CN102229640B - Application of triterpenoid saponins compound extracted from anemone taipaiensis - Google Patents
Application of triterpenoid saponins compound extracted from anemone taipaiensis Download PDFInfo
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Abstract
The invention provides a triterpenoid saponins compound, the molecular formula of which is C52H84O20 and the chemical name of which is 3b-O-[b-D-xylopyranose-(1-3)-a-L-rhamnopyranosyl-(1-2)-[b-D-glucopyranesyl-(1-4)]-a-L-arabopyranose] oleanolic acid (3b-O-[b-D-xylopyranosyl-(1-3)-a-L-rhamnopyranosyl-(1-2)-[b-D-glucopyranosyl-(1-4)]-a-L-arabinopyranosyl]oleanolicacid). An in-vitro antitumor test proves that the triterpenoid saponins compound has obvious inhibitory action on C6 rat spongioblastoma cell and four spongioblastoma cells: U87MG, U251MG, BT325 and SHG44, but has no influence on the growth of primarily cultured human neurogliocyte. The triterpenoid saponins compound can be used for preparing medicaments for treating glioma.
Description
Technical field
The present invention relates to medical technical field, be to separate and have the compound of antitumour activity from the distinctive thimbleweed in Shaanxi Province (too silver lotus flower), specifically from silver lotus flower too, extract a kind of triterpene saponin componds of being separated to and in the application of preparing in anticol matter tumor medicine.
Background technology
People's glioma is modal one in intracranial tumors, and disability rate and mortality ratio are high, and within 5 years, survival rate is 20%～30%, accounts for 5 years survival rate less thaies 5% of glioblastoma multiforme patient of half in all gliomas.At present in order to treat the chemotherapeutics of glioma, mainly contain nitrosourea alkylating agent nimustine (ACNU), carmustine, lomustine and procarbazine, Rheumatrex, endoxan, teniposide etc., but these medicines are efficient lower to glioblastoma, be generally less than 50%, to survival time, extend not obvious, and very easily cause serious liver damage and bone marrow depression, often because the toxic side effects of medicine is heavy, have to abandon chemotherapy; In addition, gliomas at least more than half are to conventional chemotherapeutics resistance.Therefore, with compared with the treatment of other tumours, more lack clinically at present the effective medicine of glioma, the exploitation of the efficient chemotherapeutics of new type of safe is this sick active demand for the treatment of.
Ranunculaceae thimbleweed is extensive in China branch, approximately have more than 50 to plant, wherein existing many as medicinal, medicinal part is mainly its flourishing root stock, wherein the rhizome of anemone raddeana Regel is that the traditional Chinese medicine that records of < < Pharmacopoeia of People's Republic of China > > is pointed at both ends, there is the effect of wind-damp dispelling and subduing inflammation, for arthralgia due to wind-cold-dampness pathogen BI syndrome, spasm of the limbs, arthralgia and carbuncle turgescence canker, the medicinal herbs most in use of this genus are crow (the shady Anemone cathayensis Kitag. rhizome of woods) and Rhizome of Irkutsk Anemone (anemone altaica rhizome) in addition.Existing more than 10 researchs of planting this platymiscium chemical composition and pharmacologically active are so far reported, altogether isolation identification comprise that anticancer active constituent Anemodeanin A etc., take triterpenoid saponin as more than 100 main chemical composition, wherein approximately has 70 new compounds for first finding from this platymiscium.Large quantity research shows, separates the triterpene saponin componds obtaining and have antitumor, anti-inflammatory, anticonvulsion, analgesia and the effect such as antibacterial from thimbleweed.
Too silver lotus flower (Anemone taipaiensis) is the distinctive thimbleweed in Shaanxi Province, about the research of this plant chemical ingredient and pharmacologically active there is not yet report.This problem is for first its chemical composition being studied, and carries out the screening of antitumor pharmacology activity to separating the compound obtaining, and for further developing this plant, provides reference, is also this Shaanxi Province's peculiar medicinal plants Resource Supply scientific basis of exploitation.
