JPS6136826B2 - - Google Patents
Info
- Publication number
- JPS6136826B2 JPS6136826B2 JP57170013A JP17001382A JPS6136826B2 JP S6136826 B2 JPS6136826 B2 JP S6136826B2 JP 57170013 A JP57170013 A JP 57170013A JP 17001382 A JP17001382 A JP 17001382A JP S6136826 B2 JPS6136826 B2 JP S6136826B2
- Authority
- JP
- Japan
- Prior art keywords
- acetone
- gall
- ppm
- galloyl
- pmr
- 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
- 229920001301 Hexahydroxydiphenic acid Polymers 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000001424 substituent group Chemical class 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 7
- IMPKVMRTXBRHRB-UHFFFAOYSA-N scyllo-Quercitol Natural products OC1CC(O)C(O)C(O)C1O IMPKVMRTXBRHRB-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 241000411851 herbal medicine Species 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000007721 medicinal effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 2
- KLGMMKCGSUTECD-UHFFFAOYSA-N 1,2,3,4,5-penta-O-galloyl proto-quercitol Natural products Oc1cc(cc(O)c1O)C(=O)OC2CC(OC(=O)c3cc(O)c(O)c(O)c3)C(OC(=O)c4cc(O)c(O)c(O)c4)C(OC(=O)c5cc(O)c(O)c(O)c5)C2OC(=O)c6cc(O)c(O)c(O)c6 KLGMMKCGSUTECD-UHFFFAOYSA-N 0.000 description 1
- MJIBZMYPBIISCU-UHFFFAOYSA-N 1,3,5-tri-O-galloyl proto-quercitol Natural products OC1C(CC(OC(=O)c2cc(O)c(O)c(O)c2)C(O)C1OC(=O)c3cc(O)c(O)c(O)c3)OC(=O)c4cc(O)c(O)c(O)c4 MJIBZMYPBIISCU-UHFFFAOYSA-N 0.000 description 1
- 241000272517 Anseriformes Species 0.000 description 1
- 235000011330 Armoracia rusticana Nutrition 0.000 description 1
- 240000003291 Armoracia rusticana 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
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940017545 cinnamon bark Drugs 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000000605 extraction Methods 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
- 239000000203 mixture Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 244000142282 water primrose Species 0.000 description 1
Description
本発明は医薬品として有用な新規タンニン及び
その製造法に関する。
タンニンは広く植物界に分布し、収劍作用のあ
ることが古くから知られ、収劍薬として、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、地楡等の生薬が、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、これらの主薬の薬効成分を検索
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、栗樹皮等の生薬から、
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 a novel tannin useful as a pharmaceutical and a method for producing the same. Tannins are widely distributed in the plant kingdom, and have long been known to have astringent properties, and have been widely used as an astringent and as a tanning agent to transform hides into leather. Tannin is a plant component with a molecular weight of 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 herbal medicines such as J. elegans have useful medicinal effects based on enzyme inhibitory effects and the like. In order to search for the medicinal properties of these main drugs, the present inventors isolated and obtained the components contained in these drugs and investigated their pharmacological effects, and luckily 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 herbal medicines such as cinnamon bark, cinchona bark, canard bark, and chestnut bark,
It can be easily obtained by known methods such as extraction with acetone, ethyl acetate:water partitioning, or column chromatography. These methods can be summarized as follows, for example.
【表】
以下実施例を掲げて詳細に説明する。
実施例 １
ウラジロガシ皮3.35Kgを水性アセトン16で３
回抽出し、水溶液を酢酸エチル１で分液を10回
繰り返した。酢酸エチル層を集め、Sephadex
LH―20でカラムクロマト分離を繰り返して精製
したところ、以下のGalloyl化新規物質を得た。
１，２，３，４，５―penta―Ｏ―galloyl
protoquercitol〔α〕D＋9.9゜収率（0.002％）
淡黄色無定形粉末
PMR（acetone d6）ppm：
2.16―2.40，2.68―2.96（each1H，ｍ，C6―
Ｈ）、
5.40―6.00（5H，ｍ，C1，C2，C3，C4，C5―
Ｈ），6.97
（2H，ｓ，gall.H），7.00，7.06（each4H，ｓ，
gall.H）
３，４―HHDP―１，５―di―Ｏ―galloyl
protoquercitol〔α〕D＋75.9゜収率（0.03％）
淡黄色無定形粉末
PMR（acetone d6）ppm：
2.24―2.60（2H，ｍ，C6―Ｈ），4.39（1H，
ｔ，Ｊ＝２Hz，C2―Ｈ）5.24―5.80（4H，ｍ，
C1，C3，C4，C5―Ｈ），6.66，6.42（each1H，
ｓ，HHDP.H）7.13，7.18（each2H，ｓ，gall.
