JPS6064983A - Tannin - Google Patents
TanninInfo
- Publication number
- JPS6064983A JPS6064983A JP16180884A JP16180884A JPS6064983A JP S6064983 A JPS6064983 A JP S6064983A JP 16180884 A JP16180884 A JP 16180884A JP 16180884 A JP16180884 A JP 16180884A JP S6064983 A JPS6064983 A JP S6064983A
- Authority
- JP
- Japan
- Prior art keywords
- bark
- tannin
- acetone
- iii
- 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.)
- Pending
Links
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (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台用なタンニン及びその製造法に
関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a tannin used as a pharmaceutical and a method for producing the tannin.
タンニンは広く植物界に分布し、収れん作用のあるとこ
ろから収れん薬として、また皮を革に変化さ・ｌるなめ
し剤とし−Ｃ多（用いら“れてきた。タンニンは分子量
６００〜２０（１０はどで複５“１［な構造を有してお
り、ｆｐ離ｔｆｊ製の困ｆｆ１ｌｔさとあいまって研究
が遅れていた。Tannins are widely distributed in the plant kingdom, and have been used as astringents due to their astringent properties, and as tanning agents for turning skin into leather. Tannins have molecular weights of 600 to 20 ( 10 has a double 5"1 structure at the end, and this combined with the problems of ff1lt produced by fp and tfj has delayed research.
一方、従来よりうらじろがし等の酵素阻古作用等に基づ
く有用な医薬的りＪ果が知られ′（才ｉす、本発明者ら
は、多くの植物より新規の夕６ンニンを単離取得して薬
理効果を検べ、酵素阻書伯用を見出だした。本発明に係
る化合物は、体中ｒＩＹ素蛋白と結合することによって
そのＷ性を低士さ廿ることが判っている。On the other hand, there have been known useful medicinal fruits based on enzyme anti-aging effects, such as vegetative action. We isolated and obtained it, examined its pharmacological effects, and found that it can be used as an enzyme inhibitor.It has been found that the compound of the present invention reduces its W properties by binding to rIY protein in the body. ing.
本発明に係る化合物は、代Ｒ１ＩＪ調節剤として有用で
ある。The compounds according to the present invention are useful as R1IJ modulators.
本発明に係る化合物はすべて文献未載の新規化合物であ
る。All the compounds according to the present invention are new compounds that have not been described in any literature.
本発明に係る化合物は、楊梅皮、桂皮、供揶子、地楡、
菱実、ウラジロガシ皮、コケモモ葉等の植物から、アセ
トンによる抽出、酢酸エチル：水の分配、カラムクロマ
ト等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 yangmei bark, cinnamon bark, citrus fruit, citrus elegans,
It can be easily obtained from plants such as rhombuses, oak bark, and lingonberry leaves by known methods such as extraction with acetone, ethyl acetate:water partitioning, and column chromatography.
本発明による抽出方法を総括して示せば例えば次のよう
である。The extraction method according to the present invention can be summarized as follows, for example.
（以下次頁） 以下実施例を掲げてｄ′Ｃ♀１１１４こ説明Ｊ゛る。(See next page) The following is an explanation of d'C♀1114 with examples.
実施例１
コケモモ葉１．８ｋｇをアセトン３１で温浸し、アセト
ンを留去後、水門こ熔解し、酢酸エチル（１１）で数回
分配した。酢・エチル移行部を５ｅｐｈａｄｅｘ ’Ｌ
ｌｌ−２０のカラムクロマトにかけ、くり返し分離し、
以降Ｍｅ２ ＳＯ４とに２ ＣＯ３を用い審決によりン
チル化して以下の物質をｌた。Example 1 1.8 kg of lingonberry leaves were digested with 31 ml of acetone, and after distilling off the acetone, the mixture was sluice-melted and distributed several times with ethyl acetate (11). Vinegar/ethyl transition part 5ephadex'L
ll-20 column chromatography, repeated separation,
Thereafter, Me2SO4 and 2CO3 were used to methylate the following substances according to the trial decision.
