Soluble polyphenols: synthesis and bioavailability of 3,4',5-tri(alpha-D-glucose-3-O-succinyl) resveratrol.
We report the development of a chemical modification method of general applicability to polyphenols, which increases solubility to influence absorption. Glucosyl groups were added to the resveratrol kernel via a succinate linker, yielding 3,4',5-tri-(alpha-D-glucose-3-O-succinyl) resveratrol. The construct was only slowly hydrolyzed in acid and at pH 6.8, but it was destroyed by blood esterases in less than 1h. In rats its administration resulted in a blood concentration versus time curve shifted to longer times in comparison to resveratrol, a useful modulation of pharmacokinetics. The area-under-curve parameter and the metabolite mix were similar to those of resveratrol. The method may be advantageously employed to solubilize other polyphenols and to make them more palatable.
Biasutto
Lucia
L
Department of Biomedical Sciences, 35131 Padova, Italy.
Marotta
Ester
E
Bradaschia
Alice
A
Fallica
Mauro
M
Mattarei
Andrea
A
Garbisa
Spiridione
S
Zoratti
Mario
M
Paradisi
Cristina
C
D000818:Animals; D001682:Biological Availability; D005419:Flavonoids / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics*; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics*; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics*; D059808:Polyphenols; D051381:Rats; D012995:Solubility; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics*; D013997:Time Factors
C546452:3,4',5-tri(glucose-3-O-succinyl)resveratrol; D005419:Flavonoids; D005960:Glucosides; D010636:Phenols; D059808:Polyphenols; D013267:Stilbenes