BIOSYNTHETIC RELATIONSHIP OF ARYLTETRALIN LACTONE LIGNANS TO DIBENZYLBUTYROLACTONE LIGNANS

Article abstract of DOI:10.1016/0031-9422(86)80072-3

Key Word Index - Podophyllum hexandrum; Podophyllaceae; lignans; aryltetralin; dibenzylbutyrolactone; biosynthesis; podophyllotoxin. Feeding experiments in Podophyllum hexandrum plants have shown that the dibenzylbutyrolactone lignan yatein is a satisfactory precursor of the aryltetralin lignan podophyllotoxin.The corresponding cis isomer of yatein was also incorporated, but to a lesser extent, and probably via yatein.Podorhizol, epipodorhizol and anhydropodorhizol were not incorporated into podophyllotoxin, despite the demonstrated presence of both podorhizol and anhydropodorhizol in P. hexandrum plants.A biosynthetic sequence from yatein to podophyllotoxin via a key quinonemethide intermediate is proposed.This intermediate is probably also the precursor of both podorhizol and anhydropodorhizol.Matairesinol is proposed as the branchpoint compound to the trimethoxy and hydroxydimethoxy series of aryltetralin lignans in Podophyllum.Labelling patterns in podophyllotoxin and 4'-demethylpodophyllotoxin derived from methionine support this suggestion.