CN102958377A - 稳定的活性化合物 - Google Patents
稳定的活性化合物 Download PDFInfo
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- CN102958377A CN102958377A CN2011800307067A CN201180030706A CN102958377A CN 102958377 A CN102958377 A CN 102958377A CN 2011800307067 A CN2011800307067 A CN 2011800307067A CN 201180030706 A CN201180030706 A CN 201180030706A CN 102958377 A CN102958377 A CN 102958377A
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- Prior art keywords
- composition
- vitamin
- oil
- stabilizing agent
- adsorbate
- Prior art date
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical group [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 claims abstract description 48
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Abstract
本发明涉及一种稳定的固体组合物，所述组合物包含第一载体和包含至少一种如维生素D衍生物等活性组分及其疏水稳定剂的吸附质，其特征在于，所述第一载体为室温下在水中的溶解度低于0.1重量%的磷酸钙或其衍生物。
Description
技术领域
本发明主要涉及包含吸附在载体上的吸附质的固体组合物领域。特别是，本发明涉及包含一种或多种吸附在载体上的组分的组合物，该组合物适于人类和动物营养和/或健康。
背景技术
包含活性化合物的制剂广泛地用于人类和动物食品、化妆品或药物组合物。活性化合物可以是维生素、附加营养物、芳香油、酶或蛋白质。
通常，这种活性化合物溶解或分散在液体溶剂中，并将由此制备的溶液包覆在颗粒状材料上或者包封在基质上，以有利于其包含到食品中或者有利于其生物吸收。所有制剂共有的问题是在工业可处理的配方中提供各自的活性化合物。现有技术公开了制备含有活性化合物的组合物的多种方法。
US 4,389,419公开了一种在微胶囊中包封油和油溶性物质的方法。首先，形成由包含碱金属藻酸盐的水溶液和醇不溶性填料的连续相和亲油性物质构成的乳液。US2003/0170324公开了一种含有溶解在油中的成分的油组合物。还公开了一种预混料组合物，其包含封入微胶囊的油和至少一种营养添加剂。
US 5,820,903公开了一种包含磷酸钙盐的营养改善型酸奶产品。该产品中的钙含量通过添加磷酸钙盐而由500mg/170g酸奶提高到1500mg/170g酸奶。
WO 98/40085公开了一种含有活性组分(例如维生素D3)和磷酸三钙的制剂。如维生素D等维生素或其代谢物已经受到很大关注。事实上，已知维生素D对控制骨代谢、免疫系统、神经退变性疾病具有重要影响。通常，术语“维生素D”指维生素D2和维生素D3及其衍生物。人类只能通过阳光中的紫外线对皮肤的作用而产生D3维生素或钙化醇。皮肤中产生的维生素D3与所谓的维生素D结合蛋白结合，后者将其输送至肝，在那里其通过25-羟基化作用而转化为25-羟基维生素D3。以往已经制得了含有维生素D成分的制剂。然而，维生素D、大多数维生素和许多活性化合物通常具有寿命有限，一般短于包含这些物质的食品或药物制剂的寿命。另外，难以将少量活性化合物均匀地分散在载体上。
US 2006/0008533公开了通过将活性化合物与稳定剂和包覆材料混合来使活性化合物稳定。将获得的制剂吸附在二氧化硅载体上。GB 405,791公开了一种制造牛用食品辅料的方法，所述方法在于使鱼肝油吸收在碳酸钙上。
然而，本领域中已知的制剂在活性组分在几天内会氧化或异构化的情况下，不能在稳定性方面提供令人满意的结果。因此，存在对于下述制剂的需求，所述制剂适于容易且均匀地将甚至很少量的活性化合物添加至如食品或药物制剂等组合物中，并且还能简单经济地增强所述活性化合物的稳定性。本发明的目的在于提供一种可满足上述需求并可克服现有技术的上述缺陷的组合物。
发明内容
本发明的一个目的是提供一种组合物，其中活性组分是稳定的。本发明的一个目的是提供一种稳定的组合物，所述组合物可以防止活性组分的氧化。本发明的另一个目的是提供一种组合物，凭借该组合物可以均匀释放(deliver)有效量的活性组分。本发明的又一目的是增强活性组分在组合物中的分散。特别是，本发明的另一目的是提供一种富含钙的组合物。特别是，本发明的又一目的是提供一种使维生素D衍生物稳定的组合物。
根据第一方面，本发明提供了一种稳定的固体组合物，所述组合物包含第一载体和其上吸附的吸附质，所述吸附质包含至少一种活性组分及其疏水稳定剂，其中所述第一载体为室温下在水中的溶解度低于0.1重量%的磷酸钙或其衍生物。所述疏水稳定剂可增强活性组分在组合物中的分散，并且如果适当选择，其可以例如通过防止活性组分氧化而有助于增强活性组分的稳定性。所述第一磷酸钙类载体与吸附质一起提供了预料不到的活性化合物稳定性的增强效果。所述载体和/或所述疏水稳定剂可以增强活性组分的稳定性。
根据第二方面，本发明提供了一种稳定的固体组合物的制备方法，所述方法包括以下步骤：
■将至少一种活性组分分散在疏水稳定剂中以形成吸附质，
