CN107033156B - Aporphine alkaloid Laurodionine B and its preparation method and application - Google Patents
Aporphine alkaloid Laurodionine B and its preparation method and application Download PDFInfo
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- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
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Abstract
The present invention provides one kind aporphine alkaloid Laurodionine B as shown in formula (I), the compound is prepared using ILLIGERA AROMATTICA rattan as raw material through methanol extraction, ethyl acetate extraction, primary column chromatography, secondary column chromatography, five step of washing impurity-removing；Extracting and developing, the purification process of aporphine alkaloid Laurodionine B of the present invention is simple, inhibit activity of tumor cells clear, it is the value of anti-tumor drug with potential exploitation, the compound chemical structure is confirmed by spectroscopy data, there is no optical isomers, can be to avoid optical isomer potential risks；
Description
(1) technical field
The present invention relates to a kind of aporphine alkaloid Laurodionine B and preparation method thereof with antitumor action
And application.
(2) background technique
Sinomenium (Illigera) plant is Hernandiaceae (Hernanadiaceae) second largest category, is distributed mainly on east half
The ball torrid zone, subtropical zone, there are about more than 30, China has more than 12 in the whole world, is distributed widely in Southwestern China portion to Taiwan.It should
Belong to various plants to use in China as medicinal plant and traditional herbal medicine.Guangxi is civil to commonly use its stem brewed for drinking, as analgesia,
Stop dysentery, antipyretic analgesics use.Traditional Chinese Medicine thinks that it has effects that nourishing the blood to expel wind, relaxing tendons and activating collaterals, removing toxicity for detumescence, is usually used in dispelling
The diseases such as wind analgesic, eliminating stasis to subdue swelling, main rheumatic arthralgia, treating swelling and pain by traumatic injury, snakebite and bugbite, lumbar muscle strain, numb limb；It is modern
Pharmacological research shows that this platymiscium has spasmolysis and analgesia, cooling, local anaesthesia isoreactivity, is chiefly used in treating rheumatic and class at present
Rheumatic arthritis, hypertrophic spondylitis etc..
Therefore the research that system, science are carried out to such plant, verifies its effective component and the mechanism of action, finds some knots
The novel active constituent of structure, by Dietotherapy health product, the exploitation therapeutic agent to deeper development and utilization Sinomenium medicinal plant
And clinical application generates significance.
ILLIGERA AROMATTICA (Illigera aromatica S.Z.Huang et S.L.Mo) is Sinomenium (Illigera) plant,
Liana, is the distinctive liana resource of China, is distributed in Chinese Guangdong, Guangxi and Yunnan, Si Chuannan by 1~8 centimetre of rattan diameter
The ground such as portion, Taiwan.
The present invention is extracted, is separated, purifying, Structural Identification obtains using ILLIGERA AROMATTICA rattan as research object
Laurodionine B, belongs to aporphine alkaloid class compound, which has a degree of anti-tumor activity.
(3) summary of the invention
The present invention is intended to provide a kind of aporphine alkaloid Laurodionine B and its preparation with antitumor action
Methods and applications.
Technical scheme is as follows:
The aporphine alkaloid Laurodionine B as shown in formula (I):
The aporphine alkaloid Laurodionine B as shown in formula (I) is prepared as follows to obtain:
(1) methanol extracts: ILLIGERA AROMATTICA rattan being crushed drying, methanol extraction is added and extracts, filters out insoluble matter, filtrate later
Evaporated under reduced pressure obtains methanol extract；
The ILLIGERA AROMATTICA rattan can be commercially available by conventional route；
Specifically, the operating method of the methanol extraction are as follows: the ILLIGERA AROMATTICA rattan after drying and methanol will be crushed with feed liquid
Mass volume ratio 1/3~1/5 (g/mL) mixing, (20~30 DEG C, similarly hereinafter) of room temperature extract 5~10 days, and methanol extraction is obtained by filtration
Liquid, filter residue repeat extraction 2~4 times, merge gained methanol extract liquid, evaporated under reduced pressure every time and obtain methanol extract；
(2) ethyl acetate extracts: methanol extract obtained by step (1) being dispersed in water, then is extracted with ethyl acetate, is extracted
Liquid evaporated under reduced pressure obtains ethyl acetate extract；
Specifically, the operating method of the ethyl acetate extraction are as follows: disperse 5~10 for methanol extract obtained by step (1)
