JP6852087B2 - デクスパンテノール配糖体含有化合物 - Google Patents
デクスパンテノール配糖体含有化合物 Download PDFInfo
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- JP6852087B2 JP6852087B2 JP2018550753A JP2018550753A JP6852087B2 JP 6852087 B2 JP6852087 B2 JP 6852087B2 JP 2018550753 A JP2018550753 A JP 2018550753A JP 2018550753 A JP2018550753 A JP 2018550753A JP 6852087 B2 JP6852087 B2 JP 6852087B2
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- dexpanthenol
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- skin
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- monosaccharide
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- 235000004866 D-panthenol Nutrition 0.000 title claims description 79
- 239000011703 D-panthenol Substances 0.000 title claims description 79
- 229960003949 dexpanthenol Drugs 0.000 title claims description 78
- 150000001875 compounds Chemical class 0.000 title claims description 44
- 229930182470 glycoside Natural products 0.000 title description 7
- -1 Dexpanthenol glycoside Chemical class 0.000 title 1
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 claims description 117
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 13
- WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 claims description 11
- 150000002772 monosaccharides Chemical class 0.000 claims description 11
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 7
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- RFSUNEUAIZKAJO-ZXXMMSQZSA-N alpha-D-fructofuranose Chemical compound OC[C@H]1O[C@@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ZXXMMSQZSA-N 0.000 description 3
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- RMZNXRYIFGTWPF-UHFFFAOYSA-N 2-nitrosoacetic acid Chemical compound OC(=O)CN=O RMZNXRYIFGTWPF-UHFFFAOYSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-UHFFFAOYSA-N 3,4,5,6-tetrahydroxyoxane-2-carboxylic acid Chemical compound OC1OC(C(O)=O)C(O)C(O)C1O AEMOLEFTQBMNLQ-UHFFFAOYSA-N 0.000 description 1
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 1
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- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 1
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- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
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- 229930091371 Fructose Natural products 0.000 description 1
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- 125000003172 aldehyde group Chemical group 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-PQMKYFCFSA-N alpha-D-mannose Chemical compound OC[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-PQMKYFCFSA-N 0.000 description 1
- 108010028144 alpha-Glucosidases Proteins 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- WQZGKKKJIJFFOK-RWOPYEJCSA-N beta-D-mannose Chemical compound OC[C@H]1O[C@@H](O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-RWOPYEJCSA-N 0.000 description 1
- 108010051210 beta-Fructofuranosidase Proteins 0.000 description 1
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- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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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
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- 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
- A61K31/7032—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a polyol, i.e. compounds having two or more free or esterified hydroxy groups, including the hydroxy group involved in the glycosidic linkage, e.g. monoglucosyldiacylglycerides, lactobionic acid, gangliosides
