JPH0761981A - New tannin - Google Patents
New tanninInfo
- Publication number
- JPH0761981A JPH0761981A JP21006893A JP21006893A JPH0761981A JP H0761981 A JPH0761981 A JP H0761981A JP 21006893 A JP21006893 A JP 21006893A JP 21006893 A JP21006893 A JP 21006893A JP H0761981 A JPH0761981 A JP H0761981A
- Authority
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- Japan
- Prior art keywords
- compound
- total
- enzyme
- lipase
- action
- 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.)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Pyrane Compounds (AREA)
Abstract
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 novel tannins useful as foods and drinks and pharmaceuticals 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 Tannin has been used as an astringent drug and a tanning agent since ancient times because it is widely present in the plant kingdom and has an astringent action. However, tannin generally has a complicated structure, and its studies have been delayed due to the difficulty of isolation and purification. On the other hand, tannin has the property of inhibiting the activity of various enzymes in addition to the above-mentioned actions, and is known to be useful as various physiological and metabolic regulators [Chemical field, 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
ｌｌｏｙｌｐｒｅｄｅｌｐｈｉｎｉｄｉｎ 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。Regarding enzyme inhibition of tannins, it has been reported that tannins of fodder plants inhibit lipase, amylase and protease, and tannins of beans (Field bean) inhibit lipase. It is (British
J. Nutrition, 60 , 275 (198
8), J. Sci. Food Agric. , 30 , 4
58 (1979)). Further, 4-di-O-galloylquinic acids (Japanese Patent Publication No. 60-50778) and 3'-O-Ga.
llloylpredelphinidin B-2 (Japanese Patent Publication 60-11912), 4 ', 6'-Gallloyl
salidroside (Japanese Patent Publication No. 63-53993)
, Has been publicly announced as a novel tannin, has an action of binding to an enzyme protein and decreasing 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）〕。A plant of the legume family, Kawaretsutsumei ( Ca
ssia name Honda = Cassia
mimosides L. var. noname
Makino = Cassia mimosides
L. subsp. noname Ohashi)
The whole plant is used as a crude drug for the purpose of diuresis, intestine regulation, stomach functioning, etc., and is also used as a substitute for tea. In addition, the extract of this plant has been shown to have 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 acquired various components from an extract of Kawara-Ketsumei, and investigated the pharmacological effects based on the enzyme inhibitory activity, for the purpose of searching for medicinal components of plants.
【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 As a result of searching for components having a high enzyme inhibitory activity from the extract of Kawara-Ketsumei, the present inventors have found a novel tannin and completed the present invention.
【０００７】本発明によれば、式（１）According to the present invention, the formula (1)
【０００８】[0008]
【化２】 [Chemical 2]
【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 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 the 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 of foods and the like due to the enzyme action.
【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。The compound according to the present invention is highly safe since it is collected from Kawara Tsutsumei, which is also used for drinking.
【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 extraction from Astragalus chinensis with acetone, partition between ether and water and 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. The present invention is not limited 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。 Example 1 (Extraction and mining from Kawaraketsumei
(Image) This substance can be separated and collected from Kawara Tsutsumei and the like by known methods such as solvent extraction, liquid-liquid partitioning, and column chromatography.
【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 Kawara Ketsumei, and the obtained extract was concentrated and extracted with ether to remove the ether layer. The aqueous layer was extracted with ethyl acetate. The ethyl acetate was applied to a Toyopearl HW-40 column and
It was eluted with 0% ethanol and fractionated. This 1 fraction was further applied to an MCI GEL CHP-20P column and eluted with methanol water of each concentration. Of this, 40% methanol eluate was collected and re-applied to the MCI GEL column.
It was eluted with aqueous methanol. Of these, the compound A was obtained in the middle of the 40% methanol elution part, and then the compound B was obtained. These yields are 0.07%, 0.0
It was 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
Jo) results the properties of the compound A collected by the method of Example 1 was measured by a conventional method, it was 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-nitrobenzyla
lcohol).
【００２０】（４）ＵＶ λｍａｘＭｅＯＨｎｍ（ｌｏ
ｇ ε）：２８２（３．９７）。(4) UV λmax MeOH nm (lo
g ε): 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−（４
β→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, 16Hz, 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 = 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) 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 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 ', which is not described in the literature,
4 ', 7'-trihydroxyflavan- (4
β → 8) -catechin.
【００２２】[0022]
【化３】 [Chemical 3]
【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 / chemical properties of the compound B
Jo) results of properties of the compound B taken by the method of Example 1 was measured by a conventional method, was 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-ion mode; 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−（４
α→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 [total 1H, q, J = 1
2.5 Hz, H-3 (U)], 2.84, 2.91 [total 1 H, 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 [total 1H, m, H-
4 (U)], 4.88, 4.90 [total 1H, 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 [total 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 {total 5H, H-5
(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 [total 1H, b
rs, H-2 '(U) or H-2' (L)]. As described above, the compound B is 3 ′, which is not described in the literature,
4 ', 7'-trihydroxyflavan- (4
α → 8) -catechin.
