CN102014648A - 咖啡绿原酸衍生的脱羧酚酸的用途和包含其的产品 - Google Patents
咖啡绿原酸衍生的脱羧酚酸的用途和包含其的产品 Download PDFInfo
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Abstract
本发明涉及咖啡绿原酸衍生的脱羧酚酸的用途,和包含咖啡绿原酸衍生的脱羧酚酸的产品,特别是咖啡提取物,以及制备这些产品的方法。咖啡包含绿原酸,根据本发明这些绿原酸可转化为脱羧酚酸。得到的脱羧酚酸具有抗氧化和/或抗炎症特性,其可用作食物或饮料产品的成分和用于治疗某些健康情况。
Description
发明领域
本发明涉及咖啡绿原酸衍生的脱羧酚酸的用途,和包含咖啡绿原酸衍生的脱羧酚酸的产品,特别是咖啡提取物,以及制备这些产品的方法。
背景
已有研究显示咖啡和咖啡活性化合物例如咖啡因和二萜(例如咖啡醇和咖啡豆醇)可诱导解毒酶(例如谷胱甘肽S转移酶)(Cavin C.等人,1998.The coffee-specific diterpenes cafestol and kahweol protect againstaflatoxin B1-induced genotoxicity trough a dual mechanism.Carcinogenesis 19,1369-1375;Cavin,C.等人,2003.Coffeediterpenes prevent benzo[a]pyrene genotoxicity in rat and humanculture systems.Biochemical Biophysical Research Communication 306,488-495;Huber,W.等人.2002a.Enhancement of the chemoprotectiveenzymes glucuronosyl transferase and glutathione transferase inspecific organs of the rat by the coffee components kahweol andcafestol.Archive of Toxicology 76,209-217)。在5天消耗800ml咖啡的人中进一步证明了咖啡可以提高GST活性(Steinkellner,H.等人.2005.Coffee consumption induces GSTP in plasma and protectslymphocytes against(+/-)-anti-benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide inducedDNA-damage:results of controlled human intervention trials.Mut.Res.591264-275)。
已知这种抗氧化活性可以对抗“氧化应激”,通过降低可能与例如癌症、心脏疾病、退行性脑疾病和衰老相关的有害自由基。
阿尔茨海默病(AD)为一种进行性神经变性疾病,最常见的形式为痴呆,其症状为例如记忆力丧失、意识混乱、情绪波动和认知功能减退。其特征是脑内细胞外淀粉样斑块和神经元内神经原纤维缠结,其中主要组成部分是一种被称为淀粉样β蛋白(Aβ)的39-42残基肽的纤维状聚集。目前认为Aβ原纤维的形成在AD病原学中发挥主要作用。已有研究显示几种致病AD突变,可导致Aβ、特别是突变体Aβ42水平的提高。因此认为淀粉样原纤维的形成是AD中疾病恶化和神经变性的原因。通过体外研究已经证明Aβ原纤维的形成通过复杂的多步骤机制发生,其中涉及离散的可溶性寡聚中间体ADDLS或称初原纤维(PF),其在原纤维形成后消失。这提示PF可能为AD的致病种群。在人和动物中许多其他疾病涉及蛋白质聚集,例如黄斑变性、牛海绵状脑病(BSE)、克-雅氏病(Creutzfeldt-Jakobdisease)和糖尿病。
