JPS6353993B2 - - Google Patents
Info
- Publication number
- JPS6353993B2 JPS6353993B2 JP20066981A JP20066981A JPS6353993B2 JP S6353993 B2 JPS6353993 B2 JP S6353993B2 JP 20066981 A JP20066981 A JP 20066981A JP 20066981 A JP20066981 A JP 20066981A JP S6353993 B2 JPS6353993 B2 JP S6353993B2
- Authority
- JP
- Japan
- Prior art keywords
- glu
- acetone
- hhdp
- gal
- present
- 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 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 9
- 229920001301 Hexahydroxydiphenic acid Polymers 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
- 238000004440 column chromatography Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 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 2
- 235000011330 Armoracia rusticana Nutrition 0.000 description 1
- 240000003291 Armoracia rusticana Species 0.000 description 1
- 241000209134 Arundinaria Species 0.000 description 1
- 235000008499 Canella winterana Nutrition 0.000 description 1
- 244000080208 Canella winterana Species 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 235000014036 Castanea Nutrition 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940017545 cinnamon bark Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- SWRFKGRMQVLMKA-UHFFFAOYSA-N galloyl-bis-HHDP glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC2C3OC(=O)C4=CC(O)=C(O)C(O)=C4C4=C(O)C(O)=C(O)C=C4C(=O)OC3C3OC(=O)C4=CC(O)=C(O)C(O)=C4C4=C(O)C(O)=C(O)C=C4C(=O)OCC3O2)=C1 SWRFKGRMQVLMKA-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000638 solvent extraction Methods 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。
以下に本発明化合物の取得方法の実施例を掲げ
て本発明の詳細に説明する。
実施例 １
ウラジロガシ皮6.3Kgを60％の水性アセトン５
で抽出し、アセトンを留去後、析出する沈澱を
濾去する。濾液を酢酸エチル１で10回分配し、
酢酸エチル可溶部をあつめ、Sephadex LH−20
でエタノールを用いカラムクロマトグラフイー分
離を行い、６個のフラクシヨンに分画する。フラ
クシヨン１を更にSephadex LH−20でアセトン
を用いてカラムクロマトグラフイー分離を行い、
ついでピリジン−水の混液から再結晶を行い1.2
ｇの黄色結晶を得た。
１（β）−galloyl pedunculagin （収率0.006
％）無色無定形粉末〔α〕D＋35.2゜（acetone、ｃ＝
1.08）
PMR（acetone−d6）ppm：3.87（1H、br.d、Ｊ＝
14Hz、glu.C6−Ｈ）、4.48（1H、dd、Ｊ＝8.6Hz、
glu.C5−Ｈ）、5.13（1H、ｔ、Ｊ＝９Hz、glu.C4
−Ｈ）、5.13（1H、ｔ、Ｊ＝８Hz、glu.C2−Ｈ）、
5.47（1H、ｔ、Ｊ＝８Hz、glu.C3−Ｈ）、5.12−
5.52（glu.C6−Ｈ）、6.22（1H、ｄ、Ｊ＝８Hz、
anom.H）、6.38、6.47、6.55、6.68（each 1H、
ｓ、HHDP.H）、7.18（2H、ｓ、gal.H）．
CMR（acetone−d6＋D2O）ppm：62.3（glu.C6）、
69.0（glu.C4）、73.2（glu.C2）、75.7（glu.C3）、
77.0（glu.C5）、91.3（glu.C1）、106.8、107.0、
107.9（HHDP、C5、C5′）、110.0（gal.C2、C6）、
114.1、114.7、115.5、115.8（HHDP.C1、C1′）、
119.1（gal.C1）、125.2、125.4、125.7（HHDP.
