Thymol analogues with antioxidant and L-type calcium current inhibitory activity

Drug Development Research

Volumn 64, Issue 4, 2005, Pages 195-202

  Shen, Ai Yu ^a   Huang, Mei Han ^a   Liao, Li Fang ^a   Wang, Try Shy ^a  

^a FOOYIN UNIVERSITY   (Taiwan)

Author keywords

Antioxidant activity; Calcium ion current; Mannich base; Thymol

Indexed keywords

4 MORPHOLINOMETHYL 2 ISOPROPYL 5 METHYLPHENOL; 4 PYRROLIDINOMETHYL 2 ISOPROPYL 5 METHYLPHENOL; ANTIOXIDANT; CALCIUM CHANNEL L TYPE; CYTOCHALASIN B; CYTOCHROME C; FORMALDEHYDE; FORMYLMETHIONYLLEUCYLPHENYLALANINE; MANNICH BASE; MORPHOLINE; NATURAL PRODUCT; PHORBOL 13 ACETATE 12 MYRISTATE; PYRROLIDINE DERIVATIVE; SCAVENGER; SUPEROXIDE; THYMOL; UNCLASSIFIED DRUG; XANTHINE OXIDASE;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; CALCIUM CURRENT; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; INCIDENCE; LIPID PEROXIDATION; MOUSE; NEUTROPHIL; NONHUMAN; OXIDATIVE STRESS; PATCH CLAMP; REGULATORY MECHANISM; WHOLE CELL;

EID: 23244447234     PISSN: 02724391     EISSN: None     Source Type: Journal    
DOI: 10.1002/ddr.10436     Document Type: Article

References (38)

