JPS6050778B2 - tannin - Google Patents
tanninInfo
- Publication number
- JPS6050778B2 JPS6050778B2 JP16180784A JP16180784A JPS6050778B2 JP S6050778 B2 JPS6050778 B2 JP S6050778B2 JP 16180784 A JP16180784 A JP 16180784A JP 16180784 A JP16180784 A JP 16180784A JP S6050778 B2 JPS6050778 B2 JP S6050778B2
- Authority
- JP
- Japan
- Prior art keywords
- gal
- acetone
- ppm
- cooh
- vii
- 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 title claims description 7
- 239000001648 tannin Substances 0.000 title claims description 7
- 235000018553 tannin Nutrition 0.000 title claims description 7
- 239000000126 substance Substances 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 229940022682 acetone Drugs 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 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
- 241000039951 Lithocarpus glaber Species 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 244000080208 Canella winterana Species 0.000 description 1
- 235000008499 Canella winterana Nutrition 0.000 description 1
- 244000077923 Vaccinium vitis idaea Species 0.000 description 1
- 235000017606 Vaccinium vitis idaea Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000011097 chromatography purification Methods 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
- 230000000694 effects Effects 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
- 239000007937 lozenge Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 230000002503 metabolic effect Effects 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
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は医薬品として有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 tannins useful as pharmaceuticals and methods for producing the same.
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 been widely used as an astringent due to their astringent properties, and as a tanning agent to transform hides into leather.
タンニンは分子量６００〜２０００ほどで複雑な構造を
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、従来よりうらじろがし等の酵素阻害作用
等に基づく有用な医薬的効果が知られており、本発明者
らは、多くの植物より新規のタンニンを単離取得して薬
理効果を検べ、酵素阻害作用を見出た七た。Tannins have a molecular weight of about 600 to 2,000 and a complex structure, which, combined with the difficulty of isolation and purification, has delayed research. On the other hand, useful medicinal effects have been known based on enzyme inhibitory effects such as tannins, and the present inventors have isolated and obtained novel tannins from many plants to demonstrate their pharmacological effects. I tested it and found that it had an enzyme inhibitory effect.
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ことが判つている。本発明
に係る化合物は、代謝調節剤として有用である。It has been found that the compounds according to the present invention reduce the activity of enzyme proteins in the body by binding to them. Compounds according to the invention are useful as metabolic regulators.
本発明に係る化合物はすへて文献未載の新規化合物であ
る。本発明に係る化合物は、楊梅皮、桂皮、机椰子、地
検、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 compound according to the present invention is a novel compound that has not yet been described in any literature. The compounds according to the present invention can be obtained from plants such as Yang Mei Peel, cinnamon bark, desk palm, district copse, lozenge, Japanese oak bark, lingonberry leaf, etc.
It can be easily obtained by known methods such as extraction with acetone, ethyl acetate: water partitioning, column chromatography, etc.
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。以下実施例を掲げて詳細に説明する。The extraction method according to the present invention can be summarized as follows, for example. Examples will be described in detail below.
実施例１
ウラジロガシ皮６．３ｋ９を８０％の水性アセトン５′
て抽出し、アセトンを留去後、水溶性を酢酸エチル１ｅ
で約１０回分液、酢酸エチル可溶部をあつめ、Ｓｅｐｈ
ａａｄｅｘｌ．Ｈ−２０で溶媒エタノール、８０％水性
メタノールを使い、カラムクロマト分離精製したところ
、以下の物質４５ｍｇを得た。Example 1 80% aqueous acetone 5'
After distilling off the acetone, remove the water solubility with ethyl acetate.
Separate the solution about 10 times, collect the ethyl acetate soluble part, and add Seph
aadexl. When column chromatographic separation and purification was performed using H-20 as a solvent and 80% aqueous methanol, 45 mg of the following substance was obtained.
無色無定形粉末。Colorless amorphous powder.
〔α〕。−１０２．８。（ｃ＝０．３２，ａｃｅｔ０ｎ
ｅ）ＰＭＲ（ＡｃｅｔＯｎｅ−Ｃｌ６）Ｐｐｍ：２．１
０−２．５０（４Ｈ，ｍ，Ｃ２，６−Ｈ），４．５０（
１Ｈ，ｄ−１１ｋｅ，Ｊ＝４Ｈｚ，Ｃ５−Ｈ），５．２
５（１Ｈ，ｄｄ，Ｊ＝７，４Ｈｚ，Ｃ，−Ｈ），５．６
０−５．９３（１Ｈ，ｍ，Ｃ３−Ｈ），７．０５，７．
１１（Ｅａｃｈ２Ｈ，ｓ，ｇａｌ，Ｈ）。[α]. -102.8. (c=0.32, acet0n
e) PMR (AcetOne-Cl6) Ppm: 2.1
0-2.50 (4H, m, C2, 6-H), 4.50 (
1H, d-11ke, J=4Hz, C5-H), 5.2
5 (1H, dd, J=7,4Hz, C, -H), 5.6
0-5.93 (1H, m, C3-H), 7.05, 7.
