JPS62142193A - Novel tannin - Google Patents
Novel tanninInfo
- Publication number
- JPS62142193A JPS62142193A JP29189386A JP29189386A JPS62142193A JP S62142193 A JPS62142193 A JP S62142193A JP 29189386 A JP29189386 A JP 29189386A JP 29189386 A JP29189386 A JP 29189386A JP S62142193 A JPS62142193 A JP S62142193A
- Authority
- JP
- Japan
- Prior art keywords
- acetone
- substance
- formula
- present
- soluble substance
- 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.)
- Granted
Links
- 229920001864 tannin Polymers 0.000 title claims description 6
- 239000001648 tannin Substances 0.000 title claims description 6
- 235000018553 tannin Nutrition 0.000 title claims description 6
- 239000000126 substance Substances 0.000 claims abstract description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 239000000043 antiallergic agent Substances 0.000 abstract description 2
- 239000003443 antiviral agent Substances 0.000 abstract description 2
- 244000173853 Sanguisorba officinalis Species 0.000 abstract 1
- 235000008282 Sanguisorba officinalis Nutrition 0.000 abstract 1
- 238000004811 liquid chromatography Methods 0.000 abstract 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 6
- 230000000694 effects Effects 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 241000209134 Arundinaria Species 0.000 description 1
- 229920001408 Casuarictin Polymers 0.000 description 1
- 241000039951 Lithocarpus glaber Species 0.000 description 1
- 244000294611 Punica granatum Species 0.000 description 1
- 235000014360 Punica granatum Nutrition 0.000 description 1
- 244000305267 Quercus macrolepis Species 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 241000218220 Ulmaceae Species 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- WZQCGDLPTFKQNG-NUGBSMSRSA-N chembl507952 Chemical compound OC1=C(O)C(O)=CC(C(=O)O[C@@H]2[C@@H]3OC(=O)C4=CC(O)=C(O)C(O)=C4C4=C(O)C(O)=C(O)C=C4C(=O)O[C@H]3[C@@H]3OC(=O)C4=C(OC=5C(=C(O)C=C(C=5)C(=O)O[C@H]5[C@@H]6OC(=O)C7=CC(O)=C(O)C(O)=C7C7=C(O)C(O)=C(O)C=C7C(=O)O[C@H]6[C@@H]6OC(=O)C7=C(OC=8C(=C(O)C=C(C=8)C(=O)O[C@@H]8[C@@H]9OC(=O)C%10=CC(O)=C(O)C(O)=C%10C%10=C(O)C(O)=C(O)C=C%10C(=O)O[C@H]9[C@@H]9OC(=O)C%10=C(OC=%11C(=C(O)C=C(C=%11)C(=O)O[C@H]%11[C@@H]%12OC(=O)C%13=CC(O)=C(O)C(O)=C%13C%13=C(O)C(O)=C(O)C=C%13C(=O)O[C@H]%12[C@@H]%12OC(=O)C%13=CC(O)=C(O)C(O)=C%13C%13=C(O)C(O)=C(O)C=C%13C(=O)OC[C@H]%12O%11)O)C(O)=C(O)C(O)=C%10C%10=C(O)C(O)=C(O)C=C%10C(=O)OC[C@H]9O8)O)C(O)=C(O)C(O)=C7C7=C(O)C(O)=C(O)C=C7C(=O)OC[C@H]6O5)O)C(O)=C(O)C(O)=C4C4=C(O)C(O)=C(O)C=C4C(=O)OC[C@H]3O2)=C1 WZQCGDLPTFKQNG-NUGBSMSRSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229960002773 hyaluronidase Drugs 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
- 238000000034 method Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】 本発明は医薬品として有用な新規タンニンに関する。[Detailed description of the invention] The present invention relates to novel tannins useful as pharmaceuticals.
タンニンは広く植物界に分布し、収斂作用のあることか
ら古くから知られ、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。Tannins are widely distributed in the plant kingdom and have long been known for their astringent properties, and have been widely used as an astringent and as a tanning agent to transform hides into leather.
タンニンは分子量６００〜２０００はどの植物の＠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
まって研究が遅れていた。Tannin has a molecular weight of 600 to 2,000 and is a component of all plants, and has a complex structure, which, combined with the difficulty of isolation and purification, has delayed research.
一方、従来より、地検等の植物が、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。On the other hand, it has been known for a long time that plants such as Chiken have useful medicinal effects based on enzyme inhibitory effects and the like.
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。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. Fortunately, the inventors discovered that a new tannin has an enzyme-inhibiting effect. The invention has been completed.
本発明に係る化合物は、体中酵素蛋白と結合することに
よってその活性を低下させる作用を有している。The compound according to the present invention has the effect of reducing the activity of enzyme proteins in the body by binding to them.
本発明に係る化合物が抗ヒアルロニダーゼ活性を有して
いることが明らかになっており、本発明化合物は抗アレ
ルギー剤として有用である。It has been revealed that the compound according to the present invention has anti-hyaluronidase activity, and the compound of the present invention is useful as an anti-allergic agent.
