Lignans, alkaloids and coumarins from Haplophyllum vulcanicum

Six lignans, (-)-haplomyrfolol, (-)-haplomyrfolin, (-)-kusunokinin, (-)-syringaresinol, diphyllin and (-)-tuberculatin, five furoquinoline alkaloids, dictamnine, gamma-fagarine, haplopine, robustine and skimmianine, and two coumarins, scopoletin and umbelliferone, have been isolated from Haplophyllum vulcanicum. (-)-Haplomyrfolol, a novel dibenzylbutyrolactol, exists as an epimeric mixture in solution. Complete assignments of the proton and carbon chemical shifts for the individual epimers were accomplished on the basis of high resolution 1D and 2D NMR data. This is the first report of (-)-syringaresinol from the genus Haplophyllum and of (-)-haplomyrfolin, (-)-tuberculatin, dictamnine, haplopine and umbelliferone from the title species.