CN102656133B - 还原型辅酶q10的制造方法、稳定化方法以及含有还原型辅酶q10的组合物 - Google Patents
还原型辅酶q10的制造方法、稳定化方法以及含有还原型辅酶q10的组合物 Download PDFInfo
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- CN102656133B CN102656133B CN201080057097.XA CN201080057097A CN102656133B CN 102656133 B CN102656133 B CN 102656133B CN 201080057097 A CN201080057097 A CN 201080057097A CN 102656133 B CN102656133 B CN 102656133B
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Abstract
本发明的目的在于提供不仅具有对氧化型辅酶Q10的还原能力、使还原型辅酶Q10稳定化的能力,而且还兼具营养素、美味、通用性等的成分及其利用方法。本发明涉及使用特定的氨基酸类将氧化型辅酶Q10还原的还原型辅酶Q10的制造方法。另外,本发明还涉及在特定的氨基酸类的共存下,将还原型辅酶Q10稳定化的方法,以及该经稳定化了的组合物。
Description
技术领域
本发明涉及还原型辅酶Q10的制造方法、稳定化方法以及含有还原型辅酶Q10的组合物。与氧化型辅酶Q10相比,还原型辅酶Q10显示出较高的口服吸收性,是作为优异的食品、健康食品、营养功能食品、特定保健用食品、添加剂、营养辅助剂、营养剂、饮料、饲料、动物药、化妆品、药品、治疗药、预防药等有用的化合物。
背景技术
与氧化型辅酶Q10相比,还原型辅酶Q10显示出较高的口服吸收性,作为抗氧化物质是非常有用的化合物。还原型辅酶Q10可以通过对例如合成、发酵、从天然产物提取等现有公知的方法得到的氧化型辅酶Q10进行还原反应而获得(专利文献1)。
作为发挥出将氧化型辅酶Q10还原为还原型辅酶Q10的效果的成分(还原剂),已知的有硼氢化钠(非专利文献1)、连二亚硫酸钠(非专利文献2)、亚硫酸类物质(亚硫酸钠等)(非专利文献3)、抗坏血酸类(专利文献2)等。
然而,这些成分,或者由于具有着火的危险性,是在制造或使用时需要注意的化合物,或者其价格昂贵,或者对生物体的安全性存在问题,或者作为食品用途使用时会影响风味等,并不能很好地满足所要求的条件,在大多数情况下,在还原反应结束后,需要分离除去还原型辅酶Q10和上述还原剂及其副产物的工序。因此,强烈期望在还原反应结束后,可以将还原剂及其副产物直接作为发挥稳定化效果的成分使用,或者适合食品、健康食品、添加剂等使用的成分。
另外,在对氧化型辅酶Q10发挥出还原效果的成分中,也存在对还原型辅酶Q10发挥出稳定化效果的成分,即,可作为抗氧剂而使用的成分。已知还原型辅酶Q10会容易地被空气中的氧氧化为氧化型辅酶Q10。因此,保护还原型辅酶Q10的制剂或含有还原型辅酶Q10的合剂不被氧化的稳定化方法极为重要。
作为有效地将还原型辅酶Q10稳定化的化合物,已知的有柠檬酸、抗坏血酸类(专利文献3)。另外,作为使还原型辅酶Q10稳定化的溶剂,已知合适的为烃类、脂肪酸酯类、醚类和腈类(专利文献4)。
然而,这些对还原型辅酶Q10有效地发挥出稳定化效果的成分和溶剂,其自身或其副产物对生物体的安全性存在问题,或者作为食品用途使用时会影响风味,或者其价格昂贵等,并不能很好地满足所要求的条件,根据需要还希望实现进一步的稳定化。
在这种背景下,强烈希望开发出很好地满足下述要求的成分:可以作为对氧化型辅酶Q10发挥出还原效果的成分和/或对还原型辅酶Q10发挥出稳定化效果的成分使用,在制造使用时的危险性也少,价格低廉,此外还具有功能性。
现有技术文献
专利文献
专利文献1:日本特开平10-109933号公报
专利文献2:WO01/52822号公报
专利文献3:WO03/032967号公报
专利文献4:WO03/006408号公报
非专利文献
非专利文献1:Journal of Applied Toxicology,28(1),55-62,2008
非专利文献2:Pharmaceutical Research,23(1),70-81,2006
非专利文献3:第7版食品添加物公定書
发明内容
发明要解决的问题
基于上述问题,本发明的目的在于:提供还原型辅酶Q10的制造方法,该制造方法包括:利用安全性高且容易适用于食品、健康食品、营养功能食品、特定保健用食品、添加剂、营养辅助剂、营养剂、动物药、饮料、饲料、宠物食品、化妆品、药品、治疗药、预防药等,而且在制造后不需要分离除去的成分,进一步提供保护该还原型辅酶Q10不被氧化,从而可以稳定化的合适的方法,以及提供经稳定化的组合物。
解决问题的方法
本发明人等经过认真的研究发现:令人惊奇的是,在特定的氨基酸类的共存下,氧化型辅酶Q10被还原从而生成还原型辅酶Q10,进一步地,在该特定的氨基酸类的共存下,还原型辅酶Q10可得到很好的保护,免受分子氧的氧化,从而完成了本发明。
即,本发明涉及一种还原型辅酶Q10的制造方法,该方法包括:使用在侧链具有包含氮原子和/或氧原子的官能团的氨基酸类作为对氧化型辅酶Q10发挥出还原效果的成分,从而将氧化型辅酶Q10还原。进一步地,本发明还涉及还原型辅酶Q10的稳定化方法,该方法包括使还原型辅酶Q10与在侧链具有包含氮原子和/或氧原子的官能团的氨基酸类共存。另外,本发明还涉及包含还原型辅酶Q10与氨基酸类的组合物,该氨基酸类在侧链具有包含氮原子和/或氧原子的官能团。
本说明书包含作为本申请的优先权基础的日本国专利申请2009-239754号的说明书等中记载的内容。
发明的效果
根据本发明可以提供还原型辅酶Q10的简便的制造方法,其使用对生物体安全的成分将氧化型辅酶Q10还原,另外,还提供使用了该成分将还原型辅酶Q10稳定化的方法。进一步地,这些对氧化型辅酶Q10发挥出还原效果的成分和/或对还原型辅酶Q10发挥出稳定化效果的成分,还可期待起到营养素的作用,因此,得到的组合物,特别是作为要求各种效果的药品、添加剂、营养功能食品、特定保健用食品、营养辅助剂、营养剂、动物药、化妆品、治疗药等是非常有益的。
具体实施方式
