CN113234047A - 一种多酚类化合物和组合物及其在制备具有抗衰老作用的产品中的应用 - Google Patents
一种多酚类化合物和组合物及其在制备具有抗衰老作用的产品中的应用 Download PDFInfo
- Publication number
- CN113234047A CN113234047A CN202110486359.4A CN202110486359A CN113234047A CN 113234047 A CN113234047 A CN 113234047A CN 202110486359 A CN202110486359 A CN 202110486359A CN 113234047 A CN113234047 A CN 113234047A
- Authority
- CN
- China
- Prior art keywords
- formula
- composition
- iii
- compound
- compounds
- 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.)
- Pending
Links
- -1 Polyphenol compound Chemical class 0.000 title claims abstract description 31
- 239000000203 mixture Substances 0.000 title claims abstract description 31
- 235000013824 polyphenols Nutrition 0.000 title claims abstract description 29
- 230000003712 anti-aging effect Effects 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 230000000694 effects Effects 0.000 claims abstract description 34
- 102000003425 Tyrosinase Human genes 0.000 claims abstract description 20
- 108060008724 Tyrosinase Proteins 0.000 claims abstract description 20
- 230000002087 whitening effect Effects 0.000 claims abstract description 9
- 239000002537 cosmetic Substances 0.000 claims abstract description 5
- 235000013305 food Nutrition 0.000 claims abstract description 5
- 230000036541 health Effects 0.000 claims abstract description 5
- 239000003112 inhibitor Substances 0.000 claims description 3
- 101710147108 Tyrosinase inhibitor Proteins 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 241000244206 Nematoda Species 0.000 abstract description 15
- 230000005764 inhibitory process Effects 0.000 abstract description 10
- 238000011160 research Methods 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 4
- 230000032683 aging Effects 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 11
- 210000002752 melanocyte Anatomy 0.000 description 11
- 241000244203 Caenorhabditis elegans Species 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 210000003491 skin Anatomy 0.000 description 6
- 230000002195 synergetic effect Effects 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000001963 growth medium Substances 0.000 description 4
- 230000003834 intracellular effect Effects 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 230000008099 melanin synthesis Effects 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000002965 ELISA Methods 0.000 description 3
