CN105848496A - 作为甜味剂或甜味增强剂的新型三萜苷 - Google Patents
作为甜味剂或甜味增强剂的新型三萜苷 Download PDFInfo
- Publication number
- CN105848496A CN105848496A CN201380081448.4A CN201380081448A CN105848496A CN 105848496 A CN105848496 A CN 105848496A CN 201380081448 A CN201380081448 A CN 201380081448A CN 105848496 A CN105848496 A CN 105848496A
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- CN
- China
- Prior art keywords
- tetrahydrochysene
- pyrans
- base
- methylol
- hydroxyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
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- 239000004323 potassium nitrate Substances 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 229940079862 sodium lauryl sarcosinate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229960004711 sodium monofluorophosphate Drugs 0.000 description 1
- ADWNFGORSPBALY-UHFFFAOYSA-M sodium;2-[dodecyl(methyl)amino]acetate Chemical compound [Na+].CCCCCCCCCCCCN(C)CC([O-])=O ADWNFGORSPBALY-UHFFFAOYSA-M 0.000 description 1
- 235000008983 soft cheese Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical compound F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- WNIFXKPDILJURQ-UHFFFAOYSA-N stearyl glycyrrhizinate Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C(=O)OCCCCCCCCCCCCCCCCCC)(C)CC5C4=CC(=O)C3C21C WNIFXKPDILJURQ-UHFFFAOYSA-N 0.000 description 1
- QFVOYBUQQBFCRH-VQSWZGCSSA-N steviol Chemical compound C([C@@]1(O)C(=C)C[C@@]2(C1)CC1)C[C@H]2[C@@]2(C)[C@H]1[C@](C)(C(O)=O)CCC2 QFVOYBUQQBFCRH-VQSWZGCSSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910001631 strontium chloride Inorganic materials 0.000 description 1
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LBDVSPIQWSQRLB-UHFFFAOYSA-N sucrononic acid Chemical compound C=1C=C(C#N)C=CC=1\N=C(/NCC(=O)O)NC1CCCCCCCC1 LBDVSPIQWSQRLB-UHFFFAOYSA-N 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
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- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
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- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- GSTCPEBQYSOEHV-QNDFHXLGSA-N trilobatin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(C=C1O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 GSTCPEBQYSOEHV-QNDFHXLGSA-N 0.000 description 1
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 description 1
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- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000011691 vitamin B1 Substances 0.000 description 1
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- 239000011726 vitamin B6 Substances 0.000 description 1
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- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
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- 229920001221 xylan Polymers 0.000 description 1
- 150000004823 xylans Chemical class 0.000 description 1
- 239000011746 zinc citrate Substances 0.000 description 1
- 235000006076 zinc citrate Nutrition 0.000 description 1
- 229940068475 zinc citrate Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
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- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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- A—HUMAN NECESSITIES
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Abstract
提出三萜苷化合物,其可通过提取罗汉果得到,在制剂和组合物,尤其是可食用组合物中用作甜味剂或甜味增强剂。
Description
发明领域
本发明涉及新型三萜苷化合物,其可以通过提取罗汉果(Momordicagrosvenorii,Siraitia grosvenori)得到,及其生理上可接受的盐,其可在制剂和组合物,尤其是可口服食用组合物中用作甜味剂或甜味增强剂。
现有技术
甜味是动物和人类的初级味觉和渴望。通常使用天然产生和合成的甜味剂以满足这种自然渴望无法剔除其伴随的生理缺陷而得到满足,例如肥胖、营养失调和蛀牙。为了克服这些不想要的缺陷已经付出了大量研究努力和金钱以研发不同的化合物,例如作为天然产生甜味剂或合成甜味剂的替代物,其不具备食品价值并且不含卡路里。这种人工合成甜味剂应用广泛,并且满足了甜味需求而无食品价值,并且其使用不会提供卡路里或损坏牙齿,通常发现它们具备固有缺陷阻碍了其用于其目的用途,例如由于其毒性(对乙氧基苯脲)或染色体损害和膀胱疾病(环己基氨基磺酸钠)。因此,这些甜味剂无法被安全地推荐用作甜味剂并且显然不可食用。由于环己氨基磺酸盐更受到政府限制,通常也使用糖精化合物作为人工甜味剂。尽管糖精化合物具备甜味性能,但是它们在大部分食品和饮料组合物中不被用作单独甜味剂,因为大部分消费者会感知到持续的苦涩后味。多年来糖精和环己氨基磺酸盐已经广泛用作人工甜味剂,近来研发出一系列新的人工甜味剂。
例如,Horowitz和Gentili,US 3,087,821,教导了各种具备糖取代基的二氢査耳酮(二氢査耳酮糖苷)作为甜味剂的用途。所有的甜味二氢査耳酮具备类甘草的后味并且在口中停留一段时间。
罗汉果,属于葫芦科,是南亚一些地区和中国的原生植物。罗汉果果实的甜味主要源自三萜苷,通常已知为罗汉果苷。罗汉果中已经确定了大量罗汉果苷,但是与其他相比罗汉果糖苷V(CAS:88901‐36‐4)通常浓度最高(表1)。罗汉果苷具备相同的核心分子——罗汉果醇或氧代罗汉果醇并且区别在于与罗汉果醇或氧代罗汉果醇分子相连的糖苷残基的数量和种类不同(US 2012/0059071,Kasai et al.Agric.Biol.Chem.(1989),3347‐3349),Matsumoto等,Chem.Pharm.Bu..(1990)2030‐2032。一些罗汉果苷特别甜,通常大于蔗糖的100倍,包括罗汉果个主要三萜苷、罗汉果糖苷V及其异构体,异罗汉果糖苷V(US2011/0027413),但是它们中的大部分具备一定的苦后味。
罗汉果中存在的主要罗汉果苷列于下表A。
表A
罗汉果苷
由于含有二萜糖苷已知罗汉果叶具有甜味。源自甜叶菊的主要甜味化合物之一是瑞鲍迪苷A,在美国(自2008)和EU(自2011)允许为天然甜味剂。除了其甜味,源自甜叶菊的所有甜味剂具备与糖相比较慢出现和较长持续,并且在高浓度下有苦味或类甘草的后味(Lemus‐Mondaca et al.Food Chemistry 132(2012)1121–1132)。
另一个实例是Symrise AG,EP 2529633 A1,其涉及三萜和三萜苷和/或其生理可接受的盐。三萜,优选源自Mycetia balansae天然产生的三萜和三萜苷,用于在口服消费制剂中产生甜味感受或用于加强口服消费制剂的甜味印象。这些三萜苷与本发明要求的三萜结构不同。
因此本发明的主要目标是提供一种新的甜味化合物和其生理可接受的盐,其在食品和口服制剂中具备积极地甜味优势。特别地,本目标是提供一种甜味化合物,其能够向可食用组合物提供甜味,从而使甜度和得到甜味效果的必须施用量之间的平衡相对低,克服所述的现有技术甜味剂的缺陷。本发明的另一个目的是提供不具备涩味或苦味后味的甜味化合物。特指的甜味化合物应当是毒理学安全的、在相对低浓度下有效、消化耐受良好的、稳定(特别是在常用化妆品和/或药品制剂中)、易于配制并且生产经济。
在甜味剂的昂贵研发过程中,本发明人成功分离了式(I)的新甜味化合物并且发现,与蔗糖和罗汉果糖苷V相比,这些式(I)的甜味化合物表现出令人惊讶地良好并且强烈的甜味。令人惊讶地是进一步观察到式(I)的甜味化合物具备显著更少的不良后味并且具备高甜度。
发明内容
本发明的主题涉及式(I)的甜味化合物
其中R1、R2、R3相互独立并且代表氢、羟基、羰基或选自组包括单糖和/或低聚糖的糖配基。
优选地在式(I)的甜味化合物中单糖和/或低聚糖的单糖单元选自组包括果糖、葡萄糖、蔗糖、木糖、麦芽糖、甘露糖、鼠李糖、半乳糖、乳糖、龙胆二糖、槐糖、β‐吡喃葡萄糖基‐(1‐2)‐[β‐吡喃葡萄糖基‐(1‐6)]‐β‐吡喃葡萄糖、纤维二糖、甘露醇、山梨糖醇、木糖醇或阿拉伯糖醇、葡糖醛酸、异鼠李糖、阿拉伯吡喃糖、阿拉伯呋喃糖、吡喃木糖、呋喃木糖和/或芹菜糖(2,3,4‐三羟基‐3‐(羟甲基)丁醛),并且其中低聚糖由2至5个单糖单元构成。
术语“单糖”是指糖的最简单形式。单糖是生物学上重要的碳水化合物的最基本单元。单糖的实例包括葡萄糖、果糖、半乳糖、木糖和核糖。单糖是二糖(如蔗糖)和聚糖(如纤维素和淀粉)的基础单元。此外各个连接羟基的碳原子(除了第一个和最后一个)是手性的,产生具备相同化学式的大量异构体形式。例如半乳糖和葡萄糖都是己醛糖,但是具备不同的化学和物理性能。
术语“低聚糖”代表含有2至10,优选2至5个相连糖单元(单糖单元)的糖类聚合物。低聚糖的单糖通常通过一个糖苷键相互连接。
术语“糖配基”等同于术语糖部分或单元。
本发明的糖配基可以为其最简单的形式,优选地,以单元式(II)代表:
其中D是O、S或N
X、Y和Z相互独立并且代表氢、羟基、羰基或其他由式(II)代表的另一糖配基。该糖配基优选通过氧或氮或硫原子,更优选氧原子,其在式(II)中以D表示,与式(I)相连。在本发明的优选实施方案中,当R1、R2、R3为相互独立的糖配基时,化合物优选通过氧原子相互连接。
单糖的三维结构可以由四种不同的形式表示:a)费歇尔(Fischer)投影式是一种描述无环单糖骨架式的系统方法,使得各个手性碳的手性可以很好确定。简单开链单糖的各个立体异构体可以通过手性羟基(与手性碳相连的羟基)在费歇尔图中的位置确定。b)哈沃斯(Haworth)投影式:在该图中,α‐异构体在碳原子平面下具备异头碳的OH,而β‐异构体具备平面上的异头碳的OH。吡喃糖通常采用类似于环己烷的椅式构型。在这种构型中,α‐异构体在轴向位置具备异头碳的OH,而β‐异构体在平伏位置具备异头碳的OH。c)一种更现实的说明是椅式构型,其表现出碳链的角形式以及同样常用的是d)例如环己烷构型的至少绝对的立体化学图示。
α‐D‐吡喃葡萄糖的不同图示:Tollens(1);哈沃斯(2);椅式(3);绝对立体(来源:Wikepedia:http://de.wikipedia.org/wiki/Monosaccharide)。
对于式(II),糖单元被表示为平面配基,并且意味着在本发明中糖单元可以具备所有可能的立体异构体形式,并且不被限于特定的异构体形式。
发明的优选实施方案
(1)在一个优选实施方案中,式(I)的化合物具备至少一个式(II)的糖单元(单糖)。在一个优选实施方案中式(II)的糖单元为重复两次、三次、四次或五次并通过糖上氧原子相连的重复糖单元。
(2)在一个优选实施方案中式(II)的糖单元在式(I)仅出现一次,其为R1、R2或R3。
(3)在本发明的一个优选实施方案中式(I)的R1、R2相互独立并且代表氢、羟基、羰基或选自组包括单糖和/或低聚糖的糖配基并且式(I)的R3代表氢、羟基或羰基。优选的单糖和/或低聚糖中的单糖单元选自组包括果糖、葡萄糖、蔗糖、木糖、麦芽糖、甘露糖、鼠李糖、半乳糖、乳糖、龙胆二糖、槐糖、β‐吡喃葡萄糖基‐(1‐2)‐[β‐吡喃葡萄糖基‐(1‐6)]‐β‐吡喃葡萄糖、纤维二糖、甘露醇、山梨糖醇、木糖醇或阿拉伯糖醇、葡糖醛酸、异鼠李糖、阿拉伯吡喃糖、阿拉伯呋喃糖、吡喃木糖、呋喃木糖和/或芹菜糖(2,3,4‐三羟基‐3‐(羟甲基)丁醛)。优选葡萄糖、麦芽糖、半乳糖、阿拉伯吡喃糖和吡喃木糖,并且最优选葡萄糖、半乳糖、阿拉伯吡喃糖和吡喃木糖作为糖配基。
