RT journal article
T1 Synthesis of Active Strigolactone Analogues Based on Eudesmane- and Guaiane-Type Sesquiterpene Lactones
A1 García Zorrilla, Jesús
A1 Cala Peralta, Antonio
A1 Rial Cumbrera, Carlos
A1 Rodríguez Mejías, Francisco Javier
A1 González Molinillo, José María
A1 Varela Montoya, Rosa María
A1 Macías Domínguez, Francisco Antonio
A2 Química Orgánica
K1 sesquiterpene lactone
K1 eudesmanolide
K1 costunolide
K1 dehydrocostuslactone
K1 strigolactone analogue
K1 parasitic weed
K1 Orobanche
K1 Phelipanche
AB Strigolactones are natural products that are exuded by plants and stimulate parasitic weed germination. Their use in herbicides is limited since they are produced in small quantities, but the synthesis of bioactive analogues provides an alternative source. In this work, eleven analogues have been synthesized. Among them, nine compounds belong to a novel family named eudesmanestrigolactones. The procedure is short (3–6 steps), the starting materials are isolated on a multigram scale, and global yields are up to 8%, which significantly enhance isolated yields. In bioassay, the compounds germinated high percentages of Phelipanche ramosa, Orobanche cumana, and Orobanche crenata seeds, even at nanogram doses (100 nM). Bioactivity was stereochemistry-dependent, and it was discussed in terms of the presence and geometry of the enol ether, orientation of the butenolide, and unsaturation of ring A. The reported compounds provide a set of readily obtained allelochemicals with potential applications as preventive herbicides.
PB ACS Publications
SN 1520-5118
YR 2020
FD 2020-08-14
LK http://hdl.handle.net/10498/33389
UL http://hdl.handle.net/10498/33389
LA eng
DS Repositorio Institucional de la Universidad de Cádiz
RD 10-nov-2026