CN110769833A - 包含源自后发酵茶的新山柰酚类化合物的抗炎组合物 - Google Patents
包含源自后发酵茶的新山柰酚类化合物的抗炎组合物 Download PDFInfo
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- CN110769833A CN110769833A CN201880039243.2A CN201880039243A CN110769833A CN 110769833 A CN110769833 A CN 110769833A CN 201880039243 A CN201880039243 A CN 201880039243A CN 110769833 A CN110769833 A CN 110769833A
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Abstract
本说明书涉及一种抗炎组合物,其包含从后发酵茶中分离的新化合物、其异构体、其药学上可接受的盐、其水合物、其溶剂化物,并且可以广泛用于与抗炎相关的各个领域。
Description
技术领域
本说明书涉及一种包含新山柰酚类化合物的抗炎组合物。
背景技术
炎症是一系列出于防御目的而发生的反应,旨在在细胞或组织由于某些原因而受损时使反应降至最低并使损伤部位恢复到原状,并且炎症引起神经和血管、淋巴管、体液的反应和细胞反应,最终导致疼痛、浮肿、发红和发热等,从而导致功能障碍。导致炎症的原因包括物理因素(例如创伤、冻伤、烧伤、辐射)、化学因素(例如酸的化学物质)和免疫因素(例如抗体反应),另外,炎症还由血管或荷尔蒙失调引起。被外部刺激损伤的细胞分泌的各种化学介质导致血管舒张,并且随着通透性增加,抗体、补体、血浆和吞噬细胞会聚集到炎症部位。这种现象导致红斑。这样的炎症引起各种疾病和皮肤老化,这是由于诸如紫外线、活性氧、自由基等的氧化应激等激活了炎性因子。炎症的特征之一是花生四烯酸的氧化反应增加,花生四烯酸通过产生前列腺素的环氧合酶(COX)和产生白三烯的5-脂氧合酶的途径来代谢。前列腺素和白三烯是炎症的介质。因此,环氧合酶包括环氧合酶-1和环氧合酶-2两种形式。后者形式,即环氧合酶-2,似乎在炎症的进展中起重要作用。因此,抑制环氧合酶-2酶可能是减轻炎症而没有与抑制不可逆环氧合酶-1相关的副作用的有效方式。
绿茶可以以叶茶的形式或为感受更深的香味而以发酵茶的形式饮用。发酵绿茶是指对绿茶叶进行氧化处理,包括由茶叶中存在的氧化酶氧化的发酵茶,以及由不在茶叶中存在的酶的其他微生物发酵的后发酵茶。根据发酵程度,可分为轻发酵茶、半发酵茶和全发酵茶等。例如,根据发酵的类型和程度,发酵绿茶被称为各种名称,例如绿茶、乌龙茶、红茶、普洱茶等。
与叶茶相比,发酵茶不仅会表现出香味差异,而且根据特定的发酵过程和微生物种类,有效成分的种类和含量也可能表现出很大差异。由于如上所述可以生产和分离各种化合物,因此一直在进行各种努力使用绿茶来分离和鉴定未知新化合物。
[引文清单]
[专利文献]
[专利文献1]韩国专利第10-0975199号
发明内容
[技术问题]
一方面,本公开的一个目的是使用源自后发酵茶的新化合物用于抗炎用途。
[技术方案]
在一种实施方式中,本公开提供了一种抗炎组合物,其包含以下物质作为有效成分:式1的化合物、其光学异构体、其药学上可接受的盐、其水合物、其溶剂化物、或包含上述物质的后发酵茶提取物。
[式1]
在上式1中,R1可以为C15H9O6,R2可以为C6H11O5,并且R3可以为C9H7O2。
另外,在本发明的另一方面,该组合物可以是抑制选自PGE2(前列腺素E2)、IL-6(白介素6)和IL-8(白介素8)中的一种或多种的产生的组合物。
根据一种实施方式,本发明提供了一种用于抗炎的方法,其包括向有需要的对象施用式1的化合物、其光学异构体、其药学上可接受的盐、其水合物、其溶剂化物、或包含上述物质的后发酵茶提取物。
根据一种实施方式,本发明提供了式1的化合物、其光学异构体、其药学上可接受的盐、其水合物、其溶剂化物、或包含上述物质的后发酵茶提取物在制备抗炎组合物中的用途。
根据一种实施方式,本发明提供了用于抗炎的式1的化合物、其光学异构体、其药学上可接受的盐、其水合物、其溶剂化物、或包含上述物质的后发酵茶提取物。
[有益效果]
在一方面,通过使得从后发酵茶中分离出的新化合物可用于抗炎领域,本发明可广泛应用于后发酵茶相关产业、抗炎相关领域等。
