22-Oxocholestanes as plant growth promoters

• Published in: Steroids Vol. 98; pp. 126 - 131
• Main Authors: Zeferino-Diaz, Reyna, Hilario-Martinez, J. Ciciolil, Rodriguez-Acosta, Maricela, Sandoval-Ramirez, Jesus, Fernandez-Herrera, Maria A.
• Format: Journal Article
• Language: English
• Published: NEW YORK Elsevier Inc 01.06.2015; Elsevier
• Subjects: 22-Oxocholestane side-chain; Biochemistry & Molecular Biology; Brassinosteroids; Cholestanes - chemical synthesis; Cholestanes - chemistry; Cholestanes - pharmacology; Endocrinology & Metabolism; Growth promoting activity; Life Sciences & Biomedicine; Oryza - growth & development; Plant Growth Regulators - chemical synthesis; Plant Growth Regulators - chemistry; Plant Growth Regulators - pharmacology; Rice lamina joint inclination bioassay; Science & Technology; Rice lamina joint inclination bioassay; Brassinosteroids; Growth promoting activity; 22-Oxocholestane side-chain; STEROIDAL SAPOGENINS; LAMINA INCLINATION; SIDE-CHAIN; ANTICANCER AGENT; OSW-1; CHOLESTANE GLYCOSIDES; AGLYCONE; BETA-D-GLUCOPYRANOSIDE
• ISSN: 0039-128X; 1878-5867
• DOI: 10.1016/j.steroids.2015.03.005

[Display omitted] •22-Oxocholestane derivatives are synthesized from steroidal sapogenins.•The new side-chain is obtained in a four-step pathway from the spiroketal moiety.•Plant growth promotion is given in Mexican rice cultivars.•22-Oxocholestanes are as active as homobrassinolide. The spirostanic steroidal side-chain of diosgenin and hecogenin was modified to produce 22-oxocholestane derivatives. This type of side-chain was obtained in good yields through a straightforward four-step pathway. These compounds show potent brassinosteroid-like growth promoting activity evaluated via the rice lamina joint inclination bioassay. This is the first report of steroidal skeletons bearing the 22-oxocholestane side-chain and preserving the basic structure (A–D rings) from their corresponding parent compounds acting as plant growth promoters.