Structure Modification of Ethyl p-methoxycinnamate Isolated from Kaempferia galanga Linn. and Citotoxicity Assay of The Products on WiDr Cells

Juni Ekowati, Marcellino Rudyanto, Shigeru Sasaki, Tutuk Budiati, Sukardiman -, Adam Hermawan, Edy Meiyanto


Ethyl p-methoxycinnamate, major ingredient of Kaempferia galanga rhizome, have been reported not only has analgesic – anti inflammatory activities like NSAIDs which inhibited cyclooxygenase, but also inhibit tumor cell proliferation in specimen of mouse epidermis. Therefore, it will be interesting to carry out synthetic studies on the derivates of ethyl p-methoxycinnamate and searching their citotoxic activity on WiDr cell. We wish to report of structure modification on carboxyl moiety of ethyl p-methoxycinnamate  and  evaluation on their citotoxic activity  on WiDr cell. Isolation of ethyl p-methoxycinnamate from Kaempferia galanga rhizome was carried out by percolation with ethanol 96% as solvent. Hydrolysis of ethyl p-methoxycinnamate in basic condition was performed to obtain p-methoxycinnamic acid. Preparation of some thiourea derivates of ethyl p-methoxycinnamate was carried out  by microwave irradiation. Citotoxicity assay was carried out by MTT method for 48 h.

Modification of carboxyl group of ethyl p-methoxycinnamate to its thiourea form could be carried out by microwave irradiation gave; (E)-3-(4-methoxyphenyl)-N-(phenylcarba- mothioyl)acrylamide (50%); (E)-3-(4-methoxyphenyl)-N-(4-methoxyphenylcarbamothi- oyl)acrylamide (26%) and (E)-3-(4-methoxyphenyl)-N-(4-methylphenylcarbamothioyl) acrylamide (54%), yield calculated for 2 step from the acid chloride. All compounds showed no citotoxic effect on WiDr cell at 48 h incubation.

Keywords :  ethyl p-methoxycinnamate, microwave irradiation, Kaempferia galanga, citotoxicity, WiDr cell

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Chabner, B.A., Amrein, P.C., Druker, B.J., et al., 2006. Chemotherapy of Neoplastic Diseases. In : Brunton, L.L., Lazo, J.S., Parker K.L., Goodman and Gilman's the Pharmacological Basis of Therapeutics, 11th Ed, New York : The McGraw- Hill Co., Inc. Chapter 51.

Doyle, A., and Griffiths, J.B., 2000, Cell and Tissue Culture for Medical Research, John Willey and Sons Ltd, New York.

Freimoser, F.M., Jakob, C.A., Aebi, M., and Tuor, U., 1999, The MTT 3-(4,5-Dimethylthiazol-2-yl)-2,5-Diphenyltetrazolium Bromide Assay Is a Fast and Reliable Method for Colorimetric Determination of Fungal Cell Densities, Applied and Environmental Microbiology, 65, (8), 3727-3729.

Giovannetti, E., Backus, H.H.J., Wouters, D., Ferreira, C.G., van Houten, V.M.M. and Brakenhoff, R.H., 2007, Changes in the Status of p53 Affect Drug Sensitivity to Thymidylate Synthase (TS) Inhibitors by Altering TS Levels, British J. Can., 96:769-775.

Lullman, H., Mohr, K., Zielger, A., Bieger, D., 2002. Color Atlas of Pharmacology, 2nd Ed, New York : Thieme Stuttgard., p.296-299.

Mavandadi, F., Lidstrom, P., 2004. Microwave-Assisted Chemistry in Drug Discovery. Medical Chemistry. Vol.4, hal. 773-792.

Medina, P.J., Davis, L.E., 2005. Colorectal Cancer. In : Dipiro, J.T., Talbert, R.L., Matzke G.R., Wells, B.G., Posey, L.M (Eds). Pharmacotherapy A Pathofisiologic Approach, 6th Ed, New York : The McGraw-Hill Co., Inc. p.2383-2415.

Mosmann, T., 1983, Rapid Colorimetric Assay for Cellular Growth & Survival: Application to Proliferation & Cytotoxicity Assays, Journal of Immunological Method, 65, 65-59.

NCI fact sheet 2007. What is cancer? accessed from October 2008

Sigmond, J., Backus, H.H., Wouters, D., Temmink, O.H., Jansen, G. and Peters, G.J., 2003, Induction of Resistance to the Multitargeted Antifolate Pemetrexed (ALIMTA) in WiDr Human Colon Cancer Cells is Associated with Thymidilate Synthase Overexpression, Biochem. Pharmacol. 25, 12, p189-201.

Tewtrakul S., Yuenyongsawad S., Kummee S. and Atsawajaruwan L. 2005. Chemical component and biological activities of volatile oil of kaempferia galanga Linn. Songklanakarin J.Sci.Technol. 27 (Suppl.2) : Thai herbs.pp.504-507.

Ueda, J.Y., Tezuka, Y., Banskota., A.H., Tran, Q.L., Tran, Q.K., Harimaya, Y., Saiki, I., dan Kadota, S, 2002, Antiproliferative Activity of Vietnamese Medicinal Plants, Biol. Pharm. Bull. 25 (6): 753-760.

Vimala S, Norhanom AW, and Yadav, 1999. Antitumor promoter activity in Malaysian ginger rhizobia used in traditional medicine.Br. J. Cancer. 80 (1-2) : pp. 110-116.

Wells, B.G., DiPiro, J., Schwinghammer, T., Hamilton, C., 2006. Pharmacotherapy Handbook, 6th Ed, Boston : The McGraw-Hill Co. pp.614-621.

Wei, T.B., Lin, Q., Zhang, Y.M., and Wei, W., 2004. Microwave Promoted Efficient Synthesis of N-Aryl-N’-Aroyl thiourea under Solvent-Free and Phase Transfer Catalysis Conditions. Journal of Synthesic Communication, 34 (1), 181-186.

Xue Y, Chen H. 2001. Abstracts of the XVIth EUCARPIA Congress.Edinburg. Scotland.

Xu, X., Qian, X., Li, Z., Huang, Q., Chen, G. 2003. J. of Fluorine Chemistry. 121 : pp. 51-54.


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