CN104892383B - Method for preparing p-hydroxybenzaldehyde from brined radish - Google Patents
Method for preparing p-hydroxybenzaldehyde from brined radish Download PDFInfo
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- CN104892383B CN104892383B CN201510257677.8A CN201510257677A CN104892383B CN 104892383 B CN104892383 B CN 104892383B CN 201510257677 A CN201510257677 A CN 201510257677A CN 104892383 B CN104892383 B CN 104892383B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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Abstract
The invention discloses a method for preparing p-hydroxybenzaldehyde from a brined radish. The method comprises the following steps: step1, preparation of dried brined radish powder: slicing the brined radish, drying the sliced brined radish at 50 DEG C, pulverizing the sliced brined radish, sieving the obtained brined radish powder through a 20-mesh sieve to obtain the dried brined radish powder, putting the dried brined radish powder into a sealed bag, and storing the sealed bag in a dryer for later use; step2, preparation of crude brined radish extract; step 4, primary separation of the crude brined radish extract; step4, separation and purification of a component Y1; and step5, separation and purification of a component 1-2: dissolving the component 1-2 with methanol, performing separation through a reverse-phase silica gel column, eluting the obtained product with 50% of CH3OH, selecting a first flowing fraction, separating the first flowing fraction with positive-phase silica gel, eluting the first flowing fraction with petroleum ether, collecting 20th to 32nd flowing fractions, merging the flowing fractions; performing concentration, and drying solutions off to prepare p-hydroxybenzaldehyde. According to the invention, p-hydroxybenzaldehyde is separated from the brined radish for the first time, wherein p-hydroxybenzaldehyde is an effective antifungal component for the brined radish. The method is of great significance to secondary development of the brined radish.
Description
Technical field
The present invention relates to the technical field of active medicine, more particularly to one kind prepares hydroxy benzaldehyde from pickled radish
Method.
Background technology
During hydroxy benzaldehyde (4- hydroxy benzaldehydes) is distributed widely in nature, it is right all to exist in plant, marine organisms
Hydroxy benzaldehyde.Or they are used as the volatile ingredient in certain plants or food, or some halobiontic metabolism produce
Some human pathogens such as staphylococcus aureuses, Candida albicans and other marine bacterias etc. are all had good by thing
Fungistatic effect.In the prior art, the presence of hydroxy benzaldehyde is also rarely reported in Radix Raphani.
In view of this, the present inventor studies and devises a kind of method that hydroxy benzaldehyde is prepared from pickled radish, this
Thus case produces.
The content of the invention
It is an object of the invention to provide a kind of method that hydroxy benzaldehyde is prepared from pickled radish, by salting
It is final to be obtained to hydroxyl after adding extract progressively to extract in Radix Raphani, and by reverse phase silica gel post and the chromatographic isolation of normal phase silicagel column
Benzaldehyde, the present invention is isolated to first hydroxy benzaldehyde from pickled radish, and the composition is to suppress funguses in pickled radish
Active substance.
For achieving the above object, the technical scheme of its technical problem of present invention solution is：
A kind of method that hydroxy benzaldehyde is prepared from pickled radish, comprises the following steps：
The preparation of step one, pickled radish dry powder：Pickled radish is thinly sliced, is dried at 50 DEG C, crushed, cross 20 mesh
Sieve, obtains pickled radish dry powder, loaded in hermetic bag, saves backup in exsiccator；
The preparation of step 2, pickled radish crude extract：2 parts of 5 years pickled radish powder of dries pulverizing are weighed, every part of 20g divides
In not being placed in 2 500mL triangular flasks, by solid-liquid ratio 1:15 are separately added into ethyl acetate and acetone, are placed in after sealing in shaking table, 40
DEG C, 6h is extracted under 150rpm, sucking filtration collects filtrate；Coordinative solvent is added to carry out second extraction in residue again, same
Under the conditions of extract 3h, sucking filtration collects filtrate, after solvent is volatilized in residue, then exchanges solvent extraction 1 time, and extraction conditions are with the
Second extraction, merging filtrate, 40 DEG C are evaporated in round-bottomed flask, recycling design, and ethyl acetate and acetone extraction are obtained respectively
Thing extractum, combined ethyl acetate and acetone extract extractum, obtain pickled radish crude extract, and 4 DEG C of storages are standby；
The initial gross separation of step 3, pickled radish crude extract：By pickled radish crude extract with filtering after methanol dissolving, 40 DEG C subtract
The upper Sephadex LH-20 gel columns containing 170g fillers, eluting, coutroi velocity are carried out with methanol as eluant after pressure concentration
For 5～9s/drop, each stream part is collected using automatic collector, 1 is collected per 60min and is managed, collected obtain 128 pipe flow parts altogether；Merge
The stream part of the 48th to the 63rd pipe, then concentrating under reduced pressure is carried out, obtain component Y1；
Step 4, component Y1 are isolated and purified：After component Y1 is with proper amount of methanol dissolving, directly above contain 170g fillers
Sephadex LH-20 gel columns, eluting is carried out with methanol as eluant, and Jing gel post separations several times, final collection obtains
31 pipe flow parts, merge the 11st to the 15th pipe flow part and obtain 310mg samples, and the part is labeled as into component 1-2；
Step 5, component 1-2 are isolated and purified：Component 1-2 adds after proper amount of methanol dissolving, and crossing reverse phase silica gel post is carried out point
From with 50%CH3OH carries out eluting, and elution volume is 1L, and 1 stream part is collected per 200mL, collects obtain 5 stream parts altogether, 45 DEG C
Concentrating under reduced pressure is removed after solvent, selects the 1st stream part to be separated with purification on normal-phase silica gel；2mg samples after purification on normal-phase silica gel is separated
Sample is mixed with 10mg silica whites, after 0.08g silica gel petroleum ether saturations post is filled, after sample upper prop, eluting is carried out with petroleum ether, collected
The stream part of the 20th to the 32nd pipe, merges and concentrated after stream part, after solvent evaporated, hydroxy benzaldehyde is obtained.
As the optimal way of embodiment, the step of the normal phase silicagel column adopted in the step 5 is separated for：
(1) silica white activation
200～300 mesh silica whites are taken in reagent bottle, with the masking foil for pricking hole bottleneck is wrapped, be placed in 110 DEG C of baking ovens living
Change 2～3h, bottleneck is sealed after cooling and is placed in exsiccator, it is standby；
(2) sample is mixed
According to amount 4mg of sample, the silica white 20mg in clean round-bottomed flask, with glue head dropper pipette samples drop extremely
On silica white in round-bottomed flask, stir rapidly and interval hair dryer is heated so that solvent is quickly waved to round-bottomed flask
It is dry, make sample in uniform powder, so repeat, until sample is all adsorbed on silica white, continue to heat, in making sample
Solvent volatilizees completely, standby in exsiccator with being placed in after filter paper sealing；
(3) post is filled
Using wet method dress post, to weigh and fill post after 0.2g silica gel petroleum ether saturations；
(4) loading
Use a dry method on a sample, the silica white for being adsorbed with sample is filled in chromatographic column so as to which uniform settlement is in layer of silica gel table
Face, treats that sample sedimentation is complete, opens valve, collects eluent；
(5) sample elution
Gradient elution：First eluting is carried out to sample with initial eluent, be then gradually increased the polarity of eluant, stripped
Pump up in journey and followed the trail of with thin layer chromatography TLC, until impact point is eluted；
(6) collection of sample with merge
With small test tube fraction collection sample, the sample cell containing impact point is merged into into several parts according to post order is gone out,
After concentrating under reduced pressure, proceed thin layer chromatography, proceeded to separate or merge 4 DEG C of storages after concentration according to the concrete condition of sample
Hide standby.
Used as the optimal way of embodiment, the thin layer chromatography TLC is followed the trail of and is：By GF254 silica gel plates in 110 DEG C of baking ovens
Activation 2～3h, after it naturally cools to room temperature take out, be placed in it is standby in exsiccator, with capillary glass tube draw appropriate amount of sample,
Point and carries out labelling on silica gel plate baseline in sampling point lower end pencil, on silica gel plate baseline distance plate bottom distance for 0.8～
The distance between 1cm, two sampling points are not less than 0.8cm, are dried up after solvent with hair-dryer, are placed in the chromatography cylinder equipped with saturation chromatographic solution
Middle expansion, when solvent front is opened up to away from lamellae top about 1cm, with tweezers take out, dry up solvent, with uv analyzer and its
Its developer is developed the color.
As the optimal way of embodiment, also including the Structural Identification of hydroxy benzaldehyde：To make after normal phase silicagel column
The hydroxy benzaldehyde for obtaining is fitted in nuclear magnetic tube, solvent evaporated, deuterated reagent is added, using TMS as internal standard, using 400MHz cores
Magnetic resonance device determines the nuclear-magnetism spectrum of compound, and measure project includes1H-NMR、13C-NMR、DEPT 90、DEPT 135、1H-1H
COSY、HSQC、HMBC；Mass spectrum, Mass Spectrometry Conditions are determined after sample is dissolved with the methanol solution containing 5% formic acid：Ionization source：EFI
Mist ionization source；It is dried temperature degree：200℃；It is dried atmospheric pressure：20psi；Atomization gas pressure：50psi；Aerochamber temperature 50 C；Pin
Hole voltage：5000V；Mask voltage：600V；Capillary voltage：80V.
The present invention is progressively extracted using after above-mentioned technical proposal by adding extract in pickled radish, and by anti-phase
The chromatographic isolation of silicagel column and normal phase silicagel column, is finally obtained hydroxy benzaldehyde, and the present invention is separated to first from pickled radish
Hydroxy benzaldehyde, the composition is the active substance for suppressing funguses in pickled radish.
Description of the drawings
Fig. 1 is the thin layer chromatography result of Y3 of the present invention；Wherein, developing solvent petroleum ether：Ethyl acetate=5:1, iodine shows；
Fig. 2 is the structure chart of Y3 of the present invention.
Specific embodiment
Present invention is disclosed a kind of method that hydroxy benzaldehyde is prepared from pickled radish, comprises the following steps：
The preparation of step one, pickled radish dry powder：Pickled radish is thinly sliced, is dried at 50 DEG C, crushed, cross 20 mesh
Sieve, obtains pickled radish dry powder, loaded in hermetic bag, saves backup in exsiccator；
The preparation of step 2, pickled radish crude extract：2 parts of 5 years pickled radish powder of dries pulverizing are weighed, every part of 20g divides
In not being placed in 2 500mL triangular flasks, by solid-liquid ratio 1:15 are separately added into ethyl acetate and acetone, are placed in after sealing in shaking table, 40
DEG C, 6h is extracted under 150rpm, sucking filtration collects filtrate；Coordinative solvent is added to carry out second extraction in residue again, same
Under the conditions of extract 3h, sucking filtration collects filtrate, after solvent is volatilized in residue, then exchanges solvent extraction 1 time, and extraction conditions are with the
Second extraction, merging filtrate, 40 DEG C are evaporated in round-bottomed flask, recycling design, and ethyl acetate and acetone extraction are obtained respectively
Thing extractum, combined ethyl acetate and acetone extract extractum, obtain pickled radish crude extract, and 4 DEG C of storages are standby；
The initial gross separation of step 3, pickled radish crude extract：By pickled radish crude extract with filtering after methanol dissolving, 40 DEG C subtract
The upper Sephadex LH-20 gel columns containing 170g fillers, eluting, coutroi velocity are carried out with methanol as eluant after pressure concentration
For 5～9s/drop, each stream part is collected using automatic collector, 1 is collected per 60min and is managed, collected obtain 128 pipe flow parts altogether；Merge
The stream part of the 48th to the 63rd pipe, then concentrating under reduced pressure is carried out, obtain component Y1；
Step 4, component Y1 are isolated and purified：After component Y1 is with proper amount of methanol dissolving, directly above contain 170g fillers
Sephadex LH-20 gel columns, eluting is carried out with methanol as eluant, and Jing gel post separations several times, final collection obtains
31 pipe flow parts, merge the 11st to the 15th pipe flow part and obtain 310mg samples, and the part is labeled as into component 1-2；
Step 5, component 1-2 are isolated and purified：Component 1-2 adds after proper amount of methanol dissolving, and crossing reverse phase silica gel post is carried out point
From with 50%CH3OH carries out eluting, and elution volume is 1L, and 1 stream part is collected per 200mL, collects obtain 5 stream parts altogether, 45 DEG C
Concentrating under reduced pressure is removed after solvent, selects the 1st stream part to be separated with purification on normal-phase silica gel；2mg samples after purification on normal-phase silica gel is separated
Sample is mixed with 10mg silica whites, after 0.08g silica gel petroleum ether saturations post is filled, after sample upper prop, eluting is carried out with petroleum ether, collected
The stream part of the 20th to the 32nd pipe, merges and concentrated after stream part, after solvent evaporated, hydroxy benzaldehyde is obtained.
As the optimal way of embodiment, the step of the normal phase silicagel column adopted in the step 5 is separated for：
(1) silica white activation
200～300 mesh silica whites are taken in reagent bottle, with the masking foil for pricking hole bottleneck is wrapped, be placed in 110 DEG C of baking ovens living
Change 2～3h, bottleneck is sealed after cooling and is placed in exsiccator, it is standby；
(2) sample is mixed
According to amount 4mg of sample, the silica white 20mg in clean round-bottomed flask, with glue head dropper pipette samples drop extremely
On silica white in round-bottomed flask, stir rapidly and interval hair dryer is heated so that solvent is quickly waved to round-bottomed flask
It is dry, make sample in uniform powder, so repeat, until sample is all adsorbed on silica white, continue to heat, in making sample
Solvent volatilizees completely, standby in exsiccator with being placed in after filter paper sealing；
(3) post is filled
Using wet method dress post, to weigh and fill post after 0.2g silica gel petroleum ether saturations；
(4) loading
Use a dry method on a sample, the silica white for being adsorbed with sample is filled in chromatographic column so as to which uniform settlement is in layer of silica gel table
Face, treats that sample sedimentation is complete, opens valve, collects eluent；
(5) sample elution
Gradient elution：First eluting is carried out to sample with initial eluent, be then gradually increased the polarity of eluant, stripped
Pump up in journey and followed the trail of with thin layer chromatography TLC, as a result as shown in figure 1, until impact point is eluted；
(6) collection of sample with merge
With small test tube fraction collection sample, the sample cell containing impact point is merged into into several parts according to post order is gone out,
After concentrating under reduced pressure, proceed thin layer chromatography, proceeded to separate or merge 4 DEG C of storages after concentration according to the concrete condition of sample
Hide standby.
Used as the optimal way of embodiment, the thin layer chromatography TLC is followed the trail of and is：By GF254 silica gel plates in 110 DEG C of baking ovens
Activation 2～3h, after it naturally cools to room temperature take out, be placed in it is standby in exsiccator, with capillary glass tube draw appropriate amount of sample,
Point and carries out labelling on silica gel plate baseline in sampling point lower end pencil, on silica gel plate baseline distance plate bottom distance for 0.8～
The distance between 1cm, two sampling points are not less than 0.8cm, are dried up after solvent with hair-dryer, are placed in the chromatography cylinder equipped with saturation chromatographic solution
Middle expansion, when solvent front is opened up to away from lamellae top about 1cm, with tweezers take out, dry up solvent, with uv analyzer and its
Its developer is developed the color.
As the optimal way of embodiment, also including the Structural Identification of hydroxy benzaldehyde：To make after normal phase silicagel column
The hydroxy benzaldehyde for obtaining is fitted in nuclear magnetic tube, solvent evaporated, deuterated reagent is added, using TMS as internal standard, using 400MHz cores
Magnetic resonance device determines the nuclear-magnetism spectrum of compound, and measure project includes1H-NMR、13C-NMR、DEPT 90、DEPT 135、1H-1H
COSY、HSQC、HMBC；Mass spectrum, Mass Spectrometry Conditions are determined after sample is dissolved with the methanol solution containing 5% formic acid：Ionization source：EFI
Mist ionization source；It is dried temperature degree：200℃；It is dried atmospheric pressure：20psi；Atomization gas pressure：50psi；Aerochamber temperature 50 C；Pin
Hole voltage：5000V；Mask voltage：600V；Capillary voltage：80V.The nuclear-magnetism modal data of hydroxy benzaldehyde is as shown in table 1.
Carry out understanding the ESI-MS of compound Y3 after mass spectroscopy：M/z=121 [M-1]+, the nuclear-magnetism modal data of comprehensive Y3
And mass spectrometric data and compare with document, thus it is speculated that compound is that (molecular formula is C to hydroxy benzaldehyde7H6O2, molecular weight is
122.1), its structure is as shown in Figure 2.
The nuclear-magnetism modal data of the compound Y3 of table 1
Pickled radish as South Fujian Province a kind of traditional pickling process food, in occupation of very in the daily life of locals
Consequence, is the crystallization of wisdom of people from the south of Fujian Province, is the succession of Chinese traditional Food Culture.At present, pickled radish is edible
It is worth and is approved by increasing people, therefore, the research that pickled radish carries out each side is had great importance and applied
Value.Mainly the Antibacterial Constituents in pickled radish are carried out by attached gel column chromatography and silica gel column chromatography in this research
Separate, and isolated hydroxy benzaldehyde first, hydroxy benzaldehyde as pickled radish anti-fungal composition, for salt
The secondary development of stain Radix Raphani is significant.
All deformations that one of ordinary skill in the art can directly derive from the disclosure of invention or associate, all should
It is considered protection scope of the present invention.
Claims (4)
1. a kind of method that hydroxy benzaldehyde is prepared from pickled radish, it is characterised in that：Comprise the following steps：
The preparation of step one, pickled radish dry powder：Pickled radish is thinly sliced, is dried at 50 DEG C, crushed, cross 20 mesh sieves, obtained
Pickled radish dry powder, loaded in hermetic bag, saves backup in exsiccator；
The preparation of step 2, pickled radish crude extract：2 parts of 5 years pickled radish powder of dries pulverizing are weighed, every part of 20g puts respectively
In 2 500mL triangular flasks, by solid-liquid ratio 1:15 are separately added into ethyl acetate and acetone, are placed in after sealing in shaking table, 40 DEG C,
6h is extracted under 150rpm, sucking filtration collects filtrate；Coordinative solvent is added to carry out second extraction in residue again, in same bar
3h is extracted under part, sucking filtration collects filtrate, after solvent is volatilized in residue, then exchanges solvent extraction 1 time, and extraction conditions are with second
Secondary extraction, merging filtrate, 40 DEG C are evaporated in round-bottomed flask, recycling design, and ethyl acetate and acetone extract are obtained respectively
Extractum, combined ethyl acetate and acetone extract extractum, obtain pickled radish crude extract, and 4 DEG C of storages are standby；
The initial gross separation of step 3, pickled radish crude extract：By pickled radish crude extract with filtering after methanol dissolving, 40 DEG C of decompressions are dense
The upper Sephadex LH-20 gel columns containing 170g fillers after contracting, eluting is carried out with methanol as eluant, and coutroi velocity is 5～
9s/drop, using automatic collector each stream part is collected, and 1 is collected per 60min and is managed, and collects obtain 128 pipe flow parts altogether；Merge the 48th
To the stream part of the 63rd pipe, then concentrating under reduced pressure is carried out, obtain component Y1；
Step 4, component Y1 are isolated and purified：After component Y1 is with proper amount of methanol dissolving, directly above contain the Sephadex of 170g fillers
LH-20 gel columns, eluting is carried out with methanol as eluant, and Jing gel post separations several times, final collection obtains 31 pipe flow parts,
Merge the 11st to the 15th pipe flow part and obtain 310mg samples, the part is labeled as into component 1-2；
Step 5, component 1-2 are isolated and purified：Component 1-2 adds after proper amount of methanol dissolving, crosses reverse phase silica gel post and is separated, with
50%CH3OH carries out eluting, and elution volume is 1L, and 1 stream part is collected per 200mL, collects obtain 5 stream parts altogether, 45 DEG C of decompressions
Concentration is removed after solvent, selects the 1st stream part to be separated with purification on normal-phase silica gel；2mg samples after purification on normal-phase silica gel is separated are used
10mg silica whites mix sample, and after 0.08g silica gel petroleum ether saturations post is filled, and after sample upper prop, carry out eluting with petroleum ether, collect the
The stream part of 20 to the 32nd pipes, merges and concentrated after stream part, after solvent evaporated, hydroxy benzaldehyde is obtained.
2. a kind of method that hydroxy benzaldehyde is prepared from pickled radish as claimed in claim 1, it is characterised in that：It is described
The step of normal phase silicagel column adopted in step 5 is separated for：
(1) silica white activation
200～300 mesh silica whites are taken in reagent bottle, with the masking foil for pricking hole bottleneck is wrapped, be placed in 110 DEG C of baking ovens and activate 2
～3h, seals bottleneck and is placed in exsiccator after cooling, standby；
(2) sample is mixed
According to amount 2mg of sample, the silica white 10mg in clean round-bottomed flask, with glue head dropper pipette samples drop to round bottom
On silica white in flask, stir rapidly and interval hair dryer is heated so that solvent is quickly volatilized to round-bottomed flask, make
Sample is in uniform powder, is so repeated, until sample is all adsorbed on silica white, continues to heat, and makes the solvent in sample
Volatilize completely, it is standby in exsiccator with being placed in after filter paper sealing；
(3) post is filled
Using wet method dress post, to weigh and fill post after 0.08g silica gel petroleum ether saturations；
(4) loading
Use a dry method on a sample, the silica white for being adsorbed with sample is filled in chromatographic column so as to which uniform settlement is treated in silica gel layer surface
Sample sedimentation is complete, opens valve, collects eluent；
(5) sample elution
Gradient elution：First eluting is carried out to sample with initial eluent, the polarity of eluant is then gradually increased, in elution process
Pump up and followed the trail of with thin layer chromatography TLC, until impact point is eluted；
(6) collection of sample with merge
With small test tube fraction collection sample, the sample cell containing impact point is merged into into several parts according to post order is gone out, reduced pressure
After concentration, proceed thin layer chromatography, proceed to separate or merge 4 DEG C of storages after concentration according to the concrete condition of sample standby
With.
3. a kind of method that hydroxy benzaldehyde is prepared from pickled radish as claimed in claim 2, it is characterised in that：It is described
Thin layer chromatography TLC is followed the trail of：GF254 silica gel plates are activated into 2～3h in 110 DEG C of baking ovens, is taken after it naturally cools to room temperature
Go out, be placed in it is standby in exsiccator, with capillary glass tube draw appropriate amount of sample, put on silica gel plate baseline, and sampling point lower end use
Pencil carries out labelling, and baseline distance plate bottom is not less than 0.8cm apart from for the distance between 0.8～1cm, two sampling points on silica gel plate,
Dried up after solvent with hair-dryer, be placed in the chromatography cylinder equipped with saturation chromatographic solution and launch, treat that solvent front is opened up to away from thin layer top of the plate
During the about 1cm of end, taken out with tweezers, dry up solvent, developed the color with uv analyzer and other developers.
4. a kind of method that hydroxy benzaldehyde is prepared from pickled radish as claimed in claim 1, it is characterised in that：Also wrap
Include the Structural Identification of hydroxy benzaldehyde：Obtained hydroxy benzaldehyde after normal phase silicagel column is fitted in nuclear magnetic tube, is evaporated
Solvent, adds deuterated reagent, using TMS as internal standard, is composed using the nuclear-magnetism of 400MHz nmr determination compounds, determines item
Mesh includes1H-NMR、13C-NMR、DEPT 90、DEPT 135、1H-1H COSY、HSQC、HMBC；Sample is used containing 5% formic acid
Mass spectrum, Mass Spectrometry Conditions are determined after methanol solution dissolving：Ionization source：Electron spray ionisation source；It is dried temperature degree：200℃；It is dried air pressure
Power：20psi；Atomization gas pressure：50psi；Aerochamber temperature 50 C；Pin hole voltage：5000V；Mask voltage：600V；Capillary tube
Voltage：80V.
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