CN115336734A - 甜菊醇糖苷组合物 - Google Patents
甜菊醇糖苷组合物 Download PDFInfo
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- CN115336734A CN115336734A CN202210989662.0A CN202210989662A CN115336734A CN 115336734 A CN115336734 A CN 115336734A CN 202210989662 A CN202210989662 A CN 202210989662A CN 115336734 A CN115336734 A CN 115336734A
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- Prior art keywords
- rebaudioside
- steviol
- reb
- steviol glycoside
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- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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Abstract
本发明涉及甜菊醇糖苷组合物。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
本申请是申请日为2016年10月26日、申请号为201680067837.5、发明名称为“甜菊醇糖苷组合物”的发明专利申请的分案申请。
发明背景
本发明涉及少量甜菊醇糖苷对甜菊甜味剂的甜味特征的积极影响。
由于意识到许多疾病与食用高糖食物和饮料相关，糖替代品正受到日益增加的关注。然而，由于对其安全性的关注，许多人造甜味剂，如甘素、环己氨基磺酸钠和糖精在一些国家是被禁止或限制的。因此，天然来源的无热量甜味剂正变得越来越普遍。甜味草本植物甜菊(Stevia rebaudiana)产生若干双萜糖苷，其特征在于高强度甜味和优于许多其他强效甜味剂甜度的感官性能。
甜菊是属于卫矛科(Astracea)的植物物种，其是南美洲天然的，并且现在在全世界的许多地方种植(Gardana等，2003；Koyama等，2003；Carakostas等，2008)。甜菊叶是天然甜味的，并且在南美洲用于食品增甜已经有几百年了(Soejarto等，1982)。在日本和其他东南亚国家，多年来甜菊提取物已经在商业上用于食品增甜(Koyama等，2003)。作为自然的产物，甜菊植物叶含有不同甜味组分，称为甜菊醇糖苷。据报道，已经鉴定出通常有超过40种甜菊醇糖苷存在于甜菊叶提取物中(Ceunen和Geuns，2013；Chaturvedula等，2011a，b，c；Chaturvedula和Prakash，2011a，b；Ohta等，2010)。这些甜菊醇糖苷中的每一种都具有其自身独特的味道特征和甜味强度，其可以比糖高达350倍，但全部共同具有相似的分子结构，其中不同的糖部分连接于糖苷配基甜菊醇(内根-贝壳杉烯(ent-kaurene)-型双萜)上。甜菊醇糖苷的通用结构呈现于图1中。
莱鲍迪苷A和甜菊苷获得了最大的商业关注，并就其作为商业高强度甜味剂的适合性进行了广泛研究和表征。在碳酸饮料中的稳定性研究证实了它们的热和pH稳定性(Chang S.S.，Cook，J.M.(1983)Stability studies of stevioside and rebaudioside Ain carbonated beverages(甜菊苷和莱鲍迪苷A在碳酸饮料中的稳定性研究)，J.Agric.Food Chem.31：409-412)。
甜菊醇糖苷不仅彼此的分子结构不同，而且其味道特性也不同。通常，发现甜菊苷比蔗糖甜110-270倍，并且莱鲍迪苷A比蔗糖甜150至320倍。莱鲍迪苷A具有最少的涩味、最少的苦味和最少的持续后味，因此在主要的甜菊醇糖苷中具有最令人满意的感官属性(Tanaka 0.(1987)Improvement of taste of natural sweeteners(天然甜味剂的味道改善)，Pure App1.Chem.69：675-683；Phillips K.C.(1989)Stevia：steps in developing anew sweetener.见：Grenby T.H.编辑，Developments in sweeteners，第3卷，E1sevierApplied Science，伦敦，1-43)。
