Antimicrobial Prenylated Dihydrochalcones from <i>Eriosema glomerata</i>

Awouafack, Maurice D.; Kouam, Siméon F.; Hussain, Hidayat; Ngamga, Dieudonne; Tané, Pierre; Schulz, Barbara; Green, Ivan R.; Krohn, Karsten

doi:10.1055/s-2007-993782

Cited by 38 publications

(29 citation statements)

References 23 publications

(38 reference statements)

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“…Compound 8 , obtained from the most antibacterial-active part, fraction A, had the highest antibacterial activity amongst all the isolated compounds with an average MIC of 55.1 μg/ml and average total activity of 20 ml/mg. The antibacterial activity of compound 8 is in agreement with previous results reported on the antimicrobial activity of similar compounds bearing the prenyl group on their structures [6,24]. Robusflavones A ( 1 ) and B ( 2 ) characterized earlier as two new antioxidant flavones [4] had moderate activities against fungi and bacteria with mean MIC values of 165, 88, 203.3 and 94 μg/ml, and average total activities of 8, 11, 7 and 12 ml/mg, respectively.…”

Section: Resultssupporting

confidence: 90%

“…Previous phytochemical study on this species led to the isolation and characterization of two flavonoids, robusflavones A and B, and five known compounds [4]. As part of our ongoing study for bioactive secondary metabolites from species of the Fabaceae family [4-6], we have re-investigated the ethanol extract of the twigs of E. robustum using bioassay-guided fractionation. To investigate the potential use of an extract, fractions or compounds, the cellular toxicity also has to be determined.…”

Section: Introductionmentioning

confidence: 99%

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Antimicrobial activity and cytotoxicity of the ethanol extract, fractions and eight compounds isolated from Eriosema robustum (Fabaceae)

Awouafack

McGaw

Gottfried

et al. 2013

BMC Complement Altern Med

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103

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BackgroundThe aim of this study was to evaluate the antimicrobial activity and the cytotoxicity of the ethanol crude extract, fractions and isolated compounds from the twigs of Eriosema robustum, a plant used for the treatment of coughs and skin diseases.MethodsColumn chromatographic and spectroscopic techniques were used to isolate and identify eight compounds, robusflavones A (1) and B (2), orostachyscerebroside A (3), stigmasterol (4), 1-O-heptatriacontanoyl glycerol (5), eicosanoic acid (6), 3-O-β-D-glucopyranoside of sitosterol (7) and 6-prenylpinocembrin (8), from E. robustum. A two-fold serial microdilution method was used to determine the minimum inhibitory concentration (MIC) against fungi and bacteria, and the 3-(4,5-dimethylthiazolyl-2)-2,5-diphenyltetrazolium bromide reduction assay was used to evaluate the cytotoxicity.ResultsFraction B had significant antimicrobial activity against Aspergillus fumigatus and Cryptoccocus neoformans (MIC 0.08 mg/ml), whilst the crude extract and fraction A had moderate activity against A. fumigatus and Candida albicans (MIC 0.16 mg/ml). Fraction A however had excellent activity against Staphylococcus aureus (MIC 0.02 mg/ml), Enterococcus faecalis and Escherichia coli (MIC 0.04 mg/ml). The crude extract had significant activity against S. aureus, E. faecalis and E. coli. Fraction B had good activity against E. faecalis and E. coli (MIC 0.08 mg/ml). All the isolated compounds had a relatively weak antimicrobial activity. An MIC of 65 μg/ml was obtained with robusflavones A (1) and B (2) against C. albicans and A. fumigatus, orostachyscerebroside A (3) against A. fumigatus, and robusflavone B (2) against C. neoformans. Compound 8 had the best activity against bacteria (average MIC 55 μg/ml). The 3 fractions and isolated compounds had LC50 values between 13.20 to > 100 μg/ml against Vero cells yielding selectivity indices between 0.01 and 1.58.ConclusionThe isolated compounds generally had a much lower activity than expected based on the activity of the fractions from which they were isolated. This may be the result of synergism between different compounds in the complex extracts or fractions. The results support the traditional use of E. robustum to treat infections. The crude extract had a good activity and low preparation cost, and may be useful in topical applications to combat microbial infections.

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Section: Resultssupporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Antimicrobial activity and cytotoxicity of the ethanol extract, fractions and eight compounds isolated from Eriosema robustum (Fabaceae)

Awouafack

McGaw

Gottfried

et al. 2013

BMC Complement Altern Med

Self Cite

103

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“…Finally, the observed fragment ions at m/z 105 and 91 in the MS of 1 confirmed a dihydrochalcone-type structure [5]. On the basis of its spectroscopic data, metabolite 1 was identified as dihydroisocordoin, a dihydrochalcone previously reported as an intermediate in the semisynthesis of tetrahydroflemichapparin-A [6], and recently reported as erioschalcone B, a novel bioactive (antimicrobial) natural product from Eriosema glomerata [7].…”

Section: Resultsmentioning

confidence: 74%

Isocordoin Derivatives From the Root Extract of Lonchocarpus xuul

Yam-Puc

Peña‐Rodríguez

2019

J. Mex. Chem. Soc.

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“…[1][2][3][4][5][6] Among the rich variety of natural prenylated molecules, chromane and chromene derivatives, with an extra pyrano or dihydropyrano ring, represent a family of compounds endowed with most interesting properties. 7 All these molecules are generally characterized by low cellular toxicity and good membrane permeability, properties that make them ideal drug template compounds.…”

Section: Introductionmentioning

confidence: 99%