CN102614208B - Application of compound (20R,24R)-24,25-16,23-23,27-triepoxy-12-acetoxyl-9,19-cyclolanostanol-3-O-beta-D xylopyranoside in pharmacy - Google Patents
Application of compound (20R,24R)-24,25-16,23-23,27-triepoxy-12-acetoxyl-9,19-cyclolanostanol-3-O-beta-D xylopyranoside in pharmacy Download PDFInfo
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Abstract
The invention relates to an application of a compound DA (20R,24R)-24,25-16,23-23,27-triepoxy-12-acetoxyl-9,19-cyclolanostanol-3-O-beta-D xylopyranoside extracted from cimicifugae foetidae in pharmacy, in particular to an application of the compound DA in preparation of medicines for resisting breast cancer as well as a preparation method for the compound DA.
Description
Affiliated field:
The invention belongs to field of pharmacology, particularly, relate to the i.e. (20R of a kind of Compound D A that from Rhizoma Cimicifugae, extracts, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-9,19-cyclolanostan-3-O-β-D-xylopyranose glucoside [(20R, 24R)-24,25-16,23-23,27-triepoxy-12-acetoxyl-9,19-Cyclolanostanol-3-O-β-D-xylopyranoside] application, the particularly application in the medicine of preparation anti-breast cancer in the preparation antitumor drug.
Background technology:
Rhizoma Cimicifugae is China's famous Chinese medicine very commonly used, is mainly the dry rhizome of ranunculaceae plant SANYE Rhizoma Cimicifugae Cimicifuga heracleifolia Kom, Cimicifuga Dahurica C.dahurica Maxim, Rhizoma Cimicifugae or RHIIZOMA CIMICIFUGAE C.foetida L..The rhizome of these three kinds of medicinal plants as Chinese medicine Rhizoma Cimicifugae medical material, records into the Pharmacopoeia of the People's Republic of China (version in 2010).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, the diseases such as uterine prolapse.Rhizoma Cimicifugae Cimicifuga foetida L. mainly originates in the ground such as Yunnan, Guizhou, Sichuan, Hubei, is a large amount of cultivations or wild parts of generic medicinal plants.
Congener Radix vernoniae asperae (Cimicifuga racemosa L.) claims again Herba ophiorrhizae japonicae, also has very long use historical in American-European countries.Indians drink the Radix vernoniae asperae medicine juice relieving fatigue of decoction, and the diseases such as treatment laryngalgia, arthritis and venom also are used for the treatment of some gynaecopathias simultaneously, and are incorporated into American Pharmacopeia at 1820-1926.Britain also is written into British Herbal Pharmacopoeia with Radix vernoniae asperae, and Linnaeus in 1749 is with Radix vernoniae asperae income " Materia Medica ", and 20 beginnings of the century became one of hahnemannian main medicine.
The chemical composition of Rattleroot plant and pharmacology activity research are domestic and international study hotspots always.Obtain more than 200 of triterpene and glycoside thereof, Phenylpropanoid Glycosides class, chromone and other type compounds from wherein separating over past ten years.In the world the research of chemical composition in the Rhizoma Cimicifugae is mainly concentrated on it and three pastes on saponins composition, to its pharmacology activity research then take oestrogen-like hormone, osteoporosis as main.All developed respectively the medicine for the treatment of climacteric syndrome and osteoporosis in developed countries such as Germany, Japan, the U.S..Different from the focus of in the world research, the present invention takes full advantage of Yunnan Province's Rhizoma Cimicifugae resource in order to expand the frontier of Rhizoma Cimicifugae triterpenoid research, develops its new purposes.
Summary of the invention:
The present invention aims to provide the i.e. (20R of a kind of Compound D A that extracts from Rhizoma Cimicifugae, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-9,19-cyclolanostan-3-O-β-D-xylopyranose glucoside [(20R, 24R)-24,25-16,23-23,27-triepoxy-12-acetoxyl-9,19-Cyclolanostanol-3-O-β-D-xylopyranoside] application in the preparation antitumor drug, and the preparation method of Compound D A.
Above-mentioned purpose of the present invention is realized with following technical scheme:
Chemical compound (20R, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-9, the application of 19-cyclolanostan-3-O-β-D-xylopyranose glucoside in the preparation antitumor drug.
