JP2018127423A - Tyrosinase activity inhibitor, medicine, cosmetic, and food browning inhibitor - Google Patents
Tyrosinase activity inhibitor, medicine, cosmetic, and food browning inhibitor Download PDFInfo
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本発明は、チロシナーゼ活性阻害剤及びこのチロシナーゼ活性阻害剤を用いた医薬品、化粧品、食品褐変防止剤に関するものである。 The present invention relates to a tyrosinase activity inhibitor and pharmaceuticals, cosmetics and food browning inhibitors using the tyrosinase activity inhibitor.
メラニンは、動物組織内にある色素であり、紫外線から皮膚や組織を保護することがその大きな役割である。しかしながら、皮膚での過剰なメラニンの産生はシミ、ソバカス、斑点などの原因になっている。そしてメラニン色素の生成に関わる酸化酵素の一つとしてチロシナーゼが知られている。 Melanin is a pigment in animal tissues, and its major role is to protect the skin and tissues from ultraviolet rays. However, excessive melanin production in the skin causes spots, freckles, and spots. Tyrosinase is known as one of the oxidases involved in the production of melanin pigment.
チロシナーゼの活性を阻害することでメラニンの生成を抑制することができれば、美白効果につながることから、チロシナーゼ活性阻害剤は化粧品素材として広く利用されている（特許文献１及び特許文献２参照）。特許文献１及び特許文献２等に開示されているチロシナーゼ活性阻害剤やメラニン生成抑制剤は、いずれも効果、安全性、安定性、コスト等の観点において必ずしも十分であるとはいえなかった。
If the production of melanin can be suppressed by inhibiting the activity of tyrosinase, it will lead to a whitening effect. Therefore, tyrosinase activity inhibitors are widely used as cosmetic materials (see
本発明は、優れたチロシナーゼ活性阻害効果を有するとともに、安心感の昂揚や積極的使用に貢献できるチロシナーゼ活性阻害剤及びこのチロシナーゼ活性阻害剤を用いた医薬品、化粧品、食品褐変防止剤を提供することを目的とする。 The present invention provides a tyrosinase activity inhibitor that has an excellent inhibitory effect on tyrosinase activity and can contribute to the promotion of active use and active use, and a pharmaceutical, cosmetic, and food browning inhibitor using the tyrosinase activity inhibitor. With the goal.
本発明者らは、上記課題を達成するために種々検討した結果、サケ鼻軟骨プロテオグリカンをタンパク質分解酵素アクチナーゼＥで消化して得られた低分子化プロテオグリカンに優れたチロシナーゼ活性阻害効果があることを見出し、本発明を完成させた。 As a result of various studies to achieve the above problems, the present inventors have found that a low molecular weight proteoglycan obtained by digesting salmon nasal cartilage proteoglycan with proteolytic enzyme actinase E has an excellent tyrosinase activity inhibitory effect. The headline and the present invention were completed.
すなわち、本発明は下記（１）〜（５）まで掲げる態様を含むものである。
（１）サケ鼻軟骨プロテオグリカンをタンパク質分解酵素アクチナーゼＥで消化して得られた低分子化プロテオグリカンを有効成分とするチロシナーゼ活性阻害剤であることを要旨とする。
（２）前記（１）に記載の低分子化プロテオグリカンを０．０００３３重量％以上含むチロシナーゼ活性阻害剤であることを要旨とする。
（３）前記（１）に記載の低分子化プロテオグリカンを含む皮膚外用剤であることを要旨とする。
（４）前記（１）に記載の低分子化プロテオグリカンを含む美白化粧料であることを要旨とする。
（５）前記（１）に記載の低分子化プロテオグリカンを含む食品褐変防止剤であることを要旨とする。
That is, the present invention includes the following aspects (1) to (5).
(1) The gist of the present invention is a tyrosinase activity inhibitor comprising a low molecular weight proteoglycan obtained by digesting salmon nasal cartilage proteoglycan with proteolytic enzyme actinase E as an active ingredient.
(2) The gist is that it is a tyrosinase activity inhibitor containing 0.00033% by weight or more of the low molecular weight proteoglycan described in (1).
(3) The gist is an external preparation for skin containing the low molecular weight proteoglycan according to (1).
(4) The gist is a whitening cosmetic comprising the low molecular weight proteoglycan according to (1).
(5) The gist of the present invention is a food browning inhibitor containing the low molecular weight proteoglycan according to (1).
