CN102824441B - Method for preparing Fructus Aurantii ingredients having anti-liquid-accumulation activity, and use - Google Patents
Method for preparing Fructus Aurantii ingredients having anti-liquid-accumulation activity, and use Download PDFInfo
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- CN102824441B CN102824441B CN201210302290.6A CN201210302290A CN102824441B CN 102824441 B CN102824441 B CN 102824441B CN 201210302290 A CN201210302290 A CN 201210302290A CN 102824441 B CN102824441 B CN 102824441B
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Abstract
The invention relates to a method for preparing Fructus Aurantii ingredients having anti-liquid-accumulation activity and a use, concretely to a Fructus Aurantii extractive containing 20 to 42 % of naringin and 20 to 48 % of neohesperidin. The Fructus Aurantii extractive is prepared by the following method comprising smashing the Fructus Aurantii medicinal materials, adding 20 to 90 % ethanol, extracting for 1 to 3 times under reflux by heating, combining filtrates to get extracting solutions, condensing the extracting solutions to get extractum, mixing the extractum with macroporous resin, purifying with a macroporous resin column, collecting 60 to 80 % ethanol eluates, condensing, purifying with a polyamide column, collecting 20 % ethanol eluates, condensing and drying to get the Fructus Aurantii ingredients. The Fructus Aurantii extractive can be used for preparing medicaments for treating non-alcoholic fatty liver.
Description
Technical field
The invention belongs to Chemistry for Chinese Traditional Medicine field, relate in particular to a kind of active component extracting and preparation method thereof from Fructus Aurantii, and this component is in the application of preparing in non-alcoholic fatty liver disease medicine.
Background technology
Hepatic injury is the complex process that is caused and had many factors to participate in by Different types of etiopathogenises.The hepatic disease that hepatic injury causes has become commonly encountered diseases, frequently-occurring disease, more seriously liver failure and the hepatic encephalopathy etc. of its initiation, and M & M is high, is greatly threatening human health.Several factors can cause hepatic injury.Non-alcoholic fatty liver disease (nonalcoholic fatty liver disease, NAFLD), claim again non-alcoholic fatty liver disease (nonalcoholic fatty liver, NAFL), be a kind of without excessive drinking history, store up the clinical pathology syndrome as feature take hepatic parenchymal cells steatosis and fat.Non-alcoholic fatty liver disease comprises a series of hepatic disease, from single steatosis to steatosis associating necrosis and fibrosis in various degree.The abnormal accumulation of hepatocyte inner lipid is the pathogenetic main factor of fatty liver disease.Oleic acid is one of fatty acid the abundantest in human body, it participates in forming the triglyceride in liver and promoting the formation that fat drips, oleic acid induction HepG2 accumulation of fat is a kind of conventional lipid accumulation cell model, can be used for evaluating the lipotropism matter cumulative function of medicine.
At present, non-alcoholic fatty liver disease Therapeutic Method has a lot, and all has certain curative effect, but also exists obvious deficiency.First, Western medicine has larger toxic and side effects, and curative effect imprecise.And on the other hand, experiment and clinical research confirmation, Chinese medicine is improving liver function, antioxidation, is improving microcirculation, is regulating the aspects such as immunologic function and anti-hepatic fibrosis to demonstrate good curative effect, safe, reliable and effective, further demonstrate the reasonability of differentiation of tcm, highlighted the good prospect of Chinese medicine aspect treatment title non-alcoholic fatty liver disease.
Fructus Aurantii is to be rutaceae Citrus aurantium Linn.
citrus aurantiumand the dry immature fruit of variety L., its nature and flavor hardship, acid, cold nature, cures mainly septum pectorale feeling of fullness, distending pain over the hypochondrium, accumulation of food in the stomach and intes tine due to indigestion, distension and fullness in the abdomen etc.Modern pharmacology research shows, Fructus Aurantii is two-way function to gastrointestinal smooth muscle, both can excited gastrointestinal smooth muscle, can reduce again gastrointestinal smooth muscular tension; Can prevent rat pylorus ligation ulcer, there is the effect of remarkable minimizing gastric secretion and reduction pepsin activity; There is in addition the coronary flow of increasing and kidney blood flow blood, reduce the effects such as myocardial oxygen consumption.But whether Fructus Aurantii component has the activity of inhibition hepatocyte lipid accumulation it be unclear that.
