A novel benzoyl glucoside (4) and 13 known phenolic compounds were isolated from the leaves of Camellia japonica by a guided 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. The structure of 4 was determined to be 4-hydroxy-2-methoxyphenol 1-O-β-D-(6'-O-p-hydroxylbenzoyl)-glucopyranoside (camelliadiphenoside). The 13 known compounds were identified as (E)-coniferyl alcohol (1), (-)-epicatechin (2), 4-hydroxyphenol 1-O-β-D-(6-O-p-hydroxybenzoyl) glucopyranoside (3), naringenin 7-O-β-D-glucopyranoside (5), quercetin 3-O-β-L-rhamnopyranosyl(1→6)-β-D-glucopyranoside (6), kaempferol 3-O-β-L-rhamnopyranosyl(1→6)-β-D-glucopyranoside (7), (+)-catechin (8), 1,6-di-O-p-hydroxybenzoyl-β-Dglucopyranoside (9), phloretin 2'-O-β-D-glucopyranoside (10), quercetin 3-O-β-D-glucopyranoside (11), quercetin 3-O-β-Dgalactopyranoside (12), kaempferol 3-O-β-D-galactopyranoside (13), and kaempferol 3-O-β-D-glucopyranoside (14). Their chemical structures were determined by the spectroscopic data of fast atom bondardment mass spectrometry (FABMS) and nuclear magnetic resonance (NMR). Flavonoids having the catechol moiety showed significantly higher DPPH radical scavenging activity than other isolated compounds having monohydroxy phenyl group.
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Abstract Introduction Material and Methods Plant material Chemicals Isolation of antioxidative compounds from hot waterextract Structural analysis Assay of DPPH radical scavenging Results and Discussion Antioxidative activity of solvent fractions Isolation of active compounds from the EtOAc-solubleneutral fraction Structure determination of a novel compound Identification of the 13 known compounds DPPH radical scavenging activity of the isolatedcompounds References