JP6189928B2 - 多糖の調整方法及び化粧品組成物とその使用方法 - Google Patents
多糖の調整方法及び化粧品組成物とその使用方法 Download PDFInfo
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- 229960002154 guar gum Drugs 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 231100000508 hormonal effect Toxicity 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- IAJILQKETJEXLJ-LECHCGJUSA-N iduronic acid Chemical compound O=C[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-LECHCGJUSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002088 nanocapsule Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 210000003757 neuroblast Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940023569 palmate Drugs 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000030393 positive regulation of fibroblast proliferation Effects 0.000 description 1
- 230000003658 preventing hair loss 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
- 239000000047 product Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9706—Algae
- A61K8/9722—Chlorophycota or Chlorophyta [green algae], e.g. Chlorella
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0003—General processes for their isolation or fractionation, e.g. purification or extraction from biomass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Botany (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dermatology (AREA)
- Sustainable Development (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
・「分子量」の語は、単一の分子又は分子の混合物について区別無しに言及し、混合物の場合は平均値を意味する。
(b)温度が20℃から100℃、溶液のpHが4から8の範囲において、過酸化水素(H2O2)を徐々に加える工程
(c)攪拌しながら、温度を20℃から100℃、溶液のpHを4から8の範囲に維持する工程
(d)室温において、濾過又は遠心沈降する工程
(e)減圧下にて濃縮する工程
(f)低分子量分子を、接線流限外濾過(tangential ultrafiltration)の後に微粒子化するか、アルコール沈殿、濾過、洗浄及び乾燥して純化する工程。
(抽出)
多糖の抽出は、50グラムのオオバアオサ藻粉末を1リットルの水に分散し、95℃にて2時間、激しく攪拌する(1000回転/分)することによって行った。続いて、混合物は、焼成ガラス1上の珪藻土(50g)を通して高温濾過した(藻の除去は、遠心沈降(10,000g、30分、22℃)によって行うこともできる)。
(低分子量オリゴ糖の生成)
得られた50gの多糖(オオバアオサから抽出されたもの)を1リットルの水(80℃、pH 7−7.5)に激しく攪拌(1500回転/分)しながら溶解する。150mlの35%H2O2溶液を、2.5ml/分の速さで1時間かけて加える。これは80℃において、NaOH(5M)を連続的に加えることによってpH 7−7.5に維持しながら行う。
(分析)
・構成糖の分析
オリゴ糖の加水分解は2NのTFAにより行った。構成糖の分析は、イオンクロマトグラフィ(HPAEC)により、単糖データベース(グルクロン酸、ラムノース)を参照して同定を行った。
・分子量の測定
