isonaringin and flavanone

Grapefruits grown under organic or conventional systems were analyzed for 6,7-dihydroxybergamottin (DHB) and flavanones using HPLC, and DPPH activity and ORAC using a micro-plate reader. Grapefruits harvested in November 2008 (E-1) and February 2010 (E-2) were stored at room temperature (RT) and 9 °C for four weeks. Higher levels of DHB were observed in conventional grapefruits during the second (4.7 ± 0.2 μg/g), third (1.5 ± 0.2 μg/g) and fourth (2.5 ± 0.2 μg/g) week of storage at room temperature in E2. Among flavonoids analyzed, narirutin (666.7 ± 33.9 μg/g), neohesperidin (17.5 ± 1.3 μg/g), didymin (75.5 ± 5.6 μg/g) and poncirin (130.8 ± 10.4 μg/g) levels were significantly higher (P⩽0.05) in organic grapefruits over conventional grapefruits at harvest and storage in E-1. Although DPPH levels were moderately correlated with grapefruit flavanone content, variability in the individual flavanone activity was pronounced, resulting in non-significant differences in antioxidant activity between organic and conventional grapefruits.

Topics: Agriculture; Antioxidants; Chromatography, High Pressure Liquid; Citrus paradisi; Disaccharides; Flavanones; Flavonoids; Food Preservation; Fruit; Furocoumarins; Organic Agriculture

The hydrolytic activity of the recombinant β-glucosidase from Pyrococcus furiosus for the flavanone glycoside hesperidin was optimal at pH 5.5 and 95 °C in the presence of 0.5% (v/v) dimethyl sulfoxide (DMSO) and 0.1% (w/v) Tween 40 with a half-life of 88 h, a Km of 1.6 mM, and a kcat of 68.4 1/s. The specific activity of the enzyme for flavonoid glycosides followed the order hesperidin > neohesperidin > naringin > narirutin > poncirin > diosmin > neoponcirin > rutin. The specific activity for flavanone was higher than that for flavone or flavonol. DMSO at 10% (v/v) was used to increase the solubility of flavanone glycosides as substrates. The enzyme completely converted flavanone glycosides (1 g/L) to flavanone aglycones and disaccharides via one-step reaction. The major flavanone in grapefruit peel, grapefruit pulp, or orange peel extract was naringin (47.5 mg/g), naringin (16.6 mg/g), or hesperidin (18.2 mg/g), respectively. β-Glucosidase from P. furiosus completely converted naringin and narirutin in 100% (w/v) grapefruit peel extract to 22.5 g/L naringenin after 12 h, with a productivity of 1.88 g L(-1) h(-1); naringin and narirutin in 100% (w/v) grapefruit pulp extract to 8.1 g/L naringenin after 9 h, with a productivity of 0.90 g L(-1) h(-1); and hesperidin in 100% (w/v) orange peel extract to 9.0 g/L hesperetin after 9 h, with a productivity of 1.00 g L(-1) h(-1). The conversion yields, concentrations, and productivities of flavanone aglycones in this study are the highest among those obtained from citrus extracts. Thus, this enzyme may be useful for the industrial hydrolysis of flavanone glycosides in citrus extracts.

Topics: beta-Glucosidase; Citrus; Detergents; Disaccharides; Flavanones; Flavonoids; Food Industry; Glycosides; Hesperidin; Hydrogen-Ion Concentration; Hydrolysis; Kinetics; Plant Extracts; Pyrococcus furiosus; Solvents; Substrate Specificity; Temperature

Molasses of tangerine orange (Citrus unshiu Markovich) is obtained as a waste product in the course of tangerine orange juice production. This molasses is expected to be a useful source of organic compounds such as flavonoids and limonoids. To elucidate a use for this molasses waste, we isolated and identified its organic constituents. Two new flavanonol glycosides were isolated from tangerine orange molasses, along with several flavonoids such as hesperidine, narirutin, eriodictyol, 3',4',5,6,7,8-hexamethoxy-3-O-beta-D-glucopyranosyloxyflavone, and 3',4',5,6,7,8-hexamethoxy- 3-beta-D-[4-O-(3-hydroxy-3-methylglutaloyl)]-glucopyranosyloxyflavone, and limonoids such as limonin, nomilin, and cyclic peptide, citrusin III. The structures of the new flavanonol glycosides were determined as (2R,3R)-7-O-(6-O-alpha-L-rahmnopyranosyl-beta-D-glucopyranosyl)-aromadendrin and 7-O-(6-O-alpha-L-rahmnopyranosyl-beta-D-glucopyranosyl)-3,3',5,7-tetrahydroxy-4'-methoxyflavanone by means of spectral analyses using (1)H-NMR, (13)C-NMR, and 2D-NMR. Of these compounds, flavanone glycoside, hesperidin and narirutin were isolated as the main constituents. Thus, molasses is a promising source of flavonoid glycosides.

Topics: Citrus; Disaccharides; Flavanones; Flavonoids; Fruit; Glycosides; Hesperidin; Limonins; Magnetic Resonance Spectroscopy; Molecular Structure