CN117500508A - 糖基化菌红素及其工业应用 - Google Patents
糖基化菌红素及其工业应用 Download PDFInfo
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- CN117500508A CN117500508A CN202180093924.9A CN202180093924A CN117500508A CN 117500508 A CN117500508 A CN 117500508A CN 202180093924 A CN202180093924 A CN 202180093924A CN 117500508 A CN117500508 A CN 117500508A
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- bilirubin
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Abstract
本发明涉及从单糖基化菌红素、二糖基化菌红素、三糖基化菌红素、四糖基化菌红素、五糖基化菌红素、六糖基化菌红素、七糖基化菌红素、八糖基化菌红素、九糖基化菌红素、十糖基化菌红素、十一糖基化菌红素和十二糖基化菌红素中分离的糖基化菌红素。具体而言,本发明涉及糖基化形式的类胡萝卜素菌红素的纯化或合成及其应用,尤其是在药物、皮肤美容产品和营养制品以及生物技术领域中的应用。
Description
技术领域
本发明涉及糖基化菌红素(bacterioruberin)。具体而言,本发明涉及糖基化形式的类胡萝卜素菌红素的纯化或合成及其应用,尤其是在药物、皮肤美容产品和营养制品以及生物技术领域中的应用。
背景技术
类胡萝卜素是高度共轭的线性类异戊二烯化合物,是在地球生物中观察到的大多数黄色、橙色和红色色素沉着的原因(Armstrong,1997)。尽管在自然界中已经鉴定了大约1000种不同的类胡萝卜素,并且它们具有非常不同的结构特征,但是所有已知的类胡萝卜素共享一个共轭的线性亲脂性主链,该主链是通过高度保守的生物合成途径获得的(Britton,2004)。类胡萝卜素由初级代谢产生的异戊二烯单元线性缩合而成(Armstrong,1994)。在链的每个末端的共价修饰产生了已知类胡萝卜素的观察到的结构多样性(Armstrong 1997)。链的去饱和产生类胡萝卜素特有的发色团,这导致容易激发的离域电子的区域;这些特性是所有类胡萝卜素共有的两个基本特征(即它们的光化学特性和抗氧化作用)的基础(Britton,1995)。
类胡萝卜素生物合成发生在所有生物中,除了通过饮食引入类胡萝卜素的动物(Britton,1995)。
术语“类胡萝卜素”包括胡萝卜素和叶黄素家族的分子。
在具有最大抗氧化潜力的类胡萝卜素中,应该提到菌红素,它是含有50个碳原子的四羟基化胡萝卜素。菌红素及其衍生物存在于嗜极细菌中,包括嗜盐古菌(haloarchaea)和某些嗜冷放线菌;在这些微生物中,它们在保护DNA和细胞膜免受太阳辐射以及这些微生物永久暴露的热应激和渗透环境应激方面发挥着重要作用(Mandelli等人,2012)。
除了天然形式的类胡萝卜素之外,一些生物体具有糖基化衍生物,即其中疏水链的末端被糖残基取代。在大多数物种中,这些糖基化形式占类胡萝卜素的一小部分,因此是很少科学研究的主题。这些糖基化形式的类胡萝卜素的实际功能尚未明确阐明。研究表明,在这组光合细菌中,糖基化类胡萝卜素位于类囊体膜上,并且需要存在于类异戊二烯链末端的糖残基,以确保叶绿体膜的正确堆叠(Mohamed等人,2005)。在非光合生物中,糖在末端的存在可以为脂质膜上的其他分子提供锚点或附着点。
尽管在对糖基化类胡萝卜素的生理功能的理解上存在差距,但是很明显,鉴于它们的物理化学性质,特别是它们的两亲性,以及它们的抗氧化潜力,这些分子可以在多个领域中找到主要的应用,特别是在美容产品、食品、营养制品和制药工业中。
众所周知,运动节杆菌(Arthrobacter agilis)能够合成糖基化类胡萝卜素,特别是糖基化菌红素。对从南极冰中分离出的这一物种的菌株进行了详细研究(Fong等人,2001)。已经表明,在该菌株中类胡萝卜素的合成是响应于培养基盐度的增加和低温而被诱导的,这间接暗示了类胡萝卜素及其糖基化形式在存在渗透或热应激的情况下稳定细菌膜。Fong等人还通过HPLC/UV分析确定,运动节杆菌产生多种非糖基化的菌红素异构体以及相同类胡萝卜素的单糖基化、二糖基化和四糖基化形式;然而,因为它们不能被单独分离,所以单个分子不能被进一步表征。因此,该研究不可能确定糖基化菌红素的特征和性质。
发明内容
本发明的目的是解决由提供糖基化菌红素,特别是分离或纯化形式的糖基化菌红素组成的技术问题。
本发明的目的是解决由提供包含一种或多种糖基化菌红素,特别是分离或纯化形式的糖基化菌红素的组合物组成的技术问题。
本发明的目的是解决由提供一种分离和纯化至少一种糖基化菌红素的方法组成的技术问题。
本发明的目的是解决由提供一种稳定蛋白质的体外方法组成的技术问题。
发明描述
令人惊讶的是,申请人开发了一种方法,使得有效分离糖基化形式的菌红素成为可能。分离的糖基化菌红素及其混合物具有特殊的和新颖的生物化学性质,这有助于它们在多个领域中的工业开发。
因此本发明涉及一种糖基化菌红素,其特征在于其分离自或选自单糖基化菌红素、二糖基化菌红素、三糖基化菌红素、四糖基化菌红素、五糖基化菌红素、六糖基化菌红素、七糖基化菌红素、八糖基化菌红素、九糖基化菌红素、十糖基化菌红素、十一糖基化菌红素和十二糖基化菌红素。
本发明涉及一种糖基化菌红素,其选自单糖基化菌红素、二糖基化菌红素、三糖基化菌红素和四糖基化菌红素。
根据一个实施方案,从嗜极细菌的提取物中分离和纯化糖基化菌红素,该嗜极细菌优选为微球菌科的细菌,有利地为运动节杆菌。
根据一个实施方案,从运动节杆菌类胡萝卜素的提取物中分离和纯化糖基化菌红素。
根据一个实施方案,糖基化菌红素的纯度为至少70重量%,或甚至80重量%,优选90重量%,甚至更有利地95重量%,或甚至99重量%。
有利地,提取物是总提取物。总提取物通常是来自所讨论的整个细菌的提取物。
根据一个实施方案,通过生物技术合成或化学合成来合成根据本发明分离的一种或多种糖基化菌红素。
术语“菌红素”特别是指(全-E)-(2S,2'S)-菌红素(CAS No 32719-43-0),也称为“α-菌红素”。
“α-菌红素”具有以下结构:
[化学式1]
α-细菌素包含4个末端羟基,每个羟基能够被与糖型基团键合的醚或甚至一个或多个共价键合的糖取代。术语“糖基化形式的菌红素”或“糖基化菌红素”是指其中至少一个羟基被一个或多个,例如两个或三个糖残基通过菌红素主链和糖之间的醚键取代的菌红素。
根据本发明的“分离的糖基化菌红素”通过生物技术合成、化学合成或天然细菌中天然含有的糖基化菌红素的纯化获得。
