CN104869848B - 用多酚增加黄烷-3-醇的生物利用度 - Google Patents
用多酚增加黄烷-3-醇的生物利用度 Download PDFInfo
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Abstract
概括而言,本发明涉及黄烷‑3‑醇领域。具体地,本发明提供了增加黄烷‑3‑醇的生物利用度的方法。本发明的实施方案涉及在包含至少一种黄烷‑3‑醇的组合物中的至少一种多酚化合物用于增加所述黄烷‑3‑醇的生物利用度的用途,其中所述的至少一种多酚化合物选自黄酮醇、黄酮、异黄酮、黄烷酮或其组合。
Description
概括而言,本发明涉及黄烷-3-醇领域。具体地,本发明提供了增加黄烷-3-醇的生物利用度的方法。本发明的实施方案涉及在包含至少一种黄烷-3-醇的组合物中的至少一种多酚化合物用于增加所述黄烷-3-醇的生物利用度的用途,其中所述的至少一种多酚化合物选自黄酮醇、黄酮、异黄酮、黄烷酮或其组合。
黄烷-3-醇(包括例如“儿茶素”)存在于多种食品来源例如可可、茶和苹果中。多种流行病学体外和体内研究已经将这些化合物的存在与健康促进作用例如抗氧化和抗炎益处相关联(Aron,P.M.等人,2008,Molecular Nutrition&Food Research 52,79–104)。
一般而言,黄烷-3-醇经受几种II期酶的作用,从而导致与甲基(儿茶酚-O-甲基转移酶-COMT)、硫酸酯基(磺基转移酶-SULT)和葡糖醛酸基(glucuronyl group)(尿苷-5’-二磷酸葡糖醛酸基转移酶(glucuronosyl transferase)-UDPGT)缀合。然而,已经报道EGCG(绿茶中存在的主要黄烷-3-醇)主要以其天然形式存在于人血浆中(Williamson等人,2011,Mol Nutr Food Res 55,864–873)。
例如,绿茶黄烷-3-醇的口服生物利用度低,导致在人体中全身黄烷-3-醇水平低于在体外系统中测定的有效浓度许多倍(Lambert等人,2007,Mol.Pharmaceutics 4,819–825)。文献中已经报道了增加来自绿茶的黄烷-3-醇的生物利用度的许多方法,例如与存在于黑胡椒中的生物碱胡椒碱组合施用茶和使EGCG过乙酰化(peracetylation)。另一种改善黄烷-3-醇吸收的策略是在禁食状态中施用,然而,重要的是要注意,一些人体研究已经证实,高剂量的绿茶制品可能具有潜在毒性(Chow等人,2005,Clinical Cancer Research11,4627–4633;Bonkovsky,2006,Ann Intern Med 144,68–71)。
因此,本领域中对于改善黄烷-3-醇的吸收、同时避免黄烷-3-醇的超剂量给予(overdosing)的可选方法存在需求。
本说明书中任何对现有技术的提及均不应理解为承认所述现有技术是广泛已知的或者形成本领域公知常识的一部分。
因此,本发明的目的是改善本领域的状态,特别是提供施用黄烷-3-醇、同时确保有效吸收和高生物利用度的方法,或至少提供本领域已知方法的有用的供替代选择的方法。
发明人令人惊讶地发现,本发明的目的能通过独立权利要求的主题来实现。从属权利要求进一步发展了本发明的理念。
因此,本发明提供了用于增加黄烷-3-醇、特别是它们的生物学活性形式、母体化合物和/或代谢物的吸收的新方法。根据本发明,这通过共同施用这些化合物与多酚、例如膳食多酚得以实现。
本说明书中所用的措词“包含”、“含有”和类似措词不应被解释为排他性的或穷尽性的含义。换言之,它们用于意指“包括、但不限于”。
