JPH07300412A - Active oxygen remover and composition containing the same - Google Patents
Active oxygen remover and composition containing the sameInfo
- Publication number
- JPH07300412A JPH07300412A JP6093286A JP9328694A JPH07300412A JP H07300412 A JPH07300412 A JP H07300412A JP 6093286 A JP6093286 A JP 6093286A JP 9328694 A JP9328694 A JP 9328694A JP H07300412 A JPH07300412 A JP H07300412A
- Authority
- JP
- Japan
- Prior art keywords
- chemical
- active oxygen
- represented
- group
- chain length
- 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
Landscapes
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Seeds, Soups, And Other Foods (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は活性酸素消去剤及びこれ
を含有する化粧料、医薬組成物、食用組成物に関する。TECHNICAL FIELD The present invention relates to an active oxygen scavenger and cosmetics, pharmaceutical compositions and edible compositions containing the same.
【0002】[0002]
【従来の技術】一般的に、活性酸素が生体に及ぼす影響
としては、コラーゲン線維の架橋や、DNA螺旋の部分
開裂、連鎖的ラジカルの発生による組織の損傷が挙げら
れ、その結果として皮膚のシワや弾力消失、脱毛といっ
た生体の老化、気管支喘息等のアレルギー反応の惹起と
ヒスタミン放出による炎症の惹起、虚血性疾患である心
筋梗塞における平滑筋の損傷、肝臓障害などの疾患の悪
化、また、脳組織の破壊による痴呆の誘発等が引き起こ
されることが知られている。更に、詳細な原因は不明で
あるがリューマチの発症にも活性酸素が関与していると
言われている。2. Description of the Related Art Generally, the effects of active oxygen on the living body include cross-linking of collagen fibers, partial cleavage of DNA helix, and tissue damage due to generation of chained radicals, resulting in skin wrinkles. Aging of the body such as loss of elasticity and loss of hair, induction of allergic reactions such as bronchial asthma and inflammation due to histamine release, damage of smooth muscle in ischemic myocardial infarction, deterioration of diseases such as liver damage, and brain It is known that tissue destruction causes dementia and the like. Furthermore, although the detailed cause is unknown, it is said that active oxygen is involved in the onset of rheumatism.
【0003】従って、生体内において活性酸素の発生を
抑制することは、これらの疾患を治療あるいは予防する
点で非常に重要なことであり、このため、従来より生体
内に発生した活性酸素を消去する作用のある物質の探索
が広く行われてきた。Therefore, suppressing the generation of active oxygen in the living body is very important in treating or preventing these diseases, and therefore, the active oxygen generated in the living body is eliminated from the conventional case. The search for substances that have the action to do so has been widely conducted.
【0004】例えば、この様な作用を有する薬剤とし
て、従来より用いられてきたものとしては、天然物由来
のものでは、脂溶性のトコフェロール(ビタミンE)、
水溶性のアスコルビン酸(ビタミンC)が挙げられ、合
成化合物では、BHT(ブチルヒドロキシトルエン)、
BHA(ブチルヒドロキシアニソール)等が挙げられ
る。しかし、これらの薬剤は活性酸素消去作用が十分で
はなく、合成化合物においては、BHTもBHAも発癌
性の疑いが持たれており、何れも活性酸素消去剤として
は実用的とは言い難かった。[0004] For example, as a drug having such an action, conventionally used are those derived from natural products such as fat-soluble tocopherol (vitamin E),
Examples include water-soluble ascorbic acid (vitamin C), and synthetic compounds include BHT (butylhydroxytoluene),
BHA (butylhydroxyanisole) etc. are mentioned. However, these agents have insufficient active oxygen scavenging action, and in synthetic compounds, both BHT and BHA are suspected to be carcinogenic, and it was difficult to say that any of them was practical as an active oxygen scavenger.
【0005】また、最近では、十分な薬効と安全性を求
めて、生薬抽出物から活性酸素消去作用を有する物質を
得ようとする試みも数多くなされており、例えば、特開
昭60−224629号、特開昭61−24522号、
特開平2−193930号、特開平2−243632
号、特開平2−264727号、特開平3−15362
9号、特開平3−221587号、特開平4−6934
3号、特開平4−202138号、特開平4−2470
10号の各公報に記載の発明は、何れも生薬由来の活性
酸素消去作用を有する物質を利用したものである。しか
し、これらの生薬抽出物では、安全性に問題がないもの
の、活性酸素消去作用の点から言えば、未だ十分なもの
は得られていなかった。In recent years, many attempts have been made to obtain a substance having an active oxygen scavenging action from a crude drug extract in search of sufficient medicinal effect and safety, for example, JP-A-60-224629. , JP-A-61-24522,
JP-A-2-193930, JP-A-2-243632
No. 2, JP-A-2-264727, JP-A-3-15362
No. 9, JP-A-3-221587, JP-A-4-6934.
3, JP-A-4-202138, and JP-A-4-2470.
The inventions described in the respective publications of No. 10 each utilize a substance having an active oxygen scavenging action derived from a crude drug. However, although these crude drug extracts have no safety problems, they have not been sufficiently obtained in terms of active oxygen scavenging action.
【0006】更に、生体内の酵素の一つスーパーオキシ
ドデスムターゼ(SOD)を投与することにより、生体
内に発生する活性酸素を消去する試みもなされてきてい
るが、SODはタンパク質であるため、その入手が困難
であるばかりでなく、消化されてしまうが故に、経口投
与は不可能であり、また、注射による投与においても、
血中半減期が短く満足の行くものではなかった。Further, attempts have been made to eliminate active oxygen generated in the living body by administering superoxide desmutase (SOD), one of the enzymes in the living body, but since SOD is a protein, Not only is it difficult to obtain, but it is digested, so oral administration is not possible, and even when administered by injection,
The blood half-life was short and it was not satisfactory.
