CN112236525A - 含有类黄酮-环糊精包合物的组合物 - Google Patents
含有类黄酮-环糊精包合物的组合物 Download PDFInfo
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- CN112236525A CN112236525A CN201880094083.1A CN201880094083A CN112236525A CN 112236525 A CN112236525 A CN 112236525A CN 201880094083 A CN201880094083 A CN 201880094083A CN 112236525 A CN112236525 A CN 112236525A
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- CN
- China
- Prior art keywords
- cyclodextrin
- glucoside
- flavonoid
- inclusion compound
- composition
- 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
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Abstract
组合物,其含有选自脂肪酸、蛋白质、肽、氨基酸、维生素、矿物质、醇、甜味剂、酸味剂、抗氧化剂、增稠稳定剂和表面活性剂中的1种以上原材料、以及类黄酮‑环糊精包合物,前述包合物包含通过对具有鼠李糖苷结构的类黄酮在环糊精存在下用具有鼠李糖苷酶活性的酶进行处理而得到的包合物。根据本发明,可抑制源自类黄酮的苦味和色调变化,此外,可改善具有不愉快味道的饮料食品等,因此可适合用于医药品、饮料食品、健康食品、特定保健用食品和化妆品等领域中。
Description
技术领域
本发明涉及含有类黄酮-环糊精包合物的组合物、包含该组合物的饮料食品、医药品或化妆品(饮料食品等)、和饮料食品等的制造方法、以及抑制饮料食品等中的源自类黄酮的苦味的方法、抑制源自类黄酮的色调变化的方法、抑制不愉快味道的方法、和对皮肤的美容改善方法。
背景技术
作为类黄酮的儿茶素、芦丁、异槲皮苷、槲皮素、橙皮苷、橙皮素-7-葡萄糖苷、柚皮素-7-葡萄糖苷、酶处理异槲皮苷、酶处理橙皮苷、异黄酮等已知具有抗肥胖、抗炎症作用、抗过敏、抗高血压、抗骨质疏松、降低体脂等生理活性。
然而,如果在饮料食品、医药品中含有类黄酮,则即使类黄酮的含量微小,有时也会感觉到苦味,有时是不令人满意的。因此,进行了用于抑制苦味的报告。
例如,报告了通过将具有苦味的类黄酮包合在环糊精中苦味减少。例如,报告了通过在含儿茶素的组合物中并用β-环糊精和γ-环糊精,减少含儿茶素的组合物的苦味。(专利文献1)
报告了异黄酮衍生物(丙二酰基黄豆苷元、丙二酰基染料木苷等)通过与β-环糊精或γ-环糊精的包合,抑制了异黄酮衍生物的苦味、涩味、收敛味。(专利文献2)
通过组合类黄酮糖苷的糖加成物和二酰基甘油,显著减少类黄酮糖苷的糖加成物的苦味、涩味、辛辣味,提供风味良好的含油脂的食品。公开了一种抑制柚皮苷的涩味或收敛味的方法,其特征在于,相对于呈现涩味或收敛味的柚皮苷1重量份,添加三氯半乳蔗糖0.001~2重量份。(专利文献3、4)
公开了为了减少在以高浓度使用异槲皮苷和其糖苷(“酶处理异槲皮苷”)时特别产生的苦味、辛辣味、还显著改善后味,含有可饮用食用的酸类、脂肪酸、糖类、糖醇、醇类、抗氧化剂、高甜味度甜味剂、蛋白质、肽类、氨基酸类、维生素类、矿物质类、增稠稳定剂、表面活性剂中的1种或2种以上。(专利文献5)
此外,类黄酮一般而言容易被氧化,因此如果长期保存含有类黄酮的饮料食品、医药品、化妆品等,则有时着色缓慢进行从而色调显著变化。因此,进行了用于抑制色调的报告。
例如,提出了配混有槲皮素糖苷的容器装填饮料,其通过在配混有槲皮素糖苷的饮料中配混在300~420nm的波长区域中具有吸收的抗氧化剂,且以饮料的彩度达到26~45的方式进行调制,即使长期保存也难以发生色调变化。(专利文献6)
提出了容器装填饮料,其通过在特定量的异槲皮苷和其糖加成物中含有特定量的脂肪族醇、赤藓糖醇、木糖醇、麦芽糖醇、海藻糖等,长时间保存时色调难以变化。(专利文献7、8)
此外,因饮料食品的甜味的留存、甜味、苦味、涩味、辛辣味、酸味等不愉快味道,限制了饮用食用。因此,还要求改善和减少这些不愉快味道。例如,公开了橙皮苷糖苷、或橙皮苷糖苷和橙皮苷的混合物、和分散橙皮素对不令人满意的饮料食品的风味改善是有效的(专利文献9、10);用于抑制软糖以外的食品、经口用医药品或化妆料的苦味、辛味、涩味、辛辣味和收敛味的味觉改质剂,其特征在于,含有甘油单或二酯与多羧酸的酯的金属盐或氨基酸盐(专利文献11)。
此外,还公开了环糊精改善各种各样原材料的苦味、涩味、收敛味。例如,为了改善酪蛋白水解物的苦味、和改善肽的苦味,提出了添加环糊精,为了掩蔽生药类的苦味·不愉快味道,提出了添加有环糊精的颗粒剂。(专利文献12~14)
此外,为了改善具有苦味、涩味等不愉快味道的食品,公开了含有作为类黄酮的酶处理异槲皮苷和环状糊精中的1种以上的味觉改变剂。(专利文献15)
此外,为了皮肤的美容用途,公开了单糖与类黄酮类等抗氧化剂的组合。(专利文献16)
现有技术文献
专利文献
专利文献1:日本特开2006-115772号公报
专利文献2:日本特开2003-183166号公报
专利文献3:日本特许4457067号公报
专利文献4:日本特许第5259149号公报
专利文献5:日本特开2015-208241号公报
专利文献6:日本特开2015-65943号公报
专利文献7:日本特许第5256370号公报
专利文献8:日本特许第5298232号公报
专利文献9:日本特许第3208113号公报
专利文献10:日本特开2016-07147号公报
专利文献11:日本特许第3419958号公报
专利文献12:日本特开平2-283246号公报
专利文献13:日本特开2006-75064号公报
专利文献14:日本特许第5552400号公报
专利文献15:日本特开2017-63742号公报
专利文献16:日本特许第6186104号公报。
发明内容
发明要解决的课题
如上述那样,提出了大量抑制源自类黄酮的苦味的方法、抑制源自类黄酮的色调变化的方法、和通过含有特定的原材料而改善不愉快味道的方法、和对皮肤的美容改善方法,但未能充分令人满意,期望进一步改良。
本发明的课题在于,提供抑制苦味和色调变化的含类黄酮的组合物。此外,提供包含该组合物的饮料食品等和其制造方法。此外,提供新的抑制饮料食品等的苦味的方法、抑制色调变化的方法、抑制不愉快味道的方法、和对皮肤的美容改善方法。
用于解决课题的手段
本发明涉及下述[1]~[7]。
[1]组合物,其含有选自脂肪酸、蛋白质、肽、氨基酸、维生素、矿物质、醇、甜味剂、酸味剂、抗氧化剂、增稠稳定剂和表面活性剂中的1种以上原材料、以及类黄酮-环糊精包合物,前述包合物包含通过对具有鼠李糖苷结构的类黄酮在环糊精存在下用具有鼠李糖苷酶活性的酶进行处理而得到的包合物。
[2]饮料食品,其包含[1]所述的组合物。
[3]医药品,其包含[1]所述的组合物。
[4]化妆品,其包含[1]所述的组合物。
[5]饮料食品、医药品或化妆品的制造方法,其包括将饮料食品原料、医药品原料或化妆品原料与[1]所述的组合物混合的步骤。
[6]抑制饮料食品或医药品中的源自类黄酮的苦味的方法,其包括将饮料食品原料或医药品原料与[1]所述的组合物混合的步骤。
[7]抑制饮料食品、医药品或化妆品中的源自类黄酮的色调变化的方法,其包括将饮料食品原料、医药品原料或化妆品原料与[1]所述的组合物混合的步骤。
发明的效果
根据本发明,能够提供抑制苦味和色调变化的含类黄酮的组合物。此外,能够提供包含该组合物的饮料食品等和其制造方法。此外,能够提供饮料食品等的新的苦味抑制方法、色调变化抑制方法、不愉快味道抑制方法、和对皮肤的美容改善方法。应予说明,本发明中所称的美容改善是指通过防护皮肤细胞不受太阳光伤害、且提高再生能力,从而提高皮肤细胞的生存率,减少皱纹出现,改善皮肤的光泽等。
具体实施方式
本发明人等针对前述课题进行研究发现,在含有特定的原材料、以及将类黄酮用环状寡糖包合的包合物(以下也简称为“包合物”)的组合物中,源自类黄酮的苦味和色调变化被抑制。进一步发现,因含有特定的原材料而导致的甜味的留存、甜味、苦味、涩味、辛辣味、酸味等不愉快味道也被抑制,此外对皮肤显示出美容改善效果。
本发明的组合物含有以下所示的原材料和包合物。
作为原材料,可以举出脂肪酸、蛋白质、肽、氨基酸、维生素、矿物质、醇、甜味剂、酸味剂、抗氧化剂、增稠稳定剂、表面活性剂。本发明的组合物中可含有1种或2种以上的原材料。
作为脂肪酸,只要能够用于饮料食品等则没有特别限制,可以举出例如己酸、辛酸、壬酸、癸酸、月桂酸、肉豆蔻酸、十五烷酸、棕榈酸、棕榈油酸、硬脂酸、油酸、异油酸、亚油酸、α-亚麻酸、β-亚麻酸、二高-γ-亚麻酸、花生四烯酸、木蜡酸、神经酸、9-十四碳烯酸、9-十五碳烯酸、二十二碳六烯酸、二十碳五烯酸等。
作为蛋白质,只要能够用于饮料食品等则没有特别限制,可以举出例如明胶、胶原蛋白、酪蛋白、酪蛋白钠、酪蛋白磷酸肽、乳清蛋白质、乳铁蛋白、大豆蛋白质、小麦谷蛋白、聚谷氨酸等。
