JP2021050179A - Hyaluronic acid production promoter and wrinkle improver or skin external preparation containing the same - Google Patents
Hyaluronic acid production promoter and wrinkle improver or skin external preparation containing the same Download PDFInfo
- Publication number
- JP2021050179A JP2021050179A JP2019175740A JP2019175740A JP2021050179A JP 2021050179 A JP2021050179 A JP 2021050179A JP 2019175740 A JP2019175740 A JP 2019175740A JP 2019175740 A JP2019175740 A JP 2019175740A JP 2021050179 A JP2021050179 A JP 2021050179A
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- JP
- Japan
- Prior art keywords
- extract
- hyaluronic acid
- acid production
- production promoter
- diacetylspermidine
- 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.)
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Abstract
Description
本発明は、アセチルスペルミン、アセチルスペルミジン、ジアセチルスペルミジンから選択される１以上を有効成分として含有するヒアルロン酸産生促進剤に関する。 The present invention relates to a hyaluronic acid production promoter containing one or more selected from acetylspermine, acetylspermidine, and diacetylspermidine as an active ingredient.
ヒアルロン酸は、β−Ｄ−Ｎ−アセチルグルコサミンとβ−Ｄ−グルクロン酸が交互に結合した直鎖状の高分子多糖であり、哺乳動物の皮膚、血管、関節、眼球硝子体などの結合組織に広く分布するグリコサミノグリカンの一種である。ヒアルロン酸の各組織での機能としては、その高い水分保持能力、粘弾性や結合性の高さからコラーゲンとともに組織の潤滑性と柔軟性、細胞の保持などに深く関与している。 Hyaluronic acid is a linear high molecular weight polysaccharide in which β-DN-acetylglucosamine and β-D-glucuronic acid are alternately bound, and is a connective tissue such as mammalian skin, blood vessels, joints, and vitreous eyeball. It is a type of glycosaminoglycan that is widely distributed in Japan. As the function of hyaluronic acid in each tissue, it is deeply involved in the lubricity and flexibility of the tissue, cell retention, etc. together with collagen due to its high water retention ability, viscoelasticity and high binding property.
皮膚組織において、ヒアルロン酸は皮膚の保水性や弾力性に大きく関与している。しかし加齢や外的ストレスにより、皮膚中のヒアルロン酸は減少し、その結果、乾燥、かさつきをはじめとしたさまざまな肌荒れ、小じわの形成、皮膚のたるみ、はりの消失等といった皮膚の老化をもたらすと言われている。すなわち、生体内のヒアルロン酸の蓄積を促進することによって、ヒアルロン酸の産生量の減少により生じるしわ・肌荒れ・皮膚バリア機能の低下などを改善することができる。 In skin tissue, hyaluronic acid is greatly involved in the water retention and elasticity of the skin. However, due to aging and external stress, hyaluronic acid in the skin decreases, and as a result, various rough skin such as dryness and dryness, formation of fine wrinkles, sagging of the skin, disappearance of swelling, etc. It is said to bring. That is, by promoting the accumulation of hyaluronic acid in the living body, it is possible to improve wrinkles, rough skin, deterioration of skin barrier function, etc. caused by a decrease in the amount of hyaluronic acid produced.
これまでに皮膚のしわなど、ヒアルロン酸の減少に伴う障害に対してヒアルロン酸を直接、外用剤、あるいは注射剤として投与する試みがなされてきた。しかし、ヒアルロン酸は高分子の多糖成分であることから経皮吸収は少なく、さらに注射剤による補充療法は、医師の処方が必要であり、苦痛を伴う治療であることから日常的に使える手法ではない。また、生体内でヒアルロン酸の合成を促進したり（特許文献１：特開２００１−１６３７９４）、分解酵素であるヒアルロニダーゼを阻害する技術（特許文献２：特開２０００−１７８１９６）が、これまでに開示されてきた。しかし、効果、安全性、供給、品質、安定性などの面から不十分であり、新規なヒアルロン酸産生促進剤の開発が望まれていた。 So far, attempts have been made to directly administer hyaluronic acid as an external preparation or an injection for disorders associated with a decrease in hyaluronic acid such as wrinkles on the skin. However, since hyaluronic acid is a high molecular weight polysaccharide component, it is less percutaneously absorbed, and replacement therapy with injections requires a doctor's prescription and is a painful treatment, so it is a method that can be used on a daily basis. Absent. In addition, techniques for promoting the synthesis of hyaluronic acid in vivo (Patent Document 1: Japanese Patent Application Laid-Open No. 2001-163794) and inhibiting hyaluronidase, which is a degrading enzyme (Patent Document 2: Japanese Patent Application Laid-Open No. 2000-178196), have been used so far. It has been disclosed. However, it is insufficient in terms of efficacy, safety, supply, quality, stability, etc., and development of a new hyaluronic acid production promoter has been desired.
