JPS5953476A - Coumarin derivative - Google Patents
Coumarin derivativeInfo
- Publication number
- JPS5953476A JPS5953476A JP57164336A JP16433682A JPS5953476A JP S5953476 A JPS5953476 A JP S5953476A JP 57164336 A JP57164336 A JP 57164336A JP 16433682 A JP16433682 A JP 16433682A JP S5953476 A JPS5953476 A JP S5953476A
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Abstract
Description
【発明の詳細な説明】
本発明は、蛇床子に含まれている新規なりマリン誘導体
に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel marine derivative contained in japonica.
蛇床子は、古く神農本草経に収載されている生薬であり
、収れん性消炎薬として使用されてきているが、その有
効成分は不明であり、有効性自体も薬理学的には積極的
に証明されていない。Snake beetroot is a herbal medicine that has long been listed in the Shennong Bencao Jing, and has been used as an astringent anti-inflammatory, but its active ingredients are unknown, and its effectiveness itself has not been actively proven pharmacologically. It has not been.
本発明者は、天然物から抗アレルギー作用を有する成分
を取り出すことを目的に数多くの実験をおこなううち、
蛇床子のメタノール抽出エキスが軽微ながらも抗アレル
ギー作用を有するとの知見を得、更に研究の結果、抗ア
レルギー作用を有する成分として下記の、新規なりマリ
ン誘導体に到達した。The present inventor conducted numerous experiments with the aim of extracting components with anti-allergic effects from natural products.
We have found that the methanol extract of Jatoko has anti-allergic effect, although it is slight.As a result of further research, we have arrived at the following new marine derivative as a component that has anti-allergic effect.
本発明は、上式の化合物中、Ｏ）式の化合物に係るもの
である。The present invention relates to a compound of formula O) among the compounds of the above formula.
蛇床子から本発明の化合物を１１（るためには、蛇床子
にアルコ−／Ｌ／ 類を抽出Ｍηνとする常用の抽出処
理を族１〜Ｃ抽出エキスを１４、次いでこの抽出エキス
全薄層クロマトグラフィーを併用しなからカラムクロマ
トグラフィーによって分画して主にクマリン誘導体を含
む分画を得る。In order to obtain the compound of the present invention from the snails, a conventional extraction process of extracting alcohol/L/ etc. Fractionation is performed by column chromatography without using chromatography to obtain a fraction mainly containing coumarin derivatives.
このクマリン誘導体を主として含む分画には、本発明の
化合物である（１）式の化合物の他、前述の（１）式の
化合物と（１）式の化合物やこれら新規化合物に構造的
に類似する既知の、下式（Ｉｖ）の化合物が混在ｌ−で
いるが、
引き続き前記クマリン誘導体を主として含む分画を、薄
層クロマトグツフィー（ｒ７併用しなからカラムクロマ
トグブフ・ｆ−によって分画すれば、本発明の化合物と
、（１）式の化合物と（１）式の化合物と、（ＩＶ）式
の化合物とを分取することができる。In addition to the compound of formula (1), which is the compound of the present invention, the fraction mainly containing coumarin derivatives includes the compound of formula (1) and compounds structurally similar to these new compounds. The compound of the following formula (Iv), which is known to have a compound of Then, the compound of the present invention, the compound of formula (1), the compound of formula (1), and the compound of formula (IV) can be fractionated.
尤も、蛇床子中の本発明の化合物を抗アレルギー剤と（
−で利用するにあたっては、本発明の化合物を完全に単
離する必要はなく、む１−ろ、本発明の化合物には、他
に（１）式の化合物や（！Ｉ）式の化合物を混在させて
抗アレルギー剤とする方が、各々即離１−で医薬品とし
て用いるよりも顕著な抗アレルギー作用を発揮させるこ
とができる。従って、蛇床子を原料と１−て抗アレルギ
ー剤を調製するにあたっては、むしろ、クマリン誘導体
以外の不純物の除去に重点をおくことが望ましい。Of course, the compound of the present invention in Jabedoko is used as an anti-allergic agent (
It is not necessary to completely isolate the compound of the present invention when using it in By mixing them together to form an anti-allergic agent, it is possible to exert a more pronounced anti-allergic effect than by using them individually as a medicine. Therefore, when preparing an anti-allergic agent using japonica as a raw material, it is preferable to focus on removing impurities other than coumarin derivatives.
以下、本発明を、製造例、薬坤試験例、毒性試験例等に
より更に具体的に説明する。Hereinafter, the present invention will be explained in more detail with reference to production examples, dosage test examples, toxicity test examples, and the like.
