JP2009221153A - Complexion improving agent - Google Patents
Complexion improving agent Download PDFInfo
- Publication number
- JP2009221153A JP2009221153A JP2008067622A JP2008067622A JP2009221153A JP 2009221153 A JP2009221153 A JP 2009221153A JP 2008067622 A JP2008067622 A JP 2008067622A JP 2008067622 A JP2008067622 A JP 2008067622A JP 2009221153 A JP2009221153 A JP 2009221153A
- Authority
- JP
- Japan
- Prior art keywords
- nitric oxide
- skin
- group
- production inhibitor
- oxide production
- 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
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims abstract description 88
- 238000004519 manufacturing process Methods 0.000 claims abstract description 35
- MMXZSJMASHPLLR-UHFFFAOYSA-N pyrroloquinoline quinone Chemical class C12=C(C(O)=O)C=C(C(O)=O)N=C2C(=O)C(=O)C2=C1NC(C(=O)O)=C2 MMXZSJMASHPLLR-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000003112 inhibitor Substances 0.000 claims abstract description 22
- 238000002360 preparation method Methods 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 239000004480 active ingredient Substances 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 230000001815 facial effect Effects 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 8
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- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
本発明は、一酸化窒素産生抑制剤及びこれを含有する皮膚外用剤に関し、詳しくは、ピロロキノリンキノン誘導体及びそれらの薬理学的に許容な塩からなる一酸化窒素産生抑制剤及びこれらを含有する顔色改善用に好適な皮膚外用剤に関する。 The present invention relates to a nitric oxide production inhibitor and a topical skin preparation containing the same, and more specifically, a nitric oxide production inhibitor comprising a pyrroloquinoline quinone derivative and a pharmacologically acceptable salt thereof, and the like. The present invention relates to a skin external preparation suitable for improving the face color.
近年の生活習慣の変化により、不規則な生活、偏食、ストレス等が原因であると考えられる肌荒れ、顔色が悪い、肌つやがない等の肌トラブルを抱える人は増加する傾向にあり、今後、これらの肌トラブルに対するさらに有効な解消方法が必要になっていくと予想される。 Due to changes in lifestyle habits in recent years, the number of people with skin troubles such as rough skin, poor complexion, and lack of glossy skin, which are thought to be caused by irregular lifestyles, unbalanced diets, stress, etc., tends to increase. It is expected that more effective solutions for these skin problems will be needed.
従来の主な肌トラブル解消方法としては、美肌作用を有する様々な成分を含有する化粧料等を使用することが上げられる。これらの有効成分は、皮膚細胞に直接働き掛け代謝を促進したり、保湿作用等により老化を防ぐことにより効果を発揮している。 As a conventional main skin trouble solving method, it is possible to use cosmetics containing various components having a beautifying skin effect. These active ingredients exert their effects by directly acting on skin cells to promote metabolism and preventing aging by moisturizing action and the like.
特に、顔色が悪いことに対する解消方法としては、肌細胞への血行を促進することにより、くすみのない健康的な顔色を実現させるという試みがある。すなわち、血行を促進して皮膚細胞層へ栄養成分や水分を十分に補給し、それによって新陳代謝が活性化され、皮膚末梢での血液循環がよく保たれた結果、皮膚細胞は理想的な状態に維持され、顔面においてくすみのない美しく健康的な皮膚色が創り出せるという考えによる。しかし単なる血行の促進は、血流再還流による一酸化窒素の生成を誘発し、発生した一酸化窒素により組織がダメ−ジを受け、その形態を可逆的或いは不可逆的に変化させる場合が存する。一酸化窒素によるダメ−ジが小さければ前記形態変化は可逆的なものになり、ダメ−ジが大きすぎると不可逆的になると言われている。この様な変化は、可逆的なものであれ、不可逆的なものであれ、顔色の悪化として認識される。この様なメカニズムの顔色の悪化の改善に有用な手段は今のところ知られていない。 In particular, as a method for resolving a bad complexion, there is an attempt to realize a healthy complexion without dullness by promoting blood circulation to skin cells. In other words, blood cells are promoted to sufficiently supply nutrient components and water to the skin cell layer, thereby activating metabolism and maintaining blood circulation well at the periphery of the skin. It is based on the idea that a beautiful and healthy skin color can be created without being dull on the face. However, the mere promotion of blood circulation induces the production of nitric oxide by reperfusion of blood flow, and there is a case where the tissue is damaged by the generated nitric oxide and its form is reversibly or irreversibly changed. It is said that if the damage caused by nitric oxide is small, the shape change becomes reversible, and if the damage is too large, it becomes irreversible. Such changes, whether reversible or irreversible, are recognized as facial color deterioration. At present, no useful means for improving the complexion of such a mechanism is known.
