JP2015074615A - Enhancers for glutathione production - Google Patents
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Abstract
Description
本発明は、コウジ酸および／またはその誘導体を有効成分とすることを特徴とするグルタチオン産生促進剤に関する。 The present invention relates to a glutathione production promoter characterized by comprising kojic acid and / or a derivative thereof as an active ingredient.
グルタチオンは、システインのアミノ基とグルタミン酸のカルボキシル基間のペプチド結合を有するトリペプチドであり、抗酸化物質の一つとして、フリーラジカルや過酸化物といった活性酸素種から細胞を保護する補助的役割を有する物質である。このグルタチオン自体が、日本薬局方に収載された医薬品であり、健康や美容の維持に有用なサプリメントとして販売されている。このグルタチオンの工業的な製法としては、グリシンやＬ−システインを原料として合成させる方法や、γ−グルタミルシステイン合成酵素やグルタチオン合成酵素を利用して酵素により合成する方法、酵母等から抽出する方法等が知られている（非特許文献１）。 Glutathione is a tripeptide having a peptide bond between the amino group of cysteine and the carboxyl group of glutamic acid, and as an antioxidant, plays an auxiliary role in protecting cells from reactive oxygen species such as free radicals and peroxides. It is a substance that has. This glutathione itself is a drug listed in the Japanese Pharmacopoeia and is sold as a supplement useful for maintaining health and beauty. As an industrial production method of this glutathione, a method of synthesizing glycine or L-cysteine as a raw material, a method of synthesizing with an enzyme using γ-glutamylcysteine synthetase or glutathione synthetase, a method of extracting from yeast, etc. Is known (Non-Patent Document 1).
このグルタチオンは、生体内に広く分布しており、細胞内に一定濃度で存在し、種々の細胞、生体保護機能を果たしているため、単に、グルタチオンを外部から添加するのみならず、細胞内でのグルタチオン産生促進を行う製剤が求められている。 This glutathione is widely distributed in the living body, exists at a constant concentration in the cell, and functions to protect various cells and living organisms. Therefore, glutathione is not only added from the outside, but also in the cell. There is a need for formulations that promote glutathione production.
一方、コウジ酸およびその誘導体は、出願人等によってそのメラニン合成抑制作用等を見出すことで皮膚外用剤等として使用されている物質である（特許文献１〜４等）。 On the other hand, kojic acid and its derivatives are substances that are used as an external preparation for skin by finding out the melanin synthesis inhibitory action and the like by the applicants and the like (Patent Documents 1 to 4, etc.).
皮膚外用等の目的でグルタチオンそのものを使用することは、生理活性について不明な点が多く、グルタチオン自体が不安定な物質であるなどの理由から、汎用するには問題が生じることがあり、生体におけるグルタチオン産生促進機能を有する物質が広く求められている。また、安全な条件のもと使用されるグルタチオンの工業的生産において、特に抽出法のような微生物等細胞増殖を利用した製造方法による場合、微生物のグルタチオン産生を促進することで、より高濃度でグルタチオンを含有させ収率を上げることができる。かかる現状に鑑み、本発明は、グルタチオンの産生促進剤およびグルタチオン産生促進方法を提供することを目的とする。 The use of glutathione itself for the purpose of external skin use has many unclear points regarding its physiological activity, and glutathione itself is an unstable substance. Substances having a glutathione production promoting function are widely demanded. In addition, in the industrial production of glutathione used under safe conditions, especially in the case of a production method utilizing cell growth such as microorganisms such as extraction methods, by promoting the production of glutathione by microorganisms, Glutathione can be contained to increase the yield. In view of the present situation, an object of the present invention is to provide a glutathione production promoter and a glutathione production promotion method.
本発明者は、上記課題を解決すべく鋭意研究を重ねた結果、下記の発明が上記目的に合致することを見出し、本発明に至った。 As a result of intensive studies to solve the above problems, the present inventor has found that the following inventions meet the above object, and have reached the present invention.
すなわち、本発明は、以下の発明に係るものである。
＜１＞コウジ酸および／またはその誘導体を含有することを特徴とするグルタチオン産生促進剤。
That is, the present invention relates to the following inventions.
<1> A glutathione production promoter comprising kojic acid and / or a derivative thereof.
本発明のグルタチオン産生促進剤によれば、細胞内でのグルタチオン産生を促進することができる。この細胞として、例えば皮膚細胞内でのグルタチオン産生促進することで、グルタチオンが寄与する生体保護機能を効率よく達成することができる。 According to the glutathione production promoter of the present invention, it is possible to promote glutathione production in cells. As this cell, for example, by promoting the production of glutathione in skin cells, it is possible to efficiently achieve a biological protective function contributed by glutathione.