また、特許文献３（特開２０１２−０４６５４４号公報）には、ポリアミンであるプトレシン、スペルミジン、スペルミンにヒアルロン酸産生促進作用があることが記載されているが、アセチルスペルミン、アセチルスペルミジン、ジアセチルスペルミジンのヒアルロン酸産生促進作用については知られていない。 Further, Patent Document 3 (Japanese Unexamined Patent Publication No. 2012-046544) describes that the polyamines putrescine, spermidine, and spermine have a hyaluronic acid production-promoting effect. It is not known about the hyaluronic acid production promoting action.
本発明は、新規なヒアルロン酸産生促進剤を提供することを課題とする。 An object of the present invention is to provide a novel hyaluronic acid production promoter.
本発明の主な構成は、次のとおりである。
１．アセチルスペルミン、アセチルスペルミジン、ジアセチルスペルミジンから選択される１以上を有効成分として含有するヒアルロン酸産生促進剤。
２．アセチルスペルミン、ジアセチルスペルミジンから選択される１以上を有効成分として含有する表皮におけるヒアルロン酸産生促進剤。
３．アセチルスペルミン、アセチルスペルミジン、ジアセチルスペルミジンから選択される１以上を有効成分として含有する真皮におけるヒアルロン酸産生促進剤。
４．１．〜３．のいずれかに記載のヒアルロン酸産生促進剤を含有するしわ改善剤。
５．１．〜３．のいずれかに記載のヒアルロン酸産生促進剤を含有する皮膚外用剤。
The main configuration of the present invention is as follows.
1. 1. A hyaluronic acid production promoter containing at least one selected from acetylspermine, acetylspermidine, and diacetylspermidine as an active ingredient.
2. A hyaluronic acid production promoter in the epidermis containing one or more selected from acetylspermine and diacetylspermidine as an active ingredient.
3. 3. A hyaluronic acid production promoter in the dermis containing one or more selected from acetylspermine, acetylspermidine, and diacetylspermidine as an active ingredient.
4.1. ~ 3. A wrinkle improving agent containing the hyaluronic acid production promoter according to any one of the above.
5.1. ~ 3. An external preparation for skin containing the hyaluronic acid production promoter according to any one of the above.
本発明で用いるアセチルスペルミン、アセチルスペルミジン、ジアセチルスペルミジンは、これまでにヒアルロン酸産生促進作用があることが知られていたプトレシン、スペルミジン、スペルミンと同等もしくは同等以上のヒアルロン酸産生促進活性を有している。特に、アセチルスペルミン、ジアセチルスペルミジンは表皮におけるヒアルロン酸産生促進作用に優れ、アセチルスペルミン、アセチルスペルミジン、ジアセチルスペルミジンは真皮におけるヒアルロン酸産生促進作用に優れている。アセチルスペルミン、アセチルスペルミジン、ジアセチルスペルミジンの１種以上を有効成分として含有するヒアルロン酸産生促進剤及びこれを利用したしわ改善剤又は皮膚外用剤を提供できる。 The acetylspermine, acetylspermidine, and diacetylspermidine used in the present invention have hyaluronic acid production-promoting activity equal to or higher than that of putrescine, spermidine, and spermine, which have been known to have a hyaluronic acid production-promoting effect. There is. In particular, acetylspermine and diacetylspermidine are excellent in promoting hyaluronic acid production in the epidermis, and acetylspermine, acetylspermidine and diacetylspermidine are excellent in promoting hyaluronic acid production in the dermis. It is possible to provide a hyaluronic acid production promoter containing at least one of acetylspermine, acetylspermidine, and diacetylspermidine as an active ingredient, and a wrinkle improving agent or an external preparation for skin using the same.
プトレシン、スペルミジン、スペルミンの構造式を、それぞれ下記（１）〜（３）に示す。 The structural formulas of putrescine, spermidine, and spermine are shown in (1) to (3) below, respectively.