Chemical compound (20R, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-9, the application of 19-cyclolanostan-3-O-β-D-xylopyranose glucoside in the preparation anti-breast cancer medicines.
Chemical compound (20R, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-9, the preparation method of 19-cyclolanostan-3-O-β-D-xylopyranose glucoside, get Rhizoma Cimicifugae Cimicifuga foetida L. dry rhizome, after pulverizing with 80% methanol extraction three times, each 4 hours; After 80% 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, use petroleum ether extraction 2-3 time, behind the recovery petroleum ether, the concentrated Petroleum ether extraction position that obtains; Then water layer is used chloroform extraction 2-3 time again, reclaims chloroform, the concentrated chloroform extraction position that obtains; Separate with silica gel column chromatography at the chloroform extraction position, eluent was with 40: 1 chloroform: methanol or chloroform: acetone is eluting repeatedly, eluting post crystallization purification gets chemical compound (20R, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-9,19-cyclolanostan-3-O-β-D-xylopyranose glucoside.
Chemical compound (20R, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-9, the preparation method of 19-cyclolanostan-3-O-β-D-xylopyranose glucoside is got Rhizoma Cimicifugae Cimicifuga foetida L. dry rhizome, after pulverizing with 90 ℃ of reflux, extract, of methanol aqueous solution of 80% 3 times, after extracting solution is removed most of methanol, use respectively petroleum ether, chloroform, n-butanol extraction; After reclaiming solvent, get petroleum ether part, chloroform part, n-butyl alcohol part; Chloroform is partly used silica gel mixed sample, silica gel column chromatography; With 1: 0,40: 1,20: 1,10: 1 chloroform: the methanol gradient elution, TLC combining data detection same section obtains four component Fr.A-D; Fr.B silica gel mixed sample wherein, silica gel column chromatography, the normal pressure chromatography, with 40: 1 chloroforms: methanol is elution chromatography repeatedly, obtain chemical compound (20R, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-9,19-cyclolanostan-3-O-β-D-xylopyranose glucoside.
Chemical compound (20R of the present invention, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-9,19-cyclolanostan-3-O-β-D-xylopyranose glucoside (be called for short DA) can be directly as drug use, and all the other adjuvants are acceptable on the materia medica, pharmaceutical carrier or the excipient of and inertia nontoxic to humans and animals.
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 extract or effective site are used with the form of per weight dose.But two kinds of form administrations of medicine oral administration of the present invention and mouthspray.
Oral available its solid or liquid preparation are such as powder, tablet, sugar coated tablet, capsule, tincture, syrup, drop pill etc.
Mouthspray can be with its solid or liquid preparation.
Medicine of the present invention can be used for treatment and prevention antitumor, is used in particular for treating breast cancer disease.Medicine of the present invention has the curative effect highly significant, and is rapid-action, and dosage is low, makes things convenient for the advantages such as patient.
Description of drawings:
Fig. 1: each group nude mice photo, Figure 1A model control group; Figure 1B tamoxifen group; Fig. 1 C Compound D A high dose; Dosage among Fig. 1 D Compound D A; Fig. 1 E Compound D A low dosage;
Fig. 2: each group tumor photo, Fig. 2 A model control group; Fig. 2 B tamoxifen group; Fig. 2 C Compound D A high dose; Dosage among Fig. 2 D Compound D A; Fig. 2 E Compound D A low dosage.
The specific embodiment:
Below in conjunction with accompanying drawing, further specify essentiality content of the present invention with embodiments of the invention, but do not limit the present invention with this.
Embodiment 1:
Chemical compound (20R, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-9, the separation preparation of 19-cyclolanostan-3-O-β-D-xylopyranose glucoside (DA):
1, plant characteristics and sample source:
RHIIZOMA CIMICIFUGAE Cimicifuga foetida L. is distributed in the provinces such as China Tibet, Yunnan, Sichuan, Gansu, Shaanxi, West Henan and Shanxi.Be born in the mountain region border woods dark and damp between height above sea level 1700-3500 rice or in the thick grass in roadside.Be herbaceos perennial, root stock is sturdy, and is solid and slightly be with woodenly, and crust black is given birth to most radiculas.Stem is single, and Chang Gaoda is upright, cylindrical, usually at top minority branch.Ye Weiyi is back to three times three and goes out or nearly winglike compound leaf, and long handle is arranged; Lobule is avette, rhombus or narrow ellipse, and the edge has the rough sawn tooth.Inflorescence is raceme, usually the integrated coniform inflorescence of 2-30 bar.Spend the annual 7-8 month open, white, petal-shaped, the shape of falling the ovum is circular.The seed minority, oval to narrow ellipse, yellowish-brown is given birth to membranous squama wing usually all around, and the horizontal squama wing of the back of the body, the outside of belly is obvious or not obvious, and the 9-10 month is ripe.