一方、ピロロキノリンキノン誘導体、特にピロロキノリンキノン（PQQ）は、メタノ−ル資化性菌の代謝産物より単離同定された物質であり、真核生物のカビ、酵母、さらには、哺乳動物にも存在することが確認されている。その生物活性としては、細胞の増殖促進作用（特許文献１）、抗白内障作用（特許文献２）、肝臓疾患予防治療作用（特許文献３）、創傷治癒作用（特許文献４）、抗アレルギ−作用（特許文献５）、逆転写酵素阻害作用（特許文献６）及びグリオキサラ−ゼＩ阻害作用−制癌作用（特許文献７）、メラニン産生抑制作用（特許文献８）等の様々な作用が明らかとなっている。 On the other hand, pyrroloquinoline quinone derivatives, especially pyrroloquinoline quinone (PQQ), are substances isolated and identified from metabolites of methanol-utilizing bacteria, and are found in eukaryotic molds, yeasts, and mammals. Has also been confirmed to exist. As its biological activity, cell growth promoting action (Patent Document 1), anti-cataract action (Patent Document 2), liver disease prevention and treatment action (Patent Document 3), wound healing action (Patent Document 4), anti-allergic action (Patent Document 5), reverse transcriptase inhibitory action (Patent Document 6) and glyoxalase I inhibitory action-anticancer action (Patent Document 7), melanin production inhibitory action (Patent Document 8) It has become.
しかしながら、上記ピロロキノリンキノン誘導体及び／又はその薬理学的に許容される塩が一酸化窒素産生抑制作用を有することは知られておらず、これを皮膚に含有させて顔色改善効果を持たせるという報告も未だなされていない。 However, it is not known that the pyrroloquinoline quinone derivative and / or a pharmacologically acceptable salt thereof has a nitric oxide production inhibitory action, and this is contained in the skin to have a facial color improving effect. No reports have been made yet.
本発明の目的は、一酸化窒素の産生により誘発される顔色の悪化を予防乃至は改善することにある。 An object of the present invention is to prevent or ameliorate facial color deterioration induced by the production of nitric oxide.
この様な実情に鑑みて、本発明者等は、一酸化窒素の産生によって誘発される顔色の悪化を予防乃至は改善するべく一酸化窒素産生抑制作用を有する化合物探索に鋭意努力を重ねた結果、顕著な一酸化窒素産生抑制作用を有するピロロキノリンキノン誘導体を見出し、発明を完成させるに至った。
すなわち、本発明によれば、以下に示す一般式（１）で表されるピロロキノリンキノン誘導体及び／又はそれらの薬理学的に許容される塩を有効成分とする一酸化窒素産生抑制剤によって前記課題を解決できる。即ち、本発明は次に示すとおりである。
＜１＞下記一般式（１）で表されるピロロキノリンキノン誘導体及び／又はそれらの薬理学的に許容される塩を有効成分とする、一酸化窒素産生抑制剤。
In view of such circumstances, the present inventors have made extensive efforts to search for compounds having an inhibitory effect on nitric oxide production in order to prevent or improve facial color deterioration induced by nitric oxide production. The present inventors have found a pyrroloquinoline quinone derivative having a remarkable inhibitory effect on nitric oxide production and have completed the invention.
That is, according to the present invention, the nitric oxide production inhibitor comprising as an active ingredient a pyrroloquinoline quinone derivative represented by the following general formula (1) and / or a pharmaceutically acceptable salt thereof: The problem can be solved. That is, the present invention is as follows.
<1> A nitric oxide production inhibitor comprising as an active ingredient a pyrroloquinoline quinone derivative represented by the following general formula (1) and / or a pharmacologically acceptable salt thereof.
［式中、Ｒ１、Ｒ２、Ｒ３はそれぞれ独立して、短鎖長のアルキル基、アルケニル基、アラルキル基、アラアリ−ル基又はフェニル基、水素原子を表す。］
[Wherein R 1,
＜２＞前記一般式（１）で表される化合物は、ピロロキノリンキノンであることを特徴とする、請求項１に記載の一酸化窒素産生抑制剤。 <2> The nitric oxide production inhibitor according to claim 1, wherein the compound represented by the general formula (1) is pyrroloquinoline quinone.
