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Synthesis of active strigolactone analogs based on eudesmane- and guaiane-type sesquiterpene lactones.

J. G. Zorrilla,Antonio Cala,C. Rial,Francisco J R Mejías,J. Molinillo,R. Varela,F. A. Macias

Published 2020 in Journal of Agricultural and Food Chemistry

ABSTRACT

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 analogs provides an alternative source. In this work eleven analogs 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 enhances 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 is 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.

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