JP2628832B2 - New tannin - Google Patents
New tanninInfo
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- JP2628832B2 JP2628832B2 JP21006893A JP21006893A JP2628832B2 JP 2628832 B2 JP2628832 B2 JP 2628832B2 JP 21006893 A JP21006893 A JP 21006893A JP 21006893 A JP21006893 A JP 21006893A JP 2628832 B2 JP2628832 B2 JP 2628832B2
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- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、飲食品および医薬品と
して有用な新規タンニンおよびその製造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel tannin useful as a food and drink and a pharmaceutical and a method for producing the same.
【０００２】[0002]
【従来の技術】タンニンは、広く植物界に存在し、収斂
作用があることから、収斂薬として、また皮なめし剤と
して、古くより使用されて来た。しかし、一般にタンニ
ンは複雑な構造を有し、また単離精製の困難さと相俟っ
て研究が遅れていた。一方、タンニンは、上記の様な作
用に加え、各種の酵素の活性を阻害する性質を有し、種
々の生理、代謝調節剤としても有用であることが知られ
ている〔化学の領域、３５、２８（１９８２）〕。BACKGROUND OF THE INVENTION Tannins are widely used in the plant kingdom and have an astringent effect. Therefore, tannins have long been used as astringents and as tanning agents. However, tannins generally have a complicated structure, and studies have been delayed due to difficulties in isolation and purification. Meanwhile, tannin, in addition to such action of the above has the property of inhibiting the activity of various enzymes, various physiological, are known to be useful as metabotropic agent [chemical areas, 35 , 28 (1982)].
【０００３】タンニン類の酵素阻害については、飼い葉
（Ｆｏｄｄｅｒ ｐｌａｎｔｓ）のタンニン類が、リパ
ーゼや、アミラーゼ、プロテアーゼを阻害すること、ま
た豆（Ｆｉｅｌｄ ｂｅａｎ）のタンニンが、リパーゼ
を阻害することが報告されている（Ｂｒｉｔｉｓｈ
Ｊ． Ｎｕｔｒｉｔｉｏｎ，６０，２７５（１９８
８）、Ｊ．Ｓｃｉ．Ｆｏｏｄ Ａｇｒｉｃ．，３０，４
５８（１９７９））。また、４−ジ−Ｏ−ガロイルキナ
酸類（特公昭６０−５０７７８）および３′−Ｏ−Ｇａ
ｌｌｏｙｌｐｒｏｄｅｌｐｈｉｎｉｄｉｎ Ｂ−２（特
公昭６０−１１９１２）、４′，６′−Ｇａｌｌｏｙｌ
ｓａｌｉｄｒｏｓｉｄｅ（特公昭６３−５３９９３）
が、新規タンニンとして公示され、酵素タンパク質と結
合し、その活性を低下させる作用があり、代謝調節剤と
しての用途が示されている。[0003] Regarding the enzyme inhibition of tannins, it has been reported that tannins in feeder plants inhibit lipase, amylase and protease, and that tannins in field bean inhibit lipase. (British
J. Nutrition, 60 , 275 (198
8); Sci. Food Agric. , 30,4
58 (1979)). Also, 4-di-O-galloylquinic acids (JP-B-60-50778) and 3'-O-Ga
lloylpr o delphinidin B-2 (JP-B-60-11912), 4 ', 6'- Galloyl
salidroside (Japanese Patent Publication No. 63-53993)
Has been disclosed as a novel tannin, has the effect of binding to an enzyme protein and reducing its activity, and has been shown to be used as a metabolic regulator.
