Stereochemical Assignment of Strigolactone Analogues Confirms Their Selective Biological Activity.
Strigolactones (SLs) are new plant hormones with various developmental functions. They are also soil signaling chemicals that are required for establishing beneficial mycorrhizal plant/fungus symbiosis. In addition, SLs play an essential role in inducing seed germination in root-parasitic weeds, which are one of the seven most serious biological threats to food security. There are around 20 natural SLs that are produced by plants in very low quantities. Therefore, most of the knowledge on SL signal transduction and associated molecular events is based on the application of synthetic analogues. Stereochemistry plays a crucial role in the structure-activity relationship of SLs, as compounds with an unnatural D-ring configuration may induce biological effects that are unrelated to SLs. We have synthesized a series of strigolactone analogues, whose absolute configuration has been elucidated and related with their biological activity, thus confirming the high specificity of the response. Analogues bearing the R-configured butenolide moiety showed enhanced biological activity, which highlights the importance of this stereochemical motif.
Department of Chemistry, University of Turin , Via P. Giuria 7, 10125 Turin, Italy.
Emma
E
Artuso
Department of Chemistry, University of Turin , Via P. Giuria 7, 10125 Turin, Italy.
Elena
E
Ghibaudi
Department of Chemistry, University of Turin , Via P. Giuria 7, 10125 Turin, Italy.
Beatrice
B
Lace
Department of Chemistry, University of Turin , Via P. Giuria 7, 10125 Turin, Italy.
Domenica
D
Marabello
Department of Chemistry, University of Turin , Via P. Giuria 7, 10125 Turin, Italy.
Daniele
D
Vinciguerra
Department of Chemistry, University of Turin , Via P. Giuria 7, 10125 Turin, Italy.
Chiara
C
Lombardi
ARO Volcani Center , Bet Dagan 50250, Israel.
Hinanit
H
Koltai
ARO Volcani Center , Bet Dagan 50250, Israel.
Yoram
Y
Kapulnik
DBIOS, University of Turin , Viale Mattioli 25, 10125 Turin, Italy.
Mara
M
Novero
Department of Chemistry "Ugo Schiff", University of Florence , Via della Lastruccia 13, 50019 Sesto Fiorentino, Italy.
Ernesto G
EG
Occhiato
Department of Chemistry "Ugo Schiff", University of Florence , Via della Lastruccia 13, 50019 Sesto Fiorentino, Italy.
Dina
D
Scarpi
Department of Chemistry, University of Turin , Via P. Giuria 7, 10125 Turin, Italy.
Stefano
S
Parisotto
Department of Chemistry, University of Turin , Via P. Giuria 7, 10125 Turin, Italy.
Annamaria
A
Deagostino
Department of Chemistry, University of Turin , Via P. Giuria 7, 10125 Turin, Italy.
Paolo
P
Venturello
ARO Volcani Center , Bet Dagan 50250, Israel.
Einav
E
Mayzlish-Gati
ARO Volcani Center , Bet Dagan 50250, Israel.
Ariel
A
Bier
Department of Chemistry, University of Turin , Via P. Giuria 7, 10125 Turin, Italy.
Cristina
C
Prandi
D018525:Germination / Q000187:drug effects; D007783:Lactones / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D010937:Plant Growth Regulators / Q000737:chemistry* / Q000494:pharmacology*; D018517:Plant Roots / Q000737:chemistry; D057685:Plant Weeds / Q000187:drug effects; D012639:Seeds / Q000187:drug effects; D013329:Structure-Activity Relationship; D013559:Symbiosis
D007783:Lactones; D010937:Plant Growth Regulators