CN104398532B - Application of cardiac glycoside compound 12beta-hydroxycalotropin - Google Patents
Application of cardiac glycoside compound 12beta-hydroxycalotropin Download PDFInfo
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- hydroxycalotropin
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Abstract
The invention discloses an application of a cardiac glycoside compound 12beta-hydroxycalotropin in preparation of medicine for treating and preventing tumors. The cardiac glycoside compound 12beta-hydroxycalotropin has remarkable antitumor activity and can be used as a lead compound for treating the tumors. Meanwhile, an extraction separation method of the cardiac glycoside compound 12beta-hydroxycalotropin is simple, practicable, low in cost, high in efficiency and yield and good in extraction quality.
Description
The application is the divisional application of " a kind of new application of cardiac glycoside compound ", and the applying date of original application is 2013 4
The moon 11, Application No.：201310124216.4.
Technical field
The present invention relates to cardiac glycoside compound is and in particular to a kind of cardiac glycoside 12 β-hydroxycalotropin and its use
On the way.
Background technology
Tumor is very big to the threat of human health and life, and it has become two big difficulties medically with cardiovascular disease,
Constitute two of the cause of death in the whole world.In the whole world 5,200,000,000 population, there are about 7,000,000 people every year and newly suffer from tumor, every year about
There are more than 500 ten thousand people to die from tumor, almost just have a tumor patient death within every 6 seconds.Every annual there are about 1,500,000 at present for China
People newly suffers from tumor, there are about 800,000 people every year and dies from tumor.Existing antitumor drug all can not thoroughly be cured effectively.Simultaneously by
In the continuous discovery of novel tumor, people are forced to strive to find new antitumor drug.For a long time, from medicinal plants especially
In tropical medicinal plants, seeking antitumor medicine becomes a common aspiration of various countries' medical science, pharmacy, chemistry and biologist.Grind
Study carefully and show, antitumor drug 70% derives from the torrid zone or subtropical plant.After vincristin, paclitaxel and its derivant
The discovery of Epothilones, makes this work achieve breakthrough progress.However, because some antineoplastic components are in plant
In-vivo content is extremely low, some plants or rareness species in imminent danger, and plant growing is slow, and excessively excavation may lead to this species
Extinction, these factors limit the development of anti-tumor botanical.
Radix Calotropis giganteae [Calotropis gigantea (L.) Dryand ex Ait.f.] is trailing plants section
(Asclepiadaceae) Calotropis (Calotropis) plant.It is distributed mainly on Hainan, Guangdong, Sichuan and Yunnan in China
Etc. ground.Radix Calotropis giganteae Herb is poisonous, and the white juice at its root, stem, leaf, flower, fruit and each position is all pharmaceutically acceptable, have antibacterial, antiinflammatory,
The effects such as anthelmintic, resolving sputum, removing toxic substances, be a kind of common medicine among the people.Research shows Radix Calotropis giganteae mainly chemical combination containing cardiac glycoside both at home and abroad
Thing, for its toxic component.But it is anti-with regard to whether the cardiac glycoside compound 12 β-hydroxycalotropin in Radix Calotropis giganteae has
Function of tumor is current or unknown.
Content of the invention
It is an object of the invention to provide a kind of cardiac glycoside compound 12 β-hydroxycalotropin has in preparation controlling
Treat and the purposes in the medicine of prophylaxis of tumours effect.
Present inventor is carried to the cardiac glycoside compounds 12 β-hydroxycalotropin in Radix Calotropis giganteae
Take, separate, purification and anti-tumor activity test find, cardiac glycoside compound 12 β in this Radix Calotropis giganteae-
Hydroxycalotropin has antineoplastic new application.
The above-mentioned purpose of the present invention is achieved by the following technical solution：Cardiac glycoside compound 12 β-
Purposes in preparation has the medicine treating and preventing function of tumor for the hydroxycalotropin, described cardiac glycoside compound
The molecular formula of 12 β-hydroxycalotropin is C29H40O10, structural formula is as follows：
Tumor of the present invention is mainly cancer of biliary duct, renal carcinoma, cancer of pancreas, colorectal carcinoma, bladder cancer, breast carcinoma, son
Palace cancer, ovarian cancer, colorectal cancer, hepatocarcinoma, gallbladder cancer, cancer of bile ducts, acute leukemia, malignant lymphoma, cerebroma, bone tumor, melanoma,
Glioma, oral cancer, nasopharyngeal carcinoma, pulmonary carcinoma or gastric cancer etc..