11 (Each2H, s, gal, H).
ＣＭＲ（ＡｃｅｔＯｎｅ−ＤＧ）Ｐｐｍ：３８．０（Ｃ
２），３９．０（Ｃ６），６８．５（Ｃ５），６８．７
（Ｃ３），７５．２（Ｃ１），７５．５（Ｃ４），１０
９．７，１０９．８（？１１．Ｃ２，６），１２０．６
（Ｇａｌ．Ｃｌ×２），１３８．７（Ｇａｌ．Ｃ４ｘ２
），１４５．５（Ｇａｌ．Ｃ３，５×２），１６６．３
，１６６．６（−ＣＯＯ−），１７７．５（ＣＯＯＨ）
。３．４−Ｄｉ−０−ＧａｌｌＯｙｌｑｕｊｎｉｃａｃ
ｉｄ．同様にして３，５−Ｄｊ−０−ＧａｌｌＯｙｌｑ
ｕｉｎｉｃＡｃｊｄ無色無定形 粉末（収率０．００６
％）を得た。CMR (AcetOne-DG) Ppm: 38.0 (C
2), 39.0 (C6), 68.5 (C5), 68.7
(C3), 75.2 (C1), 75.5 (C4), 10
9.7,109.8(?11.C2,6),120.6
(Gal.Cl×2), 138.7(Gal.C4x2
), 145.5 (Gal.C3, 5×2), 166.3
, 166.6 (-COO-), 177.5 (COOH)
. 3.4-Di-0-GallOylqujnicac
id. Similarly, 3,5-Dj-0-GallOylq
uinicAcjd Colorless amorphous powder (yield 0.006
%) was obtained.
〔α〕ｏ−６３．００（ｃ＝０．２０，ａｃｅｔ０ｎｅ
）ＰＭＲ（ＡｃｅｔＯｎｅ−（１６）Ｐｐｍ：２．３３
（４Ｈ，ｄ一１１ｋｅ，ｊ＝７Ｈｚ，Ｃ２，６−Ｈ），
４．１４（１Ｈ，ｄｄ，ｊ＝７．４Ｈｚ，Ｃ４−Ｈ），
５．４０−５．６８（２Ｈ，ｍ，Ｃ３，５−Ｈ），７．
１３，７．１９（Ｅａｃｈ２Ｈ，ｓ，ｇａｌ．Ｈ）。Ｃ
ＭＲ（ＡｃｅｔＯｎｅ−Ｄ６）Ｐｐｍ：３５．７（Ｃ６
），３７．５（Ｃ２），７０．１（Ｃ４），７２．０（
Ｃ３），７２．１（Ｃ，），７４．２（Ｃ１），１０９
．８（Ｇａｌ．Ｃ２，６×２），１２１．４，１２１．
９（Ｇａｌ．Ｃｌ），１３８．３，１３８．６（Ｇａｌ
．Ｃ４），１４５．５（Ｇａｌ．Ｃ３，５×２），１６
６．１（−ＣＯＯ−×２），１７５．８（−ＣＯＯＨ）
。同様にして４，５−Ｄｉ−０−ＧａｌｌＯｙｌｑｕｉ
ｎｉｃａＣｌｄ黄かつ色無定形粉末（収率０．００５％
）を得た。[α]o-63.00 (c=0.20, acet0ne
)PMR(AcetOne-(16)Ppm: 2.33
(4H, d-11ke, j=7Hz, C2,6-H),
4.14 (1H, dd, j=7.4Hz, C4-H),
5.40-5.68 (2H, m, C3,5-H), 7.
13, 7.19 (Each2H, s, gal.H). C
MR (AcetOne-D6) Ppm: 35.7 (C6
), 37.5 (C2), 70.1 (C4), 72.0 (
C3), 72.1 (C,), 74.2 (C1), 109
．． 8 (Gal.C2, 6×2), 121.4, 121.
9 (Gal.Cl), 138.3, 138.6 (Gal.
．． C4), 145.5 (Gal.C3, 5×2), 16
6.1 (-COO- x 2), 175.8 (-COOH)
. Similarly, 4,5-Di-0-GallOylqui
nicaCld yellow and colored amorphous powder (yield 0.005%
) was obtained.
