CN115209867A - 毛发生长促进用和/或白发改善用组合物 - Google Patents
毛发生长促进用和/或白发改善用组合物 Download PDFInfo
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- CN115209867A CN115209867A CN202180018672.3A CN202180018672A CN115209867A CN 115209867 A CN115209867 A CN 115209867A CN 202180018672 A CN202180018672 A CN 202180018672A CN 115209867 A CN115209867 A CN 115209867A
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Abstract
本发明发现了具有R‑spondin1产生促进作用的化合物,本发明使用该化合物提供促进毛发生长和/或改善白发用组合物。一种毛发生长促进用和/或白发改善用组合物,其包含下式(I)表示的化合物或其盐作为有效成分。
Description
交叉参照
本申请基于在日本于2020年3月5日提出申请的日本特愿2020-037718号主张优先权,该申请所记载的内容全部通过参照直接援用于本说明书。另外,在本申请中引用的全部的专利、专利申请及文献所记载的内容全部通过参照而直接援用于本说明书。
技术领域
本发明涉及毛发生长促进用和/或白发改善用组合物,例如,涉及含有2-O-阿魏酰基-L-苹果酸的毛发生长促进用和/或白发改善用组合物。
背景技术
作为产生头发的器官的毛囊形成于胎儿期,通过周期性的头发循环,反复进行毛囊器官的再生。毛囊形成的机理考虑如下。首先,通过来自毛乳头细胞的发毛信号而开始分裂的外根鞘细胞朝向真皮深层,同时在毛乳头细胞的正上方形成毛母区域。构成毛母区域的细胞被称为毛母细胞,进一步增殖分化而形成毛干和内根鞘细胞。在外根鞘细胞的膨胀区域和成为次级毛芽的部分,存在表达作为干细胞标志物的LGR5(Leucine-rich repeat-containing G protein-coupled receptor 5)的细胞。LGR5阳性细胞被认为是依赖于Wnt信号而增殖并有助于维持毛囊的恒定性的毛囊增殖细胞。与向生长期的导入和维持的调整密切相关的LGR5长久被作为孤儿受体,但近年来,报告了将分泌蛋白质R-spondin(RSPO:在本说明书和附图中,也记为RSPO)作为配体(非专利文献1~4)。
R-spondin是作为Wnt/β-catenin信号通路的强力增强物质而分离的4个分泌蛋白质(RSPO1-4)的家族。这些蛋白质具有40~60%的序列同一性,具有与血小板反应蛋白样结构域和弗林样结构域类似的结构。报告了作为属于十字花科的植物的Nasturtiumofficinale(豆瓣菜,日语原文オランダガラシ、和蘭芥子)的提取物促进该R-spondin1的产生(专利文献1)。R-spondin1在毛乳头细胞中产生,从毛囊形成的休止期末期到生长期的期间增加,活化毛囊干细胞,因此提出了使用其的促进毛发生长等的组合物。然而,豆瓣菜提取物中所含的与促进毛发生长等相关的有效成分尚不明确。
现有技术文献
非专利文献
非专利文献1:Carmon KS.et al.,Proc Natl Acad Sci USA.2011Jul12;108(28):11452-7.
非专利文献2:de Lau W.et al.,Nature.2011Jul 4;476(7360):293-7.
非专利文献3:Glinka A.et al.,EMBO Rep.2011Sep30;12(10):1055-61.
非专利文献4:Yoon JK,Lee JS.,Cell Signal.2012Feb;24(2):369-77.
