JP2017019725A - Melanogenesis inhibitors containing urolithins - Google Patents
Melanogenesis inhibitors containing urolithins Download PDFInfo
- Publication number
- JP2017019725A JP2017019725A JP2015136145A JP2015136145A JP2017019725A JP 2017019725 A JP2017019725 A JP 2017019725A JP 2015136145 A JP2015136145 A JP 2015136145A JP 2015136145 A JP2015136145 A JP 2015136145A JP 2017019725 A JP2017019725 A JP 2017019725A
- Authority
- JP
- Japan
- Prior art keywords
- urolithin
- melanin production
- acid
- oil
- urolithins
- 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
- 239000003112 inhibitor Substances 0.000 title claims abstract description 50
- 229930186301 urolithin Natural products 0.000 title claims abstract description 48
- 230000003061 melanogenesis Effects 0.000 title abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
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- 230000008099 melanin synthesis Effects 0.000 claims description 61
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Abstract
Description
本発明は、ウロリチン類を含有するメラニン産生抑制剤に関する。 The present invention relates to a melanin production inhibitor containing urolithins.
日焼けやシミ、ソバカス等の皮膚の色素沈着は、表皮細胞に存在する細胞メラノサイトが増殖し、増殖したメラノサイトにおいて生成された色素メラニンが隣接細胞に拡散することで生じる。メラニン産生の機序は細胞内で起こる複雑な過程を経る。メラニンの産生を抑制するには、紫外線から皮膚を防御したり、紫外線により発生する一重項酸素を除去したり、サイトカインの発生を抑制したり、チロシナーゼ活性を抑制することなどが挙げられる(非特許文献1)。例えばメラニン合成の原料となるチロシンを酸化するチロシナーゼの活性を阻害する結果、メラニン産生が抑制されることに基づいた、美白作用を発揮する薬剤等が種々知られている(特許文献1−4)。 Skin pigmentation such as sunburn, spots, and buckwheat occurs when cellular melanocytes present in epidermal cells proliferate and pigment melanin produced in the proliferated melanocytes diffuses to adjacent cells. The mechanism of melanin production is a complex process that takes place inside the cell. Inhibiting the production of melanin includes protecting the skin from ultraviolet rays, removing singlet oxygen generated by ultraviolet rays, suppressing the generation of cytokines, and suppressing tyrosinase activity (non-patented). Reference 1). For example, various agents that exhibit a whitening action based on the suppression of melanin production as a result of inhibiting the activity of tyrosinase that oxidizes tyrosine as a raw material for melanin synthesis are known (Patent Documents 1-4). .
一方で、ウロリチンという物質が存在することが知られている。ウロリチンAに代表されるウロリチン類は、ザクロ、ラズベリー、ブラックベリー、クラウドベリー、イチゴ、クルミなどに含まれるエラジタンニンに由来するエラグ酸の代謝物として知られている。エラジタンニンは加水分解性タンニンに分類され、摂取されると体内で加水分解され、エラグ酸に変換されることが知られている。このようなエラジタンニンやエラグ酸は体内の腸管吸収性は非常に低いが、これらが摂取された際、ヒト結腸微生物叢によって更に代謝されることによってウロリチン類に変換されることが知られている。このようにして生成されるウロリチン類は生体内で最も重要な化合物の1つである。近年、その腸内細菌がGordonibacter urolithinfaciensであると同定された(非特許文献2)。 On the other hand, it is known that a substance called urolithin exists. Urolithins represented by urolithin A are known as ellagic acid metabolites derived from ellagitannins contained in pomegranate, raspberry, blackberry, cloudberry, strawberry, walnut and the like. It is known that ellagitannins are classified into hydrolyzable tannins, and when ingested, they are hydrolyzed and converted to ellagic acid. Such ellagitannins and ellagic acid have very low intestinal absorption in the body, but when they are ingested, they are known to be further metabolized by the human colonic microflora and converted to urolithins. The urolithins thus produced are one of the most important compounds in the living body. In recent years, the intestinal bacterium has been identified as Gordonibacter urolithinfaciens (Non-patent Document 2).
エラジタンニンやエラグ酸を摂取した後、ウロリチンAが主な代謝物であることがラットやヒトにおいて報告されており、ウロリチンAに抗炎症作用、抗ガン作用などがあることが報告されている。特許文献5には、ウロリチンAやウロリチンB等のウロリチン類について記載されており、肥満、新陳代謝速度低下、メタボリックシンドローム等から選択される症状の治療または予防等のための、有効量のウロリチン類を含む食品等が記載されている。 After ingesting ellagitannin and ellagic acid, it has been reported in rats and humans that urolithin A is the main metabolite, and it has been reported that urolithin A has anti-inflammatory and anti-cancer effects. Patent Document 5 describes urolithins such as urolithin A and urolithin B. An effective amount of urolithin for the treatment or prevention of symptoms selected from obesity, metabolic rate decrease, metabolic syndrome, etc. Contains foods.
これらに加えて、ウロリチン類の酵素反応を用いたチロシナーゼ阻害活性の評価に係る知見はあるが、メラニン産生抑制の効果は調べられておらず、ウロリチン類が明白なメラニン産生抑制効果を有すること、及び、美白効果を有することは知られていない。 In addition to these, there is knowledge related to the evaluation of tyrosinase inhibitory activity using the enzyme reaction of urolithins, but the effect of suppressing melanin production has not been investigated, that urolithins have an obvious melanin production inhibitory effect, And it is not known to have a whitening effect.
本発明は上記状況下でなされたものであり、本発明は、ウロリチン類を含有する新規なメラニン産生抑制剤の提供を課題とする。 The present invention has been made under the above circumstances, and an object of the present invention is to provide a novel melanin production inhibitor containing urolithins.
本発明者らは、新規なメラニン産生抑制剤を探索したところ、ウロリチン類がメラニン産生抑制作用を有することを見出し、本発明を完成させた。すなわち、本発明は以下に示すとおりである。
<1>
下記一般式(1)で表されるウロリチン類を含有するメラニン産生抑制剤。
As a result of searching for a novel melanin production inhibitor, the present inventors have found that urolithins have a melanin production inhibitory action, thereby completing the present invention. That is, the present invention is as follows.
<1>
The melanin production inhibitor containing the urolithin represented by following General formula (1).
(式中、R1、R2、R3、R4、R5、及びR6は、それぞれ、水酸基、水素原子又はメトキシ基を表し、且つ、R1、R2、R3、R4、R5、及びR6のうち1つ以上は水酸基である。)
<2>
<1>に記載のメラニン産生抑制剤を含有する美白剤。
<3>
前記ウロリチン類が下記式(2)で表されるウロリチンAである、<1>に記載のメラニン産生抑制剤。
(Wherein R1, R2, R3, R4, R5, and R6 each represent a hydroxyl group, a hydrogen atom, or a methoxy group, and at least one of R1, R2, R3, R4, R5, and R6 is It is a hydroxyl group.)
<2>
Whitening agent containing the melanin production inhibitor as described in <1>.
<3>
The melanin production inhibitor according to <1>, wherein the urolithin is urolithin A represented by the following formula (2).
