CN110381936A - 包含阿魏酸乙酯作为有效成分的过敏缓解用组合物 - Google Patents
包含阿魏酸乙酯作为有效成分的过敏缓解用组合物 Download PDFInfo
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- CN110381936A CN110381936A CN201880013050.XA CN201880013050A CN110381936A CN 110381936 A CN110381936 A CN 110381936A CN 201880013050 A CN201880013050 A CN 201880013050A CN 110381936 A CN110381936 A CN 110381936A
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- ethyl ester
- acid ethyl
- ferulic acid
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Abstract
本说明书公开了含有阿魏酸乙酯作为有效成分的过敏缓解用组合物。本发明的一方面的组合物可以通过改善作为过敏反应的重要原因的皮肤屏障功能和肥大细胞的脱颗粒反应来有效地改善过敏反应。另外，最近当与作为直接接触于人体的物质的化妆料组合物、药学组合物和食品组合物并用时，具有可预防或最小化由上述组合物引起的过敏反应的优点。
Description
技术领域
本说明书公开了含有阿魏酸乙酯作为有效成分的过敏缓解用组合物。
背景技术
所谓过敏，是指由于先天性或后天性免疫功能存在异常，与过敏原(allergen)接触而引起的病理反应。代表性的过敏原包括花粉、药物、植物纤维、细菌、霉、屋尘螨、食物、灰尘、染色剂、化学物质等。另外，最近由化妆品中含有的各种化学物质和天然提取物引起的过敏疾病事例也在增加。
代表性的过敏性疾病包括异位性皮炎、支气管哮喘、过敏性鼻炎、过敏性角膜炎、皮肤荨麻疹等。对过敏反应的机制进行观察发现，当过敏原侵入活体时，T-辅助细胞(T-helper cell)和B细胞被依次激活而产生IgE。由此产生的IgE结合在肥大细胞膜的高亲和性IgE受体上，并在其中结合螨、花粉等的过敏原而形成交联时，受体会凝聚。通过受体的交联和凝聚，肥大细胞被激活而细胞质内的钙离子浓度等会上升。钙离子浓度的上升作用于细胞膜的胆固醇和细胞骨架系等多种细胞内调节因子，使颗粒移动到细胞膜上的同时，通过颗粒的空泡化、颗粒相互的融合和颗粒与细胞膜的融合等引起脱颗粒。当发生脱颗粒时，在释放出如组胺这样的预先储存在肥大细胞内的化学传递质的同时，还分泌出新合成的前列腺素白三烯等。通过脱颗粒释放的化学传递质中除了含有具有血管扩张、血管透过性亢进、支气管平滑肌的收缩或分泌亢进等的作用的组胺、血清素和白三烯之外，还含有用作嗜酸性粒细胞或中性粒细胞等炎症细胞的趋化因子的NCF、ECF、PAF等，从而引起过敏反应。
目前使用烷基胺、抗-IgE剂等作为抗过敏药物，但副作用大的情况较多，并且只是暂时缓解症状，而不是从根本上消除过敏原因。
因此，有必要开发一种能够从根本上改善过敏疾病，同时具有低副作用且效果持续的新物质。
[现有技术文献]
(非专利文献1)Kim Hyon-hui嗜碱性粒细胞在过敏炎症机制中的作用，天主教大学医学院儿科系，第46卷，第6号，2003年
发明内容
技术课题
在一方面，本发明的目的是改善皮肤过敏现象。
在一方面，本发明的目的是有效地改善由过敏现象引起的皮肤问题。
课题解决手段
在一方面，本发明提供一种过敏缓解用组合物，其包含阿魏酸乙酯、其异构体、其药学上可允许的盐、其前药、其水合物或其溶剂化物作为有效成分。
发明效果