以下に本発明の実施の形態を詳細に説明するが、以下に記載する構成要件の説明は、本発明の実施態様の一例（代表例）であり、本発明はその要旨を超えない限り、以下の内容に限定されない。 DESCRIPTION OF EMBODIMENTS Embodiments of the present invention will be described in detail below. However, the description of the constituent elements described below is an example (representative example) of an embodiment of the present invention. It is not limited to the contents.
本発明は、コウジ酸および／またはその誘導体を含有することを特徴とするグルタチオン産生促進剤である。 The present invention is a glutathione production promoter characterized by containing kojic acid and / or a derivative thereof.
［コウジ酸］
本発明は、コウジ酸および／またはその誘導体を用いる。このコウジ酸は、以下の式（１）で表される化合物であり、Ｃ6Ｈ6Ｏ4の化学式であらわされ、５−ｈｙｄｒｏｘｙ−２−ｈｙｄｒｏｘｙｍｅｔｈｙｌ−４−ｐｙｒｏｎｅ（５−ヒドロキシ−２−ヒドロキシメチル−４−ピロン）または、５−Ｈｙｄｒｏｘｙ−２−（ｈｙｄｒｏｘｙｍｅｔｈｙｌ）−４Ｈ−ｐｙｒａｎ−４−ｏｎｅ（５−ヒドロキシ２−（ヒドロキシメチル）−４Ｈ−ピラン−４−オン）、５−オキシ−２−オキシメチル−γ−ピロンとも呼ばれる。本発明においては、このコウジ酸の誘導体も用いることができ、例えば、コウジ酸のエステル化物、エーテル誘導体化物、２位のヒドロキシメチル基に糖類を結合させた配糖体類等があげられる。具体的な化合物名としては、コウジ酸グルコシド、コウジ酸マンノシド、コウジ酸グルコサミド、エチル化コウジ酸、コウジ酸フラクトシドなどが挙げられる。
[Kojic acid]
The present invention uses kojic acid and / or its derivatives. This kojic acid is a compound represented by the following formula (1), which is represented by the chemical formula of C 6 H 6 O 4 and is 5-hydroxy-2-hydroxymethyl-4-pyrone (5-hydroxy-2-hydroxy). Methyl-4-pyrone) or 5-hydroxy-2- (hydroxymethyl) -4H-pyran-4-one (5-hydroxy-2- (hydroxymethyl) -4H-pyran-4-one), 5-oxy-2 -Also called oxymethyl-γ-pyrone. In the present invention, a derivative of this kojic acid can also be used, and examples thereof include esterified products of kojic acid, ether-derivatized products, and glycosides in which a saccharide is bonded to the hydroxymethyl group at the 2-position. Specific compound names include kojic acid glucoside, kojic acid mannoside, kojic acid glucosamide, ethylated kojic acid, kojic acid fructoside and the like.
コウジ酸および／またはその誘導体は、麹菌から発見されたものであり、コウジ酸生産能を有する公知の菌株を培養して得られるコウジ酸を主成分とする発酵液、該発酵液の濃縮液、および該発酵液からコウジ酸を抽出して結晶化したものなどが使用されるほか、味噌や酒粕等の食品素材やこれらの応用素材、抽出物等の利用においてコウジ酸を含有するものを包含する概念である。 Kojic acid and / or its derivatives are those discovered from Aspergillus oryzae, fermented liquid mainly composed of kojic acid obtained by culturing a known strain having kojic acid-producing ability, concentrated liquid of the fermented liquid, In addition to those obtained by extracting and crystallizing kojic acid from the fermentation broth, including food materials such as miso and sake lees, applied materials thereof, extracts containing kojic acid, etc. It is a concept.
本発明は、グルタチオンの産生を促進することを特徴とする。グルタチオンは、前述のように生体内に広く分布するトリペプチドであり、健康や美容の目的で使用されている物質である。別名は、γ−Ｌ−グルタミル−Ｌ−システイニル−グリシンである。このグルタチオンは、動植物、微生物に存在し、細胞内に一定濃度で存在することが知られている。本発明のグルタチオン産生促進剤を用いることで、細胞内でのグルタチオン産生を促進することができる。 The present invention is characterized by promoting the production of glutathione. Glutathione is a tripeptide widely distributed in the living body as described above, and is a substance used for health and beauty purposes. Another name is γ-L-glutamyl-L-cysteinyl-glycine. It is known that this glutathione exists in animals and plants and microorganisms and exists in cells at a constant concentration. Intracellular glutathione production can be promoted by using the glutathione production promoter of the present invention.
