CN113476439A - 原花青素类化合物在制备治疗紫外线引起的皮肤损伤产品中的应用 - Google Patents
原花青素类化合物在制备治疗紫外线引起的皮肤损伤产品中的应用 Download PDFInfo
- Publication number
- CN113476439A CN113476439A CN202110687269.1A CN202110687269A CN113476439A CN 113476439 A CN113476439 A CN 113476439A CN 202110687269 A CN202110687269 A CN 202110687269A CN 113476439 A CN113476439 A CN 113476439A
- Authority
- CN
- China
- Prior art keywords
- procyanidine
- uvb
- compound
- product
- ultraviolet rays
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims description 12
- 208000028990 Skin injury Diseases 0.000 title abstract description 5
- 230000000694 effects Effects 0.000 claims abstract description 25
- 230000005779 cell damage Effects 0.000 claims abstract description 13
- 208000037887 cell injury Diseases 0.000 claims abstract description 13
- 230000004792 oxidative damage Effects 0.000 claims abstract description 8
- 210000004927 skin cell Anatomy 0.000 claims abstract description 7
- 210000004027 cell Anatomy 0.000 claims description 30
- CWEZAWNPTYBADX-UHFFFAOYSA-N Procyanidin Natural products OC1C(OC2C(O)C(Oc3c2c(O)cc(O)c3C4C(O)C(Oc5cc(O)cc(O)c45)c6ccc(O)c(O)c6)c7ccc(O)c(O)c7)c8c(O)cc(O)cc8OC1c9ccc(O)c(O)c9 CWEZAWNPTYBADX-UHFFFAOYSA-N 0.000 claims description 14
- 229920002414 procyanidin Polymers 0.000 claims description 14
- -1 procyanidin compound Chemical class 0.000 claims description 10
- 230000006378 damage Effects 0.000 claims description 9
- 210000003491 skin Anatomy 0.000 claims description 9
- XFZJEEAOWLFHDH-UHFFFAOYSA-N (2R,2'R,3R,3'R,4R)-3,3',4',5,7-Pentahydroxyflavan(48)-3,3',4',5,7-pentahydroxyflavan Natural products C=12OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C(O)C=C(O)C=1C(C1=C(O)C=C(O)C=C1O1)C(O)C1C1=CC=C(O)C(O)=C1 XFZJEEAOWLFHDH-UHFFFAOYSA-N 0.000 claims description 7
- 206010051246 Photodermatosis Diseases 0.000 claims description 7
- MOJZMWJRUKIQGL-FWCKPOPSSA-N Procyanidin C2 Natural products O[C@@H]1[C@@H](c2cc(O)c(O)cc2)Oc2c([C@H]3[C@H](O)[C@@H](c4cc(O)c(O)cc4)Oc4c3c(O)cc(O)c4)c(O)cc(O)c2[C@@H]1c1c(O)cc(O)c2c1O[C@@H]([C@H](O)C2)c1cc(O)c(O)cc1 MOJZMWJRUKIQGL-FWCKPOPSSA-N 0.000 claims description 7
- 230000008845 photoaging Effects 0.000 claims description 7
- 230000037380 skin damage Effects 0.000 claims description 7
- 210000002510 keratinocyte Anatomy 0.000 claims description 4
- 229920002770 condensed tannin Polymers 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 239000003094 microcapsule Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000002417 nutraceutical Substances 0.000 claims 1
- 235000021436 nutraceutical agent Nutrition 0.000 claims 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 abstract description 26
- 239000003642 reactive oxygen metabolite Substances 0.000 abstract description 19
