Uptake and phloem transport of glucose-fipronil conjugate in Ricinus communis involve a carrier-mediated mechanism

Journal of Agricultural and Food Chemistry
Han-Xiang WuHan-Hong Xu

Abstract

Some compounds containing glucose are absorbed via the monosaccharide transporters of the plasma membrane. A glucose-fipronil conjugate, N-[3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazol-5-yl]-1-(β-d-glucopyranosyl)-1H-1,2,3-triazole-4-methanamine (GTF), has been synthesized in our previous work. GTF exhibits moderate phloem mobility in Ricinus communis. In the current paper, we demonstrate that the uptake of GTF by Ricinus seedling cotyledon discs is partly mediated by an active carrier system (K(m)1 = 0.17 mM; V(max)1 = 2.2 nmol cm(-2) h(-1)). Four compounds [d-glucose, sucrose, phloridzin, and carbonyl cyanide m-chlorophenylhydrazone (CCCP)] were examined for their effect on GTF uptake. Phloridzin as well as CCCP markedly inhibit GTF uptake, and d-glucose weakly competes with it. The phloem transport of GTF in Ricinus seedlings is found to involve an active carrier-mediated mechanism that effectively contributes to the GTF phloem loading. The results prove that adding a glucose core is a reasonable and feasible approach to confer phloem mobility to fipronil by utilizing plant monosaccharide transporters.

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Citations

Apr 17, 2013·Journal of Agricultural and Food Chemistry·Jian-Guo YuanHan-Hong Xu
Feb 25, 2014·Journal of Photochemistry and Photobiology. B, Biology·Zhiwei LeiHanhong Xu
Feb 24, 2015·Environmental Health and Preventive Medicine·Sompon WanwimolrukVirapong Prachayasittikul
Oct 27, 2016·Bioorganic & Medicinal Chemistry Letters·Junfan NiuJunkai Li
Dec 15, 2016·Environmental Science and Pollution Research International·Hanxiang WuJean-François Chollet
Nov 1, 2017·Journal of Experimental Botany·Hanxiang WuJean-Louis Bonnemain
Nov 20, 2019·Environmental Science and Pollution Research International·Zhanfu RenFei Lin
Jun 23, 2020·Zeitschrift Für Naturforschung. C, a Journal of Biosciences·Min LvHui Xu
Dec 12, 2018·Pest Management Science·Hanxiang WuJean-François Chollet
Mar 31, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Qingqing ShengHanhong Xu
Jan 28, 2020·Natural Product Research·Yongtong XiongQinglai Wu
Aug 29, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Linhua YuJunkai Li
Jun 7, 2014·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Jin-Liang JiaHan-Hong Xu
Jul 5, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yao ChenMao Fa Yang
Aug 19, 2014·Journal of Agricultural and Food Chemistry·Jie WangHanhong Xu
Jun 12, 2014·Journal of Agricultural and Food Chemistry·Zhiwei LeiHanhong Xu
May 2, 2014·Journal of Agricultural and Food Chemistry·Pei-Wen QinHan-Hong Xu

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