专利文献
专利文献1:日本特开2019-194176号公报
发明内容
发明要解决的课题
本发明发现了一种豆瓣菜等中含有的具有R-spondin1产生促进作用的化合物,使用该化合物提供毛发生长促进用和/或白发改善用组合物等。
用于解决课题的手段
本发明是为了解决上述课题而完成的,发现通过使用柱色谱法等从豆瓣菜提取物进行分馏、精制而得到的特定的化合物具有R-spondin1产生促进作用、以及在人的毛发生长和/或抗白发作用等,从而完成了本发明。
即,本发明包括以下的实施方式。
(1)一种毛发生长促进用组合物,其含有下述式(I)表示的化合物或其盐作为有效成分:
[化学式1]
(2)一种白发改善用组合物,其包含上述式(I)所示的化合物或其盐作为有效成分。
(3)根据(1)或(2)所述的组合物,其中,上述式(I)表示的化合物为2-O-阿魏酰基-L-苹果酸。
(4)一种皮肤外用剂,其含有上述(1)或(2)所述的组合物。
(5)一种美容方法,用于促进毛发生长和/或改善白发,其包括:使用含有上述式(I)表示的化合物或其盐作为有效成分的组合物,促进毛乳头细胞中的R-spondin1的产生。
发明效果
本发明的组合物例如可以用于促进人的毛发生长和/或改善白发。
附图说明
图1为示出从豆瓣菜提取物中精制有效成分的方法的流程图。
图2是通过HPLC对将豆瓣菜提取物粗分馏而获得的Fr.01进行分析的结果。
图3是通过HPLC对将豆瓣菜提取物精制而获得的Fr.21进行分析的结果。
图4是测定在培养基中添加豆瓣菜提取物的各精制馏分来培养人乳头细胞时的RSPO1产生量的结果。
图5是示出将含有有效成分的乳液应用于被检验人时的白发改善等确认试验的结果的显微镜图像。
图6是使用人表皮角化细胞进行RSPO1的作用机理的解析的结果。
具体实施方式
(定义)
在本说明书中,“毛发生长”是指“将现在的头发保持健康,防止脱发并使毛发强壮”(日本毛发业协会对毛发生长的定义)。本发明中的毛发生长作用也基本上是指这样的作用,更具体而言,例如包括毛发的粗细、色泽、光泽的改善、特别是白发的改善。作为其作用显著的情况的例子,是指包括在头皮的已经脱发的部分再次看到头发(所谓的生发)等的广义的作用。
决定毛发、皮肤的颜色的黑色素色素在黑素细胞(黑色素合成细胞)内的黑素体中由酪氨酸生物合成。认为白发与因老化、压力等导致的黑素细胞、黑素体的减少、或者由这些细胞、器官的异常引起的酪氨酸酶的量、活性的降低、黑素体的输送阻碍等有关。日本人一般偏好黑色或茶褐色等的头发,但随着年龄增长,会大量出现白发。这是因为由于毛根部等存在的黑素细胞的数量、活性的降低而黑色素显著减少,从美容和心理方面考虑倾向于避免这种情况。
因此,在本说明书中,“白发改善”是指对黑素细胞等黑色素产生细胞起作用而促进毛发色素的生成。具体而言,例如是指预防地应用于黑发、栗发、金发、红发等状态的毛发或其头皮部,防止受到该应用的毛发成为白发或更退色的状态等,改善例如是指应用于白发或退色的状态的毛发或其头皮部,使其成为原来的黑发、栗发、金发、红发等状态,或者成为进一步着色为有色的状态等。
(有效成分)
本实施方式的毛发生长促进用和/或白发改善用组合物包含下述式(I)表示的化合物或其异构体或者它们的盐作为有效成分:
[化学式2]