■使所述吸附质与第一载体接触，并将前者吸附在第一载体上，所述第一载体是室温下在水中的溶解度低于0.1重量%的磷酸钙或其衍生物，
■使上一步骤中获得的组合物均质化，以形成稳定的固体组合物。
根据第三方面，本发明提供了本发明的组合物作为人类或动物食品中的食品成分的应用。
根据第四方面，本发明提供了本发明的组合物在药物制剂中的应用。
附图说明
图1表示从本发明活性组分浓度不同的组合物中回收的维生素D3的有效量(以μg/ml表达)在9周时间内的发展变化。
图2表示从包含多种载体和作为疏水稳定剂的黑种草籽油(Nigella sativa oil)或橄榄油的组合物中回收的维生素D3的百分比(或维生素D3收率)在1个月时间内的发展变化。
图3表示从包含多种载体的组合物中回收的维生素D3的百分比在8个月时间内的发展变化。
图4表示从包含分散在黑种草籽油(曲线A)和亚麻籽油(曲线B)中的维生素D3的吸附质中回收的维生素D3的量在7周时间内的发展变化。
图5表示从包含中性油和含抗氧化剂的油的组合物中回收的维生素D3的百分比在8个月时间内的发展变化。
图6表示溶解在多种疏水稳定剂中的维生素D3的氧化稳定性。
具体实施方式
本发明提供了一种包含活性组分的稳定的富含钙组合物，所述组合物可增强所述活性组分的稳定性。因此，本发明涉及一种稳定的固体组合物，所述组合物包含第一载体和其上吸附的吸附质，所述吸附质包含至少一种活性组分及其疏水稳定剂。根据本发明，所述载体为室温下在水中的溶解度低于0.1重量%的磷酸钙或其衍生物。认为室温是25℃。如以下实例所述，所述第一载体增强了活性组分的稳定性。相对于如碳酸钙或二氧化硅等其他已知载体的较低或中等的稳定效果，室温下在水中的溶解度低于0.1重量%的磷酸钙所提供的稳定性是预料不到的。
术语“磷酸钙”是指含有钙离子(Ca2+)以及正磷酸根(PO4 3-)、偏磷酸根(P3O9 3-)或焦磷酸根(P2O7 4-)以及偶见的氢或氢氧根离子的无机物。在一个优选实施方式中，磷酸钙可以是磷酸二钙或磷酸三钙。前缀“二”和“三”是指磷酸中分别有二或三个氢原子被钙原子替代。
在一个优选实施方式中，磷酸钙可以是磷酸三钙。术语“磷酸三钙”或“TCP”是指三碱式磷酸钙Ca3(PO4)2，并且也包括磷灰石、正磷酸钙、三代磷酸钙、碳酸磷灰石或其混合物。常见的无机磷灰石具有式Ca5(PO4)3X，其中X为F、Cl、OH、CO3或其混合物。羟基磷灰石是指式Ca5(PO4)3X中X为氢氧根的化合物。氟磷灰石是指式Ca5(PO4)3X中X为氟离子的化合物。碳酸磷灰石是指式Ca5(PO4)3X中X为(CO3)1/2的化合物。
在一个优选实施方式中，磷酸钙可以选自由三碱式磷酸钙、羟基磷灰石、氟磷灰石和碳酸磷灰石或其混合物组成的组。
所述第一载体可以为Ca/P摩尔比为0.95～2.0的磷酸钙。磷酸钙的Ca/P之比可以影响活性组分的稳定性。具体的磷酸钙的选择可以取决于其上吸附的活性组分。优选的是，磷酸钙的Ca/P摩尔比可以为1.5～2.0。更优选的是，磷酸钙的Ca/P摩尔比可以为1.5～1.75，最优选的是，Ca/P摩尔比可以为1.6～1.7。
在一个优选实施方式中，磷酸钙的水含量可以低于3.0%，优选低于1.0%，更优选低于0.5%。
如上所述，本发明的组合物包含第一载体和吸附质。本发明中所使用的术语“吸附质”是指表面或载体上吸附或者要吸附的物质或组合物。在一个优选实施方式中，第一载体与吸附质之间的重量比为200:1～2:1，优选为100:1～4:1。
本发明的吸附质含有疏水稳定剂和至少一种活性组分。因此，所述吸附质可以包含多于一种活性组分，由此本发明的组合物可以包含多于一种活性组分。术语“疏水稳定剂”是指如下文中所述的一种疏水稳定剂或包含多于一种疏水稳定剂的混合物。
吸附质中所述至少一种活性组分与所述疏水稳定剂之间的重量比可以为1:2～1:100，优选为1:10～1:40。
适当的活性组分可以为适于人类或动物消耗或健康的任何活性组分。活性组分可以是油溶性的，并且优选可溶于疏水稳定剂。所述至少一种活性组分可以选自由维生素、芳香油、风味剂、类胡萝卜素、叶黄素、抗氧化剂、不饱和脂肪酸、油溶性酶和油溶性蛋白质组成的组。认为只要活性组分室温(25℃)下在水中的溶解度落在1重量%以下，就是油溶性的。
术语“芳香油”是指天然或合成香料或其混合物。天然香料可以是以下的提取物：花(百合、薰衣草、玫瑰、茉莉、橙花、依兰)、茎和叶(天竺葵、广藿香、橙叶)、果实(茴香籽、芫荽、枯烯、刺柏)、果皮(香柠檬、柠檬、橙)、根(肉豆蔻、当归、块根芹、小豆蔻、广木香、鸢尾、石菖蒲)、木(松木、檀香、愈疮木、柏木、花梨木)、药草和草(龙嵩、柠檬草、鼠尾草、百里香)、针叶和细枝(云杉、冷杉、松树、山松)、树脂和香脂(白松香、榄香脂、安息香、没药、乳香、红没药)。另外，可以使用动物原料，例如麝猫香和海狸香。常用的合成香料化合物可以是酯类、醚类、醛类、酮类、醇类和烃类产品。酯类香料化合物可以是例如乙酸苄酯、异丁酸苯氧基乙酯、乙酸对叔丁基环己酯、乙酸芳樟酯、二甲基苄基羰基乙酸酯、乙酸苯基乙酯、苯甲酸芳樟酯、甲酸苄酯、甘氨酸乙基甲基苯酯、环己基丙酸烯丙酯、丙酸苏合香酯和水杨酸苄酯。醚类可以包括例如苄基乙基醚，醛类可以包括例如含有8～18个碳原子的线性烷醛、柠檬醛、香茅醛、香茅氧基乙醛、仙客来醛、羟基香茅醛、铃兰醛和波洁红醛(bourgeonal)，酮类可以包括例如紫罗酮、异甲基紫罗兰酮(α-isomethylion)和甲基柏木酮，其醇包括茴香脑、香茅醇、丁子香酚、异丁子香酚、香叶醇、芳樟醇、苯基乙基醇和松油醇(terpireol)；烃主要可以包括萜烯和香脂。但是，优选的是使用多种香料的混合物，其一起产生诱人的芳香气息。通常用作风味剂组分的低挥发性的精油也适于作为芳香油，例如鼠尾草油、春黄菊油、丁香油、蜜蜂花油、薄荷油、肉桂叶油、莱姆花油、杜松子油、香根草油、乳香油、白松香油、拉波拉纳姆(labolanum)油和杂薰衣草油。