Pentacyclic Triterpenoids,Phytosteroids and Fatty Acid Isolated from the Stem-bark of Cola lateritia K. Schum. (Sterculiaceae) of Cameroon origin; Evaluation of Their Antibacterial Activity |
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Affiliation: | 1. Drug Discovery and Smart Molecules Research Laboratory, Department of Chemical Sciences, University of Johannesburg, P.O. Box 17011, Doornfontein, Johannesburg 2028, South Africa;2. Centre for Natural Product Research (CNPR), Chemical Sciences Department, University of Johannesburg, Doornfontein, Johannesburg 2028, South Africa;3. Research Center for Synthesis and Catalysis, Department of Chemical Sciences, University of Johannesburg-Kingsway Campus, Auckland Park, 2008, South Africa;4. Department of Organic Chemistry, The University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon;5. Department of Microbial Drugs, Helmholtz Centre for Infection Research GmbH, Inhoffenstrasse 7, 38124 Braunschweig, Germany;6. Department of Biochemistry, The University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon;7. Department of Biotechnology and Food Technology, Faculty of Science, University of Johannesburg, Doornfontein Campus, Johannesburg 2028, South Africa |
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Abstract: | The phytochemical investigation on the chemical constituents of dichloromethane-methanol (1:1) stem-bark extract of Cola lateritia K. Schum. (Sterculiaceae) led to the isolation and characterization of five pentacyclic triterpenoids, one fatty acid and two phytosteroids. The compounds were identified as heptadecanoic acid (1), maslinic acid (2), betulinic acid (3), lupenone (4), lupeol (5), friedelin (6), β-stigmasterol (7) and ß-sitosterol-3-O-ß-D-glucoside (8). Their structures were determined by NMR analysis (1H, 13C, DEPT-135, COSY, HMBC and HSQC), high-resolution mass spectrometry (HR-ESI-MS) and comparisons with published data in the literature. This work, to the best of our knowledge, is the first isolation and identification of these compounds in pure forms from Cola lateritia. Also, compounds 1–3 are reported for the first time from Cola genus. In vitro antibacterial activity of the isolated compounds (1–8) and the crude extract were evaluated against Bacillus subtilis, Staphylococcus epidermidis, Enterococcus faecalis, Mycobacterium smegmatis, Staphylococcus aureus, Enterobacter cloacae, Klebsiella oxytoca, Proteus vulgaris, Klebsiella pneumonia, Escherichia coli, Proteus mirabilis and Klebsiella aerogenes with streptomycin, nalidixic acid and ampicillin as standard antibacterial drugs. Compound 2 was active against E. faecalis (MIC = 18.5 µg/mL), and it was 6.9 and 28 times lower and active than that of streptomycin (MIC 128 µg/mL) and nalidixic acid (MIC > 512 µg/mL) respectively. All the isolated compounds and crude extract showed significant activities against the tested bacterial strains. |
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Keywords: | Fatty acid Pentacyclic triterpenoids Phytosteroids Antibacterial activity Carbon-13 nuclear magnetic resonance Proton nuclear magnetic resonance COSY" },{" #name" :" keyword" ," $" :{" id" :" k0055" }," $$" :[{" #name" :" text" ," _" :" Correlation spectroscopy NOESY" },{" #name" :" keyword" ," $" :{" id" :" k0065" }," $$" :[{" #name" :" text" ," _" :" Nuclear Overhauser effect spectroscopy d" },{" #name" :" keyword" ," $" :{" id" :" k0075" }," $$" :[{" #name" :" text" ," _" :" Doublet dd" },{" #name" :" keyword" ," $" :{" id" :" k0085" }," $$" :[{" #name" :" text" ," _" :" Doublet of doublet DEPT-135" },{" #name" :" keyword" ," $" :{" id" :" k0095" }," $$" :[{" #name" :" text" ," _" :" Distortionless Enhancement by Polarization Transfer-135 FTIR" },{" #name" :" keyword" ," $" :{" id" :" k0105" }," $$" :[{" #name" :" text" ," _" :" Fourier-transform infrared UV" },{" #name" :" keyword" ," $" :{" id" :" k0115" }," $$" :[{" #name" :" text" ," _" :" ultra-violet HMBC" },{" #name" :" keyword" ," $" :{" id" :" k0125" }," $$" :[{" #name" :" text" ," _" :" Heteronuclear multiple bond correlation HREIMS" },{" #name" :" keyword" ," $" :{" id" :" k0135" }," $$" :[{" #name" :" text" ," _" :" High resolution electron ionisation spectroscopy HSQC" },{" #name" :" keyword" ," $" :{" id" :" k0145" }," $$" :[{" #name" :" text" ," _" :" Heteronuclear single quantum coherence J" },{" #name" :" keyword" ," $" :{" id" :" k0155" }," $$" :[{" #name" :" text" ," _" :" Coupling constant Mass/charge ratio Me" },{" #name" :" keyword" ," $" :{" id" :" k0175" }," $$" :[{" #name" :" text" ," _" :" Methyl EtOAc" },{" #name" :" keyword" ," $" :{" id" :" k0185" }," $$" :[{" #name" :" text" ," _" :" ethyl acetate MeOH" },{" #name" :" keyword" ," $" :{" id" :" k0195" }," $$" :[{" #name" :" text" ," _" :" Methanol NMR" },{" #name" :" keyword" ," $" :{" id" :" k0205" }," $$" :[{" #name" :" text" ," _" :" Nuclear magnetic resonance s" },{" #name" :" keyword" ," $" :{" id" :" k0215" }," $$" :[{" #name" :" text" ," _" :" Singlet t" },{" #name" :" keyword" ," $" :{" id" :" k0225" }," $$" :[{" #name" :" text" ," _" :" Triplet TLC" },{" #name" :" keyword" ," $" :{" id" :" k0235" }," $$" :[{" #name" :" text" ," _" :" Thin Layer Chromatography TMS" },{" #name" :" keyword" ," $" :{" id" :" k0245" }," $$" :[{" #name" :" text" ," _" :" Tetramethyl silane |
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