H）
CMR（acetone d6）ppm：
32.8，68.7，69.3，71.8，76.0，76.4
（protoquercitol Ｃ），
107.2，107.8，109.9，114.4，120.5，120.7，
126.5，126.7，136.2，136.3，136.4，139.6，
144.3，145.2，146.1（arom.C）165.9，166.6，
169.4，169.7（―COO―）[Table] A detailed explanation will be given below using examples. Example 1 3.35Kg of horseradish bark was added to 3.35kg of aqueous acetone 16
The mixture was extracted twice, and the aqueous solution was separated with 1 part of ethyl acetate 10 times. Collect the ethyl acetate layer and Sephadex
After repeated column chromatography separation and purification using LH-20, the following new Galloylated substance was obtained. 1,2,3,4,5-penta-O-galloyl
protoquercitol [α] D +9.9゜Yield (0.002%) Pale yellow amorphous powder PMR (acetone d 6 ) ppm: 2.16-2.40, 2.68-2.96 (each1H, m, C6-
H), 5.40-6.00 (5H, m, C 1 , C 2 , C 3 , C 4 , C 5 -
H), 6.97 (2H, s, gall.H), 7.00, 7.06 (each4H, s,
gall.H) 3,4-HHDP-1,5-di-O-galloyl
protoquercitol〔α〕 D +75.9゜Yield (0.03%)
Pale yellow amorphous powder PMR (acetone d 6 ) ppm: 2.24-2.60 (2H, m, C 6 -H), 4.39 (1H,
t, J = 2Hz, C 2 - H) 5.24 - 5.80 (4H, m,
C 1 , C 3 , C 4 , C 5 -H), 6.66, 6.42 (each1H,
s, HHDP.H) 7.13, 7.18 (each2H, s, gall.
H) CMR (acetone d 6 ) ppm: 32.8, 68.7, 69.3, 71.8, 76.0, 76.4 (protoquercitol C), 107.2, 107.8, 109.9, 114.4, 120.5, 120.7,
126.5, 126.7, 136.2, 136.3, 136.4, 139.6,
144.3, 145.2, 146.1 (arom.C) 165.9, 166.6,
169.4, 169.7 (-COO-)
【式】【formula】
【式】
２，４，６―tri―Ｏ―galloyl proto―
quercitol Colorless granules
mp 207〜210℃
〔α〕D＋15.0゜（ｃ＝1.63acetone）
PMR（acetone―d6＋D2O）ppm：1.88〜2.50
（2H，ｍ，C6―Ｈ），4.21（1H，br.d，Ｊ＝
4H，C1―Ｈ），4.44（1H，dd，Ｊ＝４，10
Hz，C3―Ｈ），5.46（1H，br.s，C2―Ｈ），
5.38〜5.66（1H，ｍ，C3―Ｈ），5.77（1H，
ｔ，Ｊ＝８Hz，C4―Ｈ），7.07，7.11，7.24
（each 2H，ｓ，gall―Ｈ）
CMR（acetone―d6）ppm：33.3（C6），
66.6，68.6，71.3，75.6，75.8（C1，C2，C3，
C4，C5），166.7，
166.8，167.6（―COO―）
収率：0.007％
１，４，５―tri―０―galloyl proto―
quercitol Colorless granules
mp219〜223℃
〔α〕D＋39.1゜（ｃ＝0.4MeOH）
PMR（pyridine―d5）ppm：2.60〜2.90
（2H，ｍ，C6―Ｈ），4.58（1H，dd，Ｊ＝3.8
Hz，C3―Ｈ），2.77（1H，br.s，C2―Ｈ），
5.80（1H，br.d，Ｊ＝３Hz，C1―Ｈ），
6.64（1H，ｔ，Ｊ＝９Hz，C5―Ｈ），6.58
（1H，ｔ，Ｊ＝９Hz，C4―Ｈ），7.80（2H，
ｓ，gall―Ｈ），7.86（4H，ｓ，gall―Hx2）
CMR（acetone―d6＋D2O）δ30.2（C6），
71.1，71.9，75.0（C1，C2，C3，C4，C5），
166.1，166.6，167.6（―COO―）
収率：0.005％
１，３，５―tri―Ｏ―galloyl proto―
quercitol Coloress needles
mp222〜224℃
〔α〕D―11.9゜（ｃ＝0.81acetone）
PMR（acetone―d6＋D2O）ppm：2.16―2.48
（2H）ｍ，C6―Ｈ），4.34（1H，ｔ，Ｊ＝３
Hz，C2―Ｈ），4.44（1H，Ｊ＝９Hz，C4―
Ｈ），5.30（1H，br.d，Ｊ＝３Hz，C1―Ｈ），
5.20〜5.50（1H，ｍ，C5―Ｈ），5.35（1H，
dd，Ｊ＝3.9Hz，C3―Ｈ），7.16，7.19，7.24
（each 2H，ｓ，gall―Ｈ）
CMR（acetone―d6＋D2O）ppm：29.8
（C6），68.7，70.4，72.2，73.4，75.5（C1，
C2，C3，C4，C5），
166.1，166.9，167.1（―COO―）
収率：0.005％
１，３，４，５―tetra―０―galloyl proto
―quercitol An off―white amorphous
powder
〔α〕D―2.7゜（ｃ＝0.71Me0H）
PMR（acetone―d6＋D2O）ppm：2.30〜2.60