以下,对本发明进行详细说明。首先对本发明的还原型辅酶Q10的制造方法进行说明。本发明的制造方法,是使用在侧链具有包含氮原子和/或氧原子的官能团的氨基酸类,将氧化型辅酶Q10还原的还原型辅酶Q10的制造方法。
作为本发明制造方法中的原料的氧化型辅酶Q10,可以仅为氧化型辅酶Q10,或者,也可以是氧化型辅酶Q10和还原型辅酶Q10的混合物。上述氧化型辅酶Q10为氧化型辅酶Q10和还原型辅酶Q10的混合物的情况下,氧化型辅酶Q10占辅酶Q10总量(即,还原型辅酶Q10和氧化型辅酶Q10的总量)的比例没有特别的限制,例如是1重量%以上,通常是5重量%以上,优选为10重量%以上,更优选为20重量%以上,特别优选为50重量%以上。其上限没有特别的限定,然而在氧化型辅酶Q10为氧化型辅酶Q10和还原型辅酶Q10的混合物的情况下,其上限通常为99.9重量%以下。当然,也可以是氧化型辅酶Q10为100重量%的情形,即,仅使用氧化型辅酶Q10。另外,这里使用的氧化型辅酶Q10可以通过例如合成、发酵、从天然产物提取等现有公知的方法得到。优选通过发酵、从天然产物提取而得到的物质。
在本发明的制造方法中,用于将氧化型辅酶Q10还原的成分,是在侧链具有包含特定杂原子的官能团的氨基酸类(以下也称作“本发明的氨基酸类”)。这里所述的杂原子是指氮原子、氧原子。因此,本发明中所述的在侧链具有包含杂原子的官能团的氨基酸类没有特别的限定,例如,是在侧链具有包含氮原子的官能团的氨基酸类,和/或在侧链具有包含氧原子的官能团的氨基酸类。
本发明氨基酸类的侧链杂原子是氮原子时,即,在本发明的制造方法中,将在侧链具有包含氮原子的官能团的氨基酸类作为将氧化型辅酶Q10还原的成分使用时,“包含氮原子的官能团”没有特别的限定,包括氨基、酰胺基、亚氨基、胍基、咪唑基、吲哚基等。另外,作为“在侧链具有包含氮原子的官能团的氨基酸类”,并不限于环状、非环状,另外,在环状的情况下,氮原子可以是和氨基酸的氨基共有的,具体地,可以列举出赖氨酸、精氨酸、色氨酸、脯氨酸、组氨酸、瓜氨酸、天冬酰胺、谷氨酰胺等。尤其是,从将氧化型辅酶Q10转换为还原型辅酶Q10的还原能力的观点出发,特别优选赖氨酸、精氨酸、色氨酸、脯氨酸,进一步特别优选赖氨酸、精氨酸、色氨酸。
本发明氨基酸类的侧链杂原子是氧原子时,即,在本发明的制造方法中,将在侧链具有包含氧原子的官能团的氨基酸类作为将氧化型辅酶Q10还原的成分使用时,“包含氧原子的官能团”没有特别的限定,包括羟基、羧基、羰基、醚基、酚基等。另外,作为“在侧链具有包含氧原子的官能团的氨基酸类”,具体地,可以列举出丝氨酸、酪氨酸、苏氨酸(羟丁氨酸)、天冬氨酸、谷氨酸、天冬酰胺、谷氨酰胺等,从将氧化型辅酶Q10转换为还原型辅酶Q10的还原能力的观点出发,特别优选丝氨酸。
在上述本发明的氨基酸类中,从还原反应的难易程度以及制造成本的观点出发,在侧链具有包含氮原子的官能团的氨基酸类是更有利的。
另外,这里举出的氨基酸类的形态没有特别的限定,可以是以下所述的水合物、盐、衍生物。作为氨基酸的水合物,可以列举如下:例如,赖氨酸水合物、赖氨酸盐酸盐水合物等。另外,作为盐,可以列举如下:例如,赖氨酸盐酸盐或精氨酸盐酸盐等盐酸盐、色氨酸硫酸盐等硫酸盐、赖氨酸钠盐等钠盐、赖氨酸钾盐等钾盐,等。另外,作为氨基酸的衍生物,可以列举出N-酰基体等。此外,这些氨基酸形成了肽键的多肽或蛋白质也可以包括在所述衍生物中。需要说明的是,这些氨基酸的绝对立体构型没有特别的限定,可以是L构型、D构型或消旋体。
另外,在本发明的制造方法中,反应开始时的氧化型辅酶Q10与本发明的氨基酸类的量的比,只要是能够将氧化型辅酶Q10还原为还原型辅酶Q10的有效量即可,没有特别的限定,通常,氨基酸类相对于氧化型辅酶Q10的当量通常为0.01当量以上,更优选为0.1当量以上,特别优选为1当量以上。其上限没有特别的限定,从制造成本或者作为营养素的有效性的观点出发,通常为1000当量以下,优选500当量以下,更优选250当量以下,特别优选100当量以下,尤其优选50当量以下,最优选10当量以下。
在本发明的制造方法中,只要作为原料的氧化型辅酶Q10和本发明的氨基酸类可以在反应体系中接触即可,该体系可以是均匀的,或者,也可以是不均匀的,没有特别的限定。可以列举如下:例如,氧化型辅酶Q10与本发明的氨基酸类分别以固体形式接触的情形;其中之一溶解到溶剂等中形成液体层,另一种以固体形式存在于该液体层中的情形;氧化型辅酶Q10以熔融液(融液)的形式存在,本发明的氨基酸类以固体形式存在于该熔融液中的情形;分别在液相中存在,形成液-液2层的情形;均在同一液相中存在的情形等。不言而喻,氧化型辅酶Q10和本发明的氨基酸类的接触效率高的体系,对氧化型辅酶Q10的还原更有效,基于该观点,最优选氧化型辅酶Q10和本发明的氨基酸类存在于同一液相中。
从上述观点出发,在本发明的制造方法中,进行还原反应时,为了使氧化型辅酶Q10和/或本发明的氨基酸类存在于液相中,优选使用溶剂。在本发明的制造方法中,作为还原反应时使用的溶剂没有特别的限定,可以列举如下:烃类、脂肪酸酯类、醚类、醇类、酮类、氮化合物类(包括腈类、酰胺类)、硫化合物类、脂肪酸类、萜烯类等有机溶剂,油脂,水等,它们可以单独使用,此外,也可以使用2种以上的混合溶剂。
作为上述烃类,没有特别的限定,可以列举如下:例如,脂肪烃、芳烃、卤代烃等。特别是,优选脂肪烃、芳烃,尤其优选脂肪烃。
作为脂肪烃,不限环状、非环状,也不限饱和、不饱和,没有特别的限定,特别优选使用非环状的脂肪烃。另外,通常使用碳原子数为3~20的脂肪烃、优选碳原子数为5~12的脂肪烃。作为脂肪烃的具体例子,可以列举如下:例如,丙烷、丁烷、异丁烷、戊烷、2-甲基丁烷、环戊烷、2-戊烯、己烷、2-甲基戊烷、2,2-二甲基丁烷、2,3-二甲基丁烷、甲基环戊烷、环己烷、1-己烯、环己烯、庚烷、2-甲基己烷、3-甲基己烷、2,3-二甲基戊烷、2,4-二甲基戊烷、甲基环己烷、1-庚烯、辛烷、2,2,3-三甲基戊烷、异辛烷、乙基环己烷、1-辛烯、壬烷、2,2,5-三甲基己烷、1-壬烯、癸烷、1-癸烯、对-烷、十一烷、十二烷等。其中,优选碳原子数为5~8的饱和脂肪烃,特别优选:戊烷、2-甲基丁烷、环戊烷、己烷、2-甲基戊烷、2,2-二甲基丁烷、2,3-二甲基丁烷、甲基环戊烷、环己烷、庚烷、2-甲基己烷、3-甲基己烷、2,3-二甲基戊烷、2,4-二甲基戊烷、甲基环己烷、辛烷、2,2,3-三甲基戊烷、异辛烷、乙基环己烷等。
