FR2652001A1 - Dermato-cosmetic composition based on rosmarinic acid, possessing properties of a sunscreen agent and anti-inflammatory agent - Google Patents
Dermato-cosmetic composition based on rosmarinic acid, possessing properties of a sunscreen agent and anti-inflammatory agent Download PDFInfo
- Publication number
- FR2652001A1 FR2652001A1 FR8912370A FR8912370A FR2652001A1 FR 2652001 A1 FR2652001 A1 FR 2652001A1 FR 8912370 A FR8912370 A FR 8912370A FR 8912370 A FR8912370 A FR 8912370A FR 2652001 A1 FR2652001 A1 FR 2652001A1
- Authority
- FR
- France
- Prior art keywords
- dermato
- cosmetic composition
- rosmarinic acid
- acid
- composition according
- 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
- DOUMFZQKYFQNTF-WUTVXBCWSA-N (R)-rosmarinic acid Chemical compound C([C@H](C(=O)O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-WUTVXBCWSA-N 0.000 title claims abstract description 69
- DOUMFZQKYFQNTF-MRXNPFEDSA-N rosemarinic acid Natural products C([C@H](C(=O)O)OC(=O)C=CC=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-MRXNPFEDSA-N 0.000 title claims abstract description 35
- ZZAFFYPNLYCDEP-HNNXBMFYSA-N Rosmarinsaeure Natural products OC(=O)[C@H](Cc1cccc(O)c1O)OC(=O)C=Cc2ccc(O)c(O)c2 ZZAFFYPNLYCDEP-HNNXBMFYSA-N 0.000 title claims abstract description 34
- TVHVQJFBWRLYOD-UHFFFAOYSA-N rosmarinic acid Natural products OC(=O)C(Cc1ccc(O)c(O)c1)OC(=Cc2ccc(O)c(O)c2)C=O TVHVQJFBWRLYOD-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 239000002537 cosmetic Substances 0.000 title claims abstract description 14
- 239000000203 mixture Substances 0.000 title claims abstract description 14
- 239000000516 sunscreening agent Substances 0.000 title description 2
- 239000002260 anti-inflammatory agent Substances 0.000 title 1
- 229940121363 anti-inflammatory agent Drugs 0.000 title 1
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 4
- 230000000843 anti-fungal effect Effects 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 239000003755 preservative agent Substances 0.000 claims abstract description 4
- 206010015150 Erythema Diseases 0.000 claims abstract 2
- 206010061218 Inflammation Diseases 0.000 claims abstract 2
- 229940121375 antifungal agent Drugs 0.000 claims abstract 2
- 239000003963 antioxidant agent Substances 0.000 claims abstract 2
- 231100000321 erythema Toxicity 0.000 claims abstract 2
- 230000004054 inflammatory process Effects 0.000 claims abstract 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 230000001681 protective effect Effects 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 239000002502 liposome Substances 0.000 claims description 2
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 description 10
- 210000003494 hepatocyte Anatomy 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 5
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
- 235000004883 caffeic acid Nutrition 0.000 description 4
- 229940074360 caffeic acid Drugs 0.000 description 4
- 230000002248 lipoperoxidative effect Effects 0.000 description 4
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical class O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical group OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 102000003855 L-lactate dehydrogenase Human genes 0.000 description 2
- 108700023483 L-lactate dehydrogenases Proteins 0.000 description 2
- 102000003820 Lipoxygenases Human genes 0.000 description 2
- 108090000128 Lipoxygenases Proteins 0.000 description 2
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 2
- 244000062730 Melissa officinalis Species 0.000 description 2
- IKMDFBPHZNJCSN-UHFFFAOYSA-N Myricetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC(O)=C(O)C(O)=C1 IKMDFBPHZNJCSN-UHFFFAOYSA-N 0.000 description 2
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 description 2
- 229930003427 Vitamin E Natural products 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 229940114079 arachidonic acid Drugs 0.000 description 2
- 235000021342 arachidonic acid Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229950005499 carbon tetrachloride Drugs 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 210000000170 cell membrane Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940074393 chlorogenic acid Drugs 0.000 description 2
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 description 2
- 235000001368 chlorogenic acid Nutrition 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
- 150000002215 flavonoids Chemical class 0.000 description 2
- 235000017173 flavonoids Nutrition 0.000 description 2
- 230000002440 hepatic effect Effects 0.000 description 2
- 230000004968 inflammatory condition Effects 0.000 description 2
