CN106333944A - 增加羟基肉桂酸类的生物利用度 - Google Patents
增加羟基肉桂酸类的生物利用度 Download PDFInfo
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- CN106333944A CN106333944A CN201610908574.8A CN201610908574A CN106333944A CN 106333944 A CN106333944 A CN 106333944A CN 201610908574 A CN201610908574 A CN 201610908574A CN 106333944 A CN106333944 A CN 106333944A
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Abstract
本发明涉及增加羟基肉桂酸类的生物利用度。本发明总体涉及营养、卫生和健康领域。例如，本发明涉及羟基肉桂酸类以及其健康益处。本发明公开了可以使羟基肉桂酸类的生物利用度和/或生物功效增加的组合物。根据本发明，其可以通过与羟基肉桂酸类共同施用至少一种类黄酮的糖苷结合物来完成。
Description
本申请为2012年11月22日提交的申请号为PCT/EP2012/073383、发明名称为“增加羟基肉桂酸类的生物利用度”的国际申请的分案申请，该国际申请于2014年5月28日进入中国国家阶段，申请号为201280058454.3。
技术领域
本发明总体涉及营养、卫生和健康领域。例如，本发明涉及羟基肉桂酸类以及其健康益处。本发明公开了可以使羟基肉桂酸类的生物利用度和/或生物功效增加的组合物。根据本发明，其可以通过与羟基肉桂酸类共同施用至少一种类黄酮的糖苷结合物来完成。
背景技术
羟基肉桂酸类是在我们饮食中十分丰富的酚类，并且发现它们在水果、蔬菜和咖啡中广泛存在。估计羟基肉桂酸类的日摄取量可能很高(500-1000mg/d)，喝咖啡的人尤其如此。体外和体内研究已经表明，羟基肉桂酸类的消耗具有一些有益效果，这些有益效果与它们的抗氧化能力有关[Natella F等,J Agric Food Chem 2002；50:6211-6；Natella F等,Am J Clin Nutr2007；86:604-9；Poquet L等,Arch Biochem Biophys 2008；476:196-204]。
但是，对于人类而言，羟基肉桂酸类的首过代谢在限制其生物利用度方面起着主要作用。特别是II相酶，其通过形成硫酸酯、葡萄糖醛酸苷或氨基酸结合物而直接参与饮食性羟基肉桂酸类的灭活[Poquet L等,Biochem Pharmacol 2008；75:1218-29]。一些人类和体外机理研究表明，所吸收的羟基肉桂酸盐类在小肠和肝中被广泛代谢，并且确定了磺基转移酶(SULT)是参与代谢的主要代谢酶类。因此，羟基肉桂酸类的硫酸酯结合物是在人血浆和尿中检测到的主要形式，而发现的游离酸的水平很低。在人体内，细胞溶质的SULT由催化低分子量的内源性化合物和外源性物质硫酸化的11个成员组成[Blanchard RL等,Pharmacogenetics2004；14:199-211]。羟基肉桂酸硫酸酯是人类肝和肠匀浆中形成的主要产物，表明这两种器官有助于人体内羟基肉桂酸的硫酸化。硫酸化靶向于酚羟基，该酚羟基是羟基肉桂酸强抗氧化能力的主要决定因子[Giacomelli C等,Redox Rep 2004；9:263-9]。因此，羟基肉桂酸类的硫酸化对其生物利用度有显著影响并降低了其生物效力。
然而，因为游离的羟基肉桂酸类表现出有益的抗氧化能力，因此，希望可获得一种可以使得羟基肉桂酸类的生物利用度增加的组合物。
本发明的发明人解决了这种需求。
发明内容
因此，本发明的目的是改善现有技术状态并提供一种可以使得羟基肉桂酸类的生物利用度增加并因此表现出改善的抗氧化能力的天然组合物。
本发明的发明人出人意料地发现，独立权利要求的主题可实现这一目的。从属权利要求进一步发展了本发明的思想。
发明人已经证明了类黄酮以及其结合物对五种主要的饮食性羟基肉桂酸(咖啡酸、二氢咖啡酸、二氢阿魏酸、阿魏酸和异阿魏酸)硫酸化的抑制作用。
用人类的小肠和肝匀浆证实了十一种饮食性类黄酮苷元对羟基肉桂酸类硫酸化的抑制作用。用人肝匀浆证实了槲皮素-3-葡萄糖醛酸苷、槲皮素-7-葡萄糖醛酸苷和槲皮素-3'-硫酸酯(人血浆中主要的槲皮素结合物)对硫酸化的影响。