作为芳烃,没有特别的限定,通常适宜使用碳原子数为6~20、特别是碳原子数为6~12、尤其是碳原子数为7~10的芳烃。作为芳烃的具体例子,可以列举如下:例如,苯、甲苯、二甲苯、邻二甲苯、间二甲苯、对二甲苯、乙苯、枯烯、(mesitylene)、四氢化萘、丁基苯、对甲基异丙基苯、环己基苯、二乙基苯、戊基苯、二戊基苯、十二烷基苯、苯乙烯等。芳烃优选为:甲苯、二甲苯、邻二甲苯、间二甲苯、对二甲苯、乙基苯、枯烯、四氢化萘、丁基苯、对甲基异丙基苯、环己基苯、二乙基苯、戊基苯,更优选为:甲苯、二甲苯、邻二甲苯、间二甲苯、对二甲苯、枯烯、四氢化萘,最优选为枯烯。
作为卤代烃,无论环状、非环状,也无论饱和、不饱和,没有特别的限定,通常优选使用非环状卤代烃。通常,优选氯代烃、氟代烃,特别优选氯代烃。适宜使用碳原子数为1~6,特别是碳原子数为1~4,尤其是碳原子数为1~2的卤代烃。作为卤代烃的具体例子,可以列举如下:例如,二氯甲烷、氯仿、四氯化碳、1,1-二氯乙烷、1,2-二氯乙烷、1,1,1-三氯乙烷、1,1,2-三氯乙烷、1,1,1,2-四氯乙烷、1,1,2,2-四氯乙烷、五氯乙烷、六氯乙烷、1,1-二氯乙烯、1,2-二氯乙烯、三氯乙烯、四氯乙烯、1,2-二氯丙烷、1,2,3-三氯丙烷、氯苯、1,1,1,2-四氟乙烷等。
卤代烃优选为:二氯甲烷、氯仿、四氯化碳、1,1-二氯乙烷、1,2-二氯乙烷、1,1,1-三氯乙烷、1,1,2-三氯乙烷、1,1-二氯乙烯、1,2-二氯乙烯、三氯乙烯、氯苯、1,1,1,2-四氟乙烷,更优选为:二氯甲烷、氯仿、1,2-二氯乙烯、三氯乙烯、氯苯、1,1,1,2-四氟乙烷。
作为上述脂肪酸酯类,没有特别的限定,可以列举如下:例如,丙酸酯、乙酸酯、甲酸酯等。脂肪酸酯类特别优选:乙酸酯、甲酸酯,尤其优选乙酸酯。虽然没有特别的限定,但是作为酯基,通常使用碳原子数为1~8的烷基酯或芳烷基酯,优选使用碳原子数为1~6的烷基酯,更优选使用碳原子数为1~4的烷基酯。
作为丙酸酯,可以列举如下:例如,丙酸甲酯、丙酸乙酯、丙酸丁酯、丙酸异戊基酯。
作为乙酸酯,可以列举如下:例如,乙酸甲酯、乙酸乙酯、乙酸丙酯、乙酸异丙酯、乙酸丁酯、乙酸异丁酯、乙酸仲丁酯、乙酸戊酯、乙酸异戊酯、乙酸仲己酯、乙酸环己酯、乙酸苄基酯等。乙酸酯优选为:乙酸甲酯、乙酸乙酯、乙酸丙酯、乙酸异丙酯、乙酸丁酯、乙酸异丁酯、乙酸仲丁酯、乙酸戊酯、乙酸异戊酯、乙酸仲己酯、乙酸环己酯,更优选为:乙酸甲酯、乙酸乙酯、乙酸丙酯、乙酸异丙酯、乙酸丁酯、乙酸异丁酯,最优选为乙酸乙酯。
作为甲酸酯,可以列举如下:例如,甲酸甲酯、甲酸乙酯、甲酸丙酯、甲酸异丙酯、甲酸丁酯、甲酸异丁酯、甲酸仲丁酯、甲酸戊酯等。甲酸酯优选为:甲酸甲酯、甲酸乙酯、甲酸丙酯、甲酸丁酯、甲酸异丁酯、甲酸戊酯,最优选为甲酸乙酯。
作为上述醚类,无论环状、非环状,而且无论饱和、不饱和,没有特别的限定,通常优选使用饱和的醚。通常,适宜使用碳原子数为3~20、特别是碳原子数为4~12,尤其是碳原子数为4~8的醚。作为醚类的具体例子,可以列举如下:例如,二乙基醚、甲基叔丁基醚、二丙基醚、二异丙基醚、二丁基醚、二己基醚、乙基乙烯基醚、丁基乙烯基醚、苯甲醚、苯乙醚、丁基苯基醚、甲氧基甲苯、二烷、呋喃、2-甲基呋喃、四氢呋喃、四氢吡喃、乙二醇二甲基醚、乙二醇二乙基醚、乙二醇二丁基醚、乙二醇单甲基醚、乙二醇单乙基醚、乙二醇二丁基醚等。醚类优选为:二乙基醚、甲基叔丁基醚、二丙基醚、二异丙基醚、二丁基醚、二己基醚、苯甲醚、苯乙醚、丁基苯基醚、甲氧基甲苯、二烷、2-甲基呋喃、四氢呋喃、四氢吡喃、乙二醇二甲基醚、乙二醇二乙基醚、乙二醇二丁基醚、乙二醇单甲基醚、乙二醇单乙基醚,更优选为:二乙基醚、甲基叔丁基醚、苯甲醚、二烷、四氢呋喃、乙二醇单甲基醚、乙二醇单乙基醚,进一步优选为:二乙基醚、甲基叔丁基醚、苯甲醚等,最优选为甲基叔丁基醚。
作为上述醇类,无论环状、非环状,而且也无论饱和、不饱和,没有特别的限定,一般优选使用饱和的醇。通常,优选碳原子数为1~20、特别是碳原子数为1~12、尤其是碳原子数为1~6、进一步是碳原子数为1~5的一元醇,或者优选碳原子数为2~5的二元醇,或者优选碳原子数为3的三元醇。
作为一元醇,可以列举如下:例如,甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、异丁醇、叔丁醇、1-戊醇、2-戊醇、3-戊醇、2-甲基-1-丁醇、异戊醇、叔戊醇、3-甲基-2-丁醇、新戊醇、1-己醇、2-甲基-1-戊醇、4-甲基-2-戊醇、2-乙基-1-丁醇、1-庚醇、2-庚醇、3-庚醇、1-辛醇、2-辛醇、2-乙基-1-己醇、1-壬醇、1-癸醇、1-十一醇、1-十二醇、烯丙醇、炔丙醇、苯甲醇、环己醇、1-甲基环己醇、2-甲基环己醇、3-甲基环己醇、4-甲基环己醇等。一元醇优选为:甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、异丁醇、叔丁醇、1-戊醇、2-戊醇、3-戊醇、2-甲基-1-丁醇、异戊醇、叔戊醇、3-甲基-2-丁醇、新戊醇、1-己醇、2-甲基-1-戊醇、4-甲基-2-戊醇、2-乙基-1-丁醇、环己醇,更优选为:甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、异丁醇、叔丁醇、1-戊醇、2-戊醇、3-戊醇、2-甲基-1-丁醇、异戊醇、叔戊醇、3-甲基-2-丁醇、新戊醇,进一步优选为甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、异丁醇、2-甲基-1-丁醇、异戊醇,最优选为乙醇。
作为二元醇,可以列举出1,2-乙二醇、1,2-丙二醇、1,3-丙二醇、1,2-丁二醇、1,3-丁二醇、1,4-丁二醇、2,3-丁二醇、1,5-戊二醇等。二元醇优选为:1,2-乙二醇、1,2-丙二醇、1,3-丙二醇,最优选为1,2-乙二醇。
作为三元醇,适合使用甘油等。
作为上述酮类,没有特别的限定,通常适合使用碳原子数为3~6的酮。作为酮类的具体例子,可以列举如下:例如,丙酮、甲乙酮、甲基丁基酮、甲基异丁基酮等,优选为:丙酮、甲乙酮,最优选为丙酮。
