CN112294791A - 一种虾青素酯在促毛发生长制品中的应用 - Google Patents
一种虾青素酯在促毛发生长制品中的应用 Download PDFInfo
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Abstract
本发明属于虾青素酯制备技术领域,具体涉及一种虾青素酯在促毛发生长制品中的应用。本发明本发明通过实验研究,证明虾青素及虾青素酯具有促进毛发生长的作用,同时具有缓解脱发的作用,使虾青素及虾青素酯增加了一种新的用途,具有产业利用价值,而且该结果可应用于促进毛发生长的医学临床实践,用于开发生发的药品和化妆品,具有潜在的经济和社会效益,并满足了人们对防脱发产品的需求。
Description
技术领域:
本发明属于虾青素酯制备技术领域,具体涉及一种虾青素酯在促毛发生长制品中的应用。
背景技术:
虾青素是一种非维生素A原的含氧类胡萝卜素,化学名称为3,3’-二羟基-4,4’-二酮基-β,β’-胡萝卜素,由一个共轭多烯链及两个末端环状结构构成虾青素分子结构中含有β-紫罗兰酮环和多不饱和共轭双键,使其具有很强的淬灭单线态氧的能力,是氧自由基的超强清除剂。研究表明,虾青素的抗氧化活性是其他类或萝卜素的数十倍,是维生素E的百倍以上。大量的动物实验证明,虾青素具有抗衰老,抗炎,降低氧化损伤,增强机体免疫力等生理功能,可以预防和改善一些慢性疾病如癌症,如糖尿病、心脑血管疾病等。虾青素中羟基和酮基的存在使得虾青素可以被酯化,虾青素末端环结构上的羟基可以与不同脂肪酸发生酯化反应形成虾青素酯。当一端羟基发生酯化时形成虾青素单酯,两端羟基均发生酯化时则形成虾青素双酯。酯化反应后,虾青素的疏水性增大,双酯比单酯的疏水性更强。虾青素酯在自然界中的存在形态主要为游离态和酯化态(虾青素单酯和虾青素双酯)。自然界中,不同生物体内虾青素的存在形态多种多样,主要与虾青素上所连接的脂肪酸的种类和数量有关。对虾青素酯活性的研究并不多,随着对虾青素酯研究的不断深入,其越来越多的生物活性也不断被发现,应用的领域也越来越广泛。
脱发是指头发脱落的现象。正常脱落的头发都是处于退行期及休止期的毛发,由于进入退行期与新进入生长期的毛发不断处于动态平衡,故能维持正常数量的头发。病理性脱发是指头发异常或过度的脱落,其原因很多。比如雄激素性脱发、神经性脱发、内分泌脱发、营养性脱发、物理性脱发、化学性脱发、感染性脱发、症状性脱发、先天性脱发和季节性脱发等原因。脱发问题影响着全球数以百万计的人,并可能对个人的心理和情感健康造成影响,目前应用较为广泛,研究较为深入的治疗方法主要有药剂涂抹和光刺激治疗两种,而缺乏日常饮食角度的相关研究。光刺激治疗方面,目前应用较广的是低水平激光疗法。在药剂涂抹方面,米诺地尔、非那雄胺、JAK抑制剂等为代表的化学合成物较为常见,但因其存在适应范围窄、价格高昂限制了其在脱发人群中的应用。此外,米诺地尔和马前列胺等治疗脱发药物存在头皮发炎,神经损伤等副作用。日常饮食因素已被证实与肥胖、癌症等诸多人类疾病都有密切关联,且日常饮食的改善能够起到良好的防护作用,因此在饮食方向探究脱发治疗的新途径可能具有重要意义。近年来,海洋生物功效因子的结构与功能得到了广泛研究,虾青素及虾青素酯的营养健康功效已经受到越来越多的关注。已有报道表明虾青素及其酯类化合物具有抗癌、预防胃溃疡、改善炎症等生理活性,但鲜有研究表明虾青素及虾青素酯是否会促进毛发生长。
发明内容:
