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Stimulation of Orobanche ramosa seed germination by fusicoccin derivatives: A structure–activity relationship study

2005; Elsevier BV; Volume: 67; Issue: 1 Linguagem: Inglês

10.1016/j.phytochem.2005.10.010

1873-3700

Antonio Evidente, Anna Andolfi, Michele Fiore, Angela Boari, Maurizio Vurro,

Plant and animal studies

A structure–activity relationship study was conducted assaying 25 natural analogues and derivatives of fusicoccin (FC), and cotylenol, the aglycone of cotylenins, for their ability to stimulate the seed germination of the parasitic species Orobanche ramosa. Some of the compounds tested proved to be highly active, being 8,9-isopropylidene of the corresponding FC aglycone and the dideacetyl derivative the most active FC derivatives. In both groups of glucosides and aglycones (including cotylenol), the most important structural feature to impart activity appears to be the presence of the primary hydroxy group at C-19. Furthermore, the functionalities and the conformation of the carbotricyclic ring proved to play a significant role. The dideacetyl derivative of FC, being easily and rapidly obtainable in high yield starting by FC, could be of interest for its practical application as a stimulant of Orobanche ramosa seed germination, inducing the "suicidal germination", an interesting approach for parasitic plant management.