JPS6064947A - Tannin - Google Patents

Tannin

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Publication number
JPS6064947A
JPS6064947A JP16180784A JP16180784A JPS6064947A JP S6064947 A JPS6064947 A JP S6064947A JP 16180784 A JP16180784 A JP 16180784A JP 16180784 A JP16180784 A JP 16180784A JP S6064947 A JPS6064947 A JP S6064947A
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JP
Japan
Prior art keywords
acetone
ethyl acetate
formula
column chromatography
gal
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
Application number
JP16180784A
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Japanese (ja)
Other versions
JPS6050778B2 (en
Inventor
Itsuo Nishioka
西岡　五夫
Genichiro Nonaka
源一郎 野中
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Nippon Shinyaku Co Ltd
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Nippon Shinyaku Co Ltd
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Priority to JP16180784A priority Critical patent/JPS6050778B2/en
Publication of JPS6064947A publication Critical patent/JPS6064947A/en
Publication of JPS6050778B2 publication Critical patent/JPS6050778B2/en
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

NEW MATERIAL:A compound expressed by formula I (R<15> is H or COOH; R<16> is H or OH; R<17>-R<19> are H or galloyl group expressed by formula II). EXAMPLE:3,4-Di-O-galloyl-quinic acid. USE:A metabolic regulating agent capable of exhibiting enzymic inhibitory action by bonding with enzymic proteins in the body. PREPARATION:Plants, e.g. myricae cortex, cinammon bark, betel nut, sanquisorbae radix, trapae fructs, Quercus salicina Blume, cowberry leaves, etc. are subjected to extraction with acetone, distribution with ethyl acetate and water, column chromatography, etc. to give the aimed compound expressed by formula I . For example 6.3kg Quercus salicina Blume is extracted with 5l 80% aqueous acetone, and the acetone is distilled away. The resultant aqueous solution is let to separate with 1l ethyl acetate about 10 times, and a portion soluble in ethyl acetate can be collected, separated and purified by column chromatography with ''Sephadex LH-20'' using solvent ethanol and 80% aqueous ethanol to give the exemplified compound.

Description

【発明の詳細な説明】 本発明は医薬品とｔ７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 a tannin useful in pharmaceuticals and T7, and a method for producing the tannin.

タンニンは広く漬物界に分布し、収れん作用のあるとこ
ろから収れん薬として、また皮を菫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はどで複５゛１［な構造を有しており、単離
楕関の困Ｄ’ｌｔさとあいまって研究が遅れていた。Tannins are widely distributed in the world of pickles, and have been used as an astringent due to their astringent properties, and as a tanning agent to turn the skin into violet. Tannin has a molecular weight of 600
~2000 has a complex structure, and research has been delayed due to difficulties in isolating it.

一方、従来よりうらし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だした。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ってその活性を低
下させることが判っている。On the other hand, useful medicinal effects based on enzyme inhibitory effects, such as rinsing, have been known for a long time, and the present inventors isolated and obtained novel tannins from many plants and examined their pharmacological effects. We have discovered enzyme inhibitory effects. 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.

本発明に係る化合物は、代謝調節剤として有用である。Compounds according to the invention are useful as metabolic regulators.

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、供椰子、地楡、
菱実、ウラジロガシ皮、コケモモ葉等の植物から、アセ
１−ンによる抽出、ｌ！ｉｌ：酸エチル：水の分配、カ
ラムクロ゛マド等公知の方法により容易に得ることがで
きる。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 compounds according to the present invention include Yang Mei Peel, Cinnamon Peel, Xuan Coconut, Di Yu,
Extraction using acetone from plants such as rhombus, oak bark, and lingonberry leaves. il: can be easily obtained by known methods such as ethyl acid:water partitioning and column chromatography. 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１５げて詳ａｔに説明する。(Next page below) Hereinafter, 15 examples will be explained in detail.