作为肽,只要能够用于饮料食品等则没有特别限制,可以举出例如将上述蛋白质分解而得到的物质等。
作为氨基酸,只要能够用于饮料食品等则没有特别限制,可以举出例如丙氨酸、精氨酸、天冬酰胺、天冬氨酸、半胱氨酸、谷氨酰胺、谷氨酸、甘氨酸、缬氨酸、组氨酸、异亮氨酸、亮氨酸、赖氨酸、苏氨酸、甲硫氨酸、苯丙氨酸、脯氨酸、丝氨酸、苏氨酸、色氨酸、酪氨酸、缬氨酸、茶氨酸等。
作为维生素,只要能够用于饮料食品等则没有特别限制,可以举出例如维生素A、维生素B1、维生素B2、烟酸、泛酸、维生素B6、维生素B12、生物素、抗坏血酸(维生素C)、维生素D2、维生素D3、维生素E、维生素K、叶酸等。其中,从进一步抑制类黄酮的苦味和色调变化的观点出发,此外从进一步改善含有维生素的食品和饮料食品中的酸味等不愉快味道的观点出发,优选抗坏血酸。
作为矿物质,只要能够用于饮料食品等则没有特别限制,可以举出例如钠、钾、钙、铁、镁、铜、锰、锌、硒、磷、碘、铬、钼等。
作为醇,只要能够用于饮料食品等则没有特别限制,可以举出例如甲醇、乙醇、1-丙醇、异丙醇、1-丁醇、2-丁醇、异丁醇、异戊醇、2-戊醇、3-戊醇、1-己醇、2-己醇、3-己醇、1-庚醇、2-庚醇、3-庚醇、4-庚醇等1元醇、乙二醇、丙二醇、1,3-丁二醇、丙二醇等多元醇等含香料的醇成分等。
作为甜味剂,只要赋予甜味且能够用于饮料食品等则没有特别限制,可以举出例如糖、糖醇、高甜味度甜味剂。作为糖,可以举出例如果糖、葡萄糖、鼠李糖、塔格糖、阿拉伯糖等单糖、乳糖、海藻糖、麦芽糖、蔗糖等二糖、粉末糖稀等多糖、麦芽寡糖、半乳寡糖等寡糖、糖稀、蜂蜜等。作为糖醇,可以举出例如山梨糖醇、赤藓糖醇、木糖醇、麦芽糖醇、乳糖醇、甘露醇、苏糖醇、阿拉伯糖醇、核糖醇、还原糖稀、还原异麦芽酮糖等。作为高甜味度甜味剂,可以举出例如阿斯巴甜、三氯半乳蔗糖、安赛蜜、爱德万甜、糖精、纽甜、索马甜、莫内林、monatin、罗汉果提取物、甘草提取物、甘草甜素、甜叶菊提取物、甜叶菊酶处理物、甜叶菊苷A、甜菊苷、甘草酸、马宾灵、brazzein等。其中,从进一步抑制类黄酮的苦味和色调变化的观点出发,此外从进一步改善含有甜味剂的食品和饮料食品中的甜味的留存、或者甜味的不愉快味道的观点出发,优选阿斯巴甜、三氯半乳蔗糖、安赛蜜、甜叶菊提取物、山梨糖醇、赤藓糖醇、木糖醇。此外,从进一步抑制类黄酮的后味的金属味、和/或酸味的观点出发,此外从对皮肤的美容效果的观点出发,优选鼠李糖。
作为酸味剂,只要赋予酸味且能够用于饮料食品等则没有特别限制,可以举出例如己二酸、丁酸、异丁酸、柠檬酸、葡糖酸、琥珀酸、甲酸、乙酸、酒石酸、乳酸、植酸、富马酸、苹果酸、丙酸、4-羟基苯甲酸、2,5-二羟基苯甲酸、3,4-二羟基苯甲酸、香草酸、4-羟基-3,5-二甲氧基苯甲酸、和多磷酸、焦磷酸、偏磷酸、磷酸或它们的盐等。
作为抗氧化剂,只要能够用于饮料食品等则没有特别限制,可以举出例如异抗坏血酸、亚硫酸盐类、生育酚类、二丁基羟基甲苯(BHT)、丁基羟基茴香醚(BHA)、乙二胺四乙酸类、没食子酸类、甘草油性提取物、食用美人蕉提取物、丁香提取物、鼠尾草提取物、丹贝提取物、鱼腥草提取物、生咖啡豆提取物、绿原酸、葵花籽提取物、葡萄籽提取物、蓝莓叶提取物、蜂胶提取物、银杏提取物、杨梅提取物、杨梅苷、桉树叶提取物、迷迭香提取物、丁香提取物、酶处理芦丁、酶处理异槲皮苷、异黄酮、 紫杉叶素(二氢槲皮素)、儿茶素、聚合儿茶素、茶提取物、川陈皮素、甲氧基黄酮、辅酶Q10、苹果提取物、酶分解苹果提取物、芝麻油提取物、米糠油提取物、鞣酸、咖啡因、和这些抗氧化剂的氧化物、例如脱氢抗坏血酸、异抗坏血酸氧化物、生育酚类氧化物等。其中,从在含有抗氧化剂的食品和饮料食品中对苦味、涩味、辛辣味的不愉快味道进一步显示效果的观点出发,优选儿茶素、茶提取物、绿原酸、鞣酸、咖啡因。
作为增稠稳定剂,只要能够用于饮料食品等则没有特别限制,可以举出例如茁霉多糖、葡聚糖、凝胶多糖、结冷胶、黄原胶、β-葡聚糖、瓜尔胶、瓜尔胶酶分解物、刺槐豆胶、罗望子胶、亚麻籽胶、达马树脂、阿拉伯胶、阿拉伯半乳聚糖、印度树胶、卡拉胶、琼脂、琼脂糖、岩藻依聚糖、藻酸、果胶、大豆多糖类、几丁质、壳聚糖、壳聚寡糖、氨基葡萄糖、魔芋粉、葡甘露聚糖、纤维素、羧基甲基纤维素钠、羧基甲基纤维素钙、羟基丙基纤维素、羟基丙基甲基纤维素、发酵纤维素、淀粉、羟基丙基淀粉、糊精、麦芽糖糊精、透明质酸、聚谷氨酸等。
作为表面活性剂,只要能够用于饮料食品等则没有特别限制,可以举出例如山梨糖醇脂肪酸酯、聚山梨糖醇脂肪酸酯、有机酸甘油单酯、脱水山梨糖醇脂肪酸酯、丙二醇脂肪酸酯、卵磷脂、酶分解卵磷脂、溶血卵磷脂、大豆卵磷脂、蛋黄卵磷脂、蔗糖脂肪酸酯、皂苷、皂树皂苷等。
原材料的含量从抑制苦味和色调变化的观点出发,在本发明的组合物中,优选为0.001质量%以上、更优选为0.003质量%以上、进一步优选为0.005质量%以上,此外,从对味道和色调的影响的观点出发,优选为80质量%以下、更优选为75质量%以下、进一步优选为70质量%以下。此外,从改善原材料的不愉快味道的观点出发,在本发明的组合物中,优选为0.01%以上、进一步优选为0.02质量%以上,此外,上限只要是示出不愉快味道的浓度则没有特别限制,优选为90%以下。应予说明,含有2种以上的原材料的情况中的含量是指原材料的总计量。
此外,在作为原材料而含有鼠李糖的情况下,从抑制类黄酮的后味的金属味和/或酸味的观点出发,此外从对皮肤的美容效果的观点出发,鼠李糖与包合物的类黄酮的摩尔比(鼠李糖/类黄酮)优选为0.05以上、更优选为0.1以上、进一步优选为0.5以上、进一步优选为0.8以上,此外从对味道的观点出发,此外从皮肤美容的观点出发,优选为20以下、更优选为15以下、进一步优选为10以下、进一步优选为1.2以下。
作为包合物中的类黄酮,是不具有鼠李糖苷结构的类黄酮,可以举出例如异槲皮苷、橙皮素-7-葡萄糖苷、柚皮素-7-葡萄糖苷(樱桃苷)、香叶木素-7-葡萄糖苷、杨梅黄酮、圣草酚-7-葡萄糖苷、木犀草素-7-葡萄糖苷、花翠素-3-葡萄糖苷、矢车菊素-3-葡萄糖苷、异鼠李素-3-葡萄糖苷、山柰酚-3-葡萄糖苷、芹菜素-7-葡萄糖苷、槲皮素、橙皮素、柚皮素、金合欢素-7-葡萄糖苷、黄豆苷元、染料木素、大豆黄素、黄豆苷元、染料木苷、黄豆黄苷(glycitin)、和它们的衍生物等。作为衍生物,可以举出乙酰基化物、丙二酰基化物、甲基化物等。其中,从进一步抑制类黄酮的苦味和色调变化的观点出发,此外从进一步改善具有不愉快味道的饮料食品和医药品的观点出发,此外从利用化妆品等的皮肤美容效果的观点出发,优选异槲皮苷、橙皮素-7-葡萄糖苷、柚皮素-7-葡萄糖苷。
作为包合物中的环状寡糖,表示单糖连接为环状的化合物,可以举出例如环糊精、环葡聚糖、环果聚糖、环交替聚糖( cycloalternan)、簇糊精(cluster dextrin)等。其中,从抑制类黄酮的苦味和色调变化的观点出发,此外从进一步改善具有不愉快味道的饮料食品和医药品的观点出发,此外从利用化妆品等的皮肤美容效果的观点出发,优选为环糊精、环葡聚糖,更优选为环糊精。
作为环糊精(CD),α-环糊精(α-CD)、支链环糊精等种类没有限制,可以优选使用选自β-环糊精(β-CD)、支链β-环糊精(分支β-CD)和γ-环糊精(γ-CD)中的1种以上。
环糊精是D-葡萄糖通过α-1,4糖苷键键合并采取环状结构的环状寡糖的一种,键合7个的形成β-环糊精,键合8个的形成γ-环糊精。支链β-CD是在β-CD上作为侧链而连结有1个以上的葡萄糖残基、半乳糖基或羟基丙基的物质,有麦芽糖基β-CD(G2-β-CD)、羟基丙基-β-CD(HP-β-CD)等。
包合物中的类黄酮与环糊精的摩尔比(环糊精/类黄酮)从稳定性的观点出发,优选为1.0以上、更优选为1.1以上、进一步优选为1.2以上,此外,从苦味、对色调的影响和经济性的观点出发,优选为3.0以下、更优选为2.0以下、进一步优选为1.8以下。
作为包合物,可以考虑上述的类黄酮和环状寡糖的各种组合,从抑制类黄酮的苦味、色调变化和风味的观点出发,和从改善具有不愉快味道的饮料食品和医药品的观点出发,此外从利用化妆品等的皮肤美容效果的观点出发,优选包含选自异槲皮苷-γ-环糊精包合物、橙皮素-7-葡萄糖苷-β-环糊精包合物、和柚皮素-β-环糊精包合物中的1种以上、且包合物中的类黄酮(异槲皮苷、橙皮素-7-葡萄糖苷、柚皮素-7-葡萄糖苷等)与环糊精的摩尔比(环糊精/类黄酮)为1.0~3.0,更优选为1.0~1.8。
此外,从抑制类黄酮的苦味和色调变化的观点出发,和从改善具有不愉快味道的饮料食品和医药品的观点出发,此外从利用化妆品等的皮肤美容效果的观点出发,优选通过后述的酶法而得到的包合物。其机制尚不明确,但推定为,在通过搅拌混合(溶解法、混炼法等)而利用类黄酮糖苷和环糊精制作包合物的情况下,在溶解法中,类黄酮糖苷(例如芦丁等)和环糊精包合的部位是与类黄酮糖苷的A-C环、B环、和糖部分无规包合(PLOS ONE,10(3),e0120858,2015),但在通过酶法来制作包合物的情况下,与环糊精包合的类黄酮糖苷的接合部位和比率与溶解法不同,苦味、色调变化的抑制效果、改善不愉快味道的效果、和对皮肤的美容效果更强。