（2H，ｍ，C6―Ｈ），4.46（1H，ｔ，Ｊ＝３
Hz，C2―Ｈ），5.32（1H，br，d.J＝３Hz，C1
―Ｈ），5.52（1H，dd，Ｊ＝
3.9Hz，C3―Ｈ），5.48〜5.76（1H，ｍ，C5―
Ｈ），6.90（1H，ｔ，Ｊ＝９Hz，C4―Ｈ），
7.02，7.26（each 2H，ｓ，gall―Ｈ），
7.05（4H，ｓ，gall―Hx2）
収率：0.001％
１，２，４，５―tetra―０―galloyl proto
―quercitol Ａ white amorphous powder
〔α〕D＋34.3゜（ｃ＝0.14MeOH）
PMR（acetone―d6＋D2O）ppm：1.90〜
2.20，2.20〜2.60（each 1H，ｍ，C6―Ｈ），
4.50（1H，dd，Ｊ＝
3.9Hz，C3―Ｈ），5.40〜5.68（3H，ｍ，C1，
C2，C5―Ｈ）
5.85（1H，ｔ，Ｊ＝９Hz，C4―Ｈ），7.10，
7.17，7.26，7.29（each 2H，ｓ，gall―Ｈ）
収率：0.0005％
３，４―HHDP―５―０―
galloylprotoquecitol An off―white
amorphous powder
〔α〕D＋70.1゜（ｃ＝0.65 acetone）
PMR（pyridine―d5）ppm；2.60―2.90
（2H，ｍ，C6―Ｈ），2.60（1H，br.s，C1―
Ｈ），2.78（1H，br.s，C2―Ｈ）6.20〜6.60
（3H，ｍ，C3，４，５―Ｈ），7.03，7.09
（each1H，ｓ，HHDP―Ｈ）7.80（2H，ｓ，
gall―Ｈ）
収率；0.002％
[Formula] 2,4,6-tri-O-galloyl proto-
quercitol Colorless granules mp 207-210℃ [α] D +15.0゜ (c=1.63acetone) PMR (acetone-d6+D 2 O) ppm: 1.88-2.50
(2H, m, C6-H), 4.21 (1H, br.d, J=
4H, C1-H), 4.44 (1H, dd, J=4,10
Hz, C3-H), 5.46 (1H, br.s, C2-H),
5.38-5.66 (1H, m, C3-H), 5.77 (1H,
t, J=8Hz, C4-H), 7.07, 7.11, 7.24
(each 2H, s, gall-H) CMR (acetone-d6) ppm: 33.3 (C6),
66.6, 68.6, 71.3, 75.6, 75.8 (C1, C2, C3,
C4, C5), 166.7, 166.8, 167.6 (-COO-) Yield: 0.007% 1,4,5-tri-0-galloyl proto-
quercitol Colorless granules mp219-223℃ [α] D +39.1゜ (c=0.4MeOH) PMR (pyridine-d5) ppm: 2.60-2.90
(2H, m, C6-H), 4.58 (1H, dd, J=3.8
Hz, C3-H), 2.77 (1H, br.s, C2-H),
5.80 (1H, br.d, J=3Hz, C1-H), 6.64 (1H, t, J=9Hz, C5-H), 6.58
(1H, t, J=9Hz, C4-H), 7.80 (2H,
s, gall-H), 7.86 (4H, s, gall-Hx2) CMR (acetone-d6+D 2 O) δ30.2 (C6),
71.1, 71.9, 75.0 (C1, C2, C3, C4, C5),
166.1, 166.6, 167.6 (-COO-) Yield: 0.005% 1,3,5-tri-O-galloyl proto-
quercitol Coloress needles mp222-224℃ [α] D -11.9゜ (c=0.81acetone) PMR (acetone-d6+D 2 O) ppm: 2.16-2.48
(2H) m, C6-H), 4.34 (1H, t, J=3
Hz, C2-H), 4.44 (1H, J=9Hz, C4-
H), 5.30 (1H, br.d, J=3Hz, C1-H),
5.20-5.50 (1H, m, C5-H), 5.35 (1H,
dd, J=3.9Hz, C3-H), 7.16, 7.19, 7.24
(each 2H, s, gall-H) CMR (acetone-d6+D 2 O) ppm: 29.8
(C6), 68.7, 70.4, 72.2, 73.4, 75.5 (C1,
C2, C3, C4, C5), 166.1, 166.9, 167.1 (-COO-) Yield: 0.005% 1,3,4,5-tetra-0-galloyl proto
―quercitol An off―white amorphous
powder [α] D -2.7゜ (c=0.71Me0H) PMR (acetone-d6+D 2 O) ppm: 2.30-2.60
(2H, m, C6-H), 4.46 (1H, t, J=3
Hz, C2-H), 5.32 (1H, br, dJ = 3Hz, C1
-H), 5.52 (1H, dd, J= 3.9Hz, C3-H), 5.48~5.76 (1H, m, C5-
H), 6.90 (1H, t, J=9Hz, C4-H),
7.02, 7.26 (each 2H, s, gall-H), 7.05 (4H, s, gall-Hx2) Yield: 0.001% 1,2,4,5-tetra-0-galloyl proto
-quercitol A white amorphous powder [α] D +34.3゜ (c=0.14MeOH) PMR (acetone-d6+D 2 O) ppm: 1.90~
2.20, 2.20~2.60 (each 1H, m, C6-H),
4.50 (1H, dd, J = 3.9Hz, C3-H), 5.40~5.68 (3H, m, C1,
C2, C5-H) 5.85 (1H, t, J=9Hz, C4-H), 7.10,