【００２９】[0029]
【化４】 [Chemical 4]
【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′−ｔｒｉｈｙ
ｄｒｏｘｙｆｌａｖａｎ−（４α→８）−ｃａｔｅｃｈ
ｉｎ（化合物Ｂ）のリパーゼ阻害効果を検討した。 Example 4 (Enzyme Inhibitory Action of the Compound ) One of the compounds, 3 ′, 4 ′, 7′-trihy
droxyflavan- (4α → 8) -catech
The lipase inhibitory effect of in (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 lipase activity was measured by measuring the fluorescence of the substrate 4
-Methylumbelliferone oleate (4-
MUoleate), porcine pancreatic lipase was used as an enzyme, and the fluorescence of 4-methylumbelliferone (4-MU) produced by the reaction was measured. That is, in a small test tube, 100 μl of 0.1 mM 4-MU oleate suspension and 50 μl of porcine pancreatic lipase solution (Mcl
lvaine buffer (pH 7.4)), buffer 45 μ
1, 50% tetrahydrofuran (THF) or 5 μl of 50% THF solution of the sample was taken, reacted at 37 ° C. for 20 minutes, and then added with 1 ml of 0.1N hydrochloric acid to stop the reaction,
Add 0.1 M sodium citrate solution and add
Was adjusted to around 4.3, and then 4-
The fluorescence intensity of methyl umbelliferone was measured at an excitation wavelength of 320n.
m, fluorescence wavelength 450 nm.
The inhibitory activity was shown by the amount of added sample (IC 50 (μg)) that halved the activity of the control without added sample. The results are shown in Figure 2.
【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 the lipase activity,
It was found that the activity of lipase was significantly inhibited as the amount of addition 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 of the compound B IC 50
Is 0.6 μg, and epigallocatechin gallate (IC 50 =), which is the main component of green tea known to have various enzyme-inhibiting effects, is used.
The inhibitory effect was clearly higher than that of 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。The compound according to the present invention has the property of reducing its activity by binding to the enzyme protein in the body, and is useful as a metabolic regulator. In addition, it can be used for suppressing various enzyme actions and preventing deterioration of foods and the like due to the enzyme action, for example, generation of malodor 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 highly safe since it is collected from Kawaretsu Tsumemei, which is also used for drinking.
【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 diagram showing a method for separating the novel compound from Kawara Tsutsumei 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.
It is a characteristic diagram which shows the influence of the said compound B on lipase activity.
─────────────────────────────────────────────────────
─────────────────────────────────────────────────── ───
【手続補正書】[Procedure amendment]
【提出日】平成５年９月１３日[Submission date] September 13, 1993
【手続補正１】[Procedure Amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】０００３[Name of item to be corrected] 0003
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【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。Regarding enzyme inhibition of tannins, it has been reported that tannins of fodder plants inhibit lipase, amylase and protease, and tannins of beans (Field bean) inhibit lipase. It is (British
J. Nutrition, 60 , 275 (198
8), J. Sci. Food Agric. , 30 , 4
58 (1979)). Further, 4-di-O-galloylquinic acids (Japanese Patent Publication No. 60-50778) and 3'-O-Ga.
llloypr o delphinidin B-2 (Japanese Patent Publication No. Sho 60-11912), 4 ', 6'-Gallloyl
salidroside (Japanese Patent Publication No. 63-53993)
, Has been publicly announced as a novel tannin, has an action of binding to an enzyme protein and decreasing its activity, and has been shown to be used as a metabolic regulator.
【手続補正２】[Procedure Amendment 2]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００２１[Correction target item name] 0021
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【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, 16Hz, 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 = 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) 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 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 ', which is not described in the literature,
4 ', 7- trihydroxyflavan- (4β
→ 8) -catechin.
【手続補正３】[Procedure 3]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００２８[Correction target item name] 0028
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【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 [total 1H, q, J = 1
2.5 Hz, H-3 (U)], 2.84, 2.91 [total 1 H, 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 [total 1H, m, H-
4 (U)], 4.88, 4.90 [total 1H, 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 [total 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 {total 5H, H-5
(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 [total 1H, b
rs, H-2 '(U) or H-2' (L)]. As described above, the compound B is 3 ′, which is not described in the literature,
4 ', 7- trihydroxyflavan- (4α
→ 8) -catechin.
【手続補正４】[Procedure amendment 4]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００３０[Name of item to be corrected] 0030
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【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 Inhibitory Action of the Compound ) One of the compounds, 3 ', 4', 7- trihyd
roxyflavan- (4α → 8) -catechi
The lipase inhibitory effect of n (compound B) was examined.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 志村 進 埼玉県浦和市沼影１−23−６ (72)発明者 伊東 禧男 東京都清瀬市野塩３−26−11 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Susumu Shimura 1-23-6 Numakage, Urawa-shi, Saitama (72) Ino Yoshio 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 true JPH0761981A (en) | 1995-03-07 |
| JP2628832B2 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) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5629338A (en) * | 1995-03-24 | 1997-05-13 | Lotte Co., Ltd. | Tannins and lipase inhibitors containing the same 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
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5629338A (en) * | 1995-03-24 | 1997-05-13 | Lotte Co., Ltd. | Tannins and lipase inhibitors containing the same 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2628832B2 (en) | 1997-07-09 |
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