CN116531289A - Stable olive leaf extract composition - Google Patents
Stable olive leaf extract composition Download PDFInfo
- Publication number
- CN116531289A CN116531289A CN202310405689.5A CN202310405689A CN116531289A CN 116531289 A CN116531289 A CN 116531289A CN 202310405689 A CN202310405689 A CN 202310405689A CN 116531289 A CN116531289 A CN 116531289A
- Authority
- CN
- China
- Prior art keywords
- olive leaf
- leaf extract
- oxo
- oleuropein
- composition
- 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
- 229940114496 olive leaf extract Drugs 0.000 title claims abstract description 72
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- BMLMGCPTLHPWPY-REOHCLBHSA-N (4R)-2-oxo-4-thiazolidinecarboxylic acid Chemical compound OC(=O)[C@@H]1CSC(=O)N1 BMLMGCPTLHPWPY-REOHCLBHSA-N 0.000 claims abstract description 54
- RFWGABANNQMHMZ-UHFFFAOYSA-N 8-acetoxy-7-acetyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline Natural products CC=C1C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(C(=O)OC)=COC1OC1OC(CO)C(O)C(O)C1O RFWGABANNQMHMZ-UHFFFAOYSA-N 0.000 claims abstract description 40
- HKVGJQVJNQRJPO-UHFFFAOYSA-N Demethyloleuropein Natural products O1C=C(C(O)=O)C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(=CC)C1OC1OC(CO)C(O)C(O)C1O HKVGJQVJNQRJPO-UHFFFAOYSA-N 0.000 claims abstract description 40
- RFWGABANNQMHMZ-HYYSZPHDSA-N Oleuropein Chemical compound O([C@@H]1OC=C([C@H](C1=CC)CC(=O)OCCC=1C=C(O)C(O)=CC=1)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RFWGABANNQMHMZ-HYYSZPHDSA-N 0.000 claims abstract description 40
- 235000011576 oleuropein Nutrition 0.000 claims abstract description 40
- RFWGABANNQMHMZ-CARRXEGNSA-N oleuropein Natural products COC(=O)C1=CO[C@@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)C(=CC)[C@H]1CC(=O)OCCc3ccc(O)c(O)c3 RFWGABANNQMHMZ-CARRXEGNSA-N 0.000 claims abstract description 40
- 230000015556 catabolic process Effects 0.000 claims abstract description 16
- 238000006731 degradation reaction Methods 0.000 claims abstract description 16
- 239000002537 cosmetic Substances 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000002845 discoloration Methods 0.000 claims abstract description 9
- 240000007817 Olea europaea Species 0.000 claims description 14
- 235000002725 Olea europaea Nutrition 0.000 claims description 9
- 238000009472 formulation Methods 0.000 claims description 9
- 239000000284 extract Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 7
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 abstract description 11
- 239000013543 active substance Substances 0.000 abstract description 10
- 230000003078 antioxidant effect Effects 0.000 abstract description 5
- 150000003862 amino acid derivatives Chemical class 0.000 abstract description 4
- 230000000694 effects Effects 0.000 description 13
- 235000006708 antioxidants Nutrition 0.000 description 10
- 230000008859 change Effects 0.000 description 10
- -1 glucosyl rutin Chemical compound 0.000 description 9
- JUUBCHWRXWPFFH-UHFFFAOYSA-N Hydroxytyrosol Chemical compound OCCC1=CC=C(O)C(O)=C1 JUUBCHWRXWPFFH-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 description 6
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 description 6
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 6
- 235000005493 rutin Nutrition 0.000 description 6
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 6
- 229960004555 rutoside Drugs 0.000 description 6
- SHOKSIZSCQFIRY-UHFFFAOYSA-N [3-(2-tert-butyl-2-hydroxy-4,4-dimethyl-3-phenylpentanoyl)oxy-2,2-bis[(2-tert-butyl-2-hydroxy-4,4-dimethyl-3-phenylpentanoyl)oxymethyl]propyl] 2-tert-butyl-2-hydroxy-4,4-dimethyl-3-phenylpentanoate Chemical compound C=1C=CC=CC=1C(C(C)(C)C)C(O)(C(C)(C)C)C(=O)OCC(COC(=O)C(O)(C(C=1C=CC=CC=1)C(C)(C)C)C(C)(C)C)(COC(=O)C(O)(C(C=1C=CC=CC=1)C(C)(C)C)C(C)(C)C)COC(=O)C(O)(C(C)(C)C)C(C(C)(C)C)C1=CC=CC=C1 SHOKSIZSCQFIRY-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 235000003248 hydroxytyrosol Nutrition 0.000 description 4
- 229940095066 hydroxytyrosol Drugs 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- 235000013824 polyphenols Nutrition 0.000 description 4
