Oligolignans in Norway spruce and Scots pine knots and Norway spruce stemwood

Stefan Willför, Markku Reunanen, Patrik Christoffer Eklund, Rainer Sjöholm, Leif Kronberg, Pedro Fardim, Suvi Pietarinen, Bjarne Holmbom

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    Abstract

    Oligolignans present in substantial amounts in Norway spruce and Scots pine knots were characterised. The hydrophilic knotwood substances were extracted and different chromatographic methods were applied to obtain fractions for analysis by GC, GC-MS, HR-EI-MS, LC-ESI-MS, NMR, and FTIR. beta-O-4-Linked guaiacylglyceryl ethers of hydroxymatairesinol (la, lb, Ic), secoisolariciresinol (II), lariciresinol (III), isolariciresinol (IV), lignan A (V), liovil (VI), conidendrin (VII), and pinoresinol (VIII) were identified in the spruce knotwood extract and beta-O-4-linked guaiacylglyceryl ethers of nortrachelogenin (IX) and secoisolariciresinol (II) in the pine knotwood extract. The structures of allo-hydroxymatairesinol-4'-guaiacylglyceryl ether (Ia), hydroxymatairesinol-4-guaiacylglyceryl ether (lb), hydroxymatairesinol-4'-guaiacylglyceryl ether (Ic), secoisolariciresisinol-4-guaiacylglyceryl ether (II), and lariciresinol-4'-guaiacylglyceryl ether (III) were determined via GC-MS, HR-MS, and H-1 and C-13 NMR analyses. The structures of (Ia), (Ic), (IV), (V), (VI), (VII), and (IX) have not been reported earlier. Spruce stemwood, both heartwood and sapwood, also contained oligolignans in small amounts. In addition, some dilignans with four phenylpropanoid units were tentatively identified in the hydrophilic knotwood substances.
    Original languageUndefined/Unknown
    Pages (from-to)345–354
    Number of pages10
    JournalHolzforschung
    Volume58
    Issue number4
    Publication statusPublished - 2004
    MoE publication typeA1 Journal article-refereed

    Keywords

    • ASE
    • C-13 NMR
    • dilignans
    • FTIR
    • guaiacylglycerol
    • guaiacylglyceryl ether
    • H-1 NMR
    • heartwood
    • knots
    • oligolignans
    • Picea abies
    • Pinus sylvestris
    • sesquilignans

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