〔α〕ｏ−１１６．５形（ＡｃｅｔＯｎｅ，ｃ＝０．３
６），ＭＳｍ／ｓ：７８８（Ｍ＋）ＰＭＲ（ＡｃｅｔＯ
ｎｅ−Ｄ６）Ｐｐｍ：２．２５〜２．７６（４Ｈ９ｍ９
ｃ２９６−Ｈ），５．５２（１Ｈ，ｄｄ，ｊ＝８．３Ｈ
ｚ，Ｃ４−Ｈ）″，５．７２〜５．９６（２ＦＩ，ｍ，
Ｃ３，５一Ｈ），７．０５，７．０９，７．１６（Ｅａ
ｃｈ？，Ｓ，ｇａｌ．Ｈ）。[α] o-116.5 type (AcetOne, c=0.3
6), MSm/s: 788 (M+) PMR (AcetO
ne-D6) Ppm: 2.25-2.76 (4H9m9
c296-H), 5.52 (1H, dd, j=8.3H
z, C4-H)'', 5.72-5.96 (2FI, m,
C3,5-H), 7.05, 7.09, 7.16 (Ea
Ch? , S, gal. H).
ＣＭＲ（ＡｃｅｔＯｎｅ−Ｄ６）Ｐｐｍ：３６．２（Ｔ
，Ｃ６），３８．１（Ｔ，Ｃ２），６８．８（Ｄ，Ｃ３
），６９．７（Ｄ，Ｃ５），７２．１（Ｄ，Ｃ４），７
４．１（Ｓ，Ｃｌ），１０９．８（Ｄ，ｇａｌｌ．Ｃ２
，Ｃ６×３），１２０．４，１２１．１（Ｓ，ｇａｌｌ
．Ｃｌ×３），１３８．７，１３９．８（Ｓ，ｇａＩ．
Ｃ４×３），１４５．５（Ｓ，ｇａｌ．Ｃ３，５×３）
，１６６．２（Ｓ，−ＣＯＯ−×３），１７６．２（−
ＣＯＯＨ）。同様にして３，４，５−Ｔｒｉ−０−Ｇａ
ｌｌＯｙｌｑｕｉｎｉｃａｃｉｄ無色無定形粉末（収率
０．００５％）を得た。〔α〕ｏ−３５．５ｄ（Ａｃｅ
ｔＯｎｅ，ｃ＝０．１９），ＰＭＲ（ＡｃｅｔＯｎｅ−
Ｄ６）Ｐｐｍ：２．１０−．２．５０（４Ｈ，ｍ，Ｃ２
，６−Ｈ），４．５３（１Ｈ，ｓｅｘ，ｊ＝８．６Ｈｚ
，Ｃ３−Ｈ），５．１７（１Ｈ，ｄｄ，Ｊ＝９Ｈｚ，３
Ｈｚ，Ｃ５−Ｈ），７．０８，７．１３（Ｅａｃｈ２Ｈ
，ｓ，ｇａｌ．Ｈ）。CMR (AcetOne-D6) Ppm: 36.2 (T
, C6), 38.1 (T, C2), 68.8 (D, C3
), 69.7 (D, C5), 72.1 (D, C4), 7
4.1(S,Cl), 109.8(D,gall.C2
,C6×3),120.4,121.1(S,gall
．． Cl×3), 138.7, 139.8 (S, gaI.
C4 x 3), 145.5 (S, gal. C3, 5 x 3)
,166.2(S,-COO-×3),176.2(-
COOH). Similarly, 3,4,5-Tri-0-Ga
llOylquinicacid colorless amorphous powder (yield 0.005%) was obtained. [α]o-35.5d(Ace
tOne, c=0.19), PMR(AcetOne-
D6) Ppm: 2.10-. 2.50 (4H, m, C2
, 6-H), 4.53 (1H, sex, j=8.6Hz
, C3-H), 5.17 (1H, dd, J=9Hz, 3
Hz, C5-H), 7.08, 7.13 (Each2H
,s,gal. H).