本発明は、上記ポリアミンのアセチル誘導体である、アセチルスペルミン、アセチルスペルミジン、ジアセチルスペルミジンから選択される１以上を有効成分として含有するヒアルロン酸産生促進剤、アセチルスペルミン、ジアセチルスペルミジンから選択される１以上を有効成分として含有する表皮におけるヒアルロン酸産生促進剤、アセチルスペルミン、アセチルスペルミジン、ジアセチルスペルミジンから選択される１以上を有効成分として含有する真皮におけるヒアルロン酸産生促進剤、及びこれらを利用したしわ改善剤、皮膚外用剤に関する。 The present invention comprises one or more selected from hyaluronic acid production promoters, acetylspermine, and diacetylspermidine containing one or more selected from acetylspermine, acetylspermidine, and diacetylspermidine, which are acetyl derivatives of the polyamine, as active ingredients. A hyaluronic acid production promoter in the epidermis containing as an active ingredient, a hyaluronic acid production promoter in the dermis containing one or more selected from acetylspermine, acetylspermidine, and diacetylspermidine as an active ingredient, and a wrinkle improving agent using these. Regarding external preparations for skin.
本発明のヒアルロン酸産生促進剤におけるアセチルスペルミン、アセチルスペルミジン、ジアセチルスペルミジンそれぞれの濃度は、ヒアルロン酸の産生を促進できる範囲内であれば特に制限されないが、いずれも０．０１μｇ／ｍＬ以上２００μｇ／ｍＬ以下であることが好ましい。 The concentrations of acetylspermine, acetylspermidine, and diacetylspermidine in the hyaluronic acid production promoter of the present invention are not particularly limited as long as they can promote hyaluronic acid production, but all of them are 0.01 μg / mL or more and 200 μg / mL. The following is preferable.
本発明のヒアルロン酸産生促進剤を直接化粧料成分として配合することにより、しわ改善剤を調製することができる。このしわ改善剤には、植物油、脂肪酸類、高級アルコール、シリコーン類、界面活性成分、水溶性合成高分子、増粘成分、粉体成分、保湿成分、紫外線吸収剤、紫外線遮蔽物、香料、金属キレート剤、ｐＨ調整剤などの公知の化粧料用成分を含有させることができる。さらには、抗炎症成分、活性酸素消去成分、血行促進成分、美白成分あるいは、その他の公知の添加剤である有効成分を配合することもできる。 A wrinkle improving agent can be prepared by directly blending the hyaluronic acid production promoter of the present invention as a cosmetic ingredient. These wrinkle improvers include vegetable oils, fatty acids, higher alcohols, silicones, surfactants, water-soluble synthetic polymers, thickening components, powder components, moisturizing components, UV absorbers, UV shields, fragrances, and metals. Known cosmetic ingredients such as chelating agents and pH adjusters can be contained. Furthermore, an anti-inflammatory component, an active oxygen scavenging component, a blood circulation promoting component, a whitening component, or an active ingredient which is another known additive can also be blended.
本発明のしわ改善剤は、化粧料、医薬部外品、医薬品を含むものであって、通常使用される製剤化方法にしたがって製造することができ、植物油のような油脂類、高級脂肪酸、高級アルコール、シリコーン、アニオン界面活性剤、カチオン界面活性剤、両性界面活性剤、非イオン界面活性剤、防腐剤、糖類、金属イオン封鎖剤、水溶性高分子のような高分子、増粘剤、粉体成分、紫外線吸収剤、紫外線遮断剤、ヒアルロン酸のような保湿剤、香料、ｐＨ調整剤等を含有させることができる。ビタミン類、皮膚賦活剤、血行促進剤、常在菌コントロール剤、活性酸素消去剤、抗炎症剤、美白剤、殺菌剤等の他の薬効成分、生理活性成分を含有させることもできる。 The wrinkle improving agent of the present invention contains cosmetics, nonionic pharmaceutical products, and pharmaceuticals, and can be produced according to a commonly used formulation method. Alcohol, silicone, anionic surfactants, cationic surfactants, amphoteric surfactants, nonionic surfactants, preservatives, sugars, metal ion sequestering agents, polymers such as water-soluble polymers, thickeners, powders It can contain body components, UV absorbers, UV blockers, moisturizers such as hyaluronic acid, fragrances, pH adjusters and the like. It can also contain other medicinal and physiologically active ingredients such as vitamins, skin activators, blood circulation promoters, indigenous bacteria control agents, active oxygen scavengers, anti-inflammatory agents, whitening agents and bactericidal agents.