本发明的发明人已经使用Caco-2细胞模型和体内人生物利用度研究进行了广泛的体外实验,它们能证实共同施用黄烷-3-醇与某些多酚能增加黄烷-3-醇和/或它们的代谢物的吸收。不希望收到理论约束,发明人目前认为黄烷-3-醇的吸收受其它多酚的存在调控,所述调控通过几种机制实现,例如通过与代谢酶竞争和/或通过抑制黄烷-3-醇和/或它们的代谢物从细胞中流出。
因此,本发明部分涉及在包含至少一种黄烷-3-醇的组合物中的至少一种多酚化合物用于增加所述黄烷-3-醇的生物利用度的非治疗用途,其中所述的至少一种多酚化合物选自黄酮醇、黄酮、异黄酮、黄烷酮或其组合。
在另一个方面,本发明涉及包含选自黄酮醇、黄酮、异黄酮、黄烷酮或其组合的至少一种多酚化合物和至少一种黄烷-3-醇的组合物,其用于治疗或预防能通过黄烷-3-醇施用被治疗或预防的障碍。
图1显示了可形成本发明的混合物的化合物的通式(A、B和C)。
图2显示了不同的多酚化合物与(-)-表儿茶素共同温育对(-)-3’-O-甲基-(-)-表儿茶素的顶端(apical)流出和基底外侧(basolateral)转运的作用。
图3显示了染料木素、石吊兰素、橙皮素(hesperitin)和白杨黄素与(-)-表儿茶素共同温育对3’-O-甲基-表儿茶素(代谢物)的顶端流出和基底外侧转运的剂量依赖性作用。
图4显示了不同的多酚化合物与(-)-表儿茶素共同温育对3’-O-硫酸酯-表儿茶素(代谢物)的顶端流出和基底外侧转运的作用。
表1给出了来自对照组(GT=绿茶提取物)和治疗组(GT+HG=绿茶提取物+橙皮素7-葡糖苷(hesperitin 7-glucoside))的受试者的EGCG(表棓儿茶素-3-棓酸酯(Epigallocatechin 3-gallate))的动力学参数,例如AUC(曲线下面积)和Cmax(最大浓度)。
因此,本发明部分涉及在包含至少一种黄烷-3-醇的组合物中的至少一种多酚化合物用于增加所述黄烷-3-醇的生物利用度的非治疗用途。
可以将生物利用度定义为能被吸收的且对于使用或贮存而言可利用的所施用物质的比例。
本发明还涉及包含至少一种黄烷-3-醇的组合物,其用于治疗或预防能通过黄烷-3-醇施用被治疗或预防的障碍,其中所述组合物还包含用于增加所述黄烷-3-醇的生物利用度的至少一种多酚化合物。
本发明还涉及至少一种黄烷-3-醇在制备用于治疗或预防能通过黄烷-3-醇施用被治疗或预防的障碍的组合物中的用途,其中所述组合物还包含用于增加所述黄烷-3-醇的生物利用度的至少一种多酚化合物。
能通过黄烷-3-醇施用被治疗或预防的障碍是本领域技术人员众所周知的。能通过黄烷-3-醇施用被治疗或预防的障碍的实例可以选自心血管疾病、2型糖尿病、超重、肥胖、炎性障碍、认知功能损害(cognitive impairment)和氧化性皮肤损伤(oxidative skindamage)。
发明人已经使用Caco-2细胞模型研究了如果将黄烷-3-醇与其它多酚共同施用如何影响黄烷-3-醇吸收。
发明人发现,如果将黄烷-3-醇与黄酮醇、黄酮、异黄酮和/或黄烷酮共同施用,黄烷-3-醇的吸收能被显著提高,而其它测试的多酚对黄烷-3-醇的吸收没有显著影响。
发明人还进行了人生物利用度研究以评价如果将黄烷-3-醇与其它多酚共同施用在体内如何影响黄烷-3-醇吸收、更特别是EGCG。
发明人发现,如果将黄烷-3-醇与例如黄烷酮例如橙皮素7-葡糖苷共同施用,EGCG的吸收能被显著提高。
因此,根据本发明,所述的至少一种多酚化合物可以选自黄酮醇、黄酮、异黄酮、黄烷酮或其组合。
这种吸收的增加清楚地表明,如果与测试的多酚共同施用,则黄烷-3-醇的生物利用度被改善。