【0007】一方、一般式(I)で表される化合物やそ
の塩が、活性酸素を消去する作用を有することは全く知
られていなかった。更に、化粧料、医薬品あるいは食品
等に含有させて、上述した様々な疾患の予防や治療、老
化の防止、改善に用いる試みはされていなかった。On the other hand, it has not been known at all that the compound represented by the general formula (I) or a salt thereof has a function of eliminating active oxygen. Furthermore, there has been no attempt to use it for the prevention or treatment of various diseases mentioned above, prevention of aging, or improvement by incorporating it into cosmetics, pharmaceuticals, foods, or the like.
【0008】[0008]
【発明が解決しようとする課題】本発明は、上記観点か
らなされたものであり、生体内に発生する活性酸素を消
去する作用を十分に有し、更に、安全性が高い活性酸素
消去剤及びこれを含有する化粧料、医薬品、食品等の組
成物を提供することを課題とする。SUMMARY OF THE INVENTION The present invention has been made from the above viewpoints, and has an active oxygen scavenger having a sufficient effect of scavenging active oxygen generated in the living body and having high safety. An object of the present invention is to provide a composition such as a cosmetic, a drug, a food containing the same.
【0009】[0009]
【課題を解決するための手段】本発明者らは上記課題を
解決するために、活性酸素消去作用を指標に各種化合物
を広くスクリーニングした結果、一般式(I)で表され
る化合物が優れた活性酸素消去作用を有することを見出
し、本発明を完成するに至った。In order to solve the above problems, the present inventors extensively screened various compounds using the active oxygen scavenging action as an index, and as a result, the compound represented by the general formula (I) was excellent. They have found that they have an active oxygen scavenging action, and have completed the present invention.
【0010】すなわち本発明は、下記一般式(I)で表
される化合物及び/又はその生理的に許容される塩から
なる活性酸素消去剤及びこれを含有する化粧料、医薬組
成物、食用組成物である。That is, the present invention provides an active oxygen scavenger comprising a compound represented by the following general formula (I) and / or a physiologically acceptable salt thereof, and a cosmetic, pharmaceutical composition or edible composition containing the active oxygen scavenger. It is a thing.
【0011】[0011]
【化15】 [Chemical 15]
【0012】ただし、化15中、R1、R2は、それぞれ
独立して水素原子、水酸基又は短鎖長アルコキシル基を
示し、R3は、水素原子、カルボキシル基、短鎖長アル
コキシカルボニル基、ホルミル基、短鎖長アシル基、短
鎖長カルボキシアルケニル基、短鎖長アルコキシカルボ
ニルアルケニル基、短鎖長アルケニル基又は短鎖長ヒド
ロキシアルケニル基を示す。However, in Chemical formula 15, R 1 and R 2 each independently represent a hydrogen atom, a hydroxyl group or a short chain length alkoxyl group, and R 3 is a hydrogen atom, a carboxyl group, a short chain length alkoxycarbonyl group, A formyl group, a short chain length acyl group, a short chain length carboxyalkenyl group, a short chain length alkoxycarbonylalkenyl group, a short chain length alkenyl group or a short chain length hydroxyalkenyl group is shown.
【0013】以下、本発明を詳細に説明する。The present invention will be described in detail below.
【0014】<1>本発明の活性酸素消去剤 本発明の活性酸素消去剤は、上記一般式(I)で表され
る化合物及び/又はその生理的に許容される塩からな
る。<1> Active Oxygen Scavenger of the Present Invention The active oxygen scavenger of the present invention comprises a compound represented by the above general formula (I) and / or a physiologically acceptable salt thereof.
【0015】ここで、前記一般式(I)で表される化合
物中、R1及びR2は、水素原子又は短鎖長アルコキシル
基を示し、R3は、水素原子、カルボキシル基、短鎖長
アルコキシカルボニル基、ホルミル基、短鎖長アシル
基、短鎖長カルボキシアルケニル基、短鎖長アルコキシ
カルボニルアルケニル基、短鎖長アルケニル基又は短鎖
長ヒドロキシアルケニル基を示すが、これらのうちアル
コキシル基、アルコキシカルボニル基、アシル基、アル
コキシカルボニルアルケニル基におけるアルキル部分の
炭素数は1〜10であることが好ましく、より好ましく
は1〜6であり、更には1〜4がより好ましい。また、
カルボキシアルケニル基、アルコキシカルボニルアルケ
ニル基、アルケニル基、ヒドロキシアルケニル基のアル
ケニル部分の炭素数は、2〜10であることが好まし
く、より好ましくは2〜6であり、更には2〜4がより
好ましい。Here, in the compound represented by the general formula (I), R 1 and R 2 represent a hydrogen atom or a short chain length alkoxyl group, and R 3 represents a hydrogen atom, a carboxyl group or a short chain length. An alkoxycarbonyl group, a formyl group, a short chain length acyl group, a short chain length carboxyalkenyl group, a short chain length alkoxycarbonylalkenyl group, a short chain length alkenyl group or a short chain length hydroxyalkenyl group, among them, an alkoxyl group, The number of carbon atoms in the alkyl moiety of the alkoxycarbonyl group, the acyl group and the alkoxycarbonylalkenyl group is preferably 1 to 10, more preferably 1 to 6, and further preferably 1 to 4. Also,
The alkenyl portion of the carboxyalkenyl group, the alkoxycarbonylalkenyl group, the alkenyl group, and the hydroxyalkenyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms, and further preferably 2 to 4 carbon atoms.