包合物中类黄酮部分在水中的溶解度从抑制类黄酮的苦味和色调变化的观点出发,和从改善具有不愉快味道的饮料食品和医药品的观点出发,此外从利用化妆品等的皮肤美容效果的观点出发,优选为0.001%以上、更优选为0.005%以上、进一步优选为0.01%以上、进一步优选为0.015%以上、进一步优选为0.02%以上、进一步优选为1.0%以上、进一步优选为2.0%以上、进一步优选为2.5%以上、进一步优选为3%以上。此外,上限没有特别限定,可设为例如20%以下。应予说明,本说明书中类黄酮部分在水中的溶解度是25℃下的质量百分比浓度,可以通过后述的实施例中记载的方法测定。
包合物的含量如果以包合物中的类黄酮的含量作为基准而表示,则在本发明的组合物中,优选为类黄酮达到0.001质量%以上的量、更优选为达到0.005质量%以上的量、进一步优选为达到0.01质量%以上的量,此外从抑制类黄酮的苦味和色调变化的观点出发,此外从利用化妆品等的皮肤美容效果的观点出发,优选为达到10质量%以下的量、更优选为达到9质量%以下的量、进一步优选为达到8质量%以下的量。此外,从改善具有不愉快味道的组合物的观点出发,优选为达到10质量%以下的量、更优选为达到1%质量%以下的量、进一步优选为达到0.1质量%以下的量。应予说明,含有2种以上的包合物的情况中的含量是指包合物中的类黄酮的总计量。
本发明的组合物可以任选进一步单独含有香料(包括乳化香料)、起泡剂、泡稳定剂、各种酯类、色素类(天然色素(花青苷色素、类胡萝卜素色素等)、合成色素)、乳化剂、防腐剂、调味料、碳酸盐、有机酸、食物纤维、果汁、谷物提取物、麦芽提取物、蔬菜提取物、花蜜提取物、茶提取物、红茶提取物、根茎类蔬菜提取物、植物提取物、辣木提取物、醋栗提取物、品质稳定剂等添加剂或组合含有2种以上。应予说明,添加剂的含量可以在不妨碍本发明目的的范围内适当选择。
本发明的组合物除了抗氧化效果、自由基补充效果等各种生理效果之外,抑制类黄酮的苦味和色调变化的效果、和改善饮料食品等的不愉快味道的效果也优异,因此可以适合用作饮料食品用组合物、医药用组合物、化妆用组合物、和饮料食品添加物组合物。更详细而言,可以用作用于饮料食品等的褐变防止、紫外线吸收、抗氧化、抗过敏、抗癌、抗炎症、肠内菌群改善、消臭、血浆胆固醇上升抑制、血压上升抑制、血糖上升抑制、血小板凝集抑制、痴呆预防、体脂燃烧、体脂蓄积抑制、持久力提高、抗疲劳、冷感症改善、皮肤状态改善、生发、肌肉萎缩抑制、睡眠、抗癌、抗病毒、美白、皮肤改善、去皱的原材料,此外,可以用作饮料食品添加物的抗氧化剂、褪色防止剂、香味劣化防止剂。饮料食品添加物组合物为了甜味剂、着色剂、防腐剂、增稠稳定剂、发色剂、漂白剂、防霉剂、口香糖胶基、苦味剂、光亮剂、酸味剂、调味料、乳化剂、强化剂、制造用剂、香料的劣化防止等而添加,可以制成混合制剂。
即,本发明中,可以提供包含本发明的组合物的饮料食品、医药品、化妆品等。这些饮料食品等可以通过包括将饮料食品原料、医药品原料或化妆品原料与本发明的组合物混合的步骤的制造方法而制备。此外,本发明中,还能够提供包括将饮料食品原料或医药品原料与本发明的组合物混合的步骤的抑制饮料食品或医药品中的源自类黄酮的苦味的方法;包括将饮料食品原料、医药品原料、或化妆品原料与本发明的组合物混合的步骤的抑制饮料食品、医药品、或化妆品中的源自类黄酮的色调变化的方法。应予说明,将饮料食品等的原料与本发明的组合物混合的步骤均可在饮料食品等的原料中添加本发明的组合物,也可以在饮料食品等的原料中将原材料和包合物分别添加。
饮料食品包括食品和饮料,可以举出例如营养辅助食品、健康食品、特定保健用食品、功能性表示食品、食物疗法用食品、综合健康食品、营养补品、茶饮料、咖啡饮料、果汁、清凉饮料、健康饮料等。
医药品包括医药品或医药部外品,优选为经口制剂、或皮肤用外用剂,可以制成溶液剂、片剂、颗粒剂、丸剂、糖浆剂、或洗剂、喷雾干燥剂、软膏剂的形态。
作为化妆品,可以制成霜剂、液体洗剂、乳液状洗剂、喷雾剂、化妆水等形态。
饮料食品等为液态或半固体状的情况中的本发明的组合物的含量从抑制类黄酮的苦味和色调变化的观点出发,和从改善饮料食品等不愉快味道的观点出发,此外从利用化妆品等的皮肤美容效果的观点出发,本发明的组合物中的类黄酮含量在饮料食品等中,优选为达到0.0001质量%以上的量、更优选为达到0.001质量%以上的量、进一步优选为达到0.01质量%以上的量,此外从抑制苦味和色调变化的观点出发,和从改善饮料食品等不愉快味道的观点出发,此外从利用化妆品等的皮肤美容效果的观点出发,优选为达到5质量%以下的量、更优选为达到2质量%以下的量、进一步优选为达到1质量%以下的量。
饮料食品等为固体状的情况中的本发明的组合物的含量从抑制类黄酮的苦味和色调变化的观点出发,和从改善饮料食品等不愉快味道的观点出发,此外从利用化妆品等的皮肤美容效果的观点出发,本发明的组合物中的类黄酮含量在饮料食品等中,优选为达到0.001质量%以上的量、更优选为达到0.01质量%以上的量、进一步优选为达到0.015质量%以上的量、进一步优选为达到0.02质量%以上的量,此外,从抑制类黄酮的苦味和色调变化的观点出发,和从改善饮料食品等不愉快味道的观点出发,此外从利用化妆品等的皮肤美容效果的观点出发,优选为达到30质量%以下的量、更优选为达到25质量%以下的量、进一步优选为达到20质量%以下的量、进一步优选为达到10质量%以下的量。
接着,针对本发明的组合物的制造方法进行说明。本发明的组合物可以通过利用公知的方法将原材料、包合物和任选的添加剂混合而得到。
作为制备本发明的组合物中包含的包合物的方法,没有特别限定,可以通过乳化法、饱和水溶液法、混炼法、溶解法、混合粉碎法等包合物等的公知的方法制备,从抑制类黄酮的苦味和色调变化的观点出发,和从改善饮料食品等不愉快味道的观点出发,此外从利用化妆品等的皮肤美容效果的观点出发,优选通过以下所示的酶法制备。应予说明,以下的说明中,以使用环糊精的方式为例进行了说明,但本发明不限于此,可同样使用其它的环状寡糖。
作为包合物的适合的制备方法,可以举出对具有鼠李糖苷结构的类黄酮在环糊精存在下通过具有鼠李糖苷酶活性的酶进行处理的方法(以下也称为“酶法”)。通过酶法,从具有鼠李糖苷结构的类黄酮中将鼠李糖脱去,得到不具有鼠李糖苷结构的类黄酮和环糊精的包合物。
酶法可以在水等溶剂中静置、或搅拌的同时进行,为了防止反应中的氧化、或褐变,可以将反应体系的顶部空间的空气用氮气等不活泼气体置换,此外也可以将抗坏血酸等抗氧化剂添加至反应体系中。酶反应可以通过利用对反应液加热而使酶失活的方法等公知的方法来结束。酶反应结束后,过滤,通过精制而去除鼠李糖等并干燥得到的物质形成包合物的干燥物。
应予说明,本发明中,将脱去步骤后的制备液过滤得到的液体,此外其后通过喷雾干燥器、冷冻干燥等而粉末化从而制作的含有鼠李糖的组合物称为“含类黄酮包合物的组合物”,将鼠李糖通过透析、树脂等去除了的液体、或者干燥物记作“类黄酮包合物”。
酶法中,作为成为原料的具有鼠李糖苷结构的类黄酮,可以举出选自具有鼠李糖苷结构的黄酮类、黄酮醇类、黄烷酮类、黄烷醇类和异类黄酮中的物质。例如,可以举出芦丁、橙皮苷、柚皮苷、香叶木苷、圣草次苷、杨梅苷、新橙皮苷、木犀草素-7-芸香糖苷、花翠素-3-芸香糖苷、矢车菊素-3-芸香糖苷、异鼠李素-3-芸香糖苷、山柰酚-3-芸香糖苷、金合欢素-7-芸香糖苷和它们的衍生物等,含有这些类黄酮的黑加仑提取物、银杏叶提取物、柑橘类提取物等植物提取物也可用作原料。此外,作为衍生物,可以举出乙酰基化物、丙二酰基化物、甲基化物等。
酶法中,存在的环糊精的量没有特别限定,在反应体系中,优选为0.01~60质量%、更优选为1~50质量%、进一步优选为3~40质量%。使用2种以上的环糊精的情况的量是指其总计量。
酶法中,具有鼠李糖苷结构的类黄酮与存在的环糊精的摩尔比(存在的环糊精/类黄酮)从效率性、经济性、对味道的影响的观点出发,优选为0.01以上、更优选为0.9以上、进一步优选为1.0以上,从经济性的观点出发,优选为10.0以下、更优选为6.0以下、进一步优选为4.0以下、进一步优选为3.0以下。
酶法中,具有鼠李糖苷酶活性的酶不限定其起源,可以使用动物来源、植物来源、微生物来源等所有来源的酶。进一步,可以为基因重组酶。此外,该酶的形态没有特别限定。作为具有鼠李糖苷酶活性的酶的具体例,可以举出橙皮苷酶、柚苷酶、β-葡萄糖苷酶、果胶酶等。具有鼠李糖苷酶活性的酶的使用量根据所使用的酶的种类、反应条件、成为原料的具有鼠李糖苷结构的类黄酮的种类等而不同,例如在橙皮苷酶、柚苷酶、β-葡萄糖苷酶的情况下,相对于具有鼠李糖苷结构的类黄酮1g,优选为0.01~1000U。反应条件可根据所使用的酶的特性选择反应温度、反应液的pH,优选设为pH3~7,更优选设为pH3.5~6.5。此外,还可在碱区域中溶解具有鼠李糖苷结构的类黄酮类后,在pH7以下进行酶反应。作为反应体系中使用的溶剂,可以使用水介质。本说明书中水介质是指水、或有机溶剂的水溶液。作为水,可以例示出自来水、蒸馏水、离子交换水、纯化水。作为有机溶剂,只要与水均匀混合则没有特别限定。作为有机溶剂,从能够应用于食品等的观点出发,优选乙醇。此外,反应温度优选为10~80℃、更优选为40~75℃。此外,反应时间根据酶的种类等而不同,可以设为例如1~100小时,优选为2~24小时。作为纯化方法,没有特别限制,可以通过树脂处理步骤(吸附法、离子交换法等)、膜处理步骤(超滤膜处理法、反渗透膜处理法、Zeta电位膜处理法等)、和电透析法、盐析、酸析、重结晶、溶剂分级法等纯化。
