CN108712864A - 甜菊醇糖苷组合物 - Google Patents
甜菊醇糖苷组合物 Download PDFInfo
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- CN108712864A CN108712864A CN201680079839.6A CN201680079839A CN108712864A CN 108712864 A CN108712864 A CN 108712864A CN 201680079839 A CN201680079839 A CN 201680079839A CN 108712864 A CN108712864 A CN 108712864A
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- Prior art keywords
- steviol glycoside
- steviol
- glycosides
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Classifications
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- A23L27/30—Artificial sweetening agents
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- A23L27/36—Terpene glycosides
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/54—Mixing with gases
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/60—Sweeteners
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Abstract
描述了具有改善的甜味和风味特征的甜菊醇糖苷组合物。
Description
发明背景
糖的替代品受到越来越多的关注，因为意识到许多疾病与高糖食物和饮料的消费相关。然而，许多人造甜味剂如甘素，环拉酸钠和糖精由于它们的安全问题而在某些国家被禁止或限制。因此天然来源的无热量甜味剂正变得越来越流行。甜草本(sweet herb)甜叶菊，产生了许多二萜糖苷，所述二萜糖苷特征是高强度甜味和感官性能，其优于许多其他高效甜味剂的甜味和感官性能。
甜叶菊是属于Astracea科植物物种，原产于南美和如今栽培在世界的许多地方(Gardana等人，2003；Koyama等人，2003；Carakostas等人，2008)。甜菊叶具有天然的甜味，并且在南美已被用于甜味食品产品数百年(Soejarto等，1982)。多年来，甜叶菊(Steviarebaudiana)的提取物已在日本和其他东南亚国家在商业上用于使食物变甜(Koyama等，2003)。作为自然界的产物，甜叶菊植物叶子含有不同的甜味成分，称为甜菊醇糖苷。据报道，已经鉴定出超过40种通常存在于甜菊叶提取物中的甜菊醇糖苷(Ceunen and Geuns，2013；Chaturvedula等人，2011a，b，c；Chaturvedula and Prakash，2011a，b；Ohta等人，2010)。每个甜菊醇糖苷具有其自身独特的味道特征和甜味强度，最高可达糖的甜度的350倍，但都有一个相似的分子结构，其中不同的糖部分附着到糖苷配基的甜菊醇(一种对映贝壳杉烯(ent-kaurene)类型的双萜)。该甜菊醇糖苷的一般结构在图1中呈现。
莱鲍迪苷(rebaudioside)A和甜叶菊苷已经获得了最大的商业兴趣，并且被进行了广泛研究，其特征在于，它们适合用作商业高强度甜味剂。碳酸饮料稳定性研究证实它们的热稳定性和pH稳定性(Chang S.S.，Cook，J.M.(1983)Stability studies ofstevioside and rebaudioside A in carbonated beverages.J.Agric.Food Chem.31:409-412.)。
甜菊醇糖苷不仅通过分子结构而且通过它们的味道特性彼此不同。通常发现甜叶菊苷比蔗糖甜110-270倍，莱鲍迪苷A比蔗糖甜150至320倍。莱鲍迪苷A具有最少的涩味，最少的苦味和最不持久的余味，因此在主要甜菊醇糖苷中具有最有利的感官特性(Tanaka O.(1987)Improvement of taste of natural sweeteners.Pure Appl.Chem.69:675-683；Phillips K.C.(1989)Stevia:steps in developing a new sweetener.In:GrenbyT.H.ed.Developments in sweeteners，vol.3.Elsevier Applied Science，London.1-43.)
