CN103027932A - Cortex periplocae anti-tumor effective component extractive as well as preparation method and application thereof - Google Patents
Cortex periplocae anti-tumor effective component extractive as well as preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a cortex periplocae anti-tumor effective component extractive, which is prepared by the following steps of: crushing cortex periplocae; extracting under heating by utilizing water at 90-100 DEG C, concentrating an extracting solution, carrying out alcohol precipitation, centrifuging, removing sediment and concentrating under reduced pressure to remove ethanol to obtain an extracting solution; or extracting under heating by utilizing ethanol with the concentration of 40-95% in a water bath of 80 DEG C, cooling and centrifuging, and concentrating to remove ethanol to obtain an extracting solution; sequentially extracting the extracting solution by utilizing ethyl acetate and water saturated n-butyl alcohol; subjecting a n-butyl alcohol extracted part to silica gel column separation, wherein a diluting agent is dichloromethane-methanol with the different volume ratios; collecting a diluting solution with the volume ratio of dichloromethane to methanol of 10: 1; and recycling an organic solvent to obtain the cortex periplocae anti-tumor effective component extractive. According to the cortex periplocae anti-tumor effective component extractive disclosed by the invention, in an in-vitro cellular toxicity test, the part has the obvious effects of inhibiting U251 (glioma cells), HepG2 (hepatoma carcinoma cells), SGC (stomach carcinoma cells), mcf-7 (human breast cancer cells) and SCLC (small cell lung cancer cells), and can be used for preparing an anti-tumor medicine. The invention discloses a preparation method of the cortex periplocae anti-tumor effective component extractive.
Description
Technical field
The present invention relates to Cortex Periplocae anti-cancer effective component extract and preparation method thereof and as the purposes of antitumor drug.
Background technology
Malignant tumor is one of serious disease of harm humans health in the world today, the experts and scholars of countries in the world seek method and the medicine for the treatment of tumor in active research, especially very active to the research of Chinese medicine antitumorigenic substance, in recent years, the Chinese medicine that has the advantages such as resource is extensive, many target spots has been obtained gratifying achievements at anti-tumor aspect.
Cortex Periplocae Cortex Periplocae also claim periploca sepium, derives from the dry root bark of asclepiadaceae plant P. sepium Bunge Periplocasepium Punge., is Chinese medicine commonly used.This product is warm in nature, and acrid in the mouth is bitter, and is poisonous, returns liver, kidney, heart channel.The effect that wind-damp dispelling, bone and muscle strengthening are arranged.Be used for anemofrigid-damp arthralgia, soreness of the waist and knees, shortness of breath and palpitation, edema of lower limbs.Main product in Hebei, Shanxi, Henan, Shandong 4 provinces, take Shanxi, Henan output is maximum (referring to Li Tianxiang, Zhang Lijuan, Liu Hong, Hunan, fence osmanthus, Gao Xiumei, Zhang Baili, 2008,27(12), 960).
The Chinese medicine Cortex Periplocae contains the Multiple components such as sterol, esters, glycoside, aldehydes and terpenoid, but relevant its function and efficacy research on mechanism seldom, there are indivedual scholars that the cardiotonic of Cortex Periplocae Radicis extract has been done preliminary experiment (referring to Li Yuhong, Gao Xiumei, Zhang Baili, 2005,7 (4): 396-397, Ma Li, Wang Yi 2009,41 (3): 71..).Studies show that in recent years, some composition has certain antitumous effect in the Cortex Periplocae, preliminary direction has been set up in this antitumor mechanism research to Cortex Periplocae, these monomer components comprise: glucoperiplocymarin, periplocymarin, periplogenin, baohuoside Ⅰ etc. (referring to: Zhao L M, Shan B E, Du Y Y Oncologyreports.2010,24:375-383.Jun ya UEDA, Yasuhiro TEZUKA, Arjun HariBANSKOTA, Biol.Pharm.Bull.2003,26 (10), 1431-1435.Yong Li, Yun-Bao Liu, Shi-Shan Yu, Steroids.2012,77.375-381.Song J, Shu L, Z H, Chemico-BiologicalInteractions.2012,199:9-17.).
