JPH0231074B2 - SHINTANNIN - Google Patents
SHINTANNINInfo
- Publication number
- JPH0231074B2 JPH0231074B2 JP20080186A JP20080186A JPH0231074B2 JP H0231074 B2 JPH0231074 B2 JP H0231074B2 JP 20080186 A JP20080186 A JP 20080186A JP 20080186 A JP20080186 A JP 20080186A JP H0231074 B2 JPH0231074 B2 JP H0231074B2
- Authority
- JP
- Japan
- Prior art keywords
- acetone
- present
- plants
- shintannin
- extracted
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 229920001864 tannin Polymers 0.000 description 4
- 239000001648 tannin Substances 0.000 description 4
- 235000018553 tannin Nutrition 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MOJZMWJRUKIQGL-BGYBHLRFSA-N Procyanidin C4 Natural products O[C@@H]1[C@@H](c2cc(O)c(O)cc2)Oc2c([C@@H]3[C@@H](O)[C@@H](c4cc(O)c(O)cc4)Oc4c3c(O)cc(O)c4)c(O)cc(O)c2[C@@H]1c1c(O)cc(O)c2c1O[C@H]([C@@H](O)C2)c1cc(O)c(O)cc1 MOJZMWJRUKIQGL-BGYBHLRFSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000218220 Ulmaceae 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
- 239000000706 filtrate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010985 leather Substances 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
Landscapes
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
本発明は医薬品として有用な新規タンニンに関
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、例えば、びんろうじ等
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 novel tannins useful as pharmaceuticals. 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. The present inventors isolated and obtained the components contained in these plants for the purpose of searching for medicinal components and examined their pharmacological effects. Fortunately, the inventors 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 can be extracted from plants such as bottle wax with acetone, extracted with ethyl acetate, etc.
It can be easily obtained by known methods such as water partitioning or column chromatography. These methods can be summarized as follows, for example.
【表】
〓ロサイド 〓
以下に本発明化合物の所得方法の実施例を掲げ
て本発明を詳細に説明する。
実施例 １
びんろうじ1.2ｇを60％の水性アセトン１で
抽出し、アセトンを留去後、析出する褐色沈澱を
濾去。濾液を酢酸エチル１で10回分配し、水層
をCelite545と混合し、風乾する。これをカラム
につめ、アセトンで溶出する。溶出液の溶媒を留
去後、Sephadex LH―20で水ついで順次メタノ
ールを加えて溶出したところ、40mgの黄かつ色の
無定形粉末を得た。
プロシアンニジン Ｃ―４（Procyanidin Ｃ―
４）黄かつ色無定形粉末（収率0.0028％）
［α］D―97.4゜（アセトン、Ｃ＝0.5）
PMR（DMSO―d6／Pyridin―d5）150℃ppm：
2.75〜3.20（2H，ｍ，C4―Ｈ）、4.03（1H，br.s，
C3″―Ｈ）、4.03〜4.22（1H，ｍ，C3―Ｈ）、4.28
（1H，d.J＝５Hz、C4′―Ｈ）、4.62（1H，ｔ，Ｊ＝
５Hz，C3′―Ｈ）、4.68（1H，ｄ，Ｊ＝５Hz、C2―
Ｈ）、4.80（1H，br.s，C4″―Ｈ）、4.82（1H，ｄ，
Ｊ＝５Hz，C2―Ｈ）、5.40（1H，br.s，C2″―Ｈ）、
5.86〜6.24（4H in total.6，6′，6″，8″）
[Table] 〓Roside〓
The present invention will be described in detail below with reference to examples of methods for obtaining the compounds of the present invention. Example 1 1.2 g of bottle wax was extracted with 60% aqueous acetone 1, and after distilling off the acetone, the precipitated brown precipitate was filtered off. The filtrate is partitioned 10 times with 1 portion of ethyl acetate and the aqueous layer is mixed with Celite 545 and air dried. Load this into a column and elute with acetone. After distilling off the solvent of the eluate, the eluate was eluted with Sephadex LH-20 by sequentially adding water and then methanol to obtain 40 mg of a yellow amorphous powder. Procyanidin C-4
4) Yellow and colored amorphous powder (yield 0.0028%) [α] D -97.4° (acetone, C=0.5) PMR (DMSO-d 6 /Pyridin-d 5 ) 150℃ppm:
2.75-3.20 (2H, m, C 4 - H), 4.03 (1H, br.s,
C 3 ″-H), 4.03-4.22 (1H, m, C 3 -H), 4.28
(1H, dJ=5Hz, C 4' -H), 4.62 (1H, t, J=
5Hz, C 3 '-H), 4.68 (1H, d, J = 5Hz, C 2 -
H), 4.80 (1H, br.s, C 4 ″-H), 4.82 (1H, d,
J=5Hz, C 2 ―H), 5.40 (1H, br.s, C 2 ″―H),
5.86~6.24 (4H in total.6, 6′, 6″, 8″)
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20080186A JPH0231074B2 (en) | 1986-08-26 | 1986-08-26 | SHINTANNIN |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20080186A JPH0231074B2 (en) | 1986-08-26 | 1986-08-26 | SHINTANNIN |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20066981A Division JPS58103383A (en) | 1981-12-12 | 1981-12-12 | New tannin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6248677A JPS6248677A (en) | 1987-03-03 |
| JPH0231074B2 true JPH0231074B2 (en) | 1990-07-11 |
Family
ID=16430416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20080186A Expired - Lifetime JPH0231074B2 (en) | 1986-08-26 | 1986-08-26 | SHINTANNIN |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0231074B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0520276U (en) * | 1991-08-28 | 1993-03-12 | 株式会社タムラ製作所 | Stopper for jack knife type plug |
| JPH0530303Y2 (en) * | 1991-11-27 | 1993-08-03 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2652743B1 (en) * | 1989-10-11 | 1994-05-27 | Cariel Leon | COMPOSITION BASED ON PROANTHOCYANIDOLS. THEIR PHARMACOLOGICAL APPLICATION. |
| US5211944A (en) * | 1990-10-12 | 1993-05-18 | Shaman Pharmaceuticals, Inc. | Proanthocyanidin polymers having antiviral activity and methods of obtaining same |
| US6207842B1 (en) | 1997-10-09 | 2001-03-27 | Mars Incorporated | Process for preparing procyanidin(4-6 or 4-8) oligomers and their derivatives |
| US6156912A (en) * | 1999-04-09 | 2000-12-05 | Mars, Incorporated | 88, 66, and 68 catechin and epicatechin dimers and methods for their preparation |
| US7015338B1 (en) | 1999-04-15 | 2006-03-21 | Mars Incorporated | Synthetic methods for preparing procyanidin oligomers |
| US7381434B2 (en) * | 2003-04-08 | 2008-06-03 | Herbalscience Llc | Methods and compositions of Areca catechu |
| US7067679B2 (en) | 2002-10-02 | 2006-06-27 | Mars, Inc. | Synthesis of dimeric, trimeric, tetrameric pentameric, and higher oligomeric epicatechin-derived procyanidins having 4,8-interflavan linkages and their use to inhibit cancer cell growth through cell cycle arrest |
-
1986
- 1986-08-26 JP JP20080186A patent/JPH0231074B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0520276U (en) * | 1991-08-28 | 1993-03-12 | 株式会社タムラ製作所 | Stopper for jack knife type plug |
| JPH0530303Y2 (en) * | 1991-11-27 | 1993-08-03 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6248677A (en) | 1987-03-03 |
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