＜３＞顔色改善に使用するためのものであって、前記顔色改善の対象となる人は、ヒト用一酸化窒素測定キットを用いて一酸化窒素量を測定したときに一酸化窒素産生量が×××の値を示す人であることを特徴とする＜１＞又は＜２＞の何れか一項に記載の一酸化窒素産生抑制剤。 <3> For use in improving the face color, the person who is the subject of the face color improvement has a production amount of nitric oxide when measuring the amount of nitric oxide using a human nitric oxide measurement kit. The nitric oxide production inhibitor according to any one of <1> or <2>, which is a person having a value of xxx.
＜４＞皮膚外用剤全量に対して＜１＞〜＜３＞何れか一項に記載の一酸化窒素産生抑制剤を０．０００１質量％〜１０質量％含有すうｒことを特徴とする、＜３＞に記載の皮膚外用剤。 <4> It contains 0.0001% by mass to 10% by mass of the nitric oxide production inhibitor according to any one of <1> to <3> with respect to the total amount of the external preparation for skin. 3> The external preparation for skin according to 3>.
＜５＞顔色改善を目的とすることを特徴とする、＜３＞又は＜４＞に記載の皮膚外用剤。 <5> The external preparation for skin according to <3> or <4>, which is intended to improve facial color.
＜６＞化粧料又は医薬部外であることを特徴とする、＜３＞〜＜５＞のいずれか一項に記載の顔色改善剤。 <6> The facial color improving agent according to any one of <3> to <5>, wherein the facial color improving agent is outside the cosmetics or pharmacy.
本発明によれば、一酸化窒素の産生によって誘発される顔色の悪化を予防乃至は改善することができる。 ADVANTAGE OF THE INVENTION According to this invention, the deterioration of the face color induced by the production of nitric oxide can be prevented or improved.
本発明の一酸化窒素産生抑制剤は、前記一般式（１）に表される化合物及び／又はその薬理学的に許容される塩を有効成分とすることを特徴とする。一般式（１）において、Ｒ１、Ｒ２、Ｒ３はそれぞれ独立して、短鎖長の、より具体的には炭素数１〜４の直鎖、分岐乃至は環状構造を有することのあるアルキル基、アルケニル基、アラルキル基、アラアリ−ル基、１環乃至は２環が独立に結合した乃至は縮合した芳香族基又は水素原子が好ましく、R１、R2、R3が共に水素原子であるピロロキノリンキノンが特に好適に例示できる。
The nitric oxide production inhibitor of the present invention comprises the compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof as an active ingredient. In the general formula (1), R 1,
一般式（１）に表される化合物のうち、好ましいものを具体的に例示すれば、ピロロキノリンキノン（化合物２）が好適に例示できる。一般式（１）で表されるピロロキノリンキノン誘導体はそのままで本発明の一酸化窒素産生抑制剤としても利用することもできるが、アルカリ金属を用いて使用することも可能である。たとえば、ナトリウム塩、カリウム塩等のアルカリ金属、カルシウム塩、マグネシウム塩等のアルカリ土類金属塩、トリエチルアミン塩、ピペリジン塩等の有機アミン塩が好ましく例示できる。 Of the compounds represented by the general formula (1), pyrroloquinoline quinone (compound 2) can be preferably exemplified by preferable examples. The pyrroloquinoline quinone derivative represented by the general formula (1) can be used as it is as the nitric oxide production inhibitor of the present invention, but can also be used using an alkali metal. For example, alkali metals such as sodium salts and potassium salts, alkaline earth metal salts such as calcium salts and magnesium salts, and organic amine salts such as triethylamine salts and piperidine salts can be preferably exemplified.
