CN107105733B - 甜叶菊成分、生产方法和用途 - Google Patents
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Abstract
甜叶菊组合物从甜叶菊(Stevia rebaudiana Bertoni)提取物制备。所述组合物或组分能够提供优异的味道特征,并且可以在食品、饮料、化妆品和药品中用作甜味剂,甜味增强剂,调味剂,增味剂。
Description
发明背景
本发明领域
本发明涉及一种从甜叶菊(Stevia rebaudiana Bertoni)植物生产纯化的食品成分的方法及所述食品成分在各种食品和饮料中的用途。
在相关技术的描述
目前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。
上述的甜糖苷,都有一个共同的糖苷配基,甜叶菊醇,并区别在于在C13和C19的位置的糖残基的数量和类型。甜叶菊的叶子能够积累高达10-20%(以干重量为基础)甜叶菊醇糖苷。在甜叶菊叶子中发现的主要糖苷是莱鲍迪苷A(2-10%),甜叶菊苷(2-10%),和莱鲍迪苷C(1-2%)。其他糖苷如莱鲍迪苷B,D,E和F,甜叶菊双糖苷(steviolbioside)和悬钩子苷(rubusoside)在低得多的水平(约0-0.2%)被发现。
两种主要的糖苷-甜叶菊苷和莱鲍迪苷A(reb A)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 of stevioside and rebaudioside Ain carbonated beverages.J.Agric.Food Chem.31:409-412.)。
甜叶菊醇糖苷彼此不同之处,不仅在于分子结构,而且在于它们的味道性质。一般地,甜叶菊苷被发现比蔗糖甜110-270倍,莱鲍迪苷A比蔗糖甜150至320倍,莱鲍迪苷比蔗糖甜40-60倍。甜苷A比蔗糖甜30倍。在主要的甜叶菊醇糖苷中莱鲍迪苷A具有最小的涩味,最小的苦味,并且最小的持续回味从而具有最有利的感官特性(Tanaka O.(1987)Improvement of taste of natural sweetners.Pure Appl.Chem.69:675-683;PhillipsK.C.(1989)Stevia:steps in developing a new sweetener.In:GrenbyT.H.ed.Developments in sweeteners,vol.3.Elsevier Applied Science,London.1-43.)。莱鲍迪苷A的化学结构示于图1中。
使用水或有机溶剂从甜叶菊植物中提取和纯化甜糖苷的方法描述在,例如,美国专利号4,361,697;4,082,858;4,892,938;5,972,120;5,962,678;7,838,044和7,862,845。
本发明提供了替代方法,其引入了现有技术中没有描述的用于甜叶菊醇糖苷纯化的新技术。
发明内容
本发明旨在克服现有甜叶菊醇糖苷的纯化方法的缺点。
本发明部分涉及包含甜叶菊植物的甜叶菊醇糖苷的成分。甜叶菊醇糖苷选自由以下组成的组:甜叶菊苷,莱鲍迪苷A,莱鲍迪苷B,莱鲍迪苷C,莱鲍迪苷D,莱鲍迪苷E,莱鲍迪苷F,莱鲍迪苷M,莱鲍迪苷N,莱鲍迪苷O,甜苷A,甜叶菊双糖苷,悬钩子苷,以及在甜叶菊植物中的其他甜叶菊醇糖苷,糖基化的甜叶菊醇糖苷及其混合物。
本发明部分涉及一种用于生产成分的方法,所述成分包含莱鲍迪苷A,甜叶菊苷,莱鲍迪苷B,莱鲍迪苷C,莱鲍迪苷D,莱鲍迪苷E,莱鲍迪苷F,莱鲍迪苷M,莱鲍迪苷N,莱鲍迪苷O,甜苷A,甜叶菊双糖苷,悬钩子苷,以及在甜叶菊植物中的其他甜叶菊醇糖苷,糖基化的甜叶菊醇糖苷及其混合物。
起始材料是含有甜叶菊醇的一种或多种糖苷的含水溶液或含水的醇溶液-甜叶菊醇糖苷溶液。
甜叶菊醇糖苷溶液通过树脂床,其中一些甜叶菊醇糖苷被选择性吸附至树脂,而其他甜叶菊醇糖苷通过树脂床而没有任何显著吸附。随后,选择性吸附的甜叶菊醇糖苷从树脂被洗脱以获得纯化的甜叶菊醇糖苷组合物或组分。
在另一个实施方案中,甜叶菊醇糖苷溶液经历液-液提取,其使用溶剂系统,所述溶剂系统包括水和至少一种其它溶剂,其与水基本上不混溶。一些甜叶菊醇糖苷被选择性地提取到水相中而其他甜叶菊醇糖苷被提取到水不混溶的相,随后进行相分离,以获得纯化的甜叶菊醇糖苷组合物或组分。
