CN106588992A - Luteolin-Mn complex promoting cells to consume glucose as well as preparation and application of luteolin-Mn complex - Google Patents
Luteolin-Mn complex promoting cells to consume glucose as well as preparation and application of luteolin-Mn complex Download PDFInfo
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- CN106588992A CN106588992A CN201610989237.6A CN201610989237A CN106588992A CN 106588992 A CN106588992 A CN 106588992A CN 201610989237 A CN201610989237 A CN 201610989237A CN 106588992 A CN106588992 A CN 106588992A
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- Prior art keywords
- luteolin
- complex
- preparation
- coordination compounds
- glucose
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 title claims abstract description 22
- 239000008103 glucose Substances 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 230000001737 promoting effect Effects 0.000 title abstract description 3
- 239000011572 manganese Substances 0.000 claims abstract description 36
- 235000009498 luteolin Nutrition 0.000 claims abstract description 26
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims abstract description 21
- LRDGATPGVJTWLJ-UHFFFAOYSA-N luteolin Natural products OC1=CC(O)=CC(C=2OC3=CC(O)=CC(O)=C3C(=O)C=2)=C1 LRDGATPGVJTWLJ-UHFFFAOYSA-N 0.000 claims abstract description 21
- IQPNAANSBPBGFQ-UHFFFAOYSA-N luteolin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C(O)=C1 IQPNAANSBPBGFQ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000005406 washing Methods 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000843 powder Substances 0.000 claims abstract description 7
- 239000007787 solid Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 238000001035 drying Methods 0.000 claims abstract description 5
- 235000013402 health food Nutrition 0.000 claims abstract description 5
- 239000012265 solid product Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 34
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 13
- 229940071125 manganese acetate Drugs 0.000 claims description 8
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- 238000001291 vacuum drying Methods 0.000 claims description 6
- 239000003472 antidiabetic agent Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000010792 warming Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 14
- 239000008280 blood Substances 0.000 abstract description 7
- 210000004369 blood Anatomy 0.000 abstract description 7
- 229940079593 drug Drugs 0.000 abstract description 5
- 230000004071 biological effect Effects 0.000 abstract description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 abstract description 2
- 229930014626 natural product Natural products 0.000 abstract description 2
- 238000010992 reflux Methods 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 7
- 229960003957 dexamethasone Drugs 0.000 description 7
- 241000219095 Vitis Species 0.000 description 6
- 235000009754 Vitis X bourquina Nutrition 0.000 description 6
- 235000012333 Vitis X labruscana Nutrition 0.000 description 6
- 235000014787 Vitis vinifera Nutrition 0.000 description 6
- 239000012531 culture fluid Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 5
- 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 description 4
- 238000013019 agitation Methods 0.000 description 4
- 230000010261 cell growth Effects 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229930003944 flavone Natural products 0.000 description 4
- 150000002212 flavone derivatives Chemical class 0.000 description 4
- 235000011949 flavones Nutrition 0.000 description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
- 229910052748 manganese Inorganic materials 0.000 description 4
- 239000011573 trace mineral Substances 0.000 description 4
- 235000013619 trace mineral Nutrition 0.000 description 4
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 2
- 102000004877 Insulin Human genes 0.000 description 2
- 108090001061 Insulin Proteins 0.000 description 2
- 241000282806 Rhinoceros Species 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 229940125396 insulin Drugs 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000001502 supplementing effect Effects 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 102000051325 Glucagon Human genes 0.000 description 1
- 108060003199 Glucagon Proteins 0.000 description 1
- 235000019082 Osmanthus Nutrition 0.000 description 1
- 241000333181 Osmanthus Species 0.000 description 1
- 108010019160 Pancreatin Proteins 0.000 description 1
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 1
- 229960004666 glucagon Drugs 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- -1 kaempferol class compound Chemical class 0.000 description 1
- 229910001437 manganese ion Inorganic materials 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- 229940055695 pancreatin Drugs 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
- C07F13/005—Compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- 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)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
The invention belongs to the technical field of natural product modified medicines and discloses a luteolin-Mn complex promoting cells to consume glucose as well as preparation and application of the luteolin-Mn complex. A preparation method comprises the following steps: dissolving luteolin into anhydrous alcohol, then adding acetic manganese, regulating a pH value of a reaction solution to 2-6 with hydrochloric acid, raising the temperature to 50-70 DEG C, carrying out refluxing stirring reaction for 3-7h, and separating, washing and drying a solid product to obtain luteolin-Mn complex solid powder. Compared with single luteolin, the luteolin-Mn complex prepared by the invention is obviously improved in the biological activity aspects of blood sugar reducing capability and the like and can be used for developing blood sugar reducing medicines or health food.
