Inhibitory potency of some methoxyphenyl derivatives compounds on class mu GST activity in vitro

Sudibyo Martono

Abstract


Methoxy phenyl derivative’s compounds i.e. curcumin, ferulic acid, and indomethacin have been reported to have inhibitory effects on rat’s liver glutathione S-transferases (GST) activity. Vaniline and ferulic acid have been known as degradation products of curcumin, and still have methoxy phenyl groups on the structures. Until the recent years, there is no information concerning the influences of methoxy phenyl derivative’s compounds i.e. vaniline, dimethylcurcumin and ethyl-p-methoxycinnamate on GST-activity. The aim of this research is to study the correlation of the inhibitory activity of class mu GST isolated from uninduced and phenobarbital-induced rat liver cytosol by curcumin, dimethylcurcumin, vaniline, indomethacin, ethyl pmethoxycinnamate, and ferulic acid. GST activity was measured spectrophotometrically on the conjugation of DCNB and GSH. The results showed that the inhibitory activity of mu class GST in uninduced or phenobarbital-induced rat liver GST were decreasing as follow : curcumin, dimethylcurcumin, vaniline, indomethacin, ethyl p-methoxycinnamate, and ferulic acid.
Key words: methoxyphenyl derivative’s compounds, glutathione S-transferases activity.

Full Text:

Untitled

References


Ahokas, J.T., Nichols, F.A., Ravenscroff, P.J., and Emmerson, B.T., 1985, Inhibition of purified rat liver glutathione S-transferase isoenzymes by diuretics drugs, Biochem. Pharmacol., 34, 2157-2161.

Bradford, M.M., 1976, A rapid and sensitive method of the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding, Anal. Biochem, 72, 248 - 254.

Board, P.G., Baker, R.T., Chelvanayagam, G., and Jermin, L.S., 1997, Zeta, a novel class of glutathione transferases in a range of species from plants to human, Biochem. J., 328, 929-935.

Commandeur, J.N.M., Stijntjes G., and Vermeulen N.P.E., 1995, Enzymes and transport systems involved in the formation and disposition of glutathione S-conjugates, Pharmacol. Rev., 47, (2), 271-330.

Das, M ., Bickers, D.R., and Mukhtar, H., 1984, Plant phenols as in vitro inhibitors of glutathione Stransferase, Biochem. Biophys. Res. Commun., 120 (2), 427 -433.

Flatgaard, J.E., Bauer, K.E. and Kaufar, L.M., 1993, Isoenzyme specificity of novel glutathione Stransferase inhibitors, Cancer Chemother. Pharmacol., 33, 63-70.

Fitzpatrick, P.J., Krag, T.O.B., Hojrup, P., and Sheehan, D., 1995, Characterization of a glutathione S-transferase and related glutahione-binding protein from gill of the blue mussel, Mytilus edulis, Biochem. J., 305, 145-150.

Habig, W. H., Pabst, M.J., and Jakoby, W.B., 1974, Glutathione S-transferase, the fisrt enzymatic step in mercapturic acid formation, J. Biol. Chem., 249 (22), 7130-7139.

Hall, A., Robson, C.N., Hickson, I.D., Harris, A.L., Proctor, S.J. and Cattan, A.R., 1989 Possible role of inhibition of glutathione S-transferase in the partial reversal of chlorambucil resistance by indomethacin in a chinese hamster ovary cell line, Cancer Res., 49, 6265- 6268.

Hayes, J.D. and Pulford, D.J., 1995, The glutathione S-transferase supergene family: regulation of GST and the contribution of isoenzymes to cancer chemoprotection and drug resistance, Crit. Rev. in Biochem. and Mol. Biol., 30 (6), 445-600.

Hsieh, C.H., Liu, L.F., Tsai, S.P., and Tam, M.F., 1999, Characterization and cloning of avianhepatic glutathione S-transferases, Biochem. J., 343, 87-93.

Igarashi, T., Satoh, T., Iwashita, K., Ono, S., Ueno, K., and Kitagawa, H., 1985, Sex difference in subunit composition of hepatic glutathione S-transferase in rats, J. Biochem., 98, 117-123.

Igarashi, T., Irokawa, H., Ono, S., Ohmori, S., Ueno, K., and Kitagawa, H., 1987, Difference in the effects of phenobarbital and 3-methylcholanthrene treatment on subunit composition of hepatic glutathione S-transferase in male and female rats, Xenobiotica, 17 (2), 127-137.

Lundgren, B., Meijer, J., and Depierre, J.W., 1987, Characterization of the induction of cytosolic and microsomal epoxide hydrolases by 2-ethylhexanoic acid in mouse liver, Drug Metab. Dispos., 15, 114 - 121.

Mannervik, B., Alin, P., Guthenberg, C., Jensson, H., Tahir, M. K., Warholm, M., and Jornvall, H., 1985, Identification of three classes of cytosolic glutathione transferase common to several mammalian species: correlation between structural data and enzymatic properties, Proc. Natl. Acad. Sci. U.S.A., 82, 7202-7206.

Mannervik, B. and Danielson, V.H., 1988, Glutathione transferase-structure and catalytic activity, CRC. Crit. Rev. Biochem., 23, 283-337.

Meyer, D.J., Coles, B., Pemble, S.E., Gilmore, K.S., Fraser, G.M., and Ketterer, B., 1991, Theta, a new class of glutathione transferases purified from rat and human, Biochem. J., 274, 409- 414.

Meyer, D.J. and Thomas, M., 1995, Characterization of rat spleen prostaglandin H D-isomerase as a sigma class GSH transferase, Biochem. J., 311, 739-742.

Oetari, S., Sudibyo, M., Commandeur, J.N.M., Samhoedi, R., and Vermeulen, N.P.E., 1996, Effects of curcumin on cytochrome P-450 and glutathione S-transferase activities in rat livers, Biochem. Pharmacol., 51, 39 - 45.

Sudibyo, M., 1996, Efek hambatan kurkumin dan analognya pada aktivitas glutation S-transferase liver tikus secara in vitro, Laporan Penelitian DPP-SPP Fak. Farmasi UGM 1995/1996.

Sudibyo, M., 1997, Studi inhibisi kurkumin terhadap aktivitas enzim glutation S-transferase liver tikus yang diinduksi fenobarbital, Laporan Penelitian DPP-SPP Fak. Farmasi UGM 1996/1997, Yogyakarta.

Sudibyo, M and Sugiyanti, 1998, Studi inhibisi senyawa analog kurkumin terhadap aktivitas glutation S-transferase liver tikus dengan substrat 1,2-dikloro-4-nitrobenzen, Laporan Penelitian Proyek Molnas, Fakultas Farmasi UGM, Yogyakarta.

Sudibyo, M., 1999, Uji penghambatan aktivitas glutation S-transferase liver tikus oleh 2,5-bis-(4-hidroksi-3-metoksi benzilidin) siklopentanon dan dua analognya, Laporan Penelitian Mandiri, DIKS-UGM 1998/1999, Lembaga Penelitian, UGM.

Sudibyo, M., 2000, Inhibition of glutathione S-transferases by curcumin and its derivatives, Molecular mechanisms and qualitative structure-activity relationships, Dissertation, Gadjah Mada University, Yogyakarta, Indonesia.

Tonnesen, H.H. and Karlsen, J., 1985, Studies on curcumin and curcuminoids VI. Kinetics of curcumin degradation in aqueous solution, Z. Lebensm. Unters. Forsch., 180, 402-404.

Vos, R.M.E., Snoek, M.C., Berkel, W.H.V., Muller, F., and Bladeren, P.J.V., 1988, Differential induction of rat hepatic glutathione S-transferase isoenzymes by hexachlorobenzene and benzyl isothiocyanate, Biochem. Pharmacol., 37 (6) 1077-1082.




DOI: http://dx.doi.org/10.14499/indonesianjpharm0iss0pp45-50

Refbacks

  • There are currently no refbacks.




Copyright (c) 2017 INDONESIAN JOURNAL OF PHARMACY

Creative Commons License
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

Indonesian J Pharm indexed by:

web
analytics View My Stats