Chemical synthesis of citrus flavanone glucuronides.
Flavanone glucuronides are the major phenolic metabolites detected in human plasma after consumption of citrus fruits. As such, they might display significant cardioprotective effects. In this work, glucuronides of naringenin (4'- and 7-O-beta-d-glucuronides) and hesperetin (3'- and 7-O-beta-d-glucuronides), the major flavanone aglycones in grapefruit and orange, respectively, have been chemically synthesized. On the one hand, the most reactive hydroxyl group, C7-OH, was protected by selective benzoylation to allow subsequent glucuronidation of C4'-OH (naringenin) or C3'-OH (hesperetin) (B-ring). On the other hand, the selective debenzoylation at C7-OH of the perbenzoylated flavanone aglycones allowed glucuronidation at the same position (A-ring). After careful deprotection, the target compounds were purified and characterized by nuclear magnetic resonance and mass spectrometry.
Khan
Muhammad Kamran
MK
University of Avignon, INRA, UMR408, Avignon, France.
Rakotomanomana
Njara
N
Loonis
Michele
M
Dangles
Olivier
O
D002957:Citrus / Q000737:chemistry*; D044950:Flavanones / Q000138:chemical synthesis* / Q000737:chemistry; D020719:Glucuronides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010936:Plant Extracts / Q000138:chemical synthesis* / Q000737:chemistry
D044950:Flavanones; D020719:Glucuronides; D010936:Plant Extracts