通过酶法而生成的包合物的转换率优选为10~100%、更优选为40~100%、进一步优选为70~100%、进一步优选为90~100%。转换率(%)是指从具有鼠李糖苷结构的类黄酮向不具有鼠李糖苷结构的类黄酮的转化率,可通过HPLC分析算出(不具有鼠李糖苷结构的类黄酮的峰面积×100/(具有鼠李糖苷结构的类黄酮的峰面积+不具有鼠李糖苷结构的类黄酮的峰面积)。
应予说明,在未纯化的情况下,以除了所生成的包合物之外还包含作为原料的具有鼠李糖苷结构的类黄酮(例如芦丁、橙皮苷、柚皮苷等)、有时原料中含有的类黄酮(例如槲皮素、山柰酚-3-芸香糖苷、山柰酚-3-葡萄糖苷、橙皮素、柚皮素等)、脱去的鼠李糖等的组合物形式得到。此外,作为本发明的组合物的制备中添加包合物的一个方式,还可添加包含这些鼠李糖等和包合物的组合物。在该情况中,本发明的组合物中的包合物中的类黄酮与鼠李糖的摩尔比(鼠李糖/类黄酮)优选为0.1~10.0、更优选为0.8~1.2。
实施例
以下,通过实施例具体说明本发明,但本发明不因这些实施例而受到任何限定。应予说明,在没有特别记载的情况下,“%”是指“质量%”。
<溶解度>
在加入水50ml的100ml容量的烧杯中,将制备的干燥物在50℃下在搅拌的同时添加直至无法完全溶解而析出。室温(25℃)静置后,将上清液1ml进行过滤器过滤,通过HPLC算出异槲皮苷浓度、橙皮素-7-葡萄糖苷浓度、柚皮素-7-葡萄糖苷浓度,记作溶解度。
制备例1:异槲皮苷
将芦丁(アルプス药品工业株式会社制)100g添加至1000L水溶液中,调整至70℃、pH4.5。其后,在搅拌的同时,添加柚苷酶(天野エンザイム(株)5000u/g)0.3g,在24小时酶反应后,回收沉淀物,重结晶·干燥,由此得到含量96%以上的异槲皮苷72g。使用试剂异槲皮苷(Wako),确认含量和HPLC相同。
制备例2:橙皮素-7-葡萄糖苷
将橙皮苷(浜理药品工业株式会社制)70g添加至1000L水溶液中,调整至70℃、pH4.5。其后,在搅拌的同时,添加柚苷酶(天野エンザイム(株)5000u/g)0.6g,在24小时酶反应后,回收沉淀物,重结晶·干燥,由此得到含量96%以上的橙皮素-7-葡萄糖苷42g。使用试剂橙皮素-7-葡萄糖苷(Chem Faces),确认含量和HPLC相同。
制备例3:柚皮素-7-葡萄糖苷
将柚皮苷(SIGMA公司制)20g添加至1L水溶液中,调整至70℃、pH4.5。其后,在搅拌的同时,添加柚苷酶(天野エンザイム(株)5000u/g)0.1g,在24小时酶反应后,回收沉淀物,重结晶·干燥,由此得到含量96%以上的柚皮素-7-葡萄糖苷12.6g。使用试剂柚皮素-7-葡萄糖苷(Wako),确认含量和HPLC相同。
制备例4:异槲皮苷-γ-环糊精包合物
(酶法)
在1000m1容量的烧杯中,添加芦丁80g和γ-环糊精(パールエース公司制、デキシーパールγ-100)170g,添加水制成1000g,调整至70℃、pH4.5。其后,在搅拌的同时,添加柚苷酶(天野エンザイム(株)5000u/g)0.16g,反应24小时。通过HPLC分析确认96%以上的转换率(%)=((异槲皮苷的峰面积)×100/(芦丁的峰面积+异槲皮苷的峰面积))后,通过过滤、透析而去除鼠李糖等后,通过喷雾干燥,得到异槲皮苷-γ-环糊精的包合物的干燥物(γ-环糊精与异槲皮苷的摩尔比(γ-环糊精/异槲皮苷)为1.0)207g(异槲皮苷含量26%)。水中的溶解度为9.6%。溶解度在室温25℃下对在蒸馏水中溶解的浓度通过HPLC分析异槲皮苷浓度。应予说明,异槲皮苷和γ-环糊精为包合状态通过差示扫描量热计(DSC)、核磁共振(NMR)、和傅里叶变换红外分光光度计(FT-IR)而确认。
制备例5:异槲皮苷-γ-环糊精包合物
(溶解法)
将异槲皮苷4g和γ-环糊精(パールエース公司制)以1:5的mol比混合(总计质量60g),向其中添加水,制成1000ml,升温至约85℃,搅拌1小时,由此溶解固体成分。其后,恢复至室温,进行滤纸过滤后,冷冻干燥,制备粉末状的异槲皮苷-γ-环糊精包合物54g。水中的异槲皮苷的溶解度为1.2%,与酶法的9.6%相比,溶解度低。应予说明,将异槲皮苷4g与γ-环糊精(パールエース公司制)的mol比替代1:5而设为1:1~4的情况下,形成悬浊状态,不溶解。
制备例6:橙皮素-7-葡萄糖苷-β-环糊精包合物
(酶法)
在1000m1容量的烧杯中,添加橙皮苷30g和β-环糊精(パールエース公司制、デキシーパールβ-100)84g,添加水制成1000g,调整至70℃、pH4.5。其后,在搅拌的同时,添加柚苷酶(天野エンザイム(株)5000u/g)0.16g,反应24小时后,通过HPLC确认96%以上的转换率(%)=((橙皮素-7-葡萄糖苷的峰面积)×100/(橙皮苷的峰面积+橙皮素-7-葡萄糖苷的峰面积))。其后,通过过滤、透析而去除鼠李糖等,通过喷雾干燥,得到橙皮素-7-葡萄糖苷与β-环糊精的包合物(β-环糊精-与橙皮素-7-葡萄糖苷的摩尔比(β-环糊精/橙皮素-7-葡萄糖苷)为1.5)93g(橙皮素-7-葡萄糖苷含量21%)。水中的溶解度为3.9%。关于溶解度,在室温25℃下对在蒸馏水中溶解的浓度通过HPLC分析橙皮素-7-葡萄糖苷浓度。应予说明,橙皮素-7-葡萄糖苷和β-环糊精为包合状态通过差示扫描量热计(DSC)、核磁共振(NMR)、和傅里叶变换红外分光光度计(FT-IR)而确认。
制备例7:柚皮素-7-葡萄糖苷-β-环糊精包合物
(酶法)
在1000m1容量的烧杯中,添加柚皮苷60g和β-环糊精117g,添加水制成1000g,调整至70℃、pH4.5。其后,在搅拌的同时,添加柚苷酶(天野エンザイム(株)5000u/g)0.3g,反应24小时,通过HPLC确认96%以上的转换率((柚皮素-7-葡萄糖苷的峰面积)×100/(柚皮苷的峰面积+柚皮素-7-葡萄糖苷的峰面积))。其后,通过过滤、透析而去除鼠李糖后,通过喷雾干燥,得到柚皮素-7-葡萄糖苷与β-环糊精的包合物(摩尔比(β-环糊精/柚皮素-7-葡萄糖苷)为1.0)142g(柚皮素-7-葡萄糖苷含量27%)。水中的溶解度为9.2%。溶解度在室温25℃下对在蒸馏水中溶解的浓度通过HPLC分析柚皮素-7-葡萄糖苷浓度。应予说明,柚皮素-7-葡萄糖苷和β-环糊精为包合状态通过差示扫描量热计(DSC)、核磁共振(NMR)、和傅里叶变换红外分光光度计(FT-IR)而确认。
制备例8:包含异槲皮苷-γ-环糊精包合物与鼠李糖的组合物(含IQC包合物的组合物)
制备例4中,酶反应后,不透析,通过喷雾干燥,得到包含异槲皮苷-γ-环糊精包合物与鼠李糖的组合物(220g、异槲皮苷含量24%)。该组合物中的异槲皮苷与鼠李糖的摩尔比(鼠李糖/异槲皮苷)为1.0。
制备例9:包含橙皮素-7-葡萄糖苷-β-环糊精包合物与鼠李糖的组合物(含HPT-7G包合物的组合物)
制备例6中,酶反应后,不透析,通过喷雾干燥,得到包含橙皮素-7-葡萄糖苷-β-环糊精包合物与鼠李糖的组合物(101g、橙皮素-7-葡萄糖苷含量20%)。该组合物中的橙皮素-7-葡萄糖苷与鼠李糖的摩尔比(鼠李糖/橙皮素-7-葡萄糖苷)为1.0。
制备例10:包含柚皮素-7-葡萄糖苷-β-环糊精包合物与鼠李糖的组合物(含NGN-7G包合物的组合物)
制备例7中,酶反应后,不透析,通过喷雾干燥,得到包含柚皮素-7-葡萄糖苷-β-环糊精包合物与鼠李糖的组合物(155g、柚皮素-7-葡萄糖苷含量25%)。该组合物中的柚皮素-7-葡萄糖苷与鼠李糖的摩尔比(鼠李糖/柚皮素-7-葡萄糖苷)为1.0。
制备例11:异槲皮苷-γ-环糊精包合物
(溶解法)
将异槲皮苷4g和γ-环糊精11.5g(パールエース公司制)以摩尔比(γ-环糊精/异槲皮苷)l混合,向其中添加水,制成100L(pH4、用柠檬酸调整),升温至约85℃,搅拌1小时,由此溶解固体成分。其后,恢复至室温,过滤浓缩后,冷冻干燥,制备粉末状的异槲皮苷-γ-环糊精包合物10.5g(摩尔比(γ―环糊精/异槲皮苷)l、制备例11)。
但是,将异槲皮苷30g和γ-环糊精84g以摩尔比1混合,向其中添加水,制成1L(pH4、用柠檬酸调整),升温至约85℃,即使搅拌1小时,也为悬浊状态。其后,恢复至室温,过滤浓缩后,冷冻干燥的异槲皮苷-γ-环糊精包合物75g为摩尔比(γ-环糊精/异槲皮苷)8.4。
异槲皮苷和γ-环糊精为包合状态、和摩尔比通过差示扫描量热计(DSC)、核磁共振(NMR)、傅里叶变换红外分光光度计(FT-IR)和HPLC糖分析法确认。
应予说明,为了比较,通过酶法制作的类黄酮包合物通过在酶反应时变更环糊精的含量,使类黄酮与环糊精的摩尔比(环糊精/类黄酮)为1.5、1.8、2.0、3.0等进行了制作。
(类黄酮浓度分析方法、类黄酮含量·换算值算出方法)
对比通过HPLC(SHIMADZU)分析(HPLC条件: 柱:CAPCELL PAK C18 SIZE 4.6mm×250mm(SHISEIDO)、洗脱液:20~40%(v/v)乙腈/0.1%磷酸水溶液、流速:0.4ml/min、柱温度:70℃、波长:351nm(异槲皮苷)、280nm(橙皮素-7-葡萄糖苷、柚皮素-7-葡萄糖苷))得到的峰面积与各试剂(试剂异槲皮苷(Wako)、试剂橙皮素-7-葡萄糖苷(Chem Faces)、试剂柚皮素-7-葡萄糖苷(Wako)的标准曲线,算出类黄酮浓度,算出实施例的饮料等中的类黄酮含量。应予说明,针对酶处理异槲皮苷、酶处理橙皮苷、分散橙皮素,将类黄酮部分的含量作为换算值表示。具体而言,如以下那样算出。