<4>
前記ウロリチン類が下記式(2)で表されるウロリチンAである、<2>に記載の美白剤。
<4>
The whitening agent according to <2>, wherein the urolithin is urolithin A represented by the following formula (2).
本発明によれば、新規なメラニン産生抑制剤として、ウロリチン類を含有するメラニン産生抑制剤を提供することができる。 According to the present invention, a melanin production inhibitor containing urolithins can be provided as a novel melanin production inhibitor.
本発明は、ウロリチン類を含有するメラニン産生抑制剤に係る第一の実施態様と、前記メラニン産生抑制剤を含有する美白剤に係る第二の実施態様を含む。 The present invention includes a first embodiment relating to a melanin production inhibitor containing urolithins and a second embodiment relating to a whitening agent containing the melanin production inhibitor.
<1.ウロリチン類を含有するメラニン産生抑制剤>
本発明の第一の実施態様は、下記一般式(1)で表されるウロリチン類を含有するメラニン産生抑制剤である。
<1. Melanin production inhibitor containing urolithins>
The first embodiment of the present invention is a melanin production inhibitor containing urolithins represented by the following general formula (1).
(ウロリチン類)
本実施態様におけるウロリチン類は特に限定されないが、その構造が上記一般式(1)で表される物質である。また、表1に示すように、ウロリチン類は化学式におけるR1〜R6によって、ウロリチンA、ウロリチンB、ウロリチンC、ウロリチンD、ウロリチンE、ウロリチンM3、ウロリチンM4、ウロリチンM5、ウロリチンM6、ウロリチンM7、及びイソウロリチンAなどを含む。
(Urolithins)
Although the urolithins in this embodiment are not specifically limited, The structure is a substance represented by the said General formula (1). In addition, as shown in Table 1, urolithins are represented by R1-R6 in the chemical formula, and urolithin A, urolithin B, urolithin C, urolithin D, urolithin E, urolithin M3, urolithin M4, urolithin M5, urolithin M6, urolithin M7, and Isouroritin A and the like are included.
このうち、メラニン産生抑制効果が高いことから、ウロリチンA、ウロリチンB、ウロリチンC、ウロリチンDが好ましく、ウロリチンAがより好ましい。 Among these, since melanin production inhibitory effect is high, urolithin A, urolithin B, urolithin C, and urolithin D are preferable, and urolithin A is more preferable.
ウロリチン類を得る方法は特段限定されず、市販されているものを用いてもよく、化学合成により合成してもよい。 The method for obtaining urolithins is not particularly limited, and commercially available products may be used, or they may be synthesized by chemical synthesis.
市販のウロリチン類としては、例えば、ウロリチンA、ウロリチンB、ウロリチンC、ウロリチンD(Dalton Pharma社製)などを挙げることができる。 Examples of commercially available urolithins include urolithin A, urolithin B, urolithin C, urolithin D (Dalton Pharma) and the like.
また、化学合成による合成方法としては常法に従うことができ、例えば、本明細書の実施例で説明するように、2−ブロモ−5−メトキシ安息香酸と塩化アルミニウムとを原料に用いて合成する方法が挙げられる。 In addition, as a synthetic method by chemical synthesis, a conventional method can be followed. For example, as described in Examples of the present specification, synthesis is performed using 2-bromo-5-methoxybenzoic acid and aluminum chloride as raw materials. A method is mentioned.
また、植物からエラジタンニンの一種であるプニカラジンを抽出し、これをエラグ酸に加水分解した後、もしくはエラグ酸を抽出し、微生物を用いてウロリチン類に変換してもよい。 Alternatively, punicalagin, a kind of ellagitannin, may be extracted from plants and hydrolyzed into ellagic acid, or ellagic acid may be extracted and converted to urolithins using microorganisms.
植物の種類は特段限定されず、ザクロ、ラズベリー、ブラックベリー、クラウドベリー、ボイセンベリー、イチゴ、クルミ、ゲンノショウコ等が挙げられる。このうち、エラジタンニン及び/又はエラグ酸を高含有していることから、ザクロ、ボイセンベリー、ゲンノショウコが好ましく、ザクロがより好ましい。
これらの植物は、いずれか1種のみを用いてもよいし、2種以上を併用してもよい。また、該植物からの抽出方法及び抽出条件は特段限定されず、常法に従えばよい。例えば、水抽出、熱水抽出、温水抽出、アルコール抽出、超臨界抽出等の公知の抽出方法を用いることができる。
The kind of plant is not particularly limited, and examples include pomegranate, raspberry, blackberry, cloudberry, boysenberry, strawberry, walnut, and ginger. Of these, pomegranate, boysenberry and genokosho are preferred, and pomegranate is more preferred because of its high content of ellagitannin and / or ellagic acid.
Any one of these plants may be used, or two or more thereof may be used in combination. Moreover, the extraction method and extraction conditions from this plant are not specifically limited, What is necessary is just to follow a conventional method. For example, a known extraction method such as water extraction, hot water extraction, hot water extraction, alcohol extraction, supercritical extraction or the like can be used.
溶媒抽出を行う場合、溶媒としては、例えば、水;メタノール、エタノール等の低級アルコールや、プロピレングリコール、1,3−ブチレングリコール等の多価アルコール等のアルコール類(無水、含水の別を問わない);アセトン等のケトン類、ジエチルエーテル、ジオキサン、アセトニトリル、酢酸エチルエステル等のエステル類、キシレン等が挙げられ、好ましくは水、エタノール等である。これらの溶媒は、いずれか1種のみを用い
てもよいし、2種以上を併用してもよい。
When performing solvent extraction, the solvent may be, for example, water; alcohols such as lower alcohols such as methanol and ethanol, and polyhydric alcohols such as propylene glycol and 1,3-butylene glycol (anhydrous or hydrated). ); Ketones such as acetone; esters such as diethyl ether, dioxane, acetonitrile, and ethyl acetate; xylene; and the like, preferably water and ethanol. Any one of these solvents may be used, or two or more thereof may be used in combination.
抽出したプニカラジンなどのエラジタンニンをエラグ酸に加水分解する方法としては特段限定されないが、酸、酵素、微生物によって加水分解する方法が挙げられる。 The method for hydrolyzing the extracted ellagitannin such as punicalagin to ellagic acid is not particularly limited, and examples thereof include a method of hydrolyzing with an acid, an enzyme, and a microorganism.
微生物を用いてエラグ酸をウロリチン類に変換する方法としては特段限定されないが、例えば、Food Funct., 5, 8, 1779-1784 (2014)に記載にされている公知の方法を用いる
ことができる。
The method for converting ellagic acid to urolithins using a microorganism is not particularly limited, and for example, a known method described in Food Funct., 5, 8, 1779-1784 (2014) can be used. .
得られたウロリチン類をそのままの状態で使用することもできるが、乾燥させて粉末状のものを用いてもよい。また、必要に応じて、得られたウロリチン類に精製、濃縮処理等を施してもよい。精製処理としては、濾過又はイオン交換樹脂や活性炭カラム等を用いた吸着、脱色といった処理を行うことができる。また、濃縮処理としては、エバポレーター等の常法を利用できる。 Although the obtained urolithins can be used as they are, they may be dried and used in a powder form. Moreover, you may refine | purify, a concentration process, etc. to the obtained urolithins as needed. As the purification treatment, treatment such as filtration or adsorption or decolorization using an ion exchange resin or activated carbon column can be performed. As the concentration treatment, a conventional method such as an evaporator can be used.
