CN113087899A - 一种l-抗坏血酸衍生物及其制备方法、应用 - Google Patents
一种l-抗坏血酸衍生物及其制备方法、应用 Download PDFInfo
- Publication number
- CN113087899A CN113087899A CN202110341128.4A CN202110341128A CN113087899A CN 113087899 A CN113087899 A CN 113087899A CN 202110341128 A CN202110341128 A CN 202110341128A CN 113087899 A CN113087899 A CN 113087899A
- Authority
- CN
- China
- Prior art keywords
- ascorbic acid
- solution
- pga
- acid derivative
- acid
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
-
- 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
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/55—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound the modifying agent being also a pharmacologically or therapeutically active agent, i.e. the entire conjugate being a codrug, i.e. a dimer, oligomer or polymer of pharmacologically or therapeutically active compounds
- A61K47/551—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound the modifying agent being also a pharmacologically or therapeutically active agent, i.e. the entire conjugate being a codrug, i.e. a dimer, oligomer or polymer of pharmacologically or therapeutically active compounds one of the codrug's components being a vitamin, e.g. niacinamide, vitamin B3, cobalamin, vitamin B12, folate, vitamin A or retinoic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
- A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
- A61K47/645—Polycationic or polyanionic oligopeptides, polypeptides or polyamino acids, e.g. polylysine, polyarginine, polyglutamic acid or peptide TAT
-
- 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
- A61K8/67—Vitamins
- A61K8/676—Ascorbic acid, i.e. vitamin C
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/88—Polyamides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/59—Mixtures
- A61K2800/592—Mixtures of compounds complementing their respective functions
- A61K2800/5922—At least two compounds being classified in the same subclass of A61K8/18
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
- A61K2800/782—Enzyme inhibitors; Enzyme antagonists
