CN107530315A - 肌肉细胞中的能量代谢激活剂 - Google Patents
肌肉细胞中的能量代谢激活剂 Download PDFInfo
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- CN107530315A CN107530315A CN201680021053.9A CN201680021053A CN107530315A CN 107530315 A CN107530315 A CN 107530315A CN 201680021053 A CN201680021053 A CN 201680021053A CN 107530315 A CN107530315 A CN 107530315A
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Abstract
本发明的课题在于提供新型的肌肉能量代谢激活剂等,还提供可作为医药、食品摄入的组合物。用于解决上述课题的本发明的技术特征如下所述。(1)一种糖转运体(GLUT4)基因表达促进剂,其以选自5‑羟基‑3,7‑二甲氧基黄酮、柚木柯因、3,7,4’‑三甲基山奈酚、栎精‑3,7,3’,4’‑四甲醚、五甲基槲皮素、三甲基芹菜素、四甲基山奈酚、和5,7‑二甲氧基黄酮中的至少1种为有效成分。(2)糖转运体(GLUT4)基因表达促进剂,其以柚木柯因和5,7‑二甲氧基黄酮中的至少1种为有效成分。(3)肌肉细胞中的糖转运体(GLUT4)基因表达促进剂,其包含下述化学式(1)表示的化合物中的任一种。式中,R1和R2分别为氢或碳原子数1~3的烷基。
Description
技术领域
本发明涉及新型的肌肉能量代谢激活剂。本发明广泛应用于饮食品、医药品、类医药品等。
背景技术
运动时,肌肉消耗大量的能量,已知其能量源中的大部分依赖于糖(葡萄糖等)。因此,肌肉中的糖的摄取在能量生产中发挥重要的作用。因而,肌肉中的糖的摄取量的增加,可期待提高运动时的成绩(参见非专利文献1)。
此处,与所述肌肉细胞对糖的摄取相关的是糖转运体(GLUT4:葡萄糖转运体4)。
另外,已知参与骨骼肌的能量代谢控制的因子PGC-1α(非专利文献2)。
PGC-1α是指过氧化物酶体增殖物激活受体γ辅激活因子1α(Peroxisomeproliferator-activated receptorγco-activator 1α),已知其具有促进线粒体合成的作用,且使作为将血液中的葡萄糖(血糖)摄取至骨骼肌的糖转运体的GLUT4增多。另外,人的肌肉中的PGC-1α表达量因糖尿病、老化而与线粒体功能一同下降,PGC-1α成为因能量消耗量降低而导致的代谢综合征(metabolic syndrome)等与生活方式相关的疾病的治疗靶标,这是已知的。
另外,在将小鼠置于寒冷环境下时,骨骼肌中的PGC-1α增多。由此可知,PGC-1α与骨骼肌组织的产热的控制有关。另外,在使PGC-1α强制表达时,除了可诱导促进与线粒体呼吸链有关的因子的转录的NRF、被认为在线粒体中引起能量消耗的解偶联蛋白(uncouplingprotein,UCP)的表达之外,还可诱导在线粒体的基因组复制、转录反应过程中发挥重要作用的线粒体转录因子A(mitochondrial transcription factor A,mtTFA)的表达,通过这些分子的功能表达,从而使细胞内的线粒体数增加,而且使细胞的耗氧量增大,这也是已知的。由此可知,通过在来自人的细胞中激活线粒体的功能,从而引起产热,即能量消耗,而且在细胞内激活作为能量源的糖、脂质的代谢(非专利文献3)。
此前,关于运动功能改善剂,作为抗疲劳剂,已知维生素类(专利文献1)、在鲣鱼、金枪鱼中大量含有的咪唑化合物(专利文献2)、鸟氨酸(专利文献3)等。
现有技术文献
专利文献
