CN110075000A - 一种羟基酪醇包合物及其制备方法和用途 - Google Patents
一种羟基酪醇包合物及其制备方法和用途 Download PDFInfo
- Publication number
- CN110075000A CN110075000A CN201910315938.5A CN201910315938A CN110075000A CN 110075000 A CN110075000 A CN 110075000A CN 201910315938 A CN201910315938 A CN 201910315938A CN 110075000 A CN110075000 A CN 110075000A
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- China
- Prior art keywords
- hydroxytyrosol
- inclusion compound
- cyclodextrin
- hydroxypropyl
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- JUUBCHWRXWPFFH-UHFFFAOYSA-N Hydroxytyrosol Chemical compound OCCC1=CC=C(O)C(O)=C1 JUUBCHWRXWPFFH-UHFFFAOYSA-N 0.000 title claims abstract description 206
- 229940095066 hydroxytyrosol Drugs 0.000 title claims abstract description 104
- 235000003248 hydroxytyrosol Nutrition 0.000 title claims abstract description 103
- 150000001875 compounds Chemical class 0.000 title claims abstract description 55
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 claims abstract description 38
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Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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Abstract
本发明公开了一种羟基酪醇包合物及其制备方法和其用途,羟基酪醇包合物包括下列质量分数的原料:羟基酪醇0.5~5份,羟丙基‑β‑环糊精5~55份,保护剂0.5~8份。本发明通过羟丙基‑β‑环糊精包埋羟基酪醇和保护剂的作用,可有效提高羟基酪醇对光和高温的稳定性,扩大羟基酪醇的应用范围。所得羟基酪醇包合物可用于食品、保健食品、功能食品和化妆品的制备。
Description
技术领域
本发明属于环糊精包合物的制备领域,具体涉及一种羟丙基-β-环糊精-羟基酪醇包合物,本发明还公开了此包合物的制备方法及其用途。
背景技术