酶处理异槲皮苷:通过由HPLC分析(与异槲皮苷浓度分析相同条件)得到的各峰面积的总和与试剂异槲皮苷的标准曲线的峰面积比较,算出异槲皮苷换算值。
酶处理橙皮苷:通过由PLC分析(与橙皮素-7-葡萄糖苷浓度分析相同条件)得到的各峰面积的总和与试剂橙皮素-7-葡萄糖苷的标准曲线的峰面积比较,算出橙皮素-7-葡萄糖苷换算值。
分散橙皮素:通过由HPLC分析(与橙皮素-7-葡萄糖苷浓度分析相同条件)得到的面积与试剂橙皮素-7-葡萄糖苷的标准曲线的峰面积比较,算出橙皮素-7-葡萄糖苷换算值。
(鼠李糖与类黄酮的摩尔比(鼠李糖/类黄酮)的分析法)
使用包含类黄酮包合物与鼠李糖的组合物,测定鼠李糖含量(HPLC糖分析法(下述)、用鼠李糖(Wako)制作标准曲线)后,算出鼠李糖的摩尔浓度,由包合物的类黄酮的摩尔浓度(算出),算出鼠李糖与类黄酮的摩尔比(鼠李糖/类黄酮)。
(HPLC糖分析法)
由HPLC(SHIMADZU)分析(HPLC条件:柱:Inertsil NH2(4.6×150mm(ジーエルサイエンス)、洗脱液:65%乙腈/水(v/v)、检测:差示折射率计RID-10A(SHIMADZU)、流速:1ml/min、柱温度:40℃),制作β-环糊精(Wako)、γ-环糊精(Wako)的标准曲线后,算出样品的环糊精的摩尔浓度,此外通过异槲皮苷、橙皮素-7-葡萄糖苷和柚皮素-7-葡萄糖苷的摩尔浓度,算出环糊精/异槲皮苷、环糊精/橙皮素-7-葡萄糖苷、环糊精/柚皮素-7-葡萄糖苷的摩尔比。应予说明,反应结束后过滤液的摩尔比在冷冻干燥物中也相同。
1.柠檬饮料:类黄酮的苦味的改善
实施例1
制备含有以异槲皮苷含量计达到0.007质量%的量的制备例4的异槲皮苷-γ-环糊精包合物、和三氯半乳蔗糖0.005质量%的柠檬饮料(pH3、柠檬酸0.08质量%、柠檬香精(长谷川香料(株)制)0.1质量%、用柠檬酸三钠调整pH)。
实施例2~6、比较例1~25、参考例1~2
将包合物的种类和三氯半乳蔗糖的添加量设为表1所示的成分、添加量,除此之外,与实施例1同样制备。
表1中记载的成分的详情示于以下。
三氯半乳蔗糖:(Tate&Lyle(株)制)
(1)IQC-γCD包合物(酶法):制备例4的异槲皮苷-γ-环糊精包合物
(2)IQC-γCD包合物(溶解法):制备例5的异槲皮苷-γ-环糊精包合物
(3)IQC+γCD:将制备例1的异槲皮苷0.007质量%和γ-环糊精(パールエース公司制)0.02质量%在饮料中分别添加混合
(4)酶处理IQC:酶处理异槲皮苷(三荣源エフ·エフ·アイ(株)サンメリンAO-3000、异槲皮苷换算值7.2质量%)、
(5)IQC:制备例1的异槲皮苷
(6)HPT-7G-βCD包合物(酶法):制备例6的橙皮素-7-葡萄糖苷-β-环糊精包合物
(7)酶处理HSP:糖转移橙皮苷((株)林原、橙皮苷S、橙皮苷换算值 82.7质量%)
(8)分散HPT:分散橙皮素(江崎グリコ(株)、ペレチン-D、橙皮素换算值85质量%)
(9)HPT-7G:制备例2的橙皮素-7-葡萄糖苷
(10)NGN-7G-βCD包合物(酶法):制备例7的柚皮素-7-葡萄糖苷-β-环糊精包合物
(11)NGN-7G:制备例3的柚皮素-7-葡萄糖苷
<苦味评价>
关于实施例1~6、比较例1~25、参考例1~2的因类黄酮而导致的苦味的官能评价,通过7名专门人员按照下述的基准进行5级评价,算出总计点的平均点。结果示于表1。因类黄酮而导致的苦味对苦味、涩味、和后味的不愉快味道(后味中残留的苦涩味等)进行综合官能评价,按照同种成分进行比较。即,在包含表1的(1)~(5)的饮料间的评价中,以仅含有异槲皮苷的比较例5的评价记作1,在包含(6)~(9)的饮料间的评价中,以仅含有橙皮素-7-葡萄糖苷的比较例9的评价记作1,在包含(10)~(11)的饮料间的评价中,以仅含有柚皮素-7-葡萄糖苷的比较例11的评价记作1,各自进行相对评价。此外,将各自仅添加0.0007%(饮料中的仅类黄酮的添加量的1/10量)的异槲皮苷、橙皮素-7-葡萄糖苷、柚皮素-7-葡萄糖苷的柠檬饮料记作评价5。
(评价基准)
1:同种成分中苦味最强。
2:苦味略强。与评价1相比弱。
3:苦味与评价1相比一定程度改善
4:苦味与评价1相比改善。
5:苦味与评价1相比大幅改善。
如表1所示,包含(1)~(5)的饮料间的值中,仅含有异槲皮苷的饮料(比较例5)的评价为1.0且最苦,含有异槲皮苷-环糊精包合物(酶法)和三氯半乳蔗糖0.014%的饮料(实施例4)的评价达到4.2,苦味最为改善。包含(6)~(9)的饮料间的评价中,仅含有橙皮素-7-葡萄糖苷的饮料(比较例9)的评价为1.0最苦,含有橙皮素-7-葡萄糖苷-环糊精包合物(酶法)和三氯半乳蔗糖0.014%的饮料(实施例5)的评价达到4.1,苦味最为改善。此外,包含(10)~(11)的饮料间的评价中,仅含有柚皮素-7-葡萄糖苷的饮料(比较例11)的评价为1.0最苦,含有柚皮素-7-葡萄糖苷-环糊精包合物(酶法)和三氯半乳蔗糖0.014%的饮料(实施例6)的评价达到4.1,苦味最为改善。此外,通过溶解法制作的异槲皮苷-γ-环糊精包合物尽管示出苦味的减少效果,但与酶法相比官能评价低。应予说明,(2)中示出的基于溶解法的官能评价在制备例11中制作的异槲皮苷-环糊精包合物(溶解法)中,也为相同评价。
应予说明,替代三氯半乳蔗糖0.005质量%、0.014质量%,阿斯巴甜(味之素(株)制、パルスイート)0.013质量%、0.04质量%、安赛蜜(ニュートリノヴァ公司制、サネット)0.02质量%、0.05质量%、甜叶菊提取物(东洋精糖(株)制、ステビロース90)0.02质量%、0.06质量%、赤藓糖醇(物产フードサイエンス(株)制、赤藓糖醇F)3质量%、8质量%、山梨糖醇(物产フードサイエンス(株)制、山梨糖醇SP)3质量%、9质量%、木糖醇(物产フードサイエンス(株)制、木糖醇)2质量%、6质量%、抗坏血酸(扶桑化学工业(株)制)0.03质量%、0.1质量%中,也为相同评价。
此外,以类黄酮包合物(酶法)的环糊精与类黄酮的摩尔比(环糊精/类黄酮)为1.0~3.0进行了相同的苦味的官能评价。但是,柠檬风味在摩尔比为1.0~1.8的情况下也为相同官能评价,但如果大于2.0,则柠檬风味变弱。
此外,即使使用制备例8~10中得到的组合物替代实施例1~6中的类黄酮包合物,官能评价也几乎相同。此外,饮料中的类黄酮含量或换算值即使为0.02质量%,也示出几乎相同的结果。
2.酸性饮料:因类黄酮的长期保存而导致的色调变化的改善
实施例11
制备含有以异槲皮苷含量计达到0.007质量%的量的制备例4的异槲皮苷-γ-环糊精包合物、和三氯半乳蔗糖0.005质量%的酸性饮料(pH3、柠檬酸0.08%、用柠檬酸三钠调整pH)。
实施例12~16、比较例31~55、参考例11~12
将包合物的种类和三氯半乳蔗糖的添加量设为表2所示的成分、添加量,除此之外,与实施例11同样制备。
表2中记载的成分的详情除了以下所示的之外与表1相同。
(12)HPT-7G+βCD:将制备例2的橙皮素-7-葡萄糖苷0.007质量%和β-环糊精(パールエース公司制)0.02质量%在饮料中分别添加混合
<色调评价>
实施例11~16、比较例31~55、参考例11~12的刚制造后和37℃下保存3个月后的色调使用分光光度计(Cary60 UV-VIS、Software:CaryWinUV/Color、AgilentTechnologies),将试样放入光路长10mm的石英小室,测定Lab表色系的L值、a值和b值。由刚制造后的酸性饮料的L值、a值、b值与37℃下保存3个月后的酸性饮料的L值、a值、b值,通过下述式求出ΔE值,示于表2,比较同种成分(表2的(1)~(5)、(6)~(9)、和(10)~(11))。
如表2所示,通过添加异槲皮苷-γ-环糊精包合物、橙皮素-7-葡萄糖苷-β-环糊精包合物、和柚皮素-7-葡萄糖苷-β-环糊精包合物和三氯半乳蔗糖,改善了酸性饮料中的色调变化。如表2所示,包含(1)~(5)的饮料间的值中,仅含有异槲皮苷的饮料(比较例34)的值为2.12且最高,含有异槲皮苷-环糊精包合物(酶法)和三氯半乳蔗糖0.014%的饮料(实施例14)的值达到0.65,色调变化最低。包含(6)~(9)的饮料间的值中,仅含有橙皮素-7-葡萄糖苷的饮料(比较例39)的值为1.95且最高,含有橙皮素-7-葡萄糖苷-环糊精包合物(酶法)和三氯半乳蔗糖0.014%的饮料(实施例15)的值达到0.55,色调变化最低。此外,包含(10)~(11)的饮料间的值中,仅含有柚皮素-7-葡萄糖苷的饮料(比较例41)的值为1.78且最高,含有柚皮素-7-葡萄糖苷-环糊精包合物(酶法)和三氯半乳蔗糖0.014%的饮料(实施例16)的值达到0.52,色调变化最低。此外,通过溶解法制作的异槲皮苷-γ-环糊精包合物尽管示出色调改善效果,但与酶法相比,其程度弱。应予说明,(2)中示出的基于溶解法的色调评价在制备例11中制作的异槲皮苷-环糊精包合物(溶解法)中,也为相同评价。