一般式（１）に表される化合物は、メタノ−ル資化性菌を培養して精製し得ることも出来るし、特許文献８（特開平８−２０５１２号公報）に記載の方法で合成し得ることも出来る。又、ピロロキノリンキノンについては、三菱ガス化学株式会社や同仁化学株式会社より市販されているものも存し、この様な市販品を購入し利用することも出来る。斯くして得られた一般式（１）に表される化合物及び／又は整理的に許容されるそれらの塩は、一酸化窒素が生体内に過剰に発生し、不可逆的皮膚組織変化を誘導することを防ぐ作用を有する。この様な作用を得るためには、前記一般式（１）に表される化合物及び／又はその薬理学的に許容される塩を成人１人１日あたり、０．１ｍｇ〜１０ｇ一回乃至は数回に分けて、経口的に、或いは、経皮的に投与することが好ましい。 The compound represented by the general formula (1) can be purified by culturing methanol-assimilating bacteria, or synthesized by the method described in Patent Document 8 (Japanese Patent Laid-Open No. Hei 8-205512). You can also get it. In addition, pyrroloquinoline quinone is commercially available from Mitsubishi Gas Chemical Co., Inc. and Dojin Chemical Co., Ltd., and such a commercial product can be purchased and used. The compounds represented by the general formula (1) thus obtained and / or their salts that are acceptable in an orderly manner cause excessive generation of nitric oxide in the living body and induce irreversible skin tissue changes. It has an action to prevent this. In order to obtain such an action, the compound represented by the general formula (1) and / or the pharmacologically acceptable salt thereof may be used in an amount of 0.1 mg to 10 g per day per adult. It is preferable to administer orally or transdermally in several divided portions.
本発明の皮膚外用剤においては、前記一酸化窒素産生抑制剤以外に通常の皮膚外用剤で使用される、任意の成分を含有することが出来る。この様な任意の成分としては、例えば、マカデミアナッツ油、アボガド油、トウモロコシ油、オリ−ブ油、ナタネ油、ゴマ油、ヒマシ油、サフラワ−油、綿実油、ホホバ油、ヤシ油、パーム油、液状ラノリン、硬化ヤシ油、硬化油、モクロウ、硬化ヒマシ油、ミツロウ、キャンデリラロウ、カルナウバロウ、イボタロウ、ラノリン、還元ラノリン、硬質ラノリン、ホホバロウ等のオイル、ワックス類；流動パラフィン、スクワラン、プリスタン、オゾケライト、パラフィン、セレシン、ワセリン、マイクロクリスタリンワックス等の炭化水素類；オレイン酸、イソステアリン酸、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、ベヘン酸、ウンデシレン酸等の高級脂肪酸類；セチルアルコ−ル、ステアリルアルコ−ル、イソステアリルアルコ−ル、ベヘニルアルコ−ル、オクチルドデカノ−ル、ミリスチルアルコ−ル、セトステアリルアルコ−ル等の高級アルコール等；イソオクタン酸セチル、ミリスチン酸イソプロピル、イソステアリン酸ヘキシルデシル、アジピン酸ジイソプロピル、セバチン酸ジ−２−エチルヘキシル、乳酸セチル、リンゴ酸ジイソステアリル、ジ−２−エチルヘキサン酸エチレングリコ−ル、ジカプリン酸ネオペンチルグリコ−ル、ジ−２−ヘプチルウンデカン酸グリセリン、トリ−２−エチルヘキサン酸グリセリン、トリ−２−エチルヘキサン酸トリメチロ−ルプロパン、トリイソステアリン酸トリメチロ−ルプロパン、テトラ−２−エチルヘキサン酸ペンタンエリトリット等の合成エステル油類；ジメチルポリシロキサン、メチルフェニルポリシロキサン、ジフェニルポリシロキサン等の鎖状ポリシロキサン；オクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサン、ドデカメチルシクロヘキサンシロキサン等の環状ポリシロキサン；アミノ変性ポリシロキサン、ポリエーテル変性ポリシロキサン、アルキル変性ポリシロキサン、フッ素変性ポリシロキサン等の変性ポリシロキサン等のシリコーン油等の油剤類；脂肪酸セッケン（ラウリン酸ナトリウム、パルミチン酸ナトリウム等）、ラウリル硫酸カリウム、アルキル硫酸トリエタノ−ルアミンエーテル等のアニオン界面活性剤類；塩化ステアリルトリメチルアンモニウム、塩化ベンザルコニウム、ラウリルアミンオキサイド等のカチオン界面活性剤類；イミダゾリン系両性界面活性剤（２−ココイル−２−イミダゾリニウムヒドロキサイド−１−カルボキシエチロキシ２ナトリウム塩等）、ベタイン系界面活性剤（アルキルベタイン、アミドベタイン、スルホベタイン等）、アシルメチルタウリン等の両性界面活性剤類；ソルビタン脂肪酸エステル類（ソルビタンモノステアレート、セスキオレイン酸ソルビタン等）、グリセリン脂肪酸類（モノステアリン酸グリセリン等）、プロピレングリコール脂肪酸エステル類（モノステアリン酸プロピレングリコール等）、硬化ヒマシ油誘導体、グリセリンアルキルエーテル、ＰＯＥソルビタン脂肪酸エステル類（ＰＯＥソルビタンモノオレエ−ト、モノステアリン酸ポリオキエチレンソルビタン等）、ＰＯＥソルビット脂肪酸エステル類（ＰＯＥ−ソルビットモノラウレ−ト等）、ＰＯＥグリセリン脂肪酸エステル類（ＰＯＥ−グリセリンモノイソステアレ−ト等）、ＰＯＥ脂肪酸エステル類（ポリエチレングリコ−ルモノオレ−ト、ＰＯＥジステアレ−ト等）、ＰＯＥアルキルエ−テル類（ＰＯＥ２−オクチルドデシルエ−テル等）、ＰＯＥアルキルフェニルエ−テル類（ＰＯＥノニルフェニルエ−テル等）、プルロニック型類、ＰＯＥ・ＰＯＰアルキルエーテル類（ＰＯＥ・ＰＯＰ２−デシルテトラデシルエ−テル等）、テトロニック類、ＰＯＥヒマシ油・硬化ヒマシ油誘導体（ＰＯＥヒマシ油、ＰＯＥ硬化ヒマシ油等）、ショ糖脂肪酸エステル、アルキルグルコシド等の非イオン界面活性剤類；ポリエチレングリコ−ル、グリセリン、１，３−ブチレングリコール、エリスリト−ル、ソルビト−ル、キシリト−ル、マルチト−ル、プロピレングリコ−ル、ジプロピレングリコ−ル、ジグリセリン、イソプレングリコ−ル、１，２−ペンタンジオ−ル、２，４−ヘキサンジオ−ル、１，２−ヘキサンジオ−ル、１，２−オクタンジオ−ル等の多価アルコ−ル類；ピロリドンカルボン酸ナトリウム、乳酸、乳酸ナトリウム等の保湿成分類；表面を処理されていても良い、マイカ、タルク、カオリン、合成雲母、炭酸カルシウム、炭酸マグネシウム、無水ケイ酸（シリカ）、酸化アルミニウム、硫酸バリウム等の粉体類、；表面を処理されていても良い、ベンガラ、黄酸化鉄、黒酸化鉄、酸化コバルト、群青、紺青、酸化チタン、酸化亜鉛の無機顔料類；表面を処理されていても良い、雲母チタン、魚燐箔、オキシ塩化ビスマス等のパ−ル剤類；レ−キ化されていても良い赤色２０２号、赤色２２８号、赤色２２６号、黄色４号、青色４０４号、黄色５号、赤色５０５号、赤色２３０号、赤色２２３号、橙色２０１号、赤色２１３号、黄色２０４号、黄色２０３号、青色１号、緑色２０１号、紫色２０１号、赤色２０４号等の有機色素類；ポリエチレン末、ポリメタクリル酸メチル、ナイロン粉末、オルガノポリシロキサンエラストマ−等の有機粉体類；パラアミノ安息香酸系紫外線吸収剤；アントラニル酸系紫外線吸収剤；サリチル酸系紫外線吸収剤、；桂皮酸系紫外線吸収剤、；ベンゾフェノン系紫外線吸収剤；糖系紫外線吸収剤；２−（２’−ヒドロキシ−５’−ｔ−オクチルフェニル)ベンゾトリアゾ−ル、４−メトキシ−４’−ｔ−ブチルジベンゾイルメタン等の紫外線吸収剤類；エタノール、イソプロパノ−ル等の低級アルコ−ル類；ビタミンＡ又はその誘導体、ビタミンＢ6塩酸塩、ビタミンＢ6トリパルミテ−ト、ビタミンＢ6ジオクタノエ−ト、ビタミンＢ2又はその誘導体、ビタミンＢ12、ビタミンＢ15又はその誘導体等のビタミンＢ類；α−トコフェロ−ル、β−トコフェロ−ル、γ−トコフェロ−ル、ビタミンＥアセテ−ト等のビタミンＥ類、ビタミンＤ類、ビタミンＨ、パントテン酸、パンテチン、ピロロキノリンキノン等のビタミン類等；フェノキシエタノール等の抗菌剤などが好ましく例示できる。 In the external preparation for skin of the present invention, any component used in normal external preparation for skin can be contained in addition to the nitric oxide production inhibitor. Such optional ingredients include, for example, macadamia nut oil, avocado oil, corn oil, olive oil, rapeseed oil, sesame oil, castor oil, safflower oil, cottonseed oil, jojoba oil, coconut oil, palm oil, liquid lanolin , Hardened coconut oil, hardened oil, molasses, hardened castor oil, beeswax, candelilla wax, carnauba wax, ibotarou, lanolin, reduced lanolin, hard lanolin, jojoba wax, oils, waxes; , Hydrocarbons such as ceresin, petrolatum, microcrystalline wax; higher fatty acids such as oleic acid, isostearic acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, undecylenic acid; cetyl alcohol, stearyl alcohol Le, isostear Higher alcohols such as alcohol, behenyl alcohol, octyldodecanol, myristyl alcohol and cetostearyl alcohol; cetyl isooctanoate, isopropyl myristate, hexyldecyl isostearate, diisopropyl adipate, sebacic acid Di-2-ethylhexyl, cetyl lactate, diisostearyl malate, ethylene glycol di-2-ethylhexanoate, neopentyl glycol dicaprate, glycerin di-2-heptylundecanoate, tri-2-ethylhexane Synthetic ester oils such as glyceryl acid, tri-2-ethylhexanoic acid trimethylolpropane, triisostearic acid trimethylolpropane, tetra-2-ethylhexanoic acid pentane erythritol; dimethylpolysiloxane, methylphenyl Linear polysiloxanes such as siloxane and diphenylpolysiloxane; cyclic polysiloxanes such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexanesiloxane; amino-modified polysiloxane, polyether-modified polysiloxane, alkyl-modified polysiloxane, Oil agents such as silicone oils such as modified polysiloxanes such as fluorine-modified polysiloxanes; Anionic surfactants such as fatty acid soaps (sodium laurate, sodium palmitate, etc.), potassium