Tracking leading anti-Candida compounds in plant samples; Plumbago europaea
AbstractBackground and Objectives: Due to the importance of finding new and more effective antifungal and antibacterial compounds against invasive vaginitis strains, this study was conducted for fast screening of plant samples.Materials and Methods: Thirty Iranian plant samples were successively extracted by n-hexane, ethyl acetate and methanol to obtain a total of 90 extracts. Each extract was prepared in six concentrations and evaluated for antifungal activity via a micro-broth dilution method. Further phytochemical study of the aerial parts of Plumbago europaea, as the most promising source of anti-Candida compounds (with minimum inhibitory concentration of about 7µg/ml), was carried out and antifungal activity in the ethyl acetate extract was tracked using a combination of HPLC time-based fractionation and Thin Layer Chromatography-Bioautography via a bioassay-guided fractionation procedure. The compounds in the active region of the chromatogram were purified by a combination of column chromatography and preparative TLC, and then structure elucidation was achieved by 1D and 2D NMR, mass spectrometry and UV spectra.Results: Seven compounds were isolated and identified: (1) plumbagin, (2) isoplumbagin, (3) 5, 8-dihydroxy-2-methyl-[1, 4] naphthoquinone, (4) droserone, (5) 7-methyljuglone, (6) Isozeylanone, and (7) methylene-3, 3’-diplumbagin. Antimicrobial activity of the purified compounds were also evaluated against C. albicans (MIC values ranging from 2 to 2500 µM) and Gardnerella vaginalis (MIC values ranging from 20 to 2500 µM).Conclusion: These naphthoquinone compounds could be surveyed for finding new and more effective anti-vaginitis agents via drug design approaches.
Favre-Godal Q, Queiroz EF, Wolfender JL. Latest developments in assessing antifungal activity using TLC-bioautography: a review. J AOAC Int 2013; 96:1175-1188.
Azzollini A, Favre-Godal Q, Zhang J, Marcourt L, Ebrahimi SN, Wang S, et al. Preparative scale MS-guided isolation of Bioactive compounds using high-resolution flash chromatography: Antifungals from Chiloscyphus polyanthos as a case study. Planta Med 2016; 82:1051-1057.
Cui J, Ren B, Tong Y, Dai H, Zhang L. Synergistic combinations of antifungals and anti-virulence agents to fight against Candida albicans. Virulence 2015; 6:362-371.
Adams M, Zimmermann S, Kaiser M, Brun R, Hamburger M. A protocol for HPLC-based activity profiling for natural products with activities against tropical parasites. Nat Prod Commun 2009; 4:1377-1381.
Cretton S, Dorsaz S, Azzollini A, Favre-Godal Q, Marcourt L, Ebrahimi SN, et al. Antifungal Quinoline Alkaloids from Waltheria indica. J Nat Prod 2016; 79:300-307.
Gindro K, Schnee S, Righi D, Marcourt L, Nejad Ebrahimi S, Codina JM, et al. Generation of antifungal stilbenes using the enzymatic secretome of Botrytis cinerea. J Nat Prod 2017; 80:887-898.
Navaei, MN, Mirza M, Dini M. Chemical composition of the essential oil of Plumbago europaea L. roots from Iran. Flavour Fragr J 2005; 20:213-214.
Paiva SR, Marques SS, Figueiredo MR, Kaplan MAC. Plumbaginales: A pharmacological approach. Florestae Ambiente 203; 10:98.
Cox C, McKenna JP, Watt AP, Coyle PV. New assay for Gardnerella vaginalis loads correlates with Nugent scores and has potential in the diagnosis of bacterial vaginosis. J Med Microbiol 2015; 64:978-984.
Favre-Godal Q, Dorsaz S, Queiroz EF, Marcourt L, Ebrahimi SN, Allard PM, et al. Anti-Candida cassane-type diterpenoids from the Root Bark of Swartzia simplex. J Nat Prod 2015; 78:2994-3004.
Espinel-Ingroff, A and Pfaller, MA (2007) Susceptibility test methods: yeasts and filamentous fungi, In: Murray PR, Baron EJ, Jorgensen JH, Pfaller MA, Yolken FC, Yolken RH. Manual of Clinical Microbiology. ASM Press Washington DC. 9th ed:pp 1972-1986.
Jorgensen JH, TJ, Washington DC (2007) Antibacterial susceptibility tests: dilution and disk diffusion methods, In: Murray PR, Baron EJ, Jorgensen JH, Pfaller MA, Yolken FC, Yolken RH. Manual of Clinical Microbiology. ASM Press Washington DC. 9th ed:pp 1152-1172.
Sagatova AA, Keniya MV, Wilson RK, Monk BC, Tyndall JD. Structural Insights into Binding of the Antifungal Drug Fluconazole to Saccharomyces cerevisiae Lanosterol 14α-Demethylase. Antimicrob Agents Chemother 2015; 59:4982-4989.
Hassan ST, Berchová-Bímová K, Petráš J. Plumbagin, a plant-derived compound, exhibits antifungal combinatory effect with amphotericin B against Candida albicans clinical isolates and anti-hepatitis C virus activity. Phytother Res 2016; 30:1487-1492.
Nair SV, Baranwal G, Chatterjee M, Sachu A, Vasudevan AK, Bose C, et al. Antimicrobial activity of plumbagin, a naturally occurring naphthoquinone from Plumbago rosea, against Staphylococcus aureus and Candida albicans. Int J Med Microbiol 2016; 306:237-248.
Wang SX, Wang J, Shao JB, Tang WN, Zhong JQ. Plumbagin mediates cardioprotection against myocardial ischemia/reperfusion injury through Nrf-2 signaling. Med Sci Monit 2016; 22:1250-1257.
Bentinger M, Tekle M, Dallner G. Coenzyme Q–biosynthesis and functions. Biochem Biophys Res Commun 2010; 396:74-79.