CN1846695A - Application of 3,5,7,3',4',5'-hexahydroxyl-2,3-dihydroflavone in preparing medicine - Google Patents
Application of 3,5,7,3',4',5'-hexahydroxyl-2,3-dihydroflavone in preparing medicine Download PDFInfo
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- CN1846695A CN1846695A CNA2006100337754A CN200610033775A CN1846695A CN 1846695 A CN1846695 A CN 1846695A CN A2006100337754 A CNA2006100337754 A CN A2006100337754A CN 200610033775 A CN200610033775 A CN 200610033775A CN 1846695 A CN1846695 A CN 1846695A
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Abstract
The present invention relates to the new use of 3,5,7,3',4',5'-hexahydroxy-2,3-dihydroflavone in preparing medicine. The compound 3,5,7,3',4',5'-hexahydroxy-2,3-dihydroflavone is applied in preparing saccharification end product inhibitor, antioxidant and diacyl glycerol protein kinase C inhibitor.
Description
Technical field
The present invention relates to 3,5,7; 3 ', 4 ', 5 '-hexahydroxy-2; the 3-flavanone (hereinafter to be referred as: the ZL2004) application in pharmacy relates in particular to the application in preparation glycation end product inhibitor, antioxidant and DG inhibitors of protein kinase C medicine.
Background technology
The ZL2004 chemical structural formula is:
Molecular formula is C
15H
12O
8, micro-yellow powder or white, needle-shaped crystals, relative molecular mass is 320.2, mp 246-247 ℃, be soluble in hot water, hot ethanol, be dissolved in methanol, ethanol, acetone, be slightly soluble in water, ethyl acetate, be insoluble in chloroform, petroleum ether.
This chemical compound is separated in the leaf that 1940 from Vitaceae ampelopsis fujian tea was A. Meliaefolia (A.Meliaefolia) by Kotake and Kubota first, called after Ampelopstin (ampeloptin) [Ann, 1940,544:253], after name dihydromyricetin flavin (dihydromyricetin) and ampelopsin (ampelopsin) [The Merck Index are arranged again, 12ed, 1996,97].This chemical compound extensively is present in coniferae and the timber, in Pinus (pinus) and Cedrus (cedrus) bark, also be present in woody angiosperm, in the Du Juan flower plant sand Du Juan of section (Rhodendroncinnabariunm) leaf, Cercidiphyllaceae plant Fructus Cercidiphylli Sinensis (Cercidiphyllumjaponicus) timber.This plant is present in the plants such as Myruca ceas, Du Juanke, Guttiferae, Euphorbiaceae, and tool is anticancer, function of gallbladder promoting and antiinflammatory action.Show from present research situation, this chemical compound is present in the vitaceae in a large number, as Ampelopsis grossedentata (Agrossedentata), ampelopsis cantoniensis (Cantoniensis), leatherleaf Caulis seu folium ampelopsis brevipedunculatae (Caulis Ampelopsis Brevipedunculae) (Achaffanjoni), Caulis seu folium ampelopsis brevipedunculatae (Caulis Ampelopsis Brevipedunculae) (Asinica), Northeastern Caulis seu folium ampelopsis brevipedunculatae (Abrevipedunculate), Ampelopsis (Asinicavarhancei) etc., especially in ampelopsis, exist in a large number especially, as be distributed widely in the Guangdong of China, Guangxi, Yunnan, the Hunan, Hubei, content reaches 20%～30% in the young young stem and leaf of the Ampelopsis grossedentata of provinces and regions such as Jiangxi and ampelopsis cantoniensis plant.Ampelopsis cantoniensis (" Chinese medicine dictionary " claims Radix Ampelopsis Cantoniensis) and Ampelopsis grossedentata (claim Ampelopsis grossedentata again, mutation for ampelopsis cantoniensis) dry products of this two kind of plant always be among the people do refreshing and detoxicating for the tea-drinking product, have effects such as the broken knot of heat-clearing and toxic substances removing, expelling wind and removing dampness, dissipating blood stasis, diuresis, antiinflammatory, control that lung abscess, rheumatism, carbuncle disease swell and ache, traumatic injury, scald, chronic nephritis, hepatitis, difficulty and pain in micturition, gastropyretic vomiting, flu, laryngopharynx swelling and pain etc.
