Biosynthesis of Lambertellols Based on the High Specific Incorporation of the 13C-Labeled Acetates and Their Biological Properties

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Abstract
Biosyntheses of lambertellols A (1) and B (2) as well as lambertellin (3) were investigated by isotope labeling experiments. Nearly 40% of specific incorporation of [1,2-13C2]acetate was achieved, and all the carbons in 1 and 2 were labeled. This high incorporation of the labeled acetate was realized by providing INADEQUATE spectra by employing only 0.4 and 0.7 mg of 1 and 2, respectively. Our studies revealed that 1−3 are biogenetically synthesized via loss of two carbons from octameric acetate. A biological assay against Monilinia fructicola revealed those remarkably inhibited hyphal germinations. However, neither of them killed the spores immediately, even in high concentration. These conditions induced the formation of microconidia.