A straightforward access to neohesperidose from naringin by acetolysis. Comparative behaviour of some flavonoid neohesperidosides and rutinosides under acetolysis |
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Authors: | Guy Lewin |
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Institution: | Laboratoire de Pharmacognosie (Univ. Paris-Sud BIOCIS UMR-8076 CNRS LabEx LERMIT), Faculté de Pharmacie, av. J.B. Clément, 92296 Châtenay-Malabry Cedex, France |
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Abstract: | A straightforward semisynthesis of neohesperidose was performed in three-steps with 43% overall yield starting from naringin, the main flavonoid of grapefruit. In addition, the behaviour of two pairs of flavonoid 7-O-rhamnoglucosides (neohesperidosides naringin and rhoifolin; rutinosides hesperidin and diosmin) under same acetolysis conditions was compared. Results demonstrated the crucial influence of the oxidation state of the aglycone (flavanone or flavone), and of the nature of the disaccharidic moiety on the course of the reaction. |
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Keywords: | Neohesperidose Acetolysis Naringin Flavonoids Rutinose |
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