应予说明,替代三氯半乳蔗糖0.005质量%、0.014质量%,在阿斯巴甜(味之素(株)制、パルスイート)0.013质量%、0.04质量%、安赛蜜(ニュートリノヴァ公司制、サネット)0.02质量%、0.05质量%、甜叶菊提取物(东洋精糖(株)制、ステビロース90)2质量%、6质量%、赤藓糖醇(物产フードサイエンス(株)制、赤藓糖醇F)3质量%、8质量%、山梨糖醇(物产フードサイエンス(株)制、山梨糖醇SP)3质量%、9质量%、木糖醇(物产フードサイエンス(株)制、木糖醇)2质量%、6质量%、抗坏血酸(扶桑化学工业(株)制)0.03质量%、0.1质量%的情况中,也为相同评价。此外,使类黄酮(异槲皮苷、橙皮素-7-葡萄糖苷、柚皮素-7-葡萄糖苷)包合物(酶法)的环糊精与类黄酮的摩尔比(环糊精/类黄酮)变化为1.0~3.0,也为几乎相同的评价。应予说明,含有鼠李糖的含类黄酮包合物的组合物中,进行官能评价的结果是,评价变高0.1-0.2。
3.片剂:类黄酮的苦味和色调变化的改善
实施例21
使用油压加压机(理研精机株式会社制)、以及与其对应的臼和杵,将以异槲皮苷含量计达到5质量%的量的制备例4的异槲皮苷-γ-环糊精包合物、三氯半乳蔗糖0.04质量%、微粒二氧化硅0.5质量%、柠檬酸2.5质量%、结晶纤维素(余量)的混合物各自在100kg/cm2的压力下压缩成型,制作直径9mm、重量300mg的片剂。
实施例22~26、比较例61~87
将包合物的种类和三氯半乳蔗糖的添加量设为表3、4所示的成分、添加量,除此之外,与实施例21同样制备。
表3、4中记载的成分的详情除了各成分的质量%、以下所示物质之外,与表1、2相同。
(13)NGN-7G+βCD:将制备例3的柚皮素-7-葡萄糖苷5质量%和β-环糊精(パールエース公司制)13质量%在片剂中分别添加混合
<苦味评价>
关于实施例21~26、比较例61~84的苦味的官能评价通过5名专门人员进行评价,算出总计点的平均点。结果示于表3。与柠檬饮料同样地在含有同种成分的片剂间进行比较,针对评价基准,也设为与柠檬饮料相同的基准。应予说明,片剂将2个片剂咬碎,进行吞咽时的苦味评价。
测定实施例21~26、比较例61~64、66~72、74~79、81~87的刚制造后和37℃下保存3个月后的Lab值,算出的ΔE值示于表4。即,对于Lab值,将片剂用乳钵粉碎而得到的物质以达到0.01质量%的类黄酮含量或换算值的方式,将片剂用酸性液(pH3.1 柠檬酸0.08%、用柠檬酸三钠调整)溶解过滤后,测定Lab值。测定方法、ΔE值的算出方法与酸性饮料相同。
如表3、4所示,通过添加异槲皮苷-γ-环糊精包合物、橙皮素-7-葡萄糖苷-β-环糊精包合物、和柚皮素-7-葡萄糖苷-β-环糊精包合物和三氯半乳蔗糖,改善了苦味和色调变化。
应予说明、替代三氯半乳蔗糖0.04质量%、0.2质量%,阿斯巴甜(味之素(株)制、パルスイート)0.1质量%、0.5质量%、安赛蜜(ニュートリノヴァ公司制、サネット)0.14质量%、0.7质量%、甜叶菊提取物(东洋精糖(株)制、ステビロース90)0.08质量%、0.2质量%、赤藓糖醇(物产フードサイエンス(株)制、赤藓糖醇F)14质量%、70质量%、山梨糖醇(物产フードサイエンス(株)制、山梨糖醇SP)14质量%、70质量%、木糖醇(物产フードサイエンス(株)制、木糖醇)14质量%、70质量%、抗坏血酸(扶桑化学工业(株)制)0.2质量%、1质量%中,也为相同评价。此外,使类黄酮(异槲皮苷、橙皮素-7-葡萄糖苷、柚皮素-7-葡萄糖苷)包合物(酶法)的环糊精与类黄酮的摩尔比(环糊精/类黄酮)变化为1.0~3.0,也为几乎相同的评价。
4.红茶饮料:苦味的改善
实施例31~33、比较例91~96
将表5所述的原料搅拌混合后,进行总量校正,温度达到93℃添加香精,向350mL的PET瓶中进行热包装填充,制备红茶饮料(pH5)。
表5中记载的成分的详情除了以下所示的之外与表1~4相同。
(14)含IQC包合物的组合物:包含制备例8的异槲皮苷-γ-环糊精包合物与鼠李糖的组合物
(15)含HPT-7G包合物的组合物:包含制备例9的橙皮素-7-葡萄糖苷-β-环糊精包合物与鼠李糖的组合物
(16)含NGN-7G包合物的组合物:包含制备例10的柚皮素-7-葡萄糖苷-β-环糊精包合物与鼠李糖的组合物
红茶提取液:红茶浓缩品((株)ジーエスフード制)
碳酸氢钠:(太洋制药(株)制)
甜叶菊提取物:(东洋精糖(株)制、ステビロース90)
L-抗坏血酸:(扶桑化学工业(株)制)
木糖醇:(物产フードサイエンス(株)制)
红茶香精:(小川香料(株)制)
<苦味评价>
关于实施例31~33、比较例91~96的苦味的官能评价通过7名专门人员按照下述的基准进行3级评价,算出总计点的平均点。结果示于表5。苦味对苦味、涩味、和后味的不愉快味道进行综合官能评价,按照同种成分(表5(实验例31、比较例91、比较例92)(实验例32、比较例93、比较例94、比较例95)(比较例33、比较例96))进行比较。仅含有异槲皮苷、橙皮素-7-葡萄糖苷、柚皮素-7-葡萄糖苷的比较例92、95、96的红茶饮料的苦味在同种成分比较中最强,因此将其评价记作1,仅异槲皮苷、橙皮素-7-葡萄糖苷、柚皮素-7-葡萄糖苷的添加量设为1/10的物质的评价记作3。
(评价基准)
1:同种成分中苦味最强。
2:苦味与评价1相比改善。
3:苦味与评价1相比大幅改善。
5.咖啡饮料:苦味的改善
实施例41~43、比较例101~106
将表6所述的原料搅拌混合后,进行总量校正,温度达到70℃用均化器均质化后,将200mL的罐装进行121℃15分钟蒸煮灭菌,制备咖啡饮料。以与红茶饮料相同的方式进行苦味评价。结果示于表6。
表6中记载的成分的详情除了以下所示的之外与表1~5相同。
咖啡提取液:((株)ジーエスフード制)
牛奶:(明治乳业(株)制)
脱脂奶粉:(よつ叶乳业(株)制)
砂糖:(三井精糖(株)制)
乳化剂:(太阳化学(株)制)
碳酸氢钠:(太洋制药(株)制)
咖啡香精:(小川香料(株)制)
三氯半乳蔗糖:(Tate&Lyle(株)制)
赤藓糖醇:(物产フードサイエンス(株)制)。
6.片剂:苦味的改善
实施例51~53、比较例111~116
将表7所述的原料进行粉体混合,用压片机压片(1粒300mg),制备片剂。以与红茶饮料相同的方式进行苦味评价。结果示于表7。
表7中记载的成分的详情除了以下所示的之外与表1~6相同。
蔗糖脂肪酸酯:(太阳化学(株))
柠檬酸:(大洋制药(株)制)
粉末色素:(ヤエガキ发酵技研(株)制)
阿斯巴甜:(味之素(株)制、パルスイート)
安赛蜜:(ニュートリノヴァ公司制、サネット)
结晶纤维素:(旭化成(株)制)。
7.颗粒:苦味的改善
实施例61~63、比较例121~126
将含水结晶葡萄糖、三氯半乳蔗糖、和表8所述的类黄酮进行粉体混合后,用混合搅拌机搅拌混合,同时将表8记载的剩余原料混合。混合后,用热风干燥机进行60℃·2小时干燥,制备颗粒。以与红茶饮料相同的方式进行苦味评价。结果示于表8。
表8中记载的成分的详情除了以下所示的之外与表1~7相同。
绿茶粉末:(伊藤园(株)制)
绿茶香精:(小川香料(株)制)
三氯半乳蔗糖:(Tate&Lyle(株)制)
含水结晶葡萄糖:(サンエイ糖化(株)制)。
8.硬酸奶:苦味的改善
实施例71~73、比较例131~136
将除了发酵剂和酸奶香精之外的表9所述的原料混合,进行90℃·10分钟搅拌溶解。90℃·10分钟灭菌后,冷却至40℃,将剩余原料添加混合。填充至100ml塑料杯中,在40℃的恒温槽中发酵至pH4.5冷却,制备硬酸奶。以与红茶饮料相同的方式进行苦味评价。结果示于表9。
表9中记载的成分的详情除了以下所示的之外与表1~8相同。
牛奶:(明治乳业(株)制)
脱脂奶粉:(よつ叶(株)制)
砂糖:(三井精糖(株)制)
山梨糖醇:(物产フードサイエンス(株)制、山梨糖醇SP)
胶凝剂:(新田明胶(株))
酸奶香精:(小川香料(株)制)
发酵剂:(フジッコ(株)制)。
如表5~9的实施例31~73所示,可知作为添加类黄酮包合物的方式,即使添加包含类黄酮包合物与鼠李糖的组合物,也显著改善了苦味。应予说明,表中虽未示出,但以去除了鼠李糖的类黄酮(异槲皮苷、橙皮素-7-葡萄糖苷、柚皮素-7-葡萄糖苷)包合物进行官能评价的结果是,评价变低0.1-0.2。
9.酸性溶液和市售溶液:不愉快味道的改善
实施例81~168、比较例141~318、参考例21~48
将含量和换算量达到0.003质量%的量的异槲皮苷、橙皮素-7-葡萄糖苷、柚皮素-7-葡萄糖苷添加至含有表10~13所示的各原材料的试验溶液(pH3、柠檬酸0.08质量%、用柠檬酸三钠进行pH调整)、和表14~17所示的市售饮料中。
表10~17中记载的成分的详情除了以下所示的之外与表1~9相同。
(23)IQC+γCD:将制备例1的异槲皮苷0.003质量%和γ-环糊精(パールエース公司制)0.009质量%在饮料中分别添加混合
安赛蜜:(丸善药品产业(株)制)
鞣酸:(富士化学工业(株)制)
咖啡因:(ナカライテスク(株)制)
绿原酸:(ナカライテスク(株)制)
儿茶素:(太阳化学(株)制)
茶提取物:(三菱ケミカルフーズ(株)制)
市售饮料A:Coca-cola zero(日本Coca-cola (株)制)、(含有三氯半乳蔗糖、安赛蜜)
市售饮料B:ヘルシア COFEE 无糖黑(花王(株)制)、(含有绿原酸、咖啡因)
市售饮料C:ワンダ 极 完熟深煎りブラック(アサヒ饮料(株)制)、(含有咖啡因)
