CN102133220A - 白头翁皂苷类物质的制备方法及其制剂的制备方法与其在制备治疗癌症药物中的应用 - Google Patents
白头翁皂苷类物质的制备方法及其制剂的制备方法与其在制备治疗癌症药物中的应用 Download PDFInfo
- Publication number
- CN102133220A CN102133220A CN 201010624822 CN201010624822A CN102133220A CN 102133220 A CN102133220 A CN 102133220A CN 201010624822 CN201010624822 CN 201010624822 CN 201010624822 A CN201010624822 A CN 201010624822A CN 102133220 A CN102133220 A CN 102133220A
- Authority
- CN
- China
- Prior art keywords
- pulchinenoside
- preparation
- pulsatilla saponin
- class material
- application
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 76
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 43
- 239000003814 drug Substances 0.000 title claims abstract description 28
- 229930184121 pulsatilla saponin Natural products 0.000 title abstract 6
- AMXYFWUYMQOLRN-UHFFFAOYSA-N 3-oxo-12,11E-biformen Natural products OC1C(C)OC(OC2C(OCC(O)C2O)OC2C(C3C(C4C(C5(CCC6(CCC(C)(C)CC6C5=CC4)C(O)=O)C)(C)CC3)(C)CC2)(C)CO)C(O)C1OC1OC(CO)C(O)C(O)C1O AMXYFWUYMQOLRN-UHFFFAOYSA-N 0.000 claims abstract description 50
- KEOITPILCOILGM-LLJOFIFVSA-N kalopanaxsaponin A Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@@H]2[C@@]([C@H]3[C@]([C@@H]4[C@@]([C@@]5(CC[C@]6(CCC(C)(C)C[C@H]6C5=CC4)C(O)=O)C)(C)CC3)(C)CC2)(C)CO)OC[C@H](O)[C@@H]1O KEOITPILCOILGM-LLJOFIFVSA-N 0.000 claims abstract description 50
- 230000007062 hydrolysis Effects 0.000 claims abstract description 16
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 16
- ISNDTNDJSXYNKT-DVIRKNLQSA-N (1r,3as,5ar,5br,7ar,8r,9s,11ar,11br,13ar,13br)-9-[(2s,3r,4s,5s)-4,5-dihydroxy-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-8-(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hex Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@@H]2[C@@]([C@H]3[C@]([C@@H]4[C@@]([C@@]5(CC[C@]6(CC[C@H]([C@@H]6[C@H]5CC4)C(C)=C)C(O)=O)C)(C)CC3)(C)CC2)(C)CO)OC[C@H](O)[C@@H]1O ISNDTNDJSXYNKT-DVIRKNLQSA-N 0.000 claims description 137
- ISNDTNDJSXYNKT-UHFFFAOYSA-N Pulchinenoside A Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C3C(C4C(C5(CCC6(CCC(C6C5CC4)C(C)=C)C(O)=O)C)(C)CC3)(C)CC2)(C)CO)OCC(O)C1O ISNDTNDJSXYNKT-UHFFFAOYSA-N 0.000 claims description 137
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 135
- 239000000463 material Substances 0.000 claims description 75
- 235000019441 ethanol Nutrition 0.000 claims description 58
- 239000000706 filtrate Substances 0.000 claims description 56
- 229930191447 pulchinenoside Natural products 0.000 claims description 45
- 238000011282 treatment Methods 0.000 claims description 34
- 239000009806 pulsatillae Substances 0.000 claims description 30
- 239000003560 cancer drug Substances 0.000 claims description 29
- 239000000843 powder Substances 0.000 claims description 25
- 238000004458 analytical method Methods 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- 238000003756 stirring Methods 0.000 claims description 23
- 239000003292 glue Substances 0.000 claims description 22
- 238000004321 preservation Methods 0.000 claims description 22
- 238000001914 filtration Methods 0.000 claims description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 17
- 229930182470 glycoside Natural products 0.000 claims description 17
- 150000002338 glycosides Chemical class 0.000 claims description 17
- 239000000741 silica gel Substances 0.000 claims description 17
- 229910002027 silica gel Inorganic materials 0.000 claims description 17
- 229960001866 silicon dioxide Drugs 0.000 claims description 17
- 238000010828 elution Methods 0.000 claims description 15
- 239000007921 spray Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 14
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 14
- 206010017758 gastric cancer Diseases 0.000 claims description 14
- 230000002829 reductive effect Effects 0.000 claims description 14
- 201000011549 stomach cancer Diseases 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 13
- 125000003368 amide group Chemical group 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 12
- 239000004952 Polyamide Substances 0.000 claims description 11