【０００４】マメ科の植物であるカワラケツメイ（Ｃａ
ｓｓｉａ ｎｏｍａｍｅ Ｈｏｎｄａ＝Ｃａｓｓｉａ
ｍｉｍｏｓｏｉｄｅｓ Ｌ． ｖａｒ． ｎｏｍａｍｅ
Ｍａｋｉｎｏ＝Ｃａｓｓｉａ ｍｉｍｏｓｏｉｄｅｓ
Ｌ． ｓｕｂｓｐ． ｎｏｍａｍｅ Ｏｈａｓｈｉ）
は、その全草が生薬として、利尿、整腸、健胃などの目
的で利用されており、また茶の代用としても飲用されて
いる。また、本植物の抽出物は、酵素の阻害作用が高い
ことが示されている〔薬用植物図譜、ｐ．１８２、金原
出版（１９６１）、Ｂｉｏｓｃｉ．Ｂｉｏｔｅｃｈ．Ｂ
ｉｏｃｈｅｍ．、５６、１４７８（１９９２）〕。[0004] The beetle plant, Kawataketsumei ( Ca
ssia noname Honda = Cassia
mimosoides L .; var. noname
Makino = Cassia mimosoides
L. subsp. noname Ohashi)
Is used as a crude drug for the purpose of diuresis, intestinal control, stomachic, etc., and is also used as a substitute for tea. In addition, it has been shown that the extract of the present plant has a high enzyme inhibitory action [medicinal plant chart, p. 182, Kanehara Publishing (1961), Biosci. Biotech. B
iochem. , 56 , 1478 (1992)].
【０００５】[0005]
【発明が解決しようとする課題】本発明者らは、植物の
薬効成分を検索する目的で、カワラケツメイ抽出エキス
から各種成分を単離取得して、酵素阻害活性に基づく薬
理効果を調べた。DISCLOSURE OF THE INVENTION The present inventors isolated and obtained various components from an extract of C. versicolor for the purpose of searching for a medicinal component of a plant, and examined a pharmacological effect based on the enzyme inhibitory activity.
【０００６】[0006]
【課題を解決するための手段】本発明者らは、カワラケ
ツメイ抽出エキスから酵素阻害活性の高い成分を検索し
た結果、新規タンニンを見出だし本発明を完成した。Means for Solving the Problems The present inventors have searched for a component having a high enzyme inhibitory activity from an extract of Aspergillus niger and found a novel tannin to complete the present invention.
【０００７】本発明によれば、式（１）According to the present invention, equation (1)
【０００８】[0008]
【化２】 Embedded image
【０００９】で表される新規タンニンが提供される。式
（１）で示される化合物は二つの異性体が存在する。There is provided a novel tannin represented by the formula: The compound represented by the formula (1) has two isomers.
【００１０】本発明に係る化合物は、体内酵素タンパク
質と結合することによってその活性を低下させる性質を
有し、代謝調節剤として有用である。また、種々の酵素
作用を抑制し、食品などの酵素作用に起因する劣化を防
止するのに利用することができる。The compound according to the present invention has the property of reducing its activity by binding to an in vivo enzyme protein, and is useful as a metabolic regulator. Further, it can be used for suppressing various enzyme actions and preventing deterioration caused by the enzyme action of foods and the like.
【００１１】本発明に係る化合物は、飲用にも供される
カワラケツメイから採取したもので、安全性が高い。[0011] The compound according to the present invention is collected from Kawataketsumei, which is also used for drinking, and has high safety.
【００１２】本発明に係る化合物は、例えばカワラケツ
メイからアセトンによる抽出、エーテルと水および酢酸
エチルと水への分配、およびカラムクロマトグラフィな
どの通常の分離方法により単離することができる。The compound according to the present invention can be isolated by a conventional separation method such as, for example, extraction from A. edulis with acetone, partitioning between ether and water, and between ethyl acetate and water, and column chromatography.
【００１３】[0013]
【実施例】以下、実施例により、本発明を更に詳細に説
明する。なお、本発明は以下の実施例にのみ限定される
ものではない。The present invention will be described in more detail with reference to the following examples. Note that the present invention is not limited only to the following examples.