到21世纪初，甜叶菊中甜菊醇糖苷的仅有限的化学结构被表征，所述化学结构包括甜叶菊苷，莱鲍迪苷A-F，杜尔可苷(卫矛醇苷)(dulcoside)A和甜菊双糖苷(Ceunen和Geuns，2013)。近年来，从甜叶菊(Stevia rebaudiana)叶中报道了许多具有不同化学结构的次要甜菊醇糖苷(Chaturvedula等，2011a，b，c；Chaturvedula和Prakash，2011a，b)。这些不同的甜菊醇糖苷是对映贝壳杉烯类型的二萜，通过1，2-；1，3-；1，4-或1，6-α或β-糖苷键在C-13和C-19位与各种糖如葡萄糖、鼠李糖、木糖、果糖和脱氧葡萄糖相连。表1总结了各种甜菊醇糖苷的特性和分组。由于甜菊醇糖苷的数量很多，表1列出了5组中的甜菊醇糖苷，所述组取决于与甜菊醇主链连接的糖部分，并用缩写的组成名称鉴定。
·葡萄糖基甜菊醇家族：仅含有甜菊醇和葡萄糖残基。该组可以通式“SvGn”表示，其中Sv是甜菊醇，G是葡萄糖。
·鼠李糖基甜菊醇家族：包含甜菊醇，鼠李糖和葡萄糖残基。该组可以通式“SvR1Gn”表示，其中R是鼠李糖。
·木糖基甜菊醇家族：包含甜菊醇，木糖和葡萄糖残基。该组可以通式“SvX1Gn”表示，其中X是木糖。
·果糖基甜菊醇家族：包含甜菊醇，果糖和葡萄糖残基。该组可以通式“SvF1Gn”表示，其中F是果糖。
·脱氧葡萄糖甜菊醇家族：包含甜菊醇，脱氧葡萄糖和葡萄糖残基。该组可由通式SvdG1Gn表示。
表1
自2008年以来，一些美国(U.S.)食品和药物管理局(FDA)通常认为是与具有主要个体甜菊醇糖苷(甜叶菊苷和莱鲍迪苷A，C，D和M)的甜菊醇糖苷制剂相关的安全(GRAS)通知收到来自FDA的“无反对”信函(莱鲍迪苷A：例如，美国FDA，2008a，b，2009a，b，2011a，2012a，b，c；甜叶菊苷：美国FDA，2011b，2012d；莱鲍迪苷D：美国FDA，2013a；莱鲍迪苷X或M：US FDA，2013b，2014a；莱鲍迪苷C：US FDA，2015a)。粮农组织/世卫组织食品添加剂联合专家委员会(JECFA)在1998年，2004年，2007年和2008年的四次单独会议(第51，第63，第68和第69次会议)上审查了甜菊醇糖苷的安全性(JECFA，2000，2006，2007，2009)和建立针对甜菊提取物作为高效甜味剂的规范，以及可接受的每日摄入量(ADI)。在第68次会议上，JECFA在现有规范(含有甜叶菊苷，莱鲍迪苷A，莱鲍迪苷C和杜尔可苷A)中添加了三种甜菊醇糖苷(悬钩子苷，甜菊双糖苷和莱鲍迪苷B)，并删除了对70％甜叶菊苷/莱鲍迪苷A的要求，发表在FAO JECFA专著4(JECFA，2007)。然后在第69届JECFA(2009)中建立了对于甜菊醇糖苷的0-4mg/kg体重(bw)(表示为甜菊醇)的ADI。目前的规范包含莱鲍迪苷A，B，C，D，F，甜叶菊苷，杜尔可苷A，悬钩子苷，甜菊双糖苷，其中莱鲍迪苷A和甜叶菊苷是主要的甜味剂分子(JECFA，2010)。欧盟委员会根据欧盟委员会法规(EU)No 1131/2011允许使用甜菊醇糖苷作为甜味剂，并建立了含有以下的甜菊醇糖苷规范：不低于95％甜菊醇糖苷，莱鲍迪苷A、B、C、D、E、F，甜叶菊苷，杜尔可苷A，悬钩子苷和甜菊双糖苷，总莱鲍迪苷A和/或甜菊醇糖苷含量不低于75％(EU，2011)。在2011年，食品标准委员会(CAC)通过了食品中甜菊醇糖苷的最高含量草案(Weston，2011)。食典标准由***成员委员会制定，许多国家经常使用这些标准来支持他们自己的批准程序。
