CN115915968A - 涩味抑制剂 - Google Patents
涩味抑制剂 Download PDFInfo
- Publication number
- CN115915968A CN115915968A CN202180039633.1A CN202180039633A CN115915968A CN 115915968 A CN115915968 A CN 115915968A CN 202180039633 A CN202180039633 A CN 202180039633A CN 115915968 A CN115915968 A CN 115915968A
- Authority
- CN
- China
- Prior art keywords
- astringency
- mol
- galactose
- arabinogalactan
- molecular weight
- 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.)
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- 235000019606 astringent taste Nutrition 0.000 title claims abstract description 78
- 239000003112 inhibitor Substances 0.000 title claims description 19
- 229920000189 Arabinogalactan Polymers 0.000 claims abstract description 79
- 235000019312 arabinogalactan Nutrition 0.000 claims abstract description 79
- SATHPVQTSSUFFW-UHFFFAOYSA-N 4-[6-[(3,5-dihydroxy-4-methoxyoxan-2-yl)oxymethyl]-3,5-dihydroxy-4-methoxyoxan-2-yl]oxy-2-(hydroxymethyl)-6-methyloxane-3,5-diol Chemical compound OC1C(OC)C(O)COC1OCC1C(O)C(OC)C(O)C(OC2C(C(CO)OC(C)C2O)O)O1 SATHPVQTSSUFFW-UHFFFAOYSA-N 0.000 claims abstract description 65
- 239000001904 Arabinogalactan Substances 0.000 claims abstract description 63
- 229930182830 galactose Natural products 0.000 claims abstract description 54
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- 238000002360 preparation method Methods 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 23
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- 235000005487 catechin Nutrition 0.000 claims description 15
- 230000002401 inhibitory effect Effects 0.000 claims description 9
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Abstract
本发明提供一种有效改善由多酚等带来的涩味的涩味改善剂。本发明的涩味抑制剂以分子量为10,000~1,000,000且全部半乳糖中1,3键合的半乳糖的比率为12摩尔%以上的阿拉伯半乳聚糖作为有效成分。
Description
技术领域
本发明涉及一种抑制由涩味物质产生的涩味的涩味抑制剂。
背景技术
已知多酚具有抗氧化作用,对预防动脉硬化等生活习惯疾病有效果。然而,含有高浓度的多酚的饮料等存在源自多酚的涩味过强而带来不适感或厌恶感的情况。
对于抑制该不适的涩味的方法进行了各种研究,例如报告有葡萄柚果汁或酸橙果汁对抑制源自苹果多酚的涩味有效(专利文献1)。
又,报告有包含约10%的阿拉伯半乳聚糖-蛋白质复合物的阿拉伯胶可改善甜菊提取物、三氯蔗糖或罗汉果提取物的苦味、涩味等味质(专利文献2)。
[专利文献1]日本专利特开2002-95450号公报
[专利文献2]日本专利特开2016-187344号公报
发明内容
本发明涉及以下的1)~4)。