专利文献1:日本特开2010-138170号公报
专利文献2:日本特开2002-338473号公报
专利文献3:国际公开第2007/142286号
专利文献4:日本特开2015-10078号公报
非专利文献
非专利文献1:八田秀雄著,“エネルギー代謝を活かしたスポーツトレーニング(有效利用了能量代谢的体育训练)”讲谈社,2004年发行
非专利文献2:Cell,92,829-838,1998
非专利文献3:Cell,98,115-124,1999
发明内容
发明所要解决的课题
在上述背景下,本发明人发现,小花山奈中含有的特定的化合物,促进肌肉细胞中的糖转运体(GLUT4)基因的表达,而且激活PGC-1α的基因,使线粒体DNA的产生量增多,从而完成了本发明。
即,本发明的目的在于通过提供新型的、肌肉细胞中的糖转运体(GLUT4)基因表达促进剂和PGC-1α基因激活剂、以及使用了它们的肌肉细胞中的能量代谢激活剂,从而生成具有优异的质量的肌肉。
需要说明的是,作为与本发明相关的技术,专利文献4中记载了小花山奈提取物及聚甲氧基黄酮具有增加肌肉量的作用。然而,本申请发明是明确了小花山奈提取物及聚甲氧基黄酮具有提高肌肉细胞的代谢功能的作用的发明,明确区别于着眼于肌肉量的增加的专利文献4的发明。
即,增加肌肉量、与提高肌肉的代谢功能是通过不同的机制控制的。为了增加肌肉量,增加肌肉合成、减少肌肉分解是重要的,为了提高肌肉的代谢功能,增加营养素(糖等)的摄取量、糖原的蓄积量、线粒体量是重要的。这可通过下述事实证明:即,市场上,为了增加肌肉量,常常使用来源于大豆的蛋白质、乳清蛋白(whey protein)等,而为了提高肌肉的代谢功能,常常使用肉毒碱、辅酶Q10等,根据各自不同的用途而分开使用这些物质。
专利文献4中记载,在用小鼠进行实验的情况下,其效果限于比目鱼肌,对其他运动肌肉没有效果。本发明人在后述的试验例中,用经修正的数据对其效果进行了评价,由此,确认了并非在总体上使代谢功能提高,而是使单个肌细胞的代谢功能提高,在此基础上完成了本发明。
用于解决课题的手段
用于解决上述课题的本发明的技术特征如下所述。
(1)一种糖转运体(GLUT4)基因表达促进剂,其以选自5-羟基-3,7-二甲氧基黄酮(5-Hydroxy-3,7-dimethoxyflavone)、柚木柯因(Techtochrysin)、3,7,4’-三甲基山奈酚(3,7,4’-Trimethylkaempferol)、栎精-3,7,3’,4’-四甲醚(Retusine)、五甲基槲皮素(Pentamethylquercetin)、三甲基芹菜素(Trimethylapigenin)、四甲基山奈酚(Tetramethylkaempferol)、和5,7-二甲氧基黄酮(5,7-dimethoxyflavone)中的至少1种为有效成分。
(2)一种糖转运体(GLUT4)基因表达促进剂,其以柚木柯因(Techtochrysin)和5,7-二甲氧基黄酮(5,7-dimethoxyflavone)中的至少1种为有效成分。
(3)一种肌肉细胞中的糖转运体(GLUT4)基因表达促进剂,其包含下述化学式(1)表示的化合物中的任一种。
[化学式1]
此处,R1和R2分别为氢或碳原子数1~3的烷基。
(4)一种PGC-1α基因表达促进剂,其以选自5-羟基-3,7-二甲氧基黄酮(5-Hydroxy-3,7-dimethoxyflavone)、柚木柯因(Techtochrysin)、3,7,4’-三甲基山奈酚(3,7,4’-Trimethylkaempferol)、栎精-3,7,3’,4’-四甲醚(Retusine)、五甲基槲皮素(Pentamethylquercetin)、三甲基芹菜素(Trimethylapigenin)、四甲基山奈酚(Tetramethylkaempferol)、和5,7-二甲氧基黄酮(5,7-dimethoxyflavone)中的至少1种为有效成分。