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Polymers & Plastics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明公开了一种L‑抗坏血酸衍生物及其制备方法、应用,本发明将低分子量γ‑聚谷氨酸与L‑抗坏血酸6位羟基进行连接,产生一种新的L‑抗坏血酸衍生物‑‑‑6‑O‑PGA‑L‑抗坏血酸,该衍生物稳定性强且安全无毒,可作为维生素C的前体,对酪氨酸酶活性抑制率在75%以上,有效抑制皮肤中黑色素沉着。
Description
技术领域
本发明涉及一种L-抗坏血酸衍生物及其制备方法、应用,属于化学合成领域。
背景技术
L-抗坏血酸,是一种水溶性维生素,具有增强免疫力、抗过敏、抗癌、改善血管通透性以及促进胶原、牙齿和骨骼等细胞间质的合成等作用。另外,抗坏血酸可以抑制机体中黑色素的形成从而发挥抗氧化和美白肌肤的作用。但是人体不能合成抗坏血酸,需要从食物中进行获取。抗坏血酸极不稳定,在光、氧气或高热条件下极易变质,因此在化妆品中添加的常为抗坏血酸衍生物,比如:抗坏血酸磷酸酯钠(SAP)、抗坏血酸磷酸酯镁(MAP)、抗坏血酸葡萄糖苷(AA2G)、抗坏血酸乙基醚(VITENNA COS-抗坏血酸E)。与抗坏血酸相比,抗坏血酸衍生物不仅可以发挥抗坏血酸的美白抗氧化作用,并且具有非还原性,性质稳定,具有较好的耐光性和耐热性。其中抗坏血酸葡萄糖苷(AA2G)在体外非常稳定,在体内可以通过哺乳动物的α-葡萄糖苷酶的作用产生游离抗坏血酸,表现出抗坏血酸活性。
抗坏血酸衍生物具有稳定性强、美白效果显著、作用温和等优点,因而很多研究对抗坏血酸进行结构选择性修饰,主要包括L-抗坏血酸的5、6位选择性修饰、3位羟基选择性修饰和2位羟基选择性修饰,其中对6位羟基的选择性修饰备受青睐,这是因为对6位修饰的产物相比于其它位的修饰产物具有更简便的修饰方法。对于6位修饰产物,例如抗坏血酸棕榈酸酯和抗坏血酸硬脂酸酯,稳定性较差,略低于抗坏血酸磷酸酯钠等非6位衍生物,本发明将低分子量γ-聚谷氨酸与L-抗坏血酸6位羟基进行连接,提高其稳定性。
发明内容
本发明克服了上述现有技术的不足,提供一种L-抗坏血酸衍生物及其制备方法、应用,本发明将低分子量γ-聚谷氨酸与L-抗坏血酸6位羟基进行连接,产生一种新的L-抗坏血酸衍生物---6-O-PGA-L-抗坏血酸,该衍生物稳定性强且安全无毒,可作为维生素C的前体。
一种L-抗坏血酸衍生物的制备方法,包括如下步骤:
(1)在硫酸溶液加入L-抗坏血酸、γ-聚谷氨酸,混合搅拌4-10h,静置反应20h,获得反应液;
(2)将步骤(1)中获得的反应液使用浓盐酸调节pH为6.5-7.5,旋转蒸馏将反应液浓缩到80-100mL获得浓缩液;
(3)将步骤(2)中获得的浓缩液过滤保留滤液,在滤液中加入乙醇或者丙酮溶液,析出沉淀,过滤后保留沉淀;
(4)将步骤(3)中获得沉淀干燥后即可获得L-抗坏血酸衍生物。
进一步的,步骤(1)中所述的硫酸溶液的浓度为20-40%。
进一步的,步骤(1)中所述L-抗坏血酸添加的质量体积比为硫酸溶液体积的0.5-2%,所述γ-聚谷氨酸添加的质量体积比为硫酸溶液体积的1-3%。
进一步的,步骤(3)中所述乙醇或者丙酮溶液的添加量为2-4倍体积的浓缩液体积。
进一步的,上述L-抗坏血酸衍生物,结构式如下所示:
a≥0的自然数,c≥0的自然数,b≥1的自然数。
进一步的,上述L-抗坏血酸衍生物的合成路线如下:
进一步的,上述L-抗坏血酸衍生物在抑制酪氨酸酶活性中的应用。
进一步的,上述L-抗坏血酸衍生物在抑制皮肤黑色素沉着中的应用。
在本发明中的L-抗坏血酸衍生物的合成中,以γ-聚谷氨酸和L-抗坏血酸为原料,浓硫酸为催化剂,其中L-抗坏血酸被迅速硫酸化,生成L-抗坏血酸6-硫酸盐,然后它与γ-聚谷氨酸缓慢反应,生成6-O-PGA-L-抗坏血酸。在搅拌反应过程中,运用TLC薄层层析分析方法分析L-抗坏血酸,来判断反应进行是否完全。在后处理阶段,根据原料和产物在有机溶剂中的溶解度差异,实现产物的分离提纯。
有益效果:
(1)本发明所述的L-抗坏血酸衍生物6-O-PGA-L-抗坏血酸,稳定性强且安全无毒,可作为维生素C的前体,可以通过哺乳动物的α-葡萄糖苷酶的作用分解生成L-抗坏血酸和γ- 聚谷氨酸,从而发挥L-抗坏血酸的生物活性,与γ-聚谷氨酸在美白方面发挥协同作用。
(2)该L-抗坏血酸衍生物6-O-PGA-L-抗坏血酸对酪氨酸酶活性抑制率在75%以上,可使皮肤组织黑色素细胞及含黑色素颗粒的细胞数较对照组明显减少,有效抑制皮肤中黑色素沉着,发挥美白效果。
(3)本发明所提供的6-O-PGA-L-抗坏血酸可应用于各种领域,包括但不局限于医药、化妆品、食品等领域。
具体实施方式
为了使本技术领域人员更好地理解本申请中的技术方案,下面结合实施例对本发明作进一步说明,所描述的实施例仅是本申请一部分实施例,而不是全部,本发明不受下述实施例的限制。
实施例1
实施例1L-抗坏血酸衍生物6-O-PGA-L-抗坏血酸的合成
