CN1313469C - 黄酮c糖苷的衍生物和含有其的组合物 - Google Patents
黄酮c糖苷的衍生物和含有其的组合物 Download PDFInfo
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- CN1313469C CN1313469C CNB038181061A CN03818106A CN1313469C CN 1313469 C CN1313469 C CN 1313469C CN B038181061 A CNB038181061 A CN B038181061A CN 03818106 A CN03818106 A CN 03818106A CN 1313469 C CN1313469 C CN 1313469C
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- food
- flavone
- salt
- compound
- glycoside derivatives
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Abstract
本发明涉及特别是显示抗过敏作用的黄酮C糖苷的新型衍生物或其盐以及含有其的组合物。近年来,过敏性疾病在增加,特别是花粉症和过应性皮炎的增加显著,甚至已成为了社会问题。报告指出黄酮及其糖苷具有抑制组胺从肥大细胞游离的作用和免疫抑制作用,作为过敏治疗药物的应用受到期待。但是,几乎所有的黄酮显示其效果的用量高,因此急切希望开发出以更低用量显示效果的化合物。本发明提供能以低用量治疗过敏性疾病的新型成分和含有其的组合物。
Description
技术领域
本发明涉及特别显示出抗过敏性作用的黄酮C糖苷的新型衍生物或其盐和含有其的组合物。
背景技术
近年来,根据各种流行病学调查已表明过敏性疾病在增加。特别是花粉症和特应性皮炎的增加显著,甚至已成为了社会问题。过敏素的增加以及大气污染和食品添加物、饮食习惯的变化这些围绕我们的环境的变化被推定是过敏增加的原因(伊藤,总合临床、
41:3099(1992))。过敏性疾病的治疗方法进行的是以首先将作为原因的过敏素除去或不摄取为基础,根据症状的程度和各疾病的发病机理的药物疗法。过敏反应因作为其原因的免疫球蛋白、涉及的免疫细胞的不同而被为为I型~IV型四种类型。I型~III型过敏是涉及体液性抗体的免疫反应,由于过敏反应迅速出现,因此也被称为速发型过敏,IV型过敏与抗体无关,为与致敏淋巴细胞有关的细胞性免疫反应,也被称为迟发型过敏(富冈,总合临床、
41:3103(1992))。
在这些过敏反应中,花粉症和特应性皮炎被认为与I型和IV型过敏反应有关,其治疗使用抗组织胺剂、碱性抗过敏剂或类固醇剂等。
另一方面,也申请了与利用了乌龙茶抽提物或茶中的表儿茶素没食子酸酯抗过敏剂的专利(特开平10-077231、特开平10-175874、专利3023962等)。此外,报告表明黄酮和其糖苷具有抑制组胺从肥大细胞中游离的作用和免疫抑制作用,作为过敏治疗药的应用受到期待(Kubo M.etal,Chem.Pharm.Bull.
32:5051(1984))。但是,几乎所有的黄酮显示其效果的用量高,急切希望以更低用量显示效果的化合物。
发明内容
本发明的目的在于提供将具有抗过敏作用的物质分离、鉴定,提供能以低用量治疗过敏性疾病的新型成分和含有它们的组合物。
本发明者们为了解决上述课题,将注意力集中在乌龙茶的抗过敏作用上,对乌龙茶中的抗过敏成分进行了详细的研究,其结果发现:新型黄酮C糖苷的衍生物或其盐对2,4-二硝基氟代苯(DNFB)诱发的耳肿胀形成具有抑制作用以及对组胺从腹腔肥大细胞中游离具有抑制效果。此外,发现可以将它们作为医药组合物、食品组合物或化妆品中的有效成分利用,从而完成了本发明。
附图说明
图1表示在实验例1中进行的,以本发明的化合物(1)的给予量为0.2、1.0和5.0μg/kg三种浓度和作为对照给予0.5%羧甲基纤维素钠/0.01N盐酸时对于小鼠耳廓接触性皮炎的抑制效果的差的曲线图。
