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Pekik Wiji Prasetyaningrum1,* ), Anton Bahtiar1), Catur Jatmika1) and Hayun Hayun1,* )
1
Faculty of Pharmacy, Universitas Indonesia, , Depok, 16424, West Java, Indonesia.
*)
Corresponding authors: pekikwiji@gmail.com; hayun.ms@ui.ac.id
ABSTRACT
Novel asymmetrical monocarbonyl analogues of curcumin (asymmetrical MACs) were
synthesized based on Clasein-Schmidt condensation reaction of aldehyde aromatics with
cyclohexanone. The synthesized compounds were purified by column chromatography and the
structure were confirmed on the basis of FTIR, 1H-NMR, 13C-NMR and HR-MS. The yields
obtained from this study were: 50.03%, 2.7%, 47.31%, 6.1%,13.16% and 55.53%, respectively
for 2-benzyliden-6-(4-hydroxy-3-methoxybenzylidene)cyclohexaanone, 2-(4-hydroxy-3-
methoxybenzylidene)6-(4-methoxybenzylidene)cyclohexanone, 2-(4-fluorobenzyliden)6-(4-
hydroxy-3-methoxybenzylidine)cyclohexanone, 2-(4-cholobenzylidene)-6-(4-hydroxy-
3methoxybenzylidene)cyclohexanone, 2-(4-hydroxy-3-methoxybenzylidene)-6-(4-
methylbenzylidene)cyclohexanone, and 2-benzylidene-6-(4-
hydoxybenzylidene/cyclohexanone. Cytotoxicity effect of all the compound have been
analyzed used BSLT bioassay, the result is all compund have potency as anti-carcinogenic
agents, because all of them shown LC50 < 1000 g/mL, and exhibited more active then
curcumin (curcumins LC50 is 210.30 g/mL).
INTRODUCTION
Curcumin modification becomes mono-carbonyl analogues of curcumin (MACs) can
increases the potency of 10-30 times more than curcumin in a number of cell lines and cellular
proteins (1). Monocarbonyl curcumin analogues is much more stable at pH 6.5 and higher,
suggesting better pharmacokinetic profiles and greater tumor regimens on in vivo cancer
xenografts than curcumin (2). Monocarbonyl compounds with cyclohexanone ketones can
inhibit the growth of leukemia, colon, renal, melanaoma, ovarian, CNS, prostate, and breast
cancer cells better than cisplatin (3). Derivatives of asymmetric mono-carbonyl analogues of
curcumin have been known as antioxidant, anti-inflammatory, antimicrobial and anti
carcinogenic effects (4,5,6,7,8,9). Even though, there are a little reasearch to find on asymetrical
MACs and their activities as anti-carciogenic. The synthesis of asymmetric MACs can be done
by the condensation reaction of Clasein-Schmidt (10,11).
2.1 Materials And Experimental
Apparatus
Comp. R1 R2 R3
1a -H -OCH3 -OH
1b - OCH3 -OCH3 -OH
1c -F -OCH3 -OH
1d -Cl -OCH3 -OH
1e -CH3 -OCH3 -OH
1f -H -OH -OH
2a -H -OCH3 -OH
2b -OCH3 -OCH3 -OH
2c -F -OCH3 -OH
2d -Cl -OCH3 -OH
2e -CH3 -OCH3 -OH
2f -H -OH -OH