Synthesis and antiperoxidant activity of new phenolic O-glycosides.
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.
Ponticelli
F
F
Institute of Organic Chemistry, University of Siena, Italy. ponticelli@unisi.it
Trendafilova
A
A
Valoti
M
M
Saponara
S
S
Sgaragli
G
G
D000107:Acetylation; D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology; D001205:Ascorbic Acid / Q000378:metabolism; D001557:Benzenesulfonates / Q000378:metabolism; D005947:Glucose / Q000031:analogs & derivatives* / Q000378:metabolism; D006027:Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology; D006873:Hydroquinones / Q000737:chemistry*; D007501:Iron / Q000378:metabolism; D019787:Linoleic Acid / Q000378:metabolism; D015227:Lipid Peroxidation / Q000187:drug effects*; D008862:Microsomes, Liver / Q000378:metabolism; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D051381:Rats; D013329:Structure-Activity Relationship
D000975:Antioxidants; D001557:Benzenesulfonates; D006027:Glycosides; D006873:Hydroquinones; C105128:glucose pentaacetate; D019787:Linoleic Acid; C018855:2-tert-butylhydroquinone; D007501:Iron; D005947:Glucose; D001205:Ascorbic Acid; C029501:4-toluenesulfonic acid