１、無色無定形粉末、（α）。−＋−７２，７゜Ｐｒｏ
ｔｏｎ−ＮＭＲ（ｔ’ｈＮＯ２−ｄ５．１５０°Ｃ〕２
．６５ （ＩＩＩ、ｄｄ、 Ｊ＝８．１６１１ｚ、Ｃ４
″−ＩＩ）３．１８ （ＩＩＩ、ｄｄ、 Ｊ＝、６，１
６１１ｚ、Ｃ４″−Ｉｆ）３．５４〜３．９６ （ＯＭ
ｅ ｘ １１）４．４８ （ＩＩＩ、ｄ、Ｊ ＝８１１
ｚ、Ｃ２”−１ｆ）４．６０ （ＩＩＩ、ｍ、Ｃ３’
−ＩＩ）４．９２ （ＩＩＩ、ｄ、Ｊ＝２１１’ｚ、
Ｃ４−ＩＩ）５．０３ （１１ＬＪ＝２１１２． Ｃ４
’−ＩＩ）５．９０ （１１Ｌｂｒ、ｓ、Ｃ２−ＩＩ）
６．１４ （Ｉｌｌ、ｄ、Ｊ＝２１１ｚ、Ｃｃ −Ｉｆ
）６．２９及び６．４４ （ｅａｃｂ ＩＩＩ＋ｓ＋
Ｃｃ’＋Ｃｅ″−Ｉｔ）６．３８ （ＩＩＩ、ｄ、Ｊ７
２１１ｚ、ｃａ −Ｉｔ）２、無色無定形粉末、〔α］
。＋１０７．９゜Ｐｒｏｔｏｉ＋−ＮＭＲ（ＰｈＮＯ２
’−ｄ５．１５０℃〕２．６８ （ＬＬｄｄ、Ｊ＝８，
１６１１２．Ｃ４”−１１）３．１８ （Ｉｌｌ、ｄｄ
、Ｊ＝６＋１６１１ｚ＋Ｃ４”−１１）３．２４〜３．
９９ （ＯＭｅ Ｘ１ｌ）４．４６ （ＩＩＩ、ｄ、Ｊ
＝８１１ｚ、 Ｃ２”−Ｉｔ）６．０８’（ＩＩＩ、ｄ
、Ｊ＝２１１ｚ、ＣＢ −ｔｌ）６．２４及び６．４５
（ｅａｃ＋＋ ｌ１ｌｓ、 Ｃｅ ＋Ｃｅ −Ｉｔ）
６．３５ （１１Ｌｄ、Ｊ ＝２１１ｚ、ＣＢ −ＩＩ
）実施例２
クスノキ１．８ｋｇをアセトン３ρで’ＩＡ浸し、アセ
トンを留去後、水に熔解し、酢酸エチル（１４）で数回
分配した。1. Colorless amorphous powder (α). −＋−72,7゜Pro
ton-NMR (t'hNO2-d5.150°C)2
．． 65 (III, dd, J=8.1611z, C4
″-II) 3.18 (III, dd, J=, 6, 1
611z, C4″-If) 3.54~3.96 (OM
e x 11) 4.48 (III, d, J = 811
z, C2"-1f) 4.60 (III, m, C3'
-II) 4.92 (III, d, J=211'z,
C4-II) 5.03 (11LJ=2112.C4
'-II) 5.90 (11Lbr, s, C2-II)
6.14 (Ill, d, J=211z, Cc -If
)6.29 and 6.44 (eacb III+s+
Cc'+Ce''-It)6.38 (III, d, J7
211z, ca-It)2, colorless amorphous powder, [α]
. +107.9゜Protoi+-NMR (PhNO2
'-d5.150℃]2.68 (LLdd, J=8,
16112. C4”-11) 3.18 (Ill, dd
, J=6+1611z+C4"-11) 3.24~3.
99 (OMe X1l) 4.46 (III, d, J
=811z, C2''-It)6.08'(III, d
, J=211z, CB-tl) 6.24 and 6.45
(eac++ l1ls, Ce +Ce -It)
6.35 (11Ld, J = 211z, CB-II
) Example 2 1.8 kg of camphor tree was soaked with 3 ρ of acetone in IA, and after distilling off the acetone, it was dissolved in water and distributed several times with ethyl acetate (14).
以下実施例１と同様の方法により、以下の物質を得た。The following materials were obtained in the same manner as in Example 1.
（収率 ０．０３３％）
ＫＵＳ−９無色針状晶
融点 〉３００℃ 〔α擢 ＋１０２．３° （Ｃ−０
，９９、ａｃｅｔｏｎｅ ）
ＰＭＲ（ＤＭＳＯ−ｄｅ ） ｐｐｍ ： ３．７６
（２１１，ｍ、Ｃ３゜３’Ｈ） 、 ３．８０ （Ｈ［
、ｄ、 Ｊ ＝４Ｈｚ、Ｃ３’？Ｈ） 。(Yield 0.033%) KUS-9 colorless needle crystals Melting point 〉300℃ [α 擢 +102.3° (C-0
, 99, acetone) PMR (DMSO-de) ppm: 3.76
(211, m, C3°3'H), 3.80 (H[
, d, J = 4Hz, C3'? H).
４．２３ （ＩＩＩ、ｄ、 Ｊ ＝４１１ｚ、 Ｃ４’
−旧４．４３ （Ｉ Ｈ、ｓ、 Ｃ４’−Ｈ） 、 ４
．８４ （ＩＨ，ｄ、 Ｊ ＝８１１ｚ、 Ｃ２−ｔｌ
）５．２０ （Ｉｆ−１，ｓ、Ｃ２−Ｈ）実施例３
セイロン桂皮 ２０ｋｇ から前記と概ね同様の方法に
より、以下の物質を得た。4.23 (III, d, J = 411z, C4'
-Old 4.43 (I H, s, C4'-H), 4
．． 84 (IH, d, J = 811z, C2-tl
) 5.20 (If-1,s, C2-H) Example 3 The following substance was obtained from 20 kg of Ceylon cinnamon by a method generally similar to that described above.
