Chemical characterization of polymerized products formed in the reactions of matairesinol and pinoresinol with the stable radical 2,2-diphenyl-1-picrylhydrazyl

Annika I. Smeds (Corresponding Author), Patrik C. Eklund, Evanthia Monogioudi, Stefan M. Willför

Research output: Contribution to journalArticleScientificpeer-review

30 Citations (Scopus)

Abstract

Polymerization reactions of the lignans matairesinol and pinoresinol with the stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) were studied. The reactions were rapid and almost quantitative. The molecular weight distribution (MWD) of the formed lignan dimers and polymers was determined by high-performance size-exclusion chromatography (HPSEC) combined with evaporative light-scattering detection (ELSD), and the compounds were characterized by HPLC-MS, pyrolysis-GC/MS, NMR, MALDI-ToF-MS, and GC-MS of the monomeric and dimeric units formed by KMnO4 oxidation. The yield of high-MW polymers is higher for pinoresinol (69%) than for matairesinol (43%). According to the HPSEC-ELSD analyses, the MWD is also broader for the pinoresinol polymers. The latter seem to consist mainly of hepta-hexacontalignans (MW 2.5–21.4 kDa), whereas the matairesinol polymers are mainly penta-pentadecalignans (MW 1.8–5.3 kDa). The polymers seem to contain mainly unmodified lignan units linked by 5-5′ bonds.
Original languageEnglish
Pages (from-to)283-294
JournalHolzforschung
Volume66
Issue number3
DOIs
Publication statusPublished - 2012
MoE publication typeA1 Journal article-refereed

Keywords

  • 2,2-diphenyl-1-picrylhydrazyl (DPPH)
  • evaporative light-scattering detection (ELSD)
  • high-performance size exclusion chromatography (HPSEC)
  • KMnO4 oxidation
  • lignan polymers
  • lignans
  • MALDI-ToF-MS
  • matairesinol
  • pinoresinol
  • pyrolysis-GC/MS (Py-GC/MS

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