附图说明
图1显示了根据本发明的一方面的化合物的MS光谱。
图2显示了根据本发明的一方面的化合物的1H-NMR(核磁共振)光谱。
图3显示了根据本发明的一方面的化合物的13C-NMR光谱。
图4显示了根据本发明的一方面的化合物的1H-13C HSQC(异核单量子相干)光谱。
图5显示了根据本发明的一方面的化合物的1H-13C HMBC(异核多键相干)光谱。
具体实施方式
在下文中,将详细解释本发明。
在本说明书中,“后发酵”包括由不在茶叶中存在的酶的其他微生物或物质发酵。后发酵茶包括通过上述方法发酵的绿茶。
在本说明书中,“提取物”包括通过提取天然物质内包含的成分而获得的所有物质,无论提取方法或成分如何。该术语具有广泛的概念,包括例如使用水或有机溶剂从天然物质中提取可溶于溶剂的成分而获得的物质,仅提取特定成分,例如天然物质的特定成分(例如油)所获得的物质,以及通过对如上获得的物质再次用特定溶剂等进行分级而获得的级分等。
在本说明书中,“级分”包括通过使用特定溶剂对特定物质或提取物进行分级而获得的物质或分级后剩下的物质,以及将这些物质再次用特定溶剂提取而获得的物质。分级方法和提取方法可以是本领域技术人员已知的任何方法。
在本说明书中,“异构体”不仅特别地包括光学异构体(例如,基本上纯的对映异构体、基本上纯的非对映异构体或其混合物),而且还包括构象异构体(即,仅在它们的一个或多个化学键的角度上不同的异构体)、位置异构体(特别是互变异构体)或几何异构体(例如顺反异构体)。
在本说明书中,“基本上纯的”是指,例如当与对映异构体或非对映异构体一起使用时,特定化合物例如对映异构体或非对映异构体存在的量为约90w/w%或更多、优选约95w/w%或更多、更优选约97w/w%或更多或约98w/w%或更多、甚至更优选约99w/w%或更多、甚至更进一步优选约99.5w/w%或更多。
在本说明书中,“药学上可接受的”是指当以常规药物剂量使用时通过避免显著毒性作用而可以被或被政府或等效监管机构批准用于动物,更具体地用于人类,或公认在药典中或在其他一般药典中列出。
在本说明书中,“药学上可接受的盐”是指根据本发明一方面的盐,其是药学上可接受的并且具有母体化合物的所需药理活性。该盐可包括(1)由无机酸形成的酸加成盐,所述无机酸例如盐酸、氢溴酸、硫酸、硝酸、磷酸等;或由有机酸形成的酸加成盐,所述有机酸例如乙酸、丙酸、己酸、环戊烷丙酸、乙醇酸、丙酮酸、乳酸、丙二酸、琥珀酸、苹果酸、马来酸、富马酸、酒石酸、柠檬酸、苯甲酸、3-(4-羟基苯甲酰基)苯甲酸、肉桂酸、扁桃酸、甲磺酸、乙磺酸、1,2-乙二磺酸、2-羟基乙磺酸、苯磺酸、4-氯苯磺酸、2-萘磺酸、4-甲苯磺酸、樟脑磺酸、4-甲基双环[2,2,2]-辛-2-烯-1-羧酸、葡庚酸、3-苯基丙酸、三甲基乙酸、叔丁基乙酸、月桂基硫酸、葡萄糖酸、谷氨酸、羟基萘甲酸、水杨酸、硬脂酸、粘康酸;(2)取代存在于母体化合物中的酸性质子时形成的盐。
在本说明书中,“水合物”是指与水键合的化合物,并且具有广泛的概念,包括在水与该化合物之间没有化学键合力的包合化合物。
在本说明书中,“溶剂化物”是指在溶质的分子或离子与溶剂的分子或离子之间形成的更高级的化合物。
在一个方面,本公开提供了一种抗炎组合物,其包含以下物质作为有效成分:下式1的化合物、其异构体、其药学上可接受的盐、其水合物、其溶剂化物、或包含上述物质的后发酵茶提取物。
[式1]
在上式1中,R1可以为C15H9O6,R2可以为C6H11O5,并且R3可以为C9H7O2。
在一种实施方式中,R1可以是下式2的化合物。
[式2]
在另一种实施方式中,R2可以是下式3的化合物。
[式3]
R3可以是下式4的化合物。
[式4]
在另一种实施方式中,该化合物可以是山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷])。该化合物可以由下式5表示。
[式5]
根据本发明的一个方面,一种用于制备化合物、其异构体、其药学上可接受的盐、其水合物或其溶剂化物的方法可以包括合成、从天然物质中分离等。