作为上述腈类,无论环状、非环状,而且也无论饱和、不饱和,没有特别的限定,一般优选使用饱和的腈。通常,适合使用碳原子数为2~20、特别是碳原子数为2~12、尤其是碳原子数为2~8的腈。作为腈类的具体例子,可以列举如下:例如,乙腈、丙腈、丙二腈、丁腈、异丁腈、丁二腈、戊腈、戊二腈、己腈、辛腈、壬基腈、十一腈、十二腈、十三腈、十五腈、硬脂腈、氯代乙腈、溴代乙腈、氯代丙腈、溴代丙腈、甲氧基乙腈、氰基乙酸甲酯、氰基乙酸乙酯、甲苯基腈、苯甲腈、氯代苯甲腈、溴代苯甲腈、氰基苯甲酸、硝基苯甲腈、茴香腈、酞腈、溴代甲苯基腈、氰基苯甲酸甲酯、甲氧基苯甲腈、乙酰基苯甲腈、萘甲腈、联苯基腈、苯基丙腈、苯基丁腈、甲基苯基乙腈、二苯基乙腈、萘乙腈、硝基苯基乙腈、氯代苯乙腈、环丙腈、环己腈、环庚腈、苯基环己基腈、甲苯基环己腈等。腈类优选为:乙腈、丙腈、丁二腈、丁腈、异丁腈、戊腈、氰基乙酸甲酯、氰基乙酸乙酯、苯甲腈、甲苯基腈、氯代丙腈,更优选为乙腈、丙腈、丁腈、异丁腈,最优选为乙腈。
作为上述氮化合物类,除了上述腈类以外,可以列举如下:例如,硝基甲烷、乙腈、三乙胺、吡啶、甲酰胺、N-甲基甲酰胺、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基吡咯烷酮等。
作为硫化合物类,可以列举如下:例如,二甲基亚砜、环丁砜等。
作为上述脂肪酸类,可以列举如下:例如,甲酸、乙酸、丙酸、辛酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、异硬脂酸、油酸、亚油酸、亚麻酸、花生四烯酸、二月桂酸、二十碳五烯酸、二十二碳六烯酸、二十二碳五烯酸等,优选:甲酸、乙酸、辛酸、癸酸、油酸、亚油酸、亚麻酸、花生四烯酸、二十碳五烯酸、二十二碳六烯酸、二十二碳五烯酸,特别优选:乙酸、油酸、亚油酸、亚麻酸、花生四烯酸、二十碳五烯酸、二十二碳六烯酸、二十二碳五烯酸,进一步优选为:油酸、亚油酸、亚麻酸、二十碳五烯酸、二十二碳六烯酸,最优选为油酸。
作为上述萜烯类,无论环状、非环状,而且也无论饱和、不饱和,没有特别的限定。作为萜烯类,通常,可以列举出半萜、单萜、倍半萜、二萜、三萜、四萜等。作为萜烯类的具体例子,可以列举如下:例如,普楞醇、3-基-3-丁烯-2-醇、顺芷酸、当归酸、千里光酸、异戊酸、别罗勒烯、α-甜没药萜烯、甜没药萜烯、β-波旁烯、δ-杜松烯、δ-3-蒈烯、α-丁子香烯、β-丁子香烯、对甲基异丙基苯、脱氢-对甲基异丙基苯、薄荷醇、柠檬烯、d-柠檬烯、l-柠檬烯、顺-3,7-二甲基-1,3,6,-辛三烯、δ-榄香烯、β-榄香烯、α-金合欢烯、β-金合欢烯、金合欢烯、大根香叶烯D,β-愈创烯、长叶烯、香叶烯、β-罗勒烯、α-水芹烯、α-蒎烯、β-蒎烯、松莰酮、桧烯、α-萜品烯、γ-萜品烯、萜品油烯、斧柏烯、瓦伦亚烯(Valencene)、、氢化柠檬烯二聚物、异丁子香烯、蒎烯二聚物、二戊烯二聚物、二戊烯三聚物、香叶醇、柠檬醛、香茅醛、香茅醇、1,8-桉树脑、羟基香茅醛、沉香醇、波斯菊萜、橙花醇、月桂烯醇、熏衣草醇、齿小蠹二烯醇、橙花醛、香叶醛、二萘嵌苯、玫瑰呋喃、香叶酸(geranyl acid)、硫代萜品醇、α-萜品醇、β-萜品醇、γ-萜品醇、δ-萜品醇、香芹醇、萜二醇、紫苏醛、紫苏醇、香芹酮、驱蛔素、茴香脑、侧柏酮、侧柏醇、α-紫罗酮、β-紫罗酮、γ-紫罗酮、金合欢醇、橙花叔醇、α-甜橙醛、β-甜橙醛、甜没药萜醇、叶绿醇、角鲨烯、香茅氧基乙醛(citronellyloxyacetoaldehvde)、桃金娘烯醛、紫苏醛、2-对枯醇(2-p-Cymenol)、2-乙氧基一对甲基异丙基苯、香芹烯醇、4-香芹烯醇、乙酸香芹酯、丙酸香芹酯、丁香醇、乙酸丁香醇酯、1,4-桉树脑、丁子香酚、d-芹子烯、百里香酚、d-莰烯、乙酸沉香酯等。萜烯类优选为:普楞醇、3-甲基-3-丁烯-2-醇、顺芷酸、当归酸、千里光酸、异戊酸、别罗勒烯、α-甜没药萜烯、甜没药萜烯、β-波旁烯、δ-杜松烯、δ-3-蒈烯、α-丁子香烯、β-丁子香烯、对甲基异丙基苯、脱氢-对甲基异丙基苯、柠檬烯、d-柠檬烯、l-柠檬烯、顺-3,7-二甲基-1,3,6,-辛三烯、δ-榄香烯、β-榄香烯、α-金合欢烯、β-金合欢烯、金合欢烯、大根香叶烯D,β-愈创烯、长叶烯、香叶烯、β-罗勒烯、α-水芹烯、α-蒎烯、β-蒎烯、松莰酮、桧烯、α-萜品烯、γ-萜品烯、萜品油烯、斧柏烯、瓦伦亚烯(Valencene)、、氢化柠檬烯二聚物、异丁子香烯、蒎烯二聚物、二戊烯二聚物、二戊烯三聚物、香叶醇、柠檬醛、香茅醛、香茅醇、1,8-桉树脑、羟基香茅醛、沉香醇、橙花醇、月桂烯醇、橙花醛、香叶醛、香芹酮、茴香脑、侧柏酮、叶绿醇、角鲨烯、丁子香酚、d-芹子烯、百里香酚、乙酸沉香酯,特别优选为:α-甜没药萜烯、甜没药萜烯、δ-杜松烯、α-丁子香烯、β-丁子香烯、柠檬烯、d-柠檬烯、l-柠檬烯、香叶烯、α-水芹烯、α-蒎烯、β-蒎烯、α-萜品烯、γ-萜品烯、香叶醇、柠檬醛、香茅醇、1,8-桉树脑、沉香醇、香芹酮、茴香脑、侧柏酮、丁子香酚、d-芹子烯、百里香酚、乙酸沉香酯,最优选为:柠檬烯、d-柠檬烯。
另外,还可以使用含有上述萜烯类的精油作为溶剂。关于精油没有特别的限定,可以列举出橙油、辣椒油、芥末油、大蒜油、苋蒿子(キャラゥェ一)油、丁香油、肉桂油、可可提取物、咖啡豆提取物、姜油、留兰香油、芹菜籽油、百里香油、洋葱油、肉豆蔻油、欧芹籽油、薄荷油、香草提取物、小茴香油、胡薄荷油、薄荷油、桉叶油、柠檬油、玫瑰油、迷迭香油、杏仁油、香旱芹油、茴香油、香树油、当归根油、黄葵油、龙蒿油、牛至油、鸢尾根油、乳香油、肉桂油、卡藜油、衣兰油、春黄菊油、白菖蒲油、小豆蔻油、胡萝卜籽油、荜澄茄油、枯茗油、葡萄柚油、桂叶油、杜松油、胡椒油、木香根油、康酿克油(コニャック油)、、芫荽叶油、紫苏子油、麝香、杜松子油、八角茴香油、鼠尾草油、香薄荷油、老鹳草油、红橘油、莳萝油、苦橙花油、吐鲁香脂油、罗勒油、桦木油、绿叶油、玫瑰草油、多香果油、橙叶油、桂叶油、香柠檬油、秘鲁香脂油、安息香树脂、玫瑰木油、酒花油、波罗尼花原精、甘牛至油、橘子油、香桃木油、柚子香料、白柠檬油、杂薰衣草油、熏衣草油、芸香油、柠檬草油、蘑菇香精、独活草油、月桂叶油、苦艾油等。
上述有机溶剂中,优选醇类、脂肪酸类、萜烯类,更优选醇类,醇类中,最优选乙醇。
