title: A new lariciresinol-type butyrolactone lignan derived from hydroxymatairesinol and its identification in spruce wood.
abstract: When the natural lignan hydroxymatairesinol (1) was treated with an alkaline aqueous solution, it partially rearranged to isomeric forms of a lariciresinol-type butyrolactone lignan. The two major diastereomers formed (2 and 3) were isolated by column and medium-pressure chromatography, and their structures were elucidated by MS and NMR techniques. These previously unknown butyrolactone lignans were identified as naturally occurring in spruce knotwood by GC, GC-MS, and HPLC-ESI MS/MS analyses. The formation of isohydroxymatairesinol (2) and epi-isohydroxymatairesinol (3) from hydroxymatairesinol (1), and their detection in rat urine after administration of 1, is discussed.
authors.affiliation: Department of Organic Chemistry, Process Chemistry Centre, Abo Akademi University, Biskopsgatan 8, FIN-20500, Turku/Abo, Finland. paeklund@abo.fi
authors.forename: Patrik C
authors.initials: PC
authors.lastname: Eklund
authors.forename: Stefan M
authors.initials: SM
authors.lastname: Willför
authors.forename: Annika I
authors.initials: AI
authors.lastname: Smeds
authors.forename: Fredrik J
authors.initials: FJ
authors.lastname: Sundell
authors.forename: Rainer E
authors.initials: RE
authors.lastname: Sjöholm
authors.forename: Bjarne R
authors.initials: BR
authors.lastname: Holmbom
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D000818:Animals; D017705:Lignans / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D028222:Picea / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*; D051381:Rats; D013237:Stereoisomerism; D014556:Urine / Q000737:chemistry; D014934:Wood
chemical_list: D017705:Lignans; C419306:hydroxymatairesinol; D015107:4-Butyrolactone