图2表示在实验例2中进行的,以本发明的化合物(2)的给予量为1.0、10和100μg/kg三种浓度和作为对照给予0.5%羧甲基纤维素钠/0.01N盐酸时对于小鼠耳廓接触性皮炎的抑制效果的差的曲线图。
图3表示类黄酮的结构。
具体实施方式
如上所述,本发明者为了解决上述课题,将注意力集中于乌龙茶的抗过敏作用上,对乌龙茶中抗过敏成分进行了详细的研究,其结果发现:新型黄酮C糖苷的衍生物或其盐对2,4-二硝基氟代苯(DNFB)诱发的耳肿胀形成具有抑制作用以及对组胺从腹腔肥大细胞中游离具有抑制效果。此外,发现可以将它们作为医药组合物、食品组合物或化妆品中的有效成分利用,从而完成了本发明。
因此,本发明涉及式(1)所示的黄酮C糖苷的衍生物或其盐。
此外,本发明涉及式(2)所示的黄酮C糖苷的衍生物或其盐。
本发明涉及过敏性疾病的预防和/或治疗用医药组合物,其含有上述黄酮C糖苷的衍生物或其盐的至少1种。此外,本发明涉及医药组合物,其中,该过敏性疾病为选自特应性皮炎、接触性皮炎、花粉症的至少一种疾病。
本发明涉及食品组合物,其含有上述黄酮C糖苷的衍生物(1)或(2)或其盐的至少1种。更详细来说,本发明涉及食品组合物,其中,该食品组合物为作为特定保健用食品、特殊营养食品、营养辅助食品的饮料或其他的营养饮料、健康饮料、健康茶、其他饮料。此外,本发明涉及食品组合物,其中,该食品组合物为糕点类、面包、面食类、大豆加工品、乳制品、蛋加工品、把鱼肉搅碎加其它材料制成的熟食、油脂或调味料。
此外,本发明涉及化妆料,其含有上述黄酮C糖苷的衍生物(1)或(2)或其盐的至少1种。此外,本发明涉及化妆品,其中,该化妆料为护肤品、化妆品、头发化妆料或洗浴料。
本发明所涉及的式(1)和/或式(2)的黄酮C糖苷的衍生物或其盐,可以例如,以茶叶为原料,通过实施加热和采用溶剂进行抽提、浓缩、精制等一般的化学分离精制手段(例如,分级或色谱法)而得到。
作为制造时使用的茶叶,可以使用茶树(Camellia sinensis)的叶和/或将其加工后的茶叶。特别优选使用乌龙茶。所谓乌龙茶,是指以中国福建省、广东省或台湾等为主产地的中国原产的半发酵茶。
用于溶出的溶剂可以为水系溶剂和/或有机溶剂的任何一种,优选使用水系溶剂。水系溶剂优选水、乙醇或甲醇等。可以为水单独或水与甲醇、乙醇等低级醇的任意的混合溶液。
抽提时乌龙茶和溶剂的比率也无特别限定,相对于乌龙茶1重量份,溶剂为2~1000重量份,考虑到抽提操作、效率方面,特别优选5~100重量份。
此外,溶出时的温度如果比溶剂的熔点高,比沸点低,则并无特别限定,但如果是水,优选10℃~100℃,如果是乙醇和甲醇,优选10℃~40℃。抽提时间优选为10秒~24小时的范围。
作为化学分离精制手段,可以使用作为化学分离精制手段通常使用的方法,可以使用例如液-液分离、薄层色谱法、吸附柱色谱法、分配柱色谱法、凝胶过滤柱色谱法、离子交换柱色谱法、电泳或高效液相色谱法等。此外,也可以根据需要将这些分离精制手段组合,将本发明所涉及的式(1)和式(2)的黄酮C糖苷的衍生物或其盐精制为高纯度。
本发明所涉及的式(1)和式(2)的黄酮C糖苷的衍生物或其盐由于显示抗过敏作用,因此可以在医药、食品和化妆品等各种用途中使用。作为医药,式(1)和/或(2)的化合物或其盐对DNFB诱发的耳肿胀形成显示抑制作用以及对组胺游离显示抑制作用,所以作为抗过敏剂,可以特别用于特应性皮炎、接触性皮炎和花粉症的治疗目的。作为食品,以特应性皮炎、接触性皮炎和花粉症的症状的缓和和预防为目的,可以作为食品添加物配合于特定保健用食品、特殊营养食品、营养辅助食品、健康食品等中。作为添加对象的食品,可以为各种食品。作为饮料,可以配合于特定保健用食品、特殊营养食品、营养辅助食品的饮料和其他营养饮料、健康饮料、各种健康茶、其他饮料等中。作为其他食品,可以列举糕点类、面包、面食类、大豆加工品、乳制品、蛋加工品、把鱼肉搅碎加其它材料制成的熟食、油脂、调味料等。作为化妆品,以特应性皮炎、接触性皮炎和花粉症的症状的缓和和预防为目的,可以在护肤品、粉底和化妆品等中添加式(1)和/或式(2)的化合物或其盐。
