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

ABSTRACT 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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    • "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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    • "oleifera seeds), [4] anti-inflammatory and hepatoprotective agents (M. oleifera fruits and bark), [5] while leaf extracts have been shown to regulate thyroids status and cholesterol levels in rats. [6] Recently, this plant has attracted great interest as an important food commodity because of its high nutritional value. "
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    ABSTRACT: Moringa oleifera is a medicinal plant and an excellent dietary source of micronutrients (vitamins and minerals) and health-promoting phytochemicals (phenolic compounds, glucosinolates and isothiocyanates). Glucosinolates and isothiocyanates are known to possess anti-carcinogenic and antioxidant effects and have attracted great interest from both toxicological and pharmacological points of view, as they are able to induce phase 2 detoxification enzymes and to inhibit phase 1 activation enzymes. Phenolic compounds possess antioxidant properties and may exert a preventative effect in regards to the development of chronic degenerative diseases.The aim of this work was to assess the profile and the level of bioactive compounds in all parts of M. oleifera seedlings, by using different MS approaches. First, flow injection electrospray ionization mass spectrometry (FI-ESI-MS) fingerprinting techniques and chemometrics (PCA) were used to achieve the characterization of the different plant's organs in terms of profile of phenolic compounds and glucosinolates. Second, LC-MS and LC-MS/MS qualitative and quantitative methods were used for the identification and/or determination of phenolics and glucosinolates in M. oleifera. Copyright © 2014 John Wiley & Sons, Ltd.
    Journal of Mass Spectrometry 09/2014; 49(9). DOI:10.1002/jms.3437 · 2.38 Impact Factor
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    • "Compounds 5 and 8 were extracted from fresh moringa leaves using a modified approach to previously published methods (Cheenpracha et al., 2010). Briefly, both were initially extracted from ground leaves (200 g) in MeOH (400 mL) for 4 h at room temperature. "
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    ABSTRACT: Graphical abstract Fresh leaf concentrate of Moringa oleifera (MC) utilized in situ for bioconversion of glucosinolates (1–4) to chemically stable isothiocyanates (5–8). MC significantly reduced inflammatory biomarkers in macrophages.
    Phytochemistry 07/2014; DOI:10.1055/s-0034-1382336 · 2.55 Impact Factor
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