例如,根据本发明的“糖基化菌红素”对应于以下结构:
[化学式2]
其中R独立地选自氢原子、一个或多个,例如两个或甚至三个糖残基,并且其中在至少一种情况下,R代表一个或多个,例如两个或甚至三个糖残基。
在一个优选的实施方案中,糖是己糖或脱氧己糖,选自由阿洛糖、阿卓糖、葡萄糖、甘露糖、古洛糖、艾杜糖、半乳糖、岩藻糖、果糖和岩藻糖组成的组。
本发明还涉及包含至少一种糖基化菌红素的组合物,所述组合物基本上不包含非糖基化形式的菌红素,并且所述组合物包含一种或多种人类可接受的赋形剂。
根据一个实施方案,所述组合物包含至少一种根据本发明定义的分离的糖基化菌红素。
根据一个实施方案,所述组合物包含单糖基化菌红素、二糖基化菌红素、三糖基化菌红素和四糖基化菌红素的混合物。
根据一个实施方案,所述组合物包含基本上由单糖基化菌红素和二糖基化菌红素构成的糖基化菌红素混合物,相对于糖基化菌红素混合物的总重量,所述混合物优选包含20至80重量%的单糖基化菌红素和20至80重量%的二糖基化菌红素。
本发明还涉及两种或多种分离的糖基化菌红的混合物中的任何一种,所述混合物,基本上不含非糖基化形式的菌红素,所述糖基化菌红选自单糖基化菌红素、二糖基化菌红素、三糖基化菌红素、四糖基化菌红素、五糖基化菌红素、六糖基化菌红素、七糖基化菌红素、八糖基化菌红素、九糖基化菌红素、十糖基化菌红素、十一糖基化菌红素和十二糖基化菌红素。
有利地,所述混合物基本上由单糖基化菌红素、二糖基化菌红素和四糖基化菌红素的混合物组成;并且优选由单糖基化菌红素和二糖基化菌红素的混合物组成。
本发明还涉及从含有至少一种根据本发明定义的糖基化菌红素的类胡萝卜素提取物中分离和纯化它们的方法,包括以下步骤:
(i)将所述提取物溶解在溶剂中,优选溶解在四氢呋喃中;
ii)使用洗脱剂,优选使用二氯甲烷/甲醇混合物,通过硅胶型固定相柱上的吸附层析色谱,分离含有一种或多种糖基化菌红素的级分。
在一个优选的实施方案中,二氯甲烷和甲醇的重量比为20/1至1/20,有利地为10/1至3/7。
可以使用本领域技术人员已知的定性和定量方法,例如薄层色谱法、HPLC/UV、HPLC/DAD和质谱法,进一步分析和表征通过该纯化过程获得的级分。
有利地,所述一种或多种糖基化菌红素从含有糖基化菌红素的总类胡萝卜素提取物中分离和纯化。
有利地,含有糖基化菌红素的类胡萝卜素的总提取物是细菌提取物,优选放线菌,甚至更有利地是微球菌科的细菌提取物。有利地,该物种是玫瑰色微球菌(Micrococcusroseus)和运动节杆菌(Arthrobacter agilis)。
优选地,在本发明的意义上用作糖基化菌红素来源的运动节杆菌菌株是菌株MB813(在Fong等人2001中描述)和/或SB5(在专利申请WO 2014/167247中描述)。该物种也被称为运动微球菌(Micrococcus agilis)。获得这些细菌物种的总类胡萝卜素提取物的方法是本领域技术人员已知的,并且已经在例如Strand等人1997、Fong等人2001以及专利申请WO 2014/167247中有所描述。
在一个优选的实施方案中,根据本发明的含有糖基化菌红素的类胡萝卜素的总提取物对应于由GREENTECH销售的MIRORUBERINE起始原料中所含的提取物,并且对应于INCI名微球菌裂解物(Micrococcus Lysate)。或者,根据本发明的糖基化菌红素可以通过生物技术或化学合成获得,例如通过控制天然形式的菌红素的糖基化,通常是α-菌红素的糖基化,例如从α-菌红素开始。这种糖基化可以通过化学方法或生物技术获得,优选通过生物技术,使用一种或多种合适的糖基转移酶。举例来说,由HALOTEK GmbH销售的起始材料HALORUBINE可用作本发明意义上的糖基化菌红素合成中的α-菌红素的来源。
根据本发明的糖基化菌红素以及包含它们的组合物显示出高抗氧化活性;这些分子能够保护蛋白质不被羰基化,并有助于它们的稳定。因此,糖基化菌红素适用于药物、皮肤美容产品、营养制品和生物技术领域的各种应用。
因此本发明涉及用作药物的本发明定义的分离的糖基化菌红素,所述的糖基化菌红素尤其选自单糖基化菌红素、二糖基化菌红素、三糖基化菌红素、四糖基化菌红素、五糖基化菌红素、六糖基化菌红素、七糖基化菌红素、八糖基化菌红素、九糖基化菌红素、十糖基化菌红素、十一糖基化菌红素和十二糖基化菌红素。
本发明进一步涉及一种用作药物的分离的糖基化菌红素,其选自单糖基化菌红素、二糖基化菌红素、三糖基化菌红素和四糖基化菌红素。
本发明还涉及用作药物的根据本发明的组合物。
有利地,所述组合物包含单糖基化菌红素、二糖基化菌红素、三糖基化菌红素和四糖基化菌红素的混合物,优选包含基本上由单糖基化菌红素和二糖基化菌红素构成的糖基化菌红素混合物,并且相对于糖基化菌红素混合物的总重量,所述混合物优选包含20至80重量%的单糖基化菌红素和20至80重量%的二糖基化菌红素。
本发明涉及用于人类或动物的治疗方法的根据本发明定义的糖基化菌红素、它们的混合物和组合物。例如,其涉及神经退行性疾病,例如阿尔茨海默病(AD)、帕金森病(PD)、亨廷顿病、后部皮质萎缩或肌萎缩性侧索硬化(ALS),以及选自黄斑变性、色素性视网膜炎和视网膜病的眼神经退行性疾病的治疗。
然而,糖基化菌红素也可用于治疗呈现蛋白质聚集的失调的其它病状,例如纤维化,有利地例如肺纤维化,和糖尿病。
根据本发明的药物组合物通常是剂型。因此,根据本发明的组合物可以是片剂、糖衣片剂、胶囊剂、栓剂、可注射溶液或口服溶液的形式,或者实际上是滴剂,并且它能够通过口服、口腔粘膜、直肠、阴道、胃肠外、肌内或眼部施用。
在根据本发明的药物组合物中,将更具体地提及适于口服、口腔粘膜、肠胃外(静脉内、肌内或皮下)、经皮或透皮、阴道内、直肠、鼻腔、经舌、口腔、眼部或呼吸道施用的那些药物组合物。
用于肠胃外注射的根据本发明的药物组合物尤其包括水性和非水性无菌溶液、分散剂、悬浮液或乳液以及用于重构可注射溶液或分散剂的无菌粉末。
对于固体口服施用,根据本发明的药物组合物特别包括简单片剂或糖衣片剂、舌下片剂、袋装剂、胶囊剂或颗粒剂,对于口服、鼻腔、口腔或眼部液体施用,特别包括乳液、溶液、混悬剂、滴剂、糖浆和气雾剂。
用于直肠或阴道施用的药物组合物优选为栓剂或胚珠,用于经皮或透皮施用的药物组合物尤其包括粉剂、气雾剂、霜剂、软膏剂、凝胶剂和贴剂。
上述药物组合物阐明本发明,但不以任何方式限制本发明。
惰性的、无毒的、人类可接受的或药学上可接受的赋形剂或载体的实例是稀释剂、溶剂、防腐剂、湿润剂、乳化剂、分散剂、粘合剂、发泡剂、崩解剂、阻滞剂、润滑剂、吸收剂、悬浮剂、染剂、调味剂等,它们可以作为指示引用,但不意味着任何限制。
有效剂量根据患者的年龄和体重、施用方式、所用药物组合物以及疾病的性质和严重程度而变化。举例来说,根据本发明的组合物可以每月施用一次、每周施用一次或每天施用一次,并且它可以含有1mg至1g糖基化菌红素或其任何混合物。
