JPH04368336A - Agent for inhibiting angiotensin converting enzyme activity originated from alphatochuyobeta extract - Google Patents
Agent for inhibiting angiotensin converting enzyme activity originated from alphatochuyobeta extractInfo
- Publication number
- JPH04368336A JPH04368336A JP3146175A JP14617591A JPH04368336A JP H04368336 A JPH04368336 A JP H04368336A JP 3146175 A JP3146175 A JP 3146175A JP 14617591 A JP14617591 A JP 14617591A JP H04368336 A JPH04368336 A JP H04368336A
- Authority
- JP
- Japan
- Prior art keywords
- extract
- converting enzyme
- angiotensin converting
- leaves
- water
- 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
Links
- 239000000284 extract Substances 0.000 title claims abstract description 26
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 title claims abstract description 19
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 title claims abstract description 19
- 230000000694 effects Effects 0.000 title claims abstract description 12
- 230000002401 inhibitory effect Effects 0.000 title abstract description 12
- QJVXKWHHAMZTBY-GCPOEHJPSA-N syringin Chemical compound COC1=CC(\C=C\CO)=CC(OC)=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 QJVXKWHHAMZTBY-GCPOEHJPSA-N 0.000 claims abstract description 4
- QJVXKWHHAMZTBY-KSXIZUIISA-N syringin Natural products COc1cc(C=CCO)cc(OC)c1O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O QJVXKWHHAMZTBY-KSXIZUIISA-N 0.000 claims abstract description 4
- IBIPGYWNOBGEMH-DILZHRMZSA-N asperuloside Chemical compound O([C@@H]1OC=C2C(=O)O[C@H]3C=C([C@@H]1[C@H]32)COC(=O)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O IBIPGYWNOBGEMH-DILZHRMZSA-N 0.000 claims description 5
- COUXBBBIXWWAEP-AGUBZPQCSA-N asperuloside Natural products CC(=O)OCC1=C[C@@H]2OC(=O)C3=CO[C@@H](OC[C@H]4O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]4O)[C@H]1[C@H]23 COUXBBBIXWWAEP-AGUBZPQCSA-N 0.000 claims description 5
- FFDULTAFAQRACT-NYYYOYJKSA-N (-)-syringaresinol O,O'-bis(beta-D-glucoside) Chemical compound COC1=CC([C@H]2[C@H]3[C@H]([C@@H](OC3)C=3C=C(OC)C(O[C@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)=C(OC)C=3)CO2)=CC(OC)=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O FFDULTAFAQRACT-NYYYOYJKSA-N 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- USOSNFWVEWONDB-UHFFFAOYSA-N liriodendrin Natural products COc1cc(cc(OC)c1OC2OC(CO)C(O)C(O)C2O)C3OC(C)(C)C4C(OC(C)(C)C34)c5cc(OC)c(OC6OC(CO)C(O)C(O)C6O)c(OC)c5 USOSNFWVEWONDB-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- 239000002994 raw material Substances 0.000 abstract description 7
- 239000002904 solvent Substances 0.000 abstract description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000741 silica gel Substances 0.000 abstract description 5
- 229910002027 silica gel Inorganic materials 0.000 abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003463 adsorbent Substances 0.000 abstract description 4
- 238000004440 column chromatography Methods 0.000 abstract description 4
- 238000003795 desorption Methods 0.000 abstract description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 abstract description 2
- 238000002523 gelfiltration Methods 0.000 abstract description 2
- 230000002209 hydrophobic effect Effects 0.000 abstract description 2
- 239000003456 ion exchange resin Substances 0.000 abstract description 2
- 229920003303 ion-exchange polymer Polymers 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract description 2
- 238000001179 sorption measurement Methods 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract 3
- 241000208367 Euonymus Species 0.000 abstract 2