1)一种涩味抑制剂,其中,以分子量为10,000~1,000,000且全部半乳糖中1,3键合的半乳糖的比率为12摩尔%以上的阿拉伯半乳聚糖作为有效成分。
2)一种涩味抑制方法,其中,包括向含有涩味物质的经口制品中配合如1)中所记载的涩味抑制剂的工序。
3)阿拉伯半乳聚糖在用于制造涩味抑制剂中的用途,其中,上述阿拉伯半乳聚糖的分子量为10,000~1,000,000且全部半乳糖中1,3键合的半乳糖的比率为12摩尔%以上。
4)阿拉伯半乳聚糖在用于抑制涩味中的用途,其中,上述阿拉伯半乳聚糖的分子量为10,000~1,000,000且全部半乳糖中1,3键合的半乳糖的比率为12摩尔%以上。
具体实施方式
本发明提供一种有效抑制由多酚等带来的涩味的涩味抑制剂。
本发明人对可抑制由多酚等带来的不适的涩味的素材进行了研究,结果发现,具有特定糖结构的阿拉伯半乳聚糖对抑制涩味有效。
根据本发明,可有效抑制源自多酚等涩味物质的不适的涩味。又,本发明的涩味抑制剂为天然成分,且安全性较高,因此可用于饮食品、医药品、准医药品的领域。
本发明的阿拉伯半乳聚糖的分子量为10,000~1,000,000且全部半乳糖中1,3键合的半乳糖的比率为12摩尔%以上。
“阿拉伯半乳聚糖”是指以阿拉伯糖及半乳糖作为其主成分的多糖。本发明的阿拉伯半乳聚糖是指以1,3键合的半乳糖作为主链,且具有自主链的半乳糖的6位开始分支的侧链的所谓II型阿拉伯半乳聚糖。
在本发明中,“1,3键合的半乳糖”(也称为“3-Galp”)意指处于键合状态,且仅1位羟基及3位羟基与其它糖分子的羟基形成醚键的半乳糖,即具有“3)-Gal-(1”的结构的半乳糖,可存在于主链或侧链的任一者。
再者,“主链”是指糖链分子中最长的链,“侧链”是指自主链分枝的相对较短的链。
本发明的阿拉伯半乳聚糖中,全部半乳糖中1,3键合的半乳糖的比率为12摩尔%以上,优选为16摩尔%以上,更优选为18摩尔%以上,进而优选为20摩尔%以上,进而更优选为22摩尔%以上,且优选为70摩尔%以下,更优选为60摩尔%以下,进而优选为50摩尔%以下。又,优选为12~70摩尔%,更优选为16~70摩尔%,进而优选为18~70摩尔%,进而更优选为20~60摩尔%,尤其优选为22~50摩尔%。
本发明的阿拉伯半乳聚糖中,阿拉伯半乳聚糖中的半乳糖与阿拉伯糖之和中1,3键合的半乳糖的摩尔含量(%)为8摩尔%以上,优选为10摩尔%以上,更优选为12摩尔%以上,进而优选为14摩尔%以上,且优选为70摩尔%以下,更优选为50摩尔%以下,进而优选为40摩尔%以下。又,优选为8~70摩尔%,更优选为10~70摩尔%,进而优选为12~60摩尔%,进而更优选为14~50摩尔%。
本发明的阿拉伯半乳聚糖的侧链中还可具有少量的葡萄糖、鼠李糖、岩藻糖及葡萄糖醛酸等的除半乳糖及阿拉伯糖以外的糖。在该情形时,将半乳糖的摩尔设为1时除半乳糖及阿拉伯糖以外的糖的摩尔比例如为10以下,优选为1以下。
本发明的阿拉伯半乳聚糖的分子量为10,000~1,000,000,优选为20,000以上、35,000以上、50,000以上、65,000以上,又,优选为500,000以下、350,000以下、200,000以下。又,优选为10,000~500,000,更优选为20,000~500,000,进而优选为35,000~350,000,进而更优选为50,000~350,000,尤其优选为65,000~200,000。
该阿拉伯半乳聚糖的糖链键合状态组成的解析可通过本领域技术人员所公知的方法,例如甲基化分析(F.A.Pettolino et.al.,Nature Protocols,2012,7,1590-1607.)来进行。本发明中的“全部半乳糖中1,3键合的半乳糖的比率”也为通过本甲基化分析而算出的数值。
另一方面,“不含糖链键合状态的信息的单纯半乳糖、阿拉伯糖的组成”的解析可通过组合了利用三氟乙酸等酸所进行的水解与离子色谱法的结构糖解析法等而算出。
又,分子量的测定可通过GPC(凝胶渗透色谱法)等来进行。本申请中所示的分子量表示GPC分析时的峰顶分子量,通过与标准物质Shodex Standard P-82(昭光通商株式会社)的比对而算出。
本发明的阿拉伯半乳聚糖可通过使用公知的方法自西洋梨、生咖啡、萝卜等植物中分离、纯化而获得。
这些植物可直接使用,或者使用通过对其进行压榨而获得的榨汁、对植物体本身进行干燥而成的干燥物或其粉碎物、或自它们中提取出的提取物。作为提取物,可例举在常温或加温下对植物进行提取或使用索氏提取器等提取器具进行提取而得的各种溶剂提取物、其稀释液、其浓缩液或其干燥粉末等。
提取所使用的溶剂可为水、亲水性有机溶剂、疏水性有机溶剂或包含它们的2种以上的混合物的任意种,优选为水。水的种类并无特别限定,可为纯水及自来水等。又,水可经纯化、杀菌、灭菌、过滤、渗透压调节及缓冲化等的通常的处理,例如生理盐水、磷酸缓冲液等缓冲液也可用作提取溶剂。作为亲水性有机溶剂,可例举甲醇、乙醇、丁醇、甘油、丙二醇、1,3-丁二醇等醇、丙酮、四氢呋喃、乙腈、1,4-二恶烷、吡啶、二甲基亚砜、N,N-二甲基甲酰胺及乙酸等公知的亲水性有机溶剂。作为疏水性有机溶剂,可例举己烷、环己烷、四氯化碳、氯仿、二氯甲烷、1,2-二氯乙烷、二乙醚、乙酸乙酯、苯、甲苯、正己烷及异辛烷等公知的疏水性有机溶剂。再者,在提取时,可在添加有酸或碱且调节了溶液pH值的状态下进行提取操作。