上述式(I)所示的化合物在2位含有不对称碳原子,且7’位和8’位的碳原子间的双键具有反式(Z)的构象。因此,作为有效成分,包括这些与位置相关的光学异构体、外消旋体和/或几何异构体。本发明人等发现,通过HPLC从豆瓣菜的乙醇提取液中精制而得到的式(I)所示的化合物即2-O-阿魏酰基-L-苹果酸是用于促进R-spondin1产生、以及促进人的毛发生长和/或改善白发的主要有效成分。因此,本发明的有效成分可以通过从豆瓣菜等药用植物中进行有机溶剂提取及柱色谱精制来制造。或者,也可以通过使用了公知方法的化学合成法来制造。例如,可以将作为市售的起始原料的L-苹果酸和阿魏酸通过使用碳二亚胺作为缩合剂的Steglich酯化(Steglich esterification)反应来合成(Florent Allais,Sophie Martinet,and Paul-Henri Ducrot,Synthesis 2009(21):3571-3578)。
在将本实施方式的有效成分从豆瓣菜中提取的情况下,作为能够用作提取原料的部位,例如可以举出叶、茎、花、根、地上部或这些部位的混合物等,优选为叶和地上部。作为提取方法,可以用水或有机溶剂(乙醇溶液等)进行提取,优选使用50%乙醇水溶液作为提取溶剂。在本实施方式中,优选使用乙醇提取物,该乙醇提取物使用了豆瓣菜的整个植物。
需要说明的是,本发明的有效成分可以为游离体的状态,但在羧基或羟基具有适度的酸性的情况下,也可以为盐的形态。作为羧基或羟基的盐,可以列举例如:锂盐、钠盐、钾盐等碱金属盐类;镁盐、钙盐等碱土金属盐类;三甲胺盐、三乙胺盐、二环己基胺盐、乙醇胺盐、二乙醇胺盐、三乙醇胺盐、普鲁卡因盐等脂肪族胺盐;N,N-二苄基乙二胺等芳烷基胺盐;吡啶盐、甲基吡啶盐、喹啉盐、异喹啉盐等杂环芳香族胺盐;精氨酸盐、赖氨酸盐等碱性氨基酸盐;四甲基铵盐、四乙基铵盐、苄基三甲基铵盐、苄基三乙基铵盐、苄基三丁基铵盐、甲基三辛基铵盐、四丁基铵盐等季铵盐;铵盐等。另外,本发明的化合物(1)的游离体或羧基或羟基的盐有时也以水合物的形式存在。
另外,作为本发明的有效成分的式(I)所示的化合物在分子内具有一个不对称碳,可以是任意的光学异构体,也可以是外消旋体。
(毛发生长促进用和/或白发改善用组合物中所含的上述式(I)所示的化合物的含量)
本实施方式的组合物中的上述式(I)所示的化合物的含量没有特别限定。例如,相对于本发明的组合物的总重量,上述式(I)所示的化合物的含量优选为1×10-5质量%以上,更优选为5×10-5质量%以上,进一步优选为1×10-4质量%以上。另外,优选为1质量%以下,更优选为0.5质量%以下,进一步优选为0.1质量%以下。组合物的形态不仅可以举出液体,还可以举出例如固态物等。
(皮肤外用剂中所含的上述式(I)所示的化合物的含量)
含有该组合物的本实施方式的皮肤外用剂中的上述式(I)所示的化合物的含量只要是考虑其给药方式和给药方法等而能够得到促进毛发生长和/或白发改善效果的量即可,没有特别限定。例如,相对于该皮肤外用剂的总重量,上述式(I)所示的化合物的含量优选为2.0×10-7质量%以上,更优选为1.0×10-7质量%以上,进一步优选为2.0×10-6质量%以上。另外,优选为2.0×10-2质量%以下,更优选为1.0×10-2质量%以下,进一步优选为2.0×10-3质量%以下。
(皮肤外用剂的形态)
本发明的皮肤外用剂可举出安瓶、胶囊、粉末、颗粒、液体、凝胶、气泡、乳液、片、雾、喷雾剂等适合使用的形态的1)医药品类、2)准医药品类、3)局部用或全身用的皮肤外用剂类(例如化妆水、乳液、乳霜、软膏、洗剂、油、面膜等基础化妆品、固体皂、液体皂、洗手液等洗面剂或皮肤清洁剂、按摩用剂、清洁用剂、除毛剂、脱毛剂、剃须处理剂、须后水、须前水、剃须膏、粉底、口红、腮红、眼影、眼线膏、睫毛膏等彩妆化妆品、香水类、美甲剂、指甲油、指甲油除去剂、巴布剂、膏药剂、胶带剂、片材剂、贴剂、气溶胶剂等)、4)应用于头皮·头发的药用或/和化妆用的制剂类(例如洗发剂、护发素剂、头发处理剂、头发预处理剂、烫发持久液、染发料、整发料、焗油剂、育发·养发料、巴布剂、膏药剂、胶带剂、片材剂、气溶胶剂等)、以及5)投放于沐浴水中使用的沐浴用剂、6)、其他的腋臭防止剂、除臭剂、止汗剂、卫生用品、卫生棉类、湿纸巾等。