1. Aeschbach R, Loliger J, Scott BC, Murcia A, Butler J, Halliwell B, Aruoma OI. 1994. Antioxidant actions of thymol, carvacrol, 6-gingerol, zingerone and hydroxytyrosol. Food Chem Toxicol 32:31-36.
2. 2+ currents through L-type channels in cultured rat dentate granule cells. Neurosci Lett 356:25-28.
3. Alam K, Nagi MN, Badary OA, Al-Shabanah OA, Al-Rikabi AC, Al-Bekairi A. 1999. M. The protective action of thymol against carbon tetrachloride hepatotoxicity in mice. Pharmacol Res 40:159-163.
4. Ambruso DR, Bolscher BG, Stokman PM, Verhoeven AJ, Roos D. 1990. Assembly and activation of the NADPH:O2 oxidoreductase in human neutrophils after stimulation with phorbol myristate acetate. J Biol Chem 265:924-930.
5. Benzie IF. 1996. Lipid peroxidation: a review of causes consequences measurement and dietary influences. Int J Food Sci Nutr 47:233-261.
6. Biava M, Fioravanti R, Porretta GC, Frachey G, Mencarelli P, Sleiter G, Perazzi ME, Simonetti N, Villa A. 1995. Study of the Mannich reaction: beta-amino-methylation of N-aryl and N-azaheteroaryl-substituted 2,5-dimethylpyrroles, compounds with potential biological activity. Farmco 50:431-438.
7. Chang WS, Chang YH, Lu FJ, Chiang HC. 1994. Inhibitory effects of phenolics on xanthine oxidase. Anticancer Res 14:501-506.
8. Cotelle N, Bernier JL, Catteau JP, Pommery J, Wallet JC, Gaydou EM. 1996. Antioxidant properties of hydroxy-flavones. Free Radical Biol Med 20:35-43.
9. Geng B, Fleming PR, Umlauf S, Lin A, Pallai PV. 2002. The synthesis and selective IL-2 inhibitory activity of bis piperazine-phenol Mannich adducts. Bioorg Med Chem Lett 12:775-778.
10. Gul HI, Ojanen T, Vepsalainen J, Gul M, Erciyas E, Hanninen O. 2001. Antifungal activity of some mono, bis and quaternary Mannich bases derived from acetophenone. Arzneimittel-Forsch 51:72-75.
11. Haeseler G, Maue D, Grosskreutz I, Bufler I, Nentwig B, Piepenbrock S, Dengler R, Leuwer M. 2002. Voltage-dependent block of neuronal and skeletal muscle sodium channels by thymol and menthol. Eur J Anaesth 19:571-579.
12. Halliwell B. 1987. Free radicals and metal ions in health and disease. Proc Nutr Soc 46:13-26.
13. Hamill OP, Marty A, Neher E, Sakmann B, Sigworth FJ. 1981. Improved patch-clamp techniques for high-resolution current recording from cells and cell-free membrane patches. Pflugers Arch Eur J Physiol 391:85-100.
14. House HO. 1964. The aldol condensation and related reactions. In: Breslow R, editor. Modern synthetic reactions. New York: Cambridge, p 230-234.
15. Kourie JI. 1998. Interaction of reactive oxygen species with ion transport mechanisms. Am J Physiol 275:1-24.
16. Meves H, Schwarz JR, Wulfsen I. 1999. Separation of M-like current and ERG current in NG108-15 cells. Br J Pharmacol 127:1213-1223.
17. Mihara M, Uchiyama M, Fukuzawa K. 1980. Thiobarbituric acid value on fresh homogenate of rat as a parameter of lipid peroxidation in aging CCl4 intoxication and vitamin E deficiency. Biochem Med 23:302-311.
18. Mohammadi B, Haeseler G, Leuwer M, Dengler R, Krampfl K, Bufler J. 2001. Structural requirements of phenol derivatives for direct activation of chloride currents via GABA(A) receptors. Eur J Pharmacol 421:85-91.
19. Ohkawa H, Ohishi N, Yagi K. 1979. Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction. Anal Biochem 95:351-358.
20. Olasupo NA, Fitzgerald DJ, Narbad A, Gasson MJ. 2004. Inhibition of Bacillus subtilis and Listeria innocua by nisin in combination with some naturally occurring organic compounds. J Food Protect 67:596-600.
21. Partrick DA, Moore FA, Moore EE, Barnett CC Jr, Silliman CC. 1996. Neutrophil priming and activation in the pathogenesis of postinjury multiple organ failure. New Horizons 4:194-210.
22. Rimm EB, Manson JE, Stampfer MJ, Colditz GA, Willett WC, Rosner B, Hennekens CH, Speizer FE. 1993. Cigarette smoking and the risk of diabetes in women. Am J Public Health 83:211-214.
23. Roberts PJ, Devereux S, Pilkington GR, Linch DC. 1990. Fc gamma RII- mediated superoxide production by phagocytes is augmented by GM-CSF without a change in Fc gamma RII expression. J Leukocyte Biol 48:247-257.
24. Seabrook GR, McAllister G, Knowles MR, Myers J, Sinclair H, Patel S, Freedman SB, Kemp JA. 1994. Depression of high-threshold calcium currents by activation of human D2 (short) dopamine receptors expressed in differentiated NG108-15 cells. Br J Pharmacol 111:1061-1066.
25. Sevanian A, Shen L, Ursini F. 2000. Inhibition of LDL oxidation and oxidized LDL-induced cytotoxicity by dihydropyridine calcium antagonists. Pharmaceut Res 17:999-1006.
26. Shen AY, Hwang MH, Roffler S, Chen CF. 1995. Cytotoxicity and antimicrobial activity of some naphthol derivatives. Arch Pharm 328:197-201.
27. Shen AY, Tsai CT, Chen CL. 1999. Synthesis and cardiovascular evaluation of N-substituted aminonaphthols. Eur J Med Chem 34:877-882.
28. Smith JA. 1994. Neutrophils, host defense, and inflammation: a double-edged sword. J Leukocyte Biol 56:672-686.
29. Szentandrassy N, Szentesi P, Magyar J, Nanasi PP, Csernoch L. 2003. Effect ofthymol on kinetic properties of Ca and K currents in rat skeletal muscle. BMC Pharmacol 3:9.
30. Tepe B, Daferera D, Sokmen M, Polissiou M, Sokmen A. 2004. In vitro antimicrobial and antioxidant activities of the essential oils and various extracts of Thymus eigii M. Zohary et PH. Davis. J Agric Food Chem 52:1132-1137.
31. Tomita TKM, Kanegasaki S. 1984. Staphylococcal delta toxin-induced generation of chemiluminescence by human polymorphonuclear leukocytes. Toxicon 22:957-965.
32. Vardar-Unlu G, Candan F, Sokmen A, Daferera D, Polissiou M, Sokmen M, Donmez E, Tepe B. 2003. Antimicrobial and antioxidant activity of the essential oil and methanol extracts of Thymus pectinatus Fisch, et Mey. var. pectinatus (Lamiaceae). J Agric Food Chem 51:63-67.
33. Wang SH, Zheng HJ. 1987. Cryopreservation of infective-stage larvae of Brugia malayi. Southeast Asian J Trop Med Pub Health 18:488-490.
34. Weiss SJ. 1989. Tissue destruction by neutrophils. New Engl J Med 320:365-376.
35. Windsor AC, Mullen PG, Fowler AA, Sugerman HJ. 1993. Role of the neutrophil in adult respiratory distress syndrome. Br J Surg 80:10-17.
36. + current in NG108-15 neuronal cells. Neuropharmacology 41:834-843.
37. Youdim KA, Deans SG. 2000. Effect of thyme oil and thymol dietary supplementation on the antioxidant status and fatty acid composition of the ageing rat brain. Br J Nutr 83:87-93.
38. Yucel-Lindberg T, Ahola H, Carlstedt-Duke J, Modeer T. 1999. Involvement of tyrosine kinases on cyclooxygenase expression and prostaglandin E2 production in human gingival fibroblasts stimulated with interleukin-1beta and epidermal growth factor. Biochem Biophys Res Commun 257:528-532.