Stimulation of Orobanche ramosa seed germination by fusicoccin derivatives: a structure-activity relationship study.
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.
Evidente
Antonio
A
Dipartimento di Scienze del Suolo, della Pianta e dell'Ambiente, Università degli Studi di Napoli Federico II, Via Università 100, I-80055 Portici, Italy. evidente@unina.it
Andolfi
Anna
A
Fiore
Michele
M
Boari
Angela
A
Vurro
Maurizio
M
D004224:Diterpenes / Q000737:chemistry / Q000494:pharmacology; D018525:Germination / Q000187:drug effects*; D006027:Glycosides / Q000737:chemistry / Q000494:pharmacology*; D008968:Molecular Conformation; D031672:Orobanche / Q000187:drug effects / Q000254:growth & development*; D010937:Plant Growth Regulators / Q000737:chemistry / Q000494:pharmacology*; D012639:Seeds / Q000187:drug effects / Q000254:growth & development*; D013045:Species Specificity; D013329:Structure-Activity Relationship
D004224:Diterpenes; D006027:Glycosides; D010937:Plant Growth Regulators; C007808:fusicoccin; C509528:cotylenol