提取方法并无特别限定,例如可使用固液提取、液液提取、浸渍、煎出、浸出、回流提取、索氏提取、超声波提取、微波提取、搅拌等通常方法。
作为阿拉伯半乳聚糖的分离、纯化所使用的方法,可例举再沉淀、重结晶、夹杂成分的酶分解、酸分解、膜过滤、超滤、透析、凝胶过滤色谱法、离子交换色谱法、亲和色谱法及高效液相色谱法(HPLC)等,它们可单独使用,也可组合使用多种。
本发明的阿拉伯半乳聚糖可为包含少量夹杂物的粗纯化,但优选为不含通过HPLC等检测法、生物检定等试验能够检测出的夹杂物,例如可为去除了蛋白质、脂质及糖质等其它成分的物质。
本发明的阿拉伯半乳聚糖可自西洋梨、生咖啡、萝卜等植物中纯化,也可自其它植物中纯化。可通过提取物或提取物的酸分解物的HPLC分析、离子色谱法分析、上述甲基化分析等而容易地确认植物中是否包含本发明的阿拉伯半乳聚糖。
又,本发明的阿拉伯半乳聚糖还可通过本领域技术人员所公知的多糖的化学合成法而制得。作为多糖的化学合成法,例如可例举阶段缩合法、缩聚法及开环聚合法等。
如下述实施例所示,本发明的阿拉伯半乳聚糖可抑制作为涩味物质的一种的儿茶素类的涩味。因此,本发明的阿拉伯半乳聚糖可为用于在配合于含有涩味物质的经口制品(例如医药品、准医药品、食品等)而抑制涩味中使用的涩味抑制剂,又,可用于在制造该涩味抑制剂中使用。
此处,“涩味”与味觉感受器所感觉到的苦味不同,是指味蕾或味觉细胞以外因整个口腔内的黏膜收缩而感觉到的口中发麻的感觉,不包含于“味觉”中。
作为涩味物质,只要具有涩味即可,并无特别限定,优选为具有涩味的功能性素材,例如可例示多酚、硫酸铝铵、硫酸铝钾、氯化铝等。
作为多酚,作为其代表例,可例示黄酮类、苯丙素类、水解型单宁、芪类等,黄酮类包含非聚合物儿茶素类、缩合型单宁类、茶黄素、槲皮素、芦丁、法国海岸松树皮提取物(Flavangenol)、碧萝芷;苯丙素类包含绿原酸、咖啡酸、阿魏酸、迷迭香酸;水解型单宁类包含单宁酸、五没食子酰葡萄糖、没食子酸、鞣花酸、鞣花丹宁;芪类包含白藜芦醇。
“非聚合物儿茶素类”是合并:儿茶素、没食子儿茶素、儿茶素没食子酸酯及没食子儿茶素没食子酸酯等的非表型儿茶素类;与表儿茶素、表没食子儿茶素、表儿茶素没食子酸酯及表没食子儿茶素没食子酸酯等的表型儿茶素类的总称。“非聚合物儿茶素类的没食子酸酯体”是合并:儿茶素没食子酸酯、没食子儿茶素没食子酸酯、表儿茶素没食子酸酯、表没食子儿茶素没食子酸酯等的总称。
“绿原酸类”是合并:3-咖啡酰奎尼酸、4-咖啡酰奎尼酸及5-咖啡酰奎尼酸的单咖啡酰奎尼酸;3-阿魏酰奎尼酸、4-阿魏酰奎尼酸及5-阿魏酰奎尼酸的单阿魏酰奎尼酸;以及3,4-二咖啡酰奎尼酸、3,5-二咖啡酰奎尼酸及4,5-二咖啡酰奎尼酸的二咖啡酰奎尼酸的总称。
本发明的涩味抑制剂可作为用于配合于含有涩味物质的组合物(经口制品)的素材或制剂使用。即,涩味抑制剂可包含本发明的阿拉伯半乳聚糖,又,也可为除包含阿拉伯半乳聚糖以外还包含赋形剂、粘合剂、增量剂、稀释剂等制剂载体。
作为使用本发明的涩味抑制剂的经口制品,只要含有涩味物质且可经口摄取即可,并无特别限定,可为液态,也可为固态。例如可例举具有涩味的医药品、准医药品、食品等。医药品及准医药品的剂型只要为经口给药用制剂即可,并无特别限定,例如可为颗粒剂、片剂、口含剂、糖浆剂等公知的任意剂型。作为准医药品,例如可例示牙膏(toothpaste)、漱口水(mouth wash)、含漱液(mouth rinse)等。医药品及准医药品可按照常规方法来制造,制剂化时,可配合赋形剂等公知的添加剂。
作为食品,例如可例举含有涩味物质的食品或饮料、添加有涩味物质的食品或饮料。食品可根据其种类而按照常规方法来制造。作为含有涩味物质的食品或饮料,例如可例举绿茶、红茶、乌龙茶、葡萄酒、柿叶茶、番石榴叶茶、洋葱皮茶等饮料、或含有它们的食品。
作为经口制品,就容易享有本发明的效果的方面而言,优选为食品,进而优选为饮料。作为食品,例如可例示:葡萄柚、橙子、柠檬等柑橘果实或由这些果实所获得的果汁;番茄、青椒、芹菜、葫芦、胡萝卜、马铃薯、芦笋等蔬菜或由这些蔬菜所获得的蔬菜汁或者蔬菜液;咖啡、可可、绿茶、红茶、乌龙茶、清凉饮料、葡萄酒、啤酒等饮料;沙司、酱油、味噌、辣椒、鲜味剂等调味料;豆浆等大豆食品;奶油、调味酱、蛋黄酱、人造奶油等乳化食品;鱼肉、鱼糜、鱼卵等水产加工食品;花生等坚果;纳豆等发酵食品;食用肉或其加工食品;腌菜;面;包含汤粉的汤;奶酪、牛奶等乳制品;面包、蛋糕;点心、饼干、米饼、口香糖、巧克力、糖果等甜食等。