(5)一种PGC-1α基因表达促进剂,其以柚木柯因(Techtochrysin)和5,7-二甲氧基黄酮(5,7-dimethoxyflavone)中的至少1种为有效成分。
(6)一种肌肉细胞中的PGC-1α基因表达促进剂,其包含下述化学式(1)表示的化合物中的任一种,
[化学式1]
此处,R1和R2分别为氢或碳原子数1~3的烷基。
(7)一种肌肉细胞中的能量代谢激活剂,其包含上述(1)~(6)中任一项所述的药剂。
(8)一种糖转运体(GLUT4)基因表达促进剂,其以小花山奈提取物为有效成分。
(9)一种PGC-1α基因表达促进剂,其以小花山奈提取物为有效成分。
(10)一种用于激活肌肉细胞中的能量代谢的食品组合物,其以柚木柯因(Techtochrysin)为有效成分。
(11)一种用于激活肌肉细胞中的能量代谢的食品组合物,其以5,7-二甲氧基黄酮(5,7-dimethoxyflavone)为有效成分。
(12)一种激活人的肌肉细胞中的能量代谢的方法,所述方法通过向人给予选自5-羟基-3,7-二甲氧基黄酮(5-Hydroxy-3,7-dimethoxyflavone)、柚木柯因(Techtochrysin)、3,7,4’-三甲基山奈酚(3,7,4’-Trimethylkaempferol)、栎精-3,7,3’,4’-四甲醚(Retusine)、五甲基槲皮素(Pentamethylquercetin)、三甲基芹菜素(Trimethylapigenin)、四甲基山奈酚(Tetramethylkaempferol)、和5,7-二甲氧基黄酮(5,7-dimethoxyflavone)中的至少1种而进行。
附图说明
图1为5-羟基-3,7-二甲氧基黄酮、柚木柯因、3,7,4’-三甲基山奈酚、栎精-3,7,3’,4’-四甲醚、五甲基槲皮素、三甲基芹菜素、四甲基山奈酚、和5,7-二甲氧基黄酮的分离路线(scheme)。
图2为表示小花山奈提取物(KPE)及分离组分(化合物1-8)对糖转运体(GLUT4)的mRNA表达的影响的图。
图3为表示小花山奈提取物(KPE)及分离组分(化合物1-8)对PGC-1α的mRNA表达的影响的图。
具体实施方式
以下详细说明本发明。
本发明的肌肉细胞中的能量代谢激活剂的特征在于,包含5-羟基-3,7-二甲氧基黄酮、柚木柯因、3,7,4’-三甲基山奈酚、栎精-3,7,3’,4’-四甲醚、五甲基槲皮素、三甲基芹菜素、四甲基山奈酚、和5,7-二甲氧基黄酮(以下,将这些化合物称为“化合物组”)中的至少1种。
上述化合物组是由下述化学式(2)所表示的化合物组。
[化学式2]
5-羟基-3,7-二甲氧基黄酮(1)
柚木柯因(2)
3,7,4’-三甲基山奈酚(3)
栎精-3,7,3’,4’-四甲醚(4)
五甲基槲皮素(5)
三甲基芹菜素(6)
四甲基山奈酚(7)
5,7-二甲氧基黄酮(8)
另外,在这些化合物组中,特别优选柚木柯因和5,7-二甲氧基黄酮。
得到上述化合物组的方法没有特别限制,优选通过从小花山奈中提取而得到。这是因为,小花山奈中以高浓度含有上述化合物组。
此处所谓“小花山奈”,是指学名为泰国烂姜、即Kaempferia parviflora的植物,分布于东南亚,属于姜科山奈属。
在泰国、老挝等的传统医学中,小花山奈被用于增进精力、滋养强壮、降低血糖值、恢复体力、改善消化系统、改善阴道分泌物、痔核、痔疮、恶心、口炎、关节痛、胃痛,等等。
为了得到上述化合物组而使用的小花山奈的部位没有特别限制,优选使用根茎。这是因为,小花山奈的根茎以高浓度含有上述化合物组。小花山奈的形态没有特别限制,未成熟根茎、完全成熟根茎、干燥根茎等均可。需要说明的是,绞榨根茎而得到的榨汁液也同样优选使用。榨汁液的形态没有特别限制,可以是液状,也可以是经浓缩干燥的粉末状。
然而,在生的根茎、榨汁液的情况下,需要注意保存,因而最优选将根茎切片并进行干燥而得到的产物。