- 150000002617 leukotrienes Chemical class 0.000 description 2
- 210000001853 liver microsome Anatomy 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- PCOBUQBNVYZTBU-UHFFFAOYSA-N myricetin Natural products OC1=C(O)C(O)=CC(C=2OC3=CC(O)=C(O)C(O)=C3C(=O)C=2)=C1 PCOBUQBNVYZTBU-UHFFFAOYSA-N 0.000 description 2
- 229940116852 myricetin Drugs 0.000 description 2
- 235000007743 myricetin Nutrition 0.000 description 2
- 238000006395 oxidase reaction Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000018553 tannin Nutrition 0.000 description 2
- 229920001864 tannin Polymers 0.000 description 2
- 239000001648 tannin Substances 0.000 description 2
- 239000011709 vitamin E Substances 0.000 description 2
- 235000019165 vitamin E Nutrition 0.000 description 2
- NWCHELUCVWSRRS-SECBINFHSA-N (2r)-2-hydroxy-2-phenylpropanoic acid Chemical compound OC(=O)[C@@](O)(C)C1=CC=CC=C1 NWCHELUCVWSRRS-SECBINFHSA-N 0.000 description 1
- DCEUKJMFFBNQJQ-HTYNWGMWSA-N (2r,3r)-6-[(e)-2-carboxyethenyl]-3-(3,5-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid Chemical compound C1([C@@H]2[C@@H](OC3=CC=C(C=C3O2)/C=C/C(=O)O)C(O)=O)=CC(O)=CC(O)=C1 DCEUKJMFFBNQJQ-HTYNWGMWSA-N 0.000 description 1
- KJHJAABRDASKAF-UHFFFAOYSA-N 3,7-dihydropurine-2,6-dione Chemical compound OC1=NC(O)=C2N=CNC2=N1.O=C1NC(=O)NC2=C1NC=N2 KJHJAABRDASKAF-UHFFFAOYSA-N 0.000 description 1
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 1
- 241000207965 Acanthaceae Species 0.000 description 1
- 241000208173 Apiaceae Species 0.000 description 1
- 240000006891 Artemisia vulgaris Species 0.000 description 1
- 241001480043 Arthrodermataceae Species 0.000 description 1
- 241001072256 Boraginaceae Species 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 208000005623 Carcinogenesis Diseases 0.000 description 1
- 241000588697 Enterobacter cloacae Species 0.000 description 1
- 241001480036 Epidermophyton floccosum Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241001072382 Glechoma Species 0.000 description 1
- 241000207932 Hydrophyllaceae Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241000207923 Lamiaceae Species 0.000 description 1
- 244000165082 Lavanda vera Species 0.000 description 1
- 235000002997 Lavandula Nutrition 0.000 description 1
- 241000034009 Lycopus Species 0.000 description 1
- 235000010654 Melissa officinalis Nutrition 0.000 description 1
- 241001480037 Microsporum Species 0.000 description 1
- 241001529744 Origanum Species 0.000 description 1
- 235000011203 Origanum Nutrition 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 244000124853 Perilla frutescens Species 0.000 description 1
- 241000985694 Polypodiopsida Species 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000588768 Providencia Species 0.000 description 1
- 241001529739 Prunella <angiosperm> Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241001529742 Rosmarinus Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241001072909 Salvia Species 0.000 description 1
- 235000017276 Salvia Nutrition 0.000 description 1
- 241000607720 Serratia Species 0.000 description 1
- 206010041303 Solar dermatitis Diseases 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 230000001532 anti-fungicidal effect Effects 0.000 description 1
- 230000002225 anti-radical effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical class CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000032677 cell aging Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000010874 in vitro model Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000003859 lipid peroxidation Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 210000001589 microsome Anatomy 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 102220047090 rs6152 Human genes 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/14—Liposomes; Vesicles
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
La présente invention concerne l'utilisation de l'acide rosmarinique pour la préparation d'une composition dermato-cosmétique agissant en particulier à la fois comme filtre solaire et comme anti-inflammatoire et présentant par elle-même des propriétés de conservation. The present invention relates to the use of rosmarinic acid for the preparation of a dermato-cosmetic composition which acts in particular both as a sunscreen and as an anti-inflammatory and having by itself preservation properties.
L'acide rosmarinique est un ester de l'acide caféique et de l'acide phényl lactique, dont la formule générale déterminée par cristallisation est C18H16 8, 2H20. Rosmarinic acid is an ester of caffeic acid and phenyl lactic acid, the general formula of which is determined by crystallization is C18H16 8, 2H20.
