JPH06128251A - Magnolianine compound - Google Patents
Magnolianine compoundInfo
- Publication number
- JPH06128251A JPH06128251A JP28183092A JP28183092A JPH06128251A JP H06128251 A JPH06128251 A JP H06128251A JP 28183092 A JP28183092 A JP 28183092A JP 28183092 A JP28183092 A JP 28183092A JP H06128251 A JPH06128251 A JP H06128251A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- agent
- magnolianine
- ethyl acetate
- lipoxygenase
- 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
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- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
(57)【要約】
【目的】 優れたリポキシゲナーゼ阻害作用を有し、抗
喘息剤、抗アレルギー剤、消炎鎮痛剤、抗リウマチ剤及
び皮膚疾患治療剤として有用な、新規なマグノリアニン
化合物を提供すること。
【構成】 下記一般式（１）で表されるマグノリアニン
化合物。式中、Ｒは水素原子又はアセチル基を示す。
【化１】
(57) [Summary] [Object] To provide a novel magnolianine compound having an excellent lipoxygenase inhibitory action and useful as an anti-asthma agent, an anti-allergic agent, an anti-inflammatory analgesic agent, an anti-rheumatic agent and a therapeutic agent for skin diseases. thing. [Structure] A magnolianine compound represented by the following general formula (1). In the formula, R represents a hydrogen atom or an acetyl group. [Chemical 1]
Description
【０００１】[0001]
【産業上の利用分野】本発明は、新規なマグノリアニン
化合物に関する。本発明の化合物は、リポキシゲナーゼ
阻害作用を有する。FIELD OF THE INVENTION The present invention relates to a novel magnolianine compound. The compound of the present invention has a lipoxygenase inhibitory action.
【０００２】[0002]
【従来の技術】厚朴はモクレン科（Ｍａｇｎｏｌｉａｃ
ｅａｅ）に属するホオノキ（Ｍａｇｎｏｌｉａ ｏｂｏ
ｖａｔａ ＴＵＮＢ．）の乾燥樹皮で、古くから中国、
日本で膨満感を特徴とする消化器系疾患、不定神経症に
対して処方されている重要な生薬の一つである。厚朴の
主成分としてネオリグナン類マグノロール〔薬学雑誌，
５０，１８３（１９３０）〕、ホーノキオール〔Ｃｈｅ
ｍ．Ｐｈａｒｍ．Ｂｕｌｌ．，２０，２１２（１９７
２）、オボバタオール〔Ｃｈｅｍ．Ｐｈａｒｍ．Ｂｕｌ
ｌ．，３０，３４４７（１９８２）〕、ビフェニル型ネ
オリグナンとセスキテルペンがエーテル結合したセスキ
テルペン−ネオリグナン類〔Ｔｅｔｒａｈｅｄｒｏｎ，
４８，３７７（１９９２）〕等が知られている。[Prior Art] Magnolia is a magnolia family.
honoki (Magnolia obo) belonging to eae)
vata TUNB. ) Dried bark from China,
It is one of the important herbal medicines prescribed in Japan for digestive system diseases characterized by bloating and adventitia. Neolignans magnolol as the main component of Koboku [Pharmaceutical magazine,
50 , 183 (1930)], Honokiol [Che
m. Pharm. Bull. , 20 , 212 (197)
2), ovobataol [Chem. Pharm. Bul
l. , 30 , 3447 (1982)], sesquiterpene-neolignans in which a biphenyl type neolignan and a sesquiterpene are ether-bonded [Tetrahedron,
48 , 377 (1992)] and the like are known.
【０００３】[0003]
【発明が解決しようとする課題】本発明の目的は、優れ
たリポキシゲナーゼ阻害作用を有し、抗喘息剤、抗アレ
ルギー剤、消炎鎮痛剤、抗リウマチ剤及び皮膚疾患治療
剤として有用な、新規なマグノリアニン化合物を提供す
ることにある。DISCLOSURE OF THE INVENTION The object of the present invention is to provide a novel lipoxygenase inhibitory activity, which is useful as an anti-asthma agent, anti-allergic agent, anti-inflammatory analgesic agent, anti-rheumatic agent and therapeutic agent for skin diseases. To provide a magnolianine compound.