Rhizoma Cimicifugae (Cimicifuga foetida L.) plant sample picked up from Yulong county, Lijiang County In Yunnan Province city in 2006; Plant specimen is identified by the Kunming Institute of Zoology Pei Shengji researcher of the Chinese Academy of Sciences.
2, the separation of Compound D A preparation:
10 kilograms on dry Rhizoma Cimicifugae rhizome with 90 ℃ of reflux, extract, of methanol aqueous solution of 80% 3 times, after extracting solution is removed most of methanol, is used respectively petroleum ether, chloroform, n-butanol extraction after pulverizing.After reclaiming solvent, get petroleum ether part 50 grams, chloroform part 900 grams, n-butyl alcohol part 500 grams.Chloroform part 900 restrains with 1 kilogram of silica gel mixed sample, 1 kilogram of silica gel column chromatography.Chloroform: methanol (1: 0,40: 1,20: 1,10: 1) gradient elution, TLC combining data detection same section obtains four component: Fr.A-D.Fr.B (300 gram) wherein, 300 gram silica gel mixed samples, 1 kilogram of silica gel column chromatography, the normal pressure chromatography, use chloroform: methanol (40: 1) is elution chromatography repeatedly, obtains Compound D A (1.0g).
3. the structural characterization of Compound D A:
Compound D A:C
37H
56O
10, colourless needle, mp 253-254 ℃, [α]
D=-61.2 ° of (c=0.255, CHCl
3-CH
3OH (1: 1)).
Hydrogen nuclear magnetic resonance spectrum data δ (ppm) (solvent Py-d5): 5.10 (1H, brd, J=5.3Hz, 12-H); (4.23 1H, brd, J=6.7Hz, 16-H), 4.05 (1H, d, J=10.4Hz, 26-H), 4.04 (1H, s, 24-H), 3.62 (1H, d, J=10.4Hz, 26-H), 3.44 (1H, dd, J=10.8,3.4Hz, 3-H); (1.45 3H, s, 27-H), 1.40 (3H, s, 18-H), 1.29 (3H, s, 29-H), 1.00 (3H, d, J=6.7Hz, 21-H), 0.99 (3H, s, 30-H), 0.83 (3H, s, 28-H), (0.52 1H, d, J=3.8Hz, 19-H), (0.19 1H, d, J=3.8Hz, 19-H).12-COCH
3Part: 2.12 (3H, s, 2 '-COCH
3).Xylose part: 4.83 (1H, d, J=7.2Hz, 1 '-H), 4.04 (1H, t, J=10.4Hz, 2 '-H), 4.10 (1H, t, J=8.6Hz, 3 '-H), 4.20 (1H, m, 4 '-H); 3.71 (1H, t, J=10.4Hz, 5 '-H), 3.35 (1H, dd, J=4.2,10.4Hz, 5 '-H).
Nuclear magnetic resonance of carbon spectrum data δ (ppm) (solvent Py-d5): 105.9 (s, 23-C), 88.1 (d, 3-C), 77.0 (d, 12-C), 74.5 (d, 16-C), 68.1 (t, 26-C), (62.5 s, 25-C), 62.3 (d, 24-C), 56.2 (d, 17-H), 48.8 (s, 13-C), 47.9 (s, 14-H), (47.0 s, 5-C), 45.6 (d, 8-C), (44.2 t, 15-C), 41.22 (s, 4-C), (37.6 t, 22-C), 36.6 (t, 11-C), (31.9 t, 1-C), 29.9 (t, 2-C), (29.8 t, 19-C), 26.7 (s, 10-C), (25.7 t, 7-C), 25.7 (q, 29-C), (23.3 d, 20-C), 21.3 (q, 21-C), (20.3 t, 6-C), 20.1 (s, 9-C), (19.6 q, 28-C), 15.3 (q, 30-C), (14.3 q, 18-C), 13.4 (q, 27-C).12-COCH
3Part: 171.6 (s, CO), 21.6 (q, COCH
3).Xylose part: 107.5 (d, 1 '-C), 75.6 (d, 2 '-C), 78.6 (d, 3 '-C), 71.2 (d, 4 '-C), 67.1 (t, 5 '-C).
