CN113330018A - 来自红冬蛇菰中的二氢查耳酮 - Google Patents
来自红冬蛇菰中的二氢查耳酮 Download PDFInfo
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- CN113330018A CN113330018A CN201980083233.3A CN201980083233A CN113330018A CN 113330018 A CN113330018 A CN 113330018A CN 201980083233 A CN201980083233 A CN 201980083233A CN 113330018 A CN113330018 A CN 113330018A
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- solution
- beverage
- rebaudioside
- acid
- mogroside
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Abstract
Description
相关申请的交叉引用
本申请要求2019年10月24日提交的美国临时申请号62/749,993的优先权,所述临时申请通过援引以其全文并入。
发明领域
本传授内容涉及从红冬蛇菰(Balanophora harlandii)中分离二氢查耳酮化合物的方法以及所述二氢查耳酮化合物在消费品中的用途。
发明背景
天然有热量的糖,如蔗糖、果糖和葡萄糖被用来给饮料、食品、药物、以及口腔卫生/化妆品产品提供令人愉悦的味道。特别地,蔗糖赋予消费者偏爱的味道。虽然蔗糖提供了优越的甜度特征,但它不利地是热量型的。
已经引入无热量或低热量甜味剂以满足消费者需求。然而,无热量和低热量的甜味剂以挫败消费者的方式不同于天然热量型糖。基于味道,无热量或低热量甜味剂表现出不同于糖的时间特征曲线、最大响应、风味特征曲线、口感和/或适应行为。具体地,无热量或低热量甜味剂表现出延迟的甜度起始、持久的甜余味、苦味、金属味、涩味、清凉味(cooling taste)和/或像甘草的味道。在来源基础上,许多无热量或低热量的甜味剂是合成的化学品。消费者对尝起来像蔗糖的天然无热量或低热量的甜味剂的希望仍然很高。
贝托尼甜叶菊(Stevia rebaudiana Bertoni)是原产自南美洲的某些地区的紫莞科(Asteraceae)(菊科(Compositae))多年生灌木。其叶已在巴拉圭和巴西使用了数百年来甜味化当地的茶和药物。所述植物在日本、新加坡、马来西亚、韩国、中国、以色列、印度、巴西、澳大利亚和巴拉圭有商业化种植。
植物的叶含有二萜糖苷的混合物,所述二萜糖苷的量在总干重的从约10%至15%的范围内。这些二萜糖苷比糖甜约30至450倍。在结构上,二萜糖苷的特征在于单个基础结构即甜菊醇,而不同之处在于在C13和C19位置存在碳水化合物残基。典型地,基于干重,在甜叶菊的叶中发现的四种主要的甜菊醇糖苷是杜克苷A(0.3%)、莱鲍迪苷C(0.6%-1.0%)、莱鲍迪苷A(3.8%)和甜菊苷(9.1%)。在甜叶菊提取物中鉴定的其他糖苷包括莱鲍迪苷B、D、E和F、甜菊双糖苷和甜茶苷。在这些之中,仅甜菊苷和莱鲍迪苷A是在商业规模上可供使用的。
罗汉果苷源自罗汉果,是由罗汉果(Siraitia grosvenorii)的果实制成的甜提取物的常用名称,罗汉果是一种原产自中国南方和泰国北部的葫芦科草本多年生藤本植物。罗汉果提取物比糖甜近250倍并且是无热量的。罗汉果的甜度通常归因于罗汉果苷。
迄今为止,甜菊醇糖苷和罗汉果苷的使用一直受限于某些不希望的味道特性,包括甘草味、苦味、涩味、甜余味、苦余味和甘草余味,这些味道特性在浓度增加时变得更加突出并给予添加它们的消费品(例如,饮料)不同于蔗糖的味道。此外,大多数甜菊醇糖苷和罗汉果苷的最大甜度通常低于甜味化消费品(例如,饮料)中的传统饮料配方可接受的甜度。
发明概述
本传授内容涉及从红冬蛇菰中分离的二氢查耳酮化合物及其在消费品诸如饮料中的用途。
在一个方面中,提供了一种从红冬蛇菰中纯化具有式I的二氢查耳酮化合物的方法:
其中R1和R2各自独立地选自OH和OR6;R3选自氢和CH2COOH;R4选自氢和CH3;并且R6是任选取代的糖。所述方法包括(a)提供红冬蛇菰植物材料的粗提取物;(b)将粗提取物通过填充有聚合物吸附树脂的柱,并用含有至少约75%乙醇的水性乙醇溶剂洗脱,以提供含有至少一种具有式I的二氢查耳酮的第一溶液;以及(c)用反相色谱法纯化含有至少一种具有式I的二氢查耳酮的第一溶液,以提供含有至少一种具有式I的二氢查耳酮的第二溶液。
在一个方面中,然后可对第二溶液进行进一步的一步或多步处理以提供选自CC-00487、CC-00486和CC-00474的具有式Ia的单独的二氢查耳酮,其纯度基于干基按重量计为至少约80%。
在另一个方面中,然后可对第二溶液进行进一步的一步或多步处理以提供选自CC-00549、CC-00536和CC-00537的具有式Ib的单独的二氢查耳酮,其纯度基于干基按重量计为至少约80%:
在另一个方面中,提供了包含至少一种甜味剂和至少一种本文所述的二氢查耳酮(即具有式I、式Ia和式Ib的二氢查耳酮化合物)的组合物。所述至少一种甜味剂可以是任何已知的甜味剂,并且以增甜量存在。在一个实施例中,甜味剂选自至少一种甜菊醇糖苷、至少一种罗汉果苷或其组合。
在一个具体实施例中,所述至少一种本文所述的二氢查耳酮化合物以其甜度识别阈值浓度或以下的量存在。
在一个实施例中,所述至少一种本文所述的二氢查耳酮化合物以使得当将组合物添加至消费品时,所述消费品的蔗糖等效值(SE)与所述至少一种二氢查耳酮化合物不存在下的消费品的SE相比增强至少约1.2倍(倍)的量存在于组合物中。
在另一个实施例中,所述至少一种本文所述的二氢查耳酮化合物以使得当将组合物添加至消费品时,调节甜味剂的一种或多种味道属性,从而与所述至少一种二氢查耳酮化合物不存在下的消费品相比,使所述消费品尝起来更像蔗糖甜味化的消费品的量存在于组合物中。
提供包含至少一种甜味剂和至少一种本文所述的二氢查耳酮化合物的消费品,其中甜味剂以增甜量存在。
在一个实施例中,所述至少一种本文所述的二氢查耳酮化合物以有效使消费品的蔗糖等效值(SE)与所述至少一种二氢查耳酮化合物不存在下的消费品的SE相比增强至少约1.2倍的量存在于消费品中。
在另一个实施例中,所述至少一种本文所述的二氢查耳酮化合物以有效调节甜味剂的一种或多种味道属性,从而与所述至少一种二氢查耳酮化合物不存在下的消费品相比,使所述消费品尝起来更像蔗糖甜味化的消费品的量存在于消费品中。
在一个实施例中,所述至少一种本文所述的二氢查耳酮化合物以从约1ppm至约50ppm的浓度存在于消费品中。
在一个实施例中,所述至少一种甜味剂是以从约50ppm至约600ppm的浓度存在于所述消费品中。
示例性消费品包括但不限于,药物组合物、可食用凝胶和混合物、牙科组合物、甜食、调味品、口香糖、谷物组合物、焙烤食品、乳制品、桌面(tabletop)甜味剂、饮料以及饮料产品。
在具体实施例中,所述消费品是饮料或饮料产品。在消费品是饮料的实施例中,饮料可以是富含热量饮料、中值热量饮料、低热量饮料或零热量饮料。
在另一个方面中,提供了一种增强消费品的甜度的方法,所述方法包括(i)提供包含至少一种甜味剂的消费品以及(ii)将至少一种本文所述的二氢查耳酮化合物添加到消费品中,从而提供具有增强的甜度的消费品。包含所述至少一种二氢查耳酮的消费品的SE与所述至少一种二氢查耳酮化合物不存在下的消费品的SE相比增强至少约1.2倍。
在另一个实施例中,提供了一种增强消费品的甜度的方法,所述方法包括(i)提供消费品基质以及(ii)将至少一种甜味剂和至少一种本文所述的二氢查耳酮化合物添加到消费品基质中以提供具有增强的甜度的消费品。所述至少一种二氢查耳酮化合物以有效使消费品的SE与所述至少一种二氢查耳酮不存在下的消费品的SE相比增强至少约1.2倍的量添加到消费品基质中。
还提供了使消费品尝起来更像蔗糖甜味化的消费品的方法,所述方法包括(i)提供包含至少一种甜味剂的消费品以及(ii)将至少一种本文所述的二氢查耳酮化合物以有效调节甜味剂的一种或多种味道属性以与所述至少一种二氢查耳酮化合物不存在下的消费品相比时,使消费品尝起来更像蔗糖甜味化的消费品的量添加到消费品中。
在另一个实施例中,提供了一种使消费品尝起来更像蔗糖甜味化的消费品的方法,所述方法包括(i)提供消费品基质以及(ii)将至少一种甜味剂和至少一种本文所述的二氢查耳酮化合物添加到消费品基质中。所述至少一种二氢查耳酮化合物以有效调节甜味剂的一种或多种味道属性,从而当与所述至少一种二氢查耳酮化合物不存在下的消费品相比时,使消费品尝起来更像蔗糖甜味化的消费品的量添加到消费品基质中。
附图说明
图1示出了CC-00487、CC-00486和CC-00474、CC-00536、CC-00537和CC-00549从红冬蛇菰中的分离方案。
具体实施方式
I.定义
如本文所用,术语“消费品”意指与人或动物的口接触的物质,包括被摄入并随后从口中排出的物质和被饮用、食用、吞咽或以其他方式摄入的物质,并且当以通常可接受的范围使用时对人或动物消费是健康的。
如本文所用,术语“甜度增强剂”是指以下化合物:当化合物是以处于或低于所述化合物的甜味剂识别阈值的浓度(即在一种或多种附加甜味剂不存在下化合物不会产生任何明显的甜味的浓度)存在于消费品中时增强、放大或加强消费品(例如饮料)的甜度感知的化合物。术语“甜度增强剂”与术语“甜味增效剂”、“甜度增效剂”、“甜度放大剂”和“甜度强化剂”是同义的。
如通常在本文所用,术语“甜度识别阈值”是可由人味觉感知为甜的化合物的最低已知的浓度。甜度识别阈值浓度对于特定化合物是特异性的,并且可以基于温度、基质、成分和/或风味系统而变化。
如本文所用,术语“味道调节剂”是指以使得消费品尝起来更像蔗糖甜味化的饮料的这样的方式积极影响消费品(例如饮料)中的非蔗糖甜味剂的感知的化合物。例如,可以用味道调节剂掩蔽非蔗糖甜味剂的某些消极味道特性,例如苦味、酸味、涩味、咸味和金属韵调。在另一个实例中,可以改善口感。在又一个实例中,可以减少甜度存留。在又一个实例中,可以增加甜度起始。在另一实例中,可以改善甜度起始。在仍然另一实例中,可以改善苦味存留。
II.从红冬蛇菰分离的方法
提供了一种用于从红冬蛇菰中纯化具有式I的二氢查耳酮化合物的方法,所述方法包括:
(a)提供红冬蛇菰植物材料的粗提取物;
(b)将粗提取物通过填充有聚合物吸附树脂的柱,并用含有至少约75%乙醇的水性乙醇洗脱,以提供含有至少一种具有式I的二氢查耳酮化合物的溶液;以及
(c)用反相色谱法纯化含有至少一种二氢查耳酮化合物的溶液,以提供具有式I的纯化的二氢查耳酮化合物。
红冬蛇菰是一种来自蛇菰属的寄生植物,典型地分布于温带和热带亚洲、非洲和太平洋地区。所有蛇菰属种类都充当寄主植物根部上的寄生物。蛇菰属具有地下块茎、不显眼的开花系统、彩色鳞叶和小花。
全部或部分红冬蛇菰植物可以用于本发明方法中。在一个实施例中,将红冬蛇菰植物材料在提取之前部分干燥。在另一个实施例中,将红冬蛇菰植物材料在提取之前完全干燥。在一些实施例中,将植物材料在提取之前任选地研磨。
植物材料可以通过任何适合的提取过程来提取,例如像连续或间歇回流提取、超临界流体提取、酶辅助提取、微生物辅助提取、超声辅助提取、微波辅助提取等。这些方法可以任何规模部署。
用于提取的溶剂可以是任何适合的溶剂,例如像极性有机溶剂(脱气的、抽真空的、加压的或蒸馏的)、非极性有机溶剂、水(脱气的、抽真空的、加压的、去离子的、蒸馏的、碳处理的或反渗透)或其混合物。在一个具体实施例中,溶剂包含水和一种或多种醇。在一个具体实施例中,溶剂包含水和选自以下的醇:甲醇、乙醇、正丙醇、2-丙醇、1-丁醇、2-丁醇及其混合物。在一个更具体实施例中,溶剂含有水和乙醇。
溶剂中醇的量可以在从约10%至约100%之间变化,例如像约20%、约30%、约40%、约50%、约60%、约70%、约80%、约90%或之间的任何范围。在一个具体实施例中,乙醇包含从约70%至约90%的溶剂,其余为水。
在一些实施例中,提取过程在高温下发生,例如像从约50℃至约100℃。在一个更具体实施例中,提取过程在从约60℃至约80℃、或约70℃的温度下发生。
本领域技术人员将理解,提取的持续时间将基于所使用的溶剂和植物材料的量而变化。在一些实施例中,进行提取从约1小时至约24小时,例如像至少约4小时、至少约8小时、至少约12小时、至少约16小时或至少约20小时。
可以从提取混合物中去除水和/或任何不溶性材料,以提供“粗提取物”。
不溶性植物材料可以通过例如过滤来从提取的混合物中分离出来。其他适合的分离方法包括但不限于重力过滤、板框压滤机、交叉流过滤器、滤网过滤器、Nutsche过滤器、带式过滤器、陶瓷过滤器、膜过滤器、微滤器、纳米过滤器、超滤器或离心。任选地,可以在此过程中使用各种助滤剂,诸如硅藻土、膨润土、沸石等。
然后对粗提取物进行一次或多次色谱分离以提供至少一种本文所述的二氢查耳酮化合物的溶液。
使粗提取物通过一个或多个柱,例如填充有聚合物吸附树脂的那些柱。用水性乙醇洗脱所述一个或多个柱提供了含有至少一种本文所述的二氢查耳酮化合物的溶液。在一个实施例中,首先将10%乙醇施加到柱上并收集洗脱液。典型地,所述第一洗脱液部分不含有至少一种本文所述的二氢查耳酮。用含有至少约75%乙醇(例如像约85%乙醇或约95%乙醇)的溶剂洗脱,提供了含有至少一种本文所述的二氢查耳酮化合物的溶液。
然后对含有至少一种本文所述的二氢查耳酮化合物的溶液进行反相色谱法以进一步纯化。所述柱可以填充有适合于反相色谱法的任何材料,例如MCI凝胶柱。收集这些部分,并使用LC-MS作为引导,通过在橙皮素二氢查耳酮单糖苷或其类似物的准离子或片段下的提取离子色谱图(EIC或XIC)(例如,[M-H]-,m/z 465)进一步处理。甲醇和水的梯度用于洗脱。在一个实施例中,使用1:4→4:1(甲醇:水)的梯度。梯度可以是连续的或逐步的。