优选的是，单独或以混合物使用佛手柑油、二氢月桂烯醇、铃兰醛、新铃兰醛、香茅醇、苯基乙基醇、α-己基肉桂醛、香叶醇、苄基丙酮、仙客来醛、芳樟醇、乙氧基甲氧基环十一烷(boisambrene forte)、龙涎呋喃(ambroxan)、吲哚、二氢茉莉酮酸甲酯(hedione)、sandelice、柠檬油、橘皮油、橙油、异戊氧基乙酸烯丙酯、cyclovertal、杂薰衣草油、香鼠尾草油、β-大马酮、波旁天竺葵油、水杨酸环己酯、甲基柏木酮(vertofix coeur)、龙涎酮(iso-E-super)、吐纳麝香(Fixolide NP)、橡苔(Evernyl)、α-异甲基紫罗兰酮(iraldein gamma)、苯基乙酸、乙酸香叶酯、乙酸苄酯、玫瑰醚(rose oxide)、romilat、irotyl和Floramat。
术语“类胡萝卜素和叶黄素”是指但不限于番茄红素、β-胡萝卜素、α-胡萝卜素、虾青素、虾青素酯、角黄素、桔黄素、β-阿朴-8’-胡萝卜素酸乙酯、β-阿朴-8’-胡萝卜醛、叶黄素和叶黄素酯、玉米黄质和玉米黄质酯、β-隐黄素和β-隐黄素酯、辣椒质和辣椒质酯、辣椒玉红素和辣椒玉红素酯、红木素、红木素酯及其衍生物、降红木素、降红木素酯及其衍生物、藏花酸、藏花酸酯及其衍生物，或者它们的混合物。
术语“不饱和脂肪酸”是指但不限于通式RCO2H的化合物，其中R为含有至少一个双键的C3-22线性未支化烃基自由基(hydrocarbyl radical)。术语“C3-22烃基自由基”是指具有3～22个碳原子的烃基自由基。术语“不饱和脂肪酸”包括各酸的盐和酯，特别是碱金属盐和碱土金属盐以及C1-4烷基酯。术语“烷基酯”是指具有1～4个碳原子的烃基自由基。例如，C1-4烷基酯可以是甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基和叔丁基。不饱和脂肪酸在酰基自由基中含有一、二、三、四、五或六个双键。特别合适的不饱和脂肪酸可以是ω-3、ω-6和ω-9脂肪酸。ω-3脂肪酸的实例为α-亚麻酸、油酸、棕榈油酸和肉豆蔻脑酸，ω-6脂肪酸的实例为亚油酸、γ-亚麻酸和花生四烯酸，ω-9脂肪酸的实例为油酸、芥酸和神经酸。
术语“风味剂”是指天然和合成风味物质。风味剂可以是但不限于双乙酰、乙酸异戊酯、苯甲醛、肉桂醛、丙酸乙酯、氨茴酸甲酯、柠檬油精、[[乙基-(E,Z)-2,4-癸二烯酸酯]]、己酸烯丙酯、乙基麦芽酚、乙基香草醛和水杨酸甲酯。
术语“抗氧化剂”是指能够减缓或防止其他分子氧化的化合物。
术语“油溶性酶或蛋白质”是指可溶于油中的天然或合成酶或蛋白质，或者经取代可溶于油中的酶或蛋白质。该术语包括油溶性辅酶或辅因子。
术语“维生素”是指如维生素A、维生素D、维生素E、叶绿醌(维生素K1)和甲基萘醌(维生素K2)等维生素。维生素A是指但不限于所有类视色素，其定性地表现出所有反式视黄醇及其酯(如为维生素A乙酸酯、维生素A丙酸酯、维生素A棕榈酸酯及其他酯)或维生素A衍生物的生物活性。术语“维生素E”是指但不限于母育酚和生育三烯酚的所有衍生物，其定性地表现出α-生育酚的生物活性。其包括α、β和γ-生育酚以及α、β和γ-生育三烯酚和相应的非对映异构体。术语“维生素D”是指但不限于维生素D2(钙化醇)、维生素D3(胆钙化醇)及其衍生物，及其代谢物。
在一个优选实施方式中，所述至少一种活性组分可以选自由维生素、芳香油、风味剂、类胡萝卜素、叶黄素、抗氧化剂和不饱和脂肪酸组成的组。可以预料活性组分的多种组合。本发明对维生素D衍生物如维生素D3进行了实验评价，但本发明不限于此。
在一个更优选的实施方式中，所述至少一种活性组分可以包含至少一种维生素。优选的是，所述至少一种活性组分可以包含至少一种维生素D衍生物。更优选的是，所述至少一种活性组分可以至少包含维生素D3或其衍生物。作为另一选择，所述至少一种活性组分可以是维生素D3或其衍生物。
适于本发明的疏水稳定剂可以包含一种或多种C3-22脂肪酸或者其酯或甘油酯衍生物，或者其混合物。术语“C3-22脂肪酸”是指具有3～22个碳原子的烷基。酯衍生物可以是具有1～4个碳原子的烷基自由基。术语“甘油酯”包括三、二、单甘油酯和磷酰基甘油。所述疏水稳定剂可以使所述至少一种活性组分稳定。例如，疏水稳定剂可以防止至少一种活性组分氧化。疏水稳定剂为适于使至少一种活性组分稳定的液体化合物或组合物。优选的是，疏水稳定剂可以是油。
在一个优选实施方式中，所述疏水稳定剂可以还包含一种或多种抗氧化剂。疏水稳定剂的抗氧化能力可以以所述疏水稳定剂中的多酚或生育酚的数量(degree)来表达。例如，疏水稳定剂以疏水稳定剂中多酚数量表达的抗氧化剂含量可以为至少1mg没食子酸/kg疏水稳定剂；优选的是，抗氧化剂含量可以为至少10mg没食子酸/kg疏水稳定剂。多酚的数量根据本领域中常用的Folin-Ciocalteau法确定。疏水稳定剂的抗氧化剂内容物可以进一步提高组合物的稳定性。
在一个优选实施方式中，所述疏水稳定剂可以是油。所述油可以包含至少20重量%的C10-22脂肪酸或者其酯或甘油酯衍生物。疏水稳定剂可以是包含不饱和脂肪酸或者其酯或甘油酯衍生物的油。术语“不饱和”是指脂肪酸可以在烃链中具有一个或多个碳碳双键或三键。因此，术语“不饱和脂肪酸或者其酯或甘油酯衍生物”包括聚不饱和脂肪酸或者其酯或甘油酯衍生物。优选的是，所述疏水稳定剂可以是包含至少55重量%不饱和脂肪酸或者其酯或甘油酯衍生物的油。疏水稳定剂的组合物可以进一步提高活性组分的稳定性。
疏水稳定剂例如可以是但不限于红花油、葡萄籽油、罂粟籽油、葵花油、大麻油、黑种草籽油、玉米油、麦胚芽油、棉籽油、大豆油、胡桃油、橄榄油、阿甘油(Arganoil)、豆油、菜籽油或芝麻油。
