CN1672678A - Separation and extraction of natural active long-chain fatty acid component for preventing and treating prostatosis and the prepn and application of its medicine prepn - Google Patents
Separation and extraction of natural active long-chain fatty acid component for preventing and treating prostatosis and the prepn and application of its medicine prepn Download PDFInfo
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Abstract
The present invention is separation and extraction of natural active long-chain fatty acid component for preventing and treating prostatosis and the preparation and application of its medicine preparation. The medicine preparation has the active component with chemical structure expression as shown, and consists of the long-chain derivative as active component and medicine carrier or diluent. The medicine preparation may be tablet, capsule, liquid preparation, granule, etc. and is used in preventing and treating prostate proliferation, prostatitis and prostate tumor. The preparation process includes crushing plant material, extraction with solvent, defatting of the extract with organic solvent, extraction of the residue with solvent, chromatographic separation and purification.
Description
Technical field
The present invention relates to have the extraction preparation and the clinical practice aspect the treatment prostatosis thereof of the long-chain fat acid derivative of therapeutical effect.
Background technology
Modal prostatosis comprises carcinoma of prostate and prostatic hyperplasia.Carcinoma of prostate is one of modal cancer of male.U.S.'s cancer in 1997 statistics shows that in male tumor, carcinoma of prostate occupies first of the sickness rate, accounts for 41%, occupies second of cancer mortality, accounts for that the male becomes celestial the carcinoma of prostate incidence rate up to 30% more than 14%, 50 years old.In China, from the seventies carcinoma of prostate sickness rate significantly rise.Along with the senescence of China's population and carrying out of carcinoma of prostate generaI investigation, increasing patients with prostate cancer will appear, and carcinoma of prostate has become the problem that more and more influences public health.
Prostatic hyperplasia is the hyperplasia of prostate of prostata tissue, does not have necessary connection with carcinoma of prostate, but the two sometimes and deposit.Its main performance is a urinary tract obstruction.Male's prostate was reached maturity in the time of 25 years old, not regrowth under the normal condition.Also have the people about 40 years old owing to reason generation prostatic hyperplasia such as hormone in vivo imbalances.Show that according to the investigation of the U.S. 60 years old male of 50% has prostatic hyperplasia, and in 80 years old male, this numeral rises to 80%.
At present, the treatment of this two classes prostatosis can obtain higher survival rate all based on surgical removal for the carcinoma of prostate early stage patient, but owing to lack effective Drug therapy, middle and advanced stage patient survival rate is lower.Studies show that in recent years; prostate participates in the composition of seminal fluid except that the secretion prostatic fluid; can also produce the panimmunity globulin, synthetic have an antibacterial action contain the zinc polypeptide, and prostate also has the local immunity function that the protection reproductive system exempts from antibacterial and the invasion and attack of other pathogenic microorganisms.Therefore, the someone advocates that prostate should be kept as far as possible under possible situation.Nonoperative pharmacotherapy just also gets more attractive.
At present, be used for the direction of prostatic hyperplasia treatment for eliminating the kinetic factor or the mechanical factor of prostatic hyperplasia.The medicine that is used to eliminate mechanical factor is mainly the effect that suppresses dihydrotestosterone directly, indirectly, and the medicine that is used to eliminate kinetic factor is mainly contraction and the tensity that suppresses smooth muscle.Clinical medicine mainly contains 4 classes: (1) androgen antagonist; (2) 5 inhibitor; (3) natural product preparation; (4) α 1 adrenergic receptor blocker.Part also is used for the auxiliary treatment of carcinoma of prostate in them.Because the prostatosis Drug therapy is longer the course of treatment, so the toxic and side effects of medicine attracts people's attention.In the Chinese herbal medicine treasure-house of China, the medical material and the prescription of a lot of treatment prostatic hyperplasia and carcinoma of prostate arranged, wherein there are many medicines to have curative effect preferably through clinical verification.Adopt modern biological and chemical method, extract from these Chinese crude drugs and filter out active component, be expected to obtain the new drug of resisting prostatic disorders safely and efficiently, this will produce huge economic benefit and social benefit.
Prostate specific antigen (PSA) is the most important index that is used for prostatic cancer early diagnosis at present clinically, is mainly expressed under the inducing of androgen and other somatomedin such as TGF β by prostate epithelial cell.PSA content is at 1-4ng/ml in the normal human serum, and PSA content is usually then considerably beyond this value in the patients with prostate cancer serum, and PSA content generally also is higher than normal value among the prostatic hyperplasia patients serum.The rising of PSA content mainly is the overexpression because of PSA in the prostatic cell in these patient's serum.If the patient is through treatment, PSA content obviously descends in the serum, can think tentatively that then treatment is effective.Therefore the variation of PSA content can be used as an index of this two classes prostatosis curative effect.