【0016】上記アルコキシル基としては、例えば、メ
トキシル基、エトキシル基、プロポキシル基等が、アル
コキシカルボニル基としては、例えば、メトキシカルボ
ニル基、エトキシカルボニル基、プロポキシカルボニル
基等が、アシル基としては、例えば、アセチル基、プロ
ピオニル基、ブチリル基等が、アルコキシカルボニルア
ルケニル基としては、例えば、メトキシカルボニルビニ
ル基、エトキシカルボニルアリル基、プロポキシカルボ
ニルブテニル基等が、カルボキシアルケニル基として
は、例えば、カルボキシビニル基、カルボキシアリル
基、カルボキシブテニル基等が、アルケニル基として
は、例えば、ビニル基、アリル基、ブテニル基等が、ヒ
ドロキシアルケニル基としては、例えば、ヒドロキシビ
ニル基、ヒドロキシアリル基、ヒドロキシブテニル基等
を好ましく挙げることができる。The alkoxyl group includes, for example, a methoxyl group, an ethoxyl group, a propoxyl group, etc., the alkoxycarbonyl group includes, for example, a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, etc., and the acyl group includes: For example, an acetyl group, a propionyl group, a butyryl group, and the like, an alkoxycarbonylalkenyl group, for example, a methoxycarbonylvinyl group, an ethoxycarbonylallyl group, a propoxycarbonylbutenyl group, and the like, and a carboxyalkenyl group, for example, carboxyvinyl. Groups, carboxyallyl groups, carboxybutenyl groups, etc., alkenyl groups, for example, vinyl groups, allyl groups, butenyl groups, etc., and hydroxyalkenyl groups, for example, hydroxyvinyl groups, hydroxyarites. Group, and preferably a hydroxy butenyl group.
【0017】また、この様な本発明に用いる一般式
(I)で表される化合物として、好ましくは、化16で
表される2,6−ジメトキシフェノール、化17で表さ
れるシリンゴ酸、化18で表される没食子酸、化19で
表されるカフェー酸、化20で表されるピロガロール、
化21で表されるグアヤコール、化22で表されるメチ
ルシナペート、化23で表されるシリングアルデヒド、
化24で表されるメチルガレート、化25で表されるプ
ロトカテキン酸、化26で表されるアセトシリンゴ、化
27で表されるフェルラ酸、化28で表されるコニフェ
リルアルコール等が挙げられる。The compound represented by the general formula (I) used in the present invention is preferably 2,6-dimethoxyphenol represented by the chemical formula 16, sialic acid represented by the chemical formula 17, Gallic acid represented by 18, caffeic acid represented by Chemical formula 19, pyrogallol represented by Chemical formula 20,
Guaiacol represented by Chemical Formula 21, methyl synapate represented by Chemical Formula 22, syringaldehyde represented by Chemical Formula 23,
Examples include methyl gallate represented by Chemical formula 24, protocatechinic acid represented by Chemical formula 25, acetosyringo apple represented by Chemical formula 26, ferulic acid represented by Chemical formula 27, and coniferyl alcohol represented by Chemical formula 28.
【0018】[0018]
【化16】 [Chemical 16]
【0019】[0019]
【化17】 [Chemical 17]
【0020】[0020]
【化18】 [Chemical 18]
【0021】[0021]
【化19】 [Chemical 19]
【0022】[0022]
【化20】 [Chemical 20]
【0023】[0023]
【化21】 [Chemical 21]
【0024】[0024]
【化22】 [Chemical formula 22]
【0025】[0025]
【化23】 [Chemical formula 23]
【0026】[0026]
【化24】 [Chemical formula 24]
【0027】[0027]
【化25】 [Chemical 25]
【0028】[0028]
【化26】 [Chemical formula 26]
【0029】[0029]
【化27】 [Chemical 27]
【0030】[0030]
【化28】 [Chemical 28]
【0031】なお、上記化合物は何れも既知物質であ
り、一般的な製造方法により得られる。また、これらの
化合物のほとんどは合成品が市販されているので、本発
明においては、これら市販品を用いることも可能であ
る。All the above compounds are known substances and can be obtained by a general production method. In addition, since most of these compounds are commercially available as synthetic products, these commercially available products can be used in the present invention.
【0032】本発明の活性酸素消去剤には、この様な一
般式(I)で表される化合物の他にこの化合物の生理的
に許容される塩を用いることもできる。この場合、一般
式(I)で表される化合物及びその塩の1種を単独で用
いても、又は2種以上を混合して用いてもよい。For the active oxygen scavenger of the present invention, in addition to the compound represented by the general formula (I), a physiologically acceptable salt of this compound can be used. In this case, one kind of the compound represented by the general formula (I) and a salt thereof may be used alone, or two or more kinds may be mixed and used.
【0033】また、この様な塩としては、生理的に許容
されるものであれば特に限定はされないが、例えば、ナ
トリウム、カリウム等のアルカリ金属との塩、カルシウ
ム、マグネシウム等のアルカリ土類金属との塩、アンモ
ニア、トリエチルアミン、トリエタノールアミン等のア
ミン類との塩、アルギニン、リジン等の塩基性アミノ酸
類との塩等が例示できる。There are no particular restrictions on such salts as long as they are physiologically acceptable. For example, salts with alkali metals such as sodium and potassium, alkaline earth metals such as calcium and magnesium, etc. And salts with amines such as ammonia, triethylamine and triethanolamine, and salts with basic amino acids such as arginine and lysine.
【0034】<2>本発明の活性酸素消去剤を含有する
組成物 本発明の組成物は、上記活性酸素消去剤の1種あるいは
2種以上を常法により配合したものであり、具体的に
は、化粧料、医薬品、食品等が例示できる。<2> Composition Containing Active Oxygen Scavenger of the Present Invention The composition of the present invention is prepared by blending one or more active oxygen scavengers described above by a conventional method. Examples include cosmetics, pharmaceuticals, foods, and the like.