根据本发明的糖基化菌红素适用于它们在食品和营养制品补充剂。因此,根据一个实施方案,根据本发明的组合物是食品补充剂。
配制食品补充剂的方法是本领域技术人员已知的。有利地,这些食品补充剂是片剂或胶囊的形式。举例来说,每一剂量可含有1mg至1g糖基化菌红素和/或其任何混合物。
例如,在片剂中,微晶纤维素用作增容剂。相对于食品补充剂的总重量,其用量为10-30重量%,更有利地约为20重量%。
磷酸二钙和磷酸三钙用作制备片剂的压缩剂。相对于食品补充剂的总重量,使用10重量%至30重量%的磷酸二钙,更有利地是大约15重量%。相对于食品补充剂的总重量,使用2.5重量%至7.5重量%的磷酸三钙,更有利地是大约5重量%。
水合二氧化硅、硬脂酸镁和胶态二氧化硅可以有利地用作片剂或胶囊形式的食品补充剂中的稀释剂。相对于食品补充剂的总重量,它们分别以约2重量%、1重量%和0.6重量%的量引入。
其他佐剂如调味剂(天然或化学、水果或其他调味剂)或色素被有利地掺入到食品补充剂制剂中。
当食品补充剂是软胶囊或胶囊的形式时,这些软胶囊或这些胶囊的外壳可以特别含有动物明胶如鱼明胶、甘油或植物来源的材料如纤维素或淀粉衍生物或植物蛋白。在一个优选的实施方案中,掺入胶囊中的一种或多种根据本发明的糖基化菌红素可以溶解在脂肪物质中,该脂肪物质有利地是辛酸和/或癸酸甘油三酯,并且优选用生育酚稳定。
糖基化菌红素及其组合物适用于生物技术应用。举例来说,这些分子可用于稳定蛋白质(例如酶)并防止或减缓其降解、失活、聚集等。
因此,本发明还涉及一种用于稳定蛋白质的体外方法,由将待稳定的蛋白质与一种或多种如本发明所定义的糖基化菌红素或与根据本发明所定义的组合物接触进行孵育或储存组成。
糖基化菌红素的特性,特别是它们的蛋白质保护特性和它们的两亲特性,有助于在皮肤美容产品领域开发这些分子。因此,在本发明的特别实施方案中,根据本发明的组合物是美容品组合物,其有利地适用于局部施用。
有利地,所述组合物包含至少一种糖基化菌红素,其选自单糖基化菌红素、二糖基化菌红素、三糖基化菌红素、四糖基化菌红素、五糖基化菌红素、六糖基化菌红素、七糖基化菌红素、八糖基化菌红素、九糖基化菌红素、十糖基化菌红素、十一糖基化菌红素和十二糖基化菌红素。优选地,所述组合物包含单糖基化菌红素、二糖基化菌红素和四糖基化菌红素的混合物,优选包含基本上由单糖基化菌红素和二糖基化菌红素构成的糖基化菌红素混合物;并且相对于糖基化菌红素混合物的总重量,所述混合物优选包含20至80重量%的单糖基化菌红素和20至80重量%的二糖基化菌红素。
在一个优选的实施方案中,相对于所述美容品组合物的总重量,根据本发明的糖基化菌红素占0.0001重量%至0.5重量%,有利地占0.001重量%至0.01重量%。
根据一个可供选择的实施方案,有利地,根据本发明的组合物额外包含至少一种UV滤光剂。
在本发明的上下文中,术语“UV滤光剂”包括能够过滤UV-A、UV-B和/或UV-C的有机或无机化合物。
根据本发明,这些也可以是无机滤光剂,而不是化学或有机滤光剂。
根据本发明的组合物可以包含一种或多种广谱UV滤光剂,即吸收UV-A、UV-B、UV-C和可能的可见光的化合物或混合物。
可用于本发明范围内的广谱有机滤光剂的实例包括对应于以下INCI名称的滤光剂:三联苯三嗪、双乙基己氧基苯酚甲氧基苯基三嗪、亚甲基双-苯并三唑基四甲基丁基苯酚。举例来说,它们由BASF分别以名称TINOSORB/TINOSORB/>TINOSORB/>TINOSORB/>销售。适用于本发明组合物的广谱滤光剂的另一实例对应于INCI名称二乙基己基丁酰胺基三嗪酮,例如由SIGMA 3V以名称UVASORB/>销售。
因此,在一个特定的实施方案中,根据本发明的组合物包含至少一种选自以下组的以其INCI名称标识的化合物的滤光剂:三联苯三嗪、双乙基己氧基苯酚甲氧基苯基三嗪和亚甲基双-苯并三唑基四甲基丁基苯酚、二乙基己基丁酰胺基三酮或其混合物。
有利地,该组合物包含滤光剂双-乙基己氧基苯酚甲氧基苯基三嗪。
根据另一个实施方案,代替广谱滤光剂或除了广谱滤光剂之外,组合物包含至少一种有机和/或无机的UV-A和/或UV-B滤光剂,其可以在水相(亲脂性)和/或油相(脂溶性)中。
因此,举例来说,根据本发明的组合物可以包含脂溶性UV-B滤光剂,其能够有助于稳定或溶解广谱滤光剂,或者事实上是相互稳定的,并且因此增加防晒因子(SPF)。
有利地,这种类型的滤光剂对应于以下INCI名称:胡莫柳酯(homosalate)、奥克立林(octocrylene)、水杨酸乙基己基酯、乙基己基三嗪酮。
在一个优选的实施方案中,本发明的组合物包含乙基己基三嗪酮,由BASF以名称UVINUL销售。
在另一个实施方案中,脂溶性UV-B滤光剂是α-(三甲基甲硅烷基)-ω-(三甲基甲硅烷氧基)聚[氧基(二甲基)亚甲硅基]-共-[氧基(甲基)(2-{4-[2,2-双(乙氧基羰基)乙烯基]苯氧基}-1-亚甲基乙基)亚甲硅基]-共-[氧基(甲基)(2-(4-[2,2-双(乙氧基羰基)乙烯基]苯氧基)丙-1-烯基)亚甲硅基],一种能够在UV-B范围内滤光的有机硅聚合物。该滤光剂对应于例如美容品原料Parsol由DSM以INCI名有机硅聚合物-15销售。
在一个优选的实施方案中,根据本发明的组合物包含至少一种选自以下组的以其INCI名称命名的化合物的UV-B滤光剂:胡莫柳酯、水杨酸乙基己基酯、乙基己基三嗪酮、有机硅聚合物-15或其混合物。
在一个特定的实施方案中,组合物不含以下滤光剂:4-甲基苯亚甲基樟脑、二苯甲酮-2、二苯甲酮-3、甲氧基肉桂酸乙基己酯、奥克立林。
在一个有利的实施方案中,根据本发明的组合物包含至少一种UV-A滤光剂,以确保完全屏蔽太阳光谱的有害部分。
本发明含义内的有利的UVA屏蔽剂是丁基甲氧基二苯甲酰甲烷(INCI)和二乙氨基羟基苯甲酰基苯甲酸己酯(INCI),分别对应于DSM销售的原料Parsol和BASF销售的原料/>A+。
在一个特定的实施方案中,UV-A屏蔽剂是双(二乙氨基羟基苯甲酰基)哌嗪(INCI)(CAS号919803-06-8),对应于例如BASF销售的原料
因此,在一个优选的实施方案中,根据本发明的组合物包含至少一种选自以下组的以其INCI名称标识的化合物的滤光剂:丁基甲氧基二苯甲酰基甲烷、二乙氨基羟基苯甲酰基苯甲酸己酯、双-(二乙氨基羟基苯甲酰基)哌嗪或其混合物。
在本发明范围内有利的其它UV滤光剂是水溶性滤光剂,例如:
-对应于INCI名称苯基二苯并咪唑四磺酸二钠的滤光剂,特别是以名称NeoAP(Symrise)可获得的滤光剂;
-对应于INCI名称苯基苯并咪唑磺酸的滤光剂,特别是以名称Neohydro(Symrise)可获得的,优选与碱性氨基酸,有利地为精氨酸组合。实际上,该碱性氨基酸占组合物重量的0.5%至2%,优选占组合物重量的1%至1.5%。
在一个优选的实施方案中,根据本发明的组合物包含至少一种选自以下的组的以其INCI名称标识的化合物的水溶性滤光剂:苯基二苯并咪唑四磺酸酯二钠,苯基苯并咪唑磺酸或其混合物。