- CCAIKWKFTGBEJQ-UHFFFAOYSA-N asperoside Natural products CC(CCC1(O)OC2C(CC3(C)CCC4C(CC=C5CC(CCC45C)OC6OC(CO)C(OC7OC(C)C(OC8OC(C)C(O)C(O)C8O)C(O)C7O)C(O)C6OC9OC(C)C(O)C(O)C9O)C23)C1C)COC%10OC(CO)C(O)C(O)C%10O CCAIKWKFTGBEJQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- YHKROSUJLZTZDS-IOLWVCCESA-N dichotomin Chemical compound O([C@H]1[C@H](C)O[C@H]([C@@H]([C@@H]1O)O)O[C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O[C@H]1[C@@H]([C@H](O)[C@@H](O)[C@H](C)O1)O)OC1CC2=CCC3C4CC5O[C@]([C@H](C5C4(C)CCC3C2(C)CC1)C)(O)CCC(C)CO[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O YHKROSUJLZTZDS-IOLWVCCESA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000000605 extraction Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- -1 lignan compounds Chemical class 0.000 description 3
- 102000015427 Angiotensins Human genes 0.000 description 2
- 108010064733 Angiotensins Proteins 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241000208688 Eucommia Species 0.000 description 2
- 240000007182 Ochroma pyramidale Species 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000004531 blood pressure lowering effect Effects 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 241000411851 herbal medicine Species 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 206010000234 Abortion spontaneous Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229930013686 lignan Natural products 0.000 description 1
- 235000009408 lignans Nutrition 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 208000015994 miscarriage Diseases 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 208000000995 spontaneous abortion Diseases 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Medicines Containing Plant Substances (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】この発明は、杜仲（Ｅｕｃｏｍｍ
ｉａ ｕｌｍｏｉｄｅｓ）の植物葉から得られ、かつ、
アンジオテンシン転換酵素阻害活性効果を有する杜仲葉
由来のエキスに関するものである。[Industrial Application Field] This invention is based on Eucomm
ia ulmoides), and
The present invention relates to an extract derived from Duchu leaf that has angiotensin converting enzyme inhibitory activity.
【０００２】0002
【従来技術および解決すべき課題】中国原産の落葉性植
物であるトチュウ科トチュウの樹皮は、生薬として神農
本草経の上品に収載されている。杜仲の薬効として中薬
大辞典、中華人民共和国薬典には「肝腎を補う、筋骨を
強める、胎を安らげる効能があり、腰、背の酸痛、足膝
萎弱（膝の麻痺）、残尿、女性の不正出血、早流産、高
血圧を治す」などと記載されており、薬効成分としてイ
リドイド類化合物やリグナン類化合物が報告されている
。[Prior Art and Problems to be Solved] The bark of Eucommia, a deciduous plant native to China, is listed as a herbal medicine in the Shennong Bencaojing. The Chinese Medicine Encyclopedia and the People's Republic of China Pharmacy Dictionary describe the medicinal properties of Du Zhong as follows: ``It has the effect of replenishing the liver and kidneys, strengthening the muscles and bones, and calming the womb. It is said to cure urine, abnormal bleeding in women, premature miscarriage, and high blood pressure.'' Iridoid compounds and lignan compounds are reported to be medicinal ingredients.
【０００３】現在、生薬として用いられている杜仲は、
ほとんど中国大陸その他で自生ないしは栽培されている
ものであって、樹齢２０年程度の成木を伐採し、その樹
皮を剥離し、得られた皮部分を薬用原料として用いてい
る。[0003] Du Zhong, which is currently used as a herbal medicine, is
It is mostly grown wild or cultivated in mainland China and other parts of the world, and mature trees around 20 years old are cut down, their bark is peeled off, and the resulting bark is used as a medicinal raw material.
【０００４】しかし、樹木の伐採および樹皮の剥離には
多大な労力を費やし、また樹皮を多量採取すると植物の
生存と生育に悪影響が及ぼす。そのため、薬用有効成分
の取得原料としては、樹木の伐採や樹皮の剥離を行なう
ことなく、簡単な作業で繰り返し採取できる材料が望ま
しい。[0004] However, cutting down trees and peeling off the bark takes a lot of effort, and collecting a large amount of bark has a negative impact on the survival and growth of plants. Therefore, as raw materials for obtaining medicinal active ingredients, it is desirable to use materials that can be repeatedly harvested through simple operations without cutting down trees or peeling the bark.