关于医药,可以直接或用水等稀释,经口给予式(1)和/或式(2)的化合物或其盐。或通过将其与公知的医药用载体一起制剂化而调制。例如,将式(1)和/或式(2)的化合物或其盐制成浆剂等经口液状制剂,或加工成浸膏、粉末等,与药学上允许的载体配合,作为片剂、胶囊剂、颗粒剂、散剂等经口固形制剂给予。作为药学上允许的载体,可以使用惯用的各种有机或无机载体物质作为制剂原材料,作为固形制剂中的赋形剂、润滑剂、结合剂、崩解剂,液状制剂中的溶剂、赋形剂、悬浮剂、结合剂等配合。此外,也可以根据需要使用防腐剂、抗氧化剂、着色料、甜味剂等制剂添加物。
作为赋形剂优选的例子,可以列举例如乳糖、白糖、D-甘露糖醇、淀粉、结晶纤维素、轻质硅酸酐等。作为润滑剂优选的例子,可以列举例如硬脂酸镁、硬脂酸钙、滑石、胶体二氧化硅等。作为结合剂优选的例子,可以列举例如结合纤维素、白糖、D-甘露糖醇、糊精、羟丙基纤维素、羟丙基甲基纤维素、聚乙烯基吡咯烷酮等。作为崩解剂优选的例子,可以列举例如聚乙二醇、丙二醇、D-甘露糖醇、苯甲酸苄酯、乙醇、三氨基甲烷、胆甾醇、三乙醇胺、碳酸钠、柠檬酸钠等。作为液剂优选的例子,可以列举例如精制水、醇、丙二醇等。作为悬浮剂优选的例子,可以列举例如硬脂酸乙醇胺、月桂基硫酸钠、月桂基氨基丙酸、卵磷脂、氯苄烷铵、苯索氯铵、甘油单硬脂酸酯等表面活性剂;以及例如聚乙烯醇、聚乙烯基吡咯烷酮、羧甲基纤维素钠、甲基纤维素、羟甲基纤维素、羟乙基纤维素、羟丙基纤维素等亲水性高分子。作为防腐剂的优选例,可以列举例如对羟基苯甲酸酯类、氯丁醇、苄醇、苯乙醇、脱氢乙酸、山梨酸等。作为抗氧剂的优选例,可以列举例如亚硫酸盐、抗坏血酸等。
作为剂型,其依赖于疾病的种类和程度等,例如,作为适于经口、非经口或经鼻给予的剂型,可以列举片剂或糖衣片、舌下片、明胶胶囊剂、锭剂(troche)、栓剂、膏剂、软膏剂、皮肤用凝胶剂等。此外,有效的用量因患者的年龄和体重、疾病的种类和严重程度以及给予的途经而变化。单位用量一般是每24小时给予1~3次,每次给予0.0001~100mg/kg的范围。
关于食品,可以直接或加工成浸膏、粉末等,以饮食物的形式给予式(1)和/或式(2)的化合物或其盐。此外,可以与一般使用的饮食物原材料和饮食物制造上允许的载体配合,作为饮料、糕点类、面包、面食类、大豆加工品、乳制品、蛋加工品、把鱼肉搅碎加其它材料制成的熟食、油脂或调味料等提供。
在本发明中,所谓饮料,是指乌龙茶饮料、与其他茶饮料混合的茶饮料、碳酸饮料、果实饮料、乳酸菌饮料、运动饮料、豆奶和葡萄酒、烧酒、威士忌、清酒等酒类等。
在本发明中,所谓糕点类,是指饼干类、巧克力类、糖果类、口香糖类、快餐糕点类、油炸蛋糕类、西式新鲜蛋糕类、日式蛋糕类、冰激凌类、果子冻等。
大豆加工品中包括豆腐等,乳制品中包含酸乳酪、黄油等。鸡蛋加工品中包含炒鸡蛋、碗蒸鸡蛋羹等,把肉搅碎加其它材料制成的熟食中包含鱼糕等。调味料中包含调味品(酱油)、调味品(香料)、蛋黄酱、撒在饭上吃的调味料(鱼粉、紫菜末等)等。它们可以采用通常方法制造。
作为饮食物制造上允许的载体,可以列举砂糖、葡萄糖、果糖、异构化液糖、低聚果糖、天冬甜素、山梨糖醇、甜叶菊等甜味料;甘蓝色素、葡萄果皮色素、接果木色素、焦糖色素、栀子花色素、玉米色素、藏红花色素、胡萝卜等着色料;果胶分解物、苯甲酸、山梨酸、对羟基苯甲酸酯类、山梨酸钾等保存材料;藻酸钠、藻酸丙二醇酯、纤维素乙醇酸钙、纤维素乙醇酸钠等糊料;L-抗坏血酸、生育酚、异抗坏血酸、芸香苷等抗氧剂;硫酸亚铁、亚硝酸钠、硝酸钾等发色剂;亚硫酸氢钠、偏亚硫酸钾等漂白剂;丙二醇等品质保持剂;L-半胱氨酸盐酸盐、硬脂基乳酸钙等品质改善剂;氯化铵、d-酒石酸氢钾、碳酸铵、碳酸钾、碳酸氢钠、明矾等膨胀剂;卵磷脂、神经鞘脂类、植物性胆甾醇、大豆皂苷、藻酸钠、藻酸丙二醇酯、酪蛋白钠、甘油脂肪酸酯、蔗糖脂肪酸酯、失水山梨糖醇脂肪酸酯等乳化剂;软骨素硫酸钠等乳化稳定剂;柠檬油、桉树油、薄荷油、香子兰浸膏、橙油、蒜油、乙酰乙酸乙酯、茴香醛、乙基香兰素、肉桂酸、香茅醇乙酸酯、柠檬醛、香兰素、丁酸丁酯、酯类等着香料;L-抗坏血酸、L-天冬酰胺、L-丙氨酸、肌醇、L-谷氨酰胺、胡萝卜素、生育酚、维生素A、叶酸、柠檬