実施例１ ウラジロガシ皮６　、３　ｋｇを８０％の水性アセトン
５βで抽出し、アセトンを留去後、水溶液を酢酸エチル
ｉｐで約１０回分液、酢酸エチル可溶部をあつめ、５ｅ
ｐｈａｄｅｘ　Ｌｌｌ−２０でン容媒エタノール、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４５吋を得た。Example 1 Extract 6.3 kg of the skin of the horsetail oak with 80% aqueous acetone 5β, distill off the acetone, divide the aqueous solution about 10 times with ethyl acetate IP, collect the ethyl acetate soluble part, and extract 5e.
phadex Lll-20 ethanol, 80
After column chromatographic separation and purification using % aqueous methanol, 45 inches of the following substance was obtained.

無色無定形粉末。［αｌＤ−１０２，８°　（ｃ＝０．
３２、　ａｃｅｔｏｎｅ　） １月・Ｉｌｌ　（ａｃｅｔｏｎｅ　−ｄｃ　）　ｐｐｍ
　：２．１０−２．５０　（４１１，ｍ＋Ｃ２，６−Ｉ
ｔ）　、４．５０　（ＩＩＩ、ｄ−１ｉｋｅ、Ｊ＝４１
１ｚ、ＣＳ　−Ｉｆ）　、　５．２５　’（ＩＩＩ、ｄ
ｄ、　Ｊ＝７，４１１ｚ　、Ｃ４−ＩＩ）　、　５．６
０−５、り３　（ＩＩＩ、ｍ、Ｃ３−Ｉｆ）　＋　７．
０５．７．１１　（ｅａｃｈ　２１Ｌ　ｓ、ｇａｌ、Ｉ
Ｉ）。Colorless amorphous powder. [αlD−102,8° (c=0.
32, acetone) January・Ill (acetone-dc) ppm
:2.10-2.50 (411,m+C2,6-I
t), 4.50 (III, d-1ike, J=41
1z, CS-If), 5.25'(III, d
d, J=7,411z, C4-II), 5.6
0-5, ri3 (III, m, C3-If) + 7.
05.7.11 (each 21L s, gal, I
I).

ＣＭＲ（ａｃｅｔｏｎｅ　−ｄｑ　）　ｐｐｍ　：　３
Ｂ、０　（Ｃ２Ｌ＋３９．０　（Ｃｃ　）　、　６Ｂ、
５　（Ｃ；　）　、　６８．７　（（：３）。CMR (acetone-dq) ppm: 3
B, 0 (C2L+39.0 (Cc), 6B,
5 (C; ), 68.7 ((:3).

７５．２　（Ｃ＋　）　、　７５．５　（Ｃ４）　、　
１０９．７．１０９．８　（ｇａｌｌ、ｃ２．　ｃ　）
　、　１２０．６　（ｇａｌ、　＋４　ｘ２　）　。75.2 (C+), 75.5 (C4),
109.7.109.8 (gall, c2.c)
, 120.6 (gal, +4 x2).

１．３８．７　（ｇａｌ、　Ｃ４ｘ２　）　、　’１４
５．５　（ｇａｌ、　Ｃ３。1.38.7 (gal, C4x2), '14
5.5 (gal, C3.

５Ｘ２　）　、　１６６．３．１６６．６　（−ｃｏｏ
−）　、　１７７．５　（−ＣＯＯ１１）　。5X2), 166.3.166.6 (-coo
-), 177.5 (-COO11).

３．４−Ｄｉ−０−Ｈａｌｌｏｙｌ　ｑｕｉｎｉｃ　ａ
ｃｉｄ。3.4-Di-0-Halloyl quinic a
cid.

同様にして３．５−１１４−０−（Ｈａｌｌｏｙｌ　ｑ
ｕｉｎｉｃ　Ａｃ１ｄ無色無定形粉末＜ｒｉ：ｚ率ｏ、
ｏｏｃ％）を得た。Similarly, 3.5-114-0-(Halloyl q
uinic Ac1d colorless amorphous powder <ri:z ratio o,
ooc%) was obtained.

（α）ｏ　６３．０”　（（：　＝０．２０．　ａＣｅ
ｔｏｎｃ　）！’ＭＲ（ａｃｅｔｏｎ　ｅ　−ｄｃ　）
　ｐｐｍ　：　２．３３　（４１１，ｄ−１ｉｋｅ。(α) o 63.0” ((: =0.20. aCe
tonc)! 'MR (aceton e-dc)
ppm: 2.33 (411, d-1ike.