【００１４】実施例１（カワラケツメイから抽出と分
画） 本物質はカワラケツメイ等から、溶媒抽出、液−液分
配、カラムクロマトグラフィーなど、公知の方法により
分離、採取することが可能である。[0014]Example 1 (Extraction and Mineral
Drawing) This substance can be extracted from Kawataketsumei etc. by solvent extraction, liquid-liquid separation.
By known methods, such as
It is possible to separate and collect.
【００１５】具体的には、図１に示すように、カワラケ
ツメイの果実乾燥物から７０％アセトンで抽出し、得ら
れた抽出液を濃縮後、エーテルにて抽出し、エーテル層
を除いた後、水層を酢酸エチルで抽出した。この酢酸エ
チルをＴｏｙｏｐｅａｒｌＨＷ−４０カラムに供し、７
０％エタノールで溶出し、分画した。この１分画をさら
にＭＣＩ ＧＥＬ ＣＨＰ−２０Ｐカラムに供し、各濃
度のメタノール水で溶出した。このうち４０％メタノー
ル溶出部を採取し、再度ＭＣＩ ＧＥＬカラムに供し、
メタノール水で溶出した。このうち４０％メタノール溶
出部の中間で当該化合物Ａが得られ、その後に当該化合
物Ｂが得られた。これらの収量は、０．０７％、０．０
３％であった。Specifically, as shown in FIG. 1, 70% acetone was extracted from the dried fruit of Kawataketsumei, and the obtained extract was concentrated, extracted with ether, and the ether layer was removed. The aqueous layer was extracted with ethyl acetate. This ethyl acetate was applied to a Toyopearl HW-40 column,
The fraction was eluted with 0% ethanol and fractionated. This one fraction was further applied to a MCI GEL CHP-20P column, and eluted with methanol water of each concentration. A portion eluted with 40% methanol was collected and subjected to the MCI GEL column again.
Elution was performed with methanol water. The compound A was obtained in the middle of the 40% methanol elution portion, and then the compound B was obtained. These yields were 0.07%, 0.0
3%.
【００１６】実施例２（当該化合物Ａの物理・化学的性
状） 実施例１の方法にて採取した化合物Ａの性状を常法によ
り測定した結果、以下のようであった。 Example 2 (Physical and chemical properties of the compound A)
State) The properties of Compound A collected by the method of Example 1 were measured by a conventional method, and the results were as follows.
【００１７】（１）形状：淡褐色無晶形粉末。(1) Shape: light brown amorphous powder.
【００１８】（２）旋光度：［α］Ｄ＋５９゜（ｃ＝
１，ＭｅＯＨ）。(2) Optical rotation: [α] D + 59 ° (c =
1, MeOH).
【００１９】（３）ＦＡＢ−ＭＳ ｍ／ｚ：５６９（Ｍ
＋Ｎａ）、５４７（Ｍ＋Ｈ）＋（ｐｏｓｉｔｉｖｅ−ｉ
ｏｎ ｍｏｄｅ；ｍａｔｒｉｘ，ｇｌｙｃｅｒｏｌ）、
５４５（Ｍ−Ｈ）＋（ｎｅｇａｔｉｖｅ−ｉｏｎ ｍｏ
ｄｅ；ｍａｔｒｉｘ，ｍ−ｎｉｔｒｏｂｅｎｚｙｌ ａ
ｌｃｏｈｏｌ）。(3) FAB-MS m / z: 569 (M
+ Na), 547 (M + H) + (positive-i
on mode; matrix, glycerol),
545 (M−H) + (negative-ion mo
de; matrix, m-nitrobenzyl a
lcohol).
【００２０】（４）ＵＶ λｍａｘＭｅＯＨｎｍ（ｌｏ
ｇ ε）：２８２（３．９７）。(4) UV λmax MeOH nm (lo
g?): 282 (3.97).