We from pick up from too silver lotus flower isolation identification 30 kinds of triterpenoid saponins, deep pharmacological research shows, these triterpene saponin componds majorities have significant cytotoxicity.Wherein a kind of compound 3
b-O-{
b-D-xylopyranosyl-(1 → 3)-
a-L-rhamnopyranosyl-(1 → 2)-[
b-D-glucopyranosyl-(1 → 4)]-
a-L-arabopyranose } Oleanolic Acid has significant cytotoxicity, IC to people's glioma U-251MG cell
50value and the clinical Nimustine that is usually used in malignant brain tumor treatment approach, but do not affect the neuroglia cell of human growth of former culture.This compound is compound shown in following formula Ι, and this compound chemical structure exists
(higher primary school is flat for Liao Xun, Li Baigang, and government authorities is sent out, Ding Lisheng, Chen Yaozu. the bioactive triterpene saponin(e [J] of southwestern Anemone cathayensis Kitag.. and herbal medicine, 2001,32 (6): 493-496)in be found report.And we to this compound activity research process in, its to the cytotoxicity of K-562 human leukemia cell and BEL-7402 human liver cancer cell by we report (
xiao-YangWang 1 , Xiao-Li Chen 1 *, Hai-Feng Tang 1 , Hui Gao 2 , Xiang-Rong Tian 3 , Ping-Hu Zhang 4 cytotoxic Triterpenoid Saponins from the Rhizomes of Anemone taipaiensis. Planta Med. 2011,23), but its anticol matter tumor activity there is not yet bibliographical information and patent application.
Summary of the invention
Object of the present invention aims to provide a kind of extraction from the triterpene saponin componds of silver lotus flower too in the application of preparing aspect anticol matter tumor medicine.
The object of the present invention is achieved like this, and a kind of from the triterpene saponin componds that too silver lotus flower extracts, the molecular formula that it is characterized in that this compound is C
52h
84o
21, compound shown in formula Ι
Formula I
Its chemical name of said structure is that the chemical name of above-mentioned formula Ι structure is 3
b-O-{
b-D-xylopyranosyl-(1 → 3)-
a-L-rhamnopyranosyl-(1 → 2)-[
b-D-glucopyranosyl-(1 → 4)]-
a-L-arabopyranose } Oleanolic Acid (3
b-O-{
b-D-xylopyranosyl-(1 → 3)-
a-L-rhamnopyranosyl-(1 → 2)-[
b-D-glucopyranosyl-(1 → 4)]-
a-L-arabinopyranosyl} oleanolic acid), be from the triterpene saponin componds that too silver lotus flower extracts, hereinafter to be referred as it, be XRGAO; The application of described formula I compounds X RGAO in the medicine for the treatment of glioma.
Described formula I compounds X RGAO has obvious restraining effect to C6 large mouse glioblastoma cell and U251MG, U87MG, BT325 and tetra-kinds of humanized's glioblastoma cells of SHG44, and half effective inhibition concentration (IC50 value) is between 1.69 ± 0.32 μ mol/L; And, when height to 50 μ mol/L concentration, do not affect the neuroglia cell of human growth of former culture yet.Formula I compd E HMC to the restraining effect of MKN-28 people's cancer of the stomach and A-549 human lung carcinoma cell very a little less than, show that it has selectively acting to glioma.
Get too silver lotus flower dry rhizome 5 kg, after pulverizing, with 70% alcohol heating reflux extraction, (5 L × 3, are respectively 2 h, and h), extracting liquid filtering is also merged into general extractive to 2 h and 1.General extractive concentrate drying obtains 650 g, be scattered in 8 L water, use successively again petroleum ether degreasing (8 L × 2), water-saturated n-butanol extraction (8 L × 3), obtain respectively sherwood oil (15 g) and propyl carbinol (110 g) two extract positions.(110 g) carry out silica gel column chromatography to n-butanol layer, and eluting solvent is CHCl
3: MeOH:H
2o (volume ratio is 30:1:0-6:4:0.8), gets material after chromatography (11 g) silica gel column chromatographies again, CHCl
3: n-BuOH (volume ratio is 6:1-1:3) is eluting solvent, after this (1.5 g) for material after chromatography, carry out purifying with Sephadex LH-20, MeOH wash-out, finally by high performance liquid chromatograph separation and purification, volume ratio is that the Methanol+Water of 87:13 is moving phase wash-out, obtains formula
the sterling of compounds X RGAO.
