Method of purifying dihydroquercitine and dihydrokaempferol from bioflavanoid extracts obtained in woodworking process

FIELD: woodworking industry.

SUBSTANCE: invention relates to methods for recovering and purifying native bioflavonoids: dihydroquercitine and dihydrokaempferol from larch wood extracts. Method of recovering bioflavonoids from larch wood extracts is characterized by that freeze-dried extract is dissolved in ethylacetone/water mixture composed in specified proportion, specified amount of resulting solution is introduced into column filled with urea (sorbent) preliminarily equilibrated with ethylacetate, and column is then eluted with an ester and/or ketone having boiling point below 120°C, or with ethylacetate/acetone mixture at specified ratio. Eluate is collected and evaporated until crystallization is observed and then cooled. Separated crystals are rinsed and dried.

EFFECT: enabled single-step process for separating dihydroquercitine and dihydrokaempferol from resinous impurities and other polymeric compounds, reduced process expenses, and reduced environmental impact.

4 cl, 1 dwg

 

The invention relates to methods of isolation and purification of native bioflavonoids - dihydroquercetin and dihydrocemferol, from extracts obtained during the processing of timber, such as larch. Larch wood is a source of native natural polymers, containing extractives - terpenes, resin acids, aromatic compounds, plant polyphenols, sterols, tannins, lipids, fatty acids and inorganic nitrogen-containing compounds.

In the processing of larch wood from it are biologically active compounds - bioflavonoids: dihydroquercetin and dihydrocemferol used as natural preservatives, but also finds application as a food additive.

A method of obtaining dihydroquercetin and dihydrocemferol with resultant deposition rates extracts in organic solvents (see, for example, patent RF №2034559).

The method is based on the combination of the distillation and solvent extraction and allows you to separate the DQC from a number of related substances with simultaneous regeneration of the organic solvent. The disadvantages of this method are the relatively low degree of purification of dihydroquercetin and dihydrocemferol (about 90%) and the long duration of the process of obtaining the final product.

Closest to izopet the tion is a method for dihydroquercetin and dihydrocemferol from an extract of larch wood, contains bioflavonoids, which includes a cleanup procedure using preparative chromatography dissolved in spitefire solvent lyophilized and contains bioflavonoids extract. As the sorbent during chromatographic purification of bioflavonoids use active alumina, silica gel or the polyamide resin (see, for example, patent RF №2135510, MCL. C13 To 1/02, 1998).

However, as shown by chromatographic practice, the use of sorbent active aluminum oxide, silicagel or polyamide resin is only possible when using extracts of wood, not containing impurities humic acid, pectic acid, high molecular weight resinous compounds, and substances with pronounced surface-active properties. Otherwise, there is a very rapid loss of the separation ability of the chromatographic column due to irreversible adsorption of these components on the chromatographic medium, which dramatically shortens the life of the sorbent. For regeneration of the column that requires a large time and large amounts of expensive and toxic compounds. In this regard, the above method requires chromatographic purification of dihydroquercetin and dihydrocemferol use extracts, bioflavonoids, not containing much-nor is UDI significant quantities of resinous and other above-described impurities. Otherwise, require regular regeneration of the sorbent or replacing speakers new sorbent. This increases the cost of the cleanup, a sharp increase in the time of the production cycle, and in the case of regular replacement of spent chromatographic media onto a new sorbent created environmental problems of disposal of the spent sorbent.

The invention aims to remedy these disadvantages and to develop ways chromatographic purification of dihydroquercetin and dihydrocemferol from extracts of bioflavonoids containing impurities humic acid, pectin, high molecular weight resinous compounds or with surface-active properties, which allows to significantly reduce the process of getting clean dihydroquercetin and dihydrocemferol and to decide on environmentally friendly disposal of sorbent, which allows to improve the ecology of the environment.

The problem is solved due to the fact that in the method of producing dihydroquercetin and dihydrocemferol from an extract of larch wood, containing bioflavonoids, organic solvent dissolve the lyophilized extract, then the resulting solution was applied on a column Packed with a sorbent - urea, pre-equilibrated with ethyl acetate; column elute complex ether and/and and a ketone having a boiling point below 120° C; the resulting eluate is collected, evaporated prior to the solidification and cooling, the precipitated crystals are washed and dried. As eluent possible to use ethyl acetate and acetone in the ratio of 1:1. Also as eluent may ispolzovat the ethyl acetate and acetone in the ratio of 1:2. To prevent blur peak bioflavanoid ratio of sorbent to the sample take is equal to 100:1.