为提高食物和饮料产品的健康效益,希望能够生产具有提高的抗氧化活性以及其他有益生物学活性的产品,并寻找抗氧化和其他有益生物学活性化合物的天然来源,以用于增强食物和饮料产品的特性以及用于例如化妆品和医药产品。
发明概述
发明者目前发现咖啡绿原酸衍生的脱羧酚酸具有抗氧化和抗炎症特性,并可有效抑制和/或延缓淀粉样β肽的聚集,所述脱羧酚酸可从咖啡提取物中制备,得到具有增强的抗氧化和抗炎症特性的咖啡提取物。相应的,本发明涉及制备包含咖啡绿原酸衍生的脱羧酚酸的咖啡提取物的方法,所述方法包含:a)用水和/或蒸汽提取咖啡豆以制备咖啡提取物;和b)处理咖啡提取物,将提取物中存在的绿原酸水解为酚酸,并将得到的酚酸脱羧。在另一个方面本发明涉及包含咖啡绿原酸衍生的脱羧酚酸的咖啡提取物,一种制备食物或饮料产品的方法,包含咖啡绿原酸衍生的脱羧酚酸的食物或饮料产品,以及咖啡绿原酸衍生的脱羧酚酸的用途。
附图简述
图1显示了4-乙烯基儿茶酚降低和/或阻断淀粉样β肽单体到淀粉样原纤维形成的实验结果。白色棒为对照;浅灰色棒为1∶0.5(摩尔比率)比率的Aβ42和4-乙烯基儿茶酚;深灰色棒为1∶2(摩尔比率)比率的Aβ42和4-乙烯基儿茶酚。
图2显示了4-乙烯基儿茶酚降低和/或阻断淀粉样β肽初原纤维到淀粉样原纤维形成的实验结果。白色棒为对照;浅灰色棒为1∶0.5(摩尔比率)比率的Aβ42和4-乙烯基儿茶酚;深灰色棒为1∶2(摩尔比率)比率的A β42和4-乙烯基儿茶酚。
发明详述
绿原酸是由反式桂皮酸和奎尼酸形成的酯家族。绿原酸天然存在于咖啡中,主要为奎尼酸的单或二酯形式,在不同位置上连接酚基团(例如咖啡的、阿魏酸的、香豆的和甲氧基肉桂的)。绿原酸经水解可生成酚化合物例如咖啡酸和阿魏酸。这些酚化合物可通过脱羧进一步转化。本发明涉及咖啡绿原酸衍生的脱羧酚酸。咖啡绿原酸的意思是一种或多种在咖啡中天然发现的绿原酸,所述绿原酸包含真正来自咖啡的或其他来源的酚基团。在一个优选的实施方案中,咖啡绿原酸真正来自咖啡。自然存在于咖啡中的绿原酸为例如咖啡酰奎尼酸(CQA)(例如3-、4-或5-咖啡酰奎尼酸)和二酯,阿魏酰奎尼酸(FQA)(例如3-、4-或5-阿魏酰奎尼酸)和二酯,和二甲氧基肉桂酰奎尼酸(DMCQA)(例如3-、4-或5-二甲氧基肉桂酰奎尼酸)和二酯。
咖啡绿原酸可水解生成酚酸,例如CQA可水解生成咖啡酸(CA),FQA可水解生成阿魏酸(FA),DMCQA可水解生成二甲氧基肉桂酸(DMCA)。咖啡绿原酸水解生成的酚酸可进一步脱羧生成咖啡绿原酸衍生的脱羧酚酸;例如CA可脱羧生成4-乙烯基儿茶酚,FA可脱羧生成4-乙烯基愈创木酚,DMCA可脱羧生成4-乙烯基藜芦醚。
在本发明的一个实施方案中,咖啡绿原酸衍生的脱羧酚酸为4-乙烯基儿茶酚或其甲氧基衍生物。4-乙烯基儿茶酚的甲氧基衍生物为例如4-乙烯基愈创木酚和4-乙烯基藜芦醚。在本发明的一个优选的实施方案中,咖啡绿原酸衍生的脱羧酚酸选自4-乙烯基儿茶酚、4-乙烯基愈创木酚、4-乙烯基藜芦醚和其混合物。
本发明涉及包含咖啡绿原酸衍生的脱羧酚酸的咖啡提取物,所述咖啡提取物可包含一或多种咖啡绿原酸衍生的脱羧酚酸。本发明的咖啡提取物可为烘焙咖啡豆、生咖啡豆或两者的提取物。
