JPH0114233B2 - - Google Patents
Info
- Publication number
- JPH0114233B2 JPH0114233B2 JP12912680A JP12912680A JPH0114233B2 JP H0114233 B2 JPH0114233 B2 JP H0114233B2 JP 12912680 A JP12912680 A JP 12912680A JP 12912680 A JP12912680 A JP 12912680A JP H0114233 B2 JPH0114233 B2 JP H0114233B2
- Authority
- JP
- Japan
- Prior art keywords
- catechin
- biflavonoid compound
- biflavonoid
- group
- charkanyl
- 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
- 150000001875 compounds Chemical class 0.000 claims description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 241000220479 Acacia Species 0.000 claims description 12
- 235000010643 Leucaena leucocephala Nutrition 0.000 claims description 12
- 244000184734 Pyrus japonica Species 0.000 claims description 12
- 238000004440 column chromatography Methods 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000002021 butanolic extract Substances 0.000 claims description 5
- 239000002024 ethyl acetate extract Substances 0.000 claims description 5
- 229920005654 Sephadex Polymers 0.000 claims description 3
- 239000012507 Sephadex™ Substances 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 1
- MLRHUXQCPWXFJT-UHFFFAOYSA-N Gambirin Natural products C1=CC(O)=C2C(CCN3CC(C(CC33)C(OC(C)=O)=COC)CC)=C3NC2=C1 MLRHUXQCPWXFJT-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- PFTAWBLQPZVEMU-ZFWWWQNUSA-N (+)-epicatechin Chemical compound C1([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-ZFWWWQNUSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 12
- 235000005487 catechin Nutrition 0.000 description 12
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 12
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 11
- 238000011282 treatment Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229950001002 cianidanol Drugs 0.000 description 9
- -1 s Species 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 235000007219 (+)-catechin Nutrition 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 235000012734 epicatechin Nutrition 0.000 description 6
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Natural products Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 description 6
- 229930013915 (+)-catechin Natural products 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001765 catechin Chemical class 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 235000007246 (+)-epicatechin Nutrition 0.000 description 3
- 230000005526 G1 to G0 transition Effects 0.000 description 3
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 3
- 239000006286 aqueous extract Substances 0.000 description 3
- 238000010335 hydrothermal treatment Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 229920001864 tannin Polymers 0.000 description 3
- 235000018553 tannin Nutrition 0.000 description 3
- 239000001648 tannin Substances 0.000 description 3
- RSYUFYQTACJFML-UKRRQHHQSA-N (-)-epiafzelechin Chemical group C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C=C1 RSYUFYQTACJFML-UKRRQHHQSA-N 0.000 description 2
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical group C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
- 102000005686 Serum Globulins Human genes 0.000 description 2
- 108010045362 Serum Globulins Proteins 0.000 description 2
- 244000081822 Uncaria gambir Species 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 125000004403 catechin group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000011403 purification operation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XFZJEEAOWLFHDH-UHFFFAOYSA-N (2R,2'R,3R,3'R,4R)-3,3',4',5,7-Pentahydroxyflavan(48)-3,3',4',5,7-pentahydroxyflavan Natural products C=12OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C(O)C=C(O)C=1C(C1=C(O)C=C(O)C=C1O1)C(O)C1C1=CC=C(O)C(O)=C1 XFZJEEAOWLFHDH-UHFFFAOYSA-N 0.000 description 1
- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 1
- JPFCOVZKLAXXOE-XBNSMERZSA-N (3r)-2-(3,5-dihydroxy-4-methoxyphenyl)-8-[(2r,3r,4r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-chromen-4-yl]-3,4-dihydro-2h-chromene-3,5,7-triol Chemical compound C1=C(O)C(OC)=C(O)C=C1C1[C@H](O)CC(C(O)=CC(O)=C2[C@H]3C4=C(O)C=C(O)C=C4O[C@@H]([C@@H]3O)C=3C=CC(O)=CC=3)=C2O1 JPFCOVZKLAXXOE-XBNSMERZSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 102000020018 Cystathionine gamma-Lyase Human genes 0.000 description 1
- 108010045283 Cystathionine gamma-lyase Proteins 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- XFZJEEAOWLFHDH-NFJBMHMQSA-N Epicatechin-(4beta->8)-catechin Natural products C1([C@@H]2[C@H](O)[C@H](C3=C(O)C=C(O)C=C3O2)C=2C(O)=CC(O)=C3C[C@H]([C@H](OC3=2)C=2C=C(O)C(O)=CC=2)O)=CC=C(O)C(O)=C1 XFZJEEAOWLFHDH-NFJBMHMQSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 102000006395 Globulins Human genes 0.000 description 1
- 108010044091 Globulins Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920001991 Proanthocyanidin Polymers 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241001107098 Rubiaceae Species 0.000 description 1
- 102000007562 Serum Albumin Human genes 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000001142 anti-diarrhea Effects 0.000 description 1
- 239000003793 antidiarrheal agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000019606 astringent taste Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229920002770 condensed tannin Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- QOLIPNRNLBQTAU-UHFFFAOYSA-N flavan Chemical class C1CC2=CC=CC=C2OC1C1=CC=CC=C1 QOLIPNRNLBQTAU-UHFFFAOYSA-N 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007124 immune defense Effects 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- 229930005303 indole alkaloid Natural products 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- XFZJEEAOWLFHDH-UKWJTHFESA-N procyanidin B1 Chemical compound C1([C@@H]2[C@H](O)[C@H](C3=C(O)C=C(O)C=C3O2)C=2C(O)=CC(O)=C3C[C@@H]([C@H](OC3=2)C=2C=C(O)C(O)=CC=2)O)=CC=C(O)C(O)=C1 XFZJEEAOWLFHDH-UKWJTHFESA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical group C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12912680A JPS5754181A (ja) | 1980-09-19 | 1980-09-19 | Bifurabonoidokagobutsuoyobisonoseiho |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12912680A JPS5754181A (ja) | 1980-09-19 | 1980-09-19 | Bifurabonoidokagobutsuoyobisonoseiho |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5754181A JPS5754181A (ja) | 1982-03-31 |
| JPH0114233B2 true JPH0114233B2 (enEXAMPLES) | 1989-03-10 |
Family
ID=15001725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12912680A Granted JPS5754181A (ja) | 1980-09-19 | 1980-09-19 | Bifurabonoidokagobutsuoyobisonoseiho |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5754181A (enEXAMPLES) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61112068A (ja) * | 1982-09-28 | 1986-05-30 | Nippon Shinyaku Co Ltd | 新規なタンニン |
| JP2756475B2 (ja) * | 1992-01-21 | 1998-05-25 | 誠一 北林 | 圧力充填可能であることと定量室により定量噴射し得るエアゾール噴射弁 |
| CN102302485B (zh) * | 2008-09-24 | 2013-04-10 | 中国人民解放军军事医学科学院毒物药物研究所 | 一种黄烷衍生物的制药用途 |
-
1980
- 1980-09-19 JP JP12912680A patent/JPS5754181A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5754181A (ja) | 1982-03-31 |
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