本発明の皮膚外用剤は、化粧料、医薬部外品、医薬品を含むものであって、化粧水、乳液、クリーム、ジェル等の、溶液状、乳化物状、高分子ゲル状製剤とすることができる。また、泡状製剤、多層状製剤、スプレー製剤、不織布等に含浸させたシートあるいはゲルパック製剤であってもよい。 The external preparation for skin of the present invention includes cosmetics, quasi-drugs, and pharmaceuticals, and is a solution-like, emulsion-like, or high-molecular-weight gel-like preparation such as a lotion, a milky lotion, a cream, or a gel. Can be done. Further, it may be a foam preparation, a multi-layer preparation, a spray preparation, a sheet or gel pack preparation impregnated with a non-woven fabric or the like.
本発明の皮膚外用剤には、目的に応じて任意成分として保湿剤、界面活性剤、増粘剤、抗炎症剤、ビタミン類、抗酸化剤、血行促進剤、創傷治癒剤、抗菌性物質、皮膚賦活剤、常在菌コントロール剤、活性酸素消去剤、美白剤等の薬効成分を含有させることができる。 The external preparation for skin of the present invention includes moisturizers, surfactants, thickeners, anti-inflammatory agents, vitamins, antioxidants, blood circulation promoters, wound healing agents, antibacterial substances, etc. It can contain medicinal ingredients such as skin activators, indigenous bacteria control agents, active oxygen scavengers, and whitening agents.
薬効成分としては、従来、医薬品、医薬部外品、化粧品、衛生材料等で使用されていて、水に溶解、または分散可能なものであれば特に限定されることなく使用することができる。具体的には、アシタバエキス、アボカドエキス、アマチャエキス、アルテアエキス、アルニカエキス、アンズエキス、アンズ核エキス、ウイキョウエキス、ウコンエキス、ウーロン茶エキス、エチナシ葉エキス、オウゴンエキス、オウバクエキス、オオムギエキス、オランダカラシエキス、オレンジエキス、海水乾燥物、加水分解エラスチン、加水分解コムギ末、加水分解シルク、カモミラエキス、カロットエキス、カワラヨモギエキス、甘草エキス、カルカデエキス、キウイエキス、キナエキス、キューカンバーエキス、グアノシン、クマザサエキス、クルミエキス、グレープフルーツエキス、クレマティスエキス、酵母エキス、ゴボウエキス、コンフリーエキス、コラーゲン、コケモモエキス、サイコエキス、サイタイ抽出液、サルビアエキス、サボンソウエキス、ササエキス、サンザシエキス、シイタケエキス、ジオウエキス、シコンエキス、シナノキエキス、シモツケソウエキス、ショウブ根エキス、シラカバエキス、スギナエキス、スイカズラエキス、セイヨウキズタエキス、セイヨウサンザシエキス、セイヨウニワトコエキス、セイヨウノコギリソウエキス、セイヨウハッカエキス、ゼニアオイエキス、センブリエキス、タイソウエキス、タイムエキス、チョウジエキス、チガヤエキス、チンピエキス、トウヒエキス、ドクダミエキス、トマトエキス、納豆エキス、ニンジンエキス、ノバラエキス、ハイビスカスエキス、バクモンドウエキス、パセリエキス、蜂蜜、パリエタリアエキス、ヒキオコシエキス、ビサボロール、フキタンポポエキス、フキノトウエキス、ブクリョウエキス、ブッチャーブルームエキス、ブドウエキス、プロポリス、ヘチマエキス、ペパーミントエキス、ボダイジュエキス、ホップエキス、マツエキス、マロニエエキス、ミズバショウエキス、ムクロジエキス、モモエキス、ヤグルマギクエキス、ユーカリエキス、ユズエキス、ヨモギエキス、ラベンダーエキス、リンゴエキス、レタスエキス、レモンエキス、レンゲソウエキス、ローズエキス、ローズマリーエキス、ローマカミツレエキス、ローヤルゼリーエキス等を挙げることができる。 The medicinal ingredient is conventionally used in pharmaceuticals, quasi-drugs, cosmetics, sanitary materials and the like, and can be used without particular limitation as long as it can be dissolved or dispersed in water. Specifically, Ashitaba extract, Avocado extract, Amacha extract, Artea extract, Arnica extract, Anzu extract, Anzu nucleus extract, Wikyo extract, Ukon extract, Oolong tea extract, Echinashi leaf extract, Ogon extract, Oubaku extract, Omugi extract, Netherlands Karashi extract, orange extract, dried seawater, hydrolyzed elastin, hydrolyzed wheat powder, hydrolyzed silk, chamomile extract, carrot extract, kawarayomogi extract, licorice extract, calcade extract, kiwi extract, kina extract, cucumber extract, guanosine, kumazasa