本发明的阿拉伯半乳聚糖在经口制品中的用量只要为用于抑制涩味的有效量即可,并无特别限定,可根据涩味物质或经口制品的种类、涩味强度适当地设定。例如,阿拉伯半乳聚糖的用量以其相对于涩味物质的质量比[阿拉伯半乳聚糖/涩味物质]计,优选为0.0005以上,更优选为0.001以上,进而优选为0.0025以上,且优选为0.8以下,更优选为0.1以下,进而优选为0.035以下,或优选为0.0005~0.8,更优选为0.001~0.1,进而优选为0.0025~0.035。
在该情形时,经口制品中的涩味物质的含量优选为0.001~0.8质量%,更优选为0.005~0.7质量%,进而优选为0.008~0.6质量%,进而更优选为0.03~0.4质量%。
又,就抑制涩味的观点而言,经口制品中的本发明的阿拉伯半乳聚糖的含量优选为0.0001质量%以上,更优选为0.00015质量%以上,进而优选为0.00025质量%以上,且优选为0.08质量%以下,更优选为0.01质量%以下,进而优选为0.005质量%以下。又,优选为0.0001~0.08质量%,更优选为0.00015~0.01质量%,进而优选为0.00025~0.005质量%。
关于上述实施方式,在本发明中进一步示出以下的方式。
<1>一种涩味抑制剂,其中,以阿拉伯半乳聚糖作为有效成分,上述阿拉伯半乳聚糖的分子量为10,000~1,000,000,优选为20,000以上、35,000以上、50,000以上、65,000以上,又,优选为500,000以下、350,000以下、200,000以下,且全部半乳糖中1,3键合的半乳糖的比率为12摩尔%以上。
<2>如<1>的涩味抑制剂,其中,全部半乳糖中1,3键合的半乳糖的比率优选为16摩尔%以上,更优选为18摩尔%以上,进而优选为20摩尔%以上,进而更优选为22摩尔%以上,且优选为70摩尔%以下,更优选为60摩尔%以下,进而优选为50摩尔%以下,或者优选为12~70摩尔%,更优选为16~70摩尔%,进而优选为18~70摩尔%,进而更优选为20~60摩尔%,尤其优选为22~50摩尔%。
<3>如<1>或<2>的涩味抑制剂,其中,分子量为10,000~500,000,优选为20,000~500,000,更优选为35,000~350,000,进而优选为50,000~350,000,进而更优选为65,000~200,000。
<4>如<1>至<3>中任一项的涩味抑制剂,其中,抑制由多酚带来的涩味。
<5>如<4>的涩味抑制剂,其中,多酚为非聚合物儿茶素类。
<6>一种涩味抑制方法,其中,包括向含有涩味物质的经口制品中配合如<1>至<5>中任一项的涩味抑制剂的工序。
<7>如<6>的方法,其中,阿拉伯半乳聚糖在经口制品中的用量以其相对于涩味物质的质量比[阿拉伯半乳聚糖/涩味物质]计,优选为0.0005以上,更优选为0.001以上,进而优选为0.0025以上,且优选为0.8以下,更优选为0.1以下,进而优选为0.035以下,或者优选为0.0005~0.8,更优选为0.001~0.1,进而优选为0.0025~0.035。
<8>如<6>的方法,其中,经口制品中的本发明的阿拉伯半乳聚糖的含量优选为0.0001质量%以上,更优选为0.00015质量%以上,进而优选为0.00025质量%以上,且优选为0.08质量%以下,更优选为0.01质量%以下,进而优选为0.005质量%以下,或者优选为0.0001~0.08质量%,更优选为0.00015~0.01质量%,进而优选为0.00025~0.005质量%。
<9>阿拉伯半乳聚糖在用于制造涩味抑制剂中的用途,其中,上述阿拉伯半乳聚糖的分子量为10,000~1,000,000,优选为20,000以上、35,000以上、50,000以上、65,000以上,又,优选为500,000以下、350,000以下、200,000以下,且全部半乳糖中1,3键合的半乳糖的比率为12摩尔%以上。
<10>如<9>的用途,其中,全部半乳糖中1,3键合的半乳糖的比率优选为16摩尔%以上,更优选为18摩尔%以上,进而优选为20摩尔%以上,进而更优选为22摩尔%以上,且优选为70摩尔%以下,更优选为60摩尔%以下,进而优选为50摩尔%以下,或者优选为12~70摩尔%,更优选为16~70摩尔%,进而优选为18~70摩尔%,进而更优选为20~60摩尔%,尤其优选为22~50摩尔%。
<11>如<9>或<10>的用途,其中,分子量为10,000~500,000,优选为20,000~500,000,更优选为35,000~350,000,进而优选为50,000~350,000,进而更优选为65,000~200,000。
<12>如<9>至<11>中任一项的用途,其中,涩味抑制剂抑制由多酚带来的涩味。
<13>如<12>的用途,其中,多酚为非聚合物儿茶素类。
<14>阿拉伯半乳聚糖在用于抑制涩味中的用途,其中,上述阿拉伯半乳聚糖的分子量为10,000~1,000,000,优选为20,000以上、35,000以上、50,000以上、65,000以上,又,优选为500,000以下、350,000以下、200,000以下,且全部半乳糖中1,3键合的半乳糖的比率为12摩尔%以上。
