CN104758190B - 一种含有二氢黄酮类衍生物的皮肤外用剂组合物 - Google Patents
一种含有二氢黄酮类衍生物的皮肤外用剂组合物 Download PDFInfo
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- CN104758190B CN104758190B CN201410001918.8A CN201410001918A CN104758190B CN 104758190 B CN104758190 B CN 104758190B CN 201410001918 A CN201410001918 A CN 201410001918A CN 104758190 B CN104758190 B CN 104758190B
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- compound
- skin
- flavanone derivatives
- melanin
- oil
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Abstract
本发明提供了一种含有二氢黄酮类衍生物的皮肤外用剂组合物,所述二氢黄酮类衍生物由下式表示,。所述二氢黄酮类衍生物具有很好的美白功效。
Description
技术领域
本发明属于天然产物化学领域,尤其涉及一种含有二氢黄酮类衍生物的皮肤外用剂组合物。
背景技术
近年来人们开始热衷于植物化妆品及回归自然的美容方法。随着人们生活水平和审美标准的提高,越来越多的人追求、渴望白皙及洁润的肌肤。因此,具有防止由太阳光线及其它原因引起的色斑、色素沉着作用的美白类化妆品以及皮肤美白制剂的研究与开发,正日益受到各国化妆品生产商和研究者的重视,美白化妆品已成为护肤类化妆品的主流品种之一。
在人类体内,色素沉着起因于皮肤、毛囊或头发这些角蛋白材料中黑色素的合成和分布。其受多种内部因素(遗传因素)或外部因素(紫外线、废气、活性氧等环境因素)调节。
皮肤和角蛋白纤维的色素沉着起因于特化细胞——黑色素细胞——的代谢活性。这些表皮树突状细胞来源于胚胎发生期间未分化的神经嵴前体——黑色素母细胞。黑色素细胞在称作黑色素小体的细胞器中合成黑色素,该黑色素小体通过黑色素细胞的树突破移至邻近的角质形成细胞。过量生产黑色素导致皮肤成色不均,例如雀斑的生成就是源于此。
祖国医学则认为色素沉着的主要病因是:①肝气郁结;②肾阴不足;③气血淤阻;④劳伤脾土。在治疗上,全身疗法以疏肝、补肾、活血、益气健脾为主,外用以中药面膜和霜、膏剂居多。但此类资料多以临床报道为主,缺乏严密的科研设计、实验室研究和统计学处理。至今为止,也尚末发现开发出治疗“黄褐斑”中药搽剂的文献报道。因此,寻找高效且对人体无副作用或副作用小的美白祛斑制剂已成为目前药学及化妆品领域的一个研究热点。