羟基酪醇(Hydroxytyrosol)是一种多酚类化合物,化学名称为3,4-二羟基苯乙醇,分子式为C8H10O3,相对分子量为154.16,有较高的水溶性和脂溶性。羟基酪醇作为一种从橄榄油中提取出的生物活性物质,安全性高,且具有较强的抗氧化活性和促进线粒体生成的生物学活性,具有抗炎、抗菌和抗氧化等多种生理活性。羟基酪醇以酚羟基作为氢供体,可将单线态氧还原成活性较低的三线态氧,减少氧自由基产生;羟基酪醇可与活性较高的自由基反应生成活性较低的多酚自由基,打断自由基链式反应;此外,羟基酪醇的邻位酚羟基可与金属离子鳌合,减少金属离子对氧化反应的催化。目前,羟基酪醇的粗提物和高纯度的羟基酪醇已经广泛应用于食品、保健品和化妆品中,但羟基酪醇对光、热等不稳定,使用过程中易氧化变色,限制了其在食品、饮料保健品、药品及护肤品的应用。
关于β-环糊精和羟基酪醇的包合作用已有过文献报道[羟基酪醇-β-环糊精包合工艺,四川师范大学学报(自然科学版)2018,41(4):539-543],其研究表明,羟基酪醇可被β-环糊精包合,所形成的包合物的光热稳定性大为提高,但是包封率不高,未进入环糊精内腔的羟基酪醇仍然存在不稳定,易变色等问题,另外采用45℃烘干制备羟基酪醇的方法,也会影响未包封的羟基酪醇的稳定性。
羟丙基-β-环糊精包合技术在食品与医药领域有广泛的应用。实验表明,羟丙基-β-环糊精及其衍生物是一类优质的包合材料,主要有下列几方面的应用:增加药物的水溶性;提高药物的稳定性;促进药物吸收,提高药物的生物利用度;减轻药物对机体的刺激及副作用;作为缓释和靶向制剂的载体材料。除此以外,羟丙基-β-环糊精还能使液态药物固体化,改变药物的不良气味,防止制剂中药物与药物、药物与辅料的相互作用等。
为了增加产品稳定性,本发明采用羟丙基-β-环糊精进行包合,并加入保护剂对未进入到羟丙基-β-环糊精的羟基酪醇进行稳定,提高了包合物的稳定性,拓宽了其应用领域。
发明内容
本发明目的之一是针对呈液态的羟基酪醇,在空气中很不稳定,对光、热等不稳定,易变色且不易制剂等问题,提供一种羟基酪醇羟丙基-β-环糊精包合物的制备方法。
本发明另一目的是提供一种稳定性好、生产简单、使用方便且有效的羟基酪醇组合物的应用。
本发明的目的是通过下列技术方案实现的。
一种羟基酪醇包合物,其特征在于该包合物包括下列质量分数的原料:羟基酪醇0.5~5份,羟丙基-β-环糊精5~55份,保护剂0.5~8份。
其中,所述包合物包括以下质量分数的原料:羟基酪醇1~3份,羟丙基-β-环糊精10~40份,保护剂1~5份。
其中,所述包合物包括以下质量分数的原料:羟基酪醇2份,羟丙基-β-环糊精24份,保护剂3份。
其中,所述的羟基酪醇为含量≥98%的纯品,可以是植物提取、生物发酵或者化学合成。
其中,所述的羟基酪醇包合物的制备方法是:称取羟丙基-β-环糊精溶于水中,水浴加热至50℃,称取羟基酪醇加水溶解,将羟基酪醇水溶液缓慢滴加至羟丙基-β-环糊精水溶液中,加热搅拌包合5小时,然后加入保护剂,冷冻干燥,得到羟基酪醇包合物。
其中,所述的保护剂包括维生素C、维生素C乙基醚、维生素C葡糖苷、维生素E、维生素E醋酸酯、维生素E琥珀酸酯、维生素E亚油酸脂、对羟基苯乙酮、谷胱甘肽、谷胱甘肽乙酯、N-乙酰半胱氨酸、硫辛酸、吡咯烷酮羧酸锌盐、泛醌、泛醇、亚硫酸氢钠、亚硫酸钠其中的任意一种或两种或多种。
其中,所述的包合物的制备方法中,冷冻干燥的温度是-50℃。
其中,所述的羟基酪醇包合物可用于食品、保健食品、功能食品和化妆品的制备。
制备的含有羟基酪醇包合物的食品、保健食品、功能食品可以是适于口服的任意剂型,如胶囊、口服液、微丸、片剂、口含片;还可以包括其他任何有生理活性并用于口服的物质,还可以包括药剂学或食品上可接受的辅料。
所述的含有羟基酪醇包合物的化妆品可以是水剂、乳液、精华、乳膏、面膜等形式,还可以包括其他任何有生理活性并适用于制备化妆品的物质,还可以包括制备化妆品上可接受的辅料。
本发明的有益效果:
本发明提供的羟基酪醇组合物含有羟丙基-β-环糊精和保护剂,将该组合物配成水溶液后,光照稳定性和高温稳定性明显提高,无明显变色,这是因为发明中的羟丙基-β-环糊精能与羟基酪醇形成包合物,将一部分羟基酪醇包合在羟丙基-β-环糊精分子内腔中,而未进入分子内腔的羟基酪醇在保护剂的作用下,增强了羟基酪醇的稳定性,也增加了分子的光热稳定性。本产品溶液在-20~60℃保存条件下在所测试的时间内均显示了较好的稳定性。
附图说明
图1羟基酪醇纯品与包合物DPPH清除率结果;图中:─▲─实验组一,─■─实验组二。
图2羟基酪醇包合物与维生素C的酪氨酸酶抑制作用结果;图中:─▲─实施例一,─■─实施例二,─◆─实施例三,┄×┄维生素C。
具体实施方式
以下通过实施例对本发明作进一步的阐述,但本发明不受下述实施例的限制。
实施例1
羟基酪醇 2.4g
羟丙基-β-环糊精 11.6g
维生素C 2g
维生素E琥珀酸酯 2g
泛醌 2g
水 适量
制备方法:称取11.6g羟丙基-β-环糊精溶于水中,水浴加热至50℃,称取羟基酪醇2.4g加15ml水溶解,将羟基酪醇水溶液缓慢滴加至羟丙基-β-环糊精水溶液中,加热搅拌包合5小时,然后加入维生素C 2g,继续搅拌加热半小时后,加入维生素E琥珀酸酯2g,泛醇2g,搅拌均匀后倒入表面皿中静置至室温,然后-50℃进行冻干,得到羟基酪醇包合物。
实施例2
羟基酪醇 1.5g
羟丙基-β-环糊精 60g
维生素E醋酸酯 4.5g
谷胱甘肽乙酯 60g
泛醇 24g
水 适量
制备方法:称取60g羟丙基-β-环糊精溶于水中,水浴加热至50℃,称取羟基酪醇1.5g加5ml水溶解,将羟基酪醇水溶液缓慢滴加至羟丙基-β-环糊精水溶液中,加热搅拌包合5小时,然后加维生素E醋酸酯4.5g,继续搅拌加热半小时后,加入谷胱甘肽乙酯60g,泛醇24g,搅拌均匀后倒入表面皿中静置至室温,然后-50℃进行冻干,得到羟基酪醇包合物。
实施例3
羟基酪醇 4g
羟丙基-β-环糊精 48g
维生素C乙基醚 3g
亚硫酸钠 3g
水 适量
制备方法:称取48g羟丙基-β-环糊精溶于水中,水浴加热至50℃,称取羟基酪醇4g加30ml水溶解,将羟基酪醇水溶液缓慢滴加至羟丙基-β-环糊精水溶液中,加热搅拌包合5小时,然后加入维生素C乙基醚3g,继续搅拌加热半小时后,加入亚硫酸钠3g,搅拌均匀后倒入表面皿中静置至室温,然后-50℃进行冻干,得到羟基酪醇包合物。
实施例4
羟基酪醇 3.15g
羟丙基-β-环糊精 90g
N-乙酰半胱氨酸 0.6g
吡咯烷酮羧酸锌盐 2.4g
水 适量
制备方法:称取90g羟丙基-β-环糊精溶于水中,水浴加热至50℃,称取羟基酪醇3.15g加50ml水溶解,将羟基酪醇水溶液缓慢滴加至羟丙基-β-环糊精水溶液中,加热搅拌包合5h,然后加入N-乙酰半胱氨酸0.6g,继续搅拌加热半小时后,加入吡咯烷酮羧酸锌盐2.4g,搅拌均匀后倒入表面皿中静置至室温,然后-50℃进行冻干,得到羟基酪醇包合物。
实施例5
羟基酪醇 10g
羟丙基-β-环糊精 80g
维生素C葡糖苷 8g
硫辛酸 2g
谷胱甘肽 10g
水 适量
制备方法:称取80g羟丙基-β-环糊精溶于水中,水浴加热至50℃,称取羟基酪醇10g加60ml水溶解,将羟基酪醇水溶液缓慢滴加至羟丙基-β-环糊精水溶液中,加热搅拌包合5小时,然后加入维生素C葡糖苷8g,继续搅拌加热半小时后,加入硫辛酸2g,谷胱甘肽10g,搅拌均匀后倒入表面皿中静置至室温,然后-50℃进行冻干,得到羟基酪醇包合物。
实施例6
羟基酪醇 21g
羟丙基-β-环糊精 83g
泛醇 0.8g
亚硫酸氢钠 1.2g
水 适量
制备方法:称取83g羟丙基-β-环糊精溶于水中,水浴加热至50℃,称取羟基酪醇21g加100ml水溶解,将羟基酪醇水溶液缓慢滴加至羟丙基-β-环糊精水溶液中,加热搅拌包合5小时,然后加入泛醇0.8g,继续搅拌加热半小时后,加入亚硫酸氢钠1.2g,搅拌均匀后倒入表面皿中静置至室温,然后-50℃进行冻干,得到羟基酪醇包合物。
实施例7
保健食品的制备
准确称量如下组分:取本发明实施例4的羟基酪醇包合物27g,叶黄素12克,花青素110克,牛磺酸140克,加入10%淀粉浆80克,适量滑石粉,微晶纤维素,均匀混合后粉碎,过100目筛一次,在50℃温度下真空干燥3小时后,整粒,装入胶囊。
实施例8
化妆品乳液的制备
制作工艺:将A、B两相加热到80℃至全部溶解,A相加入B相匀质5min,保温10min后,开始降温,当温度降到45℃时加入C相,搅拌均匀后,过滤出料。
实施例9
压片糖果的制备
准确称量如下组分:取本发明实施例3中的羟基酪醇包合物15g,蔓越莓粉11.6克,玫瑰粉1.48克,葡萄籽粉11.61克,加入山梨糖醇45克,微晶纤维素8克,硬脂酸镁0.5克,均匀混合后粉碎,过100目筛,压片成型,去除裂片,松片,表面粗糙不合格的压片糖果后,包装。
稳定性实验
实验组一:取羟基酪醇纯品配制成5mg/ml的水溶液。
实验组二:取本发明实施例3中制备的羟基酪醇包合物,配置成含羟基酪醇5mg/ml的水溶液。
以4500Lx强度光同时照射两组样品,以高效液相色谱为分析(分析柱:WatersSunFire C8柱,250mm×4.6mm,5μm,检测波长:210nm,流动相:流动相0.1%磷酸水溶液:乙腈=85:15,柱温35℃,流速:1.0ml/min,进样体积:10μl,等度法分析),分析其羟基酪醇含量。计算0~28d样品中羟基酪醇的含量,结果见表1。
表1羟基酪醇包合物光照稳定性性影响(mg/ml)
结果表明,实验组一和实验组二在光照28d内含量下降明显,而实验组二包合物中的羟基酪醇的含量相对实验组一稳定。
将两组实验样品分别置于40℃和60℃恒温烘箱内,以高效液相色谱条件为分析手段,通过检测羟基酪醇的含量来考察温度对各组化合物的影响,结果见表2。
表2羟基酪醇的高温稳定性实验结果(mg/ml)
结果显示,羟基酪醇对热敏感,温度越高,降解速度越快,28d内含量明显下降,而实验组二中的羟基酪醇含量相对稳定。
DPPH自由基清除能力测试
DPPH溶液浓度29μg/ml,相当于50.7μmol/L。样品配置成羟基酪醇含量0.5%的水溶液,稀释200倍后浓度16.2μmol/L。吸光度测定检测波长517nm。
清除率=[1-(Ai-Aj)/Ac]×100%式(1)
式中:Ai 2mlDPPH+2ml样品溶液,Aj 2ml样品溶液+2ml无水乙醇,Ac 2mlDPPH+2ml无水乙醇。
实验结果见图1。结果表明,随着时间延长,羟基酪醇包合物清除DPPH效率更稳定,比纯品具有更高效更持久的抗氧化活性。
酪氨酸酶抑制作用
1、溶液配制
①PBS溶液(0.05M,pH=6.8)
A.0.05M磷酸氢二钠[(无水)141.96g/mol,Na2HPO4.7H2O,268.07g/mol,(十二水)358.14g/mol)];B.0.05M磷酸二氢钾(KH2PO4,分子量136.09);A:B=1:1比例混合。
