CN107308226B - Prinsepia utilis royle extract and preparation method and application thereof - Google Patents
Prinsepia utilis royle extract and preparation method and application thereof Download PDFInfo
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- CN107308226B CN107308226B CN201610270265.2A CN201610270265A CN107308226B CN 107308226 B CN107308226 B CN 107308226B CN 201610270265 A CN201610270265 A CN 201610270265A CN 107308226 B CN107308226 B CN 107308226B
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- 241000727169 Prinsepia utilis Species 0.000 title claims abstract description 153
- 239000000284 extract Substances 0.000 title claims abstract description 66
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- 238000000605 extraction Methods 0.000 title claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 130
- 239000002904 solvent Substances 0.000 claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 230000035755 proliferation Effects 0.000 claims abstract description 19
- 239000000287 crude extract Substances 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 15
- 210000002950 fibroblast Anatomy 0.000 claims abstract description 14
- 230000001737 promoting effect Effects 0.000 claims abstract description 13
- 239000008367 deionised water Substances 0.000 claims abstract description 10
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 10
- 239000011347 resin Substances 0.000 claims abstract description 10
- 229920005989 resin Polymers 0.000 claims abstract description 10
- 239000002537 cosmetic Substances 0.000 claims abstract description 6
- 238000011068 loading method Methods 0.000 claims abstract description 3
- 238000010828 elution Methods 0.000 claims description 58
- 235000013399 edible fruits Nutrition 0.000 claims description 16
- 230000003712 anti-aging effect Effects 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 7
- 238000001179 sorption measurement Methods 0.000 claims description 6
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 claims description 3
- 229930003944 flavone Natural products 0.000 claims description 3
- 150000002212 flavone derivatives Chemical class 0.000 claims description 3
- 235000011949 flavones Nutrition 0.000 claims description 3
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- 238000001914 filtration Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 8
- 230000007760 free radical scavenging Effects 0.000 abstract description 7
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- 238000002835 absorbance Methods 0.000 description 7
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 239000006286 aqueous extract Substances 0.000 description 5
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
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- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000002292 Radical scavenging effect Effects 0.000 description 4
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- 238000012986 modification Methods 0.000 description 4
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- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
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- 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 2
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 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 2
- IKGXIBQEEMLURG-BKUODXTLSA-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-BKUODXTLSA-N 0.000 description 2
- 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 2
- 235000005493 rutin Nutrition 0.000 description 2
- 229960004555 rutoside Drugs 0.000 description 2
- 230000002000 scavenging effect Effects 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- OCZVHBZNPVABKX-UHFFFAOYSA-N 1,1-diphenyl-2-(2,4,6-trinitrophenyl)hydrazine;ethanol Chemical compound CCO.[O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NN(C=1C=CC=CC=1)C1=CC=CC=C1 OCZVHBZNPVABKX-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
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- 206010003399 Arthropod bite Diseases 0.000 description 1
- 208000010445 Chilblains Diseases 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- 108010049047 Echinocandins Proteins 0.000 description 1
- 240000008397 Ganoderma lucidum Species 0.000 description 1
- 235000001637 Ganoderma lucidum Nutrition 0.000 description 1
- 239000009429 Ginkgo biloba extract Substances 0.000 description 1
- 206010023644 Lacrimation increased Diseases 0.000 description 1
- 206010024453 Ligament sprain Diseases 0.000 description 1
- 241001149162 Mallotus japonicus Species 0.000 description 1
- 241000475481 Nebula Species 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 241000632869 Pachira glabra Species 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000003447 Pistacia vera Nutrition 0.000 description 1
- 240000006711 Pistacia vera Species 0.000 description 1
- 241001092483 Prinsepia Species 0.000 description 1
- 235000008997 Prinsepia uniflora Nutrition 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 241000220222 Rosaceae Species 0.000 description 1
- 208000010040 Sprains and Strains Diseases 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 206010053615 Thermal burn Diseases 0.000 description 1
- 206010048038 Wound infection Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 230000001153 anti-wrinkle effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000006214 castanha do maranho Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 230000009982 effect on human Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 229940068052 ginkgo biloba extract Drugs 0.000 description 1