美白剂的作用是通过抑制酪氨酸酶活性或者阻断酪氨酸生成黑色素的氧化途径,从而减少黑色素生成达到美白皮肤的效果。皮肤美白剂就是作用于皮肤黑色素生成、代谢过程中,抑制黑色素生成且符合规范的物质,但传统的皮肤美白剂,往往采用化学性物质,如具有增白作用的汞盐和祛斑作用的氢醌。这些化合物虽然有快速达到美白之功效,但对皮肤有毒副作用,长期使用会引起接触性皮炎或引起永久脱色等不良作用,在许多国家已被禁用。目前要求的皮肤美白剂应该符合两个标准:一是对酪氨酸酶活性有较高的抑制率,能显著的减少黑色素的生成;二是有较高的安全性,以人体皮肤无毒无刺激。熊果苷、VC及其衍生物和曲酸是目前国内外美白化妆品中较常使用的美白成分。为了开发符合“回归大自然”要求的化妆品,特别是安全,无副作用的美白产品,一些具有很好美白效果的中草药目前越来越受到消费者的青睐。在国际上化妆品发展最有代表性的国家如美国、日本、法国和德国等国家中,中草药因其天然药效温和且不良作用少而被广泛认同,从中了解到近年来崇尚自然,远离化学污染的理念。特别是从日本化妆品工业的发展趋势看,各化妆品公司使用的中草药已达200余种,目前,在日本含天然中草药的化妆品已占整个化妆品市场的50%以上。因此,寻找开发高效且对人体无副作用或副作用小的天然皮肤美白祛斑制剂已成为目前化妆品领域的一个较被重视的课题。
发明内容
本发明的目的在于:提供一种含有二氢黄酮类衍生物的皮肤外用剂组合物,旨在将二氢黄酮类衍生物应用于皮肤外用剂中,以起到美白的功效。
本发明的目的是这样实现的:
一种含有由以下通式(1)所表示的任何一种或一种以上的二氢黄酮类衍生物作为有效成分的皮肤外用剂组合物,
其中,R1为H、烷基或糖基,R2为H或糖基。
所述烷基具体为不饱和烷基(如甲基,乙基,异戊烯基),所述糖基为葡萄糖基、甘露糖基、鼠李糖基中的一种或者任意两种组成的双糖基。
优选R1为H,R2为葡萄糖基(Glc-)时,所述二氢黄酮类衍生物化学名为二氢桑色素-3-0-β-D-葡萄糖苷,以下简称化合物1,其化学结构式如通式(2)所示,
优选R1为烷基(如CH3),R2为葡萄糖基(Glc-)时,所述二氢黄酮类衍生物化学名为7-甲氧基-二氢桑色素-3-0-β-D-葡萄糖苷,以下简称化合物2,其化学结构式如通式(3)所示,
优选R1为葡萄糖基(G1c-),R2为H时,所述二氢黄酮类衍生物化学名为二氢桑色素-7-0-β-D-葡萄糖苷,以下简称化合物3,其化学结构式如通式(4)所示,
优选R1、R2均为H时,所述二氢黄酮类衍生物化学名为二氢桑色素,以下简称化合物4,其化学结构式如通式(5)所示,
本发明提供的上述二氢黄酮类衍生物是首次从柘木植物提取物中分离得到,该化合物也有可能从其他属植物中分离得到。
通过采集柘木,将其晒干,粉碎,用有机溶剂室温浸泡后,进行超声处理;滤出提取液之后,向滤渣中再加入有机溶剂,然后进行超声处理并过滤;合并两次提取液,真空浓缩至干,得到柘木提取物;将提取物分散到水中,依次用石油醚、乙酸乙酯、正丁醇萃取。取正丁醇萃取部位,真空减压干燥,得到正丁醇萃取部位;然后用正相、反相和凝胶柱层析法分离精制得到活性化合物。所述有机溶剂优选乙醇水溶液。
柘木(拉丁名:Cudrania amboinesis),桑科,柘属植物。国内同属植物还有柘树(拉丁名:Cudrania tricuspida ta)、构棘(别名:穿破石)(拉丁名:Cudraniacochichinesis)、柘藤(拉丁名:Cudrania fruticosa)、毛柘藤(拉丁名:Cudraniapubescens)等。柘树在全国分布较广,构棘在我国东南部有较大分布。柘木、柘藤和毛柘藤主要分布在云南南部和中南部地区。
经试验发现,上述二氢黄酮类衍生物具有显著的美白功效,所述二氢黄酮类衍生物,包括所优选的任何一种化合物1-4都可作为活性成分添加到化妆品配方中,这里所指的活性成分在某些情况下可以提供一种或一种以上的功效。
本发明中所述的活性成分还可以为泛醇、甘草酸二钾、尿囊素、烟酰胺、抗坏血酸磷酸酯钠、三色堇提取物、透明质酸钠、生育酚乙酸酯、十一碳烯酰基苯并氨酸等。此外,此类描述是为了便于理解,并不是使成分限于具体指出的应用或者所列出的应用。
所述二氢黄酮类衍生物可应用于皮肤外用剂、保健食品和医药,尤其是可应用于化妆品中,根据制剂的不同类型添加不同的用量。
所述皮肤外用剂组合物是通常用于皮肤外部的所有成分的统称概念,例如可以是化妆料组合物或药学组合物。所述化妆料组合物中可以是基础化妆料、面部妆容化妆料、身体用化妆料等,对其剂型无特殊限制,根据不同目的可合理选择。
所述化妆料组合物中根据剂型和目的的不同还含有不同的化妆品学层面允许的介质或基质赋形剂。
可以用于本发明皮肤外用剂组合物的化妆品、皮肤病学或药学上可接受的赋形剂包括,但不限于一种或多种含水系统、甘油、C2-4醇类、多元醇类、二元醇类、植物油、矿物油、硅油、水或其任意组合。
在本发明中,赋形剂可以为水相、油相、凝胶、水包蜡型乳液、水包油型乳液或油包水型乳液的形式。水相为一种或多种水溶性或分散性组分的混合物,其在室温(25℃)下可以为液体、半固体或固体。赋形剂包括或可以为在水或水-醇赋形剂中的混悬液、分散液或溶液的形式,其可以含有增稠剂或凝胶剂。本领域技术人员可以基于本领域技术人员掌握的知识选择合适的产品形式,其中包含的组分。
所述的组合物可以包括水相,该水相可以含有水或水与至少一种亲水性有机溶剂的混合物,所述的亲水性有机溶剂诸如醇,尤其是含有2-5个碳原子的直链或支链低级一元醇,如乙醇或丙醇;多元醇,如丙二醇、山梨醇、甘油、泛醇或聚乙二醇及其混合物。
当发明的组合物为乳液形式时,该组合物还可以任选包含表面活性剂。
所述的组合物还可以包含成膜聚合物,如聚氨基甲酸酯、聚丙烯酸均聚物或共聚物、聚酯、基于烃的树脂和/或硅氧烷树脂。可以将聚合物溶于或分散于化妆品可接受的赋形剂中并且任选与增塑剂合并。
本发明的组合物还可以包含油相,所述的油相含有在室温(25℃)下为液体的油溶性或油分散性组分和/或在室温下为油状或蜡状的物质,如蜡、半固体、树胶及其混合物。该油相还可以含有有机溶剂。
通常在室温下为液体,合适的油性物质包括:来源于动物的基于烃的油,如全氢化角鲨烯;基于烃的植物油,如液体的C4-10脂肪酸的甘油三酯类,例如庚酸或辛酸甘油三酯类,或油,例如向日葵油、玉米油、大豆油、葡萄籽油、蓖麻油、鳄梨油、辛酸/癸酸甘油三酯类、霍霍巴油;矿物或合成来源的直链或支链烃类,例如液体石蜡及其衍生物、凡士林;合成酯类和醚类,特别是脂肪醇的酯类,例如肉豆蔻酸异丙酯、棕榈酸2-乙基己酯、硬脂酸2-辛基十二烷基酯、异硬脂酸异硬脂醇酯;羟基化酯类,例如乳酸异硬脂醇酯、羟基硬脂酸辛酯、羟基硬脂酸辛酯、羟基硬脂酸辛基十二烷基酯、脂肪醇的庚酸酯类、辛酸酯类和癸酸脂类;多元醇酯类,例如丙二醇二辛酸酯、新戊二醇二庚酸酯、二甘醇二异壬酸酯和季戊四醇酯类;含有C12-26的脂肪醇类,例如辛基十二烷醇、2-丁基辛醇、2-己基癸醇、2-十一烷基十五烷醇、油醇;基于部分烃的氟油和/或氟硅油,硅油,在室温下为液体或半固体的挥发性或非挥发性的直链或环状聚甲基硅氧烷,例如环状聚二甲基硅氧烷和聚二甲基硅氧烷,其任选包含苯基,例如苯基三甲基硅氧烷、硅氧烷及其混合物。
本发明的组合物可以进一步包含常用于化妆品领域中的任何组分。这些组分包括防腐剂、水相增稠剂(多糖生物聚合物、合成聚合物)和脂肪相增稠剂、芳香剂、亲水性和亲脂性活性剂及其混合物。
本发明的组合物还可以包含另外的颗粒相,所述的颗粒相可以为化妆品组合物中使用的颜料和/或珠光剂和/或填充剂。
颜料可以存在于组合物中,合适的无机颜料包括氧化钛、氧化锆和氧化铈以及氧化锌、氧化铁和铁蓝;合适的有机颜料包括钡、锶、钙和铝色淀和碳黑。
珠光剂可以存在于组合物中,合适的珠光剂包括涂覆了氧化钛、氧化铁或天然颜料的云母。
填充剂可以存在于组合物中,合适的填充剂包括滑石粉、二氧化硅、硬脂酸锌、云母、高岭土、尼龙粉末、聚乙烯粉末、特氟龙、淀粉、一氮化硼、共聚物微球,例如硅氧烷树脂微珠。
本发明组合物的油相可以包含一种或多种蜡、树胶或其混合物。蜡包括基于烃的蜡、氟蜡和/或硅氧烷蜡,并且可以来源于植物、矿物、动物和/或合成来源。合适的蜡包括蜂蜡、巴西棕榈蜡、小烛树蜡、石蜡、微晶蜡、地蜡;合成蜡包括聚乙烯蜡、含有C16-45的硅氧烷蜡。树胶一般为聚二甲基硅氧烷或羧甲基纤维素钠或多糖类,并且半固体物质一般为基于烃的化合物,如羊毛脂及其衍生物。
可以将本发明的组合物配制成任何合适的产品形式。这类产品形式包括,但不限于气溶胶型喷雾剂、霜剂、乳液、固体、液体、分散体、泡沫、凝胶、化妆水、摩丝、软膏、粉剂、贴剂、润发油、溶液、手按泵型喷雾剂、棒状物、面膜和湿纸巾。可以将本发明的组合物通过本领域众所周知的各种方法便利地用于制备或作为化妆品、皮肤病学或药物局部施用产品。
本发明的皮肤外用剂组合物可以包括一种或多种下列成分:抗过敏剂、抗微生物剂、抗氧化剂、螯合剂、着色剂去色素剂、润肤剂、乳化剂、表皮脱落剂、成膜剂、香料、保湿剂、昆虫驱避剂、润滑剂、药物活性剂、增湿剂、耐光剂、防腐剂、护肤剂、皮肤渗透增强剂、防晒剂、稳定剂、表面活性剂、增稠剂、粘度调节剂、维生素或其任意组合。
附图说明
图1是抑制斑马鱼黑色素产生实验的空白对照图;
图2是熊果苷(0.2mg/ml)抑制斑马鱼黑色素产生实验的效果图;
图3是本发明提供的化合物1(0.1mg/ml)抑制斑马鱼黑色素产生实验的效果图;
图4是本发明提供的化合物2(0.1mg/ml)抑制斑马鱼黑色素产生实验的效果图。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白,以下结合附图及实施例,对本发明进行进一步详细说明。应当理解,此处所描述的具体实施例仅仅用以解释本发明,并不用于限定本发明。
实施例1:二氢黄酮类衍生物的制备
取1公斤柘木晒干,粉碎,用6升70%乙醇室温浸泡一天后,超声处理30分钟,滤出提取液之后,向滤渣中再加入5升70%乙醇,超声处理30分钟,过滤,合并两次提取液,真空浓缩至干,得到280g柘木提取物。
取250g柘木提取物加到2升水中进行分散,然后依次用石油醚、乙酸乙酯、正丁醇各1000ml进行萃取。每种溶剂分别萃取三次,并将每种溶剂的三次萃取液合并,最终形成三个部位并浓缩至干:石油醚部位(15g)、乙酸乙酯部位(81g)和正丁醇部位(120g)。
分别检测石油醚部位、乙酸乙酯部位和正丁醇部位的酪氨酸酶活性,以熊果苷为对照品。
试验方法:在样品管和样品对照管中各加入1ml不同浓度的样品溶液,阳性和阴性对照管以磷酸缓冲液代替。在样品管和阳性对照管中加入0.5ml酪氨酸酶溶液(酶活单位125u/ml),样品对照和阴性对照管以0.5ml磷酸缓冲液(pH=6.8)代替,振摇所有试管,使样品和酪氨酸酶充分混匀,37℃水槽孵育10分钟,加入2ml的0.03wt%酪氨酸溶液,反应10分钟,即刻在475nm处测定吸光度。
抑制率I(%)=[1-(T-T0)/(C-C0)]×100%
式中:T0:样品溶剂对照;
T:样品对照;
C:阳性对照;
C0:阳性对照溶剂对照。
计算半数抑制率(IC50)。IC50值定义为抑制率为50%时所需酪氨酸酶抑制剂的浓度。计算方法为以样品的浓度对酪氨酸酶的抑制率作图并进行拟合,读取计算IC50值。试验结果如表1所示:
表1
样品 | IC50(μg/ml) |
柘木提取物 | 300 |
石油醚部位 | 720 |
乙酸乙酯部位 | 240 |
正丁醇部位 | 110 |
熊果苷 | 460 |
由表1可知,乙酸乙酯部位和正丁醇部位均有较强的酪氨酸酶抑制活性,且均优于对照品熊果苷。
取正丁醇部位进行硅胶柱层析,用氯仿:甲醇的体积百分比分别为20∶1;15∶1;10∶1;5∶1;1∶1的比例进行梯度洗脱,分别得到5个部位。将其中氯仿:甲醇为5∶1洗脱的部位再用C18反相制备柱进行层析,用20%甲醇、40%甲醇、60%甲醇、90%甲醇进行梯度洗脱,将其中40%甲醇洗脱的部位再经过Sephadex LH-20凝胶柱层析,用100%乙醇洗脱,得到化合物,通过理化常数和现代波谱学手段(MS、NMR)鉴定结构。
化合物1:为淡黄色粉末,红外图谱(IR):3440显示有羟基存在,1700显示为苯环的特征吸收。ESI-MS(电喷雾质谱)给出准分子离子峰为m/z:465[M-H]-,提示其分子量为466。结合1H NMR和13C NMR,推断其分子式为C21H22012,不饱和度为10
在1H NMR中,可以观察到5个芳香质子[δ5.88(1H,d,J=2.8Hz);δ5.92(1H,d,J=2.8Hz);δ6.30(1H,d,J=2.8Hz);δ6.30(1H,d,J=8.0Hz);δ7.29(1H,d,J=2.8Hz);],6个葡萄糖基上的质子信号[δ5.10(1H,d,J=8.2Hz),3.90(1H,m);4.05(1H,m);4.21(1H,m);3.92(1H,m);4.27(2H,m)。结合其13C NMR信号:在21个碳信号中,15个归属为黄酮类化合物骨架,6个归属为葡萄糖基。初步推断化合物1为二氢黄酮苷类化合物,根基葡萄糖基异头氢的耦合常数(J=8.2Hz),推断为β-D-葡萄糖苷。
综合文献资料,发现化合物1的1H NMR和13C NMR数据跟从本属植物中分离得到的二氢桑色素非常接近,所不同的是,化合物1多出了明显属于葡萄糖的信号。根据13C NMR的化学位移变化以及相应的HMBC相关点信息(δ4.93H-3/δ101.2葡萄糖的C-1;δ5.10葡萄糖的H-1/δ75.7C-3),可以推断,化合物1中葡萄糖连接在二氢桑色素的C-3位置。因此,化合物1的结构是二氢桑色素-3-0-β-D-葡萄糖苷。
化合物2:为淡黄色粉末,红外图谱(IR):3440显示有羟基存在,1700显示为苯环的特征吸收。ESI-MS给出准分子离子峰为m/z:479[M-H]-,提示其分子量为480。结合1H NMR和13C NMR,推断其分子式为C22H24012,不饱和度为10。
