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Abstract:

In this paper we describe the synthesis of two new fluorinated brassinosteroids: (22R,23R)-22,23-dihydroxy-3α-fluorostigmastan-6-one and (22R,23R)-22,23-dihydroxy-3β-fluorostigmastan-6-one. Their bioactivities were evaluated in the rice lamina inclination test and compared with that of 28-homocastasterone, 28-homotyphasterol and 28-homoteasterone, possible biosynthetic precursors of 28-homobrassinolide. Results confirmed expected similarities between the biosynthesis of 24-ethylbrassinosteroids (named as the 28-homo series) and that described for 24-methylbrassinosteroids, and also indicated that these precursors might exhibit per se activities. © 2001 Published by Elsevier Science Ltd.

Registro:

Documento: Artículo
Título:Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide
Autor:Galagovsky, L.R.; Gros, E.G.; Ramírez, J.A.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, 1428 Buenos Aires, Argentina
Palabras clave:28-Homobrassinolide; Bioactivity; Biosynthesis; Brassinosteroids; C-3 Fluorinated analogs; 22,23 dihydroxy 3alpha fluorostigmastan 6 one; 22,23 dihydroxy 3beta fluorostigmastan 6 one; 24 ethylbrassinosteroid derivative; 24 methylbrassinosteroid derivative; 28 homobrassinolide; 28 homocastasterone; 28 homoteasterone; 28 homotyphasterol; brassinolide; cholestane derivative; fluorine; homobrassinolide; unclassified drug; article; bioassay; biosynthesis; chemical structure; chemistry; fluorination; mass spectrometry; methodology; nuclear magnetic resonance spectroscopy; plant growth; rice; synthesis; Cholestanones; Fluorine; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure
Año:2001
Volumen:58
Número:6
Página de inicio:973
Página de fin:980
DOI: http://dx.doi.org/10.1016/S0031-9422(01)00379-X
Título revista:Phytochemistry
Título revista abreviado:Phytochemistry
ISSN:00319422
CODEN:PYTCA
CAS:Cholestanones; Fluorine, 7782-41-4; homobrassinolide, 74174-44-0
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00319422_v58_n6_p973_Galagovsky

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Citas:

---------- APA ----------
Galagovsky, L.R., Gros, E.G. & Ramírez, J.A. (2001) . Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide. Phytochemistry, 58(6), 973-980.
http://dx.doi.org/10.1016/S0031-9422(01)00379-X
---------- CHICAGO ----------
Galagovsky, L.R., Gros, E.G., Ramírez, J.A. "Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide" . Phytochemistry 58, no. 6 (2001) : 973-980.
http://dx.doi.org/10.1016/S0031-9422(01)00379-X
---------- MLA ----------
Galagovsky, L.R., Gros, E.G., Ramírez, J.A. "Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide" . Phytochemistry, vol. 58, no. 6, 2001, pp. 973-980.
http://dx.doi.org/10.1016/S0031-9422(01)00379-X
---------- VANCOUVER ----------
Galagovsky, L.R., Gros, E.G., Ramírez, J.A. Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide. Phytochemistry. 2001;58(6):973-980.
http://dx.doi.org/10.1016/S0031-9422(01)00379-X