The described method of extracting separate type I compounds X RGAO from silver lotus flower too, except application conventional solvent extraction, solvent extraction and various chromatographic separation technology, when application silica gel column chromatography method is prepared total triterpenoid saponin from total glycosides extractive, the following means of definite employing for the total triterpenes saponin(e that includes XRGAO check: with silica gel thin-layer chromatography, detect, chloroform-methanol-water mixed solvent that propyl carbinol-acetic acid-water mixed solvent that employing volume ratio is 12:3:5 or volume ratio are 15:4:1 launches, and collects R
fstream part that value shows red-purple spot at 0.1～0.3 place, is too silver lotus flower total saponins.
Described formula I compounds X RGAO, when as drug use, can be independent use, can be also to mix use with other compositions.
When clinical application, with conventional preparation process, use separately or prepare into the medicine of operable various different dosage forms clinically with other drug, as injection or powder or pill or capsule or tablet or microcapsule or soft capsule or film or paste or tincture or granule or aerosol etc.
Feature of the present invention is:
Lack clinically at present the effectively medicine for the treatment of glioma, although the inventor a kind of triterpenes saponins compound XRGAO of isolation identification from silver lotus flower too also can suppress K-562 human leukemia cell and BEL-7402 hepatoma cell growth simultaneously, but than being developed as leukemia and medicines resistant to liver cancer, developing its significant anti-glioma effect and be applied to clinical treatment glioma and have more important realistic meaning.And, this compound for the restraining effect of other tumour cells such as MKN-28 people's cancer of the stomach, A-549 people's lung cancer very a little less than, show that it has certain selectivity to the restraining effect of glioma.
The structure of formula Ι compounds X RGAO is found and is reported by the inventor, but its anti-glioma effect has no any bibliographical information and patent application, its remarkable restraining effect to various human and mouse glioblastoma cell strain and the effect that does not suppress normal neurogliocyte growth show that its anticol matter tumor medicine that can be used as new high-efficiency low-toxicity researchs and develops.
Embodiment
Get too silver lotus flower dry rhizome 5 kg, after pulverizing, with 70% alcohol heating reflux extraction, (5 L × 3, are respectively 2 h, and h), extracting liquid filtering is also merged into general extractive to 2 h and 1.General extractive concentrate drying obtains 650 g, be scattered in 8 L water, use successively again petroleum ether degreasing (8 L × 2), water-saturated n-butanol extraction (8 L × 3), obtain respectively sherwood oil (15 g) and propyl carbinol (110 g) two extract positions.(110 g) carry out silica gel column chromatography to n-butanol layer, and eluting solvent is CHCl
3: MeOH:H
2o (volume ratio is 30:1:0-6:4:0.8), gets material after chromatography (11 g) silica gel column chromatographies again, CHCl
3: n-BuOH (volume ratio is 6:1-1:3) is eluting solvent, after this (1.5 g) for material after chromatography, carry out purifying with Sephadex LH-20, MeOH wash-out, finally by high performance liquid chromatograph separation and purification, volume ratio is that the Methanol+Water of 87:13 is moving phase wash-out, obtains formula
the sterling of compounds X RGAO.