有利地,无机矿物滤光剂或矿物防晒剂是难以溶解或不溶于水的金属氧化物和/或其他化合物,特别是钛(TiO2)、锌(ZnO)的氧化物,有利地掺杂有铁、铁(Fe2O3)、锆(ZrO2)、硅(SiO2)、锰(例如MnO)、铝(Al2O3)或铈(Ce2O3)、铋(Bi2O3)。
根据一个特定的实施方案,无机矿物防晒剂可以以可商购的油性或水性预分散体的形式使用。这些预分散体可以有利地补充有分散助剂和/或增溶助剂。
无机矿物滤光剂也可以进行表面处理或封装,以便为它们提供亲水、两亲或疏水特性。这种表面处理可以由为矿物防晒剂提供薄的无机和/或有机、亲水和/或疏水膜组成。
在一个优选的实施方案中,根据本发明的组合物包含至少一种选自以下组的以其INCI名称命名的化合物的矿物防晒剂:氧化锌、二氧化钛或其混合物。
在本发明的范围中可以使用的UV滤光剂的列举通过非限制性说明的方式清楚地给出。
有利地,存在于根据本发明的组合物中的如上所述的UV滤光剂占组合物重量的0.1%至30%,有利地占0.5%至20%,甚至更有利地占1%至15%。
根据一个特定的实施方案,根据本发明的组合物的防晒系数(SPF)大于或等于10,优选大于或等于20,有利地大于或等于30,甚至更有利地大于或等于50。
根据一个优选的实施方案,根据本发明的组合物具有大于或等于1/3的UV-A/UV-B防护比率。
根据本发明的防晒组合物包含至少一种选自以下组的以其INCI名称标识的化合物的防晒增溶剂:辛酸辛酯/癸酸辛酯、己二酸二丁酯、碳酸二辛酯、癸二酸二异丙酯、二辛酯醚、椰油辛酸酯、C12-15烷基苯甲酸酯、辛酸丙庚酯和二辛酸丁二酯/二癸酸丁二酯。这些增溶剂可从许多供应商处购得。举例来说,以下原料可用于本发明的组合物中:
-BASF销售的系列的多种原料,特别是/>RLF、/>B、CC、/>O、/>C5、/>AB、/>SENSOFT,分别对应于INCI名称辛酸辛酯/癸酸辛酯、己二酸二丁酯、碳酸二辛酯、二辛基醚、椰辛酸酯、苯甲酸C12-15烷基酯、辛酸丙基庚酯;
-STEARINE DUBOIS销售的DUB DIS,对应于INCI商品名癸二酸二异丙酯;
-IOIOleo GmbH销售的8810,对应于INCI商品二辛酸丁二醇酯/二癸酸丁二醇酯。
在一个优选的实施方案中,根据本发明的组合物包含至少四种选自以下组的以其INCI名称命名的化合物的增溶剂:辛酸辛酯/癸酸辛酯、己二酸二丁酯、碳酸二辛酯、癸二酸二异丙酯、二辛醚、椰油辛酸酯、C12-15烷基苯甲酸酯、辛酸丙基庚酯和丁二醇二辛酸酯/丁二醇二癸酸酯。
在特定的实施方案中,根据本发明的组合物包含对应于INCI名称己二酸二丁酯、碳酸二辛酯和癸二酸二异丙酯的增溶剂。在一个优选的实施方案中,根据本发明的组合物还包含至少一种选自以下的组的以其INCI名称标识的化合物的其它增溶剂:辛酸丙基庚酯、二辛基醚、辛酸椰油酯、苯甲酸C12-15烷基酯、辛酸辛酯/癸酸辛酯。有利地,其为辛酸丙基庚酯。
根据一个优选实施方案,如上定义的增溶剂占组合物总重量的5%至80%,有利地占10%至70%,更有利地占15%至60%。
根据本发明的组合物可另外包含SPF“增强剂”,即增强防晒因子的试剂,和/或光稳定剂,即可用于增加SPF或使滤光剂光稳定的成分,这种成分本身不被认为是防晒剂。可以引用的实例有:
-丁基辛醇水杨酸酯(INCI),该光稳定剂有利地占组合物重量的0.01%至10%,甚至更有利地占0.1%至2%。这种原料例如由HALLSTAR以BHB的名称销售;
-苯并三唑基十二烷基对甲酚(INCI),该光稳定剂有利地占组合物重量的0.01%至10%,甚至更有利地占0.1%至2%。这种原料例如由BASF以
TL的名称销售;
-水黄皮籽素(pongamol)(INCI),一种吸收UV-A的植物分子,有利地占组合物重量的0.5至2%,甚至更有利地约为1%。举例来说,由GIVAUDAN销售的原料Pongamia提取物可用于本发明的范围中;
-乙基己基甲氧基丙烯(INCI)、光稳定剂、增溶剂和SPF“增强剂”,有利地占组合物重量的1%至5%。由HALLSTAR销售的原料S1可用于本发明的范围中;
-苯乙烯-丙烯酸酯共聚物(INCI:苯乙烯/丙烯酸酯共聚物),优选占根据本发明的组合物重量的1%至10%。由DOW CHEMICALS销售的起始材料
H53和/>PGL聚合物可用于本发明的范围内;
-亚丁香基丙二酸二乙基己酯(INCI),有利地占组合物重量的1%至10%。由
MERCK销售的原料ST可用于本发明的范围中;
-水分散性聚酯,对应于INCI名称聚酯-5(和)硅铝酸钠,有利地占组合物重量的1%至10%,特别是由SAFIC-ALCAN销售的EASTMANN AQTM38s聚合物;
-具有通过差示扫描量热法测量的玻璃化转变温度为-5℃至-15℃的丙烯酸酯共聚物,所述共聚物有利地占组合物重量的1%至10%。例如,对应于INCI名称丙烯酸酯共聚物的聚合物,例如由DOW CHEMICALS销售的原料
EPITEX 66,可用于本发明的范围中。
在一个特定的实施方案中,根据本发明的组合物还包含一种或多种适于过滤可见光,特别是蓝光的物质。例如,文献EP 1 484 051中描述的化合物可以用于确保蓝光的过滤。
根据一个优选的实施方案,根据本发明的组合物还包含其它组分,这些组分通过可能由以下所组成的作用而有助于内部保护:保护DNA、减少由UV辐射诱导的免疫抑制、抗自由基作用或这些作用的组合效果。
如果根据本发明的制剂还包含一种或多种抗氧化剂,可以进一步提高其对氧化应激或自由基作用的保护作用,所述抗氧化剂可由本领域技术人员容易地选择,例如选自以下列表:生育酚及其衍生物、桃柘酚(totarol)、厚朴酚(magnolol)、和厚朴酚(honokiol)、氨基酸及其衍生物、肽(D和/或L-肌肽)及其衍生物(例如鹅肌肽、亚牛磺酸、牛磺酸)、类胡萝卜素、胡萝卜素(α-胡萝卜素、β-胡萝卜素、番茄红素)及其衍生物、绿原酸及其衍生物、硫辛酸及其衍生物(二氢硫辛酸)、金硫葡萄糖、丙基硫氧嘧啶和其他硫醇(硫氧还蛋白、谷胱甘肽、半胱氨酸、胱氨酸、胱胺和它们的糖基、N-乙酰基、甲基、乙基、丙基、戊基、丁基和月桂基、棕榈酰基、油基、γ-亚油酸、胆固醇基和甘油酯)及其盐、硫代二丙酸二月桂酯、硫代二丙酸二硬脂酯、硫代二丙酸及其衍生物、磺酰亚胺化合物(丁硫氨酸磺酰亚胺、高半胱氨酸磺酰亚胺、丁硫氨酸砜、五-、六-和庚硫醚磺酰亚胺)、螯合剂(如α-羟基脂肪酸、棕榈酸、植酸、乳铁蛋白)、α-羟基酸(如柠檬酸、乳酸或苹果酸)、腐殖酸、胆汁酸、胆汁提取物、胆红素、胆绿素、EDTA、EGTA、乙二胺四甲叉膦酸五钠及其衍生物、不饱和脂肪酸及其衍生物、维生素A及其衍生物(维生素A棕榈酸酯)、安息香树脂的苯甲酸松柏酯、芸香酸及其衍生物、α-糖基芸香苷、阿魏酸及其衍生物、呋喃甲叉葡萄糖醇、肌肽、丁基羟基甲苯、丁基羟基茴香醚、去甲羟基愈创木酸、三羟基苯丁酮、槲皮素、尿酸及其衍生物、甘露糖及其衍生物、锌及其衍生物(ZnO、ZnSO4)、硒及其衍生物(硒代甲硫氨酸)、芪(stilbene)及其衍生物(氧化芪、反式氧化芪)。