グルタチオンは、細胞内で細胞内チオール環境の維持や細胞の解毒など、様々な生理作用を通してフリーラジカルや過酸化物といった活性酸素種から細胞を保護する補助的役割を有し、生体の様々な機能を維持するために重要な役割を果たしていると注目されている物質である。 Glutathione has an auxiliary role in protecting cells from reactive oxygen species such as free radicals and peroxides through various physiological functions such as maintaining intracellular thiol environment and detoxification of cells in cells. It is a substance that has been attracting attention as playing an important role in maintaining
本発明はコウジ酸および／またはその誘導体が優れたグルタチオン産生促進作用を有していることを見出したことに基づいており、例えばこれを皮膚外用剤へ配合することで、皮膚の抗酸化機能を強化し、酸化ストレスに関連する加齢による細胞の老化を遅らせることが期待できる。さらには、グルタチオン産生促進により、適宜その使用形態を調整することでヒトにおいて、美白効果、美肌効果、疲労回復、解毒作用、二日酔い改善、肝機能改善といった機能も発揮する。 The present invention is based on the finding that kojic acid and / or its derivatives have an excellent glutathione production promoting action. For example, by adding this to a skin external preparation, the antioxidant function of the skin is improved. It can be expected to strengthen and delay aging of cells with aging associated with oxidative stress. Furthermore, by promoting the production of glutathione, the function of whitening, skin beautification, fatigue recovery, detoxification, hangover improvement, liver function improvement is also exerted in humans by appropriately adjusting the usage pattern.
本発明のグルタチオン産生促進剤は、前述のように皮膚外用剤の態様で提供されることができる。本発明を皮膚外用剤とする場合は、本発明の有効成分である前記式（１）で表される化合物および／またはその誘導体を含有する製剤の形態で提供することができる。ここで、製剤の形態は外用として提供し得るものであり、皮膚外用剤一般に許容し得る基剤を選択し患部に直接塗布して使用される。この場合には、ローションやエッセンス等に代表される均一系製剤のほか、クリームや乳液に代表されるＯ／Ｗ、Ｗ／Ｏ型などの一般乳化系、Ｗ／Ｏ／Ｗ、Ｏ／Ｗ／Ｏ型の特殊な多層エマルジョン、その他にもペースト剤、軟膏及びチンキ剤等の塗布剤型、エアゾール剤、スプレー剤等の噴霧剤型、パップ剤、プラスター剤等の貼付剤型など公知の形態の基礎基剤としても他の成分と組合せて幅広く使用に供されるものであり特段の制約はない。 The glutathione production promoter of the present invention can be provided in the form of an external preparation for skin as described above. When the present invention is used as an external preparation for skin, it can be provided in the form of a preparation containing the compound represented by the formula (1) and / or a derivative thereof as the active ingredient of the present invention. Here, the form of the preparation can be provided for external use, and an externally applied skin preparation is generally selected and applied directly to the affected area. In this case, in addition to homogeneous preparations represented by lotions and essences, general emulsification systems such as O / W and W / O types represented by creams and emulsions, W / O / W, O / W / O-type special multi-layer emulsions, other types such as pastes, ointments and tinctures, sprays such as aerosols and sprays, patch types such as poultices and plasters, etc. The basic base is also used in combination with other components and is not particularly limited.
外用の場合においてコウジ酸および／またはその誘導体の配合量は、製剤設計の形態によって変わるが、概ね製剤全体に対して、０．００１乃至２０重量％、好ましくは０．０１乃至１０重量％、さらに好ましくは０．１乃至５重量％の範囲で配合すれば十分な効果が発揮できる。また、本発明の製剤設計の際には、他の機能性素材と組み合わせて使用することができる。 In the case of external use, the amount of kojic acid and / or a derivative thereof varies depending on the form of the drug product design, but is generally 0.001 to 20% by weight, preferably 0.01 to 10% by weight, further based on the whole drug product. A sufficient effect can be exhibited if it is blended preferably in the range of 0.1 to 5% by weight. Moreover, in the formulation design of the present invention, it can be used in combination with other functional materials.