また、本発明に係る化合物には、ヘルペスウィルスの発
育を阻害する作用が認められ、抗ウィルス剤としてその
活用が期待される。Furthermore, the compound according to the present invention has been found to have an effect of inhibiting the growth of herpesvirus, and is expected to be used as an antiviral agent.
本発明に係る化合物は、地楡、ウラジロガシ皮、茶菓、
ザクロ葉、メヒルギ皮、櫟樹皮等の植物から、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。The compounds according to the present invention include elm, Japanese oak bark, tea confectionery,
It can be easily obtained from plants such as pomegranate leaves, cane bark, and oak bark by known methods such as extraction with acetone, ethyl acetate:water partitioning, or column chromatography.
以下に本発明に係る化合物の製造に関する実施例を掲げ
る。Examples related to the production of compounds according to the present invention are listed below.
実施例
地楡１６ｋｇを、８０％の水性アセトン６０βで３回抽
出し、アセトンを留去する。留去後、酢酸エチルの５β
で８回分液し、水可溶物質を集める。セライトを加えて
風乾する。これをカラムにつめてアセトンで溶出し、ア
セトン可溶物質を得る。これをさらにセファデックスＬ
Ｈ−２０クロマトで分離精製したところ、１９ｇの褐色
の無晶形粉末■を得た。EXAMPLE 16 kg of elms are extracted three times with 80% aqueous acetone 60β and the acetone is distilled off. After distillation, 5β of ethyl acetate
Separate the solution 8 times and collect water-soluble substances. Add Celite and air dry. This is packed into a column and eluted with acetone to obtain an acetone-soluble substance. Add this to Sephadex L
Separation and purification using H-20 chromatography yielded 19 g of brown amorphous powder (2).
■Ｓａｎｇｕｉｉｎ Ｈ−１１
ｒｒ Ｌａｎ ａｍｏｒｐｌ＋ｏｕｓ ｐｏｗｄｅｒ〔
αｌｏ ＋３３．９° （Ｃ＝０．９４ ａｃｅｔｏ
ｎｅ）ＰＭＲ（ａｃｅｔｏｎｅ−ｄ６）δ： ３．０９
７，３．９２８．３．９５４゜４．０３９ （ｅａｃ
ｈｌＨ，ｂｒ、ｄ、Ｊ ＝ １３．２）１ｚ、１２．７
，１２．３．１３．２１１ｚｒｅｓｐｅｃｔｉｖｅｌｙ
、 Ｈ−６，６’、６” ａｎｄ ６”’ ） 、４．
１４６．４．３６Ｑ。■Sanguiin H-11 rr Lan amorpl+ous powder
αlo +33.9° (C=0.94 aceto
ne) PMR (acetone-d6) δ: 3.09
7,3.928.3.954゜4.039 (eac
hlH, br, d, J = 13.2) 1z, 12.7
,12.3.13.211zrespectively
, H-6,6', 6" and 6"'), 4.
146.4.36Q.
４．４８５〜４．５５０ （４Ｈｉｎ ｔｏｔａｌ、ｍ
、ｌｌ−５＋５’、５” ａｎｄ ５”’）４．１１１
８１，４．９４７，５．０２２，５．０８１，５．１１
２，５．１５７ （８１１１ｎＬｏＬａｌ、ｅａｃｈ
ｔ、Ｊ＝９．５２，９．７７．１０．０１．１０．２
５，８．５５，９．７６Ｈｚ ｒｅｓｐｅｃｔｉｖｅｌ
ｙ Ｈ−２＋３＋３’＋３” ＋４＋４’＋４” ａｎ
ｄ ４”’） ＋５．２１１１ （ＩＩＩ、 ｔ、
Ｊ−ａ、 ７９１１ｚ山２’り） 、５．２９１ （
２＋１．ｄｄ、Ｊ＝３．４１，９．１０Ｈｚ、）ｌ−２
ａｎｄ ２”） 、５．３６６ （１＋ｌ、ｄｄ、Ｊ
＝６．８０゜１３．６Ｈｚ、 Ｈ−６”’） 、５
．４２６ （ＩＨ，ｔ、 Ｊ＝ ９．２８＋１ｚ
、 １１−３″）５．５２３．５．６８２ （ｅａｃ
ｈ ｉｌｌ、ｄｄ、Ｊ＝ ６．５，１３１１ｚ、Ｉｆ−
６ｏｒ ６’）、５．９２０ （１１１，ｄ、Ｊ＝８．
３１１ｚ、Ｉｔ−１’） 、 ５．９４０ （Ｉ
ＩＩ、 ｍ、 Ｉトロ′） 、 ６．１？５．
６．２１２ （ｅａｃｈ Ｉｌｌ、 ｓ、
八ｒ−Ｉｔ） 、 ６．３１１ （ＬＨ。4.485~4.550 (4Hin total, m
, ll-5+5', 5" and 5"') 4.111
81, 4.947, 5.022, 5.081, 5.11
2,5.157 (8111nLoLal, each
t, J=9.52,9.77.10.01.10.2
5, 8.55, 9.76Hz spectivel
y H-2+3+3'+3"+4+4'+4" an
d 4”') +5.2111 (III, t,
J-a, 7911z mountain 2'ri), 5.291 (
2+1. dd, J=3.41, 9.10Hz, )l-2
and 2”), 5.366 (1+l, dd, J
=6.80°13.6Hz, H-6''), 5
．． 426 (IH, t, J= 9.28+1z
, 11-3″) 5.523.5.682 (eac
h ill, dd, J= 6.5, 1311z, If-
6or 6'), 5.920 (111, d, J=8.