还用人肝细胞瘤细胞系HepG2作为人肝脏模型证实了木犀草素、槲皮素和槲皮素结合物对羟基肉桂酸类硫酸化的抑制作用。
根据这些发现，发明人确信抑制SULT是一种可能的改善未结合的羟基肉桂酸类的生物利用度的策略，并由此导致其生物功效增加。特别地，因为类黄酮在肠中的局部浓度比在血浆中高很多，因此，可以用饮食剂量的类黄酮来抑制人肠中的SULT[Manach C等,Am JClin Nutr2005；81:230S-42S]。
人的肝脏是羟基肉桂酸硫酸化的另一个重要部位。但是，这些类黄酮在体内被广泛代谢为结合物。
发明人现在发现，类黄酮结合物也是肠吸收后羟基肉桂酸类硫酸化的有效抑制剂。
由于类黄酮具有通过抑制人小肠和肝脏中的SULT1A而调节羟基肉桂酸类生物利用度的潜能，因此，同时消耗羟基肉桂酸类与类黄酮使得可以增加循环中未结合的羟基肉桂酸的浓度，并因此增加羟基肉桂酸类在摄入后的生物功效。
因此，本发明部分涉及一种用于治疗、减轻或预防与氧化性应激、炎性过程和/或免疫应答降低有关的病症的包含至少一种饮食性羟基肉桂酸的组合物，其中向该包含羟基肉桂酸的组合物中加入至少一种类黄酮和/或其结合物。
本发明还部分涉及一种用于治疗、减轻或预防与氧化性应激、炎性过程和/或免疫应答降低有关的病症的包含至少一种饮食性羟基肉桂酸的组合物，该组合物包含至少一种类黄酮的糖苷结合物和羟基肉桂酸。可以将该至少一种类黄酮的糖苷结合物加入到天然包含至少一种羟基肉桂酸的组合物中。
因此，与组合物中天然的类黄酮糖苷结合物和/或羟基肉桂酸类的含量相比，本发明的组合物可能在至少一种类黄酮的糖苷结合物和/或至少一种羟基肉桂酸方面的含量更丰富。
例如，至少一种类黄酮的糖苷结合物和/或至少一种羟基肉桂酸类的含量富集因子可以为1.2、1.5、1.7、2、5或10。
本发明还涉及至少一种饮食性羟基肉桂酸与至少一种类黄酮和/或其结合物联合在制备用于治疗、减轻或预防与氧化性应激、炎性过程和/或免疫应答降低有关的病症的组合物中的用途。
本发明还涉及至少一种类黄酮和/或其糖苷结合物在制备用于治疗、减轻或预防与氧化性应激、炎性过程和/或免疫应答降低有关的病症的组合物中的用途。然后，该至少一种类黄酮将增加日常营养消耗的羟基肉桂酸类的生物利用度和生物功效。
因此，本发明还部分涉及一种用于治疗、减轻或预防与氧化性应激、炎性过程和/或免疫应答降低有关的病症的包含至少一种类黄酮和/或其糖苷结合物的组合物。这种组合物可以在消耗天然包含羟基肉桂酸类的食物或饮料之前、之后或期间进行施用。
发明人发现，该至少一种类黄酮和/或其结合物至少部分抑制了饮食性羟基肉桂酸类的硫酸化。
所述类黄酮可选自芹菜素、木犀草素、山奈酚、异鼠李素、槲皮素、橙皮素、染料木素、黄豆苷元、(+)-儿茶素、(-)-表儿茶素、根皮素或其组合。
发明人发现，染料木素、黄豆苷元、芹菜素、根皮素、木犀草素和/或槲皮素在测试条件下特别有效。
重要的是，发明人发现，不仅类黄酮可用于本发明的目的，其糖苷结合物也可用于本发明的目的。
就结合物而言，可以使用糖苷结合物。
就糖苷而言，可以使用鼠李糖、葡萄糖、半乳糖、木糖、阿拉伯糖、海藻糖或这些糖苷的组合，例如芸香糖苷。
类黄酮糖苷结合物的实例可以是芦丁(槲皮素-3-O-芸香糖苷)和/或黄豆苷(黄豆苷元-7-O-葡萄糖苷)。
在治疗应用中，组合物以足以至少部分治愈或阻止疾病及其并发症的症状的量进行施用。足以实现这一目的的量被定义为“治疗有效剂量”。对于该目的有效的量将取决于许多本领域技术人员已知的因素，如疾病的严重程度和患者的体重以及一般状况。
在预防应用中，本发明的组合物以足以至少部分降低形成疾病风险的量被施用给易患或者有患特定疾病风险的患者。该数量被定义为“预防有效量”。准确的量也取决于许多特定的患者因素如患者的健康状态和体重。
在本申请中，羟基肉桂酸和/或类黄酮和/或其糖苷结合物以治疗或预防有效量进行施用。本领域技术人员可准确地确定该剂量。
例如，本发明的组合物每份可包含至少1mg羟基肉桂酸、至少10mg羟基肉桂酸、或至少50mg羟基肉桂酸。
例如，本发明的组合物每份可包含至少10mg、至少100mg、或至少1000mg类黄酮和/或其结合物。
例如，存在于该组合物中的类黄酮和/或其结合物和羟基肉桂酸类的摩尔比可以在100:1至约1:1，或100:1至约10:1的范围内。虽然更多的类黄酮将以剂量依赖性方式防止羟基肉桂酸类通过形成硫酸酯结合物而失活，但是，发现对于大多数应用而言，上面的比例通常是理想的。