【０００４】[0004]
【課題を解決するための手段】本発明者らは厚朴の成分
を鋭意研究した結果、極めて強いリポキシゲナーゼ阻害
活性を有する化合物を見出し、これら化合物を「マグノ
リアニン（ｍａｇｎｏｌｉａｎｉｎ）」と命名し、本発
明を完成するに至った。本発明は、一般式（１）[Means for Solving the Problems] As a result of intensive studies of the ingredients of the magnolia bark, the present inventors have found compounds having extremely strong lipoxygenase inhibitory activity, named these compounds "magnolianin", The invention was completed. The present invention has the general formula (1)
【０００５】[0005]
【化２】 [Chemical 2]
【０００６】〔式中、Ｒは水素原子又はアセチル基を示
す。〕で表されるマグノリアニン化合物に係わる。一般
式（１）で表される本発明の化合物は、優れたリポキシ
ゲナーゼ阻害作用を有している。ここで、リポキシゲナ
ーゼとしては、例えば５−リポキシゲナーゼ、１２−リ
ポキシゲナーゼ、１５−リポキシゲナーゼ等が挙げら
れ、本発明の化合物は特に５−リポキシゲナーゼに優れ
た阻害作用を有している。[In the formula, R represents a hydrogen atom or an acetyl group. ] It concerns with the magnolianine compound represented by these. The compound of the present invention represented by the general formula (1) has an excellent lipoxygenase inhibitory action. Here, examples of the lipoxygenase include 5-lipoxygenase, 12-lipoxygenase, 15-lipoxygenase and the like, and the compound of the present invention particularly has an excellent inhibitory action on 5-lipoxygenase.
【０００７】本発明の化合物は、優れたリポキシゲナー
ゼ阻害作用を有し、抗喘息剤、抗アレルギー剤、消炎鎮
痛剤、抗リウマチ剤及び皮膚疾患治療剤として有用であ
る。本発明のマグノリアニン化合物を抽出単離するには
例えば、厚朴から有効成分をメタノール、エタノール等
のアルコール類、塩化メチレン、酢酸エチル等の有機溶
媒を用いて抽出し、抽出液を濾過後、濾液を濃縮して第
一次抽出物を得、次いで該抽出物から目的化合物の理化
学的性状を利用した各種の方法により目的物を採取す
る。該目的物の採取は、通常の方法、例えば溶解度の差
を利用する方法、活性炭、アンバーライト、シリカゲ
ル、イオン交換樹脂、セファデックス、トヨパール等の
吸着剤に対する吸着親和力の差を利用する方法、二液相
関の分配率の差を利用する方法、これら各方法の組合せ
等により実施できる。The compound of the present invention has an excellent lipoxygenase inhibitory activity and is useful as an anti-asthma agent, anti-allergic agent, anti-inflammatory analgesic agent, anti-rheumatic agent and therapeutic agent for skin diseases. To extract and isolate the magnolianine compound of the present invention, for example, the active ingredient is extracted from an alcoholic solvent such as methanol, ethanol, etc. using methylene chloride, an organic solvent such as ethyl acetate, and the extract is filtered, The filtrate is concentrated to obtain a primary extract, and then the target substance is collected from the extract by various methods utilizing the physicochemical properties of the target compound. The target substance can be collected by a conventional method, for example, a method utilizing a difference in solubility, a method utilizing a difference in adsorption affinity for an adsorbent such as activated carbon, amberlite, silica gel, ion exchange resin, Sephadex, and Toyopearl. It can be carried out by a method of utilizing the difference in distribution ratio of liquid correlation, a combination of these methods, or the like.
【０００８】又、アセチル体は上記で得られた化合物を
無水酢酸又はアセチルクロライド等を触媒の存在下又は
無存在下に反応させることにより得られる。触媒として
はピリジン、トリエチルアミン、ジメチルアミノピリジ
ン等を例示することができる。溶媒としては反応に関与
しないものである限り特に制限されないが、一般にピリ
ジン、クロロホルム、ジクロロメタン等を挙げることが
できる。The acetylated compound can be obtained by reacting the compound obtained above with acetic anhydride, acetyl chloride or the like in the presence or absence of a catalyst. Examples of the catalyst include pyridine, triethylamine, dimethylaminopyridine and the like. The solvent is not particularly limited as long as it does not participate in the reaction, but generally pyridine, chloroform, dichloromethane and the like can be mentioned.