The methods such as Li Jin nanmu research and utilization column chromatography; from 95% ethanol extract of Cortex Periplocae, separate and obtain 11 chemical compounds; be respectively isovanillin (I); 4-methoxyl group salicylic acid (II); 4-methoxysalicylaldehyde (III); caffeic acetate's (IV); scopoletin (V); 5; 5 '-dimethoxy lariciresinol-4 '-O-β-D-pyranglucoside (tor-toside B) (VI); periplocoside L (VII); Δ 5-pregnene-3 β; 20 (S)-glycol (VIII); Δ 5-pregnene-3 β; 20 (S)-glycol-20-O-β-D-Glucopyranose .-3-O-β-D-pyranglucoside (IX); Δ 5-pregnene-3 β; 20 (S)-glycol-20-O-β-D-glucopyranosyl (1 → 6)-β-D-pyranglucoside (Qinling Mountains rattan glycosides C) (X); Δ 5-pregnene-3 β; 20 (S)-glycol-3-O-［ 2-O-acetyl group-β-D-pyrans Folium Digitalis Purpureae glycosyl (1 → 4)-β-D-pyrans cymarose ］-20-O-β-D-glucopyranosyl (1 → 6)-β-D-glucopyranosyl (1 → 2)-β-D-pyrans digitalis glycoside (XI); compounds Ⅳ wherein; VI; IX. and X is for obtaining from this kind medical material first (referring to Li Jinnan; Zhao Liying; in quiet; Gao Ying, Deng Yanru. Chinese patent medicine .2010.32 (9): 1552).But do not carry out pharmacological research.
Chinese patent application CN200810006406.5 " a kind of method of analyzing fatty acid chemical composition in cortex periplocae radicis ", " 200510013382.2 Cortex Periplocae cardiotonic effective site and preparation method and the pharmaceutical preparation and the purposes that contain them ", be about the preparation of fatty acid and the cardiotonic position of this medical material, do not relate to the application of this medical material aspect anti-tumor activity.
Summary of the invention
One of purpose of the present invention is that Cortex Periplocae anti-cancer effective component extract and preparation method thereof is provided.
Two of purpose of the present invention is that a kind of pharmaceutical composition with described active component extract is provided.
Three of purpose of the present invention is that the application of described active component extract in preparation antitumor and related drugs is provided.
Technical scheme of the present invention is as follows:
Cortex Periplocae anti-cancer effective component extract, it is that water is in 90-100 ℃ of heating extraction after being pulverized by Cortex Periplocae, extracting solution is concentrated, precipitate with ethanol, the centrifugal precipitation of removing, concentrating under reduced pressure is removed ethanol, gets extracting solution; Or by after the Cortex Periplocae pulverizing, extract in 80 ℃ of heating in water bath with 40%～95% ethanol, cooling, centrifugal, concentrate and remove ethanol, get extracting solution; Then extract successively the extracting solution of gained with ethyl acetate and water-saturated n-butanol, butanol extraction liquid carries out silicagel column to be separated, eluant is the methylene chloride-methanol of different volumes ratio, collecting dichloromethane and methanol volume ratio is the eluent of 10: 1 ratios, reclaims organic solvent and namely gets Cortex Periplocae anti-cancer effective component extract.
A kind of method for preparing above-mentioned Cortex Periplocae anti-cancer effective component extract, it comprises the steps:
Step 1. is pulverized Cortex Periplocae, the water reflux, extract,, and cooling, centrifugal, concentrated extracting solution carries out precipitate with ethanol with 95% ethanol, and the centrifugal precipitation of removing concentrates and removes ethanol, gets extracting solution; Perhaps Cortex Periplocae is pulverized, extracted in 80 ℃ of heating in water bath with 40%～95% ethanol, cooling, centrifugal, concentrate and remove ethanol, get extracting solution;
Step 2. extracts the extracting solution of step 1 successively with ethyl acetate, water saturated butanol solution, butanol extraction liquid liquid is carried out silicagel column to be separated, eluant is the methylene chloride-methanol mixed solvent of different volumes ratio (100: 1 ~ 1: 1), collection dichloromethane and methanol volume ratio are 10: 1 eluent, rotary evaporation namely gets Cortex Periplocae anti-cancer effective component extract after reclaiming organic solvent.