4. the chemical constitution of Compound D A:
The chemical constitution of Compound D A is deoxidation A Ke Paclitaxe (Deoxy-Actein): (20R, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-9,19-cyclolanostan-3-O-β-D-xylopyranose glucoside [(20R, 24R)-24,25-16,23-23,27-triepoxy-12-acetoxyl-9,19-Cyclolanostanol-3-O-β-D-xylopyranoside]
Embodiment 2:
Make reactive compound DA by embodiment 1, add excipient, pelletizing press sheet in DA and 1: 1 ratio of excipient weight ratio.
Embodiment 8:
Make reactive compound DA by embodiment 1, add excipient, pelletizing press sheet in DA and 1: 2 ratio of excipient weight ratio.
Embodiment 9:
Make reactive compound DA by embodiment 1, the capsule preparations method is made capsule routinely.
Embodiment 10:
Make reactive compound DA by embodiment 1, make as follows again tablet
Tablet:
Embodiment 11:
Capsule: reactive compound DA 100mg
Starch is an amount of
Magnesium stearate is an amount of
Preparation method: reactive compound DA is mixed with auxiliary agent, sieve, in suitable container, evenly mix, the mixture that the obtains hard gelatin capsule of packing into.
Embodiment 12:
Nasal spray:
Preparation method: in the double distilled water of proper volume, add a kind of composition under stirring at every turn, until fully dark solution, and then add another kind of composition.After adding water to 2ml, this solution is filtered at sterilizing filter, separate in the bottle of packing into and according to suitable dosage.
Embodiment 13
Drop pill: reactive compound DA 1g
Polyethylene glycol 6000 9g
Method for making: the preparation of reactive compound DA and polyethylene glycol 6000 fused solution: take by weighing reactive compound DA by above-mentioned recipe quantity and add an amount of dehydrated alcohol, after the slight fever dissolving, in the Polyethylene Glycol fused solution of adding recipe quantity (60 ℃ of water bath heat preservations), mix, until till ethanol waves to the greatest extent, be statically placed in 60 ℃ of water-baths and be incubated 30 minutes, treat that bubble eliminates, the above-mentioned mixing fused solution that then will eliminate bubble changes in the surge drum, under the condition of 80-85 ℃ of insulation, speed is dripped in control, splashes into dropwise in the condensed fluid, waits condensation complete, condensed fluid inclines, collect drop pill, drop is clean and remove condensed fluid on the ball with filter paper, places in the silica gel drier or natural drying gets final product.
Below further illustrate the beneficial effect of medical compounds of the present invention by test example:
Test example 1:
Compound D A is to human breast cancer cell BcAP-37 bare mouse different species Growth of Tumors Transplanted inhibitory action:
This experiment entrusts Nanjing KaiJi Biology Science Development Co., Ltd to finish experiment and data analysis is processed.
1, experiment purpose:
According to the requirement of " antitumor drug pharmacodynamics guideline " and " cell toxicant series antineoplastic medicament non-clinical study technological guidance principle ", test compounds A and Compound D A have or not inhibitory action and action intensity to human breast cancer cell BcAP-37 bare mouse different species Growth of Tumors Transplanted.
2, tested medicine: Compound D A
Compound method: be diluted to desired concn with 5% sodium carboxymethyl cellulose before each administration
3, positive control medicine: Tamoxifen Citrate (Yangzijiang Pharmaceutical Group Co., Ltd's product; Lot number: 09052001)
Compound method: before each administration with normal saline dilution to desired concn
4, group and dosage setting:
Model control group: 0.1ml/ gastric infusion of 5% sodium carboxymethyl cellulose continuous 14 days once a day;
Positive drug matched group: Tamoxifen Citrate 2mg/Kg gastric infusion continuous 14 days once a day;
Compound D A high dose group: 27mg/Kg gastric infusion continuous 14 days once a day;
Dosage group among the Compound D A: 9mg/Kg gastric infusion continuous 14 days once a day;
Compound D A low dose group: 3mg/Kg gastric infusion continuous 14 days once a day;
5, animal subject:
Source, kind system, strain: the BALB/c nude mouse provides (laboratory animal production licence: SCXK (Shanghai) 2007-0005 by Shanghai Slac Experimental Animal Co., Ltd.; Laboratory animal occupancy permit: SYXK (army) 2007-030).
