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Chromatographic fractionation of the roots of Lindera aggregata has led to the isolation of three new monomers of Lindera cyclopentenedione derivatives (1-3), a pair of new enantiomers of bi-linderone derivatives (4a/4b), and six known Lindera cyclopentenediones (5-8 and 9a/9b). Their structures were determined by NMR and MS data. The absolute configurations of the new bi-linderone derivative enantiomers (4a/4b) were determined by ECD calculation. (±)-Lindepentone A (1) presents the novel skeleton of 3,5-dioxocyclopent-1-enecarboxylate. Lindoxepines A (2) and B (3) present an unprecedented oxepine-2,5-dione derivative skeleton, which may be enlightening for the in vivo biosynthesis of the monomers of Lindera cyclopentenediones. A possible biosynthetic pathway for 1 and a plausible biosynthetic pathway from stilbenes to Lindera cyclopentenediones via the key intermediates 2 and 3 were postulated. The inhibitory activity of these compounds against three microorganisms was also evaluated.

Lindera cyclopentenedione intermediates from the roots of Lindera aggregata