市售饮料D:CC柠檬(サントリー食品インターナショナル(株)制)、(含有维生素C)
市售饮料E:午后的红茶おいしい无糖(キリンビバレッジ(株)制)、(含有鞣酸)
市售饮料F:デカビタCゼロ(サントリーフーズ(株)制)、(含有赤藓糖醇)
市售饮料G:チューハイテイスト柠檬((株)日本サンガリア ベバレッジカンパニー制)、(含有赤藓糖醇)
市售饮料H:ヘルシア绿茶(花王(株)制)、(含有儿茶素)。
<不愉快味道改善效果>
针对实施例81~168、比较例141~318、参考例21~48的关于不愉快味道的官能评价,通过10名专门人员,对甜味的留存、甜味、辛辣味、涩味、酸味的不愉快味道的改善效果,对各原材料溶液和饮料,按照同种成分((1)、(2)、(23)、(4)、(5)之间、(6)、(8)、(9)之间、(10)、(11)之间)比较,记载评价为改善了不愉快味道的人数。结果示于表10~17。应予说明,作为不愉快味道而举出的“甜味的留存”是指甜味持续而导致的后味的中断性差。此外,作为不愉快味道而举出的“甜味”是指因与砂糖不同的甜味质而导致的异常感。因此,后味的中断性提高的评价为改善了“甜味的留存”,与砂糖的甜味质接近的评价为改善了“甜味”。
如表10~17所示,包含异槲皮苷的饮料间的比较中(1)异槲皮苷-环糊精包合物(酶法),包含橙皮素的饮料间的比较中(6)橙皮素-7-葡萄糖苷包合物(酶法),包含柚皮素的饮料间的比较中(10)柚皮素-7-葡萄糖苷包合物(酶法)最为改善了试验溶液和市售饮料的不愉快味道。此外,替代通过前述(1)、(6)、(10)的酶法得到的类黄酮包合物,使用制备例8~10中得到的组合物也得到相同的结果。
10.酸性饮料和片剂:类黄酮的后味的金属味和酸味的改善
实施例171~194、比较例321~376、参考例51~58
制备含有以异槲皮苷含量计达到0.007质量%的量的制备例4的异槲皮苷-γ-环糊精包合物、和鼠李糖与异槲皮苷的摩尔比(鼠李糖/异槲皮苷)达到表18~21中记载的摩尔比的量的鼠李糖的酸性饮料(pH3、柠檬酸0.08质量%、用柠檬酸三钠进行pH调整)。
实施例201~224、比较例381~436、参考例61~68
通过与实施例21相同的方法,将以异槲皮苷含量计达到2质量%的量的制备例4的异槲皮苷-γ-环糊精包合物、和鼠李糖与异槲皮苷的摩尔比(鼠李糖/异槲皮苷)达到表22~25中记载的摩尔比的量的鼠李糖、微粒二氧化硅0.5质量%、柠檬酸2.5质量%、结晶纤维素(余量)的混合物各自在100kg/cm2的压力下压缩成型,制作直径9mm、300mg的片剂。
表18~25中记载的成分的详情与表1~9相同。
<后味的金属味·酸味评价>
针对实施例171~224、比较例321~436、参考例51~68的关于后味的金属味和/或酸味(与苦味、涩味、和苦涩味完全不同的味道)的官能评价,与前述柠檬饮料的情况同样地,在含有同种成分的酸性饮料间、片剂间比较评价。即,同种成分的比较中类黄酮的后味的金属味和/或酸味最强的记作评价1,各自进行相对评价。此外,相对于评价为1的仅类黄酮的添加量,酸性饮料中将添加0.0007质量%(饮料中仅类黄酮的添加量的1/10量)、片剂中将添加0.2质量%(片剂中仅类黄酮的添加量的1/10量)的记作评价5。通过5名专门人员评价,算出总计点的平均点。结果示于表18~25。应予说明,片剂将2片咬碎,吞咽后,用50ml的水漱口多次,其后进行吞咽唾沫后残留的金属味和/或酸味的官能评价。
(评价基准)
1:同种成分中,后味的金属味和/或酸味最强,平衡非常差。
2:后味的金属味和/或酸味较强,平衡差。
3:后味的金属味和/或酸味变得较弱。
4:后味的金属味和/或酸味变弱。
5:后味的金属味和/或酸味变得非常弱,平衡也非常良好。
如表18~25所示,通过添加利用酶法得到的异槲皮苷-γ-环糊精包合物、橙皮素-7-葡萄糖苷-β环糊精包合物、或柚皮素-7-葡萄糖苷-β-环糊精包合物,改善了类黄酮所具有的后味的金属味和/或酸味。此外,在进一步添加鼠李糖的情况下观察到显著改善,特别地,针对鼠李糖与类黄酮的摩尔比(鼠李糖/类黄酮)为0.8~1.2的,得到令人满意的结果。应予说明,虽未在表中记载,但酸性饮料中的类黄酮的含量或换算量为0.02质量%、片剂中的类黄酮的含量或换算量为5质量%的情况下,也确认了相同的效果。应予说明,(2)中示出的基于溶解法的官能评价在制备例11中制作的异槲皮苷-环糊精包合物(溶解法)中,也为相同评价。此外,使类黄酮(异槲皮苷、橙皮素-7-葡萄糖苷、柚皮素-7-葡萄糖苷)包合物(酶法)的环糊精与类黄酮的摩尔比(环糊精/类黄酮)变化为1.0~3.0,也为几乎相同评价。
11.对皮肤的美容效果
实施例231
使用制备例4的异槲皮苷-γ-环糊精包合物(异槲皮苷包合物)与鼠李糖,通过对于模拟太阳光(Oriel公司制)导致的细胞死亡的生存率,评价皮肤美容效果。
即,将人真皮成纤维细胞(PromoCell公司制)在24孔板中,使用细胞用培养基,以3×104细胞/孔的比率传代培养。接着,细胞在包含以异槲皮苷含量计达到0.007质量%的量的制备例4的异槲皮苷-γ-环糊精包合物、和鼠李糖与异槲皮苷的摩尔比(鼠李糖/异槲皮苷)达到0.1的量的鼠李糖的组合物的存在下,温育24小时后,曝露于模拟太阳光(Oriel公司制、太阳模拟器、Solar dose10KJ/m2),24小时后,分析细胞的生存率。
细胞的生存在中性红(色素)的存在下,在37℃和5%CO2中温育1小时(生存细胞摄取中性红,因此能够与死亡细胞或损伤细胞区分,将它们定量)。接着,通过添加50%乙醇和0.05M NaH2PO4的溶液,由细胞提取色素,将分光光度计540nm下的吸光度与未曝光的细胞比较,记作生存率(%)=(光照射细胞的540nm的分析值×100/光未照射细胞的540nm的分析值),示于表26。
实施例232~250、比较例441~500、参考例71~77
将24小时温育时使用的组合物设为表26~29中记载的成分,除此之外,与实施例231同样地进行评价。
表26~29中记载的成分的详情与表1~9相同。
制备例4的异槲皮苷-γ-环糊精包合物如表26~29所示,在鼠李糖/(异槲皮苷包合物中的异槲皮苷)的摩尔比0.1-10.0的情况下,对紫外线诱导性的人真皮成纤维细胞死亡,与同类的其它成分((2)~(5))相比示出高生存率。此外,在0.8-1.2的摩尔比下,生存率最高。虽未在表中示出,但在所有情况中仅添加相同浓度的鼠李糖的情况下,生存率为约5%,未添加异槲皮苷包合物和鼠李糖的情况下几乎为0%。此外可知,异槲皮苷包合物中的异槲皮苷含有0.02%的情况下,与添加0.007%时相比,生存率提高约5%,使用人表皮角化细胞(タカラバイオ公司制)时,也示出相同的效果,因此鼠李糖/异槲皮苷包合物的组合防护皮肤细胞不受太阳光伤害,且提高再生能力,由此提高生存率,减少皱纹出现,皮肤的光泽等美容效果变高。此外,制备例6的橙皮素-7-葡萄糖苷-β-环糊精包合物、另外制备例7的柚皮素-7-葡萄糖苷-β-环糊精包合物也在同类成分((6)~(9)、(10)-(11))的比较中,是包合物且鼠李糖/(类黄酮包合物中类黄酮)的摩尔比为0.8-1.2的情况下显示最高的生存率。应予说明,(2)中示出的基于溶解法的官能评价在制备例11中制作的异槲皮苷-环糊精包合物(溶解法)中,也为相同评价。此外,使类黄酮(异槲皮苷、橙皮素-7-葡萄糖苷、柚皮素-7-葡萄糖苷)包合物(酶法)的环糊精与类黄酮的摩尔比(环糊精/类黄酮)变化为1.0~3.0,也为几乎相同评价。
类黄酮包合物的配方例
配方例1:橡皮糖
制作含有制备例4的异槲皮苷-γ-环糊精包合物的干燥物的橡皮糖。本品通过添加制备例4的异槲皮苷-γ-环糊精包合物和山梨糖醇,能够适合用作源自异槲皮苷的苦味减少的食品(橡皮糖)。
(成分) (质量%)
制备例4的化合物 0.03
山梨糖醇 60.0
还原糖稀 12.0
阿拉伯胶 5.0
离子交换水 5.0
明胶 5.0
着色剂 0.2
香料 0.8
离子交换水 余量
总量 100.0。
配方例2:口香糖
制作含有制备例6的橙皮素-7-葡萄糖苷-β-环糊精包合物的干燥物的口香糖。本品通过添加制备例6的橙皮素-7-葡萄糖苷-β-环糊精包合物和甜叶菊提取物,能够适合用作源自橙皮素-7-葡萄糖苷的苦味减少的食品(口香糖)。
(成分) (质量%)
制备例6的化合物 0.05
甜叶菊提取物 0.1
口香糖胶基 20.0
碳酸钙 2.0
香料 1.0
乳糖 余量
总量 100.00。
配方例3:清凉饮料
制备清凉饮料,其含有制备例8的含异槲皮苷-γ-环糊精包合物的组合物。本品通过添加制备例8的含有鼠李糖的含异槲皮苷-γ-环糊精包合物的组合物,能够适合用作异槲皮苷的后味的金属味和酸味减少、且三氯半乳蔗糖的甜味的留存减少的食品(清凉饮料)。
(成分) (质量%)
制备例8的组合物 0.03
三氯半乳蔗糖 0.04
柠檬酸 0.2
柠檬酸三钠 0.06
香料 0.2
色素 0.1
水 余量
总量 100.00。
配方例4:果冻(咖啡果冻)
制备咖啡果冻,其含有制备例10的含柚皮素-7-葡萄糖苷-β-环糊精包合物的组合物的干燥物。本品通过添加制备例10的含柚皮素-7-葡萄糖苷-β-环糊精包合物的组合物的干燥物,能够适合用作源自咖啡因的苦味减小的食品(咖啡果冻)。
(成分) (质量%)
制备例10的组合物 0.1
咖啡因 0.05%
砂糖 15.0
明胶 1.0
