CN114209060B - Turmeric composition with high bioavailability and preparation method thereof - Google Patents
Turmeric composition with high bioavailability and preparation method thereof Download PDFInfo
- Publication number
- CN114209060B CN114209060B CN202111587358.5A CN202111587358A CN114209060B CN 114209060 B CN114209060 B CN 114209060B CN 202111587358 A CN202111587358 A CN 202111587358A CN 114209060 B CN114209060 B CN 114209060B
- Authority
- CN
- China
- Prior art keywords
- turmeric
- phospholipid
- parts
- hydroxypropyl methylcellulose
- sol
- 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.)
- Active
Links
- 235000003392 Curcuma domestica Nutrition 0.000 title claims abstract description 37
- 235000003373 curcuma longa Nutrition 0.000 title claims abstract description 37
- 235000013976 turmeric Nutrition 0.000 title claims abstract description 37
- 239000000203 mixture Substances 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 244000163122 Curcuma domestica Species 0.000 title claims description 9
- 235000020240 turmeric extract Nutrition 0.000 claims abstract description 36
- 239000008513 turmeric extract Substances 0.000 claims abstract description 36
- 229940052016 turmeric extract Drugs 0.000 claims abstract description 36
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims abstract description 26
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims abstract description 26
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims abstract description 26
- 150000003904 phospholipids Chemical class 0.000 claims abstract description 23
- 238000002156 mixing Methods 0.000 claims abstract description 17
- 238000001035 drying Methods 0.000 claims abstract description 8
- 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 claims description 77
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 10
- 241000407170 Curcuma Species 0.000 claims description 9
- 235000014375 Curcuma Nutrition 0.000 claims description 9
- 229920002774 Maltodextrin Polymers 0.000 claims description 8
- 239000005913 Maltodextrin Substances 0.000 claims description 8
- 239000000284 extract Substances 0.000 claims description 8
- 229940035034 maltodextrin Drugs 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 238000000265 homogenisation Methods 0.000 claims description 7
- 238000001694 spray drying Methods 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 238000007873 sieving Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 3
- 238000004108 freeze drying Methods 0.000 claims description 2
- 244000008991 Curcuma longa Species 0.000 abstract description 28
- 239000006185 dispersion Substances 0.000 abstract description 2
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 description 34
- 235000012754 curcumin Nutrition 0.000 description 33
- 229940109262 curcumin Drugs 0.000 description 33
- 239000004148 curcumin Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 21
- 238000004090 dissolution Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 17
- 239000008279 sol Substances 0.000 description 17
- -1 3-hydroxy-4-methoxyphenyl Chemical group 0.000 description 15
- 229920000858 Cyclodextrin Polymers 0.000 description 15
- 239000003814 drug Substances 0.000 description 13
- 239000000084 colloidal system Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 230000001186 cumulative effect Effects 0.000 description 8
- UEPVWRDHSPMIAZ-IZTHOABVSA-N (1e,4z,6e)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)hepta-1,4,6-trien-3-one Chemical compound C1=C(O)C(OC)=CC(\C=C\C(\O)=C\C(=O)\C=C\C=2C=CC(O)=CC=2)=C1 UEPVWRDHSPMIAZ-IZTHOABVSA-N 0.000 description 7
- HJTVQHVGMGKONQ-LUZURFALSA-N Curcumin II Natural products C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=CC(O)=CC=2)=C1 HJTVQHVGMGKONQ-LUZURFALSA-N 0.000 description 7
- NMRUIRRIQNAQEB-UHFFFAOYSA-N demethoxycurcumin Natural products OC(=CC(C=CC1=CC(=C(C=C1)O)OC)=O)C=CC1=CC=C(C=C1)O NMRUIRRIQNAQEB-UHFFFAOYSA-N 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- UEPVWRDHSPMIAZ-UHFFFAOYSA-N p-hydroxycinnamoyl feruloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(O)=CC(=O)C=CC=2C=CC(O)=CC=2)=C1 UEPVWRDHSPMIAZ-UHFFFAOYSA-N 0.000 description 7
- 239000001116 FEMA 4028 Substances 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 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 description 6
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 6
- 229960004853 betadex Drugs 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 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 description 6
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
- 230000002496 gastric effect Effects 0.000 description 5
- 208000002193 Pain Diseases 0.000 description 4
- JYTVKRNTTALBBZ-UHFFFAOYSA-N bis demethoxycurcumin Natural products C1=CC(O)=CC=C1C=CC(=O)CC(=O)C=CC1=CC=CC(O)=C1 JYTVKRNTTALBBZ-UHFFFAOYSA-N 0.000 description 4
