Identification of new lignans in Norway spruce knotwood extracts
-
Annika I. Smeds
,
Iveta Češková
Abstract
In a hydrophilic extract of Norway spruce knotwood, the dominating lignan, 7-hydroxymatairesinol, was partially removed by precipitation, and the resulting mixture was fractionated by flash chromatography and preparative high-performance liquid chromatography (HPLC). In the HPLC fractions, 7S- and 7R-todolactol A, 7′-hydroxylariciresinol, and two stereoisomers of 9′-hydroxylariciresinol were identified by gas chromatography-mass spectrometry (GC-MS) analyses, and their structures were confirmed by nuclear magnetic resonance spectroscopy. The 9′-hydroxylariciresinols were suggested to have the 7S,8R,8′R,9′Rand 7R,8R,8′R,9′Rconfigurations, and (-)-7′-hydroxylariciresinol 7S*,7′R*,8R*,8′S*, which indicates a configuration of this structure that has not been reported previously. 7S- and 7R-isoliovil were identified by comparison with previously published GC-MS data, and 7′-oxolariciresinol was tentatively identified on the basis of its mass spectrum. Of these lignans, only 7′-hydroxylariciresinol has been identified previously in Norway spruce. Several other lignans with similar mass spectra as the todolactols, isoliovils, and 7′-hydroxylariciresinol were detected, indicating that they are different stereoisomers of these lignans and/or of liovils. In addition to these lignans, the mass spectra of several other unidentified minor lignans indicated the presence of several tens of previously unidentified minor lignans in Norway spruce knotwood, accounting altogether for approximately 6% of the dry weight of the ethanol extract. 7S-Todolactol A, which was dominating among the new lignans, was found to be very unstable in aqueous solutions. Identification of more of these unidentified lignans may be possible only by access to pure reference compounds.
©2012 by Walter de Gruyter Berlin Boston
Articles in the same Issue
- Original Papers
- Identification of new lignans in Norway spruce knotwood extracts
- Isolation and characterization of β-cadinene synthase cDNA from Chamaecyparis formosensis Matsum
- Antioxidant activity of fractions from Quercus sideroxyla bark and identification of proanthocyanidins by HPLC-DAD and HPLC-MS
- New diarylpropanoids from Lindera glauca Bl. heartwood
- Extracting value-added products before pulping: Hemicellulosic ethanol from Eucalyptus globulus wood
- Effect of various pulp properties on the solubility of cellulose in sodium hydroxide solutions
- Dissolution and acetylation of ball-milled birch (Betula platyphylla) and bamboo (Phyllostachys nigra) in the ionic liquid [Bmim]Cl for HSQC NMR analysis
- Study of thin films of kraft lignin and two DHPs by means of single-molecule force spectroscopy (SMFS)
- Characterization of mixed-mode I/II fracture properties of adhesively bonded yellow-poplar by a dual actuator test frame instrument
- Grading of structural timber of Populus × euramericana clone I-214
- Measurement of wood shrinkage in jack pine using three dimensional digital image correlation (DIC)
- Internal stress measurement during drying of rubberwood lumber: effects of wet-bulb temperature in various drying strategies
- Tensile behaviour of radiata pine with different moisture contents at elevated temperatures
- Within-process and seasonal changes during industrial production of high-density fibreboard. Part 1: Influence of wood species composition on polyoses in the products
- Within-process and seasonal changes during industrial production of high-density fibreboard. Part 2: PLS modelling of chemical alterations, refining conditions and panel thickness swell
- Short Note
- Effect of grain angle on shear strength of Douglas-fir wood
- Meetings
- Meetings
- Masthead
- Masthead
Articles in the same Issue
- Original Papers
- Identification of new lignans in Norway spruce knotwood extracts
- Isolation and characterization of β-cadinene synthase cDNA from Chamaecyparis formosensis Matsum
- Antioxidant activity of fractions from Quercus sideroxyla bark and identification of proanthocyanidins by HPLC-DAD and HPLC-MS
- New diarylpropanoids from Lindera glauca Bl. heartwood
- Extracting value-added products before pulping: Hemicellulosic ethanol from Eucalyptus globulus wood
- Effect of various pulp properties on the solubility of cellulose in sodium hydroxide solutions
- Dissolution and acetylation of ball-milled birch (Betula platyphylla) and bamboo (Phyllostachys nigra) in the ionic liquid [Bmim]Cl for HSQC NMR analysis
- Study of thin films of kraft lignin and two DHPs by means of single-molecule force spectroscopy (SMFS)
- Characterization of mixed-mode I/II fracture properties of adhesively bonded yellow-poplar by a dual actuator test frame instrument
- Grading of structural timber of Populus × euramericana clone I-214
- Measurement of wood shrinkage in jack pine using three dimensional digital image correlation (DIC)
- Internal stress measurement during drying of rubberwood lumber: effects of wet-bulb temperature in various drying strategies
- Tensile behaviour of radiata pine with different moisture contents at elevated temperatures
- Within-process and seasonal changes during industrial production of high-density fibreboard. Part 1: Influence of wood species composition on polyoses in the products
- Within-process and seasonal changes during industrial production of high-density fibreboard. Part 2: PLS modelling of chemical alterations, refining conditions and panel thickness swell
- Short Note
- Effect of grain angle on shear strength of Douglas-fir wood
- Meetings
- Meetings
- Masthead
- Masthead