Summary of the invention
The object of this invention is to provide a kind of Fructus Aurantii active component, this active component mainly contains A naringin, two kinds of compounds of B neohesperidin, and wherein the content of A is 20%-42%, the content of B is 20%-48%.
The content that preferably content of A is 30 ~ 40%, B is 30 ~ 40%.
Another object of the present invention is to provide the preparation method of this Fructus Aurantii active component, realize by following steps: by the ethanol that adds 20% ~ 90% after Fructus Aurantii pulverizing medicinal materials, reflux 0.8 ~ 1.2 hour, extracts 1 ~ 3 time, and merging filtrate obtains extracting solution, extracting solution is condensed into extractum, and itself and macroporous resin are mixed to sample, and by macroporous resin column, it is carried out to purification, collect 70% ethanol elution, after concentrated, after polyamide column purification, collect 20% ethanol elution, after concentrate drying, obtain active component.
A further object of the present invention is to provide this Fructus Aurantii active component in the application of preparing in non-alcoholic fatty liver disease medicine.
Particularly:
First aspect present invention provides a kind of Fructus Aurantii extract (also can be described as in the present invention Fructus Aurantii active component), wherein contain naringin and neohesperidin, and wherein the content of naringin is 20%-42%, and the content of neohesperidin is 20%-48%.In one embodiment, the content of naringin is 30 ~ 40%, and the content of neohesperidin is 30 ~ 40%.In one embodiment, the content of naringin is 25 ~ 35%, and the content of neohesperidin is 20 ~ 30%.
First aspect present invention also provides a kind of Fructus Aurantii extract (also can be described as in the present invention Fructus Aurantii active component), wherein contain naringin and neohesperidin, and wherein contain the naringin of 20-42 weight portion, and content is the neohesperidin of 20-48 weight portion.In one embodiment, in this Fructus Aurantii extract, contain the naringin of 30-40 weight portion, and content is the neohesperidin of 30-40 weight portion.In one embodiment, in this Fructus Aurantii extract, contain the naringin of 25-35 weight portion, and content is the neohesperidin of 20-30 weight portion.
According to the Fructus Aurantii extract of first aspect present invention, it prepares by the following method: will after Fructus Aurantii pulverizing medicinal materials, add 20% ~ 90% (for example 60-80%, for example 65-75%) ethanol, heating and refluxing extraction 1 ~ 3 time, merging filtrate obtains extracting solution, extracting solution is condensed into extractum, and itself and macroporous resin are mixed to sample, by macroporous resin column, it is carried out to purification, collect 60 ~ 80% ethanol elution, concentrated, through polyamide column purification, collect 20% ethanol elution, through concentrate drying, to obtain final product.
According to the Fructus Aurantii extract of first aspect present invention, it prepares by the following method: 1500g Fructus Aurantii is added to 4200ml 70% ethanol extraction 2h, then add 3500ml 70% ethanol extraction 1.5h, finally add 2800ml 70% ethanol extraction 1h, merge three times extracting solution, concentrated after sucking filtration.Concentrated solution is crossed macroporous resin (D101), after first washing with water, then uses 20% ethanol elution, finally with 70% ethanol elution.Collect 70% ethanol elution, be concentrated into 150ml left and right, sucking filtration, crosses polyamide column, with 4 column volumes of 20% ethanol elution, collects eluent; Use again 5 column volumes of 40% ethanol elution, point 10 sections of collection eluents, every section of 500ml.20% ethanol elution section is revolved to steaming, after lyophilization, weigh, to obtain final product.
Second aspect present invention provides the method for preparing Fructus Aurantii extract, it comprises the following steps: will after Fructus Aurantii pulverizing medicinal materials, add 20% ~ 90% (for example 60-80%, for example 65-75%) ethanol, heating and refluxing extraction 1 ~ 3 time, merging filtrate obtains extracting solution, extracting solution is condensed into extractum, and itself and macroporous resin are mixed to sample, by macroporous resin column, it is carried out to purification, collect 60 ~ 80% ethanol elution, concentrated, through polyamide column purification, collect 20% ethanol elution, through concentrate drying, to obtain final product.