在1H NMR中,可以观察到5个芳香质子[δ5.85(1H,d,J=2.8Hz);δ5.88(1H,d,J=2.8Hz);δ6.35(1H,d,J=2.8Hz);δ6.35(1H,d,J=8.0Hz);δ7.37(1H,d,J=2.8Hz)],6个葡萄糖基上的质子信号[δ5.07(1H,d,J=8.0Hz),δ3.91(1H,m);δ4.05(1H,m);δ4.23(1H,m);δ3.94(1H,m);δ4.25(2H,m)],一个甲氧基信号(δ3.79,3H,s)。结合其13C NMR信号:在22个碳信号中,15个归属为黄酮类化合物骨架,6个归属为葡萄糖基,一个归属为甲氧基碳信号。初步推断化合物1为甲氧基取代二氢黄酮苷类化合物,根基葡萄糖基异头氢的耦合常数(J=8.2Hz),推断为[3-D-葡萄糖苷。
综合文献资料,发现化合物2的1H NMR和13C NMR数据跟从本属植物中分离得到的二氢桑色素非常接近,所不同的是,化合物2多出了明显属于葡萄糖的信号以及甲氧基的信号。根据13C NMR的化学位移变化以及相应的HMBC相关点信息[δ4.78(H-3)/δ101.5(葡萄糖的C-1);δ5.10(葡萄糖的H-1)/δ75.7(C-3);δ3.79(甲氧基氢信号)/δ165.3(C-7)],可以推断,化合物2中葡萄糖连接在二氢桑色素的C-3位置,甲氧基连接在二氢桑色素的C-7位。因此,化合物2的结构是7-甲氧基-二氢桑色素-3-0-13-D-葡萄糖苷。
化合物1、化合物2和二氢桑色素的HNMR和CNMR数据如表2所示:
表2
在对柘木的分离纯化中(活性跟踪分离纯化),除了分离得到上述化合物1、2外,还另外分离得到4个已知化合物,分别为二氢桑色素-7-0-β-D-葡萄糖苷(化合物3)、二氢桑色素(化合物4)、氧化白藜芦醇和槲皮素。根据文献报道,二氢桑色素-7-0-β-D-葡萄糖苷、二氢桑色素和氧化白藜芦醇均具有非常显著的美白活性。
二氢桑色素-7-0-β-D-葡萄糖苷的化学结构式
二氢桑色素的化学结构式
氧化白藜芦醇的化学结构式
槲皮素的化学结构式。
实施例2对化合物的美白活性研究
试验样品:由实施例1得到的化合物1和化合物2
对照品:熊果苷
2.1抑制酪氨酸酶活性的研究
试验方法:在样品管和样品对照管中各加入1ml不同浓度的样品溶液,阳性和阴性对照管以磷酸缓冲液代替。在样品管和阳性对照管中加入0.5ml酪氨酸酶溶液(酶活单位125u/ml),样品对照和阴性对照管以0.5ml磷酸缓冲液(pH=6.8)代替,振摇所有试管,使样品和酪氨酸酶充分混匀,37℃水槽孵育10分钟,加入2ml的0.03wt%酪氨酸溶液,反应10分钟,即刻在475nm处测定吸光度。
抑制率I(%)=[1-(T-T0)/(C-C0)]×100%
式中:T0:样品溶剂对照;
T:样品对照;
C:阳性对照;
C0:阳性对照溶剂对照。
计算半数抑制率(IC50)。IC50值定义为抑制率为50%时所需酪氨酸酶抑制剂的浓度。计算方法为以样品的浓度对酪氨酸酶的抑制率作图并进行拟合,读取计算IC50值。试验结果如表3所示:
表3
样品 | IC50(μM) |
化合物1 | 10.2 |
化合物2 | 23.5 |
熊果苷 | 460 |
2.2抑制B16黑色素生成的研究