酸铁、血红素铁、未煅烧钙等强化剂;过氧化苯甲酰、过硫酸铵、二氧化氯等小麦粉改良剂;漂白粉、过氧化氢、次氯酸等杀菌料;乙酰基蓖麻油酸甲酯、酯胶、醋酸乙烯酯树脂、聚异丁烯、聚丁烯等口香糖基础剂、D-甘露糖醇等防粘接剂;酸性焦磷酸钠、焦磷酸钾、焦磷酸钠等粘接剂;己二酸、柠檬酸、葡糖酸、琥珀酸、d-酒石酸、乳酸、d1-苹果酸等酸味料;海产品提取物、酵母提取物、海藻提取物、酱油、番茄酱、肉提取物、料酒、果酱、煮熟和干燥的鲣鱼肉、L-天冬氨酸钠、DL-丙氨酸、L-精氨酸、L-谷氨酸盐、5’-肌苷酸二钠、柠檬酸三钠、L-谷氨酸、L-谷氨酸钠、琥珀酸、L-酒石酸、乳酸钠等调味料等。
本发明提供的式(1)和/或式(2)的化合物或其盐可以直接或用水等稀释,或浓缩,或粉末化或颗粒化,通过与公知的载体配合,作为气雾剂、液剂、浸膏剂、悬浮剂、乳剂、软膏剂、泥敷(pap)剂、涂抹剂、洗剂等形态提供。或者根据需要适当选择用于公知的化妆品、准医药品、医药品的水性成分、表面活性剂、油性成分、可溶化剂、保湿剂、粉末成分、醇类、pH调节剂、防腐剂、抗氧剂、增粘剂、色素、颜料、香料等而调制。作为皮肤外用剂,也可以成为洗剂状、凝胶状、乳剂、软膏等剂型。
在本发明中,所谓护肤品,是指柔软性化妆水、收敛性化妆水等化妆水类,润肤膏、增湿膏、按摩膏等膏类,润肤乳液、营养乳液、清洗乳液等乳液类等。
所谓化妆料,是指洗脸料、皮肤洗涤剂、粉底、眼影、腮红、口红等。
所谓毛发化妆料,是指香波、漂洗液、头发护理剂、发乳、整发剂、头发强壮剂、养毛剂、育毛剂等。所谓洗浴剂,是指洗浴油、洗浴盐、洗浴泡沫等。
关于食品和化妆料,其配合量也无特别限定,一般换算为干燥固体成分,为0.0001~100重量%,特别优选为0.001~50重量%。
列举实验例和实施例对本发明进行更为详细的说明,但本发明的范围并不仅仅限于这些实验例和实施例。
实施例
实施例1:制造例
使用热水100L对中国福建省产的乌龙茶茶叶5.0kg进行抽提,放冷后装入填充了30L的合成吸附剂(DIAION HP-21、三菱化学社制)的柱内,再将没有吸附级分装入填充了30L的合成吸附剂(DIAION HP-20、三菱化学社制)的柱内,顺次增加乙醇相对于水的含量,使其流出(分别平均为60L),得到4个级分[乙醇浓度=0%(OHF3N)、20%(OHF4N)、40%(OHF5N)、99.5%(OHF6N)]。
将这4个级分中对DNFB诱发的耳肿胀形成具有最强抑制作用的OHF3N级分进行浓缩、冷冻干燥(517g),再用水-正丁醇进行对流分配(n=7),将转移次数7次的级分的减压浓缩物(2.1g)装入填充了Sephadex LH-20(Pharmacia Biotech社制)的柱内,用甲醇溶出,收集Kd值1.9~2.2的级分。用HPLC将该减压浓缩物分离。柱使用SENSHU PAK DIOL-1251(SENSHU化学社制、4.6×250mm),移动相使用己烷∶甲醇∶四氢呋喃=50∶35∶15的溶剂,以流速1ml/min(30℃)使其溶出,分取保留时间5.8分钟时溶出的峰(UV280nm)。减压浓缩后,通过采用了YMC-Pack ODS-A(YMC社制、4.6×150mm)的HPLC进行精制。分取后,通过减压浓缩,得到980μg的淡黄色粉末。
用NMR、MS等光谱和X射线解析进行结构解析的结果(表1和表2):本化合物被鉴定为式(1)的异牡荆葡基黄酮(Isovitexin)(参照图3)的7位的OH和糖链的1位的OH分子内脱水缩合的化合物[化合物(1)]。
表1化合物(1)由1H-NMR和13C-NMR测定的结构
部分 | 苷元 | 糖 | |||
C | H | C | H | ||
23456789101’2’3’4’5’6’ | 168.1102.9184.8168.7112.6166.591.8161.2107.9119.3130.2119.3168.1119.3130.2 | 6.58s6.64s7.80d6.80d6.80d7.80d | 1″2″3″4″5″6″ | 74.689.073.969.880.663.5 | 5.21d4.67t3.98t3.58t3.33m3.62m,3.83m |
