New chemical clues for broomrape-sunflower host-parasite interactions: synthesis of guaianestrigolactones.
A comparative structure-activity relationship (SAR) study has been conducted with several guaianolide sesquiterpene lactones (SLs) as inducers of the germination of sunflower broomrape (Orobanche cumana) seeds. Compounds were selected and synthesized to study the influence of the lactone-enol-gamma-lactone moiety on the selectivity of SLs toward the stimulation of sunflower broomrape germination. The results clearly illustrate that SLs are recognized only by O. cumana, while the introduction of a strigol-like second lactone moiety in the guaianolide backbone results in the loss of specificity and hence the germination of other broomrape species. We have named this new class of compounds guaianestrigolactones (GELs).
Macías
Francisco A
FA
Grupo de Alelopatia, Depto de Química Orgánica, Facultad de Ciencias, Universidad de Cadiz, Puerto Real, Cadiz, Spain. famacias@uca.es
García-Díaz
María D
MD
Pérez-de-Luque
Alejandro
A
Rubiales
Diego
D
Galindo
Juan C G
JC
D018525:Germination / Q000187:drug effects*; D006368:Helianthus / Q000378:metabolism*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D031672:Orobanche / Q000196:embryology*; D018517:Plant Roots / Q000378:metabolism; D012639:Seeds / Q000187:drug effects / Q000254:growth & development; D045789:Sesquiterpenes, Guaiane / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013045:Species Specificity; D013329:Structure-Activity Relationship
D007783:Lactones; D045789:Sesquiterpenes, Guaiane