On peut ltextraire de nombreuses plantes de la famille des
Lamiaceae, en particulier des genres : Melissa, Mentha,
Salvia, Lavandula, Satureia, Prunella, Lycopus, Origanum,
Thymus, Rosmarinus, Perilla, Glechoma.... Ces plantes en renferment 1 à 3 % dans la matière sèche. On en trouve également chez des Ombellifères, des Boraginaceae, des
Hydrophyllaceae, des Acanthaceae et chez certaines fougères.Many plants from the family of
Lamiaceae, in particular of the genera: Melissa, Mentha,
Salvia, Lavandula, Satureia, Prunella, Lycopus, Origanum,
Thymus, Rosmarinus, Perilla, Glechoma .... These plants contain 1 to 3% in the dry matter. They are also found in Umbelliferae, Boraginaceae,
Hydrophyllaceae, Acanthaceae and in some ferns.
L'intérêt pharmacologique de l'acide caféique (ou acide 3,4-dihydroxycinnamique) et de plusieurs dérivés naturels de celui-ci a déjà fait l'objet de nombreuses études. The pharmacological interest of caffeic acid (or 3,4-dihydroxycinnamic acid) and several natural derivatives of it has already been the subject of numerous studies.
Ainsi Kimura et al (Planta Medica, 1984, 473-477) ont étudié l'effet de divers tanins et en particulier de dérivés de l'acide caféique et caféoylquinique extraits de plantes de l'espèces Artemisia et ont montré leur effet inhibiteur sur la peroxydation des lipides dans les mitochondries et les microsomes de foie de rat. L'action inhibitrice de ces molécules sur les lipoxygénases participant au métabolisme des leucotriènes et de l'acide arachidonique et leur utilisation potentielle dans le traitement d'affections inflammatoires comme l'asthme ont aussi été publiées par Kimura et Okuda (J. of natural
Products, 1987, 50, 392-399).Thus Kimura et al (Planta Medica, 1984, 473-477) studied the effect of various tannins and in particular of caffeic and caffeoylquinic acid derivatives extracted from plants of the Artemisia species and showed their inhibitory effect on the lipid peroxidation in mitochondria and rat liver microsomes. The inhibitory action of these molecules on lipoxygenases participating in the metabolism of leukotrienes and arachidonic acid and their potential use in the treatment of inflammatory conditions such as asthma have also been published by Kimura and Okuda (J. of natural
Products, 1987, 50, 392-399).
L'activité de différents dérivés de tanins caféiques étant multiple et variable en fonction de leur structure, il est intéressant de rechercher de nouvelles molécules de cette famille, dans les plantes médicinales ou autres, et de rechercher de nouvelles activités pharmacologiques ou des performances supérieures ou de nouvelles applications, pour les dérivés déjà connus. The activity of different derivatives of caffeine tannins being multiple and variable according to their structure, it is interesting to search for new molecules of this family, in medicinal or other plants, and to search for new pharmacological activities or superior performances or new applications, for already known derivatives.
Ainsi le Demandeur a mis en évidence un certain nombre de propriétés de l'acide rosmarinique qui permettent de lui trouver une application particulièrement intéressante en dermato-cosmétologie. Thus the Applicant has highlighted a certain number of properties of rosmarinic acid which allow it to find a particularly interesting application in dermato-cosmetology.
Le Demandeur a en effet observé que le spectre d'absorption des rayons U.V.de l'acide rosmarinique correspond a la zone la plus nocive pour le peau des UV-B du rayonnement solaire (297-308 nm). The Applicant has in fact observed that the absorption spectrum of UV rays from rosmarinic acid corresponds to the area most harmful to the skin from UV-B from solar radiation (297-308 nm).
D'autre part les propriétés anti-inflammatoires de l'acide rosmarinique dues à llinhibition des lipoxygénases dans le métabolisme des leucotriènes et de l'acide arachidonique sont bien connues et font déjà l'objet d'applications thérapeutiques. On the other hand, the anti-inflammatory properties of rosmarinic acid due to the inhibition of lipoxygenases in the metabolism of leukotrienes and arachidonic acid are well known and are already the subject of therapeutic applications.
En plus de ces propriétés, le Demandeur a mis en évidence, dans plusieurs modèles in vitro, l'action protectrice de l'acide rosmarinique contre l'action toxique de diverses substances, toxicité qui est généralement attribuée à la libération de radicaux libres. En particulier sur des hépatocytes de lapin en culture primaire, en présence de générateurs de radicaux libres et par comparaison avec des molécules connues comme "piégeurs" efficaces de ces radicaux libres, comme l'a-tocophérol et les flavonoides, l'acide rosmarinique apparaît comme particulièrement efficace. In addition to these properties, the Applicant has demonstrated, in several in vitro models, the protective action of rosmarinic acid against the toxic action of various substances, toxicity which is generally attributed to the release of free radicals. In particular on rabbit hepatocytes in primary culture, in the presence of free radical generators and by comparison with molecules known as effective "scavengers" of these free radicals, such as α-tocopherol and flavonoids, rosmarinic acid appears as particularly effective.