- 108010019160 Pancreatin Proteins 0.000 description 3
- 229960000271 arbutin Drugs 0.000 description 3
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- BJRNKVDFDLYUGJ-UHFFFAOYSA-N p-hydroxyphenyl beta-D-alloside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-UHFFFAOYSA-N 0.000 description 3
- 229940055695 pancreatin Drugs 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
- 108090000631 Trypsin Proteins 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 238000004896 high resolution mass spectrometry Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000012588 trypsin Substances 0.000 description 2
- 229920000936 Agarose Polymers 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 101100447050 Caenorhabditis elegans daf-16 gene Proteins 0.000 description 1
- 101100149536 Caenorhabditis elegans skn-1 gene Proteins 0.000 description 1
- 101100203566 Caenorhabditis elegans sod-3 gene Proteins 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 241000167556 Eryngium Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 208000001382 Experimental Melanoma Diseases 0.000 description 1
- 206010020649 Hyperkeratosis Diseases 0.000 description 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
- 244000211187 Lepidium sativum Species 0.000 description 1
- 235000007849 Lepidium sativum Nutrition 0.000 description 1
- 101100083855 Rattus norvegicus Pou2f3 gene Proteins 0.000 description 1
- 101100533820 Rattus norvegicus Sod3 gene Proteins 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000001516 cell proliferation assay Methods 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000011978 dissolution method Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229960004502 levodopa Drugs 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 206010033675 panniculitis Diseases 0.000 description 1
- 210000004694 pigment cell Anatomy 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000003757 reverse transcription PCR Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000004003 subcutaneous fat Anatomy 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/14—Yeasts or derivatives thereof
- A23L33/145—Extracts
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/17—Amino acids, peptides or proteins
- A23L33/175—Amino acids
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid, pantothenic acid
