JPH0474334B2 - - Google Patents
Info
- Publication number
- JPH0474334B2 JPH0474334B2 JP61199825A JP19982586A JPH0474334B2 JP H0474334 B2 JPH0474334 B2 JP H0474334B2 JP 61199825 A JP61199825 A JP 61199825A JP 19982586 A JP19982586 A JP 19982586A JP H0474334 B2 JPH0474334 B2 JP H0474334B2
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- water
- present
- added
- inflammatory
- 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 - Lifetime
Links
- 239000002904 solvent Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000000284 extract Substances 0.000 claims description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 10
- 229940079593 drug Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 229940093265 berberine Drugs 0.000 description 5
- QISXPYZVZJBNDM-UHFFFAOYSA-N berberine Natural products COc1ccc2C=C3N(Cc2c1OC)C=Cc4cc5OCOc5cc34 QISXPYZVZJBNDM-UHFFFAOYSA-N 0.000 description 5
- 210000000265 leukocyte Anatomy 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- YBHILYKTIRIUTE-UHFFFAOYSA-N berberine Chemical compound C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 YBHILYKTIRIUTE-UHFFFAOYSA-N 0.000 description 4
- 150000003836 berberines Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- 230000034365 zymogen activation Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000287 crude extract Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 102000010911 Enzyme Precursors Human genes 0.000 description 2
- 108010062466 Enzyme Precursors Proteins 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 241000411851 herbal medicine Species 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011345 viscous material Substances 0.000 description 2
- 241000221377 Auricularia Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001142 anti-diarrhea Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 239000003793 antidiarrheal agent Substances 0.000 description 1
- 238000004820 blood count Methods 0.000 description 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000004083 gastrointestinal agent Substances 0.000 description 1
- 229940127227 gastrointestinal drug Drugs 0.000 description 1
- 229960001235 gentian violet Drugs 0.000 description 1
- 239000008236 heating water Substances 0.000 description 1
- 229960001067 hydrocortisone acetate Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、オウバクの分画精製法に関するもの
である。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a method for fractionating and purifying Aerucinifolia.
オウバクは苦味健胃薬として有用なベルベリン
の原料として有名である。ベルベリンはオウバク
を低級アルコール等で抽出する際にその溶剤中に
含まれるものであるが、本発明はそのときの残渣
の有効利用方法に係るものである。本発明は、オ
ウバクからベルベリン系アルカロイド類を除去し
た後（水及び親水性溶剤を加熱して得られた）抗
炎症効果成分の製造を特徴とするものである。 Aubaku is famous as a raw material for berberine, which is useful as a bitter stomachic. Berberine is contained in the solvent when extracting Auronicum spp. with a lower alcohol or the like, and the present invention relates to a method for effectively utilizing the residue at that time. The present invention is characterized by the production of an anti-inflammatory ingredient after removing berberine alkaloids (obtained by heating water and a hydrophilic solvent) from A.
（従来の技術）
オウバクは、古来より止瀉・消炎の要薬として
内服及び外用されている。このオウバクの苦味健
胃と整腸の薬理効果を代表するものは、一連のベ
ルベリン系アルカロイド類であり、化学構造との
関連がほぼ解明されている。近来ではオウバクは
和漢薬方剤に配合するよりベルベリン製造原料と
しての用途が甚だ大である。(Prior art) Oubaku has been used internally and externally as an essential antidiarrheal and antiinflammatory drug since ancient times. A series of berberine-based alkaloids represent the pharmacological effects of this bitter bitter stomach and intestinal regulation, and their relationship with the chemical structure has been largely elucidated. In recent years, Aubaku has been used much more widely as a raw material for the production of berberine than as a compound in Japanese and Chinese medicinal preparations.
しかしそれにひきかえ、オウバクの消炎効果に
関しては積極的な研究が行われていない。 However, on the other hand, no active research has been conducted on the anti-inflammatory effects of Aubacus.
（発明が解決しようとする問題点）
そこで本発明者らは、オウバクのもつ消炎効果
が古来より医療面で幅広く賞用されていることに
着目し、オウバク中の該薬理効果の本質解明のた
め研究を重ねた結果、新しい抗炎症効果成分を解
明することができたものである。(Problems to be Solved by the Invention) Therefore, the present inventors focused on the fact that the anti-inflammatory effect of Aubaku has been widely used in the medical field since ancient times, and aimed to elucidate the essence of the pharmacological effect of Aubaku. As a result of repeated research, we were able to uncover a new ingredient with anti-inflammatory effects.
