CN107286172B - Aporphine alkaloid Illigerine B and its preparation method and application - Google Patents
Aporphine alkaloid Illigerine B and its preparation method and application Download PDFInfo
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- CN107286172B CN107286172B CN201710444269.2A CN201710444269A CN107286172B CN 107286172 B CN107286172 B CN 107286172B CN 201710444269 A CN201710444269 A CN 201710444269A CN 107286172 B CN107286172 B CN 107286172B
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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 Illigerine 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 Illigerine B of the present invention is simple, inhibits activity of tumor cells clear, and having potential exploitation is the value of anti-tumor drug；
Description
(1) technical field
Aporphine alkaloid Illigerine B that the present invention relates to a kind of with antitumor action and preparation method thereof and
Using.
(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
Illigerine 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 Illigerine B and its preparation side with antitumor action
Method and application.
Technical scheme is as follows:
The aporphine alkaloid Illigerine B as shown in formula (I):
The present invention also provides the preparation method of aporphine alkaloid Illigerine B shown in the formula (I), the systems
Preparation Method carries out as follows:
(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 be column packing, methylene chloride, methylene chloride/methanol volume ratio 100/1~2/1 mixed liquor be eluant, eluent, carry out
Gradient elution, collects the eluent containing target compound, and evaporating solvent under reduced pressure obtains secondary column chromatography product；
Specifically, the operating method of the gradient elution are as follows: with methylene chloride, methylene chloride/methanol volume ratio 100/1,
80/1,60/1,30/1,10/1,5/1,2/1 mixed liquor is eluant, eluent, carries out gradient elution, the flow velocity of eluant, eluent is 10~
12mL/min, the elution time of the eluant, eluent of every kind of gradient are 16~20min, collect the eluent containing target compound, decompression
Solvent is evaporated off and obtains secondary column chromatography product；
(5) washing impurity-removing: carrying out washing impurity-removing with methanol for secondary column chromatography product obtained by step (4), finally dry
To aporphine alkaloid Illigerine B shown in formula (I)；
Specifically, the operating method of the washing impurity-removing are as follows: the secondary column chromatography product and methanol are pressed feed liquid quality
Volume ratio 1/5~1/10 (g/mL) is added in centrifuge tube, 40KHz ultrasound 10s, centrifugation, removal supernatant, repeated washing 3 times, most
After be dried to obtain aporphine alkaloid Illigerine 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 (Illigerine B)；When the target compound is detected with TLC, with methylene chloride: methanol volume
It is solvent, R than=10/1fValue is 0.48.
Aporphine alkaloid Illigerine B of the present invention has application prospect in preparation anti-tumor activity medicine.
The experiment proved that aporphine alkaloid Illigerine B is compared with DDP control group, to human cervical carcinoma HeLa when high concentration
Cell, human breast carcinoma Bcap37 cell and human liver cancer SMMC7721 cell have significant in-vitro multiplication inhibiting effect, and to people
Cervical Cancer HeLa Cells effect is most strong, 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 Illigerine 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.
(4) Detailed description of the invention
Fig. 1: cis-platinum (DDP), aporphine alkaloid Illigerine B (I) are to the half of three kinds of cancer cells in embodiment 5
Lethasl concentration (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:Illigerine 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 0.96g；
(4) secondary column chromatography: continue to produce primary column chromatography obtained by step (3) with 200~300 mesh column chromatography silica gel 65g
Product 0.96g carries out column chromatography for separation, with methylene chloride, methylene chloride/methanol volume ratio 100/1,80/1,60/1,30/1,10/
1,5/1,2/1 mixed liquor is eluant, eluent, carries out gradient elution, and the flow velocity of eluant, eluent is 10mL/min, the elution of every kind of gradient
The elution time of agent is 20min, collects the eluent containing target compound, and evaporating solvent under reduced pressure obtains secondary column chromatography product
52mg；
(5) washing impurity-removing: secondary column obtained by step (4) is added in centrifuge tube and chromatographs product 52mg, adds methanol
0.5mL, 40KHz ultrasound 10s, 4000rpm centrifugation 2 minutes, supernatant is removed, washes repeatedly 3 times, is finally dried to obtain product
IlligerineB 31mg。
The preparation of embodiment 2:Illigerine 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 400mL, 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 1.59g；
(4) secondary column chromatography: continue to produce primary column chromatography obtained by step (3) with 200~300 mesh column chromatography silica gel 130g
Product 1.59g carries out column chromatography for separation, with methylene chloride, methylene chloride/methanol volume ratio 100/1,80/1,60/1,30/1,10/
1,5/1,2/1 mixed liquor is eluant, eluent, carries out gradient elution, and the flow velocity of eluant, eluent is 10mL/min, the elution of every kind of gradient
The elution time of agent is 20min, collects the eluent containing target compound, and evaporating solvent under reduced pressure obtains secondary column chromatography product
63mg；
(5) washing impurity-removing: secondary column obtained by step (4) is added in centrifuge tube and chromatographs product 63mg, adds methanol
0.5mL, 40KHz ultrasound 10s, 4000rpm centrifugation 2 minutes, supernatant is removed, washes repeatedly 3 times, is finally dried to obtain product
IlligerineB 55mg。
The preparation of embodiment 3:Illigerine 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 2.76g；
(4) secondary column chromatography: continue to produce primary column chromatography obtained by step (3) with 200~300 mesh column chromatography silica gel 130g
Product 2.76g carries out column chromatography for separation, with methylene chloride, methylene chloride/methanol volume ratio 100/1,80/1,60/1,30/1,10/
1,5/1,2/1 mixed liquor is eluant, eluent, carries out gradient elution, and the flow velocity of eluant, eluent is 10mL/min, the elution of every kind of gradient
The elution time of agent is 20min, collects the eluent containing target compound, and evaporating solvent under reduced pressure obtains secondary column chromatography product
72mg；
(5) washing impurity-removing: secondary column obtained by step (4) is added in centrifuge tube and chromatographs product 72mg, adds methanol
0.5mL, 40KHz ultrasound 10s, 4000rpm centrifugation 2 minutes, supernatant is removed, washes repeatedly 3 times, is finally dried to obtain product
IlligerineB 70mg。
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 Illigerine B (I) made from embodiment 1, embodiment 2 or embodiment 3 is carried out physical and chemical
Property and Wave Spectrum analysis, ESI-MS measured value m/z:338 [M-H]-, determine that its molecular formula is C in conjunction with NMR data18H13NO6,
Molecular weight is 339, degree of unsaturation 13.
Table 5: the NMR data of gained compound Illigerine B (I)
Embodiment 5: anti-tumor activity test
Anti tumor activity in vitro survey has been carried out to aporphine alkaloid Illigerine 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 Illigerine 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, and to HeLa Cells act on it is most strong.It is potential antitumor that this, which prompts the compound,
Active drug (as shown in Figure 1).
Claims (8)
1. the aporphine alkaloid Illigerine B as shown in formula (I):
2. the preparation method of aporphine alkaloid Illigerine B shown in formula (I) as described in claim 1, which is characterized in that
The preparation method carries out as follows:
(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, methylene chloride, methylene chloride/methanol volume ratio 100/1~2/1 mixed liquor be eluant, eluent, carry out gradient
Elution, collects the eluent containing target compound, and 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 methanol, is finally dried to obtain formula
(I) B of aporphine alkaloid Illigerine shown in.
3. preparation method as claimed in claim 2, 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.
4. preparation method as claimed in claim 2, 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.
5. preparation method as claimed in claim 2, 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.
6. preparation method as claimed in claim 2, which is characterized in that in step (4), the operating method of the gradient elution
Are as follows: the mixed liquor with methylene chloride, methylene chloride/methanol volume ratio 100/1,80/1,60/1,30/1,10/1,5/1,2/1 is
Eluant, eluent carries out gradient elution, and the flow velocity of eluant, eluent is 10~12mL/min, and the elution time of the eluant, eluent of every kind of gradient is 16
~20min, collects the eluent containing target compound, and evaporating solvent under reduced pressure obtains secondary column chromatography product.
7. preparation method as claimed in claim 2, which is characterized in that the operating method of step (5) washing impurity-removing are as follows: will
The secondary column chromatography product and methanol are added in centrifuge tube by feed liquid mass volume ratio 1/5~1/10,40KHz ultrasound 10s, from
The heart removes supernatant, washes repeatedly 3 times, is finally dried to obtain aporphine alkaloid Illigerine B shown in formula (I).
8. aporphine alkaloid Illigerine B shown in formula (I) as described in claim 1 is in preparation anti-tumor activity medicine
Application.
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| CN112472729B (en) * | 2020-12-18 | 2022-03-29 | 广西壮族自治区中医药研究院 | Application of caulis sinomenii in preparing medicine for treating human glioma |
| CN114891012B (en) * | 2022-06-21 | 2023-04-25 | 海南医学院 | Aporphine alkaloid compound, and extraction method and application thereof |
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Non-Patent Citations (3)
| Title |
|---|
| Cytotoxic Aporphine Alkaloids from Cassytha filiformis;C. Stevigny,等;《Planta Medica》;20021231;第68卷(第11期);1042-1044 * |
| Cytotoxic aporphine alkaloids from Ocotea acutifolia;Fernanda R. Garcez, 等;《Planta Medica》;20111231;第77卷(第4期);383-387 * |
| 香青藤化学成分研究;谢丽莎，等;《当代医学》;20110930;第17卷(第27期);31-32 * |
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