Age in days: 35-40 days
Body weight: 18-22g
Sex: male
Number of animals: 8 every group, totally 40
6, transplanted tumor:
Human breast cancer cell BcAP-37 Nude Mice is inoculated in the nude mouse axillary fossa by human breast cancer cell BcAP-37 cell strain subcutaneous and set up.The cell inoculum concentration is 1 * 10
6, inoculation is used after forming and passing for 3 generations again in the nude mouse body after the transplanted tumor.
7, experimental technique:
The tumor tissue of getting the growth animated period cuts into 1.5mm
3About, under aseptic condition, be prepared into 1 * 10 after the homogenate
7/ ml cell suspension is inoculated in nude mouse right side axillary fossa with 0.1ml subcutaneous.Nude Mice treats that with vernier caliper measurement transplanted tumor diameter tumor growth is to 100mm
3After with the animal random packet, 5 every group.Use the method for measuring the tumor footpath, dynamically observe tested thing antineoplastic effect.Model control group intravenous injection equivalent normal saline solution.After the administration 27 days, mice is put to death, and operation strips the tumor piece and weighs.The computing formula of gross tumor volume (tumor volume, TV) is:
TV＝1/2×a×b
2
Wherein a, b represent respectively length and width.
Calculate relative tumour volume (relative tumor volume, RTV) according to the result who measures, computing formula is: RTV=V
t/ V
0V wherein
0(d during for minute cage administration
0) measurement gained gross tumor volume, V
tGross tumor volume when measuring each time.The evaluation index of anti-tumor activity is relative tumor proliferation rate T/C (%), and computing formula is as follows:
T
RTV: treatment group RTV; C
RTV: negative control group RTV.
8, experimental data (see Table 1, table 2 and Fig. 1, Fig. 2).
9, result and discussion:
Compound D A the results are shown in Table 1,2 and Fig. 1,2 to the experimental treatment of human breast cancer cell BcAP-37 Nude Mice.The experimental result demonstration, Compound D A has certain growth inhibited effect to human breast cancer cell BcAP-37 Nude Mice.
Compound D A is with 27mg/kg, 9mg/kg, 3mg/kg gastric infusion, successive administration is in the time of 14 days, T/C (%) to human breast cancer cell BcAP-37 Nude Mice is respectively 70.02%, 62.65%, 60.08%, inhibitory rate 54.8%, 50.02%, 47.5%; When Tamoxifen Citrate is take the 2mg/kg gastric infusion under the similarity condition to the T/C (%) of human breast cancer cell BcAP-37 Nude Mice as 71.46%, tumour inhibiting rate is 33.6%.Show that Compound D A is better than the inhibitory action of human breast cancer cell BcAP-37 Nude Mice or near a line clinical treatment medicine Tamoxifen Citrate sheet, be the promising treatment tumor of tool natural drug.
10, conclusion:
Compound D A has certain growth inhibited effect to human breast cancer cell BcAP-37 Nude Mice.
Table 1. Compound D A is on impact (X ± SD, n=6, the gross tumor volume: the mm of unit of human breast cancer cell BcAP-37 bare mouse different species Growth of Tumors Transplanted change in volume
3)
Compare with the blank group,
*P＜0.05,
*P＜0.01;
Table 1. Compound D A is on impact (continuing) (X ± SD, n=6, the gross tumor volume: the mm of unit of human breast cancer cell BcAP-37 bare mouse different species Growth of Tumors Transplanted change in volume
3)
Compare with the blank group,
*P＜0.05,
*P＜0.01;
Table 2. compd A and Compound D A are to the inhibitory action of human breast cancer cell BcAP-37 bare mouse different species Growth of Tumors Transplanted (X ± SD)
Compare with the blank group,
*P＜0.05,
*P＜0.01
Claims (1)
1. chemical compound (20R, 24R)-24,25-16,23-23,27-three epoxies-12-acetoxyl group-9,19-cyclolanostan-3-O-β-D-xylopyranose glucoside is as the application of unique active component in the preparation anti-breast cancer medicines.
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