]([C@@](CO)(C)[C@@H](O)[C@H](O)C4)CC3)CC=1)CC2 WYQVAPGDARQUBT-XCWYDTOWSA-N 0.000 title claims abstract description 37
- 241000167550 Centella Species 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 65
- 239000000287 crude extract Substances 0.000 claims abstract description 14
- 239000011347 resin Substances 0.000 claims abstract description 14
- 229920005989 resin Polymers 0.000 claims abstract description 14
- 238000000605 extraction Methods 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000010828 elution Methods 0.000 claims abstract description 9
- 239000000284 extract Substances 0.000 claims abstract description 9
- 238000010992 reflux Methods 0.000 claims abstract description 9
- 238000013461 design Methods 0.000 claims abstract description 7
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- 238000003756 stirring Methods 0.000 claims abstract description 7
- 238000001514 detection method Methods 0.000 claims description 6
- 238000004809 thin layer chromatography Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- OZECDDHOAMNMQI-UHFFFAOYSA-H cerium(3+);trisulfate Chemical compound [Ce+3].[Ce+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OZECDDHOAMNMQI-UHFFFAOYSA-H 0.000 claims description 3
- 229910000333 cerium(III) sulfate Inorganic materials 0.000 claims description 3
- ICAKDTKJOYSXGC-UHFFFAOYSA-K lanthanum(iii) chloride Chemical compound Cl[La](Cl)Cl ICAKDTKJOYSXGC-UHFFFAOYSA-K 0.000 claims description 3
- YWECOPREQNXXBZ-UHFFFAOYSA-N praseodymium(3+);trinitrate Chemical compound [Pr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O YWECOPREQNXXBZ-UHFFFAOYSA-N 0.000 claims description 3
- HDGGAKOVUDZYES-UHFFFAOYSA-K erbium(iii) chloride Chemical compound Cl[Er](Cl)Cl HDGGAKOVUDZYES-UHFFFAOYSA-K 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 2
- 229910052761 rare earth metal Inorganic materials 0.000 abstract description 15
- -1 rare-earth salts Chemical class 0.000 abstract description 11
- 238000002156 mixing Methods 0.000 abstract description 6
- 239000003480 eluent Substances 0.000 abstract 1
- QCYLIQBVLZBPNK-UHFFFAOYSA-N asiaticoside A Natural products O1C(C(=O)C(C)C)=CC(C)C(C2(C(OC(C)=O)CC34C5)C)C1CC2(C)C3CCC(C1(C)C)C45CCC1OC1OCC(O)C(O)C1O QCYLIQBVLZBPNK-UHFFFAOYSA-N 0.000 description 9
- BNMGUJRJUUDLHW-HLUHVYOBSA-N Madecassoside Natural products C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@@H]5[C@H](O)C[C@@]34C)[C@@H]2[C@H]1C)C(=O)O[C@@H]6O[C@H](CO[C@@H]7O[C@H](CO)[C@@H](O[C@@H]8O[C@H](C)[C@H](O)[C@@H](O)[C@H]8O)[C@H](O)[C@H]7O)[C@@H](O)[C@H](O)[C@H]6O BNMGUJRJUUDLHW-HLUHVYOBSA-N 0.000 description 7
- 229940090813 madecassoside Drugs 0.000 description 7
