CN101849935B - 芝麻素/异芝麻素组合物 - Google Patents
芝麻素/异芝麻素组合物 Download PDFInfo
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- CN101849935B CN101849935B CN201010139607XA CN201010139607A CN101849935B CN 101849935 B CN101849935 B CN 101849935B CN 201010139607X A CN201010139607X A CN 201010139607XA CN 201010139607 A CN201010139607 A CN 201010139607A CN 101849935 B CN101849935 B CN 101849935B
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Abstract
本发明提供一种增强了芝麻素类生理活性的芝麻素/异芝麻素组合物。通过以一定的重量比含有芝麻素和异芝麻素,提供增强了异芝麻素的经口吸收性及/或血中移行性的口服组合物。还通过以一定的重量比含有芝麻素和异芝麻素,提供增强了芝麻素类生理活性的口服组合物。
Description
本申请是中国专利申请第200510135319.6号的分案申请,第200510135319.6号的专利申请的申请日是2005年12月28日,发明名称是“芝麻素/异芝麻素组合物”。
技术领域
本发明涉及一种含有芝麻素及异芝麻素的组合物(芝麻素/异芝麻素组合物),其由于含有规定比例的芝麻素和为其差向异构体(异构体)的异芝麻素,所以可提高芝麻素类所具有的生理活性。
本发明还涉及添加或含有该芝麻素/异芝麻素组合物的饮食品、液体饮料及医药组合物、动物饲料或宠物食品。
背景技术
在本发明中,芝麻素类是芝麻素和异芝麻素的总称。且在本发明中,将芝麻素及异芝麻素的混合物表示为芝麻素/异芝麻素组合物。
异芝麻素及芝麻素是立体异构体的关系。即芝麻素(sesamin)是具有化学结构式I:
〔化合物1〕
所示结构的光学活性化合物,并且,其异构体异芝麻素(episesamin)是具有化学结构式II:
〔化合物2〕
所示结构的光学活性化合物。如上化学结构式所示,芝麻素具有平面对称结构,而异芝麻素具有非对称结构。
芝麻素是芝麻中主要的木脂素化合物之一,在芝麻籽中含有0.1%~0.5%。与此相对,异芝麻素在原本的芝麻籽中并不存在,是在从芝麻油到色拉油等的精炼处理(脱色、脱臭)过程中,芝麻素差向异构化而生成的次要产物(非专利文献1),并已知此由芝麻油精炼的芝麻素类含有基本上为1∶1(重量比)的芝麻素类和异芝麻素(非专利文献2)。
在以往的技术文献中,揭示了有关芝麻类的以下的生理活性。例如,从使用经精炼的芝麻素的实验中,证实了抑制肠内胆固醇或胆汁酸代谢的作用(专利文献1)、缓和酒精中毒或戒断症状的作用(专利文献2)、改善肝功能的作用(专利文献3)、多不饱和脂肪酸在体内的稳定化作用(专利文献4)、Δ5-去饱和酶抑制作用(非专利文献3~4、专利文献5)、抑制偏头疼的作用(专利文献6)、对人体白血病细胞凋亡诱导作用(专利文献7)、褐黑激素的氧化分解抑制作用(专利文献8)等。并且,上述专利文献5中的Δ5-去饱和酶抑制作用、上述专利文献7中的对人体白血病细胞凋亡诱导作用,不仅从精炼后的芝麻素中得到了确认,从异芝麻素中也得到了确认。
另外,从使用含有芝麻素的芝麻油的实验中,明示了炎症性疾病(肌肉萎缩性侧索硬化症)的改善作用(专利文献9)、抗炎症及感染防护作用(专利文献10)、与含有α-亚麻酸、二十碳五烯酸、二十二碳六烯酸中至少一种的油脂并用可预防和改善过敏的作用(专利文献11)等。
并且,有关芝麻素/异芝麻素组合物还有以下的报告。例如,从使用以木脂素类化合物为主要成分的芝麻油提取物(芝麻素19.6%、异芝麻素30.6%、芝麻素酚及异芝麻素酚10.2%、木脂素类化合物含量为60.4%)的实验中,证实了降低血液中胆固醇的作用及降低血液中中性脂肪的作用(专利文献12)、改善肝功能作用(专利文献3)等。另外,从使用经精练的芝麻素/异芝麻素组合物的试验,例如,使用芝麻素∶异芝麻素约等于6∶4的实验中,证实了改善肝功能作用(芝麻素:61.5%、异芝麻素:38.0%)(专利文献3)、去除活性氧作用(芝麻素∶异芝麻素约等于6∶4)(专利文献13)、防止恶醉作用(芝麻素:55.2%、异芝麻素:44.4%、纯度为99.6%)(专利文献14)、过敏症状的预防及改善作用(芝麻素:55.2%、异芝麻素:44.4%、纯度为99.6%)(专利文献15)等,从使用芝麻素∶异芝麻素约等于1∶1的试验中,也证实了ω6系列·ω3系列不饱和脂肪酸的平衡调节作用(芝麻素:51.3%、异芝麻素:47.8%)(专利文献16)、抑制过氧化脂质的生成(芝麻素:51.3%、异芝麻素:47.8%)(专利文献17)、抑制乳腺癌的作用(芝麻素:51.3%、异芝麻素:47.8%)(专利文献18)、抗高血压作用(芝麻素:51.5%、异芝麻素:47.8%、其他的二氧杂二环(dioxabicyclo)[3,3,0]辛烷衍生物为1.1%)(专利文献19)、减少体脂肪的作用(芝麻素∶异芝麻素约等于1∶1、纯度为99.5%)(专利文献20)、与锯棕榈油并用抑制前列腺肥大的效果(芝麻素∶异芝麻素约等于1∶1)(专利文献21)等。
