INHIBITORY POTENTIAL OF SOME SYNTHETIC CINNAMIC ACID DERIVATIVES TOWARDS TYROSINASE ENZYME
Lanny Hartanti(1*), Henry Kurnia Setiawan(2)
(1) Faculty of Pharmacy, Widya Mandala Catholic University, Jl. Dinoyo 42-44 Surabaya 60265
(2) Faculty of Pharmacy, Widya Mandala Catholic University, Jl. Dinoyo 42-44 Surabaya 60265
(*) Corresponding Author
Abstract
Cinnamic acid is one of known tyrosinase inhibitors. This study investigated the inhibition of tyrosinase activity of some cinnamic acid derivatives, i.e. 4-buthoxy-cinnamic acid, 4-n-butylcinnamic acid and 4-phenylcinnamic acid. Each inhibitor used in this research had the same type of inhibition towards enzymatic activity, i.e. mixed type inhibition of competitive and non competitive type. The potential sequence of tyrosinase inhibition based on the ratio of its IC50 compared to cinnamic acid, from the lowest to the highest were 4-buthoxycinnamic acid, 4-phenylcinnamic acid and 4-n-butylcinnamic acid. Based on the obtained results of this research, it was disclosed that n-butyl substituent on para position did not increase the inhibition effect of cinnamic acid towards tyrosinase enzymatic reaction. But in the other hand, buthoxy and phenyl substituent on para position could increase the inhibition effect of cinnamic acid towards tyrosinase enzymatic reaction because buthoxy substituent increased the similarity of its structure with the substrate of enzymatic reaction while phenyl susbtituent blocked the substrate-enzyme reaction.
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[1] Harry, R.G., 1973, Harry’s Cosmetology, 6th ed., Vol. 1, Chemical Publishing, New York.
[2] Balsam, M.S. and Sagarin, E., 1972, Cosmetics Science and Technology, 2nd ed, Vol. 3, John Wiley and Sons, New York.
[3] Avanti, C., 2002, Daya Hambat Epigalokatekin Galat (EGCG) dan Kombinasi Epigalokatekin Galat – Kojic Acid terhadap Aktivitas Tirosinase, Tesis, Universitas Airlangga.
[4] Tan, C., Zhu, W., and Lu, Y., 2002, Chin. Med. J., 115, 1859-1862.
[5] Duke, J.A., 2004, Dr. Duke’s Phytochemical and Ethnobotanical Databases, Http://www.ars-grin.gov/duke, 12 Maret 2005.
[6] Natella, F., Nardini, M., DiFelice, M., and Scaccini, C., 1999, J. Agric. Food. Chem, 47, 1453-1459.
[7] Yesilada, A., Zorlu, E., Aksu, F., and Yesilada, E., 1996, Farmaco, 51, 595-599.
[8] Sadono, S., 2001, Bioavailabilitas Etil p-metoksisinamat dari Perasan Rimpang Kencur pada Hewan Coba Kelinci, Tesis, Universitas Airlangga, Surabaya.
[9] Parfitt, K., (ed), 1999, Martindale The Complete Drug Reference, 32nd ed., Pharmaceutical Press, London.
[10] Knoerzer, T.A., 2003, Multi-step Synthesis of 3-Alkoxy-4-methoxy-6-nitro-trans-cinnamic acid, Http://www.naz.edu, diakses pada tanggal 18 Januari 2005.
[11] Sakuma, K., Ogawa, M., Sugibayashi, K., and Yamamoto, K., 1999, Acc. Pharm. Res., 22, 335-339.
[12] Kubo, I., Kinst-Hori, I., and Yokohama, Y., 1994, J. Nat. Prod., 57, 545-551.
[13] Glyglewski, R.J., “Structure-Activity Relationship of Some Prostaglandin Synthetase Inhibitors” in Prostaglandin Synthetase Inhibitors. Eds. Robinson, H.J. and Vane, J.R., Raven Press, New York, 1974.
[14] Shen, T.Y., “Nonsteroidal Antiinflamatory Agent” in Burger’s Medicinal Chemistry, Ed. Wolff, M.E., 4th ed, John Wiley and Sons, New York, 1981.
[15] Siswandono, S. and Soekardjo, B., 2000, Kimia Medisinal, Airlangga University Press, Surabaya.
[16] Rudyanto, M. and Hartanti, L., 2008, Indonesian Journal of Chemistry, 8, 226-230.
[17] Thomas, G., 2000, Medicinal Chemistry: an introduction, John Wiley and Sons, Chichester.
[18] Boyer, R.F., 1993, Modern Experimental Biochemistry, 2nd ed, Benjamin/Cumming Publishing, California.
[19] Siswandono, S. and Purwanto, “Hubungan struktur aspek stereokimia dan aktivitas biologis obat” dalam Kimia Medisinal, Eds. Siswandono dan Soekardjo, B., Airlangga University Press, Surabaya, 2000.
DOI: https://doi.org/10.22146/ijc.21579
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