- BNMGUJRJUUDLHW-HCZMHFOYSA-N Madecassoside Chemical compound O([C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)OC[C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)OC(=O)[C@]12CC[C@H]([C@@H]([C@H]1C=1[C@@]([C@@]3(C[C@@H](O)[C@H]4[C@](C)(CO)[C@@H](O)[C@H](O)C[C@]4(C)[C@H]3CC=1)C)(C)CC2)C)C)[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O BNMGUJRJUUDLHW-HCZMHFOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
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- 230000000694 effects Effects 0.000 description 4
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- 239000000047 product Substances 0.000 description 4
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- 239000000126 substance Substances 0.000 description 4
- 150000003648 triterpenes Chemical class 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 3
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
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- 244000025254 Cannabis sativa Species 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
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- 229930182470 glycoside Natural products 0.000 description 2
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 2
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- 230000010148 water-pollination Effects 0.000 description 2
- MAYVZUQEFSJDHA-UHFFFAOYSA-N 1,5-bis(methylsulfanyl)naphthalene Chemical compound C1=CC=C2C(SC)=CC=CC2=C1SC MAYVZUQEFSJDHA-UHFFFAOYSA-N 0.000 description 1
- OBOSXEWFRARQPU-UHFFFAOYSA-N 2-n,2-n-dimethylpyridine-2,5-diamine Chemical compound CN(C)C1=CC=C(N)C=N1 OBOSXEWFRARQPU-UHFFFAOYSA-N 0.000 description 1
- NGDQQLAVJWUYSF-UHFFFAOYSA-N 4-methyl-2-phenyl-1,3-thiazole-5-sulfonyl chloride Chemical compound S1C(S(Cl)(=O)=O)=C(C)N=C1C1=CC=CC=C1 NGDQQLAVJWUYSF-UHFFFAOYSA-N 0.000 description 1
- QXPQVUQBEBHHQP-UHFFFAOYSA-N 5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-amine Chemical compound C1CCCC2=C1SC1=C2C(N)=NC=N1 QXPQVUQBEBHHQP-UHFFFAOYSA-N 0.000 description 1
- 241000218208 Caltha Species 0.000 description 1
- 235000008749 Caltha palustris Nutrition 0.000 description 1
- 244000146462 Centella asiatica Species 0.000 description 1
- 235000004032 Centella asiatica Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 235000014043 Glechoma hederacea var parviflora Nutrition 0.000 description 1
- 241000196322 Marchantia Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 244000215554 Nepeta hederacea Species 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- NYEODMYOBSNUDJ-UHFFFAOYSA-N S(O)(O)(=O)=O.[Lu] Chemical compound S(O)(O)(=O)=O.[Lu] NYEODMYOBSNUDJ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- MKNZSAIPAVSJSI-UHFFFAOYSA-N [Tb].S(O)(O)(=O)=O Chemical compound [Tb].S(O)(O)(=O)=O MKNZSAIPAVSJSI-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- JXSVIVRDWWRQRT-UYDOISQJSA-N asiatic acid Chemical compound C1[C@@H](O)[C@H](O)[C@@](C)(CO)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C JXSVIVRDWWRQRT-UYDOISQJSA-N 0.000 description 1