化合物(1)由1H-NMR和13C-NMR测定的结构(ppm.in CD3OD)
表2化合物(1)由X射线解析测定的结构
结晶尺寸晶格参数空间群Z值DcalcR值 | 0.10×0.05×0.20mma=10.811(6)b=26.270(6)c=6.905(1)V=1961.0(9)3P21212141.403g/cm30.078 |
对化合物(1)的精制过程中的OHF3N级分(517g)用水-正丁醇进行对流分配(n=7),将转移次数7次的级分的减压浓缩物(2.1g)装入填充了Sephadex LH-20(Pharmacia Biotech社制)的柱内,用甲醇溶出,收集Kd值1.6~1.9的级分。用HPLC将该减压浓缩物分离。柱使用SENSHUPAK DIOL-1251(SENSHU化学社制、4.6×250mm),移动相使用己烷∶甲烷∶四氢呋喃=50∶35∶15的溶剂,以流速1ml/min(30℃)使其溶出,分取保留时间5.8分钟时溶出的峰(UV280nm)。减压浓缩后,通过采用了YMC-Pack ODS-A(YMC社制、4.6×150mm)的HPLC进行精制。分取后,通过减压浓缩,得到147μg的淡黄色粉末。
用NMR、MS等波谱和X射线解析进行结构解析的结果(表3和表4):本化合物被鉴定为式(2)的牡荆葡基黄酮(Vitexin)(参照图3)的7位的OH和糖链的1位的OH分子内脱水缩合的化合物[化合物(2)]。
表3化合物(2)由1H-NMR和13C-NMR测定的结构
部分 | 苷元 | 糖 | |||
C | H | C | H | ||
23456789101’2’3’4’5’6’ | 166.8104.3184.4166.296.3168.9108.5155.1106.7125.0130.2118.0164.9118.0130.2 | 6.66s6.39s7.90d6.93d6.93d7.90d | 1″2″3″4″5″6″ | 75.189.173.869.880.563.4 | 5.47d4.78t4.05t3.62t3.47m3.65m,3.87m |
化合物(2)由1H-NMR和13C-NMR测定的结构(ppm.in CD3OD)
表4化合物(2)由X射线解析测定的结构
结晶尺寸晶格参数空间群Z值DcalcR值 | 0.03×0.10×0.30mma=9.785(2)b=19.700(5)c=4.9357(8)V=950.1(3)3P2121.560g/cm30.058 |
实验例1:对大鼠耳廓接触性皮炎的抑制效果
使用动物为从日本クレア(株)购入的7周龄的ICR系小鼠,预饲养1周后,用于实验。将实施例1中制备的黄色粉末[化合物(1)]悬浮于0.5%羧甲基纤维素钠/0.01N盐酸中,调制给予量为0.2、1.0和5.0μg/kg的3种浓度样品,使给予量达到10ml/kg。小鼠为1组6只,向背部皮下注射1%的2,4-二硝基氟代苯(DNFB)乙醇溶液100μl,用5天时间使其感染。第6天在右耳廓涂布1%DNFB橄榄油溶液,使产生耳廓接触性皮炎。24小时后,用直径8mm的穿孔器将两耳穿孔,测定重量。从初次感染前一天到引起浮肿当天的7天间连续地进行化合物(1)的经口给予。作为对照组,给予0.5%羧甲基纤维素钠/0.01N盐酸。实验结果用右耳廓相对于左耳廓的浮肿率的平均值和标准偏差表示,组间的有意义差检验使用Student的t-检验。其结果示于图1。从图1可以看到,与给予0.5%羧甲基纤维素钠/0.01N盐酸的对照组比较,在化合物(1)的1.0和5.0μg/kg给予组中,DNFB引起的浮肿得到了有意的抑制。
实验例2:对大鼠耳廓接触性皮炎的抑制效果