所述组合物或组分在各种食品和饮料产品中可被用作甜味剂,甜味增强剂,调味剂和增味剂。食品和饮料产品的非限制性实例包括碳酸软饮料,即饮饮料,能量饮料,等渗饮料,低热量饮料,零热量饮料,运动饮料,茶,水果和蔬菜汁,汁饮料,果汁饮料,乳饮料,酸奶饮料,酒精饮料,粉状饮料(powdered beverages),焙烤产品,饼干,软烤饼(松饼),烘烤混合物,谷类,糕饼,糖果,太妃糖,口香糖,乳制品,调味奶,酸奶,调味酸奶,发酵奶(cultured milk),大豆酱油和其他大豆基产品,色拉味调料,蛋黄酱,醋,冷冻甜点,肉制品,鱼肉制品,瓶装和罐装食品,桌面甜味剂(tabletop sweetener),水果和蔬菜。
此外,所述组合物或组分可以用于药物或药物制剂和化妆品,包括但不限于牙膏,漱口水,咳嗽糖浆,咀嚼片剂,锭剂,维生素制剂等。
所述组合物或组分可以“原样”使用或与其它甜味剂、调味剂和食品成分组合使用。
甜味剂的非限定性例子包括甜叶菊醇糖苷,甜叶菊苷,莱鲍迪苷A,莱鲍迪苷B,莱鲍迪苷C,莱鲍迪苷D,莱鲍迪苷E,莱鲍迪苷F,莱鲍迪苷M,莱鲍迪苷N,莱鲍迪苷O,甜苷A,甜叶菊双糖苷,悬钩子苷,以及在甜叶菊植物中发现的其他甜叶菊醇糖苷以及它们的混合物,甜叶菊提取物,糖基化的甜叶菊醇糖苷,罗汉果提取物,罗汉果苷,糖基化的罗汉果苷,高果糖玉米糖浆,玉米糖浆,转化糖,低聚果糖,菊糖,低聚菊糖(inulooligosaccharides),偶联糖,低聚麦芽糖,麦芽糖糊精(maltodextins),玉米糖浆固体,葡萄糖,麦芽糖,蔗糖,乳糖,阿斯巴甜(阿司帕坦),糖精,三氯蔗糖(三氯半乳蔗糖),糖醇。
调味剂的非限制性实例包括柠檬调味剂,橙调味剂,水果调味剂,香蕉调味剂,葡萄调味剂,梨调味剂,菠萝调味剂,苦杏仁调味剂,可乐调味剂,肉桂调味剂,糖调味剂,棉花糖调味剂,香草调味剂。
其他食品成分的非限制性实例包括调味剂,酸化剂,有机酸和氨基酸,着色剂,填充剂,膨胀剂,改性淀粉,树胶(胶质),调质剂(texturizer),防腐剂,抗氧化剂,乳化剂,稳定剂,增稠剂,胶凝剂。
下列实施例说明本发明的优选实施方案。应当理解,本发明并不限定于在实施例中阐述的这些材料,比例,条件和程序(方法),这仅仅是说明性的。
实施例1
从乙醇水溶液由树脂选择性吸附
甜叶菊醇糖苷溶解于70%v/v含水乙醇,以制备10mL含有(w/w)0.67%的Reb D,0.51%的Reb M和0.82%的Reb A的溶液。溶液通过柱,所述柱装填有10mL的OH-形式的Amberlite FPA98C1树脂。该树脂用250mL的70%v/v含水乙醇洗脱,然后被吸附的甜叶菊醇糖苷用250mL去离子水洗脱。将两种溶液通过HPLC分析,其结果如下。
*TSG-总甜叶菊醇糖苷含量计算为所有的甜叶菊醇糖苷浓度的总和
由此可以看出,该Reb D和Reb M被树脂选择性吸附。
实施例2
由树脂处理甜叶菊醇糖苷水溶液
甜叶菊醇糖苷溶解在去离子水中,以制备10毫升含有(w/w)0.67%Reb D,0.51%Reb M和0.82%Reb A的溶液。所述溶液通过柱,所述柱装填有10mL的OH-形式的AmberliteFPA98C1树脂。树脂用250mL水洗涤,然后用250毫升70%v/v含水乙醇洗脱。将两种溶液通过HPLC分析并且结果提供在下面。
*TSG-总甜叶菊醇糖苷含量计算为所有的甜叶菊醇糖苷浓度的总和
**ND-未检测
可以看出,没有观察到从水溶液的实质性的选择性吸附。
Claims (1)
1.一种由树脂选择性吸附甜叶菊醇糖苷的方法,包括以下步骤:
(a)提供甜叶菊醇糖苷于70%v/v含水乙醇中的溶液,所述甜叶菊醇糖苷含有莱鲍迪苷M、莱鲍迪苷D和莱鲍迪苷A;
(b)提供装有树脂的树脂柱,所述树脂是OH-形式的Amberlite FPA98C1;
(c)使(a)的溶液通过(b)的树脂柱;
(d)用70%v/v含水乙醇洗涤(c)之后获得的树脂,得到包含莱鲍迪苷A的洗脱溶液;并且
(e)用去离子水洗脱(d)之后获得的树脂,得到包含莱鲍迪苷M和莱鲍迪苷D的洗脱溶液。
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Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10952458B2 (en) * | 2013-06-07 | 2021-03-23 | Purecircle Usa Inc | Stevia extract containing selected steviol glycosides as flavor, salty and sweetness profile modifier |