Cardiac glycoside compound 12 β-hydroxycalotropin of the present invention can utilize from Radix Calotropis giganteae and include adsorbent resin
Multiple separation means such as column chromatography, silica gel column chromatography, reversed-phase silica gel column chromatography, gel filtration chromatography, reduced pressure chromatography obtain, or
Obtained by synthesis and semi-synthetic means.Combine with suitable excipient, conventionally make various dosage forms.
The preferred preparation method of cardiac glycoside compound 12 β-hydroxycalotropin of the present invention is as follows：
A, selection Radix Calotropis giganteae stem, after pulverizing, add ethanol, extract 3～4 times, 6～8 days every time, merge lixiviating solution, decompression
It is concentrated into the ethanol extraction that no alcohol taste obtains Radix Calotropis giganteae；
B, the ethanol extraction of Radix Calotropis giganteae is dispersed in water and makes Radix Calotropis giganteae suspension, press respectively Radix Calotropis giganteae suspension with
The volume ratio of petroleum ether is 1:3、1:2 and 1:1, Radix Calotropis giganteae suspension is repeated, after extraction, retain petroleum ether extraction with petroleum ether
Aqueous phase afterwards；
C, the aqueous phase after petroleum ether extraction is filtered, filtrate is separated with D-101 macroporous adsorbent resin column chromatography, and successively
With water and methanol-eluted fractions, collect meoh eluate, after concentrating under reduced pressure reclaims methanol, obtain methanol extract；
D, by methanol extract through reduce pressure silica gel column chromatography, be respectively 100 with the volume ratio of chloroform and methanol:1、50:1、25:
1、10:1、5:1、2:1 and 0:100 as eluant, carries out gradient elution to decompression silicagel column, respectively crude extract Fr.1～
Fr.7；
E, by step D gained crude extract Fr.4 through silica gel column chromatography, be respectively 10 with the volume ratio of chloroform and methanol:1、8:
1、6:1、4:1、2:1、0:1, as eluant, carries out gradient elution to silicagel column, obtains 6 part Fr.4-1～Fr.4-6；
F, by the Fr.4-2 of E step through silica gel column chromatography, eluting is carried out as eluant using chloroform and acetone, during eluting
Identical composition is collected using TLC thin layer chromatography, obtains 6 part Fr.4-2-1～Fr.4-2-6；Fr.4-2-3 is entered successively
Row Sephadex LH-20 gel filtration chromatography, reversed phase column chromatography and silica gel column chromatography again, finally give cardiac glycoside compound
12β-hydroxycalotropin.
In step A of the present invention, Radix Calotropis giganteae stem and the mass volume ratio of ethanol are 1kg：1～3L；The volume basis of described ethanol
Content is 92～98%.
Radix Calotropis giganteae suspension is repeated extract after 3 times with petroleum ether in step B of the present invention, retain the water after petroleum ether extraction
Phase.
In step F of the present invention, the volume ratio of chloroform and acetone is 4:5；The gel column adopting during gel filtration chromatography is
Sephadex LH-20 gel column, the ethanol that during gel filtration chromatography, eluting solvent is 95% using volumn concentration；Silicon again
The eluting solvent adopting during plastic column chromatography is 11 for volume ratio:1:1 chloroform, methanol and acetone mixed solvent.
It is molten that solvent such as petroleum ether, chloroform, methanol, the ethanol etc. adopting in above-mentioned steps A, B, C, D, E, F is technical grade
Agent, uses after steaming again.
Used in above-mentioned D, E, F-step, silicagel column, gel column and reversed-phase column etc. are routine of the prior art and set
Standby.
The invention has the advantages that：The cardiac glycoside compound 12 β-hydroxycalotropin that the present invention provides has
Significantly anti-tumor activity, can be used as the lead compound for the treatment of tumor；Meanwhile, the extraction separation method that the present invention provides is simple
Easy, low cost, efficiency high, yield is high, and extract quality is good.
Specific embodiment
With reference to instantiation, the present invention is further elaborated, but does not limit the present invention.