特别是，疏水稳定剂可以是黑种草籽油。后者为包含至少40重量%亚油酸和至少15重量%油酸或者其酯或甘油酯衍生物的油。黑种草籽油的抗氧化剂含量为至少230mg没食子酸/kg油。
根据第二方面，本发明提供了一种稳定的固体组合物的制备方法，所述方法包括以下步骤：
■将至少一种活性组分分散在疏水稳定剂中以形成吸附质，
■使所述吸附质与第一载体接触，并将前者吸附在第一载体上，所述第一载体是室温下在水中的溶解度低于0.1重量%的磷酸钙或其衍生物，
■使上一步骤中获得的组合物均质化，以形成稳定的固体组合物。
术语“均质化”是指混合直至均匀。优选的是，所述第一载体可以是磷酸二钙或磷酸三钙。更优选的是，第一载体可以是如上所定义的磷酸三钙。最优选的是，所述第一载体可以选自由三碱式磷酸钙、羟基磷灰石、氟磷灰石和碳酸磷灰石或其混合物组成的组。
在另一优选实施方式中，所述第一载体可以为Ca/P摩尔比为0.95～2.0的磷酸钙。优选的是，磷酸钙的Ca/P摩尔比可以为1.5～2.0。更优选的是，磷酸钙的Ca/P摩尔比可以为1.5～1.75，最优选的是，Ca/P摩尔比可以为1.6～1.7。
在另一优选实施方式中，磷酸钙的水含量可以低于3.0%，优选低于1.0%，更优选低于0.5%。
在本发明的方法中，将至少一种活性组分分散在疏水稳定剂中以形成本发明的吸附质。作为另一选择，可以将一种或多种活性组分分散在一种或多种疏水稳定剂中，以形成本发明的吸附质。可以在本方法中提供多于一种活性组分，并将其同时或不同时分散在所述疏水稳定剂中。在本发明的方法中，吸附质中所述至少一种活性组分与所述疏水稳定剂之间的重量比可以为1:2～1:100，优选为1:10～1:40。
本发明的方法中使用的适当的活性组分可以是适于人类或动物消耗或健康的活性组分。活性组分可以是油溶性的，并且优选可溶于疏水稳定剂。所述活性组分可以选自由如上定义的维生素、芳香油、风味剂、类胡萝卜素、叶黄素、抗氧化剂、不饱和脂肪酸、油溶性酶和油溶性蛋白质组成的组。认为只要所述活性组分室温(25℃)下在水中的溶解度落在1重量%以下就是油溶性的。优选的是，所述至少一种活性组分可以选自由维生素、芳香油、风味剂、类胡萝卜素、叶黄素、抗氧化剂和不饱和脂肪酸组成的组。在一个优选实施方式中，本方法中使用的所述至少一种活性组分如以上关于本发明的组合物中的定义。
在本发明的方法中，所述疏水稳定剂可以包含一种或多种C3-22脂肪酸或者其酯或甘油酯衍生物，或者其混合物。酯衍生物可以是具有1～4个碳原子的烷基。术语“甘油酯”包括三、二、单甘油酯和磷酰基甘油。在一个优选实施方式中，所述疏水稳定剂可以还包含一种或多种抗氧化剂。优选的是，所述疏水稳定剂可以是包含至少20重量%C10-22脂肪酸或者其酯或甘油酯衍生物的油。疏水稳定剂可以是包含不饱和脂肪酸或者其酯或甘油酯衍生物的油。在一个优选实施方式中，疏水稳定剂可以是包含至少55重量%不饱和脂肪酸或者其酯或甘油酯衍生物的油。
因此，疏水稳定剂例如可以是但不限于红花油、葡萄籽油、罂粟籽油、葵花油、大麻油、黑种草籽油、玉米油、麦胚芽油、棉籽油、大豆油、胡桃油、橄榄油、阿甘油、豆油、菜籽油或芝麻油。优选的是，疏水稳定剂可以是黑种草籽油。
在一个优选实施方式中，本方法可以还包括使吸附质均质化的步骤。吸附质的均质化增强了至少一种活性组分在疏水稳定剂中的分散。
在吸附质形成时，其与如上定义的第一载体接触并吸附于其上。载体与吸附质之间的重量比可以为200:1～2:1。优选的是，载体与吸附质之间的重量比可以为100:1～4:1。在吸附质分散在载体上之后，使获得的组合物均质化，得到了本发明稳定的固体组合物。
根据第三方面，本发明提供了本发明的组合物作为食品成分的应用。因此，所述组合物可以用于例如乳制品、饮料(如果汁)和谷类食品等中。本发明的组合物可以用作人类或动物食品中的食品成分。因此，本发明提供了包含本发明的组合物的人类或动物食品组合物。如上所述，所述食品可以是乳制品、饮料和谷类食品等。乳制品可以是由奶牛乳、水牛乳、绵羊乳、山羊乳、骆驼乳、牦牛乳或马乳制造的食品。乳制品可以是例如奶、黄油、奶酪、酸奶、冰淇淋或意式冰激凌(gelato)。
根据本发明的另一个方面，本发明的组合物可以用于药物制剂中。所述药物制剂可以还包括赋形剂和第二载体，以及本领域公知的通常添加在此类制剂中的任何额外组分。赋形剂的实例是但不限于甘露醇、羟基丙基纤维素、乳糖、聚乙烯基吡咯烷酮、聚乙烯醇、明胶、淀粉、结晶纤维素、羟基丙基甲基纤维素、乙基纤维素、羧基甲基纤维素、糊精、乳糖、山梨糖醇、蔗糖、硅酸镁水合物、高岭土、沉淀碳酸钙、氯化钠(sodium chlorine)、二氧化钛、阿拉伯树胶和/或黄原胶。所述第二载体可以是适于口服施用并且不与化合物反应的有机物或无机物，例如明胶、大豆卵磷脂、碳水化合物(如乳糖、甘露醇或淀粉)、硬脂酸镁、滑石、纤维素。对于口服施用，使用的是片剂、包衣片剂、胶囊、悬浮液或者分散在悬浮液用小袋中的颗粒或粉末。
所述药物制剂可以适于治疗或预防骨质疏松症或者缺钙状态。所述药物制剂可以用于制造治疗或预防骨质疏松症或者缺钙状态的药剂。
在一个优选实施方式中，所述药物制剂中使用的组合物可以包含如上定义的磷酸三钙和包含至少一种维生素D衍生物和黑种草籽油的吸附质。特别是，药物制剂可以包含磷酸三钙和包含维生素D3或其衍生物和黑种草籽油的吸附质。因此，所述药物制剂可以适于治疗或预防骨质疏松症或者缺钙和/或缺维生素D状态。所述药物制剂可以用于制造治疗或预防骨质疏松症或者缺维生素D和/或缺钙状态的药剂。在一个优选实施方式中，所述维生素D3可以为活性形式。所述活性形式的维生素D3可以是但不限于1α-羟基胆钙化醇、1α,25-二羟基胆钙化醇、1α,24-二羟基胆钙化醇、1α,24,25-三羟基胆钙化醇、1α-羟基-24-氧基胆钙化醇、1α,25-二羟基-24-氧基-胆钙化醇、1α,25-二羟基-胆钙化醇-26,23-内酯、1α,25-二羟基-胆钙化醇-26,23-过氧内酯或26,26,26,27,27,27-六氟-1α,25-二羟基胆钙化醇、25-羟基胆钙化醇、24-羟基胆钙化醇、24-氧基胆钙化醇、24,25-二羟基胆钙化醇、25-羟基-24-氧基-胆钙化醇、25-羟基胆钙化醇-26,23-内酯或25-羟基胆钙化醇-26,23-过氧内酯。