并且近年来还证实了芝麻素与异芝麻素生理活性的不同之处。例如,有文献报道,从把芝麻素和异芝麻素的混合物(约为1∶1)向大鼠经口投药后在体内的分布上,可看出异芝麻素向内脏器官的移行量高于芝麻素的2倍以上(非专利文献5)。同时还有文献报道了从把芝麻素和异芝麻素分别向大鼠经口投药的试验中,与芝麻素相比,异芝麻素可使肝脏的β氧化酶的基因表达以及酶活性显著上升,而在抑制脂肪酸合成酶的活性上,芝麻素与异芝麻素则无差异(非专利文献6)。
[专利文献1]日本专利第3183664号
[专利文献2]美国专利第4427694号
[专利文献3]日本专利第3075358号
[专利文献4]日本特开平11-269456号公报
[专利文献5]日本专利第3070611号
[专利文献6]日本特开2003-183172号公报
[专利文献7]日本特开2001-151676号公报
[专利文献8]日本特开2000-143546号公报
[专利文献9]日本特表2005-533042号公报
[专利文献10]日本特表平10-500937号公报
[专利文献11]日本特开平5-58902号公报
[专利文献12]日本专利第3001589号
[专利文献13]日本特开平6-227977号公报
[专利文献14]日本专利第3124062号
[专利文献15]日本专利第3512196号
[专利文献16]日本专利第3512196号
[专利文献17]日本特开平5-051388号公报
[专利文献18]日本特开平5-43458号公报
[专利文献19]日本特开平8-268887号公报
[专利文献20]日本专利第3205315号
[专利文献21]日本特开2000-256204号公报
[非专利文献1]《芝麻的科学和功能性》、并木等、丸善PLANET株式会社(1998)
[非专利文献2]Fukuda,Y.,et al.,J.Am.Oil.Chem.Soc.,63,1027-1031(1986)
[非专利文献3]S.Shimizu,et al,J.Am.Oil Chem.Soc.,66,237-241(1989)
[非专利文献4]S.Shimizu,et al.,Lipid,26,512(1991)
[非专利文献5]Sawada R.,et al.,Lipids,34,633(1999)
[非专利文献6]Kushiro M.,et al.J.Nutr.Biochem.,13,289-295(2002)
发明内容
如上所述,芝麻素类虽具有各种生理活性,但在天然芝麻籽中只含有0.1%~0.5%左右,是一种珍贵的化合物。因此,本申请人为使芝麻素类所具有的生理活性得到更有效地发挥,而研究增强芝麻素类作用的方法,发现了α-维生素E可增强芝麻素类等的二氧杂二环(dioxabicyclo)[3,3,0]辛烷衍生物的作用(专利第3283274号)。但是,使芝麻素类自身的生理活性增强的方法还完全不得而知。
基于如下考虑,如能使芝麻类自身的生理活性增强,即可使芝麻素类所具有的有用的生理活性更高效且有效地得到发挥,所以本发明者等针对使芝麻素类自身的生理活性增强的方法进行了锐意研究。
首先,从与芝麻素相比,异芝麻素可使肝脏中的β氧化酶的基因表达以及酶活性显著上升(非专利文献6)中,设想至少在改善肝功能的作用上异芝麻素应与芝麻素具有同等以上的活性,并通过使异芝麻素在体内得到更有效地吸收,探讨使芝麻素类所具有的生理活性增强的方法。具体地说,在配制的芝麻素/异芝麻素组合物(油溶试剂)中,使其含有的芝麻素和异芝麻素具各种重量比,并探讨其在经口投药时异芝麻素的经口吸收·血中移行性。根据上述非专利文献5及6所述,曾设想在异芝麻素单独投药时血中移行性应最高,但令人惊讶的是,与此设想相反,在使用有一定量芝麻素共存的芝麻素/异芝麻素组合物时,比起异芝麻素的单独投药,其异芝麻素的经口吸收性及/或血中移行性更高。并且,在研究芝麻素类所具有的生理活性即抗高血压作用、肝脏的β氧化酶的基因表达时,令人惊讶的是,发现按规定比例(50∶50~1∶99)配合芝麻素和异芝麻素的芝麻素/异芝麻素组合物,具有比芝麻素单独投药及异芝麻素单独投药更高的活性,使本发明得以完成。
附图说明
图1是表示将种种芝麻素∶异芝麻素组成比(4∶6、5∶5、3∶7、2∶8、1∶9、0∶10)的混合物在经口投药时异芝麻素的经口吸收率的棒状图。
图2是表示将种种芝麻素∶异芝麻素组成比(1∶9、0.5∶9.5、0∶10)的混合物在经口投药时异芝麻素的经口吸收率的棒状图。
图3是表示将种种芝麻素∶异芝麻素组成比(10∶0、5∶5、0∶10)的混合物单次投药时DOCA-盐高血压大鼠的24小时的血压变化图。