该至少一种类黄酮和/或其结合物可以以任何形式，例如化学合成化合物或由天然来源精制的化合物的形式被提供。
然而，优选以天然食品或其提取物的形式将该至少一种类黄酮和/或其结合物加入到所述组合物中。
这将突出组合物的天然性。
至少一种类黄酮和/或其结合物的天然来源可选自红茶或绿茶、酸豆(capers)、拉维纪草(lovage)、苹果、洋葱(特别是红洋葱)、红葡萄、柑橘类水果、西红柿、西兰花、覆盆子、笃斯越桔(bog whortleberry)、越橘、蔓越莓、野樱桃、甜山梨(sweet rowan)、花楸浆果(rowanberry)、沙棘浆果(sea buckthorn berry)、红莓苔子、仙人球仙人掌果实(pricklypear cactus fruit)或其组合。
同样，羟基肉桂酸也可以以任何形式，例如化学合成化合物或由天然来源精制的化合物的形式被提供。羟基肉桂酸也优选以天然食品或其提取物的形式提供。
例如，羟基肉桂酸类可得自或以咖啡、可可、植物或水果的形式被提供。
该羟基肉桂酸优选是一种饮食性羟基肉桂酸并且可选自咖啡酸、二氢咖啡酸、二氢阿魏酸、阿魏酸、异阿魏酸或其组合。
饮食性羟基肉桂酸类的优选实例是咖啡酸、阿魏酸或其组合。
本发明的组合物可用于治疗、预防或减轻与氧化性应激、炎性过程和/或免疫应答降低有关的病症。
这些病症可选自高血糖症、2型糖尿病、心血管疾病、急性免疫和/或炎性反应、由紫外线(UV)辐射造成的皮肤细胞损害、细胞加速老化及其组合。
本发明的组合物还可用于美容目的，例如用作摄食的美容组合物。
就此而言，本发明还涉及包含至少一种饮食性羟基肉桂酸和至少一种类黄酮和/或其结合物的组合物用于治疗或预防氧化性损害的美容用途，其中所述组合物被口服施用。
该组合物可以是适于人或动物使用的任何组合物。例如，该组合物可选自食品、饮料、宠物食品、营养品、食品添加剂或美容产品。
就此而言，该组合物可以被施用于人或动物，例如宠物如猫或狗。
该组合物可以在一天的任何时间被消费。但是，优选在早晨施用本发明的组合物以为身体迎接一天的挑战做准备。
为了确保身体在每一天都得到良好的保护，还优选在每天当中例如与膳食一起消费本发明的组合物。就此而言，本发明的组合物可以在早晨、午餐时间和晚上进行消费。
本领域技术人员将理解，可在不脱离所公开的本发明范围的情况下对本文所记载的所有特征进行组合。具体地讲，可将关于本发明应用所述的特征应用于本发明的组合物并且反之亦然。
本发明的其它优点和特征将由下面的实施例和附图而变得显而易见。
附图说明
图1A和B显示了木犀草素、槲皮素和槲皮素结合物在HepG2细胞中对咖啡酸(A)和阿魏酸(B)硫酸化的抑制作用。将咖啡酸和阿魏酸(10μM)在存在木犀草素、槲皮素或槲皮素结合物的情况下培养4小时。
具体实施方式
实施例:
1.1.在人肝脏和小肠S9中类黄酮对羟基肉桂酸类硫酸化的抑制作用
培养混合物(终体积为50μL)由100mM磷酸钾缓冲液(pH 7.4)、100μM维生素C、100μM PAPS和1mM DTT组成。将人肝S9和小肠S9匀浆分别以1mg/mL和0.4mg/mL的浓度使用。类黄酮以5mM溶解于DMSO中的储备液的形式加入，DMSO终浓度等于0.2％。将槲皮素-3-葡萄糖醛酸苷、槲皮素-7-葡萄糖醛酸苷和槲皮素-3’-硫酸酯溶解于水中。在进行15min预培养后，通过由位于DMSO中的50mM储备液加入10μM肉桂酸和25μM二氢肉桂酸来引发反应。为了抑制槲皮素葡萄糖醛酸苷的水解，在一些分析中，加入5mM葡糖二酸单内酯。将其在37℃水浴中培养30min后，通过加入10μL包含500mM HCl的冰冷的乙腈来终止反应。在相同的条件下对对照进行处理，且对照由加入到缓冲液中的含有0.2％DMSO(终浓度)的样品组成。将样品储存在-70℃下直至进行分析。
1.2.HepG2细胞培养
将HepG2细胞(ATCC)在75cm2细胞培养瓶中在37℃下在潮湿的5％CO2/O2气氛下进行常规培养。培养基由补加有10％胎牛血清(Sigma-Aldrich)和100U/ml青霉素-链霉素的伊格尔最低基础培养基(EMEM)组成。所有的实验都是用第80至95代之间的HepG2细胞进行的。为了进行代谢研究，将HepG2细胞以每孔2x105的细胞密度接种到12-孔板中。在用于实验前，使细胞单层生长96小时以上。羟基肉桂酸代谢实验在调至pH 6.5的含有100μM维生素C和1.8mM CaCl2的无血清培养基中进行。由位于DMSO中的50mM储备液加入肉桂酸(10μM)和二氢肉桂酸(25μM)。将槲皮素和木犀草素(5mM)也溶解于DMSO中并将其加入到培养基中至0.25％的DMSO终浓度。向该HepG2细胞中加入0.4mL含或不含抑制剂的羟基肉桂酸类并将其在37℃下培养4小时。然后，收集培养基，用1mM维生素C对其进行酸化并将其真空干燥。通过超声5min和涡旋1min来对残余物进行萃取，首先用500μL乙腈，然后用500μL甲醇进行萃取。将萃取物合并并将其在17,000g下离心10min。将上清液真空蒸发。在进行HPLC分析前，将干燥了的残余物重新溶解于100μL初始流动相中。