- 229940011658 asiatic acid Drugs 0.000 description 1
- LBGFKBYMNRAMFC-PYSQTNCISA-N asiatic acid Natural products C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@@H]5CC[C@@]34C)[C@]2(C)[C@H]1C)C(=O)O LBGFKBYMNRAMFC-PYSQTNCISA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 1
- HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- FLWXWKDFOLALOB-UHFFFAOYSA-H dysprosium(3+);trisulfate Chemical compound [Dy+3].[Dy+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O FLWXWKDFOLALOB-UHFFFAOYSA-H 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
- YBYGDBANBWOYIF-UHFFFAOYSA-N erbium(3+);trinitrate Chemical compound [Er+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O YBYGDBANBWOYIF-UHFFFAOYSA-N 0.000 description 1
- SYDXSHCNMKOQFW-UHFFFAOYSA-H erbium(3+);trisulfate Chemical compound [Er+3].[Er+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O SYDXSHCNMKOQFW-UHFFFAOYSA-H 0.000 description 1
- CLXOLTFMHAXJST-UHFFFAOYSA-N esculentic acid Natural products C12CC=C3C4CC(C)(C(O)=O)CCC4(C(O)=O)CCC3(C)C1(C)CCC1C2(C)CCC(O)C1(CO)C CLXOLTFMHAXJST-UHFFFAOYSA-N 0.000 description 1
- GAGGCOKRLXYWIV-UHFFFAOYSA-N europium(3+);trinitrate Chemical compound [Eu+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O GAGGCOKRLXYWIV-UHFFFAOYSA-N 0.000 description 1
- NNMXSTWQJRPBJZ-UHFFFAOYSA-K europium(iii) chloride Chemical compound Cl[Eu](Cl)Cl NNMXSTWQJRPBJZ-UHFFFAOYSA-K 0.000 description 1
- WLYAEQLCCOGBPV-UHFFFAOYSA-N europium;sulfuric acid Chemical compound [Eu].OS(O)(=O)=O WLYAEQLCCOGBPV-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 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
- 125000000524 functional group Chemical group 0.000 description 1
- MEANOSLIBWSCIT-UHFFFAOYSA-K gadolinium trichloride Chemical compound Cl[Gd](Cl)Cl MEANOSLIBWSCIT-UHFFFAOYSA-K 0.000 description 1
- XKJJKZIBLKQSLH-UHFFFAOYSA-N gadolinium;nitric acid Chemical compound [Gd].O[N+]([O-])=O XKJJKZIBLKQSLH-UHFFFAOYSA-N 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- JTZUUBNBNBFJCX-UHFFFAOYSA-N holmium sulfuric acid Chemical compound [Ho].S(O)(O)(=O)=O JTZUUBNBNBFJCX-UHFFFAOYSA-N 0.000 description 1
- WDVGLADRSBQDDY-UHFFFAOYSA-N holmium(3+);trinitrate Chemical compound [Ho+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O WDVGLADRSBQDDY-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- FYDKNKUEBJQCCN-UHFFFAOYSA-N lanthanum(3+);trinitrate Chemical compound [La+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O FYDKNKUEBJQCCN-UHFFFAOYSA-N 0.000 description 1