- PREBVFJICNPEKM-YDWXAUTNSA-N bisdemethoxycurcumin Chemical compound C1=CC(O)=CC=C1\C=C\C(=O)CC(=O)\C=C\C1=CC=C(O)C=C1 PREBVFJICNPEKM-YDWXAUTNSA-N 0.000 description 4
- YXAKCQIIROBKOP-UHFFFAOYSA-N di-p-hydroxycinnamoylmethane Natural products C=1C=C(O)C=CC=1C=CC(=O)C=C(O)C=CC1=CC=C(O)C=C1 YXAKCQIIROBKOP-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 238000012216 screening Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000004656 cell transport Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 3
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 230000032258 transport Effects 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229940071676 hydroxypropylcellulose Drugs 0.000 description 2
- 229940067631 phospholipid Drugs 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- 206010000077 Abdominal mass Diseases 0.000 description 1
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 102000057297 Pepsin A Human genes 0.000 description 1
- 108090000284 Pepsin A Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000234299 Zingiberaceae Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 235000021438 curry Nutrition 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001341 hydroxy propyl starch Substances 0.000 description 1
- 235000013828 hydroxypropyl starch Nutrition 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940111202 pepsin Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000009048 phenolic acids Nutrition 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/262—Cellulose; Derivatives thereof, e.g. ethers
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- Botany (AREA)
- Mycology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a turmeric composition with high bioavailability and a preparation method thereof. The turmeric composition prepared by dispersing turmeric extract, mixing with the ampholytic sol and drying by utilizing phospholipid and hydroxypropyl methylcellulose to form high-dispersion ampholytic sol and having the characteristics of lipophilicity and hydrophilicity has the advantages of good solubility and stability, high bioavailability and the like.
Description
Technical Field
The invention relates to the technical fields of foods, health-care foods and the like, in particular to a turmeric composition with high bioavailability and a preparation method thereof.
Background
Turmeric is a commonly used traditional Chinese medicine derived from the dried rhizome of turmeric, a plant of the family zingiberaceae, has been used in the past to treat chest and hypochondrium stabbing pain, chest stuffiness and pain, dysmenorrhea, amenorrhea, abdominal mass, rheumatic shoulder and arm pain, traumatic swelling and pain, and the like. Turmeric is not only used as a traditional medicinal material in China, but also consumed by raw materials of curry in foreign countries, or used as a natural coloring agent, etc. In recent years, with the continuous and deep research on turmeric, more and more pharmacological activities of turmeric are discovered, such as anti-tumor, anti-inflammatory, anti-diabetes and the like, and have good development prospect.
The yellow component in turmeric is a mixture composed of various phenolic acids, and mainly comprises curcumin (1, 7-bis (4-hydroxy-3-methoxyphenyl) -1, 6-heptadiene-3, 5-dione), demethoxycurcumin (1, 5-hydroxy-7- (3-hydroxy-4-methoxyphenyl) -1- (3-hydroxyphenyl) -1,4, 6-heptatrien-3, 5-dione) and bisdemethoxycurcumin ((1E, 6E) -1, 7-bis (4-hydroxyphenyl) heptadiene-1, 5-dione), which are collectively called curcumin compounds, wherein the curcumin accounts for 70% of the 3 components and is also the main component of the curcumin compounds for playing pharmacological roles. Curcumin is orange yellow crystal powder at normal temperature, has poor solubility in water, is soluble in ethanol and propylene glycol, and is easily soluble in glacial acetic acid, methanol, ethanol, ethyl acetate and alkali liquor.
Curcumin has pharmacological effects of resisting tumor, resisting oxidation, resisting inflammation, resisting bacteria, reducing blood sugar and the like, but has poor water solubility, so that the curcumin has extremely low bioavailability, and the clinical application of the medicine is influenced. From the previous study on curcumin absorption, distribution, metabolism and excretion, it can be obtained that the poor water solubility and low absorption and utilization rate of curcumin are the main reasons for seriously reducing the pharmacodynamic value of the curcumin. To improve the bioavailability of curcumin, the first problem to be solved is how to improve the solubility of curcumin components and to increase the content level of curcumin components in blood plasma.