在本发明的一个实施方案中,咖啡提取物包含至少0.1毫克总重的4-乙烯基儿茶酚、4-乙烯基愈创木酚和4-乙烯基藜芦醚每克干物质,例如至少1、至少2、至少5或至少20毫克每克干物质。在另一个实施方案中,咖啡提取物包含至少0.1毫克4-乙烯基儿茶酚每克干物质,例如至少1、至少2、至少5或至少20毫克每克干物质。
根据本发明的方法,咖啡绿原酸衍生的绿原酸可转化为脱羧酚酸,通过将绿原酸水解为酚酸并将得到的酚酸脱羧,如上述。
水解和脱羧反应可单独进行或可在时间上重叠进行。
可通过任意合适的方法对绿原酸进行转化。在本发明的一个实施方案中,所述转化通过一或多种能够在咖啡中转化绿原酸的微生物进行。可以鉴定能够转化绿原酸的微生物,例如在此申请的实施例中所公开的。合适的微生物可为酵母,例如面包酵母;真菌,例如曲霉属(Aspergillus);或细菌,例如乳酸细菌,例如乳酸杆菌属(Lactobacillus),例如约氏乳杆菌(L.johnsonii)(CNCM I-1225)。在本发明的一个实施方案中,能够转化绿原酸的微生物为乳酸细菌。在本发明的另一个实施方案中,使用2或多种微生物转化绿原酸,例如一或多种能够将绿原酸水解为酚酸的微生物,和一或多种能够将酚酸脱羧的微生物。
绿原酸的转化可通过下述方法进行:将咖啡提取物和能够转化绿原酸的微生物,在适于特异微生物生长的条件下孵育必需的时间以得到需要的绿原酸转化。技术人员可容易的决定特异的条件,例如通过参考此处包含的实施例。
在本发明的另一个实施方案中,通过一或多种合适的微生物使用非复制型微生物(例如裂解的微生物细胞)进行绿原酸的转化。通过将咖啡提取物和裂解细胞在合适的条件下孵育,细胞裂解液中存在的酶可转化绿原酸。合适的细胞可为例如上述微生物的细胞。制备细胞裂解液的合适方法是本领域所公知的。
微生物的量和转化条件应为合适的以获得需要的绿原酸转化,并可由技术人员通过常规方法决定,例如使用此处实施例中公开的方法。
在另一个实施方案中,通过使用一或多种能够转化绿原酸的酶进行绿原酸的转化。在一个实施方案中使用了至少2种酶,至少1种能够将绿原酸水解生成酚酸的酶,和至少1种能够将得到的酚酸脱羧的酶。合适的水解绿原酸的酶为例如酯酶,例如来自日本曲霉(Aspergillus japonicus)(Kikkoman,Japan)的绿原酸酯酶。合适的将酚酸脱羧的酶为例如脱羧酶(EC 4.1.1.X),例如丙酮酸脱羧酶(EC 4.1.1.1)。可通过酶促反应的传统方法进行酶促转化,例如通过在适于需要的酶活性条件下在咖啡提取物中溶解或悬浮酶。可通过例如在转化完成后加热将酶失活。待使用的酶也可固化,例如在膜上或在惰性载体上,待处理的咖啡提取物可通过膜或载体循环直至获得期望的转化程度。当使用2种或多种酶时,可以同时使用,或相继进行处理,例如如果酶之间的最适条件不同。
待使用的酶量和条件应该适于获得期望的绿原酸水解和酚酸脱羧,并可由技术人员通过常规方法决定。
待提取的用于制备咖啡提取物的咖啡豆可为整个或磨碎的。在本发明的一个实施方案中咖啡豆为生咖啡豆。在另一个实施方案中,生咖啡豆和烘焙咖啡豆一起被提取,即在相同的提取体系同时提取生的和烘焙咖啡豆,得到混合的提取物。可在提取前从豆中汽提(strip)最具挥发性的香气成分,例如如果待使用的提取物是用于制备纯可溶咖啡。用于汽提挥发性香气成分的方法是本领域所熟知的,例如见EP 1078576。