サイズ排除クロマトグラフィー(SEC MALLS)により、2つのクロマトグラフィーカラムOHP AK SB 804 及び 806 HQ (Shodex)を用いて分析した。
・スルホン基量
スルホン基率は、Dodgson 及びPrice (1962)のバリウム/ゼラチン非濁法によって測定した。
(調製)
50gのオオバアオサ粉末を、90℃、1リットルの水に2時間激しく攪拌(1000回転/分)して分散させた。混合物を焼成ガラス1上の珪藻土(50g)により高温濾過した。不溶部の除去は、遠心沈降(10,000g、15分、22℃)により行っても良い。
(分析)
・構成糖の分析
オリゴ糖の加水分解は2NのTFAにより行った。構成糖の分析は、イオンクロマトグラフィ(HPAEC)により、単糖データベース(グルクロン酸、ラムノース)を参照して同定を行った。
・分子量の測定
サイズ排除クロマトグラフィー(SEC MALLS)により、2つのクロマトグラフィーカラムOHP AK SB 804 及び 806 HQ (Shodex)を用いて分析した。
・スルホン基量
スルホン基率は、Dodgson 及びPrice (1962)のバリウム/ゼラチン非濁法によって測定した。
50gのオオバアオサ藻粉末を1リットルの水に分散し、90℃にて2時間、激しく攪拌する(1000回転/分)。続いて、60mlの35%H2O2溶液を、1ml/分の流量で1時間かけて加える。これは、80℃において、NaOH(5M)によりpHを5−8に調製しながら行う。H2O2を加え終えた(約1時間)後、80℃、pH 5−8にて攪拌(500回転/分)を3時間続ける。続いて、混合物を焼成ガラス1上に珪藻土(50g)を通して高温濾過する。不溶粒子の除去は、遠心沈降(10,000g、15分、22℃)によって行うこともできる。
インビトロ培養したヒト繊維芽細胞について、例1から3により調製したオリゴ糖を重量で0.05%(つまり、100gの細胞培地に対して0.05g)含む場合及び含まない場合のトランスクリプトミクス的調査を行った。
本発明のオリゴ糖を含まない場合(コントロール条件)と、0.01%、0.02%及び0.05%(順に、培地100gに対して0.01g、0.02g及び0.05g)含む場合(処理条件)とにおいて、ヒト繊維芽細胞についての第2のインビトロ実験を行った。
・ELISA技術を用いた免疫組織学的分析によるヒアルロン酸
・クロマトグラフdosageによる全コラーゲン
遠心沈降の後、繊維芽細胞を含むペレットは、コラゲナーゼ(1 mg/細胞ペレット)により0.5ml/lの酢酸中で4℃にて24時間分解される。10,000gにて遠心沈降した後、コラーゲンは1Mの塩化ナトリウムにより沈殿され、沈殿は再度懸濁化されたのち透析される。1級アミノ酸は、オルトフタルアルデヒド酸(OPA)によりその阻害を排除することで得られた。続いて、ヒドロキシプロリン及びプロリンがNBD−Clを用いてアミノ基をNBD−Clとカップリングすることにより得られた。NBD−hypは逆相HPLCにより分離した。アミノ酸誘導体の分離を進めるために、ヒドロキシプロリンを含む標準のNBD−Clとのカップリングを最初に行った。ヒドロキシプロリンは、逆相HPLCにより分離した後、蛍光を測定した。
18人の志願者(18人のコーカソイド女性、56±6歳)の顔面について、二重盲検法による医学的研究を行い、本発明のオリゴ糖の再形成(reshaping)及び再構成(re-sculpting)効果を見積もった。56日間、各志願者は、本発明のオリゴ糖を2重量%含む(つまり100gの化粧品に本発明のオリゴ糖を2g含む)化粧品を顔の一方の半分に塗布し、顔の他方の半分にプラシーボ化粧品(本発明のオリゴ糖を含まない以外は同じ組成の化粧品)を塗布した。顔の半分の分配は無作為に行われた。
・硬度弾性測定(ballistometry)により、皮膚の硬さと弾力性を分析する
縞投影により、直接且つ即時に顔の形態を三次元的に得ることができ、体積を評価することができる。この技術により、顔における卵形の弛緩の軽減(再成形、再構成の効果)を評価することができる。三次元の情報は、顔の表面に投影され、デジタルカメラにより記録された縞模様の変形から計算される。この分析は、異なる測定時に撮影された画像の重ね合わせによる。このようにして、皮膚の弛緩について興味の対象である領域が定められる。この領域が同じ志願者の全ての測定時について同じ位置に特定される。これにより、当該興味の対象である領域と、その参照面への投影と間の体積が計算できる。分析されるパラメータは、mm3にて表される顎の相対体積である。このパラメータの減少は、本製品の再成形効果を意味する。
・再構成の効果(硬度弾性測定により測定される凹みのパラメータの減少)、皮膚密度の増加(硬度弾性測定により測定されるアルファパラメータの増加)及び皮膚の弛緩の減少(硬度弾性測定により測定される面積パラメータの減少)による再構成効果。
Claims (5)
- 多糖の調製方法であって、以下のステップ、つまり、
(a)藻であるオオバアオサの粉末を、温度が20℃から100℃、溶液のpHが4から8の範囲において、水に分散させる工程と、
(b)温度が20℃から100℃、溶液のpHが4から8の範囲において、過酸化水素(H2O2)を徐々に加える工程と、
(c)攪拌しながら、温度を20℃から100℃、溶液のpHを4から8の範囲に維持する工程と、
(d)室温において、濾過又は遠心沈降する工程と、
(e)減圧下にて濃縮する工程と、
(f)低分子量分子を、接線流限外濾過の後に微粒子化するか、アルコール沈殿、濾過、洗浄及び乾燥して純化する工程と、
を含み、
前記多糖は、
一般式(I)により表され、
置換基R 1 からR 4 は、互いに独立し且つそれぞれのグリクロン酸及び/又はラムノース単位毎に独立して、ヒドロキシル基又はサルフェート基であり、
nは、50以下の整数であって、且つ分子量が5,000ダルトン以上で且つ15,000ダルトン以下となるように選ばれている多糖又はその薬学的に許容されている塩を形成していている多糖である、
多糖の調製方法。
- 請求項2の多糖の調整方法において、
前記ステップ(b)及び(c)の少なくとも一つにおいて、NaOHを連続的に加えることにより前記溶液のpHを4から8の範囲とする、多糖の調整方法。 - 請求項1の化粧品組成物を、細胞外基質の構成分子の生合成及び/又は組織化を促進し、且つ/又は、その分解を低減するために用いる、化粧品組成物の使用方法。
- 請求項4の化粧品組成物の使用方法において、
皮膚及び/又は毛細血管の構造及び機能の変成、組織再生の変成、組織の弛緩、皮膚及び/又は毛細血管の微小循環の変成、皮膚の解毒作用の変成、皮膚及び/又は毛細血管の色における明るさの均一性の喪失、皺や隈の発生、皮膚の乾燥を含む皮膚表面の質感の変成、脆弱毛を含む毛細血管の質感の変成、並びに、抜け毛を含む皮膚構造及び/又は毛細血管構造の変成、を含む内因性及び/又は外因性の皮膚及び毛細血管の老化の兆候を防止且つ/又は処置するための化粧品組成物の使用方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR12/53197 | 2012-04-06 | ||
FR1253197A FR2989087B1 (fr) | 2012-04-06 | 2012-04-06 | Nouveaux composes oligosaccharides et leur utilisation cosmetique |
PCT/FR2013/050756 WO2013150253A1 (fr) | 2012-04-06 | 2013-04-05 | Nouveaux composés oligosaccharides et leur utilisation cosmétique |
Publications (2)
Publication Number | Publication Date |
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JP2015515524A JP2015515524A (ja) | 2015-05-28 |
JP6189928B2 true JP6189928B2 (ja) | 2017-08-30 |
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FR3020570B1 (fr) | 2014-04-30 | 2017-07-21 | Pierre Fabre Dermo-Cosmetique | Association d'un acide hyaluronique et d'un polysaccharide sulfate |
FR3075644B1 (fr) * | 2017-12-27 | 2020-08-28 | Oreal | Oligosaccharides sulfates et leurs utilisations cosmetiques |
CN110183544A (zh) * | 2019-06-06 | 2019-08-30 | 山东天易科技有限公司 | 一种海藻多糖的制备方法 |
CN110713626B (zh) * | 2019-10-14 | 2021-06-01 | 福建农林大学 | 一种具有辅助抗肿瘤作用的石莼寡糖复合物的制备方法 |
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FR2989087A1 (fr) | 2013-10-11 |
JP2015515524A (ja) | 2015-05-28 |
FR2989087B1 (fr) | 2016-01-01 |
KR102029078B1 (ko) | 2019-10-07 |
EP2833863A1 (fr) | 2015-02-11 |
KR20150002659A (ko) | 2015-01-07 |
WO2013150253A1 (fr) | 2013-10-10 |
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