【００２１】（５）１Ｈ−ＮＭＲ（５００ＭＨｚ，ａｃ
ｅｔｏｎｅ−ｄ６＋Ｄ２Ｏ、３０℃） δ：２．１７［１Ｈ，ｍ，Ｈ−３（Ｕ１））］，２．４
５［１Ｈ，幅広いシグナル，Ｈ−３（Ｕ）］，２．５７
［１Ｈ，ｄｄ，Ｊ＝８，１６Ｈｚ，Ｈ−４
（Ｌ２））］，２．９２［１Ｈ，ｄｄ，Ｊ＝５．５，１
６Ｈｚ，Ｈ−４（Ｌ）］，４．０２［１Ｈ，ｍ，Ｈ−３
（Ｌ）］，４．４２［１Ｈ，幅広いシグナル，Ｈ−２
（Ｌ）］，４．４７［１Ｈ，ｔ，Ｊ＝６Ｈｚ，Ｈ−４
（Ｕ）］，５．２４［１Ｈ，ｍ，Ｈ−２（Ｕ）］，６．
０８［１Ｈ，ｓ，Ｈ−６（Ｌ）］，６．２３−６．２６
［２Ｈ，ｍ，Ｈ−８（Ｕ）およびＨ−６（Ｕ）］，６．
６２［２Ｈ，ｄｄ，Ｊ＝２，８Ｈｚ，Ｈ−６′（Ｕ）お
よびＨ−６′（Ｌ）］，６．６６［１Ｈ，ｂｒｄ，Ｊ＝
８Ｈｚ，Ｈ−５（Ｕ）］，６．６９，６．７４［各１
Ｈ，ｄ，Ｊ＝８Ｈｚ，Ｈ−５′（Ｕ）およびＨ−５′
（Ｌ）］，６．８３［２Ｈ，ｄ，Ｊ＝２Ｈｚ，Ｈ−２′
（Ｕ）およびＨ−２′（Ｌ）］． 注 １）上部ユニット、２）下部ユニット 以上のように、当該化合物Ａは、文献未記載の３′，
４′，７−ｔｒｉｈｙｄｒｏｘｙｆｌａｖａｎ−（４β
→８）−ｃａｔｅｃｈｉｎである。(5) 1 H-NMR (500 MHz, ac
etone- d 6 + D 2 O, 30 ℃) δ: 2.17 [1H, m, H-3 (U 1))], 2.4
5 [1H, wide signal, H-3 (U)], 2.57
[1H, dd, J = 8, 16 Hz, H-4
(L 2) )], 2.92 [1H, dd, J = 5.5, 1
6 Hz, H-4 (L)], 4.02 [1H, m, H-3
(L)], 4.42 [1H, wide signal, H-2
(L)], 4.47 [1H, t, J = 6 Hz, H-4
(U)], 5.24 [1H, m, H-2 (U)], 6.
08 [1H, s, H-6 (L)], 6.23-6.26
[2H, m, H-8 (U) and H-6 (U)], 6.
62 [2H, dd, J = 2.8 Hz, H-6 '(U) and H-6' (L)], 6.66 [1H, brd, J =
8 Hz, H-5 (U)], 6.69, 6.74 [1 for each
H, d, J = 8 Hz, H-5 '(U) and H-5'
(L)], 6.83 [2H, d, J = 2 Hz, H-2 '
(U) and H-2 '(L)]. Note 1) Upper unit, 2) Lower unit As described above, the compound A is 3 ′,
4 ', 7- trihydroxyflavan- (4β
→ 8) -catechin.
【００２２】[0022]
【化３】 Embedded image
【００２３】実施例３（当該化合物Ｂの物理・化学的性
状） 実施例１の方法にて採取した化合物Ｂの性状を常法によ
り測定した結果、以下のようであった。 Example 3 (Physical and chemical properties of the compound B)
State) The properties of Compound B collected by the method of Example 1 were measured by a conventional method, and the results were as follows.
【００２４】（１）形状：淡褐色無晶形粉末。(1) Shape: light brown amorphous powder.
【００２５】（２）旋光度：［α］Ｄ−８５゜（ｃ＝
１，ＭｅＯＨ）。(2) Optical rotation: [α] D -85 ° (c =
1, MeOH).