It is reported that ZL2004 has antitumaous effect, prevents and treats acquired immune deficiency syndrome (AIDS) effect and antivirus action.
Summary of the invention
The object of the present invention is to provide the application of ZL2004 at preparation glycation end product inhibitor, antioxidant and DG inhibitors of protein kinase C medicine.
Essence for a better understanding of the present invention adopts pharmacological evaluation and the result of ZL2004 that its new purposes in pharmaceutical field is described.
The present invention makes positive control with vitamin C, comes comparison ZL2004 to the scavenging action of oxygen-derived free radicals and to the scavenging action of malonaldehyde in the rat cerebral tissue (MDA), and the result shows that effect all is better than the positive control drug vitamin C.
Suppress the effect test that glycation end product (AGEs) forms:, estimate the effect that AGEs forms that suppresses according to the speed that AGEs forms by the model that external glycation end product AGEs forms.The result shows: ZL2004 has the effect that the external nonenzymatic glycosylation end-product of tangible prevention forms, and effect is better than positive control drug aminoguanidine (AG).
Inhibitory action test to PKC is PepTag
The C1 peptide is a kind of small peptide that has specific fluorescence, and PKC can make its phosphorylation in the tissue, and the peptide substrate of phosphorylation has negative charge, and unphosphorylated substrate has positive charge, shows as on agarose gel to the two poles of the earth electrophoresis.If a little less than the fluorescence, show that phosphorylated substrate is few in the positive extreme direction, promptly PKC is suppressed, and the sxemiquantitative test shows, ZL2004 to the inhibitory action of the normal PKC of rat cerebral tissue near positive control drug Staurospoine.
The acute toxicity testing of white mice is: get the Kunming white mice, and pharmacology test method test routinely, the result shows that ZL2004 toxicity belongs to low toxicity～nontoxic level, the intraperitoneal administration non-toxic reaches the 1000mg/kg mice.
Can illustrate from above result and the invention has the advantages that:
(1) the present invention has excavated new medical application to compound known ZL2004, has opened up a new application.
(2) ZL2004 raw material sources of the present invention are abundant, can make peroral dosage form, injection type, tablet etc., and are easy to use.
(3), therefore can be used for treating diabetes, defying age, atherosclerosis because the medicine that material of the present invention is mixed with has the effect that remarkable inhibition glycation end product forms.
(4) because therefore the effect that the medicine that material of the present invention is mixed with has remarkable Profilin kinase c phosphorylation can be used for treating diabetes, anticancer, anti-central nervous system disease (spinal nerves pain etc.).
(5) because the medicine that is mixed with of material of the present invention has and removes free radical significantly, suppresses the effect that malonaldehyde (MDA) generates, therefore can be used for treating diabetes, anticancer, defying age, atherosclerosis, antiinflammatory, resisting hypertension hypercholesterolemia, anti-central nervous system disease (parkinson etc.).
With ZL2004 adopt acceptable accessories routinely production method be prepared on the pharmaceutics said any dosage form and comprise peroral dosage form such as tablet, electuary, capsule, oral liquid etc., also can be prepared into injection type, as powder ampoule agent for injection, injection etc.; Also can make targeting preparation, as liposome etc.
Contain the ZL2004 that weight ratio is 1-99% in the pharmaceutical dosage form of the present invention.
Amount of drug of the present invention can change according to route of administration, patient's age, body weight, tumor type.Its dosage can be 0.5-1g, can subcutaneous or intramuscular injection, or intravenous injection or instillation, also can oral medication.
Description of drawings
Fig. 1 is ZL2004 to the scavenging action of hydroxyl and superoxide ion figure as a result.The scavenging action of ZL2004 is observed in explanation in the system of two kinds of different generation hydroxyls and superoxide ion.Vertical coordinate is represented clearance rate, the abscissa indicated concentration.Data are from the meansigma methods and the standard error of six tests.
