Bioactive phenolic substances in industrially important tree species. Part 4: Identification of two new 7-hydroxy divanillyl butyrolactol lignans in some spruce, fir, and pine species

Stefan Willför, Patrik Christoffer Eklund, Rainer Sjöholm, Markku Reunanen, Reijo Sillanpää, Sebastian von Schoultz, Jarl Hemming, Linda Nisula, Bjarne Holmbom

    Research output: Contribution to journalArticleScientificpeer-review

    28 Citations (Scopus)

    Abstract

    A few lignans, that is, 7-hydroxymatairesinol, secoisolariciresinol, lariciresinol, and nortrachelogenin, predominate in a large proportion of the industrially important softwood species used. Some other lignans, of which some still are unidentified, are also present in lower amounts. Softwood knots, i.e., the branch bases inside tree stems,. commonly contain exceptionally large amounts of free aglycone lignans, which has provided a great opportunity to isolate sufficient amounts of softwood lignans for structural characterisation. Here we present the identification and characterisation of two new 9-epimers of 7-hydroxy divanillyl butyrolactol lignans, (7S,8R,8'R,9'R)-4,4',7-trihydroxy-3,3'-dimethoxylignano-9',9'-lactol and (7S,8R,8'R,9'S)-4,4',7-trihydroxy-3,3'dimethoxylignano-9',9'-lactol, in knotwood of Colorado spruce (Picea pungens), from tentative GC-MS analysis to final determination of the structure by NMR spectroscopy and X-ray analysis. Further analyses have verified the occurrence of these lignans, which were earlier incorrectly addressed by our group as isomers of liovil, in several spruce, pine, and fir species.
    Original languageUndefined/Unknown
    Pages (from-to)413–417
    Number of pages5
    JournalHolzforschung
    Volume59
    Issue number4
    DOIs
    Publication statusPublished - 2005
    MoE publication typeA1 Journal article-refereed

    Keywords

    • 7-hydroxy divanillyl butyrolactol lignans
    • Abies
    • fir
    • isoliovil
    • knots
    • knotwood
    • lignans
    • liovil
    • Picea
    • pine
    • Pinus pinaster
    • spruce
    • todolactol A

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