Chemical modification of a phenoxyfuranone-type strigolactone mimic for selective effects on rice tillering or Striga hermonthica seed germination.

We previously reported that a series of phenoxyfuranone compounds, designated 'debranones', mimic strigolactone (SL) activity. 4-Bromodebranone (4BD) is a functionally selective SL mimic that reduces the number of shoot branches on rice more potently than GR24, a typical synthetic SL analogue, but does not induce seed germination in the root-parasitic plant Striga hermonthica. To enhance the selective activity of debranones in stimulating the seed germination of root-parasitic plants, we prepared several analogues of 4BD in which the chlorine atom was substituted with an H atom at the o-, m- or p-position on the phenyl ring (designated 2-, 3-, or 4-chlorodebranone, respectively) or had a bicyclic group instead of the phenyl ring. We evaluated the biological activities of the compounds with rice tillering assays and S. hermonthica seed germination assays. Both assays showed that the substituent position affected debranone efficiency, and among the monochlorodebranones, 2-chlorodebranone was more effective than the other two isomers in both assays. When the activities of the bicyclic debranones were compared in the same two assays, one was more active than GR24 in the rice tillering assay. This debranone also stimulated the germination of S. hermonthica seeds. Thus, some debranone derivatives induced the germination of S. hermonthica seeds, although their activities were still ∼1/20 that of GR24. These results strongly suggest that further and rigorous structure-activity relationship studies of the debranones will identify derivatives that more potently stimulate the suicidal germination of S. hermonthica seeds. © 2016 Society of Chemical Industry.

Takahashi I ，Fukui K ，Asami T 《-》

Selective mimics of strigolactone actions and their potential use for controlling damage caused by root parasitic weeds.

Fukui K ，Ito S ，Asami T 《-》

The Evaluation of Debranone Series Strigolactone Agonists for Germination Stimulants in Orobanche Species.

Kawada K ，Takahashi I ，Takei S ，Nomura A ，Seto Y ，Fukui K ，Asami T ... -  《-》

On improving strigolactone mimics for induction of suicidal germination of the root parasitic plant Striga hermonthica.

Strigolactones (SLs) are plant hormones that regulate the branching of plants and seed germination stimulants of root parasitic plants. As root parasites are a great threat to agricultural production, the use of SL agonists could be anticipated to provide an efficient method for regulating root parasites as suicidal germination inducers. A series of phenoxyfuranone-type SL mimics, termed debranones, has been reported to show potent bioactivities, including reduction of the tiller number on rice, and stimulation of seed germination in the root parasite Striga hermonthica. To exert both activities, two substituents on the phenyl ring of the molecules were important but at least a substituent at the 2-position must be an electron-withdrawing group. However, little is known about the effect of the properties of the substituents at the 2-position on bioactivities. Here, we found that different substituents at the 2-position give different preferences for bioactivities. Halogenated debranones were more effective than the others and SL agonist GR24 for inhibiting rice tiller but far less effective in the induction of S. hermonthica germination. Meanwhile, nitrile and methyl derivatives clearly stimulated the germination of S. hermonthica seeds. Although their IC50 values were 100 times higher than that of GR24 in the receptor competitive binding assay, their physiological activities were approximately 1/10 of GR24. These differences could be due to their uptake in plants and/or their physicochemical stability under our experimental conditions. These findings could support the design of more potent and selective SL agonists that could contribute to solving big agricultural issues.

Takahashi I ，Fukui K ，Asami T 《-》

A Taylor-Made Design of Phenoxyfuranone-Type Strigolactone Mimic.

Fukui K ，Yamagami D ，Ito S ，Asami T ... -  《Frontiers in Plant Science》