La présente invention concerne donc une composition dermato-cosmétique comprenant comme principe actif l'acide rosmarinique ou un de ses dérivés physiologiquement acceptable, en association avec un excipient inerte et éventuellement d'autres substances actives. Selon un mode préféré de l'invention l'excipient sera constitué de liposomes, ceux-ci pouvant favoriser la résorption des substances actives. The present invention therefore relates to a dermato-cosmetic composition comprising, as active principle, rosmarinic acid or one of its physiologically acceptable derivatives, in combination with an inert excipient and optionally other active substances. According to a preferred embodiment of the invention, the excipient will consist of liposomes, which can promote the resorption of the active substances.
On choisira comme dose efficace placide rosmarinique une concentration comprise entre 0,1 et 5 %. The effective rosmarinic placid dose will be a concentration of between 0.1 and 5%.
La composition dermato-cosmétique selon la présente invention devrait être particulièrement efficace dans la prévention du vieillissement de la peau et dans le traitement des états inflammatoires qui accompagnent souvent l'érythème solaire. En effet, on sait que dans certaines conditions métaboliques ou perturbations d'origine externe comme l'exposition aux rayons ultra-violets, la réduction de l'oxygène est incomplète et aboutit à la formation de radicaux libres pouvant détériorer les phospholipides des membranes cellulaires. La production de radicaux libres entraine diverses manifestation physiopathologiques qui participent au vieillissement cellulaire et peut être à la cancérogénèse, aux phénomènes inflammatoires et au processus d'intoxication hépatique, ce qui justifie l'utilisation des hépatocytes comme système-modèle in vitro. The dermato-cosmetic composition according to the present invention should be particularly effective in the prevention of aging of the skin and in the treatment of the inflammatory conditions which often accompany solar erythema. In fact, it is known that under certain metabolic conditions or disturbances of external origin such as exposure to ultraviolet rays, the reduction of oxygen is incomplete and results in the formation of free radicals which can damage the phospholipids of cell membranes. The production of free radicals leads to various pathophysiological manifestations which participate in cell aging and can be carcinogenesis, inflammatory phenomena and the process of hepatic intoxication, which justifies the use of hepatocytes as a model system in vitro.
Le Demandeur a également mis en évidence des propriétés antibactériennes et antifongiques de l'acide rosmarinique. Ainsi la préparation dermato-cosmétique dans laquelle sera utilisé ce composé pourra ne pas être additionnée d'agent conservateur antimicrobien. The Applicant has also demonstrated the antibacterial and antifungal properties of rosmarinic acid. Thus the dermato-cosmetic preparation in which this compound will be used may not be added with an antimicrobial preservative.
De plus, les remarquables propriétés de l'acide rosmarinique comme inhibiteur de la peroxydation rendent inutile l'addition d'un agent protecteur du rancissement de l'excipient qui peut être de nature- lipidique en dermatocosmétique, le principe actif jouant lui-même ce rôle. In addition, the remarkable properties of rosmarinic acid as an inhibitor of peroxidation make it unnecessary to add a protective agent against the rancidity of the excipient which may be lipidic in dermatocosmetics, the active principle itself playing role.
L'exemple suivant illustre l'invention sans toutefois en limiter la portée. Les deux figures illustrent les résultats expérimentaux. The following example illustrates the invention without however limiting its scope. The two figures illustrate the experimental results.
La figure 1 représente l'inhibition du radical O2C dans la réaction xanthine-xanthine oxydase
la : en présence d'acide rosmarinique (A.R) ou d'acide chlorogénique (A.Cl)
lb : en présence d'acide rosmarinique et de myricétine (Myr.).FIG. 1 represents the inhibition of the O2C radical in the xanthine-xanthine oxidase reaction
la: in the presence of rosmarinic acid (AR) or chlorogenic acid (A.Cl)
lb: in the presence of rosmarinic acid and myricetin (Myr.).
La figure 2 représente la lipoperoxydation par les microsones d'hépatocytes de lapin (dosage du malonyldialdéhyde-MDA). FIG. 2 represents the lipoperoxidation by the microsones of rabbit hepatocytes (assay of malonyldialdehyde-MDA).
2a : dans les conditions standard
2b : après action de CC14
2c : après action de H2O2 (T = TéMOIN ; A.C. = acide caféique ; Vit.E = vitamine E ou a-Tocophérol ; A.R. = acide rosmarinique).2a: under standard conditions
2b: after action of CC14
2c: after the action of H2O2 (T = WITNESS; AC = caffeic acid; Vit.E = vitamin E or a-Tocopherol; AR = rosmarinic acid).
