JPH01242596A - Lignane compound - Google Patents
Lignane compoundInfo
- Publication number
- JPH01242596A JPH01242596A JP63064663A JP6466388A JPH01242596A JP H01242596 A JPH01242596 A JP H01242596A JP 63064663 A JP63064663 A JP 63064663A JP 6466388 A JP6466388 A JP 6466388A JP H01242596 A JPH01242596 A JP H01242596A
- Authority
- JP
- Japan
- Prior art keywords
- water
- butanol
- chloroform
- methanol
- extract
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title description 8
- 229930013686 lignan Natural products 0.000 claims description 6
- 235000009408 lignans Nutrition 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- -1 lignan compound Chemical class 0.000 claims description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 21
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 11
- 230000000202 analgesic effect Effects 0.000 abstract description 9
- 239000000284 extract Substances 0.000 abstract description 9
- SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002021 butanolic extract Substances 0.000 abstract description 3
- 239000000287 crude extract Substances 0.000 abstract description 3
- 239000007788 liquid Substances 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 3
- 238000010898 silica gel chromatography Methods 0.000 abstract description 3
- 238000010992 reflux Methods 0.000 abstract description 2
- 239000011877 solvent mixture Substances 0.000 abstract 4
- 241000340661 Stauntonia chinensis Species 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 229920005610 lignin Polymers 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 244000022291 Cucumis melo subsp agrestis Species 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000009831 Citrullus lanatus Nutrition 0.000 description 5
- 208000000114 Pain Threshold Diseases 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 230000037040 pain threshold Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000005692 lignans Chemical class 0.000 description 2
- 238000003819 low-pressure liquid chromatography Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010011469 Crying Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野コ
本発明は新規なり、ダナン化合物に関し、更に詳しくは
鎮痛作用を有し医薬品として有用な新規リグナン化合物
に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel danan compound, and more particularly to a novel lignan compound that has analgesic action and is useful as a pharmaceutical.
［従来の技術］
従来、野木瓜［生薬名仮菖枝根（５ｔａｕｎｔｏｎｉａ
ｃｈｉｎｅｎｓｉｓ ＤＣ，） ］は主に中国の江西、
新注、福建、湖南、広東、仏画に分布し、その根又は根
皮が鎮痛薬として用いられてきた［中薬犬辞典、第１巻
、第３３１頁（１９８５年）］。[Prior art] Conventionally, wild melon [herbal medicine name: 5tauntonia root]
chinensis DC,)] is mainly found in Jiangxi, China.
It is distributed in Xinchu, Fujian, Hunan, Guangdong, and Buddhist paintings, and its root or root bark has been used as an analgesic [Dictionary of Chinese Medicinal Dogs, Vol. 1, p. 331 (1985)].
しかし、鎮痛作用を示す化合物は報告されていない。However, no compounds that exhibit analgesic effects have been reported.
［発明が解決しようとする課題］
本発明の目的は、鎮痛作用を有する新規なリグナン化合
物を提供することにある。[Problems to be Solved by the Invention] An object of the present invention is to provide a novel lignan compound having analgesic effect.
［課題を解決するための手段］
本発明者らは、野木瓜［アケビ科（Ｌａｒｄｉｚａｂａ
−１ａｃｅａｅ ） ５ｔａｕｎｔｏｎｉａ ｃｈｉｎ
ｅｎｓｉｓ ］の主幹、分枝、葉及び全植物の抽出物を
対象にして鋭意研究を行った結果、この野木瓜抽出物中
に新規なリグナン類が含まれていること及び該リグナン
に鎮痛作用があることを見出し、本発明を完成した。[Means for Solving the Problems] The present inventors have discovered that wild melon [Lardizabaceae]
-1aceae) 5tauntonia chin
As a result of intensive research on extracts of the main stem, branches, leaves, and whole plant of the wild melon extract, we found that this wild melon extract contains novel lignans and that these lignans have analgesic effects. They discovered something and completed the present invention.
本発明により提供されるリグナン化合物は下記で示され
るリグナン化合物である。The lignan compounds provided by the present invention are shown below.
式Ｉで示される化合物は、野木瓜を原料としてこれの抽
出液を濃縮することによって得られる抽出物を分画、精
製することにより単離される。The compound represented by formula I is isolated by fractionating and purifying an extract obtained by concentrating an extract obtained from wild melon as a raw material.