图4是表示将种种芝麻素∶异芝麻素组成比(10∶0、5∶5、0∶10)的混合物投药后,第8小时的DOCA-盐高血压大鼠的血压变化图。
图5是表示将种种芝麻素∶异芝麻素组成比(5∶5、3∶7、1∶9)的混合物投药后,第8小时的DOCA-盐高血压大鼠的血压变化图。
图6是表示将种种芝麻素∶异芝麻素组成比(10∶0、5∶5、3∶7、1∶9、0∶10)的混合物投药时对β氧化基因表达的影响图。
具体实施方式
本发明涉及一种使芝麻素类的生理活性能更高效且有效地发挥的芝麻素/异芝麻素组合物,及通过使用此组合物,而使芝麻素类的生理活性增强的方法。具体地说,
1.一种芝麻素/异芝麻素组合物,其特征为含有重量比为50∶50~1∶99的芝麻素和异芝麻素。
2.上述1所述的芝麻素/异芝麻素组合物,其特征为含有重量比为39∶61~1∶99的芝麻素和异芝麻素。
3.上述1所述的芝麻素/异芝麻素组合物,其特征为含有重量比为30∶70~5∶95的芝麻素和异芝麻素。
4.上述1~3中任一项所述的芝麻素/异芝麻素组合物,其特征为芝麻素及异芝麻素的总量为等于或大于组合物的重量百分比的51%。
5.饮食品,其含有上述1~4中所述的芝麻素/异芝麻素组合物。
6.医药组合物,其含有上述1~4中所述的芝麻素/异芝麻素组合物。
7.动物饲料或宠物食品,其含有上述1~4中所述的芝麻素/异芝麻素组合物。
8.通过上述1~4中所述的芝麻素/异芝麻素组合物,使芝麻素类的生理活性增强的方法。
9.根据上述8中所述的方法,上述芝麻素类的生理活性为降低血液中胆固醇的作用、降低中性脂肪的作用、抗高血压作用、不饱和脂肪酸的抗氧化作用、改善肝功能的作用、去除活性氧的作用、Δ5去饱和酶抑制作用及多不饱和脂肪酸在体内的稳定化作用。
本发明中的芝麻素/异芝麻素组合物,其特征为含有规定比例的芝麻素和异芝麻素。芝麻素和异芝麻素的优选比例为50∶50~1∶99(重量比)、更优选为39∶61~1∶99,最优选为30∶70~5∶95。含有上述规定比例的芝麻素和异芝麻素的本发明的芝麻素/异芝麻素组合物,与异芝麻素单独投药相比,具有异芝麻素的经口吸收性及/或血中移行性更高的性质。并且,含有上述规定比例的芝麻素和异芝麻素的本发明的芝麻素/异芝麻素组合物,与芝麻素的单独投药及异芝麻素的单独投药相比,芝麻素类所具有的生理特性,即抗高血压作用、改善肝功能作用及改善脂类代谢作用得到增强,因其具有此特征,所以能更高效且有效地发挥芝麻素类所具有的生理活性。
对本发明中芝麻素/异芝麻素组合物的制造方法无特别限制,例如,本发明的组合物可将芝麻素及异芝麻素的精制品按所需比率配合制造。此时,芝麻素及异芝麻素的精制品例如可使用非专利文献2中所述的方法制成,其详细内容将在后述实施例1中阐述。但是,精制品亦可由其他适当的方法获得。
本发明的其他的形态为,可求出含有芝麻素及异芝麻素的原料混合物中两成分的重量比,在该混合物中,添加芝麻素或异芝麻素的精制品、(或者含有的芝麻素或异芝麻素的一方比另一方多的混合物),以达到本发明所规定的芝麻素-异芝麻素的组成比。
本发明还有其他的形态,可将芝麻素从芝麻素和异芝麻素的混合物(例如、组成比为1∶1)中去除而成。去除芝麻素可通过将再结晶、色谱分离法、蒸馏等方法单独或适当组合进行。
特别是在其他的形态中,本发明可通过对芝麻素、芝麻素-异芝麻素混合物或异芝麻素施以异构化反应,以调节芝麻素-异芝麻素的组成比。
并且还可使用本发明者等为提高芝麻素-异芝麻素混合物中异芝麻素的浓度,而在近年开发的如下方法。即,
在酒精或酒精水溶液中溶解芝麻素-异芝麻素混合物,之后,用再结晶的方法将异芝麻素选择性地结晶析出,以得到提高了异芝麻素浓度的芝麻素/异芝麻素混合物的方法。
另外,作为其他方法,可通过将芝麻素-异芝麻素混合物加热溶解于特定的油脂中,之后用再结晶法使异芝麻素有选择地结晶析出,以得到提高了异芝麻素浓度的芝麻素/异芝麻素混合物。
特别是还可利用将芝麻素-异芝麻素混合物溶解于水、水溶性溶剂或其混合物中,根据需要加入碱后,析出芝麻素类,以得到提高了异芝麻素浓度的芝麻素/异芝麻素混合物的方法。
在本发明实施时,原料混合物及本发明的组合物中芝麻素-异芝麻素的组成,可通过高速液体色谱法(HPLC)等公知的分析方法得到。
含有上述芝麻素及异芝麻素的原料混合物,例如,可例举为从芝麻籽、芝麻粕及芝麻油中精制的芝麻木脂素组合物。芝麻木脂素组合物可为购入的市场销售品(例如、竹本油脂制),也可从芝麻油中获得,其方法如上述非专利文献2所述,或用水蒸汽蒸馏芝麻油得到馏出物,在碱的存在下从馏出物中析出分离芝麻素类的方法(参照日本特开平10-7676号)等,已知的方法有很多。而且作为含有芝麻素及异芝麻素的原料混合物,不局限于从上述的芝麻籽、芝麻粕及芝麻油中精制的芝麻木脂素组合物,实质上含有其成分的,如五加皮、桐木、白果树皮等均可使用。
本发明的芝麻素/异芝麻素组合物具有异芝麻素的经口吸收性及/或血中移行性高的性质。异芝麻素的经口吸收性及血中移行性,例如,可通过后述的实施例2中所述的方法(通过LC-MS/MS定量)进行确认,但使用其他适当的方法也可。