- 235000020686 ginkgo biloba extract Nutrition 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 208000024963 hair loss Diseases 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 230000004317 lacrimation Effects 0.000 description 1
- 229930013686 lignan Natural products 0.000 description 1
- 150000005692 lignans Chemical class 0.000 description 1
- 235000009408 lignans Nutrition 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 231100000075 skin burn Toxicity 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000008736 traumatic injury Effects 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical group [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- 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)
- A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
-
- 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
-
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/331—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using water, e.g. cold water, infusion, tea, steam distillation, decoction
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/55—Liquid-liquid separation; Phase separation
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Microbiology (AREA)
- Botany (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Mycology (AREA)
- Dermatology (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Birds (AREA)
- Chemical & Material Sciences (AREA)
- Alternative & Traditional Medicine (AREA)
- Medical Informatics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Cosmetics (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention relates to the technical field of plant extracts, and discloses a prinsepia utilis royle extract and a preparation method and application thereof. The preparation method of the prinsepia utilis royle extract comprises the steps of extracting the prinsepia utilis royle by adding water or ethanol to obtain a prinsepia utilis royle crude extract; concentrating the crude extract of Prinsepia utilis Royle, loading to macroporous adsorbent resin, sequentially eluting with deionized water, 30% ethanol solution, 70% ethanol solution and 95% ethanol solution, collecting the eluates, distilling under reduced pressure to remove solvent to obtain water eluates, 30% ethanol solution eluates, 70% ethanol solution eluates and 95% ethanol solution eluates. The Prinsepia utilis royle non-oil extract is obtained by taking Prinsepia utilis royle as a raw material and extracting through a proper method, has obvious free radical scavenging activity and the effect of promoting human fibroblast proliferation, and can be used for skin aging resistance and related cosmetics.
Description
Technical Field
The invention relates to the technical field of plant extracts, in particular to a prinsepia utilis royle extract and a preparation method and application thereof.
Background
The Prinsepia utilis Royle is fruit of Prinsepia utilis Royle (Prinsepia utilis Royle) of Prinsepia genus of Rosaceae family, also called Prinsepia utilis Royle, cone fruit, milk hammer, egg cake, plum blossom thorn, pistachio nut, anacis, Mongolia Prinsepia utilis. The Prinsepia utilis Royle is mainly distributed in provinces such as Yunnan province, Guizhou province and Sichuan province, and is produced in pollution-free zones with the elevation above 2000m in Yunnan Lijiang. The green spiny fruit has the fruit period of 4-5 months, the mature fresh green spiny fruit is purple red, the surface is smooth, the dry fruit is dark brown or black, the fruit peel is shriveled and stuck on the fruit core, the fruit core is not easy to be broken, the section is yellow and white, the seeds are rich in grease, the oil yield is about 30%, and the green spiny fruit can be eaten and used daily. The Prinsepia utilis Royle ex Fr et Burk can be used as medicine, and has been used in the minority nationality such as Naxi nationality, Bai nationality, Yi nationality and Mozuo nationality in Yunnan province for thousands of years. According to modern data, the Prinsepia utilis Royle is mainly used for treating nebula, lacrimation, dyspepsia and the like. Medical workers at home and abroad have separated and identified the flavonoid component of the levo-epicatechin from the plant; lignan component (echinocandin); the fatty acid components include palmitic acid, stearic acid, arachidic acid, oleic acid, linoleic acid, linolenic acid, etc. In the twenties of the last century, the miracle plant prinsepia utilis, Joseph Charles Francis Rock, discovered during the investigation of the Yunnan Lijiang, and the current year's literature and plant specimens on prinsepia utilis was kept in the arnode botanical garden at Harvard university. The Prinsepia utilis Royle oil is recorded in mysterious Dongba Jing text at first and has long traditional application history and culture in the aspects of hair care and skin care, for example, the Prinsepia utilis Royle oil is smeared on the skin, can prevent mosquito bite or eliminate lumps formed by traumatic injury and sprain, prevent skin chap and pruritus and cure chilblain; the Prinsepia utilis oil can be used for rubbing hair to inhibit hair loss and blacken white hair; topical skin burn and scald can be prevented by applying Prinsepia utilis oil to affected part to prevent wound infection, accelerate wound healing and avoid scar; the Prinsepia utilis oil is smeared on the skin of a newborn infant to make the skin dry and smooth and can promote the shedding of the fetal hair of the infant; the Prinsepia utilis Royle is called the king of lucky tree and hundred flowers.