Description
Technical field
The invention belongs to natural product modification of pharmaceutical technical field, and in particular to a kind of wood of promotion cell consumption glucose
Rhinoceros grass element-Mn coordination compounds and preparation and application.
Background technology
Luteolin is a kind of natural faintly acid kaempferol class compound.There are such compound various physiology to live
Property, such as antibacterial action, antioxidation, antiinflammation, antivirus action, antitumor action should in fields such as medicine, health cares
With extensive, but luteolin effect in terms of blood sugar lowering is not obvious.
Manganese is trace element needed by human, is to participate in one of metabolic trace element of human body three nutritious elements, right
Play an important role in the vital movement of people is maintained.Trace element manganese easily causes toxic and side effects when individually supplementing, for this purpose, this yuan
The supplement of element mostly takes the form of coordination compound, such as kaempferol-manganese complex, galangin-manganese complex, the method protecting
While card original compound advantage, the trace element of needed by human body is supplemented further through coordination mode, even with the association of the two
Same-action strengthens the biological activity of former compound or produces some other active function.From flavone structural formula, flavone chemical combination
Phenolic hydroxyl group or carbonyl are usually contained in thing, one or more pairs of lone pair electrons can be provided and sent out with the metallic element ion containing unoccupied orbital
Raw reaction, meanwhile, the space structure of flavone is conducive to the formation of coordination compound, so as to obtain stable flavone coordination compound.
The content of the invention
In order to solve the shortcoming and defect part of above prior art, the primary and foremost purpose of the present invention is to provide a kind of promotion
The preparation method of the luteolin-Mn coordination compounds of cell consumption glucose.
Another object of the present invention is to provide a kind of luteolin-Mn coordination compounds prepared by said method.
It is still another object of the present invention to provide above-mentioned luteolin-Mn coordination compounds are preparing hypoglycemic drug or health care food
Application in product.
The object of the invention is achieved through the following technical solutions：
A kind of preparation method of the luteolin-Mn coordination compounds of promotion cell consumption glucose, including following preparation process：
Take luteolin to be dissolved in dehydrated alcohol, be subsequently adding manganese acetate, it is 2～6 to adjust reactant liquor pH with hydrochloric acid, is heated up
3～7h of reaction is refluxed to 50～70 DEG C, solid product separating, washing, drying obtains luteolin-Mn coordination compounds and consolidates
Body powder.
Preferably, the ratio of the amount of the material that the luteolin is added with manganese acetate is (2～4):1.
Preferably, described washing is referred to and washed with dehydrated alcohol.
Preferably, described drying refers to vacuum drying.
A kind of luteolin-Mn coordination compounds, are prepared by said method.
Application of the above-mentioned luteolin-Mn coordination compounds in hypoglycemic drug or health food is prepared.
The present invention for luteolin the characteristics of, with luteolin as raw material, dehydrated alcohol is solvent, by with manganese metal
Luteolin-Mn coordination compounds prepared and complexation reaction in ion there is.The coordination compound is supplementing the micro unit of human body in coordination ion mode
While plain manganese, also promote grape cell sugar consumption, enhance its hypoglycemic activity, can be applicable to novel blood sugar lowing medicine or
The exploitation of health food.
The invention has the advantages that and beneficial effect：
(1) luteolin after being coordinated has significant blood sugar decreasing effect；Wherein, under the conditions of without dexamethasone, sweet-scented osmanthus
Careless element-Mn coordination compounds are up to 2.17 ± 1.46 to the glucose consumption ability of HepG2 cells；Under the conditions of having dexamethasone, wood
Rhinoceros grass element-Mn coordination compounds do not possess the effect for promoting HepG2 grape cell sugar consumptions.