本発明によれば、優れたチロシナーゼ活性阻害効果を有していること、また、従来から非常に強力な活性を有することがよく知られているコウジ酸と比較しても、より強いチロシナーゼ活性阻害効果を示すことが明らかとなり、且つ天然物を原料としていることから、安心感の昂揚や積極的使用に貢献できるチロシナーゼ活性阻害剤及びこのチロシナーゼ活性阻害剤を用いた医薬品、化粧品、食品褐変防止剤が提供できる。 According to the present invention, compared with kojic acid, which is well known to have an excellent tyrosinase activity inhibitory effect and to have a very strong activity from the past, stronger tyrosinase activity inhibition Tyrosinase activity inhibitor capable of contributing to the promotion of peace of mind and active use, and pharmaceuticals, cosmetics, and food browning inhibitors using this tyrosinase activity inhibitor, since it is clear that it exhibits effects and is made from natural products. Can be provided.
以下、実施の形態をより具体的に説明するが、本発明の技術的思想を具体化するための方法を例示するものであって、本発明の技術的思想は、下記のものに特定するものではない。本発明の技術的思想は、特許請求の範囲に記載された請求項が規定する技術的範囲内において、種々の変更を加えることができる。 Hereinafter, the embodiment will be described in more detail, but it exemplifies a method for embodying the technical idea of the present invention, and the technical idea of the present invention is specified as follows. is not. The technical idea of the present invention can be variously modified within the technical scope defined by the claims described in the claims.
本発明の実施の形態に係る原料プロテオグリカンは、魚類に存在するグリコサミノグリカンとタンパク質の共有結合物からなる分子量数十万から数百万の高分子化合物である。 The raw material proteoglycan according to the embodiment of the present invention is a high molecular compound having a molecular weight of several hundred thousand to several million consisting of a covalently bonded product of glycosaminoglycan and protein present in fish.
本発明の実施の形態に係る低分子化プロテオグリカンは、サケ鼻軟骨由来原料プロテオグリカンをタンパク質分解酵素であるアクチナーゼＥにより消化することで製造することができる。 The low molecular weight proteoglycan according to the embodiment of the present invention can be produced by digesting salmon nasal cartilage-derived raw material proteoglycan with actinase E, which is a proteolytic enzyme.
前記原料プロテオグリカンは、青森県などの郷土料理としてよく知られている「氷頭なます」をヒントに工業原料として実用化されたもので、食経験のあるサケ鼻軟骨から酢酸を用いて抽出されており、安心感の昂揚や積極的使用に貢献できるものである。 The raw material proteoglycan has been put into practical use as an industrial raw material with the hint of “Hyoshina namasu”, which is well-known as a local dish in Aomori Prefecture, etc., and extracted from acetic acid from salmon nasal cartilage. It can contribute to raising the sense of security and active use.
本発明の実施の形態に係る低分子化プロテオグリカンには、優れたチロシナーゼ活性阻害効果があり、医薬品、化粧品あるいは食品褐変防止剤に利用することができる。 The low molecular weight proteoglycan according to the embodiment of the present invention has an excellent inhibitory effect on tyrosinase activity and can be used as a pharmaceutical, cosmetic or food browning inhibitor.
以下に実施例を示して本発明の実施の形態を具体的に説明するが、これは単に例示の目的で述べるものであり、本発明はこれらの実施例に限定されるものではない。 Hereinafter, embodiments of the present invention will be described in detail with reference to examples. However, these are merely described for illustrative purposes, and the present invention is not limited to these examples.
（低分子化プロテオグリカンの製造）
原料プロテオグリカン（市販の鮭由来プロテオグリカン：角弘プロテオグリカン研究所社製）を、タンパク質分解酵素アクチナーゼＥ（科研製薬製）を用いて消化し、得られた分解生成物をセファアクリルＳ−５００ＨＲゲルろ過クロマトグラフィー（Ｖ０＝２２０ｍＬ、Ｖｔ＝５８９ｍＬ）により精製し、溶出位置３５０ｍＬから５５０ｍＬまでの画分を集め（４１０ｋＤａデキストランの溶出位置は４０７ｍＬ）、低分子化プロテオグリカンとした。この低分子化プロテオグリカンを試料としてチロシナーゼ活性阻害試験を行った。
(Production of low molecular weight proteoglycans)
The raw material proteoglycan (commercially available koji-derived proteoglycan: manufactured by Kakuhiro Proteoglycan Research Institute) was digested with proteolytic enzyme actinase E (manufactured by Kaken Pharmaceutical Co., Ltd.), and the resulting degradation product was separated by Sephaacryl S-500HR gel filtration chromatography. (V 0 = 220 mL, V t = 589 mL), and fractions from elution position 350 mL to 550 mL were collected (410 kDa dextran elution position was 407 mL) to obtain a low molecular weight proteoglycan. Using this low molecular weight proteoglycan as a sample, a tyrosinase activity inhibition test was conducted.
