CN101081858A - 类黄酮糖加成产物、生产方法及其应用 - Google Patents
类黄酮糖加成产物、生产方法及其应用 Download PDFInfo
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- CN101081858A CN101081858A CNA2007101266587A CN200710126658A CN101081858A CN 101081858 A CN101081858 A CN 101081858A CN A2007101266587 A CNA2007101266587 A CN A2007101266587A CN 200710126658 A CN200710126658 A CN 200710126658A CN 101081858 A CN101081858 A CN 101081858A
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- catechin
- flavonoid
- sugar
- adduct
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- A—HUMAN NECESSITIES
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- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
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- A—HUMAN NECESSITIES
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- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
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- A—HUMAN NECESSITIES
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Landscapes
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Abstract
本发明涉及一种类黄酮糖加成产物及其制造方法。还涉及这些加成产物在修饰食物产品味道中的应用。
Description
本申请涉及类黄酮糖加成产物、它们的生产方法和其应用。
类黄酮以及它们的聚合物组成了一类营养组分，其改变了代谢过程并且对健康有积极的影响。因此，类黄酮作为营养组分或食品添加剂吸引了极大的关注。
虽然类黄酮提供了多种健康益处，但是含有类黄酮的食物经常受到苦或涩的味道的困扰。这可以通过将食物进行处理以使其含有较少的类黄酮而得到补偿。例如，在EP-A 1 106 073中公开了处理可可粉以除去或抑制这样的苦和涩味道特性的方法。此方法注意到了含水率并且提出碱性化和焙烧。JP-A 11318338公开了一种基于压力和热处理同时使用碱的方法。虽然这些方法在苦和涩味方面得到了较好的味道，但是基本上牺牲了类黄酮以及因此与之相关联的健康益处。
在一个替代方法中，人们还可以通过加入各种化合物例如甜味剂和/或脂肪组分来掩饰苦和涩的味道。在EP-B 1 364 584(油/脂肪修饰)中公开了含有功能成分的味道修饰硬糖组合物。多种其它的苦/涩味道改性剂描述于US-A 20030003212(奎宁酯和肉桂酯)、US-A 20030008046(纽甜(neotame))、WO02/100192(绿原酸)、JP-A 58162260(阿斯巴甜(aspartame)的分解产物)、P-A 10248501(甜味剂)、US 5,562,941(硫代硫酸盐)、US 3,753,726(酸)、WO04/093571(植物甾醇酯)、US 4,183,965(环四癸-1-酮)、JP-A 08298930(糊精、环糊精、淀粉和环麦芽糊精葡萄糖基转移酶)、WO 96/01568A1(杜仲橡胶叶和人参)中。然而，这些组分不仅改变了产品的特征，而且它们可能根本不是产品所希望的组分。
因此，值得注意的是现有技术没有提供不改变产品的特征或损害它们的特性而克服苦和涩味道的令人满意的解决办法。
本发明基于如下惊人的发现，即特定的类黄酮糖加成产物可以掩饰苦和涩的味道符号。出乎意料地，这些化合物将多种产品的味道曲线向更少涩味和更淡的方向修饰。多种类黄酮例如儿茶素或表儿茶素是苦和涩的，而本发明的化合物以直接相反的方式作用并且逆转苦和涩的味道特性，考虑到这样的事实，这种感觉上的影响甚至更加出人意料和令人惊奇。因此，新化合物对于食用制品、药物制品和与口腔接触的化妆品(即牙膏、漱口剂)中的涩和苦味来说是有效的味道改性剂。味道的强度和味道曲线的感觉都通过所述新化合物而得到改善。