【0035】(1)化粧料 本発明の化粧料は、シワ、脱毛等の予防、改善、体臭等
の好ましくない匂いの発生を防ぐ等の目的で、上記活性
酸素消去剤を配合したものである。(1) Cosmetics The cosmetics of the present invention contain the above active oxygen scavenger for the purpose of preventing and improving wrinkles, hair loss and the like, and preventing the generation of undesirable odors such as body odor. .
【0036】上記化粧料における本発明の活性酸素消去
剤の配合量は特に限定されないが、化粧料全量に対して
0.01〜10重量%の範囲で配合されることが好まし
く、更に、0.1〜1重量%の範囲で配合されることが
より好ましい。活性酸素消去剤の配合量が0.01%未
満では、活性酸素消去剤が有するシワ改善、脱毛改善、
体臭改善等の効果が十分に得られない場合があり、10
重量%を越えて配合しても効果が頭打ちになり経済的で
ない場合が多い。The content of the active oxygen scavenger of the present invention in the above cosmetics is not particularly limited, but it is preferably in the range of 0.01 to 10% by weight with respect to the total amount of the cosmetics. More preferably, it is blended in the range of 1 to 1% by weight. When the content of the active oxygen scavenger is less than 0.01%, it improves wrinkles and hair loss of the active oxygen scavenger.
In some cases, the effect of improving body odor may not be sufficiently obtained.
Even if it is blended in excess of weight%, the effect will reach the ceiling and it is often uneconomical.
【0037】本発明が適用される化粧料としては、剤型
は特に限定されないが、例えば、化粧水、乳液、クリー
ム等の基礎化粧料、ファンデーション、アンダーメーク
アップ、白粉等のメークアップ化粧料、ヘアトニック、
ヘアリキッド、シャンプー、リンス等の頭髪用化粧料等
を挙げることができる。これらの化粧料は、上記活性酸
素消去剤を配合する以外は、通常の化粧料と同様の方法
で製造することができる。The dosage form of the cosmetics to which the present invention is applied is not particularly limited. For example, basic cosmetics such as lotion, emulsion, cream, foundation makeup, make-up cosmetics such as white powder, Hair tonic,
Hair cosmetics such as hair liquid, shampoo, and conditioner can be used. These cosmetics can be produced by the same method as that for ordinary cosmetics except that the active oxygen scavenger is added.
【0038】また、本発明の化粧料には、上記活性酸素
消去剤の他に、化粧料に一般に用いられる各種成分、例
えば、ワセリン、流動パラフィン等の炭化水素類、ホホ
バ油、カルナバワックス等のエステル類、オリーブ油、
牛脂等のトリグリセライド類、ステアリルアルコール、
ベヘニルアルコール等の高級アルコール類、ステアリン
酸、ベヘン酸等の脂肪酸類、グリセリルモノステアレー
ト、ポリオキシエチレンステアリン酸、ポリオキシエチ
レン硬化ヒマシ油、ポリオキシエチレンステアリルエー
テル等のノニオン界面活性剤、石鹸、硫酸エステル等の
アニオン界面活性剤、ステアリルアミン等のカチオン界
面活性剤、アルキルベタイン等の両性界面活性剤、グリ
セリン、プロピレングリコール等の多価アルコール類、
各種粉末成分、保湿剤、増粘剤、色剤、香料、抗酸化
剤、pH調整剤、キレート剤、防腐剤、あるいは紫外線
防御剤、抗炎症剤、美白剤等を配合することができる。In the cosmetic of the present invention, in addition to the active oxygen scavenger, various components generally used in cosmetics, for example, hydrocarbons such as petrolatum and liquid paraffin, jojoba oil, carnauba wax, etc. Esters, olive oil,
Triglycerides such as beef tallow, stearyl alcohol,
Higher alcohols such as behenyl alcohol, stearic acid, fatty acids such as behenic acid, glyceryl monostearate, polyoxyethylene stearic acid, polyoxyethylene hydrogenated castor oil, nonionic surfactants such as polyoxyethylene stearyl ether, soap, sulfuric acid Anionic surfactants such as esters, cationic surfactants such as stearylamine, amphoteric surfactants such as alkyl betaines, polyhydric alcohols such as glycerin and propylene glycol,
Various powder components, moisturizers, thickeners, colorants, fragrances, antioxidants, pH adjusters, chelating agents, preservatives, UV protectants, anti-inflammatory agents, whitening agents and the like can be added.
【0039】更に、本発明の化粧料には、本発明の活性
酸素消去剤である一般式(I)で表される化合物及び/
又はその生理的に許容される塩以外に、SOD等の活性
酸素消去作用を有する物質を配合してもよい。Further, the cosmetic of the present invention contains the compound represented by the general formula (I) which is the active oxygen scavenger of the present invention, and / or
Alternatively, in addition to a physiologically acceptable salt thereof, a substance having an active oxygen scavenging action such as SOD may be blended.
【0040】(2)医薬品 本発明の活性酸素消去剤を医薬品として製剤化する場
合、剤型は特に限定されないが、例えば、注射剤、散
剤、顆粒剤、錠剤、カプセル剤、液剤等、通常用いられ
ている各種製剤に、通常の方法に従って剤型化すること
ができる。また、剤型化に際しては、上記活性酸素消去
剤以外に、賦形剤、結合剤、崩壊剤、滑沢剤、矯味矯臭
剤、増量剤、被覆剤等の医薬品で通常用いられる任意成
分を任意の量、用いることもできる。(2) Pharmaceutical When the active oxygen scavenger of the present invention is formulated as a pharmaceutical, the dosage form is not particularly limited, but for example, injections, powders, granules, tablets, capsules, liquids, etc. are usually used. Each of the various preparations described above can be made into a dosage form according to a usual method. In addition, in formulating the dosage form, in addition to the above active oxygen scavenger, any optional ingredient commonly used in pharmaceuticals such as an excipient, a binder, a disintegrating agent, a lubricant, a flavoring agent, a bulking agent, and a coating agent is optional. Can also be used.