The research of the Prinsepia utilis royle oil is mainly focused on the research of the Prinsepia utilis royle oil, the research on the non-oil components of the Prinsepia utilis royle is less, and the Prinsepia utilis royle oil is also taken as a main research object in the aspect of cosmetics at present. Chinese patent CN104523479A discloses an application of prinsepia utilis royle extract in whitening products and the whitening products, which are few research reports about non-oil components of prinsepia utilis royle, and discloses an extract rich in total polyphenol of the prinsepia utilis royle, in particular to an application of prinsepia utilis royle ester alcohol in the whitening products; another chinese patent CN103720635A discloses an anti-wrinkle eye cream, which comprises mallotus japonicus extract, prinsepia utilis royle extract, ganoderma lucidum extract and ginkgo biloba extract as the components, wherein the prinsepia utilis royle extract uses propane as the extraction solvent. However, in the two prior arts, the former only provides the application of the prinsepia utilis royle non-oil extract in whitening, and the latter uses propane as an extraction solvent to obtain the prinsepia utilis royle oil non-polar components, and cannot extract the components with larger polarity, such as flavone and the like. At present, the application and report of the prinsepia utilis royle non-oil extract in the anti-aging aspect in the cosmetic field are not found.
Disclosure of Invention
In view of the above, the present invention aims to provide a prinsepia utilis royle extract, a preparation method and an application thereof, so that the prinsepia utilis royle extract has significant free radical scavenging activity or/and human fibroblast proliferation promoting effect, and further can prevent skin aging and maintain a young and healthy skin state.
In order to achieve the purpose, the invention provides the following technical scheme:
a method for preparing Prinsepia utilis Royle extract comprises:
step 1, adding water or ethanol to the prinsepia utilis royle to extract to obtain a prinsepia utilis royle crude extract;
step 2, concentrating the crude extract of the Prinsepia utilis Royle, loading the concentrated extract to macroporous adsorption resin, eluting with deionized water, 30% ethanol solution, 70% ethanol solution and 95% ethanol solution in sequence, collecting the elution parts respectively, and then distilling under reduced pressure to remove the solvent, thus obtaining a water elution part, a 30% ethanol solution elution part, a 70% ethanol solution elution part and a 95% ethanol solution elution part of the Prinsepia utilis Royle correspondingly;
and 3, evaporating the crude extract of the Prinsepia utilis royle to dryness to obtain a crude extract of the Prinsepia utilis royle, wherein the water elution part, the 30% ethanol solution elution part, the 70% ethanol solution elution part and the 95% ethanol solution elution part of the Prinsepia utilis royle are all prepared Prinsepia utilis royle extracts.
The prinsepia utilis royle extract can be any one of the prinsepia utilis royle extracts, and can also be a mixture of any kinds of the prinsepia utilis royle extracts.
Preferably, the preparation method comprises the following step 1:
adding deionized water or ethanol into Prinsepia utilis Royle ex Palustre fruit according to the proportion of 1g to 20mL, ultrasonically extracting for 2 times at room temperature for 1 hour each time, centrifuging, filtering supernate, and collecting all filtrates to obtain the crude extract of Prinsepia utilis Royle ex Palustre fruit. The Prinsepia utilis royle crude extract is divided into Prinsepia utilis royle water crude extract and Prinsepia utilis royle ethanol crude extract correspondingly according to different extraction solvents, and only is a Prinsepia utilis royle crude extract after being evaporated to dryness, and the Prinsepia utilis royle crude extract is divided into Prinsepia utilis royle ethanol extract and Prinsepia utilis royle water extract correspondingly.
Preferably, the ethanol in the step 1 is a 70% ethanol solution.
Preferably, the macroporous adsorption resin is AB-8 type macroporous adsorption resin.
Meanwhile, the invention also provides the prinsepia utilis royle extract extracted by any one of the preparation methods, wherein the prinsepia utilis royle extract is a non-oil prinsepia utilis royle extract and contains more total flavonoids, and preferably, the content of the total flavonoids in the prinsepia utilis royle extract is 0.04-2.97%.
The Prinsepia utilis Royle extract obtained by the preparation method is subjected to DPPH method free radical scavenging activity determination, and the result shows that the Prinsepia utilis Royle extract has higher free radical scavenging rate, the commercially available Prinsepia utilis Royle oil has lower free radical scavenging rate, and the difference between the two is obvious; in addition, in the anti-aging activity test, namely the test on the promotion effect on human fibroblast proliferation, the result shows that the prinsepia utilis royle alcohol extract and the 30% ethanol solution elution part thereof have the effect of promoting human fibroblast proliferation, but the commercially available prinsepia utilis royle oil and other extracts have no promotion effect. Based on the beneficial effects, the invention provides the application of the prinsepia utilis royle extract in anti-aging and anti-aging cosmetic preparation, and also provides the application in scavenging free radicals and/or promoting human fibroblast proliferation, and in preparing products for scavenging free radicals and/or promoting human fibroblast proliferation.
