BENZYLIDENE CYCLOPENTANONE DERIVATIVES AS INHIBITORS OF RAT LIVER GLUTATHIONE S-TRANSFERASE ACTIVITIES

https://doi.org/10.22146/ijc.21842

Sudibyo Martono(1*)

(1) Laboratory of Pharmaceutical Chemistry, Faculty of Pharmacy, Gadjah Mada University, Yogyakarta
(*) Corresponding Author

Abstract


The effect of the curcumin analogues, 2,6-bis-(4-hydroxy-3-methoxy benzylidene) cyclopentanone (B1) and two of its derivatives on m class glutathione S-transferases (GSTs) from phenobarbital-induced and uninduced rat liver cytosol has been studied to elucidate their anti-inflammatory activity. GST activity was monitored spectrophotometrically using 1,2-dichloro-4-nitrobenzene. B1 was the most potent inhibitor of GSTs, both in uninduced and in phenobarbital-induced rat liver cytosol. These inhibitory properties might be explained as part of the anti-inflammatory activity of benzylidene cyclopentanone derivatives (B1 and B12).


Keywords


curcumin; benzylidene cyclopentanone; inhibitory potency; glutathione S-transferases mesoporous

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References

[1] Srimal, R.C. and Dhawan, B.N., 1973, J. Pharm. Pharmacol., 25, 447-452.

[2] Masuda, T., Jitoe, A., Isobe, J., Nakatani, N., and Yonemori, S., 1993, Phytochemistry, 32 (6), 1557-1560.

[3] Tonnesen, H.H. and Karlsen, J., 1985., Z. Lebensm. Unters. Forsch., 180, 132-134.

[4] Oetari, S., Sudibyo, M., Commandeur J.N.M., Samhoedi, R., and Vermeulen N.P.E., 1996, Biochem. Pharmacol., 51, 39-45.

[5] Tonnesen, H.H., Karlsen, J., and van Henegouwen, G.B., 1986, Z. Lebensm. Unters. Forsch., 183, 116-122.

[6] Dahl, T.A., Bilski, P., Reszka, K.J., and Chignell, C.F., 1994, Photochem. Photobiol., 59 (3), 290-294.

[7] Hsieh, C.H., Liu, L.F., Tsai, S.P., and Tam, M.F., 1999, Biochem. J., 343, 87-93.

[8] Timmerman, H., 1997, New Perspectives for Anti-Inflammatory Drugs, in : Suwijiyo Pramono (Ed.), Recent development in curcumin pharmacochemistry, Proceedings of the International Symposium on Curcumin Pharmaco-chemistry (ISCP), August 29-31, 1995, Yogyakarta, Indonesia, 1-12.

[9] Bach, M.K., Brashier, J.R., and Johnson, M.A., 1985, Biochem. Pharmacol., 34, 2695-2704.

[10] Hall, A., Robson, C.N., Hickson, I.D., Harris, A.L., Proctor, S.J., and Cattan, A.R., 1989, Cancer Res., 49, 6265-6268.

[11] Flatgaard, J.E., Bauer, K.E., and Kaufar, L.M., 1993, Cancer Chemother. Pharmacol., 33, 63-70.

[12] Ammon, H.P.T., Anazodo, M.I., Safayhi, H., Dhawan, B.N., and Srimal, R.C., 1992, Planta Med., 58, 226-231.

[13] Huang, M.T., Lysz T., Ferraro, T., Abidi, T.F., Laskin, F.A., and Conney A.H., 1991, Cancer Res., 51, 813-819.

[14] Sudibyo, M., 1996, Indon. J. Pharm., 7 (1), 39-51.

[15] Sudibyo, M., Hakim, L., Samhoedi, M., Commandeur, J.N.M., and Vermeulen, N.P.E., 1997, Effect of Curcumin and Its Derivatives on Glutathione S-Transferase Activity in Liver Cytosolic of b-Naphthoflavone-Treated Rats, in: Suwijiyo Pramono (Eds.), Recent Development in Curcumin Pharmacochemistry, Proceedings of the International Symposium on Curcumin Pharmacochemistry (ISCP), August 29-31, 1995, Yogyakarta, Indonesia, 126-135.

[16] Ujihara M, Tsuchida, S, Sato, H and Urade, Y, 1988, Archs. Biochem. Biophys., 264: 428-437.

[17] Sardjiman, 2000, Synthesis of Some New Series of Curcumin Analogues, Antioxidative, Antiinflammatory, Antibacterial Activities and Qualitative Structure-Activity Relationship, Dissertation, Gadjah Mada University, Yogyakarta, Indonesia.

[18] Sardjiman, 1993, Sintesis 2,6-bis-(3,5-dimetil-4-hidroksibenzilidin) sikloheksanon, 2,5-bis (3,5-dimetil-4-hidroksibenzilidin) siklopentanon dan 1,5-bis (3,5-dimetil-4-hidroksifenil)-1,3-penta-diene-3-on dan daya antioksidannya, Laporan Penelitian DPP-SPP, Fakultas Farmasi UGM, 1992/1993.

[19] Pabon, H.J.J., 1964, Rec. Trav. Chim. Pays Bas, 83, 379-386.

[20] Bradford, M.M., 1976, Anal. Biochem., 72, 248-254.

[21] Habig, W.H., Pabst, M.J., and Jakoby, W.B., 1974, J. Biol. Chem., 249 (22), 7130-7139.

[22] Cai, P., Bennet, D., Nair, R.V., Ceska, O., Smith, M.J.A., and Giovanni, J.D., 1993, Chem. Res. Toxicol., 6, 872-879.

[23] Metzler, D.E., 1977, Biochemistry. The Chemical Reactions of Living Cells, p. 301-318 Academic Press, Inc., New York.

[24] Das, M., Bickers, D.R., and Mukthar, H., 1984, Biochem. Biophys. Res. Commun., 120, 427-433.

[25] Iio, M., Kawaguchi, H., Sakota, Y., Otonari, J., and Nitahara, H., 1993, Biosci. Biotech. Biochem., 57 (10), 1678-1680.

[26] Van Bladeren P.J. and Van Ommen, B., 1991, Pharmacol. Ther., 51, 35-46.

[27] Commandeur, J.N.M., Stijntjes G., and Vermeulen N.P.E., 1995, Pharmacol. Rev., 47 (2), 271-330.

[28] Ploemen, J.H.T.M., Van Ommen, B., and Van Bladeren, P.J., 1990, Biochem. Pharmacol., 40 (7), 1631-1635.

[29] Tew, K.D., Bomber, A.M., and Hoffman, S.J., 1988, Cancer Res., 48, 3622-3625.

[30] O’Dwyer, P.J., La Creta, F., Nash, S., Tinsley, P.W., Schilder, R., Clapper, M.L., Tew, K.D., Panting, L., Litwin, S., and Comis, R.L., 1991, Cancer Res., 51, 6059-6065.



DOI: https://doi.org/10.22146/ijc.21842

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