Mimicking natural phytohormones. 26-Hydroxycholestan-22-one derivatives as plant growth promoters

• Published in: Steroids Vol. 125; pp. 20 - 26
• Main Authors: Zeferino-Diaz, Reyna, Hilario-Martinez, J. Ciciolil, Rodriguez-Acosta, Maricela, Carrasco-Carballo, Alan, Hernandez-Linares, Maria Guadalupe, Sandoval-Ramirez, Jesus, Fernandez-Herrera, Maria A.
• Format: Journal Article
• Language: English
• Published: NEW YORK Elsevier Inc 01.09.2017; Elsevier
• Subjects: 26-Hydroxycholestan-22-one derivatives; Biochemistry & Molecular Biology; Biomimetic Materials - chemical synthesis; Biomimetic Materials - chemistry; Biomimetic Materials - pharmacology; Cholestanols - chemistry; Dose-Response Relationship, Drug; Endocrinology & Metabolism; Life Sciences & Biomedicine; Mimic phytohormones; Oryza - drug effects; Oryza - growth & development; Plant growth promoting activity; Plant Growth Regulators - chemical synthesis; Plant Growth Regulators - chemistry; Plant Growth Regulators - pharmacology; Rice lamina inclination test; Science & Technology; Plant growth promoting activity; Mimic phytohormones; Rice lamina inclination test; 26-Hydroxycholestan-22-one derivatives; BRASSINOSTEROIDS; STEROIDS; BRASSINOLIDE; ANDROSTANE; BEARING; BETA-D-GLUCOPYRANOSIDE; SPIROSTANIC ANALOGS
• ISSN: 0039-128X; 1878-5867
• DOI: 10.1016/j.steroids.2017.06.004

[Display omitted] •26-Hydroxycholestan-22-one derivatives were synthesized from the steroidal sapogenin diosgenin.•The new cholestane derivatives act as phytohormones.•Plant growth promotion was measured in Mexican rice cultivars.•All the compounds show excellent activity compared to homobrassinolide. 26-Hydroxycholestan-22-one derivatives with oxygenated functions in the rings A and/or B were successfully synthesized from diosgenin. After the modifications of rings A and B, the spiroketal side chain was selectively opened through a Lewis acid mediated acetolysis to afford the cholestane derivatives. These compounds incorporate pharmacophores, which mimic the activity of natural phytohormones and show high growth promoting activity in Mexican rice cultivars using the rice lamina inclination test.