【０００９】[0009]
【実施例】次に実施例、薬理試験例を示し、本発明をさ
らに詳しく説明する。 〔実施例１〕厚朴（ホウノキの樹皮）１０ｋｇを細片し
粉砕後、メタノール９０Ｌを添加し、室温下で８日間要
して抽出した。抽出液は濾過後、メタノールを減圧下留
去し、第一次抽出物を得た。得られた第一次抽出物を酢
酸エチル−水間で溶媒分配し、酢酸エチル可溶部を１０
５６ｇ得た。この酢酸エチル可溶部５５０ｇをシリカゲ
ルカラムクロマトグラフィー（Ｍｅｒｃｋ Ｋｉｓｅｌ
ｇｅｌ ６０，２９６０ｇ）に付し、ｎ−ヘキサン−酢
酸エチル（１：１，ｖ／ｖ，１７Ｌ）、塩化メチレン−
酢酸エチル（７：３，ｖ／ｖ，１２Ｌ）で順次溶出し、
フラクション１（３５０ｇ）、フラクション２（１８５
ｇ）を得た。フラクション１を再度シリカゲルカラムク
ロマトグラフィー（Ｗａｋｏｇｅｌ Ｃ−３００，５２
００ｇ）に付し、ｎ−ヘキサン−酢酸エチル（１９：
１，１４：１，９：１，４：１，３：２，ｖ／ｖ，各１
５Ｌ）混合溶媒で順次溶出して、各約７Ｌずつのフラク
ション３〜１３に分画した。フラクション９の沈殿物を
減圧濾過で取り除いた後、濾液を減圧下濃縮した。得ら
れた残渣５ｇをメタノール１０ｍＬに溶解し、セファデ
ックスＬＨ−２０（ファルマシア社製，１０００ｍＬ）
に付し、メタノールで溶出して、各約５０ｍＬずつのフ
ラクション１４〜１８に分画し、フラクション１５を更
にシリカゲルカラムクロマトグラフィー（Ｍｅｒｃｋ
Ｋｉｓｅｌｇｅｌ ６０，２００ｇ）に付した。塩化メ
チレン−酢酸エチル（９５：５，ｖ／ｖ，３００Ｌ）で
溶出された分画５５６ｍｇを逆相中圧ローバーカラムク
ロマトグラフィーＲＰ−８（メルク社製，タイプＢ）に
付し、メタノール−水（９５：５，ｖ／ｖ）で精製し、
一般式（１）においてＲが水素原子である化合物１を３
５０ｍｇ得た。EXAMPLES Next, the present invention will be described in more detail with reference to Examples and pharmacological test examples. [Example 1] 10 kg of bark (bark of Japanese cypress) was crushed into small pieces, crushed, 90 L of methanol was added, and the mixture was extracted at room temperature for 8 days. The extract was filtered and then methanol was distilled off under reduced pressure to obtain a primary extract. The obtained primary extract was subjected to solvent partition between ethyl acetate and water, and the ethyl acetate-soluble portion was washed with 10 parts.
56 g were obtained. 550 g of this ethyl acetate-soluble portion was subjected to silica gel column chromatography (Merck Kisel).
gel 60, 2960 g), n-hexane-ethyl acetate (1: 1, v / v, 17 L), methylene chloride-
Elute sequentially with ethyl acetate (7: 3, v / v, 12 L),
Fraction 1 (350 g), Fraction 2 (185
g) was obtained. Fraction 1 was again subjected to silica gel column chromatography (Wakogel C-300, 52).
00g) and n-hexane-ethyl acetate (19:
1, 14: 1, 9: 1, 4: 1, 3: 2, v / v, 1 each
(5 L) mixed solvent was sequentially eluted and fractionated into fractions 3 to 13 of about 7 L each. The precipitate of fraction 9 was removed by vacuum filtration, and the filtrate was concentrated under reduced pressure. 5 g of the obtained residue was dissolved in 10 mL of methanol, and Sephadex LH-20 (manufactured by Pharmacia, 1000 mL).
And elute with methanol to fractionate into fractions 14 to 18 of about 50 mL each, and fraction 15 is further subjected to silica gel column chromatography (Merck).
Kiselgel 60, 200 g). The fraction 556 mg eluted with methylene chloride-ethyl acetate (95: 5, v / v, 300 L) was subjected to reverse phase medium pressure row bar column chromatography RP-8 (Merck, type B), and methanol-water. (95: 5, v / v),
Compound 1 in which R is a hydrogen atom in the general formula (1) is 3
Obtained 50 mg.