可以基于用于洗脱的%甲醇收集这些部分,例如,20%甲醇、40%甲醇、50%甲醇、60%甲醇和80%甲醇。
提取这些部分、调节pH、分配和色谱法允许分离本文所述的单独的纯化的二氢查耳酮化合物。图1示出了示例性分离方案。
如本领域技术人员将理解的,期望的二氢查耳酮化合物的质量在本文所用的整个方法中可以通过MS或HPLC-MS跟踪,以例如引导分馏和纯化步骤。
CC-00487可以通过用水稀释至少一种具有式I的二氢查耳酮化合物的溶液(例如,在上述反相色谱步骤中的20%甲醇/80%水洗脱期间获得的并用EIC追踪)、酸化、分配、碱化和浓缩来分离。可以用任何适合的酸(例如,强酸,如HCl)进行酸化至从约1至约3的pH,例如像约1的pH。可以用任何适合的有机溶剂(例如乙酸乙酯)进行分配。可以用任何适合的碱(例如,强碱,如NaOH)将水性部分碱化至从约6至约8例如像约7的pH。然后可以例如通过HPLC或其他适合的方法纯化浓缩物,以提供CC-00487。
CC-00486可以通过用水稀释至少一种具有式I的二氢查耳酮的溶液(例如,在上述反相色谱步骤中的40%甲醇/60%水洗脱期间获得的并用EIC追踪)、酸化、分配和浓缩来分离。可以用任何适合的酸(例如,强酸,如HCl)进行酸化至从约1至约3的pH,例如像约1的pH。可以用任何适合的有机溶剂(例如乙酸乙酯)进行分配。然后可以将有机部分浓缩。然后可以例如通过HPLC或其他适合的方法纯化浓缩物,以提供CC-00486。
CC-00474可以通过用水性碱稀释至少一种具有式I的二氢查耳酮的溶液(例如,在上述反相色谱步骤中的60%甲醇/40%水期间获得的并用EIC追踪)、酸化、分配、进一步酸化、进一步分配、浓缩和分离来分离。用水性碱稀释可以例如用NaOH水溶液。可以用任何适合的酸(例如,强酸,如HCl)进行酸化至从约8至约11的pH,例如像约10的pH。可以用任何适合的有机溶剂(例如正丁醇)进行分配。所述分配的水性部分可以用任何适合的酸(例如,强酸,如HCl)进一步酸化至从约4至约6例如像约5的pH。所得的酸化的水溶液可以用任何适合的有机溶剂(例如正丁醇)进一步分配。然后可以将正丁醇部分浓缩。浓缩可以是例如通过HPLC纯化浓缩物,以提供CC-00474。
CC-00549可以通过将从上述反相色谱步骤获得的材料(例如,在上述反相色谱步骤中的50%甲醇/50%水期间并用EIC追踪)进行进一步柱色谱法(例如HPLC)来分离,以提供CC-00549。
橙皮素二氢查耳酮-4'-β-D-葡糖苷(HDCG)可以通过用水性碱稀释至少一种具有式I的二氢查耳酮的溶液(例如,在上述反相色谱步骤中的60%甲醇/40%水期间获得的并用EIC跟踪)、酸化、分配、进一步酸化、进一步分配、浓缩和分离来分离。用水性碱稀释可以例如用NaOH水溶液。可以用任何适合的酸(例如,强酸,如HCl)进行酸化至从约8至约11的pH,例如像约10的pH。可以用任何适合的有机溶剂(例如正丁醇)进行分配。所述分配的水性部分可以用任何适合的酸(例如,强酸,如HCl)进一步酸化至从约4至约6例如像约5的pH。所得的酸化的水溶液可以用任何适合的有机溶剂(例如正丁醇)进一步分配。然后可以将正丁醇部分浓缩。浓缩物可以通过例如HPLC色谱法纯化以提供HDCG。
CC-00536可以通过用水性碱稀释至少一种具有式I的二氢查耳酮化合物的溶液(例如,在上述反相色谱步骤中的60%甲醇/40%水期间获得的并用EIC追踪)、酸化、分配、进一步酸化、进一步分配、浓缩和分离来分离。用水性碱稀释可以例如用NaOH水溶液。可以用任何适合的酸(例如,强酸,如HCl)进行酸化至从约8至约11的pH,例如像约10的pH。可以用任何适合的有机溶剂(例如正丁醇)进行分配。所述分配的水性部分可以用任何适合的酸(例如,强酸,如HCl)进一步酸化至从约4至约6例如像约5的pH。所得的酸化的水溶液可以用任何适合的有机溶剂(例如正丁醇)进一步分配。然后可以将正丁醇部分浓缩。浓缩物可以通过例如HPLC色谱法纯化以提供CC-00536。
CC-00537可以通过用水性碱稀释至少一种具有式I的二氢查耳酮化合物的溶液(例如,在上述反相色谱步骤中的60%甲醇/40%水期间获得的并用EIC追踪)、酸化、分配、进一步酸化、进一步分配、浓缩和分离来分离。用水性碱稀释可以例如用NaOH水溶液。可以用任何适合的酸(例如,强酸,如HCl)进行酸化至从约8至约11的pH,例如像约10的pH。可以用任何适合的有机溶剂(例如正丁醇)进行分配。所述分配的水性部分可以用任何适合的酸(例如,强酸,如HCl)进一步酸化至从约4至约6例如像约5的pH。所得的酸化的水溶液可以用任何适合的有机溶剂(例如正丁醇)进一步分配。然后可以将正丁醇部分浓缩。浓缩物可以通过例如HPLC色谱法纯化以提供CC-00537。
本文所述的方法提供了一种本文所述的二氢查耳酮化合物,其纯度基于干基按重量计为至少约80%,例如像至少约85%、至少约90%、至少约95%、至少约97%或至少约99%。本领域技术人员将理解,可以进行附加的纯化步骤,例如在各种类型的柱上进行色谱分离,以达到上述的纯度。
II.增强剂/味道调节剂
在一个实施例中,具有式I的二氢查耳酮化合物是甜度增强剂。在另一个实施例中,具有式I的二氢查耳酮化合物是味道调节剂,有或没有同时充当甜度增强剂。也就是说,在一些实施例中,二氢查耳酮化合物增强甜味剂的甜度并调节甜味剂的一种或多种味道属性。在其他实施例中,二氢查耳酮化合物增强甜味剂的甜度而不调节甜味剂的一种或多种味道属性。在仍然其他实施例中,二氢查耳酮化合物调节甜味剂的一种或多种味道属性而不增强甜味剂的甜度。
在一个实施例中,具有式I的二氢查耳酮化合物可用作甜度增强剂和/或味道调节剂:
其中R1和R2各自独立地选自OH和OR6;R3选自氢和CH2COOH;R4选自氢和CH3;并且R6是任选取代的糖。
如本文所用,“糖”是指单糖、二糖、寡糖和多糖。糖包含至少一种碳水化合物。示例性碳水化合物包括但不限于蔗糖、甘油醛、二羟基丙酮、赤藓糖、苏糖、赤藓酮糖、阿拉伯糖、来苏糖、核糖、木糖、核酮糖、木酮糖、阿洛糖、阿卓糖、半乳糖、葡萄糖、古洛糖、艾杜糖、甘露糖、塔罗糖、果糖、阿洛酮糖、山梨糖、塔格糖、甘露庚酮糖、景天庚酮糖、辛酮糖、岩藻糖、鼠李糖、阿拉伯糖、松二糖和唾液糖。
糖可以是D-或L。在一个实施例中,糖是D-葡萄糖。
此外,糖可以呈α-构型或β-构型。在一个实施例中,糖是β-D-葡萄糖。
在一些实施例中,糖被取代。如本文所用,关于糖的“取代”是指羟基(-OH)位置上的一个或多个氧上的取代。示例性取代基包括但不限于没食子酰基、香草基、阿魏酰基、任何其他单-、二-、三-羟基苯甲酰基和甲氧基苯甲酰基。
在一个具体实施例中,二氢查耳酮化合物是具有式Ia的化合物:
在另一个实施例中,二氢查耳酮化合物是具有式Ib的化合物:
本文所述的二氢查耳酮化合物可以纯形式或作为混合物的一部分提供。混合物可以是从植物或植物的部分制备的提取物,如上文所述,或者是可商购的。
在一个实施例中,本文所述的二氢查耳酮化合物按重量计占混合物的至少约50%,例如像至少约60%、至少约70%、至少约80%、至少约90%或至少约95%。在一个更具体实施例中,本文所述的二氢查耳酮化合物按重量计占混合物的至少约96%、至少约97%、至少约98%或至少约99%。
还考虑了至少两种本文所述的二氢查耳酮化合物的混合物,例如像至少三种二氢查耳酮化合物。所述至少两种本文所述的二氢查耳酮化合物可以各自独立地以纯形式或作为混合物的一部分提供。在一个实施例中,所述至少两种本文所述的二氢查耳酮化合物按重量计占混合物的至少约50%,例如像至少约60%、至少约70%、至少约80%、至少约90%或至少约95%。在一个更具体实施例中,所述至少两种本文所述的二氢查耳酮化合物按重量计占混合物的至少约96%、至少约97%、至少约98%或至少约99%。
III.甜味剂
具有式I的二氢查耳酮化合物增强和/或调节至少一种甜味剂的味道。所述至少一种甜味剂可以是任何已知的甜味剂,例如天然甜味剂、天然高效甜味剂、合成甜味剂。
所述至少一种甜味剂以增甜量存在。如本文所用,“增甜量”是指当存在于消费品(例如饮料)中时提供可检测的甜度所需的化合物的量。
如本文所用,短语“天然高效甜味剂”是指在自然界中天然地发现并且在特征方面具有大于蔗糖、果糖、或葡萄糖的甜度效力,又具有较小卡路里的任何甜味剂。天然高效甜味剂可以作为纯化合物或替代性地作为提取物的一部分来提供。如本文所用,短语“合成甜味剂”是指在自然界中未天然地发现并且在特征方面具有大于蔗糖、果糖或葡萄糖的甜度效力,又具有较小卡路里的任何组合物。
在其他实施例中,所述至少一种甜味剂是碳水化合物甜味剂。适合的碳水化合物甜味剂选自但不限于由下组,所述组由以下各项组成:蔗糖、甘油醛、二羟基丙酮、赤藓糖、苏糖、赤藓酮糖、阿拉伯糖、来苏糖、核糖、木糖、核酮糖、木酮糖、阿洛糖、阿卓糖、半乳糖、葡萄糖、古洛糖、艾杜糖、甘露糖、塔罗糖、果糖、阿洛酮糖、山梨糖、塔格糖、甘露庚酮糖、景天庚酮糖、辛酮糖、岩藻糖、鼠李糖、阿拉伯糖、松二糖、唾液糖及其组合。
在其他实施例中,所述至少一种甜味剂不包含碳水化合物甜味剂。
在另一个实施例中,附加甜味剂是稀有糖,选自山梨糖、来苏糖、核酮糖、木糖、木酮糖、D-阿洛糖、L-核糖、D-塔格糖、L-葡萄糖、L-岩藻糖、L-阿拉伯糖、松二糖以及其组合。
其他甜味剂包括赛门苷I、莫那甜(monatin)及其盐(莫那甜SS、RR、RS、SR)、仙茅甜蛋白(curculin)、甘草酸及其盐、索马甜(thaumatin)、莫内林(monellin)、马宾灵(mabinlin)、布拉齐因(brazzein)、荷南度辛(hernandulcin)、叶甘素、根皮酚苷、根皮苷、三叶苷、白元参苷(baiyunoside)、欧亚水龙骨甜素(osladin)、聚波朵苷(polypodoside)A、蝶卡苷(pterocaryoside)A、蝶卡苷B、木库罗苷(mukurozioside)、弗米索苷(phlomisoside)I、巴西甘草甜素(periandrin)I、相思子三萜苷(abrusoside)A、甜菊双糖苷和青钱柳苷I、糖醇类如赤藓糖醇、三氯蔗糖、乙酰舒泛钾、安赛蜜酸及其盐、阿司帕坦、阿力甜、糖精及其盐、新橙皮苷二氢查耳酮、环己基氨基磺酸盐、环己氨磺酸及其盐、纽甜、糖精(advantame)、糖基化的甜菊醇糖苷(GSG)以及它们的组合。
在一个实施例中,甜味剂是热量型甜味剂或热量型甜味剂的混合物。在另一个实施例中,热量型甜味剂选自蔗糖、果糖、葡萄糖、高果糖玉米/淀粉糖浆、甜菜糖、甘蔗糖以及其组合。
在其他实施例中,甜味剂包含至少一种甜菊醇糖苷,其中所述至少一种甜菊醇糖苷以增甜量存在。甜菊醇糖苷可以是天然的、合成的或天然和合成的组合。
甜菊醇糖苷可以纯形式或作为混合物(即甜菊醇糖苷共混物)的一部分提供。示例性甜菊醇糖苷包括但不限于,莱鲍迪苷M、莱鲍迪苷D、莱鲍迪苷A、莱鲍迪苷N、莱鲍迪苷O、莱鲍迪苷E、甜菊单糖苷、甜菊双糖苷、甜茶苷、杜克苷B、杜克苷A、莱鲍迪苷B、莱鲍迪苷G、甜菊苷、莱鲍迪苷C、莱鲍迪苷F、莱鲍迪苷I、莱鲍迪苷H、莱鲍迪苷L、莱鲍迪苷K、莱鲍迪苷J、莱鲍迪苷M2、莱鲍迪苷D2、莱鲍迪苷S、莱鲍迪苷T、莱鲍迪苷U、莱鲍迪苷V、莱鲍迪苷W、莱鲍迪苷Z1、莱鲍迪苷Z2、莱鲍迪苷IX、酶促糖基化的甜菊醇糖苷以及其组合。
在某些实施例中,甜菊醇糖苷共混物包含按重量计至少约5%,例如像至少约10%、至少约20%、至少约30%、至少约40%、至少约50%、至少约60%、至少约70%、至少约80%、至少约90%、至少约95%或至少约97%的甜菊醇糖苷。
在示例性实施例中,甜菊醇糖苷共混物包含按重量计至少约50%,例如像从约50%至约90%、从约50%至约80%、从约50%至约70%、从约50%至约60%、从约60%至约90%、从约60%至约80%、从约60%至约70%、从约70%至约90%、从约70%至约80%以及从约80%至约90%的甜菊醇糖苷。
在一个实施例中,甜味剂是甜菊醇糖苷共混物,共混物包含增甜量的莱鲍迪苷M。在一个实施例中,甜菊醇糖苷共混物包含按重量计至少约5%,例如像至少约10%、至少约20%、至少约30%、至少约40%、至少约50%、至少约60%、至少约70%、至少约80%、至少约90%、至少约95%或至少约97%的莱鲍迪苷M。
在另一个实施例中,甜味剂是甜菊醇糖苷共混物,共混物包含增甜量的莱鲍迪苷A。在一个实施例中,甜菊醇糖苷共混物包含按重量计至少约5%,例如像至少约10%、至少约20%、至少约30%、至少约40%、至少约50%、至少约60%、至少约70%、至少约80%、至少约90%、至少约95%或至少约97%的莱鲍迪苷A。
在又一个实施例中,甜味剂是甜菊醇糖苷共混物,共混物包含增甜量的莱鲍迪苷D。在一个实施例中,甜菊醇糖苷共混物包含按重量计至少约5%,例如像至少约10%、至少约20%、至少约30%、至少约40%、至少约50%、至少约60%、至少约70%、至少约80%、至少约90%、至少约95%或至少约97%的莱鲍迪苷D。
在又一个实施例中,甜味剂是甜菊醇糖苷共混物,共混物包含增甜量的莱鲍迪苷N。在一个实施例中,甜菊醇糖苷共混物包含按重量计至少约5%,例如像至少约10%、至少约20%、至少约30%、至少约40%、至少约50%、至少约60%、至少约70%、至少约80%、至少约90%、至少约95%或至少约97%的莱鲍迪苷N。
在另一个实施例中,甜味剂是甜菊醇糖苷共混物,共混物包含增甜量的莱鲍迪苷O。在一个实施例中,甜菊醇糖苷共混物包含按重量计至少约5%,例如像至少约10%、至少约20%、至少约30%、至少约40%、至少约50%、至少约60%、至少约70%、至少约80%、至少约90%、至少约95%或至少约97%的莱鲍迪苷O。