■Ｃｏｍｐｄ Ｉ ：黄色粉末 〔α昂 ＋７０．３
’ （ａｃｅｔｏｎｅ ） 収率（０，１％）ＰＭＲ（
ＤＭＳＯ−ｄ６，１５０℃） ｐｐｍ ： ２．７５
（２１１゜ｍ、 Ｃ４−Ｉｔ ） ３．７５ （ＩＩＩ
、ｂｒ、ｓ、Ｃ３−ＩＩ ） 、３．９１１ （ＩＩＩ
、 ｓ、Ｃ３−ＩＩ ）−、４，０４（ＩＩＬ ｄ、
Ｊ＝４１ｂ、、Ｃ３−１ｔ ） 、 ４．２４ （ＩＩ
Ｉ、 ｄ、 Ｊ−４１１ｚ、Ｃ４−Ｉｆ ） 。■Compd I: Yellow powder [α+70.3
' (acetone) Yield (0,1%) PMR (
DMSO-d6, 150℃) ppm: 2.75
(211゜m, C4-It) 3.75 (III
, br, s, C3-II) , 3.911 (III
, s, C3-II)-, 4,04(IIL d,
J=41b,, C3-1t), 4.24 (II
I, d, J-411z, C4-If).
４．４０−４．７６ （２１１，ｍ、Ｃ２，４−１１）
、 ５．３８ （ｉｌｌ。4.40-4.76 (211,m, C2,4-11)
, 5.38 (ill.
ｓ、Ｃ２−ＩＩ ）
ＣＭＲ（ａｃｅｔｏｎｅ ｄｓ ） ｐ凹：３３．Ｑ
（Ｃ４’＋４”）、 ６６．５ （Ｃ３，３’） 、
７１．６ （Ｃ３”） 、 ７Ｂ、２ （Ｃ２’） 、
７９．８ （Ｃ２） 、 ９９．５． ９６．２．９
７．９．９９．４゜９９．９ （Ｃ６，６’、８．２″
）
■Ｃｏｍｐｄ ＩＩ 黄色粉末 〔α］。＋５１．１゜
収率（０，０２％）
ＰＭＲ（ａｃｅｔｏｎｅ ｄ６） ｐｐｍ ：回転障害
のため解析不能
ＣＭＲ（ａｃｅｔｏｎｅ ｄ６） ｐｐｍ ：３６．４
＋ ３７．１ （Ｃ４４’：１″＞ 、 ６６．５ （
Ｃ３，３’） 、 ７１．３ （Ｃ３″’） 、 ７５
．８（Ｃ２”″） 、 １１．９（Ｃ２’） 、 ７９
．４ （Ｃ２） 、 ９５．７、９６．２．９８．３．
９９．５ ＜ｃ６．６’、６’：６”：８’：’２”＞
１ノ」ニs, C2-II) CMR (acetone ds) p concave: 33. Q
(C4'+4"), 66.5 (C3,3'),
71.6 (C3"), 7B,2 (C2'),
79.8 (C2), 99.5. 96.2.9
7.9.99.4゜99.9 (C6,6',8.2''
) ■Compd II Yellow powder [α]. +51.1゜Yield (0.02%) PMR (acetone d6) ppm: Unable to analyze due to rotational disturbance CMR (acetone d6) ppm: 36.4
+ 37.1 (C44':1''>, 66.5 (
C3,3'), 71.3 (C3''), 75
．． 8 (C2''), 11.9 (C2'), 79
．． 4 (C2), 95.7, 96.2.98.3.
99.5 <c6.6', 6':6":8':'2">
1 no” ni
Claims (1)
チルを表わす。）で表わされる新規タンニン。[Claims] A novel tannin represented by the following general formula (IX) (R22 and R2B are different, and hydrogen or R represents hydrogen or methyl).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16180884A JPS6064983A (en) | 1984-07-31 | 1984-07-31 | Tannin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16180884A JPS6064983A (en) | 1984-07-31 | 1984-07-31 | Tannin |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56120372A Division JPS6011912B2 (en) | 1981-07-30 | 1981-07-30 | tannin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6064983A true JPS6064983A (en) | 1985-04-13 |
Family
ID=15742303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16180884A Pending JPS6064983A (en) | 1984-07-31 | 1984-07-31 | Tannin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6064983A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004043345A3 (en) * | 2002-11-08 | 2005-02-17 | Kin-Ping Wong | Extract of trapa natans and methods of using the same |
| CN105393668A (en) * | 2015-10-30 | 2016-03-16 | 云南大学 | Method for relieving dormancy of cyclobalanopsis glaucoides schotky seeds |
-
1984
- 1984-07-31 JP JP16180884A patent/JPS6064983A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| J.CHEM.SOC.,CHEM.COMMUN.=1973 * |
| J.CHEM.SOC.,PERKIN TRANS.=1974 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004043345A3 (en) * | 2002-11-08 | 2005-02-17 | Kin-Ping Wong | Extract of trapa natans and methods of using the same |
| US7494671B2 (en) | 2002-11-08 | 2009-02-24 | Kin-Ping Wong | Extract of Trapa natans and methods of using the same |
| CN105393668A (en) * | 2015-10-30 | 2016-03-16 | 云南大学 | Method for relieving dormancy of cyclobalanopsis glaucoides schotky seeds |
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