JPS6249277B2 - - Google Patents
Info
- Publication number
- JPS6249277B2 JPS6249277B2 JP59161809A JP16180984A JPS6249277B2 JP S6249277 B2 JPS6249277 B2 JP S6249277B2 JP 59161809 A JP59161809 A JP 59161809A JP 16180984 A JP16180984 A JP 16180984A JP S6249277 B2 JPS6249277 B2 JP S6249277B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- different
- same
- tannins
- represent hydrogen
- 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 8
- 229920001864 tannin Polymers 0.000 claims description 7
- 239000001648 tannin Substances 0.000 claims description 7
- 235000018553 tannin Nutrition 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- JCGHAEBIBSEQAD-UUUCSUBKSA-N eugeniin Chemical compound OC1=C(O)C(O)=CC(C(=O)O[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(O)C(O)=C(O)C=3)[C@@H]3OC(=O)C4=CC(O)=C(O)C(O)=C4C4=C(O)C(O)=C(O)C=C4C(=O)OC[C@H]3O2)OC(=O)C=2C=C(O)C(O)=C(O)C=2)=C1 JCGHAEBIBSEQAD-UUUCSUBKSA-N 0.000 description 8
- JCGHAEBIBSEQAD-ANGOHYEVSA-N Tellimagrandin II Natural products O=C(O[C@@H]1[C@@H](OC(=O)c2cc(O)c(O)c(O)c2)O[C@@H]2[C@@H]([C@@H]1OC(=O)c1cc(O)c(O)c(O)c1)OC(=O)c1c(c(O)c(O)c(O)c1)-c1c(O)c(O)c(O)cc1C(=O)OC2)c1cc(O)c(O)c(O)c1 JCGHAEBIBSEQAD-ANGOHYEVSA-N 0.000 description 4
- 229920001990 Tellimagrandin II Polymers 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000003283 Pachira macrocarpa Nutrition 0.000 description 2
- 241001083492 Trapa Species 0.000 description 2
- 235000014364 Trapa natans Nutrition 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 235000009165 saligot Nutrition 0.000 description 2
- XFYIHRTWDXNCTA-UHFFFAOYSA-N Eugenin Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)OC1CCC2C(C)(CCC3C2(C)CCC4(C)C5CC(C)(C)CCC5(C)CCC34C)C1C XFYIHRTWDXNCTA-UHFFFAOYSA-N 0.000 description 1
- 235000016357 Mirtillo rosso Nutrition 0.000 description 1
- 241000208422 Rhododendron Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 1
- 244000223014 Syzygium aromaticum Species 0.000 description 1
- 235000017606 Vaccinium vitis idaea Nutrition 0.000 description 1
- 244000077923 Vaccinium vitis idaea Species 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- SUTUBQHKZRNZRA-UHFFFAOYSA-N eugenin Chemical compound O1C(C)=CC(=O)C=2C1=CC(OC)=CC=2O SUTUBQHKZRNZRA-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
本発明は医薬品として有用なタンニン及びその
製造法に関する。
タンニンは広く植物界に分布し、収れん作用の
あるところから収れん薬として、また皮を革に変
化させるなめし剤として多く用いられてきた。タ
ンニンは分子量600〜2000ほどで複雑な構造を有
しており、単離精製の困難さとあいまつて研究が
遅れていた。
一方、従来よりうらじろがし等の酵素阻害作用
等に基づく有用な医薬的効果が知られており、本
発明者らは、多くの植物より新規のタンニンを単
離取得して薬理効果を検べ、酵素阻害作用を見出
だした。本発明に係る化合物は、体中酵素蛋白と
結合することによつて活性を低下させることが判
つている。
本発明に係る化合物は、代謝調節剤として有用
である。
本発明に係る化合物はEugeniinを除いてすべ
て文献未載の新規化合物である。
なお、Eugeniinについて更に詳しく説明すれ
ば、次のようである。即ち本発明によれば、生ヒ
シ果皮1.6Kg（乾燥物500ｇに相当）から7.7ｇも
の大量のEugeniinを取得することができる。既
存の方法では、生薬丁子500ｇより560mgの
Eugeniinが得られることが明らかにされている
が、本発明は、ヒシ果皮という、でんぷんをとつ
た残りの果皮廃物を利用することにより、しかも
約14倍の収率でEugeniinを得ることができるの
である。
本発明に係る化合物は、楊梅皮、桂皮、梹椰
子、地楡、菱実、ウラジロガシ皮、コケモモ葉等
の植物から、アセトンによる抽出、酢酸エチル：
水の分配、カラムクロマト等公知の方法により容
易に得ることができる。
本発明による抽出方法を総括して示せば例えば
次のようである。