作为上述油脂,可以是来自动植物的天然油脂,也可以是合成油脂或加工油脂。作为植物油脂,可以列举如下:例如,椰子油、棕榈油、棕榈仁油、亚麻籽油、山茶油、糙米胚芽油、菜籽油、米油、花生油、玉米油、小麦胚芽油、大豆油、苏子油、棉籽油、葵花籽油、木棉油、月见草油、牛油树油脂、婆罗脂、可可脂、芝麻油、红花油、橄榄油、鳄梨油、罂粟子油、牛蒡子油等;作为动物油脂,可以列举:例如,猪脂、乳脂、鱼油、牛脂等,以及将上述油脂通过分级、氢化、酯交换等进行加工而得的油脂(例如硬化油)。当然也可以使用中链脂肪酸甘油三酯(MCT)、脂肪酸的部分甘油酯等。另外,还可以使用它们的混合物。作为中链脂肪酸甘油三酯没有特别的限定,可以列举如下:例如,脂肪酸的碳原子数分别为6~12、优选为8~12的甘油三酯等。
上述油脂中,从处理的容易程度、臭气等方面出发,优选植物油脂、合成油脂、加工油脂。其中,具体而言,优选:椰子油、棕榈油、棕榈仁油、菜籽油、米油、大豆油、棉籽油、红花油、橄榄油、中链脂肪酸甘油三酯(MCT)、脂肪酸的部分甘油三酯等;特别优选米油、大豆油、菜籽油、红花油、中链脂肪酸甘油三酯、脂肪酸的部分甘油三酯等,从对氨基酸类的溶解性等的观点出发,最优选使用中链脂肪酸甘油三酯或者脂肪酸的部分甘油三酯。
上述溶剂中,优选食品、药品、化妆品等可接受的溶剂,更优选食品可接受的溶剂。从不对反应产物进行加工而可以直接摄取的观点以及反应性的观点出发,优选醇类、水、油脂、脂肪酸类、萜烯类或它们的混合物,最优选乙醇或水、或者含有乙醇或水的混合溶剂。
在本发明的制造方法中,可以在上述溶剂的存在下,使作为原料的氧化型辅酶Q10和作为还原剂的本发明的氨基酸类共存,从而进行还原反应,但是并不限于该方法。
另外,在本发明的制造方法中,在还原反应时,还可以在该反应体系中添加表面活性剂,或者在大多数情况下是优选添加的。
作为上述表面活性剂,没有特别的限定,可以列举如下:例如,甘油脂肪酸酯、蔗糖脂肪酸酯、有机酸单甘油酯、山梨糖醇酐脂肪酸酯、聚氧乙烯山梨糖醇酐脂肪酸酯、丙二醇脂肪酸酯、聚甘油缩合蓖麻醇酸酯、皂角苷、磷脂等。
作为上述甘油脂肪酸酯,没有特别的限定,可以列举如下:例如,甘油的聚合度是1~10的甘油脂肪酸酯。作为构成甘油脂肪酸酯的脂肪酸残基,没有特别的限定,优选使用脂肪酸的碳原子数分别是6~18的脂肪酸残基,可以列举:例如,辛酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、异硬脂酸、油酸、亚油酸、亚麻酸等。
作为上述蔗糖脂肪酸酯,没有特别的限定,可以列举如下:蔗糖的1个以上的羟基与碳原子数分别是6~22的脂肪酸形成了酯键的蔗糖脂肪酸酯,可以列举如下:例如,蔗糖月桂酸酯、蔗糖肉豆蔻酸酯、蔗糖棕榈酸酯、蔗糖硬脂酸酯、蔗糖油酸酯、蔗糖山嵛酸酯、蔗糖芥酸酯等。
作为上述有机酸单甘油酯,没有特别的限定,可以列举如下:单甘油辛酸琥珀酸酯、单甘油硬脂酸柠檬酸酯、单甘油硬脂酸乙酸酯、单甘油硬脂酸琥珀酸酯、单甘油硬脂酸乳酸酯、单甘油硬脂酸二乙酰基酒石酸酯、单甘油油酸柠檬酸酯等。
作为上述山梨糖醇酐脂肪酸酯,没有特别的限定,可以列举如下:山梨糖醇酐的1个以上的羟基和碳原子数分别是6~18的脂肪酸形成了酯键的山梨糖醇酐脂肪酸酯,可以列举如下:例如,山梨糖醇酐单月桂酸酯、山梨糖醇酐单棕榈酸酯、山梨糖醇酐单硬脂酸酯、山梨糖醇酐单油酸酯等。作为上述聚氧乙烯山梨糖醇酐脂肪酸酯,没有特别的限定,可以列举如下:例如,加成6mol~20mol环氧乙烷链的聚氧乙烯山梨糖醇酐单棕榈酸酯、聚氧乙烯山梨糖醇酐单硬脂酸酯、聚氧乙烯山梨糖醇酐单油酸酯、聚氧乙烯山梨糖醇酐三硬脂酸酯、聚氧乙烯山梨糖醇酐三油酸酯等。
作为上述聚甘油缩合蓖麻醇酸酯,没有特别的限定,可以列举如下:例如,聚甘油的平均聚合度是2~10、聚蓖麻醇酸的平均缩合度(蓖麻醇酸的缩合数的平均值)是2~4的聚甘油缩合蓖麻醇酸酯,可以列举如下:例如,四甘油缩合蓖麻醇酸酯、五甘油缩合蓖麻醇酸酯、六甘油缩合蓖麻醇酸酯等。
作为上述丙二醇脂肪酸酯,可以没有限制地使用单酯、二酯。作为构成丙二醇脂肪酸酯的脂肪酸残基,没有特别的限定,优选使用脂肪酸的碳原子数为6~18的脂肪酸残基,可以列举如下:例如,辛酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、异硬脂酸、油酸、亚油酸、亚麻酸等。
作为上述磷脂,没有特别的限定,可以列举如下:例如,蛋黄卵磷脂、纯化大豆卵磷脂、磷脂酰胆碱、磷脂酰乙醇胺、磷脂酰丝氨酸、神经鞘髓磷酶、双十六烷基磷酸、硬脂酰胺、磷脂酰甘油、磷脂酸、磷脂酰肌醇胺、心磷脂、神经酰胺磷酰基乙醇胺、神经酰胺磷酰基甘油以及它们的混合物等。当然也可以使用实施了氢化、酶分解等加工的磷脂。从提高还原型辅酶Q10的吸收性的观点出发,优选使用经酶分解的磷脂。
作为上述皂苷没有特别的限定,可以列举出槐树皂苷、皂树皂苷、纯化大豆皂苷、丝兰皂苷等。
在本发明的制造方法中,氧化型辅酶Q10相对于开始还原反应时的反应体系(全部反应液的总重量)的浓度没有特别的限定,通常是约0.01重量%以上,优选为约0.1重量%以上,更优选为约0.2重量%以上,特别优选为约1重量%以上,进一步优选为约2重量%以上,特别是约3重量%以上。
在本发明的制造方法中,对于还原反应时的反应温度没有特别的限定,通常在20℃以上,优选在30℃以上,更优选在40℃以上,进一步优选在50℃以上,特别优选在60℃以上,最优选在75℃以上进行。
为了最大限度地发挥出本发明的效果,上述还原反应优选例如在脱氧气体氛围下进行。脱氧气体氛围可以通过非活性气体置换、减压、沸腾或其组合来实现。至少适合使用非活性气体置换,即,使用非活性气体气体氛围。作为上述非活性气体,可以列举如下:例如,氮气、氦气、氩气、氢气、二氧化碳气体等,优选为氮气。
另外,在本发明的制造方法中,还原反应可以在制剂中进行。即,制备含有氧化型辅酶Q10和本发明的氨基酸类的混合物,将该混合物加工为制剂形态后,在该形态的制剂中,将氧化型辅酶Q10还原为还原型辅酶Q10以制造还原型辅酶Q10,也属于本发明的范畴。此时的还原可以通过保存一定时间以上或加温等进行。在本发明中,所述制剂是指胶囊剂(硬胶囊、软胶囊、微胶囊)、片剂、糖浆剂、饮料等口服给药形式,或者乳膏、栓剂、牙膏剂等形式。在制剂中进行还原反应时的制剂,优选为上述口服给药的形式,更优选为胶囊剂,特别优选使用软胶囊。