該抽出液は、例えば、水、メタノール、エタノール、ア
セトン、酢酸エチルなどを単独又は２種以上混合し、室
温又は加温下、浸漬することにより調製することができ
る（前記溶媒に限らず他の適当な溶媒を用いて調製する
ことも可能である。）０式１で示される化合物を含む抽
出物については、例えば、ｎ−ブタノール、酢酸エチル
、クロロホルム、エーテル、ベンゼン、ｎ−ヘキサンな
どの有機溶媒と水との間の分配による分画法及びシリカ
ゲルカラムクロマトグラフィー、吸着樹脂カラムクロマ
トグラフィー、分子ふるいを応用するクロマトグラフィ
ー、中低圧液体クロマトグラフィー、高速液体クロマト
グラフィーなどのクロマトグラフィー法を適宜組み合わ
せることにより分画精製される。ここで用いられる溶出
溶媒は、例えば、エーテル、石油エーテル、ｎ−ヘキサ
ン、クロロホルム、ベンゼン、トルエン、酢酸エチル、
アセトン、アセトニトリル、エタノール、メタノール、
水、酢酸、蟻酸、リン酸などの単独又は混合溶媒である
。The extract can be prepared, for example, by immersing water, methanol, ethanol, acetone, ethyl acetate, etc. alone or in a mixture of two or more at room temperature or under heating (not limited to the above solvents, but also other solvents). (It is also possible to prepare using an appropriate solvent.) For extracts containing the compound represented by formula 1, for example, organic solvents such as n-butanol, ethyl acetate, chloroform, ether, benzene, n-hexane, etc. Fractionation by partitioning between a solvent and water and chromatography methods such as silica gel column chromatography, adsorption resin column chromatography, chromatography applying molecular sieves, medium-low pressure liquid chromatography, and high-performance liquid chromatography are appropriately combined. This allows for fractionation and purification. The elution solvent used here is, for example, ether, petroleum ether, n-hexane, chloroform, benzene, toluene, ethyl acetate,
Acetone, acetonitrile, ethanol, methanol,
The solvent is water, acetic acid, formic acid, phosphoric acid, etc. alone or in combination.
［発明の効果］
本発明の式Ｉで示される化合物は鎮痛作用を有し医薬品
として有用である。[Effects of the Invention] The compound represented by formula I of the present invention has an analgesic effect and is useful as a pharmaceutical.
［実施例］
次に、実施例及び試験例により本発明を更に具体的に説
明する。[Example] Next, the present invention will be explained in more detail with reference to Examples and Test Examples.
（実施例）
（１）乾燥した野木瓜全草１８ｋｇを７０％エタノール
４０２て３回還流下抽出した。抽出液を合わせて１０ｆ
Ｌまで濃縮し、これを酢酸エチルｌｉで５回洗浄した０
次いでｎ−ブタノール１０１で５回抽出し、ｎ−ブタノ
ール層を合わせて濃縮し２６６ｇの粗抽出物を得た。(Example) (1) 18 kg of dried whole wild melon plant was extracted three times with 70% ethanol 402 under reflux. Combine the extract liquid and make 10f.
This was concentrated to 0.0 L and washed 5 times with ethyl acetate.
Next, it was extracted five times with n-butanol 101, and the n-butanol layers were combined and concentrated to obtain 266 g of crude extract.
これを２．５ｆｔの水に溶解し、酢酸エチル２．５党で
２回洗浄した後、ｎ−ブタノール２党で４回抽出した。This was dissolved in 2.5 ft of water, washed twice with 2.5 parts of ethyl acetate, and extracted 4 times with 2 parts of n-butanol.
ｎ−ブタノール層を合わせて濃縮し７０ｇのｎ−ブタノ
ール抽出物を得た。The n-butanol layers were combined and concentrated to obtain 70 g of n-butanol extract.
（２） このｎ−ブタノール抽出物２７．５ ｇをシリ
カゲルカラムクロマトグラフィー（キーゼＪレゲル６０
メルク社製８０Ｍ）に付し、クロロホルム−メタノール
−水（１０： １ ：０．１）の混合溶媒４．５ｆｔ、
クロロホルム−メタノール−水（８： １ ： ０．１
）の混合溶媒４．５見及びクロロホルム−メタノール−
水（６： １ ： ０．１）の混合溶媒３．７５１．で
溶出したのち、クロロホルム−メタノール−水（４：１
：０．１＞の混合溶媒３．７５ｆｔで溶出される両分を
集めて濃縮し、３．２ｇの濃縮物を得た。(2) 27.5 g of this n-butanol extract was subjected to silica gel column chromatography (Kiese J Regel 60
80M (manufactured by Merck & Co.), 4.5ft of a mixed solvent of chloroform-methanol-water (10:1:0.1),
Chloroform-methanol-water (8:1:0.1
) mixed solvent 4.5 times and chloroform-methanol-
Mixed solvent of water (6: 1: 0.1) 3.751. After elution with chloroform-methanol-water (4:1
Both fractions eluted with 3.75 ft of a mixed solvent of :0.1> were collected and concentrated to obtain 3.2 g of concentrate.