Ｊ＝７１１ｚ　、Ｃ２，６−ｉｔ）　、４．１４　（ｌ
ＩＬｄｄ、Ｊ＝７．４ｉｌｚ、Ｃ４−ＩＩ＞　、　５．
４０−５．（ｉ８　（２１Ｌｍ、Ｃ３，ｓ　−ＩＩ）　
。J=711z, C2,6-it), 4.14 (l
ILdd, J=7.4ilz, C4-II>, 5.
40-5. (i8 (21Lm, C3,s-II)
.

”１．１３．７．１９　（ｅｌｌｃｈ　２１１．ｓ、ｇ
ａｌ、ＩＩ　）。”1.13.7.19 (ellch 211.s, g
al, II).

ＣＭＲ（ａｃｅｔｏｎｅ　−ｄｃ　）　ｐＨｍ　：　３
５．７　（Ｃ６）　＋３７．５　（Ｃ２）　、　７０．
１　（Ｃ４）　、　’７２．０　（Ｃ３）　。CMR (acetone-dc) pHm: 3
5.7 (C6) +37.5 (C2), 70.
1 (C4), '72.0 (C3).

７２．１　（Ｃ５）　、　７４．２　（Ｃ＋　）　、　
１０９．８　（ｇ＋＋Ｉ。72.1 (C5), 74.2 (C+),
109.8 (g++I.

Ｃ２、ｃ　Ｘ２　）　、　１２１．４．１２１．９　（
ｇ、］１．　Ｃ＋　）　。C2, c X2 ), 121.4.121.9 (
g,]1. C+).

１３８．３．１３８．６　（ＩＩａ１．　Ｃ４）　＋　
１４５．５　（ｇａｌ。138.3.138.6 (IIa1.C4) +
145.5 (gal.

Ｃ３，ｓ　Ｘ２　）　、　１６６．１　（−ＣＯＯ−ｘ
２　）　、ど５．８（−ＣＯＯＩＩ　＞。C3,sX2), 166.1 (-COO-x
2), do5.8(-COOII>.

しパ］ 同様にして４．５−Ｉ）ｉ−０−ｇａｌｌｏｙｌ　ｑｕ
ｉｎｉｃ　ａｃｉｄ黄かっ仏典定形粉末（収率０．００
５％）を得た。] Similarly, 4.5-I) i-0-galloyl qu
inic acid Yellow Kabutsuden powder (yield 0.00
5%).

Ｃ（Ｘ）Ｄ−１１６，５°　（ａｃｅｔｏｎｅ、ｃ　＝
０．３Ｃ４）　。C(X)D-116,5° (acetone, c =
0.3C4).

Ｍ　Ｓ　ｍ／ｓ　：　７８８　（Ｍ＋）円ＩＲ（ａｃｅ
ｔｏｎｅ　−ｄｅ　）　ｐｐｍ　：　２．２５〜２．７
６　（４１１＋ｍ、Ｃ２，６−１１）　、　５．５２　
（ＩＩＩ、ｄｄ、　Ｊ＝（１，３１１ｚ　、Ｃ４−ＩＩ
）、　５．７２〜５．９６　（２１１，ｍ、Ｃ＋　、　
５−Ｉｔ）　、　７．０５．７．０９７．１６　（ｅａ
ｃｈ　２１Ｌｓ＋ｇａ１．Ｉｌ　）。M S m/s: 788 (M+) Yen IR (ace
tone-de) ppm: 2.25-2.7
6 (411+m, C2,6-11), 5.52
(III, dd, J=(1,311z, C4-II
), 5.72-5.96 (211, m, C+,
5-It), 7.05.7.097.16 (ea
ch 21Ls+ga1. Il).

ＣＭＲ（ａｃｅｔｏｎｅ　−ｄｓ　）　ｐｐｍ　：　３
６．２　（ｔ、Ｃａ　）　。CMR (acetone-ds) ppm: 3
6.2 (t, Ca).

