CN110051550A - A kind of ar-turmerone inclusion compound and preparation method thereof with sterilization anti-inflammatory effect - Google Patents
A kind of ar-turmerone inclusion compound and preparation method thereof with sterilization anti-inflammatory effect Download PDFInfo
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- CN110051550A CN110051550A CN201910463023.9A CN201910463023A CN110051550A CN 110051550 A CN110051550 A CN 110051550A CN 201910463023 A CN201910463023 A CN 201910463023A CN 110051550 A CN110051550 A CN 110051550A
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- turmerone
- inclusion compound
- turmeric
- inflammatory effect
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- NAAJVHHFAXWBOK-ZDUSSCGKSA-N (+)-(S)-ar-turmerone Chemical compound CC(C)=CC(=O)C[C@H](C)C1=CC=C(C)C=C1 NAAJVHHFAXWBOK-ZDUSSCGKSA-N 0.000 title claims abstract description 116
- XOCANRBEOZQNAQ-KGLIPLIRSA-N ar-turmerone Natural products C[C@H](CC(=O)C=C(C)C)[C@@H]1CC=C(C)C=C1 XOCANRBEOZQNAQ-KGLIPLIRSA-N 0.000 title claims abstract description 116
- 150000001875 compounds Chemical class 0.000 title claims abstract description 35
- 230000003110 anti-inflammatory effect Effects 0.000 title claims abstract description 19
- 230000001954 sterilising effect Effects 0.000 title claims abstract description 15
- 238000004659 sterilization and disinfection Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 235000003392 Curcuma domestica Nutrition 0.000 claims abstract description 45
- 235000003373 curcuma longa Nutrition 0.000 claims abstract description 45
- 235000013976 turmeric Nutrition 0.000 claims abstract description 45
- 239000000341 volatile oil Substances 0.000 claims abstract description 28
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 14
- 239000000945 filler Substances 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 206010061218 Inflammation Diseases 0.000 claims abstract description 3
- 230000004054 inflammatory process Effects 0.000 claims abstract description 3
- 210000000988 bone and bone Anatomy 0.000 claims abstract 2
- 208000015181 infectious disease Diseases 0.000 claims abstract 2
- 210000000214 mouth Anatomy 0.000 claims abstract 2
- 244000163122 Curcuma domestica Species 0.000 claims description 46
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000000839 emulsion Substances 0.000 claims description 13
- 239000003208 petroleum Substances 0.000 claims description 12
- 239000011265 semifinished product Substances 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 10
- 239000000284 extract Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- 239000008367 deionised water Substances 0.000 claims description 7
- 229910021641 deionized water Inorganic materials 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 238000010898 silica gel chromatography Methods 0.000 claims description 7
- 238000001704 evaporation Methods 0.000 claims description 6
- 230000008014 freezing Effects 0.000 claims description 6
- 238000007710 freezing Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 238000004262 preparative liquid chromatography Methods 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 235000006886 Zingiber officinale Nutrition 0.000 claims description 5
- 235000008397 ginger Nutrition 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000012752 auxiliary agent Substances 0.000 claims description 4
- 239000002537 cosmetic Substances 0.000 claims description 4
- 229920002774 Maltodextrin Polymers 0.000 claims description 2
- 239000005913 Maltodextrin Substances 0.000 claims description 2
- 229920000881 Modified starch Polymers 0.000 claims description 2
- 239000004368 Modified starch Substances 0.000 claims description 2
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 claims description 2
- 229940035034 maltodextrin Drugs 0.000 claims description 2
- 235000019426 modified starch Nutrition 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 229920000223 polyglycerol Polymers 0.000 claims description 2
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 229920000858 Cyclodextrin Polymers 0.000 claims 2
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims 1
- 239000001116 FEMA 4028 Substances 0.000 claims 1
- 229920001213 Polysorbate 20 Polymers 0.000 claims 1
- 244000273928 Zingiber officinale Species 0.000 claims 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 claims 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims 1
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims 1
- 229960004853 betadex Drugs 0.000 claims 1
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
- 239000007787 solid Substances 0.000 abstract description 2
- 244000008991 Curcuma longa Species 0.000 abstract 2
- 210000001215 vagina Anatomy 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000003814 drug Substances 0.000 description 5
- 241000234314 Zingiber Species 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 235000014375 Curcuma Nutrition 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 description 2