【0041】上記医薬品の投与量に関しては、疾患の種
類、症状、患者の年令、体重等により異なるが、成人1
人1日あたり、活性酸素消去剤の量として10mg〜1
000mgを1回ないしは数回に分けて経口投与する
か、5mg〜500mgを注射で投与するのが適当であ
る。注射剤の投与方法としては、静脈内投与、動脈内投
与、門脈内投与、腹腔内投与、筋肉内投与、皮下投与等
が例示できる。Regarding the dose of the above-mentioned pharmaceuticals, it depends on the type of disease, symptoms, age of patient, weight, etc.
As an amount of active oxygen scavenger per person per day, 10 mg to 1
It is suitable to administer 000 mg orally in one or several divided doses or to administer 5 mg to 500 mg by injection. Examples of the administration method of the injection include intravenous administration, intraarterial administration, portal vein administration, intraperitoneal administration, intramuscular administration, subcutaneous administration and the like.
【0042】(3)食品 本発明の活性酸素消去剤を食品に配合する場合、種々の
食品へ、食品で通常用いられる任意成分と共に配合でき
る。例えば、キャンディーやグミ、ゼリーといった菓子
類やジュースの様なドリンク類、パン等の主食が挙げら
れる。配合量は、食品の種類により異なるが、食品の味
を損なわずに、且つ十分な活性酸素消去効果が期待でき
る0.01〜10重量%であることが好ましく、更に、
0.1〜1重量%であることがより好ましい。(3) Food When the active oxygen scavenger of the present invention is added to food, it can be added to various foods together with optional components usually used in foods. Examples thereof include confectionery such as candy, gummy candy, jelly, drinks such as juice, and staple food such as bread. The blending amount varies depending on the type of food, but is preferably 0.01 to 10% by weight, which can expect a sufficient active oxygen scavenging effect without impairing the taste of the food.
It is more preferably 0.1 to 1% by weight.
【0043】[0043]
【作用】本発明の活性酸素消去剤として用いる、一般式
(I)で表される化合物について、2,6−ジメトキシ
フェノール、シリンゴ酸、没食子酸、カフェー酸、ピロ
ガロール、グアヤコール、メチルシナペート、シリング
アルデヒド、メチルガレート、プロトカテキン酸、アセ
トシリンゴ、フェルラ酸及びコニフェリルアルコールを
用いて、安全性及び活性酸素消去作用に関する試験を行
った。The compound represented by the general formula (I), which is used as the active oxygen scavenger of the present invention, is 2,6-dimethoxyphenol, sialic acid, gallic acid, caffeic acid, pyrogallol, guaiacol, methyl synapate, schilling. Using aldehyde, methyl gallate, protocatechuic acid, acetosyringo, ferulic acid and coniferyl alcohol, a test for safety and active oxygen scavenging action was conducted.
【0044】なお、試験に用いた上記化合物は全てアル
ドリッチ製のものであった。All the above compounds used in the test were manufactured by Aldrich.
【0045】(1)急性毒性試験(腹腔内投与) 5匹づつ13群のICR雄性マウス(体重25〜30
g)の各群に、上記各化合物を生理食塩水に溶解して1
000mg/kgの割合でそれぞれ腹腔内投与した。投
与後14日に生死を判定したが何れの群においても死亡
例を認めなかった。これより、本発明の活性酸素消去剤
の腹腔内投与によるLD50値は1000mg/kgより
大きく、安全性に優れていることがわかる。(1) Acute toxicity test (intraperitoneal administration) 13 groups of 5 ICR male mice (body weight 25-30)
In each group of g), each compound was dissolved in physiological saline to prepare 1
Each was intraperitoneally administered at a rate of 000 mg / kg. Life or death was determined 14 days after administration, but no death was observed in any of the groups. From this, it is understood that the LD 50 value by intraperitoneal administration of the active oxygen scavenger of the present invention is larger than 1000 mg / kg, which is excellent in safety.
【0046】(2)急性毒性試験(経口投与) 6匹づつ13群のICR雄性マウス(体重25〜30
g)の各群に、上記各化合物を生理食塩水に溶解して1
000mg/kgの割合でそれぞれ経口投与した。投与
後14日目に生死を判定したが何れの群においても死亡
例を認めなかった。これより、本発明の活性酸素消去剤
の経口投与によるLD50値は1000mg/kgより大
きく、安全性に優れていることがわかる。(2) Acute toxicity test (oral administration) 13 groups of 6 ICR male mice (body weight 25-30)
In each group of g), each compound was dissolved in physiological saline to prepare 1
Each was orally administered at a rate of 000 mg / kg. Live or dead was determined 14 days after administration, but no death was observed in any of the groups. From this, it is understood that the LD 50 value by oral administration of the active oxygen scavenger of the present invention is larger than 1000 mg / kg, and the safety is excellent.
【0047】(3)活性酸素消去作用の測定 化29に示す反応式に基づき、キサンチン−キサンチン
オキシダーゼ(XOD)系により活性酸素の一つである
スーパーオキシドアニオン(O2 -)を発生させ、発生し
たO2 -の生成率を亜硝酸法により測定し、この値をキサ
ンチンオキシダーゼ阻害率値で補正して活性酸素消去作
用値を求めた。[0047] (3) based on the reaction formula shown in the measurement of 29 of active oxygen scavenging action, xanthine - superoxide anions which is one of active oxygen by xanthine oxidase (XOD) system (O 2 -) to generate, generating The production rate of O 2 − was measured by the nitrous acid method, and this value was corrected with the xanthine oxidase inhibition rate value to obtain the active oxygen elimination action value.