- 230000006837 decompression Effects 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 11
- 238000000605 extraction Methods 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 11
- 235000008216 herbs Nutrition 0.000 claims description 11
- 229920002647 polyamide Polymers 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 11
- 238000010298 pulverizing process Methods 0.000 claims description 11
- 238000001953 recrystallisation Methods 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 11
- 238000001694 spray drying Methods 0.000 claims description 11
- JKLISIRFYWXLQG-UHFFFAOYSA-N Epioleonolsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4CCC3C21C JKLISIRFYWXLQG-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- YBRJHZPWOMJYKQ-UHFFFAOYSA-N Oleanolic acid Natural products CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C1)C(=O)O YBRJHZPWOMJYKQ-UHFFFAOYSA-N 0.000 claims description 9
- MIJYXULNPSFWEK-UHFFFAOYSA-N Oleanolinsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MIJYXULNPSFWEK-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229940100243 oleanolic acid Drugs 0.000 claims description 9
- HZLWUYJLOIAQFC-UHFFFAOYSA-N prosapogenin PS-A Natural products C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC1OCC(O)C(O)C1O HZLWUYJLOIAQFC-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 claims description 8
- 238000004064 recycling Methods 0.000 claims description 8
- NWMIYTWHUDFRPL-UHFFFAOYSA-N sapogenin Natural products COC(=O)C1(CO)C(O)CCC2(C)C1CCC3(C)C2CC=C4C5C(C)(O)C(C)CCC5(CCC34C)C(=O)O NWMIYTWHUDFRPL-UHFFFAOYSA-N 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 7
- -1 cataplasma Substances 0.000 claims description 7
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 7
- 239000002775 capsule Substances 0.000 claims description 6
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000002966 varnish Substances 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 3
- 238000000638 solvent extraction Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 21
- 229930182478 glucoside Natural products 0.000 abstract 1
- 150000008131 glucosides Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 14
- 241000699660 Mus musculus Species 0.000 description 13
- 241000699670 Mus sp. Species 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 229960004397 cyclophosphamide Drugs 0.000 description 12
- 238000011580 nude mouse model Methods 0.000 description 12
- 229930182490 saponin Natural products 0.000 description 12
- 150000007949 saponins Chemical class 0.000 description 12
- 235000017709 saponins Nutrition 0.000 description 12
- 230000000259 anti-tumor effect Effects 0.000 description 11
- 241000699666 Mus <mouse, genus> Species 0.000 description 10
- 230000002401 inhibitory effect Effects 0.000 description 10
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 10
- 210000000952 spleen Anatomy 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 231100000111 LD50 Toxicity 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 210000001541 thymus gland Anatomy 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000000105 evaporative light scattering detection Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 239000008215 water for injection Substances 0.000 description 5
- 238000003556 assay Methods 0.000 description 4
- 230000004071 biological effect Effects 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- LWYXLXAMDLNBFQ-UHFFFAOYSA-N iso-6-Carnavalin Natural products CC(O)CCCCCCCCCCC1CCC(O)C(C)N1 LWYXLXAMDLNBFQ-UHFFFAOYSA-N 0.000 description 4
- 210000004698 lymphocyte Anatomy 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000012567 medical material Substances 0.000 description 4
- RNYZJZKPGHQTJR-UHFFFAOYSA-N protoanemonin Chemical compound C=C1OC(=O)C=C1 RNYZJZKPGHQTJR-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 210000004988 splenocyte Anatomy 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 210000001185 bone marrow Anatomy 0.000 description 3
- 210000002798 bone marrow cell Anatomy 0.000 description 3