製造例
１） 市販の中１〕ｊ１産蛇床子を粗粉末化（７た後、
これを５０％メタノール水溶液で３同温浸し、メタノー
ルエキスを得た。Production Example 1) Commercially available medium 1] j1-produced jaboko was coarsely powdered (after 7 hours,
This was soaked in a 50% aqueous methanol solution three times to obtain a methanol extract.
２） 上記で得たメタノールエキスを水−ｎ−ブタノー
ルとともに摂盪し、ｎ−ブタノール層に移行した成分を
、シリカゲ）ｖを吸落″剤とし、ベンゼン；アセトン５
０：１→５：１を溶出溶媒としてカラムクロマトグラフ
ィーにかけ、ベンゼン；アセトン４：１ｆｆ：展開溶媒
とする薄層クロマトグラフィーで上方に現われるヌボッ
トの成分から順に分画して分画Ｉ（収率４．３％）、分
画璽（収率５２．２％）、分画■（収率４０口％）、分
画■（収率３９．５％）を得た。2) The methanol extract obtained above was stirred with water-n-butanol, and the components transferred to the n-butanol layer were absorbed using silicage (silicage gel) as a suction agent, and benzene; acetone (5).
Column chromatography was performed using 0:1 → 5:1 as an eluent, and thin layer chromatography was performed using benzene:acetone as a 4:1ff:developing solvent. 4.3%), fraction (yield 52.2%), fraction (2) (yield 40%), and fraction (2) (yield 39.5%) were obtained.
３） 上記で１Ｍだ分画１２５．９８１を、シリカゲル
を吸着剤とし、ｎ−ヘキサン：酢酸エチル４：１→２：
１を溶出溶媒とするカラムクロマトグラフィーにかけ、
ｎ−ヘキサン：酢酸エチ／Ｌ／３：１を展開溶媒とする
薄層クロマｌ−グラフィーで上方に現第１図〜第４図は
、１１１口に（ＩＶ）式の化合物、（Ｉ）式の化合物、
（１）式の化合物、（１）式の化合物のＮＭＲスペクｌ
−／Ｌ／を、第５図〜第８図はＭＡ Ｓ （＋スペクト
ル（ＢＡｉ ＰＥＡＫ ｉ第５図Ｍ／Ｅ ２４４，０工
ＮＴ ２５．４．４ 、第６図Ｍ／Ｅｊ ２［］２．Ｑ
工ＮＴ ７１５．３、第７図”／” １９０．ＯＩＮＴ
２０４、５ 、第８図Ｍ／ＦＪ４ｓ、ｏ工ＮＴ ４２２
．７ ）を示す。3) Using the above 1M fraction 125.981, using silica gel as an adsorbent, n-hexane:ethyl acetate 4:1 → 2:
1 as an elution solvent,
Thin-layer chromatography using n-hexane:ethyl acetate/L/3:1 as the developing solvent shows that the compound of formula (IV) and formula (I) are shown in the upper part of Figures 1 to 4. compound,
Compound of formula (1), NMR spectrum of compound of formula (1)
-/L/, Fig. 5 to Fig. 8 are MA S (+ spectrum (BAi PEAK i Fig. 5 M/E 244, 0 engineering NT 25.4.4, Fig. 6 M/Ej 2[]2 ．Q
Engineering NT 715.3, Figure 7 "/" 190. OINT
204, 5, Fig. 8 M/FJ4s, o-engineering NT 422
．． 7) is shown.
薬埋試験例
１）遅延型皮膚炎に対する効果
体重２（ｌ ９前後のＢＤＦ、糸雄性マウスを１群１１
）匹とし、アレルキー反応惹、起物として塩化ピクリル
を用いて実験をおこなった。すなわち７％塩化ピクリ八
へエタノール溶液を刺毛したマウムの腹部に塗布し、第
１回目の感作をおこない、その後直ちに、蒸留水にとか
した被検薬物を１日２回１＋１日間経口投与した。Drug implantation test example 1) Effect on delayed dermatitis One group of BDF, male mice weighing 2 (l)
) experiments were conducted using picryl chloride as an allergenic reaction trigger. That is, a first sensitization was carried out by applying an ethanol solution of 7% chloride Pikurihachi to the abdomen of the mare with prickly hair, and immediately thereafter, the test drug dissolved in distilled water was orally administered twice a day for 1+1 days. .
被検薬物の投与量は次の通りである。The dosage of the test drug was as follows.