３８．１　（ｔ、　Ｃ２）　、　６８．８　（ｄ、　Ｃ
３）　、　６９．７　（ｄ。38.1 (t, C2), 68.8 (d, C
3), 69.7 (d.

Ｃ５）　、　７２．１　（ｄ、　Ｃ４）　、　７４．１
　（ｓ、自）、＝１０９．８　（ｄ、　Ｈａｌｌ、　Ｃ
２、Ｃｃ　×３　）　、　１２０．４．１２１．１（ｓ
、［！ａ１１．自ｘ３　）　、１３８．７．１３９．８
　（６，、Ｈａｌ。C5), 72.1 (d, C4), 74.1
(s, self), = 109.8 (d, Hall, C
2, Cc ×3), 120.4.121.1(s
, [! a11. Self x3), 138.7.139.8
(6,,Hal.

Ｃ４×３）、　１４５．５　（Ｓ、　ｇａｌ、Ｃ３＋　
ｓ　×３）、　１６６．２　（ｓ、　−ＣＯＯ−×３　
）　、１７６．２　（−ＣＯＯＩＩ　）。C4×3), 145.5 (S, gal, C3+
s × 3), 166.2 (s, -COO- × 3
), 176.2 (-COOII).

Ｕ實 同様にして３，４．５−ｔｒｉ−０−ｇａｌｌｏｙｌ　
ｑｕｉｎｉｃ　ａｃｉｄ無色無定形粉末（収率０．００
５％）を得た。3,4.5-tri-0-galloyl as in U.S.
quinic acid colorless amorphous powder (yield 0.00
5%).

〔α）ｏ　３５．５’　（ａｃｅｔｏｎｅ、ｃ＝０．１
９）　。[α) o 35.5' (acetone, c=0.1
9).

ＰＭＲ（ａｃｅｔｏｎｅ　−ｄ　Ｇ　）　ｐｐｌｎ　：
　２．１０〜２．５０　（４１１，ｍ＋Ｃ２，６−１１
）　＋　４．５３　（ＩＩＩ、ｓｅｘ、Ｊ＝８．６１１
ｚ　、Ｃ３−１１）、　５．１７　（ＩＩＩ、ｄｄ、　
Ｊ−９１１ｚ、　３１１２．Ｃ５−ＩＩ）　、　７．０
８゜７．１３　（ｅａｃｈ　２１Ｌｓ＋’ｇａ１．ｌＩ
　）。PMR (acetone-d G) ppln:
2.10~2.50 (411,m+C2,6-11
) + 4.53 (III, sex, J=8.611
z, C3-11), 5.17 (III, dd,
J-911z, 3112. C5-II), 7.0
8゜7.13 (each 21Ls+'ga1.lI
).

（Ｊｌｌｌ　（ａｃｅｔｏｎｅ　−ｄ　６　）　ｐｐｍ
　：’３６．１　（Ｃｃ　）　。(Jllll (acetone-d6) ppm
:'36.1 (Cc).

４１．６　（Ｃ２）　、　６５．５　（Ｃ３）　、　（
ｉ９．７　（Ｃｓ　）　。41.6 (C2), 65.5 (C3), (
i9.7 (Cs).

７４．６　（Ｃ＋　）　、　７５．９　（Ｃ４）　、　
１０９．９　（ｇａｌｌ。74.6 (C+), 75.9 (C4),
109.9 (gall.

Ｃ２、Ｃ６×２　）　、　１２１．３．１２１．７　（
ｇａｌｌ、Ｇ４　）　。C2, C6×2), 121.3.121.7 (
Gall, G4).

１３８．３．１３８．５　（ｇａｌ、　Ｃ４）　、　１
４５．５　（ｇａｌ。138.3.138.5 (gal, C4), 1
45.5 (gal.

Ｃ３＋　ｓ　×２　）　、１６５．８，１６６．１　（
−ＣＯＯ−）　。C3+ s ×2), 165.8, 166.1 (
-COO-).

１７６．５　（−ｃｏｏｎ　）。176.5 (-coon).