- 229960004050 aminobenzoic acid Drugs 0.000 abstract description 12
- 241000283690 Bos taurus Species 0.000 abstract description 9
- 239000003814 drug Substances 0.000 abstract description 9
- 230000009471 action Effects 0.000 abstract description 3
- 239000004480 active ingredient Substances 0.000 abstract description 3
- 201000010099 disease Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 239000000516 sunscreening agent Substances 0.000 abstract description 2
- 231100000331 toxic Toxicity 0.000 abstract description 2
- 230000002588 toxic effect Effects 0.000 abstract description 2
- 241001629511 Litchi Species 0.000 abstract 3
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 16
- 102000016938 Catalase Human genes 0.000 description 11
- 108010053835 Catalase Proteins 0.000 description 11
- 244000183278 Nephelium litchi Species 0.000 description 10
- 102000019197 Superoxide Dismutase Human genes 0.000 description 10
- 108010012715 Superoxide dismutase Proteins 0.000 description 10
- 230000003078 antioxidant effect Effects 0.000 description 9
- 229960003180 glutathione Drugs 0.000 description 8
- 239000000178 monomer Substances 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 230000003834 intracellular effect Effects 0.000 description 5
- HGVVOUNEGQIPMS-UHFFFAOYSA-N procyanidin Chemical class O1C2=CC(O)=CC(O)=C2C(O)C(O)C1(C=1C=C(O)C(O)=CC=1)OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1 HGVVOUNEGQIPMS-UHFFFAOYSA-N 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- 229920001722 A-type proanthocyanidin Polymers 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 210000000170 cell membrane Anatomy 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000004224 protection Effects 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 230000002087 whitening effect Effects 0.000 description 3
- 108010087230 Sincalide Proteins 0.000 description 2
- 238000010609 cell counting kit-8 assay Methods 0.000 description 2
- 230000003833 cell viability Effects 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- NSEWTSAADLNHNH-UHFFFAOYSA-N pavetannin A-2 Natural products OC1CC2=C(O)C=C3OC(C4O)(C=5C=C(O)C(O)=CC=5)OC5=CC(O)=CC(O)=C5C4C3=C2OC1C1=CC=C(O)C(O)=C1 NSEWTSAADLNHNH-UHFFFAOYSA-N 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 2
- 230000009759 skin aging Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- PFTAWBLQPZVEMU-ZFWWWQNUSA-N (+)-epicatechin Natural products C1([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-ZFWWWQNUSA-N 0.000 description 1
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 description 1
- XDFNWJDGWJVGGN-UHFFFAOYSA-N 2-(2,7-dichloro-3,6-dihydroxy-9h-xanthen-9-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1C2=CC(Cl)=C(O)C=C2OC2=CC(O)=C(Cl)C=C21 XDFNWJDGWJVGGN-UHFFFAOYSA-N 0.000 description 1