As a specific mode of the above-mentioned use, the present invention provides an anti-aging skin external preparation comprising the prinsepia utilis royle extract prepared by any one of the above-mentioned preparation methods of the present invention.
According to the technical scheme, the Prinsepia utilis Royle non-oil extract is obtained by taking Prinsepia utilis Royle as a raw material and extracting by a proper method, and the extracted Prinsepia utilis Royle extract has remarkable free radical scavenging activity and human fibroblast proliferation promoting effect, and can be used for skin aging resistance and related cosmetics.
Detailed Description
The embodiment of the invention discloses a prinsepia utilis royle extract and a preparation method and application thereof. Those skilled in the art can modify the process parameters appropriately to achieve the desired results with reference to the disclosure herein. It is expressly intended that all such similar substitutes and modifications which would be obvious to one skilled in the art are deemed to be included in the invention. While the products and applications of this invention have been described in terms of preferred embodiments, it will be apparent to those of ordinary skill in the art that variations and modifications in the products and methods described herein, as well as other suitable variations and combinations, may be made to implement and use the techniques of this invention without departing from the spirit and scope of the invention.
In order to further understand the present invention, the following examples are provided to describe the extract of Prinsepia utilis Royle and the preparation method and application thereof in detail.
Example 1: preparation of the Prinsepia utilis Royle extract of the invention
Adding 100mL of 70% ethanol into 50g of commercially available Prinsepia utilis Royle, ultrasonically extracting at room temperature for 2 times, each time for 1 hour, and mixing the 2 extractive solutions to obtain a crude Prinsepia utilis Royle ethanol extractive solution.
Dividing the crude extract of the Prinsepia utilis Royle ex Fr ethanol into two parts, directly evaporating 50ml to dryness to obtain an ethanol extract of the Prinsepia utilis Royle ex Fr, concentrating the remaining 50ml under reduced pressure to 25ml, adsorbing with an AB-8 resin column, sequentially eluting with deionized water, 30% ethanol, 70% ethanol and 95% ethanol, respectively collecting, distilling under reduced pressure to remove the solvent, and correspondingly obtaining a water elution part A, a 30% ethanol elution part B, a 70% ethanol elution part C and a 95% ethanol elution part D of the Prinsepia utilis Royle ex Fr;
the obtained prinsepia utilis royle alcohol extract, the prinsepia utilis royle water elution part A, the prinsepia utilis royle ethanol elution part B, the prinsepia utilis royle ethanol elution part C and the prinsepia utilis royle ethanol elution part D are the prinsepia utilis royle extract.
Example 2: preparation of the Prinsepia utilis Royle extract of the invention
Adding 100mL of deionized water into 50g of commercially available Prinsepia utilis Royle ex Fr, ultrasonically extracting for 2 times at room temperature for 1 hour each time, and mixing the 2 extracting solutions to obtain a crude water extracting solution of Prinsepia utilis Royle ex Fr.
Dividing the crude extract of the Prinsepia utilis Royle ex Fr water into two parts, taking 50ml, directly evaporating to dryness to obtain an aqueous extract of the Prinsepia utilis Royle ex Fr, concentrating the remaining 50ml under reduced pressure to 25ml, adsorbing with an AB-8 resin column, sequentially eluting with deionized water, 30% ethanol, 70% ethanol and 95% ethanol, respectively collecting, distilling under reduced pressure to remove the solvent, and correspondingly obtaining a water elution part E, a 30% ethanol elution part F, a 70% ethanol elution part G and a 95% ethanol elution part H of the Prinsepia utilis Royle ex Fr;
the obtained prinsepia utilis aqueous extract, the prinsepia utilis water elution part E, the 30% ethanol elution part F, the 70% ethanol elution part G and the 95% ethanol elution part H are the prinsepia utilis extract.