lauryl sulfate, triethanolamine ether alkyl sulfates; Cationic surfactants such as stearyltrimethylammonium, benzalkonium chloride and laurylamine oxide; imidazoline-based amphoteric surfactants (2-cocoyl-2-imi Amphoteric surfactants such as dacolinium hydroxide-1-carboxyethyloxy disodium salt), betaine surfactants (alkylbetaine, amidebetaine, sulfobetaine, etc.), acylmethyltaurine; sorbitan fatty acid esters ( Sorbitan monostearate, sorbitan sesquioleate, etc.), glycerin fatty acids (such as glyceryl monostearate), propylene glycol fatty acid esters (such as propylene glycol monostearate), hardened castor oil derivatives, glycerin alkyl ether, POE sorbitan fatty acid ester (POE sorbitan monooleate, polyoxyethylene sorbitan monostearate, etc.), POE sorbite fatty acid esters (POE-sorbitol monolaurate, etc.), POE glycerin fatty acid Steals (POE-glycerin monoisostearate, etc.), POE fatty acid esters (polyethylene glycol monooleate, POE distearate, etc.), POE alkyl ethers (POE2-octyldodecyl ether, etc.), POE alkylphenyl ethers (POE nonylphenyl ether, etc.), Pluronic types, POE / POP alkyl ethers (POE / POP2-decyltetradecyl ether, etc.), Tetronics, POE castor oil / cured Nonionic surfactants such as castor oil derivatives (POE castor oil, POE hydrogenated castor oil, etc.), sucrose fatty acid esters, alkylglucosides; polyethylene glycol, glycerin, 1,3-butylene glycol, erythritol, sorbitol -L, Xylitol, Multi-Tole, Propile Glycol, dipropylene glycol, diglycerin, isoprene glycol, 1,2-pentanediol, 2,4-hexanediol, 1,2-hexanediol, 1,2-octanediol, etc. Moisturizing ingredients such as sodium pyrrolidone carboxylate, lactic acid, sodium lactate; surface treated mica, talc, kaolin, synthetic mica, calcium carbonate, magnesium carbonate, silicic anhydride (Silica), powders such as aluminum oxide and barium sulfate; inorganic pigments such as bengara, yellow iron oxide, black iron oxide, cobalt oxide, ultramarine, bitumen, titanium oxide, zinc oxide, which may be treated on the surface PAR agents such as titanium mica, fish phosphorus foil, bismuth oxychloride, etc. whose surface may be treated; red 202, which may be laked, Red 228, Red 226, Yellow 4, Blue 404, Yellow 5, Red 505, Red 230, Red 223, Orange 201, Red 213, Yellow 204, Yellow 203, Blue 1 No., green 201, purple 201, red 204, etc .; organic powders such as polyethylene powder, polymethyl methacrylate, nylon powder, organopolysiloxane elastomer; paraaminobenzoic acid UV absorbers; Anthranilic acid UV absorbers; salicylic acid UV absorbers; cinnamic acid UV absorbers; benzophenone UV absorbers; sugar UV absorbers; 2- (2′-hydroxy-5′-t-octylphenyl) UV absorbers such as benzotriazole and 4-methoxy-4'-t-butyldibenzoylmethane; low such as ethanol and isopropanol Class B alcohols such as vitamin A or derivatives thereof, vitamin B6 hydrochloride, vitamin B6 tripalmitate, vitamin B6 dioctanoate, vitamin B2 or derivatives thereof, vitamin B12, vitamin B15 or derivatives thereof, etc. -Vitamin E such as tocopherol, β-tocopherol, γ-tocopherol, vitamin E acetate, vitamin D, vitamin H, pantothenic acid, panthetin, pyrroloquinoline quinone, etc .; phenoxyethanol An antibacterial agent such as
