International Journal of Molecular Sciences

Research

Jump to: Review

13 pages, 4814 KiB

Open AccessArticle

Synthesis and Biological Activity of New Brassinosteroid Analogs of Type 24-Nor-5β-Cholane and 23-Benzoate Function in the Side Chain

by Nitza Soto, Karoll Ferrer, Katy Díaz, César González, Lautaro Taborga, Andrés F. Olea, Héctor Carrasco and Luis Espinoza

Int. J. Mol. Sci. 2021, 22(9), 4808; https://doi.org/10.3390/ijms22094808 - 01 May 2021

Cited by 3 | Viewed by 2207

Abstract

Brassinosteroids are polyhydroxysteroids that are involved in different plants’ biological functions, such as growth, development and resistance to biotic and external stresses. Because of its low abundance in plants, much effort has been dedicated to the synthesis and characterization of brassinosteroids analogs. Herein, [...] Read more.

Brassinosteroids are polyhydroxysteroids that are involved in different plants’ biological functions, such as growth, development and resistance to biotic and external stresses. Because of its low abundance in plants, much effort has been dedicated to the synthesis and characterization of brassinosteroids analogs. Herein, we report the synthesis of brassinosteroid 24-nor-5β-cholane type analogs with 23-benzoate function and 22,23-benzoate groups. The synthesis was accomplished with high reaction yields in a four-step synthesis route and using hyodeoxycholic acid as starting material. All synthesized analogs were tested using the rice lamina inclination test to assess their growth-promoting activity and compare it with those obtained for brassinolide, which was used as a positive control. The results indicate that the diasteroisomeric mixture of monobenzoylated derivatives exhibit the highest activity at the lowest tested concentrations (1 × 10⁻⁸ and 1 × 10⁻⁷ M), being even more active than brassinolide. Therefore, a simple synthetic procedure with high reaction yields that use a very accessible starting material provides brassinosteroid synthetic analogs with promising effects on plant growth. This exploratory study suggests that brassinosteroid analogs with similar chemical structures could be a good alternative to natural brassinosteroids. Full article

(This article belongs to the Special Issue Plant Steroids)

► Show Figures

Figure 1

12 pages, 3010 KiB

Open AccessArticle

BODIPY Conjugate of Epibrassinolide as a Novel Biologically Active Probe for In Vivo Imaging

by Anastasiia Starodubtseva, Tetiana Kalachova, Oksana Iakovenko, Vera Stoudková, Vladimir Zhabinskii, Vladimir Khripach, Eric Ruelland, Jan Martinec, Lenka Burketová and Volodymyr Kravets

Int. J. Mol. Sci. 2021, 22(7), 3599; https://doi.org/10.3390/ijms22073599 - 30 Mar 2021

Viewed by 2919

Abstract

Brassinosteroids (BRs) are plant hormones of steroid nature, regulating various developmental and adaptive processes. The perception, transport, and signaling of BRs are actively studied nowadays via a wide range of biochemical and genetic tools. However, most of the knowledge about BRs intracellular localization [...] Read more.

Brassinosteroids (BRs) are plant hormones of steroid nature, regulating various developmental and adaptive processes. The perception, transport, and signaling of BRs are actively studied nowadays via a wide range of biochemical and genetic tools. However, most of the knowledge about BRs intracellular localization and turnover relies on the visualization of the receptors or cellular compartments using dyes or fluorescent protein fusions. We have previously synthesized a conjugate of epibrassinolide with green fluorescent dye BODIPY (eBL-BODIPY). Here we present a detailed assessment of the compound bioactivity and its suitability as probe for in vivo visualization of BRs. We show that eBL-BODIPY rapidly penetrates epidermal cells of Arabidopsis thaliana roots and after long exposure causes physiological and transcriptomic responses similar to the natural hormone. Full article

(This article belongs to the Special Issue Plant Steroids)

► Show Figures

Figure 1

13 pages, 1013 KiB

Open AccessArticle

Naturally Occurring Ecdysteroids in Triticum aestivum L. and Evaluation of Fenarimol as a Potential Inhibitor of Their Biosynthesis in Plants

by Anna Janeczko, Jana Oklestkova, Danuše Tarkowská and Barbara Drygaś

Int. J. Mol. Sci. 2021, 22(6), 2855; https://doi.org/10.3390/ijms22062855 - 11 Mar 2021

Cited by 1 | Viewed by 2578

Abstract

Ecdysteroids (ECs) are steroid hormones originally found in the animal kingdom where they function as insect molting hormones. Interestingly, a relatively high number of these substances can also be formed in plant cells. Moreover, ECs have certain regulatory effects on plant physiology, but [...] Read more.

Ecdysteroids (ECs) are steroid hormones originally found in the animal kingdom where they function as insect molting hormones. Interestingly, a relatively high number of these substances can also be formed in plant cells. Moreover, ECs have certain regulatory effects on plant physiology, but their role in plants still requires further study. One of the main aims of the present study was to verify a hypothesis that fenarimol, an inhibitor of the biosynthesis of ECs in the animal kingdom, also affects the content of endogenous ECs in plants using winter wheat Triticum aestivum L. as a model plant. The levels of endogenous ECs in winter wheat, including the estimation of their changes during a course of different temperature treatments, have been determined using a sensitive analytical method based on UHPLC-MS/MS. Under our experimental conditions, four substances of EC character were detected in the tissue of interest in amounts ranging from less than 1 to over 200 pg·g⁻¹ FW: 20-hydroxyecdysone, polypodine B, turkesterone, and isovitexirone. Among them, turkesterone was observed to be the most abundant EC and accumulated mainly in the crowns and leaves of wheat. Importantly, the level of ECs was observed to be dependent on the age of the plants, as well as on growth conditions (especially temperature). Fenarimol, an inhibitor of a cytochrome P450 monooxygenase, was shown to significantly decrease the level of naturally occurring ECs in experimental plants, which may indicate its potential use in studies related to the biosynthesis and physiological function of these substances in plants. Full article

(This article belongs to the Special Issue Plant Steroids)

► Show Figures

Figure 1

19 pages, 4440 KiB

Open AccessArticle

Synthesis of New Steroidal Carbamates with Plant-Growth-Promoting Activity: Theoretical and Experimental Evidence

by Daylin Fernández Pacheco, Leonardo González Ceballos, Armando Zaldo Castro, Marcos R. Conde González, Laura González de la Torre, Lia Pérez Rostgaard, Luis Espinoza, Katy Díaz, Andrés F. Olea and Yamilet Coll García

Int. J. Mol. Sci. 2021, 22(5), 2330; https://doi.org/10.3390/ijms22052330 - 26 Feb 2021

Cited by 4 | Viewed by 2545

Abstract

A priority of modern agriculture is to use novel and environmentally friendly plant-growth promoter compounds to increase crop yields and avoid the indiscriminate use of synthetic fertilizers. Brassinosteroids are directly involved in the growth and development of plants and are considered attractive candidates [...] Read more.

A priority of modern agriculture is to use novel and environmentally friendly plant-growth promoter compounds to increase crop yields and avoid the indiscriminate use of synthetic fertilizers. Brassinosteroids are directly involved in the growth and development of plants and are considered attractive candidates to solve this problem. Obtaining these metabolites from their natural sources is expensive and cumbersome since they occur in extremely low concentrations in plants. For this reason, much effort has been dedicated in the last decades to synthesize brassinosteroids analogs. In this manuscript, we present the synthesis and characterization of seven steroidal carbamates starting from stigmasterol, β-sitosterol, diosgenin and several oxygenated derivatives of it. The synthesis route for functionalization of diosgenin included epoxidation and epoxy opening reactions, reduction of carbonyl groups, selective oxidation of hydroxyl groups, among others. All the obtained compounds were characterized by ¹H and ¹³C NMR, HRMS, and their melting points are also reported. Rice lamina inclination test performed at different concentrations established that all reported steroidal carbamates show plant-growth-promoting activity. A molecular docking study evaluated the affinity of the synthesized compounds towards the BRI1-BAK1 receptor from Arabidopsis thaliana and three of the docked compounds displayed a binding energy lower than brassinolide. Full article

(This article belongs to the Special Issue Plant Steroids)

► Show Figures

Figure 1

15 pages, 1516 KiB

Open AccessArticle

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

by Katy Díaz, Luis Espinoza, Rodrigo Carvajal, Evelyn Silva-Moreno, Andrés F. Olea and Julia Rubio

Int. J. Mol. Sci. 2021, 22(3), 1158; https://doi.org/10.3390/ijms22031158 - 25 Jan 2021

Cited by 7 | Viewed by 2581

Abstract

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 [...] Read more.

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. Full article

(This article belongs to the Special Issue Plant Steroids)

► Show Figures

Figure 1

27 pages, 1244 KiB

Open AccessArticle

Synthesis and Biological Activity of Brassinosteroid Analogues with a Nitrogen-Containing Side Chain

by Mikhail V. Diachkov, Karoll Ferrer, Jana Oklestkova, Lucie Rarova, Vaclav Bazgier and Miroslav Kvasnica

Int. J. Mol. Sci. 2021, 22(1), 155; https://doi.org/10.3390/ijms22010155 - 25 Dec 2020

Cited by 5 | Viewed by 2786

Abstract

Brassinosteroids are a class of plant hormones that regulate a broad range of physiological processes such as plant growth, development and immunity, including the suppression of biotic and abiotic stresses. In this paper, we report the synthesis of new brassinosteroid analogues with a [...] Read more.

