CN105777824A - 一种甜菊糖衍生物及其应用 - Google Patents
一种甜菊糖衍生物及其应用 Download PDFInfo
- Publication number
- CN105777824A CN105777824A CN201610181675.XA CN201610181675A CN105777824A CN 105777824 A CN105777824 A CN 105777824A CN 201610181675 A CN201610181675 A CN 201610181675A CN 105777824 A CN105777824 A CN 105777824A
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- Prior art keywords
- stevioside
- compound
- stevioside derivative
- derivative
- product
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/256—Polyterpene radicals
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- 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
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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
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- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
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- A61K8/602—Glycosides, e.g. rutin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/56—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical directly bound to a condensed ring system having three or more carbocyclic rings, e.g. daunomycin, adriamycin
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Epidemiology (AREA)
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Abstract
本发明涉及一种甜菊糖衍生物及其应用，属于食品化工技术领域。该发明以甜菊糖衍生物化合物(Ⅰ)为底物，使所述底物在葡萄糖基供体存在下，在UDP‑葡萄糖基转移酶的催化作用下反应生成甜菊糖衍生物化合物(Ⅳ)，生产工艺绿色安全，且生产成本低、周期短，极大的提高产品的竞争力。由于本发明操作简便，转化效率高，提纯容易，所得产品纯度高，可用于食品与饮料业，具有重要的应用价值。
Description
技术领域
本发明涉及一种甜菊糖衍生物及其应用，属于食品化工技术领域。
背景技术
甜菊糖是从菊科草本植物甜叶菊的叶、茎中提取出的一种新型天然甜味剂，是一种天然、绿色、保健的功能食品，它有着芬芳、清凉的味道，还具有甜度高、热能低的特点，其甜度是蔗糖的200-300倍，而热值仅为蔗糖额1/300，是一种可替代蔗糖非常理想的甜味剂。随着人类对健康、绿色的重视，甜菊糖被食品科学家称为是未来世界最具发展前景的甜味剂。
甜菊糖被国际医学界认为是人类良好的营养补充剂和保健药品。经大量科学实验证明，甜菊糖有利于调节血糖和血压，经常食用可调节血糖水平，预防高血压，改善低血压症状；甜菊糖还具有抑制某些细菌生长和繁殖及阻止其感染的作用，能够治疗感冒和流感及预防龋齿等病症；甜菊糖能够降低人对糖和脂肪的需求，调节其日常饮食，降低人们对烟酒的需求，防止了糖尿病、肥胖症、心脏病等疾病的发生；同时，甜菊糖还具有对皮肤修复和改良作用，它能治疗皮肤疾病，消除皱纹，去除疤痕等。
甜菊糖可广泛应用于食品、饮料、调味料、医药、日用化工、酿酒、化妆品等行业，较使用蔗糖可节省成本约60％，且营养价值高。甜菊糖的稳定性、代谢途径及其安全性已被深入研究，它已经我国卫生部、轻工业部批准使用，且亦被美国食品药品监督管理局认可为“GRAS(一般认为是安全的)”的级别。甜菊糖作为蔗糖的天然替代品，其应用前景广阔。
甜菊糖虽有着众多优势，但是其严重的苦涩后味，却阻碍了其的广泛应用。目前，甜菊糖口感的改善可通过酶法生物转化来实现。已有报道，可以利用环糊精糖基转移酶改性甜菊糖，以改善其口感和味质，但是该酶转移糖基的位置不专一，产物不纯，且其甜度也严重降低。
甜菊双苷向甜菊苷和莱鲍迪苷B的转化以及甜菊苷转化为莱鲍迪苷A和D的反应等。这些研究相对于甜菊糖的众多组分而言，仍微乎其微，而且其改性后的口感和味质也是一项庞大的研究。寻求高效的生物转化酶，转化工艺以及新型甜菊糖衍生物仍是甜菊糖未来的研究趋势。
发明内容
本发明解决的技术问题是：提出一种可以较低的成本和较短的生产周期产出优质的甜菊糖衍生物及其应用，该方法以化合物(Ⅰ)为原料，在UDP-葡萄糖基转移酶的催化作用下反应生成甜菊糖衍生物化合物(Ⅳ)。
为了解决上述技术问题，本发明提出的技术方案是：一种化合物(Ⅳ)，结构式如下：
为了解决上述技术问题，本发明提出的另一技术方案是：化合物(Ⅳ)的应用，可应用于食品，饮料，烟草产品，调味品，日用化工产品，药物组分，营养保健产品，口腔卫生产品或化妆品。
有益效果：
本发明以甜菊糖衍生物化合物(Ⅰ)为底物，使所述底物在葡萄糖基供体存在下，在UDP-葡萄糖基转移酶的催化作用下反应生成甜菊糖衍生物化合物(Ⅳ)，生产工艺绿色安全，且生产成本低、周期短，极大的提高产品的竞争力。由于本发明操作简便，转化效率高，提纯容易，所得产品纯度高，可用于食品与饮料业，具有重要的应用价值。
附图说明
下面结合附图对本发明的作进一步说明。
图1是化合物(Ⅳ)的HPLC谱图
图2是化合物(Ⅳ)的MS谱图
具体实施方式
本发明的UDP-葡萄糖基转移酶(即尿苷二磷酸葡萄糖基转移酶)由南京诺云生物科技有限公司发酵生产部提供，以下将UDP-葡萄糖基转移酶简称M303。
实施例1：
重组大肠杆菌的构建及诱导表达
利用分子生物学和基因工程技术等获得含有目的基因的重组大肠杆菌表达菌株，然后将重组大肠杆菌发酵培养，诱导表达制备含有目的蛋白的重组细胞。其具体步骤如下：
1)合成所需的引物片段，通过PCR扩增获得所需的UDP-葡萄糖基转移酶M303编码DNA片段，并通过同源重组技术，整合到pNYK表达载体的表达框中。
2)将重组质粒转化到大肠杆菌中，获得含有目的基因的工程菌J303。
3)将1ml工程菌J303置于TB培养基中，250rpm、37℃振荡培养至OD600＝1.0，加入终浓度为0.1mMIPTG于25℃振荡培养16h。诱导结束后以10000g，5min离心收集细胞，置于-80℃储存备用。得到了含有M303蛋白的菌体。
实施例2：
利用化合物(Ⅰ)为底物制备化合物(Ⅳ)
取湿菌体M303444mg，用无菌水重悬细胞，并于冰浴中超声波破碎细胞，即为反应所用的粗酶液。精密称取样品，配制成1.85ml体系，其中底物化合物(Ⅰ)的终浓度2.0g/L、UDP-葡萄糖为2.70g/L，并加入0.286g/L的MgCl2；然后加入粗酶液，并加入终浓度0.1M的Tris-HCl缓冲液(pH8.0)至体系为1.85ml，起始反应。25℃恒温摇床以150rpm振荡38h，100℃煮沸终止反应。13000g离心10min，取上清作为样品，利用大孔树脂对样品进行初提纯，并使用LC-MS方法检测提纯的化合物(Ⅳ)的纯度。
实施例3：
最佳金属离子浓度的确定
取实施例1中的菌体M303444g，按照实施例2中的方法，转移至5ml离心管中，加入终浓度为2.0g/L的化合物(Ⅰ)，UDP-葡萄糖为2.70g/L及MgCl2，并加入0.1MTris-HCl缓冲液(pH8.0)。按上述方法，取平行样，加入MgCl2的终浓度分别为0、0.1、0.286g/L，反应38h后，取样品煮沸终止后离心，将上清样品进行HPLC分析。其中MgCl2为0.286时，化合物(Ⅳ)产量最高。·
实施例4：
最佳反应温度的确定
取实施例1中的菌体M303444g，按照实施例2中的方法，转移至5ml离心管中，加入终浓度为0.1M的Tris-HCl缓冲液(pH8.0)，化合物(Ⅰ)为2.0g/L，UDP-葡萄糖为2.70g/L。按上述方法取平行样，分别于20、25、30、37℃，150rpm进行催化反应，反应30h后，取样品煮沸终止后离心，将上清样品进行HPLC分析。其中温度为25℃，化合物(Ⅳ)产量最高。
实施例5：
最佳反应pH的确定
取实施例1中的菌体M303444g，按照实施例2中的方法，转移至5ml离心管中，加入终浓度为0.1M的Tris-HCl缓冲液，化合物(Ⅰ)为2.0g/L，UDP-葡萄糖为2.70g/L。按上述方法取平行样，其中pH分别调至5.0、6.0、7.0、7.5、8.0、9.0。于30℃，150rpm进行催化反应，反应38h后，取样品离心，将上清样品进行HPLC分析。其中pH为8.0时，化合物(Ⅳ)的产量最高。
实施例6：
最佳底物添加量
取实施例1中的菌体M303444g，按照实施例2中的方法，转移至5ml离心管中，加入终浓度为0.1M的Tris-HCl缓冲液(pH8.0)，UDP-葡萄糖为2.70g/L。按上述方法，取平行样，并分别加入终浓度为0.676、0.901、1.35、2.0、5.41、13.51、27.03、54.05g/L的化合物(Ⅰ)。反应38h后，取样品煮沸终止后离心，将上清样品进行HPLC分析。其中添加2.0g/L底物时，化合物(Ⅳ)的产量最高。
实施例7：
化合物(Ⅳ)结构分析
化合物(Ⅰ)的结构已通过进行氢、碳及二维核磁共振谱分析的方法解析。化合物(Ⅰ)分子量(1127)是相当于甜菊醇加五个葡萄糖，根据过量M303酶存在的特性即在β-1,2糖苷键连续加两个葡萄糖基团推断出化合物(Ⅳ)C62H100O38(1451.8)的结构，并且用LC测得分子量(1451)加以证实。化合物(Ⅳ)分子量是相当于甜菊醇加7个葡萄糖。
上述实施例只为说明本发明的技术构思及其特点，旨在让本领域的技术人员能够容易理解本发明的内容并据以实施，并不能以此来限制本发明的保护范围。但凡根据本发明精神实质所做的等效变化或者修饰，都应该·涵盖在本发明的保护范围之内。
Claims (2)
1.一种化合物(Ⅳ)，其特征在于：结构式如下：
2.根据权利要求1所述的化合物(Ⅳ)的应用，其特征在于：可应用于食品，饮料，烟草产品，调味品，日用化工产品，药物组分，营养保健产品，口腔卫生产品或化妆品。
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