EXEMPLE
A. Extraction et purification de l'acide rosmarinique.EXAMPLE
A. Extraction and purification of rosmarinic acid.
Les plantes (par exemple Melissa) sont réduites en poudre demi-fine, dégraissée et dépigmentée par extraction à l'éther de pétrole pendant 72 heures. The plants (for example Melissa) are reduced to semi-fine powder, defatted and depigmented by extraction with petroleum ether for 72 hours.
(Les " eaux-mè re s " de distillation des huiles essentielles de certaines Labiées comme la mélisse et les sauges peuvent aussi être utilisées comme matériau de départ). (The "mother liquors" for the distillation of essential oils from certain Labies such as lemon balm and sage can also be used as starting material).
Cette poudre est mise à macérer dans un mélange éthanol-eau (80:20%) à 500C. Cet infusé est concentré par évaporation de l'alcool, dans un évaporateur rotatif sous vide à 35"C. This powder is macerated in an ethanol-water mixture (80: 20%) at 500C. This infusion is concentrated by evaporation of the alcohol, in a rotary evaporator under vacuum at 35 "C.
L'extrait est passé sur colonne de chromatographie sur cellulose et élué avec de l'eau. Les fractions aqueuses contenant l'acide rosmarinique sont rassemblées puis concentrées et décolorées sur du charbon activé, en milieu aqueux. The extract is passed through a cellulose chromatography column and eluted with water. The aqueous fractions containing rosmarinic acid are combined and then concentrated and discolored on activated charcoal in an aqueous medium.
L'extrait est purifié par chromatographie sur résine Séphadex LH20 (Pharmacia). Les fractions éluées contenant l'acide rosmarinique sont rassemblées et concentrées puis mises à cristalliser à 4"C. The extract is purified by chromatography on Sephadex LH20 resin (Pharmacia). The eluted fractions containing rosmarinic acid are combined and concentrated then allowed to crystallize at 4 "C.
B. Etude du spectre d'absorption UV de l'acide rosmarinique purifié.B. Study of the UV absorption spectrum of purified rosmarinic acid.
Le spectre UV est mesuré sur une solution d'acide rosmarinique dans l'éthanol "pour spectrophotométrie UV". The UV spectrum is measured on a solution of rosmarinic acid in ethanol "for UV spectrophotometry".
Les résultats suivant sont enregistrées
X maximum : g2227 - g2347 - 290 - 330
minimum : 264.The following results are saved
Maximum X: g2227 - g2347 - 290 - 330
minimum: 264.
C. Etudes des propriétés antibactériennes et antifoncicues. C. Studies of antibacterial and antifungal properties.
Un certain nombre de dérivés de l'acide caféique présentent des propriétés antimicrobiennes. Ceci a été confirmé pour l'acide rosmarinique qui apparaît comme un des dérivés les plus efficaces. A number of derivatives of caffeic acid have antimicrobial properties. This has been confirmed for rosmarinic acid which appears to be one of the most effective derivatives.
La concentration minimale inhibitrice (CMI) est comprise entre 0,06 et 0,25 mg/ml en milieu gélosé pour les souches bactériennes (d'origines hospitalière) suivantes
Staphylococcus aureus (29 souches testées), Streptococcus (3s), Escherichia coli (5s), Klebsiella pneumoniae (6s),
Proteus (6s), Providencia (2s), Serratia marescens (ils),
Enterobacter cloacae (2s), Pseudomonas aeruginosa (23s),
Salmonella (2s). The minimum inhibitory concentration (MIC) is between 0.06 and 0.25 mg / ml in agar medium for the following bacterial strains (of hospital origin)
Staphylococcus aureus (29 strains tested), Streptococcus (3s), Escherichia coli (5s), Klebsiella pneumoniae (6s),
Proteus (6s), Providencia (2s), Serratia marescens (they),
Enterobacter cloacae (2s), Pseudomonas aeruginosa (23s),
Salmonella (2s).
L'activité antifongicide de l'acide rosmarinique a déjà été publiée par le Demandeur (Andary et al. 1981,
Cryptogamie, Mycologie 2, 119 - 130) . Des résultats complémentaires montrent que la CMI est de 0,12 mg/ml en milieu gélosé, pour les dermatophytes (d'origine hospitalière) suivantes
Microsporum gyspeum, canis et audouini, Trichophyton mentagrophytes, soudanense et rubrum, Epidermophyton floccosum.The anti-fungicidal activity of rosmarinic acid has already been published by the Applicant (Andary et al. 1981,
Cryptogamy, Mycology 2, 119 - 130). Additional results show that the MIC is 0.12 mg / ml in agar medium, for the following dermatophytes (of hospital origin)
Microsporum gyspeum, canis and audouini, Trichophyton mentagrophytes, sudanense and rubrum, Epidermophyton floccosum.
