CN101590008A - A kind of composite preparation and purifying process of 24-methylene basic ring jackfruit alcohol ferulic acid ester - Google Patents
A kind of composite preparation and purifying process of 24-methylene basic ring jackfruit alcohol ferulic acid ester Download PDFInfo
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- CN101590008A CN101590008A CN 200810113430 CN200810113430A CN101590008A CN 101590008 A CN101590008 A CN 101590008A CN 200810113430 CN200810113430 CN 200810113430 CN 200810113430 A CN200810113430 A CN 200810113430A CN 101590008 A CN101590008 A CN 101590008A
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- acid ester
- ferulic acid
- basic ring
- oryzanol
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Abstract
The invention discloses a kind of 24-methylene basic ring jackfruit alcohol ferulic acid ester compositions and preparation, with 24-methylene basic ring jackfruit alcohol ferulic acid ester method of purification, the 24-methylene basic ring jackfruit alcohol ferulic acid ester purity of using this method of purification can reach more than 80%.Compositions disclosed by the invention contains 24-methylene basic ring jackfruit alcohol ferulic acid ester and surfactant, and surfactant wherein is selected from Tween 80, PEG400 or its mixture.The invention also discloses the injection of compositions simultaneously, especially freeze-dried powder injection.
Description
Technical field
The invention discloses purifying technique and its preparation of a kind of 24-methylene basic ring jackfruit alcohol ferulic acid ester, further the invention discloses a kind of technology of using recrystallization technology purification cycloartenyl ferulate from the oryzanol raw material.
Background technology
Along with the rhythm of modern society's live and work is accelerated gradually, modern's sub-health state allows of no optimist.Suffer from autonomic nerve disorder, climacteric syndrome, primary dysmenorrhea, premenstrual tension syndrome etc. according to statistics because the vegetative nerve malfunction causes sympathetic nerve and parasympathetic nervous disequilibrium, the sickness rate of non-organic disease is the trend that rises year by year.
Autonomic nerve disorder causes by psychic trauma and long-term nervous, fatigue usually, causes corticocerebral miopragia, causes that transition is excited and tired out and fall ill rapidly.That climacteric syndrome is meant more is female in the body behind the postmenopausal women, progesterone level reduces cardiovascular, nerve, the hormonal system dysfunction that causes, causes symptom such as dysfunctional uterine hemorrhage, paroxysmal hectic fever and perspiration, pudendum and vaginal atrophy, osteoporosis and personality to change.Primary dysmenorrhea in the middle of being in a bad way but still adhering to the patient of work, causes production capacity to descend owing to its high incidence causes people's attention easily, and possibility of accident occurrence rises, degradation under the work quality.Send out the property dysmenorrhea and refer to that the genitals does not have organic disease, before and after passing through or stomachache, the soreness of waist, lower abdomen between menstrual period, occur and weigh down and expand or other are uncomfortable, influence live and work.In good 6 months～2 years of sending out after 15～25 years old and menophania.Premenstrual tension syndrome is meant that it is the clinical syndrome of main clinical manifestation with the anxiety for one group that the women produces premenstruum such as agitation, irritability, headache, insomnia, distending pain of the breast, abdominal distention etc.Premenstrual tension incidence rate height, performance is complicated, directly influences numerous women's physical and mental health.
Oryzanol is one of active drug that is used for the treatment of at present above-mentioned disease, and oryzanol has the serum cholesterol of reduction activity, also has the prevention lipid peroxidation.In opacifier, make antioxidant, in cosmetics, to make antiseptic, be used for the treatment of dermatitis, senile skin xerosis and prevent xerosis cutis. the safety evaluation oryzanol does not have heredity damage and carcinogenic activity. and have blood fat reducing simultaneously, reduce the liver lipid, prevent different physiological roles such as lipid oxidation, antioxidation.Mostly existing oryzanol medicine is to obtain from preliminary purifications such as Testa oryzaes, generally contains multiple ferulic acid esters material in the component.
Because of the oryzanol complicated component, include multiple sterols ferulic acid ester and triterpene alcohols ferulic acid ester, so the purification of oryzanol composition produces to the oryzanol related drugs, the medicine quality control has great significance.Existing oryzanol medicine mostly is to make medicament by purification from Testa oryzae oil on the market, and the purification extraction at the oryzanol one-component does not at present still have document and the open report of research.