<15>如<14>的用途,其中,全部半乳糖中1,3键合的半乳糖的比率优选为16摩尔%以上,更优选为18摩尔%以上,进而优选为20摩尔%以上,进而更优选为22摩尔%以上,且优选为70摩尔%以下,更优选为60摩尔%以下,进而优选为50摩尔%以下,或者优选为12~70摩尔%,更优选为16~70摩尔%,进而优选为18~70摩尔%,进而更优选为20~60摩尔%,尤其优选为22~50摩尔%。
<16>如<14>或<15>的用途,其中,分子量为10,000~500,000,优选为50,000~350,000,更优选为65,000~200,000。
<17>如<14>至<16>中任一项的用途,其中,抑制由多酚带来的涩味。
<18>如<17>的用途,其中,多酚为非聚合物儿茶素类。
<19>如<14>至<18>中任一项的用途,其中,阿拉伯半乳聚糖在经口制品中的用量以其相对于涩味物质的质量比[阿拉伯半乳聚糖/涩味物质]计,优选为0.0005以上,更优选为0.001以上,进而优选为0.0025以上,且优选为0.8以下,更优选为0.1以下,进而优选为0.035以下,或者优选为0.0005~0.8,更优选为0.001~0.1,进而优选为0.0025~0.035。
<20>如<14>至<18>中任一项的用途,其中,经口制品中的本发明的阿拉伯半乳聚糖的含量优选为0.0001质量%以上,更优选为0.00015质量%以上,进而优选为0.00025质量%以上,且优选为0.08质量%以下,更优选为0.01质量%以下,进而优选为0.005质量%以下,或者优选为0.0001~0.08质量%,更优选为0.00015~0.01质量%,进而优选为0.00025~0.005质量%。
[实施例]
制造例1西洋梨阿拉伯半乳聚糖的纯化
向20g的6倍浓缩西洋梨果汁(株式会社果香)中添加100mL的纯水,使用区分分子量10kDa的UF平板膜(Merck Millipore株式会社,Ultracel)进行超滤(Merck Millipore株式会社,Amicon)。进而加水,将超滤重复3次。回收未通过组分,冷冻干燥后,通过凝胶过滤色谱法(Sephadex G-100,20×280mm,洗脱液0.1%乙酸水溶液)进行纯化,获得13.1mg的西洋梨阿拉伯半乳聚糖。
制造例2生咖啡阿拉伯半乳聚糖的纯化
向200g的粉碎生咖啡豆(Brazil Santos#2,由松屋珈琲获得)中添加2000mL的纯水,于100℃下提取45-60分钟,其后,通过滤纸过滤(Advantec#1)获得提取液,进行冷冻干燥,获得44.34g的提取物粉末。将其再次溶解于440mL的纯水后,添加17.6g的甲酸,在冷却至5℃下,进行离心分离(3000rpm,30分钟),去除沉淀物。对约500mL的所获得的液体部分添加99.5v/v%乙醇2500mL后,进行离心分离,由此回收沉淀物,进行冷冻干燥而获得4.28g的粗多糖组分。
向4.28g的上述粗多糖组分中添加100mL的50mM氢氧化钠水溶液及130mL的饱和氢氧化钡水溶液,在室温下静置3小时后,进行离心分离(3000rpm,30分钟)而去除沉淀物。关于所获得的液体部分,添加1当量浓度的稀硫酸以成为pH值=4,再次进行离心分离(3000rpm,30分钟)而去除沉淀物。关于液体部分,添加99.5v/v%乙醇1450mL而形成沉淀,将其回收,进行冷冻干燥而获得1.18g的粗阿拉伯半乳聚糖组分。
关于粗阿拉伯半乳聚糖组分,利用100mL的Dowex Marathon MR-3H+/OH-型去除离子成分,其后,进行冷冻干燥,获得0.71g的生咖啡阿拉伯半乳聚糖。
制造例3萝卜阿拉伯半乳聚糖的纯化
向80g的经干燥的萝卜根部的干燥粉末(Kodama Foods)中添加800mL的纯水并进行加热,于沸水中提取4小时。放置冷却后,使用滤纸(Kiriyama 5A滤纸)进行过滤,对滤液进行冷冻干燥而获得51.7g的提取物粉末。向其中以总重量成为220g的方式添加纯水而使上述提取物粉末溶解,进而添加99.5v/v%乙醇330mL,在室温下静置一晚。其后,进行离心分离(3000rpm、30分钟)去除上清液,利用70v/v%乙醇250mL对沉淀物进行2次洗净。将所获得的沉淀物溶解于纯水中并进行冷冻干燥,获得3.74g的固形物成分。自其中量取300mg,溶解于3mL的纯水中。向其中添加0.1mL的果胶酶(SIGMA,来自棘孢曲霉(Aspergillusaculeatus)的果胶酶),于40℃下培养90分钟。其后,升温至90℃以上以使果胶酶失活,进行放置冷却,添加5mL的纯水、12mL的99.5v/v%乙醇,并于-20℃下静置一晚。对其进行离心分离(3000rpm,30分钟)去除上清液,利用70v/v%乙醇5mL对沉淀物进行2次洗净。将所获得的沉淀物溶解于纯水中,通过离心分离(3000rpm,30分钟)去除未溶解的沉淀物。对所获得的上清液进行冷冻干燥,获得84.3mg的萝卜阿拉伯半乳聚糖。
