Activity of methylgerambullin from Glycosmis species (Rutaceae) against Entamoeba histolytica and Giardia duodenalis in vitro

Mirjana Drinić1, Adriane Raninger2, Andrea Zraunig2, Florian Astelbauer1, David Leitsch1, Andreas Obwaller3,4, Julia Walochnik1, Harald Greger2, Michael Duchene1
1Institute of Specific Prophylaxis and Tropical Medicine, Center for Pathophysiology, Infectiology and Immunology, Medical University of Vienna, A-1090, Vienna, Austria
2Chemodiversity Research Group, Faculty of Life Sciences, University of Vienna, A-1030, Vienna, Austria
3Orphanidis Pharma Research GmbH, A-1160, Vienna, Austria
4CDMS Clinical Data Management and Statistics GmbH, A-1020, Vienna, Austria

Tài liệu tham khảo

Abdullah, 2006, Chemical constituents and biological actvities of Glycosmis chlorosperma var Elmeri (Merr.) stone (Rutaceae), Malays. J. Sci., 25, 45 Ahlman, 1993, Free amino acids in biopsy specimens from the human colonic mucosa, J. Surg. Res., 55, 647, 10.1006/jsre.1993.1198 Astelbauer, 2010, High antitrypanosomal activity of plant derived sulphur-containing amides, Int. J. Antimicrob. Agents, 36, 570, 10.1016/j.ijantimicag.2010.07.003 Astelbauer, 2011, Anti-leishmanial activity of plant-derived acridones, flavaglines, and sulfur-containing amides, Vector Borne Zoonotic Dis., 11, 793, 10.1089/vbz.2010.0087 Astelbauer, 2012, Activity of selected phytochemicals against Plasmodium falciparum, Acta Trop., 123, 96, 10.1016/j.actatropica.2012.04.002 Balunas, 2005, Drug discovery from medicinal plants, Life Sci., 78, 431, 10.1016/j.lfs.2005.09.012 Bendesky, 2002, Is metronidazole carcinogenic?, Mutat. Res., 511, 133, 10.1016/S1383-5742(02)00007-8 Brader, 1993, Novel prenylated 2-quinolinones from East Asian Zanthoxylum species, Liebigs Ann. Chem., 24, 355, 10.1002/jlac.199319930160 Brem, 2002 Carbonero, 2012, Microbial pathways in colonic sulfur metabolism and links with health and disease, Front. Physiol., 3, 448, 10.3389/fphys.2012.00448 Cragg, 2013, Natural products: a continuing source of novel drug leads, Biochim. Biophys. Acta, 1830, 3670, 10.1016/j.bbagen.2013.02.008 Diamond, 1978, A new medium for the axenic cultivation of Entamoeba histolytica and other Entamoeba, Trans. R. Soc. Trop. Med. Hyg., 72, 431, 10.1016/0035-9203(78)90144-X Gardner, 2001, Treatment of giardiasis, Clin. Microbiol. Rev., 14, 114, 10.1128/CMR.14.1.114-128.2001 Gargano, 2017, Mortality from selected diseases that can be transmitted by water - United States, 2003-2009, J. Water Health, 15, 438, 10.2166/wh.2017.301 Grassi, 1998 Greger, 1994, Sulfones derived from methylthiopropenoic acid-amides from Glycosmis angustifolia, Phytochemistry, 37, 1305, 10.1016/S0031-9422(00)90403-5 Greger, 2001, Insecticidal flavaglines and other compounds from Fijian Aglaia species, Phytochemistry, 57, 57, 10.1016/S0031-9422(00)00471-4 Greger, 1996, Bioactive amides from Glycosmis species, J. Nat. Prod., 59, 1163, 10.1021/np9604238 Hanna, 2000, Percutaneous catheter drainage in drug-resistant amoebic liver abscess, Trop. Med. Int. Health, 5, 578, 10.1046/j.1365-3156.2000.00586.x Havelaar, 2015, World Health Organization global estimates and regional comparisons of the burden of foodborne disease in 2010, PLoS Med., 12, 10.1371/journal.pmed.1001923 Hofer, 2000, Sulfur-containing amides from Glycosmis species (Rutaceae), vol. 80, 187 Hofer, 2000, Prenylated sulfonyl amides from Glycosmis species, Phytochemistry, 54, 207, 10.1016/S0031-9422(00)00011-X IARC, 1987, 250 Ignatius, 2012, High prevalence of Giardia duodenalis Assemblage B infection and association with underweight in Rwandan children, PLoS Neglected Trop. Dis., 6, 10.1371/journal.pntd.0001677 Jensen, 1977, Plasmodium falciparum