- A61K31/198—Alpha-aminoacids, e.g. alanine, edetic acids [EDTA]
-
- 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
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- 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
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/18—Antioxidants, e.g. antiradicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Mycology (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nutrition Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Birds (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Botany (AREA)
- Microbiology (AREA)
- Toxicology (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明涉及生物医学技术领域，具体公开了一种多酚类化合物和组合物及其在制备具有抗衰老作用的产品中的应用。所述的多酚类化合物，其具有式Ⅰ、式Ⅱ或式Ⅲ所示的结构。所述的组合物，其包含式Ⅰ、式Ⅱ和式Ⅲ所示结构的化合物。研究表明，式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物能够延长线虫的寿命，同时，式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物还具有酪氨酸酶抑制作用，能够有效地减少脂褐素合成；因此，可以将式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物或其组合物用于制备具有抗衰老作用以及美白淡斑作用的化妆品、护肤品、食品、保健品或药物。
Description
技术领域
本发明涉及生物医学技术领域，具体涉及一种多酚类化合物和组合物及其在制备具有抗衰老作用的产品中的应用。
背景技术
皮肤主要是由表皮、真皮和皮下脂肪组织这3层组成，也是人体最大的器官。皮肤可以将人体内环境与外界环境隔绝开来，起到物理屏障的作用，但也因此会遭受外界环境的物理、化学、细菌感染等多种有害刺激，长期的外界刺激会诱发皮肤ROS水平增高，导致皮肤氧化损伤、屏障功能受损，从而导致皮炎、加速衰老等。
本发明旨在开发一种具有抗衰老作用的化合物。
发明内容
鉴于此，本发明首先提供了一种多酚类化合物；研究表明所述的多酚类化合物具有抗衰老作用。
本发明的技术方案如下：
本发明提供了一种多酚类化合物，其具有式Ⅰ、式Ⅱ或式Ⅲ所示的结构；
本发明提供了一种上述全新结构的多酚类化合物；研究表明式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物能够延长线虫的寿命；因此，可以将式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物用于制备具有抗衰老作用的产品。
进一步研究表明式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物具有酪氨酸酶抑制作用；更进一步研究表明式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物可以减少脂褐素合成；由于式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物具有酪氨酸酶抑制作用以及可以减少脂褐素合成；因此，可以将式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物用于制备具有美白淡斑作用的产品。
本发明还提供一种组合物，其包含式Ⅰ、式Ⅱ和式Ⅲ所示结构的化合物。
优选地，式Ⅰ、式Ⅱ和式Ⅲ所示结构的化合物的质量比为1～10:1～10:1～10。
更优选地，式Ⅰ、式Ⅱ和式Ⅲ所示结构的化合物的质量比为1～5:1～5:1～5。
进一步优选地，式Ⅰ、式Ⅱ和式Ⅲ所示结构的化合物的质量比为1～3:1～3:1～3。
最优选，式Ⅰ、式Ⅱ和式Ⅲ所示结构的化合物的质量比为1:1:1。
本发明还提供上述化合物在制备酪氨酸酶抑制剂中的应用。
本发明还提供上述化合物在制备具有抗衰老作用或美白淡斑作用的产品中的应用。
发明人经大量的实验研究表明由式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物组成的组合物其对于酪氨酸酶的抑制活性以及对线虫寿命的延长作用均大于单独使用式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物；因此，将式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物组合后可以产生协同抑制酪氨酸酶活性作用，以及能够产生协同抗衰老以及美白淡斑作用。
优选地，所述的产品为化妆品、护肤品、食品、保健品或药物。
本发明还提供上述组合物在制备酪氨酸酶抑制剂中的应用。