通过上述的本发明的制造方法,可以简便地制造还原型辅酶Q10。此时(反应结束时),还原型辅酶Q10占据辅酶Q10总量(即,还原型辅酶Q10和氧化型辅酶Q10的总量)的比例,通常为约10重量%以上,优选为约20重量%以上,更优选为30重量%以上,特别优选为40重量%以上,尤其是50重量%以上,特别是约60重量%以上,进而是80重量%以上。
通过本发明的制造方法得到的还原型辅酶Q10,在还原反应结束后,对其进行适当除去溶剂或进行分离、纯化操作,也可以得到粗纯化的或纯的还原型辅酶Q10,或者也可以将还原反应结束后的混合组合物作为含有还原型辅酶Q10和氨基酸类的组合物,将其直接地或将其制剂化后在药品、食品等领域中使用。
接着,对本发明的稳定化方法以及通过该方法稳定化的本发明的组合物(以下,统称为“本发明的稳定化方法和组合物”)进行说明。在本发明中,通过形成上述本发明的氨基酸类和还原型辅酶Q10共存的组合物,可以形成含有对氧化而言稳定的还原型辅酶Q10的组合物。即,本发明的稳定化方法,是使还原型辅酶Q10、和在侧链具有包含氮原子和/或氧原子的官能团的氨基酸类共存的还原型辅酶Q10的稳定化方法,本发明的组合物,是包含还原型辅酶Q10、和在侧链具有包含氮原子和/或氧原子的官能团的氨基酸类的组合物。
在本发明的稳定化方法和组合物中,组合物中含有的、作为稳定化对象的还原型辅酶Q10,可以仅是还原型辅酶Q10,或者,也可以是还原型辅酶Q10和氧化型辅酶Q10的混合物。在上述还原型辅酶Q10为还原型辅酶Q10和氧化型辅酶Q10的混合物的情况下,还原型辅酶Q10占据辅酶Q10总量(即,还原型辅酶Q10和氧化型辅酶Q10的总量)的比例没有特别的限定,通常是约10重量%以上,优选为约20重量%以上,更优选为30重量%以上,特别优选为40重量%以上,尤其是50重量%以上,进一步是60重量%以上,进而是80重量%以上。其上限没有特别的限定,通常是99.9重量%以下。当然,可以为还原型辅酶Q10为100重量%的情况,即仅使用还原型辅酶Q10。
在本发明的稳定化方法中和组合物中所使用的还原型辅酶Q10,例如可以利用合成、发酵、从天然产物提取等或者将氧化型辅酶Q10还原等现有公知的方法得到。本发明的稳定化方法和组合物中使用的还原型辅酶Q10,优选使用常规的还原剂,例如连二亚硫酸钠(连二亚硫酸钠)、硼氢化钠、抗坏血酸类等,将现有的高纯度辅酶Q10等氧化型辅酶Q10、或者氧化型辅酶Q10和还原型辅酶Q10的混合物还原得到,更优选使用抗坏血酸类,将现有的高纯度辅酶Q10等氧化型辅酶Q10或氧化型辅酶Q10与还原型辅酶Q10的混合物还原得到。另外,不用说,还可以使用通过上述本发明的制造方法得到的还原型辅酶Q10。
本发明的稳定化方法和组合物中使用的氨基酸类,是和上述本发明的制造方法相同的“在侧链具有包含特定杂原子的官能团的氨基酸类”,其具体例子以及详细说明也和本发明的制造方法中说明的相同。
在本发明的稳定化方法和组合物中,所使用的或者组合物中所含有的还原型辅酶Q10与本发明的氨基酸类的量的比没有特别的限定,通常本发明的氨基酸类相对于还原型辅酶Q10的当量,通常是0.01当量以上,更优选为0.1当量以上,特别优选为1当量以上。所述当量的上限没有特别的限定,但是从经济的观点出发,通常是1000当量以下,优选为500当量以下,更优选为250当量以下,特别优选为100当量以下,尤其优选为50当量以下,最优选为10当量以下,进一步优选为5当量以下。
在本发明的稳定化方法和组合物中,还原型辅酶Q10与本发明的氨基酸类在组合物中共存。这里所述的“共存,”,是指两者以任意的形态接触。作为接触形态没有特别的限定,组合物体系可以是均匀的,也可以是不均匀的。例如,可以列举如下:还原型辅酶Q10与本发明的氨基酸类分别以固体形式接触的情形;其中之一溶解在溶剂等中形成液体层,另一种以固体的形式存在于该液体层的情形;还原型辅酶Q10以熔融液的形式存在,本发明的氨基酸类以固体的形式存在于该熔融液中的情形;分别存在于液相中,形成液-液2层的情形;均在同一液相中存在的情形等。当然,还原型辅酶Q10与本发明的氨基酸类的接触效率高的体系对还原型辅酶Q10的稳定化是有效的,基于该观点,最优选还原型辅酶Q10与本发明的氨基酸类存在于同一液相中。
基于上述观点,在本发明的稳定化方法和组合物中,优选使用溶剂使组合物中的还原型辅酶Q10和/或本发明的氨基酸类存在于液相中,使组合物中含有的还原型辅酶Q10和/或本发明的氨基酸类共存。作为本发明的稳定化方法和组合物中使用的溶剂,没有特别的限定,和上述本发明的制造方法中提及的那些相同,可以列举如下:烃类、脂肪酸酯类、醚类、醇类、酮类、脂肪酸类、萜烯类、酮类、氮化合物类(包括腈类、酰胺类)、硫化合物类等有机溶剂,油脂,水等。
上述溶剂中,优选食品、药品、化妆品等可接受的溶剂,特别优选食品中可接受的溶剂。从直接摄取含有还原型辅酶Q10和氨基酸类的组合物的观点出发,尤其优选醇类、水、油脂、脂肪酸类、萜烯类作为溶剂,特别优选乙醇、水、油脂、脂肪酸类、萜烯类或它们的混合物,最优选乙醇或水、或者含有乙醇或水的混合溶剂。
此外,本发明的稳定化方法以及组合物中所使用的溶剂的详细种类以及优选的例子,也和本发明的制造方法中所说明的相同。
另外,本发明的稳定化方法以及组合物也和本发明的制造方法同样地,可以添加表面活性剂,而且大多情况下优选添加。本发明的稳定化方法以及组合物中所使用的表面活性剂的详细种类以及优选的例子也和本发明的制造方法中说明的相同。
对于本发明的稳定化方法和组合物而言,作为形成还原型辅酶Q10与本发明的氨基酸类共存的组合物时的制备方法,没有特别的限定。例如,使用外部添加的还原型辅酶Q10时,可以仅将还原型辅酶Q10与本发明的氨基酸类混合,或者将两者混合后,进一步混合上述的溶剂。另外,还可以在上述溶剂中含有还原型辅酶Q10的溶液中,混合本发明的氨基酸类,也可以在上述溶剂中含有本发明的氨基酸类的溶液中,混合还原型辅酶Q10,也可以将这些含有还原型辅酶Q10的溶液与含有本发明的氨基酸类的溶液混合。
或者,也可以直接使用通过上述本发明的制造方法得到的还原型辅酶Q10,即,将还原反应结束后的还原型辅酶Q10与氨基酸类共存的混合物直接用于本发明的稳定化方法和组合物,该实施方式是最优选的实施方式之
对于本发明的稳定化方法和组合物而言,作为可以在组合物中含有的除了还原型辅酶Q10与本发明的氨基酸类、其它根据需要使用的溶剂、表面活性剂以外的物质,例如可以包含赋形剂、崩解剂、润滑剂、粘合剂、色素、抗凝剂、吸收促进剂、增溶剂、稳定剂、香料、还原型辅酶Q10以外的活性成分等,没有特别的限定。
