Potential anti-inflammatory phenolic glycosides from the medicinal plant Moringa oleifera fruits. Bioorg Med Chem

Department of Pharmaceutical Sciences, College of Pharmacy, University of Hawaii at Hilo, 34 Rainbow Drive, Hilo, HI 96720, USA.
Bioorganic & medicinal chemistry (Impact Factor: 2.79). 09/2010; 18(17):6598-602. DOI: 10.1016/j.bmc.2010.03.057
Source: PubMed


Bioassay-guided isolation and purification of the ethyl acetate extract of Moringa oleifera fruits yielded three new phenolic glycosides; 4-[(2'-O-acetyl-alpha-l-rhamnosyloxy) benzyl]isothiocyanate (1), 4-[(3'-O-acetyl-alpha-l-rhamnosyloxy)benzyl]isothiocyanate (2), and S-methyl-N-{4-[(alpha-l-rhamnosyloxy)benzyl]}thiocarbamate (3), together with five known phenolic glycosides (4-8). The structures of the new metabolites were determined on the basis of spectroscopic analyses including 1D- and 2D-NMR and mass spectrometry. The anti-inflammatory activity of isolated compounds was investigated with the lipopolysaccharide (LPS)-induced murine macrophage RAW 264.7 cell line. It was found that 4-[(2'-O-acetyl-alpha-l-rhamnosyloxy)benzyl]isothiocyanate (1) possessed potent NO-inhibitory activity with an IC(50) value of 1.67 microM, followed by 2 (IC(50)=2.66 microM), 4 (IC(50)=2.71 microM), and 5 (IC(50)=14.4 microM), respectively. Western blots demonstrated these compounds reduced LPS-mediated iNOS expression. In the concentration range of the IC(50) values, no significant cytotoxicity was noted. Structure-activity relationships following NO-release indicated: (1) the isothiocyanate group was essential for activity, (2) acetylation of the isothiocyanate derivatives at C-2' or at C-3' of rhamnose led to higher activity, (3) un-acetylated isothiocyanate derivatives displayed eight times less activity than the acetylated derivatives, and (4) acetylation of the thiocarbamate derivatives enhanced activity. These data indicate compounds 1, 2, 4 and 5 are responsible for the reported NO-inhibitory effect of Moringa oleifera fruits, and further studies are warranted.

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    • "microM), respectively. These isolated compounds 1, 2, 4 and 5 are responsible for the reported NO-inhibitory effect of M. oleifera fruits 29 (Cheenpracha et al., 2010 "

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    • "So far, only phospholipids, glyco-lipopeptides and a weak emulsifier glycolipid have been reported from an Aspergillus species, A. ustus and Penicillium citrinum respectively (Camargo-de-Morais et al. 2003; Hewald et al. 2006; Bhardwaj et al. 2013; Hussain et al. 2014a). Although, glycosides of phenyl oximes or phenyl cyanides like amygdalin, niazimicin, glucotropaeolin and prunasin with important medicinal properties have been reported from plants, however, data on their surface activity is lacking (Murakami et al. 1998; Cheenpracha et al. 2010). "
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    ABSTRACT: AimThis work was conducted to produce, purify and characterize biosurfactants from Aspergillus flavus AF612 isolated from citrus fruit.Methods and resultsBiosurfactant named “Uzmaq” was isolated from Aspergillus flavus AF612. The chemical characterization of the biosurfactant was conducted. Biosurfactant Uzmaq produced by A. flavus, was composed of methoxy phenyl oxime glycosides. Two molecular forms of the biosurfactant, Uzmaq-A and Uzmaq-B were isolated. Biological properties (antifungal activity) were evaluated. The fractions of the biosurfactant were isolated and their surface properties were analysed. Uzmaq-A and Uzmaq-B had critical micelle concentration (CMC) around 170 mg l-1 and 80 mg l-1, and lowered surface tension of water upto 20m Nm-1 and 25m Nm-1 respectively. The biosurfactants were stable at pH 3-12 and temperature upto 80°C. Growth and biosurfactant production kinetics were also analysed.Conclusion Novel biosurfactant Uzmaq was produced from A. flavus, which was composed of methoxy phenyl oxime glycosides. The surface activity of Uzmaq was better than the maximum values of synthetic chemical surfactants. The biosurfactant showed antifungal activity and self-assembling properties.Significance and impact of the studyAspergillus flavus AF612 can be used for commercial production of Uzmaq that may be employed for controlled drug release applications and bioremediation.This article is protected by copyright. All rights reserved.
    Journal of Applied Microbiology 08/2015; 119(4). DOI:10.1111/jam.12929 · 2.48 Impact Factor
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    • "The various extracts of its morphological parts such as seeds cotyledon, seeds' coat, stem bark, leaves, root bark have been reported to have antimicrobial potential (Arora et al., 2013). There is no major work on antimicrobial activity of pods' husks except other pharmacological potentials such as Cholesterol reduction (Mehta et al., 2003), hypotensive (Faizi et al., 1998), antiurolithiatic (Vijayalakshmi Satish et al., 2010), anti-inflammatory (Cheenpracha et al., 2010), hepatoprotective (Paliwal et al., 2011) and bioenhancer (Shanker et al., 2007). However, recently Onsare et al. (2013) have reported preliminary work on the antimicrobial activity of aqueous extract of pods' husks against Gram positive, Gram negative pathogenic bacteria and yeast strains. "

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