This active component extract contains glucoperiplocymarin and other unknown material through preparation liquid phase, carbon spectrum hydrogen analysis of spectrum.
The present invention further provides the application of Cortex Periplocae anti-cancer effective component extract in the preparation antitumor drug.Test as activity index carries out anti-tumor activity to suppress the U251 multiplication capacity.Experimental result shows, in the experiment of cell in vitro poison, can obviously suppress the propagation of U251, has cytotoxicity, can be used for preparing the antineoplaston medicine.
The present invention also provides the pharmaceutical composition with the effective site of described method preparation.Described pharmaceutical composition is as effective ingredient take effective site of the present invention, form with pharmaceutically acceptable carrier, and exist to be fit to medicinal dosage form, these dosage forms can be tablets, 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, drop, drop pill and patch etc.
Beneficial effect
(1) the present invention finds that first methylene chloride-methanol (10: 1) the eluting position of the n-butanol portion of Cortex Periplocae has anti-tumor activity, and first at the U251(glioma cell) carry out medicine efficacy screening, active good, the suitable anti-tumor Chinese medicine new drug that is developed to.
(2) the present invention has expanded the raw material channel of antitumor drug, has enlarged the purposes of Cortex Periplocae, makes Cortex Periplocae develop into the new raw material of antitumor drug, can significantly improve the added value of Cortex Periplocae.Simultaneously, find that for screening from Chinese crude drug new antitumor drug provides new approaches.
The specific embodiment
Below listed embodiment help those skilled in the art to understand better the present invention, but do not limit the present invention in any way.
The preparation of embodiment 1. Cortex Periplocae anti-cancer effective component extracts
Cortex Periplocae is dry, pulverize, the powder 400g that gets it filled, with the water reflux, extract, 4h of 10 times of quality, the residue after centrifugal repeats to extract 1 time, centrifugal, merge the intermediate water extracting solution, be concentrated into 300ml, add 95% ethanol and carry out precipitate with ethanol, the concentration of ethanol is about 60% in the medicinal liquid, standing over night, centrifugal, discard precipitation, decompression recycling ethanol, continue to be concentrated into 300ml, add isopyknic ethyl acetate extraction 4 times, after residual ethyl acetate is removed in remaining water liquid decompression, with isopyknic water saturated n-butanol extraction 3 times, merge the water-saturated n-butanol extract, reclaim n-butyl alcohol, get water-saturated n-butanol extract 8.66g;
Above-mentioned n-butanol extract is crossed silicagel column, and the dichloromethane of configuration different proportion and methyl alcohol mixed liquor (20: 1,10: 1,5: 1,1: 1) each 300ml, the collection ratio is 10: 1 eluent, concentrated, vacuum drying gets Cortex Periplocae anti-cancer effective component extract.
This extractive part contains glucoperiplocymarin and other unknown material through preparation liquid phase, carbon spectrum hydrogen analysis of spectrum.
The preparation of embodiment 2. Cortex Periplocae anti-cancer effective component extracts
Cortex Periplocae is dry, pulverize, the powder 400g that gets it filled is with the water reflux, extract, 5h of 10 times of quality, residue after centrifugal repeats to extract 1 time, centrifugal, merge the intermediate water extracting solution, be concentrated into 300ml, add 95% ethanol and carry out precipitate with ethanol, the concentration of ethanol is about 60% in the medicinal liquid, and standing over night is centrifugal, discard precipitation, decompression recycling ethanol continues to be concentrated into 200ml, adds isopyknic ethyl acetate extraction 3 times, after residual ethyl acetate is removed in remaining water liquid decompression, with the water saturated n-butanol extraction of equal-volume 4 times, merge the water-saturated n-butanol extract, reclaim n-butyl alcohol, get water-saturated n-butanol extract 9.56g
Above-mentioned n-butanol extract is crossed silicagel column, be 7: 1 dichloromethane and methyl alcohol mixed liquor isocratic elution with ratio, pass through tlc analysis, the Cortex Periplocae anti-cancer effective component extract that obtains with extraction in the example 1 has the collection liquid of same blob to merge, concentrated, vacuum drying gets Cortex Periplocae anti-tumor effective component extract.
