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The naturally occurring dinorcholanic lactone vespertilin and two other non-natural derivatives bearing the 5␣-hydroxy-6-oxo moiety were synthesized starting from the readily available steroid sapogenin diosgenin. The obtained compounds showed plant growth promoting activity in the bean's second internode elongation assay.
22-Oxocholestanes as plant growth promoters
Steroids, 2015
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.
Steroidal sapogenins LX. Survey of plants for steroidal sapogenins and other constituents
Journal of Pharmaceutical Sciences, 1961
This is a report of the chemical examination of the sixth 1,000 accessions in a survey of plants for steroidal sapogenins. Data are given for about 1,030 species in 128 families, practically all collected in the United States. I n Agaue a new record of 4.4% genin, mostly smilagenin, was established. The collections of Dioscoreu composita were uniformly high in diosgenin, with a new record of 10.1%.
International Journal of Molecular Sciences
A priority of modern agriculture is to use novel and environmentally friendly plant-growth promoter compounds to increase crop yields and avoid the indiscriminate use of synthetic fertilizers. Brassinosteroids are directly involved in the growth and development of plants and are considered attractive candidates to solve this problem. Obtaining these metabolites from their natural sources is expensive and cumbersome since they occur in extremely low concentrations in plants. For this reason, much effort has been dedicated in the last decades to synthesize brassinosteroids analogs. In this manuscript, we present the synthesis and characterization of seven steroidal carbamates starting from stigmasterol, β-sitosterol, diosgenin and several oxygenated derivatives of it. The synthesis route for functionalization of diosgenin included epoxidation and epoxy opening reactions, reduction of carbonyl groups, selective oxidation of hydroxyl groups, among others. All the obtained compounds were...
Novel steroidal penta- and hexacyclic compounds derived from 12-oxospirostan sapogenins
Steroids, 2010
The E ring regioselective acid-catalyzed opening of spirostanic sapogenins possessing a carbonyl group at C-12, such as botogenin and hecogenin, provided the new 12,23-cyclo-22,26-epoxycholesta-11,22-diene skeleton, in addition to new compounds of the already known 12,23-cyclocholest-12(23)-en-22-one frameworks. This transformation proceeds in a single step, under slightly acidic conditions. Both, pentaand hexacyclic steroids were obtained with retention of configuration of all asymmetric centers.