所述化合物提供了作为调味制品或成分以获得较少苦和/或涩味产品的机会。所述化合物可以这样使用或者更有利地在制品或来自富含类黄酮食品的提取物中使用。所述提取物是本发明的一个优选实施方式。虽然其它减少涩味的方法牺牲了类黄酮和由此它们带来的抗氧化能力，但是本发明仍保持了成分、制品或食品的抗氧化能力，即使类黄酮已经变成糖加成产物。本发明的糖加成产物不仅给予食物、药物制品或化妆品优良的味道特性，而且更有利地还增加了制品、成分和可食用的食品的抗氧化能力。
本发明还公开了制备该加成产物的方法。
类黄酮糖衍生物由例如EP A 1 260 517、JP-A07179489、JP-A05176786和JP-A2001046096而已知。所有这些参考文献都涉及O-糖苷。这些类黄酮O-糖苷制品的已知用途在US 4,906,480(甜味剂和增香剂)、JP-A 2001240532(化妆品)和JP-A 08217674(组氨酸脱羧酶抑制剂)中被公开。
类黄酮是多酚的亚类。它们通常由两个芳环组成，每一个含有至少一个羟基基团。这两个环通过形成六元杂环部分的三碳“桥”连接。类黄酮进一步被分成基于芳环到杂环的连接以及杂环氧化态和官能团的亚类。在每个亚类中，单独的化合物的特征在于具体的羟基化和共轭模式。
一般地，食物中的类黄酮具有如下所示的三环(A、B和C)和标号模式的通式结构：
取代基R3到R6可以代表氢或例如羟基、氧代基和C1到C6直链或支链烷基的各种基团。对于大部分食物类黄酮来说，R4’和R6代表氢原子而R5代表羟基。在鹰嘴豆芽素A(biochanin A)中R4’代表甲基；在芒柄花黄素(formononetin)中R4’也代表甲基而R5和R6代表氢原子；在染料木素(glycetein)中R5代表氢原子而R6代表羟基。
C-环也可以是不饱和的并且含有进一步的官能团。B和C环之间的连接可以在2或3位。
食物中类黄酮糖苷配基的结构多样性显示在第5页的表中。这样的化合物经常以O-糖基化类黄酮的形式被发现，这进一步增加了结构的多样性。
一些比较主要的食物类黄酮和它们的结构特征总结在下表中：
| 类黄酮亚类 | B/C环连接 | C-环不饱和 | C-环官能团 | 主要的食物类黄酮 | 一般来源 |
| 黄烷醇 | 2 | - | 3-OH3-O-没食子酸盐 | (+)-儿茶素(+)-没食子儿茶素(-)-表儿茶素(-)-表没食子儿茶素(-)-表儿茶素-3-没食子酸酯(-)-表没食子儿茶素-3-没食子酸酯原花青素(proanthocyanidins)，例如原花青定(pyrocyanidin)B1、B2、B5和C1 | 茶、红葡萄和红葡萄酒 |
| 黄烷酮 | 2 | - | 4-氧代 | 圣草酚(Eriodictoyl)橙皮苷(Hesperitin)4’，5，7-三羟黄烷酮(Naringenin) | 柑橘类的水果 |
| 黄酮 | 2 | 2-3双键 | 4-氧代 | 芹菜素(Apigenin)木犀草素(Luteolin) | 绿色阔叶物种(例如欧芹) |
| 异黄酮 | 3 | 2-3双键 | 4-氧代 | 大豆黄酮(Daidzein)染料木黄酮(Genistein)大豆黄素(Glycitein)鹰嘴豆芽素A(BiochaninA)芒柄花黄素(Formononentin) | 大豆、大豆食品和豆类 |
| 黄酮醇 | 异鼠李素(Isorhanmetin)山萘酚(Kaempferol)杨梅素(Myricetin)槲皮素(Quercetin) | 几乎到处存在 | |||
| 花色素 | 花青定(Cyanidin)飞燕草定(Delphinidin)锦葵素(Malvidin)天竺葵素(Pelargonidin)矮牵牛定(Petunidin)芍药定(Peonidin) | 红、紫和蓝色浆果 |
所有的类黄酮都适于在没有连接官能团的碳原子上形成本发明的加成产物。为了形成糖加成产物，类黄酮上的糖也可能连接在具有高反应活性位点的类黄酮的C-环上。特别优选在5位具有羟基的类黄酮例如儿茶素和表儿茶素。
根据本发明的类黄酮加成产物可以由纯的类黄酮起始原料或各种含类黄酮的原料例如植物部分、植物提取物等等中获得。例如，人们可以使用可可粉以及来自可可的含有较高水平类黄酮的提取物(例如来自Naturex，法国，#148200，标定为40％多酚的可可提取物)。类黄酮起始原料的其它优选来源是具有高水平儿茶素的绿茶提取物(例如来自Naturex，法国，标定为95％多酚、75％儿茶素、＜0.5％咖啡因、＞40％没食子儿茶素没食子酸酯的绿茶提取物)；葡萄种子或皮提取物(例如由Breko，德国供应的具有40％低聚原花色素的exGrape葡萄种子多酚粉末OPC40#848F/848G；由Breko，德国供应的具有80％多酚的葡萄多酚粉末P80，白色，#834F)。