According to the method for second aspect present invention, it comprises the following steps: 1500g Fructus Aurantii is added to 4200ml 70% ethanol extraction 2h, then add 3500ml 70% ethanol extraction 1.5h, finally add 2800ml 70% ethanol extraction 1h, merge three times extracting solution, and concentrated after sucking filtration.Concentrated solution is crossed macroporous resin (D101), after first washing with water, then uses 20% ethanol elution, finally with 70% ethanol elution.Collect 70% ethanol elution, be concentrated into 150ml left and right, sucking filtration, crosses polyamide column, with 4 column volumes of 20% ethanol elution, collects eluent; Use again 5 column volumes of 40% ethanol elution, point 10 sections of collection eluents, every section of 500ml.20% ethanol elution section is revolved to steaming, after lyophilization, weigh, to obtain final product.
According to the method for second aspect present invention, in its gained Fructus Aurantii extract, contain naringin and neohesperidin, and wherein the content of naringin is 20%-42%, the content of neohesperidin is 20%-48%.In one embodiment, the content of naringin is 30 ~ 40%, and the content of neohesperidin is 30 ~ 40%.In one embodiment, the content of naringin is 25 ~ 35%, and the content of neohesperidin is 20 ~ 30%.
According to the method for second aspect present invention, in its gained Fructus Aurantii extract, contain naringin and neohesperidin, and wherein contain the naringin of 20-42 weight portion, and content is the neohesperidin of 20-48 weight portion.In one embodiment, in this Fructus Aurantii extract, contain the naringin of 30-40 weight portion, and content is the neohesperidin of 30-40 weight portion.In one embodiment, in this Fructus Aurantii extract, contain the naringin of 25-35 weight portion, and content is the neohesperidin of 20-30 weight portion.
Third aspect present invention provides the Fructus Aurantii extract of first aspect present invention in the application of preparing in non-alcoholic fatty liver disease medicine.
Fourth aspect present invention provides a kind of pharmaceutical composition, comprising Fructus Aurantii extract and pharmaceutically acceptable carrier or the excipient of first aspect present invention.
Fructus Aurantii active component of the present invention can be used as active site, adds drug excipient or the carrier on pharmaceutics, accepted, makes preparation according to the method for recording on pharmaceutics.
The dosage form of described medicine comprises liquid preparation, solid preparation, capsule, soft gelatin capsule.Comprise injection, drip liquid, injectable powder, granule, tablet, electuary, powder, oral liquid, sugar coated tablet, film coated tablet, enteric coated tablet, capsule, hard capsule, soft capsule, suck agent, granule, pill, unguentum, sublimed preparation, spray, drop pill, disintegrating agent, oral cavity disintegration tablet, micropill etc.
In the present invention, term " Fructus Aurantii component " can be described as " Fructus Aurantii extract " or " Fructus Aurantii active component " etc., and these terms can exchange use.
Beneficial effect of the present invention is:
1. extraction and separation process of the present invention is simple, can obtain rapidly and accurately active component.
2. Fructus Aurantii active component chemical composition provided by the invention is simply clear and definite, is easier to illustrate its mechanism of action on pharmacological research, is easier to aborning the quality control of medicine.
3. the present invention is first at oleic acid induction HepG
2on accumulation of fat model, evaluate Fructus Aurantii extract antagonism lipid accumulation effect for reducing fat, obtained good pharmacologically active.
Accompanying drawing explanation
Fig. 1 is the HPLC analysis chart of Fructus Aurantii extract of the present invention.
Fig. 2 has shown the impact of the HepG2 cytolipin accumulation of variable concentrations Fructus Aurantii extract on the induction of 500uM oleic acid.
Fig. 3 has described the impact of variable concentrations naringin and the HepG2 cytolipin accumulation of neohesperidin on the induction of 500uM oleic acid.
The specific embodiment
The present invention by reference to the accompanying drawings and below embodiment further describes flesh and blood of the present invention, and this embodiment is the limitation of the present invention not for the present invention is described only.
The preparation of embodiment mono-Fructus Aurantii active component
1500g Fructus Aurantii is added to 4200ml 70% ethanol extraction 2h, then add 3500ml 70% ethanol extraction 1.5h, finally add 2800ml 70% ethanol extraction 1h, merge three times extracting solution, concentrated after sucking filtration.Concentrated solution is crossed macroporous resin (D101), after first washing with water, then uses 20% ethanol elution, finally with 70% ethanol elution.Collect 70% ethanol elution, be concentrated into 150ml left and right, sucking filtration, crosses polyamide column, with 4 column volumes of 20% ethanol elution, collects eluent; Use again 5 column volumes of 40% ethanol elution, point 10 sections of collection eluents, every section of 500ml.20% ethanol elution section is revolved to steaming, after lyophilization, weigh, obtain Fructus Aurantii component 47.5608g.It is for biological test below.