到21世纪早期，只有有限数量的甜菊中的甜菊醇糖苷的化学结构得到了表征，包括甜菊苷、莱鲍迪苷A-F、杜克苷A和甜菊双糖苷(Geunen和Geuns，2013)。近年来，报道了来自甜菊叶的具有不同化学结构的许多少量甜菊醇糖苷(Chaturvedula等，2011a，b，c；Chaturvedula和Prakash，2011a，b)。这些不同的甜菊醇糖苷，其是内根-贝壳杉烯-型双萜，经由1，2-；1，3-；1，4-或1，6-α或β-配糖键在C-13和C-19位置与各种糖相连，如葡萄糖、鼠李糖、木糖、果糖和脱氧葡萄糖。各种甜菊醇糖苷的性质和分组概括于表1中。由于大量的甜菊醇糖苷，根据与甜菊醇主链连接的糖部分，表1列出了5组甜菊醇糖苷，并用缩写的组成名称来识别。
·葡糖基甜菊醇家族：只包括甜菊醇和葡萄糖残基。这组可以通过通式“SvGn”来呈现，其中Sv是甜菊醇，而G是葡萄糖。
·鼠李糖基甜菊醇家族：包括甜菊醇、鼠李糖和葡萄糖残基。这组可以通过通式“SvR1Gn”来呈现，其中R是鼠李糖。
·木糖基甜菊醇家族：包括甜菊醇、木糖和葡萄糖残基。这组可以通过通式“SvX1Gn”来表示，其中X是木糖。
·果糖基甜菊醇家族：包括甜菊醇、果糖和葡萄糖残基。这组可以通过通式“SvF1Gn”来表示，其中F是果糖。
·脱氧葡萄糖甜菊醇家族：包括甜菊醇、脱氧葡萄糖和葡萄糖残基。这组可以通过通式SvdG1Gn来呈现。
表1
发明概述
本发明涉及改善甜菊醇糖苷甜味剂(如甜菊苷和莱鲍迪苷A(Reb A))的甜味特征。出乎预料地发现了某些少量甜菊醇糖苷对其他甜菊醇糖苷，包括莱鲍迪苷D(Reb D)和莱鲍迪苷M(Reb M)的甜味特征具有有利的影响。这些少量甜菊醇糖苷，尽管少量存在，但证明了对甜菊甜味剂的甜味特征的统计学显著的积极影响。如本文中使用的，少量甜菊醇糖苷是以低于5％或低于2％的量存在于组合物中的甜菊醇糖苷。
附图简述
图1显示了甜菊醇糖苷的通用结构。
图2a显示了莱鲍迪苷N的结构。图2b显示了莱鲍迪苷Q的结构。
图3a是显示出品尝小组结果的条形图。第一条表示来自品尝酸化水中的高度纯化的(至少97％纯的)莱鲍迪苷A组合物的结果。第二条表示来自品尝酸化水中的果糖化莱鲍迪苷A组合物的结果。
图3b是显示出品尝小组结果的条形图。第一条表示来自品尝包括高度纯化的RebM/Reb D混合物的减肥柠檬-酸橙碳酸软饮料的结果，其中所述混合物包括50％重量Reb M和50％重量Reb D。第二条表示来自品尝包括果糖化莱鲍迪苷A组合物的减肥柠檬-酸橙碳酸软饮料的结果。
图4a是显示出品尝小组结果的条形图。第一条表示来自品尝酸化水中的高度纯化的(至少97％纯的)莱鲍迪苷A组合物的结果。第二条表示来自品尝酸化水中的糖基化少量甜菊醇糖苷组合物的结果，其中所述糖基化少量甜菊醇糖苷组合物含有19％重量糖基化Reb Q和18％重量糖基化Reb R。
图4b是显示出品尝小组结果的条形图。第一条表示来自品尝包括高度纯化的RebM/Reb D混合物的减肥柠檬-酸橙碳酸软饮料的结果，其中所述混合物包括50％重量Reb M和50％重量Reb D。第二条表示来自品尝酸化水中包括糖基化少量甜菊醇糖苷的减肥柠檬-酸橙碳酸软饮料的结果，其中所述糖基化少量甜菊醇糖苷组合物含有19％重量糖基化RebQ和18％重量糖基化Reb R。
详述
发现包括少量糖苷(如莱鲍迪苷N和莱鲍迪苷Q)的甜菊醇糖苷组合物(SG组合物)对甜菊甜味剂的甜味特征具有正面影响。示例性甜菊醇糖苷组合物描述于表2中。
表2：甜菊醇糖苷组合物(SG组合物)
Reb D/Reb M混合物与甜菊醇糖苷组合物的比较
实施例1：酸化水-5白利糖度靶
15名专家品尝了样品溶液，如表3中概括的：
表3：酸化水5白利糖度靶-SG组合物相对于Reb D和Reb M混合物
*＝80％置信区间，**＝90％置信区间，***＝95％置信区间
如可以看到的，甜菊醇糖苷组合物(SG组合物)具有许多比Reb D/Reb M混合物更类似于5％糖溶液的属性，并且整体相似性高于Reb D/Reb M混合物。具有少量糖苷和70/30Reb D/M混合物的甜菊醇糖苷组合物甜度相当。与SG组合物相比，Reb D/Reb M70/30混合物具有明显更高的涩味、酸味、异味和甜味后味。这两种样品具有显著不同的风味特征。
实施例2：酸化水-10白利糖度靶
与实施例1一样进行了相同测试，但使用10白利糖度靶。13名专家品尝了该溶液，如表4中概括的。
表4：酸化水10白利糖度靶-SG组合物相对于Reb D和Reb M混合物
*＝80％置信区间，**＝90％置信区间，***＝95％置信区间
在此测试中，甜菊醇糖苷组合物和Reb D/Reb M混合物的糖度相似。与甜菊醇糖苷组合物相比，70/30混合物还具有明显更高的甜味后味。
尽管不打算受到理论的束缚，但认为莱鲍迪苷N和莱鲍迪苷0，尽管以少量存在于甜菊醇糖苷组合物中，对甜菊醇糖苷组合物的风味和甜度特征具有有利影响，特别是在5白利糖度靶水平下。莱鲍迪苷N和莱鲍迪苷0的结构显示于图2a和2b中。然而，即使在10白利糖度靶下，也观察到了某些优势，使得这些少量甜菊醇糖苷在甜味特征改善中是有重大意义的。
实施例3：果糖化甜菊醇糖苷