The existing solubilization treatment technology for turmeric components mainly comprises inclusion, modification treatment and the like, and the carrier mainly comprises succinic acid starch, hydroxypropyl starch, gamma cyclodextrin, beta cyclodextrin, microcrystalline cellulose, casein, povidone, polyethylene glycol and the like, wherein the most common treatment technology is the cyclodextrin inclusion treatment technology, but the product only solves the problem of dispersing curcumin substances in the carrier, and fails to solve the core problem and technical difficulty of low bioavailability of the curcumin components. Taking gamma/beta cyclodextrin inclusion technology as an example, the mechanism is that curcumin components are embedded into a bowl-shaped cavity formed by glucose units in cyclodextrin structural molecules, and the bowl-shaped cavity plays a role in dispersing and wrapping the curcumin components, and the preparation treatment technology is simple, but the result is that the problem of dispersing the curcumin components is solved, and the curcumin components are not ideal in terms of improving the dissolution and bioavailability of the curcumin components.
Disclosure of Invention
In order to overcome the defects in the prior art, the primary aim of the invention is to provide a turmeric composition with high bioavailability, which has the advantages of good solubility and stability, high bioavailability and the like.
It is another object of the present invention to provide a method for preparing the turmeric composition with high bioavailability as described above.
The invention is realized by the following technical scheme:
A turmeric composition with high bioavailability comprises turmeric extract, hydroxypropyl methylcellulose and phospholipid.
As a further preferred aspect of the present invention, the turmeric composition with high bioavailability comprises, in parts by weight:
20-30 parts of turmeric extract
10-20 Parts of hydroxypropyl methyl cellulose
1-10 Parts of phospholipid.
Preferably, the mass ratio of the hydroxypropyl methylcellulose to the phospholipid is 3:1-1:1.
Preferably, the turmeric extract is turmeric ethanol extract.
Preferably, the turmeric composition further comprises 45-65 parts by weight of maltodextrin and 0.1-2 parts by weight of citric acid.
The turmeric extract of the invention can be obtained by self-making, and the preparation method can adopt the following method:
Coarsely crushing Curcuma rhizome in a pulverizer, placing in a multifunctional extraction tank, adding 5-10 times of 60-80% ethanol by volume, reflux-extracting for 1-2 hr, filtering the extractive solution, reflux-extracting residues with 4-8 times of 60-80% ethanol for 0.5-1 hr, filtering the extractive solution, and collecting filtrate; concentrating the extractive solution under reduced pressure in a concentrator at a vacuum degree of-0.06 to-0.1 MPa and a temperature of 50-70deg.C, concentrating to a proper volume, and crystallizing to obtain Curcuma rhizome extract.
Turmeric extract of the present invention is also commercially available.
The invention also provides a preparation method of the turmeric composition with high bioavailability, which comprises the following steps:
(1) Dissolving Curcuma rhizome extract in ethanol solution, stirring, and dissolving to obtain Curcuma rhizome extract solution;
(2) Taking hydroxypropyl methylcellulose and phospholipid, adding water, stirring to dissolve uniformly, and homogenizing by a homogenizer to obtain uniform stable amphoteric sol for later use;
(3) Mixing Curcuma rhizome extract solution with amphoteric sol, homogenizing with homogenizer;
(4) Then volatilizing ethanol, adding maltodextrin and citric acid, and uniformly mixing;
(5) And (5) drying and sieving the feed liquid obtained in the step (4) to obtain the turmeric composition.
Preferably, in the step (2), the water addition amount is 12-16 times of that of the hydroxypropyl methylcellulose.
In order to ensure that the hydroxypropyl methylcellulose and the phospholipid form stable and uniform amphoteric colloid, the invention optimizes the homogenizing temperature and pressure, and the mixing is not uniform easily when the homogenizing temperature or pressure is too low, so that the inclusion effect is influenced; too high homogenization temperature or pressure can easily cause the phase disruption of the ampholytic system, and the turmeric extract cannot be effectively included. Thus, preferably, in step (2), the homogenization temperature: 55.+ -. 5 ℃ and pressure: 70+/-5 MPa.
