CN103823015B - Preparation method for chitosamine hydrochloride and thin layer chromatography scanning detection method - Google Patents
Preparation method for chitosamine hydrochloride and thin layer chromatography scanning detection method Download PDFInfo
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- CN103823015B CN103823015B CN201410075746.9A CN201410075746A CN103823015B CN 103823015 B CN103823015 B CN 103823015B CN 201410075746 A CN201410075746 A CN 201410075746A CN 103823015 B CN103823015 B CN 103823015B
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Abstract
The invention discloses a thin layer chromatography scanning detection method for chitosamine hydrochloride. The method has the advantages of simplicity and convenience, quickness, accuracy, reliability and stability, and comprises the following steps: step (1), dripping sample liquid and standard liquid on a same efficient thin layer silica gel plate GF254, unfolding, and airing; step (2), spraying the acetone solution of aniline-diphenylamine-trichloroacetic acid on the efficient thin layer silica gel plate uniformly, or soaking the plate for 1 min, airing, and baking and dyeing; step (3), adopting a thin layer scanner to conduct thin layer chromatography scanning, so that the chitosamine hydrochloride RF and the peak area integral quantity are obtained; calculating the relationship between the standard liquid quality and the peak area integral quantity through thin layer chromatograph management software, and calculating the chitosamine hydrochloride content of the sample according to the peak area integral quantity of the sample liquid. The invention further discloses a method for preparing the chitosamine hydrochloride by adopting antarctic krill as a raw material through acidolysis, so that the comprehensive utilization of the antarctic krill is enriched, the utilization ratio is increased, and the economic benefit is increased.
Description
Technical field
The present invention relates to preparation method and the thin-layer chromatography scanning detection method of aminoglucose hydrochloride.
Background technology
Aminoglucose hydrochloride, also known as aminoglucose hydrochloride, molecular formula C
6h
13nO
5hCl, it has important physiological function to human body, participates in the removing toxic substances of liver kidney, play anti-inflammatory liver protection effect, there is good curative effect to treatment rheumatism joint inflammation and gastric ulcer, be the primary raw material of synthetic antibiotic and cancer therapy drug, also can be applicable in chemical industry, food, cosmetics and feed addictive.The amino sugar Capsules of health productions principle active component sold in the market is aminoglucose hydrochloride or Glucosamine Sulphate, and it can be obtained by chitin hydrochloric acid pyrohydrolysis.Chitin is many lower animals, particularly arthropod---the important component of the shells such as shrimp crab and insect.Containing a large amount of chitin in krill body, it is one of single biology that on the earth, stock number is maximum, and krill aboundresources, the highest according to estimates have several hundred million ton, and catchability is more than 1 times of the existing fishery production in the world, has huge development and utilization potentiality.Therefore, if be that aminoglucose hydrochloride prepared by raw material with krill, can yet be regarded as a kind of effective and the method for resource can be made full use of.
Summary of the invention
For above-mentioned prior art, the invention provides with krill is the method that aminoglucose hydrochloride prepared by raw material, additionally provides the thin-layer chromatography scanning detection method of aminoglucose hydrochloride.
The present invention is achieved by the following technical solutions:
Take krill as the method that aminoglucose hydrochloride prepared by raw material, step is as follows:
(1) get krill, soak 2 ~ 6 hours with 95% ethanol (percent by volume) of 5 ~ 10 times amount (quality multiple), filter to obtain filter residue;
(2) get above-mentioned filter residue, put into closed container, add the distilled water of 5 ~ 10 times amount (quality multiple), stir 1 ~ 4 hour at 15 ~ 40 DEG C by constant temperature blender with magnetic force, filter to obtain filter residue;
(3) filter residue that step (2) is obtained is got, put into triangular flask, the concentration adding 10 ~ 20 times amount (quality multiple) is the concentrated hydrochloric acid of 5 ~ 7mol/L, connects condensation reflux unit, utilize heated at constant temperature stirring apparatus acidolysis filter residue 4 ~ 6 hours at 105 ~ 110 DEG C, obtain acid hydrolysis solution;
