Method of obtaining 7-hydroxyroyleanon, possessing antimicrobial activity

FIELD: chemistry.

SUBSTANCE: invention relates to method of obtaining 7-hydroxyroyleanon, possessing antimicrobial action. said method includes extraction of crushed roots of salvia officinalis with 96% ethyl alcohol with further extract evaporation, processing with water, alcohol distillation and processing with hydrophobic solvent or extraction of said raw material with chloroform with further extract processing with water and evaporation; after which target product is extracted from organic phase by transfer into water-soluble phenolates, with processing with sodium hydroxide water solution; alkali solution is washed with chloroform; acidified with hydrochloric or sulphuric acid; obtained sediment is filtered; dried and crushed.

EFFECT: invention is characterised by improved process manufacturability and provides obtaining individual substance with higher antimicrobial activity than previously extracted royleanon derivatives from salvia officinalis.

2 tbl, 6 ex

 

The invention relates to medicine, namely to chemical-pharmaceutical industry and relates to a method of obtaining antimicrobial agents: 7-hydroxytoluene.

The literature describes methods for isolating releasenew different from 7-hydroxytoluene and his acetoxypropionyl the structure and location of the substituents, from different raw materials:

extraction with diethyl ether (Coleus fredericii, leaves) with subsequent column chromatography [1];

extraction with diethyl ether (Coleus coerulescens, grass) followed by fractionation in a solvent system diethyl ether-acetone 1:1 and petroleum ether (30-60°) - methanol 1:9 and separated by column chromatography on silica gel [2];

extraction with diethyl ether (Plectranthus barbathus, leaves, Plectranthus sanguinens, leaves), by evaporation of the solvent and chromatographytandem on Sephadex LH-20 [3];

- extraction successively with hexane and diethyl ether (Plectranthus edulis, leaves), by evaporation of the solvent and chromatographytandem on Sephadex LH-20 [4];

- 7-acetoxysilane get from the roots of Inula roylana by extraction with methanol, concentration of the extract, from which stands out the residue the target product [5].

In all these examples aim to highlight, identify, or determine the structure of substances, where the completeness of extraction is not the main task, therefore extractants and processes �e are optimal for industrial technology.

A method of producing the amount of releasenew [6] with antimicrobial activity from the roots of Salvia officinalis, including the extraction of raw materials chloroform, filter, evaporate the chloroform extract, followed by chromatographic separation in a thin layer of sorbent and elution adsorption zone of releasenew.

This method is good at solving analytical task of determining the amount of Raileanu, but unacceptable in technology, especially large-scale, due to the presence of thin layer chromatography, eluent a large number and complexity of the process.

The aim of the invention is to provide a method of obtaining as individual drug compounds with the predominant antimicrobial activity, 7-hydroxytoluene, development of a method of purification of the target product from the impurities of the lipid nature of the reduction of the time and good reproducibility. Antimicrobial activity of 7-acetoxysilane against Golden staph is 62.5 μg/ml, 7-hydroxytoluene - 15.6 ág/ml (Table. 2).

This object is achieved in that the extractant used 96% ethanol. After distilling off the solvent to ~2% of the original volume of the distillation residue is diluted with water, completely distilled off the alcohol and treated with chloroform, followed by extraction with a�new product from chloroform with an aqueous solution of alkali, washed with an alkaline solution with chloroform, precipitated with hydrochloric or sulfuric acid, the precipitate is separated, washed with water, dried. Extraction of the target product with an alkali in the form of a phenolate, soluble in water, solved two problems at once - the less active hydrolysis of 7-acetoxysilane and separation from 7-hydroxytoluene of lipids remaining in the chloroform phase. Washing the alkaline solution of the desired product with chloroform removes lipids entering the aqueous alkaline phase with insufficient separation of organic and aqueous alkaline phase. The extraction of raw materials can be carried out directly chlorinated hydrocarbon (chloroform) followed by carrying out the process in this way. Use head on stage as the extractant ethanol, followed by evaporation and dissolution of extractives in chloroform for reasons of environmental safety.

The proposed method the criterion of "novelty" is that:

- Department of releasenew from a mixture of lipids is carried out by treating a chloroform extract of the aqueous alkali, in which oleanane transferred in the form of a phenolate,

- 7-acetoxysilane hydrolyzed to 7-hydroxytoluene, and lipids remain in chloroform,

- the final product is precipitated from alkali acid that is breitenlohner, than fill the column on the sorbent. Comparative data on the physicochemical characteristics and biological activity of 7-hydroxytoluene - drug and 7-hydroxytoluene - standard sample show that the proposed method allows to obtain the target product with the necessary qualitative and quantitative composition and biological properties.

The method consists in the extraction of the crushed roots of Salvia officinalis 96% ethyl alcohol, the evaporation of the alcohol, adding water. Next, the aqueous phase is treated with chloroform, the chloroform solution washed with water, treated with a solution of sodium hydroxide. From alkaline extraction is removed by vacuum traces of chloroform, filtered, and acidified with hydrochloric or sulfuric acid. The precipitate of the desired product was filtered off, washed with water and dried (PL. 1).