- VQEHIYWBGOJJDM-UHFFFAOYSA-H lanthanum(3+);trisulfate Chemical compound [La+3].[La+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VQEHIYWBGOJJDM-UHFFFAOYSA-H 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- PRAUVHZJPXOEIF-AOLYGAPISA-N madecassic acid Chemical compound C1[C@@H](O)[C@H](O)[C@@](C)(CO)[C@@H]2[C@H](O)C[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C PRAUVHZJPXOEIF-AOLYGAPISA-N 0.000 description 1
- PRAUVHZJPXOEIF-UHFFFAOYSA-N madecassica acid Natural products C1C(O)C(O)C(C)(CO)C2C(O)CC3(C)C4(C)CCC5(C(O)=O)CCC(C)C(C)C5C4=CCC3C21C PRAUVHZJPXOEIF-UHFFFAOYSA-N 0.000 description 1
- 239000002398 materia medica Substances 0.000 description 1
- CFYGEIAZMVFFDE-UHFFFAOYSA-N neodymium(3+);trinitrate Chemical compound [Nd+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O CFYGEIAZMVFFDE-UHFFFAOYSA-N 0.000 description 1
- OJSWEKSDNUORPG-UHFFFAOYSA-H neodymium(3+);trisulfate Chemical compound [Nd+3].[Nd+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OJSWEKSDNUORPG-UHFFFAOYSA-H 0.000 description 1
- ATINCSYRHURBSP-UHFFFAOYSA-K neodymium(iii) chloride Chemical compound Cl[Nd](Cl)Cl ATINCSYRHURBSP-UHFFFAOYSA-K 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- LHBNLZDGIPPZLL-UHFFFAOYSA-K praseodymium(iii) chloride Chemical compound Cl[Pr](Cl)Cl LHBNLZDGIPPZLL-UHFFFAOYSA-K 0.000 description 1
- HWZAHTVZMSRSJE-UHFFFAOYSA-H praseodymium(iii) sulfate Chemical compound [Pr+3].[Pr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O HWZAHTVZMSRSJE-UHFFFAOYSA-H 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- LVSITDBROURTQX-UHFFFAOYSA-H samarium(3+);trisulfate Chemical compound [Sm+3].[Sm+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O LVSITDBROURTQX-UHFFFAOYSA-H 0.000 description 1
- BHXBZLPMVFUQBQ-UHFFFAOYSA-K samarium(iii) chloride Chemical compound Cl[Sm](Cl)Cl BHXBZLPMVFUQBQ-UHFFFAOYSA-K 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- DVMZCYSFPFUKKE-UHFFFAOYSA-K scandium chloride Chemical compound Cl[Sc](Cl)Cl DVMZCYSFPFUKKE-UHFFFAOYSA-K 0.000 description 1
- 229910000346 scandium sulfate Inorganic materials 0.000 description 1
- DFCYEXJMCFQPPA-UHFFFAOYSA-N scandium(3+);trinitrate Chemical compound [Sc+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O DFCYEXJMCFQPPA-UHFFFAOYSA-N 0.000 description 1
- QHYMYKHVGWATOS-UHFFFAOYSA-H scandium(3+);trisulfate Chemical compound [Sc+3].[Sc+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O QHYMYKHVGWATOS-UHFFFAOYSA-H 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- YJVUGDIORBKPLC-UHFFFAOYSA-N terbium(3+);trinitrate Chemical compound [Tb+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O YJVUGDIORBKPLC-UHFFFAOYSA-N 0.000 description 1
- GFISHBQNVWAVFU-UHFFFAOYSA-K terbium(iii) chloride Chemical compound Cl[Tb](Cl)Cl GFISHBQNVWAVFU-UHFFFAOYSA-K 0.000 description 1
- LLZBVBSJCNUKLL-UHFFFAOYSA-N thulium(3+);trinitrate Chemical compound [Tm+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O LLZBVBSJCNUKLL-UHFFFAOYSA-N 0.000 description 1
- NEEAOWXTIOQDFM-UHFFFAOYSA-H thulium(3+);trisulfate Chemical compound [Tm+3].[Tm+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O NEEAOWXTIOQDFM-UHFFFAOYSA-H 0.000 description 1
- ILOTUXNTERMOJL-UHFFFAOYSA-K thulium(iii) chloride Chemical compound Cl[Tm](Cl)Cl ILOTUXNTERMOJL-UHFFFAOYSA-K 0.000 description 1
- PYOOBRULIYNHJR-UHFFFAOYSA-K trichloroholmium Chemical compound Cl[Ho](Cl)Cl PYOOBRULIYNHJR-UHFFFAOYSA-K 0.000 description 1
- OOTXFYSZXCPMPG-BMYLZFHVSA-N ursane Chemical compound C1CCC(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CC[C@@H](C)[C@H](C)[C@H]5[C@H]4CC[C@@H]3[C@]21C OOTXFYSZXCPMPG-BMYLZFHVSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- KUBYTSCYMRPPAG-UHFFFAOYSA-N ytterbium(3+);trinitrate Chemical compound [Yb+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O KUBYTSCYMRPPAG-UHFFFAOYSA-N 0.000 description 1
- KVCOOBXEBNBTGL-UHFFFAOYSA-H ytterbium(3+);trisulfate Chemical compound [Yb+3].[Yb+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O KVCOOBXEBNBTGL-UHFFFAOYSA-H 0.000 description 1
- CKLHRQNQYIJFFX-UHFFFAOYSA-K ytterbium(III) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Yb+3] CKLHRQNQYIJFFX-UHFFFAOYSA-K 0.000 description 1
- 229910000347 yttrium sulfate Inorganic materials 0.000 description 1
- RTAYJOCWVUTQHB-UHFFFAOYSA-H yttrium(3+);trisulfate Chemical compound [Y+3].[Y+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RTAYJOCWVUTQHB-UHFFFAOYSA-H 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Abstract
本发明公开了一种从积雪草中提取积雪草苷的方法，其特征在于：包括以下步骤：1)将积雪草粉碎，用60～70％乙醇溶液回流提取，将提取液过滤，滤液回收溶剂，再加40～50℃水溶解，得到粗提液；2)往粗提液加入稀土盐混合，搅匀，得到混合液；3)将混合液上X‑5型号大孔树脂柱，先水洗至无色，然后用体积浓度为50～70％乙醇洗脱，收集洗脱液，回收乙醇，干燥，得到积雪草苷。本发明提取的积雪草苷纯度高，收率大。
Description
技术领域
本发明属于生物提取技术领域，具体涉及一种从积雪草中提取积雪草苷的方法。
背景技术
积雪草(Centella asiatica(L.)Urban)为伞形科积雪草树植物，因其叶子酷似马蹄状或半个铜钱，所以又名马蹄草、连钱草等，民间也有地方称其为胡薄荷、地钱草等。积雪草在许多国家和地区的传统医药领域中的应用历史悠久，我国中医中药对积雪草的内服和外用已有两千年历史，最早被《神农本草经》一书所收载。据《本草纲目》记载，积雪草味苦、辛，性寒，无毒，归肝、脾、肾、胃经，其功效为活血、消肿止痛，并有清热解毒、利尿等。积雪草的化学成分主要有三萜类、黄酮类、多炔烯类和挥发油类等。三萜类主要有三萜皂苷类，如积雪草苷、羟基积雪草苷等，和三萜酸类，如积雪草酸、羟基积雪草酸等。积雪草的化学成分中，三萜类皂苷是研究最早，生物学活性研究最深入的一大类组分。积雪草总皂苷主要由积雪草苷和羟基积雪草苷组成，它们属于乌苏烷型的五环三萜皂苷，是积雪草药理活性的最主要成分。积雪草苷一般先用溶剂法提取，然后采用平均孔径较小的大孔树脂进行纯化，如HPD-100(平均孔径为8.5～9.0nm)、HPD-300(平均孔径为5.0～5.5nm),由于大孔树脂对目标成分的吸附和筛选针对性不是很强，在吸附过程中很多杂质会吸附到树脂孔隙中，而解吸时，由于孔隙较小，目标成分并不能解吸完全，因此，纯化后的积雪草苷的收率和纯度均不高。
发明内容
本发明解决的技术问题是提供一种从积雪草中提取积雪草苷的方法，该方法提取得到的积雪草苷收率大，纯度高。
本发明提供的技术方案是提供一种从积雪草中提取积雪草苷的方法，包括以下步骤：