在使用切片的干燥根茎的情况下,为了提高提取效率,优选预先用粉碎机等将根茎粉碎至40目左右。
对用于提取的溶剂、温度条件等没有特别限制,可任意地选择、设定。作为提取溶剂,可选择水、酸、碱等之类的非有机溶剂、亲水性溶剂、丙酮等之类的有机溶剂。作为亲水性溶剂,从操作性、提取效率方面考虑,优选选自由甲醇、乙醇、正丙醇、异丙醇及丁醇组成的低级醇组中的1种以上。但是,与利用有机溶剂进行的提取相比,更优选利用非有机溶剂进行的提取,其中,可选择常温水、温水、热水、及添加了少量酸的水、乙醇中的任一种。
作为此时使用的酸,没有特别限制。但是,从获得的容易性及安全性、后处理的观点考虑,优选使用乙酸。
此外,上述的提取中,优选对提取残渣再次重复进行1次或1次以上的提取工序,通过该方法,可提高提取效率。这种情况下,用于提取的溶剂可以相同也可以不同。
为了得到上述化合物组,对上述提取物进行过滤、离心分离及分馏这样的处理,将不溶性物质及溶剂除去,然后,按照常规方法,对提取液实施稀释、浓缩、干燥、纯化等处理,制成能量代谢激活剂等。
需要说明的是,作为纯化方法,例如,可举出活性炭处理、树脂吸附处理、离子交换树脂、液-液反流分布等方法,但由于添加到食品等中时不大量使用,所以也可以以未纯化的状态使用。具体而言,可按照下述实施例的图1的路线得到化合物组的组分。
虽然也可直接使用该组分,但根据需要,也可利用喷雾干燥、冷冻干燥等方法将该组分制成干燥粉末而使用。
另外,本发明的能量代谢激活剂的特征在于,以下述化学式(1)所记载的化合物为有效成分。
[化学式1]
此处,R1和R2分别为氢或碳原子数1~3的烷基。
另外,上述化学式(1)所示的化合物中,特别优选柚木柯因和5,7-二甲氧基黄酮。
得到上述化学式(1)所示的化合物的方法没有特别限制,优选通过从植物中提取而得到。
另外,上述化学式(1)所示的化合物中,得到柚木柯因和5,7-二甲氧基黄酮时,优选使用小花山奈。可利用上述方法将这些化合物提取分离。
本发明的能量代谢激活剂可用作各种饮食品的素材(食品用组合物)。
此处所谓“可用作各种饮食品的素材”,是指为了发挥本发明的能量代谢激活剂的效果,可以选择食品作为剂型,目的在于仅供期待作为能量代谢激活剂的效果的人食用,并非是指可供包括不期待能量代谢激活剂的效果的人在内的人群食用。
另外,用于作为能量代谢激活剂而发挥效果的配合量没有特别限制,相对于饮食品,有效成分的含量优选总计为1~20wt%。
另外,作为配合所述能量代谢激活剂的饮食品,没有特别限制,例如,可举出以食用油(色拉油)、糖果类(口香糖、糖果、卡拉梅尔糖、巧克力、曲奇、点心(snack)、果冻(jelly)、软糖、压片糖等)、面类(荞麦面、乌冬面、拉面等)、乳制品(牛奶、冰激凌、酸奶(yoghurt)等)、调味料(味噌、酱油等)、汤类、饮料(果汁、咖啡、红茶、茶、碳酸饮料、运动饮料等)为代表的普通食品、健康食品(片剂、胶囊等)、营养补充食品(营养饮料等)。可在这些饮食品中适当配合本发明的能量代谢激活剂等(包含上述(1)~(8)中任一项所述的药剂。)。
这些饮食品中,可以根据其种类配合加入各种成分,例如可使用葡萄糖、果糖、蔗糖、麦芽糖、山梨糖醇、甜菊糖、玉米糖浆、乳糖、柠檬酸、酒石酸、苹果酸、琥珀酸、乳酸、L-抗坏血酸、dl-α-维生素E、异抗坏血酸钠、甘油、丙二醇、甘油脂肪酸酯、聚甘油脂肪酸酯、蔗糖脂肪酸酯、山梨糖醇脂肪酸酯、丙二醇脂肪酸酯、阿拉伯胶、卡拉胶、酪蛋白、明胶、果胶、琼脂、维生素B类、烟酰胺、泛酸钙、氨基酸类、钙盐类、色素、香料、保藏剂等食品素材。