因本发明的芝麻素/异芝麻素组合物具有异芝麻素的经口吸收性及/或血中移行性更高的性质,所以可使异芝麻素所具有的各种作用更高效且有效地发挥。异芝麻素的作用可例举为提高芝麻素类向内脏器官的移行性及改善肝功能的作用等。
另外,本发明的芝麻素/异芝麻素组合物与芝麻素单独投药及异芝麻素的单独投药相比,虽其详细机理还尚不明确,但因具有芝麻素类所具有的生理活性更高的性质,所以可使芝麻素类所具有的各种生理活性得到更高效且有效地发挥。芝麻素类的生理活性可例举为降低血液中胆固醇及中性脂肪的作用、抗高血压的作用、不饱和脂肪酸的抗氧化作用、改善肝功能的作用、去除活性氧的作用、Δ5去饱和酶抑制作用及多不饱和脂肪酸在体内的稳定化作用等。
本发明的芝麻素/异芝麻素组合物也适宜以饮食品或医药品组合物的形态使用。只要具有其功能,对于添加于饮食品或医药品组合物中的本发明的芝麻素/异芝麻素组合物的比例,无特别限制,通常可从0.01%~100%(重量百分比)的范围内选择。且对于该饮食品或医药品组合物中含有的异芝麻素的含量,其一次的经口摄取量应为0.5~100mg,优选为1~60mg,更优选为3~60mg。
含有有关本发明的芝麻素/异芝麻素组合物的饮食品或医药品组合物的制造,可通过将本发明的芝麻素/异芝麻素组合物添加于饮食品中进行,也可将芝麻素、异芝麻素及/或芝麻素-异芝麻素混合物同时或分别添加,以使含有的芝麻素和异芝麻素具本发明的重量比。两化合物重量比的调节,可使用与芝麻素/异芝麻素组合物制造有关的、已被记载的方法。
对含有本发明的芝麻素/异芝麻素组合物的饮食品或医药品组合物的形态,无特别限制,例如可配制成粉状、粒状、片状等的固状,液状、乳液状等的溶液状或充填了其溶液状组合物的胶囊,或糊状等的半固体状等的任意形态。
此时,在本发明的芝麻素/异芝麻素组合物中,可进一步配合稀释剂、载体或添加剂等成分进行任意的制剂化处理,以配制制剂。只要不影响芝麻素类的生理活性,对此处的稀释剂或载体均无特别限制,可例举为蔗糖、葡萄糖、果糖、麦芽糖、海藻糖、乳糖、低聚糖、糊精、葡聚糖、环状糊精、淀粉、糖稀、异构化液糖等的糖类、乙醇、丙二醇、丙三醇等的醇类、山梨糖醇、甘露糖醇、赤藓醇、乳糖醇、木糖醇、麦芽糖醇、还原性帕拉金糖、还原淀粉分解物等的糖醇类、三乙酸甘油酯等的溶剂、阿拉伯胶、角叉菜胶、黄原胶、瓜尔豆胶、结冷胶、果胶等的多糖类或水。另外添加剂可例举为螯合剂等的辅助剂、香料、香辛料提取物、防腐剂等。
为使用方便等,使用上述稀释剂、载体或添加剂配制上述制剂时,在100%(重量百分比)的制剂中,最好配制成含有的芝麻素/异芝麻素组合物的比例为0.01%~100%(重量百分比),优选为0.1%~50%(重量百分比)。此时,作为原料的芝麻素/异芝麻素组合物,例如使用芝麻素和异芝麻素的总量小于组合物51%的组合物时,因芝麻素类含量低,如需配合需要量的芝麻素类,所得到的含有芝麻素/异芝麻素组合物的制剂的体积就会过大,摄取时会产生不便。特别是将本发明的芝麻素/异芝麻素组合物溶解于油脂中,以生产用于经口投药的软胶囊等的制剂时,或需加大制剂,或需一次服用大量粒数的制剂,不仅使服用产生障碍,还会产生服用大量超出需要量的作为溶剂的油脂的问题。因此,从服用量越少越好的观点出发,最好使用芝麻素/异芝麻素组合物,使配制后芝麻素和异芝麻素的总量等于或大于组合物的51%,且特别优选使用纯度为90%或90%以上的芝麻素/异芝麻素组合物。
作为含有芝麻素/异芝麻素组合物的饮食品,如营养补助食品,可例举为,其是直接以上述本发明的芝麻素/异芝麻素组合物为有效成分的饮食品,以及在一般的饮食品中将上述本发明的芝麻素/异芝麻素组合物作为成分之一配合,并使其具有芝麻素类的生理活性的机能性食品(包括特定保健用食品、具附加条件的特定保健食品)。且在这些饮食品中,也包含如下饮食品,其特征为将其所具有的以降低血液中胆固醇及/或中性脂肪为主的生理作用表示于容器或说明书上,并含有或添加具本发明所规定的重量比的芝麻素及异芝麻素。在可表明的饮食品的其他生理作用中,还包含抗高血压作用、不饱和脂肪酸的抗氧化作用、改善肝功能的作用、去除活性氧的作用、Δ5去饱和酶抑制作用及多不饱和脂肪酸在体内的稳定化作用等。
对作为对象的饮食品无限制,可例举为果汁饮料、清凉饮料、运动饮料、酒精饮料及茶等的饮料,面包、面条类、米饭、点心类(饼干、蛋糕、糖果、巧克力、日式点心),豆腐及其加工品等的农产食品,清酒、药用酒、甜料酒、食醋、酱油、酱等的发酵食品,调味汁、沙拉酱、黄油、人造奶油、起酥油、食用油脂等的油脂食品,酸奶、火腿、咸猪肉、香肠等的蓄产食品,鱼糕、炸鱼糕、鱼肉山芋饼等的水产食品等、另外可利用动物饲料或宠物食品。
实施例
通过以下实施例,更具体地说明本发明,但本发明不只限于此。
实施例1.芝麻素及异芝麻素的精制
芝麻素及异芝麻素混合物(含有芝麻素及异芝麻素的原料混合物),使用购入的竹本油脂制的混合物[芝麻素类的纯度:99.5%、芝麻素∶异芝麻素的配比为51.8%∶48.0%(重量百分比)]。
