JPS6352634B2 - - Google Patents
Info
- Publication number
- JPS6352634B2 JPS6352634B2 JP6150880A JP6150880A JPS6352634B2 JP S6352634 B2 JPS6352634 B2 JP S6352634B2 JP 6150880 A JP6150880 A JP 6150880A JP 6150880 A JP6150880 A JP 6150880A JP S6352634 B2 JPS6352634 B2 JP S6352634B2
- Authority
- JP
- Japan
- Prior art keywords
- glucopyranosyl
- rhamnopyranosyl
- methanol
- gynosaponin
- water
- 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.)
- Expired
Links
- 229930182490 saponin Natural products 0.000 claims description 18
- 150000007949 saponins Chemical class 0.000 claims description 18
- 235000017709 saponins Nutrition 0.000 claims description 18
- -1 β-D-glucopyranosyl Chemical group 0.000 claims description 18
- 239000001397 quillaja saponaria molina bark Substances 0.000 claims description 13
- 150000001875 compounds Chemical group 0.000 claims description 7
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000005640 glucopyranosyl group Chemical group 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 229930186669 gynosaponin Natural products 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 238000001179 sorption measurement Methods 0.000 description 9
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- CNPKNBBPPXMRCA-UHFFFAOYSA-N Gynosaponin A Natural products CC1OC(OCC2OC(OC3CCC4(C)C(CCC5(C)C4CC(O)C6C(CCC56C)C(C)(CCC=C(C)C)OC7OC(COC8OC(CO)C(O)C(O)C8O)C(O)C(O)C7O)C3(C)C)C(O)C(O)C2O)C(OC9OC(CO)C(O)C(O)C9O)C(O)C1O CNPKNBBPPXMRCA-UHFFFAOYSA-N 0.000 description 7
- 240000006509 Gynostemma pentaphyllum Species 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- SKUVMNCUDMQXMR-UHFFFAOYSA-N Gynosaponin B Natural products CC1OC(OCC2OC(OC(C)(CCC=C(C)C)C3CCC4(C)C3C(O)CC5C6(C)CCC(OC7OC(COC8OC(C)C(O)C(O)C8OC9OC(CO)C(O)C(O)C9O)C(O)C(O)C7O)C(C)(C)C6CCC45C)C(O)C(O)C2O)C(O)C(O)C1O SKUVMNCUDMQXMR-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- YQKCHRBAJSATCG-UHFFFAOYSA-N UNPD30744 Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC(C)(CCC=C(C)C)C2C3C(C4(CCC5C(C)(C)C(OC6C(C(O)C(O)C(CO)O6)OC6C(C(O)C(O)C(CO)O6)O)CCC5(C)C4CC3O)C)(C)CC2)O1 YQKCHRBAJSATCG-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 241000208340 Araliaceae Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- KKKMWZVRBJUTLX-UHFFFAOYSA-N Gynosaponin F Natural products CC1OC(OCC2OC(OC3CCC4(C)C(CCC5(C)C4CC(O)C6C(CCC56C)C(C)(CCC=C(C)C)OC7OC(CO)C(O)C(O)C7O)C3(C)C)C(O)C(O)C2O)C(OC8OC(CO)C(O)C(O)C8O)C(O)C1O KKKMWZVRBJUTLX-UHFFFAOYSA-N 0.000 description 2
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 2
- 235000003140 Panax quinquefolius Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ZNFRITHWVZXJRK-UHFFFAOYSA-N Vitalboside A Natural products C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC1OC(CO)C(O)C(O)C1O ZNFRITHWVZXJRK-UHFFFAOYSA-N 0.000 description 2
- VTXFLUJNMHWAAT-UHFFFAOYSA-N alternoside VII Natural products CC1(C)CC(O)C2(CO)C(O)CC3(C)C(=CCC4C5(C)CCC(OC6OC(C(O)C(OC7OC(CO)C(O)C(O)C7O)C6O)C(=O)O)C(C)(C)C5CCC34C)C2C1 VTXFLUJNMHWAAT-UHFFFAOYSA-N 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 235000008434 ginseng Nutrition 0.000 description 2
- 229930182494 ginsenoside Natural products 0.000 description 2