根据本发明的优选化合物通过在上述基础结构A-环的6和/或8位上添加一个糖而获得。
在本发明的理解中适当的糖是还原糖。所述还原糖是具有酮或醛基团的糖。该还原糖包括果糖、葡萄糖、半乳糖、甘油醛、乳糖、阿拉伯糖和麦芽糖。所有含有酮基的单糖作为酮糖而已知，并且含有醛基的单糖作为醛糖而已知。所有的酮糖和醛糖在本发明的方案中都是有用的。这对于非还原糖例如蔗糖也是成立的，只要它们可以通过已知的方法转化成还原糖。
另外，用于本发明的适当的还原糖可以通过酶处理或水解寡-或多糖制备。
根据本发明最优选的糖是葡萄糖和半乳糖。
虽然不希望被理论所束缚，假定儿茶素或表儿茶素与葡萄糖之间的以下示例反应代表了本发明所提出的其它类黄酮与还原糖之间的反应：
最优选其中在6和/或8位加入还原糖的根据本发明的类黄酮加成产物。这对儿茶素或表儿茶素与葡萄糖和/或半乳糖的加成产物尤其成立。根据本发明最优选的化合物是(-)-儿茶素-6-C-β-D-吡喘葡萄糖苷、(-)儿茶素-8-C-β-D-吡喃葡萄糖苷、(-)-儿茶素-6-C-8-C-β-D-二吡喃葡萄糖苷、(-)-表儿茶素-6-C-β-D-吡喃葡萄糖苷、(-)-表儿茶素-8-C-β-D-吡喃葡萄糖苷和(-)-表儿茶素-6-C-8-C-β-D-二吡喃葡萄糖苷。
根据本发明的化合物可以通过将类黄酮起始原料与还原糖反应而制备。该反应在糖过量的条件下有利地进行。例如，如果使用可可粉作为起始原料，每200g可可粉人们可以使用1到100g糖。
在pH6到14的条件下，优选pH8到12，并且特别优选在pH≥10的条件下进行处理。
反应优选在含水混合物中进行，然而其它溶剂例如醇或者溶剂混合物也是合适的，只要它们不妨碍加成反应。
加热反应混合物是有利的。优选的反应温度在20到120℃的范围，优选60到100℃并且特别是70到90℃。在80℃左右，即在75到85℃获得非常好的结果。
反应时间没有特别的限制。它通常取决于反应的进展并且进行相应的调节。然而，一般而言，反应时间在数小时的水平，例如持续2小时，优选小于一小时。
糖加成产物可以这样使用，在进一步处理例如干燥之后，在液态制备物中将其固化到载体上，等等，或者可以用选自乙醇、丙酮、乙酸乙酯等的适当的溶剂萃取。糖加成产物可以通过选择性的液-液分配和/或使用适当的固相载体例如聚合树脂、反相硅胶、离子交换树脂等的固相萃取/色谱进行进一步富集。
本发明的糖加成产物对于降低多种产品中的涩和苦味都是有效的。这包括可可及相关产品、咖啡及咖啡类的产品、茶饮料及茶叶提取物。尤其是后者对于它们健康方面的益处是有效的。在这里本发明的产品在提供了高类黄酮产品的更高数量和增加了可口性的同时，还强化了这些健康益处。而且，由于它们维持了潜在类黄酮的高抗氧化性能，因此本发明采用的产品本身也为这样的产品的有益效果作出了贡献。实际上这对于包括葡萄提取物的各种产品都是成立的。
本发明的化合物还降低了红酒中的涩味，并且通过软化单宁酸标记提供了更加醇香的味道。
本发明的化合物还可以减少出现在具有绿和红辣椒、姜等的辛辣食物中的辣椒素、姜酚等的辣味。
本化合物也减少了含酒精饮料的“锋利的、燃烧的”味道感觉。
本发明的化合物也是药物组合物和用于口腔的化妆品制备物中的有效味道改性剂。
实施例1
新化合物可以由(表)儿茶素(2mmol)与还原糖例如葡萄糖或半乳糖(20mmol)和1440mgK2CO3加入到25ml溶液(水中，pH为大约10)中并在80℃下反应20分钟而制备。
最后将所得的反应调料冷冻干燥。通过使用丙酮或甲醇水溶液的溶剂萃取以及然后在RP-18材料上使用水-甲醇梯度的色谱法分离，可以从反应调料中提取出单独的化合物。最后，将化合物在真空中蒸发，并且通过二次冷冻干燥仔细除去残存的溶剂。
实施例2
感官品尝(5个人)表明碱性化的可可粉末(5g/200ml)+50ppm 8-C-糖基化儿茶素比没有添加物的对照感觉到更少的苦味和更少的涩味。
未碱性化的可可粉末(5g/200ml)+50ppm 8-C-糖基化儿茶素比没有添加物的对照感觉更淡并且具有更少的涩味。
实施例3
品尝葡萄种子提取物(2000ppm)+ca.10ppm 8-C-糖基化儿茶素和对照葡萄种子提取物(2000ppm)，品尝者发现涩味降低了。
实施例4
可可碱(600ppm)+ca.10ppm 8-C-糖基化儿茶素。品尝者没有感觉到苦味程度的降低，但是注意到相对于纯的可可碱的苦味感觉延迟。
实施例5
向20g具有强烈涩味特征的熔化的黑巧克力中加入77mg溶解于丙二醇中(7.8％)的儿茶素-8-C-葡萄糖苷溶液。凝固之后，品尝该巧克力和未处理过的参照巧克力。发现涩味降低了而苦味没有改变。5名品尝者中的4个注意到“平滑”效果，意思是苦味和涩味没有被掩饰，但是感觉没有最前面那么强烈并且不会延续到如空白中的味道那么久。
实施例6