- QWMQFNDBELVLER-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;1-hydroxy-2,3,3,4-tetramethylpiperidin-2-ol Chemical compound CC1CCN(O)C(C)(O)C1(C)C.CC1CCN(O)C(C)(O)C1(C)C.CC1CCN(O)C(C)(O)C1(C)C.OC(=O)CC(O)(C(O)=O)CC(O)=O QWMQFNDBELVLER-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 3
- 150000008442 polyphenolic compounds Chemical class 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- TXXNVPVRPSACBM-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)[NH+]1O.CC1(C)CC(O)CC(C)(C)[NH+]1O.CC1(C)CC(O)CC(C)(C)[NH+]1O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O TXXNVPVRPSACBM-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 239000002502 liposome Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- QFRYQWYZSQDFOS-UHFFFAOYSA-N verbascoside Natural products CC1OC(COC2C(O)C(COC3OC(C(O)C(O)C3O)C(=O)O)OC(Oc4cc(O)cc5OC(=CC(=O)c45)c6ccc(O)c(O)c6)C2O)C(O)C(O)C1O QFRYQWYZSQDFOS-UHFFFAOYSA-N 0.000 description 2
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical class CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 description 1
- PPVDHXWQWABSBC-UHFFFAOYSA-N 2-(2,6-diethyl-4-hydroxy-3,5-dimethoxyphenyl)-2-hexyl-1,3-dioxane-4,6-dione Chemical compound CCC=1C(OC)=C(O)C(OC)=C(CC)C=1C1(CCCCCC)OC(=O)CC(=O)O1 PPVDHXWQWABSBC-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- UBSCDKPKWHYZNX-UHFFFAOYSA-N Demethoxycapillarisin Natural products C1=CC(O)=CC=C1OC1=CC(=O)C2=C(O)C=C(O)C=C2O1 UBSCDKPKWHYZNX-UHFFFAOYSA-N 0.000 description 1
- 244000147058 Derris elliptica Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- 241000207834 Oleaceae Species 0.000 description 1
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 1
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- FBSKJMQYURKNSU-ZLSOWSIRSA-N acteoside Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC(=O)\C=C\C=2C=C(O)C(O)=CC=2)[C@@H](CO)O[C@@H](OCCC=2C=C(O)C(O)=CC=2)[C@@H]1O FBSKJMQYURKNSU-ZLSOWSIRSA-N 0.000 description 1
- 229930185474 acteoside Natural products 0.000 description 1
- FBSKJMQYURKNSU-UKQWSTALSA-N acteoside I Natural products C[C@@H]1O[C@H](O[C@@H]2[C@@H](O)[C@H](OCCc3ccc(O)c(O)c3)O[C@H](CO)[C@H]2OC(=O)C=Cc4ccc(O)c(O)c4)[C@H](O)[C@H](O)[C@H]1O FBSKJMQYURKNSU-UKQWSTALSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- XADJWCRESPGUTB-UHFFFAOYSA-N apigenin Natural products C1=CC(O)=CC=C1C1=CC(=O)C2=CC(O)=C(O)C=C2O1 XADJWCRESPGUTB-UHFFFAOYSA-N 0.000 description 1
- 235000008714 apigenin Nutrition 0.000 description 1
- KZNIFHPLKGYRTM-UHFFFAOYSA-N apigenin Chemical compound C1=CC(O)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 KZNIFHPLKGYRTM-UHFFFAOYSA-N 0.000 description 1
- 229940117893 apigenin Drugs 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229940116365 diethylhexyl syringylidenemalonate Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 235000008777 kaempferol Nutrition 0.000 description 1
- LRDGATPGVJTWLJ-UHFFFAOYSA-N luteolin Natural products OC1=CC(O)=CC(C=2OC3=CC(O)=CC(O)=C3C(=O)C=2)=C1 LRDGATPGVJTWLJ-UHFFFAOYSA-N 0.000 description 1
- 235000009498 luteolin Nutrition 0.000 description 1
- IQPNAANSBPBGFQ-UHFFFAOYSA-N luteolin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C(O)=C1 IQPNAANSBPBGFQ-UHFFFAOYSA-N 0.000 description 1
- 238000000874 microwave-assisted extraction Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003305 rutin Chemical class 0.000 description 1
- IKGXIBQEEMLURG-NVPNHPEKSA-N rutin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-NVPNHPEKSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003815 supercritical carbon dioxide extraction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002137 ultrasound extraction Methods 0.000 description 1
- KDSWDGKIENPKLB-QJDQKFITSA-N verbascoside Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC(=O)CCC=2C=C(O)C(O)=CC=2)[C@@H](CO)O[C@@H](OCCC=2C=C(O)C(O)=CC=2)[C@@H]1O KDSWDGKIENPKLB-QJDQKFITSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Classifications
-
- 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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