【００１０】性状：白色アモルファス状粉末 比旋光度：〔α〕20 D ＝±０°（ｃ＝０．５，ＣＨＣｌ
3 ） マススペクトル（ＨＲＦＡＢ）ｍ／ｚ：８２６．３５０
５〔Ｍ〕+ 理論値：８２６．３５０５(C54H50O8として) マススペクトル（ＦＡＢ）ｍ／ｚ（rel. int.)：８４９
〔Ｍ＋Ｎａ〕+ （２５），８２６〔Ｍ〕+ （４７），５
５９〔Ｍ−２６７〕+ （１８），５４５〔Ｍ−２８１〕
+ （４５），２８１（８０），２６７（６２） 紫外線吸収スペクトル：エタノール中、λmax nm(ε)
：２２４（４２８００），２７５（８３００），２８
０（８３００） 赤外吸収スペクトル：クロロホルム中、νmax cm-1：３
５５０（ＯＨ），１６４０（Ｃ＝ＣＨ2 ），１５９０，
１４９０（芳香族），９９５，９１０1 H-NMRスペクトル（ＣＤＣｌ3 ）δ：３．２−３．４
（１０Ｈ，ｍ），４．９−５．１５（１０Ｈ，ｍ），
３．７１（１Ｈ，ｄｄ，Ｊ＝９．９，２．９Ｈｚ），
４．０５（１Ｈ，ｄｄｄ，Ｊ＝８．１，２．５，２．５
Ｈｚ），４．２９（１Ｈ，ｄｄ，Ｊ＝９．９，２．９Ｈ
ｚ），４．６３（１Ｈ，ｄ，Ｊ＝８．１Ｈｚ），５．７
５−６．０５（５Ｈ，ｍ），６．２６（１Ｈ，ｄ，Ｊ＝
１．５Ｈｚ），６．４０（１Ｈ，ｄ，Ｊ＝１．５Ｈ
ｚ），６．４１（１Ｈ，ｄ，Ｊ＝１．５Ｈｚ），６．５
４（１Ｈ，ｄ，Ｊ＝１．５Ｈｚ），６．７８（１Ｈ，
ｄ，Ｊ＝８．０Ｈｚ），６．８０（２Ｈ，ｄｄ，Ｊ＝
８．０Ｈｚ），６．８１（１Ｈ，ｄ，Ｊ＝８．１Ｈ
ｚ），６．９１（１Ｈ，ｄ，Ｊ＝２．２Ｈｚ），６．９
２（２Ｈ，ｄ，Ｊ＝８．８Ｈｚ），６．９３（１Ｈ，
ｄ，Ｊ＝２．２Ｈｚ），６．９８（１Ｈ，ｄｄ，Ｊ＝
８．０，２．２Ｈｚ），６．９８（１Ｈ，ｄｄ，Ｊ＝
８．１，２．２Ｈｚ），７．０７（２Ｈ，ｄ，Ｊ＝８．
８Ｈｚ），７．０８（２Ｈ，ｄ，Ｊ＝８．１Ｈｚ） 〔実施例２〕実施例１で得た化合物１（１５０ｍｇ）を
ピリジン１ｍＬに溶解し、無水酢酸１ｍＬを加え、室温
下２０時間放置した後、氷水を反応溶液に加え、酢酸エ
チルで抽出した。酢酸エチル層を１Ｎ塩酸溶液、飽和炭
酸水素ナトリウム溶液、飽和食塩水で順次洗浄した後、
無水硫酸マグネシウムで乾燥し、濾過し、減圧下で濃縮
して一般式（１）においてＲがアセチル基である化合物
２をアモルファス状粉末として１３７ｍｇ得た。Properties: White amorphous powder Specific optical rotation: [α] 20 D = ± 0 ° (c = 0.5, CHCl
3 ) Mass spectrum (HRFAB) m / z: 826.350
5 [M] + theoretical value: 826.3505 (as C 54 H 50 O 8 ) mass spectrum (FAB) m / z (rel. Int.): 849
[M + Na] + (25), 826 [M] + (47), 5
59 [M-267] + (18), 545 [M-281]
+ (45), 281 (80), 267 (62) UV absorption spectrum: λmax nm (ε) in ethanol
: 224 (42800), 275 (8300), 28
0 (8300) Infrared absorption spectrum: νmax cm -1 : 3 in chloroform
550 (OH), 1640 (C = CH 2), 1590,
1490 (aromatic), 995,910 1 H-NMR spectrum (CDCl 3 ) δ: 3.2-3.4
(10H, m), 4.9-5.15 (10H, m),
3.71 (1H, dd, J = 9.9, 2.9Hz),
4.05 (1H, ddd, J = 8.1, 2.5, 2.5
Hz), 4.29 (1H, dd, J = 9.9, 2.9H)
z), 4.63 (1H, d, J = 8.1 Hz), 5.7.