【００２６】（３）ＦＡＢ−ＭＳ ｍ／ｚ：５６９（Ｍ
＋Ｎａ）（ｐｏｓｉｔｉｖｅ−ｉｏｎｍｏｄｅ；ｍａｔ
ｒｉｘ，ｍ−ｎｉｔｒｏｂｅｎｚｙｌ ａｌｃｏｈｏｌ
＋ＮａＣｌ）。(3) FAB-MS m / z: 569 (M
+ Na) (positive-ionmode; mat)
rix, m-nitrobenzyl alcohol
+ NaCl).
【００２７】（４）ＵＶ λｍａｘＭｅＯＨｎｍ（ｌｏ
ｇ ε）：２８１（３．９９）。(4) UV λmax MeOH nm (lo
g ε): 281 (3.99).
【００２８】（５）１Ｈ−ＮＭＲ（５００ＭＨｚ、ａｃ
ｅｔｏｎｅ−ｄ６＋Ｄ２Ｏ） δ：１．８４，１．９７［計１Ｈ，ｄｄｄ，Ｊ＝１．
５，５．５，１２．５Ｈｚ，Ｈ＝３（Ｕ）］，２．４
８，２．６１［計１Ｈ，ｄｄ，Ｊ＝９，１６Ｈｚ，Ｈ−
４（Ｌ）］，２．６０，２．７７［計１Ｈ，ｑ，Ｊ＝１
２．５Ｈｚ，Ｈ−３（Ｕ）］，２．８４，２．９１［計
１Ｈ，ｄｄ，Ｊ＝５．５，１６Ｈｚ，Ｈ−４（Ｌ）］，
３．５６，４．０１［計１Ｈ，ｍ，Ｈ−３（Ｌ）］，
４．４３，４．６８［計１Ｈ，ｄ，Ｊ＝７．５Ｈｚ，Ｈ
−２（Ｌ）］，４．７５−４．８１［計１Ｈ，ｍ，Ｈ−
４（Ｕ）］，４．８８，４．９０［計１Ｈ，ｂｒ ｄ，
Ｊ＝１２．５Ｈｚ，Ｈ−２（Ｕ）］，６．００［１／２
Ｈ，ｄｄ，Ｊ＝２，８Ｈｚ，Ｈ−６′（Ｕ）またはＨ−
６′（Ｌ）］，６．０２，６．１７［計１Ｈ，ｓ，Ｈ−
６（Ｌ）］，６．２０，６．３０［計１Ｈ，ｄｄ，Ｊ＝
２．５，８．５Ｈｚ，Ｈ−６（Ｕ）］，６．２１−６．
２２［計１Ｈ，Ｈ−８（Ｕ）］，６．５３［１／２Ｈ，
ｄ，Ｊ＝１．５Ｈｚ，Ｈ−２′（Ｕ）またはＨ−２′
（Ｌ）］，６．５７−６．８２｛計５Ｈ，Ｈ−５
（Ｕ），Ｈ−５′（Ｕ），Ｈ−５′（Ｌ），Ｈ−６′
（Ｕ），Ｈ−６′（Ｌ）およびＨ−２′（Ｕ）［または
Ｈ−２′（Ｌ）］｝，６．９１，６．９６［計１Ｈ，ｂ
ｒ ｓ，Ｈ−２′（Ｕ）またはＨ−２′（Ｌ）］． 以上のように、当該化合物Ｂは、文献未記載の３′，
４′，７−ｔｒｉｈｙｄｒｏｘｙｆｌａｖａｎ−（４α
→８）−ｃａｔｅｃｈｉｎである。(5) 1 H-NMR (500 MHz, ac
etone- d 6 + D 2 O) δ: 1.84,1.97 [ total 1H, ddd, J = 1.