在一个特定的实施方案中,根据本发明的组合物还包含甘草次酸、该酸的衍生物或盐,用作舒缓剂(抗炎剂)并且占组合物重量的0.01%至2%,优选占0.1%至1%。
根据本发明的另一个实施方案,美容品和/或皮肤病学组合物包含下列成分的至少一种或甚至全部,这些成分分别对受到UV-A和/或UV-B辐射的皮肤、嘴唇、头发和/或粘膜的细胞产生体内生物效应:
-保存细胞结构的抗自由基剂,例如维生素E和/或其脂溶性或水溶性衍生物,特别是生育三烯酚和/或生育酚,有利地占组合物总重量的0.001%至10%,甚至更有利地占0.02%至2%,优选占约0.04%;
-限制免疫抑制的药剂,例如维生素PP,有利地占组合物总重量的0.001%至1%,更优选占0.01%至0.3%;
-p53蛋白的保护剂,例如表没食子儿茶素没食子酸酯(EGCG),有利地占组合物总重量的0.001%至0.1%,更有利地占0.005%至0.05%。
根据本发明的组合物此外还可以包含大豆和/或小麦的肽提取物,如EP 2 059230中描述的那些。
实际上,来自大豆或小麦谷物的肽提取物是通过肽酶对所述谷物进行酶水解而获得的,这意味着可以回收平均大小为700道尔顿的肽。优选地,大豆肽提取物是由CAS号68607-88-5标识的提取物,小麦肽提取物是由CAS号70084-87-6标识的提取物。小麦和大豆提取物可以分别对应于INCI名称水解小麦蛋白和水解大豆蛋白。
在一个特定的实施方案中,大豆和小麦肽提取物一起使用,例如重量比分别为80/20至20/80,有利地为70/30至30/70,优选等于60/40。
在一个有利的实施方案中,大豆和/或小麦肽提取物不含合成的GHK三肽(甘氨酰-组氨酰-赖氨酸;INCI:三肽-1)。实际上,大豆和/或小麦的肽提取物占组合物总重量的0.01%至20%,有利地占0.1%至10%,更优选占0.2%至0.7%。
在一个可替代的实施方案中,根据文献FR 2 865 398的教导,根据本发明的组合物包含至少一种选自由依克多因、肌酸、麦角硫因和/或肌肽组成的组的氨基酸或其生理上可接受的盐和甘露醇或甘露醇衍生物的组合。
优选地,根据本发明的组合物在生理上可接受的介质中包含单独的或作为混合物的氨基酸或其一种盐,其比例为组合物总重量的0.001%至10%,优选0.01%至5%。
根据本发明的组合物优选在生理上可接受的介质中包含甘露醇或其衍生物之一,其比例为组合物总重量的0.01%至30%,有利地为0.1%至10%。
在一个优选的实施方案中,根据本发明的组合物包含依克多因和甘露醇。
根据一个特定的实施方案,根据本发明的组合物包含一种或多种晒黑剂或自晒黑剂。它可以是根据美拉德反应或通过迈克尔加成与皮肤的氨基酸反应的自晒黑剂,或者事实上是促进皮肤自然晒黑的黑素生成促进剂或促色素化合物。
这种物质优选以组合物总重量的0.01%至20%存在于组合物中,有利地以0.5%至15%,甚至更有利地以1%至8%。
该自晒黑物质可以是1,3-二羟基丙酮(DHA)、甘油醛、羟甲基乙二醛、γ-二醛、赤藓酮糖、6-醛基-D-果糖、茚三酮、5-羟基-1,4-萘醌(胡桃醌)、2-羟基-1,4-萘醌(指甲花醌)或其组合。
促色素物质可以是促黑素细胞激素(α-MSH)、α-MSH的肽类似物、内皮素-1受体激动剂、μ阿片受体激动剂、AMPc刺激剂、酪氨酸酶刺激剂。
在一个特定的实施方案中,根据本发明的组合物还包含作为自晒黑剂的二羟基甲基色酮基棕榈酸酯和/或二甲基甲氧基苯并二氢吡喃醇以及亲脂形式的酪氨酸的组合。
这种活性要素(principle)的组合使得有效刺激晒黑成为可能。例如,二羟基甲基色酮基棕榈酸酯(CAS号:1387636-35-2)相当于由Merck公司以Bronzyl名称销售的美容品成分。二甲基甲氧基苯并二氢吡喃醇(CAS号:83923-51-7)相当于由LIPOTEC SA以lipochromone-6的名称销售的美容品成分。
在一个特定的实施方案中,该二羟基甲基色酮基棕榈酸酯或二甲基甲氧基苯并二氢吡喃醇在根据本发明的组合物中以组合物总重量的0.01%至10%存在,有利地为0.05%至10%,还更有利地为0.1%至5%,并且更特别地为0.1%至0.5%。
在本发明的含义中,亲脂性形式的酪氨酸是基于酪氨酸的成分,并且具有比酪氨酸更显著的亲脂性特征。亲脂性形式的酪氨酸可以特别对应于油酰酪氨酸(CAS号:147732-57-8),其存在于例如由SEDERMA销售的液体美容品成分TYR-OL中,并且包含在丁二醇(约30%+约20%的油酸)中的约50重量%的油酰酪氨酸,或者事实上存在于由SEDERMA销售的液体化妆品成分TYR-EXCEL中,其包含约50重量%的油酰酪氨酸、约20%的油酸(CAS号:112-80-1)和约30%的丝瓜油(海绵南瓜籽油;CAS号:1242417-48-6)。
根据另一个实施方案,亲脂性形式的酪氨酸对应于在制剂中包含酪氨酸的植物油。
在一个特定的实施方案中,植物油是油酸向日葵油,有利地是防臭处理过的。因此,由OLEOS销售的原料OLEOACTIF TYROSINE BASE HELIANTHUS ANNUS,对应于INCI名称向日葵(Helianthus annuus)籽油(和)酪氨酸(和)硬脂酸甘油酯,可用于本发明范围中。
实际上,如在基于油酰-酪氨酸(有利地为50重量%)的美容品成分中的亲脂性形式的酪氨酸,或在植物油中配制的亲脂性形式的酪氨酸,占组合物总重量的0.1%至10%,有利地占1%至3%,甚至更有利地占1%至1.5%。
根据本发明的组合物还可以包含具有去色素特性的活性成分,例如:
-壬二酸赖氨酸盐或壬二酸的其他衍生物或盐
-穿心莲内酯,特别是对应于INCI名称穿心莲(Andrographis paniculata)叶提取物的穿心莲提取物;
-天然抗坏血酸(维生素C)或其衍生物,特别是对应于INCI名称抗坏血酸基葡糖苷乙基抗坏血酸、抗坏血酸基甲基硅烷醇果胶酸酯、抗坏血酸磷酸钠和抗坏血酸四异棕榈酸酯;
-熊果苷或含有熊果苷的植物提取物,特别是对应于INCI名熊果(Arctostaphylosuva-ursi)叶提取物的熊果提取物;
-光甘草定或含有光甘草定的植物提取物,特别是对应于INCI名光果甘草(Glycyrrhiza glabra)根提取物、胀果甘草(Glycyrrhiza inflata)根提取物、乌拉尔甘草(Glycyrrhiza uralensis)根提取物的甘草提取物;
-对应INCI名六肽2和/或九肽1的仿生肽;
-一种名为掌叶树(Palmaria palmata)的藻类的水性提取物,特别是对应于INCI名掌叶树提取物的提取物;
-4-正丁基间苯二酚;