5-6.05 (5H, m), 6.26 (1H, d, J =
1.5Hz), 6.40 (1H, d, J = 1.5H
z), 6.41 (1H, d, J = 1.5 Hz), 6.5
4 (1H, d, J = 1.5Hz), 6.78 (1H,
d, J = 8.0 Hz), 6.80 (2H, dd, J =
8.0 Hz), 6.81 (1H, d, J = 8.1H
z), 6.91 (1H, d, J = 2.2 Hz), 6.9.
2 (2H, d, J = 8.8Hz), 6.93 (1H,
d, J = 2.2 Hz), 6.98 (1H, dd, J =
8.0, 2.2 Hz, 6.98 (1H, dd, J =
8.1, 2.2 Hz), 7.07 (2H, d, J = 8.
8 Hz), 7.08 (2H, d, J = 8.1 Hz) [Example 2] Compound 1 (150 mg) obtained in Example 1 was dissolved in 1 mL of pyridine, 1 mL of acetic anhydride was added, and the mixture was stirred at room temperature for 20 hours. After standing, ice water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with a 1N hydrochloric acid solution, a saturated sodium hydrogen carbonate solution and a saturated saline solution,
The extract was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain 137 mg of Compound 2 in which R is an acetyl group in the general formula (1) as an amorphous powder.
【００１１】マススペクトル（ＨＲＦＡＢ）ｍ／ｚ：９
５２．３８３４〔Ｍ〕+ 理論値：９５２．３８２２(C60H56O11として) マススペクトル（ＦＡＢ）ｍ／ｚ（rel. int.)：９５２
〔Ｍ〕+ （２０），９１０〔Ｍ−４２〕+ （１２），６
７１〔Ｍ−２８１〕+ （１１），６２９〔Ｍ−３２
３+ 〕（１５），５８７〔Ｍ−３６５〕+ （１０），３
６５（１０），３２３（４０），２８１（１００），２
５５（３５）1 H-NMRスペクトル（ＣＤＣｌ3 ）δ：１．８８（３Ｈ，
ｓ），２．１４（３Ｈ，ｓ），２．２４（３Ｈ，ｓ），
３．２−３．３（１０Ｈ，ｍ），４．９−５．１（１０
Ｈ，ｍ），５．８−６．０（５Ｈ，ｍ），３．７８（１
Ｈ，ｄｄ，Ｊ＝１１．０，２．８Ｈｚ），４．０４（１
Ｈ，ｄｄｄ，Ｊ＝７．２，２．８，２．８Ｈｚ），４．
２４（１Ｈ，ｄｄ，Ｊ＝１１．０，２．８Ｈｚ），４．
８１（１Ｈ，ｄ，Ｊ＝７．２Ｈｚ），６．３９（１Ｈ，
ｄ，Ｊ＝２．１Ｈｚ），６．５３（１Ｈ，ｄ，Ｊ＝２．
１Ｈｚ），６．６８（１Ｈ，ｄ，Ｊ＝１．８Ｈｚ），
６．７４（１Ｈ，ｄ，Ｊ＝８．２Ｈｚ），６．７８（２
Ｈ，ｄ，Ｊ＝８．５Ｈｚ），６．８２（１Ｈ，ｄ，Ｊ＝
１．８Ｈｚ），６．８６（２Ｈ，ｄ，Ｊ＝８．７Ｈ
ｚ），６．９３（２Ｈ，ｄ，Ｊ＝８．５Ｈｚ），６．９
３（１Ｈ，ｄ，Ｊ＝８．２Ｈｚ），６．９４（２Ｈ，
ｄ，Ｊ＝２．１Ｈｚ），７．０４５（１Ｈ．ｄ．Ｊ＝
２．１Ｈｚ），７．０５２（１Ｈ，ｄ，Ｊ＝８．２，
２．１Ｈｚ），７．０８（２Ｈ，ｄ，Ｊ＝８．７Ｈｚ） 〔薬理試験例〕５−リポキシゲナーゼ阻害作用 ケンキチ オチ（Ｋｅｎｋｉｃｈｉ Ｏｃｈｉ）ら、
Ｊ．Ｂｉｏｌ．Ｃｈｅｍ．２５８，５７５４−５７５８
（１９８３）に記載の方法に従い、試験を行った。すな
わち、モルモットの腹腔内にカゼインを注射し、多形核
白血球を採取し、その細胞質画分を酵素標本として得
た。Mass spectrum (HRFAB) m / z: 9
52.3834 [M] + theoretical value: 952.3822 (as C 60 H 56 O 11 ) mass spectrum (FAB) m / z (rel. Int.): 952
[M] + (20), 910 [M-42] + (12), 6
71 [M-281] + (11), 629 [M-32
3 + ] (15), 587 [M-365] + (10), 3
65 (10), 323 (40), 281 (100), 2
55 (35) 1 H-NMR spectrum (CDCl 3 ) δ: 1.88 (3H,
s), 2.14 (3H, s), 2.24 (3H, s),
3.2-3.3 (10H, m), 4.9-5.1 (10
H, m), 5.8-6.0 (5H, m), 3.78 (1
H, dd, J = 11.0, 2.8 Hz), 4.04 (1
H, ddd, J = 7.2, 2.8, 2.8 Hz), 4.
