Characterization and antimicrobial activity of 4-(β-d-glucopyranosyl-1→4-α-l-rhamnopyranosyloxy)-benzyl thiocarboxamide; a novel bioactive compound from Moringa oleifera seed extract

Abstract

Antimicrobial activity of crude seed extract of Moringa oleifera was investigated by thin layer chromatography bioassay against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Cladosporium cladosporioides, and Penicillium sclerotigenum; most of them were prominently inhibited by an isolate with R(F) 0.92-0.96. Characterization and identification of the extract revealed the occurrence of three bioactive compounds: 4-(α-L-rhamnopyranosyloxy)benzyl isothiocyanate, methyl N-4-(α-L-rhamnopyranosyloxy) benzyl carbamate (both known compounds), and 4-(β-D-glucopyranosyl-1→4-α-L-rhamnopyranosyloxy)-benzyl thiocarboxamide, existence of which in any Moringa spp. or plant is reported for the first time. The UV spectrum of the novel compound showed maximum absorption at 273 and 225 nm in MeOH while the IR spectrum revealed several characteristic bands at 3100, 2900, 1700, 1500, 1300, 1100 and 1000 cm(-1). The (1)H-NMR showed signals at 1.2 and 3.77 ppm and the (13)C-NMR presented signals at 155, 122, 91.7 and 98.4 ppm. All the compounds at 5 mg/L had very high bactericidal activity against some of test pathogens even at contact period 1-2 h. 4-(β-D-Glucopyranosyl-1→4-α-L-rhamnopyranosyloxy)benzyl thiocarboxamide was the most potent, with 99.2 % inhibition toward Shigella dysenteriae and 100 % toward Bacillus cereus, E. coli and Salmonella typhi within 4 h of contact.

Effect of extraction methods on physicochemical, nutritional, antinutritional, antioxidant and antimicrobial activity of Moringa (Moringa oleifera Lam.) seed kernel oil

“…The seeds can be eaten as such green and roasted; powdered and soaked seeds are used for tea as well as in curries (Anwar et al, 2006). The seeds have powerful coagulative and anti-microbial properties on pathogenic strains of Escherichia coli, Pseudomonas aeruginosa, Streptococcus faecalis, Salmonella typhi and Shigella dysenteriae (Oluduro et al, 2010). Important bioactive compounds present in the moringa seeds have been used for anti-microbial, antigenotoxic, anti-inflammatory and anti-tumour promoting activities (Prabhu et al, 2011).…”

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“…In Marumoside A, the aglycone moiety is structurally related to potential antiinflammatory active Capsaicin and hydroxyphenylacetamides, the bioactivity of these compounds strictly depend on the fatty amine moiety. In the present study, the antiinflammatory activities of all the synthesized compounds (14)(15)(16)(17)(18)(19)(20)(21)(22)(23) were tested and the inhibition of TNF-α and IL-1β secretion as a measure of anti-inflammatory activity was monitored. The data to this regard are presented in Tables 2 and 3. Antioxidant activity: Marumoside A and its synthesized derivatives were tested for the DPPH free radical scavenging activity (see Table 4).…”

“…tumor, antiinflammatory, antimicrobial, antioxidant and antihypertensive activities 11,[13][14][15][16][17] . Recently, Marumoside A and other compounds were isolated from the leaves of Moringa oleifera of Thai origin 18 .…”

Study on Processing Technology and Quality of Moringa oleifera leaves with y - Aminobutyric Acid

“…Moringa oleifera Lam, is a species belonging to the Moringa Branch and Moringaceae family, widely distributed intropical and subtropical regions of Asia, Africa [1] .The whole plant has edible value and can be useful [2] .Its roots, stems, leaves, flowers, seeds, branches and barks are rich in nutrients and medicinal ingredients [3] . Studies have shown that Moringa leaves are rich in potassium, calcium, phosphorus, iron, and essential amino acids, and having antioxidant activity of vitamin C, flavonoids and polyphenols substances [3] .…”