The analysis of embodiment bis-Fructus Aurantii active components
chromatographic conditionagilent 1100 type high performance liquid chromatographs, chromatographic column is SB-C
18chromatographic column; Take acetonitrile-water (20:80) (with phosphorus acid for adjusting pH value to 3) as mobile phase; Detection wavelength is 283nm; Liquid chromatograph flow velocity is 1ml/min, sample size 10 μ l.
the preparation of need testing solutiontake this product, in volumetric flask, be diluted to 2mg/ml with dissolve with methanol solution, shake up, to obtain final product.
assay methodthe accurate need testing solution of drawing, injection liquid chromatography, measures according to chromatographiccondition, to obtain final product.
analysis resultthe efficient liquid phase chromatographic analysis spectrogram of Fructus Aurantii active component is shown in Fig. 1, and in two figure, to be respectively the chromatographic peak of 16min and 11.5min be respectively A, two compounds of B to retention time.Use identical chromatographic conditions, analyzed naringin and neohesperidin standard substance, find that compd A is identical with naringin retention time, find that compound is identical with neohesperidin retention time, so authenticating compound A and B are respectively naringin and neohesperidin.Assay result shows, naringin and neohesperidin content in extract is respectively 31.2% and 25.8%.Have been surprisingly found that, in embodiment 1, if by concentration lower than 60% ethanol extraction, or by concentration higher than 80% ethanol extraction, or the macroporous resin of using other model instead carries out eluting, compd A and B acquisition amount are measured more than low 33% and 30% than the acquisition of embodiment 1 respectively.While preparation with 65-75% ethanol and with D101 macroporous resin, compd A and B acquisition amount be embodiment 1 acquisition amount 93% ~ 115%, and in extract, the content of compd A is between 25-35%, the content of compd B is between 20-30%.
Embodiment tri-Fructus Aurantii active component preparations
The Fructus Aurantii active component 0.5g that gets embodiment 1 gained is mixed homogeneously with 10.5g PEG-4000, and heating and melting moves to after material in drop pill drip irrigation, and medicinal liquid drops in 6 ~ 8 ℃ of liquid paraffin, and oil removing makes 400 of drop pill.
Embodiment tetra-Fructus Aurantii active component preparations
Get the Fructus Aurantii active component 0.5g of embodiment 1 gained, wear into fine powder, mix with approximately 1/3 starch, add starch slurry and mix and make soft material, 16 mesh sieves are granulated, 70 ℃ dry, dry granular is crossed 14 mesh sieve granulate, and adding remaining starch (dry at 100-105 ℃ in advance) has the Pulvis Talci (mixing during light liquid petrolatum is sprayed on to Pulvis Talci) of liquid Paraffin with absorption, then passes through 14 mesh sieves, tabletting, obtains embodiment five Fructus Aurantii active component lipotropism matter cumulated activity evaluations
Molten component to be measured, in DMSO, obtains 50 mgmL-1 storing solutions, and the final concentration of hatching with cell is 50 μ gmL-1, at the HepG of oleic acid induction
2it suppresses lipid accumulation activity hepatocyte model evaluation.
Well-grown HepG2 cell is inoculated in 24 porocyte culture plates to every hole culture fluid 1ml with the density of every hole 200,000 cells.After cell attachment (approximately 24 hours), divide matched group and the processing of administration group, parallel three experiments, add 0.5mM oleic acid in matched group, in administration group, add 0.5mM oleic acid and 75,100,150,200 ug/ml embodiment 1 gained Fructus Aurantii extracts, in 37 ℃, 5%CO
2condition under cultivate after 24h, discard every hole supernatant, enzymatic assays triglyceride, total cholesterol level.Assay method is that 24 porocyte culture plate pre-cooling PBS500ul wash twice, every hole adds 200ul cell pyrolysis liquid cracking 30min, get the total liquid of cracking in 1.5ml centrifuge tube, centrifugal 10min(12000rpm, 4 ℃), getting respectively supernatant 80ul adds the agent of 100ul triglyceride enzyme and surveys every hole triglyceride (TG) content, 80ul adds the agent of 100ul cholesterol enzyme and surveys every hole cholesterol (TC) content, 10ul surveys protein content by BCA method, calculates TG and the TC content (ug/mg protein) of Mei Kong unit's albumen.