-维生素PP,也称为烟酰胺(niacinamide)或烟碱酰胺(nicotinamide),及其衍生物;
-或其混合物。
根据本发明的组合物还可以包含具有愈合特性的活性成分,例如选自对应于以下INCI名的活性成分的抗微生物剂:硫酸铜、硫酸锌、透明质酸钠、葡萄(Vitis vinifera)藤提取物或其混合物。
根据本发明的美容品组合物还可以包含具有皮脂矫正(sebo-correcting)、角质溶解、皮脂调节(seboregulating)和/或抗痤疮性质的活性成分,以便使得配制用于治疗痤疮的防晒产品成为可能。
例如,根据本发明的美容品组合物可以包含选自对应于INCI名没食子酸丙酯、没食子酸十二烷基酯、银杏(Ginkgo biloba)叶提取物、补骨脂酚、二氢杨梅素、葡萄糖酸锌、水杨酸或其混合物的活性剂的抗微生物剂。
因此,根据本发明的组合物可以进一步包含选自以下列表的至少一种成分:
-至少一种选自木糖醇、鼠李糖、山梨醇和甘露醇的多元醇;
-藻类楔基海带(Laminaria ochroleuca)、盘苔(Blidingia minima)或糖海带(Laminaria saccharina)的提取物;
-植物竹叶花椒(Zanthoxylum alatum)的提取物;
-泛醇;
-维生素E或其亲水性或亲脂性衍生物或其盐,有利地为生育三烯酚或生育酚;
-水杨酸或其衍生物;
-刺桧(cade)木提取物;
-波尔多叶(boldo)提取物;
-绣线菊(meadowsweet)提取物;
-甘草次酸或其衍生物或盐;
-用于限制免疫抑制的试剂,有利地为维生素PP;
-p53蛋白保护剂,有利地为表没食子儿茶素没食子酸酯(EGCG);
-从无毛水黄皮(Pongamia glabra)中获得的卡兰贾(karanja)油提取物;
-线性石蜡;
-ATP(三磷酸腺苷-5)、Gp4G(四磷酸二鸟苷)或Ap4A(四磷酸二腺苷),
-限制参与自由基形成的铁离子的作用的试剂,有利地为EDTA;
-大豆和/或小麦的肽提取物;
-选自由依克多因、肌酸、麦角硫因、肌肽、酪氨酸、脱羧肌肽、谷氨酰胺及其盐组成的组的氨基酸;
-晒黑或自晒黑剂;
-去色素剂;
-治愈剂;
-皮脂矫正剂、角质层软化剂、皮脂调节剂和/或抗痤疮剂。
根据本发明的组合物还可以含有佐剂,如通常用于美容品领域的佐剂,如活性成分、防腐剂、抗氧化剂、络合剂、溶剂、芳香剂、填充剂、杀菌剂、电解质、气味吸收剂、染色剂或脂质囊泡。这些佐剂的选择以及其浓度必须以这样的方式确定,即它们不会改变本发明组合物的所需性质和优点。
根据本发明的组合物旨在用于局部施用,更具体地施用于皮肤、嘴唇、头发和/或粘膜。
根据本发明的组合物可以以任何通常用于美容品和皮肤病学领域的盖仑制剂形式存在,例如,但不限于,以任选凝胶化的水溶液、洗剂类型的分散体、(O/W)或相反的(W/O)乳液的形式,其或多或少是流体,或多重乳液,例如三重乳液(W/O/W或O/W/O),或者实际上以离子型(脂质体)和/或非离子型的多泡分散体、不含乳化剂和胶凝剂的两相组合物(其不混溶的相在储存过程中分离)、泡沫、棒、无水油、喷雾或薄雾的形式存在。
在一个优选的实施方案中,根据本发明的组合物是W/O乳液。有利地,根据本发明的W/O乳液包含乳化质量的PEG-30二聚羟基硬脂酸酯(INCI)。
在一个可供选择的实施方案中,根据本发明的组合物是O/W乳液。有利地,根据本发明的O/W乳液包含选自下列以其INCI名标识的化合物的组的乳化剂:十六烷基磷酸钾、硬脂酸甘油酯、PEG-100硬脂酸酯和C20-22烷基磷酸酯/C20-22烷基醇、硬脂酸甘油酯柠檬酸酯、三山嵛精PEG-20酯类及其混合物。
根据本发明的组合物还可以包含防腐剂。能够用于美容品或皮肤病学组合物的任何防腐剂都可以用于根据本发明组合物的制剂中。
有利地,所用的防腐剂是链烷二醇,甚至更有利地是1,2-链烷二醇或1,3-链烷二醇,以及其混合物。
在优选的实施方案中,防腐剂是选自1,2-戊二醇、1,2-己二醇、1,2-庚二醇、1,2-辛二醇和1,2-癸二醇或其混合物的1,2-二醇。
在优选的实施方案中,防腐剂是选自1,3-丙二醇和1,3-丁二醇或其混合物的1,3-二醇。实际上,这些链烷二醇由多家公司销售,特别是SYMRISE或MINACARE。
优选地,根据本发明的组合物包含0.01重量%至2重量%的二醇组合物,有利地为0.1重量%至1重量%,例如0.5重量%。
本发明还涉及一种护肤的、非治疗性的治疗方法,有利地用于对抗氧化应激,特别是皮肤的细胞老化,该方法由将根据本发明的组合物施用到有需要的受试者的皮肤上组成。
有利地,所述组合物包含单糖基化菌红素、二糖基化菌红素和四糖基化菌红素的混合物;优选包含基本上由单糖基化菌红素和二糖基化菌红素构成的糖基化菌红素混合物,并且相对于糖基化菌红素混合物的总重量,所述混合物优选包含20至80重量%的单糖基化菌红素和20至80重量%的二糖基化菌红素。
有利地局部施用的所述组合物也适用于以下用途:
-用于对抗由于全部或部分太阳辐射,通常是UV辐射或可见光引起的皮肤细胞老化的药剂;
-抗自由基剂或抗氧化剂;
-作为对抗蛋白质降解的保护剂;
-蛋白质组降解保护剂;
-细胞解毒机制的保护剂;或
-DNA修复系统的保护剂。
附图说明
通过下面的示例性实施方案,本发明可以实施的方式和伴随的优点将变得更加明显,这些示例性实施方案通过非限制性的指示并在附图的支持下给出。
[图1]图1显示了来自物种运动节杆菌的分离物SB5的类胡萝卜素提取物的成分:BR=α-菌红素,BR-MonoG:单糖基化形式,BR-DiG:二糖基化形式,BR-DiG2:BR-DiG的另一种形式,BR-TetraG:四糖基化形式。
[图2]图2显示了在正常人角质形成细胞(NHK)中由多种类胡萝卜素提供的抗UV-B诱导的蛋白质羰基化的保护作用。DMSO=二甲基亚砜(溶剂对照);BR=α-菌红素;BR-DiG=二糖基化菌红素;BR-MonoG+BR-DiG=单糖和二糖基化菌红素的混合物。
具体实施方式
实施例I.细菌运动节杆菌的类胡萝卜素提取物的糖基化菌红素的纯化
I-1研究目的
本研究的目的是分离和定量来自细菌运动节杆菌的总类胡萝卜素提取物中所含的分子。
I-2材料与方法
I-2.1提取物
在本研究中使用了来自细菌运动节杆菌的总类胡萝卜素提取物,其包含在称为“Miroruberine”的GREENTECH原料中,对应于INCI名微球菌裂解物;该提取物来源于菌株SB5。这种所谓的“SBE”提取物可以通过使用专利申请WO 2014/167247中描述的方法获得。
I-2.2柱层析色谱和薄层层析色谱
将SBE提取物与四氢呋喃(THF)混合,直至其完全溶解。在THF中稀释SBE后,在玻璃柱中通过硅胶层析色谱进行分离糖基化菌红素的步骤。
1.将硅胶悬浮在DCM/甲醇混合物(10/1)中,然后倒入柱中
2.硅胶沉淀后,加入1cm的沙子,然后用DCM/甲醇混合物洗涤3次。
3.将0.5mL在THF中稀释的SBE沉积在沙子上,并静置5分钟