This extractive part contains glucoperiplocymarin and other unknown material through preparation liquid phase, carbon spectrum hydrogen analysis of spectrum.
The preparation of embodiment 3. Cortex Periplocae anti-tumor effective component extracts
Cortex Periplocae is dry, pulverize, the material 400g that gets it filled, with 95% alcohol reflux 3h of 10 times of quality, the residue after centrifugal repeats to extract 1 time, centrifugal, merge the secondary alcohol extract, be concentrated into without the alcohol flavor, add suitable quantity of water, centrifugal, discard precipitation, be concentrated into about 300ml, with isopyknic petroleum ether extraction 3 times, after residual petroleum ether is removed in remaining water liquid decompression, add isopyknic ethyl acetate extraction 4 times, after residual ethyl acetate is removed in remaining water liquid decompression, use the water saturated n-butanol extraction of equal-volume 4 times, merge the water-saturated n-butanol extract, reclaim n-butyl alcohol, get n-butanol extract 15.76g
N-butanol extract is crossed silicagel column, and the dichloromethane of configuration different proportion and methyl alcohol mixed liquor (20: 1,10: 1,5: 1,1: 1) each 300ml, the collection ratio is 10: 1 eluent, concentrated, vacuum drying gets Cortex Periplocae anti-cancer effective component extract.
This extractive part contains glucoperiplocymarin and other unknown material through preparation liquid phase, carbon spectrum hydrogen analysis of spectrum.
The preparation of embodiment 4. Cortex Periplocae anti-cancer effective component extracts
Cortex Periplocae is dry, pulverizing, get 400g medicated powder, 45% alcohol reflux 3h with 10 times of quality amounts, residue after centrifugal repeats to extract 1 time, and is centrifugal, merges the secondary alcohol extract, be concentrated into without the alcohol flavor, add water to 300ml, centrifugal, discard precipitation, continue to be concentrated into 200ml, the ethyl acetate extraction 4 times that adds an amount of volume is after residual ethyl acetate is removed in remaining water liquid decompression, with the water saturated n-butanol extraction of equal-volume 3 times, merge the water-saturated n-butanol extract, reclaim n-butyl alcohol, get water-saturated n-butanol extract 13.45g
N-butanol extract is crossed silicagel column, with ratio is 7: 1 dichloromethane and methyl alcohol mixed liquor eluting, pass through tlc analysis, the Cortex Periplocae anti-cancer effective component extract that obtains with extraction in the example 1 has the collection liquid of same blob to merge, concentrated, vacuum drying gets Cortex Periplocae anti-tumor effective component extract.
This extractive part is glucoperiplocymarin and other unknown material through preparation liquid phase, carbon spectrum, hydrogen analysis of spectrum.
The experiment of embodiment 5 anti-tumor activities
The Cortex Periplocae active component extract that obtains take embodiment 1 is as tested medicine, In vitro culture U251, and fetching is counted the cell of trophophase, after trypsinization, 1500r ﹒ min
-1Centrifugal 5min is resuspended in cell in the culture medium, and cell concentration transfers to 2 * 10
4Individual/ml, be inoculated in the 96 porocyte culture plates, every hole 100 μ l, the placement cell culture incubator (37 ℃, 5%CO
2) the middle 24h that cultivates, adding afterwards tested medicine 20 μ l, it is 0.5%DMSO that negative control group adds final concentration, each group is all established 3 again holes.Behind dosing 48h, every hole adds 5mg ﹒ mL
-1MTT reagent 20 μ l continue to place 37 ℃ to cultivate 4h.Every hole adds DMSO100 μ l, and the vibration mixing is measured each hole at the absorbance at wavelength 570nm place.Calculate cell proliferation inhibition rate: suppression ratio (%)=(1-experimental group absorbance/matched group absorbance) * 100%.
