CN105147660A - Application of resveratrol oligomer in drug preparation - Google Patents
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Abstract
The invention discloses the application of a resveratrol oligomer or pharmaceutically acceptable salt thereof in the preparation of a fatty acid synthetase protein expression index lowering type medicine or a fatty acid synthetase restrainer type medicine. The invention further discloses a pharmaceutical composition which is prepared by taking the resveratrol oligomer or the pharmaceutically acceptable salt thereof as an active ingredient and adding pharmaceutically acceptable auxiliary materials. The resveratrol oligomer provided by the invention can effectively lower the fatty acid synthetase protein expression index and also can refrain the activity of fatty acid synthetase, can serve as a medicine for resisting tumour or preventing and curing obesity, and has a broad application prospect.
Description
Technical field
The present invention relates to resveratrol oligomer or the purposes of its pharmaceutically acceptable salt in preparation reduction fatty acid synthetase expression class medicine or fatty acid synthetase inhibitor class medicine.
Background technology
Fatty acid synthetase (Fattyacidsynthase, FAS) is the key enzyme of organism Endogenous fatty acid building-up process, and it generates long-chain fatty acid by catalysis S-acetyl-coenzyme-A and malonyl coenzyme A.
Research finds, under normal circumstances, FAS can express in the various tissues such as liver and fat, and its function is by carbohydrate synthetic fatty acid, stores with the form of triglyceride.Meanwhile, FAS is also closely related with obesity.This is because FAS has higher expression in the liver and fatty tissue of people, particularly in liver, its fatty acid synthesis ability power comparatively fatty tissue is high 8 ~ 9 times, its expression is by the impact of ingest composition and hormonal readiness simultaneously, and the diet of carbohydrate containing is by stimulating the generation of the high expressed induced lipolysis of FAS.
Studies have found that, the FAS in the tissues such as breast carcinoma, colorectal cancer, carcinoma of prostate, ovarian cancer, carcinoma of endometrium expresses far above normal structure.Further research proves, suppresses expression or the activity of FAS, effectively can control the hypertrophy of tumor cell or induce its apoptosis.
Therefore, the expression of suppression FAS or activity are for the biosynthesis suppressing Endogenous fatty acid, and then effectively control the generation of tumor, obesity and various associated metabolic syndromes etc., development has great significance (Xu Xiaowei etc., the progress of fatty acid synthetase inhibitor, Inpharm research magazine, volume the 2nd phase April the 36th in 2009,105-120 page; Zhao Liyan etc., the progress of fatty acid synthetase inhibitor antiobesity action mechanism, Chinese Pharmacological Bulletin, 2006,22 (7), 780-784 page).
Resveratrol (resveratrol) is a kind of diphenyl ethene compounds be present in various plants, and its structure is as follows:
Containing phenolic hydroxyl group and a double bond in resveratrol molecule structure, easily there is condensation dehydration or double bond addition between hydroxyl each other, thus form dimer to polymer.Such as:
ε-viniferin is a kind of dimer of resveratrol, and its structure is as follows:
VitisinA is a kind of tetramer of resveratrol, and its structure is as follows:
VitisinB is a kind of tetramer of resveratrol, and its structure is as follows:
Studies have reported that at present, the dimer of resveratrol or polymer have multiple pharmacologically active.Wherein, for the oligomer of resveratrol, the report of existing antibacterial, antiviral, antioxidation, analgesia isoreactivity.
Such as, the people such as Ye Yong report resveratrol oligomer and have certain analgesic activities, find simultaneously, two, trimerical activity is better than the tetramer (Ye Yong etc., resveratrol oligomer is to the Virtual Analysis of Fos/Jun molecular action and analgesic activities thereof, Chinese Journal of New Drugs the 23rd volume the 1st phase in 2014,80-85 page).
At present, resveratrol oligomer is not yet had to suppress the expression of FAS or the report of activity.
Summary of the invention
The invention provides resveratrol oligomer or the purposes of its pharmaceutically acceptable salt in preparation reduction fatty acid synthetase expression class medicine or fatty acid synthetase inhibitor class medicine.
Preferably, described resveratrol oligomer is resveratrol dimer or Vaticaffinol.
Preferably, described resveratrol oligomer is selected from any one in vitisinA, vitisinB and ε-viniferin:
Preferably, described medicine is the medicine of antitumor drug or control metabolism syndrome.
Further preferably, described antitumor drug is the medicine for the treatment of breast carcinoma, colorectal cancer, carcinoma of prostate, ovarian cancer or carcinoma of endometrium.
Further preferably, the medicine of described control metabolism syndrome is the medicine of control obesity or obesity complication; Still more preferably, described control medicine that is fat or obesity complication is the medicine of control non-insulin-dependent diabetes mellitus, hypertension or coronary thrombosis.
Present invention also offers a kind of pharmaceutical composition, it be with above-mentioned resveratrol oligomer or its pharmaceutically acceptable salt for active component, add the preparation that pharmaceutically acceptable adjuvant is prepared from.
Present invention also offers the purposes of described pharmaceutical composition in preparation reduction fatty acid synthetase expression class medicine or fatty acid synthetase inhibitor class medicine.
Preferably, described medicine is the medicine of antitumor drug or control metabolism syndrome; Further preferably, described antitumor drug is the medicine for the treatment of breast carcinoma, colorectal cancer, carcinoma of prostate, ovarian cancer or carcinoma of endometrium.
Preferably, the medicine of described control metabolism syndrome is the medicine of control obesity or obesity complication; Further preferably, described control medicine that is fat or obesity complication is the medicine of control non-insulin-dependent diabetes mellitus, hypertension or coronary thrombosis.
Experimental result display of the present invention, resveratrol oligomer of the present invention can effectively reduce fatty acid synthetase expression, and can also suppress the activity of fatty acid synthetase, as antitumor or can prevent and treat fat medicine, be with a wide range of applications.
Within implication of the present invention, " control " expression prevents and/or treats.
Within implication of the present invention, " treatment " also comprises recurrent (relapse) prevention or interim (phase) prevention, and the treatment of acute or chronic sign, symptom and/or malfunction.Treatment can be symptomatic treatment, such as, suppress symptom.It can realize in a short time, adjusts within mid-term, or can be described as long-term treatment, such as, inside maintenance therapy.
Obviously, according to foregoing of the present invention, according to ordinary technical knowledge and the customary means of this area, not departing under the present invention's above-mentioned basic fundamental thought prerequisite, the amendment of other various ways, replacement or change can also be made.
The detailed description of the invention of form by the following examples, is described in further detail foregoing of the present invention again.But this should be interpreted as that the scope of the above-mentioned theme of the present invention is only limitted to following example.All technology realized based on foregoing of the present invention all belong to scope of the present invention.
Accompanying drawing explanation
Fig. 1 is the T suppression cell vitality test result of the compounds of this invention;
Fig. 2 is the suppression FAS expression result of the test of the compounds of this invention;
Fig. 3 be the compounds of this invention T suppression cell in FAS result of the test;
Fig. 4 is the suppression FAS activity test result of vitisinA under variable concentrations;
Fig. 5 is the suppression FAS activity test result of ε-viniferin under variable concentrations;
Fig. 6 is the suppression FAS activity test result of vitisinB under variable concentrations.
Detailed description of the invention
The preparation of embodiment 1 vitisinA, ε-viniferin of the present invention, vitisinB
The present embodiment instrument and reagent as follows:
TBE-300C high-speed counter-current chromatograph (Shanghai Tongtian Biotechnology Co., Ltd.); Is furnished with TBP5002 constant flow pump (Shanghai Tongtian Biotechnology Co., Ltd.) simultaneously, DC-0506 low temperature thermostat bath (Shanghai Sunny Hengping Scientific Instrument Co., Ltd.), UV-2000D detector (Shanghai Tongtian Biotechnology Co., Ltd.) and EasyChrom-1000 Data Processing in Chromatography Workstation (Shanghai Tongtian Biotechnology Co., Ltd.).Agilent1260 high performance liquid chromatograph (Agilent company), is furnished with G1311C four-stage pump, G1329B automatic sampler, G1316A column oven and G1315D diode array detector.
Adopt HPLC method to carry out purity detecting (peak area normalization method) its chromatographic condition to each flow point in the present embodiment to be: EclipseXDBC18 post (250mm × 4.6mm, 5 μm); Mobile phase: methanol-acetonitrile-aqueous solution; Gradient elution program is specific as follows: 0-20min, and mobile phase is the methanol of 30-50%, 5%-5% acetonitrile; 21-35min, mobile phase is the methanol of 50-65%, 5%-5% acetonitrile; Flow velocity: 1.0ml/min; Column oven temperature is 30 DEG C; Determined wavelength is 325nm.
(1) after being pulverized by Semen Iridis, with 85% ethanol extraction 3 times, filtration, obtains alcohol extracts after concentrating under reduced pressure recycling design, i.e. sample to be separated
(2) will containing normal hexane, ethyl acetate, stratification after the organic solvent system mix homogeneously of first alcohol and water, get upper strata solvent and lower floor's solvent respectively, ultrasonic degas 20min, using upper strata solvent as immobile phase, lower floor's solvent is as mobile phase, described immobile phase is pumped in the separator tube of high-speed counter-current chromatograph, keep separator tube temperature 25 DEG C, after rotating forward 20min with the rotating speed of 900rpm, pump into mobile phase, after system balance, from injection valve sample introduction, and carry out high speed adverse current chromatogram separation with the flow velocity of 1.5ml/min, determined wavelength is 325nm, receive flow point 1 successively, flow point II and flow point 2, concentrating under reduced pressure is dried to constant weight, obtain highly purified vitisinA (flow point 1) and ε-viniferin (flow point 2), wherein flow point II is one group of mixture, wherein the volume ratio of normal hexane, ethyl acetate, first alcohol and water is 3:6.5:4.2:5.5, flow point 1, the appearance time of flow point II and flow point 2 is followed successively by 60 ~ 80min, 115 ~ 135min, 140 ~ 155min,
(3) flow point II is got, high speed adverse current chromatogram is adopted to be separated, separation method is as follows: will containing petroleum ether, ethyl acetate, stratification after the organic solvent system mix homogeneously of first alcohol and water, get upper strata solvent and lower floor's solvent respectively, ultrasonic degas 20min, using lower floor's solvent as immobile phase, upper 4 layers of solvent are as mobile phase, described immobile phase is pumped in the separator tube of high-speed counter-current chromatograph, keep separator tube temperature 35 DEG C, after rotating forward 20min with the rotating speed of 800rpm, pump into mobile phase, after system balance, from injection valve sample introduction, and carry out high speed adverse current chromatogram separation with the flow velocity of 3.5ml/min, determined wavelength is 325nm, receive flow point 4 and flow point 3 successively, concentrating under reduced pressure is dried to constant weight, obtain highly purified vitisinC (flow point 4) and vitisinB (flow point 3), wherein the volume ratio of petroleum ether, ethyl acetate, first alcohol and water is 5:5:3:6, the appearance time of flow point 4 and flow point 3 is followed successively by 135 ~ 142min and 145 ~ 155min.
The test of pesticide effectiveness of embodiment 2 the compounds of this invention
Material:
Breast carcinoma cell strain MDA-MB-231, the method that vitisinA, ε-viniferin, vitisinB lead in embodiment 1 prepares.
S-acetyl-coenzyme-A, malonyl CoA, NADPH (Triphosphopyridinenucleotide, NADPH) purchased from American Sigma company;
CellCountingKit is purchased from Japanese colleague's chemistry;
Dulbecco ' smodifiedEagle ' smedium (DMEM) and penicillin, streptomycin purchased from American Invitrogen company;
FAS and β-actin monoclonal antibody purchased from American CellSignalingTechnology (CST) company;
Horseradish peroxidase-labeled goat against murine two is anti-purchased from biotech company of Zhong Shan Golden Bridge;
ECL luminescent solution and PVDF membrane (PolyvinylideneFluoride, PVDF) film, hyclone (Fetaibovineserum) are purchased from Zhejiang Tian Hang Bioisystech Co., Ltd (Beijing);
Other chemical reagent are purchased from Beijing chemical reagent work.
1. T suppression cell vitality test
Even must being seeded in the culture dish of the slight 10cm of diameter of MDA-MB-231 cell is cultured to 80%-90%, goes down to posterity in 96 orifice plates, and about 104, every hole cell, is placed in 37 DEG C, 5%CO
2after cultivating 24h in constant temperature cell culture incubator, add the compound treatment of variable concentrations respectively, each process 6 is parallel, in cell culture incubator, process 24h.Abandon culture medium, add containing volume ratio the serum-free medium of the CCK-8 being 1/10, hatch 1-4h for 37 DEG C, survey absorbance in 450nm place.The hole not having cell is blank, has cell but not have the hole of dosing to be experiment contrast.Result of the test as shown in Figure 1.
Result shows, and vitisinA, ε-viniferin, vitisinB all can make the cell viability of the thin MDA-MB-231 of breast carcinoma decline, and make veratryl alcohol oligomer clear inhibited to tumor cell.Wherein, tetramer vitisinB no matter high-concentration and low-concentration, inhibition is all fairly obvious.
2. suppress the test of FAS expression
Cell is laid in six orifice plates uniformly, treats that cell fusion is to 80%-90%, removes culture medium, add the serum-free culture of the medicine of variable concentrations respectively based on 24h in constant incubator.Wash twice with the PBS of pre-cooling afterwards, add 200-300 μ LRIPA lysate in cell lysis on ice, collecting cell lysate after 5-10min, 12000rpm, 4 DEG C of centrifugal 15min, get supernatant.Survey protein concentration with BCA test kit, by calculating, filling into PBS or lysate, the total protein concentration of each sample is adjusted to unanimously.Add 5 × Loadingbuffer (containing DTT) in proportion, 95 DEG C heating 10min, SDS-PAGE electrophoretic separation albumen can be carried out, after albumen is forwarded on pvdf membrane.Film TBST solution (confining liquid) 4 DEG C of closed 2h of 5% (w/v) defatted milk powder after electricity turns, dilute primary antibodie according to primary antibodie description confining liquid, in 4 DEG C of hybridized overnight.Treated film cleans 3 times through TBST, each 10min, after two anti-room temperature hybridization 1h, detects determine immunoreation band with ECL luminescence method, and using β-actin as internal reference, and compare destination protein content.Result of the test as shown in Figure 2.
Result shows, and the MDA-MB-231 cell through vitisinA process significantly declines at the FAS expression at 4 and 8 μ g/mL places; ε-viniferin reduces at 2 μ g/mL place expressions; And the cell of vitisinB process is along with the increase of concentration, the expression of FAS reduces gradually.
Visible, compound of the present invention all has the effect reducing FAS expression.
3. FAS test in T suppression cell
Cell is laid in six orifice plates uniformly, treats that cell fusion is to 80%-90%, removes culture medium, add serum-free culture containing variable concentrations compound respectively based on 24h in constant incubator.Twice is washed with the PBS of pre-cooling.Survey buffer of living in sonicated cells on ice (ultrasonic 2 seconds, interval 5 seconds, 5-10 circulation) with the FAS containing 0.6mMPMSF, in 4 DEG C of centrifugal 30min of 12000g, get supernatant, carry out determination of activity with this cracking supernatant replacement FAS enzymatic solution.The survey live body system of 500 μ L is wherein containing 25mMKH
2pO
4-K
2hPO
4survey live buffer, 0.25mMEDTA, 0.25mMDTT, 30 μMs of S-acetyl-coenzyme-As, 100 μMs of malonyl CoAs, 350 μMs of NADPH (pH7.0), and 20 μ L centrifugal after supernatant.Adopt BCA method to measure protein concentration, the activity of FAS calculates with U/mg.Each sample replication 2-5 time, often group is made up of the sample of 3 or more.Result of the test as shown in Figure 3
Result shows, and vitisinA, ε-viniferin, vitisinB all can to a certain extent, and the cell FAS vigor of vitisinB process reduces gradually, and have the dependency of dosage.
4, FAS activity test is suppressed
FAS extracts in Hepar Gallus domesticus (being stored in-80 DEG C), and surveying reaction system of living is 100mMKH
2pO4-K
2hPO
4survey buffer of living, pH7.0; 1mMEDTA, 1mMDTT, 3 μMs of S-acetyl-coenzyme-As, 10 μMs of malonyl CoAs, 35 μMs of NADPH (pH7.0), reaction is totally 2ml; Add three kinds of compounds of variable concentrations respectively, and supply the DMSO (compound dissolution is in DMSO) of same volume, with the buffer containing variable concentrations compound for background returns to zero; Surveying the condition of living is 37 DEG C of constant temperature, adds the reaction that 6 μ gFAS start, and adopt the absorbance change at Shimadzu UV-1800 ultraviolet-visible spectrophotometer (Japan) continuous monitoring 340nm place, the activity of FAS calculates with U/mg.Each sample replication 2-5 time, often group is made up of the sample of 3 or more.
VitisinA determines following concentration: 0,0.3,0.6,1,1.3,1.6,2 μ g/ml;
ε-viniferin determines following concentration: 0,0.5,1,1.5,2,2.5,3 μ g/ml;
VitisinB determines following concentration: 0,0.3,0.6,1,1.3,1.6,2 μ g/ml;
Result respectively as Figure 4-Figure 6.
As calculated, the IC50 value of above-mentioned three compounds is as follows: vitisinA is 0.458 μ g/ml; ε-viniferin is 2.94 μ g/ml; VitisinB is 0.617 μ g/ml.
Visible, it is active that compound of the present invention all shows the significant FAS that suppresses.Wherein, vitisinA and vitisinB inhibit activities is stronger.
In sum, resveratrol oligomer of the present invention can effectively reduce fatty acid synthetase expression, and can also suppress the activity of fatty acid synthetase, as antitumor or can prevent and treat fat medicine, be with a wide range of applications.
Claims (10)
1. resveratrol oligomer or its pharmaceutically acceptable salt reduce the purposes in fatty acid synthetase expression class medicine or fatty acid synthetase inhibitor class medicine in preparation.
2. purposes according to claim 1, is characterized in that: described resveratrol oligomer is resveratrol dimer or Vaticaffinol.
3. purposes according to claim 1, is characterized in that: described resveratrol oligomer is selected from any one in vitisinA, vitisinB and ε-viniferin:
4. the purposes according to any one of claim 1-3, is characterized in that: described medicine is the medicine of antitumor drug or control metabolism syndrome.
5. purposes according to claim 4, is characterized in that: described antitumor drug is the medicine for the treatment of breast carcinoma, colorectal cancer, carcinoma of prostate, ovarian cancer or carcinoma of endometrium.
6. purposes according to claim 4, is characterized in that: the medicine of described control metabolism syndrome is the medicine of control obesity or obesity complication; Preferably, described control medicine that is fat or obesity complication is the medicine of control non-insulin-dependent diabetes mellitus, hypertension or coronary thrombosis.
7. a pharmaceutical composition, is characterized in that: it be with the resveratrol oligomer described in any one of claim 1-3 or its pharmaceutically acceptable salt for active component, add the preparation that pharmaceutically acceptable adjuvant is prepared from.
8. pharmaceutical composition according to claim 7 reduces the purposes in fatty acid synthetase expression class medicine or fatty acid synthetase inhibitor class medicine in preparation.
9. want the purposes described in 8 according to right, it is characterized in that: described medicine is the medicine of antitumor drug or control metabolism syndrome; Preferably, described antitumor drug is the medicine for the treatment of breast carcinoma, colorectal cancer, carcinoma of prostate, ovarian cancer or carcinoma of endometrium.
10. purposes according to claim 9, is characterized in that: the medicine of described control metabolism syndrome is the medicine of control obesity or obesity complication; Preferably, described control medicine that is fat or obesity complication is the medicine of control non-insulin-dependent diabetes mellitus, hypertension or coronary thrombosis.
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| CN106667994A (en) * | 2016-12-22 | 2017-05-17 | 河南科技大学 | Application of oligomeric polyphenol compounds to preparation of gram-positive drug-resistant bacterium resistant products |
| CN109662962A (en) * | 2018-10-26 | 2019-04-23 | 中国科学院西北高原生物研究所 | The purposes of oligomerization stilbene compound |
| CN110590881A (en) * | 2019-09-23 | 2019-12-20 | 中国科学院西北高原生物研究所 | Novel oligomeric stilbene compounds in iris lactea kernels and extraction method and application thereof |
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| CN113521055A (en) * | 2021-05-31 | 2021-10-22 | 中国科学院西北高原生物研究所 | Application of oligomeric stilbene monomeric compound VitD in preparation of products for improving deposition of animal fat |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106667994A (en) * | 2016-12-22 | 2017-05-17 | 河南科技大学 | Application of oligomeric polyphenol compounds to preparation of gram-positive drug-resistant bacterium resistant products |
| CN112236136A (en) * | 2018-10-04 | 2021-01-15 | 株式会社细田Shc | Composition for improving intestinal flora |
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| CN110590881A (en) * | 2019-09-23 | 2019-12-20 | 中国科学院西北高原生物研究所 | Novel oligomeric stilbene compounds in iris lactea kernels and extraction method and application thereof |
| CN113521055A (en) * | 2021-05-31 | 2021-10-22 | 中国科学院西北高原生物研究所 | Application of oligomeric stilbene monomeric compound VitD in preparation of products for improving deposition of animal fat |
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Application publication date: 20151216 |