7.17, 7.26, 7.29 (each 2H, s, gall-H) Yield: 0.0005% 3,4-HHDP-5-0-
galloylprotoquecitol An off-white
amorphous powder [α] D +70.1゜ (c=0.65 acetone) PMR (pyridine-d5) ppm; 2.60-2.90
(2H, m, C6-H), 2.60 (1H, br.s, C1-
H), 2.78 (1H, br.s, C2-H) 6.20-6.60
(3H, m, C3, 4, 5-H), 7.03, 7.09
(each1H, s, HHDP-H) 7.80 (2H, s,
gall-H) Yield; 0.002%
Claims (1)
水素、Ｇ（Ｇはgalloyl基【式】を 示す。）、又はHHDP（HHDPは
hexahydroxydiphenoyl基
【式】を示す。この場 合、この置換基が任意の二箇所で結びつく。）を
示す。ただし、R1，R2，R3，R4，R5が同時に水
素である場合を除く。〕で表わされる新規なタン
ニン。[Claims] First-order general formula [] [R 1 , R 2 , R 3 , R 4 , R 5 are the same or different,
Hydrogen, G (G represents galloyl group [formula]), or HHDP (HHDP is
Indicates the hexahydroxydiphenoyl group [formula]. In this case, this substituent is bonded at any two positions. ) is shown. However, this excludes the case where R 1 , R 2 , R 3 , R 4 , and R 5 are hydrogen at the same time. ] A new tannin represented by
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57170013A JPS5959638A (en) | 1982-09-28 | 1982-09-28 | Novel tannin |
| JP60245751A JPS61112068A (en) | 1982-09-28 | 1985-10-31 | Novel tannin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57170013A JPS5959638A (en) | 1982-09-28 | 1982-09-28 | Novel tannin |
Related Child Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60245750A Division JPS61118395A (en) | 1985-10-31 | 1985-10-31 | Novel tannin |
| JP60245751A Division JPS61112068A (en) | 1982-09-28 | 1985-10-31 | Novel tannin |
| JP60245748A Division JPS61112089A (en) | 1985-10-31 | 1985-10-31 | Novel tannin |
| JP60245752A Division JPS61112090A (en) | 1985-10-31 | 1985-10-31 | Novel tannin |
| JP60245749A Division JPS61112080A (en) | 1985-10-31 | 1985-10-31 | Novel tannin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5959638A JPS5959638A (en) | 1984-04-05 |
| JPS6136826B2 true JPS6136826B2 (en) | 1986-08-20 |
Family
ID=15896969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57170013A Granted JPS5959638A (en) | 1982-09-28 | 1982-09-28 | Novel tannin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5959638A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61205272A (en) * | 1985-03-08 | 1986-09-11 | Tsumura Juntendo Inc | Novel tannin |
| JPS63162685A (en) * | 1986-12-26 | 1988-07-06 | Kikkoman Corp | Production of proanthocyanidin |
| JPH1059846A (en) * | 1996-06-10 | 1998-03-03 | Kikkoman Corp | Preventive or remedy for cararacta |
| KR100644764B1 (en) | 2005-08-16 | 2006-11-14 | 주식회사 바이오랜드 | Novel method of process for genin compounds and their salt and a use for composition containing the same |
-
1982
- 1982-09-28 JP JP57170013A patent/JPS5959638A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5959638A (en) | 1984-04-05 |
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