发现了将一个或多个果糖分子添加至莱鲍迪苷A提供了风味和甜味特征优势。认为莱鲍迪苷A或其他甜菊醇糖苷(包括少量甜菊醇糖苷)的果糖化可以提供与高度纯化的甜菊醇糖苷类似于乃至优于高度纯化的甜菊醇糖苷的特征。使莱鲍迪苷A接受糖基化处理，以将果糖添加至G1和G2位置，并且与酸化水中的高度纯化的莱鲍迪苷A组合物以及减肥柠檬-酸橙碳酸软饮料中的高度纯化的Reb M/Reb D混合物进行比较。来自受过培训的测试专家小组的结果显示于图3a和3b中。
实施例4：糖基化的少量甜菊醇糖苷
发现除了它们对甜菊醇糖苷组合物的风味和甜味特征的有利影响外，当将它们糖基化时，可以提高少量糖苷的影响。糖基化甜菊醇糖苷(GSG)具有一个或多个连接于甜菊醇糖苷主链上的糖苷部分，并且发现了对甜菊醇糖苷组合物的如苦味、甜味后味等的属性具有有利影响。糖基化少量甜菊醇糖苷可以将甜菊醇糖苷组合物的风味和甜味特征改善至与高度纯化的甜菊醇糖苷的风味和甜味特征相似乃至超过高度纯化的甜菊醇糖苷的风味和甜味特征，由此提供高度纯化的甜菊醇糖苷的有效且高效的替代品。
糖苷部分可以是任何单糖、双糖或寡糖，如葡萄糖、果糖、鼠李糖、木糖等。糖苷部分可以是单个分子，或可以是分子链，例如，连接于甜菊醇糖苷上的2、3或4个葡萄糖单体。糖基化处理通常导致糖苷部分连接于甜菊醇糖苷上的C-13或C-19位置。
在一个实施方案中，将莱鲍迪苷A和少量甜菊醇糖苷组合物糖基化。少量甜菊醇糖苷含量包括约19％重量的糖基化莱鲍迪苷Q，以及约18％重量的糖基化莱鲍迪苷R。
通过受过培训的专家小组品尝含有不同含量的糖基化少量甜菊醇糖苷组合物的酸化水和减肥柠檬一酸橙糖苷组合物并且结果显示于图4a和4b中。如可以看到的，含有糖基化的少量甜菊醇糖苷的组合物在多个甜味和风味属性上与高度纯化的甜菊醇糖苷组合物(Reb A和Reb M/Reb D)几乎相同，并且在一些情况中，甚至更优。
应当理解本文中显示的之前的描述和特定的实施方案仅仅是本发明最佳方式及其原理的说明，并且所述修改和添加可以容易地由本领域技术人员来进行，而不脱离本发明的精神和范围，因此应当理解本发明的范围仅受所附权利要求的范围来限制。
Claims (3)
1.甜菊醇糖苷组合物，其包含果糖化莱鲍迪苷A。
2.如权利要求1所述的组合物，其中所述果糖化莱鲍迪苷A与莱鲍迪苷A的对比组合物相比提供降低的苦味、涩味、异味和苦味后味味道属性。
3. 一种将甜菊醇糖苷组合物的甜味特征改善至与高度纯化的莱鲍迪苷A或者莱鲍迪苷D 和莱鲍迪苷M 的混合物的甜度特征相似乃至超过高度纯化的莱鲍迪苷A或者莱鲍迪苷D 和莱鲍迪苷M 的混合物的甜度特征的方法，包括提供果糖化莱鲍迪苷A。
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Also Published As
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| EP4275516A3 (en) | 2024-01-24 |
| PL3367816T3 (pl) | 2024-05-06 |
| US20230240345A1 (en) | 2023-08-03 |
| CN108495559A (zh) | 2018-09-04 |
| US11647771B2 (en) | 2023-05-16 |
| BR122020008481B1 (pt) | 2022-10-18 |
| RU2731068C2 (ru) | 2020-08-28 |
| RU2018119142A (ru) | 2019-11-28 |
| MX2023004432A (es) | 2023-05-08 |
| ES2970118T3 (es) | 2024-05-27 |
| EP3367816C0 (en) | 2023-12-06 |
| EP3367816B1 (en) | 2023-12-06 |
| BR112018008489A2 (pt) | 2018-10-23 |
| RU2018119142A3 (zh) | 2020-02-12 |
| CN115299547A (zh) | 2022-11-08 |
| BR112018008489B1 (pt) | 2023-03-14 |
| EP3367816A1 (en) | 2018-09-05 |
| US12349709B2 (en) | 2025-07-08 |
| US20180317534A1 (en) | 2018-11-08 |
| EP4275516A2 (en) | 2023-11-15 |
| WO2017075034A1 (en) | 2017-05-04 |
| MX2018005148A (es) | 2018-08-01 |
| EP3367816A4 (en) | 2019-05-08 |
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