1)将积雪草粉碎，用60～70v％乙醇溶液回流提取，将提取液过滤，滤液回收溶剂，再加40～50℃水溶解，得到粗提液；
2)往粗提液加入稀土盐混合，搅匀，得到混合液；
3)将混合液上X-5型号大孔树脂柱，先水洗至无色，然后用体积浓度为35～45v％乙醇洗脱，薄层层析跟踪检测，收集含目标成分的乙醇洗脱液，回收乙醇，干燥，得到积雪草苷。
步骤1)中，乙醇的用量为积雪草重量的10～20倍，回流提取1～3次，每次1～3h。
体积浓度为60～70％的乙醇可充分溶解积雪草中的三萜类物质，包括三萜类总皂苷和三萜酸类物质。积雪草总皂苷由于它们的分子中往往结合有多数糖分子，羟基数目多，能表现出一定的亲水性，但是亲水性不强，微溶于水中，而三萜酸类极性较小，不能溶于水中。因此采用40～50℃温水可帮助积雪草皂苷溶解，积雪草酸类物质不溶于水中，以达到去除三萜酸类成分的目的。
步骤2)中，所述稀土盐为稀土氯化物、稀土硫酸盐或稀土硝酸盐。稀土氯化物可以是氯化镧、氯化铈、氯化镨、氯化钕、氯化钐、氯化铕、氯化钆、氯化铽、氯化镝、氯化钬、氯化铒、氯化铥、氯化镱、氯化镥、氯化钪和氯化钇；稀土硫酸盐可以是硫酸镧、硫酸铈、硫酸镨、硫酸钕、硫酸钐、硫酸铕、硫酸钆、硫酸铽、硫酸镝、硫酸钬、硫酸铒、硫酸铥、硫酸镱、硫酸镥、硫酸钪和硫酸钇；稀土硝酸盐可以是硝酸镧、硝酸铈、硝酸镨、硝酸钕、硝酸钐、硝酸铕、硝酸钆、硝酸铽、硝酸镝、硝酸钬、硝酸铒、硝酸铥、硝酸镱、硝酸镥、硝酸钪和硝酸钇。
稀土元素与积雪草苷和羟基积雪草苷上羟基、羧基上的氧原子形成配位键和，形成化学亲和力，根据软硬酸碱理论，由于稀土是硬酸，积雪草苷和羟基积雪草苷是软碱，因此，两者的结合不是特别稳固。
稀土盐占混合液总重的0.1～0.5％。此时，稀土盐可充分与目标成分进行配位。
步骤3)中，X-5型号大孔树脂为非极性树脂，粒径为0.3～1.25mm，比表面积为500～600m2/g，平均孔径为29～30nm。其孔径远远大于积雪草苷的分子粒径。而稀土的配位数较大，与其进行配位键和的含氧官能团数目往往达不到其最高配位数，因此稀土还会与大孔树脂中的C产生交联，以达到吸附的效果。
为了保证稀土元素与大孔树脂的交联，混合液的上柱速度越小，效果越好，经申请人大量实验，混合液上柱速度为0.5～0.8BV/h，交联效果最好。
由于稀土元素与积雪草苷和羟基积雪草苷的结合十分不稳固，而积雪草苷与乙醇的亲和力极强，很容易被乙醇溶液洗脱下来。又由于积雪草苷三个位点上有羟基，这三个位点都是配位原子与稀土原子进行配位，而羟基积雪草苷比积雪草苷多一个羟基，配位能力更强。因此，在洗脱时，积雪草苷先被洗脱下来。采用体积浓度为35～45％的乙醇可优先将积雪草苷洗脱，而不混入羟基积雪草苷。洗脱速度为2～2.5BV/h为宜。
与现有技术相比，本方法针对目标成分进行吸附和解吸附，提取的积雪草苷收率高达95％以上，纯度高达99.5％以上。
具体实施方式
以下具体实施例对本发明作进一步阐述，但不作为对本发明的限定。
以下百分数为体积百分数。
实施例1
1)将积雪草粉碎，加入积雪草总重10倍的60％乙醇溶液回流提取1次，每次1h，将提取液过滤，将滤液回收溶剂，再加40℃水溶解，除去滤渣，即得粗提液；
2)往粗提液加入其重量0.1％氯化镧混合，搅匀，得到混合液；
3)将混合液上X-5型号大孔树脂柱，上柱速度为0.5BV/h，先水洗至无色，然后用体积浓度为35v％乙醇洗脱，薄层层析跟踪检测，收集含目标成分的乙醇洗脱液，回收乙醇，干燥，得到积雪草苷。
经HLPC分析，积雪草苷的回收率为95.24％以上，纯度高达99.50％以上。
实施例2
1)将积雪草粉碎，加入积雪草总重20倍的70％乙醇溶液回流提取3次，每次3h，将提取液合并，过滤，将滤液回收溶剂，再加50℃水溶解，除去滤渣，即得粗提液；
2)往粗提液加入其重量0.5％硫酸铈混合，搅匀，得到混合液；
3)将混合液上X-5型号大孔树脂柱，上柱速度为0.8BV/h，先水洗至无色，然后用体积浓度为45v％乙醇洗脱，薄层层析跟踪检测，收集含目标成分的乙醇洗脱液，回收乙醇，干燥，得到积雪草苷。
经HLPC分析，积雪草苷的回收率为95.33％以上，纯度高达99.58％以上。
实施例3
1)将积雪草粉碎，加入积雪草总重15倍的65％乙醇溶液回流提取2次，每次2h，将提取液合并，过滤，将滤液回收溶剂，再加45℃水溶解，除去滤渣，即得粗提液；
2)往粗提液加入其重量0.2％硝酸镨混合，搅匀，得到混合液；
3)将混合液上X-5型号大孔树脂柱，上柱速度为0.6BV/h，先水洗至无色，然后用体积浓度为40v％乙醇洗脱，薄层层析跟踪检测，收集含目标成分的乙醇洗脱液，回收乙醇，干燥，得到积雪草苷。
经HLPC分析，积雪草苷的回收率为95.18％以上，纯度高达99.55％以上。
实施例4
1)将积雪草粉碎，加入积雪草总重10倍的70％乙醇溶液回流提取3次，每次1h，将提取液合并，过滤，将滤液回收溶剂，再加50℃水溶解，除去滤渣，即得粗提液；
2)往粗提液加入其重量0.1％氯化铒混合，搅匀，得到混合液；
3)将混合液上X-5型号大孔树脂柱，上柱速度为0.5BV/h，先水洗至无色，然后用体积浓度为45v％乙醇洗脱，薄层层析跟踪检测，收集含目标成分的乙醇洗脱液，回收乙醇，干燥，得到积雪草苷。
经HLPC分析，积雪草苷的回收率为95.09％以上，纯度高达99.63％以上。
Claims (4)
1.从积雪草中提取积雪草苷的方法，其特征在于：包括以下步骤：
1)将积雪草粉碎，用60～70v％乙醇溶液回流提取，将提取液过滤，滤液回收溶剂，再加40～50℃水溶解，得到粗提液；
2)往粗提液加入其重量0.1～0.5％的氯化镧、硫酸铈、硝酸镨或氯化铒，搅匀，得到混合液；
3)将混合液上X-5型号大孔树脂柱，先水洗至无色，然后用体积浓度为35～45v％乙醇洗脱，薄层层析跟踪检测，收集含目标成分的乙醇洗脱液，回收乙醇，干燥，得到积雪草苷。
2.根据权利要求1所述的从积雪草中提取积雪草苷的方法，其特征在于：步骤1)中，乙醇的用量为积雪草重量的10～20倍，回流提取1～3次，每次1～3h。
3.根据权利要求1所述的从积雪草中提取积雪草苷的方法，其特征在于：步骤3)中，混合液上柱速度为0.5～0.8BV/h。
4.根据权利要求1所述的从积雪草中提取积雪草苷的方法，其特征在于：步骤3)中，洗脱速度为2～2.5BV/h。
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