JPS58208300A - ギペノシド類 - Google Patents
ギペノシド類Info
- Publication number
- JPS58208300A JPS58208300A JP9179382A JP9179382A JPS58208300A JP S58208300 A JPS58208300 A JP S58208300A JP 9179382 A JP9179382 A JP 9179382A JP 9179382 A JP9179382 A JP 9179382A JP S58208300 A JPS58208300 A JP S58208300A
- Authority
- JP
- Japan
- Prior art keywords
- glucopyranosyl
- group
- ene
- beta
- dammar
- 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
- -1 beta-glucopyranosyl Chemical group 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003132 pyranosyl group Chemical group 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 28
- 229930182490 saponin Natural products 0.000 abstract description 24
- 150000007949 saponins Chemical class 0.000 abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 24
- 239000001397 quillaja saponaria molina bark Substances 0.000 abstract description 16
- 240000006509 Gynostemma pentaphyllum Species 0.000 abstract description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract description 7
- 235000002956 Gynostemma pentaphyllum Nutrition 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 abstract description 6
- 238000010828 elution Methods 0.000 abstract description 4
- 230000000767 anti-ulcer Effects 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 210000004798 organs belonging to the digestive system Anatomy 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- 229930187479 gypenoside Natural products 0.000 description 23
- 235000017709 saponins Nutrition 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- ZRBFCAALKKNCJG-UHFFFAOYSA-N gypenoside-XVII 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)OC1COC1OC(CO)C(O)C(O)C1O ZRBFCAALKKNCJG-UHFFFAOYSA-N 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- FBFMBWCLBGQEBU-RXMALORBSA-N (2s,3r,4s,5s,6r)-2-[(2r,3r,4s,5s,6r)-2-[[(3s,5r,6s,8r,9r,10r,12r,13r,14r,17s)-3,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2s)-6-methyl-2-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecah Chemical class O([C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(C[C@@H]([C@H]4C(C)(C)[C@@H](O)CC[C@]4(C)[C@H]3C[C@H]2O)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C)(C)CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O FBFMBWCLBGQEBU-RXMALORBSA-N 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229940088598 enzyme Drugs 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- PFWQCAQPDUBXKO-UHFFFAOYSA-N Gypenoside XX Natural products CC1OC(OCC2OC(OC3CCC4(C)C(CCC5(C)C4CC(O)C6C(CCC56C)C(C)(CCC=C(/C)CO)OC7OC(COC8OC(CO)C(O)C(O)C8O)C(O)C(O)C7O)C3(C)C)C(OC9OC(CO)C(O)C(O)C9O)C(O)C2O)C(O)C(O)C1O PFWQCAQPDUBXKO-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 108010059892 Cellulase Proteins 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 229940106157 cellulase Drugs 0.000 description 3
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 241001065361 Gynostemma Species 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000007071 enzymatic hydrolysis Effects 0.000 description 2
- 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 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004382 Amylase Substances 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010021511 Aspergillus oryzae carboxyl proteinase Proteins 0.000 description 1
- 229920002871 Dammar gum Polymers 0.000 description 1
- 206010061459 Gastrointestinal ulcer Diseases 0.000 description 1
- 240000003185 Gynostemma laxum Species 0.000 description 1
- PNTJFJBIKBSAOS-UHFFFAOYSA-N Gypenoside XL Natural products CC(=CCCC(C)(O)C1CCC2(C)C1C(O)CC3C2(C)CCC4C(C)(C)C(CCC34C=O)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C PNTJFJBIKBSAOS-UHFFFAOYSA-N 0.000 description 1
- YERVVNJJSVYXJR-UHFFFAOYSA-N Gypenoside XXII Natural products C1CC(C2(C)C(C3(CCC(C(C)(C)C3CC2)OC2C(C(O)C(O)C(CO)O2)OC2C(C(O)C(O)C(CO)O2)O)CO)CC2)(C)C2C1C(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O YERVVNJJSVYXJR-UHFFFAOYSA-N 0.000 description 1
- HBTODKWWQKMJQW-UHFFFAOYSA-N Gypenoside XXXIV Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC(CCC=C(C)C)C2C3C(C4(C)C(C5(CCC(C(C)(C)C5CC4)OC4C(C(O)C(O)C(CO)O4)OC4C(C(O)C(O)C(CO)O4)O)C=O)CC3)(C)CC2)O1 HBTODKWWQKMJQW-UHFFFAOYSA-N 0.000 description 1
- XZDNZWXPYVUYFI-UHFFFAOYSA-N Gypenoside XXXV Natural products C1CC(C2(C)C(C3(CCC(C(C)(C)C3CC2)OC2C(C(O)C(O)C(CO)O2)OC2C(C(O)C(O)C(CO)O2)O)C=O)CC2)(C)C2C1C(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O XZDNZWXPYVUYFI-UHFFFAOYSA-N 0.000 description 1
- OIICKOUPTAFGTH-UHFFFAOYSA-N Gypenoside XXXVI Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC(C)(CCC=C(C)C)C2C3C(C4(C)C(C5(CCC(C(C)(C)C5CC4)OC4C(C(O)C(O)C(CO)O4)OC4C(C(O)C(O)C(CO)O4)O)C=O)CC3)(C)CC2)O1 OIICKOUPTAFGTH-UHFFFAOYSA-N 0.000 description 1
- 108090000604 Hydrolases Proteins 0.000 description 1
- 102000004157 Hydrolases Human genes 0.000 description 1
- 108010059820 Polygalacturonase Proteins 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 108010028144 alpha-Glucosidases Proteins 0.000 description 1
- 102000016679 alpha-Glucosidases Human genes 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 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 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 108010093305 exopolygalacturonase Proteins 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005640 glucopyranosyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 108010030923 hesperidinase Proteins 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 108010001078 naringinase Proteins 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9179382A JPS58208300A (ja) | 1982-05-28 | 1982-05-28 | ギペノシド類 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9179382A JPS58208300A (ja) | 1982-05-28 | 1982-05-28 | ギペノシド類 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58208300A true JPS58208300A (ja) | 1983-12-03 |
| JPH0119399B2 JPH0119399B2 (enrdf_load_stackoverflow) | 1989-04-11 |
Family
ID=14036484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9179382A Granted JPS58208300A (ja) | 1982-05-28 | 1982-05-28 | ギペノシド類 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58208300A (enrdf_load_stackoverflow) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5857398A (ja) * | 1981-10-01 | 1983-04-05 | Nippon Shoji Kk | ギペノシド類 |
-
1982
- 1982-05-28 JP JP9179382A patent/JPS58208300A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5857398A (ja) * | 1981-10-01 | 1983-04-05 | Nippon Shoji Kk | ギペノシド類 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0119399B2 (enrdf_load_stackoverflow) | 1989-04-11 |
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