title: β-Glucosidase involvement in the bioactivation of glycosyl conjugates in plants: synthesis and metabolism of four glycosidic bond conjugates in vitro and in vivo.
abstract: Mobile glucose-pesticide conjugates in the phloem are often restricted by decreases in biological activity. However, plants can bioactivate endogenous glucosides, which are assumed as able to bioactivate exogenous conjugates. In this study, four glycosidic bonds (O-, S-, N-, and C-glycosidic bonds) of glucose-pesticide conjugates were designed and synthesized, and then metabolism assays were carried out in vitro and in vivo. Results showed that β-glucosidases played a role in the hydrolysis of O-glycosidic bond conjugates in Ricinus communis L. The liberated aglycons possessed insecticidal activities against Plutella xylostella L. and Spodoptera litura F. These results could help establish methods of circumventing the mutual exclusivity of phloem mobility and biological activity by hydrolyzing endogenous β-glucosidases.
authors.affiliation: 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.
authors.forename: Qing
authors.initials: Q
authors.lastname: Xia
authors.forename: Ying-Jie
authors.initials: YJ
authors.lastname: Wen
authors.forename: Hao
authors.initials: H
authors.lastname: Wang
authors.forename: Yu-Feng
authors.initials: YF
authors.lastname: Li
authors.forename: Han-Hong
authors.initials: HH
authors.lastname: Xu
mesh_terms: D000818:Animals; D055162:Biocatalysis; D002367:Ricinus communis / Q000737:chemistry / Q000201:enzymology* / Q000378:metabolism; D005947:Glucose / Q000737:chemistry / Q000378:metabolism; D005960:Glucosides / Q000737:chemistry / Q000378:metabolism*; D006868:Hydrolysis; D007306:Insecticides / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects; D052585:Phloem / Q000737:chemistry / Q000201:enzymology / Q000378:metabolism; D010940:Plant Proteins / Q000737:chemistry / Q000378:metabolism*; D018411:Spodoptera / Q000187:drug effects; D001617:beta-Glucosidase / Q000737:chemistry / Q000378:metabolism*
chemical_list: D005960:Glucosides; D007306:Insecticides; D010940:Plant Proteins; D001617:beta-Glucosidase; D005947:Glucose
keywords: glycosidic bond; glycosylation; hydrolysis; insecticidal activity; β-glucosidase