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 language | English |
|---|---|
| Pages (from-to) | 283-294 |
| Journal | Holzforschung |
| Volume | 66 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - 2012 |
| MoE publication type | A1 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