Fig. 2 is ZL2004 and vitamin C to the inhibition of malonaldehyde in the rat cerebral tissue (MDA) figure as a result.
Fig. 3 is that ZL2004, aminoguanidine suppress the hodograph that AGEs forms.
Fig. 4 is the electrophoresis result figure of ZL2004 to the inhibitory action test of PKC.Control:PKC experiment contrast wherein, Hom:SD big rat brain tissue homogenate (endochylema Partial Protein kinase c), Stau:PKC inhibitor Staurospoine, Negative: negative control.
The specific embodiment
The invention will be further described below in conjunction with embodiment, and these embodiment are to the further specifying of application of the present invention, and are construed as limiting the invention absolutely not.
Get dry Herb or the tender leaf or the root of Vitaceae ampelopsis ampelopsis cantoniensis, crude drug with 95% alcohol-pickled spending the night of 10 times of volumes, filters earlier after crushed.95% reflow of alcohol of 8 times of volumes of medicinal residues reuse is extracted 3 times.Filter.Merging filtrate.Recovered alcohol adds suitable quantity of water to there being solid to separate out, and heating makes the solid dissolving.Take advantage of heat to add the Powdered Activated Carbon of solution total amount 1%-2%, boiled 10 minutes, take advantage of heat filtering.Filtrate go up for another example method through leave standstill, crystallize, water dissolution, the activated carbon removal of impurity and recrystallization, totally 3 times.Collect crystallization at last, after 40 ℃ of dryings of vacuum, get micro-yellow powder or white, needle-shaped crystals.
Get ZL2004 100 gram of said extracted, be dissolved in an amount of 2% the tween 80, add an amount of mannitol again,, make subcutaneous or the intramuscular injection powder ampoule agent for injection through lyophilizing.
Get exsiccant Herb or the tender leaf or the root of Ampelopsis grossedentata, crude drug with medicinal alcohol (50%) soaked overnight of 8 times of volumes, filters earlier after crushed.50% reflow of alcohol of 8 times of volumes of medicinal residues reuse is extracted 3 times.Filter.Merging filtrate.Recovered alcohol adds suitable quantity of water to there being solid to separate out, and heating makes the solid dissolving.Take advantage of heat to add the Powdered Activated Carbon of solution total amount 2%-4%, boiled filtered while hot 10 minutes.Filtrate go up for another example method through leave standstill, crystallize, water dissolution, the activated carbon removal of impurity and recrystallization, totally 4 times.Collect crystallization at last, after 40 ℃ of dryings of vacuum, get micro-yellow powder or white, needle-shaped crystals.
Get the ZL2004 of said extracted, add starch and granulate, add Pulvis Talci, magnesium stearate tabletting, make the ZL2004 tablet.
Embodiment 5 changes the ampelopsis cantoniensis among the embodiment 1 into Ampelopsis, and the alcohol concentration of reflux, extract, is changed to 50%, and its extraction process is made oral liquid according to a conventional method with embodiment 1.
The test of embodiment 6ZL2004 antioxidation
The ZL2004 of embodiment 6,7,8 adopts the standard substance of this chemical compound, is prepared into the aqueous solution of 1mg/ml.
1, to the scavenging action of oxygen-derived free radicals
The OH scavenger can suppress orthophenanthroline-Fe
2+A in the oxidation system
536Reduction, and can pass through A
536Value is the removing ability of OH scavenger relatively.Under experiment condition, observe A
536Value changes, and reaction OH Oxidation and ZL2004 are to the elimination efficiency of OH.The result shows, but OH (Fig. 1), ED are removed in ZL2004 concentration dependent ground
50Be 29.4 μ M.Equally, ZL2004 is to O
2 -Also has certain removing ability (Fig. 1).O
2 -Scavenger can suppress pyrogallol autoxidation process, and the A322 characteristic absorption peak of system is weakened.ZL2004 removes O
2 -ED
50Be 88.9 μ M.150 μ M VitC are lower than the ZL2004 (59.09 ± 4.97%, p＜0.01) of 40 μ M to the clearance rate 43.07 ± 4.11% of OH; To O
2 -Clearance rate be 30.53 ± 3.03%, be lower than the ZL2004 (48.96 ± 6.21%, p＜0.01) of 80 μ M.