并且,具有健康维持功能的本能量代谢激活剂等中还可以配合加入其他抗氧化物质和健康食品素材等配合剂,例如抗氧化物质(还原型抗坏血酸(维生素C)、维生素E、还原型谷胱甘肽、生育三烯酚、维生素A衍生物、番茄烯、叶黄素、虾青素、玉米黄素、岩藻黄素、尿酸、泛醌、辅酶Q10、叶酸、大蒜提取精油/精华、大蒜素、芝麻素、木质素类、儿茶素、异黄酮、查耳酮、单宁类、类黄酮、香豆素、异香豆素、蓝莓提取精油/精华)、健康食品素材(V.(维生素)A、V.B1、V.B2、V.B6、V.B12、V.C、V.D、V.E、V.P、胆碱、烟酸、泛酸、叶酸钙、EPA、寡糖、食物纤维、鲨烯、大豆卵磷脂、牛磺酸、杜氏盐藻、蛋白质、二十八烷醇、卵黄卵磷脂、亚油酸、乳铁蛋白、镁、铬、硒、钾、血红素铁、牡蛎肉提取精油/精华、几丁聚糖(chitosan)、几丁质寡糖(chitin oligosaccharide)、胶原、软骨素、姜黄、甘草、枸杞子、桂皮、山楂、生姜、灵芝、蚬提取精油/精华、甘草、枸杞子、桂皮、山楂、生姜、灵芝、车前子、洋甘菊、德国洋甘菊、蒲公英、木槿、蜂蜜、花粉、蜂王浆、青柠、薰衣草、蔷薇果、迷迭香、鼠尾草、双歧杆菌、粪肠球菌、LACRIS菌、小麦胚芽油、芝麻油、紫苏油、大豆油、中链脂肪酸、蘑菇(agaricus)、银杏叶提取精油/精华、姜黄、软骨素、玄米胚芽提取精油/精华、灵芝、洋葱、DHA、EPA、DPA、甜茶、冬虫夏草、大蒜、蜜蜂幼虫、番木瓜、普洱、蜂胶、毛果槭、猴头菇、蜂王浆、锯叶棕、透明质酸、胶原、γ-氨基丁酸、海豹油、鲨鱼软骨粉、葡萄糖胺、卵磷脂、磷脂酰丝氨酸、田七人参、桑叶、大豆提取物、紫锥菊、刺五加、大麦提取物、橄榄叶、橄榄果、匙羹藤、大花紫薇、五层龙属植物、藤黄果、几丁聚糖(chitosan)、贯叶连翘、枣、胡萝卜/人参、西番莲属植物、西兰花、胎盘、薏苡、葡萄籽、花生种皮、欧洲越橘、黑升麻、乳蓟、月桂树、鼠尾草、迷迭香、罗布麻、黑醋、苦瓜、玛咖、红花、亚麻、乌龙茶、花棘、咖啡因、辣椒素、低聚木糖、葡萄糖胺、荞麦、柑橘、食物纤维、蛋白质、梅干、螺旋藻、大麦新叶、核酸、酵母、椎茸、梅肉、氨基酸、深海鲨鱼提取物、檄树果、牡蛎肉、中华鳖、香蕈、车前子、西印度樱桃、菠萝、香蕉、桃、杏、甜瓜、草莓、覆盆子、橙子、岩藻多糖、桑黄、蔓越莓、硫酸软骨素、锌、铁、神经酰胺、丝素肽、甘氨酸、烟酸、圣洁莓、L-半胱氨酸、红酒叶、粟、马尾草、维生素H、崩大碗、蓝靛果、碧萝芷、蜂斗菜、大黄、丁香、迷迭香、儿茶素、普洱、柠檬酸、啤酒酵母、草木犀、玄米香啡(black zinger)、生姜、莪术、纳豆激酶、红曲霉、生育三烯酚、乳铁蛋白、肉桂、苦荞麦、可可、柚子种子提取精油/精华、紫苏子提取精油/精华、荔枝种子提取精油/精华、月见草提取精油/精华、糙米提取精油/精华、α-硫辛酸、γ-氨基丁酸、生咖啡豆提取精油/精华、蜂斗菜提取精油/精华、猕猴桃种子提取精油/精华、温州蜜柑提取精油/精华、红生姜提取精油/精华、虾青素、核桃提取精油/精华、韭菜种子提取精油/精华、红米提取精油/精华、管花肉苁蓉提取精油/精华、银耳多糖、岩藻黄素、越橘提取精油/精华、樱花提取精油/精华、马基莓(maqui berry)提取精油/精华、鸡腿菇提取精油/精华、大米多胺、小麦多胺)等。
作为具体制备方法,通过将能量代谢激活剂等与粉末纤维素一同喷雾干燥或冷冻干燥,将其制成粉末、颗粒、压片或溶液,可容易地使其在饮食品(方便食品等)中含有。另外,可将能量代谢激活剂等溶解在例如油脂、乙醇、甘油或这些物质的混合物中而制成液状,添加在饮料中,或添加在固形食品中。也可以根据需要与阿拉伯胶、葡聚糖等粘合剂混合而制成粉末状或颗粒状,添加在饮料中,或添加在固形食品中。
本发明的能量代谢激活剂等也可用作为药品(包括医药品及类医药品)的素材。可在药品制剂用的原料中适当配合加入本发明的能量代谢激活剂等进行制造。作为可以在本发明的能量代谢激活剂等中配合加入的制剂原料,可以列举赋形剂(葡萄糖、乳糖、白糖、氯化钠、淀粉、碳酸钙、高岭土、结晶纤维素、可可脂、氢化植物油、高岭土、滑石等)、结合剂(蒸馏水、生理盐水、乙醇水溶液、单糖浆、葡萄糖液、淀粉液、明胶溶液、羧甲基纤维素、磷酸钾、聚乙烯吡咯烷酮等)、崩解剂(海藻酸钠、琼脂、碳酸氢钠、碳酸钙、十二烷基硫酸钠、单硬脂酸甘油酯、淀粉、乳糖、阿拉伯胶粉末、明胶、乙醇等)、崩解抑制剂(白糖、硬脂、可可脂、氢化油等)、吸收促进剂(季铵碱、十二烷基硫酸钠等)、吸附剂(甘油、淀粉、乳糖、高岭土、膨润土、硅酸等)、润滑剂(精制滑石、硬脂酸盐、聚乙二醇等)等。