-
- 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
-
- 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
-
- 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
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Botany (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Abstract
The invention provides a stable olive leaf extract composition. The composition is achieved by adding the amino acid derivative oxo-thiazolidinecarboxylic acid to olive leaf extract. In addition, the invention also provides application of the olive leaf extract and the oxo-thiazolidine carboxylic acid composition in cosmetics and a method for preparing the composition. Finally, the invention proves that the addition of the oxo-thiazolidinecarboxylic acid as an antioxidant can significantly improve the discoloration problem of the olive leaf extract, and the addition of the oxo-thiazolidinecarboxylic acid can slow down the degradation of the oleuropein as a main active substance in the olive leaf extract.
Description
Technical Field
The invention relates to the field of cosmetics, and mainly relates to an olive leaf extract composition for stabilization.
Background
Olea europaea L.) is a evergreen tree of Oleaceae, native to the Mediterranean coast, a well-known woody oil tree species in the world. The olive leaf contains abundant active ingredients including oleuropein, hydroxytyrosol, flavonoids, polyphenols, etc. The research shows that the olive leaf extract has the functions of resisting oxidation, inflammation, bacteria, viruses and the like, and is widely applied to the fields of medicines and cosmetics. However, the stability of the main active substances in olive leaves, such as oleuropein, is low, and the changes of the external environment, such as illumination, temperature, pH, acid, alkali, enzyme, etc., can cause degradation, which affects the biological activity (the original flavor, etc., the biosynthesis of olive hydroxytyrosol and the research progress of its derivatives, in the chemistry and industry of forestry, volume 35, phase 2, 154-162, 2015). The specific expression is that the color of the olive leaf extract is deepened, and the content of active substances is reduced.
Patent CN102273623a, "a preparation method of olive leaf extract", improves the stability of olive leaf extract by improving the extraction process. Patent CN115245483A, an immunocyte preparation and a preparation method thereof, improves the stability of oleuropein by forming gel, and patent CN107019672A, a preparation method of olive polyphenol extract long-circulating liposome rich in hydroxytyrosol and verbascoside, improves the stability of olive polyphenol by forming liposome. Although the above method can improve the stability of active substances in olive leaf extract, the treatment is too complicated and has limited practical significance for application in cosmetic formulations. Therefore, there is a need to develop a simple method to improve the stability of olive leaf extract and expand its application range in cosmetic formulations.
Disclosure of Invention
The method for stabilizing olive leaf extract proposed in the previous research mostly forms gel or inclusion by physical method to reduce the influence of external environment on active substance to increase its stability. This method increases the processing steps of the raw materials and limits the application of olive leaf extract in cosmetics. The addition of antioxidants or light stabilizers can increase the stability of the plant extract, but the nature of the antioxidants and light stabilizers and their effect on the formulation need to be considered.
The invention introduces a combination of an amino acid derivative and an olive leaf extract, which has good water solubility and high safety, can slow down the color change of the olive leaf extract caused by environmental change, and can reduce the degradation rate of the oleuropein as a main active substance in the olive leaf extract to a certain extent.