また、得られたウロリチン類(又は精製処理物若しくは濃縮物)を凍結乾燥処理に供して粉末化する方法、デキストリン、コーンスターチ、アラビアゴム等の賦形剤を添加してスプレードライ処理により粉末化する方法等、公知の方法に従って粉末化してもよい。さらにその後に、必要に応じて純水、エタノール等に溶解して用いてもよい。 In addition, the obtained urolithins (or purified product or concentrate) are subjected to a freeze-drying process, and powdered by spray-drying by adding excipients such as dextrin, corn starch, and gum arabic. You may powder according to well-known methods, such as a method. Further, it may be used after being dissolved in pure water, ethanol or the like as required.
(メラニン産生抑制剤)
本実施態様は、上記したウロリチン類を含有するメラニン産生抑制剤である。本実施態様に係るメラニン産生抑制剤は、上記したウロリチン類のうち一種を含有してもよく、複数種を含有してもよい。
(Melanin production inhibitor)
This embodiment is a melanin production inhibitor containing the urolithins described above. The melanin production inhibitor which concerns on this embodiment may contain 1 type among above-described urolithins, and may contain multiple types.
本実施態様に係るメラニン産生抑制剤は、メラニン産生を抑制するものである。例えば、美白の観点からいえば、細胞内においてメラニン産生が抑制されることで皮膚組織の褐変を抑えるため、結果的に美白効果が実現される。このことから、本実施態様に係るメラニン産生抑制剤は、美白の用途に好ましく用いられる。 The melanin production inhibitor which concerns on this embodiment suppresses melanin production. For example, from the viewpoint of whitening, since the browning of the skin tissue is suppressed by suppressing the production of melanin in the cells, the whitening effect is realized as a result. From this, the melanin production inhibitor which concerns on this embodiment is used preferably for the use of whitening.
本実施態様に係るメラニン産生抑制剤は、ウロリチン類を単独で含有してもよいが、ウロリチン類以外に公知の賦形剤、香料、着色料、乳化剤、安定化剤、増粘剤、酵素、防腐剤、滑沢剤、界面活性剤、崩壊剤、崩壊抑制剤、結合剤、吸収促進剤、吸着剤、保湿剤、可溶化剤、保存剤、風味剤、甘味剤等を、本実施態様の効果を損なわない範囲で必要に応じて配合することができる。 The melanin production inhibitor according to this embodiment may contain urolithins alone, but in addition to urolithins, known excipients, fragrances, colorants, emulsifiers, stabilizers, thickeners, enzymes, Preservatives, lubricants, surfactants, disintegrants, disintegration inhibitors, binders, absorption enhancers, adsorbents, moisturizers, solubilizers, preservatives, flavoring agents, sweeteners, etc. It can mix | blend as needed in the range which does not impair an effect.
メラニン産生抑制剤全量に対するウロリチン類の含有量は、本実施態様による所望の効果が奏される限り特に限定されないが、ウロリチン類の総量として、通常0.00001〜20質量%であり、好ましくは0.0001〜3質量%であり、より好ましくは0.0
01〜1質量%である。
The content of urolithins relative to the total amount of the melanin production inhibitor is not particularly limited as long as the desired effect according to this embodiment is achieved, but the total amount of urolithins is usually 0.00001 to 20% by mass, preferably 0. 0.0001-3 mass%, more preferably 0.0.
01 to 1% by mass.
<2.美白剤>
本発明の第二の実施態様は、上記メラニン産生抑制剤を含む美白剤である。
本実施態様に係る美白剤は、上記したメラニン産生抑制剤を単独で含有してもよいが、上記成分以外に公知の賦形剤、香料、着色料、乳化剤、安定化剤、増粘剤、酵素、防腐剤、滑沢剤、界面活性剤、崩壊剤、崩壊抑制剤、結合剤、吸収促進剤、吸着剤、保湿剤、可溶化剤、保存剤、風味剤、甘味剤等を、本実施態様の効果を損なわない範囲で必要に応じて配合することができる。
<2. Whitening agent>
The second embodiment of the present invention is a whitening agent containing the melanin production inhibitor.
The whitening agent according to this embodiment may contain the above-described melanin production inhibitor alone, but in addition to the above components, known excipients, fragrances, coloring agents, emulsifiers, stabilizers, thickeners, Enzymes, preservatives, lubricants, surfactants, disintegrants, disintegration inhibitors, binders, absorption enhancers, adsorbents, moisturizers, solubilizers, preservatives, flavors, sweeteners, etc. It can mix | blend as needed in the range which does not impair the effect of an aspect.
美白剤全量に対するメラニン産生抑制剤の含有量は、本実施態様による所望の効果が奏
される限り特に限定されないが、ウロリチン類の総量として、通常0.00001〜10質量%であり、好ましくは0.0001〜3質量%であり、より好ましくは0.0003〜1質量%である。
The content of the melanin production inhibitor with respect to the total amount of the whitening agent is not particularly limited as long as the desired effect according to this embodiment is achieved, but the total amount of urolithins is usually 0.00001 to 10% by mass, preferably 0. It is 0.0001-3 mass%, More preferably, it is 0.0003-1 mass%.
第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤は、実施形態に合わせ、化粧料や医薬品、食品などの素材として用いることができる。 The melanin production inhibitor according to the first embodiment or the whitening agent according to the second embodiment can be used as a material for cosmetics, pharmaceuticals, foods and the like according to the embodiment.
<3.化粧料>
第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤を化粧料の素材として用いる場合、該メラニン産生抑制剤又は美白剤を、水溶液、ローション、スプレー液、懸濁液および乳化液などの液状;粉末、顆粒およびブロック状などの固体状;クリームおよびペーストなどの半固体状;ゲル状等の各種所望の剤形の化粧料に調製することができる。このような化粧料は、洗顔料、乳液、クリーム、ゲル、エッセンス(美容液)、パック・マスク等の基礎化粧料、ファンデーション、口紅等のメーキャップ化粧料、口腔化粧料、芳香化粧料、毛髪化粧料、ボディ化粧料等の各種化粧料として有用である。
<3. Cosmetics>
When the melanin production inhibitor according to the first embodiment or the whitening agent according to the second embodiment is used as a cosmetic material, the melanin production inhibitor or whitening agent is used as an aqueous solution, lotion, spray liquid, suspension. And liquids such as emulsions; solids such as powders, granules and blocks; semi-solids such as creams and pastes; and gels and other desired dosage forms. Such cosmetics include facial cleansers, milks, creams, gels, essences (beauty serums), basic cosmetics such as packs and masks, makeup cosmetics such as foundations and lipsticks, oral cosmetics, aromatic cosmetics and hair cosmetics. It is useful as various cosmetics such as cosmetics and body cosmetics.