In the water of times quality, suspension is obtained, is extracted 3 times with isometric ethyl acetate, combined ethyl acetate phase is recovered under reduced pressure molten
Agent obtains ethyl acetate extract；
(3) primary column chromatography: column chromatography for separation is carried out to ethyl acetate extract obtained by step (2), with 200~300 mesh silicon
Glue is column packing, and the mixed liquor and ethyl acetate of petrol ether/ethyl acetate volume ratio 10/1~1/10 are eluant, eluent, carries out gradient
Elution, collects the eluent containing target compound, and evaporating solvent under reduced pressure obtains primary column chromatography product；
Specifically, the operating method of the gradient elution are as follows: with petrol ether/ethyl acetate volume ratio be respectively 10/1,8/
1,6/1,5/1,3/1,1.5/1,1/1,1/2,1/3,1/3.5,1/4.5,1/6,1/7,1/10 mixed liquor, ethyl acetate are to wash
De- agent carries out gradient elution, and the flow velocity of eluant, eluent is 18~20mL/min, and the elution time of the eluant, eluent of every kind of gradient is 360
~600min, collects the eluent containing target compound, and evaporating solvent under reduced pressure obtains primary column chromatography product；
(4) secondary column chromatography: continuing to carry out column chromatography for separation to primary column chromatography product obtained by step (3), with 200~
300 mesh silica gel are column packing, and the mixed liquor of petrol ether/ethyl acetate volume ratio 2/1 is eluant, eluent, carry out isocratic elution, collect
Eluent containing target compound, evaporating solvent under reduced pressure obtain secondary column chromatography product；
Specifically, the operating method of the isocratic elution are as follows: the mixed liquor with petrol ether/ethyl acetate volume ratio 2/1 is
Eluant, eluent carries out isocratic elution, and the flow velocity of eluant, eluent is 15~18mL/min, and elution time is 350~450min, collects and contains mesh
The eluent of compound is marked, evaporating solvent under reduced pressure obtains secondary column chromatography product；
(5) washing impurity-removing: secondary column chromatography product obtained by step (4) is subjected to washing impurity-removing with ethyl acetate, is finally done
Aporphine alkaloid Laurodionine B shown in dry formula (I) to obtain the final product；
Specifically, the operating method of the washing impurity-removing are as follows: the secondary column chromatography product and ethyl acetate are pressed feed liquid
Mass volume ratio 1/5~1/10 (g/mL) is added in centrifuge tube, 40KHz ultrasound 10s, centrifugation, removes supernatant, repeated washing 3
It is secondary, finally it is drying to obtain aporphine alkaloid Laurodionine B shown in formula (I).
Step (3) of the present invention, (4) column chromatography procedure in, can detect to collect by thin-layer chromatography (TLC) and contain target
The eluent of compound (Laurodionine B)；When the target compound is detected with TLC, with chloroform: methanol volume ratio
=10/1 mixed liquor is solvent, RfValue is 0.59.
Before aporphine alkaloid Laurodionine B of the present invention has application in preparation anti-tumor activity medicine
Scape.The experiment proved that aporphine alkaloid Laurodionine B is compared with DDP control group, to human cervical carcinoma when high concentration
HeLa cell, human breast carcinoma Bcap37 cell and human liver cancer SMMC7721 cell have significant in-vitro multiplication inhibiting effect, and
Most strong to HeLa cyto-inhibition, this prompts the compound to have potential anti-tumor activity.
The beneficial effects of the present invention are the extracting and developing of: aporphine alkaloid Laurodionine B of the present invention,
Purification process is simple, inhibits activity of tumor cells clear, and having potential exploitation is the value of anti-tumor drug, the chemical combination materialization
It learns structure to be confirmed by spectroscopy data, optical isomer is not present, it can be to avoid optical isomer potential risks.
(4) Detailed description of the invention
Fig. 1: cis-platinum (DDP) in embodiment 5, Laurodionine B (I) are to the half lethal concentrations of three kinds of cancer cells
(IC50)。
(5) specific embodiment
Below by specific embodiment, the present invention is further illustrated, but protection scope of the present invention is not limited in
This.
The ILLIGERA AROMATTICA rattan used in following embodiment is purchased from Guangxi Yulin Chinese Medicinal Materials Markets.
The preparation of embodiment 1:Laurodionine B
Table 1: experiment instrument
(1) methanol extracts: ILLIGERA AROMATTICA rattan 500g of the crushing after dry is mixed with methanol 2000mL, room temperature extracts 5 days,
Methanol extract liquid is obtained by filtration, filter residue repeats extraction 4 times, merges gained methanol extract liquid, evaporated under reduced pressure every time, obtains methanol leaching
Cream 50g.
