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Abstract:

In this paper, we report the synthesis and bioactivity of four synthetic analogues of 28-homobrassinosteroids, in order to evaluate the influence in bioactivity when the C-6 keto group is replaced by different functional groups. The synthetic analogues are 6-deoxo-28-homocastasterone [(22R,23R)-stigmasta- 2α,3α,22,23-tetraol], 6α-hydroxy-28-homocastasterone [(22R,23R)-stigmasta-2α,3α,6α,22,23-pentaol], 6β-hydroxy-28-homocastasterone [(22R,23R)-stigmasta-2α,3α, 6β,22,23-pentaol], and [(22R,23R)-6α-fluorostigmasta-2α, 3α,22,23-tetraol]. Results indicate that replacement of the 6-keto moiety by an β or α hydroxyl group led to a decrease in activity, whereas the 6-deoxo analogue showed a very low activity, confirming the importance of an electronegative moiety at C-6 to observe hormonal potency. The 6α-fluorinated analogue elicited a low activity, similar to that of the 6-deoxo analogue. © 2005 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6
Autor:Ramírez, J.A.; Brosa, C.; Galagovsky, L.R.
Filiación:Depto. de Quím. Orgán., Fac. de Ciencias Exactas Y Naturales, Ciudad Universitaria (C1428EGA), Buenos Aires 1428, Argentina
Inst. Químic de Sarrià, CETS, Universitat Ramon Llull, Via Augusta 390, 08024 Barcelona, Spain
Palabras clave:Bioactivity; Brassinosteroids; Gramineae; Oryza sativa; Synthesis of fluorinated analogues; 6 deoxo 28 homocastasterone stigmasta 2alpha,3alpha,22,23 tetraol; 6alpha fluorostigmasta 2alpha,3alpha,22,23 tetraol; 6alpha hydroxy 28 homocastasterone stigmasta 2alpha,3alpha,6alpha,22,23 pentaol; 6beta hydroxy 28 homocastasterone stigmasta 2alpha,3alpha,6beta,22,23 pentaol; brassinosteroid; functional group; hexamethonium bromide; hydroxyl group; phytohormone; unclassified drug; article; drug activity; hormone action; Poaceae; rice; synthesis; synthesis; Oryza sativa; Poaceae
Año:2005
Volumen:66
Número:5
Página de inicio:581
Página de fin:587
DOI: http://dx.doi.org/10.1016/j.phytochem.2004.12.029
Título revista:Phytochemistry
Título revista abreviado:Phytochemistry
ISSN:00319422
CODEN:PYTCA
CAS:hexamethonium bromide, 55-97-0
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00319422_v66_n5_p581_Ramirez

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Citas:

---------- APA ----------
Ramírez, J.A., Brosa, C. & Galagovsky, L.R. (2005) . Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6. Phytochemistry, 66(5), 581-587.
http://dx.doi.org/10.1016/j.phytochem.2004.12.029
---------- CHICAGO ----------
Ramírez, J.A., Brosa, C., Galagovsky, L.R. "Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6" . Phytochemistry 66, no. 5 (2005) : 581-587.
http://dx.doi.org/10.1016/j.phytochem.2004.12.029
---------- MLA ----------
Ramírez, J.A., Brosa, C., Galagovsky, L.R. "Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6" . Phytochemistry, vol. 66, no. 5, 2005, pp. 581-587.
http://dx.doi.org/10.1016/j.phytochem.2004.12.029
---------- VANCOUVER ----------
Ramírez, J.A., Brosa, C., Galagovsky, L.R. Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6. Phytochemistry. 2005;66(5):581-587.
http://dx.doi.org/10.1016/j.phytochem.2004.12.029