製造例の２）の分画１ ｉ １ｏｎ＃／＆ｑ分画薯＋
２ ｓ ｏｒｎ９／ｋｔｉ分画謹；１０口ｍｌ／ｋ
ｇ
分画１ｙ 、 ２５口ｍ９Ａｑ
薬効の判定は、１％塩化ビクリルオリーブ油溶液をマウ
スの両耳にぬり、反応直前及び反応段１２、１８．２４
並びに５６時間後の１％地化ピクリル倹布によって嵩て
起１．ノ′ζ皮Ｍ’（炎の程りりをダイアルシツクネヌ
ゲーシ（ＰＥＡＣＯＫ−Ｇ型、川崎製作所）でｌり定す
ることによりおこなった。Production example 2) fraction 1 i 1on#/&q fraction +
2s orn9/kti fraction; 10ml/k
g Fraction 1y, 25 mouths m9Aq To judge the medicinal efficacy, apply a 1% chlorinated vicryl olive oil solution to both ears of the mouse, immediately before the reaction, and at reaction stages 12 and 18.24.
After 56 hours, 1. This was done by determining the extent of the flame with a dial gauge (Model PEACOK-G, Kawasaki Seisakusho).
その結果は第９図に示す通りであり、製造例２）の分画
Ｉ（図中１の浮腫曲線）及び分１ＩｌｌＩ（図中２のｉ
”−１’ ｌｉ’Ｘ曲線）に特に効果がみられた。The results are shown in FIG.
A particular effect was seen on the ``-1'li'X curve).
製造例の２）の分画ｌについては、被検薬物としての投
与量を３５ ｎ ｒｎ９Ａｑと１〜、上記と同鴎の試験
をおこなったところ、第１（）図の結果を得た。Regarding fraction 1 of Production Example 2), the same test as above was carried out using 35 n rn9Aq at a dose of 1 to 1 as a test drug, and the results shown in FIG. 1() were obtained.
更に、躬浩例の６）の化合物についても、被検薬物と１
〜での投与ｉｉ１ｏ０ｒｎｇΔｑと【−１上記と同様の
試験をおこなった。比較のため、製造例の２）の分画欝
については、投与量を１ｏｏ ｒｎ９／ｋｑとし、再び
試験をおこなった。Furthermore, regarding the compound 6) in the example of Hiro Mitsu, the test drug and 1
Administration at ii1o0rngΔq and [-1 The same test as above was conducted. For comparison, regarding the fractionation in Production Example 2), the test was conducted again at a dosage of 10 rn9/kq.
その結果は、第１１図に示す通りであり、製造例の２）
の分１＋ｌ＋ｉ ｌ （図中２の浮腫曲線）及び製造例
の３）の（１）式の化合物（１図中６の浮腫曲線）に特
に効県がみられ、ＢＡＧ例の３）の（Ｉ）式の化合物（
図中７の浮腫曲線）及び（１）式の化合物（図中８の浮
腫曲線）に前者よりも弱いが、明らかな効果が観察され
た。製造例の３）の（ＩＶ）式の化合物（図中５の浮腫
曲線）は効果が殆んど認められなかった。The results are as shown in Figure 11, and are shown in Production Example 2)
Particularly effective effects were observed for the compound of formula (1) (edema curve 2 in Figure 1) in Production Example 3) (edema curve 6 in Figure 1); ) Compound of formula (
A clear effect, although weaker than the former, was observed for the compound of formula (1) (edema curve 7 in the figure) and the compound of formula (1) (edema curve 8 in the figure). In Production Example 3), the compound of formula (IV) (edema curve 5 in the figure) had almost no effect.
２）モルモノ） ＰＣＡ反応に対する効果抗血清の作成
法蓚 牛血清アルデミン（ＢＳＡ）を２チの割合で生理
食塩水にとかし、これにフロイントのコンブリートアジ
エバンドを１：１の割合で十分に乳化混合し、体重３０
０ｇ前後の雄性モルモットをエーテルで軽く麻酔し、前
記乳濁液を前後の足踵計４ケ所に０．１１ｔｌづ！皮下
注射１−た。この注ｎ、１の後、３００回目背部に２ケ
所０．１ｔｌづ＼前述同様抗原ＢＳＡを注射し、２回目
の感作とした。２回目の感作後１４４回目全血を採血ｌ
〜、血清を得、このものを抗ＢＳＡ血清として以下の実
験に使用した。2) Effect on PCA reaction How to prepare antiserum: Dissolve 2 parts of bovine serum aldemin (BSA) in physiological saline, and thoroughly emulsify Freund's combrito agieband in a 1:1 ratio. Mixed, weight 30
A male guinea pig weighing around 0g was lightly anesthetized with ether, and 0.11 tl of the emulsion was applied to a total of 4 locations on the front and back heels! Subcutaneous injection 1-. After this injection, the antigen BSA was injected into the back for the 300th time in 2 places at 0.1 tl in the same manner as described above for the second sensitization. 144th whole blood sample after second sensitization
~, serum was obtained and used as anti-BSA serum in the following experiment.