Embodiment 1
A, by Radix Calotropis giganteae (Calotropis gigantea) stem 25.4kg natural air drying pulverize after, by Radix Calotropis giganteae sample：Second
Alcohol-water solution is about 1:2 mass/volume ratio (kg/L), ethanol water and the 25.4kg cattle that 50L volume fraction is 95%
JIAOGUA sample is sufficiently mixed, sealing, extracts 3 times in room temperature, 7 days every time, filters and merge lixiviating solution, be evaporated to no alcohol
Taste obtains ethanol extraction；
B, at room temperature, ethanol extraction is dispersed in water and makes suspension, by ethanol extract：Petroleum ether=1:3、
1:2、1:1 volume ratio, repeats to ethanol extract to extract 3 times with petroleum ether, after concentrating under reduced pressure reclaims petroleum ether, obtains oil
Ethereal extract (254.1g)；
C, by after petroleum ether extraction aqueous filter, by filtrate with D-101 macroporous adsorbent resin column chromatography separate, successively
With water and methanol-eluted fractions, collect meoh eluate, after concentrating under reduced pressure reclaims methanol, obtain methanol extract (255.7g)；
D, by methanol extract through reduce pressure silica gel column chromatography, with chloroform：Methanol=100:1,50:1,25:1,10:1,5:1,2:
1,0:The eluant of 100 volume ratios, carries out gradient elution, respectively obtains 7 part Fr.1～Fr.7；
E, by D step chloroform：Methanol=10:1 Fr.4 affording (38.4g), through silica gel column chromatography, uses chloroform：First
Alcohol=10:1,8:1,6:Isosorbide-5-Nitrae:1,2:The eluant of 1 volume ratio carries out gradient elution, finally uses methanol-eluted fractions, obtains 6 parts
Fr.4-1～Fr.4-6；
F, by the Fr.4-2 (16.7g) of E step through silica gel column chromatography, use chloroform：Acetone=4:The eluant of 5 volume ratios enters
Row eluting, then adopt TLC thin layer chromatography collect identical composition, obtain 6 parts, this 6 partly in third portion,
Namely Fr.4-2-3, Fr.4-2-3 (2.0g) is carried out Sephadex LH-20 gel filtration chromatography successively, and (volume fraction is
95% ethanol elution), reversed phase column chromatography and silica gel column chromatography (chloroform：Methanol：Acetone=11:1:1 eluting), final
To cardiac glycoside compound 12 β-hydroxycalotropin (98.2mg).
Embodiment 2
By the Fr.4-1 (3.2g) of E step in embodiment 1 after column chromatography, use chloroform：Methanol=25:The washing of 1 volume ratio
De- agent carries out eluting, collects identical composition using TLC thin layer chromatography, obtains 7 part Fr.4-1-1～Fr.4-1-7；Will
Fr.4-1-4 (869.5mg), through silica gel column chromatography, uses chloroform successively：Methanol=40:1st, chloroform：Acetone=6:The washing of 2 volume ratios
De- agent carries out eluting, finally gives cardiac glycoside compound calotropin (109.9mg).Research find, this compound with this
Difference on bright purpose compound structure is do not have hydroxyl on the carbon of 12, and the carbon of purpose of the present invention compound 12
On have hydroxyl replace.The anti-IC of this two compounds is found in the test of further anti tumor activity in vitro50Value significant difference
(being shown in Table 2).
Embodiment 3
The Structural Identification of cardiac glycoside compound 12 β-hydroxycalotropin：
Using spectral technique, including the analysis of ultraviolet, infrared, nuclear magnetic resonance, NMR and high resolution mass spectrum, identify in embodiment 1
The structure of cardiac glycoside compound 12 β-hydroxycalotropin.With 2D-NMR technology to finding first in Radix Calotropis giganteae stem
Cardiac glycoside compound 12 β-hydroxycalotropin's13C-NMR,1H-NMR data is belonged to (see table 1).
It is below the physicochemical constant of cardiac glycoside compound 12 β-hydroxycalotropin：
12β-hydroxycalotropin：C29H40O10, white amorphous powder (methanol), 10% ethanol solution of sulfuric acid shows
Brown.m.p.214-216℃；[α]D+ 6.4 ° (c=0.045, MeOH)；HR-ESI-MS:m/z[M+Na]+583.2318
(calcd.For C29H40O10Cl,583.2310)；IRλmax(cm-1):3433cm-1,2957cm-1,2923cm-1,2852cm-1,
1712cm-1,1655cm-1,1648cm-1,1638cm-1,1630cm-1,1459cm-1,1262cm-1,1105cm-1,1025cm-1；UV
λmaxnm(MeOH):218nm.13C-NMR and1H-NMR see table 1.