European patent application EP 503650 discloses a kind of method by hydrolysis gamma oryzanol acquisition ferulic acid esters material, but this method cost is higher, and on the low side to the utilization rate of oryzanol simultaneously, yield is only about 22%.
Application number is that 971961328 Chinese patent application discloses a kind of method of obtaining the oryzanol concentrate from the oryzanol fatty material, utilize this method can obtain the concentrate of 60%-90%, but do not relate to the problem that the further separation and purification of highly purified oryzanol obtains one-component.
Application number is that 02135610.6 Chinese patent application discloses a kind of the purification with solvent extraction and obtains the method for 60-70% purity oryzanol, and it is on the low side that the oryzanol that is obtained is used for pharmaceutical purity, do not have further to study the extraction of separate constituent.
Document " research of Testa oryzae function factor gamma-Hi-Z " (Chinese grain and oil journal 2000,15 (6): 14-18) studied the method for utilizing simple high performance liquid chromatography purification oryzanol to obtain cycloartenyl ferulate, its weak point is to utilize simple high-efficient liquid phase technique cost higher, this method can be used in laboratory or small lot sample production analysis environments, but is not suitable for carrying out technical scale production.
Document " method of extraction oryzanol from Testa oryzae oil and vegetable fatty acid derivative thereof " (japanese food science and technology, 1986,23:270-27) reported a kind of four methods, comprise liquid-liquid extraction, column chromatography, crystallization and recrystallize extract oryzanol from rice bran oil soapstock.But the author does not illustrate last oryzanol purity and productive rate.When this process limitation is liquid-liquid extraction, must carry out re-extract, increase extraction process quantity, reduce the oryzanol productive rate, the document is not discussed the problem of purification oryzanol one-component 24-methylene basic ring jackfruit alcohol ferulic acid ester simultaneously.
Document " Testa oryzae oryzanol method for extraction and purification progress " (grain and oils and fats, 2007.11,1-5) analysis-by-synthesis the technical scheme of oryzanol of from raw materials such as Testa oryzae, producing now commonly used, but not have further to study with regard to the purifying technique of the pure ferulic acid ester of 24-methylene basic ring jackfruit.
Summary of the invention
The present invention has overcome present technical field and has deposited the problem that can't obtain high-purity 24-methylene basic ring jackfruit alcohol ferulic acid ester component and its actual medicinal grade in the oryzanol, uses process such as recrystallization to overcome the expensive cost that simple high performance liquid chromatogram prepares high-purity 24-methylene basic ring jackfruit alcohol ferulic acid ester.Disclosed technology is with the oryzanol medicine material of working standard, by modern separation and purification means, remove the composition of the non-24-methylene basic ring jackfruit alcohol ferulic acid ester in most of oryzanol raw material, the percentage composition that makes 24-methylene basic ring jackfruit alcohol ferulic acid ester is brought up to more than 80% by original 40% and (is contained 80%), and it is prepared into suitable dosage form.
When improving large-scale production process, except that separation efficiency (purity and product yield), mainly consider productibility (time, energy and demand of human resources), environment and healthy relevant issues, unit operations/process investment (equipment and solvent recovery).Technology disclosed in this invention has satisfied above requirement.And, adopt preparation method of the present invention, productive rate height (about 1%), cost is low, has extremely wide application prospect.
The structure of 24-methylene basic ring jackfruit alcohol ferulic acid ester is as follows:
The invention provides a kind of preparation method of 24-methylene basic ring jackfruit alcohol ferulic acid ester, may further comprise the steps: get commercially available oryzanol sample,, leave standstill and separate out crystallization, filter drying with the purification solution dissolving.Purification solution wherein is selected from ethyl acetate, interior ketone, methanol, ethanol, n-butyl alcohol.
Further, preparation method of the present invention may further comprise the steps: get 24-methylene basic ring jackfruit alcohol ferulic acid ester content greater than 70% oryzanol, with the purification solution dissolving, leave standstill and separate out crystallization, filter drying.Repeat above recrystallization process 1-20 time.Wherein, purification solution is selected from ethyl acetate or acetone; Preferred 2-10 time of the number of repetition of recrystallization process.
Preferably, the addition of purification solution is 1-30 a times of solute, and preferred 5-20 times, most preferably 5-10 doubly.
Adopt the 24-methylene basic ring jackfruit alcohol ferulic acid ester of above preparation method preparation, its purity is preferably greater than 90% greater than 80%.