(4)在本发明的一个优选实施方案中式(I)的R1、R2相互独立并且代表氢、羟基、羰基或选自组包括单糖和/或低聚糖的糖配基,其选自组包括果糖、葡萄糖、蔗糖、木糖、麦芽糖、甘露糖、鼠李糖、半乳糖、乳糖、纤维二糖、龙胆二糖、槐糖、β‐吡喃葡萄糖基‐(1‐2)‐[β‐吡喃葡萄糖基‐(1‐6)]‐β‐吡喃葡萄糖、甘露醇、山梨糖醇、木糖醇或阿拉伯糖醇、葡糖醛酸、异鼠李糖、阿拉伯呋喃糖、吡喃木糖、呋喃木糖和/或芹菜糖(2,3,4‐三羟基‐3‐(羟甲基)丁醛),并且式(I)的R3代表氢、羟基或羰基。
(5)优选的用作糖配基的成分是果糖、葡萄糖、蔗糖、麦芽糖、半乳糖、阿拉伯吡喃糖和吡喃木糖,并且最优选葡萄糖、阿拉伯吡喃和吡喃木糖作为糖配基。
(6)在另一个优选实施方案中R1和R2相互独立并且代表单糖,其优选为葡萄糖和/或阿拉伯吡喃糖和/或吡喃木糖。
(7)在另一个优选实施方案中R1和R2相互独立并且代表低聚糖,其中单糖单元优选为葡萄糖和/或半乳糖和/或阿拉伯吡喃糖和/或吡喃木糖。优选地,低聚糖含有一个、两个、三个或四个葡萄糖和/或半乳糖和/或阿拉伯吡喃糖和/或吡喃木糖。更优选地,低聚糖含有一个、两个或三个葡萄糖单元。
(8)在另一个优选实施方案中R3是氢并且式(I)的R1、R2相互独立并且代表氢、羟基、羰基或选自组包括单糖和/或低聚糖的糖配基,其选自组包括果糖、葡萄糖、蔗糖、木糖、麦芽糖、甘露糖、鼠李糖、半乳糖、乳糖、纤维二糖、甘露醇、山梨糖醇、木糖醇或阿拉伯糖醇、葡糖醛酸、异鼠李糖、阿拉伯吡喃糖、阿拉伯呋喃糖、吡喃木糖、呋喃木糖和/或芹菜糖(2,3,4‐三羟基‐3‐(羟甲基)丁醛)。
(9)在另一个优选实施方案中R3是氢并且式(I)的R1、R2相互独立并且代表选自组包括单糖和/或低聚糖的糖配基,其中低聚糖的单糖单元选自组包括果糖、葡萄糖、蔗糖、木糖、麦芽糖、甘露糖、鼠李糖、半乳糖、乳糖、龙胆二糖、槐糖、β‐吡喃葡萄糖基‐(1‐2)‐[β‐吡喃葡萄糖基‐(1‐6)]‐β‐吡喃葡萄糖、纤维二糖、甘露醇、山梨糖醇、木糖醇或阿拉伯糖醇、葡糖醛酸、异鼠李糖、阿拉伯吡喃糖、阿拉伯呋喃糖、吡喃木糖、呋喃木糖和/或芹菜糖(2,3,4‐三羟基‐3‐(羟甲基)丁醛)。
(10)在一个优选实施方案中式(I)的R1和R2相互独立并且代表羟基或选自单糖和/或低聚糖的糖配基,
·其中单糖和/或低聚糖中的单糖单元选自组包括葡萄糖、2‐吡喃葡萄糖基‐葡萄糖、3‐吡喃葡萄糖基‐葡萄糖、4‐吡喃葡萄糖基‐葡萄糖、6‐吡喃葡萄糖基‐葡萄糖、或吡喃葡萄糖基‐(1→2)‐[吡喃葡萄糖基‐(1→6)]‐葡萄糖,和
·其中在低聚糖的情况下,低聚糖的单糖单元通过糖苷键相互连接,并且
·R3代表氢、羟基或羰基。
(11)在本发明的另一优选实施方案中如果式(I)化合物的R2是具备两个单糖单元的低聚糖(二糖),并且其中R2的二糖的单糖单元通过糖苷键相连,其不是1→6连接。
(12)此外,在一个优选实施方案中R2是具备两个单糖单元的低聚糖(二糖),并且R3代表氢或羰基。
(13)在本发明的另一优选实施方案中R1代表氢、羟基、羰基或2、3、4或5个单糖单元的低聚糖,并且R2是具备两个单糖单元的低聚糖(二糖),并且R3代表羟基。
(14)在本发明的一个优选实施方案中如果R2是3个单糖单元的低聚糖(三糖),则
·R1是羰和/或
·R3不是羟基或羰基或
·R3是羟基并且R1是2、4或5个单糖单元的低聚糖,其中R1的低聚糖的单糖单元通过非1→6或1→4连接的糖苷键连接。
(15)在本发明的优选实施方案中R1是单糖或具备至少3个单糖单元的低聚糖,并且
·R2是具备3个单糖单元的低聚糖(三糖),并且
·R3是羰基。
(16)在本发明的优选实施方案中R1是具备2、4或5个单糖单元,但不是3个单糖单元的低聚糖。
(17)在本发明的优选实施方案中R2是具备2至5个单糖单元的低聚糖,但不是单糖。
(18)在本发明的优选实施方案中当R2是羰基时,则
·R3不是羰基或者
·R3是羟基。
(19)在式(I)甜味化合物的另一个优选实施方案中,如果
·R1代表具备两个糖单元的糖配基,
·R2代表具备三个糖单元的糖配基,则
·R3代表氢或羰基,优先氢和/或
·R1糖单元中的糖苷键与具备二糖配基的罗汉果糖苷V和异罗汉果糖苷V中通过1→4或1→6连接的糖苷键不同并且不是1→2糖苷键。
(20)在式(I)甜味化合物的另一个优选实施方案中,如果
·R1代表具备两个糖单元的糖配基,和
·R2代表具备三个糖单元的糖配基,和
·R3代表氢。
特别优选化合物
特别优选的式(I)化合物为:
化合物A
3,11‐二羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐羟基‐2‐甲基庚‐3‐基氧基)‐4,5‐二羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物B
4,5‐二羟基‐2‐(2‐羟基‐2‐甲基‐6‐((4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物C
4,5‐二羟基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲基庚‐2‐基)‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐3‐基氧基)‐4,5‐二羟基‐2‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物D
2‐(2‐(17‐(5‐(4,5‐二羟基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲基庚‐2‐基)‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐3‐基氧基)‐4,5‐二羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物E
2‐(4,5‐二羟基‐2‐(2‐羟基‐2‐甲基‐6‐(4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物F
2‐((6‐(6‐(3‐(4,5‐二羟基‐6‐(羟甲基)‐3‐(3,4,5‐三羟基四氢‐2H‐吡喃‐2‐基氧基)四氢‐2H‐吡喃‐2‐基氧基)‐11‐羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐羟基‐2‐甲基庚‐3‐基氧基)‐3,4‐二羟基‐5‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)四氢‐2H‐吡喃‐2‐基)甲氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物G
2‐(4,5‐二羟基‐2‐(3‐羟基‐2‐甲基‐6‐(4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐2‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物H
2‐羟基‐6‐(11‐羟基‐4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐甲基庚‐3‐酮
化合物J
17‐(5‐(4,5‐二羟基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲基庚‐2‐基)‐11‐羟基‐4,4,9,13,14‐五甲基‐4,7,8,9,10,11,12,13,14,15,16,17‐十二氢‐1H‐环戊二烯并[a]菲‐3(2H)‐酮
化合物K
2‐(4,5‐二羟基‐2‐(2‐羟基‐6‐(3‐羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐甲基庚‐3‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物L
17‐(5‐(4,5‐二羟基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲基庚‐2‐基)‐4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐3,4,7,8,9,10,12,13,14,15,16,17‐十二氢‐1H‐环戊二烯并[a]菲‐11(2H)‐酮
化合物M
2‐(4,5‐二羟基‐2‐(2‐羟基‐2‐甲基‐6‐(4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物A至M以平面形式表示并尤其优选。这意味着此处代表的A至M的所有化合物包括各个化合物可能的所有异构形式。异构体含有各个元素相同数量的原子,但是这些原子的空间排布不同。异构体不必具备类似的性能,除非他们也具备相同的官能团。存在许多不同类型的异构体,如位置异构体、顺反异构体和对映异构体等。存在两种主要形式的异构体:结构异构体和立体异构体(空间异构体)。
式(I)化合物A至M的各个异构体也包含于上述结构并且在本发明中优选。
特别地,优选式(I)化合物的以下异构体:
化合物Aa
(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐2‐((3R,6R)‐6‐((3S,8S,9R,11R,13R,14S,17R)‐3,11‐二羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐羟基‐2‐甲基庚‐3‐基氧基)‐4,5‐二羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物Bb
(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐2‐((3R,6R)‐2‐羟基‐2‐甲基‐6‐((3S,9R,13R,14S,17R)‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物Cc
(2S,3R,4S,5S,6R)‐2‐((2R,3S,4R,5R,6R)‐6‐((3S,9R,13R,14S,17R)‐17‐((2R,5R)‐5‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐3‐((2S,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲基庚‐2‐基)‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐3‐基氧基)‐4,5‐二羟基‐2‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物Dd
(2S,3R,4S,5S,6R)‐2‐((2R,3R,4S,5S,6R)‐2‐((3S,8R,9R,13R,14S,17R)‐17‐((2R,5R)‐5‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐3‐((2S,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲基庚‐2‐基)‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐3‐基氧基)‐4,5‐二羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物Ee
(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐2‐((3R,6R)‐2‐羟基‐2‐甲基‐6‐((3S,8R,9R,13R,14S,17R)‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物Ff
(2S,3R,4S,5S,6R)‐2‐((2R,3R,4S,5S,6R)‐2‐((3S,8S,9R,11R,13R,14S,17R)‐17‐((2R,5R)‐5‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐3‐((2S,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲基庚‐2‐基)‐11‐羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐3‐基氧基)‐4,5‐二羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物Gg
(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐2‐((3R,6R)‐2‐羟基‐2‐甲基‐6‐((3S,9R,13R,14S,17R)‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物Hh
(6R)‐2‐羟基‐6‐((3S,9R,10R,11R,13R,14S,17R)‐11‐羟基‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐甲基庚‐3‐酮
化合物Jj
(9R,10R,11R,13R,14S,17R)‐17‐((2R,5R)‐5‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐3‐((2S,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲基庚‐2‐基)‐11‐羟基‐4,4,9,13,14‐五甲基‐4,7,8,9,10,11,12,13,14,15,16,17‐十二氢‐1H‐环戊二烯并[a]菲‐3(2H)‐酮
化合物Kk
(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐2‐((3R,6R)‐2‐羟基‐6‐((3S,9R,10S,13R,14S,17R)‐3‐羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐甲基庚‐3‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇
化合物Ll
(3S,9R,10R,13R,14S,17R)‐17‐((2R,5R)‐5‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐3‐((2S,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲基庚‐2‐基)‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐3,4,7,8,9,10,12,13,14,15,16,17‐十二氢‐1H‐环戊二烯并[a]菲‐11(2H)‐酮
化合物Mm
(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐2‐((3R,6R)‐2‐羟基‐2‐甲基‐6‐((3S,9R,10S,13R,14S,17R)‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇.
当含有两个或多个糖成分配基时(二糖或低聚糖)式(I)化合物的糖单元通过糖苷键相互连接。糖苷键是将糖类分子与另一基团相连的共价键,另一糖类可以是或不是另一糖类。糖苷键在糖(或源自糖的分子)的半缩醛基和有些有机化合物如醇的羟基之间形成。如果连接至糖类残基的基团不是另一糖类,被称为糖苷配基。如果是另一糖类,得到的单元可以称为结构的还原性末端或末端。这是一个相对的命名,其中二糖或低聚糖的还原性末端朝向结构的最后一个异头碳,而末端在相反方向。
本发明的三萜甙化合物的糖苷键列于表B:
表B
糖苷键
化合物 | 糖苷配基 | 3‐糖苷 | 24‐糖苷 |
Aa(NP‐014774) | 罗汉果醇 | ‐ | 葡萄糖‐(1‐2)‐葡萄糖 |
Bb(NP‐019280) | 11‐脱氧罗汉果醇 | 葡萄糖‐(1‐2)‐葡萄糖 | 葡萄糖‐(1‐2)‐[葡萄糖‐(1‐6)]‐葡萄糖 |
Cc(NP‐019281) | 11‐脱氧罗汉果醇 | 葡萄糖 | 葡萄糖‐(1‐2)‐[葡萄糖‐(1‐6)]‐葡萄糖 |
Dd(NP‐019282) | 罗汉果醇 | 葡萄糖‐(1‐2)‐木糖 | 葡萄糖‐(1‐2)‐[葡萄糖‐(1‐6)]‐葡萄糖 |
Ee(NP‐019501) | 11‐脱氧罗汉果醇 | 葡萄糖 | 葡萄糖‐(1‐2)‐葡萄糖 |
Ff(NP‐019680) | 24‐氧‐罗汉果醇 | 葡萄糖‐(1‐6)‐葡萄糖 | ‐ |
Gg(NP‐019681) | 3‐氧‐罗汉果醇 | ‐ | 葡萄糖‐(1‐2)‐[葡萄糖‐(1‐6)]‐葡萄糖 |
Hh(NP‐019682) | 11‐脱氧罗汉果醇 | ‐ | 葡萄糖‐(1‐2)‐[葡萄糖‐(1‐6)]‐葡萄糖 |
Jj(NP‐019683) | 11‐氧代罗汉果醇 | 葡萄糖 | 葡萄糖‐(1‐2)‐[葡萄糖‐(1‐6)]‐葡萄糖 |
Kk(NP‐019685) | 11‐脱氧罗汉果醇 | 葡萄糖 | 葡萄糖‐(1‐2)‐[葡萄糖‐(1‐6)]‐葡萄糖 |
Ll(NP‐018148) | 11‐脱氧罗汉果醇 | 葡萄糖‐(1‐6)‐葡萄糖 | 葡萄糖‐(1‐2)‐[葡萄糖‐(1‐6)]‐葡萄糖 |
Mm(NP‐19040) | 11‐脱氧罗汉果醇 | 葡萄糖‐(1‐4)‐葡萄糖 | 葡萄糖‐(1‐2)‐[葡萄糖‐(1‐6)]‐葡萄糖 |
此外,本发明涉及含有一种多种式(I)化合物的提取物,其中该提取物通过水和/或醇提取植物罗汉果得到。
优选地,由此得到的提取物含有至少一种式(I)化合物,选自组包括:
·(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐2‐((3R,6R)‐6‐((3S,8S,9R,11R,13R,14S,17R)‐3,11‐二羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐羟基‐2‐甲基庚‐3‐基氧基)‐4,5‐二羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Aa)
·(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐2‐((3R,6R)‐2‐羟基‐2‐甲基‐6‐((3S,9R,13R,14S,17R)‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Bb)
·(2S,3R,4S,5S,6R)‐2‐((2R,3S,4R,5R,6R)‐6‐((3S,9R,13R,14S,17R)‐17‐((2R,5R)‐5‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐3‐((2S,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲基庚‐2‐基)‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐3‐基氧基)‐4,5‐二羟基‐2‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Cc)
·(2S,3R,4S,5S,6R)‐2‐((2R,3R,4S,5S,6R)‐2‐((3S,8R,9R,13R,14S,17R)‐17‐((2R,5R)‐5‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐3‐((2S,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲基庚‐2‐基)‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐3‐基氧基)‐4,5‐二羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Dd)
·(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐2‐((3R,6R)‐2‐羟基‐2‐甲基‐6‐((3S,8R,9R,13R,14S,17R)‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Ee)
·(2S,3R,4S,5S,6R)‐2‐((2R,3R,4S,5S,6R)‐2‐((3S,8S,9R,11R,13R,14S,17R)‐17‐((2R,5R)‐5‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐3‐((2S,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲基庚‐2‐基)‐11‐羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐3‐基氧基)‐4,5‐二羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Ff)
·(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐2‐((3R,6R)‐2‐羟基‐2‐甲基‐6‐((3S,9R,13R,14S,17R)‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Gg)
·(6R)‐2‐羟基‐6‐((3S,9R,10R,11R,13R,14S,17R)‐11‐羟基‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐甲基庚‐3‐one(化合物Hh)
·(9R,10R,11R,13R,14S,17R)‐17‐((2R,5R)‐5‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐3‐((2S,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲基庚‐2‐基)‐11‐羟基‐4,4,9,13,14‐五甲基‐4,7,8,9,10,11,12,13,14,15,16,17‐十二氢‐1H‐环戊二烯并[a]菲‐3(2H)‐酮(化合物Jj)
·(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐2‐((3R,6R)‐2‐羟基‐6‐((3S,9R,10S,13R,14S,17R)‐3‐羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐甲基庚‐3‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Kk)
·(3S,9R,10R,13R,14S,17R)‐17‐((2R,5R)‐5‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐3‐((2S,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲基庚‐2‐基)‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐3,4,7,8,9,10,12,13,14,15,16,17‐十二氢‐1H‐环戊二烯并[a]菲‐11(2H)‐酮(化合物Ll)
·(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐2‐((3R,6R)‐2‐羟基‐2‐甲基‐6‐((3S,9R,10S,13R,14S,17R)‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Mm).
本发明也涉及制剂,其含有一种、两种、三种或更多种式(I)的甜味化合物。该制剂含有其他成分如香味化合物和/或香料制剂和/或甜味剂和/或甜味道物质。
优选的香味化合物、香料制剂、甜味剂和甜味道物质在下文详细记载。
本发明的制剂含有至少一种式(I)的甜味化合物并且可用于赋予各种口服和食品组合物和药物组合物想要的甜味和/或香味,如饮料、可食用食品、牙膏、口红等,其能或不能被消化,使用或未使用其他香料和甜味剂。本发明也涉及含有至少一种式(I)的化合物作为甜味剂和/或香料制剂的各种口服和食品组合物等。
本发明的甜味剂在可食用物质中广泛应用,主要是食品组合物如糖果、糕点和加工食品和饮料如啤酒和软饮。同样很好地适用于向其他可食用物质如药物、牙膏、邮票和信封粘合剂、动物饲料和诱饵等赋予甜味。这些实例仅用于说明而不用于将本发明限制于任何特定类型的可食用材料。通常,本发明的甜味剂可用于需要甜味的任何应用中。本发明的甜味剂可以单独使用或者与其他甜味剂、营养物质或非营养物质结合使用。同样,如果需要,可以向甜味剂加入粘合剂或稀释剂。然而,当甜味剂是具备优异加工性能的固体时,这不是必须的。这使得将甜味剂与可食用物质相混合是简单常规的操作。如果需要甜味剂可以作为固体或溶液与可食用物质混合。
本发明进一步涉及式(I)的甜味化合物使组合物或制剂变甜或增强甜味效果的用途,其中将足以产生想要甜度的有效量的式(I)的甜味化合物施用于个体。
因此本发明进一步涉及一种一同在组合物中提供甜味效果和/或增强的甜味效果的方法,包括将足以产生想要甜度的有效量的式(I)的甜味化合物施用于个体。
该有效量优选为1ppm至2000ppm,基于组合物和所有式(I)化合物的总量计。
食品、口服和药物组合物将进一步详细描述。
食品组合物
本发明的食品组合物是任何适用于消费并用于营养或享受目的的制剂或组合物,以及旨在被引入人类或动物口腔并在其中停留一段时间并随后被食用的产品(例如即食食品或饲料,见下文)或被由口腔移除的产品(例如口香糖)。这类产品包括任何在加工、部分加工或未加工状态下被人或动物消化的任何物质或产物。它们也包括在口服消费产品生产、制备或处理过程中加入并旨在引入人或动物口腔的物质。
本发明的食品组合物也包括在未改变、处理或制备状态下被人或动物吞下并消化的物质;在这方面本发明的口服消费产品也包括其他同时被吞食或预期被吞食的肠衣、糖衣或其他胶囊。表述“口服消费产品”是指即食食品和饲料,也就是对于味道重要的物质已经完成的食品和饲料。表述“即食食品”和“即食饲料”也包括饮料以及固体或半固体即食食品或饲料。可以提及的实例是冷冻产品,其在食用前必须解冻并加热至食用温度。产品如酸奶或冰激凌以及口香糖或硬焦糖也属于即食食品或饲料。
根据本发明优选的食品组合物也包括“半成产品”。在本发明中半成产品是指口服消费产品,其由于高含量的香料和味道赋予物质不适用作即食口服产品(特别是食品或饲料)。半成产品仅通过与至少一种其他成分混合(例如通过减少所述香料或味道赋予物质的浓度)并且任选进一步加工步骤(例如加热、冷冻)转化为即食口服产品(特别是食品或饲料)。半成产品的实例此处提到。
