CN1285338C - Antilung gland cancer medicine, its preparation method and its application - Google Patents
Antilung gland cancer medicine, its preparation method and its application Download PDFInfo
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Abstract
The present invention provides lung adenocarcinoma resisting medicine, a preparation method of the medicine and the application of active compounds or active components of the present invention for preparing medicine for treating lung adenocarcinoma, and the medicine is prepared by the method that active sites BF extracted by effective quantities of compounds of (20R, 24R)-24, 25-16, 23-23, 27-triepoxy-12-acetoxy-27-hydroxy-9, 19-cyclolanostane-3-O-beta-D-xylopyranoside or cimicfuga rhizome are used as the active components, and carriers acceptable for pharmacy are matched.
Description
Technical field: the present invention relates to a kind of Antilung gland cancer medicine, the preparation method of this medicine, and the application of this active constituents of medicine in the medicine of preparation treatment adenocarcinoma of lung.
Background technology: Rhizoma Cimicifugae is China's famous Chinese medicine very commonly used, be mainly the dry rhizome of ranunculaceae plant SANYE Rhizoma Cimicifugae Cimicifuga heracleifolia Kom, the Rhizoma Cimicifugae C.dahurica Maxim of Xingan, Rhizoma Cimicifugae or RHIIZOMA CIMICIFUGAE C.foetida L., these three kinds of medicinal plants rhizome record into the Pharmacopoeia of the People's Republic of China (calendar year 2001 version) as Chinese medicine Rhizoma Cimicifugae Cimicifugafoetida L..Rhizoma Cimicifugae has the rash of delivering, heat-clearing and toxic substances removing, the effect of elevate a turnable ladder yang-energy; Often be used to headache due to pathogenic wind-heat, toothache, aphtha, laryngopharynx swelling and pain, measles without adequate eruption, YANG toxin syndrome is sent out speckle, proctoptosis, diseases such as uterine prolapse.Chinese medicine Rhizoma Cimicifugae Cimicifuga foetida L. mainly originates in ground such as Yunnan, Guizhou, Sichuan, Hubei, is the conventional Chinese medicine material of a large amount of cultivations.Do not see in the prior art chemical compound of extraction separation from the Chinese medicine Rhizoma Cimicifugae (20R is arranged, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-27-hydroxyl-9, the active site BF of 19-cyclolanostan-3-O-β-D-xylopyranose glucoside and extraction separation is as the report of Antilung gland cancer medicine active component.
Summary of the invention: the object of the present invention is to provide a kind of chemical compound (20R with effective dose, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-27-hydroxyl-9, the active site BF that 19-cyclolanostan-3-O-β-D-xylopyranose glucoside or Rhizoma Cimicifugae extract are active component and are assigned in the Antilung gland cancer medicine that pharmaceutically acceptable carrier is formed.
Another object of the present invention is to provide manufacturing method for above mentioned medicine.
Further purpose of the present invention is to provide reactive compound of the present invention or the application of active component in the medicine of preparation treatment adenocarcinoma of lung.
Above-mentioned purpose of the present invention is achieved by following technical proposals:
A kind of medicine of Antilung gland cancer, the chemical compound K-314 that wherein contains effective dose promptly (20R, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-27-hydroxyl-9,19-cyclolanostan-3-O-β-D-xylopyranose glucoside and pharmaceutically acceptable carrier.
A kind of medicine of anti-Antilung gland cancer, the Rhizoma Cimicifugae that wherein contains effective dose extracts active site BF and pharmaceutically acceptable carrier.
The preparation method of above-mentioned Antilung gland cancer medicine, get Rhizoma Cimicifugae Cimicifuga foetida L. rhizome, pulverize back methanol extraction three times, each 3-4 hour, after methanol extract liquid removes by filter medicinal residues, be evaporated to steaming and do not go out methanol, add a certain amount of water dilution again, use petroleum ether extraction 2-3 time, behind the recovery petroleum ether, concentrate and obtain the Petroleum ether extraction position, water layer reuse ethyl acetate extraction is 2-3 time then, reclaims ethyl acetate, concentrates and obtains the ethyl acetate extraction position, separate 2-3 time with silica gel column chromatography, the eluent chloroform: methanol or chloroform/acetone gradient elution, obtain active site BF, this active site BF separates with silica gel column chromatography, chloroform/methanol gradient elution, crystallization purifying obtain the chemical compound K-314; BF or K-314 add pharmaceutically acceptable carrier, get Antilung gland cancer medicine.
Preparation method is to get the dry rhizome of Rhizoma Cimicifugae Cimicifuga foetida L. more specifically, pulverize back methanol extraction three times, each 4 hours, after methanol extract liquid removes by filter medicinal residues, be evaporated to steaming and do not go out methanol, add again after a certain amount of water dilution, with petroleum ether extraction three times, after reclaiming petroleum ether, concentrate and obtain the Petroleum ether extraction position, water layer reuse ethyl acetate extraction is three times then, reclaim ethyl acetate, concentrate and obtain the ethyl acetate extraction position, reuse 1000g silica gel column chromatography separates, and the eluent chloroform: methanol was from 100: 0; 100: 1; 50: 1; 20: 1 to 1: 1 gradient elutions, by the position Fr.4 that 20: 1 eluent eluting of chloroform/methanol obtain, this separated part Fr.4 separates once more with the 2000g silica gel column chromatography, and continue with the eluent chloroform: methanol was from 50: 1; 40: 1; 30: 1; 20: 1 gradient elutions, by chloroform: the part that 40: 1 eluent eluting of methanol obtain obtains separated part Fr.4.1 after concentrating; By chloroform: the part that 30: 1 eluent eluting of methanol obtain obtains separated part Fr.4.2 after concentrating; By chloroform: the part that 20: 1 eluent eluting of methanol obtain obtains separated part Fr.4.3 after concentrating; Fr.4.2 separates once more with the 1000g silica gel column chromatography, use chloroform: methanol 40: 1, active site BF, separated part Fr.4.2.1 that 30: 1 eluent eluting must be made up of the mixture of chemical compound K-314 and other cimicifugoside compounds and separated part Fr.4.2.2 etc.; Active site BF separates with the 300g silica gel column chromatography, and use chloroform: 40: 1 eluent eluting of methanol obtain the chemical compound K-314; BF or K-314 add pharmaceutically acceptable carrier, get Antilung gland cancer medicine.
In addition, the present invention also provides chemical compound K-314 and Rhizoma Cimicifugae to extract the application of active site BF in the medicine of preparation treatment adenocarcinoma of lung.
Chemical compound K-314 of the present invention i.e. (20R, 24R)-24,25-16,23-23, when 27-three epoxies-12-acetoxyl group-27-hydroxyl-9,19-cyclolanostan-3-O-β-D-xylopyranose glucoside or active site BF are used as on the medicine, can directly use, perhaps use with the form of pharmaceutical composition, this pharmaceutical composition contains 0.1-99%, preferred 0.5-90% (20R, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-27-hydroxyl-9,19-cyclolanostan-3-O-β-D-xylopyranose glucoside or BF, all the other are acceptable on the materia medica, to nontoxic and inert pharmaceutically suitable carrier of humans and animals and/or excipient.
Described pharmaceutical carrier or excipient are that one or more are selected from solid, semisolid and liquid diluent, extra-fill material and pharmaceutical preparation adjuvant.Described effective ingredient is used with the form of per weight dose.
But medicine oral administration of the present invention administration.Oral available its solid or liquid preparation are as tablet, powder, sugar-coat agent, capsule, injection etc.
The preparation method of Antilung gland cancer medicine of the present invention can adopt: the dry rhizome of getting Chinese medicine Rhizoma Cimicifugae Cimicifuga foetida L., rhizome, pulverize back methanol extraction three times, each 3-4 hour, after methanol extract liquid removes by filter medicinal residues, be evaporated to steaming and do not go out methanol, add a certain amount of water dilution again, use petroleum ether extraction 2-3 time, behind the recovery petroleum ether, concentrate and obtain the Petroleum ether extraction position, water layer reuse ethyl acetate extraction is 2-3 time then, reclaims ethyl acetate, concentrates and obtains the ethyl acetate extraction position, separate 2-3 time with silica gel column chromatography, the eluent chloroform: methanol or chloroform/acetone gradient elution, obtain active site BF, this active site separates with silica gel column chromatography, chloroform/methanol gradient elution, crystallization purifying obtain the chemical compound K-314; BF or K-314 add pharmaceutically acceptable carrier and promptly get Antilung gland cancer medicine.
The specific embodiment: followingly further specify essence of the present invention, but content of the present invention is not limited thereto with embodiments of the invention.
Embodiment 1:
1, K-314 promptly (20R, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-27-hydroxyl-9, extraction separation and the preparation of 19-cyclolanostan-3-O-β-D-xylopyranose glucoside (hereinafter to be referred as K-314) and active site BF:
Get the dry rhizome 2.5Kg of Rhizoma Cimicifugae Cimicifuga foetida L., pulverize back methanol extraction three times, each about 4 hours; After methanol extract liquid removes by filter medicinal residues, be evaporated to steaming and do not go out methanol; Add after a certain amount of water dilution again, use petroleum ether extraction three times, behind the recovery petroleum ether, concentrate and obtain 187g Petroleum ether extraction position: water layer reuse ethyl acetate extraction is three times then, reclaims ethyl acetate, concentrates and obtains 214.5g ethyl acetate extraction position.214.5g separate with the 1000g silica gel column chromatography at the ethyl acetate extraction position, the eluent chloroform: methanol was from 100: 0; 100: 1; 50: 1; 20: 1 to 1: 1 gradient elutions, the heavily about 135g of position Fr.4 that obtains by 20: 1 eluent eluting of chloroform/methanol.This separated part 135g Fr.4 separates once more with the 2000g silica gel column chromatography, and continue with the eluent chloroform: methanol was from 50: 1; 40: 1; 30: 1; 20: 1 gradient elutions, by chloroform: the part that 40: 1 eluent eluting of methanol obtain obtains the heavily about 30g of separated part Fr.4.1 after concentrating; By chloroform: the part that 30: 1 eluent eluting of methanol obtain obtains the heavily about 80g of separated part Fr.4.2 after concentrating; By chloroform: the part that 20: 1 eluent eluting of methanol obtain obtains the heavily about 23g of separated part Fr.4.3 after concentrating.Separated part 80g Fr.4.2 separates once more with the 1000g silica gel column chromatography, use chloroform: methanol 40: 1, the eluent eluting obtained various parts in 30: 1, as the active site BF that forms by the mixture of compound K 314 and other cimicifugoside compounds, separated part Fr.4.2.1 and separated part Fr.4.2.2 three parts; Active site BF30g separates with the 300g silica gel column chromatography, and use chloroform: 40: 1 eluent eluting of methanol obtain compound K 314, and the about 850mg of pure product of K314 is separated out in crystallization.
2, the structure of K-314 chemical compound is determined:
K-314 chemical compound: C
37H
56O
11, colourless prism, mp 232-234 ℃, [α]
D=-66.0 ° (c 1.80, MeOH: CHCl
31: 1).
Hydrogen nuclear magnetic resonance spectrum data δ (ppm) (solvent Py-d5): 5.66 (1H, s, 27-H), 5.05 (1H, dd, J=9,4Hz, 12-H), 4.57 (1H, dd, J=14,7Hz, 16-H), 3.86 (1H, s, 24-H), 3.42 (1H, dd, J=11,4Hz, 3-H); 2.69 (1H, dd, J=16,9Hz) 1.20 (1H, m) (11-H); 2.23 (1H, m) 1.80 (1H, m) (2-H); 2.20 (1H, m) 1.63 (1H, m) (22-H); 1.93 (1H, m) 1.53 (1H, m) (15-H); 1.80 (1H, m, 20-H), 1.75 (1H, s, 26-H), 1.72 (1H, m, 17-H), 1.59 (1H, m, 8-H), 1.34 (3H, s, 18-H); 1.56 (1H, m) 1.15 (1H, m) (1-H); 1.43 (1H, m) 0.64 (1H, m) (6-H); 1.27 (3H, s, 29-H); 1.23 (1H, m) 0.90 (1H, m) (7-H); 1.22 (1H, s, 5-H), 0.97 (3H, d, J=6Hz, 21-H), 0.96 (3H, s.30-H), 0.79 (3H, s, 28-H), 0.59 (1H, d, J=4Hz) 0.25 (1H, d, J=4Hz) (19-H).12-COCH
3Part: 2.11 (3H, s, 2 '-COCH
3).Xylose part: 4.78 (1H, d, J=7.0Hz, 1 '-H), 3.94 (1H, t, J=6.7Hz?, 2 '-H), 4.10 (1H, dd, J=2.7,7.6Hz?, 3 '-H), 4.18 (1H, m, 4 '-H); 3.67 (1H, m, 5 '-H), 4.30 (1H, dd, J=5,10Hz, 5 '-H).
Nuclear magnetic resonance of carbon spectrum data δ (ppm) (solvent Py-d5): 105.84 (s, 23-C), 98.42 (s, 26-C), 88.08 (d, 3-C), 78.08 (d, 12-C), 73.06 (d, 16-C), 65.60 (s, 25-C), 63.46 (s, 24-C), 56.44 (d, 17-H), 48.74 (s, 13-C), 47.84 (s, 14-H), 46.98 (s, 5-C), 45.69 (s, 8-C), 43.57 (t, 15-C), 41.22 (s, 4-C), 37.61 (t, 22-C), 36.71 (t, 11-C), 31.91 (t, 1-C), 29.94 (t, 2-C), 29.52 (t, 19-C), 26.74 (s, 10-C), 26.00 (d, 20-C), 25.69 (t, 7-C), 25.69 (q, 29-C), 21.00 (q, 21-C), 20.10 (t, 6-C), 20.10 (s, 9-C), 19.50 (s, 28-C), 15.33 (q, 30-C), 13.54 (q, 18-C), 13.12 (q, 27-C).12-COCH
3Part: 171.61 (s, CO), 21.67 (q, COCH
3).Xylose part: 107.60 (s, 1 '-C), 75.63 (d, 2 '-C), 78.69 (d, 3 '-C), 71.27 (d, 4 '-C), 67.16 (t, 5 '-C).
Ir data vmax (KBr) (cm
-1): 3500-3350 (OH), 1715 (C=O).
The chemical constitution of compound K-314 is Actein:(20R, 24R) 24,25-16,23-23,27-three epoxies-12-acetoxyl group-27-hydroxyl-9,19-cyclolanostan-3-O-β-D-xylopyranose glucoside [(20R, 24R)-24,25-16,23-23,27-triepoxy-12-acetoxyl-27-hydroxyl-9,19-Cyclolanostanol-3-O-β-D-xylopyranoside]
The chemical constitution of K-314 chemical compound is:
2, anti-tumor biological is measured:
Material and method
The MMT method of improvement is adopted in the evaluation of anti-tumor activity.The MMT method is a kind of external active anticancer evaluation methodology that comes into one's own day by day, and the method objectivity is strong, can realize semi-automation, and it is easy to participate in method than isotope nucleic acid precursor.But this fado as lysate, made the reduzate of MMT with acidify isopropyl alcohol equal solvent in the past--the dissolving of-Jia Za and protein precipitation etc. is very incomplete, and it is loaded down with trivial details suddenly to cause replacing culture fluid and violent jolting etc. to relate to, and result's reliability also decreases.Zhou Jianjuns etc. have been done further improvement at some defectives of MMT method:
[3]The MMT method of improvement has adopted three strong lysates of dissolution, can not resemble in the original method, add before the MMT, need the culture fluid that suction is abandoned or centrifugal removal replacing is original, reach and remove wherein composition such as serum albumin in order to avoid cause interference, also needn't be after adding MMT generation Jia Za, thermal agitation culture plate hydrotropy.So not only operate loaded down with trivial detailsly, change the cell that culture fluid will lose 20-30%.The modification method of Zhou Jianjun etc. has been simplified operation, has also improved reliability, is more suitable for in-vitro screening and drug sensitive detection in the significant antitumor medicine.Thereby the MMT method of improvement is adopted in the experiment of the anti-tumor activity in this patent.
Prepare before the test
Sample is dissolved into 10 milligrams every milliliter concentration and is preserved as stock solution and under 4 degrees centigrade of dark with dimethyl sulfoxine.The stock solution of sample is diluted to experimental concentration with non-immune saline before use.
Cell is arranged and is cultivated
Mice ehrlich ascites tumor cell strain, human stomach cancer cell line and human breast cancer cell strain are to collect the center from the US mode strain.All cells are grown in the RPMI-1640 medium, add the immune serum of the non-activity of 10% thermal inactivation, and 2 receive the L-glutamate, Glu that rubs, 100 penicillins of tiring, the HEPES that 10 millis of the streptomycin of 100ug/ml and PH7.4 rub.Cell is stored under 37 degrees centigrade, the moist 5%CO that contains
2Incubator in.
Cell growth inhibited method
Sample is cultivated the tetrazolium analytic process to the growth inhibited of tumor cell by trace and is measured, and has only less adjustment.Simply, adherent tumor cell is seeded the micro-culture dish in 96 holes, makes its adhesion 24 hours before adding medicament, and suspension cell is sowing before medicine adds.Each tumor cell be listed in different phase (adhesive cell is 72 hours, and suspension cell is 48 hours) add 5 concentration (0.01,0.1,1,10, sample 100mg/ml), and each concentration triplicate.Join the MTT of 5mg/ml in each hole the latter stage after adding sample, and culture dish is placed under 37 degrees centigrade the condition and cultivated 4 hours, and then adding three-phase mixed solution (10% SDS, the hydrochloric acid that 5% isopropyl alcohol and 0.012 rubs), again culture dish being placed on 37 degrees centigrade cultivated 12-20 hour down.On the sensitization mirror of 570 nanometers, read optical density.Sample is to use IC to the cytotoxicity of tumor
50Value is expressed, and calculates with the LOGIT method.
The biological activity test list of references:
1.Mosmman?T.Rapid?colorimetric?assay?for?cellular?growth?and?survival：Application?to?proliferation?and?cytotoxicity?assays.J.Immunol，Meth.1983；65：55-63
2.Alley?MC，Scudiero?DA，Monks?A?et?al.Feasibility?of?drug?screenig?withpanels?of?human?tumor?cell?lines?using?a?microculture?tetrazolium?assay.CancerRes.1988；48：589-601
3.Zhou JJ, Yue XF.Han JX et al.Improved MTT assay for activity ofantitumor agents.Chin J Pharm (Chinese Journal of Pharmaceuticals) 1993,24 (10): 455-457
From table 1 and table 2 as can be seen compound K-314 have the activity of very significant inhibition human lung adenocarcinoma cell line (K549), IC
50Be 0.37 μ g/mL; Particularly the cytotoxic activity of compound K-314 pair human lung adenocarcinoma cell line (K549) has surpassed positive control famous cancer therapy drug cisplatin (cis-platin) commonly used, its IC
50Only be 0.72 μ g/mL.And cisplatin also has remarkable activity to human erythroleukemia cell's strain (K562), IC
50Be 0.34 μ g/mL.But compound K-314 pair human erythroleukemia cell's strain (K562) inhibitory action very a little less than, almost do not have activity, IC
50＞100 μ g/mL; The anti-tumor activity of compound K-314 is described, has fairly obvious selectivity, considerably beyond famous clinical antitumor drug cisplatin, compound K-314 pair human erythroleukemia cell's strain (K562) does not then suppress the activity of tumor cell basically to the inhibition activity of human lung adenocarcinoma cell line (K549).Thus can compound K-314 having suitable difference and particularity with the anti-tumor activity of cisplatin (cis-platin) on target spot, is very significant antitumoral compounds.
Table 1 compound K-5, K-6 sample are to the suppression ratio of tumor cell:
A549: human lung adenocarcinoma cell line;
K562: human erythroleukemia cell's strain;
The measurement result of K-314 anti-tumor biological:
Table 2 compound K-314 pair human lung adenocarcinoma cell line (A549), human erythroleukemia cell's strain
(K562) cytotoxic activity:
| Test compound | Molecular weight (MW) | IC 50(μg/mL) K562 | ? A549 |
| Compound K-314 cis-platin (positive control, cisplatin) | 676 ? ? | ＞100 0.34 ? | 0.37 0.72 ? |
Embodiment 2:
Make K-314 by embodiment 1, add excipient, pelletizing press sheet in K-314 and 1: 5 ratio of excipient weight ratio.
Embodiment 3:
Tablet: K-314 20mg
Starch 100mg
Semen Maydis pulp is an amount of
Magnesium stearate is an amount of
Embodiment 4:
Make K-314 by embodiment 1, the capsule preparations method is made capsule routinely.
Embodiment 5:
Capsule: K-314 20mg
Starch 100mg
Glucose 200mg
Magnesium stearate is an amount of
Preparation method: K-314 ground well with auxiliary agent mix, sieve, uniform mixing in suitable containers is the mixture that the obtains hard gelatin capsule of packing into.
Embodiment 6:
Make the active site BF of ethyl acetate extraction by embodiment 1, add excipient, pelletizing press sheet in BF and 1: 1 ratio of excipient weight ratio.
Embodiment 7:
Tablet: BF 1g
Starch 150mg
Semen Maydis pulp is an amount of
Magnesium stearate is an amount of
Embodiment 8:
Capsule: BF 1g
Starch 150mg
Glucose 300mg
Magnesium stearate is an amount of
Preparation method: BF ground well with auxiliary agent mix, sieve, uniform mixing in suitable containers is the mixture that the obtains hard gelatin capsule of packing into.
Claims (1)
1, the chemical compound K-314 promptly (20R, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-27-hydroxyl-9, the application of 19-cyclolanostan-3-O-β-D-xylopyranose glucoside in the medicine of preparation treatment adenocarcinoma of lung.
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| CN 200410079519 CN1285338C (en) | 2004-10-22 | 2004-10-22 | Antilung gland cancer medicine, its preparation method and its application |
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| CN102614208B (en) * | 2012-02-25 | 2013-09-18 | 中国科学院昆明植物研究所 | Application of compound (20R,24R)-24,25-16,23-23,27-triepoxy-12-acetoxyl-9,19-cyclolanostanol-3-O-beta-D xylopyranoside in pharmacy |
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