(皮肤外用剂的构成成分)
另外,在这样的制剂中,可以根据需要在不损害本发明的效果的范围内任意选择、并用以下例示的成分、添加剂来制造,它们在配方体系中的配混量没有特别规定,通常认为优选为0.0001~50%左右。
(1)各种油脂类
鳄梨油、杏仁油、小茴香油、紫苏油、橄榄油、橙子油、大西洋胄胸鲷油(オレンジラファー油)、芝麻油、可可脂、春黄菊油、胡萝卜油、黄瓜油、牛脂脂肪酸、石栗坚果油、红花油、乳木果油、液状乳木果油、大豆油、山茶油、玉米油、菜籽油、桃仁油、蓖麻油、棉籽油、花生油、海龟油、貂油、蛋黄油、棕榈油、棕榈仁油、木蜡、椰子油、牛脂、猪脂、角鲨烯、角鲨烷、鲨肝油烷或这些油脂类的氢化物(硬化油等)等。
(2)蜡类
蜂蜡、巴西棕榈蜡、鲸蜡、羊毛脂、液状羊毛脂、还原羊毛脂、硬质羊毛脂、小烛树蜡、褐煤蜡、虫胶蜡、米糠蜡等。
(3)矿物油
液体石蜡、凡士林、石蜡、地蜡、纯地蜡、微晶蜡等。
(4)脂肪酸类
月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、山嵛酸、油酸、亚油酸、亚麻酸、二十二碳六烯酸、二十碳五烯酸、12-羟基硬脂酸、十一碳烯酸、妥尔油、羊毛脂脂肪酸等天然脂肪酸,异壬酸、己酸、2-乙基丁酸、异戊酸、2-甲基戊酸、2-乙基己酸、异戊酸等合成脂肪酸。
(5)醇类
乙醇、异丙醇、月桂醇、鲸蜡醇、硬脂醇、油醇、羊毛脂醇、胆固醇、植物甾醇、苯氧基乙醇等天然醇,2-己基癸醇、异硬脂醇、2-辛基十二烷醇等合成醇。
(6)多元醇类
环氧乙烷、乙二醇、二乙二醇、三乙二醇、乙二醇单乙基醚、乙二醇单丁基醚、二乙二醇单甲基醚、二乙二醇单乙基醚、聚乙二醇、环氧丙烷、丙二醇、聚丙二醇、1,3-丁二醇、戊二醇、甘油、季戊四醇、苏糖醇、阿拉伯糖醇、木糖醇、核糖醇、半乳糖醇、山梨糖醇、甘露醇、乳糖醇、麦芽糖醇等。
(7)酯类
肉豆蔻酸异丙酯、棕榈酸异丙酯、硬脂酸丁酯、月桂酸己酯、肉豆蔻酸肉豆蔻酯、油酸油酯、油酸癸酯、肉豆蔻酸辛基十二烷基酯、二甲基辛酸己基癸酯、乳酸鲸蜡酯、乳酸肉豆蔻酯、邻苯二甲酸二乙酯、邻苯二甲酸二丁酯、乙酸羊毛脂、单硬脂酸乙二醇酯、单硬脂酸丙二醇酯、二油酸丙二醇酯等。
(8)金属皂类
硬脂酸铝、硬脂酸镁、硬脂酸锌、硬脂酸钙、棕榈酸锌、肉豆蔻酸镁、月桂酸锌、十一碳烯酸锌等。
(9)胶质、糖类或水溶性高分子化合物
阿拉伯胶、安息香胶、达玛树胶、愈创木脂、爱尔兰苔、刺梧桐胶、黄蓍胶、角豆胶、榅桲籽、琼脂、酪蛋白、乳糖、果糖、蔗糖或其酯、海藻糖或其衍生物、糊精、明胶、果胶、淀粉、角叉菜胶、羧甲基甲壳素或壳聚糖、环氧乙烷等附加有亚烷基(C2~C4)氧化物的羟基烷基(C2~C4)甲壳素或壳聚糖、低分子甲壳素或壳聚糖、壳聚糖盐、硫酸甲壳素或壳聚糖、磷酸化甲壳素或壳聚糖、海藻酸或其盐、透明质酸或其盐、硫酸软骨素或其盐、肝素、乙基纤维素、甲基纤维素、羧甲基纤维素、羧乙基纤维素、羧乙基纤维素钠、羟乙基纤维素、羟丙基纤维素、硝基纤维素、结晶纤维素、聚乙烯醇、聚乙烯基甲基醚、聚乙烯基吡咯烷酮、聚乙烯基甲基丙烯酸酯、聚丙烯酸盐、聚环氧乙烷或聚环氧丙烷等聚环氧烷或其交联聚合物、羧乙烯基聚合物、聚乙烯亚胺
(10)表面活性剂
阴离子表面活性剂(烷基羧酸盐、烷基磺酸盐、烷基硫酸酯盐、烷基磷酸酯盐)、阳离子表面活性剂(烷基胺盐、烷基季铵盐)、两性表面活性剂:羧酸型两性表面活性剂(氨基型、甜菜碱型)、硫酸酯型两性表面活性剂、磺酸型两性表面活性剂、磷酸酯型两性表面活性剂、非离子表面活性剂(醚型非离子表面活性剂、醚酯型非离子表面活性剂、酯型非离子表面活性剂、嵌段聚合物型非离子表面活性剂、含氮型非离子表面活性剂)、其他表面活性剂(天然表面活性剂、蛋白质水解物的衍生物、高分子表面活性剂、含钛·硅的表面活性剂、氟化碳系表面活性剂)等。
