Structure-activity relationship of brassinosteroids and their agricultural practical usages

Liu, Jinna; Zhang, Di; Sun, Xiaoyu; Ding, Tingle; Lei, Beilei; Zhang, Cunli

doi:10.1016/j.steroids.2017.05.005

Cited by 56 publications

(49 citation statements)

References 86 publications

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“…Brassinosteroids (BRs) are a large group of polyhydroxylated sterol derivatives found in the plant kingdom in extremely low amounts and eliciting very important functions, such as plant growth regulation [1,2] and cell division and differentiation in young tissues of growing plants [3][4][5]. As a result of these features, BRs were recognized as the sixth class of plant hormones [6,7].…”

Section: Introductionmentioning

confidence: 99%

“…Their natural occurrence, biological activities, and structure-activity relationships (SAR) have been reviewed by different groups [6,[8][9][10] and brassinolide (BL, 1) and castasterone (CS, 2) are the most active and widely distributed. The low amount of BRs produced in plants has prompted the quest for synthetic BRs derivatives, and so far, 137 analogs have already been reported [6]. However, structural variations arising from the type and position of functions in the A, B rings, fusion A/B ring, and alky side chain should be considered in the design of new BRs analogs.…”

Section: Introductionmentioning

confidence: 99%

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Biological Activities and Molecular Docking of Brassinosteroids 24-Norcholane Type Analogs

Díaz

Espinoza

Carvajal

et al. 2020

IJMS

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The quest and design of new brassinosteroids analogs is a matter of current interest. Herein, the effect of short alkyl side chains and the configuration at C22 on the growth-promoting activity of a series of new brassinosteroid 24-norcholan-type analogs have been evaluated by the rice leaf inclination test using brassinolide as positive control. The highest activities were found for triol 3 with a C22(S) configuration and monobenzoylated derivatives. A docking study of these compounds into the active site of the Brassinosteroid Insensitive 1(BRI1)–ligand–BRI1-Associated Receptor Kinase 1 (BAK1) complex was performed using AutoDock Vina, and protein–ligand contacts were analyzed using LigPlot+. The results suggest that the hydrophobic interactions of ligands with the receptor BRI1LRR and hydrogen bonding with BAK1 in the complex are important for ligand recognition. For monobenzoylated derivatives, the absence of the hydrophobic end in the alkyl chain seems to be compensated by the benzoyl group. Thus, it would be interesting to determine if this result depends on the nature of the substituent group. Finally, mixtures of S/R triols 3/4 exhibit activities that are comparable or even better than those found for brassinolide. Thus, these compounds are potential candidates for application in agriculture to improve the growth and yield of plants against various types of biotic and abiotic stress.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Biological Activities and Molecular Docking of Brassinosteroids 24-Norcholane Type Analogs

Díaz

Espinoza

Carvajal

et al. 2020

IJMS

View full text Add to dashboard Cite

show abstract

“…Since the discovery of brassinolide (1) [1] (Figure 1) a large number of similar compounds have been identified in many plant species [2,3]. This family of polyhydroxylated sterol derivatives, named brassinosteroids (BRs), amounts to almost 80 different molecules which have been recently recognized as the sixth class of plant hormones [4,5]. They act as regulators of plant growth in very low amounts [1][2][3], participating in processes of cell expansion, division, and differentiation in young tissues of growing plants [6,7].…”

Section: Introductionmentioning

confidence: 99%

“…The extremely low amount of BRs present in plants has prompted the chemical synthesis of BRs and 137 analogs have already been reported [4]. Structural variations of BRs arise from the type and position of functions in the A, B rings, fusion A/B ring, and alkyl side chain.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Determination of New Brassinosteroid 24-Nor-5α-Cholane Type Analogs

et al. 2019

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Natural brassinosteroids possess a 22R, 23R configuration that appears essential for biological activity. It is, therefore, interesting to elucidate if the activity of brassinosteroids with a short side chain depends on the C22 configuration. Herein, we describe the synthesis of new brassinosteroids analogs with 24-norcholane type of side chain and R configuration at C22. The initial reaction is the dihydroxylation of a terminal olefin that leads to S/R epimers. Three different methods were tested in order to evaluate the obtained S/R ratio and the reaction yields. The results indicate that Upjohn dihydroxylation is the most selective reaction giving a 1.0:0.24 S/R ratio, whereas a Sharpless reaction leads to a mixture of 1.0:0.90 S/R with 95% yield. Using the latter mixture and following a previous reported method, benzoylated derivatives and both S and R brassinosteroids analogs were synthesized. All synthesized compounds were completely characterized by NMR spectroscopy, and HRMS of new compounds are also given. In conclusion, a synthetic route for preparation of new analogs of brassinosteroids of 24-norcholane type and R configuration at C22 were described. It is expected that this will help to elucidate if a configuration at C22 is a structural requirement for hormonal growth activity in plants.

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“…Therefore, ideal sample pretreatment techniques should exhibit ultra-high sensitivity. Among the currently known BRs, brassinolide (BL) show the strongest activity, for BL fragmentation pattern, although the orientation of spatial position of the -OH in BL varies, ions generated from BL in the tandem mass spectrometry are substantially identical [139]. When BL fragmentation, as it shown in Fig.…”

Section: Neutral Plant Hormones Brassinosteroid (Br)mentioning

confidence: 98%

Recent developments and emerging trends of mass spectrometric methods in plant hormone analysis: a review

et al. 2020

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Plant hormones are naturally occurring small molecule compounds which are present at trace amounts in plant. They play a pivotal role in the regulation of plant growth. The biological activity of plant hormones depends on their concentrations in the plant, thus, accurate determination of plant hormone is paramount. However, the complex plant matrix, wide polarity range and low concentration of plant hormones are the main hindrances to effective analyses of plant hormone even when state-of-the-art analytical techniques are employed. These factors substantially influence the accuracy of analytical results. So far, significant progress has been realized in the analysis of plant hormones, particularly in sample pretreatment techniques and mass spectrometric methods. This review describes the classic extraction and modern microextraction techniques used to analyze plant hormone. Advancements in solid phase microextraction (SPME) methods have been driven by the ever-increasing requirement for dynamic and in vivo identification of the spatial distribution of plant hormones in real-life plant samples, which would contribute greatly to the burgeoning field of plant hormone investigation. In this review, we describe advances in various aspects of mass spectrometry methods. Many fragmentation patterns are analyzed to provide the theoretical basis for the establishment of a mass spectral database for the analysis of plant hormones. We hope to provide a technical guide for further discovery of new plant hormones. More than 140 research studies on plant hormone published in the past decade are reviewed, with a particular emphasis on the recent advances in mass spectrometry and sample pretreatment techniques in the analysis of plant hormone. The potential progress for further research in plant hormones analysis is also highlighted.

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Structure-activity relationship of brassinosteroids and their agricultural practical usages

Cited by 56 publications

References 86 publications

Biological Activities and Molecular Docking of Brassinosteroids 24-Norcholane Type Analogs

Biological Activities and Molecular Docking of Brassinosteroids 24-Norcholane Type Analogs

Synthesis and Structural Determination of New Brassinosteroid 24-Nor-5α-Cholane Type Analogs

Recent developments and emerging trends of mass spectrometric methods in plant hormone analysis: a review

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