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/673—Vitamin B group
-
- 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
-
- 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
-
- 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
- A61Q19/007—Preparations for dry skin
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Birds (AREA)
- Biochemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Cosmetics (AREA)
Description
デクスパンテノール(0.05モル/L)及びサッカロース(0.4モル/L)を、0.05Mのリン酸塩緩衝液(0.05モル/L、pH=6)中に溶解し、微生物(プロトアミノバクター・ルブルム(Protaminobacter rubrum)Z12(CBS 574.77))の懸濁液を加えた。
デクスパンテノール(0.05モル/L)及びセロビオース(0.4モル/L)を、酢酸ナトリウム緩衝液(0.05モル/L、pH=5.2)中に溶解し、β−グルコシダーゼ溶液(酢酸ナトリウム緩衝液中100U、アーモンド由来のβ−グルコシダーゼ、BioChemika 49290、CAS 9001−22−3)を加えた。セロビオースは、互いにβ−1,4−グルコシド結合された2つのグルコース分子からなる二糖である。酵素のβ−グルコシダーゼにより、セロビオースのグルコースへ分解が起きる。その反応の間に、グルコースは、化学的にデクスパンテノールに結合する。
デクスパンテノール(0.05モル/L)及びラクトース(0.4モル/L)を、酢酸ナトリウム緩衝液(0.05モル/L、pH=5.2)中に溶解させ、β−ガラクトシダーゼ溶液(酢酸ナトリウム緩衝液中100U、アスペルギルス・オリザエ(Aspergillus oryzae)由来のβ−ガラクトシダーゼ、Sigma G5160、CAS 9031−11−2)を加えた。ラクトースは、β−1,4−グリコシド結合を介して結合されているD−ガラクトースとD−グルコースとからなる。β−ガラクトシダーゼは、この結合の加水分解を酵素触媒して、ガラクトースを生成し、その反応の間に、ガラクトースは、化学的にデクスパンテノールに結合する。
デクスパンテノール(0.05モル/L)及びサッカロース(0.4モル/L)を、酢酸ナトリウム緩衝液(0.05モル/L、pH=5.2)中に溶解させ、フルクトシダーゼ溶液(酢酸ナトリウム緩衝液中100U、Boehringer Mannheim GmbH社、酵母由来のβ−フルクトシダーゼ 注文番号104914)を加えた。該フルクトシダーゼ溶液は、サッカロースのα−D−グルコース及びβ−D−フルクトースへの開裂を酵素触媒する。その反応の間に、β−D−フルクトースは、化学的にデクスパンテノールに結合する。
11 α−グルコシル化デクスパンテノールの13C−NMRスペクトル
21 β−グルコシル化デクスパンテノールの1H−NMRスペクトル
41 β−グルコシル化デクスパンテノールの13C−NMRスペクトル
51 β−ガラクトシル化デクスパンテノールの1H−NMRスペクトル
61 β−ガラクトシル化デクスパンテノールの13C−NMRスペクトル
71 β−フルクトシル化デクスパンテノールの1H−NMRスペクトル
81 β−フルクトシル化デクスパンテノールの13C−NMRスペクトル
Claims (8)
- 治療法及び/又は美容法において使用するための請求項1〜4のいずれか1項に記載の医薬化合物。
- スキンケアにおいて使用するための請求項1〜4のいずれか1項に記載の医薬化合物。
- 皮膚病の予防及び/又は皮膚病の治療において使用するための請求項1〜4のいずれか1項に記載の医薬化合物。
- 創傷治癒の促進のための医薬として使用するための請求項1〜4のいずれか1項に記載の医薬化合物。
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DE102016205474.0A DE102016205474A1 (de) | 2016-04-01 | 2016-04-01 | Dexpanthenol enthaltende Verbindung |
DE102016205474.0 | 2016-04-01 | ||
PCT/EP2017/057038 WO2017167652A1 (de) | 2016-04-01 | 2017-03-24 | Dexpanthenolglykosid-enthaltende verbindung |
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JP2019513141A JP2019513141A (ja) | 2019-05-23 |
JP6852087B2 true JP6852087B2 (ja) | 2021-03-31 |
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JP2018550753A Active JP6852087B2 (ja) | 2016-04-01 | 2017-03-24 | デクスパンテノール配糖体含有化合物 |
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US (1) | US10513532B2 (ja) |
EP (1) | EP3436029B1 (ja) |
JP (1) | JP6852087B2 (ja) |
CA (1) | CA3019610A1 (ja) |
DE (1) | DE102016205474A1 (ja) |
DK (1) | DK3436029T3 (ja) |
WO (1) | WO2017167652A1 (ja) |
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KR20210047318A (ko) * | 2018-08-22 | 2021-04-29 | 디에스엠 아이피 어셋츠 비.브이. | 식품 및 영양 보충제로서의 수크로스 이성질화 효소 |
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2016
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- 2017-03-24 DK DK17717093.3T patent/DK3436029T3/da active
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WO2017167652A1 (de) | 2017-10-05 |
EP3436029A1 (de) | 2019-02-06 |
DK3436029T3 (da) | 2020-05-18 |
DE102016205474A1 (de) | 2017-10-05 |
EP3436029B1 (de) | 2020-02-26 |
US20190031699A1 (en) | 2019-01-31 |
US10513532B2 (en) | 2019-12-24 |
JP2019513141A (ja) | 2019-05-23 |
CA3019610A1 (en) | 2017-10-05 |
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