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.
State Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources, and ‡Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education, South China Agricultural University , Guangzhou, Guangdong 510642, People's Republic of China.
Pei-Wen
PW
Qin
Jie
J
Wang
Hao
H
Wang
Ying-Jie
YJ
Wen
Meng-Ling
ML
Lu
Yu-Feng
YF
Li
Yue-Shuo
YS
Xu
Han-Hong
HH
Xu
D001692:Biological Transport; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D009005:Monosaccharides / Q000737:chemistry / Q000378:metabolism*; D052585:Phloem / Q000378:metabolism*; D012278:Ricinus / Q000254:growth & development / Q000378:metabolism*; D012402:Rotenone / Q000737:chemistry / Q000378:metabolism*; D036226:Seedlings / Q000254:growth & development / Q000378:metabolism
D007306:Insecticides; D009005:Monosaccharides; D012402:Rotenone