使用动物为从日本クレア(株)购入的7周龄的ICR系小鼠,预饲养1周后,用于实验。将实施例1中制备的黄色粉末[化合物(2)]悬浮于0.5%羧甲基纤维素钠/0.01N盐酸中,调制给予量为1.0、10和100μg/kg的3种浓度样品,使给予量达到10ml/kg。小鼠为1组6只,向背部皮下注射1%的2,4-二硝基氟代苯(DNFB)乙醇溶液100μl,用5天时间使其感染。第6天在右耳廓涂布1%DNFB橄榄油溶液,使产生耳廓接触性皮炎。24小时后,用直径8mm的穿孔器将两耳穿孔,测定重量。从初次传染前一天到引起浮肿当天的7天间连续地进行化合物(2)的经口给予。作为对照组,给予0.5%羧甲基纤维素钠/0.01N盐酸。实验结果用右耳廓相对于左耳廓的浮肿率的平均值和标准偏差表示,组间的有意差检验使用Student的t-检验。其结果示于图2。从图2可以看到,与给予0.5%羧甲基纤维素钠/0.01N盐酸的对照组比较,在化合物(2)100μg/kg给予组中,DNFB引起的浮肿得到了有意的抑制。
实验例3:对于组胺从腹腔肥大细胞中游离的抑制效果
使用动物为从日本クレア(株)购入的7周龄的Wistar系大鼠,预饲养1周后,用于实验。在***麻醉下将Wistar系大鼠断头处死后,在腹腔内注入Tyrode液。采用惯用方法将肥大细胞分离,悬浮于含有0.1%牛血清白蛋白(BSA)的Tyrode液中使之达到1~3×108cell/ml,调制肥大细胞浮游液。将溶解于50%甲醇的化合物(1)或化合物(2)加入上述肥大细胞浮游液中,在37℃下进行5分钟保温。然后,加入Compound48/80,在37℃下保温10分钟,冰冷后,对离心分离的上清液按照Onda等的方法[J.Med.Sci.,27,93-97(1978)],通过使用了邻苯二甲醛(OPA)的柱后法(post-column method)的高速液相色谱仪测定游离组胺量。实验结果通过相对于只用溶剂处理时的组胺游离量,用试料处理时的组胺游离抑制率表示。其结果示于表5。
表5组胺游离抑制试验结果
试料 | 浓度(μg/ml) | 组胺游离抑制率(%) |
化合物(1) | 5.0 | 62.3 |
化合物(2) | 50.0 | 51.2 |
实施例2:与甾体化合物剂和其他类黄酮的效果比较
使用与实施例1和实施例2相同的方法,将副肾皮质甾族化合物剂和多种类黄酮(图3)对DNFB诱发的耳肿胀形成的抑制作用与化合物(1)和化合物(2)进行比较。实验结果用对DNFB诱发的耳肿胀形成抑制50%的给予量表示。其结果示于表6。
与肾上腺皮质甾体化合物剂或其他类黄酮比较,化合物(1)和化合物(2)的给予以极少量就显示出对耳肿胀形成的抑制作用。
表6耳肿胀形成抑制作用的评价结果
将耳肿胀抑制50%的给予量(mg/kg p.O.) | |
化合物(1) | 0.05 |
化合物(2) | 0.17 |
*** | 1.5 |
芹菜苷配基(Apigenin) | 247 |
牡荆葡基黄酮 | 103 |
Rhamnosyl vitexin | 146 |
五羟黄酮(Quercetin) | 265 |
芸香苷 | 123 |
实施例3:片剂的制造例
将实施例1中制备的化合物(1)150g与等量的乳糖和硬脂酸镁5g混合,用单发式打片机对该混合物进行打片,制造直径10mm、重量300mg的片剂。
实施例4:颗粒剂的制造例
将实施例2中制备的片剂粉碎、制粒、筛分,得到20-50目的颗粒剂。
实施例5:糖的制造例
使用以下材料,按照通常方法制造。
粉末山梨糖醇 99.7g
香料 0.2g
化合物(1) 0.05g
山梨糖醇种 0.05g
总量 100g
实施例6:口香糖的制造例
使用以下材料,按照通常方法制造。
原料胶 20g
碳酸钙 2g
蛇菊苷(stevioside) 0.1g
化合物(1) 0.05g
乳糖 76.85g
香料 1g
总量 100g
实施例7:桔子汁的制造例
使用以下材料,按照通常方法制造。
冷冻浓缩桔子果汁 5g
果糖-葡萄糖浆 10g
柠檬酸 0.2g
L-抗坏血酸 0.02g
化合物(1) 0.05g
香料 0.2g
色素 0.1g
水 残余量
总量 100g
实施例8:果子冻的制造例
使用以下材料,按照通常方法制造。
砂糖 500g
糖稀 500g
果胶 13g
柠檬酸 4g
柠檬酸钠 1.5g
香料 1g
食用色素 0.2g
化合物(1) 0.5g
将砂糖20g混合到果胶13g中,加入水330ml,使其溶解均匀。再加入柠檬酸和柠檬酸钠,使其沸腾。向其中加入糖稀,加热到100℃后,加入剩余的砂糖,升温到109℃。静置数分钟后,加入化合物(1)、香料和色素并进行搅拌,填充到淀粉模中,在50℃以下干燥10小时以上,得到果子冻。