作为上述赋形剂,没有特别的限定,可以列举如下:例如,蔗糖、乳糖、葡萄糖、淀粉、糊精、甘露醇、晶体纤维素、磷酸钙、硫酸钙等。
作为上述崩解剂,没有特别的限定,可以列举如下:例如,淀粉、琼脂、柠檬酸钙、碳酸钙、碳酸氢钠、糊精、晶体纤维素、羧甲基纤维素、西黄蓍胶、海藻酸等。
作为上述润滑剂,没有特别的限定,可以列举如下:例如,滑石、硬脂酸镁、聚乙二醇、二氧化硅、硬化油等。
作为上述粘合剂,没有特别的限定,可以列举如下:例如,乙基纤维素、甲基纤维素、羟丙基甲基纤维素、羟丙基纤维素、西黄蓍胶、紫胶、明胶、支链淀粉、阿拉伯胶、聚乙烯吡咯烷酮、聚乙烯醇、聚丙烯酸、聚甲基丙烯酸、山梨糖醇等。
作为上述色素,没有特别的限定,可以列举如下:例如,氧化钛、食用色素、氧化铁红色素、红花色素、焦糖色素、栀子色素、焦油色素、叶绿素等色素。
作为上述抗凝剂,没有特别的限定,可以列举如下:例如,硬脂酸、滑石、轻质无水硅酸、含水二氧化硅等。
作为上述吸收促进剂,没有特别的限定,可以列举如下:例如,高级醇类、高级脂肪酸类等。
作为上述增溶剂,没有特别的限定,可以列举如下:例如,富马酸、琥珀酸、苹果酸等有机酸等。
作为上述稳定化剂,没有特别的限定,可以列举如下:例如,苯甲酸、苯甲酸钠、对羟基苯甲酸乙酯、蜂蜡、羟丙基甲基纤维素、甲基纤维素等。
作为上述香料,没有特别的限定,可以列举如下:橙油、辣椒油、芥末油、大蒜油、苋蒿子油、丁香油、肉桂油、可可提取物、咖啡豆提取物、姜油、留兰香油、芹菜籽油、百里香油、洋葱油、肉豆蔻油、欧芹籽油、薄荷油、香草提取物、小茴香油、胡薄荷油、薄荷油、桉叶油、柠檬油、玫瑰油、迷迭香油、杏仁油、香旱芹油、茴香油、香树油、当归根油、黄葵油、龙蒿油、牛至油、鸢尾根油、乳香油、肉桂油、卡藜油、衣兰油、春黄菊油、白菖蒲油、小豆蔻油、胡萝卜籽油、荜澄茄油、枯茗油、葡萄柚油、桂叶油、杜松油、胡椒油、木香根油、康酿克油(コニャック油)、、芫荽叶油、紫苏子油、麝香、杜松子油、八角茴香油、鼠尾草油、香薄荷油、老鹳草油、红橘油、莳萝油、苦橙花油、吐鲁香脂油、罗勒油、桦木油、绿叶油、玫瑰草油、多香果油、橙叶油、桂叶油、香柠檬油、秘鲁香脂油、安息香树脂、玫瑰木油、酒花油、波罗尼花原精、甘牛至油、橘子油、香桃木油、柚子香料、白柠檬油、杂薰衣草油、熏衣草油、芸香油、柠檬草油、蘑菇香精、独活草油、月桂叶油、苦艾油等。
作为上述还原型辅酶Q10以外的活性成分,可以列举如下:例如,维生素、矿物质、多酚、有机酸、糖类、肽、蛋白质等。
上述物质可以起到多种用途。例如,淀粉可以起到赋形剂和崩解剂的作用。
在本发明的稳定化方法和组合物中,相对于组合物的全部重量,本发明的氨基酸类的含量没有特别的限定,但是从充分发挥出还原型辅酶Q10的稳定化效果的观点出发,通常是约0.01重量%以上,优选为约0.1重量%以上,更优选为约1重量%以上,进一步优选为5重量%以上,特别优选为10重量%以上。本发明的氨基酸类的含量的上限没有特别的限定,但是从经济或者作为营养素的有效性等观点出发,通常是约70重量%以下,优选为约50重量%以下,更优选为约30重量%以下。
在本发明的稳定化方法和组合物中,相对于组合物的总重量,还原型辅酶Q10的含量没有特别的限定,从确保组合物中的还原型辅酶Q10的有效性的观点出发,通常是约0.001重量%以上,优选为约0.01重量%以上,更优选为约0.1重量%以上,特别优选为约1重量%以上。还原型辅酶Q10的含量的上限没有特别的限定,优选为约50重量%以下,更优选为约30重量%以下,特别优选为约20重量%以下。
为了最大限度地发挥出本发明的效果,优选在脱氧气体氛围下实施本发明的稳定化方法,或者制备和/或保存本发明的组合物。另外,加工为上述制剂或加工后的保存也优选在脱氧气体氛围下进行。脱氧气体氛围可以通过非活性气体置换、减压、沸腾或其组合来实现。至少适合使用非活性气体置换,即,使用非活性气体氛围。作为上述非活性气体,可以列举:例如,氮气、氦气、氩气、氢气、二氧化碳气体等,优选为氮气。
另外,本发明的组合物也可以直接使用,也可以加工为本发明的制造方法中记载的制剂,即,胶囊剂(硬胶囊、软胶囊、微胶囊)、片剂、糖浆剂、饮料等口服给药形式或者乳膏、栓剂、牙膏剂等形式使用。其中,优选加工为上述口服给药的形式,特别优选为胶囊剂,尤其优选加工为软胶囊形式。作为在此的胶囊基材,没有特别的限定,以来自牛骨、牛皮、猪皮、鱼皮等的明胶为代表,也可以使用其它基材(例如,能够作为食品添加剂使用的角叉菜胶、褐藻酸等来自海藻的产品、以及刺槐豆胶或瓜尔胶等来自植物种子的产品等的增稠稳定剂,或含有纤维素类的制造用材料)。
本发明的组合物,不仅可以保护作为有效成分还原型辅酶Q10不被氧化,可稳定地保存,而且稳定化中所使用的氨基酸类对生物体的安全性优异,此外,其作为营养素也是有效的,因此,可以期待本发明的组合物是安全的、而且还可以实现与还原型辅酶Q10的协同效果,得到作为营养功能食品、特定保健用食品等食品或者作为添加剂、饮料、药品、动物药、化妆品、宠物食品等有用的组合物。
另外,利用上述本发明的制造方法来制造本发明的组合物时,不仅可以使用廉价的氧化型辅酶Q10作为原料,而且证明了将氧化型辅酶Q10还原时所使用的氨基酸类对生物体的安全性,因此,在还原反应结束后无需进行分离除去,此外,还可以将组合物中残留的本发明的氨基酸类直接用于还原型辅酶Q10的稳定化,因此,从制造的观点来看,其优势高。通过利用这种可以原位得到含有还原型辅酶Q10的组合物的本发明,可以降低含有还原型辅酶Q10的组合物的制造成本,可以提供廉价的含有还原型辅酶Q10的组合物。
实施例
以下,举出实施例对本发明进行更详细地说明,但是本发明并不受到这些实施例的限定。另外,实施例中的还原型辅酶Q10的纯度、还原型辅酶Q10和氧化型辅酶Q10的重量比,通过下述HPLC分析求得,得到的还原型辅酶Q10的纯度并不是规定本发明纯度的极限值,而且同样地,还原型辅酶Q10和氧化型辅酶Q10的重量比也不规定其上限值。需要说明的是,在本实施例中,为了简便地表述还原型辅酶Q10和氧化型辅酶Q10的重量比,将还原型辅酶Q10占据辅酶Q10总量(氧化型辅酶Q10和还原型辅酶Q10的总量)的比例用百分比表示,作为“还原型辅酶Q10的重量比”。例如,记载“还原型辅酶Q10的重量比为20%”的情况下,是指还原型辅酶Q10和氧化型辅酶Q10的重量比为20/80。