(11)各种维生素类
维生素A族:视黄醇、视黄醛(维生素A1)、去氢视黄醛(维生素A2)、胡萝卜素、番茄红素(维生素A原)、维生素B族:硫胺素盐酸盐、硫胺素硫酸盐(维生素B1)、核黄素(维生素B2)、吡哆醇(维生素B6)、氰钴胺(维生素B12)、叶酸类、烟酸类、泛酸类、生物素类、胆碱、肌醇类、维生素C族:维生素C酸或其衍生物、维生素D族:麦角钙化醇(维生素D2)、胆钙化醇(维生素D3)、二氢速甾醇、维生素E族:维生素E或其衍生物、泛醌类、维生素K族:植物甲萘醌(维生素K1)、甲基萘醌(维生素K2)、2-甲萘醌(维生素K3)、氢化甲萘醌(维生素K4)、以及必需脂肪酸(维生素F)、肉碱、阿魏酸、γ-谷维素、乳清酸、维生素P类(芦丁、圣草柠檬素、橙皮苷)、维生素U等。
(12)各种氨基酸类
缬氨酸、亮氨酸、异亮氨酸、苏氨酸、蛋氨酸、苯丙氨酸、色氨酸、赖氨酸、甘氨酸、丙氨酸、天冬酰胺、谷氨酰胺、丝氨酸、半胱氨酸、胱氨酸、酪氨酸、脯氨酸、羟基脯氨酸、天冬氨酸、谷氨酸、羟基赖氨酸、精氨酸、鸟氨酸、组氨酸等、它们的硫酸盐、磷酸盐、硝酸盐、柠檬酸盐、或吡咯烷酮羧酸之类的氨基酸衍生物等。
(13)来自植物或动物系原料的各种添加物
它们可以根据要添加的产品种类、形态进行常规方法的加工(例如,任意选择、组合粉碎、制粉、洗涤、水解、发酵、精制、压榨、提取、分馏、过滤、干燥、粉末化、造粒、溶解、灭菌、pH调节、除臭、脱色等的处理),从各种原材料中任意选择并供给。
(作用效果)
认为本实施方式的组合物通过促进毛乳头细胞中的RSPO1的产生,从而促进毛发的生长,并且还具有白发改善作用。与毛囊形成相关的RSPO类在毛乳头细胞中产生,特别是RSPO1从休止期末期到生长期显著增加,使毛囊干细胞活化。即,认为毛乳头细胞的活化以及来自毛乳头细胞的RSPO1的产生促进和/或降低抑制对于隆起和外根鞘细胞中存在的LGR5阳性细胞增殖而言是优选的,与生发、生长期成熟化有关。另外,作为Wnt/β-catenin信号通路的抑制分子,已知Dickkopf1(DKK1),通过形成Wnt的共受体LRP6与DKK1受体Kremen的复合体来抑制Wnt信号。(Binnerts ME.,et al.,Proc Natl Acad Sci USA.2007Sep;11;104(37):14700-5)。DKK1作为阻碍Wnt/β-catenin信号通路的因子,被认为是使生长期毛囊转移到退化期的因素之一,也是与男性型脱发相关的因子(Journal of InvestigativeDermatology(2012),Volume 132,1554-1560)。
本发明人通过确认人表皮角化细胞的存活比例,确认了Wnt-3a、RSPO1和DKK1的相互作用对细胞增殖产生影响。认为根据后述的参考例1的结果,示出RSPO1拮抗DKK1而维持Wnt活性,通过RSPO1使DKK1无效化,促进黑素细胞的增殖和黑色素形成所涉及的因子的产生。
[美容方法]
本发明的美容方法的特征在于,使用由下述式(I)表示的化合物或其盐作为有效成分的组合物,促进毛乳头细胞中的R-spondin1的产生。
[化学式3]
如上所述,本发明人等对上述式(I)所示的化合物发现了促进毛发生长和/或改善白发的作用。而且,根据该见解,作为用于促进毛发生长和/或改善白发的美容方法,本发明人等使用上述式(I)所示的化合物或其盐,促进毛乳头细胞中的R-spondin1的产生,从而完成了本发明。另外,在本发明中,美容方法不仅包括单纯地个人进行的方法,还包括在提供与美容相关的商品时,作为与顾客匹配的化妆品的处方而提供的由医生以外的化妆品销售员、美容师提供的方法。另外,也包括在与美容相关的商品的说明书(附件等)等中作为该商品的使用方法而提供的内容。