実験方法 実験前日に電気バリカンで刺毛した体重３０
０ Ｑ 前後のハートレー系雄性モルモットを１群５匹
とし、被検薬物を経口投与後直ちに、背部に前記抗血清
希釈液を０．１ ｔｔｔｔ Ｍケ所に皮肉注射Ｉ〜た。Experiment method: Hair of 30 kg was pricked with electric clippers on the day before the experiment.
Immediately after oral administration of the test drug to a group of 5 male Hartley guinea pigs around 0 Q, the diluted antiserum was injected subcutaneously into the back at 0.1 tttt M points.
注射後３時間目に抗原であるＢＳＡｏ、２％生理食塩水
溶（４１ｎ５ｙｇｔ及びエバンスブルー５チ生理食塩水
溶液０．５ｔｌを混じ、前足静脈より注射する。静脈に
注射後３０分に放血致死させ、背部の皮膚を剥離する。Three hours after the injection, the antigen BSAo, 2% physiological saline solution (41n5ygt and 0.5 tl of Evans blue 5ti physiological saline solution) is mixed and injected into the fore leg vein. 30 minutes after the injection into the vein, the animals are killed by exsanguination and the back Exfoliate the skin.
皮膚に惹起された色素斑の面積により抗アレルギー作用
の程度をプヲニメーターで面積を求め判定した。その結
果を第１表に示１−だ。The degree of anti-allergic effect was determined based on the area of pigmented spots induced on the skin using a poonimeter. The results are shown in Table 1.
第１表
第１表から明らかな如く、比較対照薬であるプレドニゾ
ロンに比較しゃ−弱いが、製造例の２）の分＋ｉ！ｊ
ＩにけＰＣＡ反応抑制効果が明らかに認められた。まだ
小１！浩例の１）のメクノールエキスも有効であった。Table 1 As is clear from Table 1, it is weaker than prednisolone, which is a comparative drug, but the amount of production example 2) +i! j
The inhibitory effect on PCA reaction was clearly observed in I. Still in first grade! Mechnol extract in 1) of Hirosa was also effective.
急性毒性試験
体重１８〜２０１の配糸雄性マウスを１群１５匹として
被検薬物の経口投与後３日間の致死数からＬＤヵを求め
た。その結果は第２寿の通りであった。Acute Toxicity Test LD was determined from the number of deaths during 3 days after oral administration of the test drug using 15 threaded male mice weighing 18 to 20 cm per group. The result was as per the second Kotobuki.
第 ２ 表
以上の結果から、本発明の化合物である（１）式の化合
物及びこの化合物と他のクマリン誘導体とからなる混合
物である分画（璽）は、１回２００−３００１１１ｆ。From the results shown in Table 2, it can be seen that the compound of formula (1), which is the compound of the present invention, and the fraction (marker), which is a mixture of this compound and other coumarin derivatives, have a fraction of 200-300111f.
１日２〜３回の服用で、成人のアレルギー治療に有効と
推定される。It is estimated that it is effective in treating allergies in adults when taken two to three times a day.
以下、更に本発明の化合物の製剤例を挙げる。Below, further examples of formulations of the compounds of the present invention are given.
（１）式の化合物をバレイショデンプンとよく混合し、
水を加えて練合する。１１１１＃ｌ Ｘ Ｉ Ｍｍの網
目を有するスクリーンで造粒して顆粒状とする。乾燥後
Ａ１６メツシユ（Ｂ、 Ｓ、）の篩で整粒する。次にこ
の顆粒をステアリン酸マグネシウムと混和し、打錠機で
ＩＴ３００ｍｇの錠剤とした。A compound of formula (1) is thoroughly mixed with potato starch,
Add water and mix. The mixture is granulated using a screen having a mesh size of 1111#l X I Mm. After drying, sieve with A16 mesh (B, S,). The granules were then mixed with magnesium stearate and made into tablets of 300 mg IT using a tablet press.
