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The plant Centaurea cineraria L. subsp. cineraria has been investigated as a potential source of inhibitors of broomrape radicle growth. The latter are weeds that pose a threat to agriculture and for which there are few methods available for the control of infestations. Four sesquiterpene lactones have been isolated from C. cineraria L. subsp. cineraria aerial parts and identified as isocnicin, cnicin, salonitenolide, and 11β,13-dihydrosalonitenolide using spectroscopic, spectrometric, and optical methods. Salonitenolide and 11β,13-dihydrosalonitenolide have been isolated for the first time from this plant. Tested at 1.0–0.1 mM against the broomrape species Phelipanche ramosa, Orobanche minor, Orobanche crenata, and Orobanche cumana, isocnicin, cnicin, and salonitenolide demonstrated remarkable inhibitory activity (over 80% in most of the cases) at the highest concentrations. Structure-activity relationship conclusions indicated the significance of the α,β-unsaturated lactone ring. In addition, the synthetic acetylated derivative of salonitenolide showed the strongest activity among all compounds tested, with inhibitions close to 100% at different concentrations, which has been related to a different lipophilicity and the absence of H-bond donor atoms in its structure. Neither the extracts nor the compounds exhibited the stimulating activity of broomrape germination (induction of suicidal germination). These findings highlight the potential of C. cineraria to produce bioactive compounds for managing parasitic weeds and prompt further studies on its sesquiterpene lactones as tools in developing natural product-based herbicides.

Cuscuta campestris Yunck. is a parasitic weed responsible for severe yield losses in crops worldwide. The selective control of this weed is scarce due to the difficult application of methods that kill the parasite without negatively affecting the infected crop. trans-Cinnamic acid is secreted by plant roots naturally into the rhizosphere, playing allelopathic roles in plant–plant communities, although its activity in C. campestris has never been investigated. In the search for natural molecules with phytotoxic activity against parasitic weeds, this work hypothesized that trans-cinnamic acid could be active in inhibiting C. campestris growth and that a study of a series of analogs could reveal key structural features for its growth inhibition activity. In the present structure–activity relationship (SAR) study, we determined in vitro the inhibitory activity of trans-cinnamic acid and 24 analogs. The results showed that trans-cinnamic acid’s growth inhibition of C. campestris seedlings is enhanced in eight of its derivatives, namely hydrocinnamic acid, 3-phenylpropionaldehyde, trans-cinnamaldehyde, trans-4-(trifluoromethyl)cinnamic acid, trans-3-chlorocinnamic acid, trans-4-chlorocinnamic acid, trans-4-bromocinnamic acid, and methyl trans-cinnamate. Among the derivatives studied, the methyl ester derivative of trans-cinnamic acid was the most active compound. The findings of this SAR study provide knowledge for the design of herbicidal treatments with enhanced activity against parasitic weeds.

Cuscuta campestris is a parasitic weed species that inflicts worldwide noxious effects in many broadleaf crops due to its capacity to withdraw nutrients and water directly from the crop vascular system using haustorial connections. Cuscuta campestris control in the majority of crops affected is non-existent, and thus, research for the development of control methods is needed. Hydrocinnamic acid occurs naturally in the rhizosphere, playing regulatory roles in plant–plant and plant–microbe communities. The toxicity of hydrocinnamic acid against C. campestris was recently identified. In the present work, a structure–activity relationship study of 21 hydrocinnamic acid analogues was performed to identify key structural features needed for its allelopathic action against the seedling growth of this parasitic plant. The findings of this study provide the first step for the design of herbicides with enhanced activity for the control of C. campestris infection.