Biosynthetic relationship between C28-brassinosteroids and C29-brassinosteroids in rice (Oryza sativa) seedlings

Joo, Se‐Hwan; Jang, Mun-Seok; Kim, Min Kyun; Lee, Jieun; Kim, Seong‐Ki

doi:10.1016/j.phytochem.2014.11.006

Cited by 32 publications

(32 citation statements)

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“…It was recently reported that in rice the biosynthesis pathway of the C 29 homoBRs is connected to the C 28 -BR biosynthesis pathway (in which CS is produced) by C-28 demethylation, and the aim of this process is to increase biological activity. Hence, it was concluded that the C 29 -BR biosynthesis is probably an alternative route to the production of endogenous CS in rice (Joo et al, 2015). The C 29 -BR biosynthesis pathway is connected with the C 28 -BR biosynthesis pathway at several steps (Bajguz and Tretyn, 2003; Joo et al, 2015), and it seems to be true also in barley, as the analyzed NILs deficient in the biosynthesis of CS (however, at various steps, because they carry the mutations in the enzymes mediating different reactions during the biosynthesis pathway) accumulate the highest and comparable concentrations of 28-homoCS.…”

Section: Discussionmentioning

confidence: 99%

“…Hence, it was concluded that the C 29 -BR biosynthesis is probably an alternative route to the production of endogenous CS in rice (Joo et al, 2015). The C 29 -BR biosynthesis pathway is connected with the C 28 -BR biosynthesis pathway at several steps (Bajguz and Tretyn, 2003; Joo et al, 2015), and it seems to be true also in barley, as the analyzed NILs deficient in the biosynthesis of CS (however, at various steps, because they carry the mutations in the enzymes mediating different reactions during the biosynthesis pathway) accumulate the highest and comparable concentrations of 28-homoCS. Up to now, the occurrence of 28-homoCS was reported only in two monocot crop species: rice ( Oryza sativa ) (Abe et al, 1995) and rye ( Secale cereale ) (Schmidt et al, 1995), and several other species representing various taxonomic groups of the plant kingdom, however our knowledge of the C 29 -BR biosynthesis in plants is still quite limited (Joo et al, 2015).…”

Section: Discussionmentioning

confidence: 99%

“…The results of our experiments indicate that in contrast to the accumulations of CS and 24-epiBL (representing C 28 BRs), which were significantly stimulated by drought in all analyzed genotypes, the accumulation of 28-homoCS (representing C 29 BRs) is not induced by the stress condition. It may be explained by the fact, that biological activity of C 29 BRs is relatively low in comparison with the biological activity of C 28 BRs (CS in particular) (Joo et al, 2015), therefore it is likely that the drought-induced physiological reaction of barley plants is mediated by CS, which is the most bioactive form of BRs.…”

Section: Discussionmentioning

confidence: 99%

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Barley Brassinosteroid Mutants Provide an Insight into Phytohormonal Homeostasis in Plant Reaction to Drought Stress

et al. 2016

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Brassinosteroids (BRs) are a class of steroid phytohormones, which regulate various processes of morphogenesis and physiology—from seed development to regulation of flowering and senescence. An accumulating body of evidence indicates that BRs take part in regulation of physiological reactions to various stress conditions, including drought. Many of the physiological functions of BRs are regulated by a complicated, and not fully elucidated network of interactions with metabolic pathways of other phytohormones. Therefore, the aim of this study was to characterize phytohormonal homeostasis in barley (Hordeum vulgare) in reaction to drought and validate role of BRs in regulation of this process. Material of this study included the barley cultivar “Bowman” and five Near-Isogenic Lines (NILs) representing characterized semi-dwarf mutants of several genes encoding enzymes participating in BR biosynthesis and signaling. Analysis of endogenous BRs concentrations in these NILs confirmed that their phenotypes result from abnormalities in BR metabolism. In general, concentrations of 18 compounds, representing various classes of phytohormones, including brassinosteroids, auxins, cytokinins, gibberellins, abscisic acid, salicylic acid and jasmonic acid were analyzed under control and drought conditions in the “Bowman” cultivar and the BR-deficient NILs. Drought induced a significant increase in accumulation of the biologically active form of BRs—castasterone in all analyzed genotypes. Another biologically active form of BRs—24-epi-brassinolide—was identified in one, BR-insensitive NIL under normal condition, but its accumulation was drought-induced in all analyzed genotypes. Analysis of concentration profiles of several compounds representing gibberellins allowed an insight into the BR-dependent regulation of gibberellin biosynthesis. The concentration of the gibberellic acid GA7 was significantly lower in all NILs when compared with the “Bowman” cultivar, indicating that GA7 biosynthesis represents an enzymatic step at which the stimulating effect of BRs on gibberellin biosynthesis occurs. Moreover, the accumulation of GA7 is significantly induced by drought in all the genotypes. Biosynthesis of jasmonic acid is also a BR-dependent process, as all the NILs accumulated much lower concentrations of this hormone when compared with the “Bowman” cultivar under normal condition, however the accumulation of jasmonic acid, abscisic acid and salicylic acid were significantly stimulated by drought.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Barley Brassinosteroid Mutants Provide an Insight into Phytohormonal Homeostasis in Plant Reaction to Drought Stress