在另一个实施例中,甜味剂是甜菊醇糖苷共混物,共混物包含增甜量的莱鲍迪苷J。在一个实施例中,甜菊醇糖苷共混物包含按重量计至少约5%,例如像至少约10%、至少约20%、至少约30%、至少约40%、至少约50%、至少约60%、至少约70%、至少约80%、至少约90%、至少约95%或至少约97%的莱鲍迪苷J。
甜菊醇糖苷共混物甜味剂典型地具有基于干基按重量计为约95%或更高的总甜菊醇糖苷含量。剩余的5%包含其他非甜菊醇糖苷化合物,例如,来自提取或纯化过程的副产物。在一些实施例中,甜菊醇糖苷共混物甜味剂具有约96%或更大、约97%或更大、约98%或更大或约99%或更大的总甜菊醇糖苷含量。如本文所用,“总甜菊醇糖苷含量”是指样品中每种甜菊醇糖苷的相对重量贡献的总和。
在一个实施例中,甜味剂包含至少一种罗汉果苷,其中所述至少一种罗汉果苷以增甜量存在。罗汉果苷可以是天然的、合成的或天然和合成的组合。
罗汉果苷可以纯形式或作为混合物(即罗汉果苷共混物)的一部分提供。示例性罗汉果苷包括但不限于以下任一种:grosmogroside I、罗汉果苷IA、罗汉果苷IE、11-氧代罗汉果苷IA、罗汉果苷II、罗汉果苷II A、罗汉果苷II B、罗汉果苷II E、7-氧代罗汉果苷IIE、罗汉果苷III、罗汉果苷IIIe、11-氧代罗汉果苷IIIE、11-脱氧罗汉果苷III、罗汉果苷IV、罗汉果苷IVA、11-氧代罗汉果苷IV、11-氧代罗汉果苷IVA、罗汉果苷V、异罗汉果苷V、11-脱氧罗汉果苷V、7-氧代罗汉果苷V、11-氧代罗汉果苷V、异罗汉果苷V、罗汉果苷VI、罗汉果醇、11-氧代罗汉果醇、赛门苷I、赛门苷I的异构体(例如,在20170119032中披露的那些;所述专利通过援引以其全文并入)、尤其是赛门苷I的1,6-α异构体(实例7和10)及其组合。
附加的示例性罗汉果苷包括在美国专利申请公开2016039864中描述的那些,所述专利申请的内容通过援引并入本文。在具体实施例中,罗汉果苷选自(3β,9β,10α,11α,24R)-3-[(4-O-β-D-吡喃葡萄糖基-6-O-β-D-吡喃葡萄糖基]-25-羟基-9-甲基-19-去甲羊毛甾-5-烯-24-基-[2-O-β-D-吡喃葡萄糖基-6-O-β-D-吡喃葡萄糖基]-β-D-吡喃葡萄糖苷);(3β,9β,10α,11α,24R)-[(2-O-β-D-吡喃葡萄糖基-6-O-β-D-吡喃葡萄糖基-β-D-吡喃葡萄糖基)氧基]-25-羟基-9-甲基-19-去甲羊毛甾-5-烯-24-基-[2-O-β-D-吡喃葡萄糖基-6-O-β-D-吡喃葡萄糖基]-β-D-吡喃葡萄糖苷);(3β,9β,10α,11α,24R)-[(2-O-β-D-吡喃葡萄糖基-6-O-β-D-吡喃葡萄糖基-β-D-吡喃葡萄糖基)氧基]-25-羟基-9-甲基-19-去甲羊毛甾-5-烯-24-基-[2-O-β-D-吡喃葡萄糖基-6-O-β-D-吡喃葡萄糖基]-β-D-吡喃葡萄糖苷)及其组合。
罗汉果苷共混物包含增甜量的至少一种罗汉果苷。
在某些实施例中,罗汉果苷共混物包含按重量计至少约5%,例如像至少约10%、至少约20%、至少约30%、至少约40%、至少约50%、至少约60%、至少约70%、至少约80%、至少约90%、至少约95%或至少约97%的罗汉果苷。
在其他实施例中,罗汉果苷共混物具有基于干基按重量计为约95%或更大的总罗汉果苷含量。在一些实施例中,罗汉果苷共混物具有约96%或更大、约97%或更大、约98%或更大或约99%或更大的总罗汉果苷含量。如本文所用,“总罗汉果苷含量”是指样品中每种罗汉果苷的相对重量贡献的总和。
在一个实施例中,甜味剂是罗汉果苷共混物,共混物包含增甜量的赛门苷I。在一个实施例中,罗汉果苷共混物包含按重量计至少约5%,例如像至少约10%、至少约20%、至少约30%、至少约40%、至少约50%、至少约60%、至少约70%、至少约80%、至少约90%、至少约95%或至少约97%的赛门苷I。
在另一个实施例中,甜味剂是罗汉果苷混合物,共混物包含增甜量的赛门苷I的1,6-α异构体。在一个实施例中,罗汉果苷共混物包含按重量计至少约5%,例如像至少约10%、至少约20%、至少约30%、至少约40%、至少约50%、至少约60%、至少约70%、至少约80%、至少约90%、至少约95%或至少约97%的赛门苷I的1,6-α异构体。
在又一个实施例中,甜味剂是包含增甜量的罗汉果苷V的罗汉果苷共混物。在一个实施例中,罗汉果苷共混物包含按重量计至少约5%,例如像至少约10%、至少约20%、至少约30%、至少约40%、至少约50%、至少约60%、至少约70%、至少约80%、至少约90%、至少约95%或至少约97%的罗汉果苷V。
所述至少一种甜味剂与所述至少一种本文描述的二氢查耳酮化合物的重量比可以变化。典型地,所述至少一种甜味剂与所述至少一种二氢查耳酮的重量比是从约500:1至约2:1,例如像从约100:1至约2:1、从约50:1至约2:1、从约25:1至约2:1、从约10:1至约2:1、从约5:1至约2:1、从约500:1至约400:1、从约500:1至约300:1、从约500:1至约200:1、从约500:1至约100:1、从约500:1至约50:1、从约500:1至约25:1、从约500:1至约10:1、从约400:1至约300:1、从约400:1至约200:1、从约400:1至约100:1、从约400:1至约50:1、从约400:1至约25:1、从约400:1至约10:1、从约400:1至约6.67:1、从约300:1至约200:1、从约300:1至约100:1、从约300:1至约50:1、从约300:1至约25:1、从约300:1至约10:1、从约300:1至约6.67:2、从约200:1至约100:1、从约200:1至约50:1、从约200:1至约25:1、从约200:1至约10:1、从约100:1至约50:1、从约100:1至约25:1、从约100:1至约10:1、从约100:1至约6.67:1、从约50:1至约25:1、从约50:1至约25:1、从约50:1至约10:1、从约50:1至约6.65:1、从约25:1至约10:1、从约25:1至约6.67:1、从约10:1至约6.67:1以及之间的任何范围。
IV.组合物
本发明还提供了组合物,所述组合物包含至少一种本文所述的甜味剂和至少一种具有式I的二氢查耳酮化合物。
所述至少一种本文所述的二氢查耳酮化合物以使得当将组合物添加至消费品时,所述消费品的蔗糖等效值与二氢查耳酮化合物不存在下的消费品相比增加的量存在于组合物中。
所述至少一种本文所述的二氢查耳酮可以一定的量存在于组合物中,使得当将组合物添加到消费品中时,与所述至少一种二氢查耳酮不存在下的消费品的蔗糖等效值(SE)相比,消费品的SE提高至少约1.2倍,例如像至少约1.5倍、至少约1.7倍、至少约2.0倍、至少约2.5倍、至少约3.0倍、或至少约4.0倍。
可以用白利糖度(°Bx)描述在参照溶液中的蔗糖的量,并因此描述甜度的另一种度量。一白利糖度是在100克溶液中有1克蔗糖,并且表示作为重量百分比的所述溶液的强度(%w/w)(严格地说,按质量计)。
在一些实施例中,所述至少一种本文所述的二氢查耳酮化合物以一定的量存在于组合物中,使得当将组合物添加到消费品中时,消费品具有等效于至少约8度的白利糖度的甜度,例如像约8度的白利糖度、约9度的白利糖度、约10度的白利糖度、约11度的白利糖度或约12度的白利糖度。
在其他实施例中,所述至少一种本文所述的二氢查耳酮化合物以一定的量存在于组合物中,使得当将组合物添加到消费品中时,消费品的白利糖度增加至少1度的白利糖度,例如像至少2度的白利糖度、至少3度的白利糖度、至少4度的白利糖度或至少5度的白利糖度。在其他实施例中,所述至少一种本文所述的二氢查耳酮化合物以使得当将组合物添加至消费品时,调节甜味剂的一种或多种味道属性,从而与所述至少一种二氢查耳酮不存在下的消费品的相同的一种或多种味道属性相比,使消费品尝起来更像蔗糖甜味化的消费品的量存在于组合物中。示例性味道属性调节包括减少或消除苦味、减少或消除苦味存留、减少或消除酸味、减少或消除涩味、减少或消除咸味、减少或消除金属韵调、改善口感、减少或消除甜度存留以及增加甜度起始。可以同时调节甜味剂的多种味道属性,这样使得消费品总体上具有更多的蔗糖甜味化的特征。量化蔗糖甜味化的特征的改善的方法是本领域中已知的,并且包括例如味道测试和直方图绘图。
应注意,比较是在(i)含有所述至少一种甜味剂和所述至少一种本文所述的二氢查耳酮化合物的消费品与(ii)含有所述至少一种甜味剂-但不含所述至少一种本文所述的二氢查耳酮化合物的消费品之间进行的。
还提供了包含至少一种甜味剂和至少一种本文所述的二氢查耳酮化合物的消费品。
所述至少一种本文所述的二氢查耳酮化合物典型地以有效增强消费品的甜度和/或调节甜味剂的一种或多种味道属性以使消费品尝起来更像蔗糖甜味化的消费品的量存在于消费品中。在一个实施例中,所述至少一种本文所述的二氢查耳酮化合物以二氢查耳酮的甜度识别阈值浓度或以下的量存在,即当单独品尝时不提供甜度的量。
典型地,所述至少一种本文所述的二氢查耳酮化合物以有效使消费品的蔗糖等效值(SE)与所述至少一种二氢查耳酮不存在下的消费品的SE相比时,增强至少约1.2倍,例如像至少约1.3倍、至少约1.4倍、至少约1.5倍、至少约1.6倍、至少约1.7倍、至少约1.8倍、至少约1.9倍和至少约2.0倍的量存在于消费品中。
在一些实施例中,所述至少一种本文所述的二氢查耳酮化合物以有效提供等效于至少约8度的白利糖度的甜度的量存在,例如像约8度的白利糖度、约9度的白利糖度、约10度的白利糖度、约11度的白利糖度或约12度的白利糖度。
在其他实施例中,与所述至少一种二氢查耳酮不存在下的消费品的白利糖度相比,所述至少一种本文所述的二氢查耳酮化合物以有效地将消费品的白利糖度提高至少1度的量存在,例如像至少2度的白利糖度、至少3度的白利糖度、至少4度的白利糖度或至少5度的白利糖度。
在其他实施例中,所述至少一种具有式I的二氢查耳酮化合物以有效调节甜味剂的一种或多种味道属性以使消费品尝起来更像蔗糖甜味化的消费品的量存在于消费品中。示例性味道属性调节包括减少或消除苦味、减少或消除苦味存留、减少或消除酸味、减少或消除涩味、减少或消除咸味、减少或消除金属韵调、改善口感、减少或消除甜度存留以及增加甜度起始。可以同时调节甜味剂的多种味道属性,这样使得消费品总体上具有更多的蔗糖甜味化的特征。量化蔗糖甜味化的特征的改善的方法是本领域中已知的,并且包括味道测试和直方图绘图。
所述至少一种本文所述的二氢查耳酮化合物和甜味剂的具体浓度将取决于具体的一种或多种二氢查耳酮化合物和一种或多种甜味剂而变化。
在一个实施例中,所述至少一种本文所述的二氢查耳酮化合物以从约1ppm至约50ppm,例如像从约1ppm至约45ppm、从约1ppm至约40ppm、从约1ppm至约35ppm、从约1ppm至约30ppm、从约1ppm至约25ppm、从约1ppm至约20ppm、从约1ppm至约15ppm、从约1ppm至约10ppm以及从约1ppm至约5ppm的浓度存在于消费品中。在另一个实施例中,所述至少一种二氢查耳酮以从约5ppm至约40ppm,例如像从约5ppm至约35ppm、从约5ppm至约20ppm、从约20至约40ppm、从约20ppm至约30ppm或从约30ppm至约40ppm的浓度存在于消费品中。
在一个实施例中,所述至少一种本文所述的甜味剂以从约50ppm至约600ppm,例如像50ppm至约500ppm、从约50ppm至约400ppm、从约50ppm至约300ppm、从约50ppm至约300ppm、从约50ppm至约200ppm、从约50ppm至约100ppm、约100ppm至约600ppm、约100ppm至约500ppm、约100ppm至约400ppm、约100ppm至约300ppm、约100ppm至约200ppm、约200ppm至约600ppm、约200ppm至约500ppm、约200ppm至约400ppm、约200ppm至约300ppm、约300ppm至约600ppm、约300ppm至约500ppm、约300ppm至约400ppm、约400ppm至约600ppm、约400ppm至约500ppm以及约500ppm至约600ppm的浓度存在于消费品中。
至少一种甜味剂与至少一种本文所述的二氢查耳酮的重量比也可以变化,如上文所论述。
在一个具体实施例中,提供了一种包含至少一种本文所述的二氢查耳酮化合物和至少一种甜味剂的消费品,其中所述至少一种二氢查耳酮以有效使消费品的SE在与所述至少一种二氢查耳酮不存在下的消费品的SE相比时增强至少约1.2倍的量存在。
在一个实施例中,具有增强的甜度的消费品具有约2%(w/v)或更大,例如像约3%或更大、约4%或更大、约5%或更大、约6%或更大、约7%或更大、约8%或更大、约9%或更大、约10%或更大、约11%或更大、约12%或更大、约13%或更大或约14%或更大的SE。
在另一个实施例中,具有增强的甜度的消费品具有约3至约12的白利糖度水平,例如像约3白利糖度或更大、约4白利糖度或更大、约5白利糖度或更大、约5白利糖度或更大、约7白利糖度或更大、约8白利糖度或更大、约9白利糖度或更大、约10白利糖度或更大以及约11白利糖度或更大。
示例性消费品包括但不限于,可食用凝胶混合物和组合物、牙科组合物、食品(甜食、调味品、口香糖、谷物组合物、烘焙食品、乳制品、以及桌面甜味剂组合物)、饮料和饮料产品。
消费品可以任选地包括一种或多种附加添加剂。示例性添加剂包括但不限于碳水化合物、多元醇、氨基酸及其相应盐、聚氨基酸及其相应盐、糖酸及其相应盐、核苷酸、有机酸、无机酸、有机盐(包括有机酸盐和有机碱盐)、无机盐、苦味化合物、调味剂和调味成分、涩味化合物、蛋白质或蛋白质水解物、表面活性剂、乳化剂、增重剂(weighing agent)、树胶(gum)、抗氧化剂、色素、类黄酮、醇、聚合物以及其组合。