第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤を含有する化粧料は、常法に従って製造することができる。また、化粧料への第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤の、配合量、配合方法、配合時期は適宜選択することができる。さらに、必要に応じて、瓶、袋、缶、スプレー缶、噴霧容器、箱、パック等の適宜の容器に封入することができる。 The cosmetic containing the melanin production inhibitor according to the first embodiment or the whitening agent according to the second embodiment can be produced according to a conventional method. The blending amount, blending method, and blending time of the melanin production inhibitor according to the first embodiment for cosmetics or the whitening agent according to the second embodiment can be appropriately selected. Furthermore, it can be enclosed in appropriate containers, such as a bottle, a bag, a can, a spray can, a spray container, a box, and a pack, as needed.
第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤を化粧料の素材として用いる場合、化粧料全量に対する上記第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤の含有量は、各実施態様の所望の効果が奏される限り特に限定されないが、ウロリチン類の総量として、通常0.00001〜10質量%であり、好ましくは0.0001〜3質量%であり、より好ましくは0.0003〜1質量%である。 When the melanin production inhibitor according to the first embodiment or the whitening agent according to the second embodiment is used as a raw material for cosmetics, the melanin production inhibitor according to the first embodiment or the second is used with respect to the total amount of cosmetics. Although content of the whitening agent which concerns on embodiment is not specifically limited as long as the desired effect of each embodiment is show | played, As a total amount of urolithins, it is 0.00001-10 mass% normally, Preferably it is 0.0001. It is -3 mass%, More preferably, it is 0.0003-1 mass%.
第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤を化粧料の素材として用いる場合、通常用いられる公知の成分を適宜加えて用いることができる。
例えば、アニオン性界面活性剤(脂肪酸石鹸、スルホン酸塩型アニオン性界面活性剤、硫酸エステル型アニオン性界面活性剤、リン酸エステル型アニオン性界面活性剤、アシルメチルタウリン塩、モノアルキルリン酸塩、アシルグルタミン酸塩、イセチオン酸エステル塩等)、カチオン性界面活性剤(アミン塩型カチオン性界面活性剤、第四アンモニウム型カチオン性界面活性剤(テトラアルキルアンモニウム型、ピリジニウム型))、非イオン性界面活性剤(グリセリン脂肪酸エステル、プロピレングリコール脂肪酸エステル、ソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、テトラオレイン酸ポリオキシエチレンソルビット、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンポリオキシプロピレングリコール、ポリオキシエチレンポリオキシプロピレンアルキルエーテル、ポリエチレングリコール脂肪酸エステル、ポリオキシエチレンヒマシ油、ポリオキシエチレン硬化ヒマシ油、ポリグリセリン脂肪酸エステル等)、両性界面活性剤(イミダゾリン型、ベタイン型、アミノ酸型)、フッソ系界面活性剤、シリコーン系界面活性剤等の天然、合成界面活性剤、
アルギン酸ナトリウム、アルギン酸プロピレングリコールエステル、アラビアガム、キサンタンガム、ペクチン、トラガント、カルボキシメチルセルロースナトリウム、メチルセルロース、カルボキシビニルポリマー、ポリエチレングリコール、ポリビニルアルコール、ポリビニルピロリドン、カチオン化セルロース、カチオン化デキストラン、カチオン化デキストリン、キトサン、カチオン化ビニルピロリドンポリマー、塩化N,N−ジメチル−3,5−メチレンピペリジニウムポリマー、乳タンパク、大豆タンパク、ゼラチン、
卵タンパク、カゼインナトリウム、ホエータンパク等の水溶性高分子、
イチョウ、ツボクサ、トウヤク、ニンジン、シコッピ、カイカ、インチコウ、ヤシャジツ、甘草分画物、ゴカヒ、センプクカ、ヒカイ、ユズリハ、カミツレ、マロニエ、エスシン、テルミナリア、ルスコゲニン、ブッチャーブルーム、コラ、ガラナ、マテ、コーヒー、カカオ、プレクトランタス、タンジン、ビスナガ、シリマリン、ロイコシアニン、オトギリ草、クマハゼ、シソ、オウゴン、ケイガイ、ローズマリー、セージ、タイム、ヨモギ、カワラヨモギ、ソウジュツ、セイヨウノコギリソウ、シコン、ウイキョウ、オウバク、ショウキョウ、トウキ、センキュウ、チンビ、カノコソウ、ビャクシ、トウヒ、芍薬、紅花、菖蒲、ブクリョウ、ハッカ等の植物成分、
コハク酸、フマル酸、クエン酸、ピルビン酸、グルクロン酸、2−ヒドロキシ酪酸、乳酸、リンゴ酸、酒石酸、タルトロン酸、ピルビン酸メチル、ピルビン酸エチル、ビタミンA酸、ビタミンC誘導体、ビタミンD、ビタミンE、オリゴペプチド、トラネキサム酸エステル等の活性成分、
多価アルコール、アミノ酸、ムコ多糖類、蛋白質、生体抽出物、発酵代謝物、多糖類、植物抽出物、リン脂質、セラミドなどの保湿剤、
油脂類(大豆油、ヌカ油、ホホバ油、アボガド油、アーモンド油、カカオ油、オリーブ油、ゴマ油、パーシック油、ヒマシ油、ヤシ油、ミンク油、牛脂、豚脂等の天然油脂、これらの天然油脂を水素添加して得られる硬化油およびミリスチン酸グリセリド、2−エチルヘキサン酸グリセリド等の合成トリグリセリド、ジグリセリド等)、ロウ類(カルナウバロウ、鯨ロウ、ミツロウ、ラノリン等)、炭化水素類(流動パラフィン、ワセリン、パラフィン、マイクロクリスタリンワックス、セレシン、スクワラン、プリスタン等)、高級脂肪酸類(ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、ベヘニン酸、オレイン酸、リノール酸、リノレン酸、ラノリン酸、イソステアリン酸等)、高級アルコール類(ラウリルアルコール、セチルアルコール、ステアリルアルコール、オレイルアルコール、コレステロール、2−ヘキシルデカノール等)、エステル類(オクタン酸セチル、乳酸ミリスチル、乳酸セチル、ミリスチン酸イソプロピル、ミリスチン酸ミリスチル、パルミチン酸イソプロピル、アジピン酸イソプロピル、ステアリン酸ブチル、オレイン酸デシル、イソステアリン酸コレスチール等)、精油類(ハッカ油、ジャスミン油、シヨウ脳油、ヒノキ油、トウヒ油、リュウ油、テレピン油、ケイ皮油、ベルガモット油、ミカン油、シヨウブ油、パイン油、ラベンダー油、ベイ油、クローブ油、ヒバ油、バラ油、ユーカリ油、レモン油、ペパーミント油、タイム油、ローズ油、セージ油、メントール、シネオール、オイゲノール、シトラール、シトロネラール、ボルネオール、リナロール、ゲラニオール、カンファー、チモール、スピラントール、ピネン、リモネン、テルペン系化合物等)、シリコーン油類等の油脂成分(エモリエント成分)、
炭酸ナトリウム、炭酸水素ナトリウム、セスキ炭酸ナトリウム、ホウ砂、硫酸ナトリウム、硫化ナトリウム、硝酸ナトリウム、チオ硫酸ナトリウム、ポリリン酸ナトリウム、りん酸ナトリウム、塩化カリウム、硫化カリウム、酸化カルシウム、酸化マグネシウム、炭酸カルシウム、炭酸マグネシウム等の無機塩類、
ホウ酸、メタケイ酸、無水ケイ酸等の無機酸類、
黄色4号、青色1号、黄色202号、クロロフィル、リボフラビン、紅花、クロシン、アントラキノン等の色素類、
香料類、
アクリル樹脂、スチレン樹脂、エポキシ樹脂、ナイロン、ポリエチレン、ポリプロピレン、ポリ塩化ビニル、ポリエチレンテレフタレート樹脂、ポリテトラフルオロエタン等の高分子、これらの高分子のコポリマー、ケイ酸、ケイ酸カルシウム、天然ケイ酸アルミニウム、合成ケイ酸アルミニウム、ゼオライト、酸化チタン、タルク、カオリン、マイカ、ベントナイト等の微粉体、
硫黄、湯の花、鉱砂、雲母末、中性白土、いり糠、殺菌剤、防腐剤、
をはじめ、その他製剤上必要な成分などが挙げられる。
When using the melanin production inhibitor which concerns on 1st embodiment, or the whitening agent which concerns on 2nd embodiment as a raw material of cosmetics, the well-known component normally used can be added suitably and can be used.