et al. 2016

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“…For C 28 BRs, the profile of the network-like routes of BR biosynthesis has been described in great detail; however, the roles of some biosynthetic enzymes and their participation in the different subpathways still needs to be clarified (Fujioka and Yokota, 2003; Kim et al, 2008; Ohnishi et al, 2012). For C 27 BRs and C 29 BRs, which exhibit similar bioactivities to C 28 BRs, the situation was even worse because little was known about their biosynthesis pathways (Fujita et al, 2006; Joo et al, 2015). Besides a lack of biochemical and enzymatic evidence about the biosynthetic pathways of C 27 and C 29 BRs, even most of the intermediate compounds on their pathways have not been explored and identified (Fujioka et al, 1999).…”

Section: Introductionmentioning

confidence: 99%

“…Finally, the bioactivity was further tested through the bean second-internode bioassay (Mitchell et al, 1970; Grove et al, 1979). During the following decades, this method was partially simplified to provide structural information only via gas chromatography-mass spectrometry (GC-MS) subsequent to derivatization (Kim et al, 1990; Fujioka et al, 1995; Hwang et al, 2006; Bajguz, 2009; Joo et al, 2015). The method was similar to or derived from the screening of bioactive natural products based on bioactivity-guided isolation and chemical screening (Hostettmann et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

A Comprehensive and Effective Mass Spectrometry-Based Screening Strategy for Discovery and Identification of New Brassinosteroids from Rice Tissues

Xin

Yan

et al. 2016

Front. Plant Sci.

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The exploration and identification of new brassinosteroid (BR) compounds is critical to improve the biosynthetic research of BRs and expand the chemodiversity of active BRs. However, traditional methods are labor-intensive, time-consuming, and less sensitive. Here, we present a facile screening strategy for discovering and identifying novel BRs from plant tissues based on ultra-performance liquid chromatography-mass spectrometry (UPLC-MS). A total of 14 potential BRs were discovered from only 1 g of rice tissues and structurally elucidated by following a MS-based clue, acquired through multiple reaction monitoring (MRM) data-dependent enhanced product ion (EPI) scan, high resolution MS, and MS survey-dependent MS/MS. One of the 14 candidates was identified as 6-deoxo-28-homotyphasterol, a brand new BR compound that is reported for the first time in the BRs biosynthesis pathway. Detailed comparison with reference standards and quantitative level analysis in rice BR mutants confirmed the availability of the other candidates. This effective, yet simple method provides an efficient way to find more and more chemically new BR biosynthetic intermediates in plants, which is significant for complementing the biosynthesis and metabolism network of BRs. This strategy may also be used to discover unknown compounds of other plant hormone species as well as their key metabolites.

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Enantiospecific tritium labeling of 28-homocastasterone

Elbert

Patil

Marek

2017

J. Label Compd. Radiopharm

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A regiospecific and enantiospecific synthesis of tritium-labeled 28-homocastasterone is reported. Appropriate chlorocarbonate, efficiently synthesized from the starting 28-homocastasterone in an overall yield of 46%, undergoes catalytic tritium dechlorination by the T /Pd[0]/Et N system, providing 28-[3β- H]homocastasterone, in a good yield, radiochemical purity (>97%), and with a high specific activity (5.8 Ci/mmol).

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Biosynthetic relationship between C28-brassinosteroids and C29-brassinosteroids in rice (Oryza sativa) seedlings

Cited by 32 publications

References 30 publications

Barley Brassinosteroid Mutants Provide an Insight into Phytohormonal Homeostasis in Plant Reaction to Drought Stress

Barley Brassinosteroid Mutants Provide an Insight into Phytohormonal Homeostasis in Plant Reaction to Drought Stress

A Comprehensive and Effective Mass Spectrometry-Based Screening Strategy for Discovery and Identification of New Brassinosteroids from Rice Tissues

Enantiospecific tritium labeling of 28-homocastasterone

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