C6、C6′）、135.9、136.2（HHDP.C3、C3′）、
139.7（gal.C4）、144.1、144.8、144.9、145.8
（HHDP、C2、C2′、C4、C4′、gal.C3、C5）、
164.9、167.7、168.0、168.4、169.1（−COO−）．
ただし、Ｇはガロイル基
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 600 to 2,000 and has a complex structure, and research on it has been delayed due to difficulties in isolating and purifying it. 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 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, ethyl acetate:water partitioning, or column chromatography. 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 6.3 kg of horseradish skin was mixed with 60% aqueous acetone 5
After the acetone is distilled off, the precipitate is filtered off. The filtrate was partitioned 10 times with 1 part of ethyl acetate,
Collect the ethyl acetate soluble portion and store it in Sephadex LH-20.
Column chromatography separation using ethanol is performed to separate into 6 fractions. Fraction 1 was further separated by column chromatography using acetone on Sephadex LH-20.
Then recrystallize from a pyridine-water mixture 1.2
g yellow crystals were obtained. 1(β)-galloyl pedunculagin (yield 0.006
%) Colorless amorphous powder [α] D +35.2゜(acetone, c=
1.08) PMR (acetone-d 6 ) ppm: 3.87 (1H, br.d, J=
14Hz, glu.C 6 −H), 4.48 (1H, dd, J=8.6Hz,
glu.C 5 −H), 5.13 (1H, t, J=9Hz, glu.C 4
-H), 5.13 (1H, t, J=8Hz, glu.C 2 -H),
5.47 (1H, t, J=8Hz, glu.C 3 −H), 5.12−
5.52 (glu.C 6 −H), 6.22 (1H, d, J = 8Hz,
anom.H), 6.38, 6.47, 6.55, 6.68 (each 1H,
s, HHDP.H), 7.18 (2H, s, gal.H). CMR (acetone−d 6 + D 2 O) ppm: 62.3 (glu.C 6 ),
69.0 (glu.C 4 ), 73.2 (glu.C 2 ), 75.7 (glu.C 3 ),
77.0 (glu.C 5 ), 91.3 (glu.C 1 ), 106.8, 107.0,
107.9 (HHDP, C 5 , C 5 ′), 110.0 (gal.C 2 , C 6 ),
114.1, 114.7, 115.5, 115.8 (HHDP.C 1 , C 1 ′),
119.1 (gal.C 1 ), 125.2, 125.4, 125.7 (HHDP.
C 6 , C 6 ′), 135.9, 136.2 (HHDP.C 3 , C 3 ′),
139.7 (gal.C 4 ), 144.1, 144.8, 144.9, 145.8
(HHDP, C 2 , C 2 ′, C 4 , C 4 ′, gal.C 3 , C 5 ),
164.9, 167.7, 168.0, 168.4, 169.1 (−COO−). However, G is galloyl group
【式】を表す。Represents [formula].
Claims (1)
【式】を表す。[Claims] 1. The following formula [] A compound represented by However, G represents a galloyl group [Formula].
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20066981A JPS58103383A (en) | 1981-12-12 | 1981-12-12 | New tannin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20066981A JPS58103383A (en) | 1981-12-12 | 1981-12-12 | New tannin |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20080186A Division JPH0231074B2 (en) | 1986-08-26 | 1986-08-26 | SHINTANNIN |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58103383A JPS58103383A (en) | 1983-06-20 |
| JPS6353993B2 true JPS6353993B2 (en) | 1988-10-26 |
Family
ID=16428259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20066981A Granted JPS58103383A (en) | 1981-12-12 | 1981-12-12 | New tannin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58103383A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH657866A5 (en) * | 1983-07-06 | 1986-09-30 | Nestle Sa | ANTIOXYGEN PROTECTION OF FOOD AND COSMETIC PRODUCTS BY PLANT EXTRACTS. |
| JPS6116982A (en) * | 1984-07-03 | 1986-01-24 | Kikkoman Corp | Antioxidant |
| SG188529A1 (en) * | 2010-09-14 | 2013-04-30 | Chengdu Keer Pharmaceutical Co Ltd | A sanguisorba tannin extract, and preparation method and use thereof |
-
1981
- 1981-12-12 JP JP20066981A patent/JPS58103383A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58103383A (en) | 1983-06-20 |
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