（低分子化プロテオグリカンを用いたチロシナーゼ活性阻害試験）
マッシュルーム由来チロシナーゼ（シグマ社製）を０．１Ｍリン酸緩衝液（ｐＨ６．８）に溶解して酵素溶液（４０Ｕ／ｍＬ）とした。基質はＬ−ＤＯＰＡ（３，４−Ｄｉｈｙｄｒｏｘｙ−Ｌ−ｐｈｅｎｙｌａｌａｎｉｎｅ，シグマ社製）を用い、０．１Ｍリン酸緩衝液（ｐＨ６．８）に溶解して２ｍＭの基質溶液とした。各濃度の低分子化プロテオグリカン溶液を調製し、陽性対照にはコウジ酸（東京化成製）を用いた。酵素反応は、９６穴マイクロプレートにて行った。マイクロプレートの各ウェルに酵素溶液５０μＬと阻害剤５０μＬを加え、充分混合攪拌した。室温で２分間プレインキュベートした後、基質であるＬ−ＤＯＰＡ溶液を５０μＬ添加し、３７℃で１０分間インキュベートした。その後、マイクロプレートリーダー（ＴｒｉＳｔａｒ ＬＢ９４１、ベルトールドジャパン社製）を用いて、波長４５０ｎｍにおける吸光度を測定した。チロシナーゼ活性阻害剤を用いない区分（チロシナーゼの活性を阻害していないもの）の吸光度をＡ、各阻害剤を添加した区分（チロシナーゼの活性を阻害したもの）の吸光度をＢとし、チロシナーゼ阻害率を 阻害率（％）＝｛（Ａ−Ｂ）／Ａ｝×１００ として計算した。
(Tyrosinase activity inhibition test using low molecular weight proteoglycan)
Mushroom-derived tyrosinase (manufactured by Sigma) was dissolved in 0.1 M phosphate buffer (pH 6.8) to obtain an enzyme solution (40 U / mL). The substrate used was L-DOPA (3,4-Dihydroxy-L-phenylalanine, manufactured by Sigma) and dissolved in 0.1 M phosphate buffer (pH 6.8) to give a 2 mM substrate solution. Low molecular weight proteoglycan solutions of various concentrations were prepared, and kojic acid (manufactured by Tokyo Chemical Industry) was used as a positive control. The enzyme reaction was performed in a 96-well microplate. 50 μL of the enzyme solution and 50 μL of the inhibitor were added to each well of the microplate, and mixed well. After pre-incubating for 2 minutes at room temperature, 50 μL of the substrate L-DOPA solution was added and incubated at 37 ° C. for 10 minutes. Thereafter, the absorbance at a wavelength of 450 nm was measured using a microplate reader (TriStar LB941, manufactured by Bertolu Japan). Absorbance of the section without tyrosinase activity inhibitor (not inhibiting the activity of tyrosinase) is A, Absorbance of the section with each inhibitor added (inhibiting tyrosinase activity) is B, and tyrosinase inhibition rate is Inhibition rate (%) = {(A−B) / A} × 100.
低分子化プロテオグリカン及び陽性対照であるコウジ酸を用いてマッシュルーム由来チロシナーゼ活性に対する阻害効果を調べた結果を図１に示す。低分子化プロテオグリカンは陽性対照であるコウジ酸よりも強い阻害効果を示した。低分子化プロテオグリカンは濃度３．３、９．９、３３、９９、３３０、９９０μｇ／ｍＬにおいて、マッシュルーム由来チロシナーゼ活性をそれぞれ１８．０、２５．６、５３．４、７８．８、８２．９、８４．９％阻害した。一方、陽性対照であるコウジ酸は濃度２０、４０、６０、８０、１００μｇ／ｍＬにおいて、マッシュルーム由来チロシナーゼ活性をそれぞれ３６.１、５３．３、６５．１、６８．５、７０．４％阻害した。これらの結果から、マッシュルーム由来チロシナーゼ活性に対する低分子化プロテオグリカン及びコウジ酸の５０％阻害濃度ＩＣ５０は、それぞれ２８．５、３５．３μｇ／ｍＬと計算され、低分子化プロテオグリカンには、コウジ酸よりも１．２４倍の強いチロシナーゼ活性阻害効果があることが分かった。なお、原料プロテオグリカンには顕著なチロシナーゼ活性阻害効果は見られなかった。 FIG. 1 shows the results of examining the inhibitory effect on mushroom-derived tyrosinase activity using low molecular weight proteoglycan and kojic acid as a positive control. The low molecular weight proteoglycan showed a stronger inhibitory effect than kojic acid which is a positive control. The low molecular weight proteoglycans have mushroom-derived tyrosinase activity of 18.0, 25.6, 53.4, 78.8, and 82.9 at concentrations of 3.3, 9.9, 33, 99, 330, and 990 μg / mL, respectively. 84.9% inhibition. On the other hand, kojic acid as a positive control inhibits mushroom-derived tyrosinase activity by 36.1, 53.3, 65.1, 68.5, and 70.4% at concentrations of 20, 40, 60, 80, and 100 μg / mL, respectively. did. From these results, the 50% inhibitory concentrations IC50 of low molecular weight proteoglycan and kojic acid for mushroom-derived tyrosinase activity were calculated to be 28.5 and 35.3 μg / mL, respectively. It was found to have a 1.24 times stronger tyrosinase activity inhibitory effect. The proteoglycan raw material did not show a significant inhibitory effect on tyrosinase activity.
