WO2020062453A1 - 一种酪氨酸酶抑制剂在面霜、洗面奶或美白乳液中的应用 - Google Patents
一种酪氨酸酶抑制剂在面霜、洗面奶或美白乳液中的应用 Download PDFInfo
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- WO2020062453A1 WO2020062453A1 PCT/CN2018/114231 CN2018114231W WO2020062453A1 WO 2020062453 A1 WO2020062453 A1 WO 2020062453A1 CN 2018114231 W CN2018114231 W CN 2018114231W WO 2020062453 A1 WO2020062453 A1 WO 2020062453A1
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- santalene
- tyrosinase
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/39—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing seven carbon atoms
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- the invention belongs to the field of chemistry and relates to the application of a tyrosinase inhibitor in a face cream, a facial cleanser or a whitening emulsion.
- the color of the skin is related to the type and amount of pigments present in the skin, and melanin has the greatest effect on the color of the skin.
- Melanin is formed in melanocytes at the base of the epidermis. The process is that tyrosine in melanocytes generates dopa under the action of tyrosinase, and dopaquinone eventually forms melanin. Melanin is transferred to basal cells, which are carried to the entire epidermis with the migration of epidermal cells, and are finally lost as the keratinocytes fall off.
- Tyrosinase is a key enzyme for melanin production and controls the process of melanin formation.
- Natural products refer to the components or metabolites of animals, plant extracts (plant extracts) or insects, marine organisms and microorganisms, which mainly include proteins, peptides, amino acids, nucleic acids, various enzymes, monosaccharides, and oligosaccharides.
- tyrosinase inhibitors screened from natural chemical ingredients are used in the preparation of daily cosmetic products, which not only have good whitening effect but also high safety, and have been the research hotspots pursued by major research institutions.
- the object of the present invention is to provide the use of a tyrosinase inhibitor in a cream, a face wash or a whitening lotion.
- the compound ⁇ -santalene or epi- ⁇ -santalene has the chemical structural formula as follows:
- a whitening cream containing an effective amount of the above compound.
- a whitening facial cleanser containing an effective amount of the above compound.
- a whitening emulsion containing an effective amount of the above compound containing an effective amount of the above compound.
- the present invention has found that ⁇ -santolene, epi- ⁇ -santalene, alpinone, ranonone, curcumin A, rosemary amine, iso rosemylamine, and rosespirene Alcohol, ⁇ -ginsene, and ⁇ -ginsene have tyrosinase inhibitory activity similar to or better than arbutin, and have extremely broad application prospects in whitening, washing, and daily life.
- Figure 1 is the chemical structural formula of the tested compound
- Figure 2 shows the IC50 values of the tyrosinase inhibitory effect of the positive control and the tested compounds.
- Example 1 Screening of tyrosinase inhibitors (screening methods refer to the literature: Ren Hongrong et al. Research on the inhibition of tyrosinase activity by perfume lotus extract, natural product research and development Nat ProdRes Dev 2011, 23: 1122-1126)
- the tested compounds include but are not limited to the following compounds (see Figure 1 for chemical structure):
- the tested compound samples were purchased or homemade, and the purity was not less than 95%.
- L-Tyrosine (Sigma); Arbutin (Shanghai Source Bio); 95% ethanol, dimethyl sulfoxide (DMSO), phosphoric acid, disodium hydrogen phosphate, sodium dihydrogen phosphate, concentrated hydrochloric acid, all Commercially available analytical grade; experimental water was deionized water.
- L-tyrosine solution (7.5mmol / L): accurately weigh 0.2723g of L-tyrosine, add a few drops of concentrated hydrochloric acid, add about 50mL of deionized water, and dissolve slightly with heat, then adjust with sodium hydroxide solution pH to 7.0, make up to 200 mL with deionized water.
- Test solution Accurately weigh 0.1g of each of the test compound samples and dissolve them in 20mL of dimethylsulfoxide to obtain 5mg / mL of the test solution, and then dilute to 2.5, 1.25, 0.625, 0.3125mg / mL and 0.15625 mg / mL.
- Positive control accurately weigh 0.1g of arbutin and dissolve it in 20mL of deionized water to obtain 5mg / mL of the positive control mother liquor, and then dilute to 2.5, 1.2500, 0.6250, 0.3125mg / mL and 0.15625mg / mL.
- the tyrosinase solution is prepared from fresh and intact potatoes.
- the specific operation is as follows:
- the total reaction system was 5 mL and the design was as shown in the table below. Among them, when the absorbance value is measured with a spectrophotometer, the "test solution”, “standard control”, and “positive control” are respectively zeroed with “negative control 1", “negative control 2" and "negative control 3".
- the final concentration (mg / mL) gradient of the test solution is 0.015625, 0.03125, 0.0625, 0.125, 0.25, and 0.5.
- A is the absorption value of the standard control
- B is the absorption value of the test solution (or positive control).
- IC50 half inhibitory concentration
- the positive control arbutin is widely used in whitening and daily cleaning. It is a natural active substance derived from green plants. It combines the "green plants, safe and reliable” and “efficient decolorization” into a unified skin decoloration. Component, it can penetrate into the skin quickly, while not affecting the cell proliferation concentration, it can effectively inhibit the tyrosinase activity in the skin, block the formation of melanin, and directly accelerate the melanin by itself binding with tyrosinase Decomposition and excretion, thereby reducing skin pigmentation, eliminating pigmentation and freckles, and not causing side effects such as toxicity, irritation and sensitization to melanocytes, while also having bactericidal and anti-inflammatory effects.
- Example 2 A whitening cream
- ⁇ -santalene epi- ⁇ -santalene, mannalone, mannalone, curcumin A
- rosemary amine iso rosemary Elamine, rosespirenol, ⁇ -ginsene or ⁇ -ginsene, 0.1%
- squalane 10%
- propylene glycol 3%
- sodium octadecyl sulfate 4%
- lauryl alcohol PCA ester 3 %
- Hyaluronic acid 4%
- coconut oil 7%
- the balance is water.
- ⁇ -santalene 0.1% ⁇ -santalene, epi- ⁇ -santalene, mannalone, mannalone, gingerin A, rosemary amine, isomemine based on other conventional cream formulas Rosmarinamine, rosespirenol, alpha-phenylene or beta-phenylene.
- Example 3 A whitening facial cleanser
- ⁇ -santalene epi- ⁇ -santalene, mannalone, mannalone, curcumin A
- rosemary amine iso rosemary Elamine, rosespirenol, ⁇ -ginsene or ⁇ -ginsene, 0.1%
- pearl liquid 5%
- aloe vera gum 5%
- cetyl alcohol 8%
- glycerol 10%
- isopropyl alcohol 2.5%
- triethanolamine 0.5%
- sodium cocoyl glutamate 20%
- lauryl alcohol PCA ester 3%
- the balance is deionized water.
- ⁇ -santalene 0.1% ⁇ -santalene, epi- ⁇ -santalene, mannalene, mannalone, curcumin A, rosemary amine, isopropyl Rosemarylamine, rosespirenol, alpha-phenylene or beta-phenylene.
- Example 4 A whitening emulsion
- ⁇ -santalene epi- ⁇ -santalene, mannalone, mannalone, curcumin A, rosemary amine, iso rosemary Aroma, rosespirenol, ⁇ -ginsene or ⁇ -ginsene, 0.1%; glycerol, 12%; isopropanol, 2%; triethanolamine, 0.3%; propylene glycol, 5%; stearyl sulfate Sodium, 5%; Lauryl alcohol PCA ester, 3%; Hyaluronic acid, 5%; coconut oil, 5%; the balance is water.
- ⁇ -santalene 0.1% ⁇ -santalene, epi- ⁇ -santalene, mannalene, mannalone, curcumin A, rosemary amine, isoamyl on the basis of other conventional emulsion formulas Rosmarinamine, rosespirenol, alpha-phenylene or beta-phenylene.
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Abstract
本发明公开了一种酪氨酸酶抑制剂在面霜、洗面奶或美白乳液中的应用。本发明发现，β-檀香萜烯、表-β-檀香萜烯、蔓藿香烯酮、蔓藿香烷酮、姜花素A、迷迭香胺、异迷迭香胺、玫瑰螺环烯醇、α-人参烯、β-人参烯具有与熊果苷相似或更优异的酪氨酸酶抑制活性，在美白洗护日化中具有极为广阔的应用前景。
Description
本发明属于化学领域，涉及酪氨酸酶抑制剂在面霜、洗面奶或美白乳液中的应用。
皮肤的颜色与皮肤中存在的色素的种类和数量有关，黑素对皮肤颜色影响最大。黑素在表皮基底部的黑素细胞中形成。其过程为黑素细胞中的酪氨酸在酪氨酸酶的作用下生成多巴、多巴醌最终形成黑素。黑素转移至基底细胞中，随着表皮细胞的移行被带到表皮全层，最后随角化细胞的脱落而脱失。酪氨酸酶是黑素生成的关键酶，控制着黑素的形成过程，其活性程度对色素的沉积起主要作用(裘炳毅，化妆品化学与工艺技术大全，中国轻工业出版社，1997：884-888)。市场上许多美白、祛斑产品都是以抑制酪氨酸酶达到美白作用。
天然产物是指动物、植物提取物(简称植提)或昆虫、海洋生物和微生物体内的组成成分或其代谢产物，其中主要包括蛋白质、多肽、氨基酸、核酸、各种酶类、单糖、寡糖、多糖、糖蛋白、树脂、胶体物、木质素、维生素、脂肪、油脂、蜡、生物碱、挥发油、黄酮、糖苷类、萜类、苯丙素类、有机酸、酚类、醌类、内酯、甾体化合物、鞣酸类、抗生素类等。研究发现，这些天然存在的化学成分对人体的副作用较小。
从天然化学成分中筛选得到的酪氨酸酶抑制剂用于制备日化洗护用品，不仅美白效果好，而且安全性高，一直是各大研究机构的追逐的研究热点。
发明内容
本发明的目的在于提供酪氨酸酶抑制剂在面霜、洗面奶或美白乳液中的应用。
本发明上述目的通过如下技术方案实现：
化合物β-檀香萜烯或表-β-檀香萜烯，化学结构式如下：
或化合物蔓藿香烯酮或蔓藿香烷酮，化学结构式如下：
或化合物姜花素A，化学结构式如下：
或化合物迷迭香胺或异迷迭香胺，化学结构式如下：
或化合物玫瑰螺环烯醇，化学结构式如下：
或化合物α-人参烯或β-人参烯，化学结构式如下：
上述化合物用作酪氨酸酶抑制剂的用途。
上述化合物在美白洗护日化中的应用。
一种美白面霜，含有有效量的上述化合物。
一种美白洗面奶，含有有效量的上述化合物。
一种美白乳液，含有有效量的上述化合物。
本发明发现，β-檀香萜烯、表-β-檀香萜烯、蔓藿香烯酮、蔓藿香烷酮、姜花素A、迷迭香胺、异迷迭香胺、玫瑰螺环烯醇、α-人参烯、β-人参烯具有与熊果苷相似或更优异的酪氨酸酶抑制活性，在美白洗护日化中具有极为广阔的应用前景。
图1为测试的化合物的化学结构式；
图2为阳性对照及测试的化合物对酪氨酸酶抑制作用的IC50值。
下面结合附图和实施例具体介绍本发明实质性内容，但并不以此限定本发明的保护范围。
实施例1：酪氨酸酶抑制剂筛选(筛选方法参照文献：任红荣等，香水莲花提取物抑制酪氨酸酶活性的研究，天然产物研究与开发Nat Prod Res Dev 2011，23:1122-1126)
一、实验材料
测试的化合物包括但不限于如下化合物(化学结构见图1)：
测试的化合物样品购买或自制，纯度均不低于95％。
L-酪氨酸(Sigma公司)；熊果苷(上海源叶生物)；95％乙醇，二甲基亚砜(DMSO)，磷酸，磷酸氢二钠，磷酸二氢钠，浓盐酸，均为市售分析纯；实验用水为去离子水。
新鲜马铃薯，购自南京市华润苏果超市。
二、实验方法
1、试剂配制
磷酸钠缓冲液(1/15M，pH＝6.8)：精确称取1.0005g磷酸二氢钠，1.1863g磷酸氢二钠，加入少量去离子水溶解后，定容至500mL，4℃冰箱保存备用。
L-酪氨酸溶液(7.5mmol/L)：精确称取L-酪氨酸0.2723g，先加入数滴浓盐酸，加去离子水约50mL，微热完全溶解后，用氢氧化钠溶液调pH至7.0，加去离子水定容至200mL。
受试液：精确称取测试的化合物样品各0.1g，分别溶于20mL二甲基亚砜，得到5mg/mL的待测液，再对倍稀释到2.5、1.25、0.625、0.3125mg/mL和0.15625mg/mL。
阳性对照：精确称取0.1g熊果苷，溶于20mL的去离子水中，得到5mg/mL的阳性对照母液，再对倍稀释到2.5、1.2500、0.6250、0.3125mg/mL和0.15625mg/mL。
2、酪氨酸酶液的制备
以新鲜完好的马铃薯制取酪氨酸酶液，具体操作为：
将马铃薯洗净，于4℃预冷4h左右。去皮，切成约1×1×1cm
3丁状，于-20℃冷冻过夜。称重，按1:1(w:v)的比例加入4℃预冷的磷酸钠缓冲液，用组织捣碎机制成匀浆，3层纱布过滤，滤液于4000r/min离心10min，上清即为酪氨酸酶粗酶液，4℃保存，2h内用完。
3、样品对酪氨酸酶活性的抑制
总反应体系为5mL，设计如下表。其中，用分光光度计测量吸光值时，“受试液”、“标准对照”、“阳性对照”分别以“阴性对照1”、“阴性对照2”和“阴性对照3”调零。
在此体系中，受试液(包括阳性对照熊果苷)的终浓度(mg/mL)梯度为0.015625、0.03125、0.0625、0.125、0.25和0.5。
实验时，向试管中依次加入磷酸盐缓冲液、不同浓度梯度的受试液(包括阳性对照)和酶液，于30℃水浴10min。然后加入底物L-酪氨酸，立即开始计时。测定反应20min时475nm波长下的吸光值。测定时以相应的阴性对照为参比，用下列公式计算受试液(包括阳性对照)对酪氨酸酶的抑制率。抑制率(％)＝(A-B)÷A×100％
其中，“A”为标准对照的吸光值，“B”为受试液(或阳性对照)的吸光值。每个实验做3个平行。根据抑制率，用Bliss’s软件计算半数抑制浓度(IC50)值。
三、实验结果
阳性对照及测试的化合物对酪氨酸酶抑制作用的IC50值见下表和图2。
已知阳性对照熊果苷广泛用于美白洗护日化中，是源于绿色植物的天然活性物质，集“绿色植物、安全可靠”和“高效脱色”三者合谐统一于一体的皮肤脱色组份，它能迅速渗入肌肤，在不影响细胞增殖浓度的同时，能有效地抑制皮肤中的酪氨酸酶的活性，阻断黑色素的形成，通过自身与酪氨酶直接结合，加速黑色素的分解与排泄，从而减少皮肤色素沉积，祛除色斑和雀斑，而且对黑色素细胞不产生毒害性、刺激性、致敏性等副作用，同时还有杀菌、消炎的作用。它是当今流行的最为安全有效的美白原料，也是二十一世纪的理想皮肤美白祛斑活性剂。研究发现，β-檀香萜烯、表-β-檀香萜烯、蔓藿香烯酮、蔓藿香烷酮、姜花素A、迷迭香胺、异迷迭香胺、玫瑰螺环烯醇、α-人参烯、β-人参烯具有与熊果苷相似或更优异的酪氨酸酶抑制活性，在美白洗护日化中具有极为广阔的应用前景。
实施例2：一种美白面霜
由如下重量百分含量的成分制成：β-檀香萜烯、表-β-檀香萜烯、蔓藿香烯酮、蔓藿香烷酮、姜花素A、迷迭香胺、异迷迭香胺、玫瑰螺环烯醇、α-人参烯或β-人参烯，0.1％；角鲨烷，10％；丙二醇，3％；十八烷基硫酸钠，4％；月桂醇PCA酯，3％；透明质酸，4％；椰油，7％；余量为水。
或在其他常规面霜配方基础上添加0.1％的β-檀香萜烯、表-β-檀香萜烯、蔓藿香烯酮、蔓藿香烷酮、姜花素A、迷迭香胺、异迷迭香胺、玫瑰螺环烯醇、α-人参烯或β-人参烯。
实施例3：一种美白洗面奶
由如下重量百分含量的成分制成：β-檀香萜烯、表-β-檀香萜烯、蔓藿香烯酮、蔓藿香烷酮、姜花素A、迷迭香胺、异迷迭香胺、玫瑰螺环烯醇、α-人参烯或β-人参烯，0.1％；珍珠液，5％；芦荟胶，5％；十六醇，8％；甘油，10％；异丙醇，2.5％；三乙醇胺，0.5％；椰油酰谷氨酸钠，20％；月桂醇PCA酯，3％；余量为去离子水。
或在其他常规洗面奶配方基础上添加0.1％的β-檀香萜烯、表-β-檀香萜烯、蔓藿香烯酮、 蔓藿香烷酮、姜花素A、迷迭香胺、异迷迭香胺、玫瑰螺环烯醇、α-人参烯或β-人参烯。
实施例4：一种美白乳液