通过经与多酚共同施用改善黄烷-3-醇的生物利用度,所述黄烷-3-醇干预的有益改变或治疗效果的能力被改善。
因此,本发明的黄烷-3-醇与多酚的共同施用增加所述黄烷-3-醇的生物功效(bioefficacy)。
落入下文所定义的通式(I)范围内的化合物在增强黄烷-3-醇的吸收方面是特别有效的。
在一个实施方案中,所述的至少一种多酚化合物是式(I)的黄酮醇、黄酮、异黄酮和/或黄烷酮:
其中
R6选自:H、OH、OCH3和式(II)的环烃基:
R7选自:H、OH、OCH3和式(II)的环烃基;
R8选自:H、O、OH和OCH3;
每个R9取代基独立地选自:H、OH和OCH3;
式(II)的每个R10独立地选自:H、OH和OCH3;
且
式(I)中的1位与2位之间和3位与4位之间的虚线代表任选的双键;
条件是
如果R6、R7或R8是OH,则任意相邻的R6、R7或R8取代基不是OH;
如果一个R9取代基是OH,则任意相邻的R9取代基不是OH;
当R8是O时,3位与4位之间存在双键;
且
如果式(II)的一个R10取代基是OH,则式(II)的任意相邻的R10取代基不是OH。
在一个实施方案中,所述组合物包含式(I)的黄酮醇、黄酮、异黄酮和/或黄烷酮,其选自:
3-羟基黄酮、山柰素、山柰酚、异鼠李亭、柚皮黄素(Natsudaidain)、藿香黄酮醇(Pachypodol)、甲基鼠李黄素、黄酮、芹菜素、白杨黄素、橙皮素、柚苷配基(Naringinine)、樱花亭、染料木素、雌马酚、石吊兰素或其组合。
在一个实施方案中,所述组合物包含黄酮醇、黄酮、异黄酮和/或黄烷酮,其选自:异鼠李亭、山柰酚、香叶木素、石吊兰素、白杨黄素、雌马酚、染料木素、橙皮素或其组合。
在一个实施方案中,所述的至少一种多酚化合物是上文所定义的式(I)的黄酮醇、黄酮、异黄酮和/或黄烷酮,其中所述异黄酮是异黄烷二醇(isoflavandiol)。
在一个具体的实施方案中,所述的至少一种多酚化合物是上文所定义的式(I)的黄酮、异黄酮和/或黄烷酮,其中所述异黄酮是异黄烷二醇。
在一个实施方案中,所述的至少一种多酚化合物是上文所定义的式(I)的黄酮和/或黄烷酮。
在一个实施方案中,所述的至少一种多酚化合物是黄酮和/或黄烷酮,其选自:异鼠李亭、山柰酚、香叶木素、石吊兰素、白杨黄素、橙皮素或其组合。
非治疗用途可以是例如美容用途。
优选的是,所述的至少一种多酚化合物得自天然来源、例如得自膳食来源。
各种水果和蔬菜可以用作黄酮醇的来源。典型地,黄酮醇的日摄入量是20–50mg黄酮醇/天。
谷物和草药是典型的黄酮的来源。典型地,黄酮的日摄入量是20–50mg黄酮/天。
大豆是异黄酮的良好天然来源且因此是豆科(Leguminosae)植物家族的几个成员。另外的膳食来源是鹰嘴豆、苜蓿(alfalfa)和花生。
黄烷酮典型地存在于柑橘果实中,例如橘或柑或橙(oranges)、葡萄柚、柠檬和酸橙。它们还存在于常用于厨房的成分中,例如欧芹、芹菜和某些尖辣椒。
因此,本发明框架中所用的多酚化合物可以以纯化合物的形式被提供,也可以以来自膳食成分的提取物的形式被提供,或者直接以加工的或未加工的膳食成分的形式被提供。
提供来自这类众所周知的天然来源的多酚化合物具有优点—所述化合物被消费者充分接受,在合理的用量下一般被视为是安全的,并且天然来源甚至能用于在味道和种类方面丰富食物产品。
例如,所述的至少一种多酚化合物可以选自异鼠李亭、山柰酚、香叶木素、石吊兰素、白杨黄素、雌马酚、染料木素、橙皮素或其组合。
异鼠李亭和山柰酚是黄酮醇;香叶木素、石吊兰素、白杨黄素是黄酮;雌马酚和染料木素是异黄酮,橙皮素是黄烷酮。