（問題点を解決するための手段）
本発明の要旨は、オウバクより抽出した成分を
いくつかに分画し、抗炎症効果を有する成分を取
得することにある。(Means for Solving the Problems) The gist of the present invention is to fractionate the components extracted from Aerucinifolia into several components to obtain components having anti-inflammatory effects.
本発明者らは、まず消炎効果を検定するための
試験管内解析方法として、本発明者らが先に開発
したザイモーゲン活性化試験法を適用することと
した。 The present inventors first decided to apply the zymogen activation test method previously developed by the present inventors as an in vitro analysis method for testing the anti-inflammatory effect.
ザイモーゲン活性化試験法を特に用いたのは、
プロテアーゼと炎症との関係が最近明らかにされ
ていること、またザイモーゲンの活性結果と動物
試験による抗炎症効果との関連性が裏付けられて
いること、等により、本発明の薬理研究に適用す
ることが甚だ合目的的であつたからである。 The zymogen activation test method was specifically used to
The relationship between proteases and inflammation has recently been clarified, and the relationship between zymogen activity results and anti-inflammatory effects has been supported by animal tests. This was because it was extremely purposeful.
本発明者らが胃腸薬として使用される代表的な
生薬について、ザイモーゲン活性化試験法を適用
したところ、オウレン、センブリ、ゲンチアナは
活性の増強を示し、オウバク、アカメガシワが活
性の抑制作用を示した。特にオウレン及びオウバ
クの有効成分の一つであるベルベリンについてそ
の標準品が活性の増強を示すという、興味のある
知見を得た。 When the present inventors applied the zymogen activation test method to typical herbal medicines used as gastrointestinal medicines, we found that zymogen activation test method was applied to common herbal medicines used as gastrointestinal drugs. . In particular, we obtained an interesting finding that the standard product of berberine, which is one of the active ingredients of Oren and Orbaku, shows enhanced activity.
以上の結果をふまえて、オウバクの成分につい
て検討した結果、まず非極性溶剤、ついで低級ア
ルコール、さらに親水性溶剤で漸次加熱抽出し
て、各々を分画し、これら分画成分についてザイ
モーゲン活性を測定したところ、親水性溶剤の分
画部分のみが活性を抑制することが判明した。そ
こで、該分画部分を水に溶解し分散してｎ−ブタ
ノールを加えて分配して水層を分取したところ、
比較的高分子で水溶性かつ電気的に中性であり耐
熱性を有する物質が得られた。 Based on the above results, we investigated the components of Auricaria aureus and found that we first extracted it by heating with a non-polar solvent, then a lower alcohol, and then a hydrophilic solvent, fractionated each component, and measured the zymogen activity of these fractionated components. As a result, it was found that only a fraction of the hydrophilic solvent suppressed the activity. Therefore, the fractionated portion was dissolved and dispersed in water, and n-butanol was added and distributed to separate the aqueous layer.
A relatively polymeric, water-soluble, electrically neutral, and heat-resistant substance was obtained.
特にオウバク中の有効成分ベルベリン系アルカ
ロイド類を全く含有せず、従来の報告にはみられ
ない新しい物質といえる。 In particular, it does not contain any of the berberine alkaloids, which are the active ingredients in Aubacus, and can be said to be a new substance that has not been found in previous reports.
このものは動物試験による抗炎症試験でも明ら
かに抗炎症効果がみられた。これらの新知見に基
づいて、オウバクより新しい抗炎症効果成分を精
製する方法を案出することができたものである。 This product clearly showed anti-inflammatory effects in anti-inflammatory tests conducted on animals. Based on these new findings, we were able to devise a method for purifying a new anti-inflammatory ingredient from Auricaria chinensis.
本発明について詳細に説明する。 The present invention will be explained in detail.
本発明においては、まずオウバクに低級アルコ
ール類、例えば、メタノール、エタノール等を加
えて加熱抽出する。 In the present invention, first, lower alcohols such as methanol, ethanol, etc. are added to Auronicum vulgaris and the mixture is heated and extracted.
ついでその溶剤を除去し、その残渣に水、含水
メタノール又はアセトニトリルと水との混合物を
加えて加熱抽出する。 Then, the solvent is removed, and water, water-containing methanol, or a mixture of acetonitrile and water is added to the residue for heating and extraction.
