JP6364143B2 - Type17コラーゲン産生促進剤 - Google Patents
Type17コラーゲン産生促進剤 Download PDFInfo
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- JP6364143B2 JP6364143B2 JP2018518542A JP2018518542A JP6364143B2 JP 6364143 B2 JP6364143 B2 JP 6364143B2 JP 2018518542 A JP2018518542 A JP 2018518542A JP 2018518542 A JP2018518542 A JP 2018518542A JP 6364143 B2 JP6364143 B2 JP 6364143B2
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- JP
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- type
- pterostilbene
- glycoside
- compound
- Prior art date
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229940035034 maltodextrin Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- 235000021110 pickles Nutrition 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 230000003658 preventing hair loss Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000021067 refined food Nutrition 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 230000036559 skin health Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Images
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
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- A—HUMAN NECESSITIES
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Description
mは、0〜5の整数を示す。
ただし、nとmとの和は、1以上である。)
で表される化合物である、項1に記載の、Type17コラーゲン産生促進剤。
項1〜9または項11の何れか1項に記載するType17コラーゲン産生促進剤の、育毛剤の製造のための使用。
育毛を求めるヒトに対して、項1〜9または項11の何れか1項に記載するType17コラーゲン産生促進剤を肌または頭皮に適用する工程を含む、育毛方法。
本発明のType17コラーゲン産生促進剤は、スチルベン化合物およびその配糖体からなる群より選択される少なくとも一種の化合物を有効成分とする。
なお、R1およびR2が配位するベンゼン環の位置は、両者の配位される位置に関係なく、上記する位置に自由に配位することができる。
本発明の外用組成物は、上記するType17コラーゲン産生促進剤を含むものである。
上記する本発明の外用組成物の製造方法は、スチルベン化合物およびその配糖体からなる群より選択される少なくとも一種の化合物と、外用組成物に添加することが許容される成分とを混合する工程を含む。
上記する通り、本発明の外用組成物は化粧料組成物の形態とすることができる。
本発明の内用組成物は、上記するType17コラーゲン産生促進剤を含むものである。
本発明の内用組成物の製造方法とは、スチルベン化合物およびその配糖体からなる群より選択される少なくとも一種の化合物と、内用組成物に添加することが許容される成分とを混合する工程を含む。
上記する通り、本発明の内用組成物は飲食品組成物の形態とすることができる。
本発明の、プテロスチルベン化合物は下記式(2)で表される。
上記するプテロスチルベン化合物の製造方法は、特に限定されない。たとえば、以下に示す方法を挙げることができる。なお、上記する式(2)におけるpが0の場合とpが1以上の整数の場合とで、その製造方法を異なるものとすることができる。
pが0を示すプテロスチルベン化合物の製造方法を一例を以下に示す。なお、pが0を示すプテロスチルベン化合物は、下記式(3)で表される化合物である。
qは1〜5の整数を示す。)
pが1以上の整数を示す場合の式(2)で表されるプテロスチルベン化合物は、上記するpが0を示す式(3)で表されるプテロスチルベン化合物及びデンプンとを、シクロデキストリングリコシルトランスフェラーゼの存在下で反応させることによって製造することができる。
下記式(6)で表されるプテロスチルベンモノグリコシドを製造した。
1H NMR (400 MHz in CD3OD): 3.78(6H, singlet, MeO, MeO), 6.34(1H, triplet, J=2.4 Hz, H-4), 6.65(2H, doublet, J=2.4 Hz, H-2, H-6), 6.77 (2H, doublet, J=8.4 Hz, H-3', H-5'), 6.88(1H, doublet, J=16.0 Hz, H-7), 6.95(1H, doublet, J=16.0 Hz, H-8) , 7.37(2H, doublet, J=8.8 Hz, H-2', H-6').