(2) present invention is introduced to metal manganese ion on luteolin molecular structure site by coordination, and method is simply easy
OK, the physicochemical property of luteolin is not only improved, and promotes human body to luteolin, the absorption profit to minor metallic element
With.
Specific embodiment
With reference to embodiment, the present invention is described in further detail, but embodiments of the present invention not limited to this.
Embodiment 1
The dehydrated alcohol that 1mmol luteolins are dissolved in 100mL is weighed, is vibrated, ultrasonic dissolution.The amount ratio for adding material is 2:
1 (luteolin:Mn2+=2:1) manganese acetate, it is 5 to adjust reactant liquor pH using the HCl of 1mmol/L, in 60 DEG C of constant temperatures
Under, water-bath backflow magnetic agitation reacts 5h, takes out, sucking filtration, by gained solid dehydrated alcohol cyclic washing, until washing liquid becomes
Into colourless till, vacuum drying obtains luteolin-Mn coordination compound pressed powders.
Embodiment 2
The dehydrated alcohol that 1mmol luteolins are dissolved in 100mL is weighed, is vibrated, ultrasonic dissolution.The amount ratio for adding material is 2:
1 (luteolin:Mn2+=2:1) manganese acetate, it is 6 to adjust reactant liquor pH using the HCl of 1mmol/L, in 60 DEG C of constant temperatures
Under, water-bath backflow magnetic agitation reacts 6h, takes out, sucking filtration, by gained solid dehydrated alcohol cyclic washing, until washing liquid becomes
Into colourless till, vacuum drying obtains luteolin-Mn coordination compound pressed powders.
Embodiment 3
The dehydrated alcohol that 1mmol luteolins are dissolved in 100mL is weighed, is vibrated, ultrasonic dissolution.The amount ratio for adding material is 3:
1 (luteolin:Mn2+=3:1) manganese acetate, it is 4 to adjust reactant liquor pH using the HCl of 1mmol/L, in 50 DEG C of constant temperatures
Under, water-bath backflow magnetic agitation reacts 7h, takes out, sucking filtration, by gained solid dehydrated alcohol cyclic washing, until washing liquid becomes
Into colourless till, vacuum drying obtains luteolin-Mn coordination compound pressed powders.
Embodiment 4
The dehydrated alcohol that 1mmol luteolins are dissolved in 100mL is weighed, is vibrated, ultrasonic dissolution.The amount ratio for adding material is 4:
1 (luteolin:Mn2+=4:1) manganese acetate, it is 6 to adjust reactant liquor pH using the HCl of 1mmol/L, in 70 DEG C of constant temperatures
Under, water-bath backflow magnetic agitation reacts 4h, takes out, sucking filtration, by gained solid dehydrated alcohol cyclic washing, until washing liquid becomes
Into colourless till, vacuum drying obtains luteolin-Mn coordination compound pressed powders.
Gained luteolin-Mn coordination compounds of the invention promote cell consumption glucose aptitude tests：
It is prepared by drug sample to be measured：100mg luteolins are weighed respectively and embodiment of the present invention gained luteolin-Mn matches somebody with somebody
Compound, is fully dissolved with 1% DMSO, with cell growth culture fluid constant volume in the volumetric flask of 100mL, is prepared 1mg/mL and is treated
Survey mother liquid medicine.The drug sample to be measured of variable concentrations is constantly diluted to, is mixed standby.
HepG2 cell culture：From Traditional Chinese Medicine University Of Guangzhou, cell growth culture fluid is RPMI to hepatoma Hep G 2 cells
The hyclone FBS of 1640 culture medium+10%.Pancreatin digestion harvests the HepG2 cells of exponential phase, with cell growth culture
Liquid suspends, and by 8000/hole 96 orifice plates are inoculated in, and makes in cell culture incubator incubation 24h adherent.
The measure that versus glucose is consumed：Cell growth culture fluid is replaced by containing the fresh of variable concentrations medicine to be measured
The μ L/ holes of culture fluid 100, while the cell controls group without medicine to be measured is set up, four multiple holes of each concentration.For inducing cell
Insulin resistant, add 1 μm of ol/L DXMS (dexamethasone) in the culture fluid of medicine to be measured, while set up being not added with DXMS
Matched group, by cell be placed in incubator be incubated 48h after take out.Determined in each hole culture fluid using glucose determination reagent box
The concentration of remaining glucose, calculate medicine functional hole cell relative to control wells cell versus glucose consumption (RGC,
Relative Glucose Consumption).Wherein, the RGC of the cell controls group without medicine to be measured is 100%.