extract , Walnut extract, Grapefruit extract, Clematis extract, Yeast extract, Gobo extract, Confree extract, Collagen, Kokemomo extract, Psycho extract, Saitai extract, Salvia extract, Sabonsou extract, Sasa extract, Sanzashi extract, Shiitake extract, Jio extract, Shikon extract , Shinanoki extract, Shimotsukesou extract, Shobu root extract, Shirakaba extract, Sugina extract, Watermelon extract, Seiyoukizuta extract, Seiyousanzashi extract, Seiyouniwatoko extract, Seiyounokogirisou extract, Seiyouhakka extract, Zeniaoi extract, Senburi extract, Taisou extract, Thyme Extract, Chouji extract, Chigaya extract, Chinpi extract, Tohi extract, Dokudami extract, Tomato extract, Natto extract, Carrot extract, Novara extract, Hibiscus extract, Bakumondou extract, Parsley extract, Honey, Parietaria extract, Hikiokoshi extract, Bisaborol, Fukitanpopo extract , Fukinoto extract, Bukuryo extract, Butcher bloom extract, Grape extract, Propolis, Hechima extract, Peppermint extract, Bodaiju extract, Hop extract, Pine extract, Maronie extract, Mizubasho extract, Mukuroji extract, Peach extract, Yagurumagiku extract, Eucalyptus extract, Yuzu extract, Yomogi Examples thereof include extracts, lavender extracts, apple extracts, lettuce extracts, lemon extracts, astragalus extracts, rose extracts, rosemary extracts, Roman chamomile extracts, royal jelly extracts and the like.
また、アミノ酸、尿素、ピロリドンカルボン酸ナトリウム、ベタイン、ホエイ、トリメチルグリシン等の保湿剤；スフィンゴ脂質、セラミド、コレステロール、コレステロール誘導体、リン脂質等の油性成分；ε−アミノカプロン酸、グリチルリチン酸、β−グリチルレチン酸、塩化リゾチーム、グアイアズレン、ヒドロコルチゾン等の抗炎症剤；ビタミンＡ，Ｂ２，Ｂ６，Ｄ，Ｅ、パントテン酸カルシウム、ビオチン、ニコチン酸アミド等のビタミン類；トコフェロール、カロチノイド、フラボノイド、タンニン、リグナン、サポニン等の抗酸化剤；γ−オリザノール、ビタミンＥ誘導体等の血行促進剤；レチノール、レチノール誘導体等の創傷治癒剤；デオキシリボ核酸、コンドロイチン硫酸ナトリウム、コラーゲン、エラスチン、キチン、キトサン、加水分解卵殻膜等の生体高分子；アラントイン、ジイソプロピルアミンジクロロアセテート、４−アミノメチルシクロヘキサンカルボン酸等の活性成分；セファランチン、トウガラシチンキ、ヒノキチオール、ヨウ化ニンニクエキス、塩酸ピリドキシン、ｄｌ−α−トコフェロール、酢酸ｄｌ−α−トコフェロール、ニコチン酸、ニコチン酸誘導体、Ｄ−パントテニルアルコール、アセチルパントテニルエチルエーテル、ビオチン、アラントイン、イソプロピルメチルフェノール、エストラジオール、エチニルエストラジオール、塩化カルプロニウム、塩化ベンザルコニウム、塩酸ジフェンヒドラミン、タカナール、カンフル、サリチル酸、ノニル酸バニリルアミド、ノナン酸バニリルアミド、ピロクトンオラミン、ペンタデカン酸グリセリル、モノニトログアヤコール、レゾルシン、γ−アミノ酪酸、塩化ベンゼトニウム、塩酸メキシレチン、オーキシン、女性ホルモン、カンタリスチンキ、シクロスポリン、ヒドロコルチゾン、モノステアリン酸ポリオキシエチレンソルビタン等も挙げられる。 Moisturizers such as amino acids, urea, sodium pyrrolidone carboxylate, betaine, whey, trimethylglycine; oily components such as sphingolipid, ceramide, cholesterol, cholesterol derivative, phospholipid; ε-aminocaproic acid, glycyrrhizinic acid, β-glycyrrhetin Anti-inflammatory agents such as acids, lysozyme chloride, guaizrene, hydrocortisone; vitamins such as vitamins A, B2, B6, D, E, calcium pantothenate, biotin, nicotinic acid amide; tocopherol, carotinoid, flavonoid, tannin, lignan, saponin Antioxidants such as γ-orizanol, blood circulation promoters such as vitamin E derivatives; wound