黄烷-3-醇也可以从天然来源提供。它们可以以来自这些天然来源的提取物的形式或者以作为食品成分的天然来源本身的形式(加工的或未加工的)被提供。
例如,黄烷-3-醇可以来源于绿茶、白茶(white tea)、野生植物果实,特别是浆果、苹果、可可豆或其它含有黄烷-3-醇的果实。
绿茶是全世界位于水之后最常消耗的饮料,其是黄烷-3-醇的非常好的来源。尽管绿茶中存在的黄烷-3-醇的量因影响植物代谢的因素例如光、降雨、温度、营养物可利用性、叶龄和遗传组成的不同而异,但是它们通常占新鲜绿茶叶的干物质的16-24%。由于黄烷-3-醇典型地在绿茶制备期间是稳定的,所以它们是商品绿茶提取物的主要部分。
主要的绿茶黄烷-3-醇是儿茶素,即(+)-儿茶素(C)及其立体异构体和四种衍生物,即(-)-表儿茶素(EC)、(-)-表棓儿茶素(EGC)、(-)-表棓儿茶素-3-棓酸酯(EGCg)、(-)-表儿茶素-3-棓酸酯(ECg)。
黄烷-3-醇展现出多种健康益处,它们常与其抗氧化活性相关,包括清除活性氧和氮种类、游离金属螯合、抑制转录因子和抑制氧化酶例如脂氧化酶和环加氧酶(cycloxygenase)。
在一个实施方案中,黄烷-3-醇来自绿茶。或者,也可以使用黄烷-3-醇的其它来源。
绿茶或其它植物来源可以以新鲜的、浓缩的或干燥的物质形式、例如风干的或冻干的物质形式被使用。
例如,本发明中所用的黄烷-3-醇可以选自(+)-儿茶素(C)、(-)-表儿茶素(EC)、棓儿茶素(gallocatechin)(GC)、棓儿茶素棓酸酯(gallocatechingallate)(GCG)、(-)-表棓儿茶素(EGC)、(-)-表棓儿茶素-3-棓酸酯(EGCg)、(-)-表儿茶素-3-棓酸酯(ECg)或其组合。
在一个实施方案中,本发明中所用的黄烷-3-醇是(-)-表儿茶素。
在一个实施方案中,本发明中所用的黄烷-3-醇是(-)-表儿茶素-3-棓酸酯。
组合物中黄烷-3-醇的量取决于其预期的应用。
在治疗应用中,活性化合物以足以至少部分治愈或阻止障碍和/或其并发症的症状的量被施用。足以达到这一目的的量被定义为“治疗有效剂量”。对于该目的而言有效的量取决于本领域技术人员已知的许多因素,例如障碍的严重性和患者的体重和总体状况。
在预防应用中,本发明的活性化合物以足以至少部分降低发生障碍的风险的量被施用于易于罹患特定障碍或者有罹患特定障碍风险的患者。这样的量被定义为“预防有效剂量”。此外,精确的量取决于许多患者的特定因素,例如患者的健康状况和体重。
在非治疗应用例如美容应用中,本发明的活性化合物以足以至少部分减少人身体外观的可见的或可触知的缺陷的量施用于人。这样的量被定义为“美容有效剂量”。此外,精确的量取决于许多人的特定因素,例如人的性别、种族、肤色、年龄或健康状况。
在本发明的框架内,活性化合物可以以预防有效剂量、治疗有效剂量或美容有效剂量被施用。
本发明中所用的活性化合物是黄烷-3-醇。
例如,黄烷-3-醇可以以相当于组合物的干重的0.5–50重量%、例如组合物干重的1.5–20重量%或组合物干重的2–10重量%的量存在于本发明所述的组合物中。
为了最佳地改善黄烷-3-醇的吸收和生物利用度,应使用适宜比例的多酚化合物和黄烷-3-醇。
该理想的比例取决于许多因素,例如食品基质的性质、活性化合物的浓度以及贮存和消耗的细节。本领域技术人员能鉴定这类最佳比例。例如,本发明的组合物可以含有重量比在1:1至100:1范围内的、例如重量比在5:1至75:1范围内的、重量比在10:1至50:1范围内的或重量比在15:1至25:1范围内的多酚化合物和黄烷-3-醇。
