CN105816344B - 一种含有吡咯并喹啉醌和n-乙酰基神经氨酸的组合物 - Google Patents
一种含有吡咯并喹啉醌和n-乙酰基神经氨酸的组合物 Download PDFInfo
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- CN105816344B CN105816344B CN201511032793.6A CN201511032793A CN105816344B CN 105816344 B CN105816344 B CN 105816344B CN 201511032793 A CN201511032793 A CN 201511032793A CN 105816344 B CN105816344 B CN 105816344B
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- MMXZSJMASHPLLR-UHFFFAOYSA-N pyrroloquinoline quinone Chemical compound C12=C(C(O)=O)C=C(C(O)=O)N=C2C(=O)C(=O)C2=C1NC(C(=O)O)=C2 MMXZSJMASHPLLR-UHFFFAOYSA-N 0.000 title claims abstract description 90
- 239000000203 mixture Substances 0.000 title claims abstract description 40
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 title claims description 28
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 title claims description 27
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- ZIUYHTQZEPDUCZ-UHFFFAOYSA-N 7h-pyrrolo[2,3-h]quinoline Chemical group C1=CN=C2C(C=CN3)=C3C=CC2=C1 ZIUYHTQZEPDUCZ-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7012—Compounds having a free or esterified carboxyl group attached, directly or through a carbon chain, to a carbon atom of the saccharide radical, e.g. glucuronic acid, neuraminic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明涉及一种组合物,含有吡咯并喹啉醌或其盐和N‑乙酰基神经氨酸,其中吡咯并喹啉醌或其盐和N‑乙酰基神经氨酸的重量比为1∶1‑10,最优选吡咯并喹啉醌或其盐和N‑乙酰基神经氨酸的重量比为1∶5.5,所述的组合物具有很好的抗氧化效果,可以应用化妆品和食品中。
Description
技术领域
本发明涉及一种组合物,具体涉及一种含有吡咯并喹啉醌和N-乙酰基神经氨酸的组合物。
背景技术
吡咯并喹啉醌(PQQ)是最早从微生物发现的小分子化合物,在高等真核生物体内也有存在。PQQ是生物体的能力获得体系中必需的氧化还原的辅酶,可以从各种生物中提取。PQQ的生物活性已经进行了大量的研究,迄今为止已经发现的PQQ的生物活性有:提高人体免疫功能、防治肝损伤、减少自由基、调理神经系统疾病、促进氨基酸的吸收、促进合成生长因子、促进合成谷胱甘肽、抗癌、抗过敏等,PQQ的外用作用有:抗氧化、紫外线吸收、防止皮肤老化、防止光老化、除去活性氧作用等,上述用途使其广泛应用于药品、化妆品、食品等多个领域。吡咯并喹啉醌已经被提出具有成为新的维生素的可能性。