(4) above-mentioned obtained acid hydrolysis solution is got, filter, filtrate rotary evaporation is concentrated flings to hydrochloric acid (design temperature of Rotary Evaporators 40 DEG C ~ 50 DEG C), obtain crude product, adding distil water dissolves, and adds the activated charcoal stirring and adsorbing of 0.1 ~ 0.3 times of crude product quality, filters the solution obtaining faint yellow clarification, freeze drying, obtains aminoglucose hydrochloride;
Present invention also offers another with krill is the method that aminoglucose hydrochloride prepared by raw material, and step is as follows:
(1) get krill, soak 2 ~ 6 hours with 95% ethanol (percent by volume) of 5 ~ 10 times amount (quality multiple), filter to obtain filter residue; Then filter residue being added massfraction is in the watery hydrochloric acid of 3% ~ 5%, and the addition of watery hydrochloric acid is 5 ~ 10 times of filter residue quality, soaks 8 ~ 16h, and filter, filter residue is washed to neutrality, obtains shrimp slag;
(2) get the shrimp slag that above-mentioned steps (1) obtains, add the dilute alkaline soln that massfraction is 1% ~ 3%, the addition of diluted alkaline is 5 ~ 10 times of filter residue quality, heating water bath, temperature 80 DEG C ~ 95 DEG C, heat time 30min ~ 60min, filter, filter residue is washed to neutrality, obtains shrimp slag;
Described dilute alkaline soln is KOH solution or NaOH solution;
(3) get the shrimp slag that above-mentioned steps (2) obtains, adding massfraction is in the watery hydrochloric acid of 3% ~ 5%, and the addition of watery hydrochloric acid is 5 ~ 10 times of filter residue quality, soaks 1 ~ 2h, and filter, filter residue is washed to neutrality, obtains shrimp slag;
(4) get the shrimp slag that above-mentioned steps (3) obtains, add the dilute alkaline soln that massfraction is 1% ~ 3%, the addition of diluted alkaline is 5 ~ 10 times of filter residue quality, and in constant temperature blender with magnetic force, 60 DEG C ~ 70 DEG C add thermal agitation 1h ~ 2h, filters, and obtains the filter residue of white;
(5) filter residue of the obtained white of above-mentioned steps (4) is got, put into triangular flask, the concentration adding 10 ~ 20 times amount (quality multiple) is the concentrated hydrochloric acid of 5 ~ 7mol/L, connect condensation reflux unit, utilize heated at constant temperature stirring apparatus acidolysis filter residue 4 ~ 6 hours at 105 ~ 110 DEG C, obtain acid hydrolysis solution;
(6) above-mentioned obtained acid hydrolysis solution is got, filter, filtrate rotary evaporation is concentrated flings to hydrochloric acid (design temperature of Rotary Evaporators 40 DEG C ~ 50 DEG C), obtain crude product, adding distil water dissolves, and adds the activated charcoal stirring and adsorbing of 0.1 ~ 0.3 times of crude product quality, filters the solution obtaining light yellow clarification, freeze drying, obtains aminoglucose hydrochloride;
Present invention also offers a kind of thin-layer chromatography scanning detection method of aminoglucose hydrochloride, step is as follows:
Step is 1.: added by developping agent in expansion cylinder and carry out pre-equilibration, the titer of sample liquid and different volumes is put respectively on same High Performance Thin silica gel plate GF254, then High Performance Thin silica gel plate is put into expansion cylinder to launch, exhibition is apart from 8cm, and taking-up is dried;
Described developping agent is methanol-acetone-acetic acid-water-isopropyl alcohol mixed liquor, by volume, and methyl alcohol: acetone: acetic acid: water: isopropyl alcohol=3 ~ 5:3 ~ 4:0.2 ~ 0.5:0.5 ~ 1:1 ~ 2;
The temperature of described developping agent pre-equilibration and silica gel plate expansion process is 25 DEG C, time 15min ~ 20min.The double flute seal glass expansion cylinder of expansion cylinder: 12cm × 10cm × 5cm;
Described sample liquid is solution adjust pH to 6.5 ~ 6.8 gained by the solution of the faint yellow clarification of above-mentioned preparation or light yellow clarification.
The concentration of described titer is 2.55mg/ml, and the volume of point is respectively 0.25ul, 0.5ul, 1.0ul, 2.0ul, 3.0ul; The point sample amount of sample liquid is 1.0ul;
Step is 2.: be evenly sprayed onto on High Performance Thin silica gel plate by the acetone soln of aniline-diphenylamine-trichloroacetic acid, or: container High Performance Thin silica gel plate being put into the acetone soln filling aniline-diphenylamine-trichloroacetic acid soaks plate 1min, dry, baking dyeing (baking temperature is 85 DEG C, time 10min);
In the acetone soln of described every 50ml aniline-diphenylamine-trichloroacetic acid, containing aniline 0.5g, diphenylamine 0.5ml, trichloroacetic acid 2.5g, surplus is acetone;
Step is 3.: utilize thin-layer chromatogram scanner to carry out thin-layer chromatography scanning, obtain aminoglucose hydrochloride Rf(Rf value) and integrating peak areas value; Calculate titer quality and integrating peak areas value relation by thin layer chromatograph management software, the integrating peak areas value of liquid calculates the aminoglucose hydrochloride content of sample per sample.
The present invention is when carrying out thin-layer chromatography, for obtaining effective effect, explore different developping agents and coloring agent, finally determine developping agent methanol-acetone-acetic acid-water-isopropyl alcohol (3 ~ 5:3 ~ 4:0.2 ~ 0.5:0.5 ~ 1:1 ~ 2), the acetone soln coloring agent of aniline-diphenylamine-trichloroacetic acid, after aminoglucose hydrochloride derivatization, aobvious brown, in yellow green under the ultraviolet light of 365nm, it makes other sugar in different colours, and whether acidolysis is complete therefore can to judge krill.
The invention discloses with krill is the method that aminoglucose hydrochloride is produced in raw material acidolysis, has enriched the comprehensive utilization of krill, has improve utilization factor, add economic benefit; Present invention also offers the thin-layer chromatography scanning detection method of aminoglucose hydrochloride, as compared to current detection method (titrimetry, colourimetry, HPLC method and GC method), this detection method is easy, quick, accurate, reliable, stable.
Embodiment
Below in conjunction with embodiment, the present invention is further illustrated.
Embodiment 1 is that raw material is prepared aminoglucose hydrochloride and carries out thin-layer chromatography Scanning Detction with krill
Method is: get the krill that 5.01g is freezing, put into the beaker of 95% ethanol that 30ml is housed, soak 5h, filter, then filter residue is added in the beaker filling 30ml4% watery hydrochloric acid and soak 10h, filter, filter residue is washed to neutrality, put into the triangular flask filling 30ml2%KOH solution, 80 DEG C of heating water bath 45min, filter, filter residue is washed to neutrality, put into the beaker filling 30ml4% watery hydrochloric acid again and soak 1.5h, filter, filter residue is washed to neutrality, again put into the triangular flask filling 30ml2%KOH solution, 60 DEG C of heating moderate-speed mixer 1h in constant temperature blender with magnetic force, obtain the filter residue of white, put into 250ml triangular flask, add the concentrated hydrochloric acid of 100ml6mol/L, connect condensation reflux unit, at DHT type heated at constant temperature stirring apparatus, 110 DEG C of heating acidolysis filter residue 6h, obtain acid hydrolysis solution.Filter, filtrate is concentrated Rotary Evaporators 45 DEG C, reclaim the hydrochloric acid flung to, then adding distil water dissolves, and adds 0.5g303 type craboraffin stirring and adsorbing, filters the solution obtaining faint yellow clarification, is settled to 10ml(as following sample).Take the distilled water that 10.2mg standard items are dissolved in 4ml, regulate the pH value to 6.6 of sample and standard items.Sample liquid (1 μ L/ point) and titer (volume is respectively 0.25 μ L, 0.5 μ L, 1 μ L, 2 μ L, 3 μ L) are put on same GF254 High Performance Thin silica gel plate (10cm × 10cm), developping agent is methanol-acetone-glacial acetic acid-water-isopropyl alcohol, and volume ratio is 4:3:0.5:1:1.5.Developping agent is added expansion cylinder (12cm × 10cm × 5cm) pre-equilibration 20 minutes at 25 DEG C.Expansion cylinder put into by High Performance Thin plate, launches below 25 DEG C, and silica gel plate plate, apart from when reaching 8cm, takes out and dries by exhibition.Double dish plate being put into the acetone soln filling aniline-diphenylamine-trichloroacetic acid soaks plate, toasts 10min at being then placed in 85 DEG C.Sample liquid and point corresponding to standard items are dyed brown.With camag3 type thin-layer chromatogram scanner, scan with the absorbing wavelength of 365nm, obtain integrating peak areas value and aminoglucose hydrochloride migration value Rf is 0.68, the regression equation of the relation of thin-layer chromatogram scanner software winCATS1.4.1 statistical computation integrating peak areas value and titer quality (ng), correlativity Y=1.9744X-244.9822 (r=0.99988RSD=1.74%).After testing and calculate, the aminoglucose hydrochloride quality that every gram of krill acidolysis obtains is 3.554mg.
In the acetone soln of described every 50ml aniline-diphenylamine-trichloroacetic acid, containing aniline 0.5g, diphenylamine 0.5ml, trichloroacetic acid 2.5g, surplus is acetone.
Embodiment 2 is that raw material is prepared aminoglucose hydrochloride and carries out thin-layer chromatography Scanning Detction with krill
Prepare and detect aminoglucose hydrochloride: getting the krill that 5.00g is freezing, putting into the beaker of 95% ethanol that 40ml is housed, soaking 4h, filter, filter residue puts into triangular flask, adds the distilled water of 40ml, stirs 2h by constant temperature blender with magnetic force 40 DEG C, filter, filter residue joins in the 5mol/L concentrated hydrochloric acid of 80ml, connects condensation reflux unit, at DHT type heated at constant temperature stirring apparatus, 105 DEG C of heating acidolysis filter residue 6.5h, obtain acid hydrolysis solution.Other follow-up operation is identical with embodiment 1, but developping agent is methanol-acetone-glacial acetic acid-water-isopropyl alcohol, and volume ratio is 4:3.5:0.5:1:1.5.Aminoglucose hydrochloride migration value Rf is 0.66, and after testing and calculate, the aminoglucose hydrochloride quality that every gram of krill acidolysis obtains is 3.8mg.
Embodiment 3 is that raw material is prepared aminoglucose hydrochloride and carries out thin-layer chromatography Scanning Detction with krill
Prepare and detect aminoglucose hydrochloride: getting the krill that 5.00g is freezing, put into the beaker that 40ml3% watery hydrochloric acid is housed, soak 12h, filter, be washed to neutrality, filter residue puts into the triangular flask of 40ml1.5%KOH solution, 85 DEG C of heating water bath 50min, filter, filter residue is washed to neutrality, put into the beaker that 40ml3% watery hydrochloric acid is housed again and soak 2h, filter, filter residue is washed to neutrality, again puts into the triangular flask of 40ml1.5%KOH solution, in constant temperature blender with magnetic force, 70 DEG C of heating moderate-speed mixer 1h, obtain the filter residue of white; The filter residue of white puts into 250ml triangular flask, adds the concentrated hydrochloric acid of 100ml6mol/L, connects condensation reflux unit, and at DHT type heated at constant temperature stirring apparatus, 110 DEG C of heating acidolysis filter residue 6h, obtain acid hydrolysis solution.Filter, filtrate is concentrated Rotary Evaporators 50 DEG C, reclaim the hydrochloric acid flung to, then adding distil water dissolves, and adds 1.0g303 type craboraffin stirring and adsorbing, filters the solution obtaining faint yellow clarification, is settled to 10ml(as following sample).Other follow-up operation is identical with embodiment 1, but developping agent is methanol-acetone-glacial acetic acid-water-isopropyl alcohol, and volume ratio is 4:4:0.3:1:1.Aminoglucose hydrochloride migration value Rf is 0.64, and after testing and calculate, the aminoglucose hydrochloride quality that every gram of krill acidolysis obtains is 3.52mg.
Claims (7)
1. a thin-layer chromatography scanning detection method for aminoglucose hydrochloride, is characterized in that: step is as follows:
Step is 1.: added by developping agent in expansion cylinder and carry out pre-equilibration, the titer of aminoglucose hydrochloride sample liquid and different volumes is put respectively on same High Performance Thin silica gel plate GF254, then High Performance Thin silica gel plate is put into expansion cylinder to launch, exhibition is apart from 8cm, and taking-up is dried;
Described developping agent is methanol-acetone-acetic acid-water-isopropyl alcohol mixed liquor, by volume, and methyl alcohol: acetone: acetic acid: water: isopropyl alcohol=3 ~ 5:3 ~ 4:0.2 ~ 0.5:0.5 ~ 1:1 ~ 2;
Step is 2.: be evenly sprayed onto on High Performance Thin silica gel plate by the acetone soln of aniline-diphenylamine-trichloroacetic acid, or: container High Performance Thin silica gel plate being put into the acetone soln filling aniline-diphenylamine-trichloroacetic acid soaks plate 1min, dries, baking dyeing;
In the acetone soln of described every 50ml aniline-diphenylamine-trichloroacetic acid, containing aniline 0.5g, diphenylamine 0.5ml, trichloroacetic acid 2.5g, surplus is acetone;
Step is 3.: utilize thin-layer chromatogram scanner to carry out thin-layer chromatography scanning, obtain aminoglucose hydrochloride Rf and integrating peak areas value; Calculate titer quality and integrating peak areas value relation by thin layer chromatograph management software, the integrating peak areas value of liquid calculates the aminoglucose hydrochloride content of sample per sample.
2. the thin-layer chromatography scanning detection method of aminoglucose hydrochloride according to claim 1, is characterized in that: described sample liquid prepares by the following method:
(1) get krill, by 95% alcohol immersion 2 ~ 6 hours of 5 ~ 10 times amount, filter to obtain filter residue;
(2) get above-mentioned filter residue, add the distilled water of 5 ~ 10 times amount, stir 1 ~ 4 hour at 15 ~ 40 DEG C, filter to obtain filter residue;
(3) get the filter residue that step (2) is obtained, the concentration adding 10 ~ 20 times amount is the concentrated hydrochloric acid of 5 ~ 7mol/L, connects condensation reflux unit, utilizes heated at constant temperature stirring apparatus acidolysis filter residue 4 ~ 6 hours at 105 ~ 110 DEG C, obtains acid hydrolysis solution;
(4) get above-mentioned obtained acid hydrolysis solution, filter, filtrate rotary evaporation is concentrated flings to hydrochloric acid, obtain crude product, adding distil water dissolves, and adds the activated charcoal stirring and adsorbing of 0.1 ~ 0.3 times of crude product quality, filter the solution obtaining faint yellow clarification, adjust pH to 6.5 ~ 6.8, obtain sample liquid.
3. the thin-layer chromatography scanning detection method of aminoglucose hydrochloride according to claim 1, is characterized in that: described sample liquid prepares by the following method:
(1) get krill, by 95% alcohol immersion 2 ~ 6 hours of 5 ~ 10 times amount, filter to obtain filter residue; Then filter residue being added massfraction is in the watery hydrochloric acid of 3% ~ 5%, and the addition of watery hydrochloric acid is 5 ~ 10 times of filter residue quality, soaks 8 ~ 16h, and filter, filter residue is washed to neutrality, obtains shrimp slag;
(2) get the shrimp slag that above-mentioned steps (1) obtains, add the dilute alkaline soln that massfraction is 1% ~ 3%, the addition of diluted alkaline is 5 ~ 10 times of filter residue quality, heating water bath, temperature 80 DEG C ~ 95 DEG C, heat time 30min ~ 60min, filter, filter residue is washed to neutrality, obtains shrimp slag;
(3) get the shrimp slag that above-mentioned steps (2) obtains, adding massfraction is in the watery hydrochloric acid of 3% ~ 5%, and the addition of watery hydrochloric acid is 5 ~ 10 times of filter residue quality, soaks 1 ~ 2h, and filter, filter residue is washed to neutrality, obtains shrimp slag;
(4) get the shrimp slag that above-mentioned steps (3) obtains, add the dilute alkaline soln that massfraction is 1% ~ 3%, the addition of diluted alkaline is 5 ~ 10 times of filter residue quality, and 60 DEG C ~ 70 DEG C add thermal agitation 1h ~ 2h, filters, and obtains the filter residue of white;
(5) get the filter residue of the obtained white of above-mentioned steps (4), the concentration adding 10 ~ 20 times amount is the concentrated hydrochloric acid of 5 ~ 7mol/L, connects condensation reflux unit, utilizes heated at constant temperature stirring apparatus acidolysis filter residue 4 ~ 6 hours at 105 ~ 110 DEG C, obtains acid hydrolysis solution;
(6) get above-mentioned obtained acid hydrolysis solution, filter, filtrate rotary evaporation is concentrated flings to hydrochloric acid, obtain crude product, adding distil water dissolves, and adds the activated charcoal stirring and adsorbing of 0.1 ~ 0.3 times of crude product quality, filter the solution obtaining light yellow clarification, adjust pH to 6.5 ~ 6.8, obtain sample liquid.
4. the thin-layer chromatography scanning detection method of aminoglucose hydrochloride according to claim 3, is characterized in that: described dilute alkaline soln is KOH solution or NaOH solution.
5. the thin-layer chromatography scanning detection method of aminoglucose hydrochloride according to claim 1, is characterized in that: the temperature of described developping agent pre-equilibration and silica gel plate expansion process is 25 DEG C, time 15min ~ 20min; The double flute seal glass expansion cylinder of expansion cylinder: 12cm × 10cm × 5cm.
6. the thin-layer chromatography scanning detection method of aminoglucose hydrochloride according to claim 1, is characterized in that: the concentration of described titer is 2.55mg/ml, and the volume of point is respectively 0.25ul, 0.5ul, 1.0ul, 2.0ul, 3.0ul; The point sample amount of sample liquid is 1.0ul.
7. the thin-layer chromatography scanning detection method of aminoglucose hydrochloride according to claim 1, is characterized in that: during described baking dyeing, baking temperature is 85 DEG C, time 10min.
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| D-氨基葡萄糖盐酸盐的制备研究;李南等;《中国药科大学学报》;19971231;第28卷(第1期);第56-57页第2-3节 * |
| 薄层色谱法在2-氨基葡萄糖-四乙酸酯合成中的应用;赵先英等;《化学研究与应用》;20020630;第14卷(第3期);310-312 * |
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