本发明的食品组合物优选包含一种或多种用于营养或享受目的的制剂。这特别包括(低卡路里)烘焙产品(例如面包、干饼干、蛋糕、其他烘烤产品)、糕饼(例如巧克力、巧克力棒、其他棒状产品、水果软糖、糖衣片、硬的和软的焦糖、口香糖)、无醇饮料(例如可可、咖啡、绿茶、红茶、富含(绿、红)茶提取物的(绿、红)茶饮品、rooibos茶、其他草本茶、含有水果的软饮、等张饮料、清爽饮料、甜美饮料(nectars)、水果和蔬菜果汁、水果或蔬菜果汁制品)、速溶饮料(例如速溶可可饮料、速溶茶饮料、速溶咖啡饮料)、肉质品(例如火腿、新鲜香肠或生香肠制品、五香或腌制的新鲜或腌肉制品)、蛋或蛋制品(干蛋、蛋白、蛋黄)、谷物制品(例如早餐谷物、麦片棒、预煮即食米饭制品)、奶制品(例如全脂或低脂或脱脂奶饮料、米粉布丁、酸奶、克菲尔(kefir)、奶油奶酪、软奶酪、硬奶酪、干燥奶粉、乳清、黄油、白脱牛奶、含有部分或全部水解乳蛋白的制品)、由大豆蛋白或其他大豆馏分得到的制品(例如豆奶和由其制得的制品、含有分离的或酶加工的大豆蛋白的饮料、含有大豆粉的饮料、含有大豆卵磷脂的制品、发酵产品如豆腐或豆豉或由其制得的制品和与水果制品以及任选香料的混合物)、水果制品(例如果酱、果汁冰糕(sorbets)、蜜饯、水果馅料)、蔬菜制品(例如番茄酱、调味汁、干燥蔬菜、冷冻蔬菜、预煮蔬菜、熬煮蔬菜)、小吃(例如烤制或炸制薯片或土豆球产品、玉米或花生为主的挤出物)、脂肪或油基制品或其乳液(例如蛋黄酱、加料蛋黄酱、调料、各个均为全脂或低脂)、其他即食菜品和汤(例如汤粉、速溶汤粉、预煮汤)、香料、香料混合物以及特别是在例如小吃领域使用的佐料、甜味剂制品、片剂或袋剂、其他用于将饮料或其他食品调成甜味或调白的制品。本发明范围内的制品也可以半成品的形式用于生产其他用于营养或享受目的的制品。本发明范围内的制品也可以胶囊、片剂(未包衣和包衣片剂,例如肠溶衣)、糖衣片、颗粒、丸剂、固体混合物、液体相中分散体的形式、乳液形式、粉末形式、溶液形式、浆剂或其他可以被吞食或咀嚼的制剂的形式,以及食品添加剂的形式。
半成品通常用于生产用于营养或享受目的的即用或即食制剂。
用于营养或享受目的的即食制剂或半成品制品的其他成分可以是用于食品或享受食品的常规底物、辅助物质和添加剂,例如水、新鲜或加工的蔬菜或动物为主或生料混合物(例如生的、烘烤、干燥、发酵、熏制和/或煮制肉类、骨头、软骨、鱼、蔬菜、草药、坚果、蔬菜汁、蔬菜泥或其混合物)、易消化或不易消化的碳水化合物(例如蔗糖、麦芽糖、果糖、葡萄糖、糊精、直链淀粉、支链淀粉、菊粉、木聚糖、纤维素、塔格糖)、糖醇(例如山梨糖醇、赤藻糖醇)、天然或硬化脂肪(例如牛脂、猪油、棕榈脂、椰子油、氢化植物脂肪)、油(例如向日葵油、花生油、玉米油、橄榄油、鱼油、豆油、芝麻油)、脂肪酸或其盐(例如硬脂酸钾)、蛋白或非蛋白氨基酸和相关化合物(例如γ‐氨基丁酸、牛磺酸)、肽(例如谷胱甘肽)、天然或加工蛋白质(例如明胶)、酶(例如肽酶)、核酸、核苷酸、令人不愉快味道印象的味道矫正剂、用于其它通常不是令人不愉快味道印象的其它味道调节剂、其它味道调节物质(例如环己六醇磷酸酯、核苷酸如鸟苷单磷酸盐、腺苷单磷酸盐或其它物质,如谷氨酸钠或2‐苯氧基丙酸)、乳化剂(例如卵磷脂、甘油二酯、阿拉伯胶)、稳定剂(例如角叉菜胶、藻酸盐)、防腐剂(例如苯甲酸及其盐、山梨糖酸及其盐)、抗氧化剂(例如生育酚、抗坏血酸)、螯合剂(例如柠檬酸)、有机或无机酸(例如乙酸、磷酸)、苦味素(例如奎宁、咖啡因、柠檬苦素、苦龙胆脂苷、律草酮(humolone)、蛇麻酮(lupolone)、儿荼酚、鞣酸)、防止酶促褐变的物质(例如亚硫酸盐、抗坏血酸)、醚油、植物提取物、天然或合成的着色剂或着色颜料(例如类胡萝卜素、类黄酮、花色素、叶绿素及其衍生物)、辛香料、三叉神经活性物质或包含这种三叉神经活性物质的植物提取物、合成的、天然的或等同天然的香料或芳香剂以及气味矫正剂。
本发明的食品组合物,例如以制品或半成品形式的那些,优选含有调味组合物用于完善和改良味道和/或气味。一种制品可以含有固体载体和调味组合物成分。适当的调味组合物包括,例如,合成、天然或等同天然的香料、香精和味道赋予物质、反应香料、烟熏香料或其他香味赋予制品(例如蛋白(部分)水解物,优选具有高精氨酸含量的蛋白(部分)水解物、烤肉香料、植物提取物、辛香料、调味制品、蔬菜和/或蔬菜制品)以及适当的辅助物质和载体。此处特别适当的是产生烘烤、肉香(特别是鸡肉、鱼肉、海鲜、牛肉、猪肉、羔羊肉、羊肉、山羊肉)、类蔬菜(特别是番茄、洋葱、大蒜、芹菜、韭菜、蘑菇、茄子、海藻)、香辛料(特别是黑胡椒和白胡椒、小豆蔻、肉豆蔻、西班牙甘椒、芥末和芥末制品)、炸制、类酵母、煮制、脂肪、咸味和/或辛辣的味道印象并因此可以增强辣味印象。香料组合物通常含有多于一种所述的成分。
本发明的食品组合物优选自组包括
·糕饼,优选低热量或无热量糕饼,优选自组包括麦片棒产品、水果糖、糖衣片、硬焦糖和口香糖,
·无醇饮料,优选自组包括绿茶、红茶、富含(绿、红)茶提取物的(绿、红)茶饮品、rooibos茶、其他草本茶、含有水果的低糖或无糖软饮、等张饮料、甜美饮料(nectars)、水果和蔬菜果汁、水果或蔬菜果汁制品,
·速溶饮料,优选自组包括速溶(绿、红、rooibos、草本)茶饮料,
·谷物制品,优选自组包括低糖和无糖早餐谷物和麦片棒,
·奶制品,优选自组包括低脂和脱脂奶饮料、酸奶、克菲尔、乳清、白脱牛奶或冰激凌,
·由大豆蛋白或其他大豆馏分得到的制品,优选自组包括豆奶、由豆奶制得的制品、含有分离的或酶加工的大豆蛋白的饮料、含有大豆粉的饮料、含有大豆卵磷脂的制品、由含有大豆卵磷脂和水果制品以及任选香料的混合物的制品制得的产品,
·甜味剂制品、片剂或袋剂,
·无糖糖衣
·冰激凌,含有或不含奶基成分,优选无糖。
A.香味或香料化合物
本领域熟知的香味化合物或香料制剂可以加入本发明的香料组合物。这些香料制剂可以选自合成香料液体和/或源自植物叶、花、水果等的油及其结合。香料液体的代表包括:人工、天然或合成水果香料如桉树油、柠檬油、橙油、香蕉油、葡萄油、白柠檬油、杏仁油和葡萄柚油和水果香精包括苹果、草莓、樱桃、橙子、菠萝等;豆类和坚果产生的味道如咖啡、可可、可乐、花生、杏仁等;以及根产生的味道如甘草或姜。
香料制剂优选自组包括精油和提取物、酊剂和香膏,例如茴香醚、罗勒油、佛手柑油、苦杏仁油、樟脑油、香茅油、柠檬油;柠檬桉油、桉树油、茴香油、葡萄柚油、洋甘菊油、荷兰薄荷油、蒿子油、白柠檬油、橘子油、肉豆蔻油(特别是肉豆蔻花油)、没药油、丁香油、丁香花油、橙油、牛至油、欧芹(籽)油、辣薄荷油、迷迭香油、鼠尾草油(香鼠尾草油、达尔马提亚或西班牙鼠尾草油)、八角油、百里香油、香草精、桧油(特别是杜松子油)、冬青油、肉桂叶油、桂皮油及其馏分,或由其分离的成分。
特别有利是本发明的香料组合物含有至少一种,优选两种、三种、四种、五种、六种、七种、八种或更多种香料制剂,其选自以下组:薄荷醇(优选左旋薄荷醇和/或消旋薄荷醇)、茴香脑、茴香醚、茴香醛、茴香醇、(外消旋)新薄荷醇、桉树脑(1,8‐桉树脑)、薄荷酮(优选L‐薄荷酮)、异薄荷酮(优选D‐异薄荷酮)、异胡薄荷醇、乙酸薄荷酯(优选L‐乙酸薄荷酯)、丙酸薄荷酯、香芹酮(优选(‐)‐香芹酮,任选作为荷兰薄荷油的组分)、水杨酸甲酯(任选作为冬青油的组分)、丁香酚乙酸酯、异丁香酚甲醚、β‐环高柠檬醛、丁香酚、异丁醛、3‐辛醇、二甲基硫醚、己醇、己醛、反式‐2‐己醛、顺式‐3‐己烯醇、4‐萜品醇、薄荷烯酮、里哪醇、乙酸8‐罗勒烯酯、异戊醇、异戊醛、α‐蒎烯、β‐蒎烯、苧烯(优选D‐苧烯,任选作为精油的组分)、薄荷酮、反式‐水合桧烯、薄荷呋喃、石竹烯、大根香叶烯D、肉桂醛、薄荷内酯、百里酚、γ‐辛内酯、γ‐壬内酯、γ‐癸内酯、(1,3E,5Z)‐十一烷三烯、2‐丁酮、甲酸乙酯、乙酸3‐辛酯、异戊酸异戊酯、顺式‐和反式‐乙酸香芹酯、对聚伞花素、大马酮、突厥酮、顺式‐氧化玫瑰、反式‐氧化玫瑰、葑醇、乙醛二乙缩醛、乙酸1‐乙氧基乙酯、顺式‐4‐庚烯醛、顺式‐茉莉酮、二氢茉莉酸甲酯、2'‐羟基苯丙酮、薄荷基甲基醚、乙酸桃金娘烯酯、2‐苯乙醇、异丁酸2‐苯乙酯、异戊酸2‐苯乙酯、香叶醇、橙花醇和绿花白千层醇。
特别优选的香味或香料化合物含有薄荷醇、桉油酚、丁香酚、麝香草酚、肉桂醛、辣薄荷油、荷兰薄荷油、桉树油、百里香油、肉桂油、丁香油、云杉针油、茴香油、鼠尾草油、茴香油、八角油、春黄菊油、和蒿子油及其混合物。
B.甜味剂和甜味道物质
本文中术语“甜味剂”代表基于蔗糖甜度(因此甜度为1)的相对甜度至少为25的物质。根据本发明(a)在口服消费产品(特别是食品、饲料或药品)中使用的甜味剂优选防龋齿和/或每克口服消费产品的热量不大于5kcal。
在本发明优选的口服消费产品中有利的甜味剂选自下组(a1)和(a2):
(i)天然存在的甜味剂,优选自组包括
·神秘果素、莫内林、马宾灵、奇异果甜蛋白、仙茅甜蛋白、布拉齐因、皮泰亭(pentaidin)、D‐苯丙氨酸、D‐色氨酸以及获自含有这些氨基酸和/或蛋白质的自然资源中得到的提取物或馏分,以及这些氨基酸和/或蛋白质的生理上可接受的盐,尤其是钠、钾、钙或铵盐;
·新橙皮苷二氢查尔酮、柚苷二氢查尔酮、甜菊苷、甜菊双糖苷、莱鲍迪苷,尤其是莱鲍迪苷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G、莱鲍迪苷H,杜尔可苷和甜叶悬钩子苷、甜茶苷A、甜茶苷B、甜茶苷G、甜茶苷H、甜茶苷I、甜茶苷J、白元参苷1、白元参苷2、糙苏苷1、糙苏苷2、糙苏苷3和糙苏苷4、相思子三萜苷A、相思子三萜苷B、相思子三萜苷C、相思子三萜苷D、cyclocaryoside A和cyclocaryoside I、奥斯雷丁、聚波朵苷A、strogin 1、strogin 2、strogin 4、selligueain A、二氢槲皮素‐3‐醋酸酯、紫苏葶、telosmoside A15、巴西甘草甜素1‐V、蝶卡苷(pterocaryoside)、cyclocaryosides、木库罗苷(mukurozioside)、反式茴香脑、反式肉桂醛、bryosides、bryonosides、bryonodulcosides、肉质雪胆阜苷、scandenosides、绞股蓝皂苷、三叶苷、根皮苷、二氢黄酮醇、苏木精、青色素、绿原酸、合欢皂苷、telosmosides、gaudichaudioside、罗汉果苷、罗汉果糖苷V、hernandulcins、莽那亭(monatin)、叶甜素、甘草次酸及其衍生物,尤其是其苷类例如甘草甜素,以及这些化合物的生理上可接受的盐,尤其是钠、钾、钙盐或铵盐;
·提取物或提取物的富集馏分,选自组包括奇异果提取物(卡特莫夫灌木)、甜叶菊种(Stevia ssp.)(尤其是Stevia rebaudiana)的提取物、swingle提取物(苦瓜属Momordica或Siratia grosvenorii、罗汉果)、Glycerrhyzia ssp.(尤其是Glycerrhyziaglabra)的提取物、悬钩子属(Rubus ssp.)(尤其是Rubus suavissimus)的提取物、柑橘提取物以及Lippia dulcis的提取物。
(ii)合成的甜味物质,优选地选自组包括,唛甘浦(magap)、环拉酸钠或环拉酸的其它生理上可接受的盐、安赛蜜K或其它生理上可接受的盐、新橙皮苷二氢查尔酮、柚苷二氢查尔酮、沙卡林(saccharin)、沙卡林钠盐、阿斯巴甜、超级阿斯巴甜、纽甜、阿力甜、糖精、紫苏葶、三氯蔗糖、胍乙酸、卡瑞来、苏洛内特和苏洛奥内特(sucrooctate)。
适当的甜味道物质,包括这些物质的天然糖如例如
·甜味道碳水化合物或糖(例如蔗糖、海藻糖、乳糖、麦芽糖、松三糖、蜜三糖、帕拉金糖、乳果糖、D‐果糖、D‐葡萄糖、D‐半乳糖、L‐鼠李糖,D‐山梨糖、D‐甘露糖、D‐塔格糖、D‐阿拉伯糖、L‐阿拉伯糖、D‐核糖,D‐甘油醛、麦芽糊精)或
·主要含有这些糖类(例如源自甜菜(Beta vulgaris ssp.,糖馏分、糖浆、糖蜜)、源自甘蔗(Saccharum officinarum ssp.,例如糖蜜、糖浆)、源自糖槭(Acer ssp.)、源自龙舌兰(龙舌兰稠汁))的蔬菜制剂,
·淀粉或蔗糖的合成/酶水解物(例如由玉米淀粉制得的转化糖浆、果糖高富集糖浆),
·水果浓缩物(例如源自苹果或梨,苹果糖浆、梨糖浆),
·糖醇(例如赤藓糖醇、苏糖醇、阿拉伯糖醇、核糖醇、木糖醇、山梨糖醇、甘露醇、卫矛醇、乳糖醇),
·蛋白质(例如非洲奇果蛋白、莫内林、奇异果甜蛋白、仙茅甜蛋白、brazzein)
·人工甜味剂(magap、环己基氨基磺酸钠、乙酰磺胺酸钾、新橙皮苷二氢查耳酮、糖精钠、阿斯巴甜超阿斯巴甜、纽甜、阿力甜(Alitam)、三氯蔗糖(Sucralose)、Lugduname、Carrelame、Sucrononate、Sucrooctate、Monatin),
·甜味道氨基酸(甘氨酸、D‐亮氨酸、D‐苏氨酸、D‐天门冬氨酸、D‐苯丙氨酸、D‐色氨酸、L‐脯氨酸),
·其他甜味道小分子物质,例如莱鲍迪苷、甜菊苷、罗汉果糖苷、甜菊糖苷元(hernandulcin)、叶甜素(phyllodulcin)、二氢查耳酮糖苷(dihydrochalconeglycosides)、甘草甜素(glycyrrhizin)、甘草甜酸铵盐或其他甘草甜酸衍生物,