- 229920002330 B type proanthocyanidin Polymers 0.000 description 1
- 230000004543 DNA replication Effects 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- 102000006587 Glutathione peroxidase Human genes 0.000 description 1
- 108700016172 Glutathione peroxidases Proteins 0.000 description 1
- 229920001991 Proanthocyanidin Polymers 0.000 description 1
- NSEWTSAADLNHNH-TXZJYACMSA-N Proanthocyanidin A1 Chemical compound C1([C@H]2OC3=C4[C@H]5C6=C(O)C=C(O)C=C6O[C@]([C@@H]5O)(OC4=CC(O)=C3C[C@@H]2O)C=2C=C(O)C(O)=CC=2)=CC=C(O)C(O)=C1 NSEWTSAADLNHNH-TXZJYACMSA-N 0.000 description 1
- BPGGESYJUXPYQA-UHFFFAOYSA-N Procyanidin A1 Natural products COc1ccc(cc1OC)C2Oc3c(CC2OC(=O)C)c(OC)cc4OC5(Oc6cc(OC)c(OC)cc6C(C5OC(=O)C)c34)c7ccc(OC)c(OC)c7 BPGGESYJUXPYQA-UHFFFAOYSA-N 0.000 description 1
- 229920002658 Procyanidin A1 Polymers 0.000 description 1
- 229920002982 Procyanidin A2 Polymers 0.000 description 1
- 230000006819 RNA synthesis Effects 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940093797 bioflavonoids Drugs 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 230000032677 cell aging Effects 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- OPGYRRGJRBEUFK-UHFFFAOYSA-L disodium;diacetate Chemical compound [Na+].[Na+].CC([O-])=O.CC([O-])=O OPGYRRGJRBEUFK-UHFFFAOYSA-L 0.000 description 1
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Natural products Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 description 1
- 235000012734 epicatechin Nutrition 0.000 description 1
- 210000001339 epidermal cell Anatomy 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 230000007760 free radical scavenging Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 210000002824 peroxisome Anatomy 0.000 description 1
- 230000003711 photoprotective effect Effects 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- NSEWTSAADLNHNH-LSBOWGMISA-N proanthocyanidin A2 Chemical compound C1([C@H]2OC3=C4[C@H]5C6=C(O)C=C(O)C=C6O[C@]([C@@H]5O)(OC4=CC(O)=C3C[C@H]2O)C=2C=C(O)C(O)=CC=2)=CC=C(O)C(O)=C1 NSEWTSAADLNHNH-LSBOWGMISA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000037384 skin absorption Effects 0.000 description 1
- 231100000274 skin absorption Toxicity 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017454 sodium diacetate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Images
Classifications
-
- 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
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
-
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/77—Sapindaceae (Soapberry family), e.g. lychee or soapberry
-
- 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