在一个实施例中,所述消费品进一步包含一种或多种多元醇。如本文所用,术语“多元醇”是指含有超过一个羟基的分子。多元醇可以是分别含有2个、3个和4个羟基的二元醇、三元醇或四元醇。多元醇还可以含有超过4个羟基,如分别含有5个、6个或7个羟基的五元醇、六元醇、七元醇等。另外,多元醇还可以是作为碳水化合物的还原形式的糖醇、多羟基醇或多元醇,其中羰基(醛或酮,还原糖)已被还原成伯羟基或仲羟基。
在一些实施例中多元醇的非限制性实例包括麦芽糖醇、甘露糖醇、山梨糖醇、乳糖醇、木糖醇、异麦芽酮糖醇、丙二醇、甘油(丙三醇)、苏糖醇、半乳糖醇、帕拉金糖、还原性低聚异麦芽糖、还原性低聚木糖、还原性低聚龙胆糖、还原性麦芽糖糖浆、还原性葡萄糖糖浆以及糖醇或能够被还原的不会不利地影响味道的任何其他碳水化合物。
适合的氨基酸添加剂包括但不限于天冬氨酸、精氨酸、甘氨酸、谷氨酸、脯氨酸、苏氨酸、茶氨酸、半胱氨酸、胱氨酸、丙氨酸、缬氨酸、酪氨酸、亮氨酸、阿拉伯糖、反式-4-羟基脯氨酸、异亮氨酸、天冬酰胺、丝氨酸、赖氨酸、组氨酸、鸟氨酸、甲硫氨酸、肉毒碱、氨基丁酸(α-异构体、β-异构体和/或δ-异构体)、谷氨酰胺、羟基脯氨酸、牛磺酸、正缬氨酸、肌氨酸及其盐形式如钠盐或钾盐或酸盐。氨基酸添加剂还可以呈D-构型或L-构型以及呈相同或不同氨基酸的一元、二元或三元形式。另外,如果适当的话,这些氨基酸可以是α-、β-、γ-和/或δ-异构体。在一些实施例中,以上氨基酸及其相应盐(例如,其钠盐、钾盐、钙盐、镁盐或其他碱金属盐或碱土金属盐,或酸盐)的组合也是适合的添加剂。氨基酸可以是天然的或合成的。氨基酸还可以是改性的。改性的氨基酸是指其中至少一个原子已经被添加、去除、取代或其组合的任何氨基酸(例如,N-烷基氨基酸、N-酰基氨基酸或N-甲基氨基酸)。改性的氨基酸的非限制性实例包括氨基酸衍生物,如三甲基甘氨酸、N-甲基-甘氨酸、和N-甲基-丙氨酸。如本文所用,改性的氨基酸既涵盖改性的氨基酸也涵盖未改性的氨基酸。如本文所用,氨基酸还既涵盖肽也涵盖多肽(例如,二肽、三肽、四肽和五肽),如谷胱甘肽和L-丙氨酰-L-谷氨酰胺。适合的聚氨基酸添加剂包括聚-L-天冬氨酸、聚-L-赖氨酸(例如,聚-L-α-赖氨酸或聚-L-ε-赖氨酸)、聚-L-鸟氨酸(例如,聚-L-α-鸟氨酸或聚-L-ε-鸟氨酸)、聚-L-精氨酸、其他聚合物形式的氨基酸、以及其盐形式(例如钙盐、钾盐、钠盐或镁盐,如L-谷氨酸单钠盐)。聚氨基酸添加剂也可以呈D-构型或L-构型。另外,如果适当的话,聚氨基酸可以是α-、β-、γ-、δ-和ε-异构体。在一些实施例中,以上聚氨基酸及其相应盐(例如,其钠盐、钾盐、钙盐、镁盐或其他碱金属盐或碱土金属盐或酸盐)的组合也是适合的添加剂。本文描述的聚氨基酸还可以包括不同氨基酸的共聚物。聚氨基酸可以是天然的或合成的。聚氨基酸也可以是改性的,以使得至少一个原子被添加、去除、取代或其组合(例如,N-烷基聚氨基酸或N-酰基聚氨基酸)。如本文所用,聚氨基酸既涵盖改性的聚氨基酸也涵盖未改性的聚氨基酸。例如,改性的聚氨基酸包括但不限于具有不同分子量(MW)的聚氨基酸,如具有1,500的MW、6,000的MW、25,200的MW、63,000的MW、83,000的MW或者300,000的MW的聚-L-α-赖氨酸。
适合的糖酸添加剂包括但不限于醛糖酸、糖醛酸、醛糖二酸、海藻酸、葡糖酸、葡糖醛酸、葡糖二酸、半乳糖二酸、半乳糖醛酸、及其盐(例如,钠盐、钾盐、钙盐、镁盐或其他生理上可接受的盐)及其组合。
适合的核苷酸添加剂包括但不限于,单磷酸肌苷(“IMP”)、单磷酸鸟苷(“GMP”)、单磷酸腺苷(“AMP”)、单磷酸胞嘧啶(CMP)、单磷酸尿嘧啶(UMP)、二磷酸肌苷、二磷酸鸟苷、二磷酸腺苷、二磷酸胞嘧啶、二磷酸尿嘧啶、三磷酸肌苷、三磷酸鸟苷、三磷酸腺苷、三磷酸胞嘧啶、三磷酸尿嘧啶、其碱金属盐或碱土金属盐、及其组合。本文所述的核苷酸还可以包含核苷酸相关的添加剂,如核苷或核酸碱基(例如,鸟嘌呤、胞嘧啶、腺嘌呤、胸腺嘧啶、尿嘧啶)。
适合的有机酸添加剂包括包含-COOH部分的任何化合物,例如像C2-C30羧酸、取代的羟基C2-C30羧酸、丁酸(乙酯)、取代的丁酸(乙酯)、苯甲酸、取代的苯甲酸(例如,2,4-二羟基苯甲酸)、取代的肉桂酸、羟基酸、取代的羟基苯甲酸、茴香酸取代的环己基羧酸、鞣酸、乌头酸、乳酸、酒石酸、柠檬酸、异柠檬酸、葡糖酸、葡庚糖酸、己二酸、羟基柠檬酸、苹果酸、水果酒石酸(fruitaric acid)(苹果酸、富马酸和酒石酸的共混物)、富马酸、马来酸、琥珀酸、绿原酸、水杨酸、肌酸、咖啡酸、胆汁酸、乙酸、抗坏血酸、藻酸、异抗坏血酸、聚谷氨酸、葡糖酸δ内酯、及其碱金属盐或碱土金属盐衍生物。另外,有机酸添加剂也可以呈D-构型或L-构型。
适合的有机酸添加剂盐包括但不限于所有有机酸的钠盐、钙盐、钾盐、以及镁盐,如柠檬酸盐、苹果酸盐、酒石酸盐、富马酸盐、乳酸盐(例如,乳酸钠)、海藻酸盐(例如,藻酸钠)、抗坏血酸盐(例如,抗坏血酸钠)、苯甲酸盐(例如,苯甲酸钠或苯甲酸钾)、山梨酸盐以及己二酸盐。所述的有机酸添加剂的实例任选地可以被选自以下的至少一个基团取代:氢、烷基、烯基、炔基、卤素、卤代烷基、羧基、酰基、酰氧基、氨基、酰氨基、羧基衍生物、烷氨基、二烷基氨基、芳基氨基、烷氧基、芳氧基、硝基、氰基、磺基、硫醇、亚胺、磺酰基、烃硫基、亚磺酰基、氨磺酰基、羧烷氧基、碳酰胺基(carboxamido)、膦酰基、氧膦基、磷酰基、膦基、硫酯、硫醚、酸酐、肟基、肼基、氨甲酰基、磷或膦酸酯基。在具体实施例中,当存在于消费品(例如,饮料)中时,有机酸添加剂是以有效提供从约10ppm至约5,000ppm的浓度的量存在于甜味剂组合物中。
适合的无机酸添加剂包括但不限于磷酸、亚磷酸、聚磷酸、盐酸、硫酸、碳酸、磷酸二氢钠、及其碱金属盐或碱土金属盐(例如,肌醇六磷酸Mg/Ca)。
适合的苦味化合物添加剂包括但不限于咖啡因、奎宁、尿素、苦橘油、柚皮苷、苦木及其盐。
适合的调味剂和调味成分添加剂包括但不限于香草醛、香草提取物、芒果提取物、肉桂、柑橘、椰子、姜、绿花白千层醇(viridiflorol)、扁桃仁、薄荷醇(包括不含薄荷的薄荷醇)、葡萄皮提取物和葡萄籽提取物。“调味剂”和“调味成分”同义并且可以包括天然物质或合成物质或其组合。调味剂还包括赋予风味的任何其他物质并且可以包括在以通常接受的范围使用时对于人或动物是安全的天然物质或非天然(合成)物质。专有调味剂的非限制性实例包括天然调味甜度增强剂K14323(德国达姆施塔特(Darmstadt,Germany))、SymriseTM甜度天然风味遮盖剂161453和164126(SymriseTM,德国霍尔茨明登(Holzminden,Germany))、Natural AdvantageTM苦味阻滞剂1、2、9和10(NaturalAdvantageTM,美国新泽西州弗里霍尔德(Freehold,New Jersey,U.S.A.))以及SucramaskTM(美国加利福尼亚州斯托克顿市创造性科研管理处(Creative Research Management,Stockton,California,U.S.A.))。
适合的聚合物添加剂包括但不限于,壳多糖、果胶、果胶、果胶质酸、聚糖醛酸、聚半乳糖醛酸、淀粉、食品水解胶体或其粗提取物(例如,塞内加尔阿拉伯树胶(阿拉伯胶树(FibergumTM)、塞伊阿拉伯树胶、鹿角菜胶)、聚-L-赖氨酸(例如,聚-L-α-赖氨酸或聚-L-ε-赖氨酸)、聚-L-鸟氨酸(例如,聚-L-α-鸟氨酸或聚-L-ε-鸟氨酸)、聚丙二醇、聚乙二醇、聚(乙二醇甲基醚)、聚精氨酸、聚天冬氨酸、聚谷氨酸、聚乙烯亚胺、海藻酸、海藻酸钠、海藻酸丙二醇酯、以及聚乙二醇海藻酸钠、六偏磷酸钠及其盐、以及其他阳离子聚合物和阴离子聚合物。
适合的蛋白质或蛋白质水解物添加剂包括但不限于牛血清白蛋白(BSA)、乳清蛋白(包括其级分或浓缩物,例如90%即溶乳清蛋白分离物、34%乳清蛋白、50%水解乳清蛋白和80%乳清蛋白浓缩物)、可溶性大米蛋白、大豆蛋白、蛋白质分离物、蛋白质水解物、蛋白质水解物的反应产物、糖蛋白和/或含有氨基酸(例如,甘氨酸、丙氨酸、丝氨酸、苏氨酸、天冬酰胺、谷氨酰胺、精氨酸、缬氨酸、异亮氨酸、亮氨酸、正缬氨酸、甲硫氨酸、脯氨酸、酪氨酸、羟脯氨酸等)的蛋白聚糖、胶原蛋白(例如,明胶)、部分水解的胶原蛋白(例如,水解的鱼胶原蛋白)以及胶原蛋白水解产物(例如,猪胶原蛋白水解产物)。
适合的表面活性剂添加剂包括但不限于聚山梨醇酯(例如,聚氧乙烯脱水山梨糖醇单油酸酯(聚山梨醇酯80)、聚山梨醇酯20、聚山梨醇酯60)、十二烷基苯磺酸钠、磺基琥珀酸二辛酯或磺基琥珀酸二辛基酯钠、十二烷基硫酸钠、氯化十六烷基吡啶(氯化十六烷基吡啶鎓)、溴化十六烷基三甲铵、胆酸钠、氨甲酰基、氯化胆碱、甘胆酸钠、牛磺脱氧胆酸钠、月桂酰精氨酸酯、硬脂酰乳酸钠、牛磺胆酸钠、卵磷脂、蔗糖油酸酯、蔗糖硬脂酸酯、蔗糖棕榈酸酯、蔗糖月桂酸酯以及其他乳化剂等。
适合的类黄酮添加剂被分为黄酮醇、黄酮、黄烷酮、黄烷-3-醇、异黄酮或花色素。类黄酮添加剂的非限制性实例包括但不限于儿茶素(例如,绿茶提取物,如PolyphenonTM60、PolyphenonTM30和PolyphenonTM25(日本三川农林株式会社(Mitsui Norin Co.,Ltd.,Japan))、多酚、芦丁(例如,酶改性的芦丁SanmelinTMAO(日本大阪三荣源公株式会社(San-fi Gen F.F.I.,Inc.,Osaka,Japan))、新桔皮苷、柚皮苷、新橙皮苷二氢查耳酮等。
适合的醇添加剂包括但不限于乙醇。在具体的实施例中,所述醇添加剂是以从约625ppm至约10,000ppm的浓度存在于所述消费品中。
适合的涩味化合物添加剂包括但不限于鞣酸、氯化铕(EuCl3)、氯化钆(GdCl3)、氯化铽(TbCl3)、明矾、鞣酸和多酚(例如,茶多酚)。所述涩味添加剂是以从约10ppm至约5,000ppm的浓度存在于所述甜味化组合物中。
在此提供的消费品还可以含有一种或多种功能性成分,这些功能性成分为所述组合物提供了实际的或感知的健康益处。功能性成分包括但不限于,皂苷、抗氧化剂、膳食纤维源、脂肪酸、维生素、葡糖胺、矿物质、防腐剂、水合剂、益生菌、益生元、体重管理剂(weight management agent)、骨质疏松症管理剂(osteoporosis management agent)、植物雌激素、长链伯脂肪族饱和醇、植物甾醇及其组合。
功能性成分包括但不限于,皂苷、抗氧化剂、膳食纤维源、脂肪酸、维生素、葡糖胺、矿物质、防腐剂、水合剂、益生菌、益生元、体重管理剂(weight management agent)、骨质疏松症管理剂(osteoporosis management agent)、植物雌激素、长链伯脂肪族饱和醇、植物甾醇及其组合。
用于本发明的实施例的适合抗氧化剂的实例包括但不限于维生素、维生素辅因子、矿物质、激素、类胡萝卜素、类胡萝卜素萜类、非类胡萝卜素萜类、类黄酮、类黄酮多酚(如生物类黄酮)、黄酮醇类、黄酮类、酚类、多酚、酚酯、多酚酯、非类黄酮酚类、异硫氰酸酯类及其组合。在一些实施例中,抗氧化剂是维生素A、维生素C、维生素E、泛醌、矿物质硒、锰、褪黑激素、α-胡萝卜素、β-胡萝卜素、番茄红素、叶黄素、玉蜀黍黄素(zeanthin)、隐黄素(crypoxanthin)、白藜芦醇(reservatol)、丁子香酚、槲皮素、儿茶素、棉酚、橙皮素、姜黄素、阿魏酸、百里酚、羟基酪醇、姜黄、百里香、橄榄油、硫辛酸、谷胱甘肽(glutathinone)、谷氨酰胺(gutamine)、草酸、生育酚衍生化合物、丁基化羟基苯甲醚(BHA)、丁羟甲苯(BHT)、乙二胺四乙酸(EDTA)、叔丁基对苯二酚、乙酸、果胶、生育三烯酚、生育酚、辅酶Q10、玉米黄素、虾青素、斑蝥黄(canthaxantin)、皂苷、柠檬苦素、山柰酚(kaempfedrol)、杨梅酮、异鼠李素、原花色素、槲皮素、芦丁、木犀草素、芹菜素、红橘黄酮(tangeritin)、橙皮素、柚皮素、圣草酚(erodictyol)、黄烷-3-醇(例如,花青素)、没食子儿茶素、表儿茶素及其没食子酸酯形式、表没食子儿茶素及其没食子酸酯形式(ECGC)、茶黄素及其没食子酸酯形式、茶玉红精、异黄酮、植物雌激素、染料木黄酮、大豆黄素、黄豆黄素、花色素苷(anythocyanin)、氰化物(cyaniding)、飞燕草色素、锦葵花素、锦葵色素、锦葵色素、甲基花青素、矮牵牛素、鞣花酸、没食子酸、水杨酸、迷迭香酸、肉桂酸及其衍生物(例如,阿魏酸)、绿原酸、菊苣酸(chicoricacid)、五倍子鞣质、鞣花丹宁、花黄素、β-花青苷和其他植物颜料、水飞蓟素、柠檬酸、木酚素、抗营养素(antinutrient)、胆红素、尿酸、R-α-硫辛酸,N-乙酰半胱氨酸、油柑宁(emblicanin)、苹果提取物、苹果皮提取物(苹果多酚)、红路易波士提取物(rooibosextract red)、绿路易波士提取物(rooibos extract,green)、山楂果提取物、覆盆子提取物、生咖啡抗氧化剂(GCA)、野樱梅提取物20%、葡萄籽提取物(VinOseed)、可可豆提取物、啤酒花提取物、山竹果提取物、山竹果壳提取物、蔓越莓提取物、石榴提取物、石榴皮提取物、石榴籽提取物、山楂浆果提取物、波梅拉(pomella)石榴提取物、肉桂皮提取物、葡萄皮提取物、越桔提取物、松树皮提取物、碧萝芷、接骨木提取物、桑树根提取物、枸杞(gogi)提取物、黑莓提取物、蓝莓提取物、蓝莓叶提取物、树莓提取物、姜黄提取物、柑橘属生物类黄酮、黑醋栗、姜、巴西莓粉、生咖啡豆提取物、绿茶提取物以及植酸或其组合。在替代性实施例中,抗氧化剂是合成的抗氧化剂,例如像丁基化羟基甲苯或丁基化羟基苯甲醚。用于本发明的实施例的适合抗氧化剂的其他来源包括但不限于水果、蔬菜、茶、可可、巧克力、香辛料、药草、大米、来自家畜的器官肉类、酵母、全谷类(whole grain)或谷类(cereal grain)。