2, ZL2004 is to the scavenging action of malonaldehyde (MDA).
1, homogenate preparation: get piece of tissue (0.2-1g) rinsing in ice-cold normal saline, remove blood, the filter paper examination is done, and weighs, and puts into 5 or 10 milliliters small beaker.The volume total amount of homogenate medium should be 9 times of piece of tissue weight, and pipettor is got the homogenate medium of total amount 2/3 or normal saline in beaker, shreds piece of tissue (operation on ice) as early as possible with eye scissors.
2, experimental technique: earlier medicine and homogenate are put into 37 ℃ of incubation 1h, the final concentration of medicine is 1mg/ml, according to test kit explanation application of sample, with whirlpool vortex mixer mixing, the test tube mouth is tightened with the insurance film with sample, 95 ℃ of water-baths 80 minutes, take out back flowing water cooling, 3500-4000 rev/min then, centrifugal 10 minutes, get supernatant, the 532nm place, the 1cm optical path, the distilled water zeroing is measured and is respectively managed absorbance.
Inhibited from the visible ZL2004 of Fig. 2 (1mg/ml) to MDA the rat cerebral tissue, and effect is because positive control drug vitamin C (1mg/ml) (substance B, Q are that positive control and present patent application are irrelevant).
Embodiment 7ZL2004 suppresses the effect that glycation end product (AGEs) forms.
1. reagent and medicine: bovine serum albumin (Bovine albumin serumV, BSA) Amresco packing, glucose (Glucose, GLU), sigma company, aminoguanidine (AminoguanidineHydrochloride, AG, lot:219-956-7, Sigma).
2. experimental technique and step: take by weighing 0.991g glucose and 0.1g BSA, add ZL2004 (1mg/ml) and aminoguanidine monohydrochloride (1mg/ml), be dissolved among the PBS, be settled to 10ml, be provided with GLU+BSA simultaneously, 0.22 μ m membrane filtration degerming.Put into 37 ℃ of incubator incubations.Measure fluorescent value respectively at incubation the 0th, 7,14,28d, every group is taken out 1ml at every turn and measures from the incubation pipe.With excitation wavelength 370nm, emission wavelength 440nm measures fluorescent value.Deduct for the first time the value of basic fluorescent value gained the time is mapped according to each fluorescent value of surveying, estimate the influence of medicine external albumen nonenzymatic glycosylation with this.Suppress the effect of AGEs formation and estimate, promptly represent with the unit interval pace of change of AGEs fluorescence associated value according to the speed that AGEs forms.
3. experimental result:, estimate the effect that AGEs forms that suppresses according to the speed that AGEs forms by the model that external AGEs forms.Promptly use the unit change speed of AGEs fluorescence associated value, the results are shown in Figure 3, represent.From the unit interval rate of change of AGEs fluorescent value as can be seen: ZL2004 (1mg/ml) has the effect that the external nonenzymatic glycosylation end-product of tangible prevention forms, effect be better than the positive control drug aminoguanidine (AG, 1mg/ml)..
Embodiment 8 ZL2004 are to the inhibitory action of DG Protein kinase C (PKC).
1, reagent: (Promega company) provides by the PKC detection kit, Staurosporine, Sigma company.
2, Protein kinase C half purification: get 200g left and right sides SD rat, sacrificed by decapitation, take out cerebral tissue, wash with PKC extract (4 ℃), filter paper is dried, and the 1g cerebral tissue adds 5ml extract, electronic refiner homogenate (15 seconds * 5 times), the centrifugal 1h of homogenate 105000 * g separates solubility and associativity enzyme, and supernatant is an endochylema Partial Protein kinase c.