Result shows, embodiment 1 gained Fructus Aurantii extract is at 50ug/ml, and 100ug/ml, has the effect of triglyceride accumulation in obvious inhibition oleic acid induction HepG2 cell, and be dose-effect relationship under 200ug/ml concentration.Specifically see Fig. 2, it has described the impact of the HepG2 cytolipin accumulation of variable concentrations Fructus Aurantii extract on the induction of 500uM oleic acid, and wherein vertical coordinate represents that the % " Fructus Aurantii flavone " of contrast is Fructus Aurantii extract of the present invention.
In embodiment six Fructus Aurantii components, the lipotropism matter cumulated activity of main component is evaluated
Main component naringin and neohesperidin in Fructus Aurantii component are mixed with to 10,25,50,100,150,200 μ molL
-1solution, at the HepG of oleic acid induction
2it suppresses lipid accumulation activity hepatocyte model evaluation.Result shows, neohesperidin is at concentration 100u μ molL
-1when above, there is obvious inhibition oleic acid induction HepG
2the effect of cell TG and TC accumulation, and be certain concentration dependent; Naringin is 200 μ molL in concentration
-1time have an effect of obvious inhibition oleic acid induction HepG2 cell TG and TC accumulation.Specifically see Fig. 3, it has described the impact of variable concentrations naringin and the HepG2 cytolipin accumulation of neohesperidin on the induction of 500uM oleic acid, and wherein vertical coordinate represents the % of contrast.
Claims (5)
1. Fructus Aurantii extract is in the application of preparing in non-alcoholic fatty liver disease medicine, in described Fructus Aurantii extract, contain naringin and neohesperidin, and wherein the content of naringin is 20%-42%, the content of neohesperidin is 20%-48%, and described Fructus Aurantii extract prepares by the following method: 1500g Fructus Aurantii is added to 4200ml70% ethanol extraction 2h, then add 3500ml70% ethanol extraction 1.5h, finally add 2800ml70% ethanol extraction 1h, merge three times extracting solution, concentrated after sucking filtration; Concentrated solution is crossed D101 macroporous resin, after first washing with water, then uses 20% ethanol elution, finally with 70% ethanol elution; Collect 70% ethanol elution, be concentrated into 150ml left and right, sucking filtration, crosses polyamide column, with 4 column volumes of 20% ethanol elution, collects eluent; Use again 5 column volumes of 40% ethanol elution, point 10 sections of collection eluents, every section of 500ml; 20% ethanol elution section is revolved to steaming, after lyophilization, weigh, to obtain final product.
2. according to the purposes of claim 1, wherein the content of naringin is 30%-40%, and the content of neohesperidin is 30%-40%.
3. the method for the Fructus Aurantii extract for the treatment of for the preparation of non-alcoholic fatty liver disease, it comprises the following steps: 1500g Fructus Aurantii is added to 4200ml70% ethanol extraction 2h, then add 3500ml70% ethanol extraction 1.5h, finally add 2800ml70% ethanol extraction 1h, merge three times extracting solution, concentrated after sucking filtration; Concentrated solution is crossed D101 macroporous resin, after first washing with water, then uses 20% ethanol elution, finally with 70% ethanol elution; Collect 70% ethanol elution, be concentrated into 150ml left and right, sucking filtration, crosses polyamide column, with 4 column volumes of 20% ethanol elution, collects eluent; Use again 5 column volumes of 40% ethanol elution, point 10 sections of collection eluents, every section of 500ml; 20% ethanol elution section is revolved to steaming, after lyophilization, weigh, to obtain final product.
4. according to the method for claim 3, in its gained Fructus Aurantii extract, contain naringin and neohesperidin, and wherein the content of naringin is 20%-42%, the content of neohesperidin is 20%-48%.
5. according to the method for claim 3, in its gained Fructus Aurantii extract, contain naringin and neohesperidin, and wherein the content of naringin is 30%-40%, the content of neohesperidin is 30%-40%.
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