In the invention, the uniform and stable amphoteric sol and the turmeric extract solution are mixed and then homogenized, the homogenizing temperature and pressure have a certain influence on the inclusion effect, and preferably, in the step (3), the homogenizing temperature is as follows: 55.+ -. 5 ℃ and pressure: 30+/-5 MPa.
The ampholytic sol formed by hydroxypropyl methylcellulose and phospholipid has better inclusion effect on the turmeric extract, but when the turmeric extract proportion is too high, the dissolution performance of the finished product is affected, and precipitates appear, when the turmeric extract proportion is too low, the curcumin content in the finished product is too low, so that the preferable mass ratio of the turmeric extract to the ampholytic sol is 1.5-1:1.
Preferably, in step (5), the drying is spray drying or freeze drying; the air inlet temperature of the spray drying is 185-205 ℃, and the air outlet temperature is 85-105 ℃.
Compared with the prior art, the invention has the following beneficial effects:
(1) The turmeric extract is mixed with the ampholytic sol after being dispersed and dried by utilizing the characteristic that phospholipid and hydroxypropyl methylcellulose form high-dispersion ampholytic sol and have lipophilic and hydrophilic properties, and the prepared turmeric composition has the advantages of good solubility and stability, high bioavailability and the like;
(2) The invention can be carried out under conventional production conditions, does not need toxic and harmful solvents or non-food auxiliary materials in the production process, has simple production equipment requirements, does not have toxic and harmful solvents or non-food auxiliary materials, and is suitable for large-scale popularization.
Drawings
Fig. 1 is sample a: cumulative dissolution profile of three curcuminoids in non-inclusion treated turmeric extract (n=6);
Fig. 2 is sample B: cumulative dissolution profile of three curcuminoids in the gamma cyclodextrin inclusion curcumin product (n=6);
fig. 3 is sample C: cumulative dissolution profile of three curcuminoids in beta cyclodextrin-coated curcumin product (n=6);
Fig. 4 is sample D: cumulative dissolution profile (n=6) of three curcuminoids in the turmeric composition of the present invention;
FIG. 5 shows the results of liquid phase detection of Caco-2 cell transport experiments.
Detailed Description
The present invention will be further illustrated by the following examples, which are not intended to limit the scope of the invention.
According to the invention, proper auxiliary materials are screened to form the amphoteric sol, and then the turmeric extract is dispersed and then mixed with the amphoteric sol and dried, so that the solubility and stability of the turmeric composition can be improved, and the bioavailability of the turmeric composition is further improved. Many excipients are suitable for use in the art, such as hydroxypropyl methylcellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, beta cyclodextrin, gamma cyclodextrin, phospholipids, and the like, as is common. According to the invention, the research shows that factors such as the types of auxiliary materials and the compounding proportion of the auxiliary materials have great influence on the performance of the amphoteric sol, and therefore, the invention is further optimized for the factors, and the method specifically comprises the following steps:
(1) Auxiliary material screening for preparing amphoteric colloid
Respectively dissolving and mixing hydroxypropyl methylcellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, beta cyclodextrin, gamma cyclodextrin, phospholipid and the like according to a proportion, and then carrying out pressure at 55+/-5 ℃: homogenizing for 2 times under 70+ -5 MPa to obtain corresponding colloid or solution. The results of the comparison of the products under each formulation are shown in Table 1 below:
TABLE 1
From the comparison of the above results, it is clear that hydroxypropyl methylcellulose and hydroxypropyl cellulose can form stable and uniform amphoteric colloid with phospholipid, but hydroxyethyl cellulose, gamma cyclodextrin and beta cyclodextrin can not form colloid with phospholipid.