外用での適用の場合、通常に用いられる種々の公知の有効成分、例えば、美白剤として公知のアスコルビン酸、ハイドロキノン及びこれの誘導体、レゾルシン類、縮合型タンニン類、カフェー酸、イソコウジ酸、エラグ酸等のフェノール性化合物、末梢血管拡張剤としてはビタミンＥ、ビタミンＥニコチネート、ニコチン酸、ニコチン酸アミド、ニコチン酸ベンジル等の各種ビタミン類、ショウキョウチンキ、トウガラシチンキ、消炎剤としては副腎皮質ホルモン、ε−アミノカプロン酸、塩化リゾチーム、グリチルリチン、アラントイン等の各種化合物、その他にも胎盤抽出物、甘草抽出物、紫根エキス、乳酸菌培養抽出物などの動植物・微生物由来の各種抽出物等を本発明の効果を損なわない範囲で、その時々の目的に応じて適宜添加して使用することができる。 For external application, various known active ingredients that are commonly used, for example, ascorbic acid, hydroquinone and derivatives thereof known as whitening agents, resorcins, condensed tannins, caffeic acid, isokodiic acid, ellagic acid Phenolic compounds such as vitamin E, vitamin E nicotinate as peripheral vasodilators, various vitamins such as nicotinic acid, nicotinic acid amide, benzyl nicotinate, ginger tincture, chili pepper tincture, as anti-inflammatory agents, corticosteroids, Effects of the present invention include various compounds such as ε-aminocaproic acid, lysozyme chloride, glycyrrhizin, allantoin, and other extracts derived from animals, plants, and microorganisms such as placenta extract, licorice extract, purple root extract, and lactic acid bacteria culture extract. Is added as appropriate according to the purpose at the time. It can be used.
さらに、本発明の外用剤にはこれら公知の有効成分に加え、油脂類などの基剤成分のほか、必要に応じて公知の保湿剤、防腐剤、酸化防止剤、キレート剤、ｐＨ調整剤、香料、着色剤等種々の添加剤を本発明の効果を損なわない範囲で併用することができる。 Furthermore, in addition to these known active ingredients, the external preparation of the present invention, in addition to base components such as fats and oils, if necessary, known moisturizers, preservatives, antioxidants, chelating agents, pH adjusters, Various additives, such as a fragrance | flavor and a coloring agent, can be used together in the range which does not impair the effect of this invention.
本発明は、コウジ酸および／またはその誘導体を混合することによるグルタチオン産生促進方法としても達成することができる。例えば、前述のようにグルタチオンは、細胞からの抽出法によっても製造されているため、本発明のグルタチオン産生促進剤によってグルタチオンの産生を促進することで、細胞内、またタンパク質あたりのグルタチオン濃度を向上させることができる。これによって、細胞から抽出する方法によるグルタチオンの抽出効率を向上させることができる。よって、グルタチオンの製造方法において、その細胞培養工程における、細胞内のグルタチオン濃度を向上させる本発明のグルタチオン産生促進方法は最終的なグルタチオンの収率向上等に効果を発揮する。 The present invention can also be achieved as a method for promoting glutathione production by mixing kojic acid and / or its derivatives. For example, as described above, glutathione is also produced by extraction from cells. Therefore, by promoting glutathione production with the glutathione production promoter of the present invention, the glutathione concentration per cell and per protein is improved. Can be made. Thereby, the extraction efficiency of glutathione by the method of extracting from cells can be improved. Therefore, in the method for producing glutathione, the glutathione production promotion method of the present invention that improves the intracellular glutathione concentration in the cell culturing step is effective in improving the final yield of glutathione.
以下、実施例により本発明を更に詳細に説明するが、本発明は、その要旨を変更しない限り以下の実施例に限定されるものではない。 EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to a following example, unless the summary is changed.
［細胞培養によるグルタチオン濃度の変化］
以下の細胞培養用の培地を用いて、各試料を添加し、所定時間培養した後のグルタチオン濃度の変化を評価した。
[Changes in glutathione concentration by cell culture]
Each sample was added using the following medium for cell culture, and the change in glutathione concentration after culturing for a predetermined time was evaluated.
［細胞培養用の培地調整］
ヒト正常皮膚線維芽細胞Ｃｅｌｌ Ｓｙｓｔｅｍ−Ｆｂ Ｃｅｌｌｓ（ＤＳファーマバイオメディカル製）を１０％ＦＢＳ（ウシ胎児血清）および１％ＮＥＡＡ（非必須アミノ酸）含有のＭＥＭ（Ｅａｇｌｅ‘ｓ Ｍｉｎｉｍｕｍ Ｅｓｓｅｎｔｉａｌ Ｍｅｄｉｕｍ）にて培養した。
[Medium preparation for cell culture]
Cultured human normal skin fibroblasts Cell System-Fb Cells (DS Pharma Biomedical) in MEM (Eagle's Minimum Essential Medium) containing 10% FBS (fetal bovine serum) and 1% NEAA (non-essential amino acid). did.