作为本发明的能量代谢激活剂等的给药方法,通常,可以以片剂、丸剂、软/硬胶囊剂、细粒剂、散剂、颗粒剂、液剂等的形式口服给药,但也可以是肠胃外给药。以肠胃外剂形式进行给药时,可以采用溶液状态的、或添加了分散剂、悬浮剂、稳定剂等的状态的巴布剂、液剂、软膏剂、酊剂、霜剂等剂型。
给药量可根据给药方法、病情、患者的年龄等的不同而改变,对于成人,通常每天可给予0.5~1000mg有效成分,对于儿童,通常每天可给予0.5~500mg左右有效成分。
[实施例]
以下,基于实施例来说明本发明。
[实施例:小花山奈提取物及化合物组的制作]
(1)小花山奈提取物的制备
将小花山奈切片并进行干燥,得到100kg干燥物。将10kg该干燥物破碎,用乙醇浓度为70wt%的含水乙醇(70%乙醇(w/w))、于80℃提取2小时,将乙醇提取液浓缩至干,得到3.25kg小花山奈提取物。
需要说明的是,对小花山奈提取物的含有成分进行了HPLC分析,结果为:含有8wt%以上5,7-二甲氧基黄酮、35wt%以上总黄酮。
(2)化合物组的制作
使用10kg的70%乙醇(w/w),于70℃,对2.0kg经粉碎的小花山奈(Kaempferiaparviflora)进行2小时提取。对得到的提取液进行过滤,向残渣中添加8kg的70%乙醇(w/w),利用同样的操作再次进行提取。然后,将提取液合并,在减压下将溶剂馏去,在固态成分为20~30%的时间点添加2倍量的水。用乙酸乙酯对得到的加水提取液进行分配萃取,在减压下,将各迁移部的溶剂馏去,得到乙酸乙酯迁移部(90.92g,4.5%)。
按照图1的纯化路线将得到的可溶于乙酸乙酯的部分中的一部分(50.0g)分离。
即,利用正相硅胶柱色谱法[己烷-乙酸乙酯(4:1→2:1→1:1,v/v)→乙酸乙酯→氯仿-甲醇(4:1→1:1,v/v)→甲醇]进行分离,得到5种组分[级分(fraction)1(8.26g)、级分2(6.35g)、级分3(24.31g)、级分4(5.92g)、级分5(0.83g)]。
利用HPLC[甲醇,Inertsil PREP-ODS]对级分1进行分离,得到化合物1(5-羟基-3,7-二甲氧基黄酮)(32.9mg)、化合物2(柚木柯因)(30.4mg)、化合物3(3,7,4’-三甲基山奈酚)(25.2mg)。
利用正相硅胶柱色谱法[己烷-乙酸乙酯(9:1→1:1→1:2,v/v)→甲醇]对级分2进行分离,得到级分2-1(0.46g)、级分2-2(0.59g)、级分2-3(4.25g)。利用HPLC[甲醇-水(95:5),Inertsil PREP-ODS]对级分2-2进行分离,得到化合物4(栎精-3,7,3’,4’-四甲醚)(48.2mg)。
利用HPLC[甲醇-水(80:20),Inertsil PREP-ODS]对级分3进行分离,得到级分3-1(0.75g)、级分3-2(9.71g)、级分3-3(5.32g)、级分4(0.09g)。利用HPLC[甲醇-水(80:20),TSK-Gel ODS-120T]对级分3的一部分(1.06g)进行分离,得到化合物5(五甲基槲皮素)(90.0mg)、化合物6(三甲基芹菜素)(90.0mg)、化合物7(四甲基山奈酚)(100.0mg)、化合物8(5,7-二甲氧基黄酮)(160.0mg)。需要说明的是,用二维NMR鉴定化合物1-8的结构。
[试验例1:糖转运体(GLUT4)基因表达的促进作用的评价]