24 (1H, dd, J = 11.0, 2.8Hz), 4.
81 (1H, d, J = 7.2 Hz), 6.39 (1H,
d, J = 2.1 Hz), 6.53 (1H, d, J = 2.
1Hz), 6.68 (1H, d, J = 1.8Hz),
6.74 (1H, d, J = 8.2Hz), 6.78 (2
H, d, J = 8.5 Hz), 6.82 (1H, d, J =
1.8 Hz), 6.86 (2H, d, J = 8.7H)
z), 6.93 (2H, d, J = 8.5 Hz), 6.9.
3 (1H, d, J = 8.2Hz), 6.94 (2H,
d, J = 2.1 Hz), 7.045 (1H.d.J =
2.1 Hz), 7.052 (1H, d, J = 8.2,
2.1 Hz), 7.08 (2H, d, J = 8.7 Hz) [Pharmacological test example] 5-lipoxygenase inhibitory action Kenkichi Ochi et al.
J. Biol. Chem. 258 , 5754-5758
The test was conducted according to the method described in (1983). That is, casein was intraperitoneally injected into guinea pigs, polymorphonuclear leukocytes were collected, and the cytoplasmic fraction thereof was obtained as an enzyme sample.
【００１２】14Ｃ−アラキドン酸に酵素標本及び各種濃
度の化合物１を一定時間反応させ、生成する５−ヒドロ
キシエイコサテトラエン酸を薄層クロマトグラフィーに
より分離し、その放射活性を測定し、対照群との放射活
性の比較からＩＣ50を算出しした。その結果、化合物１
のＩＣ50は０．４５μＭであった。[0012] 14 C-Arachidonic acid was reacted with an enzyme sample and various concentrations of Compound 1 for a certain period of time, and 5-hydroxyeicosatetraenoic acid produced was separated by thin-layer chromatography, and its radioactivity was measured to obtain a control. IC 50 was calculated from the comparison of radioactivity with the group. As a result, compound 1
Had an IC 50 of 0.45 μM.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ａ６１Ｋ 31/335 ＡＣＤ 9360−4Ｃ ＡＤＡ 9360−4Ｃ ＡＥＤ 9360−4Ｃ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification number Reference number within the agency FI Technical display area A61K 31/335 ACD 9360-4C ADA 9360-4C AED 9360-4C
Claims (1)
れるマグノリアニン化合物。1. A general formula (1): [In the formula, R represents a hydrogen atom or an acetyl group. ] The magnolianine compound represented by these.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28183092A JPH06128251A (en) | 1992-10-20 | 1992-10-20 | Magnolianine compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28183092A JPH06128251A (en) | 1992-10-20 | 1992-10-20 | Magnolianine compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06128251A true JPH06128251A (en) | 1994-05-10 |
Family
ID=17644605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28183092A Pending JPH06128251A (en) | 1992-10-20 | 1992-10-20 | Magnolianine compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06128251A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140037772A1 (en) * | 2011-02-09 | 2014-02-06 | Wendy Lien | Cosmetic or Pharmaceutical Formulation |
-
1992
- 1992-10-20 JP JP28183092A patent/JPH06128251A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140037772A1 (en) * | 2011-02-09 | 2014-02-06 | Wendy Lien | Cosmetic or Pharmaceutical Formulation |
| US9931289B2 (en) * | 2011-02-09 | 2018-04-03 | Forward Scout Enterprises Pty Ltd | Cosmetic or pharmaceutical formulation |
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