在本发明的美容方法中,上述式(I)所示的化合物或其盐可以使用上述说明的化合物或其盐。另外,含有上述化合物或其盐的试剂和组合物也可以适合作为本发明的美容方法中的提取物使用。这样的组合物例如可以通过应用于受试者的期望部位的皮肤来使用。
对皮肤的应用例如可以进行1天1次或多次。
接着,列举实施例,更详细地说明本发明,但本发明不受这些实施例的任何限制。需要说明的是,在以下的实施例中,表示本发明的有效成分等的含量的数值的单位%是指质量%。
[实施例]
[实施例1]豆瓣菜提取物的制备
在豆瓣菜(Nasturtium officinale)的叶和茎的干燥粉碎物200g中加入1000mL的50%乙醇,在室温下一边经常搅拌一边进行7天提取。将得到的提取液过滤,除去残渣,制成粗提取物。该粗提取物中所含的固体成分为0.46%。
[实施例2]豆瓣菜提取物的精制
根据图1所示的步骤,由实施例1中制备的豆瓣菜的粗提取物进行精制。用最初填充有DIAION HP20(三菱化学株式会社制)的柱对豆瓣菜的粗提取物进行粗分馏。分取将柱吸附物用20%乙醇水溶液洗脱而成的馏分(Fr.01),使该馏分吸附于Sep-Pak C18盒(日本Waters公司制),分取用20%乙醇水溶液洗脱而成的馏分(Fr.14)。将分取的馏分的乙醇浓缩后添加丁醇进行提取,将得到的丁醇层浓缩后,再次用20%乙醇溶解,连续进行以下的液相色谱LC1和LC2,分取化合物。
上述液相色谱LC1和LC2的条件如下。
LC1:
装置:Agilent 1290Infinity II LC系统
柱:Mightysil RP-18GP(20mm×250mm)
洗脱液:MeOH:0.1%甲酸=35:65
流速:10mL/min
温度:室温
检测器:330nm
LC2:
装置:SHIMADZU LC-10A系列
柱:Unison UK-C18(4.6mm×250mm)
洗脱液:MeOH:0.1%甲酸=31:69
流速:1.0mL/min
温度:室温
检测器:330nm
将利用上述LC2对由豆瓣菜提取物精制的Fr.01和Fr.21进行分析而得到的结果分别示于图2和图3。如图2及图3所示,有效成分的化合物在保持时间为约22.1分钟的位置被洗脱。其含量以阿魏酸(194.18g/mol)为标准物质,由上述HPLC检测的峰面积算出。以阿魏酸换算的理由是基于该化合物具有阿魏酸的部分结构、以及阿魏酸的吸收光谱与该化合物的UV可见吸收光谱极其类似(λmax为325-330nm)。从豆瓣菜的50%乙醇粗提取物的该化合物的收率为约80%左右。
[实施例3]有效成分的结构确定
利用NMR对实施例2中得到的Fr.21中所含的单一成分(化合物21)进行分析,结果可知,化合物21为2-O-阿魏酰基-L-苹果酸(式(I)所示的化合物)。用核磁共振装置JEOL(日本电子株式会社)JNM-ECA500测定的化合物21的NMR测定数据如下所述。
1H-NMR(500MHz,CD3OD),δ:7.65(1H,d,J=15.9Hz,7’-H),7.21(1H,d,J=1.9Hz,2’-H),7.08(1H,dd,J=8.0,1.9Hz,6’-H),6.80(1H,d,J=8.0Hz,5’-H),6.42(1H,d,J=15.9Hz,8’-H),5.45(1H,dd,J=9.2,3.2Hz,2-H),3.89(3H,s,J=Hz,3’-OCH3),2.95(1H,dd,J=16.5,3.2Hz,3-Ha),2.85(1H,dd,J=16.5,9.2Hz,3-Hb).
