Host–guest complexation of phthalimide-derived strigolactone mimics with cyclodextrins. Application in agriculture against parasitic weeds. Issue 15 (29th March 2023)

• Record Type: Journal Article
• Authors: Cala Peralta, Antonio; Mejías, Francisco J. R.; Ayuso, Jesús; Rial, Carlos; Molinillo, José M. G.; Álvarez, José A.; Schwaiger, Stefan; Macías, Francisco A.
• Is Part Of: Organic & biomolecular chemistry. Volume 21:Issue 15(2023)
• Page Start: 3214
• Page End: 3225
• Publication Date: 2023-03-29
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d3ob00229b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A study proposing cyclodextrins as eco-friendly compounds to enhance the physicochemical properties of phthalimide-lactones to produce complexes inducing the germination of parasitic weeds even without using organic co-solvents. Abstract : Parasitic weeds are noxious plants that damage crops of economic relevance, especially in Mediterranean and African countries. The strategy of suicidal germination was proposed to deal with this plague by using seed germination inducers that work as a pre-emergence herbicide and reduce the parasitic seed load before sowing. N -Substituted phthalimides with a furanone ring were found to be efficient in inducing the germination of Phelipanche ramosa and Orobanche cumana, two of the most problematic parasitic weeds of crops. However, the solubility of these compounds in water is low. A strategy for enhancing their aqueous solubility is the synthesis of host–guest complexes with cyclodextrins. Three bioactive phthalimide-lactones (PL01, PL04, and PL07 ) were selected and studied to form complexes of increased water solubility with α-, β-, HP-β-, and γ-cyclodextrin. The complexes obtained by the coprecipitation method, with increased aqueous solubility (up to 3.8 times), were studied for their bioactivity and they showed similar or slightly higher bioactivity than free phthalimide-lactones, even without the addition of organic solvents. A theoretical study using semiempirical calculations of molecular models including a solvation system confirmed the physicochemical empirical results. These results demonstrated that cyclodextrins can be used to improve the physicochemical and biological properties of parasitic seed germination inducers.