待提取的咖啡豆可通过任何合适的方法提取,所述方法可得到包含绿原酸的提取物。用水和/或蒸汽提取咖啡豆(的方法)是本领域所熟知的,例如见EP 0916267。提取可经历浓缩步骤,并在转化绿原酸的处理前经干燥,例如通过喷雾干燥或冷冻干燥。如果提取物已经干燥,如果需要可重悬(提取物)以实现转化绿原酸的处理。在绿原酸转化之前、同时或之后,咖啡提取物可经历任意合适的处理以去除不需要的提取物组分,例如以提高在最终处理的提取物中的脱羧酚酸浓度。
可在提取之后或期间进行转化绿原酸的提取物处理。在转化绿原酸的处理之前、期间或之后,可将提取物从提取的咖啡豆中分离。在一个实施方案中,提取物在转化绿原酸的处理之后保持与提取的咖啡豆分离,即在转化绿原酸的处理之后,提取物不与提取的咖啡豆接触。可通过任意合适的方法从提取的咖啡豆中分离提取物,例如过滤或离心。可考虑提取物的期望用途进行实际和经济可行的必要的分离。因此不一定为100%完全的分离,例如在分离后咖啡豆中小部分不溶解物质可能仍在提取物中。
本发明还涉及生产食物或饮料产品的方法,其中使用本发明的咖啡提取物作为所述食物或饮料产品的成分。在本发明的一个实施方案中,提取物从提取的咖啡豆中分离使用,即咖啡豆的不溶解物质基本上通过此处描述的分离去除,并不用于食物或饮料产品的制备。食物或饮料产品可为任意本领域公知的食物或饮料产品。在一个优选的实施方案中,食物或饮料产品为咖啡饮料;纯可溶咖啡;软饮料;膳食补充剂;乳产品;谷类产品;水果或蔬菜汁产品;或糖食产品,例如巧克力产品,例如巧克力饮料。可溶咖啡产品可通过浓缩和干燥本发明的提取物制备。在干燥前,提取物可与未经绿原酸转化处理的咖啡提取物混合,例如烘焙咖啡、生咖啡或两者的提取物。从咖啡提取物中制备可溶咖啡产品的方法是本领域所熟知的。当提取物用于咖啡产品的制备时,待提取的咖啡豆可能在提取前经历汽提以去除挥发性香气,例如EP-A-1078576所描述的。在水解绿原酸的处理之后,例如在干燥后,挥发性香气可再加入提取物以制备芳香化的可溶咖啡产品。由本发明的咖啡提取物制备的可溶咖啡产品可就这样出售,或可例如与奶精(creamer)和/或甜味剂混合后出售,以制备包含奶精和/或甜味剂的咖啡饮料,例如卡布奇诺或咖啡拿铁。
在一个实施方案中本发明涉及包含至少0.1毫克4-乙烯基儿茶酚和/或其甲氧基衍生物每克干物质,例如至少1、至少2、至少5或至少20毫克每克干物质的食物或饮料产品。
当根据本发明的咖啡提取物用作食物或饮料产品的成分时,其可在所述食物或饮料产品制备过程中的任意合适步骤加入以获得预期效果。可以以获得预期效果的任意合适量加入提取物,例如抗氧化效果或抗炎症效果。
在另一个实施方案中本发明涉及包含咖啡绿原酸衍生的脱羧酚酸的食物或饮料产品。食物或饮料产品可为本领域所公知的任意食物或饮料产品。在一个优选的实施方案中,食物或饮料产品为咖啡饮料;纯可溶咖啡;软饮料;膳食补充剂;乳产品;谷类产品;水果或蔬菜汁产品;或糖食产品,例如巧克力产品,例如巧克力饮料。可通过例如此处公开的方法制备所述食物或饮料产品。
咖啡绿原酸衍生的脱羧酚酸的用途
本发明还涉及咖啡绿原酸衍生的脱羧酚酸的用途。根据本发明的待使用的脱羧酚酸可通过任意合适的方法制备,例如通过咖啡酸的脱羧,并可为任意合适的形式,例如纯化的化合物。在本发明的一个实施方案中,根据本发明的待使用的脱羧酚酸为包含此处公开的脱羧酚酸的咖啡提取物的形式。在本发明的另一个实施方案中,脱羧酚酸部分或完全的从本发明的咖啡提取物中分离。根据本发明的待使用的脱羧酚酸可通过任意合适的方法对人或动物施用,例如口服、静脉内或皮肤局部施用。如果经口服施用,所述脱羧酚酸可为例如本发明的食物或饮料产品的形式。在本发明的一个实施方案中,本发明的食物或饮料产品在出售时带有标签,指示根据本发明的用途。