咖啡提取物 5.0
水 余量
总量 100.0。
配方例5:漱口液
制作漱口液,其含有制备例9的含橙皮素-7-葡萄糖苷-β-环糊精包合物的组合物的干燥物。本品通过添加制备例9的含橙皮素-7-葡萄糖苷-β-环糊精包合物的组合物的干燥物和赤藓糖醇,能够适合用作色调变化少的化妆品(漱口液)。
(成分) (质量%)
制备例9的组合物 0.02
赤藓糖醇 5.0
月桂基硫酸钠 0.8
甘油 7.0
乙醇 15.0
l-薄荷醇 0.05
香料 0.04
水 余量
总量 100.0。
配方例6:润肤霜
制备润肤霜,其含有制备例8的含有鼠李糖的含异槲皮苷-γ-环糊精包合物的组合物的干燥物。本品通过添加制备例8的含有鼠李糖的含异槲皮苷-γ-环糊精包合物的组合物的干燥物和抗坏血酸,能够适合用作色调变化少、皱纹出现减少的化妆品(润肤霜)。
(成分) (质量%)
制备例8的组合物 0.6
抗坏血酸 0.1
蜂蜡 0.2
硬脂醇 5.0
硬脂酸 8.0
角鲨烷 10.0
自乳化型丙二醇单硬脂酸酯 3.0
聚氧乙烯鲸蜡基醚(20EO) 1.0
香料 0.5
防腐剂 微量
丙二醇 4.8
甘油 3.0
透明质酸钠 0.1
三乙醇胺 1.0
纯化水 余量
总量 100.0。
配方例7:润肤露
制备润肤霜,其含有制备例9的含橙皮素-7-葡萄糖苷-β-环糊精包合物的组合物的干燥物。本品通过添加制备例9的含橙皮素-7-葡萄糖苷-β-环糊精包合物的组合物的干燥物和赤藓糖醇,能够适合用作色调变化少的化妆品(润肤露)。
(成分) (质量%)
制备例9的组合物 0.05
赤藓糖醇 5.0
硬脂酸 2.0
鲸蜡醇 1.5
凡士林 3.0
羊毛脂醇 2.0
液体石蜡 10.0
聚氧乙烯单油酸酯(10EO) 2.0
香料 0.5
防腐剂 微量
丙二醇 4.8
甘油 3.0
透明质酸钠 0.1
三乙醇胺 1.0
纯化水 余量
总量 100.0。
配方例8:牙膏
制备牙膏,其含有制备例10的含柚皮素-7-葡萄糖苷-β-环糊精包合物的组合物的干燥物。本品通过添加制备例10的含柚皮素-7-葡萄糖苷-β-环糊精包合物的组合物的干燥物和木糖醇,能够适合用作色调变化少的化妆品(牙膏)。
(成分) (质量%)
制备例10的组合物 0.1
木糖醇 1.0
磷酸氢钙 42.0
甘油 18.0
卡拉胶 0.9
月桂基硫酸钠 1.2
对羟基苯甲酸丁酯 0.005
香料 1.0
水 余量
总量 100.0。
配方例9:冰淇淋
制备冰淇淋,其含有制备例9的含橙皮素-7-葡萄糖苷-β-环糊精包合物的组合物的干燥物。本品通过添加制备例9的含橙皮素-7-葡萄糖苷-β-环糊精包合物的组合物的干燥物,能够适合用作源自绿原酸的辛辣味少的食品(冰淇淋)。
(成分) (质量%)
制备例9的组合物 0.05
绿原酸 0.05
鲜奶油(45%脂肪) 33.8
脱脂奶粉 11.0
砂糖 14.8
加糖蛋黄 0.3
香草香精 0.1
水 余量
总量 100.0。
配方例10:片剂(片剂)
制备片剂,其含有制备例8的含异槲皮苷-γ-环糊精包合物的组合物的干燥物。本品通过添加制备例8的含异槲皮苷-γ-环糊精包合物的组合物的干燥物,能够适合用作源自赤藓糖醇的甜味得到改善的食品(片剂)。
(成分) (质量%)
制备例8的组合物 20.0
结晶纤维素 10.0
还原麦芽糖糖稀粉末 6.0
硬脂酸钙 2.0
虫胶 2.0
赤藓糖醇 60.0
总量 100.0。
工业实用性
根据本发明,能够抑制源自类黄酮的苦味和色调变化,此外能够改善具有不愉快味道的饮料食品等,因此能够适合地用于医药品、饮料食品、健康食品、特定保健用食品和化妆品等领域中。
Claims (23)
1.组合物,其含有选自脂肪酸、蛋白质、肽、氨基酸、维生素、矿物质、醇、甜味剂、酸味剂、抗氧化剂、增稠稳定剂和表面活性剂中的1种以上原材料、以及类黄酮-环糊精包合物,前述包合物包含通过对具有鼠李糖苷结构的类黄酮在环糊精存在下用具有鼠李糖苷酶活性的酶进行处理而得到的包合物。
2.根据权利要求1所述的组合物,其中,前述原材料包含选自维生素、糖醇、高甜味度甜味剂、糖和抗氧化剂中的1种以上。
3.根据权利要求1所述的组合物,其中,前述原材料包含选自抗坏血酸、山梨糖醇、赤藓糖醇、木糖醇、阿斯巴甜、三氯半乳蔗糖、安赛蜜、甜叶菊提取物、茶提取物、儿茶素、鞣酸、咖啡因、绿原酸和鼠李糖中的1种以上。
4.根据权利要求1所述的组合物,其中,前述原材料包含选自阿斯巴甜、三氯半乳蔗糖、安赛蜜和甜叶菊提取物中的1种以上。
5.根据权利要求1所述的组合物,其中,前述原材料包含选自抗坏血酸、山梨糖醇、赤藓糖醇、木糖醇和鼠李糖中的1种以上。
6.根据权利要求1所述的组合物,其中,前述原材料包含选自茶提取物、儿茶素、鞣酸、咖啡因和绿原酸中的1种以上。
7.根据权利要求1~6中任一项所述的组合物,其中,前述原材料的含量在组合物中为0.001~80质量%。
8.根据权利要求1~7中任一项所述的组合物,其中,前述包合物中的类黄酮包含选自异槲皮苷、橙皮素-7-葡萄糖苷、柚皮素-7-葡萄糖苷(樱桃苷)、香叶木素-7-葡萄糖苷、杨梅黄酮、圣草酚-7-葡萄糖苷、木犀草素-7-葡萄糖苷、花翠素-3-葡萄糖苷、矢车菊素-3-葡萄糖苷、异鼠李素-3-葡萄糖苷、山柰酚-3-葡萄糖苷、芹菜素-7-葡萄糖苷、槲皮素、橙皮素、柚皮素、金合欢素-7-葡萄糖苷、和它们的衍生物中的1种以上。
9.根据权利要求1~8中任一项所述的组合物,其中,前述包合物中的环糊精包含选自β-环糊精、支链β-环糊精和γ-环糊精中的1种以上。
10.根据权利要求1~9中任一项所述的组合物,其中,前述包合物中的类黄酮与环糊精的摩尔比(环糊精/类黄酮)为1.0~3.0。
11.根据权利要求1~10中任一项所述的组合物,其中,前述包合物包含选自异槲皮苷-γ-环糊精、橙皮素-7-葡萄糖苷-β-环糊精、和柚皮素-7-葡萄糖苷-β-环糊精中的1种以上,前述包合物中的类黄酮与环糊精的摩尔比(环糊精/类黄酮)为1.0~1.8。
12.根据权利要求1~11中任一项所述的组合物,其中,前述包合物包含异槲皮苷-γ-环糊精。
13.根据权利要求1~12中任一项所述的组合物,其中,前述包合物的含量为以类黄酮含量计在组合物中达到0.001~10质量%的量。
14.根据权利要求1~13中任一项所述的组合物,其进一步含有鼠李糖,前述包合物中的类黄酮与鼠李糖的摩尔比(鼠李糖/类黄酮)为0.1~10。
15.根据权利要求14所述的组合物,其中,前述包合物中的类黄酮与鼠李糖的摩尔比(鼠李糖/类黄酮)为0.8~1.2。
16.饮料食品,其包含权利要求1~15中任一项所述的组合物。
17.医药品,其包含权利要求1~15中任一项所述的组合物。
18.化妆品,其包含权利要求1~15中任一项所述的组合物。
19.饮料食品、医药品或化妆品的制造方法,其包括将饮料食品原料、医药品原料或化妆品原料与权利要求1~15中任一项所述的组合物混合的步骤。
20.抑制饮料食品或医药品中的源自类黄酮的苦味的方法,其包括将饮料食品原料或医药品原料与权利要求1~15中任一项所述的组合物混合的步骤。
21.抑制饮料食品、医药品中的不愉快味道的方法,其包括将饮料食品原料或医药品原料与权利要求1~15中任一项所述的组合物混合的步骤。
22.根据权利要求21的不愉快味道改善方法,其中,前述不愉快味道是源自前述原材料的甜味的留存、甜味、苦味、涩味、辛辣味或酸味。
23.抑制饮料食品、医药品或化妆品中的源自类黄酮的色调变化的方法,其包括将饮料食品原料、医药品原料或化妆品原料与权利要求1~15中任一项所述的组合物混合的步骤。
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CN115677641A (zh) * | 2022-10-26 | 2023-02-03 | 中科中山药物创新研究院 | 槲皮素包合物共晶、中药组合物及其制备方法与应用 |
CN115677641B (zh) * | 2022-10-26 | 2024-03-12 | 中科中山药物创新研究院 | 槲皮素包合物共晶、中药组合物及其制备方法与应用 |
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AU2018425646A8 (en) | 2021-11-11 |
JPWO2019230013A1 (ja) | 2020-06-11 |
JP6616046B1 (ja) | 2019-12-04 |
CA3100296A1 (en) | 2019-12-05 |
WO2019230013A1 (ja) | 2019-12-05 |
AU2018425646B2 (en) | 2021-10-14 |
AU2018425646B8 (en) | 2021-11-11 |
AU2018425646A1 (en) | 2021-01-07 |
EP3805399A4 (en) | 2022-03-09 |
EP3805399A1 (en) | 2021-04-14 |
US20210205344A1 (en) | 2021-07-08 |
CA3100296C (en) | 2022-06-07 |
US11446319B2 (en) | 2022-09-20 |
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