Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide

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-homocastas...

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Autores principales:	Gros, Eduardo Gervasio, Ramirez, Javier Alberto
Publicado:	2001
Materias:	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
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00319422_v58_n6_p973_Galagovsky http://hdl.handle.net/20.500.12110/paper_00319422_v58_n6_p973_Galagovsky
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00319422_v58_n6_p973_Galagovsky
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spelling	paper:paper_00319422_v58_n6_p973_Galagovsky2023-06-08T14:59:35Z Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide Gros, Eduardo Gervasio Ramirez, Javier Alberto 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 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. Fil:Gros, E.G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ramírez, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2001 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00319422_v58_n6_p973_Galagovsky http://hdl.handle.net/20.500.12110/paper_00319422_v58_n6_p973_Galagovsky
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	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
spellingShingle	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 Gros, Eduardo Gervasio Ramirez, Javier Alberto Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide
topic_facet	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
description	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.
author	Gros, Eduardo Gervasio Ramirez, Javier Alberto
author_facet	Gros, Eduardo Gervasio Ramirez, Javier Alberto
author_sort	Gros, Eduardo Gervasio
title	Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide
title_short	Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide
title_full	Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide
title_fullStr	Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide
title_full_unstemmed	Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide
title_sort	synthesis and bioactivity of natural and c-3 fluorinated biosynthetic precursors of 28-homobrassinolide
publishDate	2001
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00319422_v58_n6_p973_Galagovsky http://hdl.handle.net/20.500.12110/paper_00319422_v58_n6_p973_Galagovsky
work_keys_str_mv	AT groseduardogervasio synthesisandbioactivityofnaturalandc3fluorinatedbiosyntheticprecursorsof28homobrassinolide AT ramirezjavieralberto synthesisandbioactivityofnaturalandc3fluorinatedbiosyntheticprecursorsof28homobrassinolide
_version_	1768542164519747584

Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide

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