最初建立莱鲍迪苷A/甜叶菊苷安全性的关键是考虑到这两种化合物都被肠道菌群代谢为糖苷配基甜菊醇(Renwick和Tarka，2008)。体外和离体研究证实，甜菊醇糖苷不会被上消化道的消化酶水解，也不会通过胃肠道的上部被吸收(Hutapea等，1997；Geuns等，2003，2007；Koyama等，2003a，b)。因此，甜菊醇糖苷完整地进入结肠，在那里它们被拟杆菌科的成员微生物降解，导致糖苷配基甜菊醇的释放(Renwick和Tarka，2008)。一些模拟结肠厌氧条件的体外研究证实了小鼠，大鼠，仓鼠和人类的肠道微生物群完全将甜菊醇糖苷水解成甜菊醇的能力(Wingard等，1980；Hutapea等，1997；Gardana等人，2003；Koyama等人，2003a；Nikiforov等人，2013；Purkayastha等人，2014，2015，2016)。
由于最初的商业焦点是莱鲍迪苷A和/或甜叶菊苷，显然表1中的其他甜菊醇糖苷可能在甜菊醇糖苷整体的甜味效果中起作用，因此可能具有商业价值。最近的出版物指出莱鲍迪苷D和M(Prakash等2014)作为甜叶菊甜味剂制剂的主要成分的价值主张。然而，由于针对任何特定甜菊醇糖苷组合基质中的所有这些分子尚未制定目前现行质量管理规格标准，并且考虑到在动物毒性研究中测试每种甜菊醇糖苷分子和混合物组合是不切实际的，这种次要甜菊醇糖苷(无论是单独使用还是作为混合物)的商业化都非常缓慢，其原因在于各个司法管辖区的监管障碍。
为了加快在食品和饮料应用中引入模拟糖样味道特征的甜菊醇糖苷混合物的新创新，监管安全范例需要针对所有甜菊醇糖苷作为一个整体的安全性，而不是朝向单个糖苷和混合物。目前，作为可接受的食品添加剂，许多管理机构要求甜菊醇糖苷含量不低于95％，通过法规确定的9至11种主要甜菊醇糖苷中的每一种的含量计算。9至11种主要甜菊醇糖苷的这种定量被称为食品添加剂的“总甜菊醇糖苷”或“TSG”含量。从甜叶菊叶中提取的所有甜菊醇糖苷的监管批准将有助于在计算95％甜菊醇糖苷浓度时目前被排除的次要甜菊醇糖苷的创新，其目前仅包括批准的9种(JECFA)至11种(EU)糖苷。考虑到高纯度(95％)甜菊醇糖苷作为食品添加剂的要求，本发明显示这些作为甜菊醇糖苷混合物的一部分的次要糖苷分子提供优异的味道和糖样感觉属性，所述糖样感觉属性是主要分子的组合可能不能够提供的。
发明内容
本发明涉及提供甜菊醇糖苷组合物，其具有与具有9-12个主要甜菊醇糖苷分子的较高“总甜菊醇糖苷”含量(TSG)的组合物相似的性质。这些组合物需要叶提取物的较少加工，从而降低了成本并提高了操作效率，但令人惊讶的是，这些组合物的表现与较高的TSG组合物相似。较低TSG组合物含有一些主要甜菊醇糖苷(例如，莱鲍迪苷A，B，C，D和甜叶菊苷)，但也含有次要甜菊醇糖苷。这些次要甜菊醇糖苷虽然少量存在，但对甜叶菊甜味剂的甜味特征有统计学上显著的积极影响。如本文所用，次要甜菊醇糖苷是在组合物中以小于5％或小于3％的量存在的甜菊醇糖苷。
详细说明
甜菊醇糖苷组合物的总甜菊醇糖苷含量通常决定组合物的甜味和风味特征的功效和质量。从甜叶菊植物中提取甜菊醇糖苷是一个定义明确的过程，但是将植物提取物精制到某些TSG水平的选择的甜菊醇糖苷可能是耗时且昂贵的。
