CN106008423A - Phenylpropanoid compounds as well as preparation method and application thereof - Google Patents
Phenylpropanoid compounds as well as preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses phenylpropanoid compounds as well as a preparation method and an application thereof. The phenylpropanoid compounds are separated from Swertia atroviolacea, are named 3-hydroxy-1-(6-hydroxymethyl-1,3-dihydroisobenzofuran-5-yl)propan-1-one and have the structural formula shown in the specification, and a molecular formula of the phenylpropanoid compounds is C12H14O4. The preparation method of the phenylpropanoid compounds comprises the following steps: the Swertia atroviolacea is taken as the raw material and subjected to extract extraction, MCI decoloration, silica gel column chromatography and HPLC (high performance liquid chromatography) separation. 5 alpha-reductase activity tests prove that the phenylpropanoid compounds have better inhibition function on 5 alpha-reductase. The invention further discloses the preparation method and the application of the phenylpropanoid compounds. The compounds are simple in structure, have better 5 alpha-reductase inhibition function and can serve as lead compounds for preparing 5 alpha-reductase inhibitors.
Description
Technical field
The invention belongs to technical field of phytochemistry, be specifically related to a kind of extract, from black purple Herba Swertiae bimaculatae, the benzene obtained first
C prime compounds and its preparation method and application.
Background technology
Swertia (Swertia) it is a genus under Gentianaceae, about 170 kinds of the whole world, China has more than 80 to plant, and is mainly distributed
In the ground such as Yunnan, Sichuan.In China, this platymiscium is used as medicine with a long history, and medicinal have 35 kinds, has clearing heat secreting bile, removing dampness and detoxicating etc.
Effect, is usually used in treating the diseases such as acute Jaundice Jaundice, osteomyelitis.The chemical composition of this platymiscium is enriched, and mainly has a mouthful mountain
The compounds such as ketone, flavone, iridoid, triterpene and alkaloid.Black purple Herba Swertiae bimaculatae (Swertia atroviolacea) it is river deer tooth
Lepidium herbaceos perennial, is born in the patana of height above sea level 3400～4575 m, many tors top or rock seam, is Yunnan Province
The peculiar kind in Diqingzangzu area.
A class phenyl ring and three straight chain carbon that Phenylpropanoid Glycosides (phenylpropanoid) is naturally-occurring connect (C6-C3 base
Group) compound that constitutes.Phenylpropanoids such as coumarin, lignanoid etc., be widely present in plant, in a lot of fields
As medicine, food, cosmetics etc. become important raw material, many of which compound has various biological activity, medical, biological
Have broad application prospects in field.Present invention isolated one from the black purple Herba Swertiae bimaculatae has 5αThe suppression of-reductase is lived
The phenylpropanoids of property, this compound it is not yet seen relevant report.
Steroid 5α-reductase is the memebrane protein being positioned on target cell microsome, relies on nicotinamide adenine dinucleotide phosphate (NADPH)
As hydrogen donor, catalysis reduction a series of steroid substrate such as testosterone, 17α-hydroxyl progesterone, androstenedione etc..In catalysis also
During proandrogens testosterone (T) is changed into the double hydrogen testosterone (DHT) of the higher androgen of activity, 5α-reductase plays
Pivotal role.T and reductive metabolites DHT thereof is to maintain male's dominant character and sexually matured essence androgen, accounts for males
Internal hormone about 80%, wherein DHT is considered as the androgen that internal effect is the strongest.If internal DHT too high levels, it will lead
Cause the relevant endocrine disturbance of induced hormone effect, cause multiple disease, such as benign prostatic hyperplasia, acne, male baldness
With female hirsutism etc..T and 5αThe complex that-reductase and its coenzyme NADP 11 are formed combines, if there being certain inhibitor
Existing, owing to the structure of inhibitor is similar with T, inhibitor can also be combined with complex equally, and such inhibitor is just mutual with T-phase
Competition is combined with complex, thus decreases the T conversion to DHT, thus reduces the content of internal DHT, alleviate internal by
In the various diseases that DHT too high levels causes.One has 5 by isolatedαThe Phenylpropanoid Glycosides of-reductase active
Compounds, this compound relevant 5α-reductase active also has no report.