芝麻素及异芝麻素的高纯度精制品通过使用以下条件的反相系HPLC方法配制。即,将溶解于DMSO中的100mg上述混合物注入Develosil ODS-UG-5(20Φ×250mm、野村化学公司制)的色谱柱中,通过20%→80%的乙腈直线梯度(洗脱时间:100分钟,流速:5ml/分钟)洗脱,再通过在280nm吸光度的检测分离,分离获得芝麻素(保留时间:89分钟)38.9mg、异芝麻素(保留时间:94分钟)35.0mg。将反复进行10次此操作后所得到的各种精制样品(所有的纯度均为99%或99%以上)用于实施例2的试验。
实施例2.芝麻素-异芝麻素的组成比与经口吸收·血中移行性-1
从日本CHARLES RIVER公司购入SD(IGS)系雄性大鼠(6周龄),在试验环境下驯化一星期后,将发育顺利的动物供作试验。将经一夜禁食后的大鼠每组5只分成6组,把实施例1中所得到的高纯度芝麻素和异芝麻素以各种组成比配合后,将所得到的芝麻素/异芝麻素混合物[芝麻素∶异芝麻素(重量比)=6∶4、5∶5、4∶6、3∶7、1∶9、0∶10]以10mg/kg的用量溶解于橄榄油中,用经口注入器(sonde)经口投药。在投药前、投药后的1、2、4、6、8、24小时后,从尾静脉用肝素采血管采血,经离心分离操作(8,000rpm、10min)后得到血浆样品。添加内部标准,用Oasis HLB固相提取,并将提取液减压浓缩后,用甲醇悬浮,过滤器过滤后用LC-MS/MS进行芝麻素及异芝麻素的定量。芝麻素或异芝麻素的量,通过芝麻素及异芝麻素各自的峰面积与作为内部标准使用的桉脂素(FUNAKOSHI株式会社)的峰面积的比来决定。LC-MS/MS的分析条件如下所示。
(HPLC)
色谱柱:Develosil C30-UG-5(5μm、2.0Φ×50mm、野村化学公司制)
流动相:A:蒸馏水、B:甲醇、D:100mM乙酸铵水溶液
流速:0.25mL/min
梯度:B液为55%、D液为10%、2分钟,之后,3分钟、B液从55%到60%、D液为10%,2分钟、B液从60%到85%、D液为10%的线性梯度
(MS/MS)
测定模式:选择反应监测
检测:异芝麻素(保留时间:约5.6分钟);母离子m/z=372([M+NH4]+)、子离子m/z=233
:桉脂素(保留时间:约2.8分钟);母离子m/z=404([M+NH4]+)、子离子m/z=249
离子化法:ESI法
血液中异芝麻素的浓度在投药后到约6小时上升到最高值,之后逐渐减少,24小时之后基本上在血液中检测不出异芝麻素。将0-24小时血液中的浓度曲线的曲线下面积(Area under the curve;AUC)作为吸收量的指标。因各投药组中异芝麻素的投药量不同,所以应通过将各AUC用异芝麻素投药量比除后补正算出吸收率,并与其相比较。其结果如图1所示。对于异芝麻素单独投药时吸收率为72.5,用芝麻素∶异芝麻素为50∶50的配比投药时得到了76.7的更高的吸收率。特别是,随着异芝麻素重量配比的增加吸收率也随之上升,配比为30∶70时吸收率达最高值,为10∶90时其也显示了高值。换句话说,也说明将芝麻素和异芝麻素以50∶50~10∶90的组成比配合时,比异芝麻素单独(0∶100重量比)投药,其异芝麻素的吸收率更高。
因此,本实施例的结果显示了通过用一定的重量比配合芝麻素和异芝麻素,可提高异芝麻素的吸收率。
实施例3.芝麻素-异芝麻素的组成比与经口吸收·血中移行性-2
以规定有效的芝麻素配比为目的,根据实施例2的方法,评价其在进一步降低芝麻素配比时的作用。换句话说,把实施例1中得到的高纯度的芝麻素和异芝麻素以各种组成比配合,将所得到的芝麻素/异芝麻素混合物[芝麻素∶异芝麻素(重量比)=1∶9、0.5∶9.5、0∶10]以10mg/kg的用量溶解于橄榄油中,并用经口注入器(sonde)经口投药,计算出吸收率。其结果如图2所示。对于异芝麻素单独投药时吸收率为59.7,得到了用芝麻素∶异芝麻素为5∶95的配比投药时吸收率为64.7,用10∶90的配比投药时吸收率为72.4的更高的吸收率。同时也可说明,即使将芝麻素和异芝麻素以5∶95的组成比配合时,也比异芝麻素单独(0∶100重量比)投药时异芝麻素的吸收率高。
实施例4.对于脱氧皮质甾酮乙酸盐(Deoxycorticosterone
acetate-salt)(DOCA-盐salt)高血压模型大鼠的血压降低的作用
对SD系雄性大鼠(6周龄)(日本SLC株式会社)在戊巴比妥钠麻醉下施行右肾摘出手术。恢复1星期后,将DOCA-salt每周2次、以15mg/kg的用量进行皮下投药,再将1%的食盐水作为饮用水投喂。使用无创自动血压测定装置(BP-98A、Softron、东京)通过尾袖套法测定收缩期血压[Systolic blood pressure(SBP)]。DOCA-salt处理开始后第5星期进行血压测定,并使用被确认为血压充分上升了的动物进行实验。在禁食8小时的大鼠中,作为对照组将橄榄油使用经口注入器(sonde)单次经口投药,作为试验组把实施例1中得到的高纯度的芝麻素和异芝麻素以各种组成比配合后,所得到的芝麻素/异芝麻素混合物[芝麻素∶异芝麻素(重量比)=10∶0、5∶5、0∶10]以100mg/kg用量悬浮于橄榄油中,并使用经口注入器(sonde)单次经口投药。在投药前、投药后的2、4、6、8、10、12、24小时后测定SBP。从第12小时测定血压后开始喂食。试验的实施间隔设定为1星期,对同一个体的测定最多进行3次。