在500mL圆底烧瓶中加入浓度为20%-40%的硫酸溶液200mL,加入L-抗坏血酸1-2g、γ- 聚谷氨酸2-4g,将该混合物在室温下搅拌反应4-10h,静置反应20h,加入浓盐酸,调pH为 6.5-7.5,旋转蒸馏浓缩反应液至80-100mL,获得浓缩液,浓缩液经过滤纸过滤得滤液,滤液中加入2-4倍浓缩液体积的乙醇或者丙酮溶液析出沉淀,过滤沉淀,干燥后即得产物L-抗坏血酸衍生物6-O-PGA-L-抗坏血酸。
在搅拌反应过程中,取样,运用TLC薄层层析分析方法,流动相为二氯甲烷:甲醇:乙酸=80:10:0.8,当硅胶板上样品无L-抗坏血酸时,表明反应完成。
实施例2运用高效液相色谱法测定6-O-PGA-L-抗坏血酸含量
将实施例1中所得的6-O-PGA-L-抗坏血酸进行含量检测,以γ-聚谷氨酸标准溶液紫外吸收值为检测对象,具体检测方法如下。
高效液相色谱仪:岛津shimadzu,LC-20AT。色谱条件:色谱柱,TSK-GELG4000WPXL;检测器,紫外检测器;检测波长,210nm;流动相,0.3mol/L硫酸钠溶液,流速0.5mL/min,柱温30℃,进样体积20μL。
标准品处理:选择平均分子量为5kDa的γ-聚谷氨酸标准品(含量≥99.0%),用流动相溶解,分别配置成1.0mg/mL的γ-聚谷氨酸标准溶液,用孔径0.22μm的微孔滤膜过滤,超声波脱气15min。
样品处理:称取实施例1中所得的6-O-PGA-L-抗坏血酸样品,用流动相溶解,配置成 1.0mg/mL的6-O-PGA-L-抗坏血酸试样溶液,用孔径0.22μm的微孔滤膜过滤,超声波脱气15min。
实施例含量测定:将实施例1中的6-O-PGA-L-抗坏血酸试样溶液注入色谱柱中,记录峰面积,得到实施例1中的6-O-PGA-L-抗坏血酸含量为94.03%。
实施例3 6-O-PGA-L-抗坏血酸稳定性检测
试验方法如下:
试验温度选择20℃、30℃、40℃、50℃,每1h间隔取样。具体操作步骤:将6-O-PGA-L- 抗坏血酸溶液用纱布裹好分别置4个选定温度的恒温水浴箱中,当6-O-PGA-L-抗坏血酸溶液温度与水浴温度相同时,立即取样(为零时间样品)并计时,然后按设定间隔时间取样,样品取出后,应立即使之冷却或置冰箱保存,然后分别测定样品中剩余6-O-PGA-L-抗坏血酸的含量。
含量测定:将每次取样的6-O-PGA-L-抗坏血酸溶液混合均匀,精密吸取1ml置100ml 碘量瓶中,加蒸馏水15ml与丙酮2ml,摇匀,放置5min,加稀醋酸4ml与淀粉指示液1ml,用0.1mol/L碘液滴定,至溶液显蓝色并持续30s不褪。
数据记录:对在每个温度各加热时间内取出的样品与未经加热试验的原样品分别测定 6-O-PGA-L-抗坏血酸含量,采用百分含量表示,具体数据如表1所示:
表1 6-O-PGA-L-抗坏血酸含量随温度及时间变化表
在温度为20-30℃的条件下,放置5h后,6-O-PGA-L-抗坏血酸的含量大于90%;当温度上升到50℃,放置5h后,6-O-PGA-L-抗坏血酸的含量为48.95%,其稳定性数值较相关文献所述的6位抗坏血酸衍生物高,表明本发明中的6-O-PGA-L-抗坏血酸展现出了良好的稳定性。
实施例4 6-O-PGA-L-抗坏血酸对酪氨酸酶活性的抑制作用
称取L-酪氨酸25.6g,采用0.2M、pH=6.8的磷酸缓冲溶液定容于50mL容量瓶中,得L- 酪氨酸溶液。称取马铃薯适量,洗净后4℃预冷,去皮切碎,-20℃冷冻过夜,按1:1(W:V)的比例加入预冷的0.2M、pH=6.8的磷酸缓冲溶液,制成匀浆,纱布过滤,滤液于4000rpm 离心10min,上清液即酪氨酸酶粗酶液。
取熊果苷粉末溶于甲醇溶液,使其终浓度为1mg/mL,作为阳性对照;另设空白对照组1、2、3,其中对照组2初始体系中只有缓冲液,对照组1、3分别加入受试液和熊果苷溶液作为空白对照;阴性对照组则不加入任何酪氨酸酶活性抑制剂。取受试品粉末溶于甲醇溶液,使其终浓度为1mg/mL。设置空白对照组、阳性对照组、阴性对照组、受试液组,按表2比例加入到96孔板中,每组做3个复孔,吹吸均匀后,加入L-酪氨酸,37℃温育,475nm处测定吸光值。
表2各组体系中相关溶液添加量表
受试组用空白对照组1调零,阴性对照组用空白对照组2调零,阳性对照组用空白对照组3调零。受试组吸光值为A1,阴性对照组吸光值为A2,阳性对照组吸光值为A3,抑制率=1-[(A1-A2)/(A3-A2)]×100%=(A3-A1)/(A3-A2)×100%。
对酪氨酸酶活性的抑制率如表3:
表3酪氨酸酶活性抑制率
由结果可知,受试组的酪氨酸酶活性抑制率略低于熊果苷组,表明受试组中的 6-O-PGA-L-抗坏血酸对于酪氨酸酶的活性具有一定的抑制作用,从而进一步说明6-O-PGA-L-抗坏血酸可通过抑制酪氨酸酶活性来减少皮肤的色素沉着,发挥美白作用。
实施例5 6-O-PGA-L-抗坏血酸对豚鼠皮肤黑色素沉着的抑制作用
将60只白色雌性豚鼠随机分为正常组、对照组、阳性组1、阳性组2、实验组1和实验组2,每组10只。对照组、阳性组1、阳性组2、实验组1和实验组2采用UVB照射诱导皮肤产生色素沉着。具体干预方法如表4所示:
表4小鼠各组干预方法
4周后,采用苏木精-伊红、Schmorl、Imokawa方法染色,观察外用制剂涂抹后皮肤组织形态学及黑色素颗粒分布的变化。
实验结果显示,阳性组1和阳性组2中3%的γ-聚谷氨酸和L-维生素C磷酸镁酯均可使皮肤组织黑色素细胞及含黑色素颗粒的细胞数较对照组明显减少(P<0.05);实验组1和实验组2中的6-O-PGA-L-抗坏血酸均可使皮肤组织黑色素细胞及含黑色素颗粒的细胞数较对照组明显减少(P<0.05),其中浓度为3%的6-O-PGA-L-抗坏血酸与阳性组中3%的L-维生素C 磷酸镁酯的作用接近,浓度为6%的6-O-PGA-L-抗坏血酸可使皮肤组织黑色素细胞及含黑色素颗粒的细胞数减少作用大于阳性对照组。
Claims (6)
1.一种L-抗坏血酸衍生物的制备方法,其特征在于,包括如下步骤:
(1)在硫酸溶液加入L-抗坏血酸、γ-聚谷氨酸,混合搅拌4-10h,静置反应20h,获得反应液;
(2)将步骤(1)中获得的反应液使用浓盐酸调节pH为6.5-7.5,旋转蒸馏将反应液浓缩到80-100mL获得浓缩液;
(3)将步骤(2)中获得的浓缩液过滤保留滤液,在滤液中加入乙醇或者丙酮溶液,析出沉淀,过滤后保留沉淀;
(4)将步骤(3)中获得沉淀干燥后即可获得L-抗坏血酸衍生物。
2.如权利要求1所述的制备方法,其特征在于,步骤(1)中所述的硫酸溶液的浓度为20-40%。
3.如权利要求1所述的制备方法,其特征在于,步骤(1)中所述L-抗坏血酸添加的质量体积比为硫酸溶液体积的0.5-2%,所述γ-聚谷氨酸添加的质量体积比为硫酸溶液体积的1-3%。
4.如权利要求1所述的制备方法,其特征在于,步骤(3)中所述乙醇或者丙酮溶液的添加量为2-4倍体积的浓缩液体积。
5.按照权利要求1所述的制备方法制备的L-抗坏血酸衍生物在抑制酪氨酸酶活性中的应用。
6.按照权利要求1所述的制备方法制备的L-抗坏血酸衍生物在抑制皮肤黑色素沉着中的应用。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110341128.4A CN113087899B (zh) | 2021-03-30 | 2021-03-30 | 一种l-抗坏血酸衍生物及其制备方法、应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110341128.4A CN113087899B (zh) | 2021-03-30 | 2021-03-30 | 一种l-抗坏血酸衍生物及其制备方法、应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN113087899A true CN113087899A (zh) | 2021-07-09 |
CN113087899B CN113087899B (zh) | 2023-03-07 |
Family
ID=76670948
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202110341128.4A Active CN113087899B (zh) | 2021-03-30 | 2021-03-30 | 一种l-抗坏血酸衍生物及其制备方法、应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN113087899B (zh) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007075016A1 (en) * | 2005-12-29 | 2007-07-05 | Bioleaders Corporation | Collagenase inhibitor containing poly-gamma-glutamic acid-vitamin c complex and use thereof |
CN1997345A (zh) * | 2004-06-24 | 2007-07-11 | 生物领先公司 | 聚伽马谷氨酸维他命复合物及其应用 |
WO2009051460A2 (en) * | 2007-10-20 | 2009-04-23 | Seoul National University Industry Foundation | Peptide coupled ascorbic acid derivatives |
-
2021
- 2021-03-30 CN CN202110341128.4A patent/CN113087899B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1997345A (zh) * | 2004-06-24 | 2007-07-11 | 生物领先公司 | 聚伽马谷氨酸维他命复合物及其应用 |
