9.ストリゴラクトンの水中での不活性化過程における分解産物の同定(口頭発表)

概要

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Strigolactones are root apocarotenoids that act as a host-derived signal in the rhizosphere communication of plants with arbuscular mycorrhizal (AM) fungi and root parasitic weeds as well as an endogenous plant hormone regulating shoot branching in plants. The chemical lifetime of strigolactones under natural soil conditions is thought to be very short possibly because of easy cleavage of an enol ether bond connecting the C and D rings by water. A tentative reaction mechanism proposed for the water degradation of strigolactones involves a Michael addition of water to the enol ether bond, followed by elimination of the D ring. To examine this hypothetical reaction, a synthetic strigolactone analogue, GR24, was degraded in water containing 3% methanol, and the degradation products were analyzed by HPLC. Along with gradual decrease of GR24 during incubation at 32℃, two new peaks were appeared and gradually increased. The compounds corresponding to these two peaks were identified to be formylated tricyclic ABC lactone and hydroxybutenolide by the comparison of their EI-MS and ^1H-NMR spectra with those of the synthetic standards. These two degradation products did not show hyphal branching-inducing activities on an AM fungus, Gigaspora margarita, at 30 and 300ng/disc, conforming that cleavage of the enol ether bond in the strigolactone results in the loss of activity on the AM fungus.
植物化学調節学会の論文
2008-10-06