Table 1 Cortex Periplocae Radicis extract anti-tumor activity experiment (U251)
The Cortex Periplocae active component extract that obtains take embodiment 2-4 repeats above-mentioned test and obtains identical result as tested medicine.
Claims (4)
1. Cortex Periplocae anti-cancer effective component extract is characterized in that: it is that water is in 90-100 ℃ of heating extraction after being pulverized by Cortex Periplocae, and extracting solution is concentrated, precipitate with ethanol, and the centrifugal precipitation of removing, concentrating under reduced pressure is removed ethanol, gets extracting solution; Perhaps it is after being pulverized by Cortex Periplocae, to extract in 80 ℃ of heating in water bath with 40%～95% ethanol, and cooling is centrifugal, concentrates and removes ethanol, gets extracting solution; Extract successively the extracting solution of gained with ethyl acetate and water-saturated n-butanol, butanol extraction liquid carries out silicagel column to be separated, eluant is the methylene chloride-methanol of different volumes ratio, collecting dichloromethane and methanol volume ratio is the eluent of 10: 1 ratios, namely get Cortex Periplocae anti-cancer effective component extract after reclaiming organic solvent, this extract contains glucoperiplocymarin and other unknown material.
2. method for preparing Cortex Periplocae anti-cancer effective component extract claimed in claim 1, it comprises the steps:
Step 1. is pulverized Cortex Periplocae, and water cools off in 90-100 ℃ of heating extraction, and centrifugal, concentrated extracting solution carries out precipitate with ethanol with 95% ethanol, and the centrifugal precipitation of removing concentrates and removes ethanol, gets extracting solution; Perhaps Cortex Periplocae is pulverized, extracted in 80 ℃ of heating in water bath with 40%～95% ethanol, cooling, centrifugal, concentrate and remove ethanol, get extracting solution;
Step 2. extracts the extracting solution of step 1 successively with ethyl acetate, water saturated butanol solution, n-butanol extracting liquid is carried out silicagel column to be separated, eluant is the methylene chloride-methanol mixed solvent of different proportion, collection dichloromethane and methanol volume ratio are 10: 1 eluent, rotary evaporation namely gets Cortex Periplocae anti-cancer effective component extract after reclaiming organic solvent.
3. the application of Cortex Periplocae anti-cancer effective component extract claimed in claim 1 in the preparation antitumor drug.
4. application according to claim 3 is characterized in that: described antitumor drug is the medicine of antitumor cell U251.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108785322A (en) * | 2017-04-28 | 2018-11-13 | 南京葆赫生物技术有限公司 | Purposes of the Heiguteng exract C21 steroids in preparing IDO inhibitor |
| CN108785317A (en) * | 2017-04-28 | 2018-11-13 | 苏州凯祥生物科技有限公司 | Purposes of the cortex periplocae C21 steroids in preparing IDO inhibitor |
| CN113577085A (en) * | 2020-04-30 | 2021-11-02 | 中国科学院上海药物研究所 | Periploca sepium glycoside composition, preparation method thereof and application thereof in preparation of medicine for treating autoimmune diseases |
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| CN1594353A (en) * | 2004-07-12 | 2005-03-16 | 天津中医学院 | Process for preparing periplocin |
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- 2012-11-29 CN CN2012104989983A patent/CN103027932A/en active Pending
Patent Citations (1)
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| CN1594353A (en) * | 2004-07-12 | 2005-03-16 | 天津中医学院 | Process for preparing periplocin |
Non-Patent Citations (1)
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108785322A (en) * | 2017-04-28 | 2018-11-13 | 南京葆赫生物技术有限公司 | Purposes of the Heiguteng exract C21 steroids in preparing IDO inhibitor |
| CN108785317A (en) * | 2017-04-28 | 2018-11-13 | 苏州凯祥生物科技有限公司 | Purposes of the cortex periplocae C21 steroids in preparing IDO inhibitor |
| CN113577085A (en) * | 2020-04-30 | 2021-11-02 | 中国科学院上海药物研究所 | Periploca sepium glycoside composition, preparation method thereof and application thereof in preparation of medicine for treating autoimmune diseases |
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Application publication date: 20130410 |