実施例２ ウラシロカシ皮６．３ｋｇを水性アセトン５βで抽出し
、酢酸゛エチル１ρで分液、酢酸エチル可ｌ容部をあつ
め、５ｅｐｂａｄｃｘ　Ｌｌｌ−２０でカラムク１：１
７１・分離をくり返し、箱型したところ、以下のｇａｌ
ｌｏｙｌ　ｑｕｅｒｃｉｔｏｌ　’ＪＲを得ノこ。Example 2 Extract 6.3 kg of white oak bark with 5β aqueous acetone, separate the liquid with 1μ ethyl acetate, collect the 1 volume of ethyl acetate, and column mix 1:1 with 5epbadcx Lll-20.
71・After repeating the separation and making a box shape, the following gal
loyl quercitol 'JR.

■、無色無定形粉末（収率０．７％） 〔α）。−１０７，２°　（ｃ　＝０．Ｇ１．　ＭｅＯ
Ｉｌ）凹Ｉｔ　（ａｃｅｔｏｎｅ−ｄ６→−ＣＩ＋３０
０）　ｒｌｐｍ　：　２．０４−２．２０　（２１１，
ｍ、Ｃ（、−Ｉｆ）　、　３．２９−４．１６　（３１
１，ｍ、自１２　、３−Ｉｆ）　、　５．３８　（１１
Ｌｄｄ、Ｊ＝１０．６１１ｚ、Ｃ５−Ｉｔ）　。■, Colorless amorphous powder (yield 0.7%) [α). -107,2° (c = 0.G1.MeO
Il) Concave It (acetone-d6→-CI+30
0) rlpm: 2.04-2.20 (211,
m, C(,-If), 3.29-4.16 (31
1, m, self 12, 3-If), 5.38 (11
Ldd, J=10.611z, C5-It).

５、（ｉｏ　（Ｉｌｌ、Ｌ、Ｊ＝１０１１ｚ、Ｃ４−Ｉ
Ｉ）　、　Ｃｉ、９Ｂ、７．０４（ｅａｃｌ＋　２１１
．ｓ＋ｇａ１．ｌｌ　）Ｃｕｌｌ　（ａｃｅｔｏｎｅ−
ｄＧ４−ＣＤ３００）　ｐｐｍ　：　３２，７　（ｔ。5, (io (Ill, L, J=1011z, C4-I
I), Ci, 9B, 7.04 (eacl+ 211
．． s+ga1. ll ) Cull (acetone-
dG4-CD300) ppm: 32,7 (t.

Ｃｃ　）　、　６９．４　（ｄ、　Ｃ＋　）　、　７０
．７　（ｄ、　Ｃ５）　。Cc), 69.4 (d, C+), 70
．． 7 (d, C5).

７１．４　（ｄ、　Ｃ３）　、　７３．９　（ｄ、　Ｃ
２）　、　７５．６　（ｄ。71.4 (d, C3), 73.9 (d, C
2), 75.6 (d.

Ｃ４）　、　１０９．７．１０９．８　（ｄ、ｇａｌ、
　Ｃ２、ｓ　）　。C4), 109.7.109.8 (d, gal,
C2,s).

１２１．１．１２１．３　（ｓ、ｇａｌ、　Ｃ＋　）　
、　１３８．６　（ｓ、ｇａｌ。121.1.121.3 (s, gal, C+)
, 138.6 (s, gal.

Ｃ４×２　）　、　１４５．！３　（ｓ＋ｇａ１．　Ｃ
３、５Ｘ２　）　。C4×2), 145. ! 3 (s+ga1.C
3,5X2).