In one aspect, the present invention provides a composition for stabilizing olive leaf extract comprising olive leaf extract and an oxo-thiazolidinecarboxylic acid. The composition is obtained by adding an oxo-thiazolidinecarboxylic acid to olive leaf extract. Oxo-thiazolidine carboxylic acid is an amino acid derivative with a chemical formula of C 4 H 5 NO 3 S has a structural formula of L-2-oxo thiazole-4 carboxylic acid, and the structural formula is shown in formula 1:
further, the olive leaf extract in the composition may be extracted by extraction, ultrasonic-assisted extraction, microwave-assisted extraction, supercritical carbon dioxide extraction, etc., and the extraction mode is not particularly limited. The extract may be a solution or a solid, and the form thereof is not particularly limited. Olive leaves for extraction have oleuropein content of more than 5%, and are stored in cool and ventilated place to avoid degradation of active substances.
Preferably, the olive leaf extract is prepared by a leaching method and a membrane separation process.
Further, the olive leaf extract comprises the following substances: oleuropein, hydroxytyrosol, acteoside, luteolin, apigenin, quercetin, rutin, kaempferol, etc. The active material generally has a phenolic hydroxyl group and a conjugated structure, and is susceptible to deterioration by environmental influences such as oxygen, radicals, and temperature. The color and efficacy changes affect the range of application in cosmetics. The addition of antioxidants can protect the active substance and increase its shelf life.
Further, the main component of the olive leaf extract is oleuropein, and the content of the oleuropein is more than 0.1%.
Preferably, the oleuropein content of the olive leaf extract is greater than 0.6%.
Further, the ratio of the oxo-thiazolidinecarboxylic acid to oleuropein in the olive leaf extract is (0.01-10): 1.
preferably, the ratio of the oxo-thiazolidinecarboxylic acid to oleuropein in the olive leaf extract is (0.1-5): 1.
further preferably, the ratio of the oxo-thiazolidinecarboxylic acid to oleuropein in the olive leaf extract is (0.5-2): 1.
in another aspect, the present invention provides a method for stabilizing olive leaf extract by adding an oxo-thiazolidinecarboxylic acid to olive leaf extract to improve stability.
Further, the ratio of the oxo-thiazolidinecarboxylic acid to oleuropein in the olive leaf extract is (0.01-10): 1.
preferably, the ratio of the oxo-thiazolidinecarboxylic acid to oleuropein in the olive leaf extract is (0.1-5): 1.
further preferably, the ratio of the oxo-thiazolidinecarboxylic acid to oleuropein in the olive leaf extract is (0.5-2): 1.
in another aspect, the present invention provides the use of an oxo-thiazolidinecarboxylic acid for the preparation of a formulation for inhibiting the degradation of oleuropein in olive leaf extracts.
In another aspect, the present invention provides the use of an oxo-thiazolidinecarboxylic acid for the preparation of a formulation for improving the oxidative discoloration problem of olive leaf extracts.
In another aspect, the present invention provides a cosmetic comprising the stable olive leaf extract composition described above.
Further, in the cosmetic, the content of the composition ranges from 0.01 to 30%.
The beneficial effects of the invention include:
1. a stable olive leaf extract composition is provided, comprising olive leaf extract and oxo-thiazolidinecarboxylic acid.
2. The addition of the oxo-thiazolidinecarboxylic acid proved to slow down the degradation of the main active substance oleuropein in the olive leaf extract.
3. The addition of the oxo-thiazolidinecarboxylic acid proved to be able to significantly improve the oxidative discoloration problem of olive leaf extracts.
4. Greatly increases the application range of the olive leaf extract in cosmetics.
Drawings
FIG. 1 Effect of different antioxidants on stability of olive leaf extract in formulations (groups 1-10)
FIG. 2 effect of 0.15% of oxo-thiazolidinecarboxylic acid on stability of olive leaf extract (groups 11-18)
FIG. 3 effect of 0.3% of oxo-thiazolidinecarboxylic acid on stability of olive leaf extract (groups 19-30)
Detailed Description
Example 1 study of the differences in the stability improvement of different antioxidants on olive leaf extracts
First, it was investigated whether the stability of olive leaf extract was improved by oxothiazolidinecarboxylic acid as compared with pentaerythritol tetrakis (di-t-butylhydroxyhydrocinnamate), glucosyl rutin, (tris (tetramethylhydroxypiperidinol) citrate, diethylhexyl butylidene malonate and the like, ten sets of examples of group numbers 1 to 10 were used to investigate the difference in the improvement of the stability of olive leaf extract by different antioxidants, and the composition ratios are shown in table 1.
