JPS6249279B2 - - Google Patents
Info
- Publication number
- JPS6249279B2 JPS6249279B2 JP60245752A JP24575285A JPS6249279B2 JP S6249279 B2 JPS6249279 B2 JP S6249279B2 JP 60245752 A JP60245752 A JP 60245752A JP 24575285 A JP24575285 A JP 24575285A JP S6249279 B2 JPS6249279 B2 JP S6249279B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acetone
- ppm
- plants
- 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
- 229920001864 tannin Polymers 0.000 claims description 5
- 239000001648 tannin Substances 0.000 claims description 5
- 235000018553 tannin Nutrition 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 6
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 241001070941 Castanea Species 0.000 description 2
- 235000014036 Castanea Nutrition 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 241000209134 Arundinaria Species 0.000 description 1
- 235000008499 Canella winterana Nutrition 0.000 description 1
- 244000080208 Canella winterana Species 0.000 description 1
- 235000021513 Cinchona Nutrition 0.000 description 1
- 241000157855 Cinchona Species 0.000 description 1
- 241000218220 Ulmaceae Species 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940017545 cinnamon bark Drugs 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 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 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000126 substance 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新規タンニン及び
その製造法に関する。
タンニンは広く植物界に分布し、収斂作用のあ
ることが古くから知られ、収斂薬として、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ほどの植物の微量
成分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、地楡等の植物が、酵素阻害作
用等に基づく有用な医薬的効果を有することが知
られていた。
本発明者らは、これらの植物の薬効成分を検索
する目的でこれらに含まれる成分を単離取得して
薬理効果を調べた結果、幸運にも新規なるタンニ
ンに酵素阻害作用のあることを見出し本発明を完
成した。
本発明に係る化合物は、体中酵素蛋白と結合す
ることによつてその活性を低下させる作用を有し
ている。
本発明に係る化合物は、地楡、ウラジロガシ、
桂皮、キナ皮、メヒルギ、栗樹皮等の植物から、
アセトンによる抽出、酢酸エチル：水の分配、あ
るいはカラムクロマト等の公知の方法により容易
に得ることができる。
これらの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 a novel tannin useful as a pharmaceutical and a method for producing the same. Tannins are widely distributed in the plant kingdom, and have long been known to have astringent effects, and have been widely used as an astringent and as a tanning agent to transform hides into leather. Tannin is a trace component of plants with a molecular weight of about 600 to 2,000, and has a complex structure, which, combined with the difficulty of isolation and purification, has delayed research. On the other hand, it has been conventionally known that plants such as elms have useful medicinal effects based on enzyme inhibitory effects and the like. In order to search for medicinal components in these plants, the present inventors isolated and obtained the components contained in these plants and investigated their pharmacological effects, and luckily discovered that a new tannin has an enzyme-inhibiting effect. The invention has been completed. The compound according to the present invention has the effect of reducing the activity of enzyme proteins in the body by binding to them. The compound according to the present invention includes elm, elm,
From plants such as cinnamon bark, cinchona bark, cane bark, chestnut bark, etc.
It can be easily obtained by known methods such as extraction with acetone, partitioning between ethyl acetate and water, or column chromatography. These methods can be summarized as follows, for example.
【表】
以下実施例を掲げて説明する。
実施例
栗樹皮2.13Kgを水性アセトン５で抽出し、水
溶液を酢酸エチル１で分液を10回繰り返した。
酢酸エチル層を集め、Sephadex LH−20でカ
ラムクロマト分離を繰り返して精製したところ、
以下の物質を得た。
compd （収率0.003％）黄かつ色無
定形粉末
〔α〕D＋19.9゜
PMR（acetone−d6）ppm：5.20、5.28（1H in
total、each ｓ、αC1−Ｈ）、7.12、7.16
（2H in total、ｓ、galloyl−Ｈ）
CMR（acetone−d6）ppm：63.8（C2′αβ）、
64.9（C5−α）、66.6（C5−β）、71.5（C3
−α）72.9（C3−β）、78.5（C2−α）、79.9
（C4−α）、80.7（C2−β、C4−β）、98.2
（Cl−α）、103.0（Cl−β）、110.0[Table] Examples will be described below. Example 2.13 kg of chestnut bark was extracted with 5 parts of aqueous acetone, and the aqueous solution was separated with 1 part of ethyl acetate 10 times. The ethyl acetate layer was collected and purified by repeated column chromatography separation using Sephadex LH-20.