采用Hosoi等改良方法测定提取物对对黑色素抑制作用。B16黑色素细胞以1×105密度培养在96孔板中,经24h后换液,添加不同浓度的药物,72h后,经PBS洗涤两次,样品经空气干燥,溶于200μl1N NAOH(含1%DMSO),经加热80℃至1h后冷却,选择475nm波长在酶联免疫检测仪上读取吸光度值。
黑色素含量抑制率=[1-(药物孔吸光度值/药物孔细胞密度)(对照孔吸光度值/照孔细胞密度)]×100%
计算半数抑制率(IC50)。IC50值定义为抑制率为50%时所需黑色素抑制剂的浓度。计算方法为以样品的浓度对黑色素的抑制率作图并进行拟合,读取计算IC50值。试验结果如表4所示:
表4
样品 | IC50(μM) |
化合物1 | 25.2 |
化合物2 | 40.3 |
熊果苷 | 346 |
2.3化合物1和化合物2抑制斑马鱼黑色素产生实验
成年斑马鱼饲养于实验室循环水养殖系统中,饲养用水经循环系统过滤并充分曝气,选择形态正常,个体较大和健康的性成熟斑马鱼,在孵化系统按雌雄比1∶2进行配对饲养于玻璃水族箱中。在光照刺激下开始产卵,大约半小时后,开始收集胚胎。将收集的胚胎充分的清洗去除脏物后,在显微镜下挑选出健康发育正常的胚胎用于接下去的实验。
以96孔板作为试验容器,每孔中加入200u1的待测活性物溶液,胚胎发育到9hpf时,按1个胚胎/孔随机分配到96孔板中,每个浓度设置一块板。每个待测活性物设置三个浓度组。每天更换待测活性物暴露液并搅拌,以确保活性成分分布均匀。基于表型的色素沉着评估,于55hpf观察活性物对斑马鱼的黑色素抑制效果。观察前,胚胎用三卡因甲基磺酸盐溶液麻醉后,放入装有3%甲基纤维素的凹玻片上,在倒置显微镜下拍摄。实验结果见图1-4。
从实验结果图片可以看出,化合物1和化合物2均可以非常明显的抑制斑马鱼黑色素的产生,并且其抑制活性明显高于阳性对照熊果苷。化合物1和化合物2在0.1mg/ml的浓度下,其黑色素抑制活性已经高于0.2mg/ml的熊果苷的效果。
通过以上各种试验,可见所述二氢黄酮类衍生物,及其包括的任何一种化合物1-5都具有显著的美白功效。
实施例3:含有二氢黄酮类衍生物的皮肤外用剂
取实施例1中制备的一种或一种以上的二氢黄酮类衍生物,用于皮肤外用剂的制备。所述二氢黄酮类衍生物在皮肤外用剂中的重量百分比是0.001-5,优选0.01-2。以下是二氢黄酮类衍生物在皮肤外用剂中的具体应用的实施例。以下各表中“-”表示无添加。
实施例4:含有上述化合物1的皮肤外用剂
含有化合物1的美白霜的组分如表5所示:
表5
含有化合物1的精华素的组分如表6所示:
表6
实施例5:含有上述化合物2的皮肤外用剂
含有化合物2的防晒露的组分如表7所示:
表7
含有化合物2的美白面膜的组分如表8所示:
表8
实施例6:含有上述化合物3的皮肤外用剂
含有化合物3的祛斑膏的组分如表9所示:
表9
实施例7:含有上述化合物4的皮肤外用剂
含有化合物4的化妆水的组分如表10所示:
表10
以上所述仅为本发明的较佳实施例而已,并不用以限制本发明,凡在本发明的精神和原则之内所作的任何修改、等同替换和改进等,均应包含在本发明的保护范围之内。
Claims (1)
1.一种含有由以下通式所表示的二氢黄酮类衍生物作为有效成分的皮肤外用剂组合物:
其中,R1为H,R2为葡萄糖基;
所述二氢黄酮类衍生物在皮肤外用剂中的重量百分比是0.001-2。
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