根据另一种实施方式,后发酵可以通过菌株接种来进行,并且该菌株可以是选自酵母属(Saccharomyces sp.)、芽孢杆菌属(Bacillus sp.)、乳杆菌属(Lactobacillussp.)和明串珠菌属(Leuconostoc mesenteroides sp.)的菌株,并且可以优选地选自啤酒酵母(Saccharomyces cerevisiae)、干酪乳杆菌(Lactobacillus casei)、枯草芽孢杆菌(Bacillus subtlis),保加利亚乳杆菌(Lactobacillus bulgarius)和肠系膜明串珠菌(Leuconostoc mesenteroides)。根据另一种实施方式,后发酵茶可以是通过后发酵绿茶获得的茶。
在本公开的一方面,该化合物是本发明人在不断研究后发酵茶后发现的化合物,并且证实该化合物可有效抑制选自PGE2(前列腺素E2)、IL-6(白介素6)和IL-8(白介素8)中的一种或多种的产生。因此,本发明人已经证明,通过使用根据本发明的一方面的化合物,该化合物可以用于抑制、预防、治疗或减轻炎症的目的。
根据一种实施方式,提取可以是通过选自水、热水、C1至C6的低级醇及其混合溶剂中的一种或多种溶剂的提取,并且在另一种实施方式中,低级醇可以是单独的醇,也可以是本领域通常可以使用的混合物,优选可以是乙醇。
根据本发明的另一方面,该提取物可以是提取后通过用酮对提取物分级所获得的级分。
在另一种实施方式中,酮的实例可包括丙酮、香芹酮、长叶薄荷酮、异长叶烷酮、2-庚酮、2-戊酮、3-己酮、3-庚酮、4-庚酮、2-辛酮、3-辛酮、2-壬酮、3-壬酮、2-十一烷酮、2-十三烷酮、甲基异丙基酮、乙基异戊基酮、丁烯丙酮、甲基庚烯酮、二甲基辛烯酮、香叶基丙酮、法呢基丙酮、2,3-戊二酮、2,3-己二酮、3,4-己二酮、2,3-庚二酮、戊基环戊酮、戊基环戊烯酮、2-环戊基环戊酮、己基环戊酮、2-正庚基环戊酮、顺式茉莉酮、二氢茉莉酮、二甲基环戊烯醇酮(methyl corylone)、2-叔丁基环己酮、对叔丁基环己酮、2-仲丁基环己酮、芹菜酮、隐酮(krypton)、对叔戊基环己酮、甲基环柠檬酮、橙花酮、4-环己基-4-甲基-2-戊酮、酮氧化物、emoxyprone、甲基萘酮、α-甲基茴香叉丙酮、茴香基丙酮、对甲氧基苯基丙酮、亚苄基丙酮、对甲氧基苯乙酮、对甲基苯乙酮、丙苯酮、苯乙酮、α-王朝酮、埃里酮、紫罗酮、假紫罗酮、甲基紫罗酮、甲基埃里酮、2,4-二叔丁基环己酮、烯丙基紫罗酮、2-乙酰基-3,3-二甲基降冰片烷、马鞭草烯酮、葑酮、环十五烷酮、环十六烯酮等,可以包括全部酮及其混合物作为本领域中通常可以使用的溶剂,并且可以优选为丙酮。
根据本发明的一方面,基于组合物的总重量,组合物中的式1的化合物、其异构体、其药学上可接受的盐、其水合物或其溶剂化物的含量可以为0.00001重量%至10重量%。该含量可以为0.00001重量%或更多、0.00005重量%或更多、0.0001重量%或更多、0.0005重量%或更多、0.001重量%或更多、0.005重量%或更多、0.01重量%或更多、0.05重量%或更多、0.1重量%或更多、0.5重量%或更多、1重量%或更多、2重量%或更多、3重量%或更多、4重量%或更多、5重量%或更多、6重量%或更多、7重量%或更多、8重量%或更多、或9重量%或更多。另外,该含量可以为10重量%或更少、9重量%或更少、8重量%或更少、7重量%或更少、6重量%或更少、5重量%或更少、4重量%或更少、3重量%或更少、2重量%或更少、1重量%或更少、0.5重量%或更少、0.1重量%或更少、0.05重量%或更少、0.01重量%或更少、0.005重量%或更少、0.001重量%或更少、0.0005重量%或更少、0.0001重量%或更少、0.00005重量%或更少、或0.00003重量%或更少。
根据本发明的另一方面,基于组合物的总重量,组合物中后发酵茶提取物的含量可以为0.1重量%至90重量%。基于组合物的总重量,该含量可以为0.1重量%或更多、1重量%或更多、5重量%或更多、10重量%或更多、15重量%或更多、20重量%或更多、25重量%或更多、30重量%或更多、35重量%或更多、40重量%或更多、45重量%或更多、50重量%或更多、55重量%或更多、60重量%或更多、65重量%或更多、70重量%或更多、75重量%或更多、80重量%或更多、或85重量%或更多。另外,该含量可以为90重量%或更少、85重量%或更少、80重量%或更少、75重量%或更少、70重量%或更少、65重量%或更少、60重量%或更少、55重量%或更少、50重量%或更少、45重量%或更少、40重量%或更少、35重量%或更少、30重量%或更少、25重量%或更少、20重量%或更少、15重量%或更少、10重量%或更少、5重量%或更少、1重量%或更少、或0.5重量%或更少。
