Studies on the lignan chemical constituents from pine needles of Pinus massoniana Lamb.

AimTo study the chemical constituents of the pine needles from Pinus massoniana Lamb.. MethodsVarious chromatographic techniques were used for the separation and purification. The physicochemical properties and spectral data were used to elucidate the structures. ResultsThree compounds were isolated from the n-BuOH fraction of water-extracts. The structures were identified as (7S,8r)-4,9′-dihydroxyl-3,3′-dimethyoxyl-7,8-dihydrobenzofunan-1′-propanolneolignan-9-O-α-L-rhamnopyranoside (massonianoside D, 7), 4,4′,9,9′-tetrahydroxyl-3,3′-dimethyoxyl-tetrahydrocyclolignan ((+)-isolariciresinol, 8) and 4,4′,9′-trihydroxyl-3,3′-dimethyoxyl-tetrahydrocyclolignan-9-O-β-D-xylopyranoside (isolariciresinol-9-O-xyloside, 9) on the basis of spectral data (ORD, UV, IR, MS, ¹HNMR, ¹³CNMR, ¹H-¹HCOSY, HMQC and HMBC etc.). ConclusionCompound 7 is a new compound, while compounds 8 and 9 were isolated from this plant for the first time.