The carbon spectrum of table 1 cardiac glycoside compound 12 β-hydroxycalotropin and hydrogen modal data
Embodiment 4
Cardiac glycoside compound 12 β-hydroxycalotropin and the contrast of calotropin anti tumor activity in vitro test
Experiment：
Cardiac glycoside compound 12 β-hydroxycalotropin and calotropin are tested using mtt assay, to human gastric cancer
Cell (SGC-7901), human gastric adenocarcinoma (KKLS, MKN-28, MKN-45), people's chronic myeloid leukemia cells (K562),
Human mouth epidermis cancerous cell (KB), human breast cancer cell (MCF7), human lung carcinoma cell (NCI-H187), people's fibrosarcoma of bone cell
(HT-1080), human osteosarcoma cell (G-292), human osteosarcoma cell (KHOS/NP), Human Prostate Cancer Cells (LNCap) etc. are thin
The anti tumor activity in vitro (the results are shown in Table 2) of born of the same parents' strain.
Activity test method is as follows：
It is different with 8 dense that experiment sets negative control group (water), DMSO solvent control group, positive controls (ametycin)
Degree (0.1,0.3,0.9,2.7,8.1,24.3 μ g mL-1) testing sample, IC50Value ＜ 0.1 μ g mL-1Testing sample continue
Continue and down dilute, then set 6 variable concentrations (0.0003,0.001,0.004,0.011,0.033 and 0.100 μ g mL-1), each
Concentration set 3 parallel.Collect exponential phase cell, blood counting chamber counts, and is inoculated in 96 by the 4500 cancerous cell amounts in every hole
In the flat Tissue Culture Plate in hole, it is placed in 5%CO2, cultivate in more than 90%, 37 DEG C of incubators of humidity.Addition is taken out a certain amount of after 24h
Testing sample, take out after continuing culture 72h and be placed in basis of microscopic observation every hole cellular morphology, record cellular morphology change feelings
Condition, then MTT solution (being dissolved in balanced salt solution PBS) the 15 μ L of every hole addition 5mg/mL, after 37 DEG C of reaction 4h, by cell culture
Liquid suctions out, and every hole adds 100 μ L DMSO fully to dissolve Formazane, and Tissue Culture Plate is placed in MK3 microplate reader, uses
570nm wavelength surveys the absorbance (A) in each hole, seeks growth inhibition ratio by following equation.
With sample concentration as abscissa, with suppression ratio as vertical coordinate, simulated using origin software according to Concentraton gradient
Suppression ratio curve chart, the sample concentration when suppression ratio is 50% is the IC of cytotoxic activity50Value, sample activity result i.e. with
Half-inhibition concentration (IC50) represent.
As can be seen from Table 2, the difference on cardiac glycoside compound 12 β-hydroxycalotropin and calotropin structure
And then significant difference be there is also on anti-tumor activity.The cardiac glycoside compound anti-tumor activity of the present invention substantially than
Calotropin is strong.
The external tumor suppression result of table 2 cardiac glycoside compound 12 β-hydroxycalotropin
Embodiment 5
Cardiac glycoside compound 12 β-hydroxycalotropin 8g prepared by embodiment 1 and Microcrystalline Cellulose 75g and
Magnesium stearate 7g mixes, and mixture single punch tablet machine breaks into diameter 5mm, the tablet of weight 100mg.In this tablet, every contains 12
β-hydroxycalotropin 8mg.In conjunction with disease, 1 to 2 tablets once, daily 2-3 time.
Embodiment 6
The cardiac glycoside compound 12 β-hydroxycalotropin 20g that prepare embodiment 1 and Lactose 95g and stearic acid
Magnesium 6g mixes, and fills capsule with every 300mg.In this capsule, each capsule contains 12 β-hydroxycalotropin 25mg.Knot
Combination of syndromes disease, each 1-2, daily 3-4 time.
Specific embodiment listed above is the explanation that the present invention is carried out.It is pointed out that above example is only used
In the invention will be further described, do not represent protection scope of the present invention, other people according to the prompting of the present invention make non-
The modification of essence and adjustment, still fall within protection scope of the present invention.
Claims (5)
1. cardiac glycoside compound 12 β-hydroxycalotropin has the purposes in the medicine for the treatment of function of tumor in preparation,
The molecular formula of described cardiac glycoside compound 12 β-hydroxycalotropin is C29H40O10, structural formula is as follows：
Described tumor is oral cancer, pulmonary carcinoma or Human Prostate Cancer Cells LNCap.