PQQ是一种水溶性化合物,通常以红褐色粉末状存在,PQQ的结构式如下:
燕窝是人们常用的美容保健食品,其中含有多种具有生物活性的化合物,N-乙酰基神经氨酸即为其中的一种,N-乙酰基神经氨酸是一种天然存在的氨基酸糖类的碳水化合物,最初由颌下腺粘蛋白中分离而出,也因此命名为唾液酸。迄今为止已经发现的N-乙酰基神经氨酸的生物活性有:提高婴儿智力和记忆力、抗老年痴呆、抗识别、提高肠道对维生素及矿物质的吸收、抗菌排毒和抗病毒等作用。
N-乙酰基神经氨酸是一种水溶性化合物,通常以白色粉末状存在,N-乙酰基神经氨酸的结构式如下:
含有吡咯并喹啉醌的组合物已经被广泛研究,中国专利CN103458865A公开了一种含有吡咯并喹啉醌和表面活性剂且pH为4-6的外用组合物,可以提高组合物的保存稳定性。中国专利CN102688155A公开了一种含有吡咯并喹啉醌、EDTA和醇的外用组合物,具有优异的弹性蛋白酶活性抑制作用。中国专利CN102793632A公开了一种含有吡咯并喹啉醌和肽的外用组合物,用于改善皮肤粗糙和改善皱纹。
N-乙酰基神经氨酸的应用也被文献所报道,中国专利CN104586642A公开了N-乙酰基神经氨酸在个人护理用品中的应用,具有消炎抑菌,促进细胞修复的功效。中国专利CN104998292A公开了N-乙酰基神经氨酸在卫生用品中的应用,具有抗炎美白的功效。中国专利CN104083291A公开了N-乙酰基神经氨酸在化妆品中的应用,具有保湿、美白、消炎、抗老化的功效。日本专利JP平1-163110A公开了N-乙酰基神经氨酸作为皮肤老化预防剂的应用。
吡咯并喹啉醌的抗氧化作用已经被应用于药品、食品和化妆品领域,但是目前还没有文献报道N-乙酰基神经氨酸具有抗氧化作用,本发明人在研究过程中出乎意料地发现,吡咯并喹啉醌和N-乙酰基神经氨酸组合后的抗氧化作用产生了协同作用,比单独使用吡咯并喹啉醌或N-乙酰基神经氨酸的抗氧化作用要好很多,从而完成了本发明。
发明内容
本发明的一个目的是提供一种组合物。
本发明提供了一种组合物,其特征在于,所述组合物含有吡咯并喹啉醌或其盐和N-乙酰基神经氨酸。
本发明提供了一种组合物,其特征在于,组合物中吡咯并喹啉醌或其盐和N-乙酰基神经氨酸的重量比为1∶1-10。
优选地,本发明的组合物中吡咯并喹啉醌或其盐和N-乙酰基神经氨酸的重量比为1∶3-7。
更优选地,本发明的组合物中吡咯并喹啉醌或其盐和N-乙酰基神经氨酸的重量比为1∶1,1∶5.5或1∶10。
最优选地,本发明的组合物中吡咯并喹啉醌或其盐和N-乙酰基神经氨酸的重量比为1∶5.5。
本发明的吡咯并喹啉醌的盐为吡咯并喹啉醌的无机盐或有机盐,例如无机盐为钠或钾等碱金属盐、钙或镁等碱土金属盐、铵盐,有机盐为三乙醇胺或三乙胺等有机胺盐,赖氨酸或精氨酸等碱性氨基酸盐。优选吡咯并喹啉醌的盐为钠盐或钾盐。上述吡咯并喹啉醌的盐可以单独使用,也可以2种以上组合使用。
本发明的另一个目的是提供上述组合物在制备抗氧化剂的用途。
本发明的另一个目的是提供一种化妆品组合物,其特征在于,所述化妆品组合物含有吡咯并喹啉醌或其盐和N-乙酰基神经氨酸。
本发明的化妆品组合物可以加入化妆品领域可接受的辅料,所述化妆品领域可接受的辅料为:溶剂、增溶剂、防腐剂、pH调节剂、促渗剂、脂质体、保湿剂、增稠剂、螯合剂、肤感调节剂、表面活性剂、乳化剂、推进/抛射剂、香精或/和色素,所述化妆品组合物为香皂、洗面奶、沐浴露、柔肤水、护肤啫喱、护肤乳液、护肤霜、精华液、眼霜、面膜、睫毛膏或唇膏,制成气雾或喷雾形式。
本发明的另一个目的是提供一种食品,其特征在于,所述食品含有吡咯并喹啉醌或其盐和N-乙酰基神经氨酸。