在一个实施方案中本发明涉及咖啡绿原酸衍生的脱羧酚酸用于制备食物或饮料产品的用途。所述食物或饮料产品可为本领域所公知的任意食物或饮料产品。在一个优选的实施方案中,食物或饮料产品为咖啡饮料;纯可溶咖啡;软饮料;膳食补充剂;乳产品;谷类产品;水果或蔬菜汁产品;或糖食产品,例如巧克力产品,例如巧克力饮料。当脱羧酚酸用于制备食物或饮料产品时,其可在所述食物或饮料产品制备过程中的任意合适步骤加入。
在一个实施方案中本发明涉及咖啡绿原酸衍生的脱羧酚酸作为抗氧化剂的用途,例如作为产品例如食物或饮料产品的成分,其中需要抗氧化剂特性以例如避免产品组分在贮藏时被氧化。抗氧化剂广泛应用于许多产品中,咖啡绿原酸衍生的脱羧酚酸可以与传统氧化剂类似的方式使用。技术人员通过常规实验可容易的决定获得预期抗氧化效果的必需量。
在另一个实施方案中本发明涉及咖啡绿原酸衍生的脱羧酚酸用于在人或动物体内增强抗氧化和/或抗炎症能力的用途,例如通过诱导解毒酶例如谷胱甘肽S转移酶(GST)和通过提高Nrf2介导的基因表达途径。已有报导,Nrf2活性相关基因的提高可增强解毒和刺激对氧化应激的内源防御。这些作用可通过例如对人或动物口服施用或皮肤局部应用脱羧酚酸获得。
在另一个实施方案中本发明涉及咖啡绿原酸衍生的脱羧酚酸用于在人或动物中降低炎症的用途,例如通过降低前列腺素E2水平,通过例如对人或动物口服施用咖啡绿原酸衍生的脱羧酚酸。
许多健康问题和疾病与氧化应激和炎症相关。咖啡绿原酸衍生的脱羧酚酸可用于治疗或预防这些问题或疾病。相关问题和疾病有例如皮肤疾病,例如由紫外线辐射造成的光损伤、特应性皮炎、湿疹、刮治术、搔痒、过敏症状、脑功能障碍(brain disorder)、炎症、肥胖和癌症,例如皮肤癌和肺癌。
在本发明的一个实施方案中咖啡绿原酸衍生的脱羧酚酸作为抗糖尿病剂使用,例如通过降低血糖水平,和/或提高瘦蛋白、胰岛素和/或c-肽的血液水平;作为骨重构剂使用,例如通过提高骨矿物质密度,和/或通过提高雌激素和/或孕酮和/或碱性磷酸酶活性的血清水平;作为抗转移剂使用,例如具有抗血管生成作用;和/或用于脑保护。这些作用可通过例如对人或动物的口服施用获得。
在本发明的另一个实施方案中,咖啡绿原酸衍生的脱羧酚酸用于制剂的制备,所述制剂用于治疗或预防皮肤疾病、糖尿病、脑功能障碍、炎症、肥胖、癌症;神经变性疾病、认知功能减退、轻度认知功能障碍、痴呆、情绪障碍、抑郁、睡眠障碍、涉及蛋白质聚集的疾病、阿尔茨海默病(包括AD的常见病症、痴呆、轻度认知功能障碍和认知功能减退例如睡眠障碍、情绪不稳、抑郁和紧张)、黄斑变性或糖尿病。制剂可以任意合适的形式用于例如口服施用或皮肤局部施用,例如以下列形式:食物或饮料产品、营养补充剂、片剂、洗液或化妆品。在一个优选的实施方案中制剂为药物。
本发明还涉及本发明的食品、饮料产品、食物补充剂或宠物食品的非治疗用途,用于在人或动物中治疗和/或预防皮肤疾病,例如紫外线辐射造成的光损伤、特应性皮炎、湿疹、刮治术、搔痒、过敏症状、炎症、肥胖和癌症,例如皮肤癌和肺癌;认知功能减退、情绪障碍和/或睡眠问题;用于脑保护;和/或用于改善认知能力、免疫反应和/或肠屏障(gut barrier)功能。认知能力可通过例如学习的能力和速度、解决智力问题的能力和速度、形成和回忆记忆的能力、反应时间等等表达。认知功能减退可自我表现为例如记忆力减退、健忘、遗忘词语或姓名问题(word or name-findingproblem)、记忆力、专注、计划或组织能力、执行复杂任务的能力,和/或认知能力的减退,可能例如由年龄、压力、疾病或其他原因导致。认知被理解为例如理解、推理、做决定、计划、学习、记忆、联想、概念形成、语言、注意力、感知、行为、解决问题和心智图像(mental images)的心理过程。
