In the course of our mechanistic studies of mycoparasitism between
Lambertella spp. (the parasite) and
Monilinia fructigena (
M. f., the host) on apple fruits, we isolated known lambertellin (
1) and new spirobutenolides lambertellols A (
2), B (
3). Lambertellols were detected only when the host
M. f. co-inhabited in the broth of
M. f. Lambertellols
2,
3 were readily interconverted and gradually decomposed into
1. Our total syntheses enable the SAR studies to disclose that
1 should be the real active species and
2 and
3 are diffusible precursors. In order to rationally explain these observations, we performed dynamic analyses of the metabolites to disclose a novel alleropathy ‘Lambertellin system’ as described in this article. This mechanism also accords with the progress of ‘Natsu-Nenju’ disease on apple fruits, which is known to be a mysterious phyto-disease because of two unique stages of its lifecycle, anamorphic (asexual) and teleomorphic (sexual). Only organic chemistry based investigations could approach the final conclusion in this particular case.
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