·甜味道植物提取物,特别是罗汉果、绣球花(Hydrangea dulcis)或Stevia ssp.(例如甜菊)、甜茶叶(Rubus suavissimus)、欧亚多足蕨(Polypodium vulgare)、相思子(Abrus precatorius)、正青钱柳(Pterocarya paliurus)、戈迪绍旱地菊(Baccharisgaudichaudiana)、Albizia myriophylla、泻根(Bryonia dioica)、假秦艽(Phlomisbetonicoides)、肉花雪胆(Hemsleya carnosiflora)、甜舌草(Lippia dulcis)、绞股蓝(Gynostemma pentaphyllum)、或由这些植物分离的单独甜味道物质。
C.增稠剂
在本发明优选的口服消费产品(特别是食品、饲料或药品)中有利的增稠剂选自下组包括:交联聚丙烯酸及其衍生物、多糖及其衍生物,如黄原胶、琼脂、海藻酸盐或tyloses、纤维素衍生物,例如羧甲基纤维素和羟基羧甲基纤维素、脂肪醇、甘油单酯和脂肪酸、聚乙烯醇和聚乙烯吡咯烷酮。
根据本发明优选的口服消费产品(特别是食品或饲料)含有使用乳酸菌增稠的奶和/或使用乳酸菌增稠的奶油,并优选自组包括酸奶、克菲尔和夸克。
根据本发明的含有使用乳酸菌增稠奶和/或使用乳酸菌增稠奶油的食品组合物有利地是含有益生菌的口服消费产品,其中益生菌优选自组包括动物双歧杆菌乳亚种BB‐12、动物双歧杆菌乳亚种DN‐173 010、动物双歧杆菌乳亚种HN019、嗜酸乳杆菌LA5、NCFM、约氏乳酸杆菌La1、干酪乳酸杆菌immunitass/defensis、干酪乳酸杆菌代田菌(DSM 20312)、干酪乳酸杆菌CRL431、罗伊氏乳酸杆菌(ATCC 55730)和鼠李糖乳酸杆菌(ATCC 53013)。
D.口香糖添加剂
根据本发明特别优选的口服消费产品(特别是食品、饲料或药品)是口香糖并包括口香糖胶基。口香糖胶基优选自组包括口香糖或泡泡糖胶基。后者更软,从而可以形成泡泡。根据本发明优选的口香糖胶基,除了常规使用的天然树脂或latex树胶,包括弹性体如聚乙酸乙烯酯(PVA)、聚乙烯(低分子量和中等分子量)、聚异丁烯(PIB)、聚丁二烯、异丁烯‐异戊二烯共聚物(丁基橡胶)、聚乙烯基乙醚(PVE)、聚乙烯基丁醚、乙烯基酯和乙烯基醚的共聚物、苯乙烯‐丁二烯共聚物(苯乙烯‐丁二烯橡胶,SBR)或乙烯基弹性体,例如基于乙酸乙烯酯/月桂酸乙烯酯、乙酸乙烯酯/硬脂酸乙烯酯或乙酸亚乙酯/乙酸乙烯酯,及所述弹性体的混合物,例如如EP 0 242 325、US 4,518,615、US 5,093,136、US 5,266,336、US 5,601,858或US 6,986,709中所述。
此外,根据本发明优选的口香糖胶基还包含其他组分,例如(矿物)填料、增塑剂、乳化剂、抗氧化剂、蜡、脂肪或脂肪油,如硬化(氢化)植物或动物脂肪、甘油单酯、甘油二酯或甘油三酯。适合的(矿物)填料有例如碳酸钙、二氧化钛、二氧化硅、滑石、氧化铝、磷酸二钙、磷酸三钙、氢氧化镁及其混合物。适合的增塑剂或防粘剂(脱粘剂)是例如羊毛脂、硬脂酸、硬脂酸钠、乙酸乙酯、二醋精(二乙酸甘油酯)、三醋精(三乙酸甘油酯)、柠檬酸三乙酯。适合的蜡是例如石蜡、小烛树蜡、巴西棕榈蜡、微晶蜡和聚乙烯蜡。适合的乳化剂是例如磷脂如卵磷脂、脂肪酸的甘油单酯和甘油二酯,例如单硬脂酸甘油酯。
本发明的口香糖(特别是上文公开的)优选包含成分如不同类型的糖、糖替代品、其他甜味物质、糖醇(特别是山梨糖醇、木糖醇、甘露醇)、具有清凉效果的成分、令人不愉快味道印象的味道矫正剂、其他味道矫正物质(例如磷酸肌醇、核苷酸如单磷酸鸟苷、单磷酸腺苷或其他物质如谷氨酸钠或2‐苯氧基丙酸)、保湿剂、增稠剂、乳化剂、稳定剂、气味校正剂和香料(例如桉树‐薄荷脑、樱桃、草莓、葡萄柚、香草、香蕉、柑橘、桃、黑醋栗、热带水果、姜、咖啡、肉桂、(所述香料)与薄荷香料的结合以及单独的荷兰薄荷和辣薄荷)。特别优选的是香料与其他具有清凉、温暖和/或令人垂涎特性物质的结合。
E.维生素
在本发明的另一实施方案中,组合物可以含有维生素(成分e1)。维生素具有不同的生物化学功能。一些具备类激素作用作为矿物新陈代谢调节剂(例如维生素D),或细胞和组织生长以辅助酶作为催化剂在新陈代谢中的作用。及细胞分化的调节剂(例如维生素A的一些形式)。其他的是抗氧化剂(例如维生素E以及一定条件下的维生素C)。大部分维生素(例如B复合维生素)是酶辅因子的前体,因此维生素作为酶活动基的一部分与酶紧密相关:例如,生物素为酶的一部分,参与脂肪酸的产生。维生素作为辅酶也能够是与酶催化剂较弱相关,在分子间传递化学基团或电子的易于分离的分子。例如叶酸将各种形式的碳基团—甲基、甲酰基和亚甲基—运至细胞内。尽管在酶‐基料反应中的辅助作用是维生素最为已知的功能,微生物其他性能同样重要。在本发明中适当的维生素选自下组,包括:
·维生素A(视黄醇、视黄醛、β‐胡萝卜素)、
·维生素B1(硫胺素)、
·维生素B2(核黄素)、
·维生素B3(烟酸、烟酰胺)、
·维生素B5(苯多生酸)、
·维生素B6(吡哆醇、吡哆胺、吡哆醛)、
·维生素B7(生物素)、
·维生素B9(叶酸、亚叶酸)、
·维生素B12(氰钴胺、羟基钴铵、甲基钴铵)、
·维生素C(抗坏血酸)、
·维生素D(胆骨化醇))、
·维生素E(生育酚、生育三烯酚)和
·维生素K(叶绿基甲萘醌、四烯甲萘醌)。
优选的维生素是抗坏血酸和生育酚。
所述维生素在食品组合物中含量为约0.1至约0.5%体重量,并且优选约0.5至约1%体重量。
口服组合物
非食品口服组合物的典型实例包括用于清洁和保护牙齿的产品和清新口腔的产品。
本发明的口服组合物通常包括研磨体系(研磨或抛光剂),如例如二氧化硅、碳酸钙、磷酸钙、氧化铝和/或羟磷灰石、表面活性物质,如例如月桂基硫酸钠、月桂基肌氨酸钠和/或椰油酰胺丙基甜菜碱、保湿剂,如例如甘油和/或山梨糖醇、增稠剂,如例如羧甲基纤维素、聚乙二醇、角叉菜胶和或甜味剂,如例如糖精、用于令人不愉快味道印象的味道矫正剂、用于其它通常不是令人不愉快味道印象的味道矫正剂、调节味道物质(例如磷酸肌醇、核苷酸,如鸟苷单磷酸盐、腺苷单磷酸盐或其它物质,如谷氨酸钠或2‐苯氧基丙酸)、清凉活性化合物,如例如薄荷醇、薄荷醇衍生物(例如L‐乳酸薄荷酯、L‐烷基碳酸薄荷酯、薄荷缩酮、薄荷烷碳酸酰胺)、2,2,2‐三烷基乙酸酰胺(例如2,2‐二异丙基丙酸甲基酰胺)、icilin和icilin衍生物、稳定剂和活性化合物,如氟化钠、单氟磷酸钠、二氟化锡、氟化季铵盐、柠檬酸锌、硫酸锌、焦磷酸锡、二氯化锡、各种焦磷酸盐的混合物、三氯生、双氯苯双胍己烷、氯化十六烷基吡啶、乳酸铝、柠檬酸钾、硝酸钾、氯化钾、氯化锶、过氧化氢、芳香剂、碳酸氢钠和/或气味矫正剂。
包含根据本发明的口香糖形式的制剂或产品,或者特别是口腔护理口香糖含有口香糖胶基,其含有弹性体,如例如聚乙酸乙烯酯(PVA)、聚乙烯(低分子量和中等分子量)、聚异丁烯(PIB)、聚丁二烯、异丁烯‐异戊二烯共聚物(丁基橡胶)、聚乙烯基乙醚(PVE)、聚乙烯基丁醚、乙烯基酯和乙烯基醚的共聚物、苯乙烯‐丁二烯共聚物(苯乙烯‐丁二烯橡胶,SBR)或乙烯基弹性体,例如基于乙酸乙烯酯/月桂酸乙烯酯、乙酸乙烯酯/硬脂酸乙烯酯或乙酸亚乙酯/乙酸乙烯酯,及所述弹性体的混合物,例如如EP 0 242 325、US 4,518,615、US 5,093,136、US 5,266,336、US 5,601,858或US 6,986,709中所述。此外,口香糖胶基还包含其他组分,例如糖、糖替代品、甜味物质、特别是那些记载于WO 2009/21558的、(矿物)填料、增塑剂、乳化剂、抗氧化剂、蜡、脂肪或脂肪油,如硬化(氢化)植物或动物脂肪、甘油单酯、甘油二酯或甘油三酯。适合的(矿物)填料有例如碳酸钙、二氧化钛、二氧化硅、滑石、氧化铝、磷酸二钙、磷酸三钙、氢氧化镁及其混合物。适合的增塑剂或防粘剂(脱粘剂)是例如羊毛脂、硬脂酸、硬脂酸钠、乙酸乙酯、二醋精(二乙酸甘油酯)、三醋精(三乙酸甘油酯)、柠檬酸三乙酯。适合的蜡是例如石蜡、小烛树蜡、巴西棕榈蜡、微晶蜡和聚乙烯蜡。适合的乳化剂是例如磷脂如卵磷脂、脂肪酸的甘油单酯和甘油二酯,例如单硬脂酸甘油酯。
根据本发明的制剂或产品(特别是那些口腔护理制剂或产品形式的)优选还含有一种或多种香味和/或香料物质,如精油和提取物、酊剂和香膏,例如茴香醚、罗勒油、佛手柑油、苦杏仁油、樟脑油、香茅油、柠檬油;柠檬桉油、桉树油、茴香油、葡萄柚油、洋甘菊油、荷兰薄荷油、蒿子油、白柠檬油、橘子油、肉豆蔻油(特别是肉豆蔻花油)、没药油、丁香油、丁香花油、橙油、牛至油、欧芹(籽)油、辣薄荷油、迷迭香油、鼠尾草油(香鼠尾草油、达尔马提亚或西班牙鼠尾草油)、八角油、百里香油、香草精、桧油(特别是杜松子油)、冬青油、肉桂叶油、桂皮油及其馏分,或由其分离的成分。
特别有利是所述制剂或产品含有至少一种,优选2、3、4、5、6、7、8、9、10或更多种香料物质,其选自以下组:薄荷醇(优选左旋薄荷醇和/或消旋薄荷醇)、茴香脑、茴香醚、茴香醛、茴香醇、(外消旋)新薄荷醇、桉树脑(1,8‐桉树脑)、薄荷酮(优选L‐薄荷酮)、异薄荷酮(优选D‐异薄荷酮)、异胡薄荷醇、乙酸薄荷酯(优选L‐乙酸薄荷酯)、丙酸薄荷酯、香芹酮(优选(‐)‐香芹酮,任选作为荷兰薄荷油的组分)、水杨酸甲酯(任选作为冬青油的组分)、丁香酚乙酸酯、异丁香酚甲醚、β‐环高柠檬醛、丁香酚、异丁醛、3‐辛醇、二甲基硫醚、己醇、己醛、反式‐2‐己醛、顺式‐3‐己烯醇、4‐萜品醇、薄荷烯酮、里哪醇、乙酸8‐罗勒烯酯、异戊醇、异戊醛、α‐蒎烯、β‐蒎烯、苧烯(优选D‐苧烯,任选作为精油的组分)、薄荷酮、反式‐水合桧烯、薄荷呋喃、石竹烯、大根香叶烯D、肉桂醛、薄荷内酯、百里酚、γ‐辛内酯、γ‐壬内酯、γ‐癸内酯、(1,3E,5Z)‐十一烷三烯、2‐丁酮、甲酸乙酯、乙酸3‐辛酯、异戊酸异戊酯、顺式‐和反式‐乙酸香芹酯、对聚伞花素、大马酮、突厥酮、顺式‐氧化玫瑰、反式‐氧化玫瑰、葑醇、乙醛二乙缩醛、乙酸1‐乙氧基乙酯、顺式‐4‐庚烯醛、顺式‐茉莉酮、二氢茉莉酸甲酯、2'‐羟基苯丙酮、薄荷基甲基醚、乙酸桃金娘烯酯、2‐苯乙醇、异丁酸2‐苯乙酯、异戊酸2‐苯乙酯、香叶醇、橙花醇和绿花白千层醇。
药物组合物
根据本发明的药物组合物可以含有与上述食品和口服组合物类似的添加剂,如香味和香料物质。药物组合物可以进一步含有,油体或乳化剂以及特别是辅助药物活性制剂有利性能的助活性物。因此,食品组合物和药物组合物之间的界限是不定的并且应当了解一种应用中引用的成分同样推荐用于其他应用,而无需重复。
本发明的另一主题是式(I)的甜味化学物或含有至少一种式(I)的甜味化学物的制剂用于使施用至个体的组合物,如口服或食品或药物组合物变甜或增强甜味效果的用途。优选地,一种或多种式(I)化合物的用量为1重量ppm至2000重量ppm,基于组合物总量计和基于式(I)所有化合物总量计,如果使用了多于一种的式(I)化合物。更优选地,式(I)的甜味化合物的用量为10重量ppm至1000重量ppm,最优选20重量ppm至500重量ppm,基于组合物总量计和基于式(I)所有化合物总量计,如果使用了多于一种的式(I)化合物。
在另一优选实施方案中式(I)的甜味化学物或含有至少一种式(I)的甜味化学物的制剂用于在组合物中协同增效地增强甜味道物质的甜味。优选的式(I)化合物优选自组包括:
·化合物A
3,11‐二羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐羟基‐2‐甲庚‐3‐基氧基)‐4,5‐二羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇;
·化合物B
4,5‐二羟基‐2‐(2‐羟基‐2‐甲基‐6‐((4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇;
·化合物C
4,5‐二羟基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲庚‐2‐基)‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐3‐基氧基)‐4,5‐二羟基‐2‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇;
·化合物D
2‐(2‐(17‐(5‐(4,5‐二羟基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲庚‐2‐基)‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐3‐基氧基)‐4,5‐二羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇;
·化合物E
2‐(4,5‐二羟基‐2‐(2‐羟基‐2‐甲基‐6‐(4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇;
·化合物F
2‐((6‐(6‐(3‐(4,5‐二羟基‐6‐(羟甲基)‐3‐(3,4,5‐三羟基四氢‐2H‐吡喃‐2‐基氧基)四氢‐2H‐吡喃‐2‐基氧基)‐11‐羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐羟基‐2‐甲庚‐3‐基氧基)‐3,4‐二羟基‐5‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)四氢‐2H‐吡喃‐2‐基)甲氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇;
·化合物G
2‐(4,5‐二羟基‐2‐(3‐羟基‐2‐甲基‐6‐(4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐2‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇;
·化合物H
2‐羟基‐6‐(11‐羟基‐4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐甲庚‐3‐酮;
·化合物J
17‐(5‐(4,5‐二羟基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲庚‐2‐基)‐11‐羟基‐4,4,9,13,14‐五甲基‐4,7,8,9,10,11,12,13,14,15,16,17‐十二氢‐1H‐环戊二烯并[a]菲‐3(2H)‐酮;
·化合物K
2‐(4,5‐二羟基‐2‐(2‐羟基‐6‐(3‐羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐甲庚‐3‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇;
·化合物L
17‐(5‐(4,5‐二羟基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲庚‐2‐基)‐4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐3,4,7,8,9,10,12,13,14,15,16,17‐十二氢‐1H‐环戊二烯并[a]菲‐11(2H)‐one;
·化合物M
2‐(4,5‐二羟基‐2‐(2‐羟基‐2‐甲基‐6‐(4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇;
其中最优选给出的(Aa)至(Mm)的异构体形式。
本发明的其他主题是含有一种或多种式(I)化合物的提取物
其中R1、R2、R3相互独立并且代表氢、羟基、羰基
或者
选自单糖和/或低聚糖的糖配基,
其中该提取物可通过水和/或醇提取选自组包括罗汉果的植物材料的方法得到。
在本文中“植物材料”是指罗汉果各个植物部分。该植物材料包括选自组包括花、果实、芽、根、种子和/或叶的整个植物的部分或整个植物自身。
该提取物含有至少一种选自组包括化合物A、B、C、D、E、F、G、H、J、K、L、M或其混合物的式(I)化合物,
其中最优选已经列出的异构体形式(Aa)至(Mm)。
更优选地,该提取物含有至少两种、三种、四种、五种、六种、七种、八种、九种、十种或十一种式(I)化合物。优选地,该提取物含有所有式(I)的化合物I至XII,特别是已经列出的所有异构体形式(Aa)至(Mm)。
提取
根据本发明的提取物可以由本身已知的方法制备,即例如通过水、醇或水/醇提取植物或其部分或果壳。适当的提取方法是任何常规提取方法,如浸渍法、再浸渍法、消化法、搅拌浸渍法、涡流提取法、超声提取法、逆流提取法、渗滤法、再渗滤法、减压提取法、渗透萃取法和连续的固体/液体提取法。渗滤法有利于工业用途。优选使用荔枝壳作为初始原料并可以在提取步骤前机械地减小尺寸。可以使用任何专业人员已知的尺寸减小方法,例如冷冻研磨。用于提取步骤的优选溶剂是有机溶剂、水(优选温度高于80℃的热水并且特别是高于95℃或有机溶剂与水的混合物,更特别是低分子醇与高含量水的混合物)。特别优选使用甲醇、乙醇、异丙醇及其含水混合物进行提取。提取步骤通常在约20至约100℃并且优选在约50至约70℃下进行。在一个优选实施方案中,提取步骤在惰性气氛中进行以防止提取物成分的氧化。当提取在高于40℃的温度下进行时这点特别重要。可以根据初始材料、提取步骤、提取温度以及溶剂与原料的比例等选择提取时间。在提取步骤后,得到的粗提取物可以任选进行其他典型步骤,如例如纯化、浓缩和/或脱色。如果需要,由此制得的提取物可以进行例如选择性地移除单个不想要的成分。提取步骤可以进行至任意程度,但是通常持续至耗尽。初始材料提取的典型产率(=提取干物质,基于使用原料用量计)为约1至约20%,优选约2至约15并且更优选约5至约10%体重量—基于原料计。
根据使用的罗汉果果实原料提取物中化合物(A)至(M)含量每批都不相同。通常罗汉果提取物中主要的三萜苷是罗汉果糖苷V(CAS 88901‐36‐4),相对占三萜苷总量的50至90%。化合物(A)至(M)通常占罗汉果三萜苷总量的0.01至5%。
此外,本发明涉及一种为组合物,如食品或口服或药物组合物提供甜味效果和/或增强甜味效果的方法,包括向个体施用至少一种式(I)的甜味化合物或含有至少一种式(I)化合物的制剂或含有至少一种式(I)化合物的提取物。
优选的食品组合物是,例如糕点,如巧克力、口香糖、硬焦糖和乳基产品,如酸奶、白脱牛奶、奶酪、冰淇淋和饮料,如非酒精饮品、清凉饮料、含水果饮料和烘焙产品,以及肉制品,如香肠和谷类产品,如麦片、早餐谷物,以及水果制品,如果酱、果汁冰糕、水果蜜饯和半成产品。可能的应用并不限于提到的应用,而仅用于说明。可以将式(I)的甜味化合物提供给各种产品,从而提供甜味。
此外,本发明优选地涉及一种使用式(I)的甜味化合物协同增效地提高甜味道物质的甜味的方法。
本发明同样优选地涉及一种赋予或增强口服组合物甜味的方法,包括向其加入用量为约1ppm至约2000ppm的一种或多种式(I)化合物。
工业应用
更特别地,本发明也涉及一种口服可食用组合物,含有一种可食用物质和足以产生想要甜度的有效量的至少一种式(I)化合物
其中R1、R2、R3相互独立并且代表氢、羟基、羰基或选自组包括单糖和/或低聚糖的糖配基。
该有效量优选为1ppm至2000ppm(基于可食用物质),更优选10重量ppm至1000重量ppm,最优选20重量ppm至500重量ppm,基于组合物的总重量和式(I)所有化合物总量计。
优选的可食用组合物是已经描述的优选食品组合物。
此外,式(I)化合物适合在可食用组合物中作为甜味剂。
本发明进一步由以下实施例描述。这些实施例用于说明发明并且不构成对发明范围的限制。
此外,本发明涉及一种制剂,含有一种、两种、三种或更多种式(I)的甜味化合物,其中该制剂任选进一步含有香味化合物和/或香料制剂和/或甜味剂和/或甜味道物质。
该制剂优选是一种口服可食用组合物。
实施例
以下实施例用于说明本发明而不限制发明。除非另外指出所有用量、部分和百分比都是基于总重和总量或制剂的总重和总量。
实施例1
提取和确定式(I)的化合物
A)提取
在室温下,使用18l甲醇‐甲基叔丁基醚提取由德国Cfm Oskar Tropitzsch,Marktredwitz提供的2kg罗汉果干燥果实24小时(产量:275g提取物)。在室温下,使用10l甲醇提取由中国DAXINGANLING SNOW LOTUS HERB BIO‐TECHNOLOGY CO.,LTD.提供的1kg罗汉果干燥果实24小时(产量:310g提取物)。
B)富集
为了移除常见糖类将粗提取物溶解于5l水‐甲醇(9:1)并加入500ml吸收树脂HP‐20。用水洗涤过滤树脂以洗脱不想要的极性成分。使用甲醇洗脱产生37g三萜苷混合物。
C)通过常规相色谱法进行预分馏
得到的B)馏分随后在以下条件下通过中压色谱分离:
·固相:氧化硅60(Merck)
·移动相溶剂A:CHCl3–甲醇–水1680:720:120
·移动相溶剂B:CHCl3–甲醇–水1350:900:225
·梯度:40分钟100%A至50%A,10分钟50%A,10分钟90%甲醇–10%水
·柱直径:50x250mm
如下表C所示收集7个馏分并蒸发
表C
馏分
馏分 | 体积[ml] | 产量[g] |
C‐1780‐A | 150 | 5.85 |
C‐1780‐B | 220 | 4.72 |
C‐1780‐C | 450 | 3.85 |
C‐1780‐D | 550 | 2.96 |
C‐1780‐E | 410 | 2.08 |
C‐1780‐F | 500 | 2.32 |
C‐1780‐G | 550 | 13.38 |
D)通过反相色谱法进行预分馏
在以下条件下通过反相中压色谱分离300g罗汉果粗提取物:
富集三萜苷馏分的分离条件:
·固定相:RP‐18,40‐63μ(Merck)
·移动相溶剂A:水
·移动相溶剂B:甲醇
·柱直径:50x250mm
如下表D所示收集7个馏分:
表D
馏分
馏分 | 体积[ml] | 产量[g] |
H‐1714‐B | 3000 | 54.06 |
H‐1714‐C | 3000 | 32.52 |
H‐1714‐D | 3000 | 36.69 |
H‐1714‐E | 3000 | 36.87 |
H‐1714‐F | 3000 | 11.25 |
H‐1714‐G | 3000 | 3.57 |
H‐1714‐I | 3000 | 0.96 |
E)通过反相色谱最终纯化
使用由步骤D)描述的预分馏步骤产生的富集馏分通过反相色谱分离纯化合物。
表1
C‐1780‐C的分离条件
固定相 | LichrospherSelect B.10μm |
移动相溶剂A | 水+5mM甲酸铵+0.1%甲酸 |
移动相溶剂B | 乙腈/甲醇=1:1+5mM甲酸铵+0.1%甲酸铵 |
流速 | 80ml/分钟 |
梯度 | 57分钟36‐65%B |
检测 | ELSD和UV |
柱直径 | 50x250mm |
使用的预分馏样品 | 3.85g C‐1780‐C |
表2
C‐1780‐D的分离条件
固定相 | LichrospherSelect B.10μm |
移动相溶剂A | 水+5mM甲酸铵+0.1%甲酸 |
移动相溶剂B | 乙腈/甲醇=1:1+5mM甲酸铵+0.1%甲酸 |
流速 | 80ml/分钟 |
梯度 | 57分钟32–50%B |
检测 | ELSD和UV |
柱直径 | 50x250mm |
使用的预分馏样品 | 2.96g C‐1780‐D |
表3
C‐1780‐E的分离条件
固定相 | LichrospherSelect B.10μm |
移动相溶剂A | 水+5mM甲酸铵+0.1%甲酸 |
移动相溶剂B | 乙腈/甲醇=1:1+5mM甲酸铵+0.1%甲酸 |
流速 | 80ml/分钟 |
梯度 | 57分钟32–50%B |
检测 | ELSD和UV |
柱直径 | 50x250mm |
使用的预分馏样品 | 2.08g C‐1780‐E |
表4
C‐1780‐F的分离条件
固定相 | LichrospherSelect B.10μm |
移动相溶剂A | 水+5mM甲酸铵+0.1%甲酸 |
移动相溶剂B | 乙腈/甲醇=1:1+5mM甲酸铵+0.1%甲酸 |
流速 | 80ml/分钟 |
梯度 | 57分钟29–49%B |
检测 | ELSD和UV |
柱直径 | 50x250mm |
使用的预分馏样品 | 2.32g C‐1780‐F |
表5
H‐1949‐G的分离条件
固定相 | LichrospherSelect B.10μm |
移动相溶剂A | 水+5mM甲酸铵+0.1%甲酸 |
移动相溶剂B | 乙腈/甲醇=1:1+5mM甲酸铵+0.1%甲酸 |
流速 | 80ml/分钟 |
梯度 | 57分钟35–50%B |
检测 | ELSD和UV |
柱直径 | 50x250mm |
使用的预分馏样品 | 0.57g H‐1714‐G |
表6
C‐1750‐N的分离条件
固定相 | Kromasil C‐18 |
移动相溶剂A | 水+0.1%甲酸 |
移动相溶剂B | 乙腈+0.1%甲酸 |
流速 | 80ml/分钟 |
梯度 | 57分钟20–37%B |
检测 | ELSD和UV |
柱直径 | 50x250mm |
使用的预分馏样品 | 1.3g H‐1714‐F |
表7
C‐1743‐A的分离条件
固定相 | Kromasil C‐18 |
移动相溶剂A | 水+5mM甲酸铵+0.1%甲酸 |
移动相溶剂B | 甲醇=1:1+5mM甲酸铵+0.1%甲酸 |
流速 | 80ml/分钟 |
梯度 | 57分钟53–62%B |
检测 | ELSD和UV |
柱直径 | 50x250mm |
使用的预分馏样品 | 2.08g H‐1714‐F |
表8
H‐1714‐G的分离条件
固定相 | Kromasil C‐18 |
移动相溶剂A | 水+0.1%甲酸 |
移动相溶剂B | 乙腈+0.1%甲酸 |
流速 | 80ml/分钟 |
梯度 | 57分钟20–37%B |
检测 | ELSD和UV |
柱直径 | 50x250mm |
使用的预分馏样品 | 1.3g H‐1714‐F |
F)分离的三萜苷的分析表征
收集制备HPLC的馏分(各40ml)并使用HPLC‐MS分析。根据保留时间和质谱将含有相同化合物的馏分结合,蒸发并使用HPLC‐MS和NMR(1H‐NMR.HH‐COSY.HSQC.HMBC)分析。通过分析NMR和MS数据说明结构。
表9
分离化合物的HPLC‐MS的条件
G)定性:化合物的分析表征
式(I)的分离化合物通过质谱和NMR谱表征,参见图1至24。化合物定性为:
化合物Aa
化合物Bb
化合物Cc
化合物Dd
化合物Ee
化合物Ff
化合物Gg
化合物Hh
化合物Jj
化合物Kk
化合物Ll
化合物Mm
实施例2
式(I)化合物相对于蔗糖和罗汉果糖苷V的感官测试
将分离的纯化合物以浓度0.4mg/ml(400ppm)溶解于无碳酸矿泉水(“FonsanaQuelle”)。各个样品的甜味道由4名小组成员构成的小组与浓度为20mg/ml的蔗糖溶液以及浓度为0.1mg/ml(100ppm)的已知甜味剂罗汉果糖苷V的溶液(AnalytiCon由罗汉果分离)进行比较。
甜度评估如下:
3=比对比溶液甜
2=与对比溶液甜度相同
1=没有对比溶液甜,但仍然甜
表10
感官评估
化合物 | 与蔗糖相比* | 与罗汉果糖苷V相比* |
Aa | 3 | 2 |
Bb | 3 | 3 |
Cc | 3 | 3 |
Dd | 3 | 3 |
Ee | 3 | 3 |
Ff | 3 | 2 |
Gg | 3 | 3 |
Hh | 2 | 1 |
Jj | 3 | 2 |
Kk | 2 | 1 |
Ll | 3 | 3 |
Mm | 3 | 3 |
实施例3
制剂实施例
下表11至14提供了含有至少一种上文公开的甜味剂的口服制剂的一些实例
表11
口香糖,无糖,所有含量以%体重量计
表12
牙膏,所有用量以%体重量计
表13
漱口水浓缩物,所有用量以%体重量计
表14
硬糖,不含糖,所有用量以%体重量计
Claims (15)
1.一种式(I)的甜味化合物
其中R1、R2、R3相互独立并且代表氢、羟基、羰基或选自组包括单糖和/或低聚糖的糖配基,
其中单糖和/或低聚糖的单糖单元选自组包括果糖、葡萄糖、蔗糖、木糖、麦芽糖、甘露糖、鼠李糖、半乳糖、乳糖、龙胆二糖、槐糖、2‐吡喃葡萄糖基‐葡萄糖、吡喃葡萄糖基‐(1‐2)‐[吡喃葡萄糖基‐(1‐6)]‐吡喃葡萄糖、纤维二糖、甘露醇、山梨糖醇、木糖醇或阿拉伯糖醇、葡糖醛酸、异鼠李糖、阿拉伯吡喃糖、阿拉伯呋喃糖、吡喃木糖、呋喃木糖和/或芹菜糖(2,3,4‐三羟基‐3‐(羟甲基)丁醛),并且
其中低聚糖由2至5个单糖单元构成。
2.根据权利要求1所述的式(I)的化合物,其中
R1和R2相互独立并且代表羟基或选自单糖和/或低聚糖的糖配基,
其中单糖和/或低聚糖的单糖单元选自组包括葡萄糖、2‐吡喃葡萄糖基‐葡萄糖、3‐吡喃葡萄糖基‐葡萄糖、4‐吡喃葡萄糖基‐葡萄糖、6‐吡喃葡萄糖基‐葡萄糖、或吡喃葡萄糖基‐(1→2)‐[吡喃葡萄糖基‐(1→6)]‐葡萄糖,并且
其中在低聚糖情况下,低聚糖的单糖单元通过糖苷键相互连接,并且
R3代表氢、羟基或羰基。
3.根据权利要求1或2所述的式(I)化合物,其中
R2是具备两个单糖单元的低聚糖(二糖)时,R2二糖的单糖单元通过糖苷键连接,其不是1→6连接。
4.根据权利要求1至3任一项所述的式(I)化合物,其中
R2是具备两个单糖单元的低聚糖(二糖),并且
R3代表氢或羰基。
5.根据权利要求1至3任一项所述的式(I)化合物,其中
R1代表氢、羟基、羰基或具备2、3、4或5个单糖单元的低聚糖,并且
R2是具备两个单糖单元的低聚糖(二糖),并且
R3代表羟基。
6.根据权利要求1或2所述的式(I)化合物,其中
R2是具备三个单糖单元的低聚糖(三糖)时,则
R1是羰基和/或
R3不是羟基或羰基或者
R3是羟基并且R1是具备2、4或5个单糖单元的低聚糖,其中R1低聚糖的单糖单元通过不是1→6或1→4连接的糖苷键连接。
7.根据权利要求1至4任一项所述的式(I)化合物,其中
R1是单糖或具备至少三个单糖单元的低聚糖,和
R2是具备三个单糖单元的低聚糖(三塘),并且
R3是羰基。
8.根据权利要求1至5任一项所述的式(I)化合物,其中R1是具备2、4或5个单糖单元,但不是三个单糖单元的低聚糖。
9.根据权利要求1或2所述的式(I)化合物,其中R2是具备2至5个单糖单元的低聚糖,但不是单糖。
10.根据权利要求1至4任一项所述的式(I)化合物,其中
R2是羰基,则
R3不是羰基或者
R3是羟基。
11.根据权利要求1至10任一项所述的式(I)的甜味化合物,其中式(I)化合物选自组包括
‐3,11‐二羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐羟基‐2‐甲庚‐3‐基氧基)‐4,5‐二羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物A);
‐,5‐二羟基‐2‐(2‐羟基‐2‐甲基‐6‐((3S)‐4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物B);
‐4,5‐二羟基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲庚‐2‐基)‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐3‐基氧基)‐4,5‐二羟基‐2‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物C);
‐2‐(2‐(17‐(5‐(4,5‐二羟基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲庚‐2‐基)‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐3‐基氧基)‐4,5‐二羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物D);
‐2‐(4,5‐二羟基‐2‐(2‐羟基‐2‐甲基‐6‐(4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物E);
‐2‐((6‐(6‐(3‐(4,5‐二羟基‐6‐(羟甲基)‐3‐(3,4,5‐三羟基四氢‐2H‐吡喃‐2‐基氧基)四氢‐2H‐吡喃‐2‐基氧基)‐11‐羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐羟基‐2‐甲庚‐3‐基氧基)‐3,4‐二羟基‐5‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)四氢‐2H‐吡喃‐2‐基)甲氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物F);
‐2‐(4,5‐二羟基‐2‐(3‐羟基‐2‐甲基‐6‐(4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐2‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物G);
‐2‐羟基‐6‐(11‐羟基‐4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐甲庚‐3‐酮(化合物H);
‐17‐(5‐(4,5‐二羟基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲庚‐2‐基)‐11‐羟基‐4,4,9,13,14‐五甲基‐4,7,8,9,10,11,12,13,14,15,16,17‐十二氢‐1H‐环戊二烯并[a]菲‐3(2H)‐酮(化合物J);
‐2‐(4,5‐二羟基‐2‐(2‐羟基‐6‐(3‐羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐甲庚‐3‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物K);
‐17‐(5‐(4,5‐二羟基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲庚‐2‐基)‐4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐3,4,7,8,9,10,12,13,14,15,16,17‐十二氢‐1H‐环戊二烯并[a]菲‐11(2H)‐酮(化合物L);
‐2‐(4,5‐二羟基‐2‐(2‐羟基‐2‐甲基‐6‐(4,4,9,13,14‐五甲基‐3‐(3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐((3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物M)。
12.一种制剂,含有一种、两种、三种或更多种根据权利要求1至11所述的式(I)的甜味化合物,其中该制剂任选进一步含有香味化合物和/或香料制剂和/或甜味剂和/或甜味道物质。
13.根据权利要求1至11所述的式(I)的甜味化合物或根据权利要求12所述的制剂用于使组合物变甜或增强甜味效果的用途,其中将足以产生想要甜度的有效量的式(I)的甜味化合物或制剂施用于个体。
14.一种含有一种或更多种根据权利要求1至11所述的式(I)化合物的提取物,其中该提取物通过水和/或醇提取植物罗汉果的方法得到。
15.根据权利要求14所述的提取物,含有至少一种式(I)化合物,选自组包括:
‐(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐2‐((3R,6R)‐6‐((3S,8S,9R,11R,13R,14S,17R)‐3,11‐二羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐羟基‐2‐甲庚‐3‐基氧基)‐4,5‐二羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Aa)
‐(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐2‐((3R,6R)‐2‐羟基‐2‐甲基‐6‐((3S,9R,13R,14S,17R)‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Bb)
‐(2S,3R,4S,5S,6R)‐2‐((2R,3S,4R,5R,6R)‐6‐((3S,9R,13R,14S,17R)‐17‐((2R,5R)‐5‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐3‐((2S,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲庚‐2‐基)‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐3‐基氧基)‐4,5‐二羟基‐2‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Cc)