- 239000012159 carrier gas Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000007928 intraperitoneal injection Substances 0.000 description 3
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 3
- 239000006199 nebulizer Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 208000008710 Amebic Dysentery Diseases 0.000 description 2
- 206010001986 Amoebic dysentery Diseases 0.000 description 2
- JLUQTCXCAFSSLD-NXEZZACHSA-N Anemonin Chemical compound C1=CC(=O)O[C@]11[C@@]2(C=CC(=O)O2)CC1 JLUQTCXCAFSSLD-NXEZZACHSA-N 0.000 description 2
- JLUQTCXCAFSSLD-UHFFFAOYSA-N Anemonin Natural products C1=CC(=O)OC11C2(C=CC(=O)O2)CC1 JLUQTCXCAFSSLD-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 239000004375 Dextrin Substances 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 102000015696 Interleukins Human genes 0.000 description 2
- 108010063738 Interleukins Proteins 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- 208000003251 Pruritus Diseases 0.000 description 2
- 241000206469 Pulsatilla Species 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000001647 drug administration Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 210000002865 immune cell Anatomy 0.000 description 2
- 230000036039 immunity Effects 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 210000004877 mucosa Anatomy 0.000 description 2
- 210000000822 natural killer cell Anatomy 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 210000005259 peripheral blood Anatomy 0.000 description 2
- 239000011886 peripheral blood Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000002510 pyrogen Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- 238000005550 wet granulation Methods 0.000 description 2
- VZEGBIWAIFLVJH-NXEZZACHSA-N (1r,9ar)-1-methyl-2,3,4,6,7,8,9,9a-octahydro-1h-quinolizine Chemical compound C1CCC[C@@H]2[C@H](C)CCCN21 VZEGBIWAIFLVJH-NXEZZACHSA-N 0.000 description 1
- AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 1
- VCNKUCWWHVTTBY-UHFFFAOYSA-N 18alpha-Oleanane Natural products C1CCC(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C)(C)CC5C4CCC3C21C VCNKUCWWHVTTBY-UHFFFAOYSA-N 0.000 description 1
- MIJYXULNPSFWEK-GTOFXWBISA-N 3beta-hydroxyolean-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MIJYXULNPSFWEK-GTOFXWBISA-N 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- 206010065553 Bone marrow failure Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 241000123887 Pulsatilla chinensis Species 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 208000019065 cervical carcinoma Diseases 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 210000003714 granulocyte Anatomy 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- SIOMFBXUIJKTMF-UHFFFAOYSA-N hypoglauterpenic acid Natural products C1CC(O)C(C)(C)C2=CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C SIOMFBXUIJKTMF-UHFFFAOYSA-N 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 210000002429 large intestine Anatomy 0.000 description 1
- 229960003639 laurocapram Drugs 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 210000005087 mononuclear cell Anatomy 0.000 description 1
- 230000003448 neutrophilic effect Effects 0.000 description 1
- BPAWXSVOAOLSRP-UHFFFAOYSA-N oleanane Natural products CCCCCCCCCCCCCCCC(=O)OC1CCC2(C)C(CCC3(C)C2CC=C4C5CC(C)(C)CCC5(C)C(O)CC34C)C1(C)C BPAWXSVOAOLSRP-UHFFFAOYSA-N 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 229930182493 triterpene saponin Natural products 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
Images
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 201010624822 CN102133220B (zh) | 2010-04-30 | 2010-12-31 | 白头翁皂苷a的制备方法 |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201010160972.9 | 2010-04-30 | ||
CN201010160972 | 2010-04-30 | ||
CN201010175546.2 | 2010-05-18 | ||
CN201010175546 | 2010-05-18 | ||
CN 201010624822 CN102133220B (zh) | 2010-04-30 | 2010-12-31 | 白头翁皂苷a的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102133220A true CN102133220A (zh) | 2011-07-27 |
CN102133220B CN102133220B (zh) | 2013-06-19 |
Family
ID=44293233