Table 1: composition ratio of groups 1 to 10
Antioxidants in groups 1-10 include varying concentrations of oxo-thiazolidinecarboxylic acid, pentaerythritol tetrakis (di-t-butylhydroxyhydrocinnamate), glucosyl rutin, (tris (tetramethylhydroxypiperidinol) citrate, diethylhexyl butylidenimalonate, and combinations thereof.
The color change of examples 1-10 was observed after 10 days of storage at different temperature conditions (-18 ℃, 4 ℃, RT, 48 ℃, part of the samples were not tested at room temperature). The results show that under high temperature conditions, groups 3-10 all show a significant darkening, i.e. pentaerythritol tetrakis (di-tert-butylhydroxyhydrocinnamate), glucosyl rutin, (tri (tetramethylhydroxypiperidinol) citrate and diethylhexyl butylidenimalonate all failed to improve the stability of the olive leaf extract, groups 1 and 2 showed a lower degree of color change than the other groups under high temperature conditions, i.e. the oxothiazolidine carboxylic acid had a certain improvement in the stability of the olive leaf extract, and FIG. 1 lists the color change of groups 1-10 after 10 days of storage at different temperatures.
The conclusion is as follows:
pentaerythritol tetrakis (di-tert-butylhydroxyhydrocinnamate), glucosyl rutin, (tri (tetramethylhydroxypiperidinol) citrate and diethylhexyl butylidenimalonate failed to improve the stability of olive leaf extract.
Example 2 study of the Effect of oxo-thiazolidinecarboxylic acid on the stability of olive leaf extract
In order to further investigate the effect of the oxo-thiazolidine carboxylic acid on the stability of olive leaf extract, the effect of temperature (4 ℃ C. And 40 ℃ C. Respectively) and aqueous pH (5.5 and 6 respectively) on the colour of the solution was studied using groups 11-18, the composition ratios are shown in Table 2. Wherein the content of oleuropein in the olive leaf extract is more than 1%.
Table 2: composition ratio of groups 11 to 18
After adjusting the pH to a specified value by using a trace of arginine and citric acid, the groups 11 to 18 are placed in a refrigerator or an oven at a corresponding temperature, and the color change of the solution is observed after taking out on the 7 th day, the 14 th day and the 28 th day. In the sample without the addition of the antioxidant oxothiazolidine carboxylic acid, a prolonged color of the solution, an increase in temperature and a deepening of the rise in pH were observed. Compared with a sample without the oxo-thiazolidine carboxylic acid under the same treatment condition, the sample with the oxo-thiazolidine carboxylic acid has a light color, namely the oxo-thiazolidine carboxylic acid has a certain protection effect on the olive leaf extract, and can slow down the oxidative discoloration. FIG. 2 shows the color change of groups 11-18 after 10 days of standing at different temperatures.
The conclusion is as follows:
the more quickly the solution color deepens over time, the temperature increases and the pH rises. Compared with a sample without the oxo-thiazolidine carboxylic acid under the same treatment condition, the sample with the oxo-thiazolidine carboxylic acid has a light color, namely the oxo-thiazolidine carboxylic acid has a certain protection effect on the olive leaf extract, and can slow down the oxidative discoloration.
Example 3 investigation of the Effect of the content of oxothiazolidinecarboxylic acid on the stability of olive leaf extract
The color change of olive leaf extract at 0.3% of the oxothiazolidinecarboxylic acid content was investigated using a test method similar to the above example under different conditions of temperature (4 ℃ C., 40 ℃ C.) and pH values of aqueous solutions (5, 5.5, 6), the composition distribution ratios are shown in Table 3, and the color change results are shown in FIG. 3. Wherein the content of oleuropein in the olive leaf extract is more than 1%.