本发明还提供上述组合物在制备具有抗衰老作用或美白淡斑作用的产品中的应用。
优选地，所述的产品为化妆品、护肤品、食品、保健品或药物。
有益效果：本发明提供了一种全新结构的多酚类化合物，研究表明，式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物能够延长线虫的寿命，因此，可以将式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物用于制备具有抗衰老作用的产品。此外，式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物具有酪氨酸酶抑制作用，能够有效地减少脂褐素合成；因此，可以将式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物用于制备具有美白淡斑作用的产品；进一步研究表明，由式Ⅰ、式Ⅱ或式Ⅲ所示结构的多酚类化合物组成的组合物可以产生协同抗衰老作用以及协同抑制酪氨酸酶活性作用，因此，所述的组合物可以用于制备具有抗衰老作用以及美白淡斑作用的产品。
附图说明
为了更清楚地说明本发明实施例或现有技术中的技术方案，下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍，显而易见地，下面描述中的附图仅仅是本发明的一些实施例的附图，对于本领域普通技术人员来讲，在不付出创造性劳动的前提下，还可以根据这些附图获得其他的附图。
图1是EP的1H NMR谱。
图2是EP的13C NMR谱。
图3是EP的质谱。
图4是EP的HPLC图谱。
图5是BA的1H NMR谱。
图6是BA的13C NMR谱。
图7是BA的质谱。
图8是BA的HPLC图谱。
图9是PA的1H NMR谱。
图10是PA的13C NMR谱。
图11是PA的质谱结果。
图12是PA的HPLC图谱。
图13是EBP对秀丽隐杆线虫寿命、体内ROS含量及脂褐素生成的影响实验结果图。
图14是EBP对秀丽隐杆线虫抗衰老相关基因表达的影响实验结果图。
图15是EBP对细胞酪氨酸酶抑制活性及黑色素生成的影响实验结果图。
具体实施方式
下面将结合实施例对本发明技术方案进行清楚、完整地描述。显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有作出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
实施例1化合物的制备
(1)取50g二裂酵母发酵产物溶胞物，加入200mL氯仿和2000mL水混合进行萃取，重复萃取3次，取水层，经低温干燥后，然后经HPLC制备得式Ⅰ所示结构的化合物；
其中HPLC的制备条件为：高效液相色谱测定条件为采用Boston Green ODS-AQ色谱柱(250*4.6mm)，以0.1％三氟乙酸水溶液为流动相A，以0.1％三氟乙酸的甲醇溶液为流动相A，流动相A：流动相B＝50:50，流速为2mL/min，检测波长为310μm，进样量100μL。收集8.001min的色谱峰，即得式Ⅰ所示结构的化合物。
式Ⅰ所示结构的化合物为淡黄色油状物；
(c 1.0,CHCl3)；香草醛-浓硫酸加热反应(TLC)呈深蓝色斑点；UV(CH3CN)吸收特征光谱显示其最大吸收波长为195,221,237,280,338nm；高分辨质谱(HR-ESI-MS)显示准分子离子峰为m/z:499.3034[M+Na]+(calcd for C28H44NaO6,499.303)，从而确定其分子式为C28H44O6，不饱和度为7。1H NMR谱(600MHz,CDCl3)中主要显示1个次甲基[δH 2.68,2.58(each 1H,d,J＝16.0Hz)]和6个甲基信号[δH 2.54,2.09,1.35(each 3H,s)；1.17(3H,d,J＝7.3Hz)；0.85,0.84(each 3H,d,J＝6.6Hz)]。13C NMR谱(150MHz,CDCl3)则显示28个碳信号，结合DEPT-135分析，分别为9个季碳、3个次甲基、10个亚甲基及6个甲基，其中部分信号可归属为2个羰基碳信号(δC 194.6,181.8)，1组全取代的苯环信号(δC 155.5,150.0,135.4,122.9,111.8,111.0)，及1个与氧相连的季碳信号(δC 80.1)。该化合物最终鉴定为(2S,6S,10R)-13-((R)-6,7-dihydroxy-2,5,8-trimethyl-4-oxochroman-2-yl)-2,6,10-trimethyltridecanoic acid(即式Ⅰ所示结构的化合物，简写为EP)。
(2)取50g滨海剌芹(ERYNGIUM MARITIMUM)愈伤组织培养物滤液，加入200mL氯仿和2000mL水混合进行萃取，重复萃取3次，取水层，经低温干燥后，然后经HPLC制备得式Ⅱ所示结构的化合物；
其中HPLC的制备条件为：高效液相色谱测定条件为采用Boston Green ODS-AQ色谱柱(250*4.6mm)，以0.1％三氟乙酸水溶液为流动相A，以0.1％三氟乙酸的甲醇溶液为流动相A，流动相A：流动相B＝30:70，流速为2mL/min，检测波长为310μm，进样量100μL。收集8.144min的色谱峰，即得式Ⅱ所示结构的化合物。
