The interaction of selected natural products with human recombinant glutathione transferases

Phytotherapy Research

Volumn 18, Issue 11, 2004, Pages 877-883

  Hayeshi, Rose ^a   Mukanganyama, Stanley ^a   Hazra, Banasri ^b   Abegaz, Berhanu ^c   Hasler, Julia ^a  

^a UNIVERSITY OF ZIMBABWE   (Zimbabwe)

^b JADAVPUR UNIVERSITY   (India)

^c UNIVERSITY OF BOTSWANA   (Botswana)

Author keywords

Diospyrin; Ergothioneine; Geshoidin; Glutathione transferases

Indexed keywords

1 CHLORO 2,4 DINITROBENZENE; DIOSPYRIN; ETACRYNIC ACID; GESHOIDIN; GLUTATHIONE; GLUTATHIONE TRANSFERASE; GLUTATHIONE TRANSFERASE A1; GLUTATHIONE TRANSFERASE M1 1; GLUTATHIONE TRANSFERASE P1 1; NATURAL PRODUCT; RECOMBINANT ENZYME; THIONEINE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; COMPETITIVE INHIBITION; CONCENTRATION RESPONSE; DRUG PROTEIN BINDING; DRUG STRUCTURE; ENZYME ACTIVATION; ENZYME INACTIVATION; ENZYME INHIBITION; ENZYME KINETICS; HUMAN; IC 50; IN VITRO STUDY; IN VIVO STUDY; PROTEIN EXPRESSION;

DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG INTERACTIONS; ENZYME INHIBITORS; ERGOTHIONEINE; GLUCOSIDES; GLUTATHIONE TRANSFERASE; HUMANS; INHIBITORY CONCENTRATION 50; NAPHTHALENES; NAPHTHOQUINONES; PHYTOTHERAPY; PLANTS, MEDICINAL;

EID: 11144234263     PISSN: 0951418X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ptr.1481     Document Type: Article

References (32)