Table 3: composition ratio of group 19-30
In the sample without the addition of the antioxidant oxothiazolidine carboxylic acid, a prolonged color of the solution, an increase in temperature and a deepening of the rise in pH were observed. Compared with a sample without the oxo-thiazolidine carboxylic acid under the same treatment condition, the sample with the oxo-thiazolidine carboxylic acid has a light color, namely the oxo-thiazolidine carboxylic acid has a certain protection effect on the olive leaf extract, and can slow down the oxidative discoloration. FIG. 3 shows the color change of groups 19-30 after 10 days of standing at different temperatures.
The conclusion is as follows:
as can be seen by comparing the corresponding samples in fig. 2 and 3 (groups 14 and 26, groups 18 and 30): the oxidative discoloration of olive leaf extract can be further slowed down by increasing the concentration of the oxo-thiazolidinecarboxylic acid.
Example 4 investigation of the Effect of oxo-thiazolidinecarboxylic acid on Oleuropein degradation
The most important active ingredient in olive leaf extract is oleuropein. Oleuropein is easily degraded by the influence of environmental changes such as light, acid, alkali, enzyme and the like, and the biological activity of the oleuropein is influenced. The variation in the content of oleuropein in groups 11-18 over 14 days was tested by HPLC and the results are shown in Table 4.
Table 4: variation of Oleuropein content within 14 days in groups 11-18
Comparing the degradation rates of oleuropein in groups 11-18 under different aqueous conditions, it is known that increasing the pH and temperature of the aqueous solution increases the degradation rate of oleuropein. In groups 11-18, at day 7, the addition of an oxo-thiazolidinecarboxylic acid did not affect the degradation of oleuropein; on day 14, the addition of the oxo-thiazolidine carboxylic acid has no influence on the degradation rate of oleuropein at low temperature, and the oxo-thiazolidine carboxylic acid can reduce the degradation rate of oleuropein in aqueous solutions with pH=5.5 and pH=6 at high temperature. I.e. the degradation rate of oleuropein is mainly affected by the aqueous solution conditions, but at high temperature the oxo-thiazolidinecarboxylic acid can reduce the degradation rate of oleuropein to a certain extent.
The conclusion is as follows:
the oxo-thiazolidinecarboxylic acid can remarkably improve the discoloration problem of the olive leaf extract and slow down the degradation of the oleuropein which is a main active substance in the olive leaf extract to a certain extent. The addition of the oxo-thiazolidinecarboxylic acid can improve the stability of the olive leaf extract and increase the application range of the olive leaf extract in cosmetic formulations.
The present invention is not limited to the specific embodiments described above, and any equivalent modifications and substitutions easily come within the technical scope of the present invention as those skilled in the art can easily come within the scope of the present invention.
Description of efficacy and sources of drugs used in the examples:
the olive leaf is from Gansu Lonnan, and the olive leaf extract is solution with oleuropein content of more than 0.6% by leaching method and membrane separation process.
The oxo-thiazolidine carboxylic acid is an amino acid derivative, is mostly used as a whitening active ingredient in cosmetics, has good antioxidation effect, and is purchased from Nanjing Sibiraeae biochemical industry Co.
Pentaerythritol tetrakis (di-tert-butylhydroxyhydrocinnamate), a cinnamic acid derivative, is a good antioxidant available from basf (china) limited.
(Tri (tetramethyl hydroxypiperidinol) citrate is a derivative of tetramethyl piperidine, a light stabilizer with excellent properties, and is purchased from Basiff (China) Inc.
Glucosyl rutin is a derivative of rutin, and has very strong antioxidant effect, and is purchased from Xianting.
Diethylhexyl syringylidene malonate is a light stabilizer available from merck chemical technologies.
Claims (10)
1. A stable olive leaf extract composition, comprising an olive leaf extract and an oxo-thiazolidinecarboxylic acid.
2. The composition of claim 1, wherein the ratio of the oxothiazolidinecarboxylic acid to oleuropein in the olive leaf extract is (0.01-10): 1.
3. the composition of claim 2, wherein the oleuropein content of the olive leaf extract is greater than 0.1%.
4. A method for stabilizing olive leaf extract, characterized in that the stability is improved by adding an oxo-thiazolidinecarboxylic acid to the olive leaf extract.
5. The method of claim 4, wherein the ratio of the oxothiazolidinecarboxylic acid to oleuropein in the olive leaf extract is (0.01-10): 1.
6. the method of claim 5, wherein the oleuropein content of the olive leaf extract is greater than 0.1%.