单次投药后24小时的血压变化(n=5~7)如图3所示。在芝麻素单独、异芝麻素单独及橄榄油投药组中,未看出血压有大的变化,而在芝麻素/异芝麻素混合物(5∶5)投药组中,则显示了投药8小时后具有峰值的显著的血压降低的作用。将投药8小时后的血压变化在各组中进行比较,芝麻素/异芝麻素混合物(5∶5)投药组在8小时后的血压值为-32mmHg,与芝麻素单独组(-13mmHg)、异芝麻素单独组(-6mmHg)相比显著降低了(图4)。
实施例5.对于DOCA-盐高血压模型大鼠的血压降低作用-混合比的
影响
以下以效果最强的芝麻素/异芝麻素混合物(5∶5)为基准,根据实施例3的方法,对因配比不同其效果的差异进行了比较试验。且因投药量为100mg/kg时效果过强,所以为更容易看出差异,将量降到1/2进行。
把芝麻素·异芝麻素以各种组成比配合后的芝麻素/异芝麻素混合物[芝麻素∶异芝麻素(重量比)=5∶5、3∶7、1∶9]以50mg/kg用量溶解于橄榄油中,使用经口注入器(sonde)单次经口投药,并测定血压值。
投药8小时后的血压变化(n=3~4)如图5所示。在芝麻素/异芝麻素混合物(5∶5)50mg/kg用量中,未显示出血压降低的作用。而与此相对,在芝麻素/异芝麻素混合物(3∶7)及(1∶9)混合物中显示出血压降低的作用,特别是在3∶7时效果最为显著。
以上结果显示,通过将芝麻素和异芝麻素以一定的配比混合,可具有相乘地降低血压的效果。并且,其效果在配比为3∶7时最为显著。
实施例6.对β氧化基因表达的影响
从日本CLEAR购入Wistar系雄性大鼠(6周龄),在试验环境下驯化一星期后,将发育顺利的动物供作试验。将动物每组5只分成6组,对照组中将作为溶剂的橄榄油间隔24小时、3次经口投药,另外在试验组中把实施例1中得到的高纯度的芝麻素和异芝麻素以各种组成比配合后,将所得到的芝麻素/异芝麻素混合物[芝麻素∶异芝麻素(重量比)=10∶0、5∶5、3∶7、1∶9、0∶10]以200mg/kg的用量悬浮于橄榄油中,间隔24小时、3次经口投药。最后投药4小时后,用戊巴比妥钠麻醉并摘出肝脏,提取RNA后,通过使用TaqMan Chemistry定量RT-PCR法(Heid CA,Stevens J,Livak KJ,Williams PM.Real time quantitative PCR.Genome Res.1996 6(10):986-94.),探讨了对β氧化基因(10种)表达的影响。
评价后的基因如下表1所示,基因表达量如图6(图6A、B)所示。在本条件下的芝麻素单独投药组中,β氧化基因表达虽基本上未显示出上升,但在异芝麻素单独投药组中,有很多基因显示了上升。并且,不论在芝麻素/异芝麻素混合物投药组的任一组中,均比异芝麻素单独组显示出显著的基因表达的上升。对配比不同引起的基因表达的不同虽由于基因不同而有若干差异,但各组间均无太大的差异。
表1评价基因一览
以上结果显示,通过将异芝麻素和芝麻素混合,使β氧化基因的表达具有相乘的增强效果。
[制剂例]
以下注明制剂例。其“混合物”是指芝麻素∶异芝麻素的组成比在本发明的范围内(芝麻素∶异芝麻素=30∶70、纯度为99.5%)的芝麻素/异芝麻素组合物。
(制剂例1)黄油
“混合物” 1.2g
黄油脂肪 100g
乙酸维生素E 1.2g
在通过由黄油制造过程的搅拌操作(搅奶油)去除酪乳后的黄油脂肪100g中加入“混合物”1.2g,再加入1.2g的乙酸维生素E进行混匀操作(working),以得到组织均匀的含有本发明组合物的黄油。
(制剂例2)颗粒剂
“混合物” 0.25g
乙酸维生素E 0.25g
二氧化硅 20.5g
玉米淀粉 79g
将以上的粉体混合均匀后,加入10%羟丙基纤维素·乙醇溶液100ml,并用通常方法捏合、挤出、干燥,以制成颗粒剂。
(制剂例3)片剂
“混合物” 3.5g
乙酸维生素E 0.5g
二氧化硅 20g
微结晶纤维素 10g
硬脂酸镁 3g
乳糖 60g
将上述物质混合,用单冲压片机压片,以制造直径为7mm、重量为100mg的片剂。
(制剂例4)胶囊
明胶 70.0%
甘油 22.9%
对羟基苯甲酸甲酯 0.15%
对羟基苯甲酸丙酯 0.51%
水 适量
计 100%
在含有上述成分的软胶囊剂的囊皮中,用通常方法充填如下所示的组合物,制成1粒为200mg的软胶囊。
“混合物” 10.8mg
小麦蜂蜡 30mg
α-维生素E 20mg
棕榈油 10mg
小麦胚芽油 适宜
计 100%
(制剂例5)健康饮料
呈味:DL-酒石酸钠 0.1g
琥珀酸 0.009g