本发明要解决的技术问题是目前针对脱发的治疗方法存在多种缺陷,如适应范围窄、价格高昂及副作用;而在饮食方向探究脱发治疗的新途径可能具有重要意义,其中,虾青素因其清除自由基、抗癌、抗炎、抗衰老等生理活性而受到越来越多研究者的青睐,但虾青素在体内的活性偏低、体内吸少、代谢过快和生物利用度低,限制了其进一步的临床运用。
为解决上述问题,本发明本发明通过实验研究,证明虾青素及虾青素酯具有促进毛发生长的作用,同时具有缓解脱发的作用,使虾青素及虾青素酯增加了一种新的用途,具有产业利用价值,而且该结果可应用于促进毛发生长的医学临床实践,用于开发生发的药品和化妆品,具有潜在的经济和社会效益,并满足了人们对防脱发产品的需求。
为达到上述目的,本发明具体通过以下技术方案实现:
一种虾青素酯在促毛发生长制品中的应用。其中,所述虾青素酯为富含DHA/EPA的虾青素酯。W-3多不饱和脂肪酸(特别是DHA/EPA)有助于宠物的智力发育及视力保持,增进宠物毛发的光泽度;此外,多不饱和脂肪酸可通过能扩张皮肤血管、改善皮肤微循环而促进毛发生长;还可以增加磷酸化的p38丝裂原活化蛋白激酶和Akt的含量从而加速真皮成纤维细胞中Ⅰ型胶原蛋白和弹性蛋白的产生。而虾青素是一种良好的抗氧化剂,一方面可以延缓DHA/EPA的氧化,一方面可以通过缓解活性氧簇损伤、提高干细胞增殖活力进而靶向毛囊干细胞从而促进毛发生长以及抑制脱发。本发明通过改进化学法制备的虾青素酯具有虾青素和DHA/EPA的双重生物活性,且具有更高的生物利用度和良好的脂溶性,此外虾青素酯还具有良易于透皮吸收、促进毛发生长效果优异等优良特性。
进一步的,所述虾青素酯中DHA/EPA含量为30-60%。
进一步的,所述虾青素酯为虾青素单酯和虾青素双酯中的一种或一种以上的混合物。
进一步的,所述化合物其结构式如图1所示,将DHA/EPA引入虾青素类化合物中,虾青素中的酚羟基酯化后,化合物的稳定性增加从而形成一种新型的虾青素酯衍生物,改善了n-3多不饱和脂肪酸易氧化的情况;并且单独补充虾青素和DHA/EPA时,二者会在进入体内的过程中被排泄掉很大一部分,只有少部分可以进入体内继续发挥生理作用,本发明的化合物以酯的形式可以将更多虾青素和n-3多不饱和脂肪酸带入体内脏器,然后在体内再分解为虾青素和DHA/EPA起效,解决了虾青素在体内的活性偏低、体内吸少、代谢过快和生物利用度低的问题。所以本发明的化合物既能发挥虾青素的抗炎、抗氧化的作用,又发挥DHA/EPA高生物利用度、促进毛发生长的作用,且避免了虾青素在体内活性偏低、吸收少、代谢过快和生物利用度低以及DHA/EPA易氧化等缺点。
进一步的,所述制品包括功能性食品或药品,及相关制品,如乳剂等。
进一步的,所述促进毛发生长的制品优选为特医食品,保健品,药品或者生物制剂。
进一步的,所述制品包含有药理有效浓度(1%-100%)的上述虾青素酯。
一种上述虾青素酯的制备方法,包括以下步骤:
(1)量取游离DHA/EPA 1.5mL,称取游离虾青素500mg、催化剂EDCL 1600mg和DMAP400mg置于棕色小瓶中。加入5mL的二氯甲烷,充氮密封后充分混合均匀。置于25℃的震荡培养箱中反应10h。通过薄层层析TLC板确定虾青素双酯的合成情况。
(2)量取游离DHA/EPA 0.6mL,称取游离虾青素500mg、催化剂EDCL 400mg和DMAP200mg置于棕色小瓶中。加入5mL的二氯甲烷,充氮密封后充分混合均匀。置于25℃的震荡培养箱中反应1h。通过薄层层析TLC板确定虾青素单酯的合成情况。