本发明的组合物可以被口服施用,或者其可以例如被应用于体表。组合物可以是食料(foodstuff)、饮料、食品补充剂、宠物食品、营养品(nutritional)或美容组合物(cosmetic composition)。
用于人消耗的食品组合物可以是完全营养配方、乳制品、冷却或货架稳定的饮料、矿物质水或纯净水、液体饮料、汤、膳食补充剂、餐食替代物(meal replacement)、营养棒、甜食、奶或发酵奶产品、酸奶、基于奶的粉末、肠内营养产品、婴儿配方、婴儿营养产品、谷物产品或基于发酵谷物的产品、冰淇淋、巧克力、咖啡、烹调产品如蛋黄酱、番茄泥或色拉调料或宠物食品。
就摄入而言,口服组合物的许多实施方案且特别是食品补充剂的许多实施方案是可能的。它们可以被配制成包糖衣片、丸剂、糊剂、口香糖(gums)、明胶胶囊剂、凝胶剂、乳剂、片剂、胶囊剂或可饮用的溶液或乳剂的形式,然后它们可以直接与水一起被服用或者通过任意其它已知的方式服用。
食品组合物或食品补充剂还可以包含甜味剂、稳定剂、抗氧化剂、添加剂、矫味剂或着色剂。组合物还可以含有合成的或天然的生物活性成分,例如氨基酸、脂肪酸、维生素、矿物质、类胡萝卜素、多酚等,它们可以通过干或湿混合被加入到所述组合物中,然后进行巴氏灭菌和/或干燥。
根据一个实施方案,本发明的组合物可以美容使用。“美容使用”或“美容用途”是非治疗用途,其可以改善人或宠物的皮肤、皮毛和/或毛发的美学方面或舒适性。
当美容使用时,本发明的组合物可以是上述任何形式的食品组合物或补充剂。优选地,它是膳食补充剂的形式,其可以是液体或干燥形式,例如溶液、喷雾剂、片剂、胶囊剂、明胶胶囊剂、锭剂(lozenge)、散剂、凝胶剂、乳剂等。更优选地,它是胶囊剂的形式。用于美容目的的补充剂可以另外包含对皮肤具有活性的化合物。
本发明还涉及局部组合物。这类局部组合物可以被配制成例如洗剂、香波、乳膏剂、防晒剂(sun-screen)、日晒后乳膏剂(after-sun cream)、抗老化乳膏剂和/或软膏剂。可以局部使用的组合物可以另外包含能在美容用品(cosmetics)中使用的脂肪或油,例如CTFA著作Cosmetic Ingredients Handbook,华盛顿中提及的那些。还可能加入其它美容活性成分。这类组合物可以另外包含构造剂(structuring agent)和/或乳化剂。还可以向组合物中加入其它赋形剂、着色剂、香料或遮光剂。应当理解的是,美容产品可以含有本领域技术人员已知的不同成分的混合物,从而确保所述物质快速渗透入皮肤和防止其在贮存期间降解。
应当理解的是,本发明的概念同样可以用作协助目前使用的药物治疗的辅助疗法。
本领域技术人员可以理解,他们可以自由地组合本文所公开的本发明的所有特征。具体地,可以将针对本发明的非治疗用途所述的特征与针对本发明的用途所述的组合物组合,反之亦然。此外,可以组合针对本发明的不同实施方案所述的特征。
尽管已经通过实施例描述了本发明,但是应当理解的是,可以在不脱离权利要求中所定义的本发明的范围的情况下进行改变和变型。
此外,如果存在特定特征的已知等同物,则将这类等同物合并入本文,就如同在本说明书中具体提及了一样。本发明的另外的优点和特征因附图和非限制性实施例而显而易见。
实施例1:体外caco 2-细胞模型
方法:Caco-2人上皮结肠直肠腺癌细胞用于体外研究(–)-表儿茶素的转运。
使细胞在补充了20%热灭活胎牛血清、非必需氨基酸和2mM L-谷氨酰胺、两性霉素B(1μg/ml)、青霉素(100U/ml)和链霉素(100μg/ml)的高葡萄糖DMEM中生长并且维持在37℃和5%CO2下。每2天替换一次培养基,每7天重新接种一次细胞。然后,以20,000个细胞/cm2的密度将细胞接种在12孔跨孔(transwell)插入物中,每2天替换一次两侧的培养基。21天后,细胞已经分化。