The technical result of the proposal is to expand the use of plant material the roots of Salvia officinalis, to date representing waste when growing sage to obtain essential oils from the aerial parts, in the transformation of the sum of releasenew: 7-acetoxysilane and 7-hydroxytoluene in individual substance - 7-hydroxytoluene with the highest antimicrobial activity, improving the manufacturability of the process by replacing long p�of acessa chromatography on a sorbent precipitation with acid from the alkaline solution.

Example 1.

200.0 g of crushed root sage is placed in a glass flask, pour 1 liter of ethyl alcohol (1:5) and the extraction is carried out at room temperature for 16 h with stirring. The first extract is drained, pour the raw material alcohol in the merged volume of the extract and extracted as in the first case. A third extraction was carried out analogously for 16 h. the combined alcoholic extracts (about 2.3 liters) was evaporated to approximately 2% of the original volume (in the case of a continuous process third extraction served on fresh raw new download), diluted with water 3-4 times and completely distilled off the alcohol. The bottoms (150-200 ml) was treated three times with chloroform, 200, 100, 100 ml. Chloroform, the solution is extracted with 4 times 1% aqueous solution of sodium hydroxide. The ratio of water-alkaline and organic phases 0,4:1, 0,3:1, 0,3:1, 0,2:1. The combined alkaline extract was washed with chloroform (~50 ml), treated with a vacuum, filtered through cotton wool and acidified with 5% hydrochloric acid solution to pH 3. The precipitate was separated by filtration, washed with water until neutral reaction of the wash water, dried, triturated.

The yield of 0.58 g (0.3% by weight of raw materials).

The content of 7-hydroxytoluene of 53.7%.

Example 2.

200 g of crushed roots of Salvia placed in a glass flask, pour 1 liter of 95% ethyl alcohol (1:5) and the extraction is carried out at room temperature within t�e 4 h with stirring. The first extract is drained, pour the raw material alcohol in the merged volume of the extract and extracted for 3 h under the same conditions as the first extraction. A third extraction was carried out analogously to the second (3 hours, room temperature, mixing). The combined alcoholic extracts (~2.3 liters) was evaporated to ~2% of the original volume (in the case of a continuous process the third extract is served on fresh feedstock), followed by carrying out the process indicated in example 1.

Get 0,66 g (0,33% by weight of raw materials).

The content of 7-hydroxytoluene to 55.9%.

Example 3.

200 g of crushed roots of Salvia placed in a glass flask, pour 800 ml of chloroform (1:4) and the extraction is carried out three times at room temperature with stirring for 16 h. the combined chloroform extract was washed with water (~80 ml), evaporated to 340 ml and four times extracted with 2% aqueous solution of sodium hydroxide in 150 ml. combined alkaline extract was washed with chloroform (~50 ml), treated with a vacuum to remove traces of chloroform and acidified with 5% hydrochloric acid to pH 2-3. Fallen Golden yellow precipitate was filtered, washed with water until neutral, dried and milled.

Get 0,53 g (0.3% by weight of raw materials).

The content of 7-hydroxytoluene representing 54.7%.

Example 4.

1 kg ismalic�fucking raw materials are placed in the extractor in stainless steel vertical cylindrical with conical bottom, with the bottom release (d=200 mm h=360 mm), pour 5 liters of 95% ethyl alcohol (1:5) and the extraction is carried out at room temperature for 16 h with stirring. The first extract is drained, pour raw materials in the merged volume of the extract and extracted as in the first case. A third extraction is carried out in a similar mode. The combined alcoholic extract was evaporated to 200 ml, add 150 ml of water, evaporated to remove alcohol, bring the volume of the aqueous phase to 650 ml, extracted with chloroform 350, 250, 250 ml), the combined chloroform extract was washed with water (~150 ml) and extracted 4 times with 1% sodium hydroxide solution 300, 220, 220, 150 ml the combined alkaline extract was treated with vacuum to remove traces of chloroform, filtered through cotton, diluted with water twice, acidified with 5% sulfuric acid to pH 2. The yellow precipitate was filtered, washed with water until neutral, dried, ground.

Get 3,49 g (0,35% by weight of raw materials).

The content of 7-hydroxytoluene is 48.5%.

Example 5.

50.0 g of crushed roots of Salvia placed in a glass flask, pour 250 ml of ethyl alcohol (1:5) and the extraction is carried out at room temperature and with stirring for 4 hours. Receive 200 ml of the extract. A second extraction was carried out for 3 hours, volun� 200 ml of the extractant The volume of extract 195 ml Third extraction is carried out as a second for 2 hours. The volume of extractant 195 ml of the extract (200 ml). the combined extracts evaporated to ~30 ml, diluted with 120 ml of water and evaporated to remove the alcohol. Then the aqueous phase was successively extracted with methylene chloride 7×40 ml to backlash last retrieved on royleana (purple staining spots on filter paper or in a thin layer of silica gel from exposure to ammonia vapors). United chlorotoluene extract (240 ml) was treated with alkali 40 ml, 3×30 ml). the combined alkaline extract was treated with vacuum and acidified with 5% hydrochloric acid. Precipitated yellow precipitate was filtered, washed to neutral reaction and dried. Get 0,043 g (0,086% by weight of raw materials). The content of 7-hydroxytoluene 31,76%.