5, 5.5, 12.5 Hz, H = 3 (U)], 2.4
8, 2.61 [Total 1H, dd, J = 9, 16Hz, H-
4 (L)], 2.60, 2.77 [1H, q, J = 1 in total]
2.5 Hz, H-3 (U)], 2.84, 2.91 [1H, dd, J = 5.5, 16 Hz, H-4 (L)],
3.56, 4.01 [total 1H, m, H-3 (L)],
4.43, 4.68 [Total 1H, d, J = 7.5Hz, H
-2 (L)], 4.75-4.81 [1H, m, H-
4 (U)], 4.88, 4.90 [1H in total, br d,
J = 12.5 Hz, H-2 (U)], 6.00 [1/2]
H, dd, J = 2.8 Hz, H-6 '(U) or H-
6 ′ (L)], 6.02, 6.17 [1H, s, H−
6 (L)], 6.20, 6.30 [total 1H, dd, J =
2.5, 8.5 Hz, H-6 (U)], 6.21-6.
22 [total 1H, H-8 (U)], 6.53 [1 / 2H,
d, J = 1.5 Hz, H-2 '(U) or H-2'
(L)], 6.57-6.82 {5H, H-5 in total]
(U), H-5 '(U), H-5' (L), H-6 '
(U), H-6 '(L) and H-2' (U) [or H-2 '(L)]}, 6.91, 6.96 [1H, b in total
rs, H-2 '(U) or H-2' (L)]. As described above, the compound B is 3 ′,
4 ', 7- trihydroxyflavan- (4α
→ 8) -catechin.
【００２９】[0029]
【化４】 Embedded image
【００３０】実施例４（当該化合物の酵素阻害作用） 当該化合物の一つである３′，４′，７−ｔｒｉｈｙｄ
ｒｏｘｙｆｌａｖａｎ−（４α→８）−ｃａｔｅｃｈｉ
ｎ（化合物Ｂ）のリパーゼ阻害効果を検討した。 Example 4 (Enzyme-inhibiting action of the compound ) 3 ', 4', 7- trihydro which is one of the compounds
roxyflavan- (4α → 8) -catechi
The lipase inhibitory effect of n (compound B) was examined.
【００３１】リパーゼ活性の測定は、基質に蛍光性の４
−メチルウンベリフェロンのオレイン酸エステル（４−
ＭＵ ｏｌｅａｔｅ）、酵素にブタ膵リパーゼを使用
し、反応によって生成した４−メチルウンベリフェロン
（４−ＭＵ）の蛍光を測定することによって行った。即
ち、小試験管に０．１ｍＭ ４−ＭＵ ｏｌｅａｔｅ懸
濁液１００μｌ、ブタ膵リパーゼ溶液５０μｌ（Ｍｃｌ
ｌｖａｉｎｅ緩衝液（ｐＨ７．４））、緩衝液４５μ
ｌ、５０％テトラヒドロフラン（ＴＨＦ）または試料の
５０％ＴＨＦ溶液５μｌをとり、３７℃で２０分間反応
後、０．１Ｎ塩酸１ｍｌを添加して反応を停止させ、
０．１Ｍクエン酸ナトリウム溶液を添加して溶液のｐＨ
を４．３付近に調整した後、反応によって生成した４−
メチルウンベリフェロンの蛍光強度を励起波長３２０ｎ
ｍ、蛍光波長４５０ｎｍで蛍光光度計により測定した。
阻害活性は、試料無添加の対照の活性を半分にする試料
添加量（ＩＣ５０（μｇ））で示した。結果を図２に示
す。The measurement of lipase activity is performed by using a fluorescent 4
Oleic acid ester of methyl-umbelliferone (4-
MU oleate), using porcine pancreatic lipase as the enzyme, and measuring the fluorescence of 4-methylumbelliferone (4-MU) produced by the reaction. That is, 100 μl of 0.1 mM 4-MU oleate suspension and 50 μl of porcine pancreatic lipase solution (Mcl
Iveine buffer (pH 7.4), buffer 45μ
1. Take 5 μl of 50% tetrahydrofuran (THF) or a 50% THF solution of the sample, react at 37 ° C. for 20 minutes, add 1 ml of 0.1N hydrochloric acid to stop the reaction,
Add 0.1 M sodium citrate solution to pH of the solution
Was adjusted to around 4.3, and then 4-
Excitation wavelength 320n
m, measured with a fluorometer at a fluorescence wavelength of 450 nm.