本发明的食品可以加入食品领域可接受的辅料,所述食品领域可接受的辅料为:增稠剂、稳定剂、乳化剂、护色剂、金属络合剂、营养强化剂、防腐剂、着色剂、漂白剂、膨松剂、酸度调节剂、组织改良剂、抗结剂、酶制剂、增味剂或/和食用香料,所述食品为固态或液态形式。
以化妆品组合物或食品的总重量计算,本发明的组合物占上述化妆品组合物或食品的总重量的0.1%-1%,优选0.3%-0.5%。
具体实施方式
下面结合实施例对本发明作进一步的详细说明,但本发明的实施方式不限于此。下述实施例中所用方法如无特别说明均为常规方法。
实施例1:取吡咯并喹啉醌10g和N-乙酰基神经氨酸10g,溶于1000mL蒸馏水,制备成溶液。
实施例2:取吡咯并喹啉醌10g和N-乙酰基神经氨酸55g,溶于1000mL蒸馏水,制备成溶液。
实施例3:取吡咯并喹啉醌10g和N-乙酰基神经氨酸100g,溶于1000mL蒸馏水,制备成溶液。
对比例1:取吡咯并喹啉醌10g,溶于1000mL蒸馏水,制备成溶液。
对比例2:取N-乙酰基神经氨酸10g,溶于1000mL蒸馏水,制备成溶液。
对比例3:取N-乙酰基神经氨酸55g,溶于1000mL蒸馏水,制备成溶液。
对比例4:取N-乙酰基神经氨酸100g,溶于1000mL蒸馏水,制备成溶液。
实施例4:抗氧化效果实验:采用清除DPPH·自由基法测定吡咯并喹啉醌和N-乙酰基神经氨酸的抗氧化作用。
测定DPPH·清除能力的方法:精确称取0.0122gDPPH·溶于无水乙醇中,然后用50%乙醇溶液定容于50mL容量瓶,作为母液冷藏备用,用移液管准确量取10mL母液定容于100mL棕色瓶,得到浓度为0.0244mg/mL的工作液。准确量取一系列不同量的待测液,分别加入10mL比色管中,各加入浓度为0.0244mg/mL的DPPH·溶液2.5mL,用50%乙醇定容至5mL,室温静置反应20分钟后,在517nm处测定吸光度.因体系内DPPH·的浓度与其吸光度成正比,所以可以直接以下式计算待测液对DPPH·的清除率.物质对DPPH·的清除率越高,说明该物质的抗氧化能力越强。
清除率的计算公式如下:清除率(%)=(A0-A)/A0×100%,其中A0为未加待测液时测定的DPPH·溶液的吸光度;A为加入待测液后测定的DPPH·溶液的吸光度。通过测定实施例1-3和对比例1-4的清除率,结果如表1所示。
表1本发明组合物的协同清除作用
由表1的实验结果可知,吡咯并喹啉醌和N-乙酰基神经氨酸的组合对于DPPH·的清除率均大于二者在添加浓度下清除率的代数和,说明吡咯并喹啉醌和N-乙酰基神经氨酸之间存在抗氧化协同作用,可以利用抗氧化剂的协同作用,组合使用抗氧化剂,提高抗氧化效果。
Claims (9)
1.一种组合物,其特征在于,所述组合物含有吡咯并喹啉醌或其盐和N-乙酰基神经氨酸,其中吡咯并喹啉醌或其盐和N-乙酰基神经氨酸的重量比为1∶1-10。
2.根据权利要求1所述的组合物,其特征在于,吡咯并喹啉醌或其盐和N-乙酰基神经氨酸的重量比为1∶3-7。
3.根据权利要求1所述的组合物,其特征在于,吡咯并喹啉醌或其盐和N-乙酰基神经氨酸的重量比为1∶1,1∶5.5或1∶10。
4.根据权利要求1所述的组合物,其特征在于,吡咯并喹啉醌或其盐和N-乙酰基神经氨酸的重量比为1∶5.5。
5.根据权利要求1-4任一项所述的组合物,其特征在于,吡咯并喹啉醌的盐为吡咯并喹啉醌的无机盐或有机盐。
6.根据权利要求5所述的组合物,其特征在于,吡咯并喹啉醌的无机盐为钠盐或钾盐。
7.权利要求1-6任一项所述的组合物在制备抗氧化剂的用途。
8.一种化妆品组合物,其特征在于,所述化妆品组合物含有权利要求1-6任一项所述的组合物。
9.一种食品,其特征在于,所述食品含有权利要求1-6任一项所述的组合物。
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