②酪氨酸溶液(1mg/ml PBS溶液)
母液:0.1g酪氨酸标准品+10ml PBS;工作液:1ml母液+9ml PBS。
③酪氨酸酶溶液(200U/ml)
母液:2mg酪氨酸酶标准品(5771U/mg)+5.771ml PBS;工作液:1ml母液+9ml PBS。
④受试物梯度溶液(PBS溶液)
受试物:羟基酪醇包合物样品来源:实施例1、实施例2、实施例3,维生素C分别设置浓度梯度为20mg/ml、16mg/ml、12mg/ml、8mg/ml、4mg/ml。
2、反应体系
3、混匀,30℃水浴0.5h,各反应管分别取出150μl×3孔,加入96孔板,测量并记录A492。
4、计算酪氨酸酶抑制率
酪氨酸酶酶活抑制率(%)=100-(A1-A2)/(A0-1-A0-2)×100
5、实验结果见图2
结果表明,不同浓度的羟基酪醇包合物均具有良好的酪氨酸酶抑制作用,且具有浓度依赖性,其中,实施例3的羟基酪醇包合物活性最佳。由此可见,羟基酪醇包合物在天然美白化妆品领域及色素增加性皮肤疾病防治中具有良好的应用价值。
以上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。本发明的实施例的详细描述并非旨在限制要求保护的本发明的范围,而是仅仅表示本发明的选定实施例。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。
Claims (9)
1.一种羟基酪醇包合物,其特征在于所述包合物包括下列质量分数的原料:羟基酪醇0.5~5份,羟丙基-β-环糊精5~55份,保护剂0.5~8份。
2.如权利要求1所述的一种羟基酪醇包合物,其特征在于所述包合物包括下列质量分数的原料:羟基酪醇1~3份,羟丙基-β-环糊精10~40份,保护剂1~5份。
3.如权利要求1所述的一种羟基酪醇包合物,其特征在于所述包合物包括下列质量分数的原料:羟基酪醇2份,羟丙基-β-环糊精24份,保护剂3份。
4.如权利要求1所述的一种羟基酪醇包合物,其特征在于所述包合物的制备方法是,取羟丙基-β-环糊精溶于水,水浴加热至50℃,称取羟基酪醇加水溶解,将羟基酪醇水溶液缓慢滴加至羟丙基-β-环糊精水溶液中,加热搅拌包合5小时,然后加入保护剂,冷冻干燥,得到羟基酪醇包合物。
5.如权利要求1~4任一所述的一种羟基酪醇包合物,其特征在于,所述的保护剂包括维生素C、维生素C乙基醚、维生素C葡糖苷、维生素E、维生素E醋酸酯、维生素E琥珀酸酯、维生素E亚油酸脂、对羟基苯乙酮、谷胱甘肽、谷胱甘肽乙酯、N-乙酰半胱氨酸、硫辛酸、吡咯烷酮羧酸锌盐、泛醌、泛醇、亚硫酸氢钠、亚硫酸钠其中的任意一种或两种或多种。
6.如权利要求4所述的制备方法,其特征在于,所述冷冻干燥的温度为-50℃。
7.如权利要求1~4任一所述的一种羟基酪醇包合物,其特征在于,其可用于食品、保健食品、功能食品和化妆品的制备。
8.如权利要求7所述的一种羟基酪醇包合物,其特征在于,所述制备的含有羟基酪醇包合物的食品、保健食品、功能食品可以是适于口服的任意剂型,如胶囊、口服液、微丸、片剂、口含片;还可以包括其他任何有生理活性并用于口服的物质,还可以包括药剂学或食品上可接受的辅料。
9.如权利要求7所述的一种羟基酪醇包合物,其特征在于,所述制备的含有羟基酪醇包合物的化妆品可以是水剂、乳液、精华、乳膏、面膜等形式,还可以包括其他任何有生理活性并适用于制备化妆品的物质,还可以包括制备化妆品上可接受的辅料。
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