(3)将制备好的DHA/EPA单酯/双酯用100mL二氯甲烷充分溶解后,置于分液漏斗中。首先加入100mL 1mol/L的盐酸溶液,充分混匀静置分层后弃去上层,重复洗涤3次;其次加入100mL的饱和碳酸氢钠溶液,充分混匀静置分层后弃去上层,重复洗涤3次;最后加入100mL的饱和氯化钠溶液,充分混匀静置分层后弃去上层,重复洗涤3次。将最后一次下层液体低温避光旋蒸,以除去有机试剂而得到DHA/EPA单酯/双酯。样品避光充氮置于-40℃保存。
(4)称取一定量的柱层析硅胶(200-300目),置于110℃烘箱中活化2h备用。量取800mL纯硅胶,用正己烷充分溶解后装入硅胶柱(5.5cm×60cm)中,用5倍柱体积的正己烷压实硅胶柱。称取50g已活化好的纯硅胶于250mL体积的旋蒸瓶中,步骤3得到的DHA/EPA单酯/双酯用适量的二氯甲烷溶解后倒入,低温避光旋蒸至粉末状后用正己烷充分溶解,湿法上样。分别用正己烷、正己烷/丙酮(90/10)和正己烷/丙酮(80/20)的混合试剂洗脱硅胶柱中的虾青素酯。洗脱过程中通过用TLC点板的方法确定虾青素单酯和虾青素双酯的分离情况。洗脱过程中分别收集单酯和双酯的洗脱液,低温避光条件下减压浓缩,分别收集到虾青素单酯和双酯的样品,并于-40℃避光充氮保存。
在最优条件下(即步骤1和步骤2的条件参数),通过化学法合成(即步骤1和步骤2)的DHA/EPA-虾青素酯,均可经硅胶柱纯化得单一产物,高效液相色谱检测后单酯纯度在90%左右,双酯纯度高于98%。
本发明的有益效果如下:
(1)本发明首次通过改进化学法制备了富含DHA/EPA的虾青素酯,具有虾青素和DHA/EPA的双重生物活性,且具有更高的生物利用度和良好的脂溶性,此外还具有良易于透皮吸收、促进毛发生长效果优异等优异特性,满足了人们对防脱发产品的需求,具有潜在的经济和社会效益。
(2)本发明以虾青素和DHA/EPA为原料制备富含DHA/EPA的虾青素酯,进一步分离和转化,制得的纯度均在95%以上。
(3)本发明提供的制备方法成本低,步骤简单,使用的有机溶剂量少,对环境产生的有机溶剂污染小。
(4)通过动物实验验证,脱毛小鼠仅补充干预200-500mg/kg的富含DHA/EPA的虾青素酯,就明显提高了小鼠的毛发覆盖率,并且促进了小鼠的毛发生长,且虾青素双酯效果显著优于其他化合物;说明了DHA/EPA的虾青素酯能有效预防、改善或治疗脱发问题。
附图说明
图1为本发明实施例2中富含DHA/EPA的虾青素酯结构;
图2为本发明实施例2中不同小鼠的毛发生长的结果图;
图3为本发明实施例2中不同小鼠的毛发覆盖率的结果图;
图4为富含DHA/EPA的虾青素酯的TLC图谱;
图5为虾青素单酯的高效液相色谱(HPLC)结果;
图6为虾青素双酯的高效液相色谱(HPLC)结果。
具体实施方式:
为使本发明实施例的目的、技术方案和优点更加清楚,下面对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1:富含DHA/EPA的虾青素酯的制备
1)量取游离DHA/EPA 1.5mL,称取游离虾青素500mg、催化剂EDCL 1600mg和DMAP400 mg置于棕色小瓶中。加入5mL的二氯甲烷,充氮密封后充分混合均匀。置于25℃的震荡培养箱中反应10h。通过薄层层析TLC板确定虾青素双酯的合成情况。
2)量取游离DHA/EPA0.6 mL,称取游离虾青素500mg、催化剂EDCL400 mg和DMAP200mg置于棕色小瓶中。加入5mL的二氯甲烷,充氮密封后充分混合均匀。置于25℃的震荡培养箱中反应1h。通过薄层层析TLC板确定虾青素单酯的合成情况。