311z, It-1'), 5.940 (I
II, m, Itro'), 6.1?5.
6.212 (each Ill, s,
8r-It), 6.311 (LH.
ｄ、 Ｊ＝８．８）１ｚ、 Ｉｆ−１”’） 、 ６．
３３０．６．３３５．６．３６３．６．３Ｂ３゜６．３
８６．６．５１３ （ｅａｃｈ ＩＨ，ｓ、 Ａｒ−Ｉ
ｆ） 、 ６．５２５ （ＩＩＩ、 ｄ。d, J=8.8)1z, If-1"'), 6.
330.6.335.6.363.6.3B3゜6.3
86.6.513 (each IH,s, Ar-I
f), 6.525 (III, d.
Ｊ＝３．９）１ｚ、 Ｈ−１ｏｒ １” ）
、 ６．５４０ （ＬＨ，ｓ、 八ｒ−１１）
６．５４９ （ｌ）Ｉ、 ｄ、 Ｊ−３，４Ｈｚ
、 Ｈ−１ｏｒ １” ） ６．７７４゜６．
７９５． ６．８［３７，６，９０７（ｅｓｃｈ Ｉ
Ｈ，ｓ、 Ａｒ−Ｈ） ７．０１８゜？、１１６
（ｅａｃｈ ｄ、 Ｊ ＝ ２．０１１ｚ、 Ａｒ−１
１） 、 ’７．２４ （３１１，ｂｒ、ｓ。J=3.9)1z, H-1or 1”)
, 6.540 (LH,s, 8r-11)
6.549 (l) I, d, J-3,4Hz
, H-1or 1”) 6.774°6.
795. 6.8[37,6,907(esch I
H, s, Ar-H) 7.018°? , 116
(each d, J = 2.011z, Ar-1
1), '7.24 (311, br, s.
ｇａｌｌｏｙｌ−Ｈ，Ａｒ−ＩＩ）、７．１８８，７．
２０？、７．３８６ （ｅａｃｈｌｌｌ。galloyl-H, Ar-II), 7.188, 7.
20? , 7.386 (eachllll.
ｄ、 Ｊ ＝２．０ＩＩｚ、 Ａｒ−Ｉｆ ）以
上d, J = 2.0IIz, Ar-If) or more
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29189386A JPH0246598B2 (en) | 1986-12-08 | 1986-12-08 | SHINKINARUTANNIN |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29189386A JPH0246598B2 (en) | 1986-12-08 | 1986-12-08 | SHINKINARUTANNIN |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58070774A Division JPS59196884A (en) | 1983-04-20 | 1983-04-20 | Novel tannin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62142193A true JPS62142193A (en) | 1987-06-25 |
| JPH0246598B2 JPH0246598B2 (en) | 1990-10-16 |
Family
ID=17774815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29189386A Expired - Lifetime JPH0246598B2 (en) | 1986-12-08 | 1986-12-08 | SHINKINARUTANNIN |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0246598B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5159069A (en) * | 1988-12-20 | 1992-10-27 | Yamanouchi Pharmaceutical Co., Ltd. | Sulfated tannins and their salts |
| EP0727217A3 (en) * | 1995-02-10 | 1997-01-15 | Suntory Ltd | Pharmaceutical and cosmetic compositions containing ellagitannin of the god type as active ingredient |
| EP0727218A3 (en) * | 1995-02-10 | 1997-01-15 | Suntory Ltd | Anti-allergic composition containing god-type ellagitannin as active ingredient |
| JP2005179285A (en) * | 2003-12-22 | 2005-07-07 | Lotte Co Ltd | Histamine liberation inhibitor and food and drink containing the same |
-
1986
- 1986-12-08 JP JP29189386A patent/JPH0246598B2/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5159069A (en) * | 1988-12-20 | 1992-10-27 | Yamanouchi Pharmaceutical Co., Ltd. | Sulfated tannins and their salts |
| EP0727217A3 (en) * | 1995-02-10 | 1997-01-15 | Suntory Ltd | Pharmaceutical and cosmetic compositions containing ellagitannin of the god type as active ingredient |
| EP0727218A3 (en) * | 1995-02-10 | 1997-01-15 | Suntory Ltd | Anti-allergic composition containing god-type ellagitannin as active ingredient |
| JP2005179285A (en) * | 2003-12-22 | 2005-07-07 | Lotte Co Ltd | Histamine liberation inhibitor and food and drink containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0246598B2 (en) | 1990-10-16 |
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