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Botany (AREA)
- Mycology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Toxicology (AREA)
- Biotechnology (AREA)
- Medical Informatics (AREA)
- Microbiology (AREA)
- Alternative & Traditional Medicine (AREA)
- Biochemistry (AREA)
- Birds (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明公开了原花青素类化合物在制备治疗紫外线引起的皮肤损伤产品中的应用。(1)本发明首次发现荔枝皮原花青素类化合物能够治疗紫外线引起的细胞损伤，有效作用浓度较低，且无毒副作用。(2)本发明通过UVB致皮肤细胞损伤模型，发现原花青素类化合物能有效的抗氧化损伤，减少因UVB导致的ROS过量生成，且本发明活性最好的化合物原花青素A2的作用强于防晒剂对氨基苯甲酸(PABA)。本发明发掘了荔枝皮原花青素新的药用价值，拓展了其新的应用领域，为开发治疗紫外线引起的皮肤损伤相关疾病的药物的天然活性成分提供了新的来源和方向。
Description
技术领域：
本发明属于植物中天然活性化合物开发领域，特别是涉及从荔枝皮中提取的原花青素类化合物在制备治疗紫外线引起的皮肤损伤产品中的应用。
背景技术：
皮肤老化包括自然老化和光老化，研究表明，光老化占面部老化的80％以上，紫外线(UV)是造成皮肤光老化的主要原因。根据波长，UV分为UVA(320─400nm)，UVB(280─320nm)和UVC(100─280nm)。中波紫外线(UVB)主要由位于皮肤最外层的表皮吸收，是引起皮肤损伤的主要波段。氧化损伤是UVB所致皮肤损伤的重要机制，其中活性氧自由基(ROS)起着关键性的作用。UVB可以导致皮肤中的ROS过量产生，大量的ROS可直接或间接地氧化细胞膜上的不饱和脂肪酸形成脂质过氧化物(LPO)，进一步形成脂褐素，造成功能蛋白损伤、DNA复制功能减弱以及RNA合成受阻，破坏细胞的正常结构，从而引起细胞衰老和死亡。而有研究证实，一些抗氧化酶如超氧化物歧化酶(SOD)、谷胱甘肽过氧化物酶(GSH-PX)等能清除超氧负离子自由基，延缓机体衰老过程。更有学者指出：过氧化物酶体的标志酶过氧化氢酶(CAT)可以对机体起到抗氧化的防御作用，其含量上升对抑制皮肤衰老有积极效果。因此，抗氧化损伤是预防皮肤紫外损伤或延缓皮肤光老化的一个重要途径。
目前，一些具有光保护作用的天然植物提取物受到了人们的广泛关注，因其安全性更高、功能性更突出以及更易被皮肤吸收等优点逐渐成为人们开发和研究的热点。原花青素类化合物，是一种有着特殊分子结构的生物类黄酮，已被证实具有较强的自由基清除能力和抗氧化活性。荔枝皮富含原花青素类化合物，且以自然界少见的A型原花青素为主，具有较葡萄籽等来源的B型原花青素更好的抗氧化活性。研究表明，B型原花青素具有良好的抗氧化、美白、抗辐射等功效，被誉为“皮肤的维生素”，已被作为功效成分加入到美白抗皱等产品中。虽然有研究发现荔枝提取物具有良好的亮肤增白和抗衰老效果，然而，目前未直接进行有关其A型原花青素抗皮肤细胞氧化损伤作用和治疗皮肤光老化的研究，限制了其作为活性成分被开发利用。因此，本发明人直接执行有关荔枝皮A型原花青素具有的因紫外线引起的人表皮细胞损伤抑制和抗氧化酶活性的基础功效研究。
发明内容
本发明目的是提供从荔枝皮中提取得到的原花青素类化合物在制备治疗紫外线引起的皮肤损伤产品中的应用，所述原花青素类化合物具有抗氧化损伤的作用。
本发明提供原花青素类化合物在制备治疗紫外线引起的皮肤损伤的产品中的应用，所述原花青素类化合物包括式I所示的化合物中的至少一种：
优选，所述的紫外线引起的细胞损伤为紫外线引起的HaCaT人永生化角质细胞的损伤。
优选，所述的原花青素类化合物在制备抗氧化损伤产品中的应用。
进一步优选，所述的原花青素类化合物在制备抑制因UVB致HaCaT细胞SOD、CAT、GSH-Px活性和GSH水平下降以及MDA含量增多产品中的应用。
进一步优选，所述的原花青素类化合物在制备通过抗UVB致皮肤细胞损伤实现治疗皮肤光老化的产品中的应用。
进一步优选，所述的产品还包括药品、保健食品、化妆品上允许的载体、赋形剂或稀释剂。
进一步优选，所述的产品的剂型为胶囊剂、片剂、口服制剂、微囊制剂或注射剂。
本发明通过实验研究发现，上述原花青素类化合物能够提高UVB致HaCaT细胞损伤的细胞存活率，进一步实验研究发现，所述原花青素类化合物能够减少ROS的生成，提高SOD、CAT、GSH-Px活性和GSH水平，并降低脂质过氧化物MDA含量，具有有效的抗氧化损伤作用，对UVB所致皮肤细胞损伤具有显著的治疗功效。
本发明具有如下有益的效果：
(1)本发明首次发现荔枝皮原花青素类化合物能够治疗紫外线引起的皮肤细胞损伤，有效作用浓度较低，且无毒副作用。
(2)本发明通过UVB致皮肤细胞损伤模型，发现原花青素类化合物能有效的抗氧化损伤，减少因UVB导致的ROS过量生成，且本发明活性最好的化合物原花青素A2的作用强于防晒剂对氨基苯甲酸(PABA)。
本发明发掘了荔枝皮原花青素新的药用价值，拓展了其新的应用领域，为开发治疗紫外线引起的皮肤损伤相关疾病的药物的天然活性成分提供了新的来源和方向。
附图说明
图1是原花青素类化合物对UVB致HaCaT细胞损伤的保护作用
图2是原花青素类化合物对UVB诱导的HaCaT细胞内ROS水平的影响
图3是原花青素类化合物对UVB诱导的HaCaT细胞内SOD、CAT、GSH-Px活力和GSH、MDA含量的影响。
具体实施方式
下面通过具体实施例和具体实验对本发明所述应用做进一步说明。但不应将此理解为本发明上述主题的范围仅限于以下的实施例，凡基于本发明内容所实现的技术均属于本发明的范围。
实验材料、试剂与仪器
本发明受试样品：荔枝皮低聚原花青素(LPOPC)从荔枝皮中提取制得，3个原花青素类化合物Epicatechin(OPC 5-2)、ProcyanidinA2(OPC 6-3-1)、ProcyanidinA1(OPC 6-3-2)均是从LPOPC中分离纯化制得(纯度≥99.0％)，是已知化合物。阳性药物对氨基苯甲酸(PABA)购自美国Sigma公司(纯度≥99.9％).