制造例4落叶松阿拉伯半乳聚糖的纯化
将94.7mg的Resist Aid(Lonza K.K.株式会社)溶解于3mL的纯水中,使用区分分子量300Da的透析膜进行电透析(ASTOM,MICRO ACILYZER S1),获得86mg的落叶松阿拉伯半乳聚糖。
制造例5日本梨阿拉伯半乳聚糖的纯化
向480g的5倍浓缩日本梨果汁(株式会社果香)中添加1.9L的纯水,使用区分分子量10kDa的UF平板膜(Merck Millipore株式会社,Ultracel)进行超滤(Merck Millipore株式会社,Amicon)。进而加水,将超滤重复3次。回收未通过组分,进行冷冻干燥后,获得253mg的日本梨阿拉伯半乳聚糖。
制造例6烘焙咖啡阿拉伯半乳聚糖的纯化
向10g的烘焙咖啡豆的热水提取物(花王株式会社)中添加90mL的纯水,添加0.1mL的果胶酶(SIGMA,来自棘孢曲霉(Aspergillus aculeatus)的果胶酶)并于40℃下培养90分钟。其后,升温至90℃以上以使果胶酶失活,进行放置冷却。分取50mL的该溶液,添加50mL的99.5v/v%乙醇,并于-20℃下静置一晚。对其进行离心分离(3000rpm,30分钟)而去除上清液,利用10mL的50v/v%乙醇对沉淀物进行2次洗净。将所获得的沉淀物溶解于纯水中,进行冷冻干燥而获得642mg的烘焙咖啡阿拉伯半乳聚糖。
试验例阿拉伯半乳聚糖的分析
1.分子量测定
通过GPC-RI分析求出制造例1~6的各种阿拉伯半乳聚糖及阿拉伯胶(CREOInternational株式会社,CREO GUM#4810)的峰顶分子量。
<GPC-RI分析条件>
·HPLC系统:Chromaster(Hitachi High-Tech Corporation)
·管柱:TSKgel GMPWxl 7.8×300mm(TOSOH CORPORATION)
·保护管柱:TSKgel PWxl 6×40mm
·洗脱液:0.2M磷酸缓冲液(pH值为6.8)/乙腈=9:1、流速:1.0mL/min、管柱温度:40℃、检测:RI
·标准物质:Shodex Standard P-82(昭光通商株式会社)
2.L-阿拉伯糖及D-半乳糖的分析(结构糖解析)
分别称量约5mg的制造例1~6的各种阿拉伯半乳聚糖及阿拉伯胶(CREOInternational株式会社,CREO GUM#4810)置于螺纹口试验管中,添加5mL的2N的盐酸甲醇溶液,利用80℃的块加热器加热18小时。放置冷却后,于氮气流下进行浓缩,添加1mL异丙醇而再次进行浓缩。
向其中添加5mL的2N的三氟乙酸水溶液,利用110℃的块加热器加热1小时,进行水解。放置冷却后,添加10mL的1N氢氧化钠水溶液进行中和,以mL定容至20mL后,通过离子色谱法分析求出L-阿拉伯糖与D-半乳糖的构成比(摩尔%)。
<离子色谱法分析条件>
·系统:Dionex ICS-5000(Thermo Fisher Scientific株式会社)
·检测器:Dionex ICS-5000ED电化学检测器(Thermo Fisher Scientific株式会社)
·管柱:Dionex CarboPac PA1 4×250mm
·保护管柱:Dionex CarboPac PA1 4×50mm
·流速:1mL/min
·管柱温度:25℃
·柱温箱温度:35℃
·洗脱液A:超纯水
·洗脱液B:18mM氢氧化钠水溶液
·洗脱液C:200mM氢氧化钠水溶液
·洗脱液D:150mM乙酸钠、100mM氢氧化钠水溶液
·浓度梯度条件(体积%):下述表1
[表1]
时间 | 洗脱液A | 洗脱液B | 洗脱液C | 洗脱液D |
0分钟 | 95% | 0% | 5% | 0% |
25分钟 | 95% | 0% | 5% | 0% |
26分钟 | 0% | 0% | 100% | 0% |
36分钟 | 0% | 0% | 100% | 0% |
37分钟 | 95% | 0% | 5% | 0% |
47分钟 | 95% | 0% | 5% | 0% |
3.甲基化分析
甲基化分析是为了确定多糖中的各单糖相互的键合位置来进行。可算出在某位置具有键的单糖在多糖中所占的比率。操作包括以下的4个工序。
1)将多糖完全甲基化。
2)对完全甲基化多糖进行水解,制成部分甲基化单糖。
3)对未被甲基化的羟基进行乙酰化,而转化为部分甲基化、部分醛醣醇乙酸酯(partially methylated partially acetylated alditol acetates,PMAA)衍生物。
4)使用GC-MS对上述衍生物进行分离、解析。
甲基化分析使用完全甲基化法,该完全甲基化法以F.A.Pettolino等人的试验方案(Nature Protocols,2012,7,1590-1607.)为参考且使用固体氢氧化钠。再者,完全甲基化法还可利用被称为箱守法(Hakomori method)的使用甲基亚磺酰基碳负离子试剂的方法等,但分析结果并不受方法影响。
