CN107522706A - Parallel double tetrahydrofuran lignans and its preparation method and application - Google Patents
Parallel double tetrahydrofuran lignans and its preparation method and application Download PDFInfo
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- CN107522706A CN107522706A CN201710507284.7A CN201710507284A CN107522706A CN 107522706 A CN107522706 A CN 107522706A CN 201710507284 A CN201710507284 A CN 201710507284A CN 107522706 A CN107522706 A CN 107522706A
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- parallel double
- petroleum ether
- double tetrahydrofuran
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Abstract
The invention discloses a kind of parallel double tetrahydrofuran lignans and its preparation method and application, preparing for the lignanoid is as follows：1. by sorrow escape grass meal it is broken after with ethanol soak refluxing extraction, obtain the total medicinal extract of ethanol, be then dispersed in distilled water, extracted successively with petroleum ether and ethyl acetate；2. petroleum ether part medicinal extract is passed through into silica gel column chromatography, gradient elution is carried out using petroleum ether ethyl acetate solvent system, collects, concentrate, merging identical flow point；3. petroleum ether: ethyl acetate=5 will be used: 1 flow point afforded carries out reversed-phase silica gel column chromatography separation, the sephadex column chromatography for separation of Sephadex LH 20 and high performance liquid chromatography separation successively, obtains parallel double tetrahydrofuran lignans.The parallel double tetrahydrofuran lignans that the present invention extracts in escaping grass from sorrow have inhibitory activity to s, the cells of breast cancer MCF 7, Lung Adenocarcinoma A 549 Cell.
Description
Technical field
The present invention relates to a kind of natural plant extracts, and in particular to a kind of parallel double tetrahydrofuran lignans and its preparation
Methods and applications.
Background technology
Acanthaceae（Acanthaceae）Crocodile mouth flower category（Clinacanthus Nees）Plant, the whole world have 2 kinds, main distribution
In the south China torrid zone to the ground such as Malaysia, Java, Kalimantan.China is distributed a kind, i.e. sorrow is escaped grass（Clinacanthus
nutans）, also known as crocodile mouth flower, Sabah snakeweed, blue or green arrow etc..The plant mainly originates in Hainan, Guangdong, Guangxi and Yunnan etc. and saves ground,
It is mainly used in clearing heat and detoxicating, dampness removing, eliminating stasis to subdue swelling, promoting blood circulation for regulating menstruation, analgesic etc. among the people.At present, in Wuzhishan Mountain in Hainan city
There is large-scale planting.Found through consulting pertinent literature, the research report to its chemical composition and pharmacological activity is less both at home and abroad.
Parallel double tetrahydrofuran lignans are formed by the hydroxyl condensation in tetrahydrofuran lignans on fat hydrocarbon chain,
Symmetrical structure containing 18 carbon in precursor skeleton.Up to the present, two tetrahydrofuran rings in the lignanoid of this structure
Closed with cis spatial configuration a pair of horses going side by side, the skeleton of double tetrahydrofuran ring also only has a kind of structure type, i.e. 7-O-9' types and 7'-O-9
Type tetrahydrofuran ring is closed by 8,8'- carbon a pair of horses going side by side.Come from current separated obtained parallel double tetrahydrofuran lignans class compound
See, be only the species of oxygen-containing substituents and the difference of spatial configuration on their hydrocarbyl chain and phenyl ring, cause such chemical combination
The species of thing is various, and causes the difficulty of separation and Structural Identification.
The content of the invention
It is an object of the invention to solve the above problems, there is provided a kind of parallel double tetrahydrofuran lignans and preparation method thereof
And application.
Realizing the technical scheme of the object of the invention is：A kind of parallel double tetrahydrofuran lignans, its structure such as formula（Ⅰ）Institute
Show：
（Ⅰ）.
The preparation method of above-mentioned parallel double tetrahydrofuran lignans comprises the following steps：
1. by the sorrow of natural air drying escape grass meal it is broken after with ethanol soak refluxing extraction, by the phegma being collected into merge, decompression steam
Evaporate, obtain the total medicinal extract of ethanol, then the total medicinal extract of above-mentioned ethanol is dispersed in distilled water, successively with petroleum ether and acetic acid second
Ester is extracted, and obtains petroleum ether part medicinal extract and ethyl acetate extract medicinal extract；
2. 1. petroleum ether part medicinal extract that step is obtained passes through silica gel column chromatography, using petroleum ether-ethyl acetate dicyandiamide solution
Gradient elution is carried out, collects, concentrate, merging identical flow point；
It is 3. step is 2. middle using petroleum ether: ethyl acetate=5: 1 flow point afforded carries out reversed-phase silica gel column chromatography point successively
From, Sephadex LH-20 sephadexes column chromatography for separation and high performance liquid chromatography separation, parallel double tetrahydrofuran class is obtained
Lignanoid.