8个人品尝了碱性化的5g/200ml可可粉和碱性化的可可粉(5g/200ml)+50ppmCat-6-C-Glc(ppm是指1kg水)。发现相对于对照实施例最大程度地降低了苦味的强度，产生了平淡的苦味曲线以及“更加柔和的”苦味性质。
实施例7
将实施例6的改性产品进一步与碱性化可可粉(5g/200ml)+50ppm表儿茶-6-C-Glc(ppm是指1kg水)相比较。感官评价揭示相对于对照最大程度降低的苦味强度，更平淡的苦味曲线以及“更加柔和的”苦味性质。
实施例8
将实施例6的改性产品进一步与碱性化可可粉(5g/200ml)+50ppm Cat-6，8-C-二-Glc(ppm是指1kg水)相比较。感官评价揭示相对于对照最大程度降低的苦味强度，更平淡的苦味曲线以及“更加柔和的”苦味性质。
实施例9
用儿茶素和表儿茶素半乳糖苷重复实施例，得到相同的感官结果。作为一个结果，半乳糖作为还原糖以产生糖加成产物时具有与葡萄糖相等的效果。
实施例10
营养成分由绿茶提取物(5g)或葡萄种子提取物(5g)通过与葡萄糖(4g)和100ml水中的3％K2CO3反应而开始制备。反应在80℃下精确进行20分钟。将产生的调味反应混合物冷冻干燥以获得深红褐色物质，然后将其以各种水平加入到涩味巧克力中。在首次筛选感官品尝中，最优添加水平被确定为300ppm。产生的巧克力呈现了相对于未处理的参照样品具有减少涩味的更加纯净的味道。
当以300ppm加入到黑巧克力中时，由葡萄种子提取物和茶叶提取物以相同的方式制备的成分减少了黑巧克力中涩味的感觉。
实施例11
进行以下试验以证明各种起始原料的效用。下表表示基于可可粉中干重基的浓度[mg/kg]a：
| 化合物 | 原始的 | 烘烤过的 | 烘烤过的+碱性化的 |
| (+)-儿茶素 | 129.89 | 254.30 | 234.63 |
| (-)-表儿茶素 | 1382.41 | 1207.48 | 395.03 |
| 表儿茶素-(4β→8)-表儿茶素(原青花定B2) | 480.70 | 440.11 | 199.94 |
| 表儿茶素-(4β→8)2-表儿茶素(原青花定C1) | 575.77 | 386.05 | 138.61 |
a浓度以相同的方式给出。
bt.a.痕量。
cn.d.未测到。
下表表示当对可可粉进行不同碱性化处理时所获得的糖加成产物(C-葡萄糖苷)的浓度([mg/kg]a干重)(glc表示葡萄糖；gal表示半乳糖)：
| 样品名c | c-8-C-glc | c-6，8-C-diglc | c-6-C-glc | c-8-C-gal | c-6-C-gal |
| 原始 | 0.81 | t.a.b | 1.1 | 0.74 | 0.21 |
| 烘烤过的 | 2.2 | t.a.b | 2.5 | 2.0 | 1.8 |
| 改性可可粉 | 41.9 | 23.1 | 30.2 | 3.7 | 2.7 |
a浓度以完全相同的方式给出。
bt.a.痕量。
c在所有实施例中c-6，8-C-gal以痕量检出。
dn.d.未测到。
为了获得更多数量的糖加成产物，可可粉的改性以如下条件进行：
时间50分钟，T＝80℃，m＝10g葡萄糖，4.4％K2CO3(200g可可粉)。
如果使用其它类黄酮来源的其它可可粉，需要修正反应参数以实现到糖加成产物的最大转化率。
实施例12
为了研究(-)-儿茶素-8-C-β-D-吡喃葡萄糖苷相对于甘元(+)-儿茶素和(-)-表儿茶素以及进一步象芹菜素-8-C-β-D-吡喃葡萄糖苷(牡荆苷)和芹菜素-6-C-β-D-吡喃葡萄糖苷(异牡荆苷)的C-糖苷对可可碱味道改性的影响，将可可碱(3mmol/L)与不同浓度的(-)-儿茶素-8-C-β-D-吡喃葡萄糖苷、(+)-儿茶素、(-)-表儿茶素以及芹菜素-8-C-β-D-吡喃葡萄糖苷(牡荆苷)和芹菜素-6-C-β-D-吡喃葡萄糖苷(异牡荆苷)掺合。结果总结于下表中：
| 加入可可碱(3mmol/L)中的化合物 | 检测到不同的组员比例％ | 味道/强度()b |
| - | - | 苦味(5.0) |
| 2.2μmol/L(-)-儿茶素-8-C-β-D-吡喃葡萄糖苷 | 10 | 更柔和，更加舒适的，更少的苦(4.5) |
| 22.2μmol/L(-)-儿茶素-8-C-β-D-吡喃葡萄糖苷 | 50 | 更柔和，更加舒适的，更少的苦(3.5) |
| 222/Lμmol/L(-)-儿茶素-8-C-β-D-吡喃葡萄糖苷 | 100 | 更柔和，更加舒适的，更少的苦(1.0) |
| 2.2μmol/L(+)-儿茶素 | 0 | 苦味(5.0) |
| 22.2μmol/L(+)-儿茶素 | 50 | 更像可可的苦味(5.0) |
| 222/Lμmol/L(+)-儿茶素 | 50 | 更像可可的苦味(4.0) |
| 2.2μmol/L(-)-表儿茶素 | 0 | 苦味(5.0) |
| 22.2μmol/L(-)-表儿茶素 | 50 | 更像可可的苦味(5.0) |