プテロスチルベン多糖配糖体
下記式(7)で表されるプテロスチルベン多糖配糖体を製造した。
式中、プテロスチルベンとグルコピラノシド環との間に位置する酸素原子と該グルコピラノシド環の1''位とのグリコシド結合は、β結合である。
式中、グルコピラノシド環の間のグリコシド結合は、全てα(1−4)結合である。)
・展開液 :アセトニトリル35%水溶液
・流速 :1ml/分
・測定温度 :40℃
質量分析(ESI−):実測値579.2;推定値580.3
質量分析(ESI):実測値741.2;推定値742.3
プテロスチルベン配糖体の水溶性
上記するプテロスチルベン配糖体の水溶性を確認する実験を行った。具体的には、室温での100mlの蒸留水への溶解度を測定した。コントロールとして、プテロスチルベン(アグリコン)を使用した。
皮膚モデル細胞におけるType17コラーゲンタンパク質の産生を確認する実験(1)
EFT−400ヒト皮膚細胞モデル(株式会社クラボウ)を用いて作製した組織に、それぞれ25μMおよび50μMの終濃度となるように、プテロスチルベン(東京化成販売品)および上記する式(3)で表されるプテロスチルベンモノグリコシドを添加し、これを7日間培養した。コントロールとして、DMSOの添加したものを準備した。
<実施例3>
皮膚モデル細胞におけるType17コラーゲンタンパク質の産生を確認する実験(2)
上記する製造例2にて作製したプテロスチルベン二糖配糖体およびプテロスチルベン三糖配糖体を用いて、皮膚細胞モデル内のType17コラーゲンタンパク質の産生量を確かめるウエスタンブロット実験を行った。
以下の表1〜4に示す配合例に従って、各種化粧料組成物を製造する。
Claims (8)
- 式(1)において、R2で2つ示す基が、同一または異なって、メトキシ基、エトキシ基、nープロポキシ基、イソプロポキシ基、n−ブトキシ基およびt−ブトキシ基からなる群より選択される基である、請求項1に記載するType17コラーゲン産生促進剤。
- 前記スチルベン化合物が、プテロスチルベンである、請求項1または2に記載の、Type17コラーゲン産生促進剤。
- 前記配糖体が、スチルベン化合物と糖の1位の水酸基とが結合してなるものである、請求項1〜3の何れか1項に記載の、Type17コラーゲン産生促進剤。
- 前記配糖体が、スチルベン化合物と、単糖とが結合してなるものである、請求項1〜4の何れか1項に記載の、Type17コラーゲン産生促進剤。
- 前記単糖が、グルコース、トレオース、リキソース、アロース、プシコース、セドヘプツロース、およびボレミトールからなる群より選択される少なくとも1つである、請求項5に記載の、Type17コラーゲン産生促進剤。
- 前記配糖体が、スチルベン化合物と、2つ以上の糖からなる多糖とが結合してなるものである、請求項1〜4の何れか1項に記載の、Type17コラーゲン産生促進剤。
- 前記スチルベン化合物と結合する多糖の糖残基が、グルコース残基である、請求項7に記載の、Type17コラーゲン産生促進剤。
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JP2001072552A (ja) * | 1999-09-07 | 2001-03-21 | Sunstar Inc | 育毛組成物 |
JP2007129938A (ja) | 2005-11-09 | 2007-05-31 | Hokkaido Univ | ノックアウトマウス |
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JP2009161509A (ja) * | 2008-05-21 | 2009-07-23 | Kanazawa Univ | Xvii型コラーゲンに関する脱毛抑制剤、毛髪の脱色素化抑制剤 |
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US20120087888A1 (en) * | 2010-04-12 | 2012-04-12 | Pernodet Nadine A | Bio-Mechanical Stimulation Of Collagen Synthesis In Skin Cells And Reduction Of Appearance Of Fine Lines And Wrinkles On The Skin |
JP5901547B2 (ja) * | 2012-03-28 | 2016-04-13 | 富士フイルム株式会社 | 組成物、これを含む皮膚外用剤、又は機能性食品 |
WO2014095289A2 (en) * | 2012-12-20 | 2014-06-26 | Unilever Plc | Method of treating hair ageing |
JP5938834B2 (ja) * | 2013-03-08 | 2016-06-22 | 株式会社 皇漢薬品研究所 | レスベラトロール類配糖体の製造方法 |
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US20150098987A1 (en) * | 2013-10-08 | 2015-04-09 | Faith, Inc. | Trans-resveratrol polysaccharide, method of producing thereof, and composition comprising thereof |
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KR20180083324A (ko) | 2018-07-20 |
WO2018021527A1 (ja) | 2018-02-01 |
KR20190047743A (ko) | 2019-05-08 |
JPWO2018021527A1 (ja) | 2018-07-26 |
EP3492067A1 (en) | 2019-06-05 |
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