在本发明的另一个方面中，提供了包含具有增强的时间稳定性的活性化合物的吸附质。所述吸附质包含至少一种活性组分和黑种草籽油。所述至少一种活性组分可以是以上关于本发明的组合物所描述的那些组分中的任意组分。所述至少一种活性组分可以选自由维生素、芳香油、风味剂、类胡萝卜素、叶黄素、抗氧化剂和不饱和脂肪酸组成的组。在一个更优选的实施方式中，所述至少一种活性组分可以包含至少一种维生素。优选的是，所述至少一种活性组分可以包含至少一种维生素D衍生物。更优选的是，所述至少一种活性组分可以至少包含维生素D3或其衍生物。特别是，所述吸附质可以含有黑种草籽油和维生素D3衍生物。
实施例
吸附质和组合物制备过程
已知维生素D3或胆钙化醇在室温和/或光环境条件下容易在数小时内氧化或异构化。因此，维生素D3用作研究本发明的吸附质和组合物在使活性组分稳定方面的功效的典型化合物。
首先将维生素D3分散在预定量的疏水稳定剂上。在室温用磁力搅拌混合该混合物数分钟。于是获得吸附质。然后使确定量的所述吸附质吸附在第一载体上，并使所获得的反应混合物均质化以形成本发明的组合物。组合物或吸附质中的维生素D3稳定性评估通过将其从吸附质或组合物中萃取出而进行。萃取使用的非限制性有机溶剂可以是甲醇、乙醇或乙腈。维生素D3的萃取可以取决于所使用的溶剂和萃取条件而得到增强。从吸附质或从组合物取等分试样以进行各维生素D3萃取。通过HPLC测量所回收的维生素D3的量。在以下条件下进行HPLC分析：使用甲醇为洗脱剂，并使用流速为1ml/分钟的等度HPLC泵、在254.4nm处进行检测的DAD1检测器和具有非极性固定相的HPLC柱(AGILENT Technology A系列)。在制备组合物或吸附质24小时后取第一等分试样；其对应于下表中t=0的情形。在1、2、3周或数月后取其他等分试样。
实施例1
本发明的组合物
在4周内评价从本发明的组合物A中回收的维生素D3的量。所述组合物包含作为第一载体的羟基磷灰石(Ca/P比为1.67并且水含量为0.3%)和包含维生素D3和黑种草籽油的吸附质(组合物中添加了20重量%的吸附质)。吸附质包含100μg/ml维生素D3。在t=0时使用甲醇萃取的维生素D3的量为72.5μg/ml。由于所回收的维生素D3的量取决于萃取用溶剂，因此将任意值R0=100指定给在t=0时的萃取量。然后相对于在t=0时获得的初始值给出标记为R的归一化值。
将本发明的组合物A与相应的吸附质B(即，无载体)相比较。吸附质B包含维生素D3和黑种草籽油但不含载体。维生素D3在吸附质B中的浓度为100μg/ml。3周后，使用组合物A获得的归一化值R3为99.4，而使用吸附质B获得的归一化值为90.9。在本发明的组合物中，维生素D3在至少4周的时间内保持稳定。因此，本发明组合物的载体增强了活性组分的稳定性。这是本领域技术人员不曾预料到的。
在9周内进行了附加的实验。图1描绘的是在9周内从包含羟基磷灰石(Ca/P比为1.67并且水含量为0.3%)和包含黑种草籽油和维生素D3的吸附质的组合物中回收的维生素D3的量(以μg/ml表达)。该实验在吸附质中存在100μg/ml(空心)和250μg/ml(阴影线)维生素D3下进行。9周后，分别回收了66.2μg/ml和166.7μg/ml维生素D3。这说明第一载体和/或疏水稳定剂增强维生素D3稳定性的能力很强。
实施例2
载体的影响
使用如磷酸钙(两种不同等级)、二氧化硅和碳酸钙等多种载体来实施比较例。使用水含量低于0.3重量%的磷酸钙(标记为“TCP”)进行测试。还对水含量为2.31重量%的磷酸钙进行测试并将其标记为“TCP FF”。图2表示从包含维生素D3和作为疏水稳定剂的黑种草籽油或橄榄油以及四种不同载体的组合物中回收的维生素D3的发展变化。所述载体为TCP、TCP FF二氧化硅或碳酸钙(CaCO3)。1个月后评估稳定性(图2，阴影线)。数据显示，不论疏水稳定剂是何物，碳酸钙均不适于使活性组分稳定。使用黑种草籽油和橄榄油时，1个月后回收维生素D3的收率分别为32.3%和7.5%。所述本发明的第一载体，即TCP和TCP FF，显示了优异的结果，因为回收维生素D3的收率在存在黑种草籽油时高于98%。相反，使用二氧化硅载体时，在存在黑种草籽油时收率为约92%。这在使用橄榄油作为疏水稳定剂时也得到确认。实际上，使用TCP载体、TCP和TCP FF时回收维生素D3的收率均高于使用二氧化硅时，其分别为96%、88%和84%。
基于这些结果，使用作为第一载体的磷酸钙TCP和TCP FF或二氧化硅和作为疏水稳定剂的黑种草籽油进行长时间测试。在t0(24小时)、t1(3个月)、t2(6个月)和t3(8个月)取等分试样来评估维生素D3的稳定性。结果显示在图3中。与二氧化硅相比，本发明的第一载体TCP(黑色矩形)和TCP FF(阴影矩形)显示了在该时间内使维生素D3稳定的强大能力。使用本发明的组合物时组合物中的维生素D3的量保持超过80%，而在使用二氧化硅时其量降至只有15%(白色矩形)。
上述实施例意外地显示出本发明包含吸附于室温下在水中的溶解度低于0.1重量%的磷酸钙载体上的吸附质(即，至少一种活性组分和疏水稳定剂)的组合物可使如维生素D3等活性组分稳定至少8个月。因此，当使用如前文所述的磷酸钙作为组合物中的第一载体时获得了出乎意料的意外效果。
实施例3
疏水稳定剂组合物的影响
实施例3报告的是从包含维生素D3(活性组分)和作为疏水稳定剂的亚麻籽油或黑种草籽油的吸附质中回收的维生素D3的量在三周内的发展变化。表示1归纳了结果。维生素D3在吸附质中的初始浓度为100μg/ml。对照组对应于不含维生素D3的吸附质。在t=0时从包含亚麻籽油的吸附质中萃取的维生素D3的量为59.8μg/ml，而从包含黑种草籽油的吸附质中萃取的维生素D3的有效量为75.2μg/ml，这两个值均在表1中在R0=100时进行归一化。本实验在下述实验条件下进行，其中，吸附质与环境空气接触以加速氧化过程。3周后，在使用黑种草籽油时获得的归一化值R3为90.9%，而在使用亚麻籽油时归一化值为26.6%。因此，与分散在黑种草籽油中相比，分散在亚麻籽油中时维生素D3得到了中度稳定。
表1：不同组合物中萃取物的维生素D3%
| t=0 | t=1周 | t=2周 | t=3周 | |
| 黑种草籽油 | 0 | |||
| 维生素D3+亚麻籽油 | 100 | 44.1 | 32.3 | 26.6 |
| 维生素D3+黑种草籽油 | 100 | 97.2 | 94.4 | 90.9 |
在7周内回收的有效量维生素D3的收率显示在图4中。曲线A表示包含黑种草籽油的吸附质，而曲线B表示使用亚麻籽油的吸附质。7周后所回收的维生素D3的有效量(使用甲醇萃取)高于65%(图4，曲线A)。当优化萃取条件后，萃取到多于80%的维生素D3。就使如维生素D3等活性组分稳定而言，黑种草籽油比亚麻籽油更有效。
实施例3表明维生素D3可以在包含一种以上C3-22脂肪酸的疏水稳定剂存在下得到稳定化。不受限于理论，这些测试表明，疏水稳定剂组合物能够影响活性组分的稳定性。不饱和脂肪酸和/或亚油酸内容物也可以增强如维生素D3等活性组分的稳定化。
实施例4
疏水稳定剂中抗氧化剂内容物的影响
还发现，疏水稳定剂的抗氧化剂内容物也可以影响活性成分的稳定性。
实施比较例来比较中性油(即miglyol油)与富含抗氧化剂的油(即，黑种草籽油)。疏水稳定剂的抗氧化能力可以以例如所述疏水稳定剂中多酚的数量来表达。图5表示的是从包含作为载体的磷酸钙和作为疏水稳定剂的miglyol油(白色矩形)或黑种草籽油(黑色矩形)的组合物中回收的维生素D3的发展变化。已知miglyol油不含抗氧化剂，而黑种草籽油富含氧化剂，其氧化剂含量为至少230mg没食子酸/kg油。在8个月内，使用黑种草籽油所回收的维生素D3的量保持得相当稳定(例如89%)，而在miglyol油存在下该量严重降低至33%。
可以根据抗氧化剂含量而选择其他油作为疏水稳定剂。在四种不同油的存在下进行维生素D3的加速老化测试。比较维生素D3在麦胚芽油、黑种草籽油、橄榄油或miglyol油中的氧化稳定性。麦胚芽油、黑种草籽油和橄榄油中多酚的数量分别为至少13mg没食子酸/kg油、至少230mg没食子酸/kg油和至少120mg没食子酸/kg油。通过以1l/分钟的速率向含有维生素D3的溶液中鼓入氧气来进行测试，并评价油。在6、20、34和48小时后取样，数据显示在图6中。维生素D3在麦胚芽油(黑色菱形)、黑种草籽油(白色菱形)和橄榄油(圆形)中的稳定性优异，而在miglyol中很低(黑色三角形)。不受限于理论，这表明疏水稳定剂的抗氧化剂内容物可以进一步提高组合物中活性组分的稳定性。因此，在本发明中，疏水稳定剂可以是具有下述抗氧化剂含量的油，所述抗氧化剂含量以其中多酚的数量表达为高于1mg没食子酸/kg油。优选的是，适于本发明的油可以具有高于10mg没食子酸/kg油的多酚数量，例如麦胚芽油、橄榄油或黑种草籽油。
根据本发明，载体即在水中的溶解度低于0.1重量%的磷酸钙，能够在疏水稳定剂存在下使至少一种活性组分稳定化。另外，所述至少一种活性组分的稳定性可以通过选择具有所限定的氧化剂含量或不饱和脂肪酸含量的疏水稳定剂来得到进一步增强。本发明的疏水稳定剂和/或第一载体可以防止活性组分的氧化。
本说明书中所使用的术语和描述只以说明的方式提出，并不意味着成为限制。本领域技术人员将会认识到，在如以下权利要求及其等同物中所限定的本发明的实质和范围内可以有许多变化，其中除非另外指明，否则所有术语都应以其最广义的用法来理解。因此，在阅读和理解本发明的以上描述时其他技术人员可以想到所有修改和改变。特别是，可以根据应用的需要，以上描述中所给出的尺寸、材料和其他参数可以不同。
Claims (14)
1.一种稳定的固体组合物，所述组合物包含第一载体和其上吸附的吸附质，所述吸附质包含至少一种活性组分及其疏水稳定剂，其特征在于，所述第一载体为室温下在水中的溶解度低于0.1重量%的磷酸钙或其衍生物。
2.如权利要求1所述的组合物，其特征在于，所述磷酸钙的Ca/P摩尔比为0.95～2.0。
3.如权利要求1或2所述的组合物，其特征在于，所述磷酸钙的水含量低于3.0%。
4.如前述权利要求中任一项所述的组合物，其特征在于，所述第一载体与所述吸附质之间的重量比为200:1～2:1。
5.如前述权利要求中任一项所述的组合物，其特征在于，所述吸附质中的所述至少一种活性组分与所述至少一种疏水稳定剂之间的重量比为1:2～1:100。
6.如前述权利要求中任一项所述的组合物，其特征在于，所述活性组分是油溶性的和/或可溶于所述疏水稳定剂。
7.如前述权利要求中任一项所述的组合物，其特征在于，所述至少一种活性组分包含维生素D衍生物，优选维生素D3。
8.如前述权利要求中任一项所述的组合物，其特征在于，所述疏水稳定剂的抗氧化剂含量以所述疏水稳定剂中的多酚数量表达为至少1mg没食子酸/kg疏水稳定剂。
9.如前述权利要求中任一项所述的组合物，其特征在于，所述疏水稳定剂包含一种或多种C3-22脂肪酸或者其酯或甘油酯衍生物，或者其混合物。
10.如前述权利要求中任一项所述的组合物，其中，所述疏水稳定剂为含有至少55重量%不饱和脂肪酸或其酯或甘油酯衍生物的油。
11.一种权利要求1～10中任一项所述的稳定的固体组合物的制备方法，所述方法包括以下步骤：
■将至少一种活性组分分散在疏水稳定剂中以形成吸附质，
■使所述吸附质与第一载体接触，并将前者吸附在所述第一载体上，
■使上一步骤中获得的组合物均质化，以形成稳定的固体组合物，
其特征在于，所述第一载体为室温下在水中的溶解度低于0.1重量%的磷酸钙或其衍生物。
12.权利要求1～10中任一项所述的组合物作为人类或动物食品中的食品成分的应用。
13.一种动物或人类食品组合物，所述组合物包含权利要求1～10中任一项所述的组合物。
14.一种药物制剂，所述制剂包含权利要求1～10中任一项所述的组合物。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EPPCT/EP2010/059014 | 2010-06-24 | ||
| EP2010059014 | 2010-06-24 | ||
| PCT/EP2011/060618 WO2011161236A1 (en) | 2010-06-24 | 2011-06-24 | Stabilized active compound |
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| Publication Number | Publication Date |
|---|---|
| CN102958377A true CN102958377A (zh) | 2013-03-06 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011800307067A Pending CN102958377A (zh) | 2010-06-24 | 2011-06-24 | 稳定的活性化合物 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9757331B2 (zh) |
| JP (1) | JP5817067B2 (zh) |
| CN (1) | CN102958377A (zh) |
| BR (1) | BR112012030239A2 (zh) |
| CA (1) | CA2798019A1 (zh) |
| EA (1) | EA022768B1 (zh) |
| ES (1) | ES2725202T3 (zh) |
| MX (1) | MX2012014872A (zh) |
| TR (1) | TR201906042T4 (zh) |
| UA (1) | UA107599C2 (zh) |
| WO (1) | WO2011161236A1 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113163804A (zh) * | 2018-12-04 | 2021-07-23 | 帝斯曼知识产权资产管理有限公司 | 吸附物 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6171333B2 (ja) * | 2012-12-26 | 2017-08-02 | 東ソー株式会社 | 安定化したビタミンｄ類標準液 |
| WO2014158033A1 (en) | 2013-03-27 | 2014-10-02 | Psm Healthcare Limited | Stabilized vitamin d formulations |
| US10336817B2 (en) | 2016-10-14 | 2019-07-02 | Sultan Qaboos University | Therapeutic composition of camel milk |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1249689A (zh) * | 1997-03-12 | 2000-04-05 | 默克专利股份公司 | 含维生素d3和磷酸三钙的稳定固体制剂 |
| CN1747658A (zh) * | 2003-03-14 | 2006-03-15 | 巴斯夫公司 | 含有活性化合物的吸附物 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB405791A (en) | 1933-01-14 | 1934-02-15 | Bell And Sons Ltd | Improvements in and relating to the manufacture of food accessories for cattle |
| US4389419A (en) | 1980-11-10 | 1983-06-21 | Damon Corporation | Vitamin encapsulation |
| JPH085782B2 (ja) * | 1989-04-14 | 1996-01-24 | 株式会社サンギ | ハイドロキシアパタイト抗菌剤及びその製造法 |
| US5820903A (en) | 1997-06-30 | 1998-10-13 | General Mills, Inc. | Calcium fortified yogurt and methods of preparation |
| US6248363B1 (en) * | 1999-11-23 | 2001-06-19 | Lipocine, Inc. | Solid carriers for improved delivery of active ingredients in pharmaceutical compositions |