D. Etude de l'action antiradicalaire de l'acide rosmarinique
D.1. Le premier modèle expérimental choisi est l'étude de effet protecteur sur les hépatocytes de lapin intoxiqués au nitroxynyl (10-4 à 10-5 M) ou au tétrachlorométhane (10-5M). D. Study of the anti-free radical action of rosmarinic acid
D.1. The first experimental model chosen is the study of a protective effect on rabbit hepatocytes poisoned with nitroxynyl (10-4 to 10-5 M) or tetrachloromethane (10-5M).
L'examen au microscope des hépatocytes intoxiqués montre une dégénérescence des membranes cytoplasmiques et une perte de la morphologie cellulaire qui ne se manifestent pas quand les cellules sont traitées précocément avec l'acide rosmarinique (5.10-5 M). Microscopic examination of the intoxicated hepatocytes shows a degeneration of the cytoplasmic membranes and a loss of cell morphology which do not manifest themselves when the cells are treated early with rosmarinic acid (5.10-5 M).
D'autre part, quand on mesure la libération dans le milieu de culture de lactate déshydrogénase (LDH) qui est un marqueur de dégradation des hépatocytes, on observe une inhibition significative en présence d'un excès d'acide rosmarinique. On the other hand, when the release into the culture medium of lactate dehydrogenase (LDH) which is a marker of hepatocyte degradation is measured, a significant inhibition is observed in the presence of an excess of rosmarinic acid.
D2. L'activité antioxydante de l'acide rosmarinique a été mise en évidence dans un test d'inhibition du radical superoxyde 020- (réaction xanthinexanthine oxydase) - en comparaison avec un autre dérivé de l'acide caféiquer l'acide chlorogénique : la figure la montre que l'acide rosmarinique est plus efficace
- en comparaison avec le flavonoïde considéré comme le plus action, la myricétine (Rafat Husein et al., 1987, Phytochem. 26, 2489 - 2491) : la figure lb montre que l'acide rosmarinique a pratiquement la même efficacité.D2. The antioxidant activity of rosmarinic acid was demonstrated in a test for inhibition of the superoxide radical 020- (xanthinexanthine oxidase reaction) - in comparison with another derivative of caffeic acid chlorogenic acid: Figure la shows that rosmarinic acid is more effective
- in comparison with the flavonoid considered to be the most active, myricetin (Rafat Husein et al., 1987, Phytochem. 26, 2489 - 2491): Figure 1b shows that rosmarinic acid has practically the same effectiveness.
D.3. L'activité antiradicalaire de l'acide rosmarinique est particulièrement bien mise en évidence dans le test d'inhibition de la lipoperoxydation à partir des microsones hépatiques de lapin. Une réaction de lipoperoxydation se produit lorsqu'on incube des microsomes hépatiques de lapin en présence de NADPK. D.3. The anti-radical activity of rosmarinic acid is particularly well demonstrated in the test for inhibition of lipoperoxidation from hepatic rabbit microsones. A lipoperoxidation reaction occurs when incubating rabbit liver microsomes in the presence of NADPK.
Les microsomes sont récupérés après traitement des hépatocytes aux ultra-sons. The microsomes are recovered after treatment of the hepatocytes with ultrasound.
La lipoperoxydation est évaluée par la formation de malonyldialdéhyde (MDA) selon la méthode de Placer et al. Lipoperoxidation is evaluated by the formation of malonyldialdehyde (MDA) according to the method of Placer et al.
(1966, Analyt. Biochem. 16, 359 - 364) . La réaction est effectuée en absence (témoin) et en présence d'acide caféique ou d'acide rosmarinique à la concentration de 5.10-5M ou en présence d'a-tocophérol (Sigma) 5.10-5M (référence d'activité inhibitrice connue).(1966, Analyt. Biochem. 16, 359 - 364). The reaction is carried out in the absence (control) and in the presence of caffeic acid or rosmarinic acid at a concentration of 5.10-5M or in the presence of an a-tocopherol (Sigma) 5.10-5M (reference known inhibitory activity) .