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 201010624822 Active CN102133220B (zh) | 2010-04-30 | 2010-12-31 | 白头翁皂苷a的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN102133220B (zh) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102898496A (zh) * | 2012-10-12 | 2013-01-30 | 苏州世林医药技术发展有限公司 | 一种齐墩果酸型皂苷的制备方法 |
CN104857006A (zh) * | 2015-05-18 | 2015-08-26 | 苏州大学附属第一医院 | 白头翁皂苷a在治疗白血病中的药物用途 |
CN108017685A (zh) * | 2017-12-14 | 2018-05-11 | 瑞阳制药有限公司 | 新三萜皂苷类化合物及其制备方法和应用 |
CN108938654A (zh) * | 2017-07-07 | 2018-12-07 | 刘琦 | 一种白头翁皂苷b4的注射用制剂 |
CN112315934A (zh) * | 2020-10-27 | 2021-02-05 | 广西馨海药业科技有限公司 | 白头翁皂苷b4肠溶片的制备工艺 |
-
2010
- 2010-12-31 CN CN 201010624822 patent/CN102133220B/zh active Active
Non-Patent Citations (4)
Title |
---|
《Journal of Asian Natural Products Research》 20090430 Li-Hua Yan et al Triterpenoid saponins from the stems of Clematis parviloba,Journal of Asian Natural Products Research 参见第332页摘要,第336页表3 1-9 第11卷, 第4期 * |
《Planta Med》 20011231 Hee-Juhn Park et al Kalopanaxsaponin A is a Basic Saponin Structure for the Anti-Tumor Activity of Hederagenin Monodesmosides 参见第118页摘要,第119页右栏第3段,第120页表1、2 1-9 第67卷, 第2期 * |
《中药材》 20040831 钟邱等 白头翁中皂苷成分对肿瘤细胞的抑制作用 参见第604-605页 1-10 第27卷, 第8期 * |
《安徽农业科学》 20071010 王伟等 白头翁皂苷及次生物的研究 参见第8779-8780、8784页 1-10 第35卷, 第28期 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102898496A (zh) * | 2012-10-12 | 2013-01-30 | 苏州世林医药技术发展有限公司 | 一种齐墩果酸型皂苷的制备方法 |
CN104857006A (zh) * | 2015-05-18 | 2015-08-26 | 苏州大学附属第一医院 | 白头翁皂苷a在治疗白血病中的药物用途 |
CN108938654A (zh) * | 2017-07-07 | 2018-12-07 | 刘琦 | 一种白头翁皂苷b4的注射用制剂 |
CN108017685A (zh) * | 2017-12-14 | 2018-05-11 | 瑞阳制药有限公司 | 新三萜皂苷类化合物及其制备方法和应用 |
CN112315934A (zh) * | 2020-10-27 | 2021-02-05 | 广西馨海药业科技有限公司 | 白头翁皂苷b4肠溶片的制备工艺 |
CN112315934B (zh) * | 2020-10-27 | 2022-11-11 | 广西馨海药业科技有限公司 | 白头翁皂苷b4肠溶片的制备工艺 |
Also Published As
Publication number | Publication date |
---|---|
CN102133220B (zh) | 2013-06-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102008475B (zh) | 喹诺里西啶生物碱在制备用于***药物的应用 | |
WO2006034655A1 (fr) | Composition pharmaceutique a base de saponines steroidiques, son procede de preparation et son utilisation | |
CN101011435A (zh) | 一种山香圆叶提取物及其制备方法和医药用途 | |
CN102133220B (zh) | 白头翁皂苷a的制备方法 | |
CN101185671B (zh) | 从核桃树皮中提取的抗肿瘤药物及其制备方法 | |
CN100457116C (zh) | 一种具有抗肿瘤作用的“猕猴桃素”及其制备方法和应用 | |
EP3156058B1 (en) | Anti-tumor pharmaceutical application of pentacyclic triterpene saponin compounds of szechuan melandium root | |
CN100463916C (zh) | 雪胆甲素的制备方法和在制备治疗癌症的药物中的应用 | |
CN101011520A (zh) | 含有延龄草提取物的药物制备方法及其应用 | |
CN101119740A (zh) | 中药地榆及其提取物在制备升高红细胞和血红蛋白药物中的应用 | |
CN102068509B (zh) | 白头翁活性组分的含量测定方法及其制备方法 | |
CN100443498C (zh) | 白薇总皂苷及其皂苷化合物在抗炎药物中的应用 | |
CN101537036A (zh) | 一种皂荚皂苷提取物及其制备方法与应用 | |
CN100408594C (zh) | 灰毡毛忍冬活性总皂苷提取物及其制备方法和用途 | |
CN101020637A (zh) | 迷迭香酸的制备方法和应用 | |
CN103721148B (zh) | 一种治疗急慢性胃肠炎的益智仁组合物及其制备方法 | |
CN102875615B (zh) | ***药苷a和***药总皂苷的提取方法及其应用 | |
CN101721434B (zh) | 一种阿里红有效组分及其制备方法和用途 | |
CN101245089A (zh) | 一对新的人参皂苷元和其混合体的制备方法及其制剂 | |
CN100581539C (zh) | 一种白花蛇舌草有效组分及制备方法和应用 | |
CN103156891B (zh) | 预知子活性组分的制备方法及其制剂的制备方法与其在制备抗肿瘤药物中的应用 | |
CN102988525A (zh) | 山楂核中总木脂素的制备方法及新用途 | |
CN104383547B (zh) | 天山雪莲提取物磷脂复合物、口腔崩解片及其制备方法 | |
CN103083388A (zh) | 猪牙皂总皂苷的制备方法 | |
CN102295678B (zh) | 从太白银莲花提取的三萜皂苷类化合物的用途 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CP03 | Change of name, title or address |
Address after: 330006 No. 56 Yangming Road, Jiangxi, Nanchang Patentee after: JIANGXI University OF TRADITIONAL CHINESE MEDICINE Country or region after: China Address before: 330006 No. 56 Yangming Road, Jiangxi, Nanchang Patentee before: Jiangxi University of Traditional Chinese Medicine Country or region before: China |
|
CP03 | Change of name, title or address | ||
TR01 | Transfer of patent right |
Effective date of registration: 20240305 Address after: 330000 788 Torch Road, high tech Development Zone, Nanchang, Jiangxi Patentee after: JIANGXI HERBFINE HI-TECH Co.,Ltd. Country or region after: China Address before: 330006 No. 56 Yangming Road, Jiangxi, Nanchang Patentee before: JIANGXI University OF TRADITIONAL CHINESE MEDICINE Country or region before: China |
|
TR01 | Transfer of patent right |