Designing of enzyme inhibitors based on active site specificity: lessons from methyl gallate and its lipoxygenase inhibitory profile

References

• Hernandez M, Martin R, Garcia-Cubillas MD, et al. Secreted PLA2 induces proliferation in astrocytoma through the EGF receptor: another inflammation-cancer link. Neuro Oncology. 2010;12:1014–1023.
   PubMed Web of Science ®Google Scholar
• Jager AK, Hutchings A, Van Staden J. Screening of Zulu medicinal plants for prostaglandin-synthesis inhibitors. J Ethnopharmacol. 1996;52:95–100.
   PubMed Web of Science ®Google Scholar
• Alitonou GA, Avlessi F, Sohounhloue DK, et al. Investigations on the essential oil of Cymbopogon giganteus from Benin for its potential use as an anti-inflammatory agent. International J Aromather. 2006;16:37–41.
   Google Scholar
• Piper PJ, Letts LG, Samhoun MN, et al. Advances in Prostaglandin Thromboxane and Leukotriene Research. Vol9, New York: Raven Press; 1994.
   Google Scholar
• Minor W, Steczko J, Stec B, et al. Crystal structure of soybean lipoxygenase L-1 at 1.4 A resolution. Biochemistry. 1996;35:10687–10701.
   PubMed Web of Science ®Google Scholar
• Gillmor SA, Villasenor A, Fletterick R, et al. The structure of mammalian 15-lipoxygenase reveals similarity to the lipases and the determinants of substrate specificity. Nat Struct Mol Biol. 1997;4:1003–1009.
   Google Scholar
• Scarrow RC, Trimitsis MG, Buck CP, et al. X-ray spectroscopy of the iron site in soybean lipoxygenase-1: changes in coordination upon oxidation or addition of methanol. Biochemistry. 1994;33:15023–15035.
   PubMed Web of Science ®Google Scholar
• Kuban RJ, Wiesner R, Rathman J, et al. The iron ligand sphere geometry of mammalian 15-lipoxygenases. Biochem J. 1998;332:237–242.
   PubMed Web of Science ®Google Scholar
• Brash AR. Lipoxygenases: occurrence, functions, catalysis, and acquisition of substrate. J Biol Chem. 1999;274:23679–23682.
   PubMed Web of Science ®Google Scholar
• Grechkin A. Recent developments in biochemistry of the plant lipoxygenase pathway. Prog Lipid Res. 1998;37:317–352.
   PubMed Web of Science ®Google Scholar
• Funk CD. Prostaglandins and leukotrienes: advances in eicosanoid biology. Science. 2001;294:1871–1875.
   PubMed Web of Science ®Google Scholar
• Rapoport SM, Schewe T, Thiele BJ. Erythroid cells In: Harris JR, editor. Blood cell biochemistry. New York: Plenum Press; 1990.
   Google Scholar
• Leyen VK, Duvoisin RM, Engelhardt H, et al. A function for lipoxygenase in programmed organelle degradation. Nature. 1998;395:392–395.
   PubMed Web of Science ®Google Scholar
• Samuelsson B, Dahlen SE, Lindgren JA, et al. Leukotrienes and lipoxins: structures, biosynthesis, and biological effects. Science. 1987;237:171–1176.
   PubMed Web of Science ®Google Scholar
• Kuhn H, Chan L. The role of 15-lipoxygenase in atherogenesis: pro- and antiatherogenic actions. Curr Opin Lipidol. 1997;8:111–117.
   PubMed Web of Science ®Google Scholar
• Klein RF, Allard J, Avnur Z, et al. Regulation of bone mass in mice by the lipoxygenase gene Alox15. Science. 2004;303:229–332.
   PubMed Web of Science ®Google Scholar
• McMillan RM, Walker ER. Designing therapeutically effective 5-lipoxygenase inhibitors. Trends Pharmacol Sci. 1992;13:323–330.
   PubMed Web of Science ®Google Scholar
• Gorins G, Kuhnert L, Johnson CR, et al. (Carboxyalkyl) benzyl propargyl ethers as selective inhibitors of leukocyte-type 12-lipoxygenases. J Med Chem. 1998;39:4871–4878.
   Web of Science ®Google Scholar
• Malamas MS, Carlson RP, Grimes D, et al. Azole Phenoxy Hydroxyureas as Selective and Orally Active Inhibitors of 5-Lipoxygenase. J Med Chem. 1996;39:237–245.
   PubMed Web of Science ®Google Scholar
• Wenzel SE, Kamada AK. Zileuton: The First 5-Lipoxygenase Inhibitor for the Treatment of Asthma. Ann Pharmacother. 1996;30:858–864.
   PubMed Web of Science ®Google Scholar
• Drazen JM, Israel E, O’Byrne PM. Treatment of asthma with drugs modifying the leukotriene pathway. N Engl J Med. 1999;340:197–206.
   PubMed Web of Science ®Google Scholar
• Lee KH. Discovery and Development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach. J Nat Prod. 2010;73:500–516.
   PubMed Web of Science ®Google Scholar
• Rishton GM. Natural products as a robust source of new drugs and drug leads: past successes and present day issues. Am J Cardiol. 2008;101:(10A–43D. 9D).
   Web of Science ®Google Scholar
• Li JW, Vederas JC. Drug discovery and natural products: end of an era or an endless frontier? Science. 2009;325:161–165.
   PubMed Web of Science ®Google Scholar
• Harvey AL. Natural products in drug discovery. Drug Discov Today. 2008;13:894–901.
   PubMed Web of Science ®Google Scholar
• McChesney JD, Venkataraman SK, Henri JT. Plant natural products: back to the future or into extinction?. Phytochemistry. 2007;68:2015–2022.
   PubMed Web of Science ®Google Scholar
• Tan G, Gyllenhaal C, Soejarto DD. Biodiversity as a source of anticancer drugs. Curr Drug Targets. 2006;7:265–277.
   PubMed Web of Science ®Google Scholar
• Bashir S, Gilani AH. Antiurolithic effect of Bergenia ligulata rhizome: An explanation of the underlying mechanisms. J Ethnopharmacol. 2009;122:106–116.
   PubMed Web of Science ®Google Scholar
• Chandra reddy UD, Chawla AS, Mundkinajeddu D, et al. Paashaanolactone from Bergenia ligulata. Phytochemistry 1998;47:907–909.
   Web of Science ®Google Scholar
• Sadat A, Uddin G, Alam M, et al. Structure activity relationship of bergenin, p-hydroxybenzoylbergenin, 11-O-galloylbergenin as potent antioxidant and urease inhibitor isolated from Bergenia ligulata. Natural Prod Res. 2015;29:2291–2294.
   PubMed Web of Science ®Google Scholar
• Umashankar D, Chandra Reddy ASC. High pressure liquid chromatographic determination of bergenin and (+)-afzelechin from different parts of Paashaanbhed (Bergenia ligulata Yeo). Phytochem Anal. 1999;10:44–47.
   Web of Science ®Google Scholar
• Dhalwal K, Shinde VM, Biradar YS, et al. Simultaneous quantification of bergenin, catechin, and gallic acid from Bergenia ciliata and Bergenia ligulata by using thin-layer chromatography. J Food Compos Anal. 2008;21:496–500.
   Web of Science ®Google Scholar
• Anthon GE, Barrett DM. Colorimetric method for the determination of lipoxygenase activity. J Agric Food Chem. 2001;49:32–37.
   PubMed Web of Science ®Google Scholar
• Jorgensen WL, Chandrasekhar J, Madura JD, et al. Comparison of simple potential functions for simulating liquid water. J Chem Phys. 1983;79:926–935.
   Web of Science ®Google Scholar
• Jorgensen WL, Tirado-Rives J. The OPLS force field for proteins. Energy minimization of crystals of cyclic peptides and crambin. J Am Chem Soc. 1988;110:1657–1666.
   PubMed Web of Science ®Google Scholar
• Halgren TA, Nachbar RBJ. Merck molecular force field. IV. Conformational energies and geometries for MMFF94. J Comput Chem. 1996;17:587–615.
   Web of Science ®Google Scholar
• Kim SJ, Jin M, Lee E, et al. Effects of methyl gallate on arachidonic acid metabolizing enzymes: Cyclooxygenase-2 and 5-lipoxygenase in mouse bone marrow-derived mast cells. Arch Pharm Res. 2006;29:874–878.
   PubMed Web of Science ®Google Scholar
• Kamatham S, Kumar N, Gudipalli P. Isolation and characterization of gallic acid and methyl gallate from the seed coats of Givotia rottleriformis Griff. and their anti-proliferative effect on human epidermoid carcinoma A431 cells. Toxicol Rep. 2015;2:520–529.
   PubMed Web of Science ®Google Scholar
• Correa LB, Padua TA, Seito LN, et al. Anti-inflammatory effect of methyl gallate on experimental arthritis: inhibition of neutrophil recruitment, production of inflammatory mediators, and activation of macrophages. J Nat Prod. 2016;79:1554–1566.
   PubMed Web of Science ®Google Scholar
• Tomy MJ, Dileep KV, Prasanth S, et al. Cuminaldehyde as a lipoxygenase inhibitor: in vitro and in silico validation. Appl Biochem Biotechnol. 2014;174:388–397.
   PubMed Web of Science ®Google Scholar