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Chemical Compounds from the Kenyan Polypore Trametes Elegans (Spreng:Fr.) Fr (Polyporaceae) and Their Antimicrobial Activity

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Chemical Compounds from the Kenyan Polypore Trametes Elegans (Spreng:Fr.) Fr (Polyporaceae) and Their Antimicrobial Activity Available online at http://www.ifgdg.org Int. J. Biol. Chem. Sci. 13(4): 2352-2359, August 2019 ISSN 1997-342X (Online), ISSN 1991-8631 (Print) Original Paper http://ajol.info/index.php/ijbcs http://indexmedicus.afro.who.int Chemical compounds from the Kenyan polypore Trametes elegans (Spreng:Fr.) Fr (Polyporaceae) and their antimicrobial activity Regina Kemunto MAYAKA1, Moses Kiprotich LANGAT2, Alice Wanjiku NJUE1, Peter Kiplagat CHEPLOGOI1 and Josiah Ouma OMOLO1* 1Department of Chemistry, Egerton University, P.O Box 536-20115 Njoro, Kenya. 2Natural Product Chemistry in the Chemical Ecology and In Vitro Group at the Jodrell Laboratory, Kew, Richmond, UK. *Corresponding author; E-mail: [email protected]. ACKNOWLEDGEMENTS The authors are grateful to the Kenya National Research Fund (NRF)-NACOSTI for the financial assistance for the present work. ABSTRACT Over the years, natural products have been used by humans in tackling infectious bacteria and fungi. Higher fungi have potential of containing natural product agents for various diseases. The aim of the study was to characterise the antimicrobial compounds from the polypore Trametes elegans. The dried, ground fruiting bodies of T. elegans were extracted with methanol and solvent removed in a rotary evaporator. The extract was suspended in distilled water, then partitioned using ethyl acetate solvent to obtain an ethyl acetate extract. The extract was fractionated and purified using column chromatographic method and further purification on sephadex LH20. The chemical structures were determined on the basis of NMR spectroscopic data from 1H and 13C NMR, HSQC, HMBC, 1H-1H COSY, and NOESY experiments. Antimicrobial activity against clinically important bacterial and fungal strains was assessed and zones of inhibition were recorded. The polypore yielded six known compounds namely ergosta-5,7,22 trien-3-ol (1) 5α,8α–epidioxyergosta-6,9(11),22-trien-3β- ol (2), 5α,8α–epidioxyergosta-6,22-dien-3β-ol (3), ergosta-7,22-dien-3β,5α,6β-triol (4), Lupeol (5) and 9,19- cycloartane-3,30-diol (6). From this study, the isolated compounds of T. elegans displayed varying antimicrobial activities with zones of inhibition ranging from 8.0 0.58 to 9.7 0.33 mm at (p≤0.05). Thus, Trametes elegans, could be considered as a potential source of natural antimicrobials. © 2019 International Formulae Group. All rights reserved. Keywords: Higher fungi, triterpenoids, disc diffusion assay. INTRODUCTION decomposers and have enormous potential for The genus Trametes Fr. (Polyporaceae, bioremediation and biodegradation activities, higher Basidiomycetes) consist of white rot making them both ecologically and polypores, that include the Trametes economically important. Trametes elegans is versicolor commonly known as ‘turkey tail’ present in almost all forest ecosystems and are fungus (Zmitrovich et al., 2012; Carlson et al., found frequently on numerous genera of 2014). The Trametes polypore species play an deciduous hardwood forests (Carlson et al., important role in natural ecosystems as wood 2014). Trametes elegans is well known for its © 2019 International Formulae Group. All rights reserved. 8221-IJBCS DOI: https://dx.doi.org/10.4314/ijbcs.v13i4.37 R. K.MAYAKA et al. / Int. J. Biol. Chem. Sci. 13(4): 2352-2359, 2019 medicinal properties, although not much voucher specimen number JO 13020/59 of research has been carried out on the medicinal Trametes elegans species was kept as properties, especially the antimicrobial herbarium in Integrated Biotechnology activities of T. elegans (Awala and Oyetayo, Research Laboratory at Egerton University. 2015). Trametes versicolor is the most studied Chinese medicinal mushroom in the genus. Its Extraction and isolation known to possess a wide range of biological The Trametes elegans macro fungi activities including immune-enhancing samples were brush-cleaned to remove any activity (Li et al., 2011), antitumor (Standish attached soil and humus, chopped into small et al., 2008) and antiviral effects (Teplyakova pieces and then air-dried under shade to et al., 2012). A preventive bioactive constant weight. The cleaned, dried fruiting mushroom extract, known as PSK (from T. bodies were ground using a mechanical versicolor mycelia), demonstrated to be blender and stored in an air-tight container for effective against carcinogenesis (Fisher and further use. The sample material (400 gm) Yang, 2002). The extract is a protein-bound was extracted with methanol for 72 hours in polysaccharide and was approved for use in dark with occasional stirring. The extract was cancer treatment by the Japanese Ministry of filtered through Whatman No. 1 filter paper Health and Welfare in 1977 (Moon and and the filtrate evaporated by rotary Shibamoto, 2009). The need to explore natural evaporator under reduced pressure and then sources for novel bioactive agents has partitioned with ethyl acetate solvent. The increased in the last three decades. Fungi are extract was fractionated (Figure 1) and among the most creative groups of eukaryotic purified using column chromatography with organisms capable of producing many novel silica gel (0.063–0.200 mm, Merck 9385). natural products that are directly used as drugs The purity was checked using TLC plates or serve as structural backbone for synthetic (Merck Art 554, 20 cm x 20 cm, silica gel 60 modifications (Stadler and Keller, 2008). The F254 coated). The Ethyl acetate extract (4 gm) aim of the current study was to evaluate the was eluted with hexane–diethyl ether gradient antibacterial and antifungal activity of the elution to obtain fractions, Fr 1 to Fr 6 (Figure compounds isolated from Trametes elegans. 1). The fractions were further subjected to repeated silica gel column chromatography MATERIALS AND METHODS eluted with dichloromethane, ethyl acetate General experimental procedures gradients to afford six sub-fractions that were NMR analysis was performed on a also repeatedly chromatographed to yield the Bruker 500 MHz NMR spectrophotometer first four pure fractions. The last two were and spectra were recorded in CDCl3 at the obtained on further purification on Sephadex University of Surrey, United Kingdom. LH20. Structures of compounds were elucidated and they were confirmed by comparison of their Antimicrobial activity NMR data against literature values. The antibacterial assay was based on the disc diffusion assay according to (CLSI, Collection of fruiting body 2012) The pathogens included gram negative The sample fruiting body of Trametes strains; Salmonella typhi, Shigella, elegans was collected from rotten wood logs Escherichia coli (E. coli), Citobacter and stumps along from Kerio Valley, Elgeyo enterocolitica and Klebsiella pneumonia. Marakwet County and Kabarnet forest, Gram positive bacteria; Streptococcus Baringo County in Kenya. The sample pyogenes, Streptococcus pneumonia, material was collected in July 2013, when the Staphylococcus aureus and Entero feacalis, rains had ended though with high humidity Fungi; Candida albicans, and Cryptococcus and the temperatures were between 18-26 ºC. neoformans. Antimicrobial activity against The identification of the polypore mushroom clinically important strains was evaluated and was done through the examination of zones of inhibition were reported as morphological features and further molecular mean SEM. identification by Dr. Leung Siu Han from Mushroom Initiative, Hong Kong. The 2353 R. K.MAYAKA et al. / Int. J. Biol. Chem. Sci. 13(4): 2352-2359, 2019 Figure 1: Flow chart showing the isolation of compounds from T. elegans. RESULTS oxygenated tertiary carbons were observed at Compound 1 (Figure 2) was obtained δc 78.6 (C-8), 82.9 (C-5) and one secondary at 13 as a white amorphous powder. Its C-NMR δc 66.6 (C-3) ppm. The oxygenated methine (Table 1) spectrum together with DEPT-135 carbon was assigned to C-3 due to the HMBC revealed 28 carbon signals that included one cross signal between a proton at δH 4.02 (1H- 1 oxygenated methine carbon at δc 70.7 and six 3) with the C-5 resonance (δC 82.9). The H olefinic carbon signals at δC 116.6, 119.8, NMR of compound 3 also exhibited signals 1 132.2, 135.8, 140.3 and 141.8. The H NMR deshielded coupled H6–H7 pair at δH 6.23 and spectrum of compound was indicative of two 6.50 and H22–H23 pair at δH 5.17 and 5.23. tertiary methyls (δH, 0.94, 0.63) and four Two oxygenated tertiary carbons were secondary methyl signals δH 0.83, 0.84, 0.91 observed at δc 79.6 (C-8), 82.4 (C-5) and one and 1.03. The other key proton resonances are secondary at δc 66.7 (C-3) ppm. The carbon at olefin protons at δH 5.57, 5.39 and a multiplet δc 82.4 (C-5) had cross correlations with δH signal between 5.19-5.21. A broad deshielded 6.50 (H-6), 6.23 (H-7), 1.91(H-4), 1.68(H-1) proton signal at δH 3.64 typical of an and 0.88(3H-19). In addition, the δc 66.7 had oxygenated methine was assigned to position HMBC correlations with δH 2.11/1.91 (2H-4), 3 in the carbon skeleton. The 1H-1H COSY 6.50 (1H-6), 1.69(H-1) and 1.53(H-2). The spectrum showed coupling between the H-6 carbon at δc 79.6 (C-8) had HMBC and H-7 resonances with J=5.2 Hz. On the correlations with δH 6.50 (H-6). The vinyl basis of the its spectral data and further proton signal of compound 2 at δH 5.40 was comparison with reported values, the structure lacking in the proton spectrum of compound of the compound was determined to be 3. The 13C spectrum of the two compounds 2 ergosta-5,7,22-trien-3β-ol. and 3 was almost similar except for the Compounds 2 and 3 (Figure 2) were presence of a double bond signals at δc 142.8 obtained as colourless crystalline needles.
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