A new lariciresinol-type butyrolactone lignan derived from hydroxymatairesinol and its identification in spruce wood.
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.
Eklund
Patrik C
PC
Department of Organic Chemistry, Process Chemistry Centre, Abo Akademi University, Biskopsgatan 8, FIN-20500, Turku/Abo, Finland. paeklund@abo.fi
Willför
Stefan M
SM
Smeds
Annika I
AI
Sundell
Fredrik J
FJ
Sjöholm
Rainer E
RE
Holmbom
Bjarne R
BR
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
D017705:Lignans; C419306:hydroxymatairesinol; D015107:4-Butyrolactone