本发明所用的实验材料与试剂见表1。
表1实验材料与试剂
本发明所使用的实验仪器与设备见表2。
表2实验仪器与设备
实施例1原花青素类化合物对UVB致HaCaT细胞损伤的保护作用
细胞处理：将生长状态良好的HaCaT人永生化角质细胞以5000个/孔接种于96孔培养板，待细胞过夜贴壁后，分别设置正常对照组、UVB照射组、LPOPC组、PABA组、OPC 5-2组、OPC 6-3-1组和OPC 6-3-2组。其中LPOPC组更换为含12.5、25、50、100μg/mL LPOPC的1％BSADMEM，PABA和3个原花青素单体化合物组更换为含6.25、12.5、25、50μM相应化合物的1％BSADMEM，每个浓度重复6个孔，继续培养12h后，用PBS洗涤细胞两次，然后加入薄薄的一层PBS，除正常对照组外，其余各组用紫外辐照装置对细胞进行UVB照射，照射剂量为142mJ/cm2，弃去PBS，用预冷的PBS洗涤两次。另设无细胞的空白组，向每孔加入100μL新鲜1％BSADMEM和10μL CCK-8溶液，放入培养箱继续孵育1h，然后在450nm下测定各孔的吸光度值。按下列公式计算细胞存活率：
细胞存活率/％＝(样品组OD值-空白组OD值)/(对照组OD值-空白组OD值)×100％
培养基是1％BSADMEM。
通过CCK-8法检测本发明3个原花青素类单体化合物对UVB致HaCaT细胞损伤的保护作用，结果如图1所示，经142mJ/cm2UVB照射后的HaCaT细胞存活率仅为正常组的50％，而原花青素类化合物各单体作用后的细胞存活率均显著高于UVB组，对UVB致HaCaT细胞具有一定的光保护作用，其中，同一浓度下，OPC6-3-1对HaCaT细胞的光保护作用略高于阳性药物PABA，OPC6-3-1可能对HaCaT细胞光保护作用最强。随着各药物浓度的增加，细胞存活率逐渐升高，具有浓度依赖效应，因此对于后续实验选用最高浓度，即荔枝皮原花青素100μg/mL，PABA和3个单体化合物50μM作为处理浓度。
实施例2原花青素类化合物对UVB致HaCaT细胞损伤的抗氧化作用
细胞处理：将生长状态良好的HaCaT人永生化角质细胞以106个/孔接种于6孔培养板中。培养12h贴壁后，分别设置正常对照组、UVB照射组、LPOPC组、PABA组、OPC 5-2组、OPC6-3-1组和OPC 6-3-2组，每组设3个复孔。其中LPOPC组加入100μg/mL LPOPC，PABA和3个原花青素单体化合物组各加入50μM单体化合物。继续培养12h后，用PBS洗涤两次，然后加入薄薄的一层PBS，除正常对照组外，其余各组用紫外辐照装置对细胞进行UVB照射，照射剂量为142mJ/cm2，弃去PBS，用预冷的PBS洗涤两次。培养基为：1％BSADMEM。
参照试剂盒说明书，检测各组细胞中ROS、SOD、CAT、GSH-Px和GSH及MDA水平：
2.1各组细胞ROS水平的检测结果
细胞内ROS水平反映细胞氧化程度。利用特异性荧光探针2’,7’-二氢二氯荧光黄双乙酸钠(DCFH-DA)检测细胞内ROS水平变化，DCFH-DA具有脂溶性，它可以穿越细胞膜并与细胞内的酯酶反应生成DCFH。因后者不能穿过细胞膜，可使荧光探针装载在细胞内，并被细胞内的ROS氧化成具有荧光的DCF。通过荧光酶标仪在500nm激发波长和525nm发射波长下测量DCF荧光强度，最终细胞内ROS水平以荧光度值表示。结果如图2所示，经142mJ/cm2UVB照射后细胞内ROS水平显著升高，是正常组的2.94倍。各组药物作用后细胞ROS水平均显著降低，说明原花青素类各单体化合物对UVB诱导的HaCaT细胞内ROS生成具有明显的抑制作用，其中OPC6-3-1处理的细胞内ROS水平显著低于阳性药物PABA，且与正常组无显著差异，恢复UVB致HaCaT细胞氧化损伤程度。
2.2各组细胞SOD、CAT、GSH-Px酶活力和GSH、MDA含量的检测结果
细胞内SOD、CAT、GSH-Px和GSH、MDA等抗氧化指标水平变化可以间接反映细胞的损伤程度。结果如图3所示，与正常组相比，UVB照射组细胞内的SOD、CAT、GSH-Px活力和GSH含量均显著降低，MDA含量显著增加，说明UVB照射会打破HaCaT细胞内的抗氧化平衡防御，对细胞造成损伤。而阳性药物PABA和原花青素提取物及各单体化合物对UVB诱导的HaCaT细胞内SOD、CAT、GSH-Px、GSH和MDA水平变化具有明显的改善作用，其中单体化合物OPC6-3-1的作用最显著。
Claims (7)