Below in conjunction with specific embodiment, essence of the present invention is described.Should be understood that these embodiment make the said formula of the present invention
the purposes of compounds X RGAO2 is confirmed, and be not used in, limits the scope of the invention.The test method of unreceipted actual conditions in following embodiment, conventionally according to normal condition, or the condition of advising according to manufacturer.
embodiment: the extraction of compound is with separation
The raw material of Preparation Example compound is silver lotus flower dry rhizome too, and raw material weighs 5 kilograms, after shredding, adds the ethanol that 5 liters of concentration are 70% to carry out refluxing extraction, extracts altogether first twice 2 hours, 1 hour for the third time 3 times.United extraction liquid, decompression and solvent recovery (reclaim under reduced pressure is common the adopted suction filtration method of the industry, lower with), obtains 650 g of ethanol extraction concentrate drying.Extract is scattered in 8 L water, with petroleum ether degreasing 2 times, each 8 L, the water after extraction is used water saturation n-butanol extraction 3 times again, each 8 L, obtain respectively sherwood oil (15 g) and propyl carbinol (110 g) two extract positions.To n-butanol layer (110 g) extract carry out silica gel column chromatography, mixed solvent with chloroform-methanol-water carries out gradient elution, the volume ratio of elutriant is 30:1:0 (taking off layer as elutriant), 20:1:0, 10:1:1, 8:1:1, 9:2:0, 5:2:1, 7:3:1 and 6.5:3:1, each gradient eluent consumption is 2 L, by 500 mL, be that 1 stream part receives, and (it is the mixed solvent of 15:4:1 chloroform-methanol-water that thin-layer developing solvent adopts volume ratio with silica gel thin-layer chromatography detection, developer is that volume ratio is sulfuric acid-methanol solution of 1:4, after spray developer, in 105 ℃ of heating, develop the color), collect R
fvalue shows stream part of red-purple spot at 0.15～0.20 place, totally 11 g, proceed silica gel column chromatography by this 11 g material, with chloroform-water saturated n-butanol mixed solvent wash-out, the volume ratio of elutriant is 6:1,3:1,1:1,1:2 and 1:3, each gradient eluent consumption is 500 mL, by 100 mL be 1 stream part receive, thin-layer chromatography detect, merge containing as shown in the formula
19th～26 streams part of compounds X RGAO, after evaporated under reduced pressure solvent, obtain 1.5 g materials, with dissolve with methanol, adopt again Sephadex LH-20 gel column (Pharmacia company) to carry out column chromatography, carry out wash-out with methyl alcohol, by 10 milliliters be one stream part receive, thin-layer chromatography detect, merge containing as shown in the formula
15th～30 streams part of compounds X RGAO, obtain 0.65 g sample A after evaporated under reduced pressure solvent.Through high performance liquid chromatograph (Dai An company) separation and purification, (high-efficient liquid phase chromatogram condition is sample A: YMC-Pack R & D ODS-A chromatographic column, 5 mm, 20 × 250 mm I.D., 83% methyl alcohol is moving phase, flow velocity 8mL/min, room temperature, UV-VIS detector 206 nm wavelength places are detected, retention time is 16 min), obtain sterling 19.0 mg as shown in the formula I compounds X RGAO.
Formula I
Its chemical name of said structure is 3
b-O-{
b-D-xylopyranosyl-(1 → 3)-
a-L-rhamnopyranosyl-(1 → 2)-[
b-D-glucopyranosyl-(1 → 4)]-
a-L-arabopyranose } Oleanolic Acid (3
b-O-{
b-D-xylopyranosyl-(1 → 3)-
a-L-rhamnopy-
Ranosyl-(1 → 2)-[
b-D-glucopyranosyl-(1 → 4)]-
a-L-arabinopyranosyl} oleanolic acid), be from the triterpene saponin componds that too silver lotus flower extracts, hereinafter to be referred as it, be XRGAO, described formula I compounds X RGAO can be for the preparation of the medicine for the treatment of glioma.
the Structural Identification of compound
White amorphous powder, Liebermann-Burchard and Molish reaction are positive.The ESI-MS (positive) of compounds X RGAO provides
m/z1051 [M+Na]
+; ESI-MS (negative) provides
m/z1027 [M-H]
-, the molecular weight of prompting compounds X RGAO is 1028, in conjunction with to it
1h-NMR and
13the analysis of C-NMR spectrum, determines that its molecular formula is C
52h
84o
20.