式Ⅱ所示结构的化合物为白色粉末，ESI-MS显示离子峰m/z 250.1[M-H]+，离子峰m/z 274.1[M+Na]+，确定其分子式为C12H13NO5。1H NMR(600MHz,DMSO)：δH 9.40(s,1H),9.15(s,1H),8.42(t,1H),7.27(s,1H),6.97(d,1H),6.87(d,1H),6.74(d,1H),6.40(d,1H),3.95(d,1H),3.65(s,3H)；13C NMR(151MHz,DMSO)δC 171.01,166.35,147.95,146.00,140.43,126.63,121.07,118.06,116.21,114.33,52.16,41.19。该化合物最终鉴定为Methyl(E)-(3-(3,4-dihydroxyphenyl)acryloyl)glycinate(即式Ⅱ所示结构的化合物，简写为BA)。
(3)取50g啤酒酵母菌(SACCHAROMYCES CEREVISIAE)提取物)，加入200mL氯仿和2000mL水混合进行萃取，重复萃取3次，取水层，经低温干燥后，然后经HPLC制备得式Ⅲ所示结构的化合物；
其中HPLC的制备条件为：高效液相色谱测定条件为采用Boston Green ODS-AQ色谱柱(250*4.6mm)，以0.1％三氟乙酸水溶液为流动相A，以0.1％三氟乙酸的甲醇溶液为流动相A，流动相A：流动相B＝40:60，流速为2mL/min，检测波长为310μm，进样量100μL。收集15.048min的色谱峰，即得式Ⅲ所示结构的化合物。
式Ⅲ所示结构的化合物为黄色粉末，ESI-MS显示离子峰m/z 340.1[M-H]+，离子峰m/z 364.2[M+Na]+，确定其分子式为C19H19NO5。1H NMR(600MHz,DMSO)δH:8.44(d,1H),7.29(m,2H),6.93(d,1H),6.82(dd,1H),6.73(m,1H),6.38(d,1H),4.61(m,1H),3.61(s,1H),3.06(m,1H),2.95(m,1H)；13C NMR(151MHz,DMSO)δC 172.69,165.87,148.04,146.03,140.51,137.71,129.50,128.73,127.02,126.55,121.05,117.95,116.20,114.30,54.21,52.32,49.06,37.28。该化合物最终鉴定为Methyl(E)-(3-(3,4-dihydroxyphenyl)acryloyl)phenylalaninate(即式Ⅲ所示结构的化合物，简写为PA)。
实验例1
为了评估本发明所述化合物或组合物的抗衰老活性，抑制酪氨酸酶活性以及减少脂褐素合成效果，本发明进行了如下实验。
将10条秀丽隐杆线虫置于NGM平板上，接种大肠杆菌(OP50菌株)，产卵约5h。然后，将线虫放回NGM平板20℃培养，直到秀丽隐杆线虫子代到达L4幼虫。
实验第0天，将L4秀丽隐杆线虫幼虫转移到含有溶解样品EP、BA、PA以及由EP、BA、PA三者混合而成的组合物(简写为EBP，EP、BA、PA三者为等质量比的组合)0.10mg/mL的35mmNGM平板上，每天计数。不能移动的秀丽隐杆线虫记作为死亡，每组线虫数≥100条，重复3次。
实验第0天，将L4秀丽隐杆线虫幼虫转移到含有溶解样品EP、BA、PA以及由EP、BA、PA三者混合而成的组合物(简写为EBP，EP、BA、PA三者为等质量比的组合)0.10mg/mL的35mmNGM平板上培养。第6天，将线虫置于载玻片上1％琼脂糖垫上，用NaN3(20μM)麻醉，在荧光显微镜下观察线虫荧光强度。
实验第0天，将L4秀丽隐杆线虫幼虫转移到含有溶解样品EP、BA、PA以及由EP、BA、PA三者混合而成的组合物(简写为EBP，EP、BA、PA三者为等质量比的组合)0.10mg/mL的35mmNGM平板上培养。第7天，收集线虫，使用,ROS特异性荧光探针DCFH-DA测定线虫体内ROS含量。
实验第0天，将L4秀丽隐杆线虫幼虫转移到含有溶解样品EP、BA、PA以及由EP、BA、PA三者混合而成的组合物(简写为EBP，EP、BA、PA三者为等质量比的组合)0.10mg/mL的35mmNGM平板上培养。第7天，收集线虫，PBS洗涤3次。用Trizol试剂提取总RNA，进行RT-PCR实验，分析EP、BA、PA以及由EP、BA、PA三者混合而成的组合物(简写为EBP，EP、BA、PA三者具为等质量比的组合)对线虫相关抗衰老基因表达的影响。
进一步的为了评价EP、BA、PA以及由EP、BA、PA三者混合而成的组合物(简写为EBP，EP、BA、PA三者为等质量比的组合)对黑色素细胞酪氨酸酶活性及黑色素生成的影响，进行如下实验。
采用小鼠B16黑色素瘤细胞作为受试细胞，从其抑制黑色素细胞增殖、细胞内酪氨酸酶活性以及细胞内黑色素合成的影响。其中相关实验方法简要列举如下：
细胞的体外培养
将培养瓶置于含5％CO2的37℃孵育箱中培养，当黑色素细胞在培养瓶底铺满时即可进行传代。弃去培养液，加人0.25％胰酶消化2-3min，弃去胰蛋白酶，然后加入1-3mL培养液，吹打成单细胞悬液，1500r/min离心5min，弃去上清液，取适量细胞接种于新的培养瓶，置孵育箱中常规培养，每3天传代一次，每次实验取自同一传代细胞。
实验分组
无菌条件下将EP、BA、PA以及由EP、BA、PA三者混合而成的组合物(简写为EBP，EP、BA、PA三者具为等质量比的组合)用黑色素细胞培养基稀释成以下浓度：16、8、4、2、1μg/mL。用0.22μm滤膜过滤细菌，4℃避光保存。其中熊果苷作为阳性对照药物，单纯培养基为空白对照。
黑色素细胞增殖测定