（３） （２）で得た濃縮物のうち４００ｍｇを中低圧
液体クロマトグラフィー［ＯＤＳ ＣＰＯ−２２３Ｃ−
２０（２２Ｘ ３００ｍｍ） 、草野科学（株）製］
に付し、１５％アセトニトリル水５６０ｒｔｄｌで溶出
し、２０１〜２６３ｄの間に溶出する両分を得た。同じ
操作を４回繰り返し、得られた画分を合わせて濃縮乾固
し、褐色粉末２０ｍｇを得た。これを高速液体クロマト
グラフィー［カラム：センシュー科学（株）製Ａｑｕａ
ｓｉ１５５−３５２Ｎ（１０ｘ２５０ＩＩＩｆＩＩ）、
溶媒：クロロホルム−メタノール−水（４，５：１：０
．１）の混合溶媒、流速：５．Ｏｍ４！／分、温度：５
０℃、検出：吸光度（２３５ｎｍ＞ １を用いて分画し
、保持時間２０．０〜２２．０分の画分を集めて濃縮乾
固し、淡黄色粉末３．１ｍｇを得た。(3) 400 mg of the concentrate obtained in (2) was subjected to medium-low pressure liquid chromatography [ODS CPO-223C-
20 (22X 300mm), manufactured by Kusano Scientific Co., Ltd.]
and eluted with 560 rtdl of 15% acetonitrile water to obtain both fractions eluting between 201 and 263 d. The same operation was repeated four times, and the obtained fractions were combined and concentrated to dryness to obtain 20 mg of brown powder. This was subjected to high-performance liquid chromatography [column: Aqua manufactured by Senshu Kagaku Co., Ltd.].
si155-352N (10x250IIIfII),
Solvent: Chloroform-methanol-water (4,5:1:0
．． 1) Mixed solvent, flow rate: 5. Om4! /min, temperature: 5
Fractionation was carried out using 0°C, detection: absorbance (235 nm>1), and fractions with a retention time of 20.0 to 22.0 minutes were collected and concentrated to dryness to obtain 3.1 mg of pale yellow powder.
更にこれを高速液体クロマトグラフィー［カラム：ナー
ゲル社製ＮｕｃｌｅｏｓｉｌａＣ＋ ｓ（１０ｘ２５０
ｍｍ） 、溶媒：１４％アセトニトリル水、流速：５９
Ｍ／分。Furthermore, this was subjected to high performance liquid chromatography [column: Nucleosila C+ s (10x250
mm), solvent: 14% acetonitrile water, flow rate: 59
M/min.
温度＝５０°Ｃ１検出：吸光度（２１０ｎｍ）コを用い
て分画し、保持時間１８．２〜２１．１分の画分を集め
て濃縮乾固することにより１．５ｍｇの式■で示諮れる
化合物を得た。Temperature = 50°C 1 Detection: Fractionation using absorbance (210 nm), collection of fractions with a retention time of 18.2 to 21.1 minutes, concentration and dryness to obtain 1.5 mg as indicated by the formula A compound was obtained.
