24 病傷害誘導性 MAPK を活性化するタバコ内生情報伝達物質 "WAF-1" の合成と化学反応性

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In recent years, we identified a novel labdane-type diterpene, (11E, 13E)-labda-11,13-diene-8α, 15-diol (1), from tobacco mosaic virus (TMV)-infected tobacco leaves (Nicotiana tabacum cv. Samsun NN) as a wound induced activation factor-1 "WAF-1". This compound increases rapidly in tobacco leaves during a hypersensitive response to TMV-infection and after wounding, and activates mitogen-activated protein kinases (MAPKs), WIPK and SIPK, at nanomolar levels (the maximum activities are observed by exogenous application at 0.1-1.0 nM, respectively). Both MAPKs are respectively located at control points in the signal transduction network of plant defense. Thus, WAF-1 is considered to be one of the critical signal transducers in defense responses in tobacco plants. Here we report the synthesis and chemical reactivity of WAF-1. WAF-1 was synthesized from the known 8α-hydroxydriman-11-al (6), prepared from easily available sclareolide (2), via the Honoer-Wadsworth-Emmons reaction using 3-ethoxycarbonyl-2-methyl-prop-2-enylphosphonate (7) in a optically pure form. WAF-1 was measurably air-sensitive : upon exposure to air, WAF-1 suffered oxidative degradation and lost the two carbon unit, C-14 and -15,to give (11E)-8α- hydroxy-14,15-dinorlabd-11-en-13-one (14) as a major product.
植物化学調節学会の論文
2002-10-31