本发明的一方面的包含阿魏酸乙酯、其异构体、其药学上可允许的盐、其前药、其水合物或其溶剂化物作为有效成分的组合物可以通过改善作为过敏反应的重要原因的皮肤屏障功能和肥大细胞的脱颗粒反应来有效地改善过敏反应。另外，最近当与作为直接接触于人体的物质的化妆料组合物、药学组合物和食品组合物并用时，具有可预防或最小化由上述组合物引起的过敏反应的优点。
附图说明
图1是测量在肥大细胞中处理过敏原诱导物质后通过本发明的一方面的组合物处理时的β-氨基己糖苷酶的分泌量的图。
图2是确认在肥大细胞中处理过敏原诱导物质后通过本发明的一方面的组合物处理时的组胺分泌抑制效果的图。
图3是确认在人角质形成细胞中处理本发明的一方面的组合物时的丝氨酸-棕榈酰转移酶1的表达变化的图。
图4是确认在人角质形成细胞中处理本发明的一方面的组合物时的神经酰胺合成酶3的表达变化的图。
具体实施方式
以下，详细说明本发明。
在一方面，本发明是过敏缓解用组合物，其包含阿魏酸乙酯、其异构体、其药学上可允许的盐、其前药、其水合物或其溶剂化物作为有效成分。
上述阿魏酸乙酯也被称为4-羟基-3-甲氧基肉桂酸乙酯(ethyl4-hydroxy-3-methoxycinnamate)，并且是分子式为C12H14O4，分子量为224.24g/mol的物质，结构如下化学式1。
[化学式1]
在本说明书中，“异构体”尤其包括光学异构体(optical isomers)(例如，本质上纯的对映异构体(essentially pureenantiomers)、本质上纯的非对映异构体(essentially purediastereomers)或其混合物)，还包括构象异构体(conformationisomers)(即，只有一个以上的化学键的其角度不同的异构体)、位置异构体(positionisomers)(特别是，互变异构体(tautomers))或几何异构体(geometric isomers)(例如，顺反异构体)。
在本说明书中，所谓“本质上纯(essentially pure)”，是指例如当与对映异构体或非对映异构体关联地使用时，能以对映异构体或非对映异构体为例的具体化合物存在约90％以上，具体地约95％以上，更具体地约97％以上或约98％以上，更具体地约99％以上，进一步更具体地约99.5％以上(w/w)。
在本说明书中，所谓“药学上可允许”，是指以下可以得到政府或相当于政府的管制机构的认可或批准，或者被列入药典或被认知为其他一般药典：当以通常的医药服用量(medicinal dosage)利用时，避免显著的毒性效果，从而可用于动物，更具体地可用于人。
在本说明书中，“药学上可允许的盐”是指药学上可允许的并且具有母体化合物(parent compound)的优选药理活性的根据本发明的一方面的盐。上述盐可以包括(1)由诸如盐酸、氢溴酸、硫酸、硝酸、磷酸的无机酸形成；或由诸如乙酸、丙酸、己酸、环戊烷丙酸、乙醇酸、丙酮酸、乳酸、丙二酸、琥珀酸、苹果酸、马来酸、富马酸、酒石酸、柠檬酸、苯甲酸、3-(4-羟基苯甲酰基)苯甲酸、肉桂酸、扁桃酸、甲烷磺酸、乙烷磺酸、1,2-乙烷-二磺酸、2-羟基乙烷磺酸、苯磺酸、4-氯苯磺酸、2-萘磺酸、4-甲苯磺酸、樟脑磺酸、4-甲基双环[2,2,2]-辛-2-烯-1-羧酸、葡庚糖酸、3-苯丙酸、三甲基乙酸、叔丁基乙酸、十二烷基硫酸、葡萄糖酸、谷氨酸、羟基萘甲酸、水杨酸、硬脂酸、粘康酸的有机酸形成的酸加成盐(acid additionsalt)；或(2)母体化合物中存在的酸性质子被置换时形成的盐。
在本说明书中，“前药(prodrug)”是指将某种药物经过化学变化而调节物理、化学性质的药物，其本身不表现出生理活性，但投给后在体内通过化学或酶的作用转变为原始药物，从而可以发挥药效。
在本说明书中，“水合物(hydrate)”是指结合有水的化合物，并且是一个包含在水和化合物之间不具有化学结合力的包合物的广义概念。
在本说明书中，“溶剂化物”是指在溶质的分子或离子与溶剂的分子或离子之间形成的高次化合物。
上述组合物可改善由过敏引起的皮肤问题。在本说明书中，“皮肤问题”是指包括由于过敏而导致皮肤处于不正常状态的情况。