【0048】[0048]
【化29】 [Chemical 29]
【0049】上記各化合物を各種モル濃度で含有する活
性酸素消去剤水溶液0.1mLを、65mM燐酸2水素
カリウム、35mMホウ酸ナトリウム、0.5mMED
TA2ナトリウム水溶液(以下、緩衝液Aという)0.
2mL、0.5mMキサンチン溶液0.2mL、10m
Mヒドロキシルアミン塩酸塩水溶液0.1mL、純水
0.2mLの混合液に、加えてよく撹拌し試験液とし
た。同様にして、活性酸素消去剤の代わりに純水0.1
mLを用いたコントロールの溶液を作成した。0.1 mL of an active oxygen scavenger aqueous solution containing each of the above compounds at various molar concentrations was added to 65 mM potassium dihydrogen phosphate, 35 mM sodium borate, 0.5 mM ED.
TA2 sodium aqueous solution (hereinafter referred to as buffer solution A)
2 mL, 0.5 mM xanthine solution 0.2 mL, 10 m
It was added to a mixed solution of 0.1 mL of an aqueous solution of M hydroxylamine hydrochloride and 0.2 mL of pure water and well stirred to prepare a test solution. Similarly, instead of the active oxygen scavenger, pure water 0.1
A control solution using mL was prepared.
【0050】上記試験液及びコントロール溶液に、キサ
ンチンオキシダーゼを1μL/mL濃度で含有する緩衝
液Aを0.2mL加えて撹拌した後、37℃で30分イ
ンキュベーションした。ブランクとして、上記と同様に
調整された試験液及びコントロール溶液に、キサンチン
オキシダーゼを含まない緩衝液Aを0.2mL加え、上
記と同様に処理した溶液を用意した。To the test solution and control solution, 0.2 mL of buffer solution A containing xanthine oxidase at a concentration of 1 μL / mL was added and stirred, and then incubated at 37 ° C. for 30 minutes. As a blank, 0.2 mL of xanthine oxidase-free buffer solution A was added to the test solution and control solution prepared in the same manner as above, and a solution treated in the same manner as above was prepared.
【0051】この様にして得られた各溶液のそれぞれ
に、30μMのN−1−ナフチルエチレンジアミン塩酸
塩、3mMのスルファニル酸、25%氷酢酸混液2mL
を加え、30分間室温で放置した後、各溶液について5
50nmの吸光度で活性酸素の発生量を、295nmの
吸光度で尿酸の発生量を測定した。To each of the solutions thus obtained, 2 mL of a mixed solution of 30 μM N-1-naphthylethylenediamine hydrochloride, 3 mM sulfanilic acid and 25% glacial acetic acid was added.
And leave it for 30 minutes at room temperature.
The generation amount of active oxygen was measured at the absorbance of 50 nm, and the generation amount of uric acid was measured at the absorbance of 295 nm.
【0052】得られた値を用いて、以下の式に基づき、
活性酸素消去活性値を算出した。Using the values obtained, based on the following equation,
The active oxygen scavenging activity value was calculated.
【0053】[0053]
【数1】活性酸素発生率=[(A550-3−A550-4)/
(A550-1−A550-2)]×100 尿素生成率=[(A295-3−A295-4)/(A295-1−A
295-2)]×100 活性酸素消去活性=100ー(活性酸素発生率/尿酸生
成率)×100 但し、式中の記号は、表1に示す条件で調整された各溶
液の吸光度の値とする。[ Formula 1] Active oxygen generation rate = [(A 550-3 −A 550-4 ) /
(A 550-1 -A 550-2 )] x 100 Urea production rate = [(A 295-3 -A 295-4 ) / (A 295-1 -A
295-2 )] × 100 Active oxygen scavenging activity = 100− (active oxygen generation rate / uric acid production rate) × 100 However, the symbols in the formula are the absorbance values of the respective solutions adjusted under the conditions shown in Table 1. To do.
【0054】[0054]
【表1】 [Table 1]
【0055】更に、上記方法で得られた活性酸素消去活
性値を非線形最小自乗法プログラムにかけ、IC50値
(M)を算出した。結果を表2に示す。Further, the active oxygen scavenging activity value obtained by the above method was applied to a non-linear least squares program to calculate an IC 50 value (M). The results are shown in Table 2.
【0056】[0056]
【表2】 [Table 2]
【0057】この結果から明らかなように、本発明の活
性酸素消去剤として用いる上記13種類の化合物は何れ
もIC50値が極めて低く、低濃度でも優れた活性酸素消
去活性を有していることがわかる。As is apparent from these results, all of the above 13 kinds of compounds used as the active oxygen scavenger of the present invention have extremely low IC 50 values and have excellent active oxygen scavenging activity even at low concentration. I understand.
【0058】本発明の活性酸素消去剤及びこれを含有す
る化粧料、医薬品、食品等の組成物は、その有効成分で
ある一般式(I)で表される化合物及び/又はその生理
的に許容される塩のの優れた活性酸素消去作用により、
上述したような活性酸素が関与しているとされている、
シワの形成、体臭の発生、脱毛、炎症、老人性痴呆、心
筋梗塞等の虚血性疾患、あるいはアレルギー性疾患、肝
臓障害、リューマチ等様々な疾病の治療や皮膚などの生
体老化の改善に対して有効に働くものである。The active oxygen scavenger of the present invention and the composition of cosmetics, pharmaceuticals, foods, etc., containing the active oxygen scavenger, are the active ingredient of the compound represented by the general formula (I) and / or physiologically acceptable thereof. Due to the excellent active oxygen scavenging effect of the salt
It is said that active oxygen as described above is involved,
For the treatment of various diseases such as wrinkle formation, generation of body odor, hair loss, inflammation, senile dementia, myocardial infarction, or allergic diseases, liver disorders, rheumatism, and improvement of aging of the body such as skin It works effectively.
【0059】また、本発明の活性酸素消去剤及びこれを
含有する化粧料、医薬品、食品等の組成物は、上記疾病
や生体老化の予防のためにも有効に使用できる。これ
は、活性酸素消去作用を有する成分を、予め生体内に存
在させることにより、生体内で発生した活性酸素を素早
く消去し、無毒化することができるためである。The active oxygen scavenger of the present invention and the composition of cosmetics, pharmaceuticals, foods and the like containing the same can be effectively used for the prevention of the above-mentioned diseases and biological aging. This is because the active oxygen generated in the living body can be quickly eliminated and detoxified by allowing the component having the active oxygen scavenging effect to exist in the living body in advance.
【0060】[0060]
【実施例】以下に、上記一般式(I)で表される化合物
を活性酸素消去剤として含有する食品、医薬品、化粧料
等の本発明の組成物の実施例を説明する。なお、以下に
用いる配合量は、特にことわりのない限りすべて重量部
である。EXAMPLES Examples of the composition of the present invention, such as foods, pharmaceuticals, cosmetics, etc., containing the compound represented by the general formula (I) as an active oxygen scavenger will be described below. The amounts used below are all parts by weight unless otherwise specified.
【0061】また、本発明の実施例に活性酸素消去剤と
して配合した2,6−ジメトキシフェノール、シリンゴ
酸、没食子酸、カフェー酸、ピロガロール、グアヤコー
ル、メチルシナペート、シリングアルデヒド、メチルガ
レート及びコニフェリルアルコールは、全てアルドリッ
チ製のものであった。In addition, 2,6-dimethoxyphenol, sialic acid, gallic acid, caffeic acid, pyrogallol, guaiacol, methylsynapate, syringaldehyde, methylgallate and coniferyl which have been added to the examples of the present invention as active oxygen scavengers. All alcohol was from Aldrich.
【0062】[0062]
【実施例1】 キャンディー 表3のA成分を150℃で加熱溶解し120℃に冷却し
た後、B成分を添加し撹拌して均一にした。これを成形
した後、冷却してキャンディーを得た。Example 1 Candy A component of Table 3 was melted by heating at 150 ° C., cooled to 120 ° C., and then B component was added and stirred to homogenize. After molding this, it was cooled to obtain a candy.
【0063】[0063]
【表3】 [Table 3]
【0064】[0064]
【実施例2】 グミ 表4のA成分を110℃で加熱溶解し、別途膨潤させた
B成分を添加し、更にC成分を添加し、型に流し込み、
一昼夜放置後、型から外してグミを得た。Example 2 Gummies A component of Table 4 was heated and dissolved at 110 ° C., separately swollen B component was added, and further C component was added and poured into a mold,
After leaving it for a whole day and night, I removed it from the mold and got a gummy.
【0065】[0065]
【表4】 [Table 4]
【0066】[0066]
【実施例3〜6】 ジュース 表5の成分をよく撹拌可溶化し、滅菌、無菌充填、密閉
してジュースを製造した。Examples 3 to 6 Juice The components in Table 5 were well solubilized by stirring, sterilized, aseptically filled, and sealed to produce juice.
【0067】[0067]
【表5】 [Table 5]
【0068】[0068]
【実施例7】 ホットケーキ 表6の成分をよく混ぜ合わせ、油を引いたフライパンで
焼き上げてホットケーキを作製した。Example 7 Hot Cake A hot cake was prepared by thoroughly mixing the ingredients shown in Table 6 and baking them in an oiled frying pan.
【0069】[0069]
【表6】 [Table 6]
【0070】[0070]
【実施例8】 顆粒剤 表7のA成分をよく混合し、これに100mLの20%
エタノール水溶液に溶解したB成分を練合しながら徐々
に加え造粒した。これを40℃で2昼夜送風乾燥し、篩
過、整粒し顆粒剤を得た。Example 8 Granules Component A in Table 7 was mixed well and 100 mL of 20%
The B component dissolved in an ethanol aqueous solution was gradually added while kneading and granulated. This was blow-dried at 40 ° C. for 2 days, sieved and sized to obtain granules.
【0071】[0071]
【表7】 [Table 7]
【0072】[0072]
【実施例9】 注射剤 表8の成分を溶解、濾過、滅菌し、アンプル中へ無菌充
填し封入し、注射剤を得た。Example 9 Injectable Solution The components shown in Table 8 were dissolved, filtered, sterilized, and aseptically filled into an ampoule and sealed to obtain an injectable solution.
【0073】[0073]
【表8】 [Table 8]
【0074】[0074]
【実施例10、11】 化粧水 表9の成分を室温で撹拌可溶化し、化粧水を得た。Examples 10 and 11 Lotion A lotion was obtained by solubilizing the components of Table 9 at room temperature with stirring.
【0075】[0075]
【表9】 [Table 9]
【0076】[0076]
【実施例12、13】 乳液 表10のA成分、B成分、C成分をそれぞれ80℃で加
熱溶解し、A成分にB成分を加え、更にC成分を加え粗
乳化し、ホモゲナイザーで均一に乳化し冷却して乳液を
得た。Examples 12 and 13 Emulsions The components A, B and C shown in Table 10 were heated and dissolved at 80 ° C., the components B were added to the components A, the components C were further added to obtain a coarse emulsion, and the mixture was homogenized with a homogenizer. Then, it was cooled to obtain an emulsion.