根据本发明的另一方面,基于提取物的总重量,提取物包含的式1的化合物、其异构体、其药学上可接受的盐、其水合物或其溶剂化物的含量可以为0.00001重量%或更多、0.00005重量%或更多、0.0001重量%或更多、0.0005重量%或更多、0.001重量%或更多、0.005重量%或更多、0.01重量%或更多、0.05重量%或更多、0.1重量%或更多、0.5重量%或更多、1重量%或更多、3重量%或更多、5重量%或更多、7重量%或更多、10重量%或更多、12重量%或更多、15重量%或更多、或18重量%或更多。另外,该含量可以为20重量%或更少、15重量%或更少、12重量%或更少、10重量%或更少、7重量%或更少、5重量%或更少、3重量%或更少、1重量%或更少、0.5重量%或更少、0.1重量%或更少、0.05重量%或更少、0.01重量%或更少、0.005重量%或更少、0.001重量%或更少、0.0005重量%或更少、0.0003重量%或更少、0.00005重量%或更少、或0.00003重量%或更少。优选地,基于提取物的总重量,提取物包含的式1的化合物、其异构体、其药学上可接受的盐、其水合物或其溶剂化物的含量可以为0.00001重量%至20重量%。
根据本发明的另一方面,通过施用组合物,式1的化合物、其异构体、其药学上可接受的盐、其水合物或其溶剂化物的剂量可以为0.00001mg/kg/天至100mg/kg/天。该剂量可以是0.00001mg/kg/天或更多、0.0001mg/kg/天或更多、0.001mg/kg/天或更多、0.005mg/kg/天或更多、0.01mg/kg/天或更多、0.05mg/kg/天或更多、0.1mg/kg/天或更多、0.5mg/kg/天或更多、1mg/kg/天或更多、5mg/kg/天或更多、10mg/kg/天或更多、15mg/kg/天或更多、20mg/kg/天或更多、25mg/kg/天或更多、30mg/kg/天或更多、35mg/kg/天或更多、40mg/kg/天或更多、45mg/kg/天或更多、50mg/kg/天或更多、55mg/kg/天或更多、60mg/kg/天或更多、65mg/kg/天或更多、7mg/kg/天或更多、75mg/kg/天或更多、80mg/kg/天或更多、85mg/kg/天或更多、90mg/kg/天或更多、或95mg/kg/天或更多。另外,该剂量可以为100mg/kg/天或更少、95mg/kg/天或更少、90mg/kg/天或更少、85mg/kg/天或更少、80mg/kg/天或更少、75mg/kg/天或更少、70mg/kg/天或更少、65mg/kg/天或更少、60mg/kg/天或更少、55mg/kg/天或更少、50mg/kg/天或更少、45mg/kg/天或更少、40mg/kg/天或更少、35mg/kg/天或更少、30mg/kg/天或更少、25mg/kg/天或更少、20mg/kg/天或更少、15mg/kg/天或更少、10mg/kg/天或更少、5mg/kg/天或更少、1mg/kg/天或更少、0.5mg/kg/天或更少、0.1mg/kg/天或更少、0.05mg/kg/天或更少、0.01mg/kg/天或更少、0.005mg/kg/天或更少、0.003mg/kg/天或更少、0.001mg/kg/天或更少、0.0005mg/kg/天或更少、0.0001mg/kg/天或更少、或0.00005mg/kg/天或更少。
根据一种实施方式,炎症可以是由于选自PGE2(前列腺素E2)、IL-6(白介素6)和IL-8(白介素8)中的一种或多种的产生或增加而引起的。
根据本发明的另一方面,该组合物可以是食品组合物、化妆品组合物或药物组合物。
根据本发明的一方面的食品组合物可以是保健食品组合物。在保健食品组合物中,化合物的剂量确定在本领域技术人员的水平之内,并且可以根据多种因素而变化,所述因素包括待施用的对象的年龄、健康状况和并发症等。
根据本发明的一方面的保健食品组合物可以是保健功能食品,并且也可以包括任何形式的加工食品,例如各种食品类(例如口香糖、焦糖产品、糖果、冰淇淋、点心、面包等)和饮料(例如软饮料、矿泉水、酒精饮料等),并且可以是包含维生素、矿物质等的功能性食品类。