甜味:液糖 800g
酸味:柠檬酸 12g
维生素:维生素C 10g
“混合物” 1g
维生素E 30g
环糊精 5g
香料 15ml
氯化钾 1g
硫酸镁 0.5g
配合上述成分,加水制成10升。此健康饮料的1次饮用量约为100ml。
通过服用本发明的芝麻素/异芝麻素组合物,可使芝麻素类所具有的各种生理活性得到更有效地发挥。特别是,因本发明的芝麻素/异芝麻素组合物具有良好的异芝麻素的经口吸收性及血中移行性,所以可使异芝麻素类所具有的各种生理活性得到更有效地发挥。并且,在异芝麻素中通过配合一定比例的芝麻素,可相乘地增强芝麻素类所具有的降低血压的作用及β氧化基因的表达。再加上因芝麻素及异芝麻素来源于植物,所以具有温和的作用且安全性极高。因此,本发明组合物非常有效,其应用范围不只限于健康食品,在医药品上同样适用。
Claims (8)
1.芝麻素在制造用于提高异芝麻素的经口吸收性及/或血中移行性的组合物中的用途,其中,所述组合物含有重量比为50∶50~10∶90的芝麻素和异芝麻素。
2.根据权利要求1所述的用途,其中所述组合物含有重量比为39∶61~10∶90的芝麻素和异芝麻素。
3.根据权利要求1所述的用途,其中所述组合物含有重量比为30∶70~10∶90的芝麻素和异芝麻素。
4.芝麻素和异芝麻素在制造用于提高芝麻素类的生理活性的组合物中的用途,其中,所述组合物含有重量比为50∶50~10∶90的芝麻素和异芝麻素。
5.根据权利要求4所述的用途,其中所述组合物含有重量比为39∶61~10∶90的芝麻素和异芝麻素。
6.根据权利要求4所述的用途,其中所述组合物含有重量比为30∶70~10∶90的芝麻素和异芝麻素。
7.根据权利要求1~6中任一项所述的用途,其中所述组合物为饮食品。
8.根据权利要求1~6中任一项所述的用途,其中所述组合物为医药组合物。
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US (1) | US20080275110A1 (zh) |
EP (1) | EP1842540A4 (zh) |
JP (1) | JP4995567B2 (zh) |
KR (1) | KR101244586B1 (zh) |
CN (2) | CN101849935B (zh) |
AU (1) | AU2005320579B2 (zh) |
CA (1) | CA2592532C (zh) |
HK (2) | HK1088333A1 (zh) |
MY (1) | MY148121A (zh) |
SG (1) | SG158183A1 (zh) |
TW (1) | TW200633696A (zh) |
WO (1) | WO2006070856A1 (zh) |
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KR101327649B1 (ko) | 2005-03-31 | 2013-11-12 | 산토리 홀딩스 가부시키가이샤 | 리그난류 화합물 함유 수중 유적형 에멀션 및 그것을함유하는 조성물 |
KR101303435B1 (ko) * | 2005-09-30 | 2013-09-05 | 산토리 홀딩스 가부시키가이샤 | 에피세사민 고함유 조성물의 제조 방법 및 장치 |
EP2002832A4 (en) | 2006-03-31 | 2009-11-11 | Suntory Holdings Ltd | COMPOSITION WITH A LIGNAN CONNECTION |
JP5409989B2 (ja) * | 2006-04-03 | 2014-02-05 | サントリーホールディングス株式会社 | セサミン類含有動物用飲食物 |
WO2008044550A1 (fr) * | 2006-10-04 | 2008-04-17 | Suntory Limited | Émulsion de type huile/eau/huile contenant un composé de lignane, et composition la contenant |
JP5276316B2 (ja) * | 2007-12-28 | 2013-08-28 | サントリーホールディングス株式会社 | セサミン類及びケルセチン配糖体を含有する組成物 |
CN101342148B (zh) * | 2008-07-03 | 2012-09-05 | 姚英 | 一种速效抗菌消炎、抗病毒的超浓缩天然蒜素片及其制备方法 |
JP5547891B2 (ja) * | 2008-12-26 | 2014-07-16 | サントリーホールディングス株式会社 | セサミン類とエピガロカテキンガレートとを含有する組成物 |
WO2013187391A1 (ja) * | 2012-06-14 | 2013-12-19 | サントリーホールディングス株式会社 | セサミン類とγ-オリザノールと米胚芽油とを含有する組成物 |