The inhibitory activity was represented by the amount of the sample added (IC 50 (μg)) that halved the activity of the control with no sample added. The results are shown in FIG.
【００３２】当該化合物Ｂは、リパーゼ活性を抑制し、
添加量の増加とともにリパーゼの活性が著しく阻害され
ることが認められた。The compound B suppresses lipase activity,
It was found that the activity of lipase was significantly inhibited as the amount added increased.
【００３３】当該化合物Ｂのリパーゼ阻害効果ＩＣ５０
は０．６μｇであり、各種酵素阻害作用が知られる緑茶
の主成分であるエピガロカテキンガレート（ＩＣ５０＝
１．０μｇ）よりも明らかに高い阻害効果が認められ
た。Lipase inhibitory effect IC 50 of Compound B
Is 0.6 μg, and epigallocatechin gallate (IC 50 =
1.0 μg).
【００３４】[0034]
【発明の効果】本発明に係る化合物は、体内酵素タンパ
ク質と結合することによって、その活性を低下させる性
質を有し、代謝調節剤として有用である。また、種々の
酵素作用を抑制し、食品などの酵素作用に起因する劣
化、例えば悪臭発生および物性低下を防止するのに利用
することができる。Industrial Applicability The compound according to the present invention has a property of reducing its activity by binding to an enzyme protein in the body, and is useful as a metabolic regulator. Further, it can be used for suppressing various enzyme actions and preventing deterioration due to the enzyme action of foods and the like, for example, generation of bad smell and deterioration of physical properties.
【００３５】本発明に係る化合物は、飲用にも供される
カワラケツメイから採取したもので、安全性が高い。The compound according to the present invention is obtained from Kawataketsumei, which is also used for drinking, and has high safety.
【図１】本発明の実施例１で行ったカワラケツメイから
当該新規化合物を分離する方法を示すフローチャート図
である。FIG. 1 is a flow chart showing a method for separating the novel compound from C. versicolor performed in Example 1 of the present invention.
【図２】本発明の実施例４で得られた実験結果につき、
当該化合物Ｂのリパーゼ活性に対する影響を示す特性線
図である。FIG. 2 shows the experimental results obtained in Example 4 of the present invention.
FIG. 4 is a characteristic diagram showing the effect of Compound B on lipase activity.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 伊東 禧男 東京都清瀬市野塩３−26−11 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Yoshio Ito 3-26-11 Noshio, Kiyose-shi, Tokyo
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21006893A JP2628832B2 (en) | 1993-08-25 | 1993-08-25 | New tannin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21006893A JP2628832B2 (en) | 1993-08-25 | 1993-08-25 | New tannin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0761981A JPH0761981A (en) | 1995-03-07 |
| JP2628832B2 true JP2628832B2 (en) | 1997-07-09 |
Family
ID=16583294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21006893A Expired - Lifetime JP2628832B2 (en) | 1993-08-25 | 1993-08-25 | New tannin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2628832B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3532999B2 (en) * | 1995-03-24 | 2004-05-31 | 株式会社ロッテ | Novel tannins and lipase inhibitors containing them as active ingredients |
| JPH09291039A (en) * | 1995-12-26 | 1997-11-11 | Suntory Ltd | Antiobestic medicine comprising procyanidin as active ingredient |
| JP2013079276A (en) * | 2013-01-04 | 2013-05-02 | Lotte Co Ltd | Methioninase inhibitor, and oral cavity composition and food and drink, containing the same |
-
1993
- 1993-08-25 JP JP21006893A patent/JP2628832B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0761981A (en) | 1995-03-07 |
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