CN103054889A - Antineoplastic application of Hederagenin-3-O-arabinopyranoside - Google Patents
Antineoplastic application of Hederagenin-3-O-arabinopyranoside Download PDFInfo
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- CN103054889A CN103054889A CN2012105661707A CN201210566170A CN103054889A CN 103054889 A CN103054889 A CN 103054889A CN 2012105661707 A CN2012105661707 A CN 2012105661707A CN 201210566170 A CN201210566170 A CN 201210566170A CN 103054889 A CN103054889 A CN 103054889A
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- hederagenin
- arabinopyranoside
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Abstract
The invention relates to application of hederagenin-3-O-arabinopyranoside (hederagenin-3-O-arabinopyranoside). The Hederagenin-3-O-arabinopyranoside is obtained by utilizing a chemical extraction separation method. The chemical compound structure of the hederagenin-3-O-arabinopyranoside is identified by utilizing physical constants and spectroscopy methods to carry out an antineoplastic pharmacological testing for the hederagenin-3-O-arabinopyranoside, a result shows that the hederagenin-3-O-arabinopyranoside has good effect on antineoplastic aspects ,especially has good effects on restraining human breast cancer cells, sarcoma cells, gastric carcinoma cells, hepatoma carcinoma cells and prostate cancer cells. The hederagenin-3-O-arabinopyranoside can be used for preparing medicines for curing breast cancer, solid tumor, gastric cancer, liver cancer and prostate cancer.
Description
Technical field
The present invention relates to Hederagenin-3-O-arabinopyranoside(helexin-3-O-galactoside) application aspect anti-curing oncoma, belong to field of medicaments.
Background technology
Cancer is one of current harm humans health and principal disease of orthobiosis, particularly in recent years, deterioration along with environment, obvious ascendant trend has appearred in the sickness rate of malignant tumor, the research and development of cancer therapy drug are the hot subjects that scientist selects always, and researching and developing antitumor drug novel, efficient and low toxicity has become the task of top priority.The anticancer active constituent that filters out from higher plant has in the world at present reached 6.7 ten thousand kinds, for great scope of land has been opened up in the treatment of malignant tumor.China also belongs to 28 sections, and the Chinese herbal medicine more than 3000 kinds has carried out the antitumor screening, and wherein effectively about 200 kinds, the hit rate of a large amount of research work proof screening antineoplastic agents from natural animal and plant medicine is more much higher than synthetic drug.In addition, because the toxic and side effects of natural drug is little, promote people to produce the idea of " going back to nature ", so the extremely people's attention of screening natural antitumor medicine, the work of particularly seeking anticarcinogen from Chinese herbal medicine is just in the ascendant.
Hederagenin-3-O-arabinopyranoside is a saponins compound, is present in the various plants such as Radix Caulophylli, Radix Anemones Tomentosae, Viscum avalifolium according to this chemical compound of bibliographical information, and its pharmacodynamic study has no report.The present invention separates from Radix Anemones Rivularis first and obtains Hederagenin-3-O-arabinopyranoside, and has carried out the test of antitumor pharmacology.The result shows that Hederagenin-3-O-arabinopyranoside has good effect aspect antineoplaston, and is especially better at the action effect that suppresses human breast cancer cell, sarcoma cell, stomach cancer cell, hepatoma carcinoma cell and prostate gland cancer cell.