‐(2S,3R,4S,5S,6R)‐2‐((2R,3R,4S,5S,6R)‐2‐((3S,8R,9R,13R,14S,17R)‐17‐((2R,5R)‐5‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐3‐((2S,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲庚‐2‐基)‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐3‐基氧基)‐4,5‐二羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Dd)
‐(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐2‐((3R,6R)‐2‐羟基‐2‐甲基‐6‐((3S,8R,9R,13R,14S,17R)‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Ee)
‐(2S,3R,4S,5S,6R)‐2‐((2R,3R,4S,5S,6R)‐2‐((3S,8S,9R,11R,13R,14S,17R)‐17‐((2R,5R)‐5‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐3‐((2S,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲庚‐2‐基)‐11‐羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐3‐基氧基)‐4,5‐二羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Ff)
‐(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐2‐((3R,6R)‐2‐羟基‐2‐甲基‐6‐((3S,9R,13R,14S,17R)‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Gg)
‐(6R)‐2‐羟基‐6‐((3S,9R,10R,11R,13R,14S,17R)‐11‐羟基‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐甲庚‐3‐酮(化合物Hh)
‐(9R,10R,11R,13R,14S,17R)‐17‐((2R,5R)‐5‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐3‐((2S,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲庚‐2‐基)‐11‐羟基‐4,4,9,13,14‐五甲基‐4,7,8,9,10,11,12,13,14,15,16,17‐十二氢‐1H‐环戊二烯并[a]菲‐3(2H)‐酮(化合物Jj)
‐(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐2‐((3R,6R)‐2‐羟基‐6‐((3S,9R,10S,13R,14S,17R)‐3‐羟基‐4,4,9,13,14‐五甲基‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)‐2‐甲庚‐3‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Kk)
‐(3S,9R,10R,13R,14S,17R)‐17‐((2R,5R)‐5‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐3‐((2S,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐2‐基氧基)‐6‐羟基‐6‐甲庚‐2‐基)‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐3,4,7,8,9,10,12,13,14,15,16,17‐十二氢‐1H‐环戊二烯并[a]菲‐11(2H)‐one(化合物Ll)
‐(2S,3R,4S,5S,6R)‐2‐((2S,3R,4S,5S,6R)‐4,5‐二羟基‐2‐((3R,6R)‐2‐羟基‐2‐甲基‐6‐((3S,9R,10S,13R,14S,17R)‐4,4,9,13,14‐五甲基‐3‐((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐十四氢‐1H‐环戊二烯并[a]菲‐17‐基)庚‐3‐基氧基)‐6‐(((2R,3R,4S,5S,6R)‐3,4,5‐三羟基‐6‐(羟甲基)四氢‐2H‐吡喃‐2‐基氧基)甲基)四氢‐2H‐吡喃‐3‐基氧基)‐6‐(羟甲基)四氢‐2H‐吡喃‐3,4,5‐三醇(化合物Mm)。
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CN111108213A (zh) * | 2017-05-03 | 2020-05-05 | 弗门尼舍公司 | 制备高强度甜味剂的方法 |
CN112334012A (zh) * | 2018-04-23 | 2021-02-05 | 可口可乐公司 | 新型罗汉果苷、获得新型罗汉果苷的方法及用途 |
CN113646321A (zh) * | 2019-02-26 | 2021-11-12 | 可口可乐公司 | 新颖的罗汉果苷及其用途 |
CN114127084A (zh) * | 2020-03-05 | 2022-03-01 | 弗门尼舍有限公司 | 11-氧代-葫芦烷及其作为风味改良剂的用途 |
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EP2970370B1 (en) | 2013-03-15 | 2019-12-04 | The Coca-Cola Company | Novel mogrosides, compositions and purification methods |
EP3108754B1 (en) * | 2015-06-24 | 2019-01-30 | Analyticon Discovery GmbH | Novel triterpene glycosides as sweeteners or sweetener enhancer |
BR112018008710B1 (pt) | 2015-10-29 | 2022-04-12 | Firmenich Incorporated | Adoçantes de alta intensidade |
MX2019003086A (es) | 2016-09-16 | 2019-11-18 | Pepsico Inc | Composiciones y metodos para mejorar el sabor de edulcorantes no nutritivos. |
SG11201809025YA (en) * | 2017-03-01 | 2018-11-29 | Guilin Layn Natural Ingredients Corp | Method for increasing content of mogroside v in siraitia grosvenorii suspended cells |
EP3461349B1 (en) | 2017-09-27 | 2020-12-09 | Analyticon Discovery GmbH | Novel diterpene glycosides as sweeteners or sweetener enhancer |
EP3501296A1 (en) | 2017-12-22 | 2019-06-26 | Analyticon Discovery GmbH | Novel triterpene-glycosides as sweeteners or sweetener enhancer |
JP6814182B2 (ja) * | 2018-09-10 | 2021-01-13 | アナリティコン ディスカバリー ゲーエムベーハー | 甘味料または甘味増強剤として使用される新規なトリペルテングリコシド |
JP2022514177A (ja) * | 2018-11-08 | 2022-02-10 | ミドリ ユーエスエー,インコーポレーテッド | オリゴ糖調製物を定量する方法 |
WO2020200916A1 (en) | 2019-04-04 | 2020-10-08 | Firmenich Sa | Mogroside compounds and uses thereof |
EP3858155A1 (en) * | 2020-01-30 | 2021-08-04 | Analyticon Discovery GmbH | A sweetener or sweetness enhancer composition |
GB202013491D0 (en) * | 2020-08-27 | 2020-10-14 | Nicoventures Holdings Ltd | Oral Product |
WO2023131545A1 (en) | 2022-01-07 | 2023-07-13 | BRAIN Biotech AG | A sweetener or sweetness enhancer composition |
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CN111108213A (zh) * | 2017-05-03 | 2020-05-05 | 弗门尼舍公司 | 制备高强度甜味剂的方法 |
CN112334012A (zh) * | 2018-04-23 | 2021-02-05 | 可口可乐公司 | 新型罗汉果苷、获得新型罗汉果苷的方法及用途 |
CN110790806A (zh) * | 2018-08-01 | 2020-02-14 | 中国药科大学 | 新型罗汉果苷衍生物及其用途 |
CN110790806B (zh) * | 2018-08-01 | 2021-10-29 | 中国药科大学 | 新型罗汉果苷衍生物及其用途 |
CN113646321A (zh) * | 2019-02-26 | 2021-11-12 | 可口可乐公司 | 新颖的罗汉果苷及其用途 |
CN114127084A (zh) * | 2020-03-05 | 2022-03-01 | 弗门尼舍有限公司 | 11-氧代-葫芦烷及其作为风味改良剂的用途 |
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US10472385B2 (en) | 2019-11-12 |
CN105848496B (zh) | 2021-02-23 |
AU2019200938B2 (en) | 2020-07-30 |
EA030673B1 (ru) | 2018-09-28 |
WO2015082012A1 (en) | 2015-06-11 |
CA2931536A1 (en) | 2015-06-11 |
BR112016012682A2 (pt) | 2017-08-08 |
AU2019200938A1 (en) | 2019-02-28 |
BR112016012682B1 (pt) | 2021-12-07 |
AU2013407055A1 (en) | 2016-06-09 |
US20200017541A1 (en) | 2020-01-16 |
US20170029458A1 (en) | 2017-02-02 |
JP2016540507A (ja) | 2016-12-28 |
US10808004B2 (en) | 2020-10-20 |
KR20160093704A (ko) | 2016-08-08 |
MX2016007178A (es) | 2016-09-29 |
EP3099186B1 (en) | 2021-05-19 |
EA201690900A1 (ru) | 2017-03-31 |
CA2931536C (en) | 2021-08-31 |
EP3099186A1 (en) | 2016-12-07 |
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