1)完全甲基化
分别称量约0.6mg的制造例1~6的各种阿拉伯半乳聚糖置于螺纹口试验管中,溶解于0.5mL的脱水DMSO中,使试验管内成为氮气氛围下。将分散于脱水DMSO中的粉末氢氧化钠(120mg的NaOH/1mL的DMSO)连同DMSO一起进行添加计0.5mL,进行30分钟超声波处理。向其中添加0.1mL的碘甲烷并进行10分钟超声波处理。进而添加0.1mL的碘甲烷并进行10分钟超声波处理后,添加0.2mL的碘甲烷并进行20分钟超声波处理。继而添加2mL的超纯水及1.5mL的二氯甲烷并进行漩涡搅拌,去除水层。向二氯甲烷层中添加2mL的超纯水,进行漩涡搅拌,将水层去除,将此工序重复3次,将所获得的二氯甲烷层转移至另一螺纹口试验管。吹送氮气以去除二氯甲烷,进行干燥硬化而获得完全甲基化多糖。
2)水解
向所获得的完全甲基化多糖中添加0.2mL的超纯水以使之溶解,添加0.2mL的4N的TFA并利用120℃的块加热器加热1小时,进行水解。放置冷却后,进行离心浓缩,添加0.5mL的超纯水并进行离心浓缩,将该工序重复3次,获得部分甲基化单糖。
3)转化为PMAA衍生物
向所获得的部分甲基化单糖中添加0.5mL的2M氨水及10mg的硼氢化钠,在室温下反应2个半小时。反应后,利用90μL的乙酸进行中和,进行离心浓缩。向其中添加250μL的5v/v%乙酸-甲醇溶液并进行离心浓缩,将此工序重复2次。进而添加250μL的甲醇并进行离心浓缩,将此工序重复2次,进行干燥硬化。继而,添加250μL的乙酸酐并利用100℃的块加热器加热2个半小时。放置冷却后,添加2mL的超纯水与1.5mL的二氯甲烷并利用试验管混合机加以混合,去除水层。向二氯甲烷层中添加2mL的超纯水并利用试验管混合机加以混合,去除水层,将此工序重复3次,将所获得的二氯甲烷层转移至另一螺纹口试验管。吹送氮气以去除二氯甲烷,获得PMAA衍生物。
4)GC-MS解析
将所获得的PMAA衍生物溶解于50μL的氯仿中,利用GCMS进行解析。
<GCMS测定条件>
·GC:Agilent 7890B
·MS:Agilent 5977B
·管柱:DB-5ms+DG(Agilent J&W,30m×0.25mm)
·进样器温度:210℃
·接口温度:270℃
·管柱温度:150℃(5min)→250℃(5℃/min)→250℃(5min)
·载气:氦气
4.涩味强度的测定
将儿茶素制剂(Teavigo,由DSM Nutrition Japan株式会社获得,含有94质量%以上的表没食子儿茶素没食子酸酯)的添加浓度以表2方式阶段性地进行调节,由此制作具有不同涩味强度的10种标准水溶液。又,将各种阿拉伯半乳聚糖以成为0.00025w/v%的方式添加于1.0g/L的儿茶素制剂溶液中而制作受验饮料。4名专业评价小组成员通过感官评价而自10种标准水溶液中选择出识别为涩味强度与受验饮料同等的标准水溶液。对于所选择的标准水溶液的涩味强度,求出小组成员间的平均值以作为受验饮料的涩味强度的值。
[表2]
标准水溶液
涩味强度 | 儿茶素制剂的浓度(g/L aq.) |
1 | 0.1 |
2 | 0.2 |
3 | 0.3 |
4 | 0.4 |
5 | 0.5 |
6 | 0.6 |
7 | 0.7 |
8 | 0.8 |
9 | 0.9 |
10 | 1.0 |
实施例1、比较例1
将制造例1~6的各种阿拉伯半乳聚糖及阿拉伯胶(CREO International株式会社,CREO GUM#4810)的分析、涩味强度的测定结果示于表3。关于抑制涩味的评价基准,如果涩味强度小于8,则评价为具有涩味抑制效果。再者,阿拉伯胶的甲基化分析结果是基于文献(TALANTA,1983,30,11,887-893)而作成。由表3可知,此次评价所使用的各种阿拉伯半乳聚糖为以3-Galp作为主成分的II型阿拉伯半乳聚糖,并无以4-Galp作为主成分的I型阿拉伯半乳聚糖。其中可知,具有涩味抑制效果的阿拉伯半乳聚糖在半乳糖、阿拉伯糖的构成比的方面并无特征,在全部半乳糖中的3-Galp的摩尔比率为12%以上(主链的分支较少)且分子量为1万以上时表现出效果。
在甲基化分析中,虽获得有关作为阿拉伯半乳聚糖的结构糖的阿拉伯糖、半乳糖、其它全部糖残基的键合位置信息,但此处,示出了只是所有半乳糖残基加到一起成为100摩尔%时的各半乳糖残基的比率。就抑制涩味的观点而言,重要的是主链的分支较少,II型阿拉伯半乳聚糖的主骨架包含半乳糖,阿拉伯糖或其它微量糖全部键合于侧链,因此仅以半乳糖残基来比较。
又,烘焙咖啡阿拉伯半乳聚糖与生咖啡阿拉伯半乳聚糖同样地,3-Galp的摩尔比率较高但分子量较小,没有涩味抑制效果。认为其原因在于:生咖啡阿拉伯半乳聚糖的糖苷键因烘焙的热而断裂,在结构维持的同时成为小片段。由此认为涩味抑制效果得到减弱,因此推定出,要想表现出效果,分子量需为1万以上。
[表3]
*甲基化分析:阿拉伯糖残基与半乳糖残基合计为100%时的各残基的摩尔比率