1.3.羟基肉桂酸类的HPLC法
用Agilent 1200系列液相色谱系统来进行HPLC分析。对于咖啡酸、阿魏酸、异阿魏酸、二氢阿魏酸及其结合物的分析而言，色谱法是用Zorbax XDB-C18柱(4.6x150mm,5μm)进行的。流动相组成为20mM甲酸铵,pH 2.8(A)和甲醇(B)。对于咖啡酸及结合物的分析而言，以1mL/min的流速，用20min内5％至25％B，然后2min 80％B和再回到5％B洗脱3min来对样品进行洗脱。对于阿魏酸和异阿魏酸及其结合物的分析而言，梯度为10分钟内10％至20％B，15分钟内至60％B，然后80％B 2min和恢复至10％B洗脱3min，流速为1mL/min。二氢阿魏酸及结合物的分析是以1mL/min的流速，在15min内从10％至20％B，10min内至60％B，2min高至80％B和最后至10％B洗脱3min的方式进行的。对于二氢咖啡酸及结合物而言，用Zorbax XDB-C18柱(4.6x 50mm,1.8μm)进行分析，用20mM甲酸铵,pH 4.5(A)和甲醇(B)作为流动相。梯度由3％(B)开始并保持15min，然后在5min内增至40％B，然后回到3％B洗脱5min。将样品离心并将25μL上清液注射到柱中。UV检测是在280nm和310nm下用光电二极管阵列检测器进行的。咖啡酸、阿魏酸和异阿魏酸在310nm下进行定量，二氢阿魏酸和二氢咖啡酸在280nm下进行定量。
2.结果
在表1、2和3中给出了类黄酮及其结合物的抑制作用(IC50)。
表1.类黄酮在人小肠S9中对咖啡酸和阿魏酸硫酸化的抑制作用
表2.类黄酮在人肝脏S9中对咖啡酸和阿魏酸硫酸化的抑制作用
表3.槲皮素结合物在肝S9中对咖啡酸和阿魏酸硫酸化的抑制作用
发现类黄酮是羟基肉桂酸硫酸化的有效抑制剂。异黄酮是小肠S9最强的抑制剂，而槲皮素和木犀草素是肝S9最有效的抑制剂。槲皮素结合物(在血液中发现的形式)也有效，其IC50值位于低的微摩尔范围内。
在图1A和1B中概述了类黄酮及结合物在HepG2细胞中对羟基肉桂酸类硫酸化的影响。
Claims (13)
1.用于治疗、减轻或预防与氧化性应激、炎性过程和/或免疫应答降低有关的病症的包含至少一种饮食性羟基肉桂酸的组合物，其中向该包含羟基肉桂酸的组合物中加入至少一种类黄酮的糖苷结合物。
2.权利要求1的组合物，其中所述至少一种类黄酮的糖苷结合物至少部分抑制了饮食性羟基肉桂酸类的硫酸化。
3.前述权利要求之一的组合物，其每份包含至少1mg羟基肉桂酸。
4.前述权利要求之一的组合物，其以100:1至10:1的摩尔比包含类黄酮的糖苷结合物和羟基肉桂酸。
5.前述权利要求之一的组合物，其中以天然食品或其提取物的形式向所述组合物中加入所述至少一种类黄酮的糖苷结合物。
6.权利要求5的组合物，其中所述天然食品选自红茶或绿茶、酸豆、拉维纪草、苹果、洋葱、特别是红洋葱、红葡萄、柑橘类水果、西红柿、西兰花、覆盆子、笃斯越桔、越橘、蔓越莓、野樱桃、甜山梨、花楸浆果、沙棘浆果、红莓苔子、仙人球仙人掌果实或其组合。
7.前述权利要求之一的组合物，其中所述饮食性羟基肉桂酸得自咖啡、可可、蔬菜或水果。
8.前述权利要求之一的组合物，其中所述饮食性羟基肉桂酸选自咖啡酸、二氢咖啡酸、二氢阿魏酸、阿魏酸、异阿魏酸或其组合。
9.前述权利要求之一的组合物，其中所述类黄酮的糖苷结合物选自槲皮素的糖苷结合物。
10.前述权利要求之一的组合物，其中所述与氧化性应激、炎性过程和/或免疫应答降低有关的病症选自高血糖症、2型糖尿病、心血管疾病、急性免疫和/或炎性反应、由紫外线(UV)辐射造成的皮肤细胞损害、细胞加速老化及其组合。
11.前述权利要求之一的组合物，其中该组合物选自食品、饮料、宠物食品、营养品、食品添加剂或美容产品。
12.用于在早晨进行施用的前述权利要求之一的组合物。