For example, anionic surfactants (fatty acid soaps, sulfonate type anionic surfactants, sulfate ester type anionic surfactants, phosphate ester type anionic surfactants, acylmethyl taurine salts, monoalkyl phosphates , Acyl glutamate, isethionate, etc.), cationic surfactant (amine salt type cationic surfactant, quaternary ammonium type cationic surfactant (tetraalkylammonium type, pyridinium type)), nonionic Surfactant (glycerin fatty acid ester, propylene glycol fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, tetraoleic acid polyoxyethylene sorbit, polyoxyethylene alkyl ether, polyoxyethylene polyoxypropylene Recall, polyoxyethylene polyoxypropylene alkyl ether, polyethylene glycol fatty acid ester, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, polyglycerin fatty acid ester, etc.), amphoteric surfactant (imidazoline type, betaine type, amino acid type) , Natural surfactants such as fluorosurfactants and silicone surfactants, synthetic surfactants,
Sodium alginate, propylene glycol alginate, gum arabic, xanthan gum, pectin, tragacanth, sodium carboxymethylcellulose, methylcellulose, carboxyvinyl polymer, polyethylene glycol, polyvinyl alcohol, polyvinylpyrrolidone, cationized cellulose, cationized dextran, cationized dextrin, chitosan, Cationized vinylpyrrolidone polymer, N, N-dimethyl-3,5-methylenepiperidinium chloride polymer, milk protein, soy protein, gelatin,
Water-soluble polymers such as egg protein, sodium caseinate, whey protein,
Ginkgo biloba, pearl oyster, carrot, shikoppi, caika, inchko, yashajitsu, licorice fraction, gokahi, sempukuka, hikai, yuzuuriha, chamomile, maronier, escin, terminaria, ruscogenin, butcher bloom, cola, guarana, mate, coffee, Cacao, Plectrantus, Tandin, Bisnaga, Silymarin, Leucocyanin, Hypericum Grass, Bear Goose, Perilla, Ogon, Keigai, Rosemary, Sage, Thyme, Artemisia, Paramecium, Prunus , Plant components such as Toki, Senkyu, Chimbu, Kanokosou, Bakushi, Spruce, Glaze, safflower, camellia, Bukkuri, mint
Succinic acid, fumaric acid, citric acid, pyruvic acid, glucuronic acid, 2-hydroxybutyric acid, lactic acid, malic acid, tartaric acid, tartronic acid, methyl pyruvate, ethyl pyruvate, vitamin A acid, vitamin C derivative, vitamin D, vitamin E, active ingredients such as oligopeptide, tranexamic acid ester,
Moisturizers such as polyhydric alcohols, amino acids, mucopolysaccharides, proteins, biological extracts, fermented metabolites, polysaccharides, plant extracts, phospholipids, ceramides,
Fats and oils (soybean oil, nutka oil, jojoba oil, avocado oil, almond oil, cacao oil, olive oil, sesame oil, persic oil, castor oil, coconut oil, mink oil, beef fat, pork fat, and other natural fats and oils Hydrogenated hardened oil and synthetic triglycerides such as myristic acid glyceride and 2-ethylhexanoic acid glyceride, diglyceride etc.), waxes (carnauba wax, whale wax, beeswax, lanolin etc.), hydrocarbons (liquid paraffin, Petrolatum, paraffin, microcrystalline wax, ceresin, squalane, pristane, etc.), higher fatty acids (lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, linolenic acid, lanolinic acid, isostearic acid, etc. ), Higher alcohols (lauryl alcohol, Alcohol, stearyl alcohol, oleyl alcohol, cholesterol, 2-hexyldecanol, etc.), esters (cetyl octoate, myristyl lactate, cetyl lactate, isopropyl myristate, myristyl myristate, isopropyl palmitate, isopropyl adipate, butyl stearate, Decyl oleate, Colesteel isostearate, etc., essential oils (mint oil, jasmine oil, cypress brain oil, cypress oil, spruce oil, ryu oil, turpentine oil, cinnamon oil, bergamot oil, mandarin oil, shibu oil, pine Oil, Lavender oil, Bay oil, Clove oil, Hiba oil, Rose oil, Eucalyptus oil, Lemon oil, Peppermint oil, Thyme oil, Rose oil, Sage oil, Menthol, Cineol, Eugenol, Citral, Citronellal, Borne Lumpur, linalool, geraniol, camphor, thymol, spilanthol, pinene, limonene, terpene compounds), fats and oils such as silicone oils (emollient component),
Sodium carbonate, sodium bicarbonate, sodium sesquicarbonate, borax, sodium sulfate, sodium sulfide, sodium nitrate, sodium thiosulfate, sodium polyphosphate, sodium phosphate, potassium chloride, potassium sulfide, calcium oxide, magnesium oxide, calcium carbonate, Inorganic salts such as magnesium carbonate,
Inorganic acids such as boric acid, metasilicic acid, silicic anhydride,
Yellow No. 4, Blue No. 1, Yellow No. 202, pigments such as chlorophyll, riboflavin, safflower, crocin, anthraquinone,
Fragrances,
Polymers such as acrylic resin, styrene resin, epoxy resin, nylon, polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate resin, polytetrafluoroethane, copolymers of these polymers, silicic acid, calcium silicate, natural aluminum silicate , Fine powders such as synthetic aluminum silicate, zeolite, titanium oxide, talc, kaolin, mica, bentonite,
Sulfur, Yunohana, mineral sand, mica powder, neutral white clay, rice cake, fungicide, preservative,
And other ingredients necessary for the preparation.
<4.医薬品>
第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤を医薬品の素材として用いる場合、その剤形は、予防または治療しようとする疾患や医薬品の使用形態、投与経路等に応じて選択することができる。例えば、錠剤、被覆錠剤、丸剤、カプセル剤、顆粒剤、散剤、液剤、懸濁剤、乳剤、シロップ剤、注射剤、坐剤、浸剤、煎剤、チンキ剤等が挙げられる。これらの各種製剤は、常法に従って主薬に対して必要に応じて充填剤、増量剤、賦形剤、結合剤、保湿剤、崩壊剤、界面活性剤、滑沢剤、着色剤、矯味矯臭剤、溶解補助剤、懸濁剤、コーティング剤などの医薬の製剤技術分野において通常使用し得る既知の補助剤を用いて製剤化することができる。また、この医薬製剤中に着色剤、保存剤、香料、風味剤、甘味剤等や他の医薬品を含有させてもよい。
<4. Pharmaceuticals>
When the melanin production inhibitor according to the first embodiment or the whitening agent according to the second embodiment is used as a pharmaceutical material, the dosage form is the disease to be prevented or treated, the mode of use of the drug, the administration route, etc. Can be selected. Examples include tablets, coated tablets, pills, capsules, granules, powders, solutions, suspensions, emulsions, syrups, injections, suppositories, dip agents, decoction, tinctures and the like. These various preparations are prepared according to conventional methods as necessary with respect to the active ingredient, such as fillers, extenders, excipients, binders, humectants, disintegrants, surfactants, lubricants, coloring agents, flavoring agents. The pharmaceutical composition can be formulated using known adjuvants that can be usually used in the pharmaceutical preparation technical field, such as solubilizing agents, suspension agents, and coating agents. Moreover, you may contain a coloring agent, a preservative, a fragrance | flavor, a flavoring agent, a sweetening agent, etc. and other pharmaceuticals in this pharmaceutical formulation.
第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤の素材として用いる場合、医薬品全量に対する上記第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤の含有量は、各実施態様による所望の効果が奏される限り特に限定されないが、ウロリチン類の総量として、通常0.0001〜20質量%であり、好ましくは0.001〜5質量%であり、より好ましくは0.003〜1質量%である。 When used as a raw material for the melanin production inhibitor according to the first embodiment or the whitening agent according to the second embodiment, the melanin production inhibitor according to the first embodiment or the second embodiment with respect to the total amount of the pharmaceutical product The content of the whitening agent is not particularly limited as long as the desired effect according to each embodiment is exhibited. However, the total amount of urolithins is usually 0.0001 to 20% by mass, preferably 0.001 to 5% by mass. More preferably, it is 0.003-1 mass%.
<5.食品>
第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤を食品の素材として用いる場合、一般の食品の他、特定保健用食品、栄養補助食品、機能性食品、病者用食品、食品添加物等として使用できる。食品の形態としては、第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤を含む、清涼飲料、ミルク、プリン、ゼリー、飴、ガム、グミ、ヨーグルト、チョコレート、スープ、クッキー、スナック菓子、アイスクリーム、アイスキャンデー、パン、ケーキ、シュークリーム、ハム、ミートソース、カレー、シチュー、チーズ、バター、ドレッシング等を例示することができる。
<5. Food>
When the melanin production inhibitor according to the first embodiment or the whitening agent according to the second embodiment is used as a food material, in addition to general foods, foods for specified health use, nutritional supplements, functional foods, sick people It can be used as food for food, food additive, etc. As a form of food, soft drink, milk, pudding, jelly, rice cake, gum, gummi, yogurt, chocolate, soup containing the melanin production inhibitor according to the first embodiment or the whitening agent according to the second embodiment Cookies, snacks, ice cream, popsicles, bread, cakes, cream puffs, ham, meat sauce, curry, stew, cheese, butter, dressing and the like.
第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤は、水、タンパク質、糖質、脂質、ビタミン類、ミネラル類、有機酸、有機塩基、果汁、フレーバー類等を主成分として使用することができる。タンパク質としては、例えば、全脂粉乳、脱脂粉乳、部分脱脂粉乳、カゼイン、大豆タンパク質、鶏卵タンパク質、肉タンパク質等の動植物性タンパク質、及びこれらの加水分解物、バターなどが挙げられる。糖質としては、糖類、加工澱粉(デキストリンのほか、可溶性澱粉、ブリティッシュスターチ、酸化澱粉、澱粉エステル、澱粉エーテル等)、食物繊維などが挙げられる。脂質としては、例えば、ラード、サフラワー油、コーン油、ナタネ油、ヤシ油、これらの分別油、水素添加油、エステル交換油等の植物性油脂などが挙げられる。ビタミン類としては、例えば、ビタミンA、カロチン類、ビタミンB群、ビタミンC、ビタミンD群、ビタミンE、ビタミンK群、ビタミンP、ビタミンQ、ナイアシン、ニコチン酸、パントテン酸、ビオチン、イノシトール、コリン、葉酸などが挙げられ、ミネラル類としては、例えば、カルシウム、カリウム、マグネシウム、ナトリウム、銅、鉄、マンガン、亜鉛、セレン、乳清ミネラルなどが挙げられる。有機酸としては、例えば、リンゴ酸、クエン酸、乳酸、酒石酸などが挙げられる。これらの成分は、2種以上を組み合わせて使用してもよく、合成品及び/又はこれらを多く含む食品を用いてもよい。 The melanin production inhibitor according to the first embodiment or the whitening agent according to the second embodiment includes water, protein, carbohydrates, lipids, vitamins, minerals, organic acids, organic bases, fruit juices, flavors and the like. It can be used as a main component. Examples of the protein include whole milk powder, skim milk powder, partially skim milk powder, casein, soybean protein, chicken egg protein, meat protein, and other animal and vegetable proteins, and their hydrolysates and butter. Examples of the saccharide include saccharides, processed starch (in addition to dextrin, soluble starch, British starch, oxidized starch, starch ester, starch ether, etc.), dietary fiber, and the like. Examples of lipids include lard, safflower oil, corn oil, rapeseed oil, coconut oil, fractionated oils thereof, hydrogenated oil, and vegetable oils such as transesterified oil. Examples of vitamins include vitamin A, carotene, vitamin B group, vitamin C, vitamin D group, vitamin E, vitamin K group, vitamin P, vitamin Q, niacin, nicotinic acid, pantothenic acid, biotin, inositol, choline. And minerals include, for example, calcium, potassium, magnesium, sodium, copper, iron, manganese, zinc, selenium, and whey minerals. Examples of the organic acid include malic acid, citric acid, lactic acid, and tartaric acid. Two or more of these components may be used in combination, or a synthetic product and / or a food containing a large amount thereof may be used.
第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤を含有する食品は、常法に従って製造することができる。また、食品への第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤の、配合量、配合方法、配合時期は適宜選択することができる。さらに、必要に応じて、瓶、袋、缶、箱、パック等の適宜の容器に封入することができる。
第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤を食品の素材として用いる場合、食品全量に対する上記第一の実施態様に係るメラニン産生抑制剤又
は第二の実施態様に係る美白剤の含有量は、各実施態様による所望の効果が奏される限り特に限定されないが、ウロリチン類の総量として、通常0.00001〜3質量%であり、好ましくは0.0001〜1質量%であり、より好ましくは0.001〜0.3質量%である。
The food containing the melanin production inhibitor according to the first embodiment or the whitening agent according to the second embodiment can be produced according to a conventional method. Moreover, the compounding quantity of the melanin production inhibitor which concerns on 1st embodiment to a foodstuff, or the whitening agent which concerns on 2nd embodiment, a compounding method, and a compounding time can be selected suitably. Furthermore, it can be enclosed in appropriate containers, such as a bottle, a bag, a can, a box, and a pack, as needed.