第１図〜第４図は、順ｉ＋′Ｃ（ｆｖ）式の化合物、（
１）式の化合物、（１）式の化合物、（Ｉｎ式の化合物
のＮＭＲスペクトルを、第５〜第８図はＭＡＳＳスペク
トルを示す。
第９図〜第１１図は、遅延型皮崩炎（塩化ピクリルによ
る）に苅する試験結果を示すグラフであり、図中の符号
中、１（）は盲検群の浮腫曲線を、λ）は対照群の浮腫
曲線を意味する。またその他の符号は次の通りの意味を
有する。
第９図における符号の意味
１逼 製造例の２）の分画１ （１００ｍｆＡｇ投与）
の浮腫曲線２； 〃 分画１ （２ｓｏｒｎｇ
Ａ＋投与）３； Ｉ 分画璽（１１００ｒｎ
／＆ｇ投与）４； ｌ 分画ｒｉ ＜ ２５ｏ
＃Ａａ与）第１Ｏ図における符号の意味
２； 製造＠］の２）の分画１ （３５０暉Δり投与）
の浮腫曲線第１１図における符号の意味
２； 製造例の２）の分画ｉ Ｉ （１ｏｏｔ＃Ａ＋投
与）ｏ浮ｍ曲ｍ５； 製造例の３）の（ＩＶ）式の化合
物（＃） １６； ＃ （＋）式の
化合物（＃） ＃７ｉ ＃ （１）
カゴヒ合物（＃） ＃８３ ＃ （
１）式の化合物（＃） ＃特許出願人
（財）生産開発科学研究所
８１．：。 １９図
第１１図Figures 1 to 4 show compounds of formula i+'C(fv), (
1), the compound of formula (1), and the compound of formula (In). Figures 5 to 8 show the MASS spectra. Figures 9 to 11 show the NMR spectra of the compound of formula (1), and the compound of formula (In). This is a graph showing the results of a test using picryl chloride), where 1 ( ) means the edema curve of the blind group, and λ) means the edema curve of the control group. In addition, other symbols have the following meanings. Meanings of symbols in Figure 9 1 Fraction 1 of production example 2) (100 mfAg administration)
Edema curve 2; Fraction 1 (2sorng
A+ administration) 3; I fractionation seal (1100rn
/&g administration) 4; l fraction ri < 25o
#Aa) Meaning of symbols in Figure 1O 2; Fraction 1 of 2) of [Production @] (Administered for 350 days)
Meaning of the symbols in the edema curve of FIG. 11 2; Fraction i of Production Example 2) I (1oot#A+administration) o float m curve m5; Compound of formula (IV) (#) of Production Example 3) 16 ; # Compound (+) formula (#) #7i # (1)
Kagohi compound (#) #83 # (
1) Compound of formula (#) #Patent applicant (Incorporated) Institute of Production Development Science 81. :. Figure 19Figure 11
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57164336A JPS5953476A (en) | 1982-09-20 | 1982-09-20 | Coumarin derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57164336A JPS5953476A (en) | 1982-09-20 | 1982-09-20 | Coumarin derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5953476A true JPS5953476A (en) | 1984-03-28 |
Family
ID=15791230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57164336A Pending JPS5953476A (en) | 1982-09-20 | 1982-09-20 | Coumarin derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5953476A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1486213A4 (en) * | 2002-02-27 | 2006-04-26 | Liping Yang | The use of the total coumarins of cnidium monnieri in preparation of the medicament for treating psoriasis |
| CN104127339A (en) * | 2014-07-09 | 2014-11-05 | 扬州中汇生物技术有限公司 | Fructus cnidii anti-allergic effective component, extracting method and applications thereof |
| CN107764927A (en) * | 2017-10-24 | 2018-03-06 | 广州智妥科技有限公司 | A kind of assay method of Himalayan mayapple fruit |
-
1982
- 1982-09-20 JP JP57164336A patent/JPS5953476A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1486213A4 (en) * | 2002-02-27 | 2006-04-26 | Liping Yang | The use of the total coumarins of cnidium monnieri in preparation of the medicament for treating psoriasis |
| US8124133B2 (en) | 2002-02-27 | 2012-02-28 | Liping Yang | Use of the total coumarins of Cnidium monnieri in preparation of the medicament for treating psoriasis |
| CN104127339A (en) * | 2014-07-09 | 2014-11-05 | 扬州中汇生物技术有限公司 | Fructus cnidii anti-allergic effective component, extracting method and applications thereof |
| CN107764927A (en) * | 2017-10-24 | 2018-03-06 | 广州智妥科技有限公司 | A kind of assay method of Himalayan mayapple fruit |
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