Brassinosteroids are a class of plant hormones that regulate a broad range of physiological processes such as plant growth, development and immunity, including the suppression of biotic and abiotic stresses. In this paper, we report the synthesis of new brassinosteroid analogues with a nitrogen-containing side chain and their biological activity on Arabidopis thaliana. Based on molecular docking experiments, two groups of brassinosteroid analogues were prepared with short and long side chains in order to study the impact of side chain length on plants. The derivatives with a short side chain were prepared with amide, amine and ammonium functional groups. The derivatives with a long side chain were synthesized using amide and ammonium functional groups. A total of 25 new brassinosteroid analogues were prepared. All 25 compounds were tested in an Arabidopsis root sensitivity bioassay and cytotoxicity screening. The synthesized substances showed no significant inhibitory activity compared to natural 24-epibrassinolide. In contrast, in low concentration, several compounds (8a, 8b, 8e, 16e, 22a and 22e) showed interesting growth-promoting activity. The cytotoxicity assay showed no toxicity of the prepared compounds on cancer and normal cell lines. Full article

(This article belongs to the Special Issue Plant Steroids)

► Show Figures

Graphical abstract

20 pages, 6256 KiB

Open AccessArticle

Functional Characterization of BRASSINAZOLE-RESISTANT 1 in Panax Ginseng (PgBZR1) and Brassinosteroid Response during Storage Root Formation

by Hyeona Hwang, Hwa-Yong Lee, Hojin Ryu and Hyunwoo Cho

Int. J. Mol. Sci. 2020, 21(24), 9666; https://doi.org/10.3390/ijms21249666 - 18 Dec 2020

Cited by 7 | Viewed by 2754

Abstract

Brassinosteroids (BRs) play crucial roles in the physiology and development of plants. In the model plant Arabidopsis, BR signaling is initiated at the level of membrane receptors, BRASSINOSTEROIDS INSENSITIVE 1 (BRI1) and BRI1-ASSOCIATED RECEPTOR KINASE 1 (BAK1) complex, thus activating the transcription [...] Read more.

Brassinosteroids (BRs) play crucial roles in the physiology and development of plants. In the model plant Arabidopsis, BR signaling is initiated at the level of membrane receptors, BRASSINOSTEROIDS INSENSITIVE 1 (BRI1) and BRI1-ASSOCIATED RECEPTOR KINASE 1 (BAK1) complex, thus activating the transcription factors (TFs) BRASSINAZOLE RESISTANT 1/BRI1-EMS-SUPPRESSOR 1 (BZR1/BES1) to coordinate BR responsive genes. BRASSINOSTEROIDS INSENSITIVE 2 (BIN2), glycogen synthase kinase 3 (GSK3) like-kinase, negatively regulates BZR1/BES1 transcriptional activity through phosphorylation-dependent cytosolic retention and shuttling. However, it is still unknown whether this mechanism is conserved in Panax ginseng C. A. Mayer, a member of the Araliaceae family, which is a shade-tolerant perennial root crop. Despite its pharmacological and agricultural importance, the role of BR signaling in the development of P. ginseng and characterization of BR signaling components are still elusive. In this study, by utilizing the Arabidopsisbri1 mutant, we found that ectopic expression of the gain of function form of PgBZR1 (Pgbzr1-1D) restores BR deficiency. In detail, ectopic expression of Pgbzr1-1D rescues dwarfism, defects of floral organ development, and hypocotyl elongation of bri1-5, implying the functional conservation of PgBZR1 in P. ginseng. Interestingly, brassinolide (BL) and BRs biosynthesis inhibitor treatment in two-year-old P. ginseng storage root interferes with and promotes, respectively, secondary growth in terms of xylem formation. Altogether, our results provide new insight into the functional conservation and potential diversification of BR signaling and response in P. ginseng. Full article

(This article belongs to the Special Issue Plant Steroids)

► Show Figures

Figure 1

Review

Jump to: Research

18 pages, 2592 KiB

Open AccessReview

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

by Juan Pablo Figueroa-Macías, Yamilet Coll García, María Núñez, Katy Díaz, Andres F. Olea and Luis Espinoza

Int. J. Mol. Sci. 2021, 22(2), 693; https://doi.org/10.3390/ijms22020693 - 12 Jan 2021

Cited by 42 | Viewed by 4441

Abstract

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 [...] Read more.

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. Full article

(This article belongs to the Special Issue Plant Steroids)

► Show Figures

Figure 1

Journal Menu

Journal Browser

Plant Steroids

Share This Special Issue

Special Issue Editor

Special Issue Information

Keywords

Published Papers (8 papers)

Research

Review

Further Information

Guidelines

MDPI Initiatives

Follow MDPI