除上述之外,根据本发明的一方面的保健食品组合物可以包含各种营养物、维生素、矿物质(电解质)、调味剂(例如合成调味剂和天然调味剂)、着色剂和增强剂(奶酪、巧克力等)、果胶酸及其盐、藻酸及其盐、有机酸、保护性胶体增稠剂、pH调节剂、稳定剂、防腐剂、甘油、醇类和用于碳酸化饮料的碳酸化剂等。另外,本发明的保健食品组合物可包含天然果汁和用于生产果汁饮料和蔬菜饮料的果肉。这些成分可以单独使用或组合使用。这样的添加剂的比例不是很关键,但是根据本发明的一方面,每100重量份的组合物通常包含0至约50重量份的添加剂。
根据本发明的一方面的化妆品组合物是用于皮肤、指甲和/或头发的组合物,并且可以具有例如以下的剂型:柔软化妆水、收敛化妆水、滋养化妆水、滋养霜、按摩霜、眼霜、眼部精华液、精华液、洁面霜、洁面乳、洁面泡沫、洁面水、面膜、粉末、身体乳、身体霜、身体精华液、沐浴露、染发剂、洗发水、润发素、护发素、养发剂、软膏、凝胶、霜、贴剂、喷雾剂和皮肤贴类型等,但不限于此。
另外,在每种制剂中,本领域技术人员可以根据其他外用制剂的种类或使用目的适当地选择并掺混除上述必需成分以外的其他成分。
化妆品组合物可以以适合局部应用的任何剂型提供。例如,可以以溶液、通过使油相在水相中分散而获得的乳液、通过使水相在油相中分散而获得的乳液、悬浮液、固体、凝胶、粉末、糊剂、微针、泡沫或气雾剂组合物的形式提供。这些剂型的组合物可以根据相关领域中的常规方法来制备。
除了本说明书的化合物、提取物或级分之外,根据本说明书的化妆品组合物还可包含在一般化妆品组合物中包含的功能添加剂和成分。功能添加剂可包括选自水溶性维生素、油溶性维生素、聚合物肽、聚合物多糖、鞘脂和海藻提取物的成分。在不损害主要作用的范围内,根据本说明书的化妆品组合物优选可以包含可对主要作用产生协同作用的其他成分。另外,根据本说明书的化妆品组合物还可包含保湿剂、润肤剂、表面活性剂、紫外线吸收剂、防腐剂、杀菌剂、抗氧化剂、pH调节剂、有机和无机颜料、香料、冷感剂或止汗剂。本领域技术人员可以在不损害本说明书的目的和效果的范围内容易地选择各成分的掺混量,基于组合物的总重量,该掺混量可以为0.001至10重量%,特别是0.01至3重量%。
根据另一种实施方式,该组合物可以是皮肤外用剂组合物。皮肤外用剂组合物可以是诸如化妆品、口腔制剂、清洁剂、药物和准药物的组合物,但不限于此。皮肤外用剂的剂型没有特别限制。
另外,本说明书的皮肤外用剂组合物可以进一步包括选自用于特定目的的功能性盐和用于调节pH的pH调节剂中的一种或多种。在这种情况下,该盐可以选自用于离子屏蔽、保湿、防紫外线等的无机盐、有机盐和/或有机-无机盐。作为具体的实例,该盐可以选自氯化钠(NaCl)、磷酸钠(Na3PO4),氯化钙(CaCl2)等。pH调节剂可以选自酸和碱,例如选自盐酸、硫酸、酒石酸、柠檬酸、磷酸、乙酸、乳酸、乳酸钠、氢氧化钠、氢氧化钾、烷基胺、烷醇胺和氨等。
本说明书的皮肤外用剂组合物可以是化妆品、药物或准药物组合物,其中所述化妆品、药物或准药物组合物可以另外包含防腐剂、稳定剂、水合剂或乳化剂、用于控制渗透压的盐和/或缓冲液等助剂和其他治疗上有用的物质。可以将组合物配制成洗剂、霜剂、软膏、凝胶等。皮肤外用剂组合物可优选经皮施用。
药物或准药物组合物的有效成分的剂量可以根据待治疗的对象的年龄、性别和体重、待治疗的具体疾病或病理、疾病或病理状态的严重程度、给药途径和处方者的判断而变化。基于这些因素的剂量确定在本领域技术人员的水平之内。通常,有效成分的剂量可以为0.00001mg/kg/天至15mg/kg/天,但不限于此。
根据本发明的一方面的药物组合物可以口服、胃肠外、直肠、局部、经皮、静脉内、肌内、腹膜内、皮下等施用。口服施用的剂型可以是但不限于片剂、丸剂、软胶囊剂和硬胶囊剂、颗粒剂、粉剂、细颗粒剂、溶液剂、乳浊剂或小丸剂。肠胃外施用的剂型可以是但不限于溶液剂、悬浊剂、乳液剂、凝胶、注射剂、滴剂、栓剂、贴剂或喷雾剂。该制剂可以根据相关领域的常规方法容易地制备,并且可以另外包含表面活性剂、赋形剂、水合剂、乳化剂、悬浊剂、用于控制渗透压的盐或缓冲剂、着色剂、香料、稳定剂、防腐剂、保存剂或其他可商购的助剂。
根据本发明的一方面的药物组合物的量或剂量可以根据要施用的对象的年龄、性别、体重、病理状态和严重性、给药途径或处方者的判断而变化。基于这些因素的剂量确定在本领域技术人员的水平之内。
食品组合物的剂型没有特别限制,例如可以配制成片剂、颗粒剂、丸剂、粉剂、液体(如饮料)、焦糖、凝胶、棒、茶袋等。在每种剂型的食品组合物中,除了有效成分之外,相关领域中通常使用的成分可以由本领域技术人员容易地根据剂型或使用目的适当地选择和掺混,并且当该组合物与其他原料同时应用时,可能会产生协同效应。
