SINTESIS BEBERAPA SENYAWA ANALOG KURKUMIN SEBAGAI SENYAWA ANTIMALARIA TERHADAP PLASMODIUM FALCIPARUM DAN PENAMBATAN MOLEKULER TERHADAP PROTEIN PfATP6

PUTRA M BOANGMANALU, Dr. Endang Astuti, M.Si.; Dr. Tri Joko Raharjo, M.Si.

2020 | Skripsi | S1 KIMIA

Sintesis senyawa analog kurkumin 2,6-bis(3-hidroksibenzaliden)sikloheksanon (A); 2,6-bis(3-hidroksibenzaliden)siklopentanon (B); dan 2,6-bis(3-hidroksifenil)penta-1,4-diena-3-on (C) telah berhasil dilakukan. Sintesis senyawa analog kurkumin tersebut dilakukan menggunakan metode reaksi Claisen-Schmidt, mereaksikan 3-hidroksibenzaldehida dengan sikloheksanon, siklopentanon, dan aseton menggunakan pelarut THF dan katalis HCl 37%. Elusidasi struktur senyawa produk dianalisis dengan KLT, TLC scanner, spektrofotometer FTIR, 1H-NMR, 13C-NMR, dan LC-MS/MS. Uji aktivitas antiplasmodium diuji secara in vitro terhadap Plasmodium falciparum 3D7, dilanjutkan dengan kajian interaksi penambatan molekuler terhadap protein PfATP6. Hasil sintesis senyawa 2,6-bis(3-hidroksibenziliden)sikloheksanon; 2,6-bis(3-hidroksibenziliden)siklopentanon; dan 1,5-bis(3-hidroksifenil)penta-1,4-diena-3-on diperoleh persentase hasil produk berturut-turut sebesar 78,87%; 53,44%; dan 64,16%. Hasil uji antiplasmodium senyawa analog kurkumin A, B, dan C tersebut diperoleh nilai IC50 menggunakan analisis probit SPSS dengan taraf signifikansi 95% berturut-turut sebesar 16,93; 31,88; dan 39,04 ������¯���¯���¿���½������­M. Berdasarkan penambatan molekuler, diperoleh nilai afinitas ikatan berturut-turut sebesar -8,5; -8,4; dan -8,1 kkal/mol.

Synthesis of curcumin analogues 2,6-bis(3-hydroxybenzylidene)cyclohexanone (A); 2,6-bis(3-hydroxybenzylidene)cyclopentanone (B), and 1.5-bis(3-hydroxyphenyl)penta-1,4-diene-3-on (C) have been successfully accomplished. Synthesis of the curcumin analogues was carried out by condensation Claisen-Schmidt between 3-hidroxybenzaldehyde with cyclohexanone, cyclopentanone, and acetone, respectively. These curcumin analogues compound were characterized by TLC, TLC scanner, FTIR Spectrophotometer 1H-NMR, 13C-NMR, and LC-MS/MS. Antimalarial activity of the analog compounds was tested by antiplasmodium assay of Plasmodium falciparum 3D7 and the results were evaluated the interaction and affinity bonding by molecular docking. The spectroscopy characterization show that the reaction have been succesfully produce 2,6-bis(3-hydroxybenzylidene)cyclohexanone; 2,6-bis(3-hydroxybenzylidene)cyclopentanone, and 1.5-bis(3-hydroxyphenyl)penta-1,4-diene-3-on with yield of 78.87, 53.44, dan 64,16%, respectively. The IC50 value, represent against P. falciparum of the curcumin analogues were at IC50 16.93, 31.88, and 39.04 ������¯���¯���¿���½������­M, respectively. Then, based on compound A, B, and C were calculated by molecular docking, it was obtained that the value of affinity bonding -8.5, -8.4, dan -8.1 kkal/mol, respectively.

Kata Kunci : 3-hidroksibenzaldehida, antiplasmodium, penambatan molekuler, sintesis