Biomaterial Database

Synthesis and bioactivity of C-29 brassinosteroid analogues with different functional groups at C-6. 2005

Javier A Ramírez, and Carme Brosa, and Lydia R Galagovsky

Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria (C1428EGA), Buenos Aires 1428, Argentina.

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-2alpha,3alpha,22,23-tetraol], 6alpha-hydroxy-28-homocastasterone [(22R,23R)-stigmasta-2alpha,3alpha,6alpha,22,23-pentaol], 6beta-hydroxy-28-homocastasterone [(22R,23R)-stigmasta-2alpha,3alpha,6beta,22,23-pentaol], and [(22R,23R)-6alpha-fluorostigmasta-2alpha,3alpha,22,23-tetraol]. Results indicate that replacement of the 6-keto moiety by an beta or alpha 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 6alpha-fluorinated analogue elicited a low activity, similar to that of the 6-deoxo analogue.

UI	MeSH Term	Description	Entries
D008958	Models, Molecular	Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures.	Molecular Models,Model, Molecular,Molecular Model
D008968	Molecular Conformation	The characteristic three-dimensional shape of a molecule.	Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D010937	Plant Growth Regulators	Any of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.	Phytohormone,Phytohormones,Plant Growth Regulator,Plant Hormone,Plant Hormones,Growth Regulators, Plant,Regulators, Plant Growth,Growth Regulator, Plant,Hormone, Plant,Hormones, Plant,Regulator, Plant Growth
D002778	Cholestanones	CHOLESTANES substituted with any number of keto groups.
D012275	Oryza	A genus of grass family (Poaceae) that include several rice species.	Oryza sativa,Rice,Rices
D013265	Stigmasterol		Poriferasterol
D036226	Seedlings	Young plants produced at the completion of GERMINATION of SEEDS.	Seedling,Malted Grain,Sprouted Seeds,Sprouts, Plant,Grain, Malted,Grains, Malted,Malted Grains,Plant Sprout,Plant Sprouts,Seed, Sprouted,Seeds, Sprouted,Sprout, Plant,Sprouted Seed