| 222/L μmol/L(-)-表儿茶素 | 50 | 更像可可的苦味(4.0) |
| 2μmol/L 牡荆苷 | 0 | 苦味(5.0) |
| 22.2μmol/L牡荆苷 | 0 | 苦味(5.0) |
| 222/Lμmol/L牡荆苷 | 50 | 苦味(4.5) |
| 2.2μmol/L异牡荆苷 | 0 | 苦味(5.0) |
| 22.2μmol/L异牡荆苷 | 0 | 苦味(5.0) |
| 222/Lμmol/L异牡荆苷 | 50 | 苦味(4.5) |
a要求八个组员通过三角试验的方式将可可碱溶液(3mmol/L)与掺合了不同量(-)-儿茶素-8-C-β-D-吡喃葡萄糖苷、(+)-儿茶素、(-)-表儿茶素、牡荆苷和异牡荆苷的可可碱溶液(3mmol/L)相比较。
b如果样品被准确地检测(c.f.a)，在与参照可可碱溶液的比较中，评价味道和味道强度的变化，所述参照可可碱溶液被定为5.0的苦味。
Claims (18)
1.一种类黄酮糖-加成产物，其是(-)-儿茶素-6-C-β-D-吡喃葡萄糖苷、(-)-儿茶素-8-C-β-D-吡喃葡萄糖苷、(-)-儿茶素-6-C-8-C-β-D-二吡喃葡萄糖苷或(-)-表儿茶素-6-C-β-D-吡喃葡萄糖苷或者具有半乳糖苷残基或具有另一种还原糖的相同糖苷。
2.一种含有如权利要求1所述加成产物的组合物。
3.如权利要求2所述的组合物，其是可食用的产品。
4.如权利要求3所述的组合物，其是改生植物提取物。
5.如权利要求2到4任意一项所述的组合物，其中该组合物是可可或可可类产品例如巧克力，尤其是黑巧克力。
6.如权利要求2到3任意一项所述的组合物，其中该组合物是咖啡或咖啡类产品。
7.一种类黄酮糖-加成产物的用途，其特征在于所述类黄酮是用还原糖C-糖基化过的，或者具有含有所述加成产物作为食物产品、药用制品或与口腔接触的化妆品的味道改性剂的组合物。
8.一种类黄酮糖-加成产物的用途，其特征在于所述类黄酮是用还原糖C-糖基化过的，或者具有含有所述加成产物以给予食物产品或药用产品滑润、柔软的口感的组合物。
9.如权利要求7或8所述的用途，其中食物产品是可可、咖啡或来源于它们的产品。
10.如权利要求7到9任意一项所述的用途，其中将还原糖加入到未取代的C-原子上，优选在6和/或8位。
11.如权利要求7到10任意一项所述的用途，其中所述类黄酮是黄烷、黄烷低聚物、黄烷聚合物、黄酮、黄酮醇或黄烷酮、儿茶素、儿茶素和表儿茶素。
12.如权利要求7到11任意一项所述的用途，其中还原糖是己糖或戊糖，例如葡萄糖和半乳糖，二糖或低聚糖。
13.如权利要求7到12任意一项所述的用途，其中糖-加成产物是(-)-儿茶素-6-C-β-D-吡喃葡萄糖苷、(-)-儿茶素-8-C-β-D-吡喃葡萄糖苷和(-)-儿茶素-6-C-8-C-β-D-二吡南葡萄糖苷或者具有半乳糖苷残基的相同糖苷，或者具有糖苷表儿茶素相同的糖苷。
14.如权利要求7到13任意一项所述的用途，其中组合物是可食用的产品。
15.如权利要求7到14任意一项所述的用途，其中组合物是改性植物提取物。
16.如权利要求7到15任意一项所述的用途，其中组合物是可可或可可类产品例如巧克力，尤其是黑巧克力。
17.如权利要求14或15所述的用途，其中组合物是咖啡或咖啡类产品。
18.一种制备如权利要求1所述加成产物的方法，其包括将含有类黄酮的起始原料与糖在pH 8到12的条件下反应的步骤，其中所述起始原料是儿茶素或表儿茶素，并且其中所述糖是葡萄糖或半乳糖或另一种还原糖。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06010370.2 | 2006-05-19 | ||
| EP06010370.2A EP1856988B1 (en) | 2006-05-19 | 2006-05-19 | Flavonoid sugar addition products, method for manufacture and use thereof |
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| Publication Number | Publication Date |
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| CN101081858A true CN101081858A (zh) | 2007-12-05 |
| CN101081858B CN101081858B (zh) | 2013-04-10 |
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| CN2007101266587A Active CN101081858B (zh) | 2006-05-19 | 2007-05-18 | 类黄酮糖加成产物、生产方法及其应用 |