The present invention relates to tannins useful as pharmaceuticals and methods for producing the same. Tannins are widely distributed in the plant kingdom, and have been widely used as an astringent due to their astringent properties, and as a tanning agent to transform hides into leather. Tannins have a molecular weight of 600 to 2,000 and a complex structure, which, combined with the difficulty of isolating and purifying them, has delayed research into tannins. On the other hand, useful medicinal effects have been known based on enzyme inhibitory effects such as tannins, and the present inventors have isolated and obtained novel tannins from many plants to demonstrate their pharmacological effects. We tested it and found that it has an enzyme-inhibiting effect. It has been found that the compounds according to the present invention reduce the activity of enzyme proteins in the body by binding to them. Compounds according to the invention are useful as metabolic regulators. All the compounds according to the present invention, except for Eugeniin, are new compounds that have not been described in any literature. A more detailed explanation of Eugenin is as follows. That is, according to the present invention, a large amount of 7.7 g of Eugeniin can be obtained from 1.6 kg of raw water chestnut peel (equivalent to 500 g of dry matter). In the existing method, 560 mg of herbal medicine cloves are
It has been revealed that eugeniin can be obtained, but the present invention makes it possible to obtain eugeniin at a yield approximately 14 times higher by using the remaining pericarp waste from which starch has been removed, called water chestnut peel. be. The compound according to the present invention can be extracted from plants such as Yang Mei Peel, Cinnamon Peel, Cinnamon Palm, Earth Elm, Rhododendron Peel, Cinnamon Peel, Cowberry Leaf, etc. with acetone, ethyl acetate, etc.
It can be easily obtained by known methods such as water partitioning and column chromatography. The extraction method according to the present invention can be summarized as follows, for example.
【表】
↓
[Table] ↓
Claims (1)
ル、又はガロイル基【式】以下 「Ｇ」と略す。）を表わす。）で表わされる化合
物、 次の式〔〕 で表わされる化合物、 次の式〔〕 （R11、R12、R13、R14は同一又は異なつて水素又
はＧを表わし、R10は水素又は水酸基を表わす。）
で表わされる化合物、及び、次の一般式〔〕 （R20、R21は同一又は異なつて水素又はメチルを
表わす。）で表わされる化合物、により構成され
る群から選ばれる新規タンニン。[Claims] First-order general formula [] (R 5 , R 6 and R 7 are the same or different and represent hydrogen, methyl, or galloyl group [formula] hereinafter abbreviated as "G"). ), the following formula [] A compound represented by the following formula [] (R 11 , R 12 , R 13 and R 14 are the same or different and represent hydrogen or G, and R 10 represents hydrogen or a hydroxyl group.)
Compounds represented by and the following general formula [] (R 20 and R 21 are the same or different and represent hydrogen or methyl.) A novel tannin selected from the group consisting of a compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59161809A JPS6064996A (en) | 1984-07-31 | 1984-07-31 | Tannin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59161809A JPS6064996A (en) | 1984-07-31 | 1984-07-31 | Tannin |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56120372A Division JPS6011912B2 (en) | 1981-07-30 | 1981-07-30 | tannin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6064996A JPS6064996A (en) | 1985-04-13 |
| JPS6249277B2 true JPS6249277B2 (en) | 1987-10-19 |
Family
ID=15742320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59161809A Granted JPS6064996A (en) | 1984-07-31 | 1984-07-31 | Tannin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6064996A (en) |
-
1984
- 1984-07-31 JP JP59161809A patent/JPS6064996A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6064996A (en) | 1985-04-13 |
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