3)将制备好的DHA/EPA单酯/双酯用100mL二氯甲烷充分溶解后,置于分液漏斗中。首先加入100mL 1mol/L的盐酸溶液,充分混匀静置分层后弃去上层,重复洗涤3次;其次加入100mL的饱和碳酸氢钠溶液,充分混匀静置分层后弃去上层,重复洗涤3次;最后加入100mL的饱和氯化钠溶液,充分混匀静置分层后弃去上层,重复洗涤3次。将最后一次下层液体低温避光旋蒸,以除去有机试剂而得到DHA/EPA单酯/双酯。样品避光充氮置于-40℃保存。
4)称取一定量的柱层析硅胶(200-300目),置于110℃烘箱中活化2h备用。量取800mL纯硅胶,用正己烷充分溶解后装入硅胶柱(5.5cm×60cm)中,用5倍柱体积的正己烷压实硅胶柱。称取50g已活化好的纯硅胶于250mL体积的旋蒸瓶中,将单/双酯反应后的溶液倒入,再倒入适量的二氯甲烷于旋蒸瓶中充分混匀,确保样品与硅胶充分结合。低温避光旋蒸至粉末状后用正己烷充分溶解,湿法上样。分别用正己烷、正己烷/丙酮(90/10)和正己烷/丙酮(80/20)的混合试剂洗脱硅胶柱中的虾青素酯。洗脱过程中通过用TLC点板的方法确定虾青素单酯和虾青素双酯的分离情况。洗脱过程中分别收集单酯和双酯的洗脱液,低温避光条件下减压浓缩,分别收集到虾青素单酯和双酯的样品,并于-40℃避光充氮保存。
5)在最优条件下,通过化学法合成的DHA/EPA-虾青素酯,均可经硅胶柱纯化得单一产物,高效液相色谱检测后单酯纯度在90%左右,双酯纯度高于98%。
实施例2:动物实验
2.1.材料和方法
(1)动物喂养和行为学分析
实验动物采用雄性KM小鼠,体重20-22g,购自北京维通利华实验动物技术有限公司。动物房湿度65±15%,室温23±2℃,12h:12h明暗交替,小鼠可自由摄食和饮水。64只雄性KM小鼠适应性喂养一周后,根据体重将小鼠分为正常组、模型对照组、DHA/EPA组、AST组、DHA/EPA单酯组、DHA/EPA双酯组、虾青素+DHA/EPA组(1:1)、虾青素+DHA/EPA组(1:2)。饲料参照AIN-93G啮齿动物饲料配方并加以改良,记录和统计摄食量。随即对所有小鼠进行背部毛发脱除处理采用化学法脱毛,配制6%的硫化钠酒精溶液,用脱脂棉蘸取脱毛剂涂抹在小鼠背部,脱毛区域为前腿连线至后腿连线处的矩形区域,待脱毛剂作用后,用温水冲洗,则毛发脱落。分组后随即进行第一次脱毛处理,6%硫化钠酒精溶液作用2min后,用温水冲洗干净;为保证所有小鼠毛发脱除程度一致,三天后进行第二次脱毛处理,6%硫化钠酒精溶液作用1min后,用温水冲洗干净。定时饲养小鼠并记录体重、摄食量、毛发生长等日常生长指标。对新生毛发的长度、覆盖面积定期监测,根据T.-R.Kwon等人的方法,对小鼠皮肤裸露区域的新生毛发覆盖率进行评分:0=0%,1=0%-20%,2=20%-40%,3=40%-60%,4=60%-80%,5=80%-100%。
(2)统计学处理
实验数据以x±SEM表示,采用SPSS 18.0软件进行Student’s t test and Tukey’s test分析,以P<0.05为有显著差异。
(3)实验结果
富含DHA/EPA的虾青素酯对脱毛小鼠的毛发生长影响结果如图2所示,对小鼠进行二次脱毛处理后记录小鼠毛发长度,然后进行显著性分析,各组间毛发长度无显著性差异。将毛发长度记为y,将毛发生长天数记为x,选用S型函数logistic模型进行拟合,得到如图2和表1所示的函数拟合结果,其更精确的显示出了各组的毛发生长特征,且与观测结果较为一致。最大生长速率Kmax可以代表毛囊细胞的活跃程度,结果显示DHA/EPA双酯、DHA/EPA单酯、虾青素+DHA/EPA组(1:1)、虾青素+DHA/EPA组(1:2)均具有良好的保持毛囊细胞活跃的作用,其中DHA/EPA双酯最为显著;结果为DHA/EP双酯>DHA/EPA单酯>虾青素+DHA/EPA(1:2)>虾青素组+DHA/EPA(1:1)>虾青素>DHA/EPA>模型。
