SINTESIS 3,6-DIHIDROKSISANTON DAN 3,4,6-TRIHIDROKSISANTON SERTA UJI AKTIVITASNYA PADA PENGHAMBATAN POLIMERISASI HEM

RIZALINA TAMA SARAGI, Prof. Drs. Jumina, Ph.D.

2014 | Skripsi | KIMIA

Synthesis of 3,6-dihydroxyxanthone and 3,4,6-trihydroxyxanthone and evaluation of theirs antimalarial activities have been carried out. The objective of this study was to synthesis 3,6-dihydroxyxanthone and 3,4,6-trihydroxyxanthone and to know theirs antimalarial activity by heme polymerization inhibitory test and in vitro test. The first step was carboxylation of resorcinol by carbon dioxide gas to provide 2,4-dihydroxybenzoic acid. It was conducted by refluxing in water for 2 hours. The next step was synthesis 3,6-dihydroxyxanthone by reacting 2,4-dihydroxybenzoic acid and resorcinol. The procedure was conducted by heating the mixture with Eaton’s reagent at 60-80 °C for 3 hours. Synthesis of 3,4,6-trihydroxyxanthone was done in same procedure by replacing resorcinol with pyrogallol. The chemical structures were confirmed by FTIR, 1H-NMR, and MS spectrometers. Antimalarial test of hydroxyxanthone derivatives was conducted by heme polymerization inhibitory test and in vitro test against Plasmodium falciparum strain 3D7. Based on research 2,4-dihydroxybenzoic acid was obtained as white solid in 41% yield, 3,6-dihydroxyxanthone and 3,4,6-trihydroxyxanthone were obtained as red solid in 43% and 43% yield. Heme polymerization inhibitory test showed that IC50 number for 3,6-dihydroxyxanthone and 3,4,6-trihydroxyxanthone were 47,23 mM and 4,14 mM respectively, and for chloroquine was 7,86 mM. In vitro test showed for 3,6-dihydroxyxanthone and 3,4,6-trihydroxyxanthone give IC50 number 0,720 μM and 0,111 μM respectively. As a result, 3,4,6-trihydroxyxanthone was indicated to give better activity than 3,6-dihydroxyxanthone as antimalaria.

Synthesis of 3,6-dihydroxyxanthone and 3,4,6-trihydroxyxanthone and evaluation of theirs antimalarial activities have been carried out. The objective of this study was to synthesis 3,6-dihydroxyxanthone and 3,4,6-trihydroxyxanthone and to know theirs antimalarial activity by heme polymerization inhibitory test and in vitro test. The first step was carboxylation of resorcinol by carbon dioxide gas to provide 2,4-dihydroxybenzoic acid. It was conducted by refluxing in water for 2 hours. The next step was synthesis 3,6-dihydroxyxanthone by reacting 2,4-dihydroxybenzoic acid and resorcinol. The procedure was conducted by heating the mixture with Eaton’s reagent at 60-80 °C for 3 hours. Synthesis of 3,4,6-trihydroxyxanthone was done in same procedure by replacing resorcinol with pyrogallol. The chemical structures were confirmed by FTIR, 1H-NMR, and MS spectrometers. Antimalarial test of hydroxyxanthone derivatives was conducted by heme polymerization inhibitory test and in vitro test against Plasmodium falciparum strain 3D7. Based on research 2,4-dihydroxybenzoic acid was obtained as white solid in 41% yield, 3,6-dihydroxyxanthone and 3,4,6-trihydroxyxanthone were obtained as red solid in 43% and 43% yield. Heme polymerization inhibitory test showed that IC50 number for 3,6-dihydroxyxanthone and 3,4,6-trihydroxyxanthone were 47,23 mM and 4,14 mM respectively, and for chloroquine was 7,86 mM. In vitro test showed for 3,6-dihydroxyxanthone and 3,4,6-trihydroxyxanthone give IC50 number 0,720 μM and 0,111 μM respectively. As a result, 3,4,6-trihydroxyxanthone was indicated to give better activity than 3,6-dihydroxyxanthone as antimalaria.

Kata Kunci : 3,6-dihidroksisanton, 3,4,6-trihidroksisanton, polimerisasi hem, in vitro, P. falciparum, antimalaria.