Example 6.

50.0 g of crushed roots of Salvia three times extracted as in example 5, 4, 3 and 2 hours. The ratio of the volume of the extractant and the weight of the raw material 5:1. The volume of the extractant on the 1st extraction of 250 ml for each additional equal to the merged volume of the extract, i.e., 200 and 195 ml) Then the combined extract is evaporated to remove the alcohol dichloroethane is treated with 6×40 ml. of the United dichlorethane extract in the amount of 232 ml was filtered through cotton wool and treated with 1% aqueous NaOH 50 ml,42 ml, 2×30 ml). The combined alkaline extract (151 ml) was filtered, treated with vacuum and acidified with 5% hydrochloric acid. The precipitate was filtered off and washed until neutral, dried, crushed.

Get of 0.036 g (0,072% by weight of raw materials). The content of 7-hydroxytoluene 38,63%.

The technology comparison with the prototype presented in the table. 1.

Using the proposed method in comparison with the known provides the following benefits:

- use head on the stage of production is practically non-toxic extractant - ethanol;

- lack of heating processes toxic and flammable solvents;

- conversion of the less active 7-acetoxysilane more active in 7-hydroxytoluene (62,5 µg/ml and 15.5 µg/ml, respectively);

- carrying out hydrolysis of 7-acetoxysilane and the separation of lipophilic contaminants in one operation: royleana in the form of phenolate passes into the aqueous phase and the lipophilic impurities remain in chloroform;

- target product deposition from an aqueous solution of sodium hydroxide acid more technologically advanced and well reproducible operation compared to chromatographytandem on the sorbent.

Antimicrobial activity of individual substances and the amount of 7-guide�of axiallary and related substances of lipid nature was studied in experiments in vitro, using the method of twofold serial dilutions of substances in liquid nutrient media: mesopatamia broth - for the study of bacteriostatic activity and environment Saburo for study fungistatic activity (7).

In determining the antimicrobial spectrum of the studied samples used 6 pathogenic test microorganisms: gram-positive bacteria Staphylococcus aureus, gram-negative bacteria Escherichia coli, Proteus vulgaris and Pseudomonas bacteria as well as filamentous fungi of the genus MICROSPORUM and yeast-like fungi of the genus CANDIDA.

As a result of study set (table. 2) that the individual 7-hydroxytoluene has a high bacteriostatic activity against Staphylococcus aureus at a concentration of 15.6 μg/ml, which is about 4 times higher than the activity of individual 7-acetoxysilane. From previous research it is evident that the variation of the % content of releasenew (36÷57%) in the samples does not affect the value bacteriostatic activity against Staphylococcus aureus corresponds to 31.2 µg/ml (table. 2), while in all samples observed partial delay the growth of bacteria to a concentration of 15.6-7,8 µg/ml.

Sources of information

1. Zhen-Yan Zhu, N. Nayeshiro, R. Prewo, P. Rüedi, C. H. Eugster. Helvetica Chim Acta, v. 71, p. 577 (1988).

2. K. Grob, P. Rüedi, C. H. Eugster. Helvetica Chim Acta, v. 61, Fasc. 2, p. 871 (1978).

3. P. Rüedi. Helvetica Chim Acta, v. 69, p. 972 (1986).

4. J. M. Künde, P. Rüedi, C. H. Eugster. Helvetica Chim Acta, v. 70, p. 1911 (1987).

5. O. E. Edwards, G. Feniak, M. Los. Canadian J. of Chemistry, v. 40, p. 1540 (1962).

6. B. A. Kriwet, L. P. Tolstykh, N. And. Fedyunina. Method of quantitative determination of derivatives of oleanane (oxy - and acetoxyvalerenic) in the roots of Salvia officinalis. Chem.-Pharm. W., 1980, No. 12, pp. 66-68.

7. The report of the group of chemotherapy Department of medicine VILAR 2012

A method of producing 7-hydroxytoluene having antimicrobial activity, comprising the extraction of crushed roots of Salvia officinalis with 96% ethanol, followed by evaporation of the extract, water treatment, distillation of alcohol and a hydrophobic treatment with a solvent or extraction of the specified raw materials chloroform with subsequent treatment of the extract with water and evaporation; then the target product is extracted from the organic phase transfer in water-soluble phenolate, treating with an aqueous sodium hydroxide solution; washed with an alkaline solution of chloroform; acidified with hydrochloric or sulfuric acid; the resulting precipitate was filtered; dried and pulverized.



 

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