［実施例、比較例および参考例における試料の添加］
「実施例１、２」
２４ウェルプレートに０．８×１０5ｃｅｌｌｓ／wellの細胞を播種し、一晩培養後、１％ＦＢＳおよび１％ＮＥＡＡ含有のＭＥＭにて培地交換すると同時にコウジ酸（三省製薬社内製）の水溶液を添加した。培地中のコウジ酸濃度が２．５ｍＭとなるように添加したものを実施例１とし、コウジ酸濃度が５．０ｍＭとなるように添加したものを実施例２とした。
[Addition of samples in Examples, Comparative Examples and Reference Examples]
"Examples 1 and 2"
A cell of 0.8 × 10 5 cells / well is seeded on a 24-well plate, and after overnight culture, the medium is changed with MEM containing 1% FBS and 1% NEAA, and at the same time, an aqueous solution of kojic acid (manufactured by Sansho Pharmaceutical) Was added. What was added so that the kojic acid concentration in a culture medium might be 2.5 mM was set as Example 1, and what was added so that a kojic acid concentration might be set to 5.0 mM was set as Example 2.
「参考例１」
コントロールとして、コウジ酸の添加に代え試料無添加のものを参考例１として後述の培養後のグルタチオンの定量をおこなった。
"Reference Example 1"
As a control, glutathione after culturing described below was quantified as Reference Example 1 in which no sample was added instead of kojic acid.
「比較例１」
比較対照として、グルタチオンの構成アミノ酸、システインの誘導体であるＮ−アセチル−Ｌ−システイン（ＮＡＣ、ナカライテスク製）を添加したものを比較例１とした。ＮＡＣの添加量は、培地中のＮＡＣ濃度が１０ｍＭとなるように添加した。
"Comparative Example 1"
As a comparative control, Comparative Example 1 was obtained by adding N-acetyl-L-cysteine (NAC, manufactured by Nacalai Tesque), which is a derivative of glutathione and a derivative of cysteine. The amount of NAC added was such that the NAC concentration in the medium was 10 mM.
［グルタチオンの定量］
前述の各試料添加４８時間後、Ｍ−ＰＥＲ（Ｔｈｅｒｍｏ）にて細胞のタンパク質を抽出し、これを測定試料としてＢＣＡ法によるタンパク質定量、およびＴｏｔａｌ Ｇｌｕｔａｔｈｉｏｎｅ Ｑｕａｎｔｉｆｉｃａｔｉｏｎ Ｋｉｔ（ＤＯＪＩＮＤＯ製）を用いたグルタチオン定量を行った。
[Quantification of glutathione]
48 hours after the addition of each sample described above, cellular protein was extracted with M-PER (Thermo), and this was used as a measurement sample for protein quantification by BCA method and glutathione quantification using Total Glutathione Quantification Kit (manufactured by DOJINDO). went.
「試験結果」
細胞タンパク質量あたりのグルタチオン濃度を表１に示す。実施例１、２に示すコウジ酸には濃度依存的なグルタチオン産生促進作用が認められ、その作用は２．５ｍＭを添加した実施例１で、Ｎ−アセチル−Ｌ−システイン（ＮＡＣ）１０ｍＭ（比較例１）と同等であり、ＮＡＣよりも低濃度で優れたグルタチオン産生促進作用を示すことを確認することができた。
"Test results"
The glutathione concentration per cell protein amount is shown in Table 1. Kojic acid shown in Examples 1 and 2 has a concentration-dependent glutathione production promoting action, and the action is that of Example 1 to which 2.5 mM is added, and N-acetyl-L-cysteine (NAC) 10 mM (comparison) It was the same as Example 1), and it was confirmed that the glutathione production promoting action was excellent at a lower concentration than NAC.
本発明は、コウジ酸および／またはその誘導体を用いたグルタチオン産生促進剤に関するものであり、これによって、皮膚外用剤等のヒト細胞におけるグルタチオン産生を促進することで美白や老化防止等の機能を発揮させたり、抽出法等によりグルタチオンを製造するときに酵母等の微生物の細胞内でのグルタチオン濃度を向上させることができ有用である。 The present invention relates to a glutathione production promoter using kojic acid and / or a derivative thereof, thereby exerting functions such as whitening and anti-aging by promoting glutathione production in human cells such as a topical skin preparation. When glutathione is produced by an extraction method or the like, the glutathione concentration in the cells of microorganisms such as yeast can be improved.
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