Technology contents
One of the object of the invention is to disclose the pharmaceutical formulation of the natural long-chain fat acid derivative of a class;
Two of the object of the invention is to disclose the preparation method of the natural long-chain fat acid derivative of this class;
Three of the object of the invention is to disclose the clinical practice of the natural long-chain fat acid derivative of this class at treatment prostate relevant disease.
The present invention has found to prevent and the active ingredient of treatment prostatosis is made up of the chemical compound of the following chemical structure general formula I.
General formula (I)
A:(CH
2)
N2Or (C
3H
4) n
3n
1, n
2, n
3It is 1～20 integer
The B:N-ethoxy, 1-O-fructoside, glyceryl, OH
A in general formula (I) is (C
3H
4)
3, n
1Be 7, B is a glyceryl, and the chemical compound of general formula (I) representative is a glyceryl linolenate.
A in general formula (I) is (C
3H
4)
3, n
1Be 7, B is the N-ethoxy, and the chemical compound of general formula (I) representative is N-(2-ethoxy) 9,12,15-octadecane triolefin amide.
A in general formula (I) is (C
3H
4)
3, n
1Be 7, B is the O fructoside, and the chemical compound of general formula (I) representative is 9,12,15-octadecane trienic acid 1-O-β-D fructoside [9,12,15-Octadecatrienoic acid 1-O-β-D-fructoside].
A in general formula (I) is (CH
2)
13, n
1Be 1, B is the O-fructoside, the chemical compound hexadecanoic acid 1-O-β-D fructoside [Hexadecanoic 1-O-β-D-fructoside] of general formula (I) representative.
The active ingredient preparation method concrete steps of prevention of the present invention and treatment prostatosis are as follows:
Preparation method one:
1, the extraction of solvent: after former plant is pulverized, water, methanol, ethanol or contain water beetle, ethanol (30～95%), acetone, aqueous acetone or ethyl acetate, heating extraction (comprising backflow) or supersound extraction, the solvent for use amount is 8～15: 1 with former plant weight ratio, can repeat to extract 1～3 time, remove medicinal residues; Filtrate is concentrated into relative density 1.10～1.15 under normal pressure or reduced pressure.
2, organic solvent degreasing: above-mentioned concentrated solution is added the suitable quantity of water dissolving,, discard organic solvent with normal hexane, cyclohexane extraction, chloroform, petroleum ether or ether extraction.
3, column chromatography: above-mentioned water layer is concentrated into relative density 1.10～1.15, carry out silica gel (100～140 order) column chromatography, carry out eluting with petroleum ether-ethyl acetate, cyclohexane extraction-ethyl acetate, normal hexane-ethyl acetate, petroleum ether-acetone, cyclohexane extraction-acetone or normal hexane-acetone, collect 8: 2～6: 4 eluting parts of above-mentioned mixed solvent, the solvent evaporate to dryness.
4, purification: the product of above-mentioned steps gained is carried out polydextran gel (sephadex LH20) column chromatography,, collect each eluting part, volatilize solvent and get chemical compound with 6: 4 eluting of chloroform-methanol.
Preparation method two:
1, uses organic solvent degreasing: after former plant is pulverized,, discard organic solvent with normal hexane, cyclohexane extraction, chloroform, petroleum ether or ether heating and refluxing extraction or supersound extraction.
2, the extraction of solvent: medicinal residues water, methanol, the ethanol after the defat or contain water beetle, ethanol (30～95%), acetone, aqueous acetone or ethyl acetate, heating (comprising backflow) or soaking at room temperature are extracted, the solvent for use amount is 8～15: 1 with former plant weight ratio, can repeat to extract 1～3 time, remove medicinal residues, filtrate is concentrated into relative density 1.10～1.15 under normal pressure or under the reduced pressure.
3, column chromatography: above-mentioned concentrated solution is carried out silica gel (100～140 order) column chromatography, carry out eluting with petroleum ether-ethyl acetate, cyclohexane extraction-ethyl acetate, normal hexane-ethyl acetate, petroleum ether-acetone, cyclohexane extraction-acetone or normal hexane-acetone, collect 8: 2～6: 4 eluting parts of above-mentioned mixed solvent, solvent evaporated.
4, purification: the product of above-mentioned steps gained is carried out polydextran gel (sephadex LH20) column chromatography, use the chloroform-methanol eluting, collect each eluting part, volatilize solvent, get chemical compound.
The present invention be used to prevent and the content of active ingredient for the treatment of prostatosis between 0.01～1000mg.
The present invention is used to prevent and treat the active ingredient of prostatosis, its application mode is: add relevant excipient in each single-activity composition or the mixture be made up of two and two above active ingredients, make tablet, capsule, soft capsule, liquid preparation, granule, soft extract, pill, powder, suspending agent, dispersant, syrup, suppository, injection.Excipient wherein comprises binding agent, as polyvinylpyrrolidone, hypromellose etc.; Disintegrating agent is as sodium carboxymethyl cellulose, low-substituted hydroxypropyl cellulose etc.; Diluent is as starch, Icing Sugar, dextrin, microcrystalline Cellulose, mannitol, lactose, Semen sojae atricolor wet goods; Lubricant is as magnesium stearate, Pulvis Talci; Sweeting agent is as sucrose, fructose, aspartame etc.; Stabilizing agent is as sodium carboxymethyl cellulose, cyclodextrin etc.; Antiseptic is as ethylparaben, sodium benzoate etc.
Fatty glyceride is distributed in the vegetable oil such as coffee bean, olive oil, vegetable oil, has bibliographical information glyceride to can be used for treating diabetes and obesity.Tripalmitin, glyceryl linolenate, glyceryl linoleate have antiinflammatory, anti-allergic effects.Glyceryl linolenate remains in the fruit and seed that is the Chinese medicine Caulis Akebiae, in the fragrant gong Herba Ainsliaeae Glabrae of Fructus Pruni platymiscium and in the Aceraceae distribution is arranged also, but does not see that the report that this product or these plants is used for prostata disease treating is arranged.9,12,15-octadecane trienic acid 1-O-β-D fructoside and hexadecanoic acid 1-O-β-D fructoside are new chemical constitution body.
Description of drawings
Fig. 1 is the inhibitory action sketch map of several chemical compounds of the present invention to androgen third testis.
The following example will further specify the present invention, and embodiment should not be regarded as limiting the scope of the invention.
Embodiment 1
Get Pollen Brassicae campestris 3Kg, pulverize, add 18L chloroform heating and refluxing extraction 1 hour, put coldly, filter.Medicinal residues add 24L ethyl acetate heating and refluxing extraction twice, filter.Merge extractive liquid,, decompression and solvent recovery, adding the doubling dose column chromatography mixes thoroughly with silica gel, vacuum drying, porphyrize, the chromatographic column of packing into is with cyclohexane extraction-acetone (9: 1～6: 4) solvent system gradient elution, collect 8: 2～6: 4 elution fractions, continue with Sephadex LH-20 post once more separation and purification obtain nine chemical compounds.
Embodiment 2
Long-chain amide, linolenic acid glyceride and hexadecanoic acid fructoside demonstrate in experiment in vitro and suppress the excretory activity of PSA (prostate specific antigen), see Table one. adopt of the influence of the above-mentioned several materials of enzyme linked immunological measuring to LNCaP emiocytosis PSA.
At first will wrap by multi-resistance and be diluted to 4ug/ml, and add in the ELISA Plate, every hole 100ul places more than 12 hours for 4 ℃.Add the sealing fluid-tight after washing with PBST and close, 37 ℃ 1 hour.The cells and supernatant of adding behind drug effect, 37 ℃ of temperature were bathed 2 hours.The washing back adds an anti-solution, 200ng/ml, and 37 ℃ of temperature were bathed 1 hour.The washing back adds two anti-solution of dilution in 1: 8000, room temperature 1 hour, lucifuge.The washing back adds colour developing liquid, and the lucifuge temperature adds 2N sulphuric acid after bathing 10min, in 492nm measure light absorption value.
Embodiment 3
Long-chain amide, octadecane trienic acid-fructoside and hexadecanoic acid fructoside demonstrate the activity of androgen antagonist in the cell in vitro experiment.Be the inhibitory action sketch maps of several chemical compounds as described in Figure 1 to androgen third testis.
LUC Photinus pyralis LUC Photinus pyralis FL reporter gene system activates active analysis to androgen receptor AR:
From people's fatty tissue, be cloned into the AR cDNA of total length with the method for PCR, used primer sequence 1 is 5 '-cgggatcctggaagattcagccaagctcaagg-3 ', sequence 2 is 5 '-gctctagaatgggagggttagatagggaggga-3 ', the PCR product that increases inserted expression vector after order-checking identify.Reporter gene detects carrier pGL3-Promoter with the luciferase of Promega company and makes up, and has inserted the AR response element (sequence 3 be 5 '-gatctggctctttcagttctaggaagaactgaaagagcctttgggctctttcagtt ctaggaagaactgaaagagcctttg-3 ') of three copies in its upstream.Transfection experiment carries out in 96 orifice plates with the U2OS cell, corotation AR gene when transit telegram is accused gene, and transfection added 10nM androlin and medicine to be detected in every hole after 24 hours, and made the final concentration of solvent DMSO remain on 0.1%.Drug effect cell lysis and carry out the detection of uciferase activity after 24 hours.
Table one
| Medicine name | Suppression ratio (%) | ||||||
| Concentration (ug/ml) | ????5 | ????10 | ????12.5 | ????20 | ????25 | ????50 | ????100 |
| The long-chain amide | ????9.7 | ????nd | ????31 | ????52 | ????63 | ????71 | ????nd |
| The linolenic acid glyceride | ????23 | ????40 | ????57 | ????nd | ????76 | ????nd | ????nd |
| The hexadecanoic acid fructoside | ????4.5 | ????nd | ????8.4 | ????nd | ????26 | ????42 | ????76 |
Annotate: nd represents that this concentration do not test activity.
Claims (15)
1, a kind of natural product pharmaceutical formulation of being made up of long-chain fatty acid derivative is characterized in that, the active ingredient of this pharmaceutical formulation chemical compound that following chemical structure of general formula is formed of serving as reasons, and its chemical structure of general formula is:
Wherein:
A is (CH
2)
N2Or (C
3H
4)
N3n
1, n
2, n
3It is 1～10 integer;
B is the N-ethoxy, 1-O-fructoside, glyceryl, OH;
2, chemical compound as claimed in claim 1 is characterized in that, described compound substituent structure is:
A is (C
3H
4) n
2, n
2Equal 3;
B is a glyceryl;
n
1Equal 7;
This chemical compound is a glyceryl linolenate.
3, chemical compound as claimed in claim 1 is characterized in that, the substituent structure of described chemical compound is:
A is (C
3H
4) n
2, n
2Equal 3;
B is the N-ethoxy;
n
1Equal 7;
This chemical compound is that glyceryl linolenate is N-(2-ethoxy) 9,12,15-octadecane triolefin amide.
4, chemical compound as claimed in claim 1 is characterized in that, in the substituent structure of described chemical compound:
A is (C
3H
4) n
2, n
2Equal 3;
n
1Equal 7;
B is the 1-O fructoside
This chemical compound is 9,12, and 15-octadecane trienic acid 1-O fructoside (9,12,15-Octadecatrienoicacid 1-O-β-D-fructoside).
5, chemical compound as claimed in claim 1 is characterized in that, in the substituent structure of described chemical compound:
A is (CH
2) n
2, n
2Equal 13;
n
1Equal 1;
This chemical compound is hexadecanoic acid 1-O-fructoside (Hexadecanoic 1-O-β-D-fructoside).
6, the pharmaceutical formulation formed of the long-chain compound represented of general structure according to claim 1 is characterized in that, this pharmaceutical preparation is made up of such long-chain derivative active component or component and pharmaceutical carrier or diluent.
7, pharmaceutical formulation as claimed in claim 6, it is characterized by tablet, capsule, soft capsule, liquid preparation, granule, soft extract, pill, powder, suspending agent, dispersant, syrup, injection that long-chain derivative active ingredient that this pharmaceutical preparation is represented by described general structure or component are made.
8, the purposes of pharmaceutical formulation as claimed in claim 6 is characterized in that, described pharmaceutical formulation is used for prevention and treatment prostatic hyperplasia, prostatitis and tumor of prostate.
9, pharmaceutical formulation as claimed in claim 6 is characterized in that, the content of its contained active ingredient is between 0.01～1000mg.
10, pharmaceutical formulation as claimed in claim 6 is characterized in that, the preferred content of its contained active component is between 0.50～500mg.
11, the long-chain compound active component represented of general structure according to claim 1, it is characterized in that the preparation method of these active ingredients is: former plant is pulverized, and solubilizer extracts; Extract organic solvent degreasing, medicinal residues continue and use solvent extraction, and chromatography and purification are prepared from.
12, preparation method as claimed in claim 11 is characterized in that, extracts solvent and is water, methanol, ethanol or contain a kind of in water beetle, ethanol (30-95%), acetone, aqueous acetone or the ethyl acetate; Extract and adopt reflux or supersound extraction.
13, preparation method as claimed in claim 11 is characterized in that, the organic solvent that is used for defat is normal hexane or cyclohexane extraction or chloroform or petroleum ether or ether.
14, preparation method as claimed in claim 11 is characterized in that, a kind of in column chromatography available silicon plastic column chromatography, polyamine column chromatography and the polydextran gel column chromatography.
15, preparation method as claimed in claim 11 is characterized in that, silica gel column chromatography can be used by following any two kinds of solvents, as: the mixed solvent that petroleum ether, ethyl acetate, cyclohexane extraction, acetone, normal hexane are formed carries out gradient elution.
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