Example 3: determination of total flavone content in prinsepia utilis royle extract
The extract of each prinsepia utilis royle in example 1 and example 2 is used as a detection object, and rutin is used as a standard substance according to a method of pharmacopoeia of the people's republic of China (2010 version), so that the content of total flavonoids in the extract is measured. The determination steps are as follows: 1) and (3) standard curve preparation: 1ml, 2ml, 3ml, 4ml, 5ml and 6ml of the reference substance solution are precisely measured and respectively placed in a 25ml measuring flask, 30% ethanol is added to 6.0ml, and 1ml of 5% sodium nitrite solution is added. Mixing, standing for 6 min, adding 10% aluminum nitrate solution 1ml, shaking, and standing for 6 min. Adding 10ml of sodium hydroxide test solution, adding 30% ethanol to scale, shaking, standing for 15 min, measuring absorbance at 510nm wavelength by ultraviolet-visible spectrophotometry with corresponding reagent as blank, and drawing standard curve with absorbance as ordinate and concentration as abscissa. 2) Taking a certain amount of sample to be placed in a 25ml volumetric flask, and according to other standard curve preparation steps, measuring the absorbance by a method from the step of adding 1ml of sodium nitrite solution, taking 3ml of sample solution, taking the rest as blank except the sodium hydroxide test solution, and calculating the content of total flavonoids (calculated by rutin) in the extract. The results are shown in Table 1.
TABLE 1 Total Flavonoids content in Prinsepia utilis Royle extract
| Sample name | Content of total flavonoids% |
| Prinsepia utilis Royle alcohol extract | 1.35 |
| Prinsepia utilis solvent elution part A | 0.04 |
| Prinsepia utilis solvent elution part B | 0.89 |
| Prinsepia utilis solvent elution part C | 2.71 |
| Prinsepia utilis solvent elution part D | 0.93 |
| Prinsepia utilis aqueous extract | 1.46 |
| Prinsepia utilis solvent elution part E | 0.05 |
| Prinsepia utilis solvent elution part F | 0.93 |
| Prinsepia utilis solvent elution part G | 2.97 |
| Prinsepia utilis solvent elution part H | 1.10 |
As can be seen from Table 1, the Prinsepia utilis Royle extract of the invention contains more total flavonoids, and after separation by macroporous resin, the content of the total flavonoids is obviously improved and the activity is also obviously enhanced.
Example 4: measurement of antioxidant Activity (measurement of radical scavenging Activity by DPPH method)
The respective Prinsepia utilis extracts prepared in example 1 and example 2 were measured for radical scavenging activity by DPPH method. The determination steps are as follows: preparing sample into water solution with deionized water, transferring 2mL into 10mL test tube with plug, and adding 2mL DPPH ethanol solution (2 x 10)-4mol/L), mixing, standing at room temperature, measuring absorbance A at wavelength of 517nm with spectrophotometer after 30min517(ethanol as reference); simultaneously measuring the absorbance A of 2mL of DPPH solution mixed with 2mL of ethanolcAnd absorbance A obtained by mixing 2mL of the extract with 2mL of an ethanol solution0. The measurements were performed in triplicate, averaged, and the radical clearance calculated according to the following formula, reported in Table 2.
Radical clearance rate ═ 1- (A)517-A0)/Ac)*100％。
TABLE 2 measurement results of radical scavenging activity by DPPH method
| Sample name | Sample concentration mg/ml | Free radical scavenging rate% |
| Prinsepia utilis Royle oil (sold in market) | 5 | 25 |
| Prinsepia utilis Royle alcohol extract | 0.05 | 74 |
| Prinsepia utilis solvent elution part A | 0.05 | 56 |
| Prinsepia utilis solvent elution part B | 0.05 | 88 |
| Prinsepia utilis solvent elution part C | 0.05 | 84 |
| Prinsepia utilis solvent elution part D | 0.05 | 67 |
| Prinsepia utilis aqueous extract | 0.05 | 81 |
| Prinsepia utilis solvent elution part E | 0.05 | 73 |
| Prinsepia utilis solvent elution part F | 0.05 | 96 |
| Prinsepia utilis solvent elution part G | 0.05 | 91 |
| Green thornFruit solvent elution site H | 0.05 | 85 |
As can be seen from table 2, each of the prinsepia utilis royle extracts of the present invention has an excellent radical scavenging effect, can be used as an antioxidant, and has far higher antioxidant activity than commercially available prinsepia utilis royle oil. Therefore, each prinsepia utilis royle extract can be used alone or in combination in a skin external preparation as an antioxidant active substance for preventing skin aging and maintaining a young and healthy skin state.