これらの必須成分、任意成分を常法に従って処理し、ロ−ション、乳液、エッセンス、クリ−ム、パック化粧料、洗浄料などに加工することにより、本発明の皮膚外用剤は製造できる。本発明の皮膚外用剤としては、皮膚に外用で適用されるものであれば特段の限定はなく応用でき、例えば、医薬部外品を含む化粧料、皮膚外用医薬、皮膚外用雑貨等が好ましく例示できる。 The skin external preparation of this invention can be manufactured by processing these essential components and arbitrary components according to a conventional method and processing them into lotions, emulsions, essences, creams, pack cosmetics, cleansing agents and the like. The skin external preparation of the present invention can be applied without particular limitation as long as it is applied externally to the skin, for example, cosmetics including quasi-drugs, skin external medicines, skin external goods and the like are preferable examples it can.
以下に、本発明について、実施例を挙げて更に詳細に説明を加えるが、本発明がかかる実施例にのみ、限定されないことは言うまでもない。 Hereinafter, the present invention will be described in more detail with reference to examples, but it is needless to say that the present invention is not limited to such examples.
＜本発明の一酸化窒素産生抑制剤である、ピロロキノリンキノン＞
本発明における一酸化窒素産生抑制作用を評価するために用いたピロロキノリンキノンは、同仁化学株式会社より購入し、使用した。
<Pyrroquinoline quinone which is a nitric oxide production inhibitor of the present invention>
The pyrroloquinoline quinone used for evaluating the inhibitory effect on nitric oxide production in the present invention was purchased from Dojin Chemical Co., Ltd.
＜本発明の一酸化窒素産生抑制作用＞
マウス由来のマクロファージ様細胞であるRAW264.7（１０６／ｍｌ）を９６ウェルプレートに播種し、一夜培養後、インターフェロンγ（ＩＦＮγ）（１０ng／ｍｌ）（R&D Systems，Inc.）とリポポリサッカライド（ＬＰＳ）（１０μｇ／ｍｌ）（List Biological Laboratories，Inc）およびＰＱＱを添加し、インキュベーターで３７℃、２４時間培養した。培養液（１００μｌ）にGriess試薬（１００μｌ）(Jounal of Leukocyte Biology Volume 54，August 1993，199-124)を加えて、５５０ｎｍでの吸光度の変化により、生成されたＮＯ2 の量を測定し、ＮＯ合成酵素の阻害活性とした。
<Nitric oxide production inhibitory action of the present invention>
RAW264.7 (10 6 / ml), a macrophage-like cell derived from a mouse, was seeded in a 96-well plate, cultured overnight, then interferon γ (IFNγ) (10 ng / ml) (R & D Systems, Inc.) and lipopolysaccharide. (LPS) (10 μg / ml) (List Biological Laboratories, Inc) and PQQ were added, and cultured in an incubator at 37 ° C. for 24 hours. Griess reagent (100 μl) (Jounal of Leukocyte Biology Volume 54, August 1993, 199-124) is added to the culture solution (100 μl), and the amount of NO 2 produced is measured by the change in absorbance at 550 nm. Synthetic enzyme inhibitory activity.
この様に評価された、本発明の一酸化窒素産生抑制剤の一酸化窒素産生抑制作用を後記の図１に示す。この図より、本発明の一酸化窒素産生抑制剤は優れた一酸化窒素産生抑制作用を有することがわかる。
The nitric oxide production inhibitory action of the present nitric oxide production inhibitor evaluated in this manner is shown in FIG. This figure shows that the nitric oxide production inhibitor of the present invention has an excellent nitric oxide production inhibitory action.