Radix Anemones Rivularis is the dry root of ranunculaceae plant Radix Anemones Rivularis Anemone rivularis Buch.-Ham., and is all on the books in " the southern regions of the Yunnan Province book on Chinese herbal medicine " and " choosing of Yunnan Chinese herbal medicine ", is Yunnan Province Yi nationality, distributed over Yunnan, Sichuan and Guizhou medical material, records the drug standard in Yunnan Province.Radix Anemones Rivularis nature and flavor Gan Xinping, slightly poisonous, function heat-clearing and toxic substances removing, relaxing muscles and tendons to promote blood circulation, soothing the liver eliminating the phlegm.Be distributed in the ground such as Guizhou, Yunnan, Sichuan, Tibet, Gansu.Adopt herb summer, uproot autumn.At present less to the research of Radix Anemones Rivularis, only there are the people such as Liao Xun, Li Baigang that Radix Anemones Rivularis has been carried out chemical constitution study, therefrom separate obtaining 8 chemical compounds such as Herba Veronicastri Sibirici glycosides A, Herba Veronicastri Sibirici glycosides B, Anemonolide.The research of Radix Anemones Rivularis was once done by Yunnan Pharmaceutical Institute in the seventies: the Radix Anemones Rivularis effective ingredient is saponin component, and aglycon mostly is oleanolic acid, the separation of total saponins being carried out chemical composition obtains Radix Anemones Rivularis saponin first and Radix Anemones Rivularis saponin second, and total saponins has good antitussive, eliminates the phlegm and bacteriostasis.Yunnan Pharmaceutical Institute has carried out chemical constitution study and pharmacodynamic study to Radix Anemones Rivularis at present, select the mice-transplanted tumor model that the crude extract of Radix Anemones Rivularis has been carried out preliminary anti-malignant tumor screening active ingredients, the result shows that dosage can obviously suppress mouse bearing liver cancer H in the Radix Anemones Rivularis alcohol extract
22Growth.
Summary of the invention
The invention provides compound H ederagenin-3-O-arabinopyranoside(helexin-3-O-galactoside) in the application of preparation in the antitumor drug.
The present invention is achieved through the following technical solutions:
1.Hederagenin-3-O-arabinopyranoside be the following chemical compound of structure,
2.Hederagenin-3-O-arabinopyranoside antitumor use and to be that this chemical compound can be for the preparation of the application of medicine for treating tumor object space face, particularly Hederagenin-3-O-arabinopyranoside has good therapeutic effect to breast carcinoma, solid tumor, gastric cancer, hepatocarcinoma and carcinoma of prostate, can be used for preparing the medicine that treatment includes but not limited to above-mentioned tumor.
3. chemical compound of the present invention can be used as the crude drug useful in preparing drug formulations.
4. chemical compound of the present invention, can be by including but not limited to that following method obtains:
Take by weighing Radix Anemones Rivularis medicinal material coarse powder 10kg, add 6 times of amount methanol, room temperature merceration 5 times is no less than 24h at every turn, filter, and merging filtrate, reclaim under reduced pressure filtrate, vacuum drying is pulverized, and obtains dry extract 1.Take by weighing above-mentioned dry extract 1, add the ethyl acetate be equivalent to 5 times of extractum amounts, reflux, extract, four times, two hours for the first time, second and third, four times each one hour, filter, merging filtrate, filtrate decompression is concentrated, vacuum drying obtains the ethyl acetate extraction part.Get the ethyl acetate extraction part, silica gel (80～100 order) is mixed silica gel column chromatography (200～300 order) behind the sample, use successively chloroform, chloroform-methanol (9: 1), chloroform-methanol (8: 2), chloroform-methanol (7: 3), chloroform-methanol (6: 4) to carry out gradient elution, equivalent is collected, carry out TLC point plate, merge same stream part, separate out the Hederagenin-3-O-arabinopyranoside crude product in the eluent, crude product gets the Hederagenin-3-O-arabinopyranoside sterling with the chloroform repeated crystallization.
5. chemical compound of the present invention can obtain by the method for chemosynthesis.
In order to understand better essence of the present invention, the present invention describes with following test data:
One, the Structural Identification of the compounds of this invention
This chemical compound is white powder, is dissolved in methanol, dimethyl sulfoxine, ESI-MS: 603[M-1]+.In conjunction with
1HNMR,
13The CNMR spectrum determines that molecular formula is C
35H
56O
8 1H-NMR(400MHz，MeOD)δ：5.24(1H，s，H-12)，4.31(1H，d，J=6.7Hz，H-1')，1.17(3H，s，H-27)，0.97(3H，s，H-26)，0.94(3H，s，H-30)，0.91(3H，s，H-25)，0.81(3H，s，H-29)，0.71(3H，s，H-24)；
13C-NMR(100MHz，MeOH)δ：39.5(C-1)，26.4(C-2)，83.2(C-3)，43.8(C-4)，48.1(C-5)，18.4(C-6)，33.1(C-7)，40.5(C-8)，48.6(C-9)，37.3(C-10)，24.1(C-11)，123.6(C-12)，145.3(C-13)，42.9(C-14)，28.6(C-15)，23.9(C-16)，46.7(C-17)，42.7(C-18)，46.6(C-19)，31.6(C-20)，34.4(C-21)，33.1(C-22)，64.8(C-23)，13.4(C-24)，16.4(C-25)，17.8(C-26)，26.4(C-27)，182.0(C-28)，33.6(C-29)，24.0(C-30)，106.4(Ara-1)，72.9(Ara-2)，74.5(Ara-3)，69.8(Ara-4)，66.8(Ara-5)。Above data through with the Hederagenin-3-o-arabinopyranoside(helexin of bibliographical information-3-O-galactoside) spectral data is more consistent, is Hederagenin-3-o-arabinopyranoside(helexin-3-O-galactoside therefore identify this chemical compound).
Two, Hederagenin-3-o-arabinopyranoside acute toxicity test
Select single oral gavage Hederagenin-3-o-arabinopyranoside in the KM kind mice 24 hours, observe the acute toxic reaction symptom and the death condition that produce after the administration.70 mices are divided into 7 groups at random, be the solvent matched group and take Cmax 700mg/kgbw as Hederagenin-3-o-arabinopyranoside maximum dosage, increase by 5 various dose apart from downwards by 0.70 times of group again, be respectively 490,343,240,168,118mg/kgbw, every group 10, each 5 of male and female.After fasting be can't help water 10-12 hour, each dosage group with 40ml/kgbw administration volume oral administration gavage Hederagenin-3-o-arabinopyranoside variable concentrations solution each 1 time, the solvent matched group gives the purified water of same dose with method.Observe various toxic reaction symptoms and the death condition that mice occurs in continuous 6 hours after the administration, observe continuous 14 days later every day 1 time.Respectively at administration the 3rd, weighed in 7,14 days; Observe to finish put to death animal, the volume, color, quality of each animal viscera, organ etc. observed in gross anatomy Non Apparent Abnormality.The result shows, Hederagenin-3-o-arabinopyranoside acute toxicity test in mice median lethal dose(LD 50) (LD50) is 373.033mg/kgbw, the 95% credible 308.666-450.823mg/kgbw that is limited to.This poison of drug effect may relate to nervus centralis, kidney, autonomic nerve, respiratory center and gastrointestinal motility.
Three, Hederagenin-3-O-arabinopyranoside Pharmacodynamics in vitro test
1. experiment purpose
Use srb assay research Hederagenin-3-O-arabinopyranoside to breast cancer cell (MDA-MB-468, MDA-MB-231, MCF7), sarcoma cell (MG63, Soas-2), stomach cancer cell (NCI-N87), the impact of the growth in vitro of hepatoma carcinoma cell (HepG2) and prostate gland cancer cell (PC-3).
2. experiment material
Subject cell: breast cancer cell (MDA-MB-468, MDA-MB-231, MCF7), sarcoma cell (MG63, Soas-2), stomach cancer cell (NCI-N87), hepatoma carcinoma cell (HepG2) and prostate gland cancer cell (PC-3)
Culture medium: DMEM; DMEM-F12; MEM; RPMI1640
Hyclone (FBS), penicillin/streptomycin, pancreatin, SRB(0.4% acetate dissolution)
Positive control: amycin (Doxorubicin), negative control: DMSO
3. experimental technique
Breast cancer cell (MDA-MB-468, MDA-MB-231) (adds 5%FBS with the DMEM culture medium, 1%penicillin/streptomycin) cultivate, breast cancer cell MCF7, sarcoma cell MG63, hepatoma carcinoma cell HepG2 cultivate with MEM culture medium (adding 5%FBS, 1%PS).Sarcoma cell (Soas-2), stomach cancer cell (NCI-N87) is cultivated with RPMI1640 culture medium (adding 5%FBS, 1%PS).Prostate gland cancer cell (PC-3) is cultivated with DMEM-F12 culture medium (adding 5%FBS, 1%PS).
The storing solution of cancer therapy drug is 100mM, and working solution concentration is 8mM, 6mM, 5mM, 4mM, 2mM, 1mM.Cultured cell is in advance made cell suspension after with trypsinization, adjusting density is 3000/100 μ l, every hole 100 μ l are seeded to 96 orifice plates, and preculture is after 24 hours, and every hole adds the culture medium (medicine working solution 1 μ l joins the culture medium of 99 μ l) that 100 μ l added medicine.The volume in the every hole of 96 orifice plates this moment is 200 μ l, and the medicine final concentration is 40 μ M, 30 μ M, 25 μ M, 20 μ M, 10 μ M, 5 μ M.Every kind of medicine is established 3 parallel repetitions, continues to support 48 hours in incubator.
Taking out 96 orifice plates, to get rid of culture fluid air-dry.Every hole adds the ice-cold 10%TCA fixative of 100 μ l fixedly more than the 60min, with distillation washing 5 times, drying.Every hole adds the 0.4%SRB effect 5min of 50 μ l, and 1% acetic acid is washed 5 times, drying.The 10mM unbuffered Tris-base that every hole adds 100 μ l shakes evenly, at the oscillator plate 20min that vibrates.
Measure the OD value in microplate reader, with the blank zeroing, used wavelength is 500nm.Data are added up with Microsoft Excel worksheet, the meansigma methods of the meansigma methods of survival rate=3 a parallel repetition/DMSO negative control hole * 100%
IC
50Calculating: adopt Microsoft Excel worksheet that survival rate data is generated the XY scatterplot, read survival rate (Y-axis) at 0.5 o'clock, the corresponding readings of drug level (X-axis) is IC
50Value.
4. experimental result
Adopt the SRB method, with the positive contrast of amycin (ADR), the tested medicine of preliminary assessment is to the inhibited proliferation of tumor cell, and the result is as follows:
Table 1: tested medicine is to the inhibited proliferation of tumor cell table as a result
Above result of the test shows: Hederagenin-3-O-arabinopyranoside is to breast cancer cell MDA-MB-468, MDA-MB-231, MCF7, sarcoma cell MG63, Soas-2, stomach cancer cell NCI-N87, hepatoma carcinoma cell HepG2 and prostate gland cancer cell PC-3 all have the effect that suppresses survival, show that Hederagenin-3-o-arabinopyranoside of the present invention has antitumor action, particularly to cancer and solid tumor, include but not limited to that breast carcinoma, hepatocarcinoma, gastric cancer, carcinoma of prostate have good therapeutical effect.
The specific embodiment
The preparation of embodiment 1Hederagenin-3-O-arabinopyranoside
Take by weighing Radix Anemones Rivularis medicinal material coarse powder 10kg, add 6 times of amount methanol, room temperature merceration 5 times is no less than 24h at every turn, filter, and merging filtrate, reclaim under reduced pressure filtrate, vacuum drying is pulverized, and obtains dry extract 1.Take by weighing above-mentioned dry extract 1, add the ethyl acetate be equivalent to 5 times of extractum amounts, reflux, extract, four times, two hours for the first time, second and third, four times each one hour, filter, merging filtrate, filtrate decompression is concentrated, vacuum drying obtains the ethyl acetate extraction part.Get the ethyl acetate extraction part, silica gel (80～100 order) is mixed silica gel column chromatography (200～300 order) behind the sample, use successively chloroform, chloroform-methanol (9: 1), chloroform-methanol (8: 2), chloroform-methanol (7: 3), chloroform-methanol (6: 4) to carry out gradient elution, equivalent is collected, carry out TLC point plate, merge same stream part, separate out the Hederagenin-3-O-arabinopyranoside crude product in the eluent, crude product gets the Hederagenin-3-O-arabinopyranoside sterling with the chloroform repeated crystallization.This sterling can be for the preparation of anti-tumor drug.
Embodiment 2
Get Hederagenin-3-O-arabinopyranoside5.0g and starch 10.0g, microcrystalline Cellulose 7.85g, by 80 mesh sieves, mixing adds an amount of stirring of 3% hydroxypropyl cellulose and makes soft material, crosses 16 mesh sieves and granulates, wet grain is in oven dry below 50 ℃, dry granular adds cross-linking sodium carboxymethyl cellulose 1.0g and magnesium stearate 0.75g, mixing by 16 mesh sieve granulate, be pressed into 100, and get final product.Every heavy 0.25g contains Hederagenin-3-O-arabinopyranoside50mg, can be used for the treatment of gastric cancer.
