Abstract
Two new polyphenolic glucosides, 6'-O-acetylisobiflorin (1) and (2S)-3-(4-hydroxy-3-methoxyphenyl)-propane-1,2-diol 1-O-(6'-O-galloyl)-β-D-glucoside (2), were respectively isolated from the flower buds of Syzygium aromaticum and berries of Pimenta dioica. Each structure was elucidated on the basis of spectral analyses (NMR, MS and [α](D)) and chemical conversion. A total of twenty-seven known compounds from the plants were also characterized. The antioxidative activity of their extracts and the twenty-nine isolates including gallo- and ellagitannins was estimated by oxygen radical absorbance capacity (ORAC) assay, and eugenol (3), which was the most abundant ingredient in each plant extract, showed the most potent antioxidative activity [ORAC value of 39,270 µmol TE (trolox equivalent)/g].
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antioxidants / chemistry*
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Antioxidants / isolation & purification
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Antioxidants / pharmacology*
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Flowers / chemistry
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Fruit / chemistry
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Gallic Acid / analogs & derivatives*
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Gallic Acid / chemistry
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Gallic Acid / isolation & purification
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Gallic Acid / pharmacology
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Glucosides / chemistry*
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Glucosides / isolation & purification
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Glucosides / pharmacology*
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Molecular Structure
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Naphthoquinones / chemistry*
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Naphthoquinones / isolation & purification
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Naphthoquinones / pharmacology*
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Pimenta / chemistry*
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Plant Extracts / chemistry
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Plant Extracts / isolation & purification
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Plant Extracts / pharmacology
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Reactive Oxygen Species / chemistry
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Syzygium / chemistry*
Substances
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(2S)-3-(4-hydroxy-3-methoxyphenyl)-propane-1,2-diol-1-O-(6'-O-galloyl)-beta-D-glucoside
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6'-O-acetylisobiflorin
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Antioxidants
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Glucosides
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Naphthoquinones
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Plant Extracts
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Reactive Oxygen Species
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Gallic Acid