【０００５】本発明者らは、鋭意研究の結果、薬用成分
を調製する過程において杜仲葉抽出エキス中にアンジオ
テンシン転換酵素活性を有する成分が存在するという知
見を得、先に特許出願を行なった（特願平１−２００８
３３号）。この成分の研究をさらに進めた結果、先願と
異なる画分が、アンジオテンシン転換酵素阻害活性を有
することを見い出し、この発明を完成した。[0005] As a result of intensive research, the present inventors obtained the knowledge that a component having angiotensin converting enzyme activity was present in the Morifolia extract during the process of preparing medicinal ingredients, and filed a patent application ( Patent application Hei 1-2008
No. 33). As a result of further research into this component, it was discovered that a fraction different from that in the previous application had angiotensin converting enzyme inhibitory activity, and the present invention was completed.
【０００６】すなわち、この発明は、杜仲は落葉性であ
ることを利用し、杜仲の有効成分の取得原料部位として
、樹皮より簡単な操作で繰り返し採取できる材料である
葉を抽出処理することによって得られ、かつアンジオテ
ンシン転換酵素活性阻害効果を有する杜仲葉由来の抽出
エキスを提供することを目的とする。[0006] In other words, the present invention takes advantage of the fact that Mori mori is deciduous, and extracts the active ingredients of Mori mori as a raw material for obtaining the active ingredients by extracting the leaves, which are materials that can be repeatedly collected with simpler operations than the bark. It is an object of the present invention to provide an extract derived from Duchu leaf that has the effect of inhibiting angiotensin converting enzyme activity.
【０００７】[0007]
【課題を解決するための手段】この発明による杜仲葉エ
キス由来のアンジオテンシン転換酵素活性阻害剤は、杜
仲の植物葉を抽出処理し、得られた抽出液から調製する
ことを特徴とし、有効性分としてリリオデンドリン、ア
スペルロサイドおよびシリンジンを含むものである。[Means for Solving the Problems] The angiotensin converting enzyme activity inhibitor derived from Morifolia leaf extract according to the present invention is characterized in that it is prepared from the extract obtained by extracting the leaves of Moriflora, and has a high efficacy. These include liriodendrin, asperuloside and syringin.
【０００８】ここで、抽出原料としては、大量かつ容易
に繰り返し確保することが出来ることが必要であるので
葉が適当である。杜仲は落葉性植物であり、秋葉の採取
は、樹木に悪影響を与えることなく、かつ、大量の材料
を容易に確保できる点で有利である。ただし、抽出原料
は秋葉に限定されるものではない。原料葉は好ましくは
自然乾燥される。抽出用の溶媒の代表的な例は、水、特
に加熱水である。その他、抽出溶媒としては、メタノー
ル、エタノールなどの低級アルコールや、各種の有機溶
媒などが例示される。これらの有機溶媒は単独でまたは
２以上の組み合わせで使用される。エキスを飲用にする
には水で抽出するのが好ましい。抽出は加熱下に行なわ
れるが、室温でも良い。抽出回数は多いほど良いが、通
常は数回である。[0008] Here, leaves are suitable as the raw material for extraction, since it is necessary to be able to easily and repeatedly secure large quantities. Morifolia is a deciduous plant, and collecting autumn leaves is advantageous in that it does not have a negative impact on the trees and it is easy to secure a large amount of material. However, the extraction raw material is not limited to autumn leaves. The raw material leaves are preferably naturally dried. A typical example of a solvent for extraction is water, especially heated water. Other examples of extraction solvents include lower alcohols such as methanol and ethanol, and various organic solvents. These organic solvents may be used alone or in combination of two or more. To make the extract drinkable, it is preferable to extract it with water. Extraction is carried out under heating, but may be carried out at room temperature. The higher the number of extractions, the better, but usually several times.
【０００９】抽出液からエキスを調製するには、抽出液
を吸着カラムに通すことによって抽出液中の含有成分を
吸着剤に吸着させ、ついで脱着溶媒を同じカラムに通す
ことによって同成分を脱着させる。吸着剤としては、活
性炭、疎水性イオン交換樹脂、例えば三菱化成社製のダ
イヤイオンＨＰ−２０などが用いられる。また、脱着溶
媒の代表的な例としては水−エタノール系が挙げられる
。脱着液はついで濃縮され、さらにゲル濾過法などによ
り、成分の分画を行なう。さらに必要に応じてシリカゲ
ル等を用いたカラムクロマトグラフィーで精製する。To prepare an extract from an extract, the components contained in the extract are adsorbed onto an adsorbent by passing the extract through an adsorption column, and then the same components are desorbed by passing a desorption solvent through the same column. . As the adsorbent, activated carbon, hydrophobic ion exchange resin, for example, Diaion HP-20 manufactured by Mitsubishi Chemical Corporation, etc. are used. Furthermore, a typical example of the desorption solvent is a water-ethanol system. The desorption solution is then concentrated, and the components are further fractionated by gel filtration or the like. Further, if necessary, it is purified by column chromatography using silica gel or the like.