Contrast by the percentage composition of chromatography the 24-methylene cycloartenyl ferulate of commercially available oryzanol medicine material and the present invention's acquisition.
The percentage composition contrast of the 24-methylene cycloartenyl ferulate that the commercially available oryzanol medicine material of table 1 and the present invention obtain
Show by above-mentioned test data, technology of the present invention has obtained better controlled from purity, make the main component in the oryzanol raw material: the content of 24-methylene basic ring jackfruit alcohol ferulic acid ester can be controlled accurately, and pharmacological research, preparation research and the quality research in future laid a good foundation.
A large number of experiments show that the present invention is owing to contain highly purified 24-methylene basic ring jackfruit alcohol ferulic acid ester, it has more advantage than the miscellaneous oryzanol of multiple composition aspect active.
On the other hand, the present invention also provides a kind of pharmaceutical preparation, contains 24-methylene basic ring jackfruit alcohol ferulic acid ester and pharmaceutically acceptable carrier, and wherein the purity of 24-methylene basic ring jackfruit alcohol ferulic acid ester is more than 80%, and is preferred more than 90%.Pharmaceutical preparation of the present invention can be oral formulations or injections such as tablet, capsule, powder, granule, pill, is the preparation that the injection for intravenous of non-oily solvent is used especially.
Vein of the present invention contains 24-methylene basic ring jackfruit alcohol ferulic acid ester and surfactant with injection, described surfactant can be anion, cation or non-ionic surface active agent, include but not limited to the polyoxyethylene sorbitan ester class, for example, polyoxyethylene sorbitan fatty acid ester, Polyethylene Glycol, sodium lauryl sulphate, dodecyl sodium sulfate, lithium dodecyl sulfate, chenodeoxycholic acid, NaTDC, Sodium glycodeoxycholate., N-lauryl sarcosine, cetylpyridinium chloride, phospholipid.Preferred surfactants is tween, Polyethylene Glycol or its mixture.Tween wherein can be a polysorbas20,40,60,80; Polyethylene Glycol can be a Macrogol 200,400,600,800,1000,2000,4000,8000 or its mixture, preferred Macrogol 200,400,800 or its mixture; Most preferably be Tween 80, PEG400 or its mixture.
Injection of the present invention also can randomly further comprise other acceptable accessories such as excipient, antioxidant, PH regulator, antiseptic, isotonic agent.Wherein can be selected from but to be not limited to be in mannitol, lactose, glucose, sorbitol, sodium chloride, gelatin hydrolysate, dextran, sucrose, glycine, the polyvinylpyrrolidone etc. one or more to excipient; Be preferably mannitol or glucose.Antiseptic can be selected from but be not limited to is in phenol, cresol, three tert-butyl alcohols, benzyl alcohol, the nipalgin one or more.Stabilizing agent can be selected from but be not limited in sodium sulfite, sodium sulfite, sodium pyrosulfite, sodium thiosulfate, thiourea, vitamin C, butylated hydroxyarisol, dibutyl phenol, propyl gallate, tocopherol, ascorbyl palmitate, ethylenediaminetetraacetic acid, the disodiumedetate one or more.PH regulator PH regulator can be the acceptable organic acid of pharmacy, organic base, mineral acid, inorganic base, include but not limited to hydrochloric acid, citric acid, tartaric acid, phosphoric acid, Metaphosphoric acid, poly-Metaphosphoric acid, carbonic acid, sulphuric acid, nitric acid, acetic acid, sodium hydroxide, potassium hydroxide, sodium citrate, potassium citrate, sodium bicarbonate, potassium bicarbonate, amine carbonate, sodium hydrogen phosphate, dipotassium hydrogen phosphate, ethanolamine, diethanolamine, triethanolamine, 1, one or more in 2-hexamethylene diamine, sodium carbonate, potassium sodium tartrate, potassium metaphosphate, Kurrol's salt, the Polymeric sodium metaphosphate..
The injection that provides of the present invention can be water soluble parenteral solution, transfusion, lyophilized injectable powder, preferred water soluble parenteral solution and lyophilized injectable powder, most preferably lyophilized injectable powder.
Injection of the present invention can adopt all attainable injection preparation methoies of this area to prepare.
According to the difference of finally utilizing purposes, the crystal that the present invention obtained can be used for preparing the medicine for the treatment of disease, perhaps is used for function food additive, and consumption and quality are decided according to concrete purposes.
