Brassinosteroids: synthesis and biological activities

Oklešťková, Jana; Rárová, Lucie; Kvasnica, Miroslav; Strnad, Miroslav

doi:10.1007/s11101-015-9446-9

Cited by 73 publications

(68 citation statements)

References 131 publications

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“…31) As a result of intensive BR synthetic research, numerous synthetic analogs including natural and artificial chemicals have been developed and have successfully revealed various BR physiological functions, such as cell elongation, cell division, and stress tolerance. Even today, the study of the structure-activity relationships of BR analogs to BRI1 plays an important role in understanding the physiological functions of BRs in developing PGRs.…”

Section: Pgrs For Regulating Br Activitiesmentioning

confidence: 99%

“…Even today, the study of the structure-activity relationships of BR analogs to BRI1 plays an important role in understanding the physiological functions of BRs in developing PGRs. 31,32) Triazole-type chemicals have been widely utilized as PGRs. 33) Some triazole-type chemicals have fungicidal properties associated with the inhibition of sterol biosynthesis, whereas others are potent inhibitors of elongation growth in plants.…”

Section: Pgrs For Regulating Br Activitiesmentioning

confidence: 99%

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Recent advances in brassinosteroid biosynthetic pathway: insight into novel brassinosteroid shortcut pathway

Ohnishi

2018

Journal of Pesticide Science

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Brassinosteroids (BRs) are plant steroid hormones involved in plant growth and environmental adaptation. It is well known that oxidation/hydroxylation steps in the BR biosynthetic pathway are catalyzed by cytochrome P450 enzymes. It has been proposed that brassinolide is biosynthesized from campesterol via campestanol (CN) in the original BR biosynthetic pathway. However, a recent enzymatic analysis of cytochrome P450 enzymes and re-evaluation of the endogenous amount of BRs in BR-deficient mutants included an investigation of the novel BR biosynthetic pathway (CN-independent pathway) not via CN. This review highlights comprehensive recent advances in the biochemical research of BR biosynthetic enzymes and the CN-independent pathway. This review also focuses the biosynthesis inhibitors and the antagonists/agonists that are utilized not only as plant growth regulators but also as tools for the chemical and biological investigation of the physiological functions of BRs.

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Section: Pgrs For Regulating Br Activitiesmentioning

confidence: 99%

Section: Pgrs For Regulating Br Activitiesmentioning

confidence: 99%

Recent advances in brassinosteroid biosynthetic pathway: insight into novel brassinosteroid shortcut pathway

Ohnishi

2018

Journal of Pesticide Science

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“…The widespread use of isotopically labeled compounds have become well established and an essential tool for the identification of drug candidates; drugs; and drug metabolites in complex analytical and biochemical schemes of pharmaceutical, biological, and agrochemical research . The visualization of synthetized or isolated natural compounds is a fundamental aspect for studies of their action, affinity, and toxicity.…”

Section: Introductionmentioning

confidence: 99%

Frustrated Lewis pairs: A real alternative to deuteride/tritide reductions

Doubková

Marek

2019

Labelled Comp Radiopharmac

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Deuterium‐ and tritium‐labeled compounds play a principal role in tracing of biologically active molecules in complicated biochemical systems. The state‐of‐the‐art techniques using noble metal catalysts or strong reducing agents often suffers from low functional group tolerances, poor selectivity, tricky or multistep synthesis of reagents, and low specific activity of the labeled product. Herein, we demonstrate a mild and nonmetallic technique of deuteration and tritiation of polarized double bonds, such as carbonyl compounds, yielding labeled alcohols of high specific activities. This one‐pot synthesis uses carrier‐free hydrogen gas in situ activated by a freshly prepared frustrated Lewis pair, generating reducing reagents. This labeling strategy shows better selectivity and functional group tolerances compared with current reductive methods. Reported is an example of the selective reduction of the aldehyde moiety of 3‐acetylbenzaldehyde. What makes this technology groundbreaking is its mildness, selectivity, and generation of limited amount of radioactive waste as almost no byproducts were generated after use of (B(C6F5)33H)(3HTMP) reducing reagent. Radiochemical purity of desired 3H‐labeled product in a crude reaction mixture was determined of over 94%. This work provides, to the community of radiochemists, a practical protocol for frustrated Lewis pairs (FLP)‐assisted deuterium/tritium labeling technology.

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“…Over the last decades, several research groups have prepared and studied synthetic analogs of brassinosteroids with the aim of understanding the structure–activity relationship (SAR) of this fascinating plant hormone and optimizing their biological performance for applications in agriculture . However, while there is a wealth of information available, it is very difficult to compare the numerous analogs reported by different research groups, as frequently different testing conditions were used to evaluate their biological potency.…”

Section: Introductionmentioning

confidence: 99%

Biological Activity of Brassinosteroids – Direct Comparison of Known and New Analogs in planta

Wendeborn

Lachia

Jung

et al. 2017

Helvetica Chimica Acta

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A systematic investigation of structural modifications of brassinosteroids is presented. We describe in detail their synthetic preparation, which includes significant improvements of previously reported protocols as well as access to new analogs with functional modifications of the steroid skeleton and of the C(17)‐attached side chain. We report the biological potency of the prepared brassinosteroid analogs as plant hormones, which were carefully established in the French bean second internode elongation assay and discuss our observations in light of the recently reported structural data detailing the molecular interactions between brassinolide in the trimeric complex with the protein receptors kinases BRASSINOSTEROID INSENSITIVE 1 (BRI1) and SOMATIC EMBRYOGENESIS RECEPTOR KINASE 1 (SERK1). In a further part of this work we describe the preparation of H2O‐soluble pro‐forms of 24‐epicastasterone and we discuss their physical properties, hydrolytic stabilities and biological activity.

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Brassinosteroids: synthesis and biological activities

Cited by 73 publications

References 131 publications

Recent advances in brassinosteroid biosynthetic pathway: insight into novel brassinosteroid shortcut pathway

Recent advances in brassinosteroid biosynthetic pathway: insight into novel brassinosteroid shortcut pathway

Frustrated Lewis pairs: A real alternative to deuteride/tritide reductions

Biological Activity of Brassinosteroids – Direct Comparison of Known and New Analogs in planta

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