JP5339847B2 - 育毛剤 - Google Patents
育毛剤 Download PDFInfo
- Publication number
- JP5339847B2 JP5339847B2 JP2008271069A JP2008271069A JP5339847B2 JP 5339847 B2 JP5339847 B2 JP 5339847B2 JP 2008271069 A JP2008271069 A JP 2008271069A JP 2008271069 A JP2008271069 A JP 2008271069A JP 5339847 B2 JP5339847 B2 JP 5339847B2
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- JP
- Japan
- Prior art keywords
- group
- hair
- extract
- general formula
- component
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 210000004209 hair Anatomy 0.000 title claims description 37
- 239000004480 active ingredient Substances 0.000 claims description 27
- -1 isovaleroyl group Chemical group 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000005601 angeloyl group Chemical group 0.000 claims description 15
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 10
- HQKAYCHMYMSSEQ-YADHBBJMSA-N 3'-angeloyloxy-4'-isovaleryloxy-2',3'-dihydrooroselol Natural products CC=C(C)C(=O)O[C@H]1[C@H](Oc2ccc3ccc(=O)oc3c12)C(C)(C)OC(=O)CC(C)C HQKAYCHMYMSSEQ-YADHBBJMSA-N 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 150000004775 coumarins Chemical class 0.000 claims description 5
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000284 extract Substances 0.000 description 35
- 230000003779 hair growth Effects 0.000 description 23
- 230000000694 effects Effects 0.000 description 19
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- 239000001569 carbon dioxide Substances 0.000 description 3
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- 230000001737 promoting effect Effects 0.000 description 3
- ZCCUUQDIBDJBTK-UHFFFAOYSA-N psoralen Chemical class C1=C2OC(=O)C=CC2=CC2=C1OC=C2 ZCCUUQDIBDJBTK-UHFFFAOYSA-N 0.000 description 3
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 description 2
- 235000001287 Guettarda speciosa Nutrition 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
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- VTAJIXDZFCRWBR-UHFFFAOYSA-N Licoricesaponin B2 Natural products C1C(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2)C(O)=O)C)(C)CC2)(C)C2C(C)(C)CC1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O VTAJIXDZFCRWBR-UHFFFAOYSA-N 0.000 description 2
- ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 description 2
- 239000004909 Moisturizer Substances 0.000 description 2
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- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
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- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
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- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
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- 238000012258 culturing Methods 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- QMDNUCYGVSWWRO-UHFFFAOYSA-N edulisin ii Chemical compound C1=CC(=O)OC2=C3C(OC(=O)C=C(C)C)C(C(C)(C)OC(=O)C=C(C)C)OC3=CC=C21 QMDNUCYGVSWWRO-UHFFFAOYSA-N 0.000 description 2
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Description
本発明に係る育毛剤は、アメリカンアンジェリカ植物又は当該植物の抽出物に含まれ、育毛活性を有する活性成分を有効成分としている。ここで、アメリカンアンジェリカとは、学名をAngelica atropurpureaと称し、セリ科に分類される植物である。
〔実施例1〕アメリカンアンジェリカからの活性成分類の単離
(1)図1に示す工程に従って、アメリカンアンジェリカ(Angelica atropurpurea(セリ科)の根茎から本発明の化合物「成分A」及び「成分B」を単離した。
fr. A: 0.23 g
fr. B: 0.01 g
fr. C: 0.03 g
fr. D: 0.07 g
fr. E: 0.05 g
fr. F: 0.02 g
fr. G: 0.02 g
fr. H: 0.15 g
fr. I: 0.24 g
fr. J: 0.10 g
fr. K: 0.03 g
fr. I - 1: 46.5 mg
fr. I - 2: 27.6 mg
fr. I - 3: 3.4 mg
fr. I - 4: 6.3 mg
fr. I - 5: 18.8 mg
fr. I - 6: 84.6 mg
fr. I - 7: 5.4 mg
fr. I - 8: 46.9 mg
本発明の化合物は、分析の結果、fr. I-6(成分A)及びfr. I-8(成分B)にほぼ単一化合物として得られた。
(1)実施例1で得られた化合物について、1H NMR解析及び13C NMR解析を行った。
1H NMR(500 MHz, CDCl3)及び13C NMR(125 MHz, CDCl3)解析の結果として得られたデータを表1に示す。
本例では、実施例1及び2で成分Aとして単離したアルカンジェリシンの脱アシル化を行った。まず、成分A(70mg)を7mLのアセトンに溶解後、濃アンモニア水7mLを添加し、室温で一昼夜攪拌した。反応液を濃縮後(75mg)、分取高速液体クロマトグラフィ(内径10×250mm)に付し、0.1%ギ酸-アセトニトリル系で溶出し、主生成物を分取した(17mg)。
(1)実施例3で得られた化合物について、1H NMR解析及び13C NMR解析を行った。1H NMR(500 MHz, CDCl3)及び13C NMR(125 MHz, CDCl3)解析の結果として得られたデータを表2に示す。
本例では、対象物質の育毛効果を検証できるin vitroの実験系を用いて実施例1で得られた成分A及び成分Bの育毛効果を検証した。
食肉用豚種の臀部皮膚を適当な大きさに切り分け、余分な脂肪組織を除いた。豚皮は無菌下でヒビテン液(5%ヒビテン液(住友製薬)を水で5〜20倍に希釈)に5分〜10分浸することにより消毒を行った後にD-PBSで数回洗浄した。その後、実体顕微鏡下にて洗浄した豚皮から毛包を単離してWilliam's Medium E培地(Invitrogen)培地中に集めた。
毛伸長率を算出した結果を図2に示す。図2から判るように、実施例1で得られた成分A及び成分Bの添加群においては、溶媒コントロール群と比較して有意な毛伸長が認められた。この結果から、実施例1で得られた成分A及び成分BCは育毛効果を有することが明らかとなった。すなわち、実施例1で得られた成分A及び成分Bは、育毛効果を示す活性成分であり、育毛剤として、或いは外用剤として使用できることが明らかとなった。
Claims (3)
- 上記一般式(I)中R1がアンゲロイル基、イソバレロイル基及びセネシオイル基からなる群から選ばれる少なくとも1種の官能基であり、R2はアンゲロイル基、イソバレロイル基、2メチルブチル基及びセネシオイル基からなる群から選ばれる少なくとも1種の官能基であることを特徴とする請求項1記載の育毛剤。
- 上記一般式(I)で表されるクマリン誘導体が、アルカンジェリシン、3’-angeloyloxy-4’-isovaleryloxy-2’,3’-dihydrooroselol、及び3’-hydroxy-4’-angeloyloxy-2’,3’-dihydrooroselolからなる群より選択される少なくとも1種の化合物であることを特徴とする請求項1記載の育毛剤。
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JP2008271069A JP5339847B2 (ja) | 2008-10-21 | 2008-10-21 | 育毛剤 |
US13/124,521 US8420836B2 (en) | 2008-10-21 | 2009-10-21 | NFAT signal inhibitor and hair-growing agent |
PCT/JP2009/005523 WO2010047103A1 (ja) | 2008-10-21 | 2009-10-21 | Nfatシグナル阻害剤及び育毛剤 |
CN200980140484.7A CN102177162B (zh) | 2008-10-21 | 2009-10-21 | Nfat信号抑制剂以及育发剂 |
EP09821803.5A EP2348025B1 (en) | 2008-10-21 | 2009-10-21 | Nfat signal inhibitor and hair-growing agent |
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