- 210000005069 ears Anatomy 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- -1 infiltrate 20 min Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000001151 other effect Effects 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 240000006409 Acacia auriculiformis Species 0.000 description 1
- 238000011725 BALB/c mouse Methods 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000006937 anti-inflammatory bioactivity Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940126678 chinese medicines Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000005906 menstruation Effects 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
-
- 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
- A61K8/35—Ketones, e.g. benzophenone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/02—Local antiseptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- 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
- A61Q17/005—Antimicrobial preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
- A61K2236/37—Extraction at elevated pressure or temperature, e.g. pressurized solvent extraction [PSE], supercritical carbon dioxide extraction or subcritical water extraction
-
- 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
-
- 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
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
-
- 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
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/84—Products or compounds obtained by lyophilisation, freeze-drying
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Pain & Pain Management (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The present invention relates to a kind of to extract the ar-turmerone inclusion compound and preparation method thereof that the high turmeric volatile-oil of ar-turmerone content is raw material preparation tool sterilization anti-inflammatory effect from turmeric.Ar-turmerone inclusion compound of the present invention is made of following components weight percent: ar-turmerone 1% ~ 20%, emulsifier 1% ~ 50%, filler are surplus.Ar-turmerone inclusion compound of the present invention is prepared into solid pharmaceutical preparation using self-emulsifying is dry-mixed, efficiently solves that ar-turmerone poorly water-soluble, mouthfeel are bad etc. to use restricted problem.Ar-turmerone inclusion compound of the present invention has sterilization anti-inflammatory effect, and can be used as improves infection and the relevant function raw materials of inflammation such as oral cavity, vagina, enteron aisle and Bones and joints.
Description
Technical field
The invention belongs to the technical fields such as daily cosmetics and medical auxiliary agent, and the present invention relates to one kind to have sterilization anti-
The ar-turmerone inclusion compound and preparation method thereof of inflammation effect, in particular to one kind are with ar-turmerone, food emulsifying agent, filler
Supplementary material preparation has the ar-turmerone inclusion compound and preparation method thereof of sterilization anti-inflammatory effect.
Background technique
Chinese medicine of the turmeric as traditional dual-purpose of drug and food, is planted extensively in the southeast in China and the west and south.Turmeric has promoting menstruation
Analgesic, cold extermination anti-inflammatory, relieve heat promoting blood circulation and other effects, the field of Chinese medicines is using more.Turmeric volatile-oil is the main active of turmeric
One of.And ar-turmerone is one of the main component in the volatile oil of zingiberaceous plant root, wherein Turmeric (Curcuma longa L.) content highest in root block, it is one of compound that curcuma oil or turmeric volatile-oil have special odor.It is existing
Show that ar-turmerone has anti-oxidant, removing free radical, anti-inflammatory, antitumor, antibacterial, inhibition melanin raw for pharmaceutical research
At etc. multiple biological activities, and the gradually concern by numerous researchers, in the fields such as daily cosmetics and medical auxiliary agent
With very big application potential.
Ar-turmerone is mainly used in drug field at present, this research team finds that ar-turmerone has significant anti-silver bits
Disease, prevention and treatment neuroinflamation and other effects.Since ar-turmerone water solubility is poor, mouthfeel is bad, assists in daily cosmetics and medicine
Formulation application difficulty is big, at present mainly using turmeric essential oil as raw material be prepared into microcapsules, inclusion compound, dripping pill etc. research it is more, it is fresh
About using ar-turmerone as primary raw material Transformation Application research, patent CN1319524C is mentioned with the curcuma oil containing ar-turmerone
It takes object as active constituent, the dripping pill drug of inhibition or treating cancer purposes is prepared using dripping pill matrix.This patent is for existing
The limitation of the preparation and application research of technology, exploitation have the ar-turmerone inclusion compound of sterilization, anti-inflammatory properties, are applied to daily makeup
The fields such as product and medical auxiliary agent.