7. Use of an oxo-thiazolidinecarboxylic acid for the preparation of a formulation for inhibiting the degradation of oleuropein in olive leaf extracts.
8. Use of an oxo-thiazolidinecarboxylic acid for the preparation of a formulation for improving the oxidative discoloration problem of olive leaf extracts.
9. A cosmetic product comprising a composition according to any one of claims 1 to 3.
10. The cosmetic product of claim 9, wherein the composition is present in an amount ranging from 0.01% to 30%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310405689.5A CN116531289A (en) | 2023-04-17 | 2023-04-17 | Stable olive leaf extract composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310405689.5A CN116531289A (en) | 2023-04-17 | 2023-04-17 | Stable olive leaf extract composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116531289A true CN116531289A (en) | 2023-08-04 |
Family
ID=87442661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310405689.5A Pending CN116531289A (en) | 2023-04-17 | 2023-04-17 | Stable olive leaf extract composition |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116531289A (en) |
-
2023
- 2023-04-17 CN CN202310405689.5A patent/CN116531289A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Peixoto et al. | Grape pomace as a source of phenolic compounds and diverse bioactive properties | |
| Wissam et al. | Effective extraction of polyphenols and proanthocyanidins from pomegranate’s peel | |
| Maisarah et al. | Antioxidant analysis of different parts of Carica papaya | |
| Hanen et al. | Interspecific variability of antioxidant activities and phenolic composition in Mesembryanthemum genus | |
| Akinpelu et al. | The in vitro antioxidant property of methanolic extract of Afzelia africana (Smith.) | |
| Karima et al. | Antioxidant and antimicrobial activities of Plantago major | |
| Haghgoo et al. | Antibacterial effects of different concentrations of Althaea officinalis root extract versus 0.2% chlorhexidine and penicillin on Streptococcus mutans and Lactobacillus (in vitro) | |
| Marina et al. | Quantification of total phenolic compound and in vitro antioxidant potential of fruit peel extracts. | |
| Tan et al. | Protective effects of papaya extracts on tert-butyl hydroperoxide mediated oxidative injury to human liver cells (An in-vitro study) | |
| Wang et al. | Physicochemical properties, chemical composition, and antioxidant activity of Dendropanax dentiger honey | |
| Tuan Putra et al. | Chemical characterization of ethanolic extract of Butterfly pea flower (Clitoria ternatea) | |
| Bonacci et al. | Peracetylation as a strategy to improve oleuropein stability and its affinity to fatty foods | |
| Benslama et al. | Phenolic compounds, antioxidant and antibacterial activities of Zizyphus lotus L. leaves extracts | |
| Abdulkadir et al. | In vitro antioxidant activity of the ethanolic extract from fruit, stem, and leaf of Solanum torvum | |
| Meechai et al. | Antioxidant Properties and Phytochemical Contents of Garcinia schomburgkiana Pierre. | |
| Sani et al. | Effects of standardized stem bark extract of Mangifera indica L. in wistar rats with 2, 4-dinitrophenylhydrazine-induced haemolytic anaemia | |
| Nofouzi | Study on the antioxidant activity and in vitro antifungal activity of Verbascum speciosum methanolic extract | |
| Umamahesh et al. | In vitro anti-oxidant, anti-microbial and anti-inflammatory activities of five Indian cultivars of mango (Mangifera indica L.) fruit peel extracts | |
| CN110446486A (en) | Novel antioxidant for the cosmetics containing glycerol alkyl ether and pharmaceutical composition | |
| Ginovyan et al. | Antioxidant potential of some herbs represented in Armenian flora and characterization of phytochemicals | |
| Özkan et al. | LC-MS/MS analyses of Ziziphora clinopodioides Lam. from Turkey: Antioxidant, anticholinesterase, antimicrobial and, anticancer activities | |
| Bodoira et al. | Impact of storage conditions on the composition and antioxidant activity of peanut skin phenolic‐based extract | |
| Torshabi et al. | Preparation of Citrus reticulata peel nano‐encapsulated essential oil and in vitro assessment of its biological properties | |
| Kumari et al. | Characterization of phenolic compounds in petal extracts of rose | |
| Brahmi et al. | Effect of growth stage and solvent extract on the antioxidant potential of olive leaves |
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 |