4.缓慢加入50mL DCM/甲醇混合物(10/1),收集级分1、2、3和4
5.缓慢加入40mL DCM/甲醇混合物(8/2),收集级分5和6
6.缓慢加入40mL DCM/甲醇混合物(5/5),收集级分7
7.缓慢加入40mL DCM/甲醇混合物(3/7)以收集级分
8.然后通过TLC(DCM/甲醇(10/1))将所有的级分与SBE进行比较,并通过(使用每个级分的吸收最大值)吸收进行定量。
I-2.3通过HPLC分离级分
仪器:Nexera XR,二元泵(Shimadzu)
柱:C18;可持续Swift 5μm 4.6x 150mm,制造商:GL Sciences
流动相:
A:甲醇中20%H2O
B甲醇中20%EtOAc
流速:1.5mL/min
注射体积:50μL
[表1]
A | B | |
1min | 100 | 0 |
20min | 0 | 100 |
I-3结果与讨论
在该纯化中,通过柱层析色谱进行分离的第一步使得收集各种级分成为可能,通过将其与天然提取物的吸收光谱进行比较,用TLC和HPLC-DAD证实了各种级分的纯度;通过500nm的UV吸收度对各种形式进行定量。
使用AUTOFLEX仪器(Brucker:方法:CHCA和DHB矩阵,在反射镜采样中不含TFA)通过Maldi-TOF-TOF光谱学鉴定通过层析色谱收集的每个级分的每个分子。通过将获得的结果与通过HPLC-DAD对这些级分进行的定量相结合,计算不同形式之间的分布(图1)。级分1对应于β-胡萝卜素,菌红素合成中的一种副产物,但该分子仅占提取物的0.79%。级分4具有相同的盐生盐杆菌(Halobacter salinarium,Halorubin)提取物特征,其大部分分子是菌红素(BR)。该分子约占干提取物的一半(图1)。
鉴定出两种单独迁移的二糖基化形式(BR-DiG1和BR-DiG2)。二糖基化形式占提取物的22%以上。
单糖基化形式BR-MonoG占提取物的26%以上。四糖基化形式(BR-tetra)仅占提取物的0.01%(图1)。
实施例II.多种类胡萝卜素提供的抗人角质形成细胞中UV-B诱导的羰基化的保护作用
II-1研究目的
本研究的目的是比较根据实施例I.的来源于放线杆菌运动节杆菌SB5菌株的类胡萝卜素提取物的各种分子保护角质形成细胞蛋白免受UV应激的效果。
特别地,以下分子是所述研究的对象:
-α菌红素(BR)
-单糖基化形式的菌红素(MonoG-BR)
-两种二糖基化形式的菌红素(BR-DiG1和BR-DiG2);这些形式被结合并一起研究(BR-DiG)
还测试了已知的胡萝卜素、叶黄素和糖基化类胡萝卜素:
-番茄红素(胡萝卜素)
-虾青素(叶黄素)
-藏红花素(糖基化类胡萝卜素)。
在存在或不存在UV-B应激的情况下测量蛋白质的总羰基化。
II-2材料与方法
II-2.1实验设计
1-在12wp(“孔板”)上测试不同的应激剂量(UV)(聚集):
·UV-B(80;40;20;15;10mJ/cm2)
2-在1-的基础上,在小烧瓶上测试2种不同的应激剂量(UV)的羰基化;
3-在用于羰基化的54个烧瓶上检测分子对UV应激的抗性:8个分子+对照,一式三份,有和无UV;
4-测量108个条件下的羰基化(一式两份)。
II-2.2细胞处理和辐照
UV-B应激:灯的波长为313nm,剂量为80;40;20;剂量选择为10mJ/cm2,分子检测为15mJ/cm2
II-2.3测试分子和浓度
-BR,100nM
-BR-DiG,100nM
-BR-MonoG+BR-DiG 100nM(50+50nM)
-番茄红素100nM
-虾青素100nM
-藏红花素100nM。
-溶剂(DMSO)代表对照。
II-2.4角质形成细胞的培养和处理
在108个平板(直径:100mm,56cm2)中以大约一百万个细胞/平板接种永生化的NHEK/SVTERT 3-5角质形成细胞,对应于生物学一式三份中的36个条件-在37℃和5%CO2下,在角质形成细胞培养基(来自Gibco,17005075的角质形成细胞-SFM)中培养细胞至90-95%聚集。
细胞与检测分子一起孵育2小时。
预处理2小时后,除去培养基并用PBS替换。一半的板用15mJ/cm2的UV-B辐照。
在每个平板中辐照后,加入角质形成细胞-SFM培养基,并将细胞在37℃、5%CO2下孵育24小时。
从所有平板上除去培养基后,用PBS洗涤细胞,然后在酚红(CapricornScientific,TRY-3B)存在下用HBSS(1x)中的胰蛋白酶-EDTA(0.25%)进行胰蛋白酶化。收集平板后,对细胞进行计数,转移到1.5mL试管中,并在-80℃下储存沉淀。
II-2.5蛋白质羰基化的测量
通过向每个含有细胞沉淀的试管中加入100μL UTC裂解缓冲液(UTC:尿素、硫脲和CHAPS)来裂解细胞。在4℃的温度下以600rpm在微管振荡器上进行45分钟细胞的裂解。
之后,将样品离心,收集上清液;丢弃颗粒。
将上清液转移至3kDa Amicon过滤器中,用PBS冲洗(大约100μL蛋白质用400μLPBS)。在+4℃下以14000rpm离心样品40min。对于每个样品,该过程重复3次。第三次离心后,将Amicon过滤器置于新管中,并以2000rpm离心3min;洗脱液用于剩余的分析。
蛋白质浓度通过Bradford蛋白质定量分析方法来测量。
每个15μg蛋白质样品用0.15μL 5mM CF647染料染色。在+4℃、600rpm下进行过夜染色。
将蛋白质样品装载到12.5%丙烯酰胺凝胶上。电泳在80V下进行,直到样品从堆积凝胶中去除,之后电压增加至120V,直到样品到达凝胶末端。
然后收集凝胶,并在超纯水中冲洗多次。接下来,用来自250x浓缩形式的1x紫色染料(SERVA Purple-43386.01)对凝胶进行染色,以检测蛋白质的表达。该步骤在环境温度下在振荡器上以50rpm进行10min。
使用AmershamTMTyphoonTM生物分子成像仪对两种染料的图像进行数字化处理。CF647的荧光扫描波长为635nm,SERVA violet的荧光扫描波长为532nm。
随后,使用Life Science Research Bio-Rad的Image Lab软件,通过选择每个通道并对背景噪声进行标准化,对扫描图进行分析。
最后使用蛋白质印迹法(Oxy-blot)测量每种培养物的总羰基化。
II-3结果与讨论
实验的总体结果如图2所示。在该图中,比较了UV-B应激前后的羰基化水平。与不应提供显著保护的DMSO溶剂相比,可以确定一种化合物或化合物的混合物是否保护细胞蛋白质免受UV-B诱导的羰基化。令人惊讶的是,二糖基化菌红素(BR-DiG)和单糖基化菌红素和二糖基化菌红素的混合物(BR-MonoG+BR-DiG)比所有其他被检测的胡萝卜素和叶黄素,包括藏红花素(一种糖基化的类胡萝卜素)保护更有效。在每种情况下赋予的保护作用都大于用α-菌红素(BR)观察到的保护作用。