The following substances were obtained. compd (Yield 0.003%) Yellow and colored amorphous powder [α] D +19.9゜ PMR (acetone−d 6 ) ppm: 5.20, 5.28 (1H in
total, each s, αC1−H), 7.12, 7.16
(2H in total, s, galloyl-H) CMR (acetone-d 6 ) ppm: 63.8 (C2′αβ),
64.9 (C5−α), 66.6 (C5−β), 71.5 (C3
−α) 72.9 (C3−β), 78.5 (C2−α), 79.9
(C4−α), 80.7 (C2−β, C4−β), 98.2
(Cl−α), 103.0 (Cl−β), 110.0
【式】 121.2【formula】 121.2
【式】 139.0【formula】 139.0
【式】 146.0【formula】 146.0
【式】
167.3（Ｃ＝０）
compd （収率0.006％）無色結晶
〔α〕D−60.0゜
PMR（acetone−d6）ppm：6.44（1H、ｓ、Cl
−Ｈ）、7.08、7.10、7.12（each 2H、ｓ、
galloyl−Ｈ）
CMR（acetone−d6）ppm：67.0（C5、C2′）、
74.1（C3）80.4（C2）、82.5（C4）、100.6
（C1）、110.0[Formula] 167.3 (C=0) compd (Yield 0.006%) Colorless crystal [α] D −60.0゜ PMR (acetone−d 6 ) ppm: 6.44 (1H, s, Cl
-H), 7.08, 7.10, 7.12 (each 2H, s,
galloyl-H) CMR (acetone-d 6 ) ppm: 67.0 (C5, C2′),
74.1 (C3) 80.4 (C2), 82.5 (C4), 100.6
(C1), 110.0
【式】 120.9【formula】 120.9
【式】 139.2【formula】 139.2
【式】 146.0【formula】 146.0
【式】
165.7、167.2、167.3、（Ｃ＝０）
compd （収率0.00065％）無色針状
結晶〔α〕D−47.7゜、mp＞290℃
PMR（acetone−d6）ppm：5.65（ｄ、Ｊ＝８
Hz、C3−Ｈ）、6.60（1H、ｓ、C1−Ｈ）、
7.08、7.16、7.24、7.28（each 2H、ｓ、
galloy−Ｈ）
[Formula] 165.7, 167.2, 167.3, (C=0) compd (Yield 0.00065%) Colorless needle crystals [α] D -47.7°, mp>290℃ PMR (acetone-d 6 ) ppm: 5.65 (d, J=8
Hz, C3-H), 6.60 (1H, s, C1-H),
7.08, 7.16, 7.24, 7.28 (each 2H, s,
galloy-H)
Claims (1)
て、水素又はＧ（Ｇはgalloyl基
【式】を示す。）を示す。ただし、 R51、R52、R53、R54、R55が同時に水素である場
合を除く。また、R52、R54、R55が同時にＧでか
つR51、R53がともに水素である場合を除く。〕で
表わされる新規なタンニン。[Claims] First-order general formula [] [R 51 , R 52 , R 53 , R 54 , and R 55 are the same or different and represent hydrogen or G (G represents a galloyl group [Formula]). However, this excludes the case where R 51 , R 52 , R 53 , R 54 , and R 55 are hydrogen at the same time. Further, the case where R 52 , R 54 and R 55 are G at the same time and R 51 and R 53 are both hydrogen is excluded. ] A new tannin represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60245752A JPS61112090A (en) | 1985-10-31 | 1985-10-31 | Novel tannin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60245752A JPS61112090A (en) | 1985-10-31 | 1985-10-31 | Novel tannin |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57170013A Division JPS5959638A (en) | 1982-09-28 | 1982-09-28 | Novel tannin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61112090A JPS61112090A (en) | 1986-05-30 |
| JPS6249279B2 true JPS6249279B2 (en) | 1987-10-19 |
Family
ID=17138267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60245752A Granted JPS61112090A (en) | 1985-10-31 | 1985-10-31 | Novel tannin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61112090A (en) |
-
1985
- 1985-10-31 JP JP60245752A patent/JPS61112090A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61112090A (en) | 1986-05-30 |
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