Analysis of compounds XRGAO2's
1h-NMR composes (500 MHz, pyridine-
d 5) and
13c-NMR composes (125 MHz, pyridine-
d 5), judging that it is oleanane-type triterpene saponin, aglycon is Oleanolic Acid, and 3 of aglycons, connect into glycosides with sugar, sugar chain is comprised of 4 sugar units, after acid hydrolysis, derives through GC and analyzes and detect L-Ara, L-Rha, D-Glc and D-Xyl (1:1:1:1), by with compound
24carbon spectrum data compare, find to have lacked three groups of sugar signals that connect on C-28, other comprise aglycon and 4 sugared carbon spectrum data of residue basically identical, can judge that compounds X RGAO structure is 3
b-O-{
b-D-xylopyra-nosyl-(1 → 3)-
a-L-rhamnopyranosyl-(1 → 2)-[
b-D-glucopyranosyl-(1 → 4)]-
a-L-arabinopyranosyl} oleanolic acid, carbon spectrum data are shown in
table 1, consistent with bibliographical information (higher primary school is flat for Liao Xun, Li Baigang, and government authorities is sent out, Ding Lisheng, Chen Yaozu. the bioactive triterpene saponin(e [J] of southwestern Anemone cathayensis Kitag.. and herbal medicine, 2001,32 (6): 493-496).
13C-NMR?(125?MHz)?chemical?shifts?of?saponins?
9,?
10,?
11?and
?13?in?pyridine-
d 5
the research of compound In Vitro Anti glioma effect
Embodiment formula I compounds X RGAO has been carried out to the test of In Vitro Anti glioma, and the cell strain that test adopts is respectively: 4 kinds of people's glioblastoma cells such as C6 large mouse glioblastoma cell and U251MG, U87MG, BT325 and SHG44.For the test implementation example formula I selectivity of compd E HMC to glioma and the toxicity to normal neurocyte, the neuroglia cell of human of separately getting MKN-28 people's cancer of the stomach and A-549 human lung carcinoma cell line and former culture is measured the cytotoxicity of embodiment formula I compounds X RGAO simultaneously.Adopt conventional mtt assay test.
Concrete grammar is: according to cell growth rate, cell in logarithmic phase is inoculated in to 96 well culture plates with 4000 cells/well, after adherent growth 24 hours, discard original fluid, add the solution 200 μ L containing different concns the compounds of this invention that prepare with DMEM nutrient solution, each concentration is established 3 multiple holes, and establishes Nimustine (ACNU) positive control, physiological saline contrast and acellular zeroing hole.Cell is at 37 ℃, 5% CO
295% O
2under condition, cultivate 48 hours, the concentration that then adds PBS to dissolve is MTT (Sigma company) the 20 μ L of 10 mg/mL, hatches 4 hours under similarity condition.Finally, every hole adds the dimethyl sulfoxide (DMSO) of 200 μ L, mixes.96 orifice plates are put and in microplate reader, measured absorbancy (OD) value of each hole at 490 nm places.Be calculated as follows the inhibiting rate of analyte cell growth:
Cell inhibitory rate=(1-treatment group OD value/control group OD value) × 100%
Half effective inhibition concentration IC
50value adopts Logit method to calculate.Test-results is in Table 2.
