Tracking leading anti-Candida compounds in plant samples; Plumbago europaea
Background 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.
|Issue||Vol 10 No 3 (2018)|
|Bio-autography Plumbagin Candida albicans Gardnerella vaginalis|
|Rights and permissions|
|This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.|