t-Galp:末端半乳吡喃糖,3-Galp:在1位及3位具有键的半乳吡喃糖,6-Galp:在1位及6位具有键的半乳吡喃糖,3,6-Galp:在1位、3位及6位具有键的半乳吡喃糖,t-Araf:末端阿拉伯呋喃糖,3-Araf:在1位及3位具有键的阿拉伯呋喃糖,5-Araf:在1位及5位具有键的阿拉伯呋喃糖
实施例2
(1)饮料的制备
受验饮料2-1
将西洋梨阿拉伯半乳聚糖以成为0.01w/v%的方式添加于浓度1.0g/L的茶黄素水溶液(1%的茶黄素粉末,由横滨油脂工业株式会社获得)中,制作受验饮料2-1。
受验饮料2-2
将西洋梨阿拉伯半乳聚糖以成为0.01w/v%的方式添加于浓度1.0g/L的单宁酸水溶液(单宁酸AL,由富士化学工业株式会社获得)中,制作受验饮料2-2。
受验饮料2-3
将番石榴叶茶2g×4包(蕃贵糖茶,Yuukisy制药株式会社制造)于1L的沸水中煮10分钟,获得茶水,将西洋梨阿拉伯半乳聚糖以成为0.01w/v%的方式添加于该茶水中,制作受验饮料2-3。
受验饮料2-4
将洋葱皮茶1g×8包(洋葱皮茶,Orihiro Plantdew株式会社制造)于1L的沸水中煮10分钟,获得茶水,将西洋梨阿拉伯半乳聚糖以成为0.01w/v%的方式添加于该茶水中,制作受验饮料2-4。
(2)涩味评价
对于受验饮料2-1~4,由4名专业评价小组成员按照下述评价基准,对各饮料的涩味进行感官评价。各小组成员于西洋梨阿拉伯半乳聚糖添加前后进行比较,评价涩味是否得到抑制。在评价为涩味得到抑制的小组成员的人数为4人的情形时判定为◎,在3人的情形时判定为○,在2人的情形时判定为△,在1~0人的情形时判定为×。
<评价基准>
◎:涩味得到显著抑制○:涩味得到抑制
△:涩味几乎未被抑制×:涩味未被抑制
[表4]
实施例2-1 | 实施例2-2 | 实施例2-3 | 实施例2-4 | |
涩味评价 | ◎ | ◎ | ◎ | ○ |
Claims (16)
1.一种涩味抑制剂,其中,
以分子量为10,000~1,000,000且全部半乳糖中1,3键合的半乳糖的比率为12摩尔%以上的阿拉伯半乳聚糖作为有效成分。
2.如权利要求1所述的涩味抑制剂,其中,
全部半乳糖中1,3键合的半乳糖的比率为18~70摩尔%。
3.如权利要求1或2所述的涩味抑制剂,其中,
分子量为10,000~500,000。
4.如权利要求1~3中任一项所述的涩味抑制剂,其中,
抑制由多酚带来的涩味。
5.如权利要求4所述的涩味抑制剂,其中,
多酚为非聚合物儿茶素类。
6.一种涩味抑制方法,其中,
包括向含有涩味物质的经口制品中配合权利要求1~5中任一项所述的涩味抑制剂的工序。
7.阿拉伯半乳聚糖在用于制造涩味抑制剂中的用途,其中,
所述阿拉伯半乳聚糖的分子量为10,000~1,000,000且全部半乳糖中1,3键合的半乳糖的比率为12摩尔%以上。
8.如权利要求7所述的用途,其中,
全部半乳糖中1,3键合的半乳糖的比率为18~70摩尔%。
9.如权利要求7或8所述的用途,其中,
分子量为10,000~500,000。
10.如权利要求7~9中任一项所述的用途,其中,
涩味抑制剂抑制由多酚带来的涩味。
11.如权利要求10所述的用途,其中,
多酚为非聚合物儿茶素类。
12.阿拉伯半乳聚糖在用于抑制涩味中的用途,其中,
所述阿拉伯半乳聚糖的分子量为10,000~1,000,000且全部半乳糖中1,3键合的半乳糖的比率为12摩尔%以上。
13.如权利要求12所述的用途,其中,
全部半乳糖中1,3键合的半乳糖的比率为18~70摩尔%。
14.如权利要求12或13所述的用途,其中,
分子量为10,000~500,000。
15.如权利要求12~14中任一项所述的用途,其中,
抑制由多酚带来的涩味。
16.如权利要求15所述的用途,其中,
多酚为非聚合物儿茶素类。
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JP2018174758A (ja) * | 2017-04-07 | 2018-11-15 | 花王株式会社 | 渋味抑制剤 |
JP2019000099A (ja) * | 2017-06-15 | 2019-01-10 | 花王株式会社 | クロロゲン酸類含有組成物 |
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JP6084373B2 (ja) | 2011-05-27 | 2017-02-22 | 三栄源エフ・エフ・アイ株式会社 | 高甘味度甘味料の味質改善剤 |
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JP2018174758A (ja) * | 2017-04-07 | 2018-11-15 | 花王株式会社 | 渋味抑制剤 |
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