Easy Access to Alkoxy, Amino, Carbamoyl, Hydroxy, and Thiol Derivatives of Sesquiterpene Lactones and Evaluation of Their Bioactivity on Parasitic Weeds

Article abstract of DOI:10.1021/acs.jafc.9b03098

It has been hypothesized that the α-methylene-?-lactone moiety of sesquiterpene lactones is a key unit for their bioactivity. As a consequence, modifications of these compounds have been focused on this fragment. In the work reported here, two sesquiterpene lactones, namely, dehydrocostuslactone and β-cyclocostunolide, a eudesmanolide obtained by controlled cyclization of costunolide, were chosen for modification by Michael addition at C-13. On applying this reaction to both compounds, it was possible to introduce the functional groups alkoxy, amino, carbamoyl, hydroxy, and thiol to give products in good to high yields, depending on the base and solvent employed. In particular, the introduction of a thiol group at C-13 in both compounds was achieved with outstanding yields (>90%) and this is unprecedented for these sesquiterpene lactones. The bioactivities of the products were evaluated on etiolated wheat coleoptile elongation and germination of seeds of parasitic weeds, with significant activity observed on Orobanche cumana and Phelipanche ramosa. The structure-activity relationships are discussed.

Full text of DOI:10.1021/acs.jafc.9b03098

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Functional Structure/Activity Relationships
Easy access to alkoxy, amino, carbamoyl, hydroxy and thiol derivatives of
sesquiterpene lactones and evaluation of their bioactivity on parasitic weeds
Antonio Cala, Jesús G Zorrilla, Carlos Rial, José M. G. Molinillo, Rosa M. Varela, and Francisco A. Macías
J. Agric. Food Chem., Just Accepted Manuscript • DOI: 10.1021/acs.jafc.9b03098 • Publication Date (Web): 05 Sep 2019
Downloaded from pubs.acs.org on September 9, 2019
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Journal of Agricultural and Food Chemistry
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Journal of Agricultural and Food Chemistry
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Journal of Agricultural and Food Chemistry
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Journal of Agricultural and Food Chemistry
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Journal of Agricultural and Food Chemistry
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