L'oxydation des lipides membranaîres peut être potentialisée par l'addition dans le- milieu réactionnel de molécules productrices de radicauxx libres comme le CC14 (tétrachlorure de carbone) et l'H2O2 (eau oxygénée). Même dans ces conditions, l'activité inhibitrice de l'acide rosmarinique est nettement plus forte que celle de lsa- tocophérol. The oxidation of membrane lipids can be potentiated by the addition in the reaction medium of molecules producing free radicals such as CC14 (carbon tetrachloride) and H2O2 (hydrogen peroxide). Even under these conditions, the inhibitory activity of rosmarinic acid is clearly stronger than that of santocopherol.
Claims (7)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8912370A FR2652001B1 (en) | 1989-09-20 | 1989-09-20 | DERMATO-COSMETIC COMPOSITION BASED ON ROSMARINIC ACID HAVING PROPERTIES OF SUN FILTER AND ANTI-INFLAMMATORY AGENT. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8912370A FR2652001B1 (en) | 1989-09-20 | 1989-09-20 | DERMATO-COSMETIC COMPOSITION BASED ON ROSMARINIC ACID HAVING PROPERTIES OF SUN FILTER AND ANTI-INFLAMMATORY AGENT. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2652001A1 true FR2652001A1 (en) | 1991-03-22 |
| FR2652001B1 FR2652001B1 (en) | 1994-09-09 |
Family
ID=9385705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8912370A Expired - Fee Related FR2652001B1 (en) | 1989-09-20 | 1989-09-20 | DERMATO-COSMETIC COMPOSITION BASED ON ROSMARINIC ACID HAVING PROPERTIES OF SUN FILTER AND ANTI-INFLAMMATORY AGENT. |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2652001B1 (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992013523A1 (en) * | 1991-02-07 | 1992-08-20 | A. Nattermann & Cie. Gmbh | Pharmaceutical product for treating viral diseases |
| FR2676361A1 (en) * | 1991-05-17 | 1992-11-20 | Oreal | Process for enhancing the activity of a rosemary extract constituting an active ingredient in a composition for cosmetic and/or dermopharmaceutical use and composition for carrying out the aforementioned process |
| EP0582147A3 (en) * | 1992-08-03 | 1994-08-24 | Nestle Sa | Anti-urease cosmetic or dermatologic composition |
| WO2000039248A1 (en) * | 1998-12-24 | 2000-07-06 | Rad Natural Technologies Ltd. | Method for protecting a substance liable to oxidative deterioration |
| WO2000041674A1 (en) * | 1999-01-15 | 2000-07-20 | L'oreal | Use of a plant extract of the genus rosmarinus in compositions for treating ageing skin symptoms |
| US6383543B1 (en) | 1998-12-24 | 2002-05-07 | Rad Natural Technologies Ltd. | Process for the extraction of an organic salt from plants, the salt, and other similar salts |
| EP1260212A1 (en) * | 2001-05-21 | 2002-11-27 | Cognis France S.A. | Cosmetic composition |
| CN116650462A (en) * | 2023-05-31 | 2023-08-29 | 湖北中医药大学 | New application of rosmarinic acid, gel containing rosmarinic acid and preparation method |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2596986A1 (en) * | 1986-04-11 | 1987-10-16 | Sederma Sa | Use of lactoferrin in cosmetic preparations acting against free radicals |
| JPS63162611A (en) * | 1986-12-24 | 1988-07-06 | Pola Chem Ind Inc | Cosmetic |
| JPH01121217A (en) * | 1987-11-05 | 1989-05-12 | Advance Co Ltd | 5-lipoxigenase inhibitor |
-
1989
- 1989-09-20 FR FR8912370A patent/FR2652001B1/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2596986A1 (en) * | 1986-04-11 | 1987-10-16 | Sederma Sa | Use of lactoferrin in cosmetic preparations acting against free radicals |
| JPS63162611A (en) * | 1986-12-24 | 1988-07-06 | Pola Chem Ind Inc | Cosmetic |
| JPH01121217A (en) * | 1987-11-05 | 1989-05-12 | Advance Co Ltd | 5-lipoxigenase inhibitor |
Non-Patent Citations (2)
| Title |
|---|
| PATENT ABSTRACTS OF JAPAN, vol. 12, no. 438 (C-544)[3285], 17 novembre 1988; & JP-A-63 162 611 (POLA CHEM. IND. INC.) 06-07-1988 * |
| PATENT ABSTRACTS OF JAPAN, vol. 13, no. 362 (C-625)[3710], 14 août 1989; & JP-A-1 121 217 (ADVANCE CO. LTD) 12-05-1989 * |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992013523A1 (en) * | 1991-02-07 | 1992-08-20 | A. Nattermann & Cie. Gmbh | Pharmaceutical product for treating viral diseases |