この際、含水メタノールを溶剤とするときは、
その含水率を50〜90％とすることが望ましい。ま
た、アセトニトリルと水との混合溶剤を溶剤とす
るときは、その含水率を50〜90％とするのが抽出
溶剤として適している。 At this time, when using water-containing methanol as the solvent,
It is desirable that the moisture content be 50 to 90%. Further, when a mixed solvent of acetonitrile and water is used as the solvent, it is suitable as an extraction solvent that the water content is 50 to 90%.
得られた抽出液は溶剤を留去して後、粗エキス
を得る。 After distilling off the solvent from the obtained extract, a crude extract is obtained.
この粗エキスに水を加え、非親水性溶剤を加え
て分配する。 Water is added to this crude extract, and a non-hydrophilic solvent is added for distribution.
この場合の溶剤としては、例えば、ｎ−ブタノ
ール、ベンゼン、酢酸エチル、イソブタノール、
ｎ−ヘキサン等を用いることができる。 Examples of the solvent in this case include n-butanol, benzene, ethyl acetate, isobutanol,
n-hexane etc. can be used.
粗エキスを分配した溶剤層のうち、水層を分取
し、溶剤を留去することにより黒褐色のやや粘性
を帯びた物質を得ることができる。 From the solvent layer into which the crude extract has been distributed, the aqueous layer is separated and the solvent is distilled off to obtain a dark brown, slightly viscous substance.
本発明に係る物質の抗炎症試験は、以下のよう
にしてすることができる。 Anti-inflammatory testing of the substances according to the invention can be carried out as follows.
CMC−pouch法による白血球遊走試験を行つ
た。ラツトの背部皮下に予め空気嚢を作つてお
き、ここに試料を溶剤又は懸濁させた２％カルボ
キシメチルセルロースナトリウム溶液を注入す
る。一定時間ごとに嚢内液を採取し、遊出白血球
数を測定する。 A leukocyte migration test was performed using the CMC-pouch method. An air pouch is created in advance under the skin on the back of the rat, and a 2% sodium carboxymethylcellulose solution containing the sample as a solvent or suspended therein is injected into the pouch. Intracapsular fluid is collected at regular intervals and the number of extravasated white blood cells is measured.
既知薬物としてフエニルブタゾンと酢酸ヒドロ
コルチゾンを用いた。なお、白血球数の算定は、
CMC嚢内液を0.1ml採取し、これに３mlの0.01％
ゲンチアナバイオレツト0.9％食塩水溶液を加え
て混和染色し、Fucks Rosenthal血球計算盤を用
いて計数した。これらの結果を第１図に示した。 Phenylbutazone and hydrocortisone acetate were used as known drugs. In addition, the calculation of white blood cell count is as follows:
Collect 0.1ml of CMC intracapsular fluid and add 3ml of 0.01%
A gentian violet 0.9% saline solution was added for mixed staining, and the cells were counted using a Fucks Rosenthal hemocytometer. These results are shown in FIG.
本発明に係る物質は、既知薬物とほぼ同等の白
血球遊走抑制効果がみられた。また本発明物質の
抑制効果には用量依存性がみられた。 The substance according to the present invention exhibited almost the same leukocyte migration inhibitory effect as known drugs. Furthermore, the inhibitory effect of the substance of the present invention was dose-dependent.
本発明物質は、そのまま又は他の薬物と配合し
て、内用、外用等の製剤を形で抗炎症剤として用
いることができる。 The substance of the present invention can be used as an anti-inflammatory agent as it is or in combination with other drugs in the form of preparations for internal or external use.
本発明物質は、ベルベリン系アルカロイド類を
全く含有しないことから、従前は廃棄されていた
ものである。本発明は、資源を有効に活用するも
のとして、経済的効率の高いものであり、またオ
ウバクのもつ抗炎症効果を分離精製することによ
つて裏付けたものとして、甚だ実用的価値の高い
ものであるということができる。 The substance of the present invention was previously discarded because it does not contain any berberine alkaloids. The present invention is highly economically efficient as it makes effective use of resources, and has extremely high practical value as it proves the anti-inflammatory effect of Auronica spp. by separating and purifying it. It can be said that there is.
（実施例）
以下に本発明の実施例を掲げて本発明を更に詳
しく説明する。(Example) The present invention will be described in more detail below with reference to Examples of the present invention.