(2) ethyl acetate extracts: dispersing methanol extract 30g obtained by step (1) in water 250mL, obtains suspension, uses
Isometric ethyl acetate extracts 3 times, and solvent is recovered under reduced pressure in combined ethyl acetate phase, obtains ethyl acetate extract 12g.
(3) primary column chromatography: with 200~300 mesh column chromatography silica gel 450g to ethyl acetate extract 12g obtained by step (2)
Column chromatography for separation is carried out, is respectively 10/1,8/1,6/1,5/1,3/1,1.5/1,1/1,1/ with petrol ether/ethyl acetate volume ratio
2,1/3,1/3.5,1/4.5,1/6,1/7,1/10 mixed liquor and ethyl acetate it is (pure) be eluant, eluent, carry out gradient elution, wash
The flow velocity of de- agent is 18mL/min, and the elution time of the eluant, eluent of every kind of gradient is 400min, collects washing containing target compound
De- liquid, evaporating solvent under reduced pressure obtain primary column chromatography product 2g；
(4) secondary column chromatography: continue to produce primary column chromatography obtained by step (3) with 200~300 mesh column chromatography silica gel 220g
Product 2g carries out column chromatography for separation, using the mixed liquor of petrol ether/ethyl acetate volume ratio 2/1 as eluant, eluent, carries out isocratic elution, washes
The flow velocity of de- agent is 15mL/min, and the elution time of eluant, eluent is 350min, collects the eluent containing target compound, and decompression is steamed
Except solvent obtains secondary column chromatography product 9mg；
(5) washing impurity-removing: secondary column obtained by step (4) is added in centrifuge tube and chromatographs product 10mg, adds acetic acid second
Ester 0.10mL, 40KHz ultrasound 10s, 4000rpm centrifugation 2 minutes, supernatant is removed, washes repeatedly 3 times, is finally dried to obtain production
Object Laurodionine B 5mg.
The preparation of embodiment 2:Laurodionine B:
Table 2: experiment instrument
(1) methanol extracts: ILLIGERA AROMATTICA rattan 1000g of the crushing after dry being mixed with methanol 3000mL, room temperature extraction 5
It, is obtained by filtration methanol extract liquid, and filter residue repeats extraction 4 times, merges gained methanol extract liquid, evaporated under reduced pressure every time and obtains first
Alcohol medicinal extract 50g.
(2) ethyl acetate extracts: dispersing methanol extract 50g obtained by step (1) in water 500mL, obtains suspension, uses
Isometric ethyl acetate extracts 3 times, and solvent is recovered under reduced pressure in combined ethyl acetate phase, obtains ethyl acetate extract 23g.
(3) primary column chromatography: with 200~300 mesh column chromatography silica gel 450g to ethyl acetate extract 23g obtained by step (2)
Column chromatography for separation is carried out, is respectively 10/1,8/1,6/1,5/1,3/1,1.5/1,1/1,1/ with petrol ether/ethyl acetate volume ratio
2,1/3,1/3.5,1/4.5,1/6,1/7,1/10 mixed liquor and ethyl acetate it is (pure) be eluant, eluent, carry out gradient elution, wash
The flow velocity of de- agent is 18mL/min, and the elution time of the eluant, eluent of every kind of gradient is 400min, collects washing containing target compound
De- liquid, evaporating solvent under reduced pressure obtain primary column chromatography product 5g；
(4) secondary column chromatography: continue to produce primary column chromatography obtained by step (3) with 200~300 mesh column chromatography silica gel 300g
Product 5g carries out column chromatography for separation, using the mixed liquor of petrol ether/ethyl acetate volume ratio 2/1 as eluant, eluent, carries out isocratic elution, washes
The flow velocity of de- agent is 15mL/min, and the elution time of eluant, eluent is 400min, collects the eluent containing target compound, and decompression is steamed
Except solvent obtains secondary column chromatography product 22mg；
(5) washing impurity-removing: secondary column obtained by step (4) is added in centrifuge tube and chromatographs product 22mg, adds acetic acid second
Ester 0.20mL, 40KHz ultrasound 10s, 4000rpm centrifugation 2 minutes, supernatant is removed, washes repeatedly 3 times, is finally dried to obtain production
Object Laurodionine B 11mg.
The preparation of embodiment 3:Laurodionine B:
Table 3: experiment instrument
(1) methanol extracts: ILLIGERA AROMATTICA rattan 25kg of the crushing after dry being mixed with methanol 100L, room temperature extracts 5 days, mistake
Filter obtains methanol extract liquid, and filter residue repeats extraction 4 times, merges gained methanol extract liquid, evaporated under reduced pressure every time and obtains methanol extract
1kg。
(2) ethyl acetate extracts: it disperses methanol extract 1kg obtained by step (1) in water 5000mL, obtains suspension,
It is extracted 3 times with isometric ethyl acetate, solvent is recovered under reduced pressure in combined ethyl acetate phase, obtains ethyl acetate extract 293g.
(3) primary column chromatography: with 200~300 mesh column chromatography silica gel 1.7kg to ethyl acetate extract obtained by step (2)
293g carries out column chromatography for separation, is respectively 10/1,8/1,6/1,5/1,3/1,1.5/1,1/ with petrol ether/ethyl acetate volume ratio
1,1/2,1/3,1/3.5,1/4.5,1/6,1/7,1/10 mixed liquor and ethyl acetate it is (pure) be eluant, eluent, carry out gradient wash
De-, the flow velocity of eluant, eluent is 18mL/min, and the elution time of the eluant, eluent of every kind of gradient is 500min, collects and contains target compound
Eluent, evaporating solvent under reduced pressure obtains primary column chromatography product 5g；
(4) secondary column chromatography: continue to produce primary column chromatography obtained by step (3) with 200~300 mesh column chromatography silica gel 130g
Product 5g carries out column chromatography for separation, using the mixed liquor of petrol ether/ethyl acetate volume ratio 2/1 as eluant, eluent, carries out isocratic elution, washes
The flow velocity of de- agent is 15mL/min, and the elution time of eluant, eluent is 350min, collects the eluent containing target compound, and decompression is steamed
Except solvent obtains secondary column chromatography product 62mg；
(5) washing impurity-removing: secondary column obtained by step (4) is added in centrifuge tube and chromatographs product 62mg, adds acetic acid second
Ester 0.5mL, 40KHz ultrasound 10s, 4000rpm centrifugation 2 minutes, supernatant is removed, washes repeatedly 3 times, is finally dried to obtain product
Laurodionine B 52mg。
Embodiment 4: compound test
Table 4: experiment instrument
Reagent: nuclear magnetic resonance uses deuterated DMSO (dimethyl sulfoxide) reagent, and mass spectrum uses Merck KGaA (Merck) chromatographically pure
Reagent.
Aporphine alkaloid Laurodionine B (I) made from embodiment 1, embodiment 2 or embodiment 3 is carried out physical and chemical
Property and Wave Spectrum analysis, ultraviolet spectra UV (nm): 265,347.Infrared spectroscopy IR (cm-1): 3438,1720,1618,1585,
1466,1120,1103.Electrospray ionization mass spectrum (ESI-MS) measured value m/z:362 [M-H]-, molecular weight 363, in conjunction with NMR data
Determine that its molecular formula is C20H13NO6, degree of unsaturation 15.
Table 5: the NMR data of gained compound L aurodionine B (I)
Embodiment 5: anti-tumor activity test
Anti tumor activity in vitro survey has been carried out to aporphine alkaloid Laurodionine B (I) made from above-described embodiment
Examination.
Method: logarithmic growth phase tumour cell adjusts concentration of cell suspension, and every 100 μ L cell suspension inoculation of hole is in 96
In porocyte culture plates, (100 hole μ L/) is administered afterwards for 24 hours in inoculation, sets cell controls group and 4 concentration of test medicine groups respectively.
Continue every hole after cultivating 72h and 100 μ L MTT (1mg/mL, with the dissolution of DMEM culture solution) is added, 37 DEG C of incubation 2h are discarded in each hole
150 μ L acidification isopropanol (HCl containing 0.04mol/L), the inspection of avoid light place 30min, DG3022A type enzyme linked immunological are added after liquid
Absorbance at instrument measurement 570nm is surveyed, each test medicine is calculated to the proliferation inhibition rate of tumour cell, is write with professor Sun Ruiyuan
NDST computer program calculates the half-inhibitory concentration (IC of each test medicine50)。
As a result: aporphine alkaloid Laurodionine B (I) is compared with DDP control group obtained by above-described embodiment
To HeLa Cells when compared with, high concentration, human breast carcinoma Bcap37 cell and human liver cancer SMMC7721 cell have significant
In-vitro multiplication inhibiting effect, wherein the inhibition to HeLa Cells is most strong.It is potential anti-that this, which prompts the compound,
The drug (as shown in Figure 1) of tumor promotion.