出乎意料地发现，在提取物浓缩过程中获得的某些“上游”中间体组合物具有令人惊讶的所需性质。在一些情况下，这些中间体组合物的表现与更浓缩的最终产物相当，即使在这些中间体组合物中主要分子的TSG含量低于最终产物。使用这些较少纯化的甜叶菊叶提取物提供了有效提供具有所需感官特性的甜菊醇糖苷成分的有效方法。
在一个实施方案中，在设计用于获得高水平的莱鲍迪苷A和甜叶菊苷的方法中，从甜叶菊叶提取物中获得具有主要甜菊醇糖苷的较低TSG组合物。虽然含有9种甜菊醇糖苷(经JECFA批准)的PCRA50样品的TSG小于95％；另外的分析评价表明，在表2所示的复杂提取物混合物中存在几种次要甜菊醇糖苷(尚未经JECFA批准)。表2还列出了下游纯化的甜叶菊提取物产品PCSG9，其具有高于95％的纯度，含有9种甜菊醇糖苷。
表2：甜菊醇糖苷组合物
实施例1：50％糖减少的碳酸软饮料
用200ppm的PCRA50制备50％糖减少的可乐味碳酸软饮料饮料。制备另一种含有200ppm PCSG9的可乐样品作为对照样品(表2)。训练有素的感官小组评估饮料样品，结果如图2所示。
使用表2中含有250ppm PCRA50组合物的50％减少的糖柠檬-酸橙(lemon-lime)味碳酸软饮料进行类似的评价。使用250ppm的PCSG9制备对比对照饮料。训练有素的感官小组评估饮料样品，结果如图3所示。值得注意的是，在柠檬-酸橙饮料中，含有次要糖苷的样品在苦味余味、苦味和酸味方面优于PCSG9样品。
从数据中可以看出，即使甜菊醇糖苷组合物具有降低的TSG含量的9种经批准的甜菊醇糖苷，但它在许多味道和风味属性上与含有更高TSG的组合物相当，并且在一些情况下更好。鉴于次要甜菊醇糖苷组分的浓度相对较低，该结果特别令人惊讶。
在另一个实施方案中，将含有少于95％TSG含量的11种公认的甜菊醇糖苷的甜叶菊叶提取物(PCA9)(委员会规则(COMMISSION REGULATION)(EU)2016/1814)与主要含有莱鲍迪苷D和M的更纯化的样品(PCRebDM)进行比较。PCA9可用作纯化的Reb D和/或Reb M产物的来源。表3中描述了根据该实施方案的示例性甜菊醇糖苷组合物。PCA9含有几种可测量量的次要甜菊醇糖苷，如表3所示。
表3：甜菊醇糖苷组合物
实施例2：含糖和甜菊醇糖苷组合物的酸化水
为了测试次要糖苷对酸化水的味道和风味特征的贡献，用300ppm柠檬酸制备三种酸化样品，并用5％糖、200ppm的PCA9或PCRebDM增甜。样品以2盎司杯供应，并由15名受过训练的小组成员品尝，以在预定的相对测量尺度上识别和量化不同的感官属性。指示小组成员啜饮以评价样品的口感和味道/风味，并且在摄取后15秒，他们评定甜味逗留和余味。
表3：酸化水5白利糖度目标-PCA9对比PCRebDM样品
*＝80％置信区间，**＝90％置信区间，***＝95％置信区间
感官小组发现PCA9和PCRebDM的甜味与5％糖溶液相当。然而，与PCA9相比，高度纯化的样品PCRebDM具有显著更高的涩味，酸味，异常特征和甜味余味。如表3所示，PCA9样品在几种味道属性中更接近糖溶液。总之，PcRebDM在关键属性方面与PCA9和糖显著不同，具有95％置信水平。由于组合物中次要甜菊醇糖苷的浓度相对较低，该结果是出乎意料的。