四甲基偶氮唑蓝比色(MTT)法测定不同浓度EP、BA、PA以及由EP、BA、PA三者混合而成的组合物(简写为EBP，EP、BA、PA三者具为等质量比的组合)对黑色素细胞增殖的影响。收集对数期细胞，用0.25％胰蛋白酶消化，调整细胞密度为6×104个/mL，每孔200μL接种于96孔培养板。37℃，5％CO2孵育24h，细胞贴壁，弃上清，按照实验分组分别加入不同浓度的受试物180μL，每个浓度设置3个复孔。孵育48h后，每孔加人20μL MTT(5mg/mL)继续孵育4h。小心吸去孔内培养液，然后加人150μL的DMSO，置摇床上低速振荡10min，使结晶物充分溶解，在酶联免疫检测仪测定490nm处吸光度。计算各组黑色素细胞增殖抑制率。
细胞内酪氨酸酶活力测定
取对数生长的细胞，将细胞浓度调节至6×104个/mL；后加入24孔板，每孔lmL，设3个复孔。24h细胞贴壁，弃培养液，加入不同浓度条件培养基，继续培养48h，弃培养基，0.25％胰酶消化，以5000r/min离心10min，用pH7.4的PBS(0.01mol/L)洗涤2次，各加入1％TritonX-100溶液200μL；迅速置-80℃冻存30min，反复冻融2次以溶解细胞；吸取100μL转移至96孔板，每孔再加20μL质量分数为0.1％的左旋多巴溶液，振摇5min后放入37℃培养箱孵育1h，于分光光度计上测A490值。对照组方法同上，酪氨酸酶活性抑制率＝(1-实验组A490值/空白组A490平均值)×100％。
细胞内黑色素合成测定
用NaOH溶解法对黑色素细胞中黑色素进行测定，处理同上。培养72h，弃培养液，用0.25％胰酶消化，以1000r/min离心5min，弃上清，每个处理因素下的细胞加入200μL含10％DMSO的NaOH(1mol/L)溶液，于65℃水浴完全溶解黑色素颗粒，酶联免疫检测仪检侧490nm处吸光度A值。黑色素形成率＝实验组A490值/空白组A490平均值×100％。
实验结果如下：
与正常组相比，EP组、BA组、PA组以及EBP组均能够延长线虫寿命，这说明说明化合物EP、BA、PA以及由EP、BA、PA三者组成的组合物其均具有抗衰老功能。与正常组相比，EP组，BA组，PA组及EBP组线虫平均寿命延长14.2％,16.1％,21.8％,28.4％(图13A)。与化合物单独作用相比，EBP具有更佳的抗衰老活性。我们推测，三种单体化合物可能具有一定的协同效应从而发挥更佳优异的抗衰老活性。
此外，EP，BA，PA及EBP还能够抑制秀丽隐杆线虫体内ROS的生成(图13B)，减少氧化性物对线虫的损伤，类似的，相同浓度条件下，EBP抑制秀丽隐杆线虫体内ROS的生成能力强于EP，BA，PA。进一步的我们研究发现，EP，BA，PA及EBP能够抑制秀丽隐杆线虫体内脂褐素的生成(图13C)，进一步说明EP，BA，PA及EBP具有抗衰老活性，可以通过调节体内ROS产生及抑制氧化损伤性物质的生成及抑制脂褐素的产生发挥抗衰老活性。进一步的实验研究说明，EP，BA，PA及EBP还可通过调控秀丽隐杆线虫相关基因的表达发挥抗衰老活性。如，通过促进sod-3、daf-16及skn-1基因的表达发挥抗衰老活性(图14)。
EP，BA，PA及EBP在浓度为16μg/mL对B16黑色素细胞活性无显著影响。
EP，BA，PA及EBP和熊果苷对照组均可抑制黑色素细胞的酪氨酸酶活性；其中，EBP在相同浓度条件下(16μg/mL)对B16黑色素细胞酪氨酸酶活性抑制率与熊果苷类似，且强于EP，BA，PA(图15A)。这说明EP、BA以及PA组合后产生了协同抑制酪氨酸酶活性作用。
EP，BA，PA及EBP和熊果苷组细胞黑色素合成量随用药浓度的增加而降低。其中16μg/mL EP，BA，PA及EBP和熊果苷对细胞黑色素的抑制率大约为13.1％，17.2％，22.4％，35.4％，39.1％(图15B)。以上实验结果说明，EP，BA，PA及EBP在对黑色素细胞无细胞活性影响条件下可通过调控酪氨酸酶活性等方式抑制黑色素的生成。
以上所揭露的仅为本发明较佳实施例而已，当然不能以此来限定本发明之权利范围，本领域普通技术人员可以理解实现上述实施例的全部或部分流程，并依本发明权利要求所作的等同变化，仍属于发明所涵盖的范围。
Claims (10)
1.一种多酚类化合物，其特征在于，具有式Ⅰ、式Ⅱ或式Ⅲ所示的结构；
2.一种组合物，其特征在于，包含式Ⅰ、式Ⅱ和式Ⅲ所示结构的化合物。
3.根据权利要求1所述的组合物，其特征在于，式Ⅰ、式Ⅱ和式Ⅲ所示结构的化合物的质量比为1～10:1～10:1～10。
4.根据权利要求3所述的组合物，其特征在于，式Ⅰ、式Ⅱ和式Ⅲ所示结构的化合物的质量比为1～5:1～5:1～5；进一步优选地，式Ⅰ、式Ⅱ和式Ⅲ所示结构的化合物的质量比为1～3:1～3:1～3；最优选，式Ⅰ、式Ⅱ和式Ⅲ所示结构的化合物的质量比为1:1:1。
5.权利要求1所述的化合物在制备酪氨酸酶抑制剂中的应用。
6.权利要求1所述的化合物在制备具有抗衰老作用或美白淡斑作用的产品中的应用。
7.根据权利要求6所述的应用，其特征在于，所述的产品为化妆品、护肤品、食品、保健品或药物。
8.权利要求2～4任一项所述的组合物在制备酪氨酸酶抑制剂中的应用。
9.权利要求2～4任一项所述的组合物在制备具有抗衰老作用或美白淡斑作用的产品中的应用。