in culture: use of outdated erythrocytes and description of the candle jar method, J. Parasitol., 63, 883, 10.2307/3279900 Keister, 1983, Axenic culture of Giardia lamblia in TYI-S-33 medium supplemented with bile, Trans. R. Soc. Trop. Med. Hyg., 77, 487, 10.1016/0035-9203(83)90120-7 Leitsch, 2007, Nitroimidazole action in Entamoeba histolytica: a central role for thioredoxin reductase, PLoS Biol., 5, 10.1371/journal.pbio.0050211 Leitsch, 2012, Nitroimidazole drugs vary in their mode of action in the human parasite Giardia lamblia, Int. J. Parasitol. Drugs Drug Resist., 2, 166, 10.1016/j.ijpddr.2012.04.002 Leitsch, 2017, Drug susceptibility testing in microaerophilic parasites: cysteine strongly affects the effectivities of metronidazole and auranofin, a novel and promising antimicrobial, Int. J. Parasitol. Drugs Drug Resist., 7, 321, 10.1016/j.ijpddr.2017.09.001 Limpert, 2001, Log-normal distributions across the sciences: keys and clues, Bioscience, 51, 341, 10.1641/0006-3568(2001)051[0341:LNDATS]2.0.CO;2 Lipinski, 1997, Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv. Drug Deliv. Rev., 23, 4, 10.1016/S0169-409X(96)00423-1 Lipinski, 2016, Rule of five in 2015 and beyond: target and ligand structural limitations, ligand chemistry structure and drug discovery project decisions, Adv. Drug Deliv. Rev., 101, 34, 10.1016/j.addr.2016.04.029 Minetti, 2016, Giardiasis, BMJ, 355 Mohamed, 2000, Apoptotic and necrotic cell death manifestations in leukemic cells treated with methylgerambullin a sulphone from Glycosmis calcicola, J. Biochem. Mol. Biol. Biophys., 4, 253 Moon, 2010, Total synthesis and biological evaluation of methylgerambullone, Bioorg. Med. Chem. Lett, 20, 52, 10.1016/j.bmcl.2009.11.040 Moreno, 1984, Distinct reduction of nitrofurans and metronidazole to free radical metabolites by Tritrichomonas foetus hydrogenosomal and cytosolic enzymes, J. Biol. Chem., 259, 8252, 10.1016/S0021-9258(17)39721-1 Müller, 1983, Mode of action of metronidazole on anaerobic bacteria and protozoa, Surgery, 93, 165 Newman, 2016, Natural products as sources of new drugs from 1981 to 2014, J. Nat. Prod., 79, 629, 10.1021/acs.jnatprod.5b01055 Nillius, 2011, Nitroreductase (GlNR1) increases susceptibility of Giardia lamblia and Escherichia coli to nitro drugs, J. Antimicrob. Chemother., 66, 1029, 10.1093/jac/dkr029 Noedl, 2008, Evidence of artemisinin-resistant malaria in western Cambodia, N. Engl. J. Med., 359, 2619, 10.1056/NEJMc0805011 Stanley, 2003, Amoebiasis, Lancet, 361, 1025, 10.1016/S0140-6736(03)12830-9 Szabo, 1985, Coumarin-hemiterpene ethers from Artemisia species, Phytochemistry, 24, 537, 10.1016/S0031-9422(00)80763-3 Tu, 2016, Artemisinin-a gift from traditional Chinese medicine to the world (Nobel Lecture), Angew Chem. Int. Ed. Engl., 55, 10210, 10.1002/anie.201601967 Turkeltaub, 2015, The intestinal protozoa: emerging impact on global health and development, Curr. Opin. Gastroenterol., 31, 38, 10.1097/MOG.0000000000000135 Upcroft, 2001, Drug targets and mechanisms of resistance in the anaerobic protozoa, Clin. Microbiol. Rev., 14, 150, 10.1128/CMR.14.1.150-164.2001 Vajrodaya, 1998 Vajrodaya, 1998, Organ-specific chemical differences in Glycosmis trichanthera, Phytochemistry, 48, 897, 10.1016/S0031-9422(97)00986-2 Wassmann, 1999, Metronidazole resistance in the protozoan parasite Entamoeba histolytica is associated with increased expression of iron-containing superoxide dismutase and peroxiredoxin and decreased expression of ferredoxin 1 and flavin reductase, J. Biol. Chem., 274, 26051, 10.1074/jbc.274.37.26051 Wink, 2012, Medicinal plants: a source of anti-parasitic secondary metabolites, Molecules, 17, 12771, 10.3390/molecules171112771