Nuxia oppositifolia is traditionally used in diabetes treatment in many Arabian countries; however, scientific evidence is lacking. Hence, the present study explored the antidiabetic and antioxidant activities of the plant extracts and their purified compounds. The methanolic crude extract of N. oppositifolia was partitioned using a two-solvent system. The n-hexane fraction was purified by silica gel column chromatography to yield several compounds including katononic acid and 3-oxolupenal. Antidiabetic activities were assessed by α-amylase and α-glucosidase enzyme inhibition. Antioxidant capacities were examined by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) scavenging assays. Further, the interaction between enzymes (α-amylase and α-glucosidase) and ligands (3-oxolupenal and katononic acid) was followed by fluorescence quenching and molecular docking studies. 3-oxolupenal and katononic acid showed IC50 values of 46.2 μg/mL (101.6 µM) and 52.4 μg/mL (119.3 µM), respectively against the amylase inhibition. 3-oxolupenal (62.3 µg/mL or 141.9 μM) exhibited more potent inhibition against α-glucosidases compared to katononic acid (88.6 µg/mL or 194.8 μM). In terms of antioxidant activity, the relatively polar crude extract and n-butanol fraction showed the greatest DPPH and ABTS scavenging activity. However, the antioxidant activities of the purified compounds were in the low to moderate range. Molecular docking studies confirmed that 3-oxolupenal and katononic acid interacted strongly with the active site residues of both α-amylase and α-glucosidase. Fluorescence quenching results also suggest that 3-oxolupenal and katononic acid have a good affinity towards both α-amylase and α-glucosidase enzymes. This study provides preliminary data for the plant’s use in the treatment of type 2 diabetes mellitus.

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Two new flavonol glycosides, myricetin 4'-O-α-l-rhamnopyranoside (1) and quercetin 3'-O-α-l-rhamnopyranoside (2), together with a novel biflavonol compound, speciin (3), as well as eleven phenolic metabolites, namely myricitrin (4), europetin 3-O-α-l-1C4-rhamnopyranoside (5), quercitrin (6), hyperin (7), rhamnetin 3-O-β-galacto-pyranoside (8), caffeic acid (9), caffeic acid methyl ester (10), chlorogenic acid (11), chlorogenic acid methyl ester (12), gallic acid (13) and gallic acid methyl ester (14), were identified from the 80 % methanol extract of the aerial parts (leaves and stems) of Oenothera speciosa Nutt. (Onagraceae). In addition myricetin (15), quercetin (16) and ellagic acid (17) were identified from the chloroform extract. The structures were established depending on their chemical and physical analyses (UV, HR-ESIMS, 1D and 2D NMR). It was found that 80 % aqueous methanol extract of O. speciosa is non-toxic to mice up to 5 g kg-1b.wt. The investigated extract exhibited significant antihyperglycaemic and anti-inflammatory activities in a dose dependant manner. Also, the 80 % methanol extract, myricitrin (4) and hyperin (7) showed potent antioxidant activity in vitro using 1,1-diphenyl 2-picryl hydrazyl (DPPH) radical assay.

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2 new flavonoid glycosides, kaempferol 3-O-(4",6"-di-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside (1) and quercetin 3-O-(4",6"-di-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside (2), were isolated from the n-butanol soluble fraction of the methanol extract (BF) of Astragalus abyssinicus aerial parts, together with 3 known compounds, rutin (3), kaempferol 3-O-β-D-rutinoside (4) and 5,7,4'-trihydroxy-3'-methoxyisoflavone (5). The structures of the isolated compounds were characterized on the basis of UV, NMR and negative ESI-MS analyses. The BF fraction showed in vitro weak antibacterial activity against Staphylococcus aureus, while 2 and 3 exhibited in vitro antioxidant activity higher than ascorbic acid using DPPH free radical scavenging activity method.

The promising compounds could be employed as useful scaffolds for building of new derivatives with more potent antimicrobial effects.