CN112608305B - 一种芒果苷衍生物及其制备方法与在美白产品中的用途 - Google Patents
一种芒果苷衍生物及其制备方法与在美白产品中的用途 Download PDFInfo
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Abstract
本发明提供了一种如下式所示的芒果苷月桂酸酯及其制备方法与应用，本发明首次公开了芒果苷月桂酸酯在美白领域的应用，所述芒果苷月桂酸酯为实验室通过酶法合成的新化合物，采用体外酪氨酸酶抑制评价以及通过建立豚鼠皮肤色素沉着模型，体外涂抹芒果苷月桂酸酯，检测皮肤白度的评价等方法研究，结果表明芒果苷月桂酸酯具有很好的美白作用，效果显著强于阳性对照药物，在美白产品领域具有良好的应用前景；
Description
技术领域
本发明涉及一种芒果苷衍生物及其制备方法，以及在美白领域的应用。
背景技术
随着生活水平的渐渐改善和生活质量的提升，人们爱美之心以及对自己皮肤健康问题越来越关注。解决老年斑、黄褐斑等的肌肤问题最终达到美白的效果一直以来都是东西方女性的终极目标。随着时间的推移科技的不断进步，人们对皮肤美白的观念也发生了翻天覆地的变化，已从物理性的擦粉底遮盖来达到表面美白转向在生理上把黑色素还原达到美白效果。因此，开发安全高效的美白怯斑产品一直备受关注，并一直是人们不懈的追求。现在用于美白的护肤产品往往采用添加酪氨酸酶抑制剂的方法来减少黑色素的生成来达到美白目的。
芒果苷植物来源丰富，广泛存在于百合科植物知母的根、茎和叶，鸢尾科植物射干的叶和花，漆树科植物芒果的树皮、叶和果实中，具有丰富的药理作用，例如抗病毒、抗肿瘤、降糖、抗氧化、降脂等。然而芒果苷的生物利用度很低，这归因于它的低溶解性，由于其亲脂性与亲水性均很差，稳定性不好，因此应用受到了很大的限制。芒果苷酯化后可以提高化合物稳定性，而且研究结果表明酯化后酪氨酸酶抑制活性大幅提高，增强了美白效果。
发明内容
本发明提供了一种具有美白作用的化合物芒果苷月桂酸酯及其合成方法，以及在美白产品中的应用。经检索，未见芒果苷月桂酸酯在美白方面的应用报道，为本发明首次提出。
本发明的技术方案如下：
如下式所示的芒果苷月桂酸酯：
所述芒果苷月桂酸酯的制备方法为：
将芒果苷、月桂酸、叔戊醇(溶剂)混合，加入TLIM脂肪酶，在40～60℃(优选50℃)下反应20～25h(优选21h)，之后反应液经后处理，得到芒果苷月桂酸酯；
所述芒果苷、月桂酸、TLIM脂肪酶的质量比为1：5～10：0.5～1，优选1：8：0.58；
所述叔戊醇的体积用量以芒果苷的物质的量计为0.05～0.15L/mmol，优选0.1L/mmol；
所述后处理的方法为：反应结束后，反应液过滤，滤液旋蒸除去有机溶剂得到粗产品，进行柱层析纯化，先以石油醚洗脱未反应的月桂酸，再以二氯甲烷/乙酸乙酯体积比2：1的混合液为洗脱剂，收集含目标化合物的洗脱液，蒸除溶剂并干燥，得到芒果苷月桂酸酯；
所述芒果苷的结构式为：
所述月桂酸的结构式为：
本发明所述芒果苷月桂酸酯可应用于美白护肤产品中，具体的应用方法例如：
将芒果苷月桂酸酯添加到普通的保湿产品中混匀，即可起到良好的美白效果；
所述芒果苷月桂酸酯的添加量为保湿产品质量的0.05～0.2％；
所述保湿产品例如：面部卸妆湿巾保湿液、保湿面霜、面膜乳霜。
本发明的有益效果在于：
本发明首次公开了芒果苷月桂酸酯在美白领域的应用，所述芒果苷月桂酸酯为实验室通过酶法合成的新化合物，采用体外酪氨酸酶抑制评价以及通过建立豚鼠皮肤色素沉着模型，体外涂抹芒果苷月桂酸酯，检测皮肤白度的评价等方法研究，结果表明芒果苷月桂酸酯具有很好的美白作用，效果显著强于阳性对照药物，在美白产品领域具有良好的应用前景。
具体实施方式
下面通过具体实施例进一步阐述本发明，但本发明的保护范围并不仅限于此。
实施例1芒果苷月桂酸酯的制备
取60克芒果苷，480克月桂酸，以叔戊醇作为溶剂配成芒果苷浓度为10mmol/L的反应液10L，加入35克TLIM脂肪酶(北京高瑞森科技有限公司)；于温度50℃反应时间21小时；收集反应液过滤，旋蒸除去有机溶剂，粗产品约63克，采用190克硅胶吸附后，利用300mL石油醚分三次洗涤脱去剩余的月桂酸，然后采用二氯甲烷/乙酸乙酯2:1混合液400mL洗脱芒果苷月桂酸酯，经旋蒸脱溶剂后得产物约48克。
获得的芒果苷酯化衍生物分子离子峰[M-H]-：603.2，结合碳谱氢谱数据判断分子式为C31H40O12。
1HNMR(500MHz，DMSO-d6)：δ13.78(s，1H，1-OH)，7.38(s，1H，8-H)，6.86(s，1H，5-H)，6.37(s，1H，4-H)，4.61(d，1H，9.8Hz，1’-H)，4.36(d，1H，10.5Hz，6’-H)，4.10(t，1H，8.0Hz，2’-H)，3.96(dd，1H，4.85Hz，6”-H)，3.20(m，3H，3’，4’，5’-H)，2.23(t，2H，7.1Hz，CH2)，1.46(m，2H，CH2)，1.18(m，16H，8CH2)，0.82(t，3H，7.0Hz，CH3)
13CNMR(125MHz，DMSO-d6)：δ179.18(C＝O，C-9)，173.01(C＝O，C-1”)，163.87(C-3)，161.99(C-1)，158.34(C-4a)，154.12(C-6)，150.86(C-4b)，143.81(C-7)，111.80(C-8a)，108.13(C-8)，107.34(C-2)，102.64(C-5)，101.40(C-8b)，93.34(C-4)，78.84(C-5’)，78.19(C-3’)，73.21(C-1’)，70.61(C-4’)，70.08(C-2’)，64.26(C-6’)，33.57(C-2”)，31.37(C-3”)，29.10(C-4”)，29.07(C-5”)，28.92(C-6”)，28.80(C-7”)，28.76(C-8”)，28.41(C-9”)，24.53(C-10”)，22.16(C-11”)，13.99(C-12”)。
将所得芒果苷月桂酸酯的碳谱与文献(Gomez-Zaleta B,Ramirez-Silva MT,Gutierrez A,et al.UV/vis,1H,and 13C NMR spectroscopic studies to determinemangiferin pKa values[J].Spectrochimica Acta Part A 2006,64,1002–1009.)中芒果苷的碳谱比较，发现芒果苷酯化衍生物仅在5’、6’位有明显的化学位移变化，证明芒果苷的酯化反应发生在6’位上，该化合物为一新化合物。
实施例2酪氨酸酶抑制率测定方法
在多只试管中各自加入2mL 1mg/mL的左旋多巴溶液，再分别加入1mL 5种不同浓度的芒果苷月桂酸酯水溶液(0.1mg/mL,0.2mg/mL,0.4mg/mL,0.8mg/mL,1.6mg/mL)，芒果苷水溶液(1.6mg/mL)，采用阳性对照(0.2mg/mL曲酸溶液)后，加入Ph 6.8磷酸氢二钠-柠檬酸缓冲液补齐至反应体系总体积为3.5mL，每组设置3个平型管，于37℃条件下保持10min后，加入比活力为120U/mL的酪氨酸酶溶液0.5mL，继续保持5min后，在分光光度计475nm处测定酪氨酸酶的抑制率，测试结果如表1所示：
表1芒果苷月桂酸酯对酪氨酸酶抑制效果
#：芒果苷对照表明酯化后效果增加
*：曲酸为阳性对照
由表1所示：芒果苷月桂酸酯对酪氨酸酶具有较好的抑制活性，优于阳性对照曲酸。说明芒果苷月桂酸酯可能有较好的美白效果。
实施例3动物试验：芒果苷月桂酸酯添加入湿巾保湿液对豚鼠紫外照射模型肤色的影响
实验方法：
将野白菊纯露1.5g、丙二醇20g、椰油酰胺丙基甜菜碱-35(CAB-35)5g、苯扎溴铵0.1g、水1kg配成湿巾保湿液，然后将该保湿液分成5组，每组约200g。第一组保湿液不添加作为空白对照，第二组加入20mg左旋维生素C作为阳性对照，第三、四、五组分别加入10mg，20mg，40mg芒果苷月桂酸酯，形成配方1-5。
取6-8周龄雌性棕黄色豚鼠10只，给豚鼠背部去毛，每只豚鼠背部皮肤分成6个2*2cm区域，对每个区域进行紫外照射，照射强度为2mW/cm2，每日照射时间10min，共照射7天，7天后使用色差仪测量每个区域的皮肤白度值(记为L1)，数值比未照射前数值(L0)降低20表明造模成功。将豚鼠背部6块区域编号为1、2、3、4、5、6，其中1号不涂抹任何物质，2号涂保湿液空白对照配方1，3号涂阳性对照配方2，4-6号分别涂抹三种美白配方3-5。
对10只豚鼠连续涂抹7周，每天一次，5周后测定白度值(记为L2)，按公式：(L2-L1)/L1*100％计算白度增长率，判断各种配方的美白效果，测试结果如表2所示：
表2各配方对豚鼠皮肤白度影响
#：保湿液组；*：阳性对照组(左旋维生素C)
如表2所示，经过7周的美白配方涂布，采用添加了芒果苷月桂酸酯的美白产品与不涂布，和不添加芒果苷月桂酸酯的保湿液比较，体现出明显的美白效果，配方5涂布后白度增长率达85.9％，明显优于左旋维生素C的美白效果。
Claims (6)
1.如下式所示的芒果苷月桂酸酯在制备美白护肤产品中的应用；
2.如权利要求1所述的应用，其特征在于，所述芒果苷月桂酸酯的制备方法为：
将芒果苷、月桂酸、叔戊醇混合，加入TLIM脂肪酶，在40~60℃下反应20~25h，之后反应液经后处理，得到芒果苷月桂酸酯。
3.如权利要求2所述的应用，其特征在于，所述芒果苷、月桂酸、TLIM脂肪酶的质量比为1：5~10：0.5~1。
4.如权利要求2所述的应用，其特征在于，所述叔戊醇的体积用量以芒果苷的物质的量计为0.05~0.15L/mmol。
5.如权利要求2所述的应用，其特征在于，所述后处理的方法为：反应结束后，反应液过滤，滤液旋蒸除去有机溶剂得到粗产品，进行柱层析纯化，先以石油醚洗脱未反应的月桂酸，再以二氯甲烷/乙酸乙酯体积比2：1的混合液为洗脱剂，收集含目标化合物的洗脱液，蒸除溶剂并干燥，得到芒果苷月桂酸酯。
6.如权利要求1所述的应用，其特征在于，所述应用的方法为：
将芒果苷月桂酸酯添加到普通的保湿产品中混匀，即得美白护肤产品；
所述芒果苷月桂酸酯的添加量为保湿产品质量的0.05~0.2%。
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