When the melanin production inhibitor according to the first embodiment or the whitening agent according to the second embodiment is used as a food material, the melanin production inhibitor according to the first embodiment or the second embodiment with respect to the total amount of food. The content of the whitening agent according to the present invention is not particularly limited as long as the desired effect according to each embodiment is exhibited. However, the total amount of urolithins is usually 0.00001 to 3% by mass, preferably 0.0001 to 1%. It is mass%, More preferably, it is 0.001-0.3 mass%.
第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤を含有する、化粧料、医薬品、食品等は、メラニン産生抑制又は美白のために用いられるものである旨の表示を付した化粧料、医薬品、食品等として販売することができる。 An indication that cosmetics, pharmaceuticals, foods, etc. containing the melanin production inhibitor according to the first embodiment or the whitening agent according to the second embodiment are used for melanin production inhibition or whitening. Can be sold as cosmetics, pharmaceuticals, foods, etc.
前記「表示」とは、需要者に対して上記用途を知らしめるための全ての行為を意味し、上記用途を想起・類推させうるような表示であれば、表示の目的、表示の内容、表示する対象物・媒体等の如何に拘わらず、すべてが各実施態様における「表示」に該当する。しかしながら、需要者が上記用途を直接的に認識できるような表現により表示することが好ましい。具体的には、化粧料、医薬品、食品等に係る商品又は商品の包装に上記用途を記載する行為、商品又は商品の包装に上記用途を記載したものを譲渡し、引き渡し、譲渡若しくは引渡しのために展示し、輸入する行為、商品に関する広告、価格表若しくは取引書類に上記用途を記載して展示し、若しくは頒布し、又はこれらを内容とする情報に上記用途を記載して電磁気的(インターネット等)方法により提供する行為、等が例示できる。 The “display” means all acts for informing the consumer of the use, and if it is a display that can recall and analogize the use, the purpose of the display, the content of the display, the display Regardless of the object, medium, etc. to be performed, all correspond to “display” in each embodiment. However, it is preferable to display in such an expression that the consumer can directly recognize the application. Specifically, the act of describing the above-mentioned use in cosmetics, medicines, foods, etc. or the packaging of the product, the thing describing the above-mentioned use in the packaging of the product or the merchandise, and delivery, transfer or delivery Exhibiting and importing, displaying advertisements related to products, price lists or transaction documents for display or distribution, or describing the above uses in information containing these contents (such as the Internet) ) The act provided by the method can be exemplified.
一方、表示としては、行政等によって認可された表示(例えば、行政が定める各種制度に基づいて認可を受け、そのような認可に基づいた態様で行う表示)であることが好ましく、特に包装、容器、カタログ、パンフレット、POP等の販売現場における宣伝材、その他の書類等への表示が好ましい。 On the other hand, the display is preferably a display approved by the government or the like (for example, a display which is approved based on various systems determined by the government and is performed in a mode based on such approval). Display on advertising materials at sales sites such as catalogs, pamphlets, and POPs, and other documents is preferable.
また、例えば、第一の実施態様に係るメラニン産生抑制剤又は第二の実施態様に係る美白剤を含有する食品であれば、健康食品、機能性食品、特別用途食品、栄養機能食品、医薬用部外品等としての表示を例示することができ、その他厚生労働省によって認可される表示、例えば、特定保健用食品、これに類似する制度にて認可される表示を例示できる。後者の例としては、特定保健用食品としての表示、条件付き特定保健用食品としての表示、身体の構造や機能に影響を与える旨の表示、疾病リスク低減表示等を例示することができ、詳細にいえば、健康増進法施行規則(平成15年4月30日日本国厚生労働省令第86号)に定められた特定保健用食品としての表示(特に保健の用途の表示)、及びこれに類する表示が、典型的な例として列挙することが可能である。 For example, if it is a food containing the melanin production inhibitor according to the first embodiment or the whitening agent according to the second embodiment, it is a health food, a functional food, a special-purpose food, a nutritional functional food, and a pharmaceutical product. Indications such as quasi-drugs can be exemplified, and other indications approved by the Ministry of Health, Labor and Welfare, for example, foods for specific health use and indications approved under a similar system. Examples of the latter can include a display as a food for specified health use, a display as a condition specific food for specified health use, a display that affects the structure and function of the body, a display for reducing disease risk, etc. Speaking of the health promotion law enforcement regulations (April 30, 2003 Ministry of Health, Labor and Welfare Ordinance No. 86) labeling as food for specified health use (especially labeling the use of health), and similar The display can be listed as a typical example.
以下、具体的な実施例により本発明をさらに詳細に説明するが、本発明はこれらの実施例に限定されるものではない。 Hereinafter, the present invention will be described in more detail with reference to specific examples, but the present invention is not limited to these examples.
(ウロリチンの分析方法)
ウロリチン類の一例としてウロリチンAを用いた場合を説明する。ウロリチンAの分析はHPLCを用いて行った。即ち、ウロリチンA(Dalton Farma社製)を適当な溶媒に溶解させて調製した溶液を下記のHPLC条件下で分析し、純度(%)(A)およびHPLCにおけるピーク面積値(B)を用いて、下記式(1)及び式(2)によりウロリチンAのファクター及びサンプルのウロリチンA濃度を算出した。
(Method for analyzing urolithin)
A case where urolithin A is used as an example of urolithins will be described. Analysis of urolithin A was performed using HPLC. That is, a solution prepared by dissolving urolithin A (Dalton Farma) in an appropriate solvent was analyzed under the following HPLC conditions, and the purity (%) (A) and the peak area value (B) in HPLC were used. The urolithin A factor and the urolithin A concentration of the sample were calculated by the following formulas (1) and (2).
(ウロリチンAのファクター算出式)
ウロリチンAのファクター=(B)/(ウロリチンAの標準液の濃度(mg/L)×(A)/100)・・・(1)
(サンプルのウロリチンA濃度算出式)
サンプルのウロリチンA濃度(mg/L)=サンプル中のウロリチンAのピーク面積値/
ウロリチンAのファクター・・・(2)
(Calculation factor of urolithin A factor)
Factor of urolithin A = (B) / (concentration of standard solution of urolithin A (mg / L) × (A) / 100) (1)
(Sample urolithin A concentration calculation formula)
Sample urolithin A concentration (mg / L) = peak area value of urolithin A in the sample /
Factor of urolithin A (2)
(分析条件)
分析カラム:Inertsil ODS−3(250×4.6mm)(GL Science社製)
検出波長:305nm
移動相:水/アセトニトリル/酢酸 = 74/25/1
カラム温度:40℃
流速:1.0mL/min
上記条件下、ウロリチンAは16.5分に保持時間を有した。
(Analysis conditions)
Analytical column: Inertsil ODS-3 (250 × 4.6 mm) (manufactured by GL Science)
Detection wavelength: 305 nm
Mobile phase: water / acetonitrile / acetic acid = 74/25/1
Column temperature: 40 ° C
Flow rate: 1.0 mL / min
Under the above conditions, urolithin A had a retention time of 16.5 minutes.