1. Abegaz BM, Kebede T. 1995. Geshoidin: A bitter principle of Rhamnus prinoides and other constituents of the leaves. Bull Chem Soc Ethiop 9: 107-114.
2. Adeniyi BA, Fong HHS, Pezzuto JM, Luyengi L, Odelola HA. 2000. Antibacterial activity of diospyrin, isodiospyrin, and bisisodiospyrin from the root of Diospyros piscatoria (Gurke) (Ebenaceae). Phytother Res 14: 112-117.
3. Adler V, Yin Z, Fuchs SY, et al. 1999. Regulation of JNK signalling by GSTp. EMBO J 18: 1321-1334.
4. Akanmu D, Cecchini R, Aruoma OI, Halliwell B. 1991. The antioxidant action of ergothioneine. Arch Biochem Biophys 288: 10-16.
5. Asmus K-D, Bensasson RV, Bernier J-L, Houssin R, Land EJ. 1996. One-electron oxidation of ergothioneine and analogues investigated by pulse radiolysis: redox reaction involving ergothioneine and vitamin C. Biochem J 315: 625-629.
6. Burg D, Mulder GJ. 2002. Glutathione conjugates and their synthetic derivatives as inhibitors of glutathione-dependent enzymes involved in cancer and drug resistance. Drug Metab Rev 34: 821-863.
7. Chakrabarty S, Roy M, Hazra B, Bhattacharya RK. 2002. Induction of apoptosis in human cancer cell lines by diospyrin, a plant-derived bisnaphthoquinonoid, and its synthetic derivatives. Cancer Lett 188: 85-93.
8. Chang M, Shin, YG, van Breemen RB, Blond SY, Bolton JL. 2001. Structural and functional consequences of inactivation of human glutathione S-transferase P1-1 mediated by the catechol metabolite of equine estrogens, 4-hydroxyquilenin. Biochemistry 40: 4811-4820.
9. Coles B, Ketterer B. 1990. The role of glutathione and glutathione transferases in chemical carcinogenesis. Crit Rev Biochem Mol Biol 25: 47-64.
10. Cowan MM. 1999. Plant products as antimicrobial agents. Clin Microbiol Rev 12: 564-582.
11. Eaton DL, Bammler TK. 1999. Concise review of the glutathione S-transferases and their significance to toxicology. Toxicol Sci 49: 154-164.
12. Gaudiano G, Koch TH, Lo Bello M, et al. 2000. Lack of glutathione conjugation to adriamycin in human breast cancer mcf-7/dox cells: Inhibition of glutathione S-transferase P1-1 by glutathione conjugates from anthracyclines. Biochem Pharmacol 60: 1915-1923.
13. Ghazali R, Waring RH. 1999. Effects of flavonoids on glutathione-S- transferase in human blood platelets, rat liver, rat kidney, and HT-29 colon adenocarcinoma cell-lines: potential in drug metabolism and chemoprevention. Med Sci Res 27: 449-451.
14. Hazra B, Saha AK, Ray R, Roy DK, Sur P, Banerjee A. 1987. Antiprotozoal activity of diospyrin towards Leishmania donovani. Trans Roy Soc Trop Med Hyg 81: 738-741.
15. Hazra B, Sur P, Roy DK, Sur B, Banerjee A. 1984. Biological activity of diospyrin towards Ehrlich ascites carcinoma in Swiss A mice. Planta Med 51: 295-297.
16. Johansson A, Mannervik B. 2001. Inter-individual variability of glutathione transferase expression. In Inter-individual Variability in Human Drug Metabolism, Pacifici GM, Pelkonen O (eds). Taylor & Francis: London; 460-519.
17. Lall N, Das Sarma M, Hazra B, Meyer JJM. 2003. Anti-mycobacterial activity of diospyrin derivatives and a structural analogue of diospyrin against Mycobacterium tuberculosis in vitro. J Antimicrob Chemother 51: 435-438.
18. Mannervik B, Widersten M. 1995. Human glutathione transferases: classification, tissue distribution, structure, and functional properties. In Advances in Drug Metabolism in Man, Pacifici G, Fracchia F (eds). European Commission: Luxembourg; 408-459.
19. Maurer T, Fung H-L. 2000. Comparison of methods for analyzing kinetic data from mechanism-based enzyme inactivation: application to nitric oxide synthase. AAPS PharmSci 2: article 8,: 1-10. www.aapspharmsci.org.
20. Mukanganyama S, Widersten M, Naik YS, Mannervik B, Hasler JA. 2002. Inhibition of glutathione S-transferases by anti-malarial drugs possible implications for circumventing anticancer drug resistance. Int J Cancer 37: 700-705.
21. Norhanom AW, Hazra B. 1997. Inhibition of tumour promoter-induced Epstein-Barr virus activation by diospyrin, a plant-derived antitumour compound, and its synthetic derivatives. Phytother Res 11: 588-590.
22. Oxis International, Inc., http://www.oxis.com
23. Schipper DL, Wagenmans MJH, Wagener DJT, Peters WHM. 1997. Glutathione S-transferases and cancer (review). Int J Oncol 10: 1261-1264.
24. Segel IH. 1975. Enzyme Kinetics. John Wiley and Sons: Toronto.
25. Shen H, Tamai K, Satoh K, Hatayama I, Tsuchida S, Sato K. 1991. Modulation of class Pi glutathione transferase activity by sulfhydryl group modification. Arch Biochem Biophys 286: 178-182.
26. Terradez P, Asensi M, Lasso de la Vega MC, Puertes IR, Vina J, Estrela JM. 1993. Depletion of tumour glutathione in vivo by buthionine sulphoximine: modulation by the rate of cellular proliferation and inhibition of cancer growth. Biochem J 292: 477-483.
27. van Bladeren PJ. 2000. Glutathione conjugation as a bioactivation reaction. Chem Biol Interact 129: 61-76.
28. van Haaften RIM, den Hartog GJM, Evelo CTA, Haenen GRMM, Bast A. 2001. Hypochlorous acid is a potent inhibitor of GST P1-1. Chem Biol Interact 138: 77-83.
29. van Iersel MLPS, Ploemen JHTM, Lo BeIIo M, Federici G, van Bladeren PJ. 1997. Interactions of α,β-unsaturated aldehydes and ketones with human glutathione S-transferase P1-1. Chem Biol Interact 108: 67-68.
30. Waxman DJ. 1990. Glutathione S-transferases: role in alkylating agent resistance and possible target for modulation chemotherapy - a review. Cancer Res 50: 6449-6454.
31. Yoshida M, Mori K. 1995. Synthesis of diospyrin, a potential agent against leishmaniasis, and related parasitic protozoan diseases. Eur J Org Chem 2000: 1313-1317.
32. Zhou S, Gao Y, Jiang W, Huang M, Xu A, Paxton JW. 2003. Interactions of herbs with cytochrome P450. Drug Metab Rev 35: 35-98.