Summary of the invention
It is an object of that present invention to provide a kind of ar-turmerone inclusion compounds and preparation method thereof with sterilization anti-inflammatory effect.
The problem of in view of above-mentioned and/or existing ar-turmerone application process, propose invention technology.
Therefore, to solve the problems, such as above-mentioned technology, the invention provides the following technical scheme: from the ginger of ar-turmerone high-content
Xanthate material extracts turmeric volatile-oil through steam distillation, using silica gel column chromatography and preparation chromatography, isolate and purify to obtain content >=
90% ar-turmerone
It further is prepared into solid pharmaceutical preparation, i.e. ar-turmerone inclusion compound using self-emulsifying is dry-mixed, efficiently solves ar-turmerone
Poorly water-soluble, mouthfeel are bad etc. to use restricted problem.
A kind of ar-turmerone inclusion compound with sterilization anti-inflammatory effect, which is characterized in that the ar-turmerone inclusion compound
Be made of following components weight percent: ar-turmerone 1% ~ 20%, emulsifier 1% ~ 50%, filler are surplus.
A kind of ar-turmerone inclusion compound with sterilization anti-inflammatory effect provided by the invention, is prepared by following steps:
(1) the turmeric medicinal material of the ar-turmerone containing high-content is taken, 24 meshes are smashed it through, turmeric medicinal powder is obtained, by solid-liquid ratio 1:4 ~ 1:
15 are added deionized water, infiltrate 15 ~ 25 min, extract 4 ~ 10 h in 100 DEG C of heating distillations, collect through separating and extracting, obtain ginger
Yellow volatile oil；
(2) silica gel column chromatography is used, using ethyl acetate: petroleum ether is 1-10:5-100 as mobile phase, to turmeric in step (1)
Volatile oil preliminary concentration purifies to obtain ar-turmerone semifinished product, detects ar-turmerone content using GC-MS；
(3) ar-turmerone semifinished product in step (2) is further purified using preparative liquid chromatography, chromatographic condition are as follows: preparative
C18 Reversed Phase High Performance, 4 mL/min of flow velocity, methanol: water (volume ratio) is 80:20, collects evaporating at 30 ~ 34 min
Point, ar-turmerone sterling solution is obtained, petroleum ether extraction separation further is added by 1:1 ~ 1:3 volume ratio, under the conditions of 30 DEG C
Vacuum drying, obtains ar-turmerone sterling, content >=90%；
(4) ar-turmerone that step (3) are prepared is measured by formula, 1% ~ 50% emulsifier is added, stirred in 3000 rpm molten
Xie Hou continues to stir the h of 0.5h ~ 1.5, obtains ar-turmerone emulsion；
(5) it weighs filler by formula ratio to be added in step (4) resulting ar-turmerone emulsion, freezing is dry after mixing
Dry, obtaining content is 1% ~ 20% ar-turmerone inclusion compound.
Preferably, the emulsifier is polyglycerol monooleate, rilanit special polyethers.
Preferably, the filler is hydroxypropyl-β-cyclodextrin, maltodextrin, modified starch.
Preferably, it is 1:10 ~ 1:12 that the turmeric volatile-oil, which extracts solid-liquid ratio,.
Preferably, the turmeric medicinal material for taking the ar-turmerone containing high-content, smashes it through 24 meshes, turmeric medicinal powder is obtained, by feed liquid
Deionized water is added than 1:10, infiltrates 25 min, extracts 6 h in 100 DEG C of heating distillations, is collected through separating and extracting, obtain turmeric
Volatile oil.
Preferably, the ar-turmerone inclusion compound is made of following components weight percent: ar-turmerone 10%, emulsification
Agent 10%, filler 80%.
Beneficial effects of the present invention:
(1) present invention takes turmeric medicinal material to extract turmeric volatile-oil, remaining non-turmeric in extraction process through steam distillation first
Volatile oil component is less, ar-turmerone content >=90% in turmeric volatile-oil after isolating and purifying, and detects fragrant ginger using GC-MS
Flavones content and as technical process critical control point.