healing agents such as retinol and retinol derivatives; deoxyribonucleic acid, sodium chondroitin sulfate, collagen, elastin, chitin, chitosan, hydrolyzed eggshell membranes, etc. Biopolymers; Active ingredients such as allantin, diisopropylamine dichloroacetate, 4-aminomethylcyclohexanecarboxylic acid; cepharanthin, togarashitinki, hinokithiol, garlic iodide extract, pyridoxin hydrochloride, dl-α-tocopherol, dl-α-tocopherol acetate , Nicotinic acid, nicotinic acid derivative, D-pantothenyl alcohol, acetylpantothenyl ethyl ether, biotin, allantin, isopropylmethylphenol, estradiol, ethynyl estradiol, carpronium chloride, benzalkonium chloride, diphenhydramine hydrochloride, takanal, camphor, salicylic acid, Nonylic acid vanillylamide, nonanoic acid vanillylamide, pyrocton olamine, glyceryl pentadecanoate, mononitroguayacol, resorcin, γ-aminobutyric acid, benzethonium chloride, mexiretin hydrochloride, auxin, female hormone, cantalistinki, cyclosporin, hydrocortisone, monostearic acid Polyoxyethylene sorbitan and the like can also be mentioned.
以下、実施例に基づいて本発明について詳細に説明するが、本発明はこれに限定されるものではない。 Hereinafter, the present invention will be described in detail based on examples, but the present invention is not limited thereto.
＜ヒアルロン酸産生促進確認試験 ＞
正常ヒト新生児表皮角化細胞を用いてヒアルロン酸産生促進作用を確認した。
プトレシン二塩酸塩；（ナカライテスク社、商品コード２９４２８−０１）
スペルミジン三塩酸塩；（ナカライテスク社、商品コード３２１１０−４１）
スペルミン四塩酸塩；（ナカライテスク社、商品コード３２１１３−１１）
Ｎ８−アセチルスペルミジン二塩酸塩；（Ｓｉｇｍａ−Ａｌｄｒｉｃｈ社、商品コードＡ３６５８）
Ｎ１，Ｎ８−ジアセチルスペルミジン；（Ｔｏｒｏｎｔｏ Ｒｅｓｅａｒｃｈ Ｃｈｅｍｉｃａｌｓ Ｉｎｃ、商品コードＤ３６７０００）
Ｎ１−アセチルスペルミン三塩酸塩；（Ｓｉｇｍａ−Ａｌｄｒｉｃｈ社、商品コード０１４６７）
<Hyaluronic acid production promotion confirmation test>
Hyaluronic acid production promoting action was confirmed using normal human neonatal epidermal keratinocytes.
Putrescine dihydrochloride; (Nacalai Tesque, product code 29428-01)
Spermidine trichloride; (Nacalai Tesque, product code 32110-41)
Spermine tetrachloride; (Nacalai Tesque, product code 32113-11)
N8-Acetylspermidine dihydrochloride; (Sigma-Aldrich, product code A3658)
N1, N8-diacetylspermidine; (Toronto Research Chemicals Inc, product code D367000)
N1-Acetylspermine Trihydrochloride; (Sigma-Aldrich, Commodity Code 01467)
（試験１：表皮）
正常ヒト新生児表皮角化細胞（ＮＨＥＫ）を表皮角化細胞増殖培地（ＫＧＭ）を用いて培養した後、トリプシン処理により細胞を回収した。回収した細胞を１．０×１０５ｃｅｌｌｓ／ｍＬの濃度になるようにＫＧＭ培地で希釈した後、９６ｗｅｌｌプレートに１ｗｅｌｌ当たり１００μＬずつ播種し、２４時間培養した。
培養終了後、ＫＧＭ培地に所定濃度となるように溶解した被験試料を各ｗｅｌｌに１００μＬずつ添加し、３日間培養した。培養後、各ｗｅｌｌの培地中のヒアルロン酸量を、ヒアルロン酸結合タンパクを用いたサンドイッチ法により測定した。試験は、各試料ｎ＝５で行った。
(Test 1: Epidermis)
Normal human neonatal epidermal keratinocytes (NHEK) were cultured in epidermal keratinocyte proliferation medium (KGM), and then the cells were recovered by trypsin treatment. After dilution with KGM media as recovered cells to a concentration of 1.0 × 10 5 cells / mL, seeded by 100μL per 1well in 96well plates and incubated for 24 hours.