具体的抗氧化剂属于称为多元酚(也称为“多酚”)的植物营养素类,它是在植物中可见的一组化学物质,其特征在于每个分子存在超过一个酚基团。用于本发明的实施例的适合的多酚包括儿茶素、原花色素、原花青素、花青素、槲皮素、芦丁、白藜芦醇、异黄酮、姜黄素、安石榴苷、鞣花单宁、橙皮苷、柚皮苷、柑橘类黄酮、绿原酸、其他类似材料及其组合。
在具体实施例中,抗氧化剂是儿茶素,例如像表没食子儿茶素没食子酸酯(EGCG)。用于本发明的实施例的儿茶素的适合来源包括但不限于绿茶、白茶、红茶、乌龙茶、巧克力、可可、红葡萄酒、葡萄籽、红葡萄皮、紫色葡萄皮、红葡萄汁、紫葡萄汁、浆果、碧萝芷和红苹果皮。
在一些实施例中,抗氧化剂选自原花色素、原花青素或其组合。用于本发明的实施例的原花色素和原花青素的适合来源包括但不限于红葡萄、紫色葡萄、可可、巧克力、葡萄籽、红葡萄酒、可可豆、蔓越莓、苹果皮、李子、蓝莓、黑醋栗、花楸果(choke berry)、绿茶、高粱、肉桂、大麦、红芸豆、黑白斑豆、啤酒花、杏仁、榛子、山核桃、阿月浑子果实、碧萝芷和彩莓。
在具体实施例中,抗氧化剂是花青素。用于本发明的实施例的花青素的适合来源包括但不限于红莓、蓝莓、越桔、蔓越莓、覆盆子、樱桃、石榴、草莓、接骨木、花楸果、红葡萄皮、紫葡萄皮、葡萄籽、红酒、黑醋栗、红醋栗、可可、李子、苹果皮、桃、红梨、红球甘蓝、红洋葱、红橙和黑莓。
在一些实施例中,抗氧化剂选自槲皮素、芦丁或其组合。用于本发明的实施例的槲皮素和芦丁的适合来源包括但不限于红苹果、洋葱、羽衣甘蓝、笃斯越桔、越橘、花楸果、蔓越莓、黑莓、蓝莓、草莓、覆盆子、黑醋栗、绿茶、红茶、李子、杏、欧芹、韭、西兰花、红辣椒、浆果酒和银杏。
在一些实施例中,抗氧化剂是白藜芦醇。用于本发明的实施例的白藜芦醇的适合来源包括但不限于红葡萄、花生、蔓越莓、蓝莓、越桔、桑葚、日本板取茶(Japanese Itadoritea)和红酒。
在具体实施例中,抗氧化剂是异黄酮。用于本发明的实施例的异黄酮的适合来源包括但不限于大豆、大豆产物、豆科植物、苜蓿芽、鹰嘴豆、花生和红三叶草。
在一些实施例中,抗氧化剂是姜黄素。用于本发明的实施例的姜黄素的适合来源包括但不限于姜黄和芥末。
在具体实施例中,抗氧化剂选自槲皮素、鞣花单宁或其组合。用于本发明的实施例的槲皮素和鞣花单宁的适合来源包括但不限于石榴、覆盆子、草莓、胡桃和年代悠久的红葡萄酒。
在一些实施例中,抗氧化剂是柑橘类黄酮,诸如橙皮苷或柚皮苷。用于本发明的实施例的柑橘类黄酮如橙皮苷或柚皮苷的适合来源包括但不限于,橙、葡萄柚、以及柑橘果汁。
在具体实施例中,抗氧化剂是绿原酸。用于本发明的实施例的绿原酸的适合来源包括但不限于生咖啡、巴拉圭茶、红葡萄酒、葡萄籽、红葡萄皮、紫葡萄皮、红葡萄汁、紫葡萄汁、苹果汁、蔓越莓、石榴、蓝莓、草莓、向日葵、紫锥花、碧萝芷和苹果皮。
适合的膳食纤维包括但不限于非淀粉多糖、木质素、纤维素、甲基纤维素、半纤维素、β-葡聚糖、果胶、树胶、粘液、蜡、菊糖、寡糖、低聚果糖、环糊精、壳质及其组合。
膳食纤维的食物来源包括但不限于谷物、豆类、水果和蔬菜。提供膳食纤维的谷物包括但不限于燕麦、黑麦、大麦、小麦。提供纤维的豆类包括但不限于豌豆和菜豆诸如大豆。提供纤维来源的水果和蔬菜包括但不限于苹果、橙、梨、香蕉、浆果、西红柿、青豆、西兰花、花椰菜、胡萝卜、马铃薯、芹菜。植物性食物诸如麸、坚果和种子(诸如亚麻籽)也是膳食纤维来源。提供膳食纤维的植物部分包括但不限于茎、根、叶、种子、果肉和皮。
脂肪酸任何直链单羧酸并且包括饱和脂肪酸、不饱和脂肪酸、长链脂肪酸、中链脂肪酸、短链脂肪酸、脂肪酸前体(包括ω-9脂肪酸前体)和酯化脂肪酸。如本文所用,“长链多元不饱和脂肪酸”是指具有长脂肪族尾部的任何多元不饱和羧酸或有机酸。适合的ω-3脂肪酸包括但不限于亚麻酸、α-亚麻酸、二十碳五烯酸、二十二碳六烯酸、十八碳四烯酸、二十碳四烯酸及其组合。适合的ω-6脂肪酸包括但不限于亚油酸、γ-亚麻酸、二高-γ-亚麻酸、花生四烯酸、二十碳二烯酸、二十二碳二烯酸、肾上腺酸、二十二碳五烯酸及其组合。用于本发明的实施例的适合的酯化脂肪酸包括但不限于,含有ω-3和/或ω-6脂肪酸的单酰基甘油、含有ω-3和/或ω-6脂肪酸的二酰基甘油或者含有ω-3和/或ω-6脂肪酸的三酰基甘油及其组合。
适合的维生素包括维生素A、维生素D、维生素E、维生素K、维生素B1、维生素B2、维生素B3、维生素B5、维生素B6、维生素B7、维生素B9、维生素B12、和维生素C。多种其他化合物已被一些官方分类为维生素。这些化合物可以被称为假维生素,并且包括但不限于如泛醌(辅酶Q10)、潘氨酸、二甲基甘氨酸、taestrile、苦杏仁苷、类黄酮、对-氨基苯甲酸、腺嘌呤、腺苷酸和s-甲基甲硫氨酸等的化合物。如本文所用,术语维生素包括假维生素。
矿物质是选自主体矿物质、微量矿物质或其组合。主体矿物质的非限制性实例包括钙、氯、镁、磷、钾、钠和硫。微量矿物质的非限制性实例包括铬、钴、铜、氟、铁、锰、钼、硒、锌和碘。尽管碘通常被分类为微量矿物质,但是它需要比其他微量矿物质更大的量并且常常被分类为主体矿物质。
在本发明的其他具体实施例中,矿物质是被认为对于人类营养所必需的微量矿物质,其非限制性实例包括铋、硼、锂、镍、铷、硅、锶、碲、锡、钛、钨和钒。
防腐剂选自抗微生物剂、抗氧化剂、抗酶剂或其组合。抗微生物剂的非限制性实例包括亚硫酸盐、丙酸盐、苯甲酸盐、山梨酸盐、硝酸盐、亚硝酸盐、细菌素、盐、糖、乙酸、二碳酸二甲酯(DMDC)、乙醇和臭氧。亚硫酸盐包括但不限于二氧化硫、亚硫酸氢钠和亚硫酸氢钾。丙酸盐包括但不限于丙酸、丙酸钙和丙酸钠。苯甲酸盐包括但不限于苯甲酸钠和苯甲酸。山梨酸盐包括但不限于山梨酸钾、山梨酸钠、山梨酸钙和山梨酸。硝酸盐和亚硝酸盐包括但不限于硝酸钠和亚硝酸钠。在又一个具体实施例中,所述至少一种防腐剂是细菌素,例如像尼生素(nisin)。在另一个具体实施例中,防腐剂是乙醇。在又一个具体实施例中,防腐剂是臭氧。适合用作本发明的具体实施例中的防腐剂的抗酶剂包括抗坏血酸、柠檬酸和金属螯合剂诸如乙二胺四乙酸(EDTA)。
水合产物可以是电解质,其非限制性实例包括钠、钾、钙、镁、氯化物、磷酸盐、碳酸氢盐及其组合。在美国专利号5,681,569中也描述了用于本发明的具体实施例中的适合电解质,所述专利的披露内容明确地通过援引并入本文。用于具体实施例中的盐的非限制性实例包括氯化物、碳酸盐、硫酸盐、乙酸盐、碳酸氢盐、柠檬酸盐、磷酸盐、磷酸氢盐、酒石酸盐、山梨酸酯、柠檬酸盐、苯甲酸盐或其组合。在本发明的具体实施例中,水合产物是补充肌肉所燃烧的能量存储的碳水化合物。在美国专利号4,312,856、4,853,237、5,681,569和6,989,171中描述了用于本发明的具体实施例中的适合碳水化合物,所述专利的披露内容明确地通过援引并入本文。适合碳水化合物的非限制性实例包括单糖、二糖、寡糖、复合多糖或其组合。用于具体实施例中的适合类型的单糖的非限制性实例包括丙糖、丁糖、戊糖、己糖、庚糖、辛糖和壬糖。特定类型的适合单糖的非限制性实例包括甘油醛、二羟基丙酮、赤藓糖、苏阿糖、赤藓酮糖、阿拉伯糖、来苏糖、核糖、木糖、核酮糖、木酮糖、阿洛糖、阿卓糖、半乳糖、葡萄糖、古洛糖、艾杜糖、甘露糖、塔洛糖、果糖、阿洛酮糖、山梨糖、塔格糖、甘露庚酮糖、景天庚酮糖(sedoheltulose)、辛酮糖(octolose)和唾液糖(sialose)。适合二糖的非限制性实例包括蔗糖、乳糖和麦芽糖。适合寡糖的非限制性实例包括蔗糖、麦芽三糖和麦芽糖糊精。在其他具体实施例中,碳水化合物通过玉米糖浆、甜菜糖、甘蔗糖、果汁或茶提供。在另一个具体实施例中,水合是提供细胞再水合的黄烷醇。用于本发明的具体实施例中的适合黄烷醇的非限制性实例包括儿茶素、表儿茶素、没食子儿茶素、表没食子儿茶素、表儿茶素没食子酸酯、表没食子儿茶素3-没食子酸酯、茶黄素、茶黄素3-没食子酸酯、茶黄素3’-没食子酸酯、茶黄素3,3’-没食子酸酯、茶红素或其组合。在具体实施例中,水合产物是增强运动耐力的甘油溶液。
益生菌包括当以有效量消耗时有益于健康的微生物。益生菌可以包括而不限于细菌、酵母和真菌。益生菌的实例包括但不限于乳酸杆菌(Lactobacilli)属、双歧杆菌(Bifidobacteria)属、链球菌(Streptococci)属或其组合的细菌。在本发明的具体实施例中,所述至少一种益生菌选自乳酸杆菌属。乳酸杆菌(即乳酸菌属的细菌,在下文中“L.”)。人胃肠道内可见的乳酸杆菌种类的非限制性实例包括嗜酸乳杆菌(L.acidophilus)、干酪乳杆菌(L.casei)、发酵乳杆菌(L.fermentum)、唾液乳杆菌(L.saliva roes)、短乳杆菌(L.brevis)、赖氏乳杆菌(L.leichmannii)、植物乳杆菌(L.plantarum)、纤维二糖乳杆菌(L.cellobiosus)、罗伊氏乳杆菌(L.reuteri)、鼠李糖乳杆菌(L.rhamnosus)、GG乳杆菌(L.GG)、保加利亚乳杆菌(L.bulgaricus)、以及嗜热乳酸菌(L.thermophilus)。根据本发明的其他具体实施例,益生菌选自双歧杆菌属。在人胃肠道中可见的双歧杆菌的非限制性种类包括婴儿双歧杆菌(B.angulatum)、动物双歧杆菌(B.animalis)、海星纲双歧杆菌(B.asteroides)、双叉双歧杆菌(B.bifidum)、布姆双歧杆菌(B.boum)、短双歧杆菌(B.breve)、链状双歧杆菌(B.catenulatum)、小猪双歧杆菌(B.choerinum)、棒状双岐杆菌(B.coryneforme)、串孔双歧杆菌(B.cuniculi)、齿双歧杆菌(B.dentium)、高卢氏双歧杆菌(B.gallicum)、鸡胚双歧杆菌(B.gallinarum)、野菊双歧杆菌(B indicum)、长双歧杆菌(B.longum)、玛格南双歧杆菌(B.magnum)、瘤胃双歧杆菌(B.merycicum)、最小双歧杆菌(B.minimum)、伪链状双歧杆菌(B.pseudocatenulatum)、伪长双歧杆菌(B.pseudolongum)、B.psychraerophilum、雏双歧杆菌(B.pullorum)、反刍兽双歧杆菌(B.ruminantium)、波伦亚双歧杆菌(B.saeculare)、B.scardovii、猿双歧杆菌(B.simiae)、微秒双歧杆菌(B.subtile)、B.thermacidophilum、嗜热双歧杆菌(B.thermophilum)、尿路双歧杆菌(B.urinalis)、以及双歧杆菌某种。根据本发明的其他具体实施例,益生菌选自链球菌属(Streptococcus)。嗜热链球菌(Streptococcus thermophilus)是一种格兰阳性兼性厌氧菌。此细菌的其他非限制性益生菌种类包括唾液链球菌(Streptococcus salivarus)和乳脂链球菌(Streptococcus cremoris)。
益生元是促进有利细菌在肠内的生长的组合物。益生元包括但不限于粘多糖、寡糖、多糖、氨基酸、维生素、营养物前体,蛋白质及其组合。根据本发明的具体实施例,益生元选自膳食纤维,包括而不限于多糖和寡糖。根据本发明的具体实施例被分类为益生元的寡糖的非限制性实例包括低聚果糖、菊糖、低聚异麦芽糖、乳糖醇(lactilol)、低聚乳果糖、乳果糖、焦糊精、大豆寡糖、低聚反式半乳糖和低聚木糖。根据本发明的其他具体实施例,益生元是氨基酸。
如本文所用,“体重管理剂”包括食欲抑制剂和/或生热作用剂。如本文所用,短语“食欲抑制剂”、“食欲饱腹组合物”、“饱腹剂”和“饱腹成分”同义。短语“食欲抑制剂”描述了当以有效量递送时抑制、禁止、减少或以其他方式缩减人的食欲的大量营养素、草本植物提取物、外源性激素、减食欲药、食欲不振药、药物及其组合。短语“生热作用剂”描述了当以有效量递送时刺激或以其他方式增强人的生热作用或代谢的大量营养素、草本植物提取物、外源性激素、减食欲药、食欲不振药、药物及其组合。
适合的体重管理剂包括选自由以下组成的组的大量营养素:蛋白质、碳水化合物、膳食脂肪、及其组合。碳水化合物通常包括被身体转化成用于能量的葡萄糖的糖、淀粉、纤维素和树胶。碳水化合物的非限制性实例包括聚葡萄糖;菊糖;单糖衍生的多元醇如赤藓糖醇、甘露糖醇、木糖醇和山梨糖醇;二糖衍生的醇如异麦芽酮糖醇、乳糖醇和麦芽糖醇;以及氢化淀粉水解产物。下文更详细地描述碳水化合物。膳食脂肪是包含饱和脂肪酸和不饱和脂肪酸的组合的脂质。多元不饱和脂肪酸已显示具有比单不饱和脂肪酸更大的饱腹能力。因此,本文呈现的膳食脂肪理想地包括多元不饱和脂肪酸,其非限制性实例包括三酰基甘油。