表1
各组小鼠的毛发覆盖率-时间图像如图3所示,与毛发长度的观测结果一致,DHA/EPA双酯、DHA/EPA单酯、虾青素+DHA/EPA(1:2)和虾青素+DHA/EPA(1:1)毛发生长较早。对小鼠毛发覆盖率进行显著性分析,各组间毛发覆盖率显著性差异。将新生毛发面积评分记为y,将毛发生长天数记为x,同样用S型函数logistic模型进行拟合,得到如图3和表2所示的函数拟合结果,最终新生毛发覆盖程度排序为DHA/EPA双酯>DHA/EPA单酯>>虾青素组+DHA/EPA(1:2)>虾青素组+DHA/EPA(1:1)>虾青素>DHA/EPA>模型。从覆盖率结果可以得知:DHA/EPA双酯作用效果最明显。
表2
以上所述,仅是本发明的较佳实施例而已,并非是对本发明作其它形式的限制,任何熟悉本专业的技术人员可能利用上述揭示的技术内容加以变更或改型为等同变化的等效实施例。但是凡是未脱离本发明技术方案内容,依据本发明的技术实质对以上实施例所作的任何简单修改、等同变化与改型,仍属于本发明技术方案的保护范围。
Claims (10)
1.一种虾青素酯在促毛发生长制品中的应用;其中,所述虾青素酯为富含DHA/EPA的虾青素酯。
2.一种权利要求1中的虾青素酯,其特征在于:DHA/EPA的含量为30-60%。
3.如权利要求2所述的虾青素酯,其特征在于:所述虾青素酯为虾青素单酯和虾青素双酯中的一种或一种以上的混合物。
5.如权利要求1所述的应用,其特征在于:所述制品包括功能性食品或药品,及相关制品。
6.如权利要求1所述的应用,其特征在于:所述促毛发生长的制品优选为特医食品,保健品,药品或者生物制剂。
7.如权利要求1所述的应用,其特征在于:所述制品包含有药理有效浓度(1%-100%)的所述的权利要求1所述的虾青素酯。
8.一种权利要求1中虾青素酯的制备方法,其特征在于包括以下步骤:
(1)量取游离DHA/EPA,称取游离虾青素、催化剂EDCL和DMAP置于棕色小瓶中;加入二氯甲烷,充氮密封后充分混合均匀;置于25℃的震荡培养箱中反应;
(2)制备好的DHA/EPA单酯或双酯用二氯甲烷充分溶解后,置于分液漏斗中;首先加入盐酸溶液,充分混匀静置分层后弃去上层,重复洗涤3次;其次加入饱和碳酸氢钠溶液,充分混匀静置分层后弃去上层,重复洗涤3次;最后加入饱和氯化钠溶液,充分混匀静置分层后弃去上层,重复洗涤3次;将最后一次下层液体低温避光旋蒸,以除去有机试剂而得到DHA/EPA单酯/双酯;样品避光充氮置于-40℃保存;
(3)经硅胶柱层析洗脱、收集,得到虾青素酯。
9.如权利要求8所述的虾青素酯的制备方法,其特征在于:制备DHA/EPA单酯时,步骤(1)具体为量取游离DHA/EPA 1.5mL,称取游离虾青素500mg、催化剂EDCL 1600mg和DMAP400mg置于棕色小瓶中;加入5mL的二氯甲烷,充氮密封后充分混合均匀;置于25℃的震荡培养箱中反应10h;通过薄层层析TLC板确定虾青素双酯的合成情况。
10.如权利要求8所述的虾青素酯的制备方法,其特征在于:制备DHA/EPA双酯时,步骤(1)具体为量取游离DHA/EPA 0.6mL,称取游离虾青素500mg、催化剂EDCL 400mg和DMAP200mg置于棕色小瓶中;加入5mL的二氯甲烷,充氮密封后充分混合均匀;置于25℃的震荡培养箱中反应1h;通过薄层层析TLC板确定虾青素单酯的合成情况。
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