A New Sphingolipid and Furanocoumarins with Antimicrobial Activity from &lt;i&gt;Ficus exasperata&lt;/i&gt;

Dongfack, Marlise Diane Jiofack; Lallemand, Marie‐Christine; Kuete, Victor; Mbazoa, Céline Djama; Wansi, Jean-Duplex; Trinh‐Van‐Dufat, Hanh; Michel, Sylvie; Wandji, Jean

doi:10.1248/cpb.c12-00279

Cited by 36 publications

(17 citation statements)

References 13 publications

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“…57 (dd, J = 10.4, 5.3 Hz, H-1a, 1H), 4.40 (dd, J = 10.4, 3.1 Hz, H-1b, 1H), 5.08 (m, H-2, 1H), 4.32 (dd, J = 4.7, 3.2 Hz, H-3, 1H), 4.25(td, J = 5.5, 4.7, Hz, 1H) and 4.56 (t, J = 6.5 Hz, H-2′, 1H), whereas the carbons shifts of the respective centres were appeared at δ C 61.4, 52.0, 75.5, 72.4 and 72.7, respectively, which were in complete agreement with those of sphingolipids with a 2S,3S,4R,2R′ configuration(Muralidhar et al 2005;Kang et al 2007;Riaz et al 2007;Dongfack et al 2012). The optical rotations of 1 ([α] D = +41.0) and its methanolysis products ([α] D = 8.1 and +18.9) which were comparable with those of sphingolipids with a 2S,3S,4R,2′R configurations(Muralidhar et al 2005;Kang et al 2007;Dongfack et al 2012).…”

supporting

confidence: 65%

“…The optical rotations of 1 ([α] D = +41.0) and its methanolysis products ([α] D = 8.1 and +18.9) which were comparable with those of sphingolipids with a 2S,3S,4R,2′R configurations(Muralidhar et al 2005;Kang et al 2007;Dongfack et al 2012). Based on the above data and discussion, compound 1 was finally characterised as (2S,3S,4R)-2-{[(2R,5E)-2-hydroxyoctadec-5-enoyl] amino}hexaeicosane-1,3,4-triol.Compound 2 was isolated as colourless gummy solid.…”

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confidence: 89%

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New lipoxygenase and cholinesterase inhibitory sphingolipids from Carthamus oxyacantha

Dilshad

Riaz

Saleem

et al. 2015

Natural Product Research

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Two new sphingolipids: oxyacanthin A [(2S,3S,4R)-2-{[(2R,5E)-2-hydroxyoctadec-5-enoyl]amino}hexaeicosane-1,3,4-triol; 1] and B [(2S,3S,4R)-2-{[(2R,5E)-2-hydroxyoctadec-5-enoyl]amino}hexaeicosane-1,3,4-triol-1-O-β-D-glucopyranoside; 2], together with 1-octacosanol, β-sitosterol, β-sitosterol 3-O-β-D-glucopyranoside and luteolin 7-O-β-glucopyranoside were isolated from the methanolic extract of the whole plant of Carthamus oxyacantha. Their structures were elucidated using (1)H and (13)C NMR spectra and 2D NMR analyses (HMQC, HMBC and COSY) in combination with mass spectrometry (EI-MS, HR-EI-MS, FAB-MS and HR-FAB-MS) experiments and in comparison with the literature data of the related compounds. Both the compounds 1 and 2 showed inhibitory potential against lipoxygenase (LOX) in a concentration-dependent manner with IC50 values 83.3 ± 1.3 and 245.7 ± 1.1 µM, whereas compound 2 showed inhibition against enzymes acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with IC50 values 65.3 ± 0.1 and 93.6 ± 0.1 µM, respectively.

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supporting

confidence: 65%

mentioning

confidence: 89%

New lipoxygenase and cholinesterase inhibitory sphingolipids from Carthamus oxyacantha

Dilshad

Riaz

Saleem

et al. 2015

Natural Product Research

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“…Previous studies have demonstrated that numerous sphingolipids, extracted and purified from natural sources, can act as bactericidal agents against various microorganisms 4 , 6 – 10 , 31 . Sphingolipids showed growth inhibitory activity against Gram-positive and Gram-negative bacteria, fungi or microalgae 6 – 8 , 10 , 31 . The degree of the antibacterial activity depends on the sphingolipid structure and the microorganism tested.…”

Section: Discussionmentioning

confidence: 99%

Antibacterial activity of ceramide and ceramide analogs against pathogenic Neisseria

Bécam

Walter²,

Burgert

et al. 2017

Sci Rep

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Certain fatty acids and sphingoid bases found at mucosal surfaces are known to have antibacterial activity and are thought to play a more direct role in innate immunity against bacterial infections. Herein, we analysed the antibacterial activity of sphingolipids, including the sphingoid base sphingosine as well as short-chain C6 and long-chain C16-ceramides and azido-functionalized ceramide analogs against pathogenic Neisseriae. Determination of the minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) demonstrated that short-chain ceramides and a ω-azido-functionalized C6-ceramide were active against Neisseria meningitidis and N. gonorrhoeae, whereas they were inactive against Escherichia coli and Staphylococcus aureus. Kinetic assays showed that killing of N. meningitidis occurred within 2 h with ω–azido-C6-ceramide at 1 X the MIC. Of note, at a bactericidal concentration, ω–azido-C6-ceramide had no significant toxic effect on host cells. Moreover, lipid uptake and localization was studied by flow cytometry and confocal laser scanning microscopy (CLSM) and revealed a rapid uptake by bacteria within 5 min. CLSM and super-resolution fluorescence imaging by direct stochastic optical reconstruction microscopy demonstrated homogeneous distribution of ceramide analogs in the bacterial membrane. Taken together, these data demonstrate the potent bactericidal activity of sphingosine and synthetic short-chain ceramide analogs against pathogenic Neisseriae.

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“…F. exasperata was mentioned for the treatment of malaria, wound, shingles, and abnormal foetus position in the study area. Ficusamide and bergapten were isolated from the stem bark of F. exasperata and reported to be antimicrobial [128].…”

Section: Potential Allelopathic Activity By Leachates Of Medicinal Plantmentioning

confidence: 99%

Exploring Alternative Use of Medicinal Plants for Sustainable Weed Management

et al. 2017

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This paper presents the first application of ethnobotanical studies to screen for allelopathic species among medicinal plants for sustainable weed management. This study assesses the possible relationship between ethnobotanical indices and allelopathy of medicinal plants. Ethnobotanical data were collected in 2016 by using semi-structured interviews with 140 informants in the Ejisu-Juaben Municipality, Ghana. Data were analysed using statistical tool and ethnobotanical indices including use value (UV), Fidelity Level (FL), Relative Frequency of Citation (RFC). The Sandwich and Dish pack methods were respectively used to evaluate allelopathy through leachates and volatiles of collected samples. Ninety-five species belonging to 43 families are reported in this study, with leaves (52%) cited the most utilised plant part. Cleistopholis patens (UV = 0.54; FL = 90.7%; RFC = 0.37) and Ocimum gratissimum (UV = 0.37; FL = 38.4%; RFC = 0.35) were among the most cited species. Thirty-two species showed inhibition (≥49.3%) by leachates, while twenty-four species were found with potential volatile inhibitory compounds against lettuce radicle growth. There was a significant positive correlation (Pearson) between the UV and RFC of medicinal plants and allelopathy by leaf leachates (r = 0.639 **; p = 0.01 and r = 0.653 **; p = 0.01 respectively). This systematic documentation of medicinal plants in Ejisu-Juaben Municipality shows medicinal plants with ethnomedicinal values and potential allelopathy that can be utilised in sustainable weed control.

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A New Sphingolipid and Furanocoumarins with Antimicrobial Activity from <i>Ficus exasperata</i>

Cited by 36 publications

References 13 publications

New lipoxygenase and cholinesterase inhibitory sphingolipids from Carthamus oxyacantha

New lipoxygenase and cholinesterase inhibitory sphingolipids from Carthamus oxyacantha

Antibacterial activity of ceramide and ceramide analogs against pathogenic Neisseria

Exploring Alternative Use of Medicinal Plants for Sustainable Weed Management

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