(2) emulsifier is added in high-content ar-turmerone under normal temperature conditions, carries out emulsion dispersion, avoids and reduce temperature pair
The influence of ar-turmerone.On the basis of improving ar-turmerone dispersibility in water, the bad equal use of ar-turmerone mouthfeel is solved
Restricted problem, further improves antibacterial, the anti-inflammatory bioactivity of ar-turmerone, and preparation process of the present invention is green
Colour circle is protected, and industrialization promotion application can be carried out.
Specific embodiment
Below in conjunction with specific embodiment, invention is further explained.
The invention is further illustrated by the following examples, but the present invention is not limited in the embodiment.
Embodiment 1
(1) the turmeric medicinal material for taking the ar-turmerone containing high-content, smashes it through 24 meshes, obtains turmeric medicinal powder, is added by solid-liquid ratio 1:4
Deionized water infiltrates 20 min, extracts 4 h in 100 DEG C of heating distillations, collects through separating and extracting, obtain turmeric volatile-oil；
(2) silica gel column chromatography is used, using ethyl acetate: petroleum ether is 1:100 as mobile phase, is volatilized to turmeric in step (1)
Oily preliminary concentration purifies to obtain ar-turmerone semifinished product, detects ar-turmerone content using GC-MS；
(3) ar-turmerone semifinished product in step (2) is further purified using preparative liquid chromatography, chromatographic condition are as follows: preparative
C18 Reversed Phase High Performance, 4 mL/min of flow velocity, methanol: water (volume ratio) is 80:20, collects evaporating at 30 ~ 34 min
Point, ar-turmerone sterling solution is obtained, petroleum ether extraction separation, the vacuum under the conditions of 30 DEG C further is added by 1:1 volume ratio
It is dry, obtain ar-turmerone sterling, content 91.2%；
(4) ar-turmerone that step (3) are prepared is measured by formula, 3% emulsifier is added, after 3000 rpm stirring and dissolvings,
Continue to stir 0.5h, obtains ar-turmerone emulsion；
(5) it weighs filler by formula ratio to be added in step (4) resulting ar-turmerone emulsion, freezing is dry after mixing
Dry, obtaining content is 5% ar-turmerone inclusion compound.
Embodiment 2
(1) the turmeric medicinal material for taking the ar-turmerone containing high-content, smashes it through 24 meshes, obtains turmeric medicinal powder, is added by solid-liquid ratio 1:8
Deionized water infiltrates 25 min, extracts 6 h in 100 DEG C of heating distillations, collects through separating and extracting, obtain turmeric volatile-oil；
(2) silica gel column chromatography is used, using ethyl acetate: petroleum ether is 1:90 as mobile phase, to turmeric volatile-oil in step (1)
Preliminary concentration purifies to obtain ar-turmerone semifinished product, detects ar-turmerone content using GC-MS；
(3) ar-turmerone semifinished product in step (2) is further purified using preparative liquid chromatography, chromatographic condition are as follows: preparative
C18 Reversed Phase High Performance, 4 mL/min of flow velocity, methanol: water (volume ratio) is 80:20, collects evaporating at 30 ~ 34 min
Point, ar-turmerone sterling solution is obtained, petroleum ether extraction separation, the vacuum under the conditions of 30 DEG C further is added by 1:3 volume ratio
It is dry, obtain ar-turmerone sterling, content 93.6%；
(4) ar-turmerone that step (3) are prepared is measured by formula, 5% emulsifier is added, after 3000 rpm stirring and dissolvings,
Continue to stir 0.5h, obtains ar-turmerone emulsion；
(5) it weighs filler by formula ratio to be added in step (4) resulting ar-turmerone emulsion, freezing is dry after mixing
Dry, obtaining content is 10% ar-turmerone inclusion compound.