该组合物可以通过各种方法施用,例如简单的摄入、饮用、注射施用、喷雾施用或挤压施用等。
在下文中,将参考实施例、实验例和剂型例更详细地描述本说明书的配置和效果。然而,提供这些实施例仅出于说明的目的,以促进对本说明书的理解,并且本说明书的范畴和范围不受以下实施例的限制。
[实施例]
[实施例1]后发酵茶样品的制备
通过将水添加到由绿茶(Camellia sinensis var.Yabukita)叶制成的绿茶中,将水含量调节至40重量%。然后对绿茶接种5×106cfu/g枯草芽孢杆菌(Bacillussubtillis),在50℃下发酵3天,然后在80℃下发酵4天。
将发酵的茶样品粉碎15秒,并通过网眼尺寸为1mm的不锈钢筛过滤。然后,将50mg的粉碎样品添加到1.5ml Eppendorf管中,添加1ml去离子水,并在60℃恒温水浴中恒速搅拌30分钟,然后在25℃,13,000rpm下离心15分钟。从离心的发酵绿茶提取物中仅分离出不溶于水的部分。
[实施例2]级分的获得和化合物的分离
将150g的后发酵茶样品用丙酮分级分离以去除儿茶素衍生物和咖啡因,并获得其中浓缩了其他化合物的可溶物。对于40g的丙酮可溶物,主要使用硅胶柱色谱法,使用5:1(v/v)的氯仿:甲醇的混合物作为溶剂获得级分。
使用大容量高效逆流色谱法(HPCCC,Dynamic Extractions Ltd,UK)将8.9g不含咖啡因的5:1(v/v)的氯仿:甲醇级分分级。然后使用的溶剂是正己烷-TBME(甲基叔丁基醚)-BuOH-MeCN-水(0.25:3:1:1:5,v/v),流速为25ml/分钟。使用上述条件,级分总共分出10个子级分,并再次使用小容量HPCCC(Dynamic Extractions Ltd,UK)、高效液相色谱(HPLC)、Sephadex LH-20色谱柱(GE Healthcare Bio-Sciences,Sweden)等分离各级分中所含的成分。
结果,从级分中可以分离出山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷],这是一种以前未知的化合物。通过使用1H-NMR、13C-NMR(核磁共振波谱)、UV(紫外光谱)和ESI-MS(电喷雾电离质谱)鉴定结构,确定每种化合物的结构。在1H和13C核磁共振(NMR)的情况下,使用甲醇-d3作为溶剂,并使用Bruker Advance DPX-500(BRUKER,USA)作为装置。使用6200Series Accurate-Mass Time-of-Flight(TOF)LC/MS(Agilent,US)分析每种化合物的MS质谱图。
作为分析的结果,每种化合物都是以前未知的新化合物,并被确认为山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷](“新物质33”),其是C42H46O22,分子量为902.2481的。
山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷]的化学式和NMR数据如下。
[表1]
山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷]的MS质谱如图1所示,1H-NMR谱和13C-NMR谱分别如图2和图3所示,HSQC(异核单量子相干)光谱如图4所示。HMBC(异核多键相干)光谱如图5所示。
[实验例1]用于抑制PGE2、IL-6和IL-8的产生的实验
将人成纤维细胞(PromoCell,Germany)以1×105细胞的浓度接种到6孔培养板中,并在37℃,5%CO2的培养箱中培养24小时。在孔中用500μM H2O2处理并刺激24小时后,各自用山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷](“新物质33”)以100μg/ml的浓度处理,并反应48小时。反应完成后,收集培养基并进行ELISA分析。同时将作为常用的抗炎剂和缓和剂的α-没药醇用作对照。对于PGE2使用Assay Design的试剂盒,对于IL-6和IL-8使用Endogen的试剂盒,并根据各公司手册中指定的方法进行实验。根据以下等式1计算抑制效果,并且测量结果示于下表3中。(“33”表示新物质33)
<等式1>