JP2015140315A (ja) * | 2014-01-29 | 2015-08-03 | 中日本カプセル 株式会社 | ソフトカプセル用の充填組成物 |
CN107405329B (zh) * | 2015-03-23 | 2021-04-09 | 三得利控股株式会社 | 昼夜节律改善用组合物 |
CN114514022A (zh) * | 2019-10-04 | 2022-05-17 | 三得利控股株式会社 | 维持生活活动量、预防其降低、抑制或改善其降低用组合物 |
CN113812618A (zh) * | 2020-06-18 | 2021-12-21 | 陈信行 | 腐植酸芝麻素复方及其制程 |
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CA2172855C (en) * | 1989-07-21 | 2000-02-15 | Yoshifumi Shinmen | Cholesterol or neutral fat level reducer |
US5211953A (en) * | 1989-07-21 | 1993-05-18 | Suntory, Limited | Liver function improver |
JP3001589B2 (ja) * | 1989-07-21 | 2000-01-24 | サントリー株式会社 | リグナン類含有飲食物 |
JP3075358B2 (ja) * | 1990-04-03 | 2000-08-14 | サントリー株式会社 | 肝機能改善剤 |
JP3283274B2 (ja) * | 1991-06-15 | 2002-05-20 | サントリー株式会社 | 新規組成物 |
JPH08268887A (ja) * | 1995-02-01 | 1996-10-15 | Suntory Ltd | 高血圧症又はそれに起因する医学的症状の予防又は改善剤 |
JP3512196B2 (ja) * | 1995-07-04 | 2004-03-29 | サントリー株式会社 | オメガ6系・オメガ3系不飽和脂肪酸のバランス調節剤を配合してなる食品組成物 |
JP3205315B2 (ja) * | 1999-04-28 | 2001-09-04 | リノール油脂株式会社 | ジオキサビシクロ〔3.3.0〕オクタン誘導体を有効成分とする体脂肪低減剤 |
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- 2005-12-28 EP EP05844845A patent/EP1842540A4/en not_active Withdrawn
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Also Published As
Publication number | Publication date |
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MY148121A (en) | 2013-02-28 |
EP1842540A4 (en) | 2011-12-28 |
AU2005320579B2 (en) | 2011-09-22 |
TWI368506B (zh) | 2012-07-21 |
CN101849935A (zh) | 2010-10-06 |
EP1842540A1 (en) | 2007-10-10 |
SG158183A1 (en) | 2010-01-29 |
HK1088333A1 (en) | 2006-11-03 |
WO2006070856A1 (ja) | 2006-07-06 |
JP4995567B2 (ja) | 2012-08-08 |
KR101244586B1 (ko) | 2013-03-25 |
CN1796388A (zh) | 2006-07-05 |
JPWO2006070856A1 (ja) | 2008-06-12 |
US20080275110A1 (en) | 2008-11-06 |
CN1796388B (zh) | 2011-01-26 |
TW200633696A (en) | 2006-10-01 |
HK1148465A1 (en) | 2011-09-09 |
CA2592532A1 (en) | 2006-07-06 |
KR20070089752A (ko) | 2007-08-31 |
CA2592532C (en) | 2015-02-17 |
AU2005320579A1 (en) | 2006-07-06 |
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