(ウロリチンAの調製)
2−ブロモ−5−メトキシ安息香酸5g(和光純薬工業株式会社製)と塩化アルミニウム15gを150mLのクロロベンゼン中で2.5時間還流した。冷却後、反応液を氷水に移し、250mLのジエチルエーテルを用いて3回抽出を行った。得られた抽出液を減圧濃縮してジエチルエーテルを留去し、2−ブロモ−5−ヒドロキシ安息香酸4.2gを得た。得られた2−ブロモ−5−ヒドロキシ安息香酸3.9gとレゾルシノール3.9g(東京化成工業株式会社製)を9mLの4M NaOH水溶液中で60℃、30分間加熱
した。この反応液に10%硫酸銅水溶液1.8mLを加えた後、更に80℃、10分間の加熱を行った。生成した沈殿物をろ過によって回収し、ウロリチンAの白色粉末を得た。
(Preparation of urolithin A)
2-Bromo-5-methoxybenzoic acid 5 g (manufactured by Wako Pure Chemical Industries, Ltd.) and aluminum chloride 15 g were refluxed in 150 mL of chlorobenzene for 2.5 hours. After cooling, the reaction solution was transferred to ice water and extracted three times with 250 mL of diethyl ether. The obtained extract was concentrated under reduced pressure, and diethyl ether was distilled off to obtain 4.2 g of 2-bromo-5-hydroxybenzoic acid. 3.9 g of the obtained 2-bromo-5-hydroxybenzoic acid and 3.9 g of resorcinol (manufactured by Tokyo Chemical Industry Co., Ltd.) were heated in 9 mL of 4M NaOH aqueous solution at 60 ° C. for 30 minutes. After adding 1.8 mL of 10% aqueous copper sulfate solution to the reaction solution, heating was further performed at 80 ° C. for 10 minutes. The produced precipitate was collected by filtration to obtain a white powder of urolithin A.
<1.メラニン産生抑制能の評価試験>
[実施例1]
EPI−100長期維持培地(倉敷紡績社)を添加した6wellプレートに皮膚3次元モデルMEL−300(倉敷紡績社)(以下、「皮膚モデル」と称することがある。)をセットし、5%CO2存在下で37℃、18時間培養した。培養後、皮膚モデルの上層に終濃度が1、10又は100mg/Lに調製したウロリチンA溶液を0.1mL添加し、5%CO2存在下で37℃、3週間培養した。培養中、メラニン産生を誘導するためにUV照射装置を用いて1J/cm2の強度の紫外線(UV−A)照射を行った。培養後、皮膚モデルを回収し、1%SDS−EDTA含有10mM Tris−HCl緩衝液を添加して皮膚モデル中のメラニンを抽出した後、475nmの吸光度を測定することにより各皮膚モデルにおけるメラニン生成量を測定した。
<1. Evaluation test of ability to suppress melanin production>
[Example 1]
A skin three-dimensional model MEL-300 (Kurashiki Spinning Co., Ltd.) (hereinafter sometimes referred to as “skin model”) is set on a 6-well plate to which EPI-100 long-term maintenance medium (Kurashiki Spinning Co., Ltd.) is added. 2 and cultured at 37 ° C. for 18 hours. After culturing, 0.1 mL of urolithin A solution prepared to a final concentration of 1, 10 or 100 mg / L was added to the upper layer of the skin model, and cultured at 37 ° C. for 3 weeks in the presence of 5% CO 2 . During the culture, ultraviolet rays (UV-A) having an intensity of 1 J / cm 2 were irradiated using a UV irradiation apparatus in order to induce melanin production. After culturing, the skin model is recovered, 1 mM SDS-EDTA-containing 10 mM Tris-HCl buffer solution is added to extract melanin in the skin model, and then the absorbance at 475 nm is measured to measure the amount of melanin produced in each skin model. Was measured.
[比較例1]
ウロリチンA溶液を添加しなかったこと以外は上記実施例1と同様にしたものをコントロールとし、比較例1として用いた。
[Comparative Example 1]
A control similar to Example 1 except that no urolithin A solution was added was used as a control and used as Comparative Example 1.
比較例1におけるメラニン生成量を100とした場合の相対値を算出し、各ウロリチンA濃度におけるメラニン産生率(%)とした。 The relative value when the amount of melanin production in Comparative Example 1 was set to 100 was calculated, and the melanin production rate (%) at each urolithin A concentration was calculated.
ウロリチンA濃度とメラニン産生率との関係を表すグラフを図1に示す。図1に示すように、ウロリチンAは濃度依存的にメラニン産生抑制効果を有することが確認された。 A graph showing the relationship between the urolithin A concentration and the melanin production rate is shown in FIG. As shown in FIG. 1, it was confirmed that urolithin A has a melanin production inhibitory effect in a concentration-dependent manner.
<2.官能試験>
(1)化粧クリームの官能試験
表2に記載の処方に基づいて、試験品1、試験品2、対照品1の化粧クリームを製造した。具体的には、以下のようにして製造した。
まず、精製水にグリセリンを加えて70℃に加熱し、これを水相とした。一方、スクワラン、ミツロウ、精製ホホバ油、グリセリンモノステアレート、ポリオキシエチレン(20)ソルビタン・モノステアレートを加熱しながら攪拌混合し、70℃にし、これを油相
とした。水相を攪拌しながら、ウロリチンAを含む、又は、含まない50%エタノール水溶液を添加後、予め加温しておいた油相を滴下した。全量滴下後、ミキサーで乳化させ、脱気し、冷却することにより化粧クリームとした。
<2. Sensory test>
(1) Sensory test of cosmetic cream Based on the formulation described in Table 2, cosmetic creams of
First, glycerin was added to purified water and heated to 70 ° C. to obtain an aqueous phase. On the other hand, squalane, beeswax, refined jojoba oil, glycerin monostearate, polyoxyethylene (20) sorbitan monostearate were stirred and mixed while heating to 70 ° C., and this was used as the oil phase. While stirring the aqueous phase, a 50% ethanol aqueous solution containing or not containing urolithin A was added, and then the oil phase which had been heated in advance was added dropwise. After dropping the whole amount, it was emulsified with a mixer, degassed, and cooled to obtain a cosmetic cream.
<実施例2−1、2−2>
試験品1、2(それぞれ実施例2−1、2−2)、対照品(比較例2−1)の化粧クリームを用いて官能試験を実施した。
パネラーは、40代の女性7名で、上腕側部の皮膚表面に被験区と対照区を設け、被験区には各試験品のクリームを、対照区には対照品1を使用し、家庭用タンニングマシーンNEOTAN C−120で毎日30分間UVを照射し、5日後に日焼けの度合いを比較した。その結果を表3に示す。
<Examples 2-1 and 2-2>
A sensory test was carried out using the cosmetic creams of the
The panelists were seven women in their 40s. A test zone and a control zone were prepared on the surface of the upper arm side skin, each test product cream was used in the test zone, and the
本発明は、化粧料や医薬、食品等の製剤技術に適用できる。 The present invention can be applied to formulation techniques for cosmetics, medicines, foods and the like.
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