Synthesis of Active Strigolactone Analogues Based on Eudesmane- and Guaiane-Type Sesquiterpene Lactones

• Published in: Journal of agricultural and food chemistry Vol. 68; no. 36; pp. 9636 - 9645
• Main Authors: Zorrilla, Jesús G, Cala, Antonio, Rial, Carlos, R. Mejías, Francisco J, Molinillo, José M. G, Varela, Rosa M, Macías, Francisco A
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 09-09-2020
• Subjects: Agricultural and Environmental Chemistry; Germination - drug effects; Herbicides - chemical synthesis; Herbicides - chemistry; Herbicides - pharmacology; Heterocyclic Compounds, 3-Ring - chemical synthesis; Heterocyclic Compounds, 3-Ring - chemistry; Heterocyclic Compounds, 3-Ring - pharmacology; Lactones - chemical synthesis; Lactones - chemistry; Lactones - pharmacology; Orobanchaceae - drug effects; Orobanchaceae - growth & development; Orobanche - drug effects; Orobanche - growth & development; Seeds - drug effects; Seeds - growth & development; Sesquiterpenes - chemistry; Sesquiterpenes - pharmacology; Sesquiterpenes, Eudesmane - chemistry; Sesquiterpenes, Eudesmane - pharmacology; Sesquiterpenes, Guaiane - chemistry; Orobanche; parasitic weed; Phelipanche; eudesmanolide; dehydrocostuslactone; sesquiterpene lactone; costunolide; strigolactone analogue
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/acs.jafc.0c02361

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.