WO2007075016A1 (en) * | 2005-12-29 | 2007-07-05 | Bioleaders Corporation | Collagenase inhibitor containing poly-gamma-glutamic acid-vitamin c complex and use thereof |
WO2009051460A2 (en) * | 2007-10-20 | 2009-04-23 | Seoul National University Industry Foundation | Peptide coupled ascorbic acid derivatives |
Non-Patent Citations (1)
Title |
---|
梁国栋: "多功能抗氧化剂L-抗坏血酸衍生物的合成及其性能研究", 《中国优秀硕士论文全文数据库 工程科技I辑》 * |
Also Published As
Publication number | Publication date |
---|---|
CN113087899B (zh) | 2023-03-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
RU2435579C2 (ru) | Способ получения проантоцианидинового олигомера | |
JP5324084B2 (ja) | コケモモ抽出物並びにその製造方法及び使用 | |
AU2012361496A2 (en) | Maillard reaction inhibitor | |
JP2009013159A6 (ja) | コケモモ抽出物並びにその製造方法及び使用 | |
Nitta et al. | Inhibitory activity of Filipendula ulmaria constituents on recombinant human histidine decarboxylase | |
JPH10226620A (ja) | 桑枝抽出物を含有する美白化粧料 | |
EP2623107B1 (en) | Arctigenin-containing bardanae fructus extract and method for producing same | |
CN112545962B (zh) | 一种含木立芦荟提取物的保湿、抑菌凝胶及其制备方法 | |
JPH1179936A (ja) | マルベリンを含有する美白化粧料 | |
CN113087899B (zh) | 一种l-抗坏血酸衍生物及其制备方法、应用 | |
WO2022215441A1 (ja) | 新規ポリフェノール化合物 | |
WO2015052849A1 (ja) | コラーゲン産生作用を有する新規な誘導体及びその製造方法 | |
KR20140108796A (ko) | 등심초 추출물을 유효 성분으로 포함하는 항암 효과를 갖는 약제학적 조성물 | |
JP3071610B2 (ja) | エピガロカテキンガレート誘導体 | |
JP6143167B2 (ja) | 小眼球症関連転写因子抑制剤、メラニン産生抑制剤、化粧品組成物及び抗ガン剤 | |
KR100519695B1 (ko) | 포도와 오이 혼합액을 이용한 동충하초 균사체 액상배양액을 포함하는 피부 미백용 화장료 조성물 | |
JP6108472B2 (ja) | ブドウ梗由来抽出物 | |
KR20120092467A (ko) | 효소를 이용한 6-o-시나밀-l-아스코르브산 유도체의 합성방법 | |
JP2003277271A (ja) | 抗癌剤 | |
JPH11323326A (ja) | 活性酸素消去剤、皮膚保全剤および変色防止剤 | |
JP2017002031A (ja) | リグナン系化合物 | |
CN112851756A (zh) | 一种酚酸多肽偶联物及其制备方法和应用 | |
KR20110035127A (ko) | 곰피와 감태 추출물 유래의 플로로탄닌을 유효성분으로 하는 염증억제용 조성물 | |
WO2009102083A1 (en) | Novel clitocybin derivatives, preparation method thereof and composition containing the extract of clitocybe aurantiaca kctc 11143bp or the novel clitocybin derivatives for prevention of aging as an active ingredient | |
KR20190063600A (ko) | 홍해삼 추출물을 포함하는 미백용 조성물 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |