CN1524532A - Antineoplastic effect of a group of cycloart-one triterpene compound - Google Patents
Antineoplastic effect of a group of cycloart-one triterpene compound Download PDFInfo
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- CN1524532A CN1524532A CNA031571727A CN03157172A CN1524532A CN 1524532 A CN1524532 A CN 1524532A CN A031571727 A CNA031571727 A CN A031571727A CN 03157172 A CN03157172 A CN 03157172A CN 1524532 A CN1524532 A CN 1524532A
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Abstract
The invention relates to a the antineoplastic action of a group of looped pineapple confectionery terpenoid, which is three 9, 19 looped lanolinum alkyl triterpenoid (23-oxygen-acetyl cimicifugol - 3 -oxygen - beta - D - xyloside, 24 - oxygen - acetyl cimicifugol - 3 -oxygen-beta-D-xyloside and 25-oxygen-acetyl cimicifugol - 3 -oxygen - beta - D - xyloside) extracted from cimicifuga rhizome. Experimental investigation has shown that they have cell toxic action for blood tumor and entity tumor.
Description
Technical field:
The present invention relates to one group of cycloartane that from the plant Rhizoma Cimicifugae, obtains (9,19 ring lanoline alkane) triterpenoid compound to cytotoxicity, the apoptosis-induced effect of blood tumor and solid tumor, influence cell cycle effect, antioxidation and the clinical prevention of tumor with treat in application.
Background technology:
Rhizoma Cimicifugae is Ranunculaceae Rattleroot (Cimicifuga I.) plant, comprises RHIIZOMA CIMICIFUGAE FOETIDAE or RHIIZOMA CIMICIFUGAE from Northwest of China (Cimicifugafoetida), rhizoma cimicifugae dahuricae or the Rhizoma Cimicifugae Cimicifuga dahurica of Xingan) and Cimicifuga nanchuanensis) etc.According to record, the Rhizoma Cimicifugae medical material has heat-clearing and toxic substances removing, elevate a turnable ladder yang-energy, delivers the function of rash, cures mainly diseases such as headache due to pathogenic wind-heat, toothache, laryngopharynx swelling and pain, uterine prolapse.Xingan's Rhizoma Cimicifugae (C.dahurica Turcz.Maxim.) rhizome is as the loaded Chinese Pharmacopoeia of conventional Chinese medicine (2000 editions), and aerial parts Chang Zuowei garbage.Just begin the aerial parts chemical constituent is studied nearly one or two years, and the result shows that triterpene and Saponin thereof are its main component.Yet the pharmacological research of aerial parts still is blank so far.Total triterpene of rattleroot (C.racemosa) and homemade Rhizoma Cimicifugae (C.foetida) and Saponin thereof can improve castrated rats serum estradiol level, and luteotropic hormone (LH) concentration is reduced, and can suppress the osteoporosis and the climacteric syndrome that cause owing to endocrine regulation, estrogen deficiency.Ferulic acid in the Rhizoma Cimicifugae, Hesperetic acid etc. have anti-inflammatory and analgesic effect, and caffeic acid and derivant thereof have antioxidant activity.Take 40% isopropanol extraction thing of rattleroot rhizome simultaneously, can strengthen the estrogenic antagonist in the estrogen-dependent oncotherapy, in the external inhibitory action that strengthens tamoxifen to the MCF-7 cell proliferation.Compound c imigenol 3-O-a-L-arabinopyranoside that extracts from the rattleroot rhizome and 23-O-acetylshengmanol 3-O-a-L-arabinopyranoside have inhibitory action to human mouth squamous cell carcinoma (HSC-2), and the half suppression ratio is respectively 30um and 18um.Three 9,19 ring lanoline alkane triterpenoid compound 23-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xylosides (23-O-acetylcimigenol-3-O-β-D-xylopyranoside), 24-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside (24-O-acetylcimigenol-3-O-β-D-xylopyranoside), 25-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside (25-O-acetylcimigenol-3-O-β-D-xylopyranoside), all extract Rhizoma Cimicifugae aerial parts, do not see any relevant its active report up to now from the Xingan.
The objective of the invention is on the basis of cytotoxicity, morphocytology, cell cycle experiment and antioxidation experiment at this group chemical compound of research, its practical application in clinical therapy of tumor is released in exploitation.
Summary of the invention:
The invention provides cycloartane (9, the 19 ring lanoline alkane) application of triterpenoid compound in pharmacy.
The present invention includes provides a kind of with cycloartane (9,19 ring lanoline alkane) triterpenoid compound is the pharmaceutical composition of active constituents of medicine, and with cycloartane (9,19 ring lanoline alkane) triterpenoid compound or a kind of antitumor drug of its preparation of pharmaceutical compositions, antitumor medicine-resistant medicine, anti-oxidation medicine, chemoprophylactic drug.Cycloartane triterpenoid compound of the present invention is preferably: 23-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside, 24-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside, 25-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside.
Pharmaceutical composition of the present invention, the cycloartane triterpenoid compound and/or the medicine acceptable carrier that contain the physiology effective dose, the said weight ratio of cycloartane triterpenoid compound in compositions is 0.1-99.9%, and the weight ratio of medicine acceptable carrier in compositions is 0.1-99.9%.
Pharmaceutical composition of the present invention exists to be fit to medicinal dosage form, and these dosage forms are: tablet, sugar coated tablet, film coated tablet, enteric coated tablet, slow releasing tablet, capsule, hard capsule, soft capsule, slow releasing capsule, oral liquid, mixture, suck agent, granule, electuary, pill, powder, unguentum, sublimed preparation, suspensoid, solution, injection, injectable powder, lyophilized injectable powder, suppository, ointment, plaster, cream, spray, aerosol, drop, patch.
Pharmaceutical composition of the present invention, as dosage form, the cycloartane triterpenoid compound 0.1mg-1000mg that contains in every dose, described every dose refers to, and each preparation unit is as every of tablet, capsular every, also can refer to each taking dose, as take 100mg at every turn.
Said one group 9 of the present invention, 19 ring lanoline alkane triterpenoid compound (1), (2), (3) be respectively 23-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside (23-O-acetylcimigenol-3-O-β-D-xylopyranoside), 24-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside (24-O-acetylcimigenol-3-O-β-D-xylopyranoside), 25-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside (25-O-acetylcimigenol-3-O-β-D-xylopyranoside)
Its chemical constitution is as follows:
Chemical compound (1)
23-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside
Chemical compound (2)
24-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside
Chemical compound (3)
25-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside
This group chemical compound all extracts from Xingan's Rhizoma Cimicifugae (Cimicifuga dahrica) aerial parts.Raw material picks up from Inner Mongolia Autonomous Region noise made in coughing or vomiting loudspeaker and secretes flag Mao Jingba, through being accredited as the aerial parts of Rattleroot plant Xingan Rhizoma Cimicifugae (Cimicifuga dahuricaTurcz.Maxim.).To carry out the chemical constituent trial test behind the raw material crushing screening, show that Xingan's Rhizoma Cimicifugae aerial parts mainly contains the triterpenoid saponin constituents.Adopt 80% ethanol to extract thus, obtain ethanol extract.With behind itself and the kieselguhr uniform mixing, carry out column chromatography, carry out eluting with ethyl acetate, the ethyl acetate part (containing total Saponin) that obtains goes up silicagel column, uses the chloroform-methanol gradient elution.Obtain fraction 30-50 part and 68-90 and partly distinguish upper prop once more, 30-50 partly uses hexane-acetone eluting, and the fraction 12-15 part and the fraction 22-26 part that obtain go up the Rp-18 post respectively, use the methanol-water eluting, partly get chemical compound (1) from 12-15; 22-26 part behind the Rp-18 column chromatography, be further purified handle chemical compound (3); 68-90 partly uses chloroform-methanol (95: 5) eluting, and the fraction 18-25 that obtains further uses column chromatography and HPLC purification, gets chemical compound (2).Detailed extraction separation step, available flow chart are illustrated (Fig. 1).
Chemical compound (1) is colourless needle, fusing point 283-285 ℃, and FABMS, IR, 1HNMR, 13CNMR four big spectral datas are consistent with bibliographical information, are 23-O-acetyl cimigenol xyloside so infer chemical compound (1); Chemical compound (2) is a white powder, fusing point 188-190 ℃, and FABMS, IR, 1HNMR, 13CNMR four big spectral datas are consistent with bibliographical information, are 24-O-acetyl cimigenol xyloside so infer chemical compound (2); Chemical compound (3) is colourless needle, fusing point 227-228 ℃, and FABMS, IR, 1HNMR, 13CNMR four big spectral datas are consistent with bibliographical information, are the 25-O-acetylcimigenol xyloside so infer chemical compound (3).
Three chemical compounds that obtain are dissolved the concentrated solution that is made into 20mM with DMSO, carry out cell toxicity test, morphocytology test (cell cycle and apoptosis), cell cycle test and antioxidation test respectively.Cell toxicity test result shows that three chemical compounds all have tumor-inhibiting action preferably to blood tumor, solid tumor and persister.The IC50 value of mice normal liver cell all greater than other tumor cell line, is illustrated that three chemical compounds are lower to Normocellular toxicity when suppressing tumor cell.Cytotoxicity test research also shows, the cytotoxicity that the different side chain of 9,19 ring lanoline alkane triterpenoid compound, different glycosyl all can showed different; The morphocytology result of the test shows that three chemical compounds all can cause with apoptosis and G2/M with the HL-60 cell strain HepG2 stagnates relevant morphological change; The cell cycle result of the test shows that three chemical compounds can make HepG2 stop at the G2/M phase at 30um, and are time-dependent relation.20um 12 hours, make the HL-60 cell stop at the G2/M phase and follow obvious apoptosis; The antioxidation result of the test shows that three chemical compounds all can make absorbance reduce, and the effect of good removing free radical is arranged, and be dose-dependence.
The invention effect:
Three chemical compounds that the present invention relates to all have good lethal effect external to blood tumor (HL-60) and solid tumor (HepG2) and persister, and it is faint relatively to normal mouse liver cell lethal effect, morphocytology and cell cycle evidence, said chemical compound are mainly blocked by cell death inducing and G2/M and are worked.This group chemical compound has the effect of good removing free radical, can prevent the damage of radical pair biomacromolecule.Therefore, said three the cycloartane triterpenoids of the present invention
Can be used asClinical tumor prevention and medicine.
The specific embodiment:
Below listed embodiment help those skilled in the art to understand the present invention better, but do not limit the present invention in any way.
Embodiment 1
Cell toxicity test:
1. material: human hepatoma cell strain (HepG2), people's acute promyelocytic leukemia cell strain (HL-60), all enough in U.S. ATCC (American Type Culture Collection), human liver cancer cell persister (HepG2-R) is an adriamycin-resistant cell (City University of Hong Kong is so kind as to give).Mouse liver cell separate from Kunming mouse (available from Traditional Chinese Medicine University Of Guangzhou's Experimental Animal Center, the animal quality certification number: liver Guangdong probatio inspectionem pecuoarem word 2001A054 number), through former be commissioned to train to support obtain.Culture medium RPMI1640, DMEM, hyclone are all available from Gibico company.MTT (3-(4,5-DIMETHYLTHIAZOL-2-YL)-2,5-diphenyl tetrazolium bromide) be AMRESCO company product, by Shanghai biological engineering company limited packing, lot number: 0481B50.Amycin (doxirubicine), Sigma company product.
Mouse liver cell former be commissioned to train foster: sterilization exposes liver behind the mouse anesthesia, portal catheterization, use heparin, preceding filling liquid, collagenase perfusion successively, take off liver and clean twice with no calcium magnesium Hanks liquid, be transferred to then in the clean culture dish hepatocyte is shaken off in the collagenase solution, it is centrifugal to sieve, wash 3 times with the DMEM culture medium, use the DMEM10% hyclone resuspended then, the trypan blue dyeing counting, living cell rate is more than 80%.
3. tissue culture: HepG2 and HL-60 cell all add conventional cultivation of 10% hyclone with the RPMI1640 culture medium and go down to posterity.The HepG2-R cell culture needs to add amycin again in containing the RPMI1640 culture medium of 10% hyclone, and final concentration is 1.2um.Mouse liver cell is former is commissioned to train to support and adds 10% hyclone with the DMEM culture medium.The conventional method inoculating cell is to 96 orifice plates, and inoculum density is the 10000-20000/ hole.The 5%CO2 incubator is cultivated after 24 hours for 37 ℃, dosing routinely, and matched group adds the DMSO of equivalent.Continuation in the 5%CO2 incubator 37 ℃ cultivated 48 hours.Add MTT, final concentration is 50ug/ml.After 37 ℃ of 5%CO2 incubators are hatched 4 hours, measure absorbance on the Bio-RAD Model 680 MicroPlate Reader, calculate suppression ratio.
4. result:
Three chemical compound 23-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xylosides, 24-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside, 25-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xylosides all can suppress the growth (Fig. 2) of HepG2, HL-60, HepG2-R and mice normal liver cell.Three chemical compounds are close to the IC50 value of HepG2, HL-60, HepG2-R, illustrate that three chemical compounds all have tumor-inhibiting action preferably to blood tumor, solid tumor and persister.To the IC50 value of mice normal liver cell all greater than other tumor cell line, illustrate three chemical compounds when suppressing tumor cell to Normocellular toxicity weak (table 1).
Three chemical compounds of table 1. are to the IC50 value of four cell strains
| Cell strain | Chemical compound (1) (um) | Chemical compound (2) (um) | Chemical compound (3) (um) |
| HepG2 | ????27 | ????13 | ????22 |
| HL-60 | ????13 | ????12 | ????10 |
| HepG2-R | ????20 | ????10 | ????30 |
| Mice?hepatocyte | ????43 | ????38 | ????35 |
Embodiment 2
Morphocytology test (cell cycle and apoptosis):
1. method: contain in the culture dish of HepG2 and HL-60 cell at 35 * 10mm, administration respectively is after effect a period of time, add 400ulAO/EB staining solution (100ug/ml AO solution, 100ug/ml EB solution is prepared with PBS), mixing is observed under 40 * 10 fluorescence inverted microscopes immediately.AO solution all can dye to living cells and dead cell, and EB solution is only to losing the cell dyeing of film conformability, and living cells still presents uniform green.It is green that viable apoptotic cell is, because chromatin agglutination and karyorhexis have viridian speckle in its nucleus.Apoptosis cell in late period can be dyed orange by EB, but different with dead cell, and the nuclear of apoptosis cell in late period presents cohesion and usually cracking.Non-viable non-apoptotic cell is dyed orange, but possesses the nuclear morphology of living cells sample, does not present chromatin agglutination.
2. result: observe of the influence of three chemical compounds to HepG2 and HL-60 morphocytology, find that it all can cause the morphological change that apoptosis and G2/M stagnate to two cell strains, and can make the HL-60 cell elongated, be a kind of rare morphological change relevant with the G2/M stagnation with apoptosis.The positive drug harringtonine can cause two typical apoptosis morphological change of cell strain (Fig. 3-15).
Embodiment 3
The cell cycle test:
1. material: RNase A (USB company product), 81.4units/mg, lot number: 110266-007; PI (propidiumiodide) (Sigma company product, lot number: 042k3655).
2. method: conventional method is cultivated HepG2 and HL-60 cell, and collecting cell after the administration is washed twice back with PBS and spent the night with 70% alcohol fixation.The centrifugal ethanol that goes of 1000rpm/10min, wash twice with the PBS that contains 1% hyclone, it is resuspended to contain the PBS of 1% hyclone with 2ml again, adds RNase enzyme (final concentration 0.5mg/ml) digestion 1 hour, add PI (2.5ug/ml) dyeing then, place 20min on ice after the up flow type cell instrument detect.
3. result: three chemical compounds can make HepG2 stop at the G2/M phase at 30um, and are time-dependent relation (table 2).20um 12 hours, make the HL-60 cell stop at the G2/M phase and follow obvious apoptosis (table 3) (Figure 16-19).
Three chemical compounds of table 2. are to the influence of HepG2 cell cycle
| Chemical compound | Time (hour) | Apoptosis % | ?G0/G1％ | ?S％ | ?G2/M％ |
| Contrast | ?- | ?0±0 | ?62.68±2.49 | ?31.62±2.07 | ?8.33±1.53 |
| Chemical compound 1 | ?6 | ?0.89±0.82 | ?42.9±0.49 | ?34.32±0.43 | ?22.78±0.16 |
| ?10 | ?0±0 | ?35.51±0.32 | ?37.48±0.68 | ?27.01±0.95 | |
| ?12 | ?10.23±2.97 | ?29.71±2.50 | ?39.87±4.05 | ?30.41±1.55 | |
| Chemical compound 2 | ?6 | ?1.07±1.73 | ?38.02±1.04 | ?44.31±1.50 | ?17.68±2.41 |
| ?10 | ?1.85±1.31 | ?37.04±0.87 | ?38.34±0.91 | ?24.62±0.52 | |
| ?12 | ?13.64±5.00 | ?42.45±0.43 | ?28.90±1.09 | ?28.65±1.11 | |
| Chemical compound 3 | ?6 | ?0±0 | ?40.59±0.15 | ?35.84±0.51 | ?23.57±0.51 |
| ?10 | ?0±0 | ?34.56±0.29 | ?39.27±1.14 | ?26.17±1.31 | |
| ?12 | ?16.44±1.20 | ?44.40±1.90 | ?30.09±2.39 | ?53.46±42.31 |
Three chemical compounds of table 3. are to the influence of HL-60 cell cycle
| Chemical compound | Apoptosis % | ?G0/G1％ | ?S％ | ?G2/M％ |
| Contrast | ?0.33±0.24 | ?38.03±0.86 | ?48.46±1.10 | ?13.52±0.32 |
| Chemical compound 1 | ?47.94±4.73 | ?17.24±2.64 | ?57.29±4.21 | ?26.80±43.64 |
| Chemical compound 2 | ?13.64±5.00 | ?42.45±0.43 | ?28.90±1.09 | ?28.65±1.10 |
| Chemical compound 3 | ?44.40±1.90 | ?16.44±1.20 | ?30.09±2.39 | ?53.46±2.31 |
Embodiment 4
The antioxidation test:
1. materials and methods
DPPH (1, be a kind of more stable free radical 1-Diphenyl-2-picrylhydrazyl), 1 free electron is arranged on its N, therefore maximum absorption honeybee is arranged at the 517nm place, its methanol solution is purple.Add after the antioxidant, DPPH catches 1 electronics and free electron pairing, and the absorption at the 517nm place disappears, and purple takes off.Therefore by DPPH is in the decline of 517nm place absorption value behind the mensuration adding antioxidant, antioxidant is to the scavenging action of DPPH as can be seen.
Add chemical compound to DPPH (concentration is 2.4mg/ml MeOH), react after 1.5 hours, measure its absorbance on UV, the detection wavelength is 515nm.
Blank: sample+MeOH
Contrast: DMSO+DPPH
Sample: sample+DPPH
Free radical scavenging activity: SR=(1-A
1/ A
0) * 100%
A
1: the absorbance of sample
A
0: the absorbance of contrast
2. result: three chemical compounds all can make absorbance reduce, and the effect of good removing free radical (antioxidation) is arranged, and be dose-dependence (Figure 20).
Embodiment 5
The preparation of capsule
Chemical compound 1 240g
Microcrystalline cellulose vegetable dish 40g
Pulvis Talci 1.4%
3% polyvidone alcoholic solution is an amount of
Make 1000 altogether
Get prescription quantification compound 1 and recipe quantity microcrystalline Cellulose mix homogeneously, add 3% polyvidone alcoholic solution system soft material, cross 18 mesh sieve system granules, 50 ℃ (the gained granule was held dried granule with hand-tight, and hands loosens and causes granule and should not bond agglomerating in dry 30-45 minute, palm does not have that fine powder adheres to yet or should pulverize immediately when being twined with forefinger and thumb granule, the free from dampness sense) granulate adds Pulvis Talci, mixing, fill in No. 1 capsule, promptly get every and contain the 240mg capsule.
Embodiment 6:
The preparation of tablet
Chemical compound 2 10g
Microcrystalline Cellulose 40g
Pulvis Talci 1.4%
3% polyvidone alcoholic solution is an amount of
Make 1000 altogether
Get prescription quantification compound 2 and recipe quantity microcrystalline Cellulose mix homogeneously, add 3% polyvidone alcoholic solution system soft material, cross 18 mesh sieve system granules, 50 ℃ (the gained granule was held dried granule with hand-tight, and hands loosens and causes granule and should not bond agglomeratingly, and palm does not have that fine powder adheres to yet or should pulverize immediately when being twined with forefinger and thumb granule in dry 30-45 minute, the free from dampness sense) granulate, add Pulvis Talci, mixing, tabletting.
Embodiment 7
The preparation of granule
Chemical compound 3 500g
Microcrystalline cellulose vegetable dish 40g
Pulvis Talci 1.4%
3% polyvidone alcoholic solution is an amount of
Make 500 bags altogether
EGCG is pulverized, cross 80 mesh sieves, get recipe quantity EGCG and recipe quantity microcrystalline Cellulose mix homogeneously, add 3% polyvidone alcoholic solution system soft material, cross 18 mesh sieve system granules, 50 ℃ (the gained granule was held dried granule with hand-tight in dry 30-45 minute, hands loosens and causes granule and should not bond agglomerating, palm does not have that fine powder adheres to yet or should pulverize the free from dampness sense immediately when being twined with forefinger and thumb granule) granulate, pack
Embodiment 8
The preparation of injection
Chemical compound 3 100g
Soil temperature-80 40g
Sorbitol 10g
Add normal saline to 1000ml
Make 1000 bottles altogether
Get prescription quantification compound 3 and recipe quantity soil temperature-80 and sorbitol mix homogeneously, add an amount of normal saline and make dissolving, filter, packing, sterilization, packing is promptly.
Description of drawings:
Fig. 1: the separation and Extraction flow chart of three chemical compounds
Fig. 2: the cell toxicity test of three chemical compounds
Fig. 3: HepG2 normal cell form
Fig. 4: HepG2 harringtonine-20um-6 hour positive control
Fig. 5: HepG2 chemical compound (1)-20um-12 hour
Fig. 6: HepG2 chemical compound (2)-20um-12 hour
Fig. 7: HepG2 chemical compound (3)-20um-12 hour
Fig. 8: HL-60 normal cell form
Fig. 9: HL-60 harringtonine-20um-6 hour positive control
Figure 10: HL-60 chemical compound (1)-20um-12 hour
Figure 11: HL-60 chemical compound (2)-20um-12 hour
Figure 12: HL-60 chemical compound (3)-20um-12 hour
Figure 13: HL-60 chemical compound (1)-20um-24 hour
Figure 14: HL-60 chemical compound (2)-20um-24 hour
Figure 15: HL-60 chemical compound (3)-20um-24 hour
Figure 16: HL-60 normal cell periodogram
Figure 17: HL-60 chemical compound (1)-20um-12 hour cell periodogram
Figure 18: HL-60 chemical compound (2)-20um-12 hour cell periodogram
Figure 19: HL-60 chemical compound (3)-20um-12 hour cell periodogram
Figure 20: the antioxidation of three chemical compounds
Claims (10)
1. pharmaceutical composition, it is characterized in that: contain the cycloartane triterpenoid compound and/or the medicine acceptable carrier of physiology effective dose, described cycloartane triterpenoid compound is: 23-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside, 24-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside, 25-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside.
2. the compositions of claim 1, it is characterized in that: the weight ratio of described cycloartane triterpenoid compound in compositions is 0.1-99.9%, and the weight ratio of medicine acceptable carrier in compositions is 0.1-99.9%.
3. the compositions of claim 1 is characterized in that, described cycloartane triterpenoid compound is: 23-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside.
4. the compositions of claim 1 is characterized in that, described cycloartane triterpenoid compound is: 24-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside.
5. the compositions of claim 1 is characterized in that, described cycloartane triterpenoid compound is: 25-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside.
6. each compositions among the claim 1-5, it is characterized in that, be to be fit to medicinal dosage form, these dosage forms are: tablet, sugar coated tablet, film coated tablet, enteric coated tablet, slow releasing tablet, capsule, hard capsule, soft capsule, slow releasing capsule, oral liquid, mixture, suck agent, granule, electuary, pill, powder, unguentum, sublimed preparation, suspensoid, solution, injection, injectable powder, lyophilized injectable powder, suppository, ointment, plaster, cream, spray, aerosol, drop, patch.
7. cycloartane triterpenoid compound or its compositions treat and/or prevent application in the tumour medicine in preparation, and described cycloartane triterpenoid compound is: 23-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside, 24-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside, 25-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside.
8. cycloartane triterpenoid compound or its compositions application in preparation antitumor medicine-resistant medicine, described cycloartane triterpenoid compound is: 23-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside, 24-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside, 25-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside.
9. cycloartane triterpenoid compound or its compositions application in the preparation anti-oxidation medicine, described cycloartane triterpenoid compound is: 23-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside, 24-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside, 25-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside.
10. cycloartane triterpenoid compound or its compositions application in the preparation chemoprophylactic drug, described cycloartane triterpenoid compound is: 23-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside, 24-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside, 25-oxygen-acetyl cimicifugol .-3-oxygen-β-D-xyloside.
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| CN101463058B (en) * | 2007-12-18 | 2011-04-20 | 中国科学院上海药物研究所 | Lanoline alkane type triterpenoid sexangulic acid, derivative thereof and preparation and use thereof |
| CN102391279A (en) * | 2011-10-06 | 2012-03-28 | 中国科学院昆明植物研究所 | Methyl 3,4-seco-4-hydroxy-3-cimigenolate, medicinal composition containing same and preparation method and application thereof |
| CN108530509A (en) * | 2018-05-31 | 2018-09-14 | 中国科学院昆明植物研究所 | A kind of macrotin glycosides-cimicifugae foetidae triterpene glycosides condensation product and its isolation and purification method and purposes |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100443495C (en) * | 2006-06-07 | 2008-12-17 | 肖培根 | Triterpene saponin compound of cycro jackfruit alkyl, and effect for anti tumor |
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2003
- 2003-09-17 CN CN 03157172 patent/CN1225248C/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101463058B (en) * | 2007-12-18 | 2011-04-20 | 中国科学院上海药物研究所 | Lanoline alkane type triterpenoid sexangulic acid, derivative thereof and preparation and use thereof |
| CN102391279A (en) * | 2011-10-06 | 2012-03-28 | 中国科学院昆明植物研究所 | Methyl 3,4-seco-4-hydroxy-3-cimigenolate, medicinal composition containing same and preparation method and application thereof |
| CN102391279B (en) * | 2011-10-06 | 2013-08-21 | 中国科学院昆明植物研究所 | Methyl 3,4-seco-4-hydroxy-3-cimigenolate, medicinal composition containing same and preparation method and application thereof |
| CN108530509A (en) * | 2018-05-31 | 2018-09-14 | 中国科学院昆明植物研究所 | A kind of macrotin glycosides-cimicifugae foetidae triterpene glycosides condensation product and its isolation and purification method and purposes |
| CN108530509B (en) * | 2018-05-31 | 2020-06-19 | 中国科学院昆明植物研究所 | Shengma glucoside-cimicifuga triterpenoid glycoside condensate, and separation and purification method and application thereof |
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| Publication number | Publication date |
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| CN1225248C (en) | 2005-11-02 |
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