抑制作用={1-(测试样品-对照)/(H2O2-对照)}×100
[表2]
PGE<sub>2</sub>(pg/ml) | IL-6(pg/ml) | IL-8(pg/ml) | |
H<sub>2</sub>O<sub>2</sub>(500μM) | 350 | 245 | 290 |
对照(α-没药醇) | 205 | 180 | 200 |
H<sub>2</sub>O<sub>2</sub>+33(100μg/ml) | 231 | 198 | 210 |
根据等式1的33的抑制作用 | 82.07 | 72.31 | 88.89 |
如上表2所示,新物质33具有减少H2O2所增加的PGE 2、IL-6和IL-8的作用。这意味着新物质33分别具有抗炎作用,因此证实了新物质33可用于预防、治疗、改善每种炎症的目的。
[实验例2]皮肤蓄积刺激实验
进行了人重复性损伤性斑贴试验(HRIPT),以确认山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷]的皮肤蓄积刺激,并计算可用于皮肤的浓度范围。
具体地,随机选择15名健康的成年人测试者,并且将包含0.5重量%、1重量%和3重量%的化合物的测试组合物(除了该化合物之外还包含乳化剂、稳定剂、纯净水等的皮肤组合物)逐滴添加20μl到每个小室(IQ chamber,Epitest Ltd,Finland)中。贴附在测试者的上背部右侧部位24小时后,将其替换为新的斑贴。以此方式,总共进行了9次斑贴试验,每周3次,共3周,每次检查贴附之前和之后的皮肤反应,并观察皮肤反应直到最后的斑贴去除后48小时,观察了平均反应度。结果显示在下表3中。
[表3]
皮肤反应是根据国际接触性皮肤炎研究小组(ICDRG)的标准确定的。上表中的“新物质33”是山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷]。也就是说,所有物质在该含量范围内均显示出(-)反应度(没有对象表现出±、+、++或+++反应度),由此证实该物质对皮肤没有蓄积刺激性并且可以在皮肤上安全使用。
在下文中,将解释根据本发明的一个方面的组合物的剂型例,但是本发明的范围不限于此。
[剂型例1]软胶囊剂
根据常规方法,将10mg山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷]、80至140mg L-肉碱、180mg大豆油、2mg棕榈油、8mg植物硬化油、4mg黄蜡和6mg卵磷脂混合并填充至一个胶囊中,制备软胶囊剂。
[剂型例2]片剂
将10mg山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷]、200mg低聚半乳糖、60mg乳糖和140mg麦芽糖混合并使用流化床干燥机制粒,然后添加6mg糖酯,并用压片机压片以制备片剂。
[剂型例3]颗粒剂
将5mg山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷]、250mg无水结晶葡萄糖和550mg淀粉混合,使用流化床制粒机模制成颗粒,然后填充到袋中以制备颗粒剂。
[剂型例4]饮料
将2mg山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷]、10g葡萄糖、0.6g柠檬酸和25g液态低聚糖混合,然后添加300ml纯净水。每个瓶子装入200ml。装入瓶子后,将它们在130℃的温度下灭菌4至5秒以制备饮料。
[剂型例5]注射剂
根据常规方法,使用20mg山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷]、适量的注射用无菌蒸馏水和适量的pH调节剂,制备注射剂。
[剂型例6]保健食品
保健食品是根据下表4所示的组成以常规方法制备的。
[表4]
维生素和无机混合物的组成比只是相对适合于保健食品的成分的混合物的例子,可以对混合比进行任意的变形,上述成分可以根据用于制备保健食品的常规方法混合,然后可以根据常规方法用于制备保健食品组合物。
[剂型例7]保健饮料
[表5]
如上表5所示,添加余量的纯净水以使总体积为900ml,并且根据用于制备保健饮料的常规方法将上述成分混合,搅拌并在85℃下加热约1小时,然后将所得溶液过滤至灭菌的2L容器中,灭菌并密封,然后冷藏以制备保健饮料。