(2) Inclusion contrast of ampholytic colloids with turmeric extract
Respectively mixing the hydroxypropyl methylcellulose-phospholipid amphoteric colloid and hydroxypropyl cellulose-phospholipid amphoteric colloid prepared under the above conditions with Curcuma rhizome extract at a certain proportion, homogenizing for 2 times (55+ -5deg.C, pressure: 30+ -5 MPa), mixing with maltodextrin as diluent and citric acid as acidity regulator, lyophilizing to obtain clathrate curcumin product, and comparing according to solubility evaluation method of 2020 edition Chinese pharmacopoeia, wherein the results are shown in Table 2 below:
TABLE 2
As is clear from the comparison of the above results, the hydroxypropyl methylcellulose-phospholipid and the hydroxypropyl cellulose-phospholipid both have certain inclusion ability, wherein the hydroxypropyl methylcellulose-phospholipid has the best inclusion performance, can obtain uniform yellow powder, is easy to dissolve in water, and has poor inclusion ability, and the obtained product has poor water solubility or is insoluble in water, so that the hydroxypropyl methylcellulose-phospholipid amphiprotic colloid is preferable.
(3) Screening optimization of hydroxypropyl methylcellulose and phospholipid dosage
The invention further optimizes the dosage of the hydroxypropyl methylcellulose and the phospholipid, and the process is as follows:
respectively taking hydroxypropyl methylcellulose and phospholipid raw materials, comparing the samples according to the proportion shown in the table 3, and comparing the finished products according to the solubility evaluation method of the 2020 edition Chinese pharmacopoeia.
TABLE 3 Table 3
As can be seen from the comparison results of the above tables, the ratio of the hydroxypropyl methylcellulose to the phospholipid affects the characteristics of the finished product, and when the mass ratio of the hydroxypropyl methylcellulose to the phospholipid is 3:1-1:1, the finished product is uniform yellow powder, is easy to dissolve in water and has no precipitate.
(4) Proportioning screening of amphoteric colloid and turmeric
The inclusion effect of the ampholytic colloid and the turmeric extract is inspected according to the optimized formula proportion, and the finished product is compared according to the solubility evaluation method of the 2020 edition Chinese pharmacopoeia, as shown in the following table 4:
TABLE 4 Table 4
As can be seen from the comparison of the table, the colloid formed by hydroxypropyl methylcellulose-phospholipid has better inclusion effect on turmeric extract, but when the turmeric extract proportion is too high, the solubility of the finished product is affected, and precipitates appear, preferably the mass ratio of turmeric extract to amphoteric sol is 1.5-1:1.
Example 1:
Taking 1000kg of turmeric medicinal material, coarsely crushing in a crusher, placing in a multifunctional extraction tank, adding 70% ethanol with the weight of 8 times of the medicinal material, heating and reflux-extracting for 2.0 hours, filtering the extracting solution, and then heating and reflux-extracting the residues with 6 times of 70% ethanol for 1.0 hour, filtering the extracting solution for later use; concentrating the extractive solution under reduced pressure in a concentrator at a vacuum degree of-0.06 to-0.1 MPa and a temperature of 50-70deg.C until the relative density is 1.05-1.3, and crystallizing at constant volume to obtain curcumin effective component. Dissolving 25 parts by weight of turmeric extract in a proper amount of ethanol solution, and stirring and dissolving uniformly to obtain turmeric extract solution for later use; another 16 parts by weight of hydroxypropyl methylcellulose and 5 parts by weight of phospholipid were placed in a formulation tank, water 15 times as much as the hydroxypropyl methylcellulose was added and stirred to dissolve, and then a homogenizer was used to homogenize the temperature: 55 ℃, pressure: 70MPa, obtaining uniform and stable hydroxypropyl methyl cellulose-phospholipid sol for standby; mixing the turmeric extract solution and hydroxypropyl methylcellulose-phospholipid sol in a preparation tank, homogenizing by using a homogenizer at the homogenization temperature: 55 ℃, pressure: 30MPa; and then adding 53 parts by weight of maltodextrin and 1 part by weight of citric acid, uniformly mixing, drying the material taking liquid in a spray dryer, wherein the air inlet temperature is 185-205 ℃, the air outlet temperature is 85-105 ℃, collecting turmeric extract obtained by spray drying, sieving with a 60-mesh sieve, and mixing to obtain the final product 1.