实施例9:鱼糕的制造例
使用以下材料,按照通常方法制造。
鳕鱼的肉馅 100g
食盐 20g
调味料 2g
蛋清 10g
化合物(1) 0.5g
在鳕鱼的肉馅中加入食盐、调味料和化合物(1)搅拌混合,熟化后成型,在预先加热到约90~95℃的蒸器中蒸煮,然后放冷,得到鱼糕。
实施例10:润肤膏的制造例
使用以下材料,按照通常方法制造。
蜂蜡 2.0g
硬脂醇 5.0g
硬脂酸 8.0g
角鲨烷 10.0g
自乳化型丙二醇单硬脂酸酯 3.0g
聚氧乙烯十六烷基醚 1.0g
香料 0.5g
防腐剂 适量
抗氧剂 适量
丙二醇 7.8g
甘油 4.0g
透明质酸钠 0.15g
化合物(1) 0.05g
三乙醇胺 1.0g
精制水 57.5g
实施例11:香波的制造例
使用以下材料,按照通常方法制造。
烷基醚硫酸钠 16.0g
月桂酸二乙醇酰胺 4.0g
丙二醇 1.95g
防腐剂、色素、香料 适量
抗氧剂 适量
化合物(1) 0.05g
精制水 78.0g
如上所述,根据本发明发现乌龙茶中含有的新型黄酮C糖苷的衍生物或其盐具有显著的抗过敏作用,可以提供以它们为有效成分的医药组合物、食品组合物、或化妆料。
Claims (10)
1.式(1)所示的黄酮C糖苷衍生物或其盐。
3.过敏性疾病的预防和/或治疗用医药组合物,其含有权利要求1或2所述的黄酮C糖苷衍生物或其盐的至少1种。
4.权利要求3所述的医药组合物,其中,该过敏性疾病为选自特应性皮炎、接触性皮炎、花粉症的至少一种疾病。
5.食品组合物,其含有权利要求1或2所述的黄酮C糖苷衍生物或其盐的至少1种作为抗过敏性成分。
6.权利要求5所述的食品组合物,其是以饮料的形式。
7.权利要求5所述的食品组合物,其中,该食品组合物为糕点类、面食类、大豆加工品、乳制品、蛋加工品、把鱼肉搅碎加其它材料制成的熟食、油脂或调味料。
8.化妆料,其含有权利要求1或2所述的黄酮C糖苷衍生物或其盐的至少1种作为抗过敏性成分。
9.权利要求8所述的化妆料,其中,该化妆料为护肤品、化妆品、毛发化妆料或洗浴料。
10.权利要求1或2所述的黄酮C糖苷衍生物或其盐的至少1种在具有抗过敏性作用的医药组合物、食品组合物或化妆料的制造中的使用。
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JP2005289888A (ja) * | 2004-03-31 | 2005-10-20 | Suntory Ltd | フラボンc配糖体誘導体の製造方法 |
JP2005314260A (ja) * | 2004-04-28 | 2005-11-10 | Japan Science & Technology Agency | フラボンc配糖体の製法 |
JP2006342103A (ja) * | 2005-06-09 | 2006-12-21 | National Cancer Center-Japan | ウーロン茶葉抽出物otacを有効成分とする発癌抑制剤 |
JP5214226B2 (ja) * | 2007-11-02 | 2013-06-19 | 株式会社 資生堂 | チャフロサイド高含有茶葉およびその製造方法 |
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JP5597142B2 (ja) | 2009-01-03 | 2014-10-01 | 静岡県公立大学法人 | 硫酸化c−配糖体及びその単離方法並びに合成方法 |
EP2359698B1 (en) * | 2010-01-22 | 2013-12-04 | Symrise AG | Compositions with a surfactant system comprising saponins, and lecithin |
JP2012219076A (ja) * | 2011-04-12 | 2012-11-12 | Shizuokaken Koritsu Daigaku Hojin | 美白剤およびメラニン生成抑制剤 |