3, test method: with reaction system PKC Reaction 5 * Buffer (5 μ l), C1Peptide (0.4g/ μ l) (5 μ l), PKC Activator 5 * Solution (5 μ l), PeptideProtection Solution (optional) (1 μ l) puts into 37 ℃ of incubation casees and reacts 2min.Add medicine and homogenate and 37 ℃ of incubation 30min of PKC (control), 95 ℃ of water are educated the 10min cessation reaction.Sample is put into 4 ℃ of refrigerators, note lucifuge.Sample is mixed 0.8% agarose gel electrophoresis 100V 15 minutes with 1 μ l, 80% glycerol.After seeing the band sharp separation, gel is put under the gel imaging system UV lamp visible clear band.With scalpel glue is downcut, make its volume near 250 μ l as far as possible, put it into a 1.5ml and have in the graduated centrifuge tube, 95 ℃ are heated to peptization and separate.If the not enough 250 μ l of volume of glue, water is supplied.Get the hot agarose of 125 μ l, mix rapid mixing with 75 μ l glue lysates (be preheated to room temperature, and by abundant mixing) and 50 μ l glacial acetic acid.Get 250 μ l and place 96 orifice plates.570nm reads absorbance.Blank group is the liquid agarose.
4. experimental procedure:
(1) the PKC standard substance is used PKC diluted to 2.5 μ g/ml.
(2) warm with PKC Activator 5 * Solution ultrasonic 20-30 second or to liquid.
(3), before application of sample, keep operating on ice carrying out according to following ratio mix reagent and sample in the 0.5mL centrifuge tube.
Positive control
PKC?Reaction?5×Buffer 5μl
C1?Peptide(0.4g/μl) 5μl
PKC Activator 5 * Solution (ultrasonic back) 5 μ l
Peptide Protection Solution (optional) 1 μ l
PKC(2.5μg/ml)
4μl
Add deionized water to 25 μ l
The sample contrast
PKC?Reaction?5×Buffer 5μl
C1?Peptide(0.4g/μl) 5μl
PKC Activator 5 * Solution (ultrasonic back) 5 μ l
Peptide Protection Solution (optional) 1 μ l
Add deionized water to 25 μ l
Negative control
PKC?Reaction?5×Buffer 5μl
C1?Peptide(0.4?g/μl) 5μl
PKC Activator 5 * Solution (ultrasonic back) 5 μ l
Peptide Protection Solution (optional)
1 μ l
Add deionized water to 25 μ l
Standerd?PKC?assay
PKC?Reaction?5×Buffer 5μl
C1?Peptide(0.4g/μl) 5μl
PKC Activator 5 * Solution (ultrasonic back) 5 μ l
Peptide Protection Solution (optional) 1 μ l
ZL2004?(Staurospoine)
4μl
Add deionized water to 25 μ l
(ZL2004 concentration is 1mg/ml, and Staurospoine concentration is 1 * 10
-5Mol/l)
Reaction system is put into 37 ℃ of incubation casees react 2min.Add medicine and homogenate and 37 ℃ of incubation 30min of PKC (control), 95 ℃ of water are educated the 10min cessation reaction.Sample is put into 4 ℃ of refrigerators, note lucifuge.Sample is mixed 0.8% agarose gel electrophoresis 100V 15 minutes with 1 μ l, 80% glycerol.After seeing the band sharp separation, gel is put under the gel imaging system UV lamp visible clear band.With scalpel glue is downcut, make its volume near 250 μ l as far as possible, put it into a 1.5ml and have in the graduated centrifuge tube, 95 ℃ are heated to peptization and separate.If the not enough 250 μ l of volume of glue, water is supplied.Get the hot agarose of 125 μ l, mix rapid mixing with 75 μ l glue lysates (be preheated to room temperature, and by abundant mixing) and 50 μ l glacial acetic acid.Get 250 μ l and place 96 orifice plates.570nm reads absorbance.Blank group is the liquid agarose.