Embodiment 3
Hederagenin-3-O-arabinopyranoside is ground into powder, crosses 80 mesh sieves, get 5.0g and starch 11.5g, micropowder silicon 8.5g mixing, sieve, incapsulate, make 100, and get final product.Every heavy 0.25g contains Hederagenin-3-O-arabinopyranoside50mg, can be used for the treatment of hepatocarcinoma.
Embodiment 4
Get Hederagenin-3-o-arabinopyranoside5.0g and microcrystalline Cellulose 5.0g, can press starch 14.7g, mix homogeneously, add 2.5% Polyethylene Glycol an amount of, mix homogeneously, extrude spheronization and make microspheric granula, micropill incapsulates, and makes 100, and get final product.Every heavy 0.25g contains Hederagenin-3-O-arabinopyranoside50mg, can be used for the treatment of carcinoma of prostate.
Embodiment 5
Hederagenin-3-O-arabinopyranoside is ground into fine powder, cross 100 mesh sieves, get 5.0g and polyoxyethylene 16.0g, sodium chloride 3.0g crosses 100 mesh sieve mix homogeneously, adds 2% polyvidone (95% ethanol) adhesive soft material processed, crossing 20 mesh sieves granulates, in 40 ℃ of dryings, cross 18 mesh sieve granulate, tabletting, take cellulose acetate as framework material, Polyethylene Glycol is that porogen (coated solid amount 10%) carries out the semipermeable membrane coating, makes slow releasing tablet, and get final product.Every heavy 0.30g contains Hederagenin-3-O-arabinopyranoside50mg, can be used for the treatment of breast carcinoma.
Above-described embodiment includes but not limited to above-mentioned.
Claims (6)
1. the application of compound H ederagenin-3-O-arabinopyranoside helexin-3-O-galactoside in the preparation antitumor drug.
2. antineoplastic Hederagenin-3-o-arabinopyranoside according to claim 1 is characterized in that the structure of this chemical compound is following:
Hederagenin-3-O-arabinopyranoside antineoplastic according to claim 1 is used, and it is characterized in that described tumor is solid tumor.
3. Hederagenin-3-O-arabinopyranoside antitumor according to claim 1 is used, and it is characterized in that described tumor is breast carcinoma.
4. Hederagenin-3-O-arabinopyranoside antitumor according to claim 3 is used, and it is characterized in that described tumor is hepatocarcinoma.
5. Hederagenin-3-O-arabinopyranoside antitumor according to claim 3 is used, and it is characterized in that described tumor is gastric cancer.
6. Hederagenin-3-O-arabinopyranoside antitumor according to claim 3 is used, and it is characterized in that described tumor is carcinoma of prostate.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103463098A (en) * | 2013-09-28 | 2013-12-25 | 杨小林 | Application of hederagenin for preparing antineoplastic drugs |
| CN104170821A (en) * | 2014-05-22 | 2014-12-03 | 江苏省中国科学院植物研究所 | Application of Hederagenin-3-Oarabinopyranoside in resisting of phytopathogen |
| CN104546866A (en) * | 2013-09-28 | 2015-04-29 | 杨小林 | Application of hederagenin in preparation of medicine for resisting tumors of esophageal squamous carcinoma cell Eca-109 |
-
2012
- 2012-12-24 CN CN2012105661707A patent/CN103054889A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| BARTHOMEUF C ET AL: "In vitro activity of Hederacolchisid A1compared with other saponins from hedera colchica against proliferation of human carcinoma and melanoma cells", 《PLANTA MED》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103463098A (en) * | 2013-09-28 | 2013-12-25 | 杨小林 | Application of hederagenin for preparing antineoplastic drugs |
| CN104546866A (en) * | 2013-09-28 | 2015-04-29 | 杨小林 | Application of hederagenin in preparation of medicine for resisting tumors of esophageal squamous carcinoma cell Eca-109 |
| CN103463098B (en) * | 2013-09-28 | 2015-05-13 | 杨小林 | Application of hederagenin for preparing antineoplastic drugs |
| CN104170821A (en) * | 2014-05-22 | 2014-12-03 | 江苏省中国科学院植物研究所 | Application of Hederagenin-3-Oarabinopyranoside in resisting of phytopathogen |
| CN104170821B (en) * | 2014-05-22 | 2016-05-18 | 江苏省中国科学院植物研究所 | The application of the anti-phytopathogen of Hederagenin-3-O-arabinopyranoside |
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Application publication date: 20130424 |