The calculating of grape cell sugar consumption ability：By the insulin resistant HepG2 cell models for setting up DXMS inductions, survey
Grape cell sugar consumption ability (GCA, Glucose Consumption Ability) is made, as the life of glucagon opposing
The evaluation index of thing activity, can be used to treat the related symptoms of diabetes.GCA presses column count under formula：
When GCA >=1, represent that medicine to be measured enhances the glucose consumption ability of IR cells, with obvious biological living
Property.
Tested by said method, variable concentrations luteolin is to HepG2 cells propagation and the shadow of glucose consumption ability
Ring result as shown in table 1；Variable concentrations luteolin-Mn coordination compounds are to HepG2 cells propagation and the shadow of glucose consumption ability
Ring result as shown in table 2.
Table 1
Table 2
Tables 1 and 2 result shows：During luteolin-Mn coordination compound individualisms, HepG2 grape cell sugar can be promoted to disappear
The effect of consumption, is now up to 2.17 ± 1.46 to the glucose consumption ability of HepG2 cells, when coexisting with dexamethasone, does not have
The effect of standby promotion HepG2 grape cell sugar consumptions.Single luteolin is compared, the luteolin after Mn coordinations is in blood sugar lowering energy
The biological activity aspect of power is obviously improved, and can be used for the exploitation of novel blood sugar lowing medicine or health food.
Above-described embodiment is the present invention preferably embodiment, but embodiments of the present invention not by above-described embodiment
Limit, other any spirit and the changes, modification, replacement made under principle without departing from the present invention, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (6)
1. it is a kind of promote cell consumption glucose luteolin-Mn coordination compounds preparation method, it is characterised in that including as follows
Preparation process：
Take luteolin to be dissolved in dehydrated alcohol, be subsequently adding manganese acetate, it is 2～6 to adjust reactant liquor pH with hydrochloric acid, is warming up to 50
～70 DEG C are refluxed 3～7h of reaction, and solid product separating, washing, drying obtains luteolin-Mn coordination compound solid powder
End.
2. it is according to claim 1 it is a kind of promote cell consumption glucose luteolin-Mn coordination compounds preparation method,
It is characterized in that：The ratio of the amount of the material that the luteolin is added with manganese acetate is (2～4):1.
3. it is according to claim 1 it is a kind of promote cell consumption glucose luteolin-Mn coordination compounds preparation method,
It is characterized in that：Described washing is referred to is washed with dehydrated alcohol.
4. it is according to claim 1 it is a kind of promote cell consumption glucose luteolin-Mn coordination compounds preparation method,
It is characterized in that：Described drying refers to vacuum drying.
5. a kind of luteolin-Mn coordination compounds, it is characterised in that：It is prepared into by the method described in any one of Claims 1 to 4
Arrive.
6. application of the luteolin-Mn coordination compounds described in claim 5 in hypoglycemic drug or health food is prepared.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610989237.6A CN106588992B (en) | 2016-11-10 | 2016-11-10 | It is a kind of promote cell consumption glucose luteolin-Mn complex and preparation and application |
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| CN112442051A (en) * | 2020-12-03 | 2021-03-05 | 南开大学 | Flavone metal complex for inhibiting citrus canker pathogenic bacteria |
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| CN1817896A (en) * | 2006-03-10 | 2006-08-16 | 中山大学 | Compounds like quercetol and metal complex of their glycosides and uses |
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| CN1817896A (en) * | 2006-03-10 | 2006-08-16 | 中山大学 | Compounds like quercetol and metal complex of their glycosides and uses |
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| JING ZHOU等: ""Antioxidative and anti-tumour activities of solid quercetin metal(II) complexes"", 《TRANSITION METAL CHEMISTRY》 * |
| 李学洁等: ""山奈酚-锰配合物合成工艺的研究"", 《山西中医学院学报》 * |
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| CN112442051A (en) * | 2020-12-03 | 2021-03-05 | 南开大学 | Flavone metal complex for inhibiting citrus canker pathogenic bacteria |
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