实施例III.O/W SPF50+乳液
下表中给出的百分比表示产品重量相对于组合物总重量的百分比。
[表2]
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实施例IV-日霜-O/W乳液
[表3]
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实施例V-日霜-精华液
[表4]
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参考文献
Armstrong GA(1994)Eubacteria show their true colors-genetics ofcarotenoid pigment biosynthesis from microbes to plants.J Bacteriol.176:4795-4802.
Armstrong,GA(1997).Genetics of eubacterial carotenoid biosynthesis:Acolorful tale.In:Ornston,LN.,editor.Annu Rev Microbiol.USA:Annual ReviewsInc.;629-659.
Britton G.(1995)Structure and properties of carotenoids in relationto function.FASEBJ.9:1551–1558.
Britton,GL-JSPH.(2004)Carotenoids handbook.Basel;Boston:Verlag./>
Fong N,Burgess M,Barrow K,Glenn D(2001)Carotenoid accumulation in thepsychrotrophic bacterium Arthrobacter agilis in response to thermal and saltstress Appl Microbiol Biotechnol 56:750–756.
Mandelli F,Miranda VS,Rodrigues E,Mercadante AZ(2012)Identificationof carotenoids with high antioxidant capacity produced by extremophilemicroorganisms.world J Microbiol Biotechnol 28:1781-1790.
Mohamed HE,van de Meene AML,Roberson RW,Vermaas WFJ.Myxoxanthophyllis required for normal cell wall structure and thylakoid organization in thecyanobacterium,Synechocystis sp strain PCC 6803(2005)J Bacteriol.187:6883-6892.
Strand A,Shivaji,S,Liaaen-Jensen(1997)Bacterial carotenoids 55.C50-carotenoids 25:revised structures of carotenoids associated with membranes inpsychrotrophic Micrococcus roseus.Bioch.Syst.&Eco.25:547-552.
Claims (15)
1.一种糖基化菌红素,其特征在于其分离自或选自单糖基化菌红素、二糖基化菌红素、三糖基化菌红素、四糖基化菌红素、五糖基化菌红素、六糖基化菌红素、七糖基化菌红素、八糖基化菌红素、九糖基化菌红素、十糖基化菌红素、十一糖基化菌红素和十二糖基化菌红素,并且特征在于其具有的纯度为至少70重量%,或者甚至80重量%,优选90重量%,更有利地95重量%,或者甚至99重量%。
2.根据权利要求1所述的糖基化菌红素,其特征在于,其选自单糖基化菌红素、二糖基化菌红素、三糖基化菌红素和四糖基化菌红素。
3.根据权利要求1或2所述的糖基化菌红素,其特征在于,其是从嗜极细菌的提取物中分离和纯化的,所述嗜极细菌优选为微球菌科细菌,有利地为运动节杆菌。
4.一种组合物,其特征在于其包含至少一种糖基化菌红素,并且其特征在于所述组合物不包含非糖基化形式的菌红素,并且其特征在于所述组合物包含一种或多种人类可接受的赋形剂。
5.根据权利要求4所述的组合物,其特征在于所述组合物包含至少一种如权利要求1至3中任一项所定义的分离的糖基化菌红素。
6.根据权利要求4或5所述的组合物,其特征在于所述组合物包含单糖基化菌红素、二糖基化菌红素、三糖基化菌红素和四糖基化菌红素的混合物。
7.根据权利要求4至6中任一项所述的组合物,其特征在于所述组合物包含由单糖基化菌红素和二糖基化菌红素构成的糖基化菌红素混合物,并且相对于糖基化菌红素混合物的总重量,所述混合物优选包含20至80重量%的单糖基化菌红素和20至80重量%的二糖基化菌红素。
8.一种从含有权利要求1至3中定义的至少一种糖基化菌红素的类胡萝卜素提取物中分离和纯化它们的方法,包括以下步骤:
(i)将所述提取物溶解在溶剂中,优选溶解在四氢呋喃中;
(ii)使用洗脱剂,优选使用二氯甲烷/甲醇混合物,通过硅胶型固定相柱上的吸附层析色谱,分离含有一种或多种糖基化菌红素的级分。
9.一种用于稳定蛋白质的体外方法,所述方法在于:将待稳定的蛋白质与权利要求1至3中任一项所定义的一种或多种糖基化菌红素或与权利要求4至7中任一项所定义的组合物接触进行孵育或储存。
10.根据权利要求4至7中任一项所述的组合物,其用作人类或动物的治疗方法中的药物。
11.根据权利要求4至7中任一项所述的组合物,其特征在于所述组合物为食品补充剂的形式。
12.根据权利要求4至7中任一项所述的组合物,其特征在于所述组合物为美容品组合物的形式,有利地为适于局部施用的形式。
13.根据权利要求12所述的组合物,其特征在于相对于所述美容品组合物的总重量,所述糖基化菌红素占0.0001至0.5重量%,有利地占0.001至0.01重量%。
14.根据权利要求12至13中任一项所述的组合物,其用作:
-用于对抗由于全部或部分太阳辐射,通常是UV辐射或可见光引起的皮肤细胞老化的药剂;
-抗自由基剂或抗氧化剂;
-蛋白质降解保护剂;
-蛋白质组降解保护剂;
-细胞解毒机制的保护剂;或
-DNA修复系统的保护剂。
15.根据权利要求12至13中任一项所述的组合物,其用于对抗氧化应激、尤其是皮肤细胞老化的方法中,所述方法在于将所述组合物施用于有此需要的受试者的皮肤。
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