US20220175002A1 (en) * | 2020-12-02 | 2022-06-09 | Epc Natural Products Co., Ltd. | Compositions comprising mogrosides, steviol glycosides and glycosylated derivatives thereof and methods of enhancing the mouthfeel or sweetness of consumables |
WO2017106577A1 (en) * | 2015-12-15 | 2017-06-22 | Purecircle Usa Inc. | Steviol glycoside compositions |
CA3050310A1 (en) | 2017-02-03 | 2018-08-09 | Codexis, Inc. | Engineered glycosyltransferases and steviol glycoside glucosylation methods |
KR20200125927A (ko) * | 2018-02-26 | 2020-11-05 | 피르메니히 에스아 | 글리코실화된 텔펜 배당체, 텔펜 배당체 및 시클로덱스트린을 포함하는 조성물 |
CN108864222A (zh) * | 2018-06-22 | 2018-11-23 | 南京亘闪生物科技有限公司 | 一种高纯度甜菊糖苷rd和rm的制备方法 |
CN109349596A (zh) * | 2018-09-29 | 2019-02-19 | 四川盈嘉合生科技有限公司 | 甜味剂组合物 |
CN109704966B (zh) * | 2018-12-25 | 2021-08-20 | 中化健康产业发展有限公司 | 一种超临界萃取技术分离甜菊叶中组份的方法 |
CN112006264B (zh) * | 2020-09-08 | 2023-12-05 | 江西福美泰生物技术有限公司 | 一种甜菊糖复合甜味剂及其制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102060892A (zh) * | 2010-12-30 | 2011-05-18 | 青岛润浩甜菊糖高科有限公司 | 甜菊糖甙rd的提纯方法 |
CN102786565A (zh) * | 2012-09-07 | 2012-11-21 | 谱赛科(江西)生物技术有限公司 | 多柱树脂串联及带醇吸附提纯甜菊糖甙的方法 |
WO2013096420A9 (en) * | 2011-12-19 | 2013-10-17 | The Coca-Cola Company | Methods for purifying steviol glycosides and uses of the same |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4361697A (en) | 1981-05-21 | 1982-11-30 | F. K. Suzuki International, Inc. | Extraction, separation and recovery of diterpene glycosides from Stevia rebaudiana plants |
ES2046979T3 (es) | 1987-07-21 | 1994-02-16 | Roger H Giovanetto | Procedimiento para la obtencion de esteviosidos a partir de material vegetal bruto. |
US8298601B2 (en) * | 2005-10-11 | 2012-10-30 | Purecircle Sdn Bhd | Process for manufacturing a sweetener and use thereof |
US7862845B2 (en) | 2005-10-11 | 2011-01-04 | Purecircle Sdn Bhd | Process for manufacturing a sweetener and use thereof |
CN101200480B (zh) * | 2006-12-15 | 2011-03-30 | 成都华高药业有限公司 | 莱鲍迪甙a的提取方法 |
