Dataset Information

Cytokinin N-glucosides: Occurrence, Metabolism and Biological Activities in Plants.

ABSTRACT: Cytokinins (CKs) are a class of phytohormones affecting many aspects of plant growth and development. In the complex process of CK homeostasis in plants, N-glucosylation represents one of the essential metabolic pathways. Its products, CK N7- and N9-glucosides, have been largely overlooked in the past as irreversible and inactive CK products lacking any relevant physiological impact. In this work, we report a widespread distribution of CK N-glucosides across the plant kingdom proceeding from evolutionary older to younger plants with different proportions between N7- and N9-glucosides in the total CK pool. We show dramatic changes in their profiles as well as in expression levels of the UGT76C1 and UGT76C2 genes during Arabidopsis ontogenesis. We also demonstrate specific physiological effects of CK N-glucosides in CK bioassays including their antisenescent activities, inhibitory effects on root development, and activation of the CK signaling pathway visualized by the CK-responsive YFP reporter line, TCSv2::3XVENUS. Last but not least, we present the considerable impact of CK N7- and N9-glucosides on the expression of CK-related genes in maize and their stimulatory effects on CK oxidase/dehydrogenase activity in oats. Our findings revise the apparent irreversibility and inactivity of CK N7- and N9-glucosides and indicate their involvement in CK evolution while suggesting their unique function(s) in plants.

SUBMITTER: Pokorna E

PROVIDER: S-EPMC7824008 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Cytokinin N-glucosides: Occurrence, Metabolism and Biological Activities in Plants.

Pokorná Eva E Hluska Tomáš T Galuszka Petr P Hallmark H Tucker HT Dobrev Petre I PI Záveská Drábková Lenka L Filipi Tomáš T Holubová Katarína K Plíhal Ondřej O Rashotte Aaron M AM Filepová Roberta R Malbeck Jiří J Novák Ondřej O Spíchal Lukáš L Brzobohatý Břetislav B Mazura Pavel P Zahajská Lenka L Motyka Václav V

Biomolecules 20201228 1

Cytokinins (CKs) are a class of phytohormones affecting many aspects of plant growth and development. In the complex process of CK homeostasis in plants, N-glucosylation represents one of the essential metabolic pathways. Its products, CK N7- and N9-glucosides, have been largely overlooked in the past as irreversible and inactive CK products lacking any relevant physiological impact. In this work, we report a widespread distribution of CK N-glucosides across the plant ...[more]

PMID: 33379369

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Project description:The purpose of this study was to evaluate the response of estrogen target cells to a series of isoflavone glucosides and aglycones from Genista halacsyi Heldr. The methanolic extract of aerial parts of this plant was processed using fast centrifugal partition chromatography, resulting in isolation of four archetypal isoflavones (genistein, daidzein, isoprunetin, 8-C-?-D-glucopyranosyl-genistein) and ten derivatives thereof. 7-O-?-D-glucopyranosyl-genistein and 7,4?-di-O-?-D-glucopyranosyl-genistein were among the most abundant constituents of the isolate. All fourteen, except genistein, displayed low binding affinity for estrogen receptors (ER). Models of binding to ER? could account for the low binding affinity of monoglucosides. Genistein and its glucosides displayed full efficacy in inducing alkaline phosphatase (AlkP) in Ishikawa cells, proliferation of MCF-7 cells and ER-dependent gene expression in reporter cells at low concentrations (around 0.3 ?M). ICI182,780 fully antagonized these effects. The AlkP-inducing efficacy of the fourteen isoflavonoids was more strongly correlated with their transcriptional efficacy through ER?. O-monoglucosides displayed higher area under the dose-response curve (AUC) of AlkP response relative to the AUC of ER?-transcriptional response compared to the respective aglycones. In addition, 7-O-?-D-glucopyranosyl-genistein and 7,4?-di-O-?-D-glucopyranosyl-genistein displayed estradiol-like efficacy in promoting differentiation of MC3T3-E1 cells to osteoblasts, while genistein was not convincingly effective in this respect. Moreover, 7,4?-di-O-?-D-glucopyranosyl-genistein suppressed lipopolysaccharide-induced tumor necrosis factor mRNA expression in RAW 264.7 cells, while 7-O-?-D-glucopyranosyl-genistein was not convincingly effective and genistein was ineffective. However, genistein and its O-glucosides were ineffective in inhibiting differentiation of RAW 264.7 cells to osteoclasts and in protecting glutamate-challenged HT22 hippocampal neurons from oxidative stress-induced cell death. These findings suggest that 7-O-?-D-glucopyranosyl-genistein and 7,4?-di-O-?-D-glucopyranosyl-genistein display higher estrogen-like and/or anti-inflammatory activity compared to the aglycone. The possibility of using preparations rich in O-?-D-glucopyranosides of genistein to substitute for low-dose estrogen in formulations for menopausal symptoms is discussed.

Dataset Information

Cytokinin N-glucosides: Occurrence, Metabolism and Biological Activities in Plants.

Publications

Cytokinin <i>N</i>-glucosides: Occurrence, Metabolism and Biological Activities in Plants.

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