| FR2676361A1 (en) * | 1991-05-17 | 1992-11-20 | Oreal | Process for enhancing the activity of a rosemary extract constituting an active ingredient in a composition for cosmetic and/or dermopharmaceutical use and composition for carrying out the aforementioned process |
| EP0582147A3 (en) * | 1992-08-03 | 1994-08-24 | Nestle Sa | Anti-urease cosmetic or dermatologic composition |
| WO2000039248A1 (en) * | 1998-12-24 | 2000-07-06 | Rad Natural Technologies Ltd. | Method for protecting a substance liable to oxidative deterioration |
| US6383543B1 (en) | 1998-12-24 | 2002-05-07 | Rad Natural Technologies Ltd. | Process for the extraction of an organic salt from plants, the salt, and other similar salts |
| WO2000041674A1 (en) * | 1999-01-15 | 2000-07-20 | L'oreal | Use of a plant extract of the genus rosmarinus in compositions for treating ageing skin symptoms |
| FR2788435A1 (en) * | 1999-01-15 | 2000-07-21 | Oreal | USE OF AN EXTRACT OF A PLANT OF THE GENUS ROSMARINUS IN COMPOSITIONS FOR TREATING SKIN SIGNS OF AGING |
| EP1260212A1 (en) * | 2001-05-21 | 2002-11-27 | Cognis France S.A. | Cosmetic composition |
| WO2002094210A3 (en) * | 2001-05-21 | 2004-10-21 | Cognis France Sa | Cosmetic agents |
| CN116650462A (en) * | 2023-05-31 | 2023-08-29 | 湖北中医药大学 | New application of rosmarinic acid, gel containing rosmarinic acid and preparation method |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2652001B1 (en) | 1994-09-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20210154155A1 (en) | Compositions of bakuchiol and methods of making the same | |
| EP0576420B1 (en) | Novel derivative of caffeic acid, oraposide, cosmetic or pharmaceutical, particularly dermatological, composition containing it | |
| KR102642352B1 (en) | Bakuchiol compositions for treatment of post inflammatory hyperpigmentation | |
| EP0810222B1 (en) | Process for extraction of polyphenolic compounds of catechin type from plants, the so obtained extract and its use | |
| FR2652001A1 (en) | Dermato-cosmetic composition based on rosmarinic acid, possessing properties of a sunscreen agent and anti-inflammatory agent | |
| CA2747681C (en) | Polyunsaturated fatty acid and diol ester as an anti-acne agent | |
| FR2714054A1 (en) | 4-Hydroxy-5-methyl-3-Ý2H¨-furanone extn. from Pinaceae | |
| JP2017119635A (en) | Cyclooxygenase-2 inhibitor derived from juncus effusus l. var.decipiens buchen. | |
| FR2652086A1 (en) | New compound of plant origin, derived from caffeic acid, oraposide; composition for therapeutic use and dermocosmetic composition containing it | |
| El-Haci et al. | Total phenolic content and antioxidant activity of a medicinal plant endemic to the Algerian Sahara | |
| WO2012093919A2 (en) | Composition for treating leukemia and method for preparing myrrh extract | |
| JP3976890B2 (en) | Novel compounds or pharmacologically acceptable salts thereof and antioxidants containing them as active ingredients | |
| Marszalek et al. | Larrea tridentata Extracts and the Capacity of Its Biocompounds in Medicine and Agriculture | |
| EP4304622A1 (en) | Combination of a myrtle extract and a tripterygium wilfordii extract for controlling c. acnes-induced inflammation | |
| FR2758086A1 (en) | Use of shogaols and gingerols | |
| Boukacem et al. | Etude phytochimique et évaluation des activités antibactérienne et antifongique des extrais de Henné «Lawsonia inermis» | |
| FR2933300A1 (en) | Composition, useful e.g. in medicament and dermatological composition to treat acne, hyperseborrhea and rosacea, comprises at least one lignan and/or neolignan, or their plant extract, in combination with a compound active against acne | |
| FR2988563A1 (en) | Ludwigia grandiflora plant extract, useful as antibacterial agent against e.g. Clostridium botulinum for treating e.g. skin infections and as antimicrobial agent in product for cleaning, decontaminating and disinfecting surfaces of human | |
| FR2988562A1 (en) | Ludwigia peploides plant extract useful as antibacterial agent against e.g. Bacillus anthracis and Haemophilus influenzae to treat e.g. skin infection and antimicrobial agent in product to clean and disinfect e.g. body surface of human | |
| HK1120743B (en) | Compositions of bakuchiol and methods of making the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |
Effective date: 20060531 |