13C-NMR(125MHz,CD3OD),δ:168.2(C-9’),150.7(C-4’),149.4(C-3’),147.5(C-7’),127.7(C-1’),124.3(C-6’),116.4(C-5’),114.9(C-8’),111.6(C-2’),56.4(3’-OCH3),37.5(C-3).
[试验例1]RSPO1产生促进作用的评价
将传代5(P5、已传代5次)的人毛乳头细胞(Dermal papilla cell、Promocell制)以5000个/孔的密度接种在塑料制的96孔板上。次日,将实施例2中分馏的各样品(Fr.01和Fr.11~Fr.14)以培养基中的最终浓度为0.25%的方式添加到1%FBS/DMEM培养基中。作为阴性对照,以培养基中的最终浓度成为0.125%的方式添加乙醇。将这些毛乳头细胞培养2天,采集培养上清液作为ELISA测定样品。
关于上述乳头细胞培养上清液中的RSPO1含量,使用人RSPO1/RSPO ELISA试剂盒(LSbio制),对从毛乳头细胞分泌的RSPO1的量进行定量。RSPO1的产生量使用以活细胞数校正后的值。活细胞数使用Cell Counting Kit-8(CCK-8、Dojindo制)进行。
将其结果示于图4。如图4所示,在Fr.14中回收的单个峰的化合物21显示出与Fr.01相同程度的RSPO1产生促进作用,可以确认是RSPO1产生促进剂的有效成分。
[试验例2]白发改善等确认试验
制备含有以阿魏酸换算计为89.4ppb(8.94×10-6质量%)的化合物21(2-O-阿魏酰基-L-苹果酸)的15%乙醇水溶液。将其用作头皮用乳液对51岁的男性受试者使用喷雾器容器以早晚1天2次进行10次按压(0.12g×10=1.2g)/次、6个月期间每天,按照以下的方案进行白发改善等确认试验。
在使用该乳液的2天前,将头部的一处剃毛。通过从剃毛起第2天(试验开始0个月)用显微镜拍摄剃毛部位来进行评价。在试验开始1个月后,将相同的部分剃毛,在从剃毛开始第2天进行同样的评价。从试验开始到6个月的期间反复上述操作。作为评价方法,将用显微镜拍摄的图像输入TrichoScan(Tricholog公司制),解析毛发的根数和密度等。
作为该解析的结果,将头皮的显微镜图像示于图5,将头部的每1平方厘米的头发的粗细、根数、生长速度(0个月与6个月的比较)的平均值示于以下的表1。
[表1]
在表1中,示出了通过使用含有化合物21(式(I)所示的化合物)的乳液,使头发的粗细、根数增加,并且促进了头发的生长的结果。根据该结果,认为化合物21(式(I)所示的化合物)具有毛发生长促进作用。
图5中示出了通过使用含有化合物21(式(I)所示的化合物)的乳液而使头发变黑的实验结果。根据该结果,认为化合物21(式(I)所示的化合物)具有白发改善作用。
[参考例1]RSPO1的作用机理的分析
为了分析RSPO1的作用机理,使用人表皮角化细胞,确认了Wnt-3a、RSPO1和DKK1的相互作用对细胞增殖产生影响。以5000个/孔的密度将传代4(P4)的人表皮角化细胞(KURABO公司制)接种在塑料制的96孔板上。次日,更换培养基,在第3天,与Wnt-3a(R&Dsystems公司制)一起添加DKK1(R&D systems公司制)或DKK1和RSPO1(R&D systems公司制)这两者,在37℃下培养48小时,在第6天,利用细胞增殖检测试剂盒CCK-8测定人表皮角化细胞的细胞数。
将其结果示于图6。图6的纵轴表示在将仅添加了200ng/mL的Wnt-3a时的细胞存活比例设为1时,添加了Wnt-3a和DKK1或者Wnt-3a、DKK1和RSPO1时的细胞存活比例。横轴所示的数值单位为各添加物的量(ng/mL)。
将仅添加Wnt-3a的组的细胞存活比例设为1时,添加了Wnt-3a和DKK1两者的组的细胞数平均值为0.83,添加了Wnt-3a、DKK1和RSPO1的组的细胞数平均值为1.05。
这些结果示出,通过DKK1抑制了细胞增殖(Wnt活性),但如果添加RSPO1,则拮抗DKK1而维持(辅助)Wnt活性,示出RSPO1具有使DKK1无效化的作用。
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