在另一个实施方案中,本发明涉及改善认知能力和治疗或预防以下疾病的方法:皮肤疾病例如紫外线辐射造成的光损伤、特应性皮炎、湿疹、刮治术、搔痒、过敏症状;炎症;肥胖;癌症,例如皮肤癌和肺癌;神经变性疾病;认知功能减退;轻度认知功能损害;痴呆;涉及蛋白质聚集的疾病;阿尔茨海默病;黄斑变性或糖尿病;所述方法包含对人或动物施用包含有效剂量的咖啡绿原酸衍生的脱羧酚酸的食品、饮料产品或宠物食品。所述食品、饮料产品或宠物食品可伴随药物施用以提高药物的效力和/或降低药物的剂量。
在另一个实施方案中,本发明涉及治疗或预防以下疾病的方法:皮肤疾病例如紫外线辐射造成的光损伤、特应性皮炎、湿疹、刮治术、搔痒、过敏症状;炎症;肥胖;癌症,例如皮肤癌和肺癌;神经变性疾病;认知功能减退;轻度认知功能损害;痴呆;涉及蛋白质聚集的疾病;阿尔茨海默病;黄斑变性;或糖尿病;所述方法包含对有需要的人或动物施用有效量的包含咖啡绿原酸衍生的脱羧酚酸的药物。所述食品、饮料产品或宠物食品可伴随药物施用以提高药物的效力和/或降低药物的剂量。
实施例
实施例1
用约氏乳杆菌(Lactobacillus johnsonii)(CNCM I-1225)的喷雾干燥制品处理生咖啡提取物
将30mg干燥的生咖啡提取物溶解于1ml磷酸缓冲液(50mM,pH 7.0)或1ml水中。将10mg约氏乳杆菌(Lactobacillus johnsonii)(CNCM I-1225)的喷雾干燥制品(3.3E9cfu/g)加入此溶液。将混合物置于37℃孵育,在不同反应时间取出样品。在离心(3000g,5min)和过滤(0.45μm孔径注射器滤器,Millipore SLHA 025BS)后,用HPLC分析样品。
HPLC分析
咖啡提取物样品稀释至1%w/w,并用RP-HPLC分析,使用CC 250/4Nucleosil 1005-C18柱(Macherey-Nagel)。洗脱剂体系为Millipore水、0.1%TFA和CH3CN,以1mL/min的流速。所述方法允许同时测定CQA、FQA、di-CQA、咖啡酸(CA)、阿魏酸(FA)和4-乙烯基儿茶酚(在325nm的吸光度),使用外标校准曲线。结果以时间为零时(t0)的参考的相对值表示。
抗氧化剂应答元件(ARE)荧光素酶实验
将包含8个拷贝大鼠谷胱甘肽-S-转移酶A2(GSTA2)中存在的ARE的pGL-8xARE和包含新霉素选择标记的质粒pcDNA3.1一同稳定转染进人MCF7细胞(Wang等人.,Cancer Res.66,10983-10994,2006)。ARE(抗氧化剂应答元件)为转录因子Nrf2的结合位点,Nrf2调节涉及解毒和对抗氧化应激的内源防御基因。质粒pGL-8xARE在8个Nrf2结合位点下游包含可监控Nrf2活性的荧光素酶基因。将AREc 32细胞接种于96孔微滴定板中,使用DMEM生长培养基。在用4-乙烯基儿茶酚处理24h以后测定萤火虫荧光素酶活性。
前列腺素E2形成实验
用4-乙烯基儿茶酚处理人结肠HT-29细胞15h后,将细胞与促炎剂TNF-α(10ng/ml)共同孵育6h。使用竞争酶免疫测定(EIA)对HT-29细胞中产生的PGE2进行分析(Cavin等人.,BBRC 327,742-49,2005)。
结果
在2种不同的生Robus ta咖啡豆提取物经孵育或发酵制备的发酵后的咖啡提取物的HPLC分析中观察到一个未知峰。所述化合物通过LC-MS-ToF和NMR组合鉴定为4-乙烯基儿茶酚。生咖啡提取物经上述方法处理并用HPLC分析。结果显示于表1。
表1.用约氏乳杆菌处理生咖啡提取物特定时间后的组成。除了以HPLC信号区域表示4-乙烯基儿茶酚的量以外,其他物质的量以未处理的提取物量的%表示,在未处理的提取物中未检测到4-乙烯基儿茶酚。
4-乙烯基儿茶酚诱导的Nrf2活性显示于表2。
表2.4-乙烯基儿茶酚诱导的Nrf2活性(萤火虫荧光素酶活性,AU)
HT-29细胞中产生的PGE2显示于表3。
表3.相对未处理的对照样品,HT-29细胞中产生的PGE2
4-乙烯基儿茶酚(μg/ml) | PGE2形成(相对对照的%) |
0 | 100 |
3.13 | 58 |
6.25 | 46 |
9.38 | 21 |
15.63 | 12 |
31.25 | 5 |
62.5 | 2 |
实施例2
生咖啡提取物样品以1%w/w稀释,并用RP-HPLC分析,使用CC 250/4Nucleosil 1005-C18柱(Macherey-Nagel)。洗脱剂体系为Millipore水、0.1%TFA和CH3CN,以1mL/min的流速。通过在265nm的吸光度检测4-乙烯基儿茶酚。通过4-乙烯基愈创木酚的外部校准得到4-乙烯基儿茶酚的标准校准曲线,因为4-乙烯基儿茶酚在分离形式下不稳定。结果显示于表4。
表4.用约氏乳杆菌处理生咖啡提取物特定时间后的组成。量以毫克每克干咖啡提取物表示。在未处理的提取物中未检测到4-乙烯基儿茶酚。
时间(h) | 16 | 24 |
4-乙烯基儿茶酚 | 11 | 35 |
实施例3
单体Aβ
单体Aβ42肽通过尺寸排阻层析纯化,以10μM浓度与4-乙烯基儿茶酚以1∶0.5和1∶2(摩尔比率)的Aβ42∶待测化合物的比率在37℃孵育。在24和48小时通过硫磺素T(ThT)荧光评估聚集的程度。除了不含有待测化合物,对照以同样方式处理。ThT为疏水染料,在结合淀粉样原纤维后展示增强的荧光。ThT特异性结合淀粉样原纤维,而不是单体Aβ。在此实验中,ThT荧光的降低或缺乏提示待测的分子降低和/或阻碍淀粉样原纤维的形成。此实验的结果显示于图1。
初原纤维Aβ
尺寸排阻纯化的Aβ初原纤维混合物以10μM浓度与4-乙烯基儿茶酚以1∶0.5和1∶2(摩尔比率)的Aβ42∶待测化合物的比率在37℃孵育。在24和48小时通过硫磺素T(ThT)荧光评估聚集的程度。除了不含有待测化合物,对照以同样方式处理。初原纤维ThT荧光信号增加的降低或缺乏提示待测的分子降低和/或阻碍淀粉样原纤维的形成。此实验的结果显示于图2。
Claims (17)
1.制备包含咖啡绿原酸衍生的脱羧酚酸的咖啡提取物的方法,所述方法包含:
a)用水和/或蒸汽提取咖啡豆以制备咖啡提取物;和
b)处理咖啡提取物,将提取物中存在的绿原酸水解为酚酸,并将得到的酚酸脱羧。
2.权利要求1的方法,其中步骤b中绿原酸的水解和酚酸的脱羧通过微生物进行。
3.权利要求2的方法,其中所述微生物为乳酸菌。
4.权利要求1-3中任一项的方法,其中待提取的咖啡豆为生咖啡豆。
5.每克干物质包含至少0.1毫克4-乙烯基儿茶酚和/或其甲氧基衍生物的咖啡提取物。
6.权利要求5的咖啡提取物,其中所述甲氧基衍生物为4-乙烯基愈创木酚、4-乙烯基藜芦醚或其混合物。
7.权利要求5或6中任一项的咖啡提取物,其为生咖啡豆提取物。
8.制备食物或饮料产品的方法,其中使用根据权利要求5或6中任一项的咖啡提取物作为所述食物或饮料产品的成分。
9.权利要求8的方法,其中所述食物或饮料产品为咖啡饮料;纯可溶咖啡;软饮料;膳食补充剂;乳产品;谷类产品;水果或蔬菜汁产品;或糖食产品。
10.每克干物质包含至少0.1毫克4-乙烯基儿茶酚和/或其甲氧基衍生物的食物或饮料产品。
11.咖啡绿原酸衍生的脱羧酚酸作为抗氧化剂的用途。
12.咖啡绿原酸衍生的脱羧酚酸用于制备药物的用途。
13.咖啡绿原酸衍生的脱羧酚酸用于制备制剂的用途,所述制剂用于治疗或预防皮肤疾病、糖尿病、脑功能障碍、炎症、肥胖、癌症、神经变性疾病、认知功能减退、轻度认知功能损害、痴呆、情绪障碍、抑郁、睡眠障碍、涉及蛋白质聚集的疾病、阿尔茨海默病、黄斑变性或糖尿病。
14.权利要求13的用途,其中所述制剂为食物或饮料产品。
15.咖啡绿原酸衍生的脱羧酚酸用于促进骨重构的用途。
16.咖啡绿原酸衍生的脱羧酚酸用于提高人或动物的体内抗氧化能力和/或脑保护的用途。
17.咖啡绿原酸衍生的脱羧酚酸用于制备食物或饮料产品的用途。
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CN103298354A (zh) * | 2010-11-12 | 2013-09-11 | 雀巢产品技术援助有限公司 | 改善个体的精神或身体健康状况的方法 |
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CA2723054A1 (en) | 2009-11-05 |
PL2282642T3 (pl) | 2013-12-31 |
EP2282642A1 (en) | 2011-02-16 |
EP2282642B1 (en) | 2013-07-24 |
AU2009242334B2 (en) | 2014-05-01 |
WO2009132889A1 (en) | 2009-11-05 |
MX2010011060A (es) | 2010-11-22 |
HRP20130882T1 (hr) | 2013-10-25 |
BRPI0910839A2 (pt) | 2015-07-28 |
ZA201008552B (en) | 2012-05-30 |
PE20100129A1 (es) | 2010-03-02 |
KR20110008200A (ko) | 2011-01-26 |
CO6280591A2 (es) | 2011-05-20 |
MY161337A (en) | 2017-04-14 |
PT2282642E (pt) | 2013-08-27 |
UY31797A (es) | 2009-11-10 |
RU2010148751A (ru) | 2012-06-10 |
AU2009242334A1 (en) | 2009-11-05 |
TW200944132A (en) | 2009-11-01 |
CA2723054C (en) | 2016-12-13 |
ES2425691T3 (es) | 2013-10-16 |
JP2011518570A (ja) | 2011-06-30 |
UA103765C2 (uk) | 2013-11-25 |
AR071425A1 (es) | 2010-06-16 |
US20110046235A1 (en) | 2011-02-24 |
JP5504254B2 (ja) | 2014-05-28 |
CL2009001030A1 (es) | 2010-06-11 |
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