将小鼠成肌细胞株C2C12(用DMEM FCS10%进行培养)接种于24孔板(用于定量mRNA表达)(1×104个细胞/ml),培养24h。24h后,向分化诱导用的培养基(DMEM FCS1%)中添加10μg/mL小花山奈提取物,并且以成为1μM或10μM(分别为:溶解于DMSO中的样品相对于培养基而言为0.1%(v/v))的浓度的方式添加分离组分(化合物1-8),培养1周。另外,作为对照,以相对于培养基而言为0.1%(v/v)的浓度添加DMSO。培养1周后,回收细胞,提取RNA。针对得到的RNA,使用定量型RT-PCR法对糖转运体(GLUT4)的mRNA表达量进行定量。此时,作为内源性对照,使用GAPDH。将其结果示于图2。
[结果及试验例1中的实施例的效果]
如图2所示那样,可知小花山奈提取物(KPE)在C2C12中促进糖转运体(GLUT4)的表达。另一方面,从KPE中分离纯化8种化合物,对这8种级分对糖转运体(GLUT4)表达的促进作用进行了评价。结果,观察到这些分离组分促进表达。其中,对于化合物2(柚木柯因)、化合物3(3,7,4’-三甲基山奈酚)、化合物7(四甲基山奈酚)、化合物8(5,7-二甲氧基黄酮)而言,确认到表达增加显著,进而,对于其中化合物2及化合物8而言,确认到表达增加特别显著。
[试验例2:促进PGC-1α表达的作用的评价]
将小鼠成肌细胞株C2C12(用DMEM FCS10%进行培养)接种于24孔板(用于定量mRNA表达)(1×104个细胞/ml),培养24h。24h后,向分化诱导用的培养基(DMEM FCS1%)中添加10μg/mL小花山奈提取物,或者以成为1μM或10μM(分别为:溶解于DMSO中的样品相对于培养基而言为0.1%(v/v))的浓度的方式添加分离组分(化合物1-8),培养1周。另外,作为对照,以相对于培养基而言为0.1%(v/v)的浓度添加DMSO。培养1周后,回收细胞,提取RNA。
针对得到的RNA,使用定量型RT-PCR法对PGC-1α的mRNA表达量进行定量。此时,作为内源性对照,使用GAPDH。将其结果示于图3。
[结果及试验例2中的实施例的效果]
如图3所示那样,可知小花山奈提取物(KPE)在C2C12中促进PGC-1α的表达。另一方面,从KPE中分离纯化8种化合物,对于这8种级分,对促进PGC-1α表达的作用进行评价。结果,观察到促进PGC-1α表达的作用,进而,对于其中化合物2(柚木柯因)及化合物8(5,7-二甲氧基黄酮)而言,确认到表达增加特别显著。
[实施例的效果]
通过上述化合物组,糖转运体(GLUT4)及PGC-1α的表达增加(图2及图3)。此外,关于糖转运体(GLUT4)及PGC-1α的表达上升,确认了活性与结构相关。可知在化合物组中,B环上甲氧基少时,活性强。由此,确认了上述化学式(1)所示的化合物的上述活性强。
实际上,活性高的是在B环上不具有甲氧基的化合物2(柚木柯因)和化合物8(5,7-二甲氧基黄酮),活性低的是在B环上具有2个甲氧基的化合物4(栎精-3,7,3’,4’-四甲醚(Retsine))、化合物5(五甲基槲皮素)(图3)。
由此确认,对于上述化合物组及上述化学式(1)表示的化合物而言,通过促进作为糖代谢输送因子的糖转运体(GLUT4)及参与能量代谢控制的因子PGC-1α的基因的表达,从而具有能量代谢激活作用。
由此确认,上述化合物组、化学式(1)所示的化合物可作为糖转运体(GLUT4)基因表达促进剂、PGC-1α基因表达促进剂、能量代谢激活剂使用,另外,小花山奈提取物可作为PGC-1α基因表达促进剂使用。
以下列举本发明的能量代谢激活剂的配合例,但下述配合例不限制本发明。
配合例1:口香糖
配合例2:软糖
配合例3:糖果
配合例4:酸奶(硬、软)
配合例5:清凉饮料
配合例6:软胶囊
配合例7:片剂
配合例8:颗粒内服剂(医药品)
配合例9:压片糖
配合例10:猫粮
配合例11:狗粮
工业实用性
