RT journal article
T1 Easy Access to Alkoxy, Amino, Carbamoyl, Hydroxy, and Thiol Derivatives of Sesquiterpene Lactones and Evaluation of Their Bioactivity on Parasitic Weeds
A1 Cala Peralta, Antonio
A1 García Zorrilla, Jesús
A1 Rial Cumbrera, Carlos
A1 González Molinillo, José María
A1 Varela Montoya, Rosa María
A1 Macías Domínguez, Francisco Antonio
A2 Química Orgánica
K1 sesquiterpene lactone
K1 etiolated wheat coleoptiles
K1 seed germination
K1 dehydrocostuslactone
K1 costunolide
K1 Michael addition
AB It has been hypothesized that the α-methylene-γ-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.
PB ACS Publications
SN 1520-5118
YR 2019
FD 2019-09-05
LK http://hdl.handle.net/10498/33392
UL http://hdl.handle.net/10498/33392
LA eng
DS Repositorio Institucional de la Universidad de Cádiz
RD 07-nov-2026