1.原花青素类化合物在制备治疗紫外线引起的皮肤损伤产品中的应用，所述原花青素类化合物包括式I所示的化合物中的至少一种：
2.根据权利要求1所述的应用，其特征在于，所述的紫外线引起的皮肤损伤为紫外线引起的HaCaT人永生化角质细胞的损伤。
3.根据权利要求1或2所述的应用，其特征在于，所述的原花青素类化合物在制备抗氧化损伤产品中的应用。
4.根据权利要求1或2所述的应用，其特征在于，所述的原花青素类化合物在制备抑制因UVB致HaCaT细胞SOD、CAT、GSH-Px活性和GSH水平下降以及MDA含量增多产品中的应用。
5.根据权利要求1或2所述的应用，其特征在于，所述的原花青素类化合物在制备通过抗UVB致皮肤细胞损伤实现治疗皮肤光老化的产品中的应用。
6.根据权利要求1或2所述的应用，其特征在于，所述的产品还包括药品、保健食品、化妆品上允许的载体、赋形剂或稀释剂。
7.根据权利要求1或2所述的应用，其特征在于，所述的产品的剂型为胶囊剂、片剂、口服制剂、微囊制剂或注射剂。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110687269.1A CN113476439A (zh) | 2021-06-21 | 2021-06-21 | 原花青素类化合物在制备治疗紫外线引起的皮肤损伤产品中的应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110687269.1A CN113476439A (zh) | 2021-06-21 | 2021-06-21 | 原花青素类化合物在制备治疗紫外线引起的皮肤损伤产品中的应用 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113476439A true CN113476439A (zh) | 2021-10-08 |
Family
ID=77935711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110687269.1A Pending CN113476439A (zh) | 2021-06-21 | 2021-06-21 | 原花青素类化合物在制备治疗紫外线引起的皮肤损伤产品中的应用 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113476439A (zh) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103494800A (zh) * | 2013-10-18 | 2014-01-08 | 武汉大学 | 原花青素b2在制备抗氧化损伤和抑制细胞凋亡药物中的应用 |
-
2021
- 2021-06-21 CN CN202110687269.1A patent/CN113476439A/zh active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103494800A (zh) * | 2013-10-18 | 2014-01-08 | 武汉大学 | 原花青素b2在制备抗氧化损伤和抑制细胞凋亡药物中的应用 |
Non-Patent Citations (4)
| Title |
|---|
| HUIWEN ZHANG等: "Structures and Antioxidant and Intestinal Disaccharidase Inhibitory Activities of A-Type Proanthocyanidins from Peanut Skin", 《JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY》 * |
| SHARMILA BASU-MODAK等: "Epicatechin And Its Methylated Metabolite Attenuate UVA induced Oxidative Damage To Human Skin Fibroblasts", 《FREE RADICAL BIOLOGY & MEDICINE》 * |
| SUWEN LIU等: "Hawthorn Polyphenol Extract Inhibits UVB-Induced Skin Photoaging by Regulating MMP Expression and Type I Procollagen Production in Mice", 《JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY》 * |