WO2012141255A1 (ja) * | 2011-04-12 | 2012-10-18 | 株式会社 資生堂 | 美白剤およびメラニン生成抑制剤 |
CN109157465B (zh) * | 2018-08-08 | 2020-11-13 | 浙江大学 | 高纯竹叶碳苷黄酮纳米粒子及其制备方法和用途 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03157330A (ja) * | 1989-11-13 | 1991-07-05 | Itouen:Kk | 抗アレルギー剤 |
JPH1077231A (ja) * | 1996-07-12 | 1998-03-24 | Suntory Ltd | 抗アレルギー剤 |
EP0853943A1 (en) * | 1996-12-19 | 1998-07-22 | Suntory Limited | Antiallergic agent |
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JP2006176407A (ja) | 2003-04-18 | 2006-07-06 | Daiichi Asubio Pharma Co Ltd | 新規フラボン誘導体、その製造法およびそれらを含む医薬組成物 |
-
2002
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2003
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03157330A (ja) * | 1989-11-13 | 1991-07-05 | Itouen:Kk | 抗アレルギー剤 |
JPH1077231A (ja) * | 1996-07-12 | 1998-03-24 | Suntory Ltd | 抗アレルギー剤 |
EP0853943A1 (en) * | 1996-12-19 | 1998-07-22 | Suntory Limited | Antiallergic agent |
Non-Patent Citations (3)
Title |
---|
'A new convenient synthesis of benzofuroflavones' AHLUWALIA V.K. ET AL,INDIAN JOURNAL OF CHEMIS TRY,Vol.26B No.3 1987 * |
'Claisen rearrangement of 7-prenyl ethers of chrysin &3-0-methylgalangin: a novel 3-0-demethylation' JAIN A.C. ET AL,INDIAN JOURNAL OF CHEMISTRY,Vol.11 No.8 1973 * |
Fuether prenylflavonoids from artocarpus elasticus. Kijjoa,A. et al,Phytochemistry,Vol.47 No.5 1998 * |
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CA2491027C (en) | 2011-01-04 |
CN1671713A (zh) | 2005-09-21 |
KR20050016934A (ko) | 2005-02-21 |
DE60321924D1 (de) | 2008-08-14 |
ATE399785T1 (de) | 2008-07-15 |
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JP4549009B2 (ja) | 2010-09-22 |
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