Embodiment 3
(1) the turmeric medicinal material for taking the ar-turmerone containing high-content, smashes it through 24 meshes, obtains turmeric medicinal powder, add by solid-liquid ratio 1:12
Enter deionized water, infiltrate 20 min, extracts 6 h in 100 DEG C of heating distillations, collected through separating and extracting, obtain turmeric volatile-oil；
(2) silica gel column chromatography is used, using ethyl acetate: petroleum ether is 1:86 as mobile phase, to turmeric volatile-oil in step (1)
Preliminary concentration purifies to obtain ar-turmerone semifinished product, detects ar-turmerone content using GC-MS；
(3) ar-turmerone semifinished product in step (2) is further purified using preparative liquid chromatography, chromatographic condition are as follows: preparative
C18 Reversed Phase High Performance, 4 mL/min of flow velocity, methanol: water (volume ratio) is 85:15, collects evaporating at 30 ~ 34 min
Point, ar-turmerone sterling solution is obtained, petroleum ether extraction separation further is added by 1:2.5 volume ratio, it is true under the conditions of 30 DEG C
Sky is dry, obtains ar-turmerone sterling, content 92.7%；
(4) ar-turmerone that step (3) are prepared is measured by formula, 4% emulsifier is added, after 3000 rpm stirring and dissolvings,
Continue to stir 1.0 h, obtains ar-turmerone emulsion；
(5) it weighs filler by formula ratio to be added in step (4) resulting ar-turmerone emulsion, freezing is dry after mixing
Dry, obtaining content is 12% ar-turmerone inclusion compound.
Embodiment 4
(1) the turmeric medicinal material for taking the ar-turmerone containing high-content, smashes it through 24 meshes, obtains turmeric medicinal powder, add by solid-liquid ratio 1:12
Enter deionized water, infiltrate 20 min, extracts 6 h in 100 DEG C of heating distillations, collected through separating and extracting, obtain turmeric volatile-oil；
(2) silica gel column chromatography is used, using ethyl acetate: petroleum ether is 1:86 as mobile phase, to turmeric volatile-oil in step (1)
Preliminary concentration purifies to obtain ar-turmerone semifinished product, detects ar-turmerone content using GC-MS；
(3) ar-turmerone semifinished product in step (2) is further purified using preparative liquid chromatography, chromatographic condition are as follows: preparative
C18 Reversed Phase High Performance, 4 mL/min of flow velocity, methanol: water (volume ratio) is 80:10, collects evaporating at 30 ~ 34 min
Point, ar-turmerone sterling solution is obtained, petroleum ether extraction separation, the vacuum under the conditions of 30 DEG C further is added by 1:3 volume ratio
It is dry, obtain ar-turmerone sterling, content 93.9%；
(4) ar-turmerone that step (3) are prepared is measured by formula, 5% emulsifier is added, after 3000 rpm stirring and dissolvings,
Continue to stir 1.5 h, obtains ar-turmerone emulsion；
(5) it weighs filler by formula ratio to be added in step (4) resulting ar-turmerone emulsion, freezing is dry after mixing
Dry, obtaining content is 20% ar-turmerone inclusion compound.
Embodiment 5
The anti-inflammatory experiment of ar-turmerone inclusion compound
1. experimental material
Ar-turmerone inclusion compound in embodiment 1 ~ 4, turmeric volatile-oil (ar-turmerone content 20%), TPA, acetone, the reagents such as DMSO
Consumptive material.
2. experimental animal and group
(1) male BALB/c mouse, 18-22 g；
(2) model group, turmeric volatile-oil (ar-turmerone content 20%) group, ar-turmerone inclusion compound group are set, 6 groups, every group 6,
24 mouse.
3. solution is prepared
TPA solution: taking 0.01 g TPA to be dissolved in acetone, be settled to 10 mL with acetone after dissolution, and being made into concentration is 100 μ g/
ML, -4 DEG C save backup；Sample sets: turmeric volatile-oil (ar-turmerone content 20%), ar-turmerone inclusion compound group sample is taken to be dissolved in
10%PEG400 aqueous solution, ultimate density are that 100 mg/kg(are calculated with ar-turmerone), smearing dosage is 10 μ L.