（物性）
’ ” Ｃ−Ｎ Ｍ Ｒ（ＣＤ＊ＯＤ、 １００ＭＨｚ
＞下記第１表参照
第 １ 表
分子ｍ ： Ｓ Ｉ Ｍ Ｓ ｍ／ｚ ６９３（Ｍ＋
Ｎ ａ ）”分子式：Ｃ□Ｈ４ｆｆ１Ｏ１１
比旋光度：［α］”−−４２，７２°（Ｃ＝０．０８
、 ＣＨｓＯＨ）（試験例）鎮痛作用
高木上亀山の方法［薬学雑誌、第７８巻、第５５３頁（
１９５３年）コに準じ、圧刺激装置（骨上器械製）を用
いて検討した。４週齢（体重２０〜２４ｇ）のＩＣＲ雄
性マウス（チャールス・リバー）を１群１０匹として用
いた。加圧刺激部位はマウスの尾根部、仮性疼痛反応は
加圧部位への噛み付き行動、もがきあるいは啼鳴反応を
指標とした。被験物質投与前に３０分間隔で２回疼痛閾
値を測定し、２回とも疼痛閾値が３０〜６０ｍｍＨｇの
マウスを選び実験に使用した。被験物質は水溶液として
、０．２−を尾静脈投与し、１５分後の疼痛閾値を測定
した。対照群には生理食塩水０．２−を尾静脈投与し、
被験物質の場合と同様に測定した。被験物質投与１５分
後の疼痛閾値が、被験物質投与前の平均疼痛閾値の１．
５倍以上の場合を鎮痛効果陽性とみなし、陽性画数の使
用回数に対する割合を有効率〈％）とした。(Physical properties) ``C-NMR (CD*OD, 100MHz
>See Table 1 below Table 1 Molecule m: S I M S m/z 693 (M+
N a )”Molecular formula: C□H4ff1O11 Specific rotation: [α]”--42,72° (C=0.08
, CHsOH) (Test example) Analgesic effect Takagi Kamikameyama's method [Pharmaceutical Journal, Vol. 78, p. 553 (
(1953), a pressure stimulation device (manufactured by Suprabone Instruments) was used. Four-week-old (weight 20-24 g) ICR male mice (Charles River) were used in groups of 10 mice. The pressure stimulation site was the ridge of the mouse, and the pseudo-pain response was determined by biting, struggling, or crying at the pressure site. Before administration of the test substance, pain thresholds were measured twice at 30-minute intervals, and mice with pain thresholds of 30 to 60 mmHg both times were selected and used in the experiment. The test substance was administered as an aqueous solution at a dose of 0.2 to the tail vein, and the pain threshold was measured 15 minutes later. In the control group, 0.2- of physiological saline was administered through the tail vein.
Measurements were made in the same manner as for the test substance. The pain threshold 15 minutes after administration of the test substance is 1.0% of the average pain threshold before administration of the test substance.
A case of 5 times or more was regarded as a positive analgesic effect, and the ratio of the number of positive strokes to the number of times of use was defined as the effectiveness rate (%).
式■で示きれる化合物のＳａ効果を第２表に示す。Table 2 shows the Sa effect of the compound represented by formula (2).
第 ２ 表 特許出願人 チュングオ イーシュエ クウーシュエユアンヤオ ウーイエンデウスウオ 同 大正製薬株式会社 代理人 弁理士 北 川 富 造Table 2 Patent applicant Chunguo Yixue Kwushueyuanyao Uiendeusuuo Same as Taisho Pharmaceutical Co., Ltd. Agent Patent Attorney Tomizo Kitagawa
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63064663A JPH01242596A (en) | 1988-03-17 | 1988-03-17 | Lignane compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63064663A JPH01242596A (en) | 1988-03-17 | 1988-03-17 | Lignane compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01242596A true JPH01242596A (en) | 1989-09-27 |
Family
ID=13264673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63064663A Pending JPH01242596A (en) | 1988-03-17 | 1988-03-17 | Lignane compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01242596A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102697883A (en) * | 2012-06-04 | 2012-10-03 | 蒋月芳 | Plaster for treating osteoarthritis |
| CN103826651A (en) * | 2011-08-18 | 2014-05-28 | 财团法人全南生物产业振兴院 | Medical composition containing stauntonia hexaphylla extract |
-
1988
- 1988-03-17 JP JP63064663A patent/JPH01242596A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103826651A (en) * | 2011-08-18 | 2014-05-28 | 财团法人全南生物产业振兴院 | Medical composition containing stauntonia hexaphylla extract |
| EP2774617A4 (en) * | 2011-08-18 | 2015-02-18 | Jeonnam Bioindustry Foundation | Medical composition containing stauntonia hexaphylla extract |
| US9370542B2 (en) | 2011-08-18 | 2016-06-21 | Jeonnam Bioindustry Foundation | Medical composition containing Stauntonia hexaphylla extract |
| EP3097920A1 (en) * | 2011-08-18 | 2016-11-30 | Jeonnam Bioindustry Foundation | Medical composition comprising stauntonia hexaphylla extract |
| CN102697883A (en) * | 2012-06-04 | 2012-10-03 | 蒋月芳 | Plaster for treating osteoarthritis |
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