PL210084B1 - The manner of production of 4'-O- -D-glucosylo-2'-4-dihydroxy-6'-metoxy-3'-prenylochalcone - Google Patents

Description

The present invention relates to a process for the preparation of 4'-e-O-D-glucosyl-2 ', 4-dihydroxy-6'-methoxy-3'-prenylchalcone of the formula 2 shown in the drawing.

This compound is biologically active and can be used in the food and pharmaceutical industries.

There is a known microbiological method of obtaining 4'-0-eD-glucosyl-2 ', 4-dihydroxy-6'-methoxy-3'-prenylchalcone by transformation of xanthohumol by Penicillium chrysogenum fungi (Kim HJ, Lee IS, 2006. Microbial) metabolism of the prenylated chalcone xanthohumol. J. Nat. Prod., 69, pp. 1522-1524). This method achieved an efficiency of 5.5%.

The invention relates to a microbial process for the preparation of 4'-O-e-D-glucosyl-2 ', 4-dihydroxy-6'-methoxy-3'-prenylchalcone of formula 2 from the substrate xanthohumol.

The essence of the invention consists in that the substrate is biotransformed with a culture of fungi of the species Absidia coerulea or Absidia glauca.

It is advantageous if the reaction is carried out with aqueous fungal cultures, with constant stirring of the reactants, at a temperature of 285-313 K.

Following the inventions, glucosidation reactions take place as a result of the enzyme systems contained in living cells of Absidia coerulea or Absidia glauca cultures. The identical products obtained in this way are separated from the aqueous cultures of the said microorganisms by known methods by extraction with ethyl acetate.

The main advantage of the inventions is to obtain, under mild conditions, 4'-O-eD-glucosyl-2 ', 4-dihydroxy-6'-methoxy-3'-prenylchalcone as the main reaction product, with a yield of 18.3 to 24, 2%.

The invention is explained in more detail in the working examples.

EXAMPLE 1 To a flask of 300 cm ^3, which is 100 cm ^{3 of} sterile medium containing 3 g of glucose and 1 g aminobaku be introduced fungus Absidia coerulea. After 2 days of microbial growth, 30 mg of xanthohumol, formula I, dissolved in 1.5 cm ^{3 of} acetone, are added at the temperature of 303 K and with continuous shaking. The transformation is carried out under continuous shaking for approximately 9 days. Thereafter, the resulting transformation solution was extracted three times with ethyl acetate, dried with magnesium sulfate and the solvent was evaporated. 80 mg of crude product are obtained, which product is purified by chromatography using a 6: 1 mixture of chloroform-methanol as eluent. In this way, 10.6 mg of 4'-O-eD-glucosyl-2 ', 4-dihydroxy-6'-methoxy-3'-prenylchalcone are obtained (yield 24.2%).

Example 2 The procedure is analogous to that of Example 1, except that substrate biotransormation is carried out using Absidia glauca mushrooms for about 7 days. 48 mg of crude product are obtained, of which 8 mg of 4'-O-eD-glucosyl-2 ', 4-dihydroxy-6'-methoxy-3'-prenylchalcone are obtained after chromatographic purification (18.3% yield) .

The resulting product is characterized by the following spectral data: ¹ H NMR: δ = 14.21 (1H, s, 2'-OH); 10.13 (1H, s, 4-OH); 7.77 (1H, J = 15.5Hz, Ha C = O); 7.72 (1H, d, J = 15.5Hz, Hp C = O); 7.61 (2H, J = 8.5Hz, H -2, H-6); 6.86 (2H, d, J = 8.5Hz, H-3, H-5); 6.42 (1H, 5, H-5 '); 5.35 (1H, d, J = 4.6 Hz, 2'-OH); 5.19 (1H, m, H -2); 5.15 (1H, 3'-OH); 5.11 (1H, d, J = 4.9 Hz, 4'-OH); 5.01 (1H, t, J = 3.7Hz, H -1 '); 4.75 (1H, d, J = 5.4Hz, 6'-OH); 3.94 (3H, s, C-6'-O-Me); 3.76 (1H, H-6 '); 3.45 (1H, H-5 '); 3.43 (1H, m, H-6 '); 3.37 (1H, m, H -1); 3.36 (1H, m, H-3 '); 3.33 (1H, m, H -2 '); 3.13 (1H, m, H -1); 3.13 (1H, m, H-4 '); 1.74 (3H, s, H-4); 1.61 (3H, H-5).

¹³ C NMR:? = 193.0 (C = O); 163.6 (C-2 '); 161.6 (C-4 '); 160.9 (C-6 '); 160.7 (C-4); 143.8 (C-β);

130.6 (C-3); 131.2 (C-2. C-6); 126.3 (C-1); 124.0 (C-α); 123.3 (C-2); 116.5 (C-3, C-5); 110.0 (C-3 ');

106.7 (C-1 '); 100.6 (C-1 '); 91.1 (C-5 '); 78.0 (C-5 '); 77.4 (C-3 '); 73.8 (C-2 '); 70.6 (C-4 '); 61.4 (C-6 '); 56.5 (C-6'-O-Me); 26.0 (C-5); 21.7 (C-1); 18.2 (C-4).

Claims (4)

Method for the preparation of 4'-0-eD-glucosyl-2 ', 4-dihydroxy-6'-methoxy-3'-prenylchalcone of formula 2 by microbiological route from a substrate which is xanthohumol of formula 1, characterized by that the glucosidation process is carried out by the culture of the fungi of the genus Absidia coerulea. PL 210 084 B1 Process for the preparation of 4'-0-eD-glucosyl-2 ', 4-dihydroxy-6'-methoxy-3'-prenylchalcone of formula 2 by microbiological route from a substrate which is xanthohumol of formula 1 characterized by that the substrate glucosidation is carried out by the culture of Absidia glauca fungi. 3. The method according to p. The method of claim 1 or 2, characterized in that the glucosidation process is carried out in an aqueous culture of the strain under continuous shaking. 4. The method according to p. 1 or 2, characterized in that the glucosidation process is carried out at a temperature of 285-313 K.