The above-mentioned steps dicyandiamide solution that 3. middle reversed-phase silica gel column chromatography separation uses is water: methanol=1: 1, Sephadex
The dicyandiamide solution that LH-20 sephadex column chromatography for separation uses is chloroform: methanol=1: 1, what high performance liquid chromatography separation used
Flow visualizing composition is 48% acetonitrile and 52% water.
Application of the above-mentioned parallel double tetrahydrofuran lignans on tumour cell is suppressed, the tumour cell is cervical carcinoma
Hela cells, MCF-7 Breast Cancer Cell or Lung Adenocarcinoma A 549 Cell.
The good effect that the present invention has：The parallel double tetrahydrofuran lignans that the present invention extracts in escaping grass from sorrow are to uterine neck
Cancer Hela cells, MCF-7 Breast Cancer Cell, Lung Adenocarcinoma A 549 Cell have inhibitory activity.
Brief description of the drawings
Fig. 1 is the parallel double tetrahydrofuran lignans of the present invention1H-NMR is composed（Proton nmr spectra）Figure.
Fig. 2 is the parallel double tetrahydrofuran lignans of the present invention13C-NMR is composed（Carbon-13 nmr spectra）Figure.
Fig. 3 is the DEPT-NMR spectrums of the parallel double tetrahydrofuran lignans of the present invention（Nuclear magnetic resonance is undistorted polarization transfer
Enhancing spectrum）Figure.
Fig. 4 is the parallel double tetrahydrofuran lignans of the present invention1H-1H COSY are composed（Hydrogen hydrogen Correlated Spectroscopy）Figure.
Fig. 5 is the hsqc spectrum figure of the parallel double tetrahydrofuran lignans of the present invention.
Fig. 6 is the HMBC spectrograms of the parallel double tetrahydrofuran lignans of the present invention.
Fig. 7 is the NOESY spectrograms of the parallel double tetrahydrofuran lignans of the present invention.
Fig. 8 is the HRESIMS of the parallel double tetrahydrofuran lignans of the present invention（High-resolution electrospray ionization mass spectrometry）Spectrum
Figure.
Embodiment
（Embodiment）
The structural formula such as formula of the parallel double tetrahydrofuran lignans of the present embodiment（Ⅰ）It is shown：
（Ⅰ）.
The preparation method of the parallel double tetrahydrofuran lignans comprises the following steps：
1. by the sorrow of 9.5kg natural air dryings escape grass meal it is broken after, soak refluxing extraction 3 times with the ethanol that volume fraction is 85%, every time
7 days, the phegma being collected into is merged, is evaporated under reduced pressure, obtains the 550.2g total medicinal extract of ethanol, medicinal extract is in thick brown.So
The total medicinal extract of above-mentioned ethanol is dispersed in 3.0L distilled water afterwards, uses petroleum ether successively（3×3.5L）And ethyl acetate（4×
4.0L）Extracted, obtain petroleum ether part medicinal extract（200g）, ethyl acetate extract medicinal extract（10.2g）.
The escape stem of grass of sorrow used in the present embodiment picks up from Wuzhishan Mountain in Hainan city, and sample deposits in Hainan Normal University torrid zone
Key lab of the medicinal plant chemistry building by province and ministry Ministry of Education.
2. 1. 200g petroleum ether parts medicinal extract that step is obtained passes through silica gel column chromatography, using petroleum ether-ethyl acetate
Dicyandiamide solution, according to 100: 0~0: 100（V/V）Carry out gradient elution, per 500mL collect flow point, concentrate flow point, pass through TLC
（Thin-layer chromatography）Detection, merges identical flow point.
It is 3. step is 2. middle using petroleum ether: ethyl acetate=5: 1 flow point afforded carries out reverse phase silica gel post color successively
Spectrum separation, Sephadex LH-20 sephadexes column chromatography for separation and high performance liquid chromatography separation, obtain parallel double tetrahydrochysene furans
Mutter lignans.
The dicyandiamide solution that wherein reversed-phase silica gel column chromatography separation uses is water: methanol=1: 1, Sephadex LH-20 Portugals gather
The dicyandiamide solution that sugared gel filtration chromatography separation uses is chloroform: methanol=1: 1, the mobile phase body that high performance liquid chromatography separation uses
System's composition is 48% acetonitrile and 52% water.
（Test case）
The parallel double tetrahydrofuran lignans obtained to embodiment carry out product analysis：
（1）The parallel double tetrahydrofuran lignans1H-NMR spectrums are shown in Fig. 1（Solvent C D3OD, 400Hz）.
（2）The parallel double tetrahydrofuran lignans13C-NMR spectrums are shown in Fig. 2（Solvent C D3OD, 100MHz）.
Specific data are shown in Table 1.
Table 1
（3）The DEPT-NMR spectrums of the parallel double tetrahydrofuran lignans（Polarization transfer enhancing spectrum that nuclear magnetic resonance is undistorted）See
Fig. 3（Solvent C DCl3）.
（4）The parallel double tetrahydrofuran lignans1H-1H COSY are composed（Hydrogen hydrogen Correlated Spectroscopy）See Fig. 4（Solvent C DCl3）.
（5）The hsqc spectrum of the parallel double tetrahydrofuran lignans is shown in Fig. 5（Solvent C DCl3）.
（6）The HMBC spectrums of the parallel double tetrahydrofuran lignans are shown in Fig. 6（Solvent C DCl3）.
（7）The NOESY spectrums of the parallel double tetrahydrofuran lignans are shown in Fig. 7（Solvent C DCl3）.
（8）The high-resolution electrospray ionization mass spectrometry figure of the parallel double tetrahydrofuran lignans（Q-Trap LC/MS/MS
System mass spectrographs, ESI sources）Fig. 8 is seen, by [M+H] in Fig. 8+Theoretical value 423.105【Measured value is 423.105】Extrapolate
The molecular formula of the compound is C21H20O8, degree of unsaturation 11.
Pass through control compounds13C-NMR is composed and DEPT-NMR spectrums：21 carbon signals are shown altogether, wherein 1 company's oxygen first
Base carbon signal（δC56.7）, 2 company's dioxymethylene carbon signals（δC102.3、102.5）.Remaining 18 carbon signals, wherein 12
Individual carbon is two groups of aromatic ring carbon signals, including：5 company's oxygen carbon signals（δC148.8、142.6、153.0、149.3、148.5）, 5
Even hydrogen carbon signal（δC95.7、106.3、108.7、107.9、120.8）, 2 quaternary carbon signals（δC138.3、124.5）.It can see
Go out compound and contain five company's hydrogen fragrance carbon signals, thus it is speculated that compound contains 1 trisubstituted benzene ring and 1 four substituted benzene ring.Also
It is left 6 carbon signals（δC80.9、63.6、103.8、88.5、55.0、72.9）For aliphatic carbon signal, in conjunction with DEPT-NMR
Spectrum, find δ in 6 aliphatic carbon signalsC72.9 be mesomethylene carbon signal, and remaining is methine carbon signal.Thus can guess
The oxide precursor skeleton is typical parallel tetrahydrofuran lignans compound, wherein being substituted in No. 9 positions or 9' positions.
11 methyl hydrogen signal δ is observed in H-NMR spectrumsH3.82（3H）, 2 typically connect dioxymethylene hydrogen letter
Number：δH5.90（2H）, 5.93（2H）；With reference to hsqc spectrum：δC56.7 with δH3.82 have directly related signal, δH 5.89,
5.92 respectively with δC102.5,102.3 directly related signal be present.It is that skeleton is containing 1 first further to have proved compound
The parallel double tetrahydrofuran lignans of epoxide, 2 company's dioxymethylene fragments.In HMBC spectrums, δ is foundH3.81（3H）Only
With C-6（δC153.0）There is long-range correlation, thus can speculate that methoxyl group fragment is connected on C-6 positions.δ is also observed simultaneouslyH
5.92（2H,-OCH2O-）With C-3'（δC149.3）、C-4'（δC148.5）In the presence of long-range related, δH5.90（2H,-OCH2O-）
With C-3（δC148.8）、C-4（δC142.6）In the presence of long-range correlation, it thereby it is assumed that 2 company's dioxymethylenes connect respectively
On C-3, C-4 and C-3', C-4' positions.In addition, on hsqc spectrum, it was observed that δH5.65 and δC103.8 is directly related,
And δ in DEPT spectrumsC103.8 be methine carbon signal, further demonstrate the guess that No. 9 positions or 9' positions are substituted, with reference to
High-resolution data, thus it is speculated that substituent is hydroxyl, referring concurrently to pertinent literature【Wang Rui, Tong Ling, teacher's man of virtue and ability's equality,《1 in lilac daphne
New tetrahydrofuran type lignanoid》, Chinese herbal medicine】, No. 9 positions of discovery1H-NMR、13C-NMR and analogue compounds 4- hydroxyl sesames
It is plain consistent, in conjunction with1H-1H COSY are composed, and find δH5.65 only with δH2.70（H-8）It is directly related, therefore speculate that hydroxyl is substituted in
On C-9 positions.Further look at1H-1H COSY are composed, δH5.65（H-9）And δH2.70（H-8）、δH2.70（H-8）And δH
5.10（H-7）、δH2.70（H-8）And δH3.03（H-8'）、δH3.03（H-8'）And δH4.86（H-7'）、δH3.03（H-
8'）And δH4.04（H-9'α）、δH4.15（H-9'β）There is directly related signal, it is determined that the link situation of bifuran.HMBC
In spectrum, it was observed that δH5.10（1H, d, J = 6.4, H-7）With C-1（δC124.5）、C-2（δC106.3）、C-6（δC
153.0）, and δH4.86（1H, d, J = 6.8, H-7'）With C-1'（δC138.3）、C-2'（δC107.9）、C-6'
（δC120.8）Between exist long-range related, further proved the connected mode of aromatic ring substituents and double tetrahydrofuran ring.It is comprehensive
Analyzed more than closing, it is determined that the planar structure of compound.
Determine its relative configuration, two tetrahydrofuran rings are with suitable in the parallel double tetrahydrofuran lignans in natural products
Formula is simultaneously closed, if the aromatic substituent of 7 and 7' positions two is in trans horizontal key with double tetrahydrofuran ring simultaneously or cis axial bond is referred to as
Symmetric form, it is referred to as asymmetric if cis and trans are respectively at, and when the substitution position of 7 and 7' positions two is a symmetric form knot
During structure,1The H of 9 and 9' positions is dd peaks in H-NMR spectrums, otherwise is multiplet.Observe compound hydrogen spectrum and find δH4.04（1H, dd,
J = 1.2, 8.8, H-9'α）、δH4.15（1H, dd, J = 4.8, 8.8, H-9'β）, No. 9 hydrogen of position one are taken by hydroxyl
For δH5.65 （1H, s, H-9）, 9' positions hydrogen is dd peaks, thus speculates that the compound substitutes position to be one for two for 7 and 7' positions
Symmetrical structure, the homonymy in double tetrahydrofuran ring.Meanwhile according to data【Xu appoints life, Yeyang, Zhao Weimin etc.,《Natural products
Chemistry（The second edition》, Beijing Science Press, 2004,631-634】Record, the H-7 or H-7' of asymmetrical type structure, because by virtue
The shielding action of fragrant substituent, in most High-Field（δ ＜ 4.50）, the symmetrical axial bond of aryl two substitution H-7 or H-7' of equal value, place
In most low field（δ~4.90）, symmetrical two horizontal key of aryl substitution H-7 or H-7' of equal value, therebetween（δ 4.67~
4.75）.And the δ of compoundH5.10（1H, d, J=6.4, H-7）And δH4.86（1H, d, J=6.8, H-7'）It is in
Most High-Field, it further demonstrate that the diaryl of compound is substituted by symmetrical two axial bonds substitution, be α-configuration.
Found with reference to Fig. 7 NOESY spectrograms, H-7（δH5.10）With H-8, H-9' α, between H-9, H-7'；H-7'（δH
4.86）Between H-9' α, H-7, H-9；H-8'（δH 3.03）Coherent signal be present between H-8, H-9' α, it was demonstrated that：H-7、H-
7', H-8, H-8', H-9, H-9' α are α-configuration in the same side.Analysis determines that the relative configuration of compound is more than：9
Beta-hydroxy -6- methoxyl groups-sesamin.
（Test example, anti tumor activity in vitro evaluation）
Test method：The isolated parallel double tetrahydrofuran lignans of Example carry out antitumor activity.
Tumor cell line：S, MCF-7 Breast Cancer Cell, Lung Adenocarcinoma A 549 Cell（University Of Hebei's pharmacy
Institute provides）.
Positive control：Adriamycin.
Instrument：Refrigerator, autoclave, ELIASA（BioTek ELx800）, microscope, freeze drier, CO2Constant temperature trains case,
96 orifice plates, pipettor, electric heating constant-temperature blowing drying box, microstrainer and 0.22 μm of filter membrane, supercentrifuge.
Reagent：RPMI1640 nutrient solutions, pancreatin, MTT, DMSO, top grade NBCS.
Specific experiment method：
(1) inoculating cell：With the nutrient solution containing 10% hyclone（DMEM）Individual cells suspension is made into, with every hole 5 × 104、5
×105Individual/mL is inoculated into 96 orifice plates, and per the μ L of pore volume 100, attached cell shifts to an earlier date 12 hours inoculated and cultureds.
