Variation of stilbene glucosides in bark extracts obtained from roots and stumps of Norway spruce (Picea abies [L.] Karst.) (original) (raw)
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Biomass Conversion and Biorefinery
Polyphenolic stilbene glucosides are abundant in the fresh bark of Norway spruce (Picea abies [L.] Karst.) trees. Stilbene-rich bark extracts could be industrially utilized as preservatives due to their antioxidative, antifungal, and antibacterial properties. The postharvesting conditions, especially industrial debarking, influence the chemical properties of bark. Inherent variation in high-value compounds of bark is assumed to be offset by modifications within the bark supply chain; however, essential quantitative information is still rare. This study elucidated the magnitude of variation in the stilbenoid content and composition of Norway spruce bark due to (1) the geographical origin of Norway spruce seeds, (2) the geographical location of the growing site, (3) within-tree variability, and (4) industrial handling and pilot-scale extraction and fractioning processes. The inherent variation in stilbenoid content was large: the total average stilbenoid content of the inner bark vari...
Phytochemical Analysis, 2014
Introduction -Stilbenes are plant secondary metabolites that have shown promising and varied biological activities. Stilbenes are presently actively studied for the exploitation of this primary raw material resource, involving the concept of biorefining. Methods for the rapid discovery of new and known stilbene structures from various plant sources are thus keenly sought. Objective -To establish a simple and rapid technique of off-line HPLC with a diode-array detector (DAD) and NMR for the unambiguous structural elucidation of stilbene structures in the root bark of Norway spruce [Picea abies (L.) Karst.]. Material and methods -The stilbene containing fraction was extracted from the plant bark with an ethanol:water mixture (95:5, v/v) preceded by defatting of hydrophobic compounds with n-hexane using the accelerated solvent extraction technique. A portion of the ethanol-water soluble extract was hydrolysed with β-glucosidase to prepare stilbene aglycones. The extracts were further purified and enriched using a polymeric adsorbent. Stilbene-enriched extracts were directly characterised by off-line HPLC/DAD-NMR in conjunction with HPLC/DAD and HPLC/DAD with electrospray ionisation MS n . Results -Trans-isorhapontin and trans-astringin were identified as the major, and trans-piceid as a minor, stilbene glucosides of the bark of roots of Picea abies. Not only stilbene glucosides but also the corresponding stilbene aglycones, such as trans-resveratrol, trans-piceatannol and trans-isorhapontigenin, were rapidly identified from the hydrolysed extract. The acquired heteronuclear single-quantum coherence and heteronuclear multiple bond correlation spectra were used to assign the complete carbon NMR chemical shifts of trans-isorhapontin and trans-astringin without the need of acquiring a 13 C-NMR spectrum. Conclusion -The off-line HPLC/DAD-NMR method is expedient for the unambiguous identication of structurally similar stilbenes in plant extracts.
Holzforschung, 2000
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,89R,99R)-4,49,7-trihydroxy-3,39-dimethoxylignano-99,99-lactol and (7S,8R,89R,99S)-4,49,7-trihydroxy-3,39dimethoxylignano-99,99-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.
Wood Extractives in Conifers - A Study of Stemwood and Knots of Industrially Important Species
2018
Study of lipophilic and hydrophilic extractives in heartwood, sapwood and knots of 39 industrially important conifer species: 14 pines (Pinus), 7 spruces (Picea), 9 firs (Abies), 5 larches (Larix), 3 hemlocks (Tsuga) and Douglas-fir (Pseudotsuga). The wood samples were sequentially extracted, and the amount and composition of resin acids, fatty acids, sterols, steryl esters, acylglycerols, juvabiones, lignans, oligolignans, flavonoids and stilbenes were analysed by gas chromatography (GC) and GC-mass spectrometry.
Screening Analyses of Pinosylvin Stilbenes, Resin Acids and Lignans in Norwegian Conifers
Molecules, 2006
The content and distribution of stilbenes and resin acids in Scots pine (Pinus sylvestris) and spruce (Picea abies), sampled in central Norway, have been examined. The contents of pinosylvin stilbenes in pine heartwood/living knots were 0.2-2/2-8 % (w/w