１６Ｇ、６．１６７．４　（ｓ、　−ＣＯＯ−）１−１ ４．５−Ｄｉ−０−ｇａｌｌｏｙｌ　ｑｕｒｅｃｉＬｏ
１２、無色旧状晶（収率０．００Ｇ％） ｍｐ　２５５−２５８℃ 〔αｌｏ　ｉＯ，５°　（ｃ　＝　０．６８＋　ａｃｅ
ｔｏｎｅ）Ｉ’Ｍｌｌ　（ａｃｅｔｏｎｅ−ｄ６）　ｐ
ｐｍ　：　２．１０−２．３０　（２１１，ｍ＋Ｃｅ　
−ＩＩ）　＋　４．１８＋　４．２９　（ｅａｃｌ＋　
ＩＩＩ、５−１ｉｋｅ、ＣＩ。16G, 6.167.4 (s, -COO-)1-1 4.5-Di-0-galloyl qureciLo
12. Colorless old-state crystal (yield 0.00G%) mp 255-258℃ [αlo iO, 5° (c = 0.68+ ace
tone) I'Mll (acetone-d6) p
pm: 2.10-2.30 (211, m+Ce
-II) + 4.18+ 4.29 (eacl+
III, 5-1ike, CI.

２−ＩＩ）　１５．４０−５．７（ｉ　（２１１，ｎ、
Ｃ３、５−ＩＩ）　、　５．９０（ＩＩＩ、ｔ、Ｊ＝１
０１１ｚ、Ｃ４−Ｉり　、　７．００．７．０５．７．
０ＥＩ（ｅａｃｔ＋　２１１．ｓ、ｇａｌ、ＩＩ　）。2-II) 15.40-5.7(i (211,n,
C3, 5-II), 5.90 (III, t, J=1
011z, C4-Iri, 7.00.7.05.7.
0EI (eact+ 211.s, gal, II).

にＭＲ（ａｃｅｔｏｎｅ　ｄａ　）　ｐｐｍ　：　３２
．３　（ｔ、Ｃ６）　＋６９．３　（ｄ、　ＣＩ）　、
　７１．２　（ｄ、　Ｃ２、３）　、　７２．４　（ｄ
、　Ｃ４）　、　７３．２　（＋４．　Ｇ５）　＋　１
０９．７　（ｄ、（、：ａｔ。MR (acetone da) ppm: 32
．． 3 (t, C6) +69.3 (d, CI),
71.2 (d, C2, 3), 72.4 (d
, C4) , 73.2 (+4. G5) + 1
09.7 (d, (,:at.

Ｃ２＋　ｅ　×３　）　、　１２０．５　（ｓ、ｇａｌ
、　Ｃ１ｘ３　）　。C2+ e ×3), 120.5 (s, gal
, C1x3).

１３８．９　（ｓ、Ｂａ１．　Ｃ４×３　）　、　１４
５．５　（ｓ、ｇａｌ、　Ｃ３、５×３　）　、　１（
ｉ６．５　（ｓ、−ＣＯＯ−×２　）　、　ｌＧ７．１
（ｓ、−ＣＯＯ−）。138.9 (s, Ba1. C4×3), 14
5.5 (s, gal, C3, 5×3), 1(
i6.5 (s, -COO-x2), lG7.1
(s, -COO-).

ＱＨ ３＋４＋５−Ｔｒｉ−０−Ｂａｌｌｏｙｌ　ｑｕｅｒｃ
ｉｔｏ＋以上QH 3+4+5-Tri-0-Balloyl querc
ito+ or higher

Claims (1)

【特許請求の範囲】 次の一般式〔■〕 （ＲＩｓは水素又は−ＣＯＯＩＩを表わし、Ｒ１６は水
素又は水酸ハを表わし、Ｒ１７、Ｒ１８，１７１″は同
一以下ｒＧＪと略す６）を表わす。）で表わされる新規
タンニン。[Scope of Claims] The following general formula [■] (RIs represents hydrogen or -COOII, R16 represents hydrogen or hydroxyl, R17, R18, 171'' are the same and hereinafter abbreviated as rGJ6). ) is a new tannin.
JP16180784A 1984-07-31 1984-07-31 tannin Expired JPS6050778B2 (en)

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 true JPS6064947A (en) 1985-04-13
JPS6050778B2 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)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR19980034292A (en) * 1996-11-06 1998-08-05 성재갑 Skin whitening composition containing galloylquinic acid

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR19980034292A (en) * 1996-11-06 1998-08-05 성재갑 Skin whitening composition containing galloylquinic acid

Also Published As

Publication number Publication date
JPS6050778B2 (en) 1985-11-11

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