本発明のチロシナーゼ活性阻害剤は、従来のチロシナーゼ活性阻害剤と同様に、医薬品、化粧品及び食品褐変防止剤の有効成分として利用可能である。この場合、チロシナーゼ阻害剤の添加量は、特に限定されるものではなく、皮膚外用剤や化粧料、食品褐変防止剤の種類によって異なるが、目的にあわせて適宜配合すればよい。 The tyrosinase activity inhibitor of the present invention can be used as an active ingredient of pharmaceuticals, cosmetics, and food browning inhibitors, similarly to conventional tyrosinase activity inhibitors. In this case, the addition amount of the tyrosinase inhibitor is not particularly limited, and may vary depending on the type of external preparation for skin, cosmetics, and food browning inhibitor, but may be appropriately blended according to the purpose.
本発明のチロシナーゼ活性阻害剤を皮膚外用剤として利用する場合、その形態としては、軟膏剤、クリーム剤、乳剤、ゲル剤、ローション剤、トリートメント剤、貼付剤などが挙げられる。 When the tyrosinase activity inhibitor of the present invention is used as an external preparation for skin, examples of the form include ointments, creams, emulsions, gels, lotions, treatments, patches and the like.
また、本発明のチロシナーゼ活性阻害剤を化粧料として利用する場合、その形態としては、クリーム、乳液、ローション、化粧水、ジェル、美容液、パックなどの基礎化粧品、また、日焼け止めクリーム、日焼け止めローション、日焼け止めリップクリームなどの日焼け止め化粧料、また、メイクアップベースクリーム、パウダーファンデーション、リキッドファンデーション、口紅などのメイクアップ化粧料、さらには、ハンドクリーム、レッグクリーム、ボディローション、浴用剤などのボディ用化粧料などが挙げられる。 Further, when the tyrosinase activity inhibitor of the present invention is used as a cosmetic, the forms thereof include basic cosmetics such as creams, emulsions, lotions, lotions, gels, serums, packs, sunscreen creams, sunscreens Sunscreen cosmetics such as lotion and sunscreen lip balm, makeup cosmetics such as makeup base cream, powder foundation, liquid foundation and lipstick, hand cream, leg cream, body lotion, bath preparation, etc. Examples include body cosmetics.
さらに、本発明のチロシナーゼ活性阻害剤を食品褐変防止剤として利用する場合、その対象となる食品としては、各種フルーツ、椎茸、マッシュルームなどのきのこ類、カニやエビなどの海産物などが挙げられる。その使用方法としては、本発明の阻害剤を適当な媒体で希釈し、この溶液を対象物に噴霧、浸漬させることで食品表面の褐変を防止することができる。 Furthermore, when the tyrosinase activity inhibitor of the present invention is used as a food browning inhibitor, foods to be targeted include various fruits, mushrooms such as shiitake mushrooms and mushrooms, and marine products such as crabs and shrimps. As the method of use, browning of the food surface can be prevented by diluting the inhibitor of the present invention with an appropriate medium and spraying and immersing this solution on the object.
本発明の低分子化プロテオグリカンは、優れたチロシナーゼ阻害活性を有し、しかも、青森県などの郷土料理としてよく知られている「氷頭なます」をヒントに工業原料として実用化されたプロテオグリカンから酵素分解により得られる物質であるため、安心感の昂揚や積極的使用に貢献できるものである。従って、低分子化プロテオグリカンを有効成分とするチロシナーゼ活性阻害剤は、医薬品、化粧品あるいは食品褐変防止剤の分野で広く利用することが可能である。
The low molecular weight proteoglycan of the present invention has an excellent tyrosinase inhibitory activity, and is also a proteoglycan that has been put into practical use as an industrial raw material with hints of “Hyoshinaru”, a well-known local dish such as Aomori Prefecture Because it is a substance obtained by enzymatic degradation, it can contribute to the promotion of safe use and active use. Therefore, tyrosinase activity inhibitors containing low molecular weight proteoglycans as active ingredients can be widely used in the fields of pharmaceuticals, cosmetics, and food browning inhibitors.
Claims (5)
The food browning prevention agent containing the low molecular weight proteoglycan of Claim 1.
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| KR102464344B1 (en) * | 2022-02-08 | 2022-11-04 | 주식회사 코씨드바이오팜 | Cosmetic Composition for Prohibiting Skin Pigmentation by Personal DTC Gene Comprising Proteoglycan From Salmon as Active Ingredient |
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