After completion of the culture, 100 μL of a test sample dissolved in KGM medium to a predetermined concentration was added to each well, and the cells were cultured for 3 days. After culturing, the amount of hyaluronic acid in the medium of each well was measured by a sandwich method using a hyaluronic acid-binding protein. The test was performed on each sample n = 5.
（試験２：真皮）
ヒト正常線維芽細胞（ＮＢ１ＲＧＢ）を１０％ＦＢＳ（牛胎児血清）含有ダルベッコＭＥＭ培地を用いて培養した後、トリプシン処理により細胞を回収した。回収した細胞を１．６×１０５ｃｅｌｌｓ／ｍＬの濃度に上記培地で希釈した後、９６ｗｅｌｌマイクロプレートに１ｗｅｌｌ当たり１００μＬずつ播種し、一晩培養した。
培養終了後、０．２５％ＦＢＳ含有ダルベッコＭＥＭ培地に所定濃度となるように溶解した被験試料を各ｗｅｌｌに１００μＬ添加し、３日間培養した。培養後、各ｗｅｌｌの培地中のヒアルロン酸量をヒアルロン酸結合タンパクを用いたサンドイッチ法により測定した。試験は、各試料ｎ＝５で行った。
(Test 2: Dermis)
Human normal fibroblasts (NB1RGB) were cultured in Dulbecco MEM medium containing 10% FBS (fetal bovine serum), and then the cells were recovered by trypsin treatment. After dilution with the medium recovered cells to a concentration of 1.6 × 10 5 cells / mL, seeded by 100μL per 1well in 96well microplate, and cultured overnight.
After completion of the culture, 100 μL of a test sample dissolved in Dulbecco MEM medium containing 0.25% FBS to a predetermined concentration was added to each well and cultured for 3 days. After culturing, the amount of hyaluronic acid in the medium of each well was measured by a sandwich method using a hyaluronic acid-binding protein. The test was performed on each sample n = 5.
ヒアルロン酸産生促進率は、以下の式より算出した。平均値を表１、２に示す。
ヒアルロン酸産生促進率（％）＝Ａ／Ｂ×１００
Ａ：被験試料添加時のヒアルロン酸量
Ｂ：被験試料無添加時のヒアルロン酸量
The hyaluronic acid production promotion rate was calculated from the following formula. The average values are shown in Tables 1 and 2.
Hyaluronic acid production promotion rate (%) = A / B x 100
A: Amount of hyaluronic acid when test sample is added B: Amount of hyaluronic acid when no test sample is added
（結果）
アセチルスペルミン、アセチルスペルミジン、ジアセチルスペルミジンは、プトレシン、スペルミジン、スペルミンと同等もしくは同等以上のヒアルロン酸産生促進活性を有していた。アセチルスペルミン、ジアセチルスペルミジンは、表皮におけるヒアルロン酸産生促進活性、アセチルスペルミン、アセチルスペルミジン、ジアセチルスペルミジンは、真皮におけるヒアルロン酸産生促進活性に優れていた。
(result)
Acetylspermine, acetylspermidine, and diacetylspermidine had hyaluronic acid production-promoting activity equal to or higher than that of putrescine, spermidine, and spermine. Acetylspermine and diacetylspermidine were excellent in hyaluronic acid production promoting activity in the epidermis, and acetylspermine, acetylspermidine and diacetylspermidine were excellent in hyaluronic acid production promoting activity in the dermis.