5. result of the test:
PepTag
The C1 peptide is a kind of small peptide that has specific fluorescence, and PKC can make its phosphorylation in the tissue, and the peptide substrate of phosphorylation has negative charge, and unphosphorylated substrate has positive charge, shows as on agarose gel to the two poles of the earth electrophoresis.If a little less than the fluorescence, show that phosphorylated substrate is few in the positive extreme direction, promptly PKC is suppressed, from the visible ZL2004 of Fig. 4 (1mg/ml) to the inhibitory action of the normal PKC of rat cerebral tissue near positive control drug Staurospoine (1 * 10
-5Mol/l).This is the sxemiquantitative experiment.
Claims (10)
1,3,5,7,3 ', 4 ', 5 '-hexahydroxy-2, the application of 3-flavanone in preparation glycation end product inhibitor medicaments.
2, according to claim 13,5,7,3 ', 4 ', 5 '-hexahydroxy-2, the application of 3-flavanone in preparation glycation end product inhibitor medicaments is characterized in that the injection that adopts acceptable accessories to be prepared into.
3, according to claim 13,5,7,3 ', 4 ', 5 '-hexahydroxy-2, the application of 3-flavanone in preparation glycation end product inhibitor medicaments is characterized in that the peroral dosage form that adopts acceptable accessories to be prepared into.
4,3,5,7,3 ', 4 ', 5 '-hexahydroxy-2, the application of 3-flavanone in preparation antioxidant medicine.
5, according to claim 43,5,7,3 ', 4 ', 5 '-hexahydroxy-2, the application of 3-flavanone in preparation glycation end product inhibitor medicaments is characterized in that the injection that adopts acceptable accessories to be prepared into.
6, according to claim 43,5,7,3 ', 4 ', 5 '-hexahydroxy-2, the application of 3-flavanone in preparation glycation end product inhibitor medicaments is characterized in that the peroral dosage form that adopts acceptable accessories to be prepared into.
7,3,5,7,3 ', 4 ', 5 '-hexahydroxy-2, the application of 3-flavanone in preparation DG inhibitors of protein kinase C medicine.
8, according to claim 73,5,7,3 ', 4 ', 5 '-hexahydroxy-2, the application of 3-flavanone in preparation glycation end product inhibitor medicaments is characterized in that the injection that adopts acceptable accessories to be prepared into.
9, according to claim 73,5,7,3 ', 4 ', 5 '-hexahydroxy-2, the application of 3-flavanone in preparation glycation end product inhibitor medicaments is characterized in that the peroral dosage form that adopts acceptable accessories to be prepared into.
10, according to claim 73,5,7,3 ', 4 ', 5 '-hexahydroxy-2, the application of 3-flavanone in preparation glycation end product inhibitor medicaments is characterized in that the targeting preparation that adopts acceptable accessories to be prepared into.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105061533A (en) * | 2015-09-18 | 2015-11-18 | 福州大学 | Hexamethoxyflavanone-rhamnosyl-rhamnoside and application thereof |
| CN114831979A (en) * | 2022-03-27 | 2022-08-02 | 广西大学 | Application of 5-methoxyflavone in preparing medicine for treating obesity, hypercholesterolemia and fatty liver |
-
2006
- 2006-02-21 CN CNA2006100337754A patent/CN1846695A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105061533A (en) * | 2015-09-18 | 2015-11-18 | 福州大学 | Hexamethoxyflavanone-rhamnosyl-rhamnoside and application thereof |
| CN105061533B (en) * | 2015-09-18 | 2018-02-09 | 福州大学 | Hexa methoxy flavanone rhamnopyranosyl rhamnoside and its application |
| CN114831979A (en) * | 2022-03-27 | 2022-08-02 | 广西大学 | Application of 5-methoxyflavone in preparing medicine for treating obesity, hypercholesterolemia and fatty liver |
| CN114831979B (en) * | 2022-03-27 | 2024-01-12 | 广西大学 | Application of 5-methoxy flavone in preparing medicine for treating obesity, high cholesterol and fatty liver |
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