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Synthesis and antiperoxidant activity of new phenolic O-glycosides |
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| Authors: | Ponticelli F Trendafilova A Valoti M Saponara S Sgaragli G |
| Institution: | a Institute of Organic Chemistry, University of Siena, I-53100 Siena, Italy b Institute of Pharmacological Sciences, University of Siena, 53100 Siena, Italy |
| Abstract: | We describe the synthesis of some 3-tert-butyl-4-hydroxyphenyl D-glycopyranosides by reaction of tert-butylhydroquinone with beta-D-pentaacetyl-glucose, beta-D-pentaacetyl-galactose, 2-acetamido- and 3,4,6-tri-O-acetyl-2-butanamido-2-deoxy-beta-D-glucopyranosyl chlorides as well as the formation of anomeric 3-tert-butyl-4-hydroxyphenyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-eno-pyranosides by reaction between tert-butylhydroquinone and 3,4,6-tri-O-acetyl-D-glucal. All compounds, except 3-tert-butyl-4-hydroxyphenyl alpha- and beta-D-glucopyranosides, inhibited lipid peroxidation with a degree of potency comparable to that of tert-butyl hydroxyanisole. |
| Keywords: | Antioxidants O-Glycosylated tert-butylhydroquinones Glucals Inhibition of lipid peroxidation |
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