如上文中所说明那样,本发明可提供安全、副作用少的肌肉细胞的能量代谢激活剂。
Claims (11)
1.一种糖转运体GLUT4基因表达促进剂,其以选自5-羟基-3,7-二甲氧基黄酮、柚木柯因、3,7,4’-三甲基山奈酚、栎精-3,7,3’,4’-四甲醚、五甲基槲皮素、三甲基芹菜素、四甲基山奈酚、和5,7-二甲氧基黄酮中的至少1种为有效成分。
2.一种糖转运体(GLUT4)基因表达促进剂,其以柚木柯因和5,7-二甲氧基黄酮中的至少1种为有效成分。
3.一种肌肉细胞中的糖转运体(GLUT4)基因表达促进剂,其包含下述化学式(1)表示的化合物中的任一种,
化学式(1)
此处,R1和R2分别为氢或碳原子数1~3的烷基。
4.一种PGC-1α基因表达促进剂,其以选自5-羟基-3,7-二甲氧基黄酮、柚木柯因、3,7,4’-三甲基山奈酚、栎精-3,7,3’,4’-四甲醚、五甲基槲皮素、三甲基芹菜素、四甲基山奈酚、和5,7-二甲氧基黄酮中的至少1种为有效成分。
5.一种PGC-1α基因表达促进剂,其以柚木柯因和5,7-二甲氧基黄酮中的至少1种为有效成分。
6.一种肌肉细胞中的PGC-1α基因表达促进剂,其包含下述化学式(1)表示的化合物中的任一种,
化学式(1)
此处,R1和R2分别为氢或碳原子数1~3的烷基。
7.一种能量代谢激活剂,其包含所述权利要求1~6中任一项所述的药剂。
8.一种糖转运体GLUT4基因表达促进剂,其以小花山奈提取物为有效成分。
9.一种PGC-1α基因表达促进剂,其以小花山奈提取物为有效成分。
10.一种用于激活肌肉细胞中的能量代谢的食品组合物,其以柚木柯因为有效成分。
11.一种用于激活肌肉细胞中的能量代谢的食品组合物,其以5,7-二甲氧基黄酮为有效成分。
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US11452756B2 (en) | 2019-07-31 | 2022-09-27 | Tokiwa Phytochemical Co., Ltd. | Composition and method for improving quantity of tear fluid, composition, treating constipation and improving skin quality |
WO2022269931A1 (ja) * | 2021-06-25 | 2022-12-29 | 大塚製薬株式会社 | 筋損傷抑制用組成物 |
CN115028754B (zh) * | 2022-06-30 | 2023-08-11 | 上海市农业科学院 | 硫酸化猴头菌子实体β-葡聚糖、硫酸化β-葡聚糖-壳聚糖纳米颗粒及其制备方法和应用 |
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JP2013241354A (ja) * | 2012-05-18 | 2013-12-05 | Oriza Yuka Kk | ホスホジエステラーゼ2阻害剤 |
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US20190328701A1 (en) | 2019-10-31 |
HK1248591A1 (zh) | 2018-10-19 |
JPWO2016163245A1 (ja) | 2018-02-22 |
JP6751709B2 (ja) | 2020-09-09 |
US20180117000A1 (en) | 2018-05-03 |
US20200360338A1 (en) | 2020-11-19 |
WO2016163245A1 (ja) | 2016-10-13 |
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