4. experimental method
Using mouse own control, the TPA of 10 μ L is smeared inside and outside model group and the left ear of sample each group mouse respectively, inside and outside auris dextra
The acetone of 10 μ L is smeared respectively.After smearing 1 h of TPA, applying 10 μ L dosage in the left ear of sample sets outside respectively is 100 mg/kg
Turmeric volatile-oil, ar-turmerone inclusion compound.After smearing 6 h of TPA, all mouse are put to death, two ears drill (6 mm of diameter), take
Out, it is weighed with a ten thousandth balance, records weight.The following formula of inhibiting rate calculates:
The results are shown in Table 1, and the inhibiting rate of 1 ~ 4 ar-turmerone inclusion compound of embodiment prepared by the present invention is respectively 41.75%, ginger
Yellow volatile oil inhibiting rate is to illustrate there is good anti-inflammatory activity, prompts the advantage of inventive formulation and technology.
1 anti-inflammatory experimental result (n=6) of table
| Group | Inhibiting rate (%) |
| Model group | — |
| Turmeric volatile-oil | 33.55 |
| Embodiment 1 | 40.47 |
| Embodiment 2 | 73.91 |
| Embodiment 3 | 68.33 |
| Embodiment 4 | 84.58 |
The above, preferable specific embodiment only of the invention, but scope of protection of the present invention is not limited thereto, and it is any
Those familiar with the art in the technical scope disclosed by the present invention, according to the technique and scheme of the present invention and its conceives
It is subject to equivalent substitution or change, should be covered by the scope of protection of the present invention.
Claims (5)
1. it is a kind of with sterilization anti-inflammatory effect ar-turmerone inclusion compound, which is characterized in that the ar-turmerone inclusion compound by
Following components weight percent composition: ar-turmerone 1% ~ 20%, emulsifier 1% ~ 50%, filler are surplus.
2. a kind of ar-turmerone inclusion compound with sterilization anti-inflammatory effect according to claim 1, it is characterised in that described
Emulsifier include Tween-20, polyglycerol monooleate, rilanit special polyethers, PEG-400 often use one of emulsifier or
A variety of mixtures.
3. a kind of ar-turmerone inclusion compound with sterilization anti-inflammatory effect according to claim 1, it is characterised in that described
Filler include alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin, hydroxypropyl-β-cyclodextrin, maltodextrin, in modified starch
One or more mixtures.
4. a kind of preparation method of ar-turmerone inclusion compound with sterilization anti-inflammatory effect according to claim 1, special
Sign is to be prepared by following step:
(1) the turmeric medicinal material for taking the ar-turmerone containing high-content, smashes it through 24 meshes, obtains turmeric medicinal powder, by solid-liquid ratio 1:4 ~ 1:
15 are added deionized water, infiltrate 15 ~ 25 min, extract 4 ~ 10 h in 100 DEG C of heating distillations, collect through separating and extracting, obtain ginger
Yellow volatile oil；
(2) silica gel column chromatography is used, using ethyl acetate: petroleum ether is 1-10:5-100 as mobile phase, to turmeric in step (1)
Volatile oil preliminary concentration purifies to obtain ar-turmerone semifinished product, detects ar-turmerone content using GC-MS；
(3) ar-turmerone semifinished product in step (2) is further purified using preparative liquid chromatography, chromatographic condition are as follows: preparative
C18 Reversed Phase High Performance, 4 mL/min of flow velocity, methanol: water (volume ratio) is 80:20, collects evaporating at 30 ~ 34 min
Point, ar-turmerone sterling solution is obtained, petroleum ether extraction separation further is added by 1:1 ~ 1:3 volume ratio, under the conditions of 30 DEG C
Vacuum drying, obtains ar-turmerone sterling, content >=90%；
(4) ar-turmerone that step (3) are prepared is measured by formula, 1% ~ 50% emulsifier is added, stirred in 3000 rpm molten
Xie Hou continues to stir the h of 0.5 h ~ 1.5, obtains ar-turmerone emulsion；
(5) it weighs filler by formula ratio to be added in step (4) resulting ar-turmerone emulsion, freezing is dry after mixing
Dry, obtaining content is 1% ~ 20% ar-turmerone inclusion compound.
5. a kind of ar-turmerone inclusion compound described in claim 1 ~ 4 has sterilization anti-inflammatory effect, can be used as improves oral cavity, yin
The infection such as road, enteron aisle and Bones and joints and the relevant function raw material of inflammation are applied to the neck such as daily cosmetics and medical auxiliary agent
Domain.
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