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| Country | Link |
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| US (1) | US8003150B2 (zh) |
| EP (1) | EP1856988B1 (zh) |
| JP (1) | JP5441318B2 (zh) |
| KR (1) | KR101457680B1 (zh) |
| CN (1) | CN101081858B (zh) |
| AR (1) | AR061035A1 (zh) |
| AU (1) | AU2007202198B2 (zh) |
| BR (1) | BRPI0702295A (zh) |
| CA (1) | CA2588882C (zh) |
| NO (1) | NO343256B1 (zh) |
| NZ (1) | NZ555168A (zh) |
| PL (1) | PL1856988T3 (zh) |
| RU (1) | RU2433824C2 (zh) |
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| CN102471363A (zh) * | 2009-07-31 | 2012-05-23 | 国立大学法人冈山大学 | 新型黄烷酮衍生物 |
| CN102526170A (zh) * | 2011-12-31 | 2012-07-04 | 许学志 | 抗结核杆菌的儿茶提取物组合物、其制备方法及含有它们的药物制剂和应用 |
| CN102573503A (zh) * | 2009-07-29 | 2012-07-11 | 雀巢产品技术援助有限公司 | 含有黄烷酮的食品组合物 |
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| FI20075086L (fi) * | 2007-02-07 | 2008-08-08 | Slk Foundation | Aromikoostumus |
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| EP2571502B1 (en) | 2010-05-19 | 2016-04-27 | Unilever N.V. | Theobromine for increasing hdl-cholesterol |
| JP5744471B2 (ja) * | 2010-10-22 | 2015-07-08 | 花王株式会社 | 苦味抑制剤 |
| JP5830267B2 (ja) * | 2011-04-22 | 2015-12-09 | 花王株式会社 | 容器詰飲料 |
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| CA2903770C (en) * | 2013-03-14 | 2022-07-12 | Mars, Incorporated | Flavor composition containing 3-hydroxy-3-methylglutaric acid (hmg) glucosides |
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| WO2015094224A1 (en) * | 2013-12-18 | 2015-06-25 | Nestec S.A. | Methods for increasing the clarity and refreshing attributes and reducing the bitterness and astringency of green tea |
| EP2952103B1 (de) | 2014-06-05 | 2019-05-08 | Symrise AG | Stoffgemische |
| US10301275B2 (en) | 2017-03-17 | 2019-05-28 | Altria Client Services Llc | Sweet taste modulators |
| WO2020061223A1 (en) | 2018-09-18 | 2020-03-26 | Ohio State Innovation Foundation | Novel small molecules that enhance flavor qualities of coffee and related beverages |