在本说明书中，所谓“皮肤”，是指覆盖动物体表的组织，并且是一个不仅包括覆盖脸部或身体等的体表的组织，还包括头皮的广义概念。
在本说明书中，“过敏”是一种最广义的概念，是指生物体与某种外来性物质(allergen)接触后因抗原抗体反应而表现出的活体内反应变化而出现的身体变化。在本说明书中，上述外来性物质的种类没有限制，具体地，可以包括花粉、药物、植物纤维、细菌、食物、染色剂或化学物质等，但不限于此。在本说明书中，由上述外来性物质引起变化的身体的特定部位不受限制。
另外，在本说明书中，过敏是指还包括根据由内因性因素(例如，激素变化、压力、情绪障碍、疲劳、睡眠不足等)引起的活体内反应变化而出现的身体的变化。
上述过敏疾病可以是选自由浮肿(edema)、过敏症(anaphylaxis)、过敏性鼻炎(allergic rhinitis)、过敏性哮喘(allergic asthma)、枯草热(hay fever)、昆克浮肿(Quincke's edema)、过敏性结膜炎(allergic conjunctivitis)、过敏性角膜炎(allergickeratitis)、过敏性皮炎(allergic dermatitis)、异位性皮炎(atopic dermatitis)、接触性皮炎(contact dermatitis)、荨麻疹(hives)、瘙痒症(pruritus)、昆虫过敏、食品过敏和药品过敏组成的组中的一种以上，但不限于此，并且包括因外来性因素或内因性因素而引起的活体的所有变化。
另一方面，皮肤是一种保持体内水分，并且起到保护外部侵入因子(抗原、感染原等)的内部侵入的必要屏障功能，同时表现出免疫反应的代表性的器官，这种屏障功能对皮肤健康产生全面影响。因此，如果强化皮肤屏障功能，则可以缓解或改善包含过敏的皮肤问题。
上述组合物可抑制肥大细胞的脱颗粒反应或强化皮肤屏障功能。具体地，当引发肥大细胞脱颗粒时，可能分泌组胺，由此引起炎症、瘙痒症或皮肤发红现象等的皮肤问题，而上述组合物可以缓解由分泌组胺引起的皮肤问题，从而抑制皮肤屏障损伤。
具体地，上述组合物可以包括下述中一种以上的特征：1)抑制从肥大细胞分泌β-氨基己糖苷酶(β-hexosaminidase)；2)抑制从肥大细胞分泌组胺；3)增加丝氨酸-棕榈酰转移酶(Serine-Palmitoyltransferase，SPTLC)的表达；以及4)增加神经酰胺合成酶(Ceramide Synthase，CerS)的表达。
具体地，当投给含有20ppm的阿魏酸乙酯的上述组合物时，与仅投给作为过敏诱导化学物质的PMA 50nM和A23187 1μM的情况相比，可以将组胺的分泌量抑制至35％以上。另外，当投给含有50ppm的阿魏酸乙酯的上述组合物时，与未投给的组相比，SPTLC的表达可以促进50％以上，并且CerS的表达可以促进30％以上。
在一实施例中，上述组合物可能是在角质形成细胞中增加丝氨酸-棕榈酰转移酶或神经酰胺合成酶的表达。
上述丝氨酸-棕榈酰转移酶可以是丝氨酸-棕榈酰转移酶1，上述神经酰胺合成酶可以是神经酰胺合成酶3。
即，根据本发明的组合物可以抑制过敏诱导物质的生成本身，因此通过含有对于已经生成而分泌的过敏诱导物质的受体的拮抗剂作为其成分，可以解决不能从根本上解决过敏原因的现有的用于改善、缓解或治疗过敏疾病的组合物所具有的局限性。因此，根据本发明的抗过敏用组合物可以有用地用作对预防、改善或治疗过敏疾病(例如，哮喘、异位性皮炎、鼻炎等)具有优异效能的组合物。
在一实施例中，上述组合物可以包含0.0001～5重量％的其异构体、其药学上可允许的盐、其前药、其水合物或其溶剂化物。当上述组合物中包含的阿魏酸乙酯、其异构体、其药学上可允许的盐、其前药、其水合物或其溶剂化物的含量小于0.0001重量％时，无法获得有效的抗过敏效果，当超过5重量％时，由于剂型内有效成分的结晶而存在剂型稳定性降低的问题。上述阿魏酸乙酯、其异构体、其药学上可允许的盐、其前药、其水合物或其溶剂化物的含量可以优选为0.0001～3重量％，更优选为0.001～2重量％，甚至更优选为0.01～1重量％。
在一实施例中，上述组合物可以是药学组合物、食品组合物或化妆料组合物。
在本说明书中，化妆料组合物的剂型没有特别限制，可根据目的适当地选择。
例如，可以制造成溶液、通过将油相分散在水相中而获得的乳液、通过将水相分散在油相中而获得的乳液、悬浮液、固体、凝胶、粉末、膏、泡沫(foam)或气溶胶组合物的剂型，但不限于此。
另外，除了上述物质之外，化妆料组合物在不损害主要效果的范围内，优选地还可以包含对主要效果有协同效果的其他成分。另外，上述化妆料组合物还可以包含保湿剂、润肤剂、紫外线吸收剂、防腐剂、杀菌剂、抗氧化剂、pH调节剂、有机和无机颜料、香料、冷感剂或制汗剂。本领域技术人员可以在不损害本说明书的目的和效果的范围内容易地选择并使用上述成分的配合量。
另外，食品组合物在不损害有效成分所期望的主要效果的范围内，还可以包含对主要效果有协同效果的其他成分等。例如，为了改善物理性质，还可以包含香料、色素、杀菌剂、抗氧化剂、防腐剂、保湿剂、增稠剂、无机盐类、乳化剂和合成聚合物物质等的添加剂。除此之外，还可以包含水溶性维生素、油溶性维生素、聚合物肽、聚合多糖和海藻提取物等的辅助成分。本领域技术人员可根据剂型或使用目的，毫无困难地选择并配合上述成分，并且其添加量可以在不损害本说明书的目的和效果的范围内选择。
在本说明书中，药学组合物可以是包含皮肤外用剂组合物的那些。药学组合物的剂型可以是溶液剂、悬浮剂、乳液剂、凝胶剂、点滴剂、栓剂(坐剂)、乳膏剂、软膏剂、贴剂、片剂或喷雾剂，但不限于此。上述剂型可根据本领域的常规方法容易地制备，并且可以适当地使用赋形剂、水和剂、乳化促进剂、悬浮剂、用于调节渗透压的盐或缓冲剂、着色剂、香辛料、稳定剂、防腐剂、保存剂或其他常用的辅助剂。
其每日投给用量可以是，例如，0.1mg/g/日至100mg/g/日，更具体地，5mg/g/日至50mg/g/日，但不限于此。
上述组合物优选地可以为水包油型，并且在一实施例中可以为水包油型的乳膏剂型。
根据一实施例的乳膏剂型如下表1。
[表1]
| 成分 | 含量(重量％) |
| 乙二胺四乙酸二钠 | 0.02 |
| 甘油 | 5.00 |
| 丁二醇 | 5.00 |
| 卡波姆 | 0.30 |
| 单硬脂酸甘油酯 | 1.50 |
| PEG-40硬脂酸酯 | 1.00 |
| 鲸蜡硬脂醇 | 1.50 |
| 脱水山梨醇硬脂酸酯 | 0.50 |
| 氢化聚癸烯 | 4.00 |
| 鲸蜡醇乙基己酸酯 | 5.00 |
| 聚二甲基硅氧烷 | 1.00 |
| 苯氧乙醇 | 0.50 |
| 阿魏酸乙酯 | 0.20 |
| 水 | 至100 |
以下，将例举实施例和试验例更具体地说明本发明的构成和效果。然而，这些实施例和试验例只是为了帮助理解本发明而以示例的目的提供的，并且本发明的范畴和范围不局限于以下例。
[实施例1]阿魏酸乙酯的抗过敏效果确认实验-抑制存在于肥大细胞的颗粒内的过敏诱导物质的分泌
[实施例1-1]抑制β-氨基己糖苷酶的活性
将作为过敏诱导物质的PMA(Phorbol 12-myristate 13-acetate)和钙离子载体A23187各自混合50nM和1μM，从而对肥大细胞进行处理，并通过各浓度(12.5ppm、25ppm、50ppm、100ppm)阿魏酸乙酯进行处理后，测量并决定作为脱颗粒的标记物的β-氨基己糖苷酶的活性，并且β-氨基己糖苷酶的活性通过从对硝基苯基-乙酰基-β-D-氨基葡萄糖苷(p-nitrophenyl-acetyl-β-Dglucosaminide)释放的对硝基苯基(p-nitrophenol)的量决定。将未通过过敏诱导物质进行处理的组作为阴性对照组(without PMA)，将仅通过过敏诱导物质进行处理的组作为阳性对照组((-)Con)。
其结果，如图1所示，显示出阿魏酸乙酯抑制作为肥大细胞脱颗粒的标志物的β-氨基己糖苷酶的分泌。因此，可以确认阿魏酸乙酯具有优异的抑制存在于肥大细胞的颗粒内的过敏诱导物质的分泌的效果。
[实施例1-2]确认组胺分泌抑制能力
将RBL-2H3细胞(购自韩国细胞株银行)以2.5×105细胞/孔的浓度接种并培养于96孔板中。细胞附着后，在台氏缓冲液(10mM Hepes、130mM NaCl、5mM KCl、1.4mM CaCl2，1mM MgCl2，5.6mM glucose和0.1％BSA，pH 7.4)中分别处理各浓度阿魏酸乙酯后培养24小时。添加50nM PMA和A23187 1μM后，在培养基中进行反应1小时，回收上清液以测定是否阻碍组胺释放。组胺释放根据组胺试剂盒(cisbio assays)的方法测定。
其结果，可以确认阿魏酸乙酯抑制组胺的分泌量最少37％以上，从而对改善过敏有效果(图2)。
[实施例2]确认皮肤屏障功能改善效果
将人角质形成细胞(human keratinocyte，HaCaT)在包含10％FBS、1％青霉素/链霉素的培养基中培养后，接种于各孔使得6-孔板中细胞的浓度为1×105细胞/孔后，培养48小时，并分别添加各浓度阿魏酸乙酯后培养24小时。为了进行评价，与未处理对照组一起使用，反应结束后，收集上清液，用PBS(Phosphate BufferSaline)清洗细胞，回收细胞并根据RNA小量试剂盒(ambion by life technologies)方法提取mRNA。之后，根据高容量RNA-to-cDNA试剂盒(Applid Biosystems)方法合成cDNA，然后对试验细胞和对照组细胞进行实时定量荧光PCR以分析CerS3、SPTLC1基因表达水平。PCR中使用的引物信息如下表2所示。
[表2]
| 引物种类 | 序列 |
| CerS3(正向) | TGG TTC TGG TCG GAG AGA TAC TGG C |
| CerS3(反向) | GAA GCT CAT CAG ACT AAT AGC AGC C |
| SPTLC1(正向) | TGG AAG AGA GCA CTG GGT CT |
| SPTLC1(反向) | GCT ACC TCC TTG ATG GTG GA |
其结果，确认了在通过阿魏酸乙酯进行处理的情况下，对促进神经酰胺的合成有直接影响的丝氨酸-棕榈酰转移酶和神经酰胺合成酶3的表达分别促进50％以上，25％以上，从而对改善皮肤屏障功能有效果(图3和图4)。
Claims (6)
1.一种过敏缓解用组合物，其包含阿魏酸乙酯(ethyl ferulate)、其异构体、其药学上可允许的盐、其前药、其水合物或其溶剂化物作为有效成分。
2.根据权利要求1所述的过敏缓解用组合物，其中，
上述组合物抑制肥大细胞的脱颗粒反应或强化皮肤屏障功能。
3.根据权利要求2所述的过敏缓解用组合物，其中，上述组合物包含下述中一种以上的特征：
1)抑制从肥大细胞分泌β-氨基己糖苷酶(β-hexosaminidase)；
2)抑制从肥大细胞分泌组胺；
3)增加丝氨酸-棕榈酰转移酶(Serine-Palmitoyltransferase)的表达；以及
4)增加神经酰胺合成酶(Ceramide Synthase)的表达。
4.根据权利要求1所述的过敏缓解用组合物，其中，
上述组合物包含0.0001重量％～5重量％的上述阿魏酸乙酯、其异构体、其药学上可允许的盐、其前药、其水合物或其溶剂化物。
5.根据权利要求1至4中的任意一项所述的过敏缓解用组合物，其中，
上述组合物是药学组合物、食品组合物或化妆料组合物。
6.根据权利要求5所述的过敏缓解用组合物，其中，
上述组合物是水包油型。
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| Publication number | Publication date |
|---|---|
| KR20180098104A (ko) | 2018-09-03 |
| KR101981482B1 (ko) | 2019-05-23 |
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