在一个具体实施例中,体重管理剂是草本提取物。其提取物具有食欲抑制特性的植物的非限制性实例包括火地亚(Hoodia)属、亚罗汉(Trichocaulon)属、水牛掌(Caralluma)属、豹皮花(Stapelia)属、奥贝亚(Orbea)属、马利筋(Asclepias)属以及山茶花(Camelia)属的植物。其他实施例包括源于匙羹藤(Gymnema Sylvestre)、可乐果(KolaNut)、酸橙(Citrus Auran tium)、巴拉圭茶(Yerba Mate)、加纳谷物(GriffoniaSimplicifolia)、瓜拉那(Guarana)、没药(myrrh)、香胶树脂质(guggul Lipid)和黑醋栗籽油(black current seed oil)的提取物。在一个具体实施例中,草本提取物是源于火地亚属的植物,火地亚属的种类包括H.alstonii、H.currorii、H.dregei、火地亚黄花(H.flava)、火地亚仙人掌(H.gordonii)、H.jutatae、H.mossamedensis、火地亚地榆(H.officinalis)、H.parviflorai、火地亚同瓣草(H.pedicellata)、H.pilifera、H.ruschii、以及H.triebneri。火地亚属植物是原产自南非的肉茎植物。在另一个具体实施例中,草本提取物源自水牛掌(Caralluma)属植物,水牛掌属的种类包括印度水牛掌(C.indica)、芬布里塔水牛掌(C.fimbriata)、减弱水牛掌(C.attenuate)、结节水牛掌(C.tuberculata)、伊杜利水牛掌(C.edulis)、艾德森丹水牛掌(C.adscendens)、史塔拉米费拉水牛掌(C.stalagmifera)、恩伯来水牛掌(C.umbellate)、笔状水牛掌(C.penicillata)、罗塞利安那水牛掌(C.russeliana)、雷托斯比森水牛掌(C.retrospicens)、阿拉比卡水牛掌(C.Arabica)以及来西恩撒水牛掌(C.lasiantha)。水牛掌植物属于与火地亚属相同的亚科即萝摩科。在另一个具体实施例中,所述至少一种草本植物提取物是源于亚罗汉属植物。亚罗汉属植物是通常原产自南非的肉质植物,与火地亚属类似,并且包括摩耶夫人(T.piliferum)和T.officinale。在另一个具体实施例中,草本植物提取物源于豹皮花属或奥贝亚属植物,它们的种类分别包括长须地毯海葵(S.gigantean)和杂色豹皮花(O.variegate)。豹皮花属和奥贝亚属植物二者属于与火地亚属相同的子族萝摩科。在另一个具体实施例中,草本植物提取物源于马利筋属植物。马利筋属植物也属于萝摩科族植物。马利筋属植物的非限制性实例包括沼泽乳草(A.incarnate)、黄冠马利筋(A.curassayica)、叙利亚马利筋(A.syriaca)、以及柳叶马利筋(A.tuberose)。不希望受任何理论的束缚,据信这些提取物包含具有食欲抑制作用的甾族化合物,如孕烷糖苷和孕烷苷元。在一个具体实施例中,体重管理剂是具有体重管理作用的外源性激素。此类激素的非限制性实例包括CCK、肽YY、胃饥饿素、铃蟾肽和胃泌素释放肽(GRP)、肠抑素、载脂蛋白A-IV、GLP-1、淀粉不溶素、体抑素(somastatin)和瘦素。
在某些实施例中,骨质疏松症治疗剂是至少一种钙源,即含有钙的任何化合物,包括钙的盐络合物、溶解物质和其他形式。钙源的非限制性实例包括氨基酸螯合钙、碳酸钙、氧化钙、氢氧化钙、硫酸钙、氯化钙、磷酸钙、磷酸氢钙、磷酸二氢钙、柠檬酸钙、苹果酸钙、柠檬酸苹果酸钙、葡萄糖酸钙、酒石酸钙、乳酸钙、其溶解物质及其组合。根据具体实施例,骨质疏松症管理剂是镁源,即含有镁的任何化合物,包括镁的盐络合物、溶解物质和其他形式。镁源的非限制性实例包括氯化镁、柠檬酸镁、葡庚糖酸镁、葡糖酸镁、乳酸镁、氢氧化镁、吡啶甲酸镁(magnesium picolate)、硫酸镁、其溶解物质及其混合物。在另一个具体实施例中,镁源包括氨基酸螯合镁或肌酸螯合镁。在其他实施例中,骨质疏松症剂选自维生素D、C、K、其前体和/或β-胡萝卜素及其组合。多种植物和植物提取物也已被认定为对于防止和治疗骨质疏松症是有效的。在不希望受任何理论约束的情况下,认为这些植物和植物提取物刺激了成骨蛋白和/或抑制了骨再吸收,从而促进骨再生和强度。作为骨质疏松症管理剂的适合植物和植物提取物的非限制性实例包括如美国专利公开号2005/0106215中所披露的蒲公英属(Taraxacum)和唐棣属(Amelanchier)种类、以及如美国专利公开号2005/0079232所披露的山胡椒属(Lindera)、艾属(Artemisia)、菖蒲属(Acorus)、红花属(Carthamus)、葛缕子属(Carum)、蛇床属(Cnidium)、姜黄属(Curcuma)、莎草属(Cyperus)、刺柏属(Juniperus)、李属(Prunus)、鸢尾花属(Iris)、菊苣属(Cichorium)、坡柳属(Dodonaea)、淫羊藿属(Epimedium)、绒毛属(Erigonoum)、大豆属(Soya)、薄荷属(Mentha)、罗勒属(Ocimum)、百里香属(thymus)、菊蒿属(Tanacetum)、车前属(Plantago)、留兰香属(Spearmint)、红木属(Bixa)、葡萄属(Vitis)、迷迭香属(Rosemarinus)、漆树属(Rhus)、以及莳萝属(Anethum)的种类。
用于本发明的实施例的适合植物雌激素的实例包括但不限于,异黄酮、芪类、木酚素、雷琐酸内酯(resorcyclic acid lactone)、香豆素、香豆雌醇(coumestan)、香豆雌酚(coumestroI)、雌马酚及其组合。异黄酮属于称为多元酚的植物营养素组。通常,多元酚(也称为“多酚类”)是在植物中发现的一组化学物质,其特征在于每个分子存在超过一个酚基团。根据本发明的实施例的适合植物雌激素异黄酮包括染料木黄酮、黄豆苷元、黄豆黄素、鹰嘴豆素A、芒柄花黄素、其各自天然存在的糖苷和糖苷缀合物、马台树脂醇、开环异落叶松脂素、肠内二酯、肠二醇、植物组织蛋白及其组合。
长链脂肪族饱和伯醇是不同组的有机化合物。术语长链是指以下事实:在这些化合物中的碳原子数目是至少8个碳。用于本发明的具体实施例的具体长链脂肪族饱和伯醇的非限制性实例包括8碳原子1-辛醇、9碳1-壬醇、10碳原子1-癸醇、12碳原子1-十二烷醇、14碳原子1-十四烷醇、16碳原子1-十六烷醇、18碳原子1-十八烷醇、20碳原子l-二十烷醇、22碳1-二十二烷醇、24碳1-二十四烷醇、26碳1-二十六烷醇、27碳1-二十七烷醇、28碳1-二十八烷醇(octanosol)、29碳1-二十九烷醇、30碳1-三十烷醇、32碳1-三十二烷醇、以及34碳1-三十四烷醇。在本发明的一个特别期望的实施例中,长链伯脂肪族饱和醇是普利醇。普利醇是关于主要由以下成分组成的长链脂肪族饱和伯醇的混合物的术语:28碳1-二十八烷醇和30碳1-三十烷醇以及较低浓度的其他醇如22碳1-二十二烷醇、24碳1-二十四烷醇、26碳1-二十六烷醇、27碳1-二十七烷醇、29碳1-二十九烷醇、32碳1-三十二烷醇和34碳1-三十四烷醇。
已发现至少44种天然存在的植物甾醇,并且它们通常源于植物,诸如玉米、大豆、小麦和桐油;然而,它们还可以按合成方式产生以形成与天然的那些相同的组合物或者具有与天然存在的植物甾醇特性相似的特性的组合物。根据本发明的具体实施例,本领域普通技术人员已熟知的植物甾醇的非限制性实例包括4-去甲基甾醇(例如,β-谷甾醇、菜油甾醇、豆甾醇、菜籽甾醇、22-脱氢菜籽甾醇、以及Δ5-燕麦甾醇)、4-单甲基甾醇和4,4-二甲基甾醇(三萜烯醇)(例如,环阿屯醇、24-亚甲基环木菠萝烷醇和环甾烷醇(cyclobranol))。
根据本发明的具体实施例,植物甾烷醇的非限制性实例包括β-谷甾烷醇、菜油甾烷醇、环木菠萝烷醇以及其他三萜醇类的饱和形式。
如本文所用的植物甾醇和植物甾烷醇包括多种异构体诸如α和β异构体(例如,α-谷甾醇和β-谷甾醇,它们分别包括用于降低哺乳动物中的血清胆固醇的最有效的植物甾醇和植物甾烷醇之一)。本发明的植物甾醇和植物甾烷醇也可以呈它们的酯形式。适合的植物甾醇和植物甾烷醇的酯的非限制性实例包括乙酸谷甾醇酯、油酸谷甾醇酯、油酸豆甾醇酯及其相应的植物甾烷醇酯。本发明的植物甾醇和植物甾烷醇还可以包括其衍生物。
通常,在组合物中的功能性成分的量根据具体组合物和期望的功能性成分而广泛地改变。本领域普通技术人员将容易确定用于每种组合物的功能性成分的适当量。
在一个实施例中,所述消费品是饮料或饮料产品。
如本文所用,“饮料产品”是立即可饮的饮料、饮料浓缩物、饮料糖浆或饮料粉冲泡饮料。适合的立即可饮的饮料包括碳酸饮料和非碳酸饮料。碳酸饮料包括但不限于,冷冻的碳酸饮料、增强的起泡饮料、可乐、水果风味的起泡饮料(例如柠檬-酸橙、橙、葡萄、草莓和菠萝)、姜汁汽水、软饮品和根汁汽水。非碳酸饮料包括但不限于果汁、水果风味果汁、果汁饮品、花蜜、蔬菜汁、蔬菜风味汁、运动饮品、能量饮品、增强水饮品、具有维生素的增强水、近水饮品(例如,具有天然的或合成的调味剂的水)、椰子汁、茶类饮品(例如,黑茶、绿茶、红茶、乌龙茶)、咖啡、可可饮品、含有乳成分的饮料(例如,乳饮料、含有乳成分的咖啡、欧蕾咖啡(café au lait)、奶茶、果乳饮料)、含有谷物提取物的饮料以及冰沙。
饮料浓缩物和饮料糖浆用初始体积的液体基质(例如,水)和期望的饮料成分制备。然后通过添加另外体积的水来制备全强度饮料。固体饮料通过在不存在液体基质的情况下对所有饮料成分进行干混而制备。然后通过添加全部体积的水来制备全强度饮料。
饮料含有基质,即其中溶解了这些成分(包括本发明的组合物)的基础成分。在一个实施例中,饮料包含饮料品质的水作为基质,例如像可以使用去离子水、蒸馏水、反渗透水、碳处理水、纯水、软化水及其组合。附加的适合基质包括但不限于磷酸、磷酸盐缓冲液、柠檬酸、柠檬酸盐缓冲液和碳处理水。
所述饮料或饮料产品可以进一步包含至少一种附加甜味剂。可以使用本文详述的任何甜味剂,包括天然甜味剂、非天然甜味剂或合成甜味剂。在某些实施例中,饮料或饮料产品不含有碳酸化合物甜味剂。
考虑到消费品(例如饮料)的pH不会实质上或不利地影响甜味剂的味道。饮料的pH范围的非限制性实例可以是从约1.8至约10。另一个实例包括从约2至约5的pH范围。在具体实施例中,饮料的pH可以是从约2.5至约4.2。本领域技术人员将理解,饮料的pH可以基于饮料的类型而改变。例如,乳品饮料可以具有大于4.2的pH。
饮料的可滴定酸度的范围可以例如是按饮料重量计从约0.01%至约1.0%。
在一个实施例中,起泡饮料产品具有按饮料的重量计从约0.01%至约1.0%、例如像按饮料的重量计从约0.05%至约0.25%的酸度。
起泡饮料产品的碳酸化作用具有0至约2%(w/w)二氧化碳或其等效物,例如从约0.1%至约1.0%(w/w)。
所述饮料可以是含咖啡因的或不含咖啡因的。
饮料的温度范围可以例如是从约4℃至约100℃,例如像从约4℃至约25℃。
饮料可以是富含热量的饮料,它具有最高达约120卡路里/8盎司份量。
饮料可以是中值热量的饮料,它具有最高达约60卡路里/8盎司份量。
饮料可以是低热量的饮料,它具有最高达约40卡路里/8盎司份量。
饮料可以是零热量的饮料,它具有小于约5卡路里/8盎司份量。
在一个具体实施例中,消费品是可乐饮料。所述可乐饮料可以是低热量、中值热量或零热量的饮料。
在一个具体实施例中,饮料是低热量(diet)饮料。在一个更具体实施例中,饮料是低热量碳酸饮料。
在一个具体实施例中,本发明的饮料是调味水饮料。
V.使用方法
提供了增强消费品的甜度和/或调节甜味剂的一种或多种味道属性以使所述消费品尝起来更像蔗糖甜味化的消费品的方法。
在一个实施例中,增强消费品的甜度的方法包括(i)提供包含至少一种甜味剂的消费品以及(ii)将至少一种具有式I的二氢查耳酮化合物添加到消费品中以提供具有增强的甜度的消费品。
在另一个实施例中,增强消费品的甜度的方法包括(i)提供消费品基质以及(ii)将至少一种甜味剂和至少一种具有式I的二氢查耳酮化合物添加到消费品基质中以提供具有增强的甜度的消费品。所述至少一种甜味剂和至少一种具有式I的二氢查耳酮化合物可以一起添加,即以组合物的形式添加,或者分开添加。
如本文所用,术语“消费品基质”是指含有除甜味剂或甜味剂组分以外的所有典型成分的消费品。
在一个具体实施例中,包含所述至少一种具有式I的二氢查耳酮化合物和至少一种甜味剂的消费品的SE与所述至少一种具有式I的二氢查耳酮化合物不存在下的消费品的SE相比增强至少约1.2倍,例如像至少约1.3倍、至少约1.4倍、至少约1.5倍、至少约1.6倍、至少约1.7倍、至少约1.8倍、至少约1.9倍和至少约2.0倍。
在另一个实施例中,与不含具有式I的二氢查耳酮化合物的消费品的白利糖度相比,将所述至少一种具有式I的二氢查耳酮化合物添加到消费品或消费品基质中将白利糖度提高至少1度的白利糖度,例如像至少2度的白利糖度、至少3度的白利糖度或至少4度的白利糖度。
在一个具体实施例中,所述消费品是饮料。
因此,增强饮料的甜度的方法包括(i)提供包含至少一种甜味剂的饮料以及(ii)将至少一种具有式I的二氢查耳酮化合物添加到饮料中以提供具有增强的甜度的饮料。
在另一个实施例中,增强饮料的甜度的方法包括(i)提供饮料基质以及(ii)将至少一种甜味剂和至少一种具有式I的二氢查耳酮化合物添加到饮料基质中以提供具有增强的甜度的饮料。所述至少一种甜味剂和至少一种具有式I的二氢查耳酮化合物可以一起添加,即以组合物的形式添加,或者分开添加。
在另一方面中,使消费品尝起来更像蔗糖甜味化的消费品的方法包括(i)提供包含至少一种甜味剂的消费品以及(ii)添加有效调节甜味剂的一种或多种味道属性以与至少一种具有式I的二氢查耳酮化合物不存在下的消费品相比,使消费品尝起来更像蔗糖甜味化的消费品的量的至少一种具有式I的二氢查耳酮化合物。
在另一个实施例中,使消费品尝起来更像蔗糖甜味化的消费品的方法包括(i)提供消费品基质以及(ii)将至少一种甜味剂和至少一种具有式I的二氢查耳酮化合物添加到消费品基质中以提供尝起来更像蔗糖甜味化的消费品的消费品,其中所述至少一种具有式I的二氢查耳酮化合物以有效调节所述甜味剂的一种或多种味道属性以与所述至少一种具有式I的二氢查耳酮化合物不存在下的消费品相比,使消费品尝起来更像蔗糖甜味化的消费品的量存在。所述至少一种甜味剂和至少一种具有式I的二氢查耳酮化合物可以一起添加,即以组合物的形式添加,或者分开添加。
如上所论述,在本发明方法中,所述至少一种具有式I的二氢查耳酮化合物可以所鉴定的浓度存在于消费品中。
还提供了制备具有增强的甜度的消费品的方法。
在一个方面中,制备消费品的方法包括(i)提供包含至少一种甜味剂的消费品以及(ii)将至少一种具有式I的二氢查耳酮化合物添加到消费品中以提供消费品。
在另一个方面中,提供了一种制备消费品的方法,所述方法包括(i)提供消费品基质以及(ii)将至少一种甜味剂和至少一种具有式I的二氢查耳酮化合物添加到消费品基质中以提供消费品。所述至少一种甜味剂和至少一种具有式I的二氢查耳酮化合物可以一起添加,即以组合物的形式添加,或者分开添加。
在又一个方面中,提供了一种制备消费品的方法,所述方法包括(i)提供消费品基质以及(ii)将包含至少一种甜味剂和至少一种具有式I的二氢查耳酮化合物的组合物添加到消费品基质中以提供消费品。