| JP2002080358A (ja) * | 2000-09-07 | 2002-03-19 | Noevir Co Ltd | 皮膚外用剤 |
| US6790462B2 (en) | 2001-08-09 | 2004-09-14 | Rhodia Inc. | Calcium dietary supplement |
| US7632518B2 (en) | 2002-01-15 | 2009-12-15 | Dsm Ip Assets B.V. | 25-hydroxy vitamin D3 compositions |
| CA2669094A1 (en) * | 2006-11-08 | 2008-05-29 | Novavax,Inc. | Method of preparing solid dosage forms of multi-phasic pharmaceutical compositions |
| US20100204204A1 (en) * | 2007-06-06 | 2010-08-12 | University Of South Florida | Nutraceutical co-crystal compositions |
| EP2368440B1 (en) * | 2007-06-29 | 2014-06-04 | DSM IP Assets B.V. | Feed additive composition comprising benzoic acid and a mixture of adsorbed essential oil compounds |
-
2011
- 2011-06-24 CN CN2011800307067A patent/CN102958377A/zh active Pending
- 2011-06-24 BR BR112012030239A patent/BR112012030239A2/pt not_active IP Right Cessation
- 2011-06-24 JP JP2013515911A patent/JP5817067B2/ja not_active Expired - Fee Related
- 2011-06-24 US US13/701,054 patent/US9757331B2/en active Active
- 2011-06-24 ES ES11727187T patent/ES2725202T3/es active Active
- 2011-06-24 MX MX2012014872A patent/MX2012014872A/es not_active Application Discontinuation
- 2011-06-24 UA UAA201300751A patent/UA107599C2/uk unknown
- 2011-06-24 WO PCT/EP2011/060618 patent/WO2011161236A1/en active Application Filing
- 2011-06-24 CA CA2798019A patent/CA2798019A1/en not_active Abandoned
- 2011-06-24 TR TR2019/06042T patent/TR201906042T4/tr unknown
- 2011-06-24 EA EA201270826A patent/EA022768B1/ru not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1249689A (zh) * | 1997-03-12 | 2000-04-05 | 默克专利股份公司 | 含维生素d3和磷酸三钙的稳定固体制剂 |
| CN1747658A (zh) * | 2003-03-14 | 2006-03-15 | 巴斯夫公司 | 含有活性化合物的吸附物 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113163804A (zh) * | 2018-12-04 | 2021-07-23 | 帝斯曼知识产权资产管理有限公司 | 吸附物 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2725202T3 (es) | 2019-09-20 |
| UA107599C2 (xx) | 2015-01-26 |
| EA201270826A1 (ru) | 2013-05-30 |
| EA022768B1 (ru) | 2016-02-29 |
| US20130095150A1 (en) | 2013-04-18 |
| CA2798019A1 (en) | 2011-12-29 |
| MX2012014872A (es) | 2013-01-24 |
| BR112012030239A2 (pt) | 2015-09-08 |
| JP5817067B2 (ja) | 2015-11-18 |
| US9757331B2 (en) | 2017-09-12 |
| JP2013532157A (ja) | 2013-08-15 |
| TR201906042T4 (tr) | 2019-05-21 |
| WO2011161236A1 (en) | 2011-12-29 |
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| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20130306 |