13.包含至少一种饮食性羟基肉桂酸和至少一种类黄酮的糖苷结合物的组合物用于治疗或预防氧化性损伤的美容应用，其中该组合物被口服施用。
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| CN (2) | CN106333944A (zh) |
| DK (1) | DK2785203T3 (zh) |
| ES (1) | ES2669311T3 (zh) |
| TR (1) | TR201808127T4 (zh) |
| WO (1) | WO2013079394A1 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018228430A1 (zh) * | 2017-06-13 | 2018-12-20 | 首都医科大学附属北京地坛医院 | 异阿魏酸、含异阿魏酸中药提取物及升麻的用途 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE202016008641U1 (de) | 2015-12-18 | 2018-10-15 | Mary Kay Inc. | Topische Kosmetikzusammensetzungen |
| RU2615474C1 (ru) * | 2016-01-20 | 2017-04-04 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Орловский государственный аграрный университет" | Биологически активная добавка для крупного рогатого скота на основе лецитина из подсолнечника |
| WO2023213813A1 (en) * | 2022-05-03 | 2023-11-09 | Universiteit Maastricht | Compound for use in the regulation of saccharide absorption via the gastrointestinal tract and compositions thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1931269A (zh) * | 2006-10-13 | 2007-03-21 | 深圳市生物谷科技有限公司 | 含有芦丁的药物组合物 |
| CN101721400A (zh) * | 2008-10-13 | 2010-06-09 | 青岛启元生物技术有限公司 | 阿魏酸在增加某些药物的药效作用及其用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09252746A (ja) * | 1996-03-22 | 1997-09-30 | Nippon Kankyo Yakuhin Kk | 栄養補助食品 |
| JP4082823B2 (ja) * | 1999-05-06 | 2008-04-30 | 日本メナード化粧品株式会社 | 光毒性抑制剤 |
| FR2822466B1 (fr) * | 2001-03-23 | 2004-07-02 | Diana Ingredients | Fraction phenolique riche en phloridzine et son utilisation en tant qu'agent cosmetique, alimentaire ou nutraceutique |
| FR2836336B1 (fr) * | 2002-02-26 | 2004-08-27 | Diana Ingredients | Utilisation dans un traitement cosmetique d'une fraction phenolique riche en dihydrochalcones |
| BRPI0802004A2 (pt) * | 2008-05-19 | 2010-01-12 | Univ Minas Gerais | extrato e fração padronizados de folhas de hancornia speciosa e sua composição farmacêutica |