Claims (6)
1. the preparation method of aporphine alkaloid Laurodionine B as shown in formula (I),
It is characterized in that, it is described the preparation method comprises the following steps:
(1) methanol extracts: ILLIGERA AROMATTICA rattan being crushed drying, methanol extraction is added and extracts, filters out insoluble matter, filtrate decompression later
It is evaporated to obtain methanol extract；
(2) ethyl acetate extracts: methanol extract obtained by step (1) being dispersed in water, then is extracted with ethyl acetate, extract liquor subtracts
Pressure is evaporated to obtain ethyl acetate extract；
(3) primary column chromatography: column chromatography for separation is carried out to ethyl acetate extract obtained by step (2), is with 200~300 mesh silica gel
Column packing, the mixed liquor and ethyl acetate of petrol ether/ethyl acetate volume ratio 10/1~1/10 are eluant, eluent, carry out gradient and wash
It is de-, the eluent containing target compound is collected, evaporating solvent under reduced pressure obtains primary column chromatography product；
(4) secondary column chromatography: continue to carry out column chromatography for separation to primary column chromatography product obtained by step (3), with 200~300 mesh
Silica gel is column packing, and the mixed liquor of petrol ether/ethyl acetate volume ratio 2/1 is eluant, eluent, carries out isocratic elution, collects and contain target
The eluent of compound, evaporating solvent under reduced pressure obtain secondary column chromatography product；
(5) washing impurity-removing: secondary column chromatography product obtained by step (4) is subjected to washing impurity-removing with ethyl acetate, finally drying is
Obtain aporphine alkaloid Laurodionine B shown in formula (I).
2. preparation method as described in claim 1, which is characterized in that the operating method of step (1) the methanol extraction are as follows: will
ILLIGERA AROMATTICA rattan after crushing drying is mixed with methanol with feed liquid mass volume ratio 1/3~1/5, and room temperature extracts 5~10 days, filtering
Methanol extract liquid is obtained, filter residue repeats extraction 2~4 times, merges gained methanol extract liquid, evaporated under reduced pressure every time, obtains methanol leaching
Cream.
3. preparation method as described in claim 1, which is characterized in that the operating method of step (2) the ethyl acetate extraction
Are as follows: it disperses methanol extract obtained by step (1) in the water of 5~10 times of quality, suspension is obtained, with isometric ethyl acetate
Extraction 3 times, combined ethyl acetate phase is recovered under reduced pressure solvent, obtains ethyl acetate extract.
4. preparation method as described in claim 1, which is characterized in that in step (3), the operating method of the gradient elution
Are as follows: with petrol ether/ethyl acetate volume ratio be respectively 10/1,8/1,6/1,5/1,3/1,1.5/1,1/1,1/2,1/3,1/3.5,
1/4.5,1/6,1/7,1/10 mixed liquor, ethyl acetate are eluant, eluent, carry out gradient elution, the flow velocity of eluant, eluent is 18~
20mL/min, the elution time of the eluant, eluent of every kind of gradient are 360~600min, collect the eluent containing target compound, subtract
Pressure is evaporated off solvent and obtains primary column chromatography product.
5. preparation method as described in claim 1, which is characterized in that in step (4), the operating method of the isocratic elution
Are as follows: using the mixed liquor of petrol ether/ethyl acetate volume ratio 2/1 as eluant, eluent, carrying out isocratic elution, the flow velocity of eluant, eluent is 15~
18mL/min, elution time are 350~450min, collect the eluent containing target compound, evaporating solvent under reduced pressure obtains secondary
Column chromatographs product.
6. preparation method as described in claim 1, which is characterized in that the operating method of step (5) washing impurity-removing are as follows: will
The secondary column chromatography product and ethyl acetate are added in centrifuge tube by feed liquid mass volume ratio 1/5~1/10,40KHz ultrasound
10s, centrifugation remove supernatant, wash repeatedly 3 times, are finally drying to obtain aporphine alkaloid shown in formula (I)
Laurodionine B。
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Non-Patent Citations (3)
| Title |
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| Aporphinoid alkaloids and other constituents from Lettowianthus stellatus;Mayunga H.H. Nkunya, et al.;《Phytochemistry》;20001231;第53卷;第1067-1073页 * |
| The constituents of Michelia compressa var. formosana and their bioactivities;Yu-Yi Chan, et al.;《Int. J. Mol. Sci.》;20140617;第15卷;第10926-10935页 * |
| 陵水暗罗枝、叶中的阿朴菲生物碱;吕子明等;《中国中药杂志》;20090930;第34卷(第18期);第2343-2345页 * |
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