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

Galagovsky, L R; Gros, E G; Ramírez, J A

Galagovsky, L R; Gros, E G; Ramírez, J A.

Afiliação

Galagovsky LR; Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, 1428, Buenos Aires, Argentina. lyrgala@qo.fcen.uba.ar

Phytochemistry ; 58(6): 973-80, 2001 Nov.

Article em En | MEDLINE | ID: mdl-11684198

RESUMO

In this paper we describe the synthesis of two new fluorinated brassinosteroids: (22R,23R)-22,23-dihydroxy-3alpha-fluorostigmastan-6-one and (22R,23R)-22,23-dihydroxy-3beta-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.

Assuntos

Colestanonas/síntese química; Colestanonas/farmacologia; Flúor/química; Colestanonas/química; Espectroscopia de Ressonância Magnética; Espectrometria de Massas/métodos; Estrutura Molecular

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Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Colestanonas / Flúor Idioma: En Revista: Phytochemistry Ano de publicação: 2001 Tipo de documento: Article País de afiliação: Argentina País de publicação: Reino Unido

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