ABSTRACT
BACKGROUND: Strigolactones play an important role in the rhizosphere as signalling molecules stimulating the seed germination of parasitic weed seeds and hyphal branching of arbuscular micorrhiza, and also act as hormones in plant roots and shoots. Strigolactone derivatives, e.g. strigolactams, could be used as suicidal germination inducers in the absence of a host crop for the decontamination of land infested with parasitic weed seeds. RESULTS: We report the stereoselective synthesis of novel strigolactams, together with some of their critical physicochemical properties, such as water solubility, hydrolytic stability, as well as their short soil persistence. In addition, we show that such strigolactams are potent germination stimulants of O. cumana parasitic weed seeds and do not affect the seed germination and the root growth of sunflower. CONCLUSIONS: The novel strigolactam derivatives described here compare favourably with the corresponding GR-28 strigolactones in terms of biological activity and physicochemical properties. However, we believe strigolactone and strigolactam derivatives require further structural optimisation to improve their soil persistence to demonstrate a potential for agronomical applications. © 2016 Society of Chemical Industry.
Subject(s)
Germination/drug effects , Helianthus/drug effects , Lactams/pharmacology , Orobanche/drug effects , Helianthus/growth & development , Lactams/chemical synthesis , Lactams/chemistry , Lactones/chemistry , Orobanche/growth & development , Plant Roots/drug effects , Plant Roots/growth & development , Seeds/drug effects , Seeds/growth & developmentABSTRACT
Very recently, strigolactones have been conclusively identified as phytohormones. The progresses achieved in this field are culminating in the identification of the molecular receptors involved in the signal transduction mechanism. The exact mechanism of the mode of action of strigolactones still remains to be fully elucidated and we were interested to gain some insight into the mechanism of action of strigolactones by selectively modifying the reactivity of the lactone C-ring. Therefore, we report here the synthesis of strigolactams 1 and 16 and their surprisingly good activity on the germination of Orobanche cumana parasitic weed seeds.
Subject(s)
4-Butyrolactone/analogs & derivatives , 4-Butyrolactone/pharmacology , Heterocyclic Compounds, 3-Ring/chemical synthesis , Heterocyclic Compounds, 3-Ring/pharmacology , Lactones/chemistry , Orobanche/drug effects , Seeds/drug effects , 4-Butyrolactone/chemical synthesis , 4-Butyrolactone/chemistry , Germination/drug effects , Heterocyclic Compounds, 3-Ring/chemistry , Lactones/pharmacology , Molecular Structure , Orobanche/chemistryABSTRACT
Strigolactones have been the latest identified phytohormones. Among the strigolactones analogues described recently, GR-24 remains the most studied derivative which is used as standard in this field. In order to improve several properties of GR-24 for potential agronomical applications, we investigated the effect of substituents on the B and C-rings on the activity for seed germination induction. We report here the synthesis of 9 GR-24 analogues via a [2+2] intramolecular cycloaddition of ketene-iminium salts and a summary of their activity for the germination of Orobanche cumana (broomrape) seeds.