Synthesis of Rotenone-O-monosaccharide Derivatives and Their Phloem Mobility

Six monosaccharide derivatives of rotenone were designed and synthesized to assess whether rotenone could become phloem mobile by the addition of a monosaccharide group. Phloem mobility experiments showed that only d-glucose conjugates exhibit phloem transport properties in castor bean (Ricinus communis L.) seedlings. Two d-glucose conjugates, 2-O-β-d-glucopyranosyldemethylrotenone and 6′-O-β-d-glucopyranosyldalpanol, had significantly obtained systemicity compared with that of rotenone, and 6′-O-β-d-glucopyranosyldalpanol was more mobile than 2-O-β-d-glucopyranosyldemethylrotenone. Coupling with a monosaccharide core is a reasonable method for conferring phloem mobility on insecticides, but phloem mobility is also affected by the parent molecule and the position of the monosaccharide.