Galloylglucosides from berries of Pimenta dioica.
Three new galloylglucosides, (4S)-alpha-terpineol 8-O-beta-D-(6-O-galloyl)glucopyranoside (1); (4R)-alpha-terpineol 8-O-beta-D-(6-O-galloyl)glucopyranoside (2), and 3-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol 2-O-beta-D-(6-O-galloyl)glucopyranoside (3), were isolated from the berries of Pimenta dioica together with three known compounds, gallic acid (4), pimentol (5), and eugenol 4-O-beta-D-(6-O-galloyl)glucopyranoside (6). The structures of 1-3 were elucidated on the basis of MS and NMR spectral data and enzymatic hydrolysis. These galloylglucosides (1-3, 5, and 6) showed radical-scavenging activity nearly equivalent to that of gallic acid (4) against 1,1-diphenyl-2-picrylhydrazyl radical.
Kikuzaki
H
H
Department of Food and Nutrition, Faculty of Human Life Science, Osaka City University, Sumiyoshi, Osaka 558-8585, Japan.
Sato
A
A
Mayahara
Y
Y
Nakatani
N
N
D000081005:Cyclohexane Monoterpenes; D005609:Free Radicals; D005638:Fruit / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D039821:Monoterpenes; D010936:Plant Extracts / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D019685:Rosales / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification*
D000081005:Cyclohexane Monoterpenes; D005609:Free Radicals; D005960:Glucosides; D039821:Monoterpenes; D010936:Plant Extracts; D013729:Terpenes; C412942:terpineol-8-O-(6-O-galloyl)glucopyranoside