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 description 2
- KRPNOGQPDNCBAB-UHFFFAOYSA-N gynosaponin I Natural products CC1OC(OC2C(O)C(O)C(CO)OC2OC(C)(CCC=C(C)C)C3CCC4(C)C3C(O)CC5C6(C)CCC(O)C(C)(C)C6CCC45C)C(O)C(O)C1O KRPNOGQPDNCBAB-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- PIGTXFOGKFOFTO-UHFFFAOYSA-N prosapogenin Chemical compound C12CC(C)(C)CCC2(C(O)=O)C(O)CC(C2(CCC3C4(C=O)C)C)(C)C1=CCC2C3(C)CCC4OC1OC(C(O)=O)C(O)C(O)C1O PIGTXFOGKFOFTO-UHFFFAOYSA-N 0.000 description 2
- OILHVNROWDFZDW-UHFFFAOYSA-N prosapogenin Natural products CC1(C)CCC2(C(O)CC3(C)C(=CCC4C5(C)CCC(OC6OC(CO)C(O)C(O)C6O)C(C)(C=O)C5CCC34C)C2C1)C(=O)O OILHVNROWDFZDW-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- IAGSHEHQJJTLLR-UHFFFAOYSA-N sapindoside B 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)C1OC1OCC(O)C(O)C1O IAGSHEHQJJTLLR-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000219104 Cucurbitaceae Species 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- KPOSIVPPNIGLFV-UHFFFAOYSA-N Saponin H Chemical compound CC(C)=CC(O)CC1(C)OC1C1C2(CC(=O)OC2)C2(C)CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC1 KPOSIVPPNIGLFV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 229940089161 ginsenoside Drugs 0.000 description 1
- GZYPWOGIYAIIPV-JBDTYSNRSA-N ginsenoside Rb1 Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)O[C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(CC[C@H]4C(C)(C)[C@@H](O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O)CC[C@]4(C)[C@H]3C[C@H]2O)C)(C)CC1)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GZYPWOGIYAIIPV-JBDTYSNRSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6150880A JPS56127400A (en) | 1980-05-08 | 1980-05-08 | Preparation of saponin by acid hydrolysis |
| US06/205,377 US4339442A (en) | 1980-03-11 | 1980-11-07 | Gynosaponins, their use and a process for preparing the same |
| DE19803042117 DE3042117A1 (de) | 1980-03-11 | 1980-11-07 | Gynosaponine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6150880A JPS56127400A (en) | 1980-05-08 | 1980-05-08 | Preparation of saponin by acid hydrolysis |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55030636A Division JPS6043359B2 (ja) | 1980-03-11 | 1980-03-11 | ギノサポニン類およびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56127400A JPS56127400A (en) | 1981-10-06 |
| JPS6352634B2 true JPS6352634B2 (enrdf_load_stackoverflow) | 1988-10-19 |
Family
ID=13173098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6150880A Granted JPS56127400A (en) | 1980-03-11 | 1980-05-08 | Preparation of saponin by acid hydrolysis |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56127400A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100486988C (zh) | 2004-02-13 | 2009-05-13 | 云南白药集团天然药物研究院 | 一种20（R）—人参皂苷Rh2的制备方法 |
| CN102759597B (zh) * | 2011-04-29 | 2016-02-10 | 天津药物研究院 | 一种七叶皂苷类成分的快速检测方法 |
| CN112588318B (zh) * | 2020-12-15 | 2022-02-15 | 江南大学 | 一种白首乌短糖链c21甾苷的绿色高效制备方法 |
-
1980
- 1980-05-08 JP JP6150880A patent/JPS56127400A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56127400A (en) | 1981-10-06 |
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