Synthesis and plant growth promoting activity of dinorcholanic lactones bearing the 5α-hydroxy-6-oxo moiety

Rosado‐Abón, Anielka; Dios-Bravo, Guadalupe de; Rodríguez‐Sotres, Rogelio; Iglesias-Arteaga, Martı́n A.

doi:10.1016/j.jsbmb.2012.10.007

Cited by 23 publications

(5 citation statements)

References 20 publications

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“…This test has been used in both gibberellins and BRs. For gibberellins, only elongation can be detected, while for BRs curvature, swelling and division of the internode are easily measured [ 46 , 47 , 53 , 54 , 55 , 56 , 57 , 58 ]. The effect on plant tissues depends not only on the structural conformation of the phytohormones but also on the concentration applied, so a dose–response curve of 1 (1 × 10 −5 –1 × 10 −10 M, Figure 4 a,b) was obtained to determine the optimal concentration at which tested molecules should be applied.…”

Section: Resultsmentioning

confidence: 99%

New Brassinosteroid Analogs with 23,24-Dinorcholan Side Chain, and Benzoate Function at C-22: Synthesis, Assessment of Bioactivity on Plant Growth, and Molecular Docking Study

Aitken,

Diaz,

Soto

et al. 2023

IJMS

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The synthesis and biological evaluation of brassinosteroids (BRs) analogs with chemical modification in the side alkyl chain is a matter of current interest. Recently, a series of BR analogs with phenyl or benzoate groups in the alkyl chain have been reported. The effect of substitution in the aromatic ring on the biological activities of these new analogs has been evaluated, and the results suggest that the bioactivity is enhanced by substitution with an F atom. In this context, we have synthesized, characterized, and evaluated a series of new analogs of 23,24-bisnorcholenic type in which the benzoate group at the C-22 position is substituted with an F atom at “ortho or para” positions. Plant growth-promoting activities were evaluated by using the rice lamina inclination test and bean second internode biotest. The results obtained with both bioassays indicate that the compound with an F atom in the para position on the aromatic ring is the most active BR analog and in some cases is even more active than brassinolide. The docking study confirmed that compounds with an F atom adopt an orientation similar to that predicted for brassinolide, and the F atom in the “para” position generates an extra hydrogen bond in the predicted binding position.

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Section: Resultsmentioning

confidence: 99%

New Brassinosteroid Analogs with 23,24-Dinorcholan Side Chain, and Benzoate Function at C-22: Synthesis, Assessment of Bioactivity on Plant Growth, and Molecular Docking Study

Aitken,

Diaz,

Soto

et al. 2023

IJMS

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“…These compounds have to meet certain requirements [46]. To avoid possible interferences with the peaks [M+1] and [M+2] belonging to natural 13 with methyl(trifluoromethyl)-dioxirane followed by dehydration of intermediate alcohol (97). To avoid possible interferences with the peaks [M+1] and [M+2] belonging to natural 13 with methyl(trifluoromethyl)-dioxirane followed by dehydration of intermediate alcohol (97).…”

Section: Isotopically Labeled Bsmentioning

confidence: 99%

“…The synthesis of BS analogs (225, 226) with a (22→16b) lactone moiety was performed as described in Scheme 6.39 [96,97]. Treatment of diosgenin acetate (221) with NaNO 2 and BF 3 •Et 2 O in acetic acid followed by chromatography on neutral alumina gave the ketone (222).…”

Section: Bs Analogsmentioning

confidence: 99%

Synthetic Aspects of Brassinosteroids

Хрипач

Жабинский

Ermolovich

2015

Studies in Natural Products Chemistry

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“…In addition to their intrinsic biological activity, many naturally occurring steroids have been employed as starting materials for the synthesis of bioactive compounds that include drugs [1], ecdysteroids [2], citotoxic steroids [3][4][5], and plant growth promoting substances [6][7][8].…”

Section: Introductionmentioning

confidence: 99%

NMR Characterization and Crystal Structure of 22-Phenyl-3β-acetoxy-bisnorchol-5-en-22-one

2014

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Palladium catalyzed cross coupling between 3b-acetoxy-bisnorchol-5-en-22-oic acid and phenylboronic acid produced the hereto unknown 22-phenyl-3b-acetoxybisnorchol-5-en-22-one which crystallizes in the monoclinic system with space group P2 1 . The presence of 17b-substituent that bears both the C21 methyl group and the introduced phenylketone moiety provides a twisted conformation on C13-C14 for the D ring with asymmetry parameters (Altona et al., Tetrahedron 24:13-32, 1968): D = 711.4, s m = 47.3 (2), DC 2 (C13-C14) = 5.7 (3), DC s (C13) = 14.0 (3) and DC s (C14) = 21.6 (3)°. The angle 77.20 (8)°between planes of the steroid-ABCD framework and phenyl ring evidences the relative orthogonal positions of these fragments. The 1 H and 13 C NMR characterization of the obtained compound are described.

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Synthesis and plant growth promoting activity of dinorcholanic lactones bearing the 5α-hydroxy-6-oxo moiety

Cited by 23 publications

References 20 publications

New Brassinosteroid Analogs with 23,24-Dinorcholan Side Chain, and Benzoate Function at C-22: Synthesis, Assessment of Bioactivity on Plant Growth, and Molecular Docking Study

New Brassinosteroid Analogs with 23,24-Dinorcholan Side Chain, and Benzoate Function at C-22: Synthesis, Assessment of Bioactivity on Plant Growth, and Molecular Docking Study

Synthetic Aspects of Brassinosteroids

NMR Characterization and Crystal Structure of 22-Phenyl-3β-acetoxy-bisnorchol-5-en-22-one

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