ＣＭＲ（ＡｃｅｔＯｎｅ−Ｄ６）Ｐｐｍ：３６・７（Ｃ
６）９４１・６（Ｃ２），６５．５（Ｃ３），６９．７
（Ｃ５），７４．６（Ｃ１），７５．９（Ｃ４），１０
９．９（Ｇａｌｌ．Ｃ２，Ｃ６×２），１２１．３，１
２１．７（？１１．Ｃ１），１３８．３，１３８．５（
？１．Ｃ４），１４５．５（？１．Ｃ３，５×２），１
６５．８，１６６．１（−ＣＯＯ−），１７６．５（−
ＣＯＯＨ）。実施例２
ウラジロガシ皮６．３ｋｇを水性アセトン５′で抽出し
、酢酸エチル１′で分液、酢酸エチル可溶部をあつめ、
ＳｅｐｈａｄｅｘＬＨ−２０でカラムクロマト分離をく
り返し、精製したところ、以下のＧａＩｌＯｙｌｑｕｅ
ｒｉｔＯｌ類を得た。CMR (AcetOne-D6) Ppm: 36.7 (C
6) 941.6 (C2), 65.5 (C3), 69.7
(C5), 74.6 (C1), 75.9 (C4), 10
9.9 (Gall. C2, C6 x 2), 121.3, 1
21.7 (?11.C1), 138.3, 138.5 (
? 1. C4), 145.5 (?1.C3,5×2), 1
65.8, 166.1 (-COO-), 176.5 (-
COOH). Example 2 Extract 6.3 kg of the skin of Japanese oak with 5' aqueous acetone, separate the liquid with 1' ethyl acetate, collect the ethyl acetate soluble part,
After repeated column chromatography separation using Sephadex LH-20 and purification, the following GaIlOylque was obtained.
ritOls were obtained.
１無色無定形粉末（収率０．７％）
〔α〕Ｄ−１０７．７（ｃ＝０．６７，Ｍｅ０Ｈ）ＰＭ
Ｒ（ＡｃｅｔＯｎｅ−Ｄ６＋ＣＤ３ＯＤ）Ｐｐｍ：２．
０４−２．２０（２１１，ｍ，Ｃ６−Ｈ），３．２９−
４．１６（３Ｈ，ｍ，Ｃ１，２，３−Ｈ），５．３８（
１Ｈ，ｄｄ，Ｊ＝１０，６Ｈｚ，Ｃ５−Ｈ），５．６０
（１Ｈ，ｔ，Ｊ＝１０Ｈｚ，Ｃ４−Ｈ），６．９８，７
．０４（Ｅａｃｈ２ｌ（，Ｓ，ｇａｌ．Ｈ）ＣＭＲ（Ａ
ｃｅｔＯｎｅ−Ｄ６＋ＣＤ３ＯＤ）Ｐｐｍ：３２．７（
Ｔ，Ｃ６），６９．４（Ｄ，Ｃｌ），７０．７（Ｄ，Ｃ
６），７１．４（Ｄ，Ｃ３），７３．９（Ｄ，Ｃ２），
７５．６（Ｄ，Ｃ４），１０９．７，１０９．８（Ｄ，
ｇａｌ．Ｃ２，６），１２１．１，１２１．３（Ｓ，ｇ
ａｌ．Ｃｌ），１３８．６（Ｓ，ｇａＩ．Ｃ４×２），
１４５．８（Ｓ，ｇａｌ．Ｃ３，５×２），１６６．６
，１６７．４（Ｓ，−ＣＯＯ−）４，５−Ｄｉ−０−Ｇ
ａＩｌＯｙｌｑｕｒｅｃｉｔＯｌ２無色針状晶（収率０
．００６％）Ｍｐ２５５−２５８０Ｃ
〔α〕ｏ−１０．５０（ｃ＝０．６８，ａｃｅｔ０ｎｅ
）ＰＭＲ（ＡｃｅｔＯｎｅ−Ｄ６）Ｐｐｍ：２．１０−
２．３０（２Ｈ，ｍ，Ｃ６−Ｈ），４．１８，４．２９
（ＥａｃｈｌＨ，ｓ−１１ｋｅ，Ｃ１９２−Ｈ）９５．
４０−５●７６（？９ｎ９ｃ３９５−Ｈ），５．９０（
１Ｈ，ｔ，Ｊ＝１０Ｈｚ，Ｃ４−Ｈ），７．００，７．
０５，７．０８（Ｅａｃｈ２Ｈ，ｓ，ｇａｌ，Ｈ）。1 Colorless amorphous powder (yield 0.7%) [α]D-107.7 (c=0.67, Me0H) PM
R(AcetOne-D6+CD3OD)Ppm:2.