The drawing shows a graph of optical density in units of optical density (units OF) from time (T, min) for chromatography. Indicate on the drawing:

1 is a chromatographic peak output unbound with sorbent compounds after application of the sample,

2 - chromatographic peak output of the pure dihydroquercetin and dihydrocemferol,

3 - time application of the sample,

4 - start time output peak unbound with sorbent compounds after application of the sample,

5 - the end time of the output of the impurities, the beginning of the elution with a mixture of ethyl acetate - acetone and collection of chromatographically purified dihydroquercetin and dihydrocemferol,

6 - time of completion of the output of the peak and collection of chromatographically purified dihydroquercetin and dihydrocemferol.

Conditions of chromatography

Sample commercial on bioflavonoidnogo complex sebell for the food and perfume products, dissolved in a mixture of ethyl acetate - acetone in soo is wearing a 1:1 at a concentration of 600 mg/ml

Column size: length=12 cm; diameter=0.8 cm

Sorbent - urea, balanced solution of ethyl acetate. The ratio of the sorbent and the sample is 100:1. Speed of application and elution of the sample to 1 ml/min Eluent a mixture of ethyl acetate and acetone in the ratio (1:2).

For carrying out the process used on bioflavonoidnogo commercial complex sebell for the food and perfume products obtained according to the technology described in the patent of Russian Federation №2186097 dated July 6, 2001 (000 manufacturer "Cyberax") and represents the dry extract bioflavonoids containing dihydroquercetin and dihydrocemferol.

On bioflavonoidnogo complex sebell, representing the dry powder was dissolved in a mixture of ethyl acetate - acetone (ratio of ethyl acetate : acetone 1:1) at a concentration of 600 mg/ml the ratio of substances in solution remained the same ratio of dry extract bioflavonoids. The resulting solution was applied (point 3) with a speed of 1 ml/min on a glass column (length - 12 cm; diameter 0.8 cm) in total volume of 6 ml of filled urea, pre-equilibrated in ethyl acetate.

The column was washed with a solution of ethyl acetate at 1 ml/min for 5 min (the time between points 3 and 5) until full output is not bound peroxidase on the speaker connections (see, peak 1, wavelength 280 nm).

Then the column was suirable (point 5) mixture e is elzett - acetone (ratio 1:2) at a rate of 1 ml/min for 7 min (time between points 5 and 6) to the full output of the first peak of the eluate (peak 2), containing dihydroquercetin and dihydrocemferol. The obtained eluate was collected and evaporated to the onset of crystallization in a stream of nitrogen at room temperature, and then was cooled to - 20°C. the Precipitated crystals were collected, washed with deionized water and dried for use. The remaining solution containing not fallen into the sediment bioflavonoids and other impurities were also dried and the precipitate was included in the raw material for the next use.

Column before applying drained from the used sorbent and filled with fresh portion of urea, prepared as described above, the entire purification procedure of dihydroquercetin and dihydrocemferol from extracts of bioflavonoids repeated again.

Analysis of the purity of the final mixture of dihydroquercetin and dihydrocemferol was performed using thin-layer chromatography, NMR spectroscopy and high-performance chromatography. The analysis showed that obtained after purification of the crystals content of dihydroquercetin and dihydrocemferol is not less than 98%. The output of dihydroquercetin and dihydrocemferol from the source of the drug varies between 70% and 80%. The analysis also showed that the obtained crystals are not sod is Ritsa resinous and other polymerbased impurities.

Thus, the proposed method of cleaning allows you to:

- conduct one-step separation of dihydroquercetin and dihydrocemferol from impurity resins and other polymerbased connections

- significantly reduce the cost of the process of obtaining pure dihydroquercetin and dihydrocemferol due to the very low cost of urea,

- reduce the amount of used high-purity solvents (acetone and ethyl acetate) due to the lack of procedures for the purification of the sorbent after chromatography bound peroxidase from impurities and subsequent equilibration in the starting solution,

- use proven and dried urea as fertilizer, which addresses the issue of environmentally friendly utilization of the sorbent and can improve the ecology of the environment.

All the above allows to conclude that the practical applicability of the method.

1. The method of obtaining dihydroquercetin and dihydrocemferol from an extract of larch wood, containing bioflavonoids, characterized in that the organic solvent is dissolved lyophilized extract, then the resulting solution was applied on a column Packed with a sorbent - urea, pre-equilibrated with ethyl acetate; column elute the complex ester and/or ketone having a boiling point below 120°With; the resulting eluate is collected is, evaporated prior to the solidification and cooling, the precipitated crystals are washed and dried.

2. The method according to claim 1, characterized in that the organic solvent used ethyl acetate and acetone in the ratio of 1:1.

3. The method according to claim 1, characterized in that as the eluent using ethyl acetate and acetone in the ratio of 1:2.

4. The method according to claim 1, characterized in that the ratio of sorbent to the sample 100:1.



 

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