（処方例）
（化粧水）
１．精製水 残余
２．グリセリン ５．０％
３．ジグリセリン ７．０％
４．１，３−ブチレングリコール ５．０％
５．ベタイン １．０％
６．アセチルスペルミン ０．００１％
７．フェノキシエタノール ０．３％
１〜７を撹拌混合し、化粧水を得た。
(Prescription example)
(Toner)
1. 1. Purified water residue 2. Glycerin 5.0%
3. 3. Diglycerin 7.0%
4.1,3-butylene glycol 5.0%
5. Betaine 1.0%
6. Acetyl spermine 0.001%
7. Phenoxyethanol 0.3%
1 to 7 were stirred and mixed to obtain a lotion.
（美容ジェル）
１．精製水 残余
２．ジプロピレングリコール ６．０％
３．ＰＥＧ−７５ ０．５％
４．ラフィノース ２．０％
５．フェノキシエタノール ０．２％
６．ペンチレングリコール １．０％
７．キサンタンガム ０．１％
８．スクワラン ３．０％
９．ＳＩＭＵＬＧＥＬ ＮＳ ２．５％
１０．アセチルスペルミジン ０．０００１％
１１． エタノール ２．０％
６に７を分散させる（分散物）。８と９を混合する（混合物）。分散物を加熱溶解した１から５に徐々に添加し、さらに混合物を添加したのちホモミクサーで撹拌する。冷却後、１０、１１を加えた後、再度ホモミクサーで撹拌させる。
※ＳＩＭＵＬＧＥＬ ＮＳ（ＳＥＰＰＩＣ社製；（アクリル酸ヒドロキシエチル/アクリロイルジメチルタウリンＮａ）コポリマー、スクワラン、ポリソルベート６０、水、イソステアリン酸ソルビタンの混合物）
(Beauty gel)
1. 1. Purified water residue 2. Dipropylene glycol 6.0%
3. 3. PEG-75 0.5%
4. Raffinose 2.0%
5. Phenoxyethanol 0.2%
6. Pentylene glycol 1.0%
7. Xanthan gum 0.1%
8. Squalene 3.0%
9. SIMULGEL NS 2.5%
10. Acetyl spermidine 0.0001%
11. Ethanol 2.0%
Disperse 7 in 6 (dispersion). Mix 8 and 9 (mixture). The dispersion is gradually added to 1 to 5 which have been dissolved by heating, and after further adding the mixture, the mixture is stirred with a homomixer. After cooling, 10 and 11 are added, and then the mixture is stirred again with a homomixer.
* SIMULGEL NS (manufactured by SEPPIC; (hydroxyethyl acrylate / acryloyldimethyltaurine Na) copolymer, squalane, polysorbate 60, water, mixture of sorbitan isostearate)
（乳液）
１．オリーブ油 ５．０％
２．ホホバ油 １．０％
３．ジメチコン ０．５％
４．ステアリン酸ポリグリセリル−１０ １．０％
５．グリセリン ７．０％
６．ジプロピレングリコール ６．０％
７．フェノキシエタノール ０．５％
８．１，３−ブチレングリコール ３．０％
９．キサンタンガム １．０％
１０．カルボキシビニルポリマー ０．１％
１１．水酸化カリウム ０．０２％
１２．ジアセチルスペルミジン ０．００２％
１３．精製水 残余
８に９を分散させる（分散物）。１０を１３に撹拌溶解させたものに、分散物を添加、さらに５から７を添加し加熱溶解させる（溶解物）。１から４を加熱溶解させ、溶解物を徐々に添加し、ホモミクサーで撹拌する。次いで、１３の一部に１１を溶解させたものを添加、冷却後、１３の一部に溶解させた１２を加えた後、再度ホモミクサーで撹拌させる。
(Emulsion)
1. 1. Olive oil 5.0%
2. Jojoba oil 1.0%
3. 3. Dimethicone 0.5%
4. Polyglyceryl stearate-10 1.0%
5. Glycerin 7.0%
6. Dipropylene glycol 6.0%
7. Phenoxyethanol 0.5%
8.1,3-butylene glycol 3.0%
9. Xanthan gum 1.0%
10. Carboxyvinyl polymer 0.1%
11. Potassium hydroxide 0.02%
12. Diacetyl spermidine 0.002%
13. 9 is dispersed in the residual 8 of purified water (dispersion). A dispersion is added to a mixture of 10 to 13 with stirring, and 5 to 7 are further added and dissolved by heating (dissolved product). 1 to 4 are dissolved by heating, the lysate is gradually added, and the mixture is stirred with a homomixer. Next, a part of 13 in which 11 is dissolved is added, and after cooling, the dissolved 12 is added in a part of 13, and then the mixture is stirred again with a homomixer.
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