A method of obtaining a triterpene glycoside 3 - 0 -- d - glyukopiranozil- (1 _2) -- z - arabinopyranoside hederagenin

 

(57) Abstract:

The use of bio-organic chemistry and relates to a method of obtaining biologically active glycoside-cauloside With, which can be used as a biochemical tool for the controlled change of the permeability of biological membranes and as a growth regulator of cell cultures. The inventive product: 3-0- -D-glyukopiranozil-((1 _ 2))- -L-arabinopyranoside hederagenin, which is derived from crushed roots rhizomes of tablelist powerful Caulophyllum robustum Maxim degreasing chloroform, extraction of the aqueous solution of alkali when heated, and then the extract is separated, acidified with sulfuric acid, extracted with n-butanol, the extract washed with water, evaporated, the residue from evaporation, containing a total triterpene glycosides, purified using alumina, and the amount of purified triterpene glycosides crystallized from ethanol.

The invention relates to the field of Bioorganic chemistry and relates to a method of obtaining biologically active glycoside 3-0- -D-glyukopiranozil-((1 _ 2))--L-arabinopyranoside hederagenin (cauloside S, I), which can be used as a biochemical tool for the regulated permeability changes biomoby obtain 3-0--D-glyukopiranozil-((1 _ 2))--L-arabinopyranoside hederagenin from the roots and rhizomes of plants of tablelist powerful Caulophyllum robustum Maxim. based on the extraction of triterpene glycosides from plant material boiling methanol and include distillation of the methanol, the distribution of extractives in the system of immiscible liquids, separation and evaporation of the organic layer, multiple chromatographic separation of components and crystallization from methanol [3-5] is the closest to the proposed method of obtaining 3-0-b-D-glyukopiranozil-((1 _ 2))--L-arabinopyranoside hederagenin technical solution enables the extraction of ground roots of tablelist powerful boiling methanol, the separation of the methanol extract, purification of the methanol extract of activated carbon, distillation of methanol, dissolving the obtained residue in n-butanol, chromatography on silica gel with subsequent evaporation of the obtained fractions and crystallization from methanol fractions and crystallization from methanol fraction containing 3-0-b-D-glyukopiranozil-((1 _ 2))--L-arabinopyranoside hederagenin with the release of 0.08% for raw materials [3]

The disadvantages of the prototype and other ways of getting 3-0-b-D-glyukopiranozil-((1 _ 2))--L-arabinopyranoside hederagenin are the complexity and intensity of the process of chromatographic separation, the application for the extraction of significant amounts of vysokotochnoye, reduction of toxicity and fire hazard process, and increase output 3-0-b-D-glyukopiranozil-((1 _ 2))--L-arabinopyranoside hederagenin.

This is achieved by the fact that the crushed root and rhizome of tablelist powerful Caulophyllum robustum Maxim. degrease chloroform, extracted with aqueous solution of alkali when heated, the extract is separated, acidified with sulfuric acid, extracted with n-butanol, the extract washed with water, evaporated, the residue from evaporation, containing a total triterpene glycosides, purified using alumina, and the amount of purified triterpene glycosides crystallized from ethanol, receiving 3-0-b-D-glyukopiranozil-((1 _ 2))--L-arabinopyranoside hederagenin (cauloside S, I) with the release of 1.7%

Application for extraction of plant materials triterpene glycosides aqueous alkali solution allows you to avoid highly toxic and flammable methanol, and at the same time to increase the output of cauloside With due to concomitant triterpene glycoside caulosideG(2) [5] While heating cauloside Glye is the cleavage of carbohydrate chain from carboxyl groups and is formed more cauloside With, which leads to an increase of the yield of the target product.

Example. 120 g of the powder milled air-dried roots rhizome of tablelist powerful Caulophellum robustum Maxim. will permalert 4 liters of chloroform. Chloroform extract (weight of residue 1.3 g, 1,1) cast. Dried in air, the powder is placed in a glass heat-resistant flask containing 1 l of 1 n KOH. The flask is heated at the boiling temperature of the reaction mixture for 3 hours, the Cooled mixture is centrifuged, the precipitate washed with water (0.4 l x 3) and discard. To the combined supernatant added under stirring to 100 ml of 20% H2SO4, remove n-butanol (0.5 l x 3), butanolide hoods combine, washed with water (0.25 l x 3) and evaporated to dryness (dry weight balance to 11.28 g, 9.4 per raw). The obtained dry residue purified on an aluminum oxide (14 x 4.4 cm) in the system chloroform-methanol/H2O 9:1 (1 l), 4:1 (4.5 l), 2:1 (0.6 l), 1:1 (0.9 liters). The eluate analyzed using 2SO4in ethanol. Obtain 1.3 g (1,1) hederagenin and 5.4 g (4,5) the amount of triterpene glycosides. The amount of glycosides crystallized from ethanol and receive 2,03 g (1.7 percent) 3-0-b-D-glyukopiranozil-1(1 _ 2))--L-arabinopyranoside hederagenin (cauloside S, I) with so pl. 248-251oC []2D2+ 58,12o(0,125, chloroform-methanol 1:1).

1. A method of obtaining a triterpene glycoside 3 - 0 - - D-glyukopiranozil- (1 _ 2) - - Z-arabinopyranoside hederagenin, including extraction of roots from a rhizome of tablelist powerful Caulophyllum robustum Maxim, purification, and crystallization of the desired product, characterized in that the powder raw material is extracted with an aqueous solution of alkali, the extract is separated, acidified, extracted by n-butanol, butanolide extract washed with water, evaporated, and purified on an aluminum oxide and crystallized from ethanol.

 

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