[剂型例8]柔软化妆水(皮肤乳液)
使用0.2wt%山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷]、1.00wt%L-抗坏血酸-2-磷酸镁盐、5.00wt%水溶性胶原蛋白(1%水溶液)、0.10wt%柠檬酸钠、0.05wt%柠檬酸、0.20wt%甘草提取物、3.00wt%的1,3-丁二醇和其余量的纯净水制备柔软化妆水(皮肤乳液)。
[剂型例9]霜剂
使用0.2wt%山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷]、2.00wt%聚乙二醇单硬脂酸酯、5.00wt%自乳化甘油单硬脂酸酯、4.00wt%丙二醇、6.00wt%角鲨烯、6.00wt%三2-乙基己烷甘油酯、1.00wt%神经鞘氨糖脂、7.00wt%1,3-丁二醇、5.00wt%蜂蜡和余量的纯净水制备霜剂。
[剂型例10]面膜
0.2wt%山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷]、21.00wt%聚乙烯醇、3.00wt%L-抗坏血酸-2-磷酸镁、5.00wt%月桂酰羟脯氨酸、8.00wt%水溶性胶原蛋白(1%水溶液)、7.00wt%1,3-丁二醇、7.00wt%的乙醇和余量的纯净水制备组合物,然后制备面膜。
根据前述内容,已经参考本说明书的特定实施例描述了本发明,并且对于本领域技术人员而言显而易见的是,这些特定技术仅仅是优选实施方式,而不旨在限制本说明书的范围。因此,本说明书的实质范围将由所附权利要求及其等同物来限定。
Claims (15)
5.根据权利要求1所述的抗炎组合物,其特征在于,所述化合物为山柰酚3-O-[2-O”-(E)-对香豆酰基][β-D-吡喃葡萄糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷]。
6.根据权利要求1所述的抗炎组合物,其特征在于,所述提取是通过选自热水、C1至C6的低级醇及其混合溶剂中的一种或多种溶剂的提取。
7.根据权利要求6所述的抗炎组合物,其特征在于,所述低级醇是乙醇。
8.根据权利要求1所述的抗炎组合物,其特征在于,所述提取物是提取后通过用酮对提取物分级所获得的级分。
9.根据权利要求8所述的抗炎组合物,其特征在于,所述酮是丙酮。
10.根据权利要求1所述的抗炎组合物,其特征在于,基于所述组合物的总重量,所述式1的化合物、其光学异构体、其药学上可接受的盐、其水合物或其溶剂化物的含量为0.00001重量%至10重量%。
11.根据权利要求1所述的抗炎组合物,其特征在于,基于所述组合物的总重量,所述组合物中所述后发酵茶提取物的含量为0.1重量%至90重量%。
12.根据权利要求1所述的抗炎组合物,其特征在于,基于所述提取物的总重量,所述提取物包含的所述式1的化合物、其光学异构体、其药学上可接受的盐、其水合物或其溶剂化物的含量0.00001重量%至20重量%。
13.根据权利要求1所述的抗炎组合物,其特征在于,所述式1的化合物、其光学异构体、其药学上可接受的盐、其水合物或其溶剂化物的剂量为0.00001mg/kg/天至100mg/kg/天。
14.根据权利要求1至13中任一项所述的抗炎组合物,其特征在于,所述组合物抑制选自PGE2(前列腺素E2)、IL-6(白介素6)和IL-8(白介素8)中的一种或多种的产生。
15.根据权利要求1至13中任一项所述的抗炎组合物,其特征在于,所述组合物为食品组合物、化妆品组合物或药物组合物。
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WO2018230909A1 (ko) | 2018-12-20 |
JP2020523299A (ja) | 2020-08-06 |
US20200115409A1 (en) | 2020-04-16 |
JP7179025B2 (ja) | 2022-11-28 |
KR102359443B1 (ko) | 2022-02-09 |
US11248017B2 (en) | 2022-02-15 |
CN110769833B (zh) | 2023-05-12 |
KR20180135304A (ko) | 2018-12-20 |
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