(2) testing compound solution is added（The μ g/mL primary dcreening operations of fixed concentration 40, growth of tumour cell is suppressed in the concentration
Compound near 50% sets 5 concentration and enters gradient secondary screening, i.e. detectable concentration is respectively 5,1,0.2,0.04,0.008 μ g/
ML, testing sample is diluted with nutrient solution）100 μ L, per the μ L of hole final volume 100, every kind of processing is all provided with 3 multiple holes.
(3) develop the color：After 37 degrees Celsius are cultivated 48 hours, add the μ L of MTT solution 20 per hole.Continue to be incubated 4 hours, terminate training
Support, culture supernatant in hole is abandoned in suction, and 150 μ L DMSO solution is added per hole, crystal is fully melted.
(4) colorimetric：Select 490nm wavelength, ELIASA（BioTek ELx800）Each hole absorbance value is read, records result.
Calculate the IC of compound50Value.
Data analysis：
Ordinate is made with cell inhibitory rate, the logarithm value of concentration is abscissa, makees regression curve, calculates IC50Value.Wherein, suppress
Rate=（Add the OD values of OD values-test group of PBS control group）/ plus PBS control group OD value × 100%.
Antitumor activity of compound test result is as follows：
Table 2
Result of the test shows parallel double tetrahydrofuran lignans produced by the present invention to s, breast cancer
MCF-7 cells, Lung Adenocarcinoma A 549 Cell have inhibitory activity.
Claims (4)
1. a kind of parallel double tetrahydrofuran lignans, its structure such as formula（Ⅰ）It is shown：
（Ⅰ）.
2. the preparation method of the parallel double tetrahydrofuran lignans described in claim 1, it is characterised in that comprise the following steps：
1. by the sorrow of natural air drying escape grass meal it is broken after with ethanol soak refluxing extraction, by the phegma being collected into merge, decompression steam
Evaporate, obtain the total medicinal extract of ethanol, then the total medicinal extract of above-mentioned ethanol is dispersed in distilled water, successively with petroleum ether and acetic acid second
Ester is extracted, and obtains petroleum ether part medicinal extract and ethyl acetate extract medicinal extract；
2. 1. petroleum ether part medicinal extract that step is obtained passes through silica gel column chromatography, using petroleum ether-ethyl acetate dicyandiamide solution
Gradient elution is carried out, collects, concentrate, merging identical flow point；
It is 3. step is 2. middle using petroleum ether: ethyl acetate=5: 1 flow point afforded carries out reversed-phase silica gel column chromatography point successively
From, Sephadex LH-20 sephadexes column chromatography for separation and high performance liquid chromatography separation, parallel double tetrahydrofuran class is obtained
Lignanoid.
3. the preparation method of parallel double tetrahydrofuran lignans according to claim 2, it is characterised in that：Step 3. in it is anti-
The dicyandiamide solution that the separation of phase silica gel column chromatography uses is water: methanol=1: 1, Sephadex LH-20 sephadexes column chromatography point
It is chloroform: methanol=1 from the dicyandiamide solution used: 1, the flow visualizing composition that high performance liquid chromatography separation uses is 48% acetonitrile
With 52% water.
4. application of the parallel double tetrahydrofuran lignans on tumour cell is suppressed described in claim 1, the tumour cell
For s, MCF-7 Breast Cancer Cell or Lung Adenocarcinoma A 549 Cell.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111004247A (en) * | 2019-12-01 | 2020-04-14 | 福建农林大学 | New plant source raw material for preparing 4-hydroxy sesamin and method thereof |
| CN111671780A (en) * | 2020-05-20 | 2020-09-18 | 沈阳化工大学 | Preparation method and application of tuberculate speranskia herb lignan with nerve cell protection activity |
| CN111748007A (en) * | 2020-07-01 | 2020-10-09 | 济南大学 | Two lignan glycoside compounds and preparation method and application thereof |
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2017
- 2017-06-28 CN CN201710507284.7A patent/CN107522706B/en active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111004247A (en) * | 2019-12-01 | 2020-04-14 | 福建农林大学 | New plant source raw material for preparing 4-hydroxy sesamin and method thereof |
| CN111004247B (en) * | 2019-12-01 | 2024-02-06 | 福建农林大学 | New plant source raw material for preparing 4-hydroxy sesamin and method thereof |
| CN111671780A (en) * | 2020-05-20 | 2020-09-18 | 沈阳化工大学 | Preparation method and application of tuberculate speranskia herb lignan with nerve cell protection activity |
| CN111748007A (en) * | 2020-07-01 | 2020-10-09 | 济南大学 | Two lignan glycoside compounds and preparation method and application thereof |
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