| JP5765879B2 (ja) * | 2008-08-01 | 2015-08-19 | 小林製薬株式会社 | 蜂の子、プロポリス、およびローヤルゼリーを含有する経口摂取用組成物 |
| CA2798874C (en) * | 2010-05-10 | 2018-01-02 | Dalhousie University | Phenolic compositions derived from apple skin and uses thereof |
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2011
- 2011-11-28 EP EP11190863.8A patent/EP2596704A1/en not_active Withdrawn
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2012
- 2012-11-22 US US14/360,841 patent/US20140329904A1/en not_active Abandoned
- 2012-11-22 CN CN201610908574.8A patent/CN106333944A/zh active Pending
- 2012-11-22 DK DK12790898.6T patent/DK2785203T3/en active
- 2012-11-22 JP JP2014542835A patent/JP2015505821A/ja active Pending
- 2012-11-22 EP EP12790898.6A patent/EP2785203B1/en not_active Not-in-force
- 2012-11-22 ES ES12790898.6T patent/ES2669311T3/es active Active
- 2012-11-22 CN CN201280058454.3A patent/CN103974630B/zh not_active Expired - Fee Related
- 2012-11-22 TR TR2018/08127T patent/TR201808127T4/tr unknown
- 2012-11-22 WO PCT/EP2012/073383 patent/WO2013079394A1/en active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1931269A (zh) * | 2006-10-13 | 2007-03-21 | 深圳市生物谷科技有限公司 | 含有芦丁的药物组合物 |
| CN101721400A (zh) * | 2008-10-13 | 2010-06-09 | 青岛启元生物技术有限公司 | 阿魏酸在增加某些药物的药效作用及其用途 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018228430A1 (zh) * | 2017-06-13 | 2018-12-20 | 首都医科大学附属北京地坛医院 | 异阿魏酸、含异阿魏酸中药提取物及升麻的用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| TR201808127T4 (tr) | 2018-07-23 |
| ES2669311T3 (es) | 2018-05-24 |
| US20140329904A1 (en) | 2014-11-06 |
| DK2785203T3 (en) | 2018-05-28 |
| EP2596704A1 (en) | 2013-05-29 |
| WO2013079394A1 (en) | 2013-06-06 |
| EP2785203A1 (en) | 2014-10-08 |
| EP2785203B1 (en) | 2018-03-07 |
| CN103974630A (zh) | 2014-08-06 |
| JP2015505821A (ja) | 2015-02-26 |
| CN103974630B (zh) | 2016-11-16 |
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