Example 5: measurement of anti-aging Activity (measurement of promotion of human fibroblast proliferation)
Each of the prinsepia utilis royle extracts prepared according to the examples 1 and 2 is prepared into a 0.01% solution by mass percentage by using deionized water, and the solution is added into a human fibroblast culture solution, and the deionized water without a sample is used as a blank control. After 48 hours of culture, a part of cell samples are randomly taken, after the cells are stained, the absorbance at 475nm is measured by using an enzyme-labeling instrument, the effect of promoting the proliferation of the human fibroblasts is evaluated, the proliferation rate of a blank control is 100%, if the proliferation rate is higher than 100%, the effect of promoting the proliferation of the cells is achieved, if the proliferation rate is higher than 120%, the effect of remarkably promoting the proliferation of the cells is achieved, and the results are shown in Table 3.
TABLE 3 anti-aging Activity test
| Sample name | Human fibroblast proliferation Rate% |
| Prinsepia utilis Royle oil (sold in market) | 99.03±1.69 |
| Prinsepia utilis Royle alcohol extract | 104±1.37 |
| Prinsepia utilis solvent elution part A | 83.3±6.83 |
| Prinsepia utilis solvent elution part B | 138.63±3.71 |
| Prinsepia utilis solvent elution part C | 96.77±6.08 |
| Prinsepia utilis solvent elution part D | 94.63±5.03 |
| Prinsepia utilis aqueous extract | 97.35±3.14 |
| Prinsepia utilis solvent elution part E | 88.11±2.85 |
| Prinsepia utilis solvent elution part F | 89.42±5.58 |
| Prinsepia utilis solvent elution part G | 98.82±8.71 |
| Prinsepia utilis solvent elution part H | 92.25+7.72 |
| Blank control | 100 |
As can be seen from table 3, the echinacea purpurea ethanol extract and the 30% ethanol elution part B have the proliferation promoting effect on human fibroblasts, wherein the proliferation promoting effect of the echinacea purpurea 30% ethanol elution part B is more remarkable, and compared with commercially available prinsepia utilis royle oil, the echinacea purpurea ethanol extract and the 30% ethanol elution part B have no effect of promoting the proliferation of human fibroblasts. Therefore, the prinsepia utilis royle extract can be blended with a skin external preparation to be used as an anti-aging agent for preventing skin aging and maintaining a young and healthy skin state.
The above description of the embodiments is only intended to facilitate the understanding of the method of the invention and its core idea. It should be noted that, for those skilled in the art, it is possible to make various improvements and modifications to the present invention without departing from the principle of the present invention, and those improvements and modifications also fall within the scope of the claims of the present invention.
Claims (9)
1. A preparation method of a prinsepia utilis royle extract is characterized by comprising the following steps:
step 1, adding ethanol into prinsepia utilis royle fruits for extraction to obtain prinsepia utilis royle fruit crude extract;
step 2, concentrating the crude extract of the Prinsepia utilis Royle, loading the concentrated extract to macroporous adsorption resin, eluting with deionized water, 30% ethanol solution, 70% ethanol solution and 95% ethanol solution in sequence, collecting the elution parts respectively, and then distilling under reduced pressure to remove the solvent, thus obtaining a water elution part, a 30% ethanol solution elution part, a 70% ethanol solution elution part and a 95% ethanol solution elution part of the Prinsepia utilis Royle correspondingly;
and 3, eluting the part of the green spiny fruit by using the 30% ethanol solution to obtain the prepared green spiny fruit extract.
2. The method according to claim 1, wherein step 1 is:
adding ethanol into the Prinsepia utilis Royle ex Fr according to the proportion of 1g to 20mL, ultrasonically extracting for 2 times at room temperature for 1 hour each time, centrifuging, filtering supernate, and collecting all filtrates to obtain a Prinsepia utilis Royle ex Fr crude extract.
3. The preparation method according to claim 1, wherein the macroporous adsorption resin is AB-8 type macroporous adsorption resin.
4. The method according to claim 1, wherein the ethanol in step 1 is a 70% ethanol solution.
5. The Prinsepia utilis royle extract prepared by the preparation method according to any one of claims 1 to 4.
6. The prinsepia utilis royle extract of claim 5, wherein the total flavone content is 0.04-2.97%.
7. Use of the prinsepia utilis royle extract of claim 5 for preparing an anti-aging cosmetic.
8. Use of the prinsepia utilis royle extract of claim 5 for the preparation of a product for promoting human fibroblast proliferation.
9. An anti-aging skin external preparation comprising the prinsepia utilis royle extract according to claim 5.
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Non-Patent Citations (3)
| Title |
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| 青刺尖果中黄酮的提取及结构鉴定;杨惠等;《昆明医科大学学报》;20151231;第36卷(第3期);1-3 * |
| 青刺果研究概述;和琼姬等;《中国农学通报》;20160305;74-78 * |
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