WO2009140394A1 (en) * | 2008-05-13 | 2009-11-19 | Cargill, Incorporated | Separation of rebaudioside a from stevia glycosides using chromatography |
WO2011112892A1 (en) | 2010-03-12 | 2011-09-15 | Purecircle Usa Inc. | High-purity steviol glycosides |
US20120083593A1 (en) | 2010-10-01 | 2012-04-05 | Shanghai Yongyou Bioscience Inc. | Separation and Purification of Stevioside and Rebaudioside A |
EP2640736B1 (en) | 2010-11-19 | 2016-08-31 | Cargill, Incorporated | Method for the enrichment of rebaudioside b and/or rebaudioside d in stevia-derived glycoside compositions using adsorb-desorb chromatography with a macroporous neutral adsorbent resin |
WO2012088598A1 (en) | 2010-12-30 | 2012-07-05 | Glg Life Tech Corporation | Processes of purifying steviol glycosides |
US8962698B2 (en) | 2011-01-28 | 2015-02-24 | Tate & Lyle Ingredients Americas Llc | Rebaudioside-mogroside V blends |
EA201400836A8 (ru) | 2012-01-23 | 2016-03-31 | ДСМ АйПи АССЕТС Б.В. | Получение дитерпена |
CA2899276C (en) | 2013-02-06 | 2022-11-01 | Evolva Sa | Methods for improved production of rebaudioside d and rebaudioside m |
US9522929B2 (en) | 2014-05-05 | 2016-12-20 | Conagen Inc. | Non-caloric sweetener |
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---|---|---|---|---|
CN102060892A (zh) * | 2010-12-30 | 2011-05-18 | 青岛润浩甜菊糖高科有限公司 | 甜菊糖甙rd的提纯方法 |
WO2013096420A9 (en) * | 2011-12-19 | 2013-10-17 | The Coca-Cola Company | Methods for purifying steviol glycosides and uses of the same |
CN102786565A (zh) * | 2012-09-07 | 2012-11-21 | 谱赛科(江西)生物技术有限公司 | 多柱树脂串联及带醇吸附提纯甜菊糖甙的方法 |
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US11155888B2 (en) | 2021-10-26 |
EP3197469A4 (en) | 2018-05-16 |
US20170298460A1 (en) | 2017-10-19 |
WO2016049315A1 (en) | 2016-03-31 |
US20200032358A9 (en) | 2020-01-30 |
EP3197469B1 (en) | 2023-08-09 |
EP3197469A1 (en) | 2017-08-02 |
CN107105733A (zh) | 2017-08-29 |
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