从数据中可以看出，即使本发明的甜菊醇糖苷组合物具有降低的TSG含量的被批准为甜味剂的主要分子，它们在许多味道和风味属性上表现与含有更高TSG的组合物相当，并且在某些情况下比含有更高TSG的组合物更好。在所述实施方案中，甜菊醇糖苷成分的TSG含量可比高TSG对照成分低约3％至约7％，同时提供相似或相当的感官结果。在其他实施方案中，较低TSG含量可以是少于约99％TSG，或比高TSG成分少约0.5％至约75％，或1％至约50％，同时为成品提供相似或相当的感官结果。
总之，表1中列出的次要甜菊醇糖苷可以显著改善具有较低的TSG的甜菊醇糖苷组合物的味道，其中较低的TSG由9至11种经批准的甜菊醇糖苷作为主要甜味剂化合物制成。具体而言，几种次要化合物(Reb J，K，H，N，O，甜叶菊苷A，Reb C2及它们的异构体)，各自浓度范围在0.1％和5％之间，可显著改善食品和饮料应用中的味道和风味特征。鉴于组合物中这些次要甜菊醇糖苷的低浓度，它们对味道和风味特征的显著有利影响是出乎意料的。
应当理解，此处所示的前述描述和具体实施方案仅仅是对本发明的最佳模式及其原理的说明，并且本领域技术人员可以容易地进行修改和添加而不脱离本发明的精神和原理，这是因此被理解为仅受所附权利要求的范围限制。
Claims (8)
1.一种甜菊醇糖苷食品添加剂组合物，其包含少于95％的主要甜菊醇糖苷。
2.权利要求1的甜菊醇糖苷食品添加剂组合物，还包含次要甜菊醇糖苷，其中主要甜菊醇糖苷和次要甜菊醇糖苷的总和不少于95％。
3.权利要求1的甜菊醇糖苷食品添加剂组合物，包含少于75％的主要甜菊醇糖苷。
4.包含甜菊醇糖苷食品添加剂组合物的饮料，其中所述食品添加剂组合物包含少于95％的主要甜菊醇糖苷。
5.如权利要求4所述的饮料，其中所述食品添加剂组合物还包含次要甜菊醇糖苷，并且其中主要甜菊醇糖苷和次要甜菊醇糖苷的总和不少于95％。
6.如权利要求4所述的饮料，其中所述食品添加剂组合物包含少于75％的主要甜菊醇糖苷。
7.甜菊醇糖苷提取物，其包含少于95％的主要甜菊醇糖苷。
8.如权利要求6所述的甜菊醇糖苷提取物，还包含次要甜菊醇糖苷，其中主要甜菊醇糖苷和次要甜菊醇糖苷的总和不少于95％，并且所述提取物具有与可比较的甜菊醇糖苷提取物实质相似的味道和风味特性，所述可比较的甜菊醇糖苷提取物包含不少于95％的主要甜菊醇糖苷。
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Also Published As
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|---|---|
| EP3389403A1 (en) | 2018-10-24 |
| US20190008193A1 (en) | 2019-01-10 |
| MX2018007241A (es) | 2018-11-09 |
| BR112018012251A2 (pt) | 2018-12-04 |
| EP3389403A4 (en) | 2019-09-04 |
| RU2018125946A (ru) | 2020-01-16 |
| RU2764635C2 (ru) | 2022-01-19 |
| RU2018125946A3 (zh) | 2020-04-17 |
| WO2017106577A1 (en) | 2017-06-22 |
| US11653686B2 (en) | 2023-05-23 |
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