Restraining effect (the IC of the neuroglia cell of human of table 2 embodiment formula I compounds X RGAO to 5 kinds of glioblastoma cells, 2 kinds of other tumour cells and former culture
50value, μ mol/L)
| Cell strain | U87MG | U251MG | BT325 | SHG44 | C6 | MKN-28 | A-549 | Neurogliocyte |
| XRGAO2 | 0.835 ± 0.32 | 1.41 ± 0.25 | 0.78 ± 0.16 | 1.04 ± 0.27 | 1.18± 0.41 | 68.12 ±7.8 | 79.04 ± 6.3 | >100 |
| ACNU | 0.94 ± 0.24 | 1.08 ± 0.26 | 1.26 ± 0.41 | 2.41 ± 0.14 | 1.94 ± 0.06 | Do not survey | Do not survey | >100 |
Visible, embodiment formula I compounds X RGAO all has remarkable restraining effect, IC to 4 kinds of people's glioblastoma cells and a kind of large mouse glioblastoma cell
50value and the clinical Nimustine that is usually used in malignant brain tumor treatment approach, but to the restraining effect of other 2 kinds of tumour cells very a little less than, show that it has selectively acting to glioma.Embodiment formula I compounds X RGAO does not affect the neuroglia cell of human growth (IC of former culture
50value >100 μ mol/L), in concrete test, find, both made when embodiment formula I compounds X RGAO is 100 μ mol/L concentration, to the inhibiting rate of neurogliocyte also only have 8.2% (
p>0.05), but the inhibiting rate of positive control Nimustine when 100 μ mol/L concentration can reach 28.3% (
p<0.05), visible, embodiment formula I compounds X RGAO, to the basic nontoxicity of normal neurogliocyte, can be used for the medicine of preparation treatment glioma.
the preparation of medicine
Injection formula: 2 mg XRGAO, 50 mmol/L phosphoric acid buffers, pH 7.0, cumulative volume 1 mL.Method for making: get embodiment formula I compounds X RGAO 10 mg, add 50 mmol/L phosphoric acid buffers (pH 7.0), 5 mL, dissolve completely under aseptic condition, through G3 and G6 glass sand filter, filter respectively, embedding is in 1 mL ampoule, and 100 ℃ of sterilizings 30 minutes, obtain 5.
Oral preparations formula: 5mgXRGAO, 50mg N.F,USP MANNITOL, 100mg Zulkovsky starch.Method for making: get embodiment formula I compounds X RGAO 5mg, add 50mg N.F,USP MANNITOL and 100mg Zulkovsky starch, fully mix rear granulation, made granule packaging obtains granule; Made particle is loaded in hungry area softgel shell, obtains capsule; Made particle direct compression, film coating, obtains tablet; In addition, can also make powder as lactose etc. by adding different auxiliary material; Also can be capsule material with polyethylene glycol 6000, carry out packing, make pill, microcapsule and soft capsule etc.
External preparation formula: 5mg XRGAO, stearic acid 100g, Viscotrol C 100mg, whiteruss 100mg, trolamine 8mg, glycerine 40mg.Method for making: get embodiment formula I compounds X RGAO 5mg, add stearic acid 100g, Viscotrol C 100mg, whiteruss 100mg, trolamine 8mg and glycerine 40mg, stir, fully emulsified, can make paste; Can also be by adding other auxiliary materials to make tincture and film as phenylformic acid and ethanol etc.; In addition, can also add ethanol and F12 etc., refill and in special container, make aerosol.
Claims (2)
1. the triterpene saponin componds extracting from silver lotus flower is too in a purposes of preparing anticol matter tumor medicine, and its chemical structural formula is as follows:
Formula Ι.
2. a kind of triterpene saponin componds extracting from silver lotus flower too according to claim 1 is in the purposes of preparing anticol matter tumor medicine, it is characterized in that: described formula I compound can be used separately or mix with other auxiliary materials, be mixed with the injection or powder or pill or tablet or microcapsule or soft capsule or film or paste or tincture or granule or the aerosol that use clinically.
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Non-Patent Citations (2)
| Title |
|---|
| EloirPaulo Schenkel et al..Die Saponine aus Thinouia coriacea Saponins from Thinouia coriaceae.《Planta Med.》.1991,第57卷463-467. * |
| 廖循等.西南银莲花的活性三萜皂苷.《中草药》.2001,第32卷(第6期),493-496. * |
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