Bioactive compounds of Crocus sativus L. and their semi-synthetic derivatives as promising anti-Helicobacter pylori, anti-malarial and anti-leishmanial agents

References

• Cui R, Zhou L. Helicobacter pylori infection: an overview in 2013, focus on therapy. Chin Med J 2014;127:568–573
   PubMed Web of Science ®Google Scholar
• Ardekani LS, Gargari SL, Rasooli I, et al. A novel nanobody against urease activity of Helicobacter pylori. Int J Infect Dis 2013;17:e723–8
   PubMed Web of Science ®Google Scholar
• Aslam MA, Mahmood SU, Shahid M, et al. Synthesis, biological assay in vitro and molecular docking studies of new Schiff base derivatives as potential urease inhibitors. Eur J Med Chem 2011;46:5473–9
   PubMed Web of Science ®Google Scholar
• Fahey JW, Stephenson KK, Wade KL, Talalay P. Urease from Helicobacter pylori is inactivated by sulforaphane and other isothiocyanates. Biochem Biophys Res Commun 2013;435:1–7
   PubMed Web of Science ®Google Scholar
• Shin IS, Masuda H, Naohide K. Bactericidal activity of wasabi (Wasabia japonica) against Helicobacter pylori. Int J Food Microbiol 2004;94:255–61
   PubMed Web of Science ®Google Scholar
• Xiao ZP, Peng ZY, Dong JJ, et al. Synthesis, structure-activity relationship analysis and kinetics study of reductive derivatives of flavonoids as Helicobacter pylori urease inhibitors. Eur J Med Chem 2013;63:685–95
   PubMed Web of Science ®Google Scholar
• Xiao ZP, Wang XD, Peng ZY, et al. Molecular docking, kinetics study, and structure-activity relationship analysis of quercetin and its analogous as Helicobacter pylori urease inhibitors. J Agric Food Chem 2012;60:10572–7
   PubMed Web of Science ®Google Scholar
• Cui K, Lu W, Zhu L, et al. Caffeic acid phenethyl ester (CAPE), an active component of propolis, inhibits Helicobacter pylori peptide deformylase activity. Biochem Biophys Res Commun 2013;435:289–94
   PubMed Web of Science ®Google Scholar
• Paz S, Tizón L, Otero JM, et al. Tetrahydrobenzothiophene derivatives: conformationally restricted inhibitors of type II dehydroquinase. Chem Med Chem 2011;6:266–72
   Web of Science ®Google Scholar
• Basarab GS, Hill P, Eyermann CJ, et al. Design of inhibitors of Helicobacter pylori glutamate racemase as selective antibacterial agents: incorporation of imidazoles onto a core pyrazolopyrimidinedione scaffold to improve bioavailabilty. Bioorg Med Chem Lett 2012;22:5600–7
   PubMed Web of Science ®Google Scholar
• Zhang L, Kong Y, Wu D, et al. Three flavonoids targeting the beta-hydroxyacyl-acyl carrier protein dehydratase from Helicobacter pylori: crystal structure characterization with enzymatic inhibition assay. Protein Sci 2008;17:1971–8
   PubMed Web of Science ®Google Scholar
• Chen J, Zhang L, Zhang Y, et al. Emodin targets the beta-hydroxyacyl-acyl carrier protein dehydratase from Helicobacter pylori: enzymatic inhibition assay with crystal structural and thermodynamic characterization. BMC Microbiol 2009;9:91
   PubMed Web of Science ®Google Scholar
• Cheng CS, Jia KF, Chen T, et al. Experimentally validated novel inhibitors of Helicobacter pylori phosphopantetheine adenylyltransferase discovered by virtual high-throughput screening. PLoS One 2013;8:e74271
   Google Scholar
• Fonvielle M, Coinçon M, Daher R, et al. Synthesis and biochemical evaluation of selective inhibitors of class II fructose bisphosphate aldolases: towards new synthetic antibiotics. Chemistry 2008;14:8521–9
   PubMed Web of Science ®Google Scholar
• Cho SO, Lim JW, Kim H. Red ginseng extract inhibits the expression of MCP-1 and iNOS in Helicobacter pylori-infected gastric epithelial cells by suppressing the activation of NADPH oxidase and Jak2/Stat3. J Ethnopharmacol 2013;150:761–4
   PubMed Web of Science ®Google Scholar
• Kappe SH, Vaughan AM, Boddey JA, Cowman AF. That was then but this is now: malaria research in the time of an eradication agenda. Science 2010;328:862–6
   PubMed Web of Science ®Google Scholar
• Pohlit AM, Lima RB, Frausin G, et al. Amazonian plant natural products: perspectives for discovery of new antimalarial drug leads. Molecules 2013;18:9219–40
   PubMed Web of Science ®Google Scholar
• Rasoanaivo P, Wright CW, Willcox ML, Gilbert B. Whole plant extracts versus single compounds for the treatment of malaria: synergy and positive interactions. Malar J 2011;10:S1–4
   PubMedGoogle Scholar
• Glaser J, Schultheis M, Hazra S, et al. Antileishmanial lead structures from nature: analysis of structure-activity relationships of a compound library derived from caffeic acid bornyl ester. Molecules 2014;19:1394–410
   PubMed Web of Science ®Google Scholar
• Sharma M, Chauhan K, Shivahare R, et al. Discovery of a new class of natural product-inspired quinazolinone hybrid as potent antileishmanial agents. J Med Chem 2013;56:4374–92
   PubMed Web of Science ®Google Scholar
• Chowdhury S, Mukherjee T, Sengupta S, et al. Novel betulin derivatives as antileishmanial agents with mode of action targeting type IB DNA topoisomerase. Mol Pharmacol 2011;80:694–703
   PubMed Web of Science ®Google Scholar
• Bathaie SZ, Mousavi SZ. New applications and mechanisms of action of saffron and its important ingredients. Crit Rev Food Sci Nutr 2010;50:761–86
   PubMed Web of Science ®Google Scholar
• (a) Sengul M, Yildiz H, Gungor N, et al. Total phenolic content, antioxidant and antimicrobial activities of some medicinal plants. Pak J Pharm Sci 2009;22:102–106; (b) Zheng CJ, Li L, Ma WH, et al. Chemical constituents and bioactivities of the liposoluble fraction from different medicinal parts of Crocus sativus. Pharm Biol 2011;49:756–63; (c) Motamedi H, Daabpou E, Gholipour M, et al. In vitro assay for the anti-brucella activity of medicinal plants against tetracycline-resistant Brucella melitensis. J Zhejiang Univ Sci B 2010;11:506–11
   Google Scholar
• Yousefi E, Eskandari A, Gharavi MJ, Khademvatan S. In vitro activity and cytotoxicity of Crocus sativus extract against Leishmania major (MRHO/IR/75/ER). Infect Dis – Drug Targets 2014;14:56–60
   PubMedGoogle Scholar
• Chimenti F, Bizzarri B, Bolasco A, et al. Synthesis and in vitro selective anti-Helicobacter pylori activity of N-substituted-2-oxo-2H-1-benzopyran-3-carboxamides. Eur J Med Chem 2006;41:208–12
   PubMed Web of Science ®Google Scholar
• Chimenti F, Bizzarri B, Bolasco A, et al. A novel class of selective anti-Helicobacter pylori agents 2-oxo-2H-chromene-3-carboxamide derivatives. Bioorg Med Chem Lett 2007;17:3065–71
   PubMed Web of Science ®Google Scholar
• Chimenti F, Bizzarri B, Bolasco A, et al. Synthesis, selective anti-Helicobacter pylori activity, and cytotoxicity of novel N-substituted-2-oxo-2H-1-benzopyran-3-carboxamides. Bioorg Med Chem Lett 2010;20:4922–6
   PubMed Web of Science ®Google Scholar
• Chimenti F, Bizzarri B, Bolasco A, et al. Synthesis and anti-Helicobacter pylori activity of 4-(coumarin-3-yl)thiazol-2-ylhydrazone derivatives. J Heterocyclic Chem 2010;47:1269–74
   Web of Science ®Google Scholar
• De Monte C, Carradori S, Chimenti P, et al. New insights into the biological properties of Crocus sativus L.: chemical modifications, human monoamine oxidases inhibition and molecular modelling studies. Eur J Med Chem 2014;82:164–71
   PubMed Web of Science ®Google Scholar
• Sisto F, Scaltrito MM, Russello G, et al. Antimicrobial susceptibility testing of Helicobacter pylori determined by microdilution method using a new medium. Curr Microbiol 2009;58:559–63
   PubMed Web of Science ®Google Scholar
• National Committee for Clinical Laboratory Standards. Methods for antimicrobial susceptibility testing of anaerobic bacteria. Approved standard M11-A6. 6th ed. Villanova, PA: National Committee for Clinical Laboratory Standards; 2004
   Google Scholar
• Trager W, Jensen JB. Human malaria parasites in continuous culture. Science 1976;193:673–5
   PubMed Web of Science ®Google Scholar
• Makler MT, Hinrichs DJ. Measurement of the lactate dehydrogenase activity of Plasmodium falciparum as an assessment of parasitemia. Am J Trop Med Hyg 1993;48:205–10
   PubMed Web of Science ®Google Scholar
• Sereno D, Lemesre JL. Use of an enzymatic micromethod to quantify amastigote stage of Leishmania amazonensis in vitro. Parasitol Res 1997;83:401–3
   PubMed Web of Science ®Google Scholar
• Berman HM, Westbrook J, Feng Z, et al. The Protein Data Bank. Nucleic Acids Res 2000;28:235–42
   PubMed Web of Science ®Google Scholar
• Schrödinger Suite 2013 Protein Preparation Wizard; Epik version 2.7, Impact version 6.2, Prime version 3.4. New York (NY): Schrödinger, LLC; 2013
   Google Scholar
• Maestro, version 9.7. New York (NY): Schrödinger, LLC; 2014
   Google Scholar
• LigPrep, version 2.9. New York (NY): Schrödinger, LLC; 2014
   Google Scholar
• Glide, version 6.2. New York (NY): Schrödinger, LLC; 2014
   Google Scholar
• Prime version 3.4. New York (NY): Schrödinger, LLC; 2014
   Google Scholar
• (a) Desmond Molecular Dynamics System, version 3.7. New York (NY): D. E. Shaw Research; 2014. (b) Maestro-Desmond Interoperability Tools, version 3.7. New York (NY): Schrödinger; 2014
   Google Scholar
• The PyMOL Molecular Graphics System, Version 1.7.0.0. New York (NY): Schrödinger, LLC
   Google Scholar