10.根据权利要求9所述的应用，其特征在于，其特征在于，所述的产品为化妆品、护肤品、食品、保健品或药物。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110486359.4A CN113234047A (zh) | 2021-04-30 | 2021-04-30 | 一种多酚类化合物和组合物及其在制备具有抗衰老作用的产品中的应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110486359.4A CN113234047A (zh) | 2021-04-30 | 2021-04-30 | 一种多酚类化合物和组合物及其在制备具有抗衰老作用的产品中的应用 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113234047A true CN113234047A (zh) | 2021-08-10 |
Family
ID=77131936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110486359.4A Pending CN113234047A (zh) | 2021-04-30 | 2021-04-30 | 一种多酚类化合物和组合物及其在制备具有抗衰老作用的产品中的应用 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113234047A (zh) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113968795A (zh) * | 2021-07-26 | 2022-01-25 | 潍坊市人民医院(潍坊市传染病医院) | 一种化合物、组合物及其在制备具有治疗心肌炎作用的药物中的应用 |
| CN114712346A (zh) * | 2022-04-20 | 2022-07-08 | 深圳海创生物科技有限公司 | 一种山楂多酚、山楂多糖或组合物在制备具有降血脂和/或减肥作用的药物或食品中的应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004175778A (ja) * | 2002-10-03 | 2004-06-24 | Sogo Pharmaceutical Co Ltd | 新規桂皮酸類 |
| CN103479611A (zh) * | 2012-06-12 | 2014-01-01 | 中国科学院上海药物研究所 | 蜂斗菜酚化合物在制备酪氨酸酶抑制剂中的应用 |
-
2021
- 2021-04-30 CN CN202110486359.4A patent/CN113234047A/zh active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004175778A (ja) * | 2002-10-03 | 2004-06-24 | Sogo Pharmaceutical Co Ltd | 新規桂皮酸類 |
| CN103479611A (zh) * | 2012-06-12 | 2014-01-01 | 中国科学院上海药物研究所 | 蜂斗菜酚化合物在制备酪氨酸酶抑制剂中的应用 |
Non-Patent Citations (4)
| Title |
|---|
| LYUBOMIR GEORGIEV ET AL.,: "Anti-tyrosinase,antioxidant and antimicrobial activities of hydroxycinnamoylamides", 《MED CHEM RES》 * |
| SEUNG UK LEE ET AL.,: "Caffeoylglycolic and caffeoylamino acid derivatives, halfmers of L-chicoric acid, as new HIV-1 integrase inhibitors", 《EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY》 * |
| 胡泳华 等: "酪氨酸酶抑制剂的应用研究进展", 《厦门大学学报（自然科学版)》 * |
| 陈良华 等: "福建绞股蓝对色素沉着性疾病酪氨酸酶的抑制和抗氧化应激作用", 《第十一届全国中西医结合基础理论学术研讨会论文集》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113968795A (zh) * | 2021-07-26 | 2022-01-25 | 潍坊市人民医院(潍坊市传染病医院) | 一种化合物、组合物及其在制备具有治疗心肌炎作用的药物中的应用 |
| CN114712346A (zh) * | 2022-04-20 | 2022-07-08 | 深圳海创生物科技有限公司 | 一种山楂多酚、山楂多糖或组合物在制备具有降血脂和/或减肥作用的药物或食品中的应用 |
| CN114712346B (zh) * | 2022-04-20 | 2023-08-08 | 深圳海创生物科技有限公司 | 一种山楂多酚、山楂多糖或组合物在制备具有降血脂和/或减肥作用的药物或食品中的应用 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Saha et al. | Evaluation of antioxidant and nitric oxide inhibitory activities of selected Malaysian medicinal plants | |
| CN113234047A (zh) | 一种多酚类化合物和组合物及其在制备具有抗衰老作用的产品中的应用 | |
| KR100825450B1 (ko) | 연교추출물을 함유하는 피부 주름개선용 화장료 조성물 | |