【００１０】こうして得られた杜仲葉抽出エキスは、ア
ンジオテンシン転換酵素阻害活性を有する。アンジオテ
ンシン転換酵素阻害活性は血圧降下成分のスクリーニン
グにおいて簡便なアッセイ系として用いられる。この発
明による抽出エキスはまた、血圧降下作用をもつことが
期待される。[0010] The thus obtained Mori annua leaf extract has angiotensin converting enzyme inhibitory activity. Angiotensin converting enzyme inhibitory activity is used as a simple assay system in screening for blood pressure lowering components. The extract according to the present invention is also expected to have a blood pressure lowering effect.
【００１１】[0011]
【発明の効果】この発明によれば、杜仲の有効成分の取
得原料部位として、樹皮より簡単な操作で繰り返し採取
できる材料である葉を抽出処理することによってアンジ
オテンシン転換酵素活性阻害剤が提供せられる。[Effects of the Invention] According to the present invention, an angiotensin converting enzyme activity inhibitor can be provided by extracting and treating the leaves, which are materials that can be repeatedly collected with simpler operations than the bark, as the source material for obtaining the active ingredients of Eucommia mori. .
【００１２】0012
【実施例】つぎに、この発明をその実施例によって具体
的に説明する。[Examples] Next, the present invention will be specifically explained with reference to Examples.
【００１３】ａ） エキスの製造法
落葉する前に採取した杜仲葉を、水分含量が１０重量％
以下になるまで乾燥させた。この杜仲葉１ｋｇに蒸留水
１０Ｌを加え、杜仲葉を１００℃で３時間加熱下に抽出
処理した。ついで、得られた抽出液を、予め蒸留水で洗
浄した疎水性イオン交換樹脂（三菱化成社製のダイヤイ
オンＨＰ−２０）を充填したカラム（カラム体積８００
ｍＬ）に通した。カラムを蒸留水で洗浄した後、エタノ
ールを３Ｌ流し、吸着成分を脱着させた。この画分を濃
縮し、３０重量％メタノールに溶かした。これをさらに
、３０重量％メタノールを移動相としたＴＯＹＯ Ｐ
ＥＡＲＬ製のＨＷ−４０Ｓゲルを用いたカラムクロマト
グラフィーで３つの画分に分画した。これら３つの画分
をそれぞれ濃縮し、ポリアミドＣ−２００を充填したカ
ラムクロマトグラフィーに通して脱色し、さらにシリカ
ゲルを充填したカラムに付し（移動相クロロホルム：メ
タノール：水＝７０：３０：５）、精製した。得られた
フラクションをそれぞれ濃縮し、凍結乾燥した。こうし
て、杜仲由来の３つの抽出エキスが得られた（Ｅ−１、
Ｅ−２およびＥ−３）。a) Extract manufacturing method Mori leaves collected before falling are collected until the moisture content is 10% by weight.
It was dried until below. 10 L of distilled water was added to 1 kg of this Mori foliage, and the Mori foliage was extracted under heating at 100° C. for 3 hours. Next, the obtained extract was poured into a column (column volume: 800
mL). After washing the column with distilled water, 3 L of ethanol was flowed to desorb the adsorbed components. This fraction was concentrated and dissolved in 30% by weight methanol. This was further mixed with TOYO P using 30% methanol as a mobile phase.
It was fractionated into three fractions by column chromatography using HW-40S gel manufactured by EARL. These three fractions were each concentrated, decolored by passing through column chromatography packed with polyamide C-200, and further applied to a column packed with silica gel (mobile phase chloroform:methanol:water = 70:30:5). , purified. The resulting fractions were each concentrated and lyophilized. In this way, three extracts derived from Morizhong were obtained (E-1,
E-2 and E-3).
【００１４】ｂ） エキスの分析
Ｅ−１、Ｅ−２およびＥ−３をクロロホルム：メタノー
ル：水＝７０：３０：５の展開溶媒を用いてシリカゲル
薄層クロマトグラフィーに付し、それぞれの分析を行な
った。その展開状態を添付した図１に示す。図１中の抽
出エキスＥ−２のＲｆ値は０．６である。b) Analysis of extracts E-1, E-2 and E-3 were subjected to silica gel thin layer chromatography using a developing solvent of chloroform:methanol:water=70:30:5, and the respective analyzes were performed. I did it. Its unfolded state is shown in FIG. 1 attached. The Rf value of extract E-2 in FIG. 1 is 0.6.
【００１５】それぞれの主要成分（図１中に矢印で示し
た成分）をＮＭＲを用いて構造解析した結果、Ｅ−１、
Ｅ−２およびＥ−３はそれぞれリリオデンドリン、アス
ペルロサイドおよびシリンジンであることが判った。画
分Ｅ−２に含まれるアスペルロサイドのＮＭＲ分析スペ
クトルを図２に示す。As a result of structural analysis of each main component (components indicated by arrows in FIG. 1) using NMR, E-1,
E-2 and E-3 were found to be liriodendrin, asperuloside and syringin, respectively. FIG. 2 shows the NMR analysis spectrum of asperuloside contained in fraction E-2.
【００１６】ｃ） アンジオテンシン転換酵素阻害活
性こうして得られた、杜仲葉由来の抽出エキス中の成分
について、アンジオテンシン転換酵素阻害活性を検討し
た。アンジオテンシン転換酵素としてはＳｉｇｍａ 社
製のものを使用し、また反応系には同社のアンジオテン
シン転換酵素臨床キットを用いた。同キットの反応液の
組成を表１に示す。c) Angiotensin converting enzyme inhibitory activity The angiotensin converting enzyme inhibitory activity of the components in the thus obtained extract derived from Duchu leaf was examined. As angiotensin converting enzyme, one manufactured by Sigma was used, and the same company's angiotensin converting enzyme clinical kit was used for the reaction system. Table 1 shows the composition of the reaction solution of the kit.
【００１７】[0017]
【表１】[Table 1]
【００１８】反応は３０℃で１５分間行なった。この反
応系で通常は、ＡＣＥｒｅａｇｅｎｔ 中に含まれる合
成基質フリルアクリロイルフェニルアラニルグリシンが
ＡＣＥｃａｌｉｂｒａｔｏｒ中に含まれるウサギのアン
ジオテンシン転換酵素により分解され、３４０ｎｍの吸
光度が減少するが、サンプル液中に阻害活性物質が存在
すると吸光度の減少度合がなくなる。The reaction was carried out at 30°C for 15 minutes. In this reaction system, the synthetic substrate furyl acryloyl phenylalanylglycine contained in ACEreagent is usually decomposed by the rabbit angiotensin convertase contained in ACEcalibrator, and the absorbance at 340 nm decreases, but inhibitory active substances are present in the sample solution. In the presence of , the degree of decrease in absorbance disappears.
【００１９】杜仲葉由来の抽出エキスＥ−１、Ｅ−２お
よびＥ−３を約３ｍｇ／ｍＬの濃度で０．１ｍＬ反応系
に添加し、アンジオテンシン転換酵素活性の阻害を調べ
た。その結果を表２に示す。表２から明らかなように、
Ｅ−２はアンジオテンシン転換酵素活性を著しく阻害し
た。[0019] Extracts E-1, E-2, and E-3 derived from Morifolia leaves were added to a 0.1 mL reaction system at a concentration of about 3 mg/mL, and the inhibition of angiotensin converting enzyme activity was examined. The results are shown in Table 2. As is clear from Table 2,
E-2 significantly inhibited angiotensin convertase activity.
【００２０】[0020]
【表２】[Table 2]
【００２１】アンジオテンシン転換酵素阻害活性は簡便
なアッセイ系として用いられており、Ｅ−２は血圧降下
作用を持つことが期待される。[0021] Angiotensin converting enzyme inhibitory activity is used as a simple assay system, and E-2 is expected to have a blood pressure lowering effect.
【図１】アンジオテンシン転換酵素阻害活性を有する画
分Ｅ−２（Ｒｆ値：０．６）のシリカゲル薄層クロマト
グラフィーの展開状態を示す図である。FIG. 1 is a diagram showing the development state of silica gel thin layer chromatography of fraction E-2 (Rf value: 0.6) having angiotensin converting enzyme inhibitory activity.
【図２】抽出エキスＥ−２に含まれるアスペルロサイド
のＮＭＲ分析スペクトルである。FIG. 2 is an NMR analysis spectrum of asperuloside contained in extract E-2.
Claims (1)
、アスペルロサイドおよびシリンジンを含むアンジオテ
ンシン転換酵素活性阻害剤。1. An angiotensin converting enzyme activity inhibitor containing liriodendrin, asperuloside, and syringin derived from Morifolia extract.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3146175A JP2579255B2 (en) | 1991-06-18 | 1991-06-18 | Angiotensin converting enzyme activity inhibitor from Tochu leaf extract |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3146175A JP2579255B2 (en) | 1991-06-18 | 1991-06-18 | Angiotensin converting enzyme activity inhibitor from Tochu leaf extract |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04368336A true JPH04368336A (en) | 1992-12-21 |
| JP2579255B2 JP2579255B2 (en) | 1997-02-05 |
Family
ID=15401835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3146175A Expired - Lifetime JP2579255B2 (en) | 1991-06-18 | 1991-06-18 | Angiotensin converting enzyme activity inhibitor from Tochu leaf extract |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2579255B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007102439A1 (en) * | 2006-03-03 | 2007-09-13 | Kobayashi Pharmaceutical Co., Ltd. | Fractionation product of aqueous extract of eucommia ulmoides oliver leaf, and composition for oral ingestion comprising the fractionation product |
| WO2007102438A1 (en) * | 2006-03-03 | 2007-09-13 | Kobayashi Pharmaceutical Co., Ltd. | Fractionation product of aqueous extract of eucommia ulmoides oliver leaf, and anti-obesity agent comprising the fractionation product |
| CN100425243C (en) * | 2005-08-19 | 2008-10-15 | 李斌 | Application of woodruff glycoside in preparing medication for treating rheumatoid arthritis |
| CN104495840A (en) * | 2014-11-28 | 2015-04-08 | 河南恒瑞源实业有限公司 | Method for extracting eucommia ulmoides gum from eucommia ulmoides and preparing active carbon |
Families Citing this family (1)
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|---|---|---|---|---|
| CN103819230A (en) * | 2014-03-05 | 2014-05-28 | 吉首大学 | Novel edible fungi cultivation medium and production method thereof |
-
1991
- 1991-06-18 JP JP3146175A patent/JP2579255B2/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100425243C (en) * | 2005-08-19 | 2008-10-15 | 李斌 | Application of woodruff glycoside in preparing medication for treating rheumatoid arthritis |
| WO2007102439A1 (en) * | 2006-03-03 | 2007-09-13 | Kobayashi Pharmaceutical Co., Ltd. | Fractionation product of aqueous extract of eucommia ulmoides oliver leaf, and composition for oral ingestion comprising the fractionation product |
| WO2007102438A1 (en) * | 2006-03-03 | 2007-09-13 | Kobayashi Pharmaceutical Co., Ltd. | Fractionation product of aqueous extract of eucommia ulmoides oliver leaf, and anti-obesity agent comprising the fractionation product |
| JP2007238449A (en) * | 2006-03-03 | 2007-09-20 | Kobayashi Pharmaceut Co Ltd | Fractionated material of water extract of leaf of eucommia ulmoides oliver and antiobestic agent containing the fractionated material |
| JP2007238456A (en) * | 2006-03-03 | 2007-09-20 | Kobayashi Pharmaceut Co Ltd | Fractionated material of water extract of leaf of eucommia ulmoides oliver and antiobestic agent containing the same |
| CN104495840A (en) * | 2014-11-28 | 2015-04-08 | 河南恒瑞源实业有限公司 | Method for extracting eucommia ulmoides gum from eucommia ulmoides and preparing active carbon |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2579255B2 (en) | 1997-02-05 |
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