64.飽和型ストリゴラクトンアナログのAM菌菌糸分岐誘導における立体特異性(口頭発表)

概要

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Strigolactones are plant apocarotenoids capable of acting as a host-recognition signal for both beneficial arbuscular mycorrhizal (AM) fungi and devastating root parasitic weeds. A tentative molecular mechanism proposed for the stimulation of seed germination by Strigolactones in root parasitic weeds involves the addition of a nucleophilic species, present at a putative receptor site, to the enol ether carbon double bond in a Michael fashion. The enol ether bond connecting the C and D rings has also been suggested to be essential for hyphal branching-inducing activity in AM fungi. To test this hypothesis, we synthesized and purified four optically-pure diastereomers of 3,6'-dihydro-GR24, in which the enol ether carbon double bond is reduced to a single bond, and examined their activities on an AM fungusGigaspora margarita. Among the four compounds tested, only one diastereomer was highly active on hyphal branching in the fungus. The activity of this compound was comparable to that of GR24 (2.5 ng/disc). This indicates that the enol ether carbon bond is not essential for hyphal branching-inducing activity in AM fungi.
植物化学調節学会の論文
2007-10-05