Embodiment 1
Get oryzanol 1kg, with 8kg left and right sides acetone heating for dissolving, room temperature leaves standstill separates out crystallization, filters drying.Again exsiccant crystallization is repeated above process 10 times.The content that gets 24-methylene basic ring jackfruit alcohol ferulic acid ester reaches more than 99%.
Embodiment 2
1. chromatographic condition and system suitability test: with the octadecylsilane chemically bonded silica is filler; Methanol-acetonitrile (40: 60) is a mobile phase; Flow velocity is 1.5ml/min; The detection wavelength is 327nm; Sensitivity is 0.005AUFS.Theoretical cam curve should be not less than 2000 by calculating.
2. need testing solution preparation: precision takes by weighing commercially available oryzanol raw material, each 10mg of the present invention, to the 10ml measuring bottle, is dissolved in water and standardize solution, shakes up, and is need testing solution.
3. measure: the accurate need testing solution 10 μ l that draw, inject chromatograph of liquid, write down chromatogram, check the percentage composition of each component with area normalization method.
4. measurement result
Table 2 measurement result
The very effective 24-methylene cycloartenyl ferulate content that improved of technology of the present invention is described
Embodiment 3
Prescription
1000 bottles of injection freeze-dried powders of the present invention (containing 18mg/ bottle of the present invention):
The present invention product 18g that purifies
PEG400 250g
Tween 80 250g
10% mannitol 6000g
Water for injection adds to 5000ml
Be lyophilized into 1000 altogether
Be principal agent with raw material of the present invention in the prescription, Tween 80 is solubilizing agent, and PEG400 is a cosolvent, and mannitol is proppant, and water for injection is freezing solvent.
The preparation process
The present invention who takes by weighing recipe quantity water for injection of product, tween 80, PEG-400, mannitol and 80% recipe quantity of purifying, stirring makes it to be dissolved to the solution clarification, stirring at room 20 minutes, with 0.45 μ m microporous filter membrane coarse filtration, filtrate adds to the full amount of water for injection, reuse 0.22 μ m microporous filter membrane aseptic filtration.Gained filtrate is carried out visible foreign matters, pH and content check.
Import cillin bottle, plug and fine straining liquid after cleaning, sterilizing into bottling department, determine that according to content the packing volume carries out fill false add plug simultaneously.
The cillin bottle that branch the is installed sample lyophilizing dish of packing into is put into freeze drying box, lyophilizing, and lyophilizing finishes, and plug is pressed in the cillin bottle fully, and logical at last atmosphere takes out freeze dried sample.Promptly get injection freeze-dried powder of the present invention.
Embodiment 4
Raw material of the present invention merges the influence that chronic stress causes the mice climacteric syndrome to castration
96 of female ICR mices, be divided into 19 cages at random by body weight, every cage 5-6 only, take out 10 at random as sham operated rats, all the other 86 mices are all as animal pattern, and mouse peritoneal is anaesthetized, and (sham operated rats is only cut to remove bilateral ovaries, do not remove ovary), sew up back benzylpenicillin sodium for injection infection 4d.Postoperative the 4th day beginning give in the following order the chronic imprevision of mice stress, (1) foot-shock: the 36V alternating current, stimulate once every 1min, continue 10s, totally 15 times; (2) frozen water swimming: 4 ℃, 5min; (3) thermostimulation: 45 ℃, 5min; (4) rock: 140 times/min, 1.5hr; (5) folder tail: apart from the 1cm of root of the tail place, 1min; (6) prohibit water: 24hr; (7) fasting: 24hr; (8) put upside down round the clock: 24hr; Every kind stimulates 3 times.Model mice is divided into 7 groups (10 every group) at random behind the chronic stress: 1. model group, 2. nilestriol group (0.25mg/kg/d), raw material I group 3. of the present invention (25mg/kg); 4. raw material II group of the present invention (50mg/kg); 5. raw material II I group of the present invention (100mg/kg); 6.; Oryzanol group (100mg/kg); 7. oryzanol group (200mg/kg).
Press 20ml/kg volume gastric infusion every day twice (sham operated rats and model group only give solvent), continuously 16d.Behind the last administration 45min, mouse orbit is got blood, and separation of serum is measured E2, FSH; Rapidly broken end is got brain afterwards, gets the uterus, the adrenal gland weighs, and calculates organ index.The result carries out statistical procedures (t check).
The result: after the modeling, model group uterus index significantly reduces (P＜0.01); Compare with model group, positive drug nilestriol and oryzanol (200mg/kg/d) group uterus weight and index be obviously rising (P＜0.01) all, after the filling stomach gives raw material of the present invention, high dose group (100mg/kg/d) and middle dosage group (50mg/kg/d) uterus index significantly raise (P＜0.01), see table 3 for details.
Table 3 pair climacteric model mice uterus, the exponential influence of adrenal gland (X ± SD)
Compare with model group:
*P＜0.05,
*P＜0.01; Compare with sham operated rats:
△P＜0.05,
△ △P＜0.01.
Embodiment 7
Get the commercially available molten injection of oryzanol oil and carry out irritation test, the result shows injection site and slight red and swollen, the appearance scleroma of surrounding tissue thereof, tissue slice is checked the visible vessels expansion obviously, pipe has inflammatory exudate in week, shows that the molten injection of oryzanol oil produces tangible stimulation to intramuscular injection site under experiment condition.
The freeze-dried powder that embodiment 2 makes carries out the zest of animal blood vessels.Get 6 of health, ear edge not damaged rabbit, be divided into two groups at random by body weight, i.e. test group and sodium chloride injection matched group.Absorb with oryzanol oil with clinical adult that to penetrate the liquor amount serve as according to design rabbit dosage, slowly inject administration from rabbit left side auricular vein, matched group gives the isometric(al) sodium chloride injection, gives 5 days continuously.Result of the test shows, compare with the sodium chloride injection group, the intravenous injection freeze-dried powder of feedstock production of the present invention, reach the last administration during the administration after 24 hours, blood vessel and surrounding tissue redness are not seen in perusal, the visible rabbit ear vein clear in structure of tissue slice inspection, indivedual vasodilation are obvious, the tube wall thickness is even, and inwall is level and smooth, the Guan Zhouwu inflammatory exudate.Show that the freeze-dried powder with feedstock production of the present invention does not have the obvious stimulation effect to the rabbit auricular vein under the experiment condition.
Claims (13)
1. the pharmaceutical composition of an injection contains 24-methylene basic ring jackfruit alcohol ferulic acid ester and surfactant.
2. according to the pharmaceutical composition of claim 1, surfactant wherein is selected from tween, Polyethylene Glycol or its mixture.
3. according to the pharmaceutical composition of claim 1 or 2, wherein the purity of 24-methylene basic ring jackfruit alcohol ferulic acid ester is greater than 80%.
4. according to the pharmaceutical composition of each claim among the claim 1-3, surfactant wherein is selected from Tween 80, PEG400 or its mixture.
5. the method for a purification 24-methylene basic ring jackfruit alcohol ferulic acid ester from oryzanol is characterized in that comprising crude product is dissolved with purification solution that leave standstill and separate out crystalline step, purification solution wherein is selected from acetone or ethyl acetate.
6. according to the method for claim 5, purification solution wherein is an ethyl acetate.
7. according to the method for claim 5, purification solution wherein is an acetone.
8. according to the method for each claim among the claim 5-7, comprising crystallization is filtered, exsiccant step.
9. method according to Claim 8 comprises the crystallization in the claim 8, filtration, exsiccant step is repeated 1-20 time.
10. according to the method for claim 9, the wherein crystallization in the claim 8, filtration, exsiccant step repeat 1-10 time.
11. according to each method among the claim 4-10, the addition of purification solution be solute 1-30 doubly.
12. according to the method for claim 11, the addition of purification solution is 5-20 a times of solute.
13. according to the method for claim 12, the addition of purification solution is 5-10 a times of solute.
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| CN102125565A (en) * | 2011-01-11 | 2011-07-20 | 北京世纪博康医药科技有限公司 | Medicinal composition of 24-methylene cycloartenyl ferulate |
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| CN100386082C (en) * | 2005-12-22 | 2008-05-07 | 济南百诺医药科技开发有限公司 | Oryzanol composition and its preparation method |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102125565A (en) * | 2011-01-11 | 2011-07-20 | 北京世纪博康医药科技有限公司 | Medicinal composition of 24-methylene cycloartenyl ferulate |
| CN102125565B (en) * | 2011-01-11 | 2014-08-27 | 北京世纪博康医药科技有限公司 | Medicinal composition of 24-methylene cycloartenyl ferulate |
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