New strigolactone mimics: structure-activity relationship and mode of action as germinating stimulants for parasitic weeds.
Strigolactones (SLs) are new plant hormones with varies important bio-functions. This Letter deals with germination of seeds of parasitic weeds. Natural SLs have a too complex structure for synthesis. Therefore, there is an active search for SL analogues and mimics with a simpler structure with retention of activity. SL analogues all contain the D-ring connected with an enone moiety through an enol ether unit. A new mechanism for the hydrolysis SL analogues involving bidentate bound water and an α,β-hydrolase with a Ser-His-Asp catalytic triad has been proposed. Newly discovered SL mimics only have the D-ring with an appropriate leaving group at C-5. A mode of action for SL mimics was proposed for which now supporting evidence is provided. As predicted an extra methyl group at C-4 of the D-ring blocks the germination of seeds of parasitic weeds.
Radboud University Nijmegen, Institute for Molecules and Materials, Cluster of Organic Chemistry, Nijmegen, The Netherlands. B.Zwanenburg@science.ru.nl
Binne
B
Zwanenburg
Sandip K
SK
Nayak
Tatsiana V
TV
Charnikhova
Harro J
HJ
Bouwmeester
D018525:Germination / Q000187:drug effects*; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D015394:Molecular Structure; D010937:Plant Growth Regulators / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D057685:Plant Weeds / Q000737:chemistry / Q000187:drug effects*; D012639:Seeds / Q000737:chemistry / Q000187:drug effects*; D034362:Striga / Q000737:chemistry / Q000187:drug effects*; D013329:Structure-Activity Relationship
D007783:Lactones; D010937:Plant Growth Regulators
Design and synthesis; Germination parasitic weeds; Mode of action; New plant hormones; Strigolactone analogues; Strigolactones; Structure–activity relationship