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

Díaz, Katy; Espinoza, Luis; Carvajal, Rodrigo; Conde-González, Marcos; Niebla, Vladimir; Olea, Andrés F.; Coll, Yamilet

doi:10.3390/ijms21051832

Cited by 15 publications

(32 citation statements)

References 64 publications

(92 reference statements)

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“…More recently, 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 and benzoylated analogs (BRs derivatives 4 – 7 , Figure 2 ) have been evaluated by the rice leaf inclination test using BL as positive control [ 70 , 71 ]. Molecular docking of compounds 4 – 7 indicated a possible interaction with BRI1 receptor and that ligand recognition could be enhanced by hydrophobic interactions of ligands with the BRI1LRR receptor and hydrogen bonding with BAK1 in the complex [ 71 ]. Anyhow, in all these cases it has been shown that synthetic analogs exhibit similar hormonal activity as natural BL.…”

Section: Design and Synthesis Of Molecules For The Exogenous Stimumentioning

confidence: 99%

Plant Growth-Defense Trade-Offs: Molecular Processes Leading to Physiological Changes

Figueroa-Macías

García

Núñez

et al. 2021

IJMS

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In order to survive in a hostile habitat, plants have to manage the available resources to reach a delicate balance between development and defense processes, setting up what plant scientists call a trade-off. Most of these processes are basically responses to stimuli sensed by plant cell receptors and are influenced by the environmental features, which can incredibly modify such responses and even cause changes upon both molecular and phenotypic level. Therefore, significant differences can be detected between plants of the same species living in different environments. The comprehension of plant growth-defense trade-offs from the molecular basis to the phenotypic expression is one of the fundamentals for developing sustainable agriculture, so with this review we intend to contribute to the increasing of knowledge on this topic, which have a great importance for future development of agricultural crop production.

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Section: Design and Synthesis Of Molecules For The Exogenous Stimumentioning

confidence: 99%

Plant Growth-Defense Trade-Offs: Molecular Processes Leading to Physiological Changes

Figueroa-Macías

García

Núñez

et al. 2021

IJMS

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“…In previous work, it has been shown that the growth-promoting effect is not affected by changing one -OH by a benzoyl group. Results obtained in a molecular docking study suggest that the alkyl side chain in BL contributes significantly to recognition through the interactions of the hydrophobic end with BAK1 [ 57 ]. Thus, high promoting activities of BRs analogs with shortest side chain can be explained by the presence of slightly bulky and hydrophobic substituent in the chain end.…”

Section: Resultsmentioning

confidence: 99%

Exogenous Application of Brassinosteroid 24-Norcholane 22(S)-23-Dihydroxy Type Analogs to Enhance Water Deficit Stress Tolerance in Arabidopsis thaliana

Díaz

Espinoza

Carvajal

et al. 2021

IJMS

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Brassinosteroids (BRs) are plant hormones that play an essential role in plant development and have the ability to protect plants against various environmental stresses, such as low and high temperature, drought, heat, salinity, heavy metal toxicity, and pesticides. Mitigation of stress effects are produced through independent mechanisms or by interaction with other important phytohormones. However, there are few studies in which this property has been reported for BRs analogs. Thus, in this work, the enhancement of drought stress tolerance of A. thaliana was assessed for a series of 2-deoxybrassinosteroid analogs. In addition, the growth-promoting activity in the Rice Lamina Inclination Test (RLIT) was also evaluated. The results show that analog 1 exhibits similar growth activity as brassinolide (BL; used as positive control) in the RLIT bioassay. Interestingly, both compounds increase their activities by a factor of 1.2–1.5 when they are incorporated to polymer micelles formed by Pluronic F-127. On the other hand, tolerance to water deficit stress of Arabidopsis thaliana seedlings was evaluated by determining survival rate and dry weight of seedlings after the recovery period. In both cases, the effect of analog 1 is higher than that exhibited by BL. Additionally, the expression of a subset of drought stress marker genes was evaluated in presence and absence of exogenous applied BRs. Results obtained by qRT-PCR analysis, indicate that transcriptional changes of AtDREBD2A and AtNCED3 genes were more significant in A. thaliana treated with analog 1 in homogeneous solution than in that treated with BL. These changes suggest the activation of alternative pathway in response to water stress deficit. Thus, exogenous application of BRs synthetic analogs could be a potential tool for improvement of crop production under stress conditions.

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“…In this work, the activity of new BR 24-norcholane type analogs conjugated at the C-3 position was evaluated using the Rice Lamina Inclination Test. The results of this test were compared with those obtained for other free analogs of 24-norcholane type (analogs 20a and 20b [ 38 ]) and with brassinolide. This assay was used because of its specificity and high sensitivity for 1 and their analogs [ 31 , 52 , 53 ].…”

Section: Resultsmentioning

confidence: 99%

“…Several studies have proved that synthetic BRs analogs with significant structural changes and different substituents, both in the ring and the alkyl chain, can induce similar or even higher biological effects in plants as compared to natural BRs [ 30 , 31 , 32 , 33 , 34 , 35 , 36 ]. Some recent reviews of the growth-promoting activity of BRs and their analogs have established novel structural requirements for the existence of biological activity [ 23 , 37 , 38 , 39 ]. For example, it has been shown that methyl ethers at C-3 are more active than 1 in the RLIT [ 40 ], whereas benzoate esters in the C-3 position were found to be less active than 24-epibrassinolide in the BSIB test [ 22 ].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of New Brassinosteroid 24-Norcholane Type Analogs Conjugated in C-3 with Benzoate Groups

et al. 2021

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The metabolism of brassinosteroid leads to structural modifications in the ring skeleton or the side alkyl chain. The esterification and glycosylation at C-3 are the most common metabolic pathways, and it has been suggested that conjugate brassinosteroids are less active or inactive. In this way, plants regulate the content of active brassinosteroids. In this work, the synthesis of brassinosteroid 24-norcholane type analogs conjugated at C-3 with benzoate groups, carrying electron donor and electron attractant substituents on the aromatic ring, is described. Additionally, their growth-promoting activities were evaluated using the Rice Lamina Inclination Test (RLIT) and compared with that exhibited by brassinolide (used as positive control) and non-conjugated analogs. The results indicate that at the lowest tested concentrations (10−8–10−7 M), all analogs conjugated at C-3 exhibit similar or higher activities than brassinolide, and the diasteroisomers with S configuration at C-22 are the more active ones. Increasing concentration (10−6 M) reduces the biological activities of analogs as compared to brassinolide.

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

Cited by 15 publications

References 64 publications

Plant Growth-Defense Trade-Offs: Molecular Processes Leading to Physiological Changes

Plant Growth-Defense Trade-Offs: Molecular Processes Leading to Physiological Changes

Exogenous Application of Brassinosteroid 24-Norcholane 22(S)-23-Dihydroxy Type Analogs to Enhance Water Deficit Stress Tolerance in Arabidopsis thaliana

Synthesis of New Brassinosteroid 24-Norcholane Type Analogs Conjugated in C-3 with Benzoate Groups

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