Summary of the invention
It is an object of the invention to provide a kind of new phenylpropanoids；Second purpose is to provide described Phenylpropanoid Glycosides
The preparation method of compounds；3rd purpose is to provide described phenylpropanoids in preparation 5αIn-reductase inhibitor
Application.
The first object of the present invention is achieved in that described phenylpropanoids is from dry black purple Herba Swertiae bimaculatae
(Swertia atroviolacea) isolated in herb, named 3-hydroxyl-1-(6-methylol-1, the different benzo of 3-dihydro
Furan-5-base) propane-1-ketone, English entitled: 3-hydroxy-1-(6-hydroxymethyl-1,3-
Dihydroisobenzofuran-5-yl) propan-1-one, its molecular formula is C12H14O4, there is following structural formula:
This compound is light yellow gum thing.
The second object of the present invention is achieved in that the preparation method of described phenylpropanoids, is to be dried
Black purple Herba Swertiae bimaculatae herb be raw material, through extractum extraction, MCI decolouring, silica gel column chromatography, high pressure liquid chromatography step, particularly as follows:
A, extractum extract: pulverized by the herb of black purple Herba Swertiae bimaculatae, with extracting under 95% ethanol room temperature 3 ~ 5 times, each 3 days, merge
Extracting solution, filtration, concentrating under reduced pressure extracting solution, stand, filter precipitate, be condensed into extractum a；
B, MCI decolour: extractum a MCI post decolours, and with 80%-95% methanol/water eluting, merge organic facies, and concentrating under reduced pressure becomes extractum
b；
C, silica gel column chromatography: 100 ~ 200 mesh silica gel dry column-packings of extractum b weight ratio 8 ~ 10 times amount carry out silica gel column chromatography；
With volume proportion as 1:0, the chloroform/acetone solution of 9:1,8:2,7:3,6:4,1:1 and 0:1 carry out gradient elution, collect gradient
Eluent, concentration, merge identical part；
D, high pressure liquid chromatography separate: the inverted C of 8:2 part of step C eluent18Medium pressure liquid chromatography is isolated and purified, gained
The eluent that 14 ~ 18 min chromatographic peaks are corresponding, isolated and purified through high pressure liquid chromatography further, obtain described Phenylpropanoid Glycosides class
Compound.
The structure of phenylpropanoids prepared by method described above is identified out by the following method:
The compounds of this invention is light yellow gum thing；Ultraviolet spectra (solvent is methanol), λmax (log ε) 275 (3.74)、
232 (3.86)、210 (4.05) nm；Infrared spectrum (pressing potassium bromide troche) νmax 3387、3086、2946、1658、1610、
1574、1456、1348、1267、1164、1038、876 cm-1；High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/
z 245.0783 [M+Na]+(value of calculation 245.0790).In conjunction with1H and13C H NMR spectroscopy provides molecular formula C12H14O4, no
Saturation is 6.Ir data confirms to there are hydroxyl (3387 cm in compound-1) and aromatic ring (1610,1574,1456 cm-1) functional group.From1H and13C H NMR spectroscopy (attribution data is shown in Table-1) signal can be seen that 12 carbon of compound include five methylenes
Base (C-8, C-9, C-1, C-2, C-3), two olefinic carbon methines (C-3, C-6) and five quaternary carbons (include a carbonyl C-
7 and four olefinic carbons C-1, C-2, C-4, C-5), these signals show that compound is phenylpropanoids.According to H-1 and C-1,
Relevant (Fig. 3) the susceptible of proof methylol of the HMBC of C-2, C-3 is substituted in the C-2 position of phenyl ring；H-8 and C-1, the HMBC phase of C-7, C-9
Close display propyl group and be substituted in the C-1 position of phenyl ring；Calculate according to degree of unsaturation and find, compound also has another one ring exist,
In HMBC spectrum, H-3 and C-2, relevant and H-2 and C-3, the relevant confirmation C-2 of C-3, C-4, C-5 of C-4, C-5, C-6
, C-3, C-4, C-5 form a furan nucleus；There is HMBC relevant according to H-6, H-8, H-9 to carbonyl, it can be verified that carbonyl is positioned at C-
7, so far the structure of this compound is determined.
Table-1. compound1H NMR and13(solvent is CDCl to C NMR data3)
| No. | d C | d H (m, J, Hz) | No. | d C | d H (m, J, Hz) |
| 1 | 133.6 s | 7 | 201.5 s | ||
| 2 | 136.6 s | 8 | 43.5 t | 3.36 (t) 7.0 | |
| 3 | 128.0 d | 6.75 s | 9 | 57.3 t | 4.38 (t) 7.0 |
| 4 | 146.1 s | 1′ | 63.3 t | 4.46 s | |
| 5 | 138.9 s | 2′ | 74.3 t | 5.33 s | |
| 6 | 126.6 d | 7.75 s | 3′ | 73.5 t | 5.40 s |
The third object of the present invention is achieved in that described phenylpropanoids is in preparation 5αIn-reductase inhibitor
Application.
The compounds of this invention is separated, by nuclear magnetic resonance, NMR and measuring method of mass spectrum first from black purple Herba Swertiae bimaculatae
It is defined as phenylpropanoids, and characterizes its concrete structure.This compound shows through active testing, result, and it is to 5α -
Reductase suppression ratio is 45.6 ± 2.85%, shows that this compound has certain 5α-reductase active.Chemical combination of the present invention
Thing simple in construction activity preferably, can be as 5αThe guiding compound of-reductase inhibitor, has a good application prospect.
Accompanying drawing explanation
Fig. 1 is the proton nmr spectra of phenylpropanoids of the present invention；
Fig. 2 is the carbon-13 nmr spectra of phenylpropanoids of the present invention；
Fig. 3 is the main HMBC relevant indicators of phenylpropanoids of the present invention.
Detailed description of the invention
The present invention is described in further detail with embodiment below in conjunction with the accompanying drawings, but never in any form to the present invention
Being any limitation as, based on present invention teach that any conversion or improvement made, each falling within protection scope of the present invention.
Except as otherwise noted, the percent employed in the present invention is percentage by volume.
Phenylpropanoids of the present invention, be from dry black purple Herba Swertiae bimaculatae (Swertia atroviolacea)
Isolated in herb, its molecular formula is C12H14O4, there is following structural formula:
This compound is light yellow gum thing, named 3-hydroxyl-1-(6-methylol-1,3-dihydroisobenzofuran-5-base)
Propane-1-ketone, English entitled: 3-hydroxy-1-(6-hydroxymethyl-1,3-dihydroisobenzofuran-5-
yl)propan-1-one。
The preparation method of phenylpropanoids of the present invention, is with dry black purple Herba Swertiae bimaculatae herb as raw material,
Through extractum extraction, MCI decolouring, silica gel column chromatography, high pressure liquid chromatography step, particularly as follows:
A, extractum extract: pulverized by the herb of black purple Herba Swertiae bimaculatae, with extracting under 95% ethanol room temperature 3 ~ 5 times, each 3 days, merge
Extracting solution, filtration, concentrating under reduced pressure extracting solution, stand, filter precipitate, be condensed into extractum a；
B, MCI decolour: extractum a MCI post decolours, and with 80%-95% methanol/water eluting, merge organic facies, and concentrating under reduced pressure becomes extractum
b；
C, silica gel column chromatography: 100 ~ 200 mesh silica gel dry column-packings of extractum b weight ratio 8 ~ 10 times amount carry out silica gel column chromatography；
With volume proportion as 1:0, the chloroform/acetone solution of 9:1,8:2,7:3,6:4,1:1 and 0:1 carry out gradient elution, collect gradient
Eluent, concentration, merge identical part；
D, high pressure liquid chromatography separate: the inverted C of 8:2 part of step C eluent18Medium pressure liquid chromatography is isolated and purified, gained
The eluent that 14 ~ 18 min chromatographic peaks are corresponding, isolated and purified through high pressure liquid chromatography further, obtain described Phenylpropanoid Glycosides class
Compound.
The extractum b of described step C, before silica gel column chromatography, mixes molten by the chloroform/methanol of weight ratio 1.5～3 times amount
Agent is dissolved, and then weighs the 80～100 mesh silica gel mixed samples of 1 ~ 1.5 times with extractum.
The anti-phase C of described D step18Medium pressure liquid chromatography is isolated and purified is with 21.2 mm × 250 mm, the C of 5 μm18
Chromatographic column is fixing phase, and the acetonitrile with 45% is flowing phase, and flow velocity is 20 mL/min, UV-detector detection wavelength is 210 ~
230 nm, each sample introduction 2 mL, collect the chromatographic peak of 14 ~ 18 min.
Eluent corresponding to 14 ~ 18 min chromatographic peaks of described D step before high pressure liquid chromatography is isolated and purified, removing
Dissolve with methanol after solvent.
The high pressure liquid chromatography of described D step is isolated and purified be with 40% acetonitrile for flowing phase, flow velocity 3 mL/min, 9.4
Mm × 250 mm, the C of 5 μm18Chromatographic column is fixing phase, and UV-detector detection wavelength is 210 ~ 280 nm, each sample introduction 50
μ L, collects the chromatographic peak of 15.2 min, is evaporated after repeatedly adding up.
The application of the present invention is that described phenylpropanoids is in preparation 5αApplication in-reductase inhibitor.
Black purple Herba Swertiae bimaculatae of the present invention, not by territorial restrictions, all can realize the present invention, below to pick up from Yunnan Province
The black purple Herba Swertiae bimaculatae in enlightening celebrating area is raw material, and the present invention will be further described:
Unreceipted concrete technology or condition person in embodiment, according to technology or the condition described by the document in this area or press
Carry out according to product description.Agents useful for same or instrument unreceipted production firm person, be the conventional product that can be obtained by purchase
Product.If the solution in the present invention only gives solute, do not disclose solvent, then those skilled in the art should know solvent and are
Water.In the present invention, pure chloroform refers to 100% chloroform, and pure acetone refers to that 100% acetone, pure methanol refer to 100% methanol.
Embodiment 1
To pick up from the regional black purple Herba Swertiae bimaculatae of Yunnan Province's enlightening celebrating as raw material.Black purple Herba Swertiae bimaculatae herb is sampled 2.5 kg pulverize, with
Extracting 4 times under the ethanol room temperature of 95%, extract 3 days, each 3.5 L of extracting solution every time, extracting solution merges, and filters, and concentrating under reduced pressure becomes
Extractum, obtains extractum 86 g.Extractum MCI post decolours, and with 90% methanol/water eluting, the extractum after decolouring is by 55 g chloroform/methanol
Mixed solvent dissolves, and is subsequently adding 80 mesh silica gel 52 g and mixes sample.After mixing sample, with 100 ~ 200 mesh silica gel 1 kg dry column-packings；Use body
The chloroform/acetone solution that long-pending ratio is followed successively by 1:0,9:1,8:2,7:3,6:4,1:1 and 0:1 carries out gradient elution, collects gradient and washes
De-liquid, concentration, merge identical part, and wherein volume is 8:2 part 1 g；8:2 elution fractions is passed through anti-phase C18Middle hydraulic fluid phase
Chromatograph, this medium pressure liquid chromatography uses 21.2 mm × 250 mm, the C of 5 μm18Chromatographic column, flow rate of mobile phase is 20 mL/
Min, flowing is the acetonitrile of 45% mutually.UV-detector is dual wavelength detector, and detection wavelength is 210,230 nm, each sample introduction 2
ML, collects the eluent corresponding to 14 ~ 18 min chromatographic peaks, dissolves with methanol after eluent desolvation, and lysate is passed through again
High pressure liquid chromatography carries out isolated and purified, and this high pressure liquid chromatography uses 9.4 mm × 250 mm, the C of 5 μm18Chromatographic column, stream
Dynamic phase flow velocity is 3 mL/min, and flowing is the acetonitrile of 40% mutually, and UV-detector detection wavelength is 210,254,280 nm, every time
Sample introduction 50 μ L, collects eluent corresponding when chromatographic peak retention time is 15.2 min, is evaporated, obtains institute after repeatedly adding up
State phenylpropanoids.
Embodiment 2
To pick up from the regional black purple Herba Swertiae bimaculatae of Yunnan Province's enlightening celebrating as raw material.Black purple Herba Swertiae bimaculatae herb is sampled 2.5 kg pulverize, with
Extracting 4 times under the ethanol room temperature of 95%, extract 3 days, each 3.5 L of extracting solution every time, extracting solution merges, and filters, and concentrating under reduced pressure becomes
Extractum, obtains extractum 86 g.Extractum MCI post decolours, and with 90% methanol/water eluting, the extractum after decolouring is by 55 g chloroform/methanol
Mixed solvent dissolves, and is subsequently adding 80 mesh silica gel 52 g and mixes sample.After mixing sample, with 100 ~ 200 mesh silica gel 1 kg dry column-packings；Use body
The chloroform/acetone solution that long-pending ratio is followed successively by 1:0,9:1,8:2,7:3,6:4,1:1 and 0:1 carries out gradient elution, collects gradient and washes
De-liquid, concentration, merge identical part, and wherein volume is 8:2 part 1 g；8:2 elution fractions is passed through anti-phase C18Middle hydraulic fluid phase
Chromatograph, this medium pressure liquid chromatography uses 21.2 mm × 250 mm, the C of 5 μm18Chromatographic column, flow rate of mobile phase is 20 mL/
Min, flowing is the acetonitrile of 45% mutually.UV-detector is dual wavelength detector, and detection wavelength is 210,230 nm, each sample introduction 2
ML, collects the eluent corresponding to 14 ~ 18 min chromatographic peaks, dissolves with methanol after eluent desolvation, and lysate is passed through again
High pressure liquid chromatography carries out isolated and purified, and this high pressure liquid chromatography uses 9.4 mm × 250 mm, the C of 5 μm18Chromatographic column, stream
Dynamic phase flow velocity is 3 mL/min, and flowing is the acetonitrile of 40% mutually, and UV-detector detection wavelength is 210,254,280 nm, every time
Sample introduction 50 μ L, collects eluent corresponding when chromatographic peak retention time is 15.2 min, is evaporated, obtains institute after repeatedly adding up
State phenylpropanoids.
Embodiment 3
The compound of Example 1 preparation, for light yellow gum thing；
Assay method is: with nuclear magnetic resonance, NMR, identify structure in conjunction with other spectroscopic technique.
(1) ultraviolet spectra (solvent is methanol), λmax (log ε) 275 (3.74)、232 (3.86)、210
(4.05) nm；
(2) infrared spectrum (pressing potassium bromide troche) νmax 3387、3086、2946、1658、1610、1574、1456、1348、
1267、1164、1038、876 cm-1；
(3) high resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z 245.0783 [M+Na]+(value of calculation
245.0790).In conjunction with1H and13C H NMR spectroscopy provides molecular formula C12H14O4, degree of unsaturation is 6.Ir data confirms
Compound exists hydroxyl (3387 cm-1) and aromatic ring (1610,1574,1456 cm-1) functional group.From1H and13C H NMR spectroscopy (number
It being shown in Table-1 according to ownership) signal can be seen that 12 carbon of compound include five methylene (C-8, C-9, C-1, C-2, C-3
), two olefinic carbon methines (C-3, C-6) and five quaternary carbons (include a carbonyl C-7 and four olefinic carbon C-1, C-2, C-4,
C-5), these signals show that compound is phenylpropanoids.HMBC according to H-1 with C-1, C-2, C-3 is relevant (Fig. 3)
Susceptible of proof methylol is substituted in the C-2 position of phenyl ring；H-8 with C-1, the HMBC relevant display propyl group of C-7, C-9 are substituted in phenyl ring
C-1 position；Calculate according to degree of unsaturation and find, compound also has another one ring exist, in HMBC spectrum, H-3 and C-2, C-
4, relevant and H-2 and C-3 of C-5, C-6, relevant confirmation C-2, C-3, C-4, C-5 of C-3, C-4, C-5 form one
Furan nucleus；There is HMBC relevant according to H-6, H-8, H-9 to carbonyl, it can be verified that carbonyl is positioned at C-7 position, the so far structure of this compound
Determined.
Table-1. compound1H NMR and13(solvent is CDCl to C NMR data3)
| No. | d C | d H (m, J, Hz) | No. | d C | d H (m, J, Hz) |
| 1 | 133.6 s | 7 | 201.5 s | ||
| 2 | 136.6 s | 8 | 43.5 t | 3.36 (t) 7.0 | |
| 3 | 128.0 d | 6.75 s | 9 | 57.3 t | 4.38 (t) 7.0 |
| 4 | 146.1 s | 1′ | 63.3 t | 4.46 s | |
| 5 | 138.9 s | 2′ | 74.3 t | 5.33 s | |
| 6 | 126.6 d | 7.75 s | 3′ | 73.5 t | 5.40 s |
Embodiment 4
In Example 1, the phenylpropanoids of preparation carries out 5α-reductase active is tested, and test case is as follows:
The method that active testing uses dispersive liquid-liquid microextraction-makings to be used in conjunction is tested, and concrete operations are: by 50μG prostatitis
Gland microsomal protein, 500nM testosterone (T), 1mM dithiothreitol, DTT (DTT), 25μL DMSO is dissolved in 40mM sodium phosphate delays
Dissolved liquid (pH 6.5) is configured to reactant liquor, and is dissolved to 0.5 ml, adds 250 in reactant liquorμM nicotinamide adenine dinucleotide phosphate
(NADPH) start enzymatic reaction, and cultivate 60 minutes in 37 DEG C of vibration water-baths.500 are added to reactant liquor afterwards in ice bathμL MeCN stops enzymatic reaction.Phenylpropanoids, testosterone and the mode of dihydrotestosterone dispersive liquid-liquid microextraction of preparation
Extract.Reactant liquor continuously adds 50μL internal standard substance T-d3(175 nM) and DHT-13C3(175 nM) and 50μL trichlorine
Ethylene, and be transferred in the conical pipe equipped with 3 ml water.Close conical pipe, manually after concussion, be centrifuged 3 minutes with 5000 × g,
After being centrifuged, the 30 of the phenylpropanoids of preparation will be comprisedμL lower floor material is transferred in new bottle, uses
Gentle nitrogen stream is dried at room temperature for.30 are added after being driedμl MSTFA+NH4I+DTE(500:4:2 vol/wt/wt)
Under domestic microwave (600 w), reaction makes compound carry out silylation reactive for 5 minutes.After having reacted, extract 1μL is anti-
Thing is answered to carry out GC/MS analysis.T/ T-d3With DHT/ DHT-13C3Between ratio can be to testosterone with through 5α-reductase is anti-
The dihydrotestosterone that should generate quantifies, and the amount of the dihydrotestosterone by generating after contrast enzymatic reaction determines test compound
5α-reductase active.
The phenylpropanoids 5 using finasteride to be test preparationαThe positive of-reductase active is right
According to, finasteride is dissolved in DMSO, and with 40mM buffer solution of sodium phosphate (pH 6.5) is diluted, and extracts 1μM's
Diluent carries out enzymatic reaction.For determining the finasteride IC to 5α-reductase inhibitory activity50Value, uses variable concentrations
Finasteride (0.01～1μM) test, the equal parallel assay of each concentration 3 times.
By above method of testing, determine preparation phenylpropanoids 5α-reductase suppression ratio is 45.6 ±
2.85%, display compound has certain 5α-reductase active.
Claims (7)
1. a phenylpropanoids, it is characterised in that described phenylpropanoids is from dry black purple Herba Swertiae bimaculatae
(Swertia atroviolacea) isolated in herb, named 3-hydroxyl-1-(6-methylol-1, the different benzo of 3-dihydro
Furan-5-base) propane-1-ketone, English entitled: 3-hydroxy-1-(6-hydroxymethyl-1,3-
Dihydroisobenzofuran-5-yl) propan-1-one, its molecular formula is C12H14O4, there is following structural formula:
。
2. the preparation method of phenylpropanoids described in a claim 1, it is characterised in that with dry black purple Herba Swertiae bimaculatae
Herb is raw material, through extractum extraction, MCI decolouring, silica gel column chromatography, high pressure liquid chromatography step, particularly as follows:
A, extractum extract: pulverized by the herb of black purple Herba Swertiae bimaculatae, with extracting under 95% ethanol room temperature 3 ~ 5 times, each 3 days, merge
Extracting solution, filtration, concentrating under reduced pressure extracting solution, stand, filter precipitate, be condensed into extractum a；
B, MCI decolour: extractum a MCI post decolours, and with 80%-95% methanol/water eluting, merge organic facies, and concentrating under reduced pressure becomes extractum
b；
C, silica gel column chromatography: 100 ~ 200 mesh silica gel dry column-packings of extractum b weight ratio 8 ~ 10 times amount carry out silica gel column chromatography；
With volume proportion as 1:0, the chloroform/acetone solution of 9:1,8:2,7:3,6:4,1:1 and 0:1 carry out gradient elution, collect gradient
Eluent, concentration, merge identical part；
D, high pressure liquid chromatography separate: the inverted C of 8:2 part of step C eluent18Medium pressure liquid chromatography is isolated and purified, gained
The eluent that 14 ~ 18 min chromatographic peaks are corresponding, isolated and purified through high pressure liquid chromatography further, obtain described Phenylpropanoid Glycosides class
Compound.
The preparation method of phenylpropanoids the most according to claim 2, it is characterised in that the extractum b of described step C
Before silica gel column chromatography, dissolve with the chloroform/methanol mixed solvent of weight ratio 1.5～3 times amount, then weigh 1 ~ 1.5 with extractum
80～100 mesh silica gel mixed samples again.
The preparation method of phenylpropanoids the most according to claim 2, it is characterised in that the anti-phase C of described D step18
Medium pressure liquid chromatography is isolated and purified is with 21.2 mm × 250 mm, the C of 5 μm18Chromatographic column is fixing phase, with the acetonitrile of 45%
For flowing phase, flow velocity is 20 mL/min, UV-detector detection wavelength be 210 ~ 230 nm, each sample introduction 2 mL, collect 14 ~
The chromatographic peak of 18 min.
The preparation method of phenylpropanoids the most according to claim 2, it is characterised in that the 14 ~ 18 of described D step
Eluent corresponding to min chromatographic peak, before high pressure liquid chromatography is isolated and purified, dissolves with methanol after desolvation.
The preparation method of phenylpropanoids the most according to claim 2, it is characterised in that the high pressure liquid of described D step
Phase chromatographic separation and purification be with 40% acetonitrile for flowing phase, flow velocity 3 mL/min, 9.4 mm × 250 mm, the C of 5 μm18Color
Spectrum post is fixing phase, and UV-detector detection wavelength is 210 ~ 280 nm, and each sample introduction 50 μ L collects the chromatograph of 15.2 min
Peak, is evaporated after repeatedly adding up.
7. the phenylpropanoids described in a claim 1 is in preparation 5αApplication in-reductase inhibitor.
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| CN113899839A (en) * | 2021-10-11 | 2022-01-07 | 江南大学 | Extraction method of coumarin compound in morinda officinalis |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113899839A (en) * | 2021-10-11 | 2022-01-07 | 江南大学 | Extraction method of coumarin compound in morinda officinalis |
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