【0077】[0077]
【表10】 [Table 10]
【0078】[0078]
【実施例14】 クリーム 表11のA成分、B成分、C成分をそれぞれ80℃に加
熱溶解し、A成分にB成分を加え、更にC成分を加え、
乳化し冷却してクリームを得た。Example 14 Cream Ingredients A, B, and C in Table 11 were dissolved by heating at 80 ° C., and ingredient B was added to ingredient A, followed by addition of ingredient C.
It was emulsified and cooled to obtain a cream.
【0079】[0079]
【表11】 [Table 11]
【0080】[0080]
【発明の効果】本発明の活性酸素消去剤は活性酸素消去
作用に優れ、更に安全性も高い。従って、これを配合し
た化粧料、医薬品、食品、あるいは飲料等の組成物は活
性酸素が関与する疾患の予防と治療に長期にわたって有
効に使用することができる。The active oxygen scavenger of the present invention is excellent in the active oxygen scavenging action and has high safety. Therefore, a composition such as a cosmetic, a drug, a food, or a beverage containing the same can be effectively used for a long period of time for the prevention and treatment of diseases associated with active oxygen.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 FI 技術表示箇所 A61K 7/48 31/085 AGZ 9455−4C 31/09 9455−4C 31/11 9455−4C 31/12 9455−4C 31/19 ADS 9455−4C 31/215 ADD 9455−4C 31/235 9455−4C ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI technical display location A61K 7/48 31/085 AGZ 9455-4C 31/09 9455-4C 31/11 9455-4C 31 / 12 9455-4C 31/19 ADS 9455-4C 31/215 ADD 9455-4C 31/235 9455-4C
Claims (5)
/又はその生理的に許容される塩からなる活性酸素消去
剤。 【化1】 ただし、化1中、R1、R2は、それぞれ独立して水素原
子、水酸基又は短鎖長アルコキシル基を示し、R3は、
水素原子、カルボキシル基、短鎖長アルコキシカルボニ
ル基、ホルミル基、短鎖長アシル基、短鎖長カルボキシ
アルケニル基、短鎖長アルコキシカルボニルアルケニル
基、短鎖長アルケニル基又は短鎖長ヒドロキシアルケニ
ル基を示す。1. An active oxygen scavenger comprising a compound represented by the following general formula (I) and / or a physiologically acceptable salt thereof. [Chemical 1] However, in Chemical formula 1 , R 1 and R 2 each independently represent a hydrogen atom, a hydroxyl group or a short chain length alkoxyl group, and R 3 is
Hydrogen atom, carboxyl group, short chain length alkoxycarbonyl group, formyl group, short chain length acyl group, short chain length carboxyalkenyl group, short chain length alkoxycarbonylalkenyl group, short chain length alkenyl group or short chain length hydroxyalkenyl group. Show.
化2で表される2,6−ジメトキシフェノール、化3で
表されるシリンゴ酸、化4で表される没食子酸、化5で
表されるカフェー酸、化6で表されるピロガロール、化
7で表されるグアヤコール、化8で表されるメチルシナ
ペート、化9で表されるシリングアルデヒド、化10で
表されるメチルガレート、化11で表されるプロトカテ
キン酸、化12で表されるアセトシリンゴ、化13で表
されるフェルラ酸、化14で表されるコニフェリルアル
コールから選ばれることを特徴とする請求項1記載の活
性酸素消去剤。 【化2】 【化3】 【化4】 【化5】 【化6】 【化7】 【化8】 【化9】 【化10】 【化11】 【化12】 【化13】 【化14】 2. The compound represented by the general formula (I) is
2,6-dimethoxyphenol represented by Chemical formula 2, sialic acid represented by Chemical formula 3, gallic acid represented by Chemical formula 4, caffeic acid represented by Chemical formula 5, pyrogallol represented by Chemical formula 6, Guaiacol represented by the formula, methyl synapate represented by the chemical formula 8, syringaldehyde represented by the chemical formula 9, methyl gallate represented by the chemical formula 10, protocatechuic acid represented by the chemical formula 11, represented by the chemical formula 12. The active oxygen scavenger according to claim 1, wherein the active oxygen scavenger is selected from acetosyringo, ferulic acid represented by Chemical formula 13, and coniferyl alcohol represented by Chemical formula 14. [Chemical 2] [Chemical 3] [Chemical 4] [Chemical 5] [Chemical 6] [Chemical 7] [Chemical 8] [Chemical 9] [Chemical 10] [Chemical 11] [Chemical 12] [Chemical 13] [Chemical 14]
含有する化粧料。3. A cosmetic containing the active oxygen scavenger according to claim 1.
含有する医薬組成物。4. A pharmaceutical composition containing the active oxygen scavenger according to claim 1 or 2.
含有する食用組成物。5. An edible composition containing the active oxygen scavenger according to claim 1.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP09328694A JP3665360B2 (en) | 1994-05-02 | 1994-05-02 | Active oxygen scavenger and composition containing the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP09328694A JP3665360B2 (en) | 1994-05-02 | 1994-05-02 | Active oxygen scavenger and composition containing the same |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH07300412A true JPH07300412A (en) | 1995-11-14 |
JP3665360B2 JP3665360B2 (en) | 2005-06-29 |
Family
ID=14078174
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP09328694A Expired - Fee Related JP3665360B2 (en) | 1994-05-02 | 1994-05-02 | Active oxygen scavenger and composition containing the same |
Country Status (1)
Country | Link |
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JP (1) | JP3665360B2 (en) |
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