実施例 １
オウバク1000ｇを細刻し、メタノール3000mlを
加え、４時間還流加熱する。溶剤を変えてこの操
作をもう一度繰り返した後、溶剤を留去する。残
渣にアセトニトリル・水（１：１）の混合溶剤
3000mlを加え、４時間加熱して還流抽出する。溶
剤を変えてこの操作をもう一度繰り返した後、抽
出液を合わせて減圧下で溶剤を留去する。ついで
残留物に水300mlを加えて溶解、分散させ、それ
にｎ−ブタノール300mlを加えて30分間振盪する。
静置することにより分配して、得られた水層を分
取し、減圧下で溶剤を留去して、黒褐色の粘性物
質35ｇを得た。Example 1 Finely chop 1,000 g of Auricularia japonica, add 3,000 ml of methanol, and heat under reflux for 4 hours. After changing the solvent and repeating this operation once again, the solvent is distilled off. Mixed solvent of acetonitrile and water (1:1) to the residue
Add 3000 ml, heat for 4 hours, and extract under reflux. After changing the solvent and repeating this operation once more, the extracts are combined and the solvent is distilled off under reduced pressure. Next, 300 ml of water was added to the residue to dissolve and disperse it, and 300 ml of n-butanol was added thereto, followed by shaking for 30 minutes.
The resulting aqueous layer was separated by standing, and the solvent was distilled off under reduced pressure to obtain 35 g of a dark brown viscous substance.
第１図は、ラツト背部皮下にCMC−Na溶液を
注射し、炎症を惹起させて同時投与の薬物による
抗炎症効果をみたときの経時変化を表わす。縦軸
は嚢内液中に遊出した白血球数（個／mm3）を、
横軸は経過時間（時間）を、それぞれ表わす。
●はコントロールを、▲はフエニルブタゾン
（４mg／ml）を、○は本発明物質（0.2ｇ／ml：原
生薬換算量）を、また△は本発明物質（1.0ｇ／
ml：原生薬換算量）を、それぞれ表わす。
FIG. 1 shows the change over time when a CMC-Na solution was subcutaneously injected into the back of a rat to induce inflammation and the anti-inflammatory effect of the simultaneously administered drug was observed. The vertical axis represents the number of white blood cells (cells/mm 3 ) that migrated into the intracapsular fluid.
The horizontal axis represents elapsed time (time). ● indicates control, ▲ indicates phenylbutazone (4 mg/ml), ○ indicates the substance of the present invention (0.2 g/ml: equivalent amount of the original drug), and △ indicates the substance of the present invention (1.0 g/mL).
ml: equivalent amount of crude drug).
Claims (1)
剤を除去して残渣を得、これに(a)水、(b)含水率
50％以上の含水アルコール類、(c)含水率50％以上
の含水アセトニトリルの(a)、(b)、(c)のいずれかを
加えて抽出し、その後溶剤を除去して残渣を
得、これに水を加え、その後非親水性溶剤を
加えて分配し、水層を分取して溶剤を除去し、
上記〜の操作をこの順に行うことを特徴とす
る、オウバクの分画精製法。1. Extract Auricaria with lower alcohol and remove the solvent to obtain a residue, which contains (a) water and (b) water content.
Extract by adding any of (a), (b), and (c) of hydrous alcohol with a water content of 50% or more, (c) water-containing acetonitrile with a water content of 50% or more, and then remove the solvent to obtain a residue, Water is added to this, then a non-hydrophilic solvent is added and distributed, the aqueous layer is separated and the solvent is removed.
1. A method for fractionating and purifying Aerucinifolia, the method comprising performing the above operations in this order.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61199825A JPS6354324A (en) | 1986-08-25 | 1986-08-25 | Fractional purification of 'oubaku' |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61199825A JPS6354324A (en) | 1986-08-25 | 1986-08-25 | Fractional purification of 'oubaku' |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6354324A JPS6354324A (en) | 1988-03-08 |
| JPH0474334B2 true JPH0474334B2 (en) | 1992-11-26 |
Family
ID=16414269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61199825A Granted JPS6354324A (en) | 1986-08-25 | 1986-08-25 | Fractional purification of 'oubaku' |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6354324A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56164711A (en) * | 1980-05-22 | 1981-12-17 | Iseki Agricult Mach | Pick up device of reaper |
| KR100317112B1 (en) | 1999-03-18 | 2001-12-22 | 한영복 | Pharmaceutical composition comprising mixed-extract of phellodendron cortex and anemarrhena rhizoma for alalgesic and anti-inflammation |
| CN104623033B (en) * | 2015-02-04 | 2018-02-13 | 北京全净通一科技有限公司 | A kind of toxin expelling patch and preparation method |
-
1986
- 1986-08-25 JP JP61199825A patent/JPS6354324A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6354324A (en) | 1988-03-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |