CN111978199A - 马齿苋酰胺及其用途 - Google Patents
马齿苋酰胺及其用途 Download PDFInfo
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- CN111978199A CN111978199A CN202010875796.0A CN202010875796A CN111978199A CN 111978199 A CN111978199 A CN 111978199A CN 202010875796 A CN202010875796 A CN 202010875796A CN 111978199 A CN111978199 A CN 111978199A
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- purslane
- cream
- lotion
- cosmetic
- amide
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Abstract
本发明涉及化妆品的技术领域，特别涉及一类马齿苋酰胺化合物及其用途；本发明通过制备具有抗炎、抗组胺、抗氧化和美白系列化合物，使得到的化合物可以用于制备化妆品试剂或药物试剂，本发明中的化妆品试剂和药物试剂没有特定限制。例如可以是柔肤化妆水、营养化妆水、按摩霜、润肤乳、凝胶、营养霜、面膜、啫喱类或沐浴露洗发水等洗去类型的化妆品，也可以是以类似乳霜、软膏、霜、贴膏或喷雾剂等药物制剂产品；作为敏感性皮肤使用，婴儿和儿童化妆品中也可以添加来降低刺激。
Description
技术领域
本发明涉及化妆品的技术领域，特别涉及一类马齿苋酰胺及其用途。
背景技术
马齿苋又名长命菜、马苋菜，为马齿苋科植物。广布于全世界温带和热带地区，在我国和其他许多国家作为药食两用植物使用。
现代药理研究表明马齿苋具有抗菌、松弛骨骼肌、兴奋子宫、降血脂、降血糖、抗炎镇痛、促进伤口愈合、抗氧化、抗衰老和神经保护等多方面作用。马齿苋主要化学成分包括黄酮类、香豆素、萜类、甾类、生物碱、氨基酸、各种色素类和矿物质类等。其中生物碱是马齿苋中一类主要的化学成分。
炎症作为一种重要的病理过程在人体中十分常见，它本身是作为机体对于外来的或者异体的刺激的一种自身免疫应答。而当这种应答失调或者过分应答导致机体的自损伤时，就演变成了炎症。在这些过程中，促炎因子如TNF-α、IL-6、IL-1β等都起到了重要的作用。肥大细胞主要分布于结缔组织和黏膜下层，嗜碱粒细胞主要分布于外周血液。这两类细胞表面均表达高亲和性IgEFc受体，可与IgE的Fc段结合，使机体处于致敏状态。在I型超敏反应的发生的发敏阶段，当相同变应原再次进入机体时，与致敏靶细胞(即肥大细胞和嗜碱性粒细胞)表面IgEFab段特异性结合，触发靶细胞(即肥大细胞和嗜碱性粒细胞)的细胞膜变化，使其脱颗粒及合成新的活性介质。这些介质作用于相应的效应器官，引起效应器官病理改变。肥大细胞和嗜碱粒细胞活化后释放的活性介质主要有组胺、激肽原酶、白三烯、前列腺素D2、血小板活化因子。
抗氧化的作用机理可以是直接作用在自由基，或是间接消耗掉容易生成自由基的物质，防止发生进一步反应。目前对自由基清除剂的研究方法主要有2类，一类是体外模型，另一类是体内模型，其中DPPH法是体外模型中最常用的方法。
酪氨酸酶具有多种特征性催化活性，酪氨酸酶活性对皮肤黑色素沉积起着主要作用。而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或者降低酪氨酸酶的表达，从而减少黑色素生成达到美白皮肤的效果。
因此，针对现有产品的不足，需要提供一种具有抗炎、抗组胺、抗氧化及美白的产品是目前亟需解决的问题。
发明内容
本发明所要解决的技术问题是：如何通过合成一类化合物，使其具有抗炎、抗组胺、抗氧化及美白的功效，使其可用于制备化妆品试剂。
为了解决上述技术问题，本发明采用的技术方案为：
本发明提出
一类马齿苋酰胺，其结构通式如下：
其中，R1、R2、R3、R4为H、OH或OCH3；
列举马齿苋酰胺的结构式如下：
本发明还提出将上述通式1化合物作为制备抗炎的化妆品试剂的用途；
本发明还提出将上述通式1化合物作为制备抗组胺的化妆品试剂的用途；
本发明还提出将上述通式1化合物作为制备抗氧化的化妆品试剂的用途；
本发明还提出将上述通式1化合物作为制备美白的化妆品试剂的用途。
本发明的有益效果在于：本发明通过制备具有抗炎、抗组胺、抗氧化及美白功能的系列化合物，使得到的化合物可以用于制备化妆品试剂或药物试剂，本发明中的化妆品试剂和药物试剂没有特定限制。例如可以是柔肤化妆水、营养化妆水、按摩霜、润肤乳、凝胶、营养霜、面膜、啫喱类或沐浴露洗发水等洗去类型的化妆品，也可以是以类似乳霜、软膏、霜、贴膏或喷雾剂等药物制剂产品；作为敏感性皮肤使用，婴儿和儿童化妆品中也可以添加来降低刺激。
附图说明
图1为本发明实施例1制得的马齿苋酰胺1的核磁氢谱图；
图2为本发明实施例1制得的马齿苋酰胺1的核磁碳谱图；
图3为本发明实施例1制得的马齿苋酰胺1的质谱图；
图4为本发明实施例2制得的马齿苋酰胺2的核磁氢谱图；
图5为本发明实施例2制得的马齿苋酰胺2的核磁碳谱图；
图6为本发明实施例2制得的马齿苋酰胺2的质谱图。
具体实施方式
为详细说明本发明的技术内容、所实现目的及效果，以下结合实施方式并配合附图予以说明。
本发明最关键的构思在于：合成一类化合物，使其具有抗炎、抗组胺、抗氧化、美白的功效，使其可用于制备化妆品试剂。
请参照图1至图6，本发明提出一类马齿苋酰胺，其结构通式如下：
其中，R1、R2、R3、R4为H、OH或OCH3；
列举马齿苋酰胺的结构式如下。
本发明还提出将上述通式1化合物作为制备抗炎的化妆品试剂的用途；本发明还提出将上述通式1化合物作为制备抗组胺的化妆品试剂的用途；
本发明还提出将上述通式1化合物作为制备抗氧化的化妆品试剂的用途；
本发明还提出将上述通式1化合物作为制备美白的化妆品试剂的用途。
实施例1
1.对乙酰氧基苯丙酸的合成
50g对羟基苯丙酸，加150ml乙腈搅拌至完全溶清，22.5g氢氧化钠用150ml水溶解，加入反应液中，46.5g醋酐滴加进反应液中，滴加完成，室温搅拌1h，TLC监测反应完全，向反应液中加入6M盐酸酸化溶液pH＝1，加150ml乙酸乙酯萃取分层，有机相用水洗涤至中性，有机相浓缩至干，得59.2g白色固体产物。
2.缩合
59g对乙酰氧基苯丙酸，39g酪胺，7.1gDMAP，用300ml四氢呋喃溶解，35.9g DIC用120ml四氢呋喃溶解，滴加进反应液中，室温搅拌1h，TLC监测反应完全。
3.水解、酸化
浓缩除去四氢呋喃，向残留物加180ml水，180ml无水乙醇，加入氢氧化钠调节pH＝13，升温至50℃，水解30min，降温至室温，过滤除去不溶物，滤液浓缩除去乙醇，残留水相加6M盐酸酸化至pH＝1，固体析出，过滤，滤饼用水洗涤至中性，85℃烘干，烘干后固体加180ml乙醇，加热至70℃溶解，加3g(5％)活性炭脱色30min，过滤除炭，向滤液中加入180ml水，降温至4-10℃，固体析出，过滤，85℃烘干，得60g白色固体产物。
实施例1制得的马齿苋酰胺1核磁数据如下：
核磁氢谱(400MHz,DMSO-d6)δ：9.20(s，2H)，7.85(d，J＝4.0Hz，1H)，6.97(m，4H)，6.71(d，J＝8.0Hz，4H)，3.22(t，J＝12.0Hz，2H)，2.73(t，J＝12.0Hz，2H)，2.58(t，J＝16.0Hz，2H)，2.34(t，J＝12.0Hz，2H)。
核磁碳谱(100MHz,DMSO-d6)δ:172.09，156.07，155.91，131.85，130.03，129.96，129.54，115.58，115.52，41.09，38.04，34.89，30.88。
实施例2
50g酪胺，73g二氢咖啡酸，4.5gN,N’-二甲氨基吡啶用300ml无水四氢呋喃溶解，降温至0℃，50.6g二异丙基碳二亚胺用200ml无水四氢呋喃溶解，0℃下滴加至前述混合液中，滴加完成后，升温至室温，搅拌20h，过滤除去不溶物，浓缩除去四氢呋喃，残留物加300ml1M氢氧化钠溶解，过滤除去不溶物，滤液用1M盐酸酸化至pH＝1，析出类白色固体，过滤，滤饼用水洗涤至呈中性，固体85℃烘干，得92g产物，收率：83.8％。
实施例2制得的马齿苋酰胺2核磁数据如下：
核磁氢谱(400MHz,DMSO-d6)δ：6.94(d，J＝8.0Hz，2H)，6.67(t，J＝12.0Hz，2H)，6.63(s，2H)，6.50(m，1H)，3.28(t，J＝16.0Hz，2H)，2.72(t，J＝16.0Hz，2H)，2.60(t，J＝16.0Hz，2H)，2.36(t，J＝16.0Hz，2H)。
核磁碳谱(100MHz,DMSO-d6)δ:176.61，160.73，150.12，148.44，137.36，134.74，134.65，123.92，120.83，120.56，120.24，45.75，42.76，39.61，35.80。
应用例1
本申请实施例1提供的马齿苋酰胺1应用于抗敏膏霜中，配方表1所示：
表1
工艺流程：
1、准确称取A相并投入到乳化锅中，加热至85℃，保温搅拌1小时；
2、准确称取B相，加热至85℃后，投入A相中，均质搅拌1小时；
3、降温至50℃，将C相投入乳化锅中，搅拌10分钟，出锅。
应用例2
本申请实施例2提供的马齿苋酰胺2应用于抗敏精华液中，配方表2所示：
表2
工艺流程：
1、准确称取A相并投入到乳化锅中，加热至85℃，保温搅拌1小时；
2、准确称取B相，溶解完全后，投入A相中，均质搅拌1小时；
3、降温至50℃，将C相投入乳化锅中，搅拌10分钟，出锅。
一、抗炎活性测试：
本发明马齿苋酰胺抑制二甲苯致小鼠耳肿胀试验：取体重18～22g雄性昆明种小鼠50只，随机分为5组，每组10只，测试组(1、2、3)包括实施例2制备马齿苋酰胺2(用10％DMSO溶解，制成不同浓度(5mg/mL、10mg/mL、20mg/mL的供试样品溶液)，阳性对照组(阿司匹林，以10％DMSO溶解，制成浓度为10mg/mL供试样品溶液)，空白组(10％DMSO)。各组按20mL·kg-1的剂量灌胃给药，每日1次，连续7d，末次给药30min后，在小鼠右耳涂20μL二甲苯致炎，左耳为空白。2h后将小鼠断颈椎处死，剪下两耳，用直径9mm打孔器切下双耳片称重，以右耳重量减去左耳重量的差值作为炎性肿胀程度的评价标准，并按下述公式计算各组小鼠耳肿胀抑制率。
小鼠耳朵肿胀抑制率％＝(对照组平均耳朵肿度-给药组平均耳朵肿度)/对照组平均耳朵肿度*100％
表3各组对二甲苯所致小鼠耳肿胀的影响(n，X±s)
表3
| 组别 | n | 剂量 | 耳朵肿度(mg) | 抑制率(％) |
| 空白组 | 10 | 200mg/kg | 17.36±0.27*Δ | - |
| 阳性对照组 | 10 | 200mg/kg | 6.34±1.1* | 60.7 |
| 测试组1 | 10 | 200mg/kg | 7.85±1.0*Δ | 50.3 |
| 测试组2 | 10 | 200mg/kg | 6.81±0.74** | 58.9 |
| 测试组3 | 10 | 200mg/kg | 5.35±0.85**Δ | 68.4 |
注:*代表与空白对照组相比，P＜0.01；**代表与测试组1相比，P＜0.01；Δ代表与测试组1相比，P＜0.01。
各组对二甲苯所致小鼠耳肿胀的影响由实验结果可知，与空白对照组相比，各给药组均表现出较强的抑制小鼠耳肿胀活性，表明马齿苋酰胺2能显著抑制二甲苯所致小鼠耳肿胀。
二、抗组胺活性实验
将RBL-2H3细胞培养在24孔板上，用PBS洗涤细胞两次，加入新的含有10％胎牛血清的DMEM培养基0.5ml，继续培养30min。每孔加入不同浓度的含马齿苋酰胺溶液20μl(样品用乙醇溶解)作为测试组1、测试组2、测试组3，加入相同体积的PBS作为正常对照组，另外加入5μM的地塞米松作为阳性对照。30min后再分别加入终浓度为10μg/ml的C48/8020μl，继续培养1h。吸取细胞培养上清50μl，加入到96孔板中，随后加入50μl底物溶液(2mM的p-硝基苯-N-乙酰基-β-D-氨基葡萄糖胺，0.2M柠檬酸，pH4.5)，37℃反应2h。加入1MTris缓冲液(pH9)100μl终止反应，405nm波长下测定吸光度。相应地，用0.1％TritonX-100破碎细胞后离心去除沉淀，同法测定细胞中的β-氨基己糖苷酶。每孔细胞进行蛋白定量，平衡细胞数目差异。根据β-氨基己糖苷酶标准曲线分别计算细胞上清中与细胞中β-氨基己糖苷酶含量，β-氨基己糖苷酶释放率＝上清的β-氨基己糖苷酶/(上清β-氨基己糖苷酶+胞内β-氨基己糖苷酶)×100％。
数据处理结果表示为平均值±标准差，分别为3复孔，重复3次实验的结果。
RBL-2H3细胞分别用浓度(体积比)为0.1％、0.5％及1.0％的马齿苋酰胺溶液或地塞米松(10μM)处理，分别测定对C48/80引起的细胞脱颗粒、组织胺及β-氨基己糖苷酶释放的影响，结果见表4
表4
与阴性对照组相比***P<0.05与C48/80组(模型组)相比#P<0.05，##P<0.01,###P<0.001.由上表4结果可见，与C48/80组相比较，马齿苋酰胺中剂量和高剂量组的脱颗粒率、组织胺和β-氨基己糖苷酶释放率均显著降低，而高剂量组和地塞米松组的效果相当。
三、抗氧化活性测试
清除超氧阴离子抗氧化能力的测定：分别测定壳聚糖、透明质酸钠和实施例1制备的马齿苋酰胺1的清除超氧阴离子能力并做对比(表5)：将实施例1中制备的马齿苋酰胺1在真空冷冻干燥至恒重后，分别用Tris-HCl缓冲溶液(1.9155gTris+0.8mL浓HCl，加水定容至1000mL)配制浓度为0.2、0.4、1.6、3.2mg/mL的溶液。取1.5mL不同浓度的样品溶液，1.5mLTris-HCl缓冲溶液、0.5mlNADH(468μM)，然后在反应液中加入0.5mLPMS(60μM)，在试管中混匀后，样品的最终浓度为0.1、0.2、0.8、1.6mg/mL，室温下静置5min，在560nm处测定吸光度，空白组0.5mLTris-HCl缓冲溶液代替NADH(注：被测样品均测三次，取平均值)。
清除超氧阴离子能力(％)＝[(A空白-A样品)/A空白]×100
表5，测试样品的抗氧化活性(％)
| 0.1mg/mL | 0.2mg/mL | 0.8mg/mL | 1.6mg/mL | |
| 壳聚糖 | 11.23 | 15.41 | 19.78 | 24.36 |
| 透明质酸钠 | 22.14 | 25.36 | 27.16 | 29.45 |
| 马齿苋酰胺1 | 47.54 | 56.54 | 63.27 | 71.39 |
实验结果：本发明所合成的马齿苋酰胺具有抗氧化活性，比壳聚糖及透明质酸钠的抗氧化活性更强。
四、酪氨酸酶活性的抑制实验
实验用含10％胎牛血清、青霉素100U/mL及链霉素100U/mLDMEM细胞培养液将B16黑色素细胞密度调为1×105个/mL，以每孔3mL接种于6孔细胞培养板中，在37℃，5％CO2条件下培养24h后，给予1μMα-MSH，每孔分别给予1ml浓度为100μg/ml的应用例2(含0.5％、1.0％、2.0％实施例2马齿苋酰胺2)的抗敏精华液，分别为测试组1、测试组2和测试组3。对照组加入与组合物同体积的培养基，阳性对照组给予等体积的含有熊果苷的培养基，终浓度为100μg/ml。药物作用3d后，弃除上清液，用PBS冲洗2遍。每孔添加180μL含1％TritonX-100的PBS溶液后，冰浴中超声破碎，每孔加人20μL10mmol/L/的L-DOPA，37℃孵育60min，1500r/min/离心5min，分别取100μL移到96孔细胞培养板，酶标仪检测492nm吸光度值，计算细胞内酪氨酸酶活性。
酪氨酸酶活性＝(A/B)×100％
A为药物组平均吸光度，B为对照组平均吸光度
表6
(n＝4，
)(**，P＜0.01vs对照组；#，P＜0.05vs模型组；##，P＜0.01vs模型组)
由上表可知，本发明组合物能够显著降低B16细胞中酪氨酸酶活性，测试组3对酪氨酸酶的抑制率最高。
综上所述，本发明通过制备具有抗炎、抗组胺、抗氧化及美白功能的系列化合物，使得到的化合物可以用于制备化妆品试剂或药物试剂，本发明中的化妆品试剂和药物试剂没有特定限制。例如可以是柔肤化妆水、营养化妆水、按摩霜、润肤乳、凝胶、营养霜、面膜、啫喱类或沐浴露洗发水等洗去类型的化妆品，也可以是以类似乳霜、软膏、霜、贴膏或喷雾剂等药物制剂产品；作为敏感性皮肤使用，婴儿和儿童化妆品中也可以添加来降低刺激。
以上所述仅为本发明的实施例，并非因此限制本发明的专利范围，凡是利用本发明说明书及附图内容所作的等同变换，或直接或间接运用在相关的技术领域，均同理包括在本发明的专利保护范围内。
Claims (5)
1.马齿苋酰胺，其结构通式如下：
其中，R1、R2、R3、R4为H、OH或OCH3；
列举马齿苋酰胺的结构式如下：
2.权利要求1所述的马齿苋酰胺作为制备抗炎的化妆品试剂的用途。
3.权利要求1所述的马齿苋酰胺作为制备抗组胺的化妆品试剂的用途。
4.权利要求1所述的马齿苋酰胺作为制备抗氧化的化妆品试剂的用途。
5.权利要求1所述的马齿苋酰胺作为制备美白的化妆品试剂的用途。
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