| 顾恒等: "《光皮肤病学》", 31 January 2009, 人民军医出版社 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101100867B1 (ko) | 주목의 형성층 또는 전형성층 유래 식물줄기세포주를 유효성분으로 함유하는 항산화, 항염증 또는 항노화용 조성물 | |
| KR102121944B1 (ko) | 해죽순 추출물을 포함하는 화장료 조성물 | |
| KR101194907B1 (ko) | 모려 추출물을 포함하는 자외선으로 인한 피부 손상 예방 및 치료용 의약품 조성물 | |
| KR20080001791A (ko) | 연교추출물을 함유하는 피부 주름개선용 화장료 조성물 | |
| KR102063686B1 (ko) | 콩뿌리 추출물을 함유하는 피부 외용제 조성물 | |
| KR101558182B1 (ko) | 흰감국 추출물을 함유하는 피부 외용제 조성물 | |
| KR20120057370A (ko) | 은행나무과의 형성층 유래 식물줄기세포를 유효성분으로 함유하는 항노화용 조성물 | |
| EP3305370B1 (en) | Algae autophagy activator | |
| US20050053560A1 (en) | Use of a composition containing extracts of Vitis vinifera and lycopersicum for protecting the skin | |
| KR101558184B1 (ko) | 적포도잎 추출물, 베리 혼합물 및 셀레늄을 함유하는 항산화용 조성물 | |
| CN113476439A (zh) | 原花青素类化合物在制备治疗紫外线引起的皮肤损伤产品中的应用 | |
| KR20030062562A (ko) | 피부재생 및 피부 노화지연 효과를 가지는 콤부차 발효배양액 및 이를 함유하는 조성물 | |
| Krutmann et al. | Modern photoprotection of human skin | |
| KR101190201B1 (ko) | 소나무 뿌리 추출물을 함유하는 화장료 조성물 | |
| KR102526200B1 (ko) | 데쿠시놀을 유효성분으로 포함하는 피부 보습 및 미백용 조성물 | |
| JP2023149101A (ja) | 組成物及び食品 | |
| KR101989067B1 (ko) | 쿠메스트린을 함유하는 조성물 | |
| KR102370802B1 (ko) | 민들레 뿌리 추출물, 카페인 및 토코페롤의 혼합물을 포함하는 피부 외용제 조성물 | |
| KR100604068B1 (ko) | 자유라디칼 소거제 혹은 항산화제로서 폴리에톡실레이티드 비타민 씨 유도체를 함유하는 조성물 | |
| CN115887311A (zh) | 一种皮肤外用组合物及其作为蓝光吸收剂和抗氧化剂的应用 | |
| KR101146133B1 (ko) | 토후박 추출물을 함유하는 항노화 기능성 화장료 조성물 | |
| Kondo et al. | Cytoprotective effect of fruit extracts associated with antioxidant activity against ultraviolet rays | |
| KR20030024284A (ko) | 장목 추출물을 주요 활성성분으로 함유하는 항노화용화장료 조성물 | |
| KR101404967B1 (ko) | 광노화로 인한 피부 손상 개선 및 예방용 피부 미용 조성물 | |
| KR20140059419A (ko) | 한방 열매 발효오일 추출물을 함유하는 화장료 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 | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20211008 |