JPS6222990B2 - - Google Patents
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- Publication number
- JPS6222990B2 JPS6222990B2 JP58070774A JP7077483A JPS6222990B2 JP S6222990 B2 JPS6222990 B2 JP S6222990B2 JP 58070774 A JP58070774 A JP 58070774A JP 7077483 A JP7077483 A JP 7077483A JP S6222990 B2 JPS6222990 B2 JP S6222990B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- acetone
- plants
- compound according
- formula
- 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 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- 150000001875 compounds Chemical class 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 244000305267 Quercus macrolepis Species 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000209134 Arundinaria Species 0.000 description 1
- 244000294611 Punica granatum Species 0.000 description 1
- 235000014360 Punica granatum Nutrition 0.000 description 1
- 235000012377 Salvia columbariae var. columbariae Nutrition 0.000 description 1
- 240000005481 Salvia hispanica Species 0.000 description 1
- 235000001498 Salvia hispanica Nutrition 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- CTVAVEOYQKVFFY-WDLJOSFISA-N Theasinensin B Natural products O=C(O[C@H]1[C@@H](c2c(c(O)c(O)c(O)c2)-c2c(O)c(O)c(O)cc2[C@@H]2[C@@H](O)Cc3c(O)cc(O)cc3O2)Oc2c(c(O)cc(O)c2)C1)c1cc(O)c(O)c(O)c1 CTVAVEOYQKVFFY-WDLJOSFISA-N 0.000 description 1
- CTVAVEOYQKVFFY-DUSGSIEYSA-N Theasinensin B Chemical compound O([C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C(O)=C1C1=C(O)C(O)=C(O)C=C1[C@H]1OC2=CC(O)=CC(O)=C2C[C@H]1O)C(=O)C1=CC(O)=C(O)C(O)=C1 CTVAVEOYQKVFFY-DUSGSIEYSA-N 0.000 description 1
- 241000218220 Ulmaceae Species 0.000 description 1
- 241001106462 Ulmus Species 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000014167 chia Nutrition 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
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 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
- 239000007788 liquid 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
- 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
- 238000000926 separation method Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YUULFXAQUWEYNP-GXAWFILRSA-N theasinensin A Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C(=C(O)C(O)=C(O)C=1)C=1C(=CC(O)=C(O)C=1O)[C@@H]1[C@@H](CC2=C(O)C=C(O)C=C2O1)OC(=O)C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 YUULFXAQUWEYNP-GXAWFILRSA-N 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
Landscapes
- Medicines Containing Plant Substances (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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。 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.
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。 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.
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, and luckily 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
ることによつ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つており、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、ヘルペスウイ
ルスの発育を阻害する作用が認められ、抗ウイル
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、茶葉、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 compound according to the present invention can be extracted from plants such as elm tree, oak bark, tea leaves, pomegranate leaves, cane bark, and oak bark by known methods such as extraction with acetone, ethyl acetate:water partitioning, or column chromatography. 〓〓〓
can be obtained more easily.
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
新鮮チヤ葉15Kgを、80％の水性アセトン40で
３回抽出し、アセトンを留去する。留去後、析出
する沈澱を濾去する。濾液は酢酸エチルの３で
10回分液し、酢酸エチル可溶物質を集めて水で洗
浄し、セフアデツクスLH−20、ダイヤイオンHP
−20で分離精製したところ、73mgの淡褐色の無晶
形粉末と、20mgの淡褐色の無晶形粉末を得
た。EXAMPLE 15 kg of fresh chia leaves are extracted three times with 80% aqueous acetone 40 and the acetone is distilled off. After distilling off, the precipitate that precipitates out is filtered off. The filtrate is diluted with ethyl acetate.
Separate the liquid 10 times, collect the ethyl acetate soluble substances, wash with water, and add Sephadex LH-20 and Diaion HP.
Separation and purification at −20°C yielded 73 mg of light brown amorphous powder and 20 mg of light brown amorphous powder.
Theasinensin Ａ（Compd.X）
ａ tan amorphous powder
〔α〕D−226.8゜（ｃ＝0.73acetone）
元素分析値（C30H26O14・１1/2H2Oとして）
計算値：Ｃ 56.51；Ｈ 4.35
実測値：Ｃ 56.28；Ｈ 4.44
PMR（acetone−d6）ppm：2.40〜3.10（4H、
ｍ、C4−Ｈ）、4.80（2H、ｓ、C2−Ｈ）、
3.35（2H、br、ｓ、C3−Ｈ）、5.92〜6.81
（4H、ｍ、C6、８−Ｈ）、6.88（2H、ｓ、C6
−Ｈ）、7.00（4H、ｓ、galloyl−Ｈ）
CMR（acetone−d6＋D2O）δ：26.8（C4）、68.9
（C3）、76.0（C2）、95.5、96.4（C6、８）、
98.3（C4a）、108.0（C2′）、110.0（C6″）、
112.7（C2″）、121.3（C1″）、129.0（C1′）、
133.0（C4′）、139.0（C4″）144.9、145.8、
145.9、145.6（C3′、5′、3″、5″）、157.0、
157.3（C5、７、９）、167.0（−COO−）
C.D.（MeOH）（Ｃ＝0.0293） 〔θ〕220−4.64×
105、〔θ〕244＋4.09×104、〔θ〕265−2.05×
104
収率 0.00049％
Theasinensin Ｂ（Compd.XI）
ａ tan amorphous powder
〔α〕D−147.2゜（ｃ＝0.5acetone）
PMR（acetone−d6）ppm：2.25〜3.04（4H、
ｍ、C4、C4′−Ｈ）、4.07（1H、br.s、C3−
Ｈ）、4.62（1H、ｓ、C2−Ｈ）、4.78（1H、
ｓ、C2′−Ｈ）、5.30（1H、ｍ、C3′−Ｈ）
5.82〜6.04（4H、ｍ、C6、８、6′、8′−
Ｈ）、6.82、6.89（each1H、ｓ、C6″−Ｈ
or C6−Ｈ）、6.96（2H、ｓ、galloyl−
Ｈ）
CMR（acetone−d6）δ：26.8、28.6（C4、
C4′）64.9（C3）、68.6（C3″）、76.1（C2）、
77.2（C2′）、95.7、95.9、96.1、96.5（C6、
８、6′、8′）、98.5、99.4（C4a、4a′）、
107.9、108.8（C6″、６）、110.0（C2〓、
６〓）111.3、111.8（C2″、２）121.6（C1
〓）、129.1、130.3（C1″、１）133.3、
133.6（C4″、４）、138.9（C1〓）、144.9、
145.8、146.1、146.3（C3″、３、5″、５
、３〓、５〓）157.3、157.7（C5、７、
９、5′、7′、9′）、166.7（−COOH）
収率 0.00013％
〓〓〓〓〓
〓〓〓〓〓
Theasinensin A ( Compd . Actual value: C 56.28; H 4.44 PMR (acetone-d6) ppm: 2.40-3.10 (4H,
m, C4-H), 4.80 (2H, s, C2-H),
3.35 (2H, br, s, C3-H), 5.92-6.81
(4H, m, C6, 8-H), 6.88 (2H, s, C6
-H), 7.00 (4H, s, galloyl-H) CMR (acetone-d6+D 2 O) δ: 26.8 (C4), 68.9
(C3), 76.0 (C2), 95.5, 96.4 (C6, 8),
98.3 (C4a), 108.0 (C2′), 110.0 (C6″),
112.7 (C2″), 121.3 (C1″), 129.0 (C1′),
133.0 (C4′), 139.0 (C4″) 144.9, 145.8,
145.9, 145.6 (C3′, 5′, 3″, 5″), 157.0,
157.3 (C5, 7, 9), 167.0 (−COO−) CD (MeOH) (C=0.0293) [θ] 220 −4.64×
10 5 , [θ] 244 +4.09×10 4 , [θ] 265 −2.05×
10 4 Yield 0.00049% Theasinensin B ( Compd.
m, C4, C4'-H), 4.07 (1H, br.s, C3-
H), 4.62 (1H, s, C2-H), 4.78 (1H,
s, C2'-H), 5.30 (1H, m, C3'-H)
5.82~6.04 (4H, m, C6, 8, 6', 8'-
H), 6.82, 6.89 (each1H, s, C6″-H
or C6−H), 6.96 (2H, s, galloyl−
H) CMR (acetone-d6) δ: 26.8, 28.6 (C4,
C4′) 64.9 (C3), 68.6 (C3″), 76.1 (C2),
77.2 (C2′), 95.7, 95.9, 96.1, 96.5 (C6,
8, 6′, 8′), 98.5, 99.4 (C4a, 4a′),
107.9, 108.8 (C6″, 6), 110.0 (C2〓,
6〓) 111.3, 111.8 (C2″, 2) 121.6 (C1
〓), 129.1, 130.3 (C1″, 1) 133.3,
133.6 (C4″, 4), 138.9 (C1〓), 144.9,
145.8, 146.1, 146.3 (C3″, 3, 5″, 5
, 3〓, 5〓) 157.3, 157.7 (C5, 7,
9, 5′, 7′, 9′), 166.7 (−COOH) Yield 0.00013% 〓〓〓〓〓
〓〓〓〓〓
Claims (1)
びR21は、同一又は異なつて、水素又はＧを表わ
す。Ｇはガロイル基【式】を表わ す。）で表わされる新規なるタンニン。[Claims] First-order general formula [] (In the formula, R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 and R 21 are the same or different and represent hydrogen or G. G represents a galloyl group [Formula] A new tannin expressed by .).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58070774A JPS59196884A (en) | 1983-04-20 | 1983-04-20 | Novel tannin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58070774A JPS59196884A (en) | 1983-04-20 | 1983-04-20 | Novel tannin |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61291892A Division JPS62142181A (en) | 1986-12-08 | 1986-12-08 | Novel tannin |
| JP29189386A Division JPH0246598B2 (en) | 1986-12-08 | 1986-12-08 | SHINKINARUTANNIN |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59196884A JPS59196884A (en) | 1984-11-08 |
| JPS6222990B2 true JPS6222990B2 (en) | 1987-05-20 |
Family
ID=13441199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58070774A Granted JPS59196884A (en) | 1983-04-20 | 1983-04-20 | Novel tannin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59196884A (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63162685A (en) * | 1986-12-26 | 1988-07-06 | Kikkoman Corp | Production of proanthocyanidin |
| JPH0211520A (en) * | 1988-06-29 | 1990-01-16 | Momotani Jiyuntenkan:Kk | Hyaluronidase inactivation agent |
| FR2652743B1 (en) * | 1989-10-11 | 1994-05-27 | Cariel Leon | COMPOSITION BASED ON PROANTHOCYANIDOLS. THEIR PHARMACOLOGICAL APPLICATION. |
| JP2727471B2 (en) * | 1989-09-14 | 1998-03-11 | 三井農林株式会社 | Influenza virus infection prevention agent |
| JP2888554B2 (en) * | 1989-09-20 | 1999-05-10 | 三井農林株式会社 | Mycoplasma infection preventive agent |
| US5211944A (en) * | 1990-10-12 | 1993-05-18 | Shaman Pharmaceuticals, Inc. | Proanthocyanidin polymers having antiviral activity and methods of obtaining same |
| AU1669395A (en) * | 1994-02-17 | 1995-09-04 | Merck Patent Gmbh | Antiviral or antifungal composition and method |
| 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 |
| EP0896792A1 (en) * | 1997-08-13 | 1999-02-17 | Julphar Pharma GmbH | Antiviral agent |
| ES2245610B1 (en) * | 2004-06-23 | 2007-03-16 | Investigacion Y Nutricion, S.L. | PRODUCT OF VEGETABLE ORIGIN AND ITS OBTAINING PROCEDURE. |
| WO2006112496A1 (en) | 2005-04-15 | 2006-10-26 | Toyo Shinyaku Co., Ltd. | Method of producing proanthocyanidin-containing material |
| JP5290558B2 (en) * | 2007-10-10 | 2013-09-18 | 株式会社エヌ・ティー・エイチ | Natural henna extract and its use |
-
1983
- 1983-04-20 JP JP58070774A patent/JPS59196884A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59196884A (en) | 1984-11-08 |
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