(HPLC分析条件)
柱:SYMMETRY C18(Waters制造)250mm(长度)、4.6mm(内径),流动相:C2H5OH:CH3OH=4:3(v:v),检测波长:210nm,流速:1ml/分钟,还原型辅酶Q10的保留时间:9.1分钟,氧化型辅酶Q10的保留时间:13.3分钟。
(实施例1)
分别将0.3g(0.36mmol)的氧化型辅酶Q10晶体和6当量(2.16mmol)的表1记载的氨基酸加入到4.5g的乙醇中,在氮气体氛围、78℃下边加热边搅拌16小时。反应后的反应液中的还原型辅酶Q10的重量比通过HPLC分析的结果示于表1中。
[表1]
实施例1
(实施例2)
将0.3g(0.36mmol)氧化型辅酶Q10晶体和6当量(2.16mmol)的色氨酸加入到Span80(0.4g)、甘油(0.3g)、Tween80(4.9g)、MCT(1.4g)的混合液中,在氮气体氛围、80℃下边加热边搅拌16小时。反应后的反应液中的还原型辅酶Q10的重量比通过HPLC分析的结果示于表2中。
(比较例1)
将0.3g(0.36mmol)氧化型辅酶Q10晶体和6当量(2.16mmol)的L-半胱氨酸以及N-乙酰基半胱氨酸,分别加入Span80(0.4g)、甘油(0.3g)、Tween80(4.9g)、MCT(1.4g)的混合液中,在氮气体氛围、80℃下边加热边搅拌16小时。反应后的反应液中的还原型辅酶Q10的重量比通过HPLC分析的结果示于表2中。
[表2]
实施例2
还原型辅酶Q10的重量比 | |
色氨酸 | 33% |
比较例1
(实施例3)
相对于0.3g(0.36mmol)氧化型辅酶Q10晶体,在4.5g柠檬烯中分别加入6当量(2.16mmol)的脯氨酸或6当量(2.16mmol)的丝氨酸,在氮气体氛围、85℃下边加热边搅拌16小时。反应后的反应液中的还原型辅酶Q10的重量比通过HPLC分析的结果,分别为8%、3%。
(实施例4)
将0.3g(0.36mmol)的氧化型辅酶Q10晶体和6当量(2.16mmol)的色氨酸加入到缩合蓖麻醇酸酯(CR-310,阪本药品工业制造)(3.8g)、MCT(3.8g)的混合液中,在氮气体氛围、80℃下边加热边搅拌16小时。反应后的反应液中的还原型辅酶Q10的重量比通过HPLC分析的结果为5%。
(比较例2)
分别将0.3g(0.36mmol)的氧化型辅酶Q10晶体和6当量(2.16mmol)的表3记载的氨基酸加入到4.5g乙醇中,在氮气体氛围、78℃下边加热边搅拌16小时。反应后的反应液中的还原型辅酶Q10的重量比通过HPLC分析的结果示于表3中。
(比较例3)
分别将0.3g(0.36mmol)的氧化型辅酶Q10晶体和6当量(2.16mmol)的表3记载的氨基酸加入到Span80(0.4g)、甘油(0.3g)、Tween80(4.9g)、MCT(1.4g)的混合液中,在氮气体氛围、80℃下边加热边搅拌16小时。反应后的反应液中的还原型辅酶Q10的重量比通过HPLC分析的结果示于表3中。
(比较例4)
分别将0.3g(0.36mmol)的氧化型辅酶Q10晶体和6当量(2.16mmol)的表3记载的氨基酸加入到4.5g柠檬烯中,在氮气体氛围、85℃下边加热边搅拌16小时。反应后的反应液中的还原型辅酶Q10的重量比通过HPLC分析的结果示于表3中。
(比较例5)
分别将0.3g(0.36mmol)的氧化型辅酶Q10晶体和6当量(2.16mmol)的表3记载的氨基酸加入到缩合蓖麻醇酸酯(CR-310,阪本药品工业制造)(3.8g)、MCT(3.8g)的混合液中,在氮气体氛围、80℃下边加热边搅拌16小时。反应后的反应液中的还原型辅酶Q10的重量比通过HPLC分析的结果示于表3中。
[表3]
比较例2~5
比较例2 | 比较例3 | 比较例4 | 比较例5 | |
甘氨酸 | 0% | 0% | 0% | 1% |
缬氨酸 | 1% | 0% | 0% | 0% |
异亮氨酸 | 1% | 1% | 0% | 0% |
亮氨酸 | 0% | 0% | 0% | 1% |
丙氨酸 | 0% | 0% | 0% | 0% |
本说明书中引用的所有的刊物、专利和专利申请直接作为参考引入本说明书中。
Claims (13)
1.还原型辅酶Q10的制造方法,该方法包括:使用在侧链具有包含氮原子和/或氧原子的官能团的氨基酸类,将氧化型辅酶Q10还原,其中氨基酸类为选自赖氨酸、精氨酸、色氨酸和脯氨酸中的至少1种氨基酸和/或丝氨酸。
2.根据权利要求1所记载的制造方法,其中,还原反应在有机溶剂、油脂、水或它们的混合物的共存下进行。
3.根据权利要求2所记载的制造方法,其中,有机溶剂是选自醇类、脂肪酸类和萜烯类中的至少1种。
4.根据权利要求1所记载的制造方法,其中,还原反应在制剂中进行。
5.根据权利要求4所记载的制造方法,其中,制剂是胶囊剂。
6.根据权利要求1所记载的制造方法,其中,还原反应在脱氧气体氛围下进行。
7.还原型辅酶Q10的稳定化方法,该方法包括使还原型辅酶Q10与在侧链具有包含氮原子和/或氧原子的官能团的氨基酸类共存,其中氨基酸类为选自赖氨酸、精氨酸、色氨酸和脯氨酸中的至少1种氨基酸和/或丝氨酸。
8.组合物,其包含还原型辅酶Q10与氨基酸类,所述氨基酸类在侧链具有包含氮原子和/或氧原子的官能团,其中氨基酸类为选自赖氨酸、精氨酸、色氨酸和脯氨酸中的至少1种氨基酸和/或丝氨酸。
9.根据权利要求8所记载的组合物,其中,在组合物中进一步含有有机溶剂、油脂、水或它们的混合物。
10.根据权利要求9所记载的组合物,其中,有机溶剂是选自醇类、脂肪酸类和萜烯类中的至少1种。
11.根据权利要求8所记载的组合物,其中,组合物中的还原型辅酶Q10的含量是0.01重量%以上。
12.根据权利要求8所记载的组合物,其中,组合物中的还原型辅酶Q10是通过在侧链具有包含氮原子和/或氧原子的官能团的氨基酸类还原而得到的物质,其中氨基酸类为选自赖氨酸、精氨酸、色氨酸和脯氨酸中的至少1种氨基酸和/或丝氨酸。
13.根据权利要求8所记载的组合物,其中,组合物中的还原型辅酶Q10是外部添加的物质。
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