| Huang et al. | Intestinal α-glucosidase inhibitory activity and toxicological evaluation of Nymphaea stellata flowers extract | |
| Wang et al. | The anti-aging activity of Lycium barbarum polysaccharide extracted by yeast fermentation: In vivo and in vitro studies | |
| Bralley et al. | Topical anti-inflammatory activities of Vitis rotundifolia (muscadine grape) extracts in the tetradecanoylphorbol acetate model of ear inflammation | |
| KR100731613B1 (ko) | 산뽕나무 줄기 심재 추출물을 포함하는 미백 및 항노화화장료 조성물 | |
| Lee et al. | Determination of phytochemical contents and biological activities from the fruits of Elaeagnus multiflora | |
| Ichiyanagi et al. | Gastrointestinal uptake of nasunin, acylated anthocyanin in eggplant | |
| WO2017217695A1 (ko) | 알파-망고스틴, 베타-망고스틴, 감마-망고스틴 또는 가르탄닌 화합물을 유효성분으로 함유하는 피부 주름 개선 또는 피부 보습용 조성물 | |
| Wang et al. | Isolation and identification of four antioxidants from Rhodiola crenulata and evaluation of their UV photoprotection capacity in vitro | |
| KR20190088156A (ko) | 항노화, 항산화, 항염증 및 주름개선 활성을 갖는 진주조개 점액 여과물 및 그 제조방법과 이를 유효성분으로 하는 화장료 조성물 | |
| TW201031433A (en) | Skin-whitening agent, anti-aging agent, and anti-oxidant agent | |
| KR100904759B1 (ko) | 감태 추출물을 포함하는 미백 화장용 조성물 | |
| KR20070024147A (ko) | 리포좀으로 안정화 된 우렁쉥이 또는 멍게 외막 추출물을함유하는 피부 노화 억제 및 주름 개선 화장료 조성물 | |
| Song et al. | Lactobacillus plantarum fermented Laminaria japonica alleviates UVB-induced epidermal photoinflammation via the Keap-1/Nrf2 pathway | |
| Thomas-Oates et al. | Cell protective antioxidants from the root bark of Lannea velutina A. Rich., a Malian medicinal plant | |
| KR20070005049A (ko) | 미백활성을 갖는 제주조릿대 잎 추출물 | |
| CN108464949B (zh) | 一种抗氧化美白组合物及其应用 | |
| KR102471009B1 (ko) | 왕자귀나무 추출물을 함유하는 피부미백 또는 주름개선용 화장료 조성물 | |
| KR20090089973A (ko) | 털산박하 추출물을 유효성분으로 함유하는 항산화 및미백용 화장료 조성물 | |
| Ramalingam et al. | Phytochemical analysis, HPTLC finger printing, in vitro antioxidant and cytotoxic activity of Cymodocea serrulata | |
| CN102250161B (zh) | 具有酪氨酸酶抑制活性的紫罗兰酮类衍生物及其制备方法和用途 | |
| Park | Analysis of antioxidant efficacy of Ginkgo biloba leaves and Acer palmatum Leaves | |
| JP2009126810A (ja) | ツバキ由来のアントシアニン色素、その製造方法及び用途、並びにツバキの品種識別方法 |
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 | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20210810 |
|
| WD01 | Invention patent application deemed withdrawn after publication |