在又一个方面中,提供了一种制备饮料的方法,所述方法包括(i)提供饮料基质以及(ii)将至少一种甜味剂和至少一种具有式I的二氢查耳酮化合物添加到饮料基质中以提供饮料。所述至少一种甜味剂和至少一种具有式I的二氢查耳酮化合物可以一起添加,即以组合物的形式添加,或者分开添加。
在另一方面中,提供了一种制备饮料的方法,所述方法包括(i)提供饮料基质以及(ii)将包含至少一种甜味剂和至少一种具有式I的二氢查耳酮化合物的组合物添加到饮料基质中以提供饮料。
在又一个方面中,提供了一种制备甜味化饮料的方法,所述方法包括(i)提供未甜味化的饮料以及(ii)将至少一种甜味剂和至少一种具有式I的二氢查耳酮化合物添加到未甜味化的饮料中以提供甜味化饮料。所述至少一种甜味剂和至少一种具有式I的二氢查耳酮化合物可以一起添加,即以组合物的形式添加,或者分开添加。
在另一方面中,提供了一种制备甜味化饮料的方法,所述方法包括(i)提供未甜味化的饮料以及(ii)将包含至少一种甜味剂和至少一种具有式I的二氢查耳酮化合物的组合物添加到未甜味化的饮料中以提供甜味化饮料。
实例1:来自红冬蛇菰的类似物的分离和表征
仪器:在Bruker Avance III 500或600HD光谱仪上记录1D和2D NMR数据,并且1H和13C NMR化学位移参考甲醇-d4(δH 3.31和δC 49.0)和DMSO-d6(δH 2.50和δC 39.52)的残留溶剂峰。用Sciex Triple TOF 4600光谱仪在负离子模式下进行高分辨率电喷雾电离质谱法(HRESIMS)。在使用Agilent HP-5MS柱(30m×0.25mm×0.25μm)的Agilent 7890A/5977A GC/MSD系统上进行GC-MS。在使用Boston Green ODS-AQ柱(10×250mm,5μm)的带有UV检测器的Agilent 1260infinity上进行半制备HPLC。在使用YMC Actus HydrosphereC18柱(30×250mm,5μm)或YMC Triart ODS柱(50×250mm,7μm)的Shimadzu LC-20AP系统上进行制备HPLC。使用AB-8树脂(西安蓝晓科技新材料股份有限公司(Sunresin NewMaterials Co.Ltd.),中国)、MCI凝胶CHP-20(三菱化学系统株式会社(MitsubishiChemical Systems,Inc.),日本)和Sephadex LH-20(通用电气健康护理生物科学股份公司(GE Healthcare Bio-Sciences AB),瑞典)进行柱色谱法(CC)。在Scientz-18N冷冻干燥机(宁波新芝生物科技股份有限公司(Ningbo Scientz Biotechnology Co.))上进行冻干。化学试剂的信息如下:95%EtOH、MeOH、MeCN、n-BuOH、EtOAc,均为A.R.级(上海星可高纯溶剂有限公司(Cinc High Purity Solvents(Shanghai)Co.,Ltd.));盐酸、NaOH、吡啶、正己烷,均为A.R.级(国药集团化学试剂有限公司(Sinopharm Chemical Reagent Co.Ltd.));用于半制备HPLC的乙腈,HPLC级(默克公司(Merck KGaA));以及L-半胱氨酸甲酯盐酸盐、L-三甲基硅咪唑、D-葡萄糖参考标准、L-葡萄糖参考标准,均为L.R.级(上海麦克林生化科技有限公司(Shanghai Macklin Biochemical Co.,Ltd.))。
来源:风干的红冬蛇菰的整个植株是从贵州安顺收集的。通过LC-MS确认暂定的橙皮素二氢查耳酮-4'-β-D-葡糖苷(HDCG)及六种类似物的存在。
提取:在70℃下用80%乙醇(100L)对红冬蛇菰的干燥粉末(10kg)提取4h。乙醇蒸发后,将溶液浓缩至小体积(5L)。
LC-MS引导的分离
使浓缩的溶液经受AB-8树脂柱,并用10%乙醇(100L)和95%乙醇(60L)洗脱。将95%乙醇洗脱液施加到MCI柱上,并用MeOH/H2O逐渐洗脱(1:4→4:1)以提供5个部分。靶向HDCG及其可能类似物的准离子的EIC(例如,[M-H]-,m/z为465)用于引导分馏和分离。将部分1(70g)用水(3L)溶解,用盐酸将pH调节至1,并用EtOAc(3L)分配。将水部分(30g)用1%NaOH溶液将pH调节至7,并浓缩至20mL。使20mL样品经受Sephadex LH-20柱,之后经受在以30mL/min的水-乙腈(74:26)下的制备HPLC(YMC Actus Hydrosphere C18,30×250mm,5μm),以产生CC-00487(180mg)。
将部分2(60g)溶解于水(3L)中,并用盐酸将pH调节至1,然后用EtOAc(3L)提取两次。将EtOAc部分合并并浓缩以获得半固体(20g),将其溶解于50mL甲醇-水(1:1)中并在MCI柱、Sephadex LH-20柱上进行色谱法,最后在以30mL/min的水-乙腈(79:21)下的制备HPLC上纯化以获得CC-00486(12mg)。
将部分3(20g)溶解于100mL甲醇-水(7:3)中并在Sephadex LH-20柱上进行色谱法,在以60mL/min的水-乙腈(78:22)下的制备HPLC上进一步纯化以获得CC-00549(3mg)。
将部分4(60g)用4%NaOH溶解,并用盐酸将pH调节至10,随后用正丁醇(4L)提取。将水相调节至pH 5,并再次用正丁醇(4L)分配。将第二正丁醇部分(25g)在Sephadex LH-20上进行色谱法,用50%乙醇洗脱,以产生含有目标质量的两种混合物。将混合物1在以3.5mL/min的水-乙腈(74:26)下的使用Boston Green ODS-AQ(10×250mm,5μm)的半制备HPLC上进一步纯化,以产生橙皮素二氢查耳酮-4'-β-D-葡糖苷(HDCG,2.3mg)和CC-00474(250mg)。将混合物2在以60mL/min的水-乙腈(72:28)下的制备HPLC上进一步纯化,以得到化合物CC-00536(34mg)和CC-00537(16mg)。
葡萄糖的绝对构型测定
将2.4mg CC-00486和2.6mg CC-00487分别溶解于1M HCl水(5mL)中。将每种溶液在100℃下加热至回流1.5h。将混合物冷却至室温,并用EtOAc(5mL/每次)提取两次。将水层在减压下蒸发至干以提供葡萄糖残余物。将残余物/D-葡萄糖/L-葡萄糖分别溶解于吡啶(0.5mL)中,向其中添加0.5mL L-半胱氨酸甲酯盐酸盐。将混合物保持在60℃下2h,在减压下干燥,并用1-三甲基硅咪唑(0.5mL)三甲基甲硅烷基化2h。将混合物在正己烷和水(各1.0mL)之间分配,并在以下条件下通过GC-MS分析己烷提取物:柱温,230℃;注射温度,250℃;载体,He气;分流比,10:1;流速,0.8mL/min;MS扫描范围,50-500。
结果
HDCG作为白色无定形粉末获得,并且具有通过HRESIMS分析([M-H]-,m/z465.1422,计算值465.1412,Δ=2.1ppm)的分子式C22H26O11。从MS/MS观察到的m/z303.0873下的一个单位162道尔顿的损失以及异头质子(δ4.85,d,J=7.7Hz,H-1”)表明结构中有一个β-葡萄糖部分。其苷元的1H NMR谱(表1)与3-羟基根皮素-4'-O-β-D-葡糖苷的1HNMR谱类似,除了是甲氧基而不是羟基,这表明存在间苯三酚环[δ6.12(2H,s,H-3’和H-5’)]、儿茶酚环[δ6.65(d,J=1.8Hz,H-2)、6.79(d,J=8.2Hz,H-5)和6.59(dd,J=1.8,8.2Hz,H-6)]。
表1 HDCG和CC-00474的NMR光谱数据a
a在DMSO-d6中,在Bruker Avance 600上记录NMR数据,1H:600MHz,13C:150MHz
在1H-1H COSY实验中两个亚甲基相互耦合[δ3.26(2H,t,J=7.6Hz,H-8)和2.74(2H,t,J=7.6Hz,H-7)]。OCH3/H-5的关键ROESY相关性将甲氧基固定在C-4处,这由HMBC实验中的OCH3/C-4、H-2/C-4和H-6/C-4的相关性网络进一步确定。类似地,葡萄糖基单元通过H-1”/C-4’的相关性连接到C-4’。综上所述,HDCG被鉴定为已知的橙皮素二氢查耳酮-4'-O-β-D-葡糖苷。HDCG的关键相关性如下所示:
CC-00474作为白色无定形粉末获得,并且具有通过HRESIMS分析([M-H]-,m/z465.1408,计算值465.1402,Δ=1.3ppm)的与HDCG相同的分子式。对其1H-NMR和13C-NMR谱(表1)与HDCG的综合比较分析表明,唯一的区别是儿茶酚环中甲氧基和羟基的位置。通过ROESY实验中OCH3/H-2的交叉峰显示甲氧基连接到C-3而不是C-4,这由HMBC实验中OCH3/C-3和H-5/C-3的相关性网络进一步确定。基于上述证据,CC-00474被鉴定为新化合物,命名为3-甲氧基根皮素-4'-O-β-D-葡糖苷。CC-00474的关键相关性如下所示:
CC-00486作为白色无定形粉末获得,并且具有通过HRESIMS分析([M-H]-,m/z465.1414,计算值465.1402,Δ=2.6ppm)的相同的分子式。所述化合物的1H NMR谱(表2)与3-羟基根皮素-2'-O-β-D-葡糖苷的1H NMR谱类似,除了是甲氧基而不是羟基,这表明存在间苯三酚环[δ6.15(1H,d,J=1.7Hz,H-3’)和5.92(1H,d,J=1.7Hz,H-5’)]、儿茶酚环[δ6.80(d,J=1.2Hz,H-2)、6.65(d,J=8.0Hz,H-5)和6.62(dd,J=1.3,8.0Hz,H-6)]。
表2 CC-00486和CC-00487的NMR光谱数据a
a在DMSO-d6中,在Bruker Avance 600上记录NMR数据,1H:600MHz,13C:150MHz
在1H-1H COSY实验中两个亚甲基相互耦合[δ3.43(1H,m,H-8)、3.34(1H,m,H-8)和2.80(2H,t,J=8.0Hz,H-7)]。OCH3/H-2的关键ROESY相关性将甲氧基固定在C-3处,这由HMBC实验中的OCH3/C-3、H-2/C-4和H-5/C-3的相关性网络进一步确定。类似地,通过ROESY实验中的H-1”/H-3’和HMBC实验中的H-1”/C-2’的相关性显示葡萄糖基单元连接到C-2’。使用上述方法将葡萄糖部分的绝对构型确定为D-构型。基于上述证据,CC-00486被鉴定为新化合物3-甲氧基根皮素-2'-O-β-D-葡糖苷。CC-00486的关键相关性如下所示:
CC-00487作为白色无定形粉末获得。它的HRESIMS表现出准分子离子峰,m/z627.1931[M-H]-,计算值627.1931,Δ=0.1ppm,这符合分子式C28H36O16。1H NMR谱(表2)显示出两组糖部分信号,并且糖部分质子的耦合常数[(δ5.01,d,J=7.4Hz,H-1”)和(δ4.96,d,J=7.4Hz,H-1”’)]表明存在两个β-连接的葡萄糖。另外,非糖部分的1H NMR谱与CC-00486的1H NMR谱类似,这表明存在间苯三酚环[δ6.35,d,J=2.3Hz,H-3’和δ6.16,d,J=2.3Hz,H-5’)]、儿茶酚环[δ6.79(d,J=1.6Hz,H-2)、6.65(d,J=8.0Hz,H-5)和6.62(dd,J=1.7,8.0Hz,H-6)]。在1H-1H COSY实验中两个亚甲基相互耦合[δ3.45(1H,m,H-8)、3.32(1H,m,H-8)和2.81(2H,t,J=7.5Hz,H-7)]。OCH3/H-2的关键ROESY相关性将甲氧基固定在C-3处,这由HMBC实验中的OCH3/C-3、H-2/C-4和H-5/C-3的相关性网络进一步确定。类似地,在HMBC实验中,通过H-1”’/C-4’的相关性显示一个葡萄糖基单元连接到C-4’,通过H-1”/C-2’的相关性显示另一个连接到C-2’。使用上述方法将葡萄糖部分的绝对构型确定为D-构型。基于上述证据,CC-00487被鉴定为新化合物3-甲氧基根皮素-2’,4’-O-β-D-葡糖苷。关键相关性如下所示:
CC-00549作为棕色无定形粉末获得,分子式C23H26O13由负离子模式HRESIMS(m/z509.1314[M-H]-,计算值509.1301,Δ=2.6ppm)推导出。1H-NMR数据(表3)表现出一组ABX型芳香族H原子的信号,δ6.70(1H,d,重叠,H-2)、6.71(1H,d,J=8.0Hz,H-5)和6.56(1H,dd,J=8.0,1.5Hz,H-6),一个单峰在芳香区的高场δ6.30(1H,s,H-5’),以及两个相互耦合的亚甲基信号δ3.34(2H,m,H-8)和2.80(2H,t,J=8.0Hz,H-7)。数据表明,分子中存在二氢查耳酮骨架和五取代的B环。此外,一个吡喃葡萄糖基单元(异头H原子和C原子信号,分别在δ4.94(1H,d,重叠,H-1”)和δ101.4(C-1”))由CC-00549的1H-NMR和13C-NMR数据证明。
表3 CC-00549、CC-00536和CC-00537的NMR光谱数据a
a在薄荷醇-d4中,在Bruker AvanceⅢ500上记录NMR数据,1H:500MHz,13C:125MHz
葡萄糖基H-1”/C-4’的HMBC相关性以及葡萄糖基H-1”和H-5’之间的ROESY相关性确认了吡喃葡萄糖基在C-4'的位置。另外,在HMBC实验中,通过H-7’/C-2’、C-3’、C-4’和羧基C-8’的长程相关性显示亚甲基C-7’连接到C-3’。关键相关性如下所示:
CC-00536作为淡黄色无定形粉末获得,分子式C28H28O15由负离子HRESIMS中m/z603.1354([M-H]-计算值603.1355,Δ=-0.2ppm)处的峰指定。1H-NMR(500MHz,甲醇-d4)和13C-NMR(125MHz,甲醇-d4,表3)允许CC-00536被鉴定为已知的3-羟基根皮素4'-O-[6”-O-没食子酰基]-β-D-吡喃葡萄糖苷。
CC-00537作为淡绿色无定形粉末获得。它具有通过HRESIMS分析(m/z 603.1377([M-H]-计算值603.1355,Δ=3.6ppm))的与CC-00536相同的分子式。CC-00537(表3)和CC-00536具有相同的骨架,因为在NMR数据中非常相似,除了葡萄糖基单元不同。基于与CC-00536相比,低场位移为H-4”[δ5.04(m)]且高场位移为H-6’[δ3.70(d,J=12.2Hz),3.59(m)],没食子酰基基团在CC-00537中的位置被确定为在葡萄糖C-4”而不是C-6”处。这也通过HMBC实验中的没食子酰基单元中H-4”和羰基的长程相关性(δ167.7,C-7”’)得到支持。因此,CC-00537被推导为新化合物3-羟基根皮素4'-O-[4'’-O-没食子酰基]-β-D-吡喃葡萄糖苷。关键相关性如下所示:
实例2:甜度增强
制备具有以下成分的样品:
表1:PG中的2%CC-00474
成分 | 量 |
CC-00474 | 2mg |
丙二醇 | 98mg |
表2:酸性水中的250ppm的莱鲍迪苷M
成分 | 量 |
莱鲍迪苷M | 125mg |
水 | 499.75g |
柠檬酸 | 125mg |
表3:酸性水中的20ppm的CC-00474和250ppm的莱鲍迪苷M
成分 | 量 |
酸性水中的250ppm的莱鲍迪苷M(表2) | 100g |
PG中的CC-00474(表1) | 0.1g |
表4:酸性水中的250ppm的莱鲍迪苷M和PG(对照)
成分 | 量 |
酸性水中的250ppm的莱鲍迪苷M(表2) | 100g |
PG | 98mg |
在称量舟中制备PG中的CC-00474,并在搅拌下将其加入Reb M溶液中。用Reb M溶液冲洗称量舟。将溶液搅拌到目视透明,然后将样品倒入玻璃瓶中,并储存在4℃下。
将瓶子从冰箱中取出并将约25ml的饮料倾倒入4盎司塑料杯中。在品尝之前并且在品尝不同的样品之间,将矿泉水给予专家组成员以清洗他们的口腔。在品尝下一个样品之前,还将未加盐的饼干给予专家组成员食用,接着用矿泉水清洗他们的口腔。
将莱鲍迪苷M在酸性水中的样品以及CC-00474和莱鲍迪苷M在酸性水中的样品给予专家组成员。要求专家组成员评价样品的甜度,并描述味道特征的差异。指示专家组成员啜饮,评价甜度,然后将样品吐入为此目的提供的杯子中。
所有专家组成员都同意,发现含有CC-00474和莱鲍迪苷M的样品比只含有莱鲍迪苷M的样品更甜。
Claims (18)
2.如权利要求1所述的方法,其中,所述至少一种具有式I的二氢查耳酮化合物是CC-00487,并且所述方法进一步包括:
(d)用水稀释所述第二溶液以提供稀释溶液;
(e)通过使所述稀释溶液与酸接触,将所述稀释溶液酸化至从约1至约3的pH以提供酸化溶液;
(f)用有机溶剂对所述酸化溶液进行分配以提供水性部分和有机部分;
(g)通过使所述水性部分与碱接触,将所述水性部分碱化至从约6至约8的pH以提供含有CC-00487的溶液;
(h)将所述含有CC-00487的溶液浓缩以提供浓缩溶液;以及
(i)将所述浓缩溶液纯化以提供包含具有按重量计至少约80%的纯度的CC-00487的组合物。
3.如权利要求1所述的方法,其中,所述至少一种具有式I的二氢查耳酮化合物是CC-00474,并且所述方法进一步包括:
(d)用水性碱稀释所述第二溶液以提供稀释溶液;
(e)通过使所述稀释溶液与酸接触,将所述稀释溶液酸化至从约8至约10的pH以提供酸化溶液;
(f)用有机溶剂对所述酸化溶液进行分配以提供水性部分和有机部分;
(g)通过使所述水性部分与酸接触,将所述水性部分酸化至从约4至约6的pH以提供第二酸化溶液;
(h)用有机溶剂对所述第二酸化溶液进行分配以提供第二水性部分和第二有机部分;
(i)将所述第二有机部分浓缩以提供浓缩溶液;以及
(j)将所述浓缩溶液纯化以提供包含具有按重量计至少约80%的纯度的CC-00474的组合物。
4.如权利要求1所述的方法,其中,所述至少一种具有式I的二氢查耳酮化合物是CC-00486,并且所述方法进一步包括:
(d)用水稀释所述第二溶液以提供稀释溶液;
(e)通过使所述稀释溶液与酸接触,将所述稀释溶液酸化至从约1至约3的pH以提供酸化溶液;
(f)用有机溶剂对所述酸化溶液进行分配以提供水性部分和有机部分;
(h)将所述有机部分浓缩以提供浓缩溶液;以及
(i)将所述浓缩溶液纯化以提供包含具有按重量计至少约80%的纯度的CC-00486的组合物。
5.如权利要求1所述的方法,其中,所述至少一种具有式I的二氢查耳酮化合物是CC-00549,并且所述方法进一步包括:
(d)将所述第二溶液浓缩;以及
(e)通过制备HPLC纯化所述第二溶液以提供包含具有按重量计至少约80%的纯度的CC-00549的组合物。
6.如权利要求1所述的方法,其中,所述至少一种具有式I的二氢查耳酮化合物是CC-00536,并且所述方法进一步包括:
(d)用水性碱稀释所述第二溶液以提供稀释溶液;
(e)通过使所述稀释溶液与酸接触,将所述稀释溶液酸化至从约8至约10的pH以提供酸化溶液;
(f)用有机溶剂对所述酸化溶液进行分配以提供水性部分和有机部分;
(g)通过使所述水性部分与酸接触,将所述水性部分酸化至从约4至约6的pH以提供第二酸化溶液;
(h)用有机溶剂对所述第二酸化溶液进行分配以提供第二水性部分和第二有机部分;
(i)将所述第二有机部分浓缩以提供浓缩溶液;以及
(j)将所述浓缩溶液纯化以提供包含具有按重量计至少约80%的纯度的CC-00536的组合物。
7.如权利要求1所述的方法,其中,所述至少一种具有式I的二氢查耳酮化合物是CC-00537,并且所述方法进一步包括:
(d)用水性碱稀释所述第二溶液以提供稀释溶液;
(e)通过使所述稀释溶液与酸接触,将所述稀释溶液酸化至从约8至约10的pH以提供酸化溶液;
(f)用有机溶剂对所述酸化溶液进行分配以提供水性部分和有机部分;
(g)通过使所述水性部分与酸接触,将所述水性部分酸化至从约4至约6的pH以提供第二酸化溶液;
(h)用有机溶剂对所述第二酸化溶液进行分配以提供第二水性部分和第二有机部分;
(i)将所述第二有机部分浓缩以提供浓缩溶液;以及
(j)将所述浓缩溶液纯化以提供包含具有按重量计至少约80%的纯度的CC-00537的组合物。
9.如权利要求8所述的饮料,其中,所述至少一种具有式I的二氢查耳酮化合物选自下组,所述组由以下各项组成:CC-00474、CC-00486、CC-00487、CC-00549、CC-00536、CC-00537及其组合。
10.如权利要求8或9所述的饮料,其中,所述至少一种甜味剂是选自下组的甜菊醇糖苷,所述组由以下各项组成:莱鲍迪苷M、莱鲍迪苷D、莱鲍迪苷A、莱鲍迪苷N、莱鲍迪苷O、莱鲍迪苷E、甜菊单糖苷、甜菊双糖苷、甜叶悬钩子苷、杜克苷B、杜克苷A、莱鲍迪苷B、莱鲍迪苷G、甜菊苷、莱鲍迪苷C、莱鲍迪苷F、莱鲍迪苷I、莱鲍迪苷H、莱鲍迪苷L、莱鲍迪苷K、莱鲍迪苷J、莱鲍迪苷M2、莱鲍迪苷D2、莱鲍迪苷S、莱鲍迪苷T、莱鲍迪苷U、莱鲍迪苷V、莱鲍迪苷W、莱鲍迪苷Z1、莱鲍迪苷Z2、莱鲍迪苷IX、酶促葡萄糖基化的甜菊醇糖苷及其组合。
11.如权利要求8或9所述的饮料,其中,所述至少一种甜味剂是选自下组的罗汉果苷,所述组由以下各项组成:grosmogroside I、罗汉果苷IA、罗汉果苷IE、11-氧代罗汉果苷IA、罗汉果苷II、罗汉果苷II A、罗汉果苷II B、罗汉果苷II E、7-氧代罗汉果苷II E、罗汉果苷III、罗汉果苷IIIe、11-脱氧罗汉果苷III、罗汉果苷IV、11-氧代罗汉果苷IV、11-氧代罗汉果苷IV A、罗汉果苷V、异罗汉果苷V、11-脱氧罗汉果苷V、7-氧代罗汉果苷V、11-氧代罗汉果苷V、异罗汉果苷V、罗汉果苷VI、罗汉果醇、11-氧代罗汉果醇、赛门苷I、赛门苷I的1,6-α异构体及其组合。
12.如权利要求8-11中任一项所述的饮料,其中,与不含所述至少一种二氢查耳酮的饮料的蔗糖等效值相比,所述饮料的蔗糖等效值提高至少约1.2倍。
13.如权利要求8-11中任一项所述的饮料,其中,与不含所述至少一种二氢查耳酮的饮料的至少一种味道属性相比,所述饮料的至少一种味道属性得到改善。
14.如权利要求8-11中任一项所述的饮料,其中,所述饮料选自低卡路里或零卡路里饮料。
15.如权利要求8-11中任一项所述的饮料,其中,所述饮料选自下组,所述组由以下各项组成:冷冻的碳酸饮料、增强的起泡饮料、可乐、水果风味的起泡饮料、姜汁汽水、软饮品、沙士、果汁、水果风味果汁、果汁饮品、花蜜、蔬菜汁、蔬菜风味汁、运动饮品、能量饮品、增强水饮品、具有维生素的增强水、近水饮品、椰子汁、茶类饮品、咖啡、可可饮品、含有乳成分的饮料、含有谷物提取物的饮料以及冰沙。
16.如权利要求14所述的饮料,其中,所述饮料是低卡路里或零卡路里的水果风味的起泡饮料。
17.如权利要求15所述的饮料,其中,所述饮料是增强水饮料。
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US201862749993P | 2018-10-24 | 2018-10-24 | |
US62/749,993 | 2018-10-24 | ||
PCT/US2019/057410 WO2020086559A1 (en) | 2018-10-24 | 2019-10-22 | Dihydrochalcones from balanophora harlandii |
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US (1) | US20210386098A1 (zh) |
EP (1) | EP3870592A4 (zh) |
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CN117430649B (zh) * | 2023-12-21 | 2024-02-13 | 四川省中医药转化医学中心 | 根皮苷衍生物及其制备方法和在变叶海棠质量标志物中的应用 |
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US3087821A (en) * | 1961-11-28 | 1963-04-30 | Robert M Horowitz | Dihydrochalcone derivatives and their use as sweetening agents |
ES2139518B1 (es) * | 1997-09-16 | 2000-10-16 | Zoster Sa | Nuevas composiciones edulcorantes de solubilidad instantanea en agua compuestas de neohesperidina dihidrochalcona con otro u otros edulcorantes de alta intensidad. |
EP2368442B1 (en) * | 2005-07-27 | 2014-12-17 | Symrise AG | Use of hesperetin for enhancing the sweet taste |
CN101528059B (zh) * | 2006-10-24 | 2012-12-05 | 奇华顿股份有限公司 | 消费品 |
US20080226799A1 (en) * | 2007-03-14 | 2008-09-18 | Concentrate Manufacturing Company Of Ireland | Diet Cola Beverages |
US20180235259A1 (en) * | 2007-06-08 | 2018-08-23 | Givaudan Sa | Consumables |
EP2220945B1 (en) * | 2008-12-11 | 2013-03-27 | Symrise AG | Aroma composition to reduce or suppress undesirable bitter and astringent taste impressions of sweeteners |
EP3614860A4 (en) * | 2017-04-25 | 2021-01-13 | The Coca-Cola Company | SWEET AND TASTE IMPROVEMENT OF STEVIOL GLYCOSIDE OR MOGROSIDE SWEETEN WITH DIHYDROCHALCONES |
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- 2019-10-22 WO PCT/US2019/057410 patent/WO2020086559A1/en unknown
- 2019-10-22 US US17/287,345 patent/US20210386098A1/en active Pending
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WO2020086559A1 (en) | 2020-04-30 |
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