以下に示す処方に従って、本発明の皮膚外用剤である化粧料（ロ−ション）を作製した。即ち、処方成分を８０℃に加熱し、撹拌し、溶解させ、撹拌冷却し、ロ−ション１を得た。 A cosmetic (lotion) which is an external preparation for skin of the present invention was prepared according to the formulation shown below. That is, the ingredients were heated to 80 ° C., stirred, dissolved, stirred and cooled to obtain Lotion 1.
＜評価＞
実施例２のローションについて、顔色改善効果を調べた。比較の為、ピロロキノリンキノンを水に置換した比較例１も同様に製造した。無作為に集めた顔色の優れない自覚のあるパネラー２０名を２群に分け、１群にはローション１を、残りの１群には比較例１を渡し、朝晩２回３０日連日使用してもらった。使用終了後４８時間にアンケートで顔色の改善度合いを、スコア０：改善無し、スコア１：殆ど改善を感じない、スコア２：少し改善を感じる、スコア３：明確に改善を感じるの４段階評価を行い、使用前と、使用後４８時間にコニカミノルタ色彩色差計ＣＲ−４００で測色を行い、ΔＬを求めた。結果を表２、表３に示す。これより、本発明の皮膚外用剤であるローション１により、顔色が改善していることがわかる。
<Evaluation>
The lotion of Example 2 was examined for the effect of improving the face color. For comparison, Comparative Example 1 in which pyrroloquinoline quinone was replaced with water was also produced in the same manner. Randomly collected 20 panelists with poor facial color and consciousness were divided into 2 groups. One group was given lotion 1 and the other group was given comparative example 1, which was used twice a day in the morning and evening for 30 days. received. 48 hours after the end of use, the questionnaire shows the degree of improvement in facial color, score 0: no improvement, score 1: almost no improvement, score 2: slight improvement, score 3: clear improvement The color was measured with a Konica Minolta color difference meter CR-400 before use and 48 hours after use to obtain ΔL. The results are shown in Tables 2 and 3. From this, it can be seen that the lotion 1 which is an external preparation for skin of the present invention improves the face color.
本発明は化粧料などの皮膚外用剤に応用できる。 The present invention can be applied to skin external preparations such as cosmetics.
Claims (6)
［式中、Ｒ１、Ｒ２、Ｒ３はそれぞれ独立して、短鎖長のアルキル基、アルケニル基、アラルキル基、アラアリ−ル基又はフェニル基、水素原子を表す。］ A nitric oxide production inhibitor comprising a pyrroloquinoline quinone derivative represented by the following general formula (1) and / or a pharmacologically acceptable salt thereof as an active ingredient.
[Wherein R 1, R 2 and R 3 each independently represents a short-chain alkyl group, alkenyl group, aralkyl group, araryl group or phenyl group, or a hydrogen atom. ]
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012224625A (en) * | 2011-04-07 | 2012-11-15 | Rohto Pharmaceutical Co Ltd | Composition for external application |
| JP2014131993A (en) * | 2012-12-04 | 2014-07-17 | Rohto Pharmaceut Co Ltd | External composition |
| EP2717693A4 (en) * | 2011-06-06 | 2015-06-24 | Us Cosmeceutechs Llc | Skin treatments containing pyrroloquinoline quinine (pqq) esters and methods of preparation and use thereof |
-
2008
- 2008-03-17 JP JP2008067622A patent/JP2009221153A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012224625A (en) * | 2011-04-07 | 2012-11-15 | Rohto Pharmaceutical Co Ltd | Composition for external application |
| JP2014198721A (en) * | 2011-04-07 | 2014-10-23 | ロート製薬株式会社 | External composition |
| JP2017025110A (en) * | 2011-04-07 | 2017-02-02 | ロート製薬株式会社 | External composition |
| EP2717693A4 (en) * | 2011-06-06 | 2015-06-24 | Us Cosmeceutechs Llc | Skin treatments containing pyrroloquinoline quinine (pqq) esters and methods of preparation and use thereof |
| US10799441B2 (en) | 2011-06-06 | 2020-10-13 | Pcr Technology Holdings, Lc | Skin treatments containing pyrroloquinoline quinone (PQQ) esters and methods of preparation and use thereof |
| JP2014131993A (en) * | 2012-12-04 | 2014-07-17 | Rohto Pharmaceut Co Ltd | External composition |
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