在实验的当天,除去培养基,替换为补充了25mM葡萄糖、10mMHEPES和1.8mM CaCl2的HBSS。加入过氧化氢酶(189U/ml)和抗坏血酸(0.5mM)以防止测试化合物氧化。然后,将单独的(–)-表儿茶素(100μM)或(–)-表儿茶素(100μM)+多酚(2-100μM)放入细胞单层的顶端侧并且温育2h。将所有化合物加入到来自在DMSO中的储备液的暴露培养基中。每个实验中顶端侧的DMSO浓度保持在0.05%。使用装配有HSS C18VanGuard预柱(Waters,瑞士)的Acquity UPLC HSS C182.1x100mm,1.8μm柱(Waters,瑞士)用超效液相色谱法检测细胞培养基中的缀合化合物(代谢物)。
结果:由于(-)-表儿茶素以缀合物(代谢物)的形式存在于血浆中,所以这些化合物是在血液中循环并且最可能达到不同作用部位并发挥文献中报道的有益效果的化合物。
由该体外模型获得的结果表明,当与一些选择的多酚组合时,基底室中甲基和/或硫酸酯表儿茶素代谢物的浓度有显著的增加(图2和3),表明这些代谢物被更好地吸收了。
此外,还观察到了所选择的多酚与(-)-表儿茶素共同温育的剂量依赖性作用(图4)。
实施例2:体内人生物利用度干预研究
方法:12位健康男性(20-50岁)入选了随机化双盲交叉设计的4个治疗,在应用每个治疗之间有最少1周的洗脱期。
在本发明中,仅2个治疗是研究目标:绿茶提取物(对照)和绿茶提取物+橙皮素7-葡糖苷(干预)。
每个治疗被配制含有Choladi绿茶提取物的1g等价物。干预组中的受试者接受1g绿茶提取物和100mg橙皮素-7-葡糖苷的混合物。
摄取后,历经24h采集血浆。通过偶联电化学检测的HPLC进行血浆EGCG分析。
通过测定其浓度-时间曲线下面积(AUC)根据血浆动力学计算了EGCG的生物利用度。
结果:与(-)-表儿茶素不同,EGCG主要以其天然形式(母体化合物)存在于血浆中,这意味着母体化合物最可能是达到不同作用部位且发挥文献中报道的有益效果的化合物。
结果表明,与公开的数据相比,来自绿茶提取物的EGCG被良好地吸收。然而,在含有橙皮素7-葡糖苷的绿茶制剂中的EGCG的AUC比对照(绿茶提取物)高约25%(表1)。
来自该生物利用度研究的结果表明,当与一些选择的多酚例如橙皮素7-葡糖苷组合时,血浆EGCG浓度有显著的增加,这表明该化合物被更好地吸收了。
Claims (6)
1.至少一种多酚化合物在制备用于增加黄烷-3-醇的生物利用度的组合物中的用途,其中所述的至少一种多酚化合物选自异鼠李亭、山柰酚、香叶木素、石吊兰素、白杨黄素、雌马酚、橙皮素或其组合,并且其中所述的黄烷-3-醇是(-)-表儿茶素(EC)。
2.根据权利要求1所述的用途,其中所述的至少一种多酚化合物是从天然来源获得的。
3.根据权利要求1所述的用途,其中所述的黄烷-3-醇源自绿茶和含有所述黄烷-3-醇的野生植物果实。
4.根据权利要求3所述的用途,其中所述的野生植物果实是浆果、苹果、可可豆或其它含有所述黄烷-3-醇的果实。
5.根据权利要求1至4之一所述的用途,其中所述组合物是食料、饮料、食品补充剂、宠物食品、营养品或美容组合物。
6.根据权利要求1至4之一所述的用途,其中紧接着所述黄烷-3-醇的生物利用度的增加,其生物功效增加。
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