由如下重量百分含量的成分制成：β-檀香萜烯、表-β-檀香萜烯、蔓藿香烯酮、蔓藿香烷酮、姜花素A、迷迭香胺、异迷迭香胺、玫瑰螺环烯醇、α-人参烯或β-人参烯，0.1％；甘油，12％；异丙醇，2％；三乙醇胺，0.3％；丙二醇，5％；十八烷基硫酸钠，5％；月桂醇PCA酯，3％；透明质酸，5％；椰油，5％；余量为水。
或在其他常规乳液配方基础上添加0.1％的β-檀香萜烯、表-β-檀香萜烯、蔓藿香烯酮、蔓藿香烷酮、姜花素A、迷迭香胺、异迷迭香胺、玫瑰螺环烯醇、α-人参烯或β-人参烯。
上述实施例的作用在于具体介绍本发明的实质性内容，但本领域技术人员应当知道，不应将本发明的保护范围局限于该具体实施例。
Claims (6)
- 化合物β-檀香萜烯或表-β-檀香萜烯，其特征在于，化学结构式如下：
或化合物蔓藿香烯酮或蔓藿香烷酮，化学结构式如下：
或化合物姜花素A，化学结构式如下：
或化合物迷迭香胺或异迷迭香胺，化学结构式如下：
或化合物玫瑰螺环烯醇，化学结构式如下：
或化合物α-人参烯或β-人参烯，化学结构式如下：
- 权利要求1所述的化合物用作酪氨酸酶抑制剂的用途。
- 权利要求1所述的化合物在美白洗护日化中的应用。
- 一种美白面霜，其特征在于，含有有效量的权利要求1所述的化合物。
- 一种美白洗面奶，其特征在于，含有有效量的权利要求1所述的化合物。
- 一种美白乳液，其特征在于，含有有效量的权利要求1所述的化合物。
Applications Claiming Priority (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811150841.5 | 2018-09-29 | ||
| CN201811150810.X | 2018-09-29 | ||
| CN201811150841.5A CN109232162A (zh) | 2018-09-29 | 2018-09-29 | 酪氨酸酶抑制剂β-檀香萜烯和表-β-檀香萜烯在面霜、洗面奶或美白乳液中的应用 |
| CN201811149421.5 | 2018-09-29 | ||
| CN201811150824.1 | 2018-09-29 | ||
| CN201811149425.3A CN109232490A (zh) | 2018-09-29 | 2018-09-29 | 一种酪氨酸酶抑制剂迷迭香胺和异迷迭香胺在面霜、洗面奶或美白乳液中的应用 |
| CN201811149418.3A CN109251122A (zh) | 2018-09-29 | 2018-09-29 | 一种酪氨酸酶抑制剂α-人参烯和β-人参烯在面霜、洗面奶或美白乳液中的应用 |
| CN201811150824.1A CN109265430A (zh) | 2018-09-29 | 2018-09-29 | 一种酪氨酸酶抑制剂蔓藿香烯酮和蔓藿香烷酮在面霜、洗面奶或美白乳液中的应用 |
| CN201811149425.3 | 2018-09-29 | ||
| CN201811149421.5A CN109251129A (zh) | 2018-09-29 | 2018-09-29 | 一种酪氨酸酶抑制剂玫瑰螺环烯醇在面霜、洗面奶或美白乳液中的应用 |
| CN201811150810.XA CN108947944A (zh) | 2018-09-29 | 2018-09-29 | 一种酪氨酸酶抑制剂姜花素a在面霜、洗面奶或美白乳液中的应用 |
| CN201811149418.3 | 2018-09-29 |
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| WO2024107999A1 (en) * | 2022-11-16 | 2024-05-23 | ExxonMobil Technology and Engineering Company | Heterodimers of terpenes and linear or branched alkenes |
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