2. cardiac glycoside compound 12 β-hydroxycalotropin according to claim 1 has treatment tumor in preparation
Purposes in the medicine of effect, is characterized in that：The preparation method of described cardiac glycoside compound 12 β-hydroxycalotropin is such as
Under：
A, selection Radix Calotropis giganteae stem, after pulverizing, add ethanol, extract 3～4 times, 6～8 days every time, merge lixiviating solution, concentrating under reduced pressure
Obtain the ethanol extraction of Radix Calotropis giganteae to no alcohol taste；
B, the ethanol extraction of Radix Calotropis giganteae is dispersed in water and makes Radix Calotropis giganteae suspension, press Radix Calotropis giganteae suspension and oil respectively
The volume ratio of ether is 1:3、1:2 and 1:1, Radix Calotropis giganteae suspension is repeated after extraction with petroleum ether, after retaining petroleum ether extraction
Aqueous phase；
C, the aqueous phase after petroleum ether extraction is filtered, filtrate is separated with D-101 macroporous adsorbent resin column chromatography, and uses water successively
And methanol-eluted fractions, collect meoh eluate, after concentrating under reduced pressure reclaims methanol, obtain methanol extract；
D, by methanol extract through reduce pressure silica gel column chromatography, be respectively 100 with the volume ratio of chloroform and methanol:1、50:1、25:1、
10:1、5:1、2:1 and 0:100 as eluant, carries out gradient elution to decompression silicagel column, respectively crude extract Fr.1～
Fr.7；
E, by step D gained crude extract Fr.4 through silica gel column chromatography, be respectively 10 with the volume ratio of chloroform and methanol:1、8:1、6:
1、4:1、2:1、0:1, as eluant, carries out gradient elution to silicagel column, obtains 6 part Fr.4-1～Fr.4-6；
F, by the Fr.4-2 of E step through silica gel column chromatography, eluting is carried out as eluant using chloroform and acetone, during eluting adopt
TLC thin layer chromatography collects identical composition, obtains 6 part Fr.4-2-1～Fr.4-2-6；Fr.4-2-3 is carried out successively
Sephadex LH-20 gel filtration chromatography, reversed phase column chromatography and silica gel column chromatography again, finally give cardiac glycoside compound 12
β-hydroxycalotropin.
3. cardiac glycoside compound 12 β-hydroxycalotropin according to claim 2 has treatment tumor in preparation
Purposes in the medicine of effect, is characterized in that：In step A, Radix Calotropis giganteae stem and the mass volume ratio of ethanol are 1kg：1～3L；Described
The volumn concentration of ethanol is 92～98%.
4. cardiac glycoside compound 12 β-hydroxycalotropin according to claim 2 has treatment tumor in preparation
Purposes in the medicine of effect, is characterized in that：Radix Calotropis giganteae suspension is repeated extract after 3 times with petroleum ether in step B, retain stone
Aqueous phase after oily ether extraction.
5. cardiac glycoside compound 12 β-hydroxycalotropin according to claim 2 has treatment tumor in preparation
Purposes in the medicine of effect, is characterized in that：In step F, the volume ratio of chloroform and acetone is 4:5；Adopt during gel filtration chromatography
Gel column is Sephadex LH-20 gel column, the second that during gel filtration chromatography, eluting solvent is 95% using volumn concentration
Alcohol；The eluting solvent adopting during silica gel column chromatography again is 11 for volume ratio:1:1 chloroform, methanol and acetone mixed solvent.
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| CN201410662253.5A CN104398532B (en) | 2013-04-11 | 2013-04-11 | Application of cardiac glycoside compound 12beta-hydroxycalotropin |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310124216.4A CN103191143B (en) | 2013-04-11 | 2013-04-11 | New application of cardiac glycoside compound |
| CN201410662253.5A CN104398532B (en) | 2013-04-11 | 2013-04-11 | Application of cardiac glycoside compound 12beta-hydroxycalotropin |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1711099A (en) * | 2002-10-09 | 2005-12-21 | 优尼拜尔斯金股份有限公司 | Extract with anti-tumor and anti-poisonous activity |
| CN101156865A (en) * | 2007-10-26 | 2008-04-09 | 中国热带农业科学院热带生物技术研究所 | Antineoplastic new usage of cardiac glycoside compound in antiar |
-
2013
- 2013-04-11 CN CN201410662253.5A patent/CN104398532B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1711099A (en) * | 2002-10-09 | 2005-12-21 | 优尼拜尔斯金股份有限公司 | Extract with anti-tumor and anti-poisonous activity |
| CN101156865A (en) * | 2007-10-26 | 2008-04-09 | 中国热带农业科学院热带生物技术研究所 | Antineoplastic new usage of cardiac glycoside compound in antiar |
Non-Patent Citations (1)
| Title |
|---|
| Cytotoxicity of cardenolides and cardenolide glycosides from Asclepias curassavica;Jun-zhu Li,等;《Bioorganic ＆ Medicinal Chemistry Letters》;20090214;第19卷;1956-1959 * |
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