Flavonoid glycosides and limonoids from Citrus molasses.
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.
Kuroyanagi
Masanori
M
Faculty of Life and Environmental Sciences, Prefectural University of Hiroshima, 560 Nanatsuka, Shobara, Hiroshima, 727-0023, Japan. kuroyang@pu-hiroshima.ac.jp
Ishii
Hiromi
H
Kawahara
Nobuo
N
Sugimoto
Hiroyuki
H
Yamada
Hideo
H
Okihara
Kiyoshi
K
Shirota
Osamu
O
D002957:Citrus / Q000737:chemistry*; D004187:Disaccharides / Q000302:isolation & purification; D044950:Flavanones / Q000302:isolation & purification; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification*; D005638:Fruit; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification*; D006569:Hesperidin / Q000302:isolation & purification; D036701:Limonins / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D004187:Disaccharides; D044950:Flavanones; D005419:Flavonoids; D006027:Glycosides; D036701:Limonins; C500601:narirutin; D006569:Hesperidin; C028610:flavanone