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- 2006-05-19 PL PL06010370T patent/PL1856988T3/pl unknown
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- 2007-05-15 NZ NZ555168A patent/NZ555168A/en unknown
- 2007-05-16 CA CA2588882A patent/CA2588882C/en active Active
- 2007-05-16 AU AU2007202198A patent/AU2007202198B2/en active Active
- 2007-05-17 US US11/750,121 patent/US8003150B2/en active Active
- 2007-05-18 KR KR1020070048683A patent/KR101457680B1/ko not_active IP Right Cessation
- 2007-05-18 BR BRPI0702295-6A patent/BRPI0702295A/pt not_active Application Discontinuation
- 2007-05-18 AR ARP070102170A patent/AR061035A1/es unknown
- 2007-05-18 CN CN2007101266587A patent/CN101081858B/zh active Active
- 2007-05-18 RU RU2007118606/13A patent/RU2433824C2/ru not_active IP Right Cessation
- 2007-05-18 NO NO20072524A patent/NO343256B1/no unknown
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102573503A (zh) * | 2009-07-29 | 2012-07-11 | 雀巢产品技术援助有限公司 | 含有黄烷酮的食品组合物 |
| CN102471363A (zh) * | 2009-07-31 | 2012-05-23 | 国立大学法人冈山大学 | 新型黄烷酮衍生物 |
| CN102526170A (zh) * | 2011-12-31 | 2012-07-04 | 许学志 | 抗结核杆菌的儿茶提取物组合物、其制备方法及含有它们的药物制剂和应用 |
| CN102526170B (zh) * | 2011-12-31 | 2015-04-29 | 许学志 | 抗结核杆菌的儿茶提取物组合物、其制备方法及含有它们的药物制剂和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| NO343256B1 (no) | 2019-01-02 |
| CA2588882C (en) | 2015-02-24 |
| PL1856988T3 (pl) | 2018-02-28 |
| RU2433824C2 (ru) | 2011-11-20 |
| US20070269570A1 (en) | 2007-11-22 |
| BRPI0702295A (pt) | 2008-01-15 |
| NO20072524L (no) | 2007-11-20 |
| KR20070112052A (ko) | 2007-11-22 |
| KR101457680B1 (ko) | 2014-11-03 |
| NZ555168A (en) | 2009-11-27 |
| US8003150B2 (en) | 2011-08-23 |
| JP5441318B2 (ja) | 2014-03-12 |
| AR061035A1 (es) | 2008-07-30 |
| CN101081858B (zh) | 2013-04-10 |
| EP1856988A1 (en) | 2007-11-21 |
| EP1856988B1 (en) | 2017-09-13 |
| RU2007118606A (ru) | 2008-11-27 |
| AU2007202198B2 (en) | 2012-04-26 |
| AU2007202198A1 (en) | 2007-12-06 |
| CA2588882A1 (en) | 2007-11-19 |
| JP2007314535A (ja) | 2007-12-06 |
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