Uniformly tritiated triterpene glycosides of holothurians cucumaria

FIELD: chemistry.

SUBSTANCE: invention refers to production of new tritiated analogues of physiologically active compounds - triterpene glycosides of holothurians Cucumaria of formula: .

EFFECT: there are produced new tritiated analogues of physiologically active compounds.

2 cl, 2 ex

 

The invention relates to the field of organic chemistry and can find application in analytical chemistry, Bioorganic chemistry, biochemistry and applied medicine.

In the study of physiologically active compounds may be necessary for their labeled counterparts.

Known triterpene glycosides holothurians Cucumaria formula:

Data triterpene glycosides have a strong immunomodulatory effect (Sedov A.M.; Apollonin, A.V.; Sevastyanova E.K. Stimulation of mice non-specific antibacterial resistance to conditionally pathogenic gram-negative microorganisms. Antibiot. Khimioter. 1990, 35 (1), 23-26) [I].

However, these tritium-labeled triterpene glycosides are not described.

The technical result achieved by the present invention, is expanding the range labeled analogs of the physiologically active compounds.

Achieved the specified technical result obtaining wisokomernix tritium triterpene glycosides of the formula:

It is known that substitution of atoms of compounds for their labeled counterparts does not change any properties of the original compound (E.A. Evans - Tritium and its compounds London Butterworths, 1974, p.48).

Below are examples of implementation of the invention.

Example 1

In a vial was placed 70 mg of 5% Pd/C was added thereto a solution of 10 mg of unsaturated triterpene glycoside in 0.1 ml dimethyl sulfoxide. Soda is one of the vials were frozen with liquid nitrogen, was evacuated to a pressure of 0.1 PA, filled with gaseous tritium to a pressure of 400 hPa and kept at 25°C for 6 hours and Then the contents of the ampoule were again frozen with liquid nitrogen and was evacuated to a pressure of 0.1 PA to remove gaseous tritium. In a vial was added 4 ml of water and the contents of the vial were stirred on a magnetic stirrer for 10 minutes the Aqueous solution was filtered, the material of the catalyst was extracted with methanol (5×2 ml). The filtrates were combined and evaporated on a rotary evaporator. After separation of unsaturated triterpene glycoside by HPLC (Kromasil column S, 7 μm, 10×8 mm system: a mixture of methanol with 5 mm H3PO43:1, flow rate of eluent 2 ml/min, retention time - 3.70 min) output labeled drug - 26%, molar radioactivity - 22 CI/mmol, radiochemical purity of 96-98%.

Example 2

In a vial was placed 1 mg labeled with tritium in unsaturated triterpene glycoside (22 CI/mmol), 40 mg of 5% Pd/C and 2 ml of water. The contents of the vials were frozen with liquid nitrogen, was evacuated to a pressure of 0.1 PA, filled with gaseous tritium to a pressure of 400 hPa, was heated to 25°C and stirred on a magnetic stirrer for 15 hours and Then the contents of the ampoule were again frozen with liquid nitrogen and was evacuated to a pressure of 0.1 PA to remove gaseous tritium. The aqueous solution was filtered, the material of the catalyst of the extras who were garofali with methanol (5×2 ml). The filtrates were combined and evaporated on a rotary evaporator. Rich triterpene glycoside was isolated by HPLC as described in example 1 (retention time - 5.23 min).

The output labeled saturated triterpene glycoside reached 12%, the molar radioactivity - 71 CI/mmol. After the first purification allocated 6.5 MCI of labeled product with a radiochemical purity of 93-95%, after the second purification obtained 4.5 MCI busy triterpene glycoside with a radiochemical purity of 96-98%.

The thus obtained new visokomerniye tritium physiologically active compounds.

Visokomerniye tritium triterpene glycosides holothurians Cucumaria formula



 

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