04-2.20 (211, m, C6-H), 3.29-
4.16 (3H, m, C1,2,3-H), 5.38 (
1H, dd, J=10,6Hz, C5-H), 5.60
(1H, t, J=10Hz, C4-H), 6.98, 7
．． 04(Each2l(,S,gal.H)CMR(A
cetOne-D6+CD3OD)Ppm:32.7(
T, C6), 69.4 (D, Cl), 70.7 (D, C
6), 71.4 (D, C3), 73.9 (D, C2),
75.6 (D, C4), 109.7, 109.8 (D,
gal. C2, 6), 121.1, 121.3 (S, g
al. Cl), 138.6 (S, gaI.C4×2),
145.8 (S, gal. C3, 5×2), 166.6
,167.4(S,-COO-)4,5-Di-0-G
aIlOylqurecitOl2 colorless needle crystals (yield 0
．． 006%) Mp255-2580C [α]o-10.50 (c=0.68, acet0ne
) PMR (AcetOne-D6) Ppm: 2.10-
2.30 (2H, m, C6-H), 4.18, 4.29
(EachlH, s-11ke, C192-H)95.
40-5●76(?9n9c395-H), 5.90(
1H, t, J=10Hz, C4-H), 7.00, 7.
05, 7.08 (Each2H, s, gal, H).
Claims (1)
５は水素又は−ＣＯＯＨを表わし、Ｒ＾１＾６は水素又
は水酸基を表わし、Ｒ＾１＾７、Ｒ＾１＾８、Ｒ＾１＾
９は同一又は異なつて水素又はガロイル基▲数式、化学
式、表等があります▼以下「Ｇ」と略す。 ）を表わす。ただし、Ｒ＾１＾７、Ｒ＾１＾８、Ｒ＾１
＾９のうちいずれか２つ以上がガロイル基である場合に
限る。）で表わされる新規タンニン。[Claims] 1 The following general formula [VII] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [VII] (R^1^
5 represents hydrogen or -COOH, R^1^6 represents hydrogen or a hydroxyl group, R^1^7, R^1^8, R^1^
9 is the same or different hydrogen or galloyl group ▲ Numerical formula, chemical formula, table, etc. ▼ Hereinafter abbreviated as "G". ). However, R^1^7, R^1^8, R^1
Only when any two or more of ^9 are galloyl groups. ) is a new tannin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16180784A JPS6050778B2 (en) | 1984-07-31 | 1984-07-31 | tannin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16180784A JPS6050778B2 (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 (2)
| Publication Number | Publication Date |
|---|---|
| JPS6064947A JPS6064947A (en) | 1985-04-13 |
| JPS6050778B2 true JPS6050778B2 (en) | 1985-11-11 |
Family
ID=15742285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16180784A Expired JPS6050778B2 (en) | 1984-07-31 | 1984-07-31 | tannin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6050778B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR19980034292A (en) * | 1996-11-06 | 1998-08-05 | 성재갑 | Skin whitening composition containing galloylquinic acid |
-
1984
- 1984-07-31 JP JP16180784A patent/JPS6050778B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6064947A (en) | 1985-04-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0264173B1 (en) | Bryostatins | |
| US4210581A (en) | Organic compounds | |
| Fried et al. | The hypotensive principles of Veratrum viride | |
| US5441932A (en) | Sugar compounds for inhibition of the biosynthesis of sugar chains containing sialic acid | |
| JPS62142181A (en) | Novel tannin | |
| JPS6248677A (en) | Novel tannin | |
| JPH0229078B2 (en) | ||
| JPS6050778B2 (en) | tannin | |
| JPS6011912B2 (en) | tannin | |
| US4895852A (en) | Antitumor alkaloids | |
| JPS6157594A (en) | Galactosphingolipid and its production | |
| JPH0246598B2 (en) | SHINKINARUTANNIN | |
| JPWO1995004041A1 (en) | Carbazole compounds | |
| JPS6353993B2 (en) | ||
| US4092412A (en) | Treatment of herpes simplex infections | |
| DE69323998T2 (en) | PHARMACEUTICAL ACTIVE FLAVILIUM COMPOUNDS | |
| JPH01500516A (en) | Guaiazulene derivatives and their usage | |
| DK160828B (en) | METHOD FOR PREPARING A REACTION PRODUCT OF 2-METHYL-2,5-DIMETHOXY-2,5-DIHYDRO-FURAN AND L-ASCORBIC ACID | |
| JPS61112090A (en) | Novel tannin | |
| JPS6249277B2 (en) | ||
| JPH07285877A (en) | Reverse transcriptase inhibitor of hiv-1 | |
| JPS6348213A (en) | Antitumor agent | |
| Gramshaw et al. | 571. Gallotannins. Part V. The structure of penta-and tetra-O-galloylglucoses, and some observations on the molecular weights of the gallotannins | |
| JPS6249278B2 (en) | ||
| JPS59184158A (en) | Clavulone derivative |