Example 2:
Dissolving 20 parts by weight of turmeric extract in a proper amount of ethanol solution, and stirring and dissolving uniformly to obtain turmeric extract solution for later use; another 15 parts by weight of hydroxypropyl methylcellulose and 5 parts by weight of phospholipid are placed in a preparation tank, water which is 15 times of the hydroxypropyl methylcellulose is added and stirred to be uniformly dissolved, and then a homogenizer is used for homogenizing at the temperature: 50 ℃, pressure: 75MPa, obtaining uniform and stable hydroxypropyl methyl cellulose-phospholipid sol for standby; mixing the turmeric extract solution and hydroxypropyl methylcellulose-phospholipid sol in a preparation tank, homogenizing by using a homogenizer at the homogenization temperature: 50 ℃, pressure: 35MPa; then adding 59.5 parts by weight of maltodextrin and 0.5 part by weight of citric acid, and uniformly mixing; drying the material liquid in a spray dryer, wherein the air inlet temperature is 185-205 ℃, the air outlet temperature is 85-105 ℃, collecting turmeric extract obtained by spray drying, sieving with a 60-mesh sieve, mixing and the like to obtain the final product 2.
Example 3:
Dissolving 20 parts by weight of turmeric extract in a proper amount of ethanol solution, and stirring and dissolving uniformly to obtain turmeric extract solution for later use; placing 10 parts by weight of hydroxypropyl methylcellulose and 10 parts by weight of phospholipid into a preparation tank, adding 15 times of water equivalent to the hydroxypropyl methylcellulose, stirring to dissolve uniformly, and using a homogenizer at the following homogenizing temperature: 60 ℃, pressure: 65MPa, obtaining uniform and stable hydroxypropyl methyl cellulose-phospholipid sol for standby; mixing the turmeric extract solution and hydroxypropyl methylcellulose-phospholipid sol in a preparation tank, homogenizing by using a homogenizer at the homogenization temperature: 60 ℃, pressure: 25MPa; then 58.5 parts by weight of maltodextrin and 1.5 parts by weight of citric acid are added and uniformly mixed; drying the material liquid in a spray dryer, wherein the air inlet temperature is 185-205 ℃, the air outlet temperature is 85-105 ℃, collecting turmeric extract obtained by spray drying, sieving with a 60-mesh sieve, mixing and the like to obtain the final product 3.
1 Dissolution contrast:
The dissolution rate measurement is an important index for evaluating the drug characteristics and the rationality of the preparation process, and is used for evaluating the dissolution performance of the drug and optimizing the preparation process, so that the solubility of the indissolvable drug is improved, and the drug achieves the expected use purpose; however, the unreasonable preparation process is counterproductive, so that the solvent property of the medicine is reduced, and the treatment effect of the medicine is affected. The difference in dissolution rate of turmeric products was evaluated by collecting commercially available turmeric formulations claiming high bioavailability and comparing the dissolution rate of turmeric products of the present invention.
The measuring method comprises the following steps: dissolution and release measurement method according to the second method (China pharmacopoeia 2015 edition, fourth division, general rule 0931). Sample list 5, results are shown in table 6:
TABLE 5
Table 6 cumulative dissolution average at each time point of three curcuminoids in each sample (n=6)
From the above data, the cumulative dissolution rates of 3 curcumin components (curcumin, demethoxycurcumin, bisdemethoxycurcumin) in the turmeric extract of sample a are all very low; while the sample B and the sample C are turmeric products subjected to inclusion treatment of different cyclodextrins, the differences of the accumulated dissolution rates of curcumin, demethoxycurcumin and bisdemethoxycurcumin can be known that the inclusion process has obvious influence on the dissolution of various curcumin components; sample D is a turmeric product prepared by the invention, and the cumulative dissolution rate data shows that the cumulative dissolution rates of curcumin, demethoxycurcumin and bisdemethoxycurcumin are optimal, so that the dissolution of each component of curcumin is obviously improved.
2 Bioavailability contrast
The content of the effective components in the simulated gastric fluid is measured, and the samples are shown in table 7:
TABLE 7 list of samples to be tested
The samples were taken and placed in simulated gastric fluid (NaCl (AR) 0.4g, pepsin 0.64g, dissolved in deionized water, concentrated hydrochloric acid 1.4ml, constant volume to 200 ml) and mixed well before shaking in a water bath at 37℃for 1h at 100 r/min. After centrifugation at 12000r/min for 5min, the supernatant was filtered through a 0.22 μm filter, and subjected to liquid phase analysis, each sample was tested in triplicate, and the mean value was obtained as shown in Table 8 below:
table 8 sample effective ingredient content change after 1h of simulated gastric fluid digestion (n=3)
The above results suggest that, of the 4 samples, sample D had a relatively good release property in simulated gastric fluid, the content of the active ingredient thereof was further increased after gastric fluid digestion, while sample a was a turmeric extract which was not subjected to inclusion treatment, so that each curcumin component was lower than the detection limit, and samples B and C were only eluted in small amounts.
Transport of Caco-2 cells
The Caco-2 cell model is a rapid screening tool for drug absorption research, and can provide comprehensive information of absorption, distribution, metabolism, transportation and the like of drug molecules through small intestinal mucosa on the cellular level. The Caco-2 cell model is used for researching good correlation and high reproducibility between the transportation and metabolism of the intestinal tract medicine and the absorption of the medicine in the intestines. The transmembrane resistance was measured by washing the monolayer of cells 3 times with HBSS at pH7.4 at 37℃and discarding cells having a transmembrane resistance value of less than 500. OMEGA.times.cm 2. After cells were incubated in buffer for 30min, the incubation medium was aspirated away, 0.5mL of solution containing the drug to be tested was added to the AP side, 2.0mL of uniculture was added to the BL side, and the AP side liquid was collected after 60 min. Each group was provided with 3 parallel wells, the concentration of the transport fluid samples was measured by HPLC, the bioavailability differences of the turmeric preparations were compared with the curcumin component content, the test samples are shown in table 9, and the experimental results are shown in table 10.
TABLE 9 list of samples to be tested
Table 10 Caco-2 liquid phase test results of cell transport experiments
Note that: compared to sample 2, p < 0.05, # p < 0.05; △△ p < 0.01 compared to sample 1.
The cell transport experiment results indicate that the effective components in the sample D are absorbed to different degrees, wherein the absorption amount of the double demethoxycurcumin is maximum, the demethoxycurcumin is secondary, and the curcumin is lower; sample a did not detect transported curcuminoids due to poor solubility; the transport of each component of curcumin in the sample B is lower than that in the sample D, and only demethoxycurcumin in the sample C is absorbed and transported.
Claims (4)
1. The preparation method of the turmeric composition with high bioavailability is characterized by comprising the following steps of:
Turmeric extract 20-30 parts
10-20 Parts of hydroxypropyl methyl cellulose
1-10 Parts of phospholipid;
the mass ratio of the hydroxypropyl methylcellulose to the phospholipid is 3:1-1:1;
The preparation method of the turmeric composition with high bioavailability comprises the following steps:
(1) Dissolving Curcuma rhizome extract in ethanol solution, stirring, and dissolving to obtain Curcuma rhizome extract solution;
(2) Adding water into hydroxypropyl methylcellulose and phospholipid, stirring to dissolve uniformly, and homogenizing
Homogenizing to obtain uniform stable amphoteric sol for use; the homogenization temperature: 55.+ -. 5 ℃ and pressure: 70+/-5 MPa;
(3) Mixing Curcuma rhizome extract solution with amphoteric sol, homogenizing with homogenizer; the homogenization temperature: 55 + -5 deg.C,
Pressure: 30+/-5 MPa; the mass ratio of the turmeric extract to the amphoteric sol is 1.5-1:1, a step of;
(4) Then volatilizing ethanol, adding maltodextrin and citric acid, and uniformly mixing;
(5) And (5) drying and sieving the feed liquid obtained in the step (4) to obtain the turmeric composition.
2. The method for preparing a turmeric composition of claim 1, wherein said turmeric composition further comprises 45-65 parts by weight maltodextrin and 0.1-2 parts by weight citric acid.
3. The process according to claim 1, wherein in the step (2), the water addition amount is 12 to 16 times the amount of hydroxypropyl methylcellulose.
4. The method of claim 1, wherein in step (5), the drying is spray drying or freeze drying; the air inlet temperature of spray drying is 185-205 ℃, and the air outlet temperature is 85-105 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111587358.5A CN114209060B (en) | 2021-12-23 | 2021-12-23 | Turmeric composition with high bioavailability and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111587358.5A CN114209060B (en) | 2021-12-23 | 2021-12-23 | Turmeric composition with high bioavailability and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114209060A CN114209060A (en) | 2022-03-22 |
| CN114209060B true CN114209060B (en) | 2024-07-19 |
Family
ID=80705283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111587358.5A Active CN114209060B (en) | 2021-12-23 | 2021-12-23 | Turmeric composition with high bioavailability and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114209060B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113573722A (en) * | 2019-03-18 | 2021-10-29 | 因德纳有限公司 | Composition comprising curcumin and coenzyme Q10 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1274300C (en) * | 2003-12-11 | 2006-09-13 | 中国科学院生物物理研究所 | Combination of medication in use for improving dissolution of curcumin and bioavailability as well as preparation method |
| CN104013601A (en) * | 2014-06-06 | 2014-09-03 | 重庆医科大学 | Curcumine hydroxypropyl cyclodextrin phospholipid nanoparticles and preparation method thereof |
| CN104873983A (en) * | 2015-05-25 | 2015-09-02 | 福建省力菲克药业有限公司 | Curcumin cyclodextrin clathrate compound and preparation method thereof |
| CN107213467A (en) * | 2017-05-22 | 2017-09-29 | 江苏大学 | A kind of preparation method of phospholipid complexes of curcumin |
| CN109589410B (en) * | 2018-12-26 | 2022-02-01 | 晨光生物科技集团股份有限公司 | Curcumin preparation and preparation method thereof |
-
2021
- 2021-12-23 CN CN202111587358.5A patent/CN114209060B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113573722A (en) * | 2019-03-18 | 2021-10-29 | 因德纳有限公司 | Composition comprising curcumin and coenzyme Q10 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114209060A (en) | 2022-03-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Luo et al. | Herbal medicine derived carbon dots: synthesis and applications in therapeutics, bioimaging and sensing | |
| Schiborr et al. | The oral bioavailability of curcumin from micronized powder and liquid micelles is significantly increased in healthy humans and differs between sexes | |
| JP2014224113A (en) | Chinese-medicine composition having lipid-lowering and liver-protecting effects, and preparing method and application thereof | |
| CN104739751B (en) | A kind of tetrahydro curcumin solid dispersions and preparation method thereof | |
| CN114209060B (en) | Turmeric composition with high bioavailability and preparation method thereof | |
| CN112535717A (en) | Turmeric extract and preparation method thereof | |
| RU2712264C2 (en) | Composition for silybin-based injections and method for production thereof | |
| Jiang et al. | Erzhi formula extracts reverse renal injury in diabetic nephropathy rats by protecting the renal podocytes | |
| CN102018736B (en) | Natural indigo decoction piece and preparation method thereof | |
| CN116440290A (en) | Berberine oxide cyclodextrin inclusion compound, and preparation method and application thereof | |
| CN1853627B (en) | Cyclodextrin of bibenziisosehenazole ethane or cyclodextrin derivative inclusion compound, and preparation and use thereof | |
| JP7462744B2 (en) | Compositions and methods for treating diabetes | |
| CN115137693A (en) | Carbocisteine oral preparation and preparation method thereof | |
| CN1857400A (en) | Coated selfheal tablet and its preparing method | |
| JP4896401B2 (en) | Ursolic acid-soybean lecithin freeze-dried nanoparticle injection and method for producing the same | |
| CN106749174A (en) | A kind of sitafloxacin dihydrate crystal formation, preparation method and combinations thereof tablet | |
| CN102204960A (en) | Chinese medicinal composition for treating hepatopathy and preparation method thereof | |
| CN111467502A (en) | Water-soluble coenzyme Q10 composition and preparation method thereof | |
| CN110090216A (en) | The application of indole alkaloids compound and its derivative or salt in prevention and treatment diabetic nephropathy product | |
| CN109771596A (en) | A kind of Antibicrobial anti inflammatory capsule and preparation method thereof | |
| CN102793740B (en) | Nutrient particles with auxiliary protecting function on chemical liver injury | |
| CN116270821B (en) | Perilla Huang Zhihai granule and preparation method thereof | |
| Yong et al. | Study on the pharmacokinetics of Polygonatum cyrtonema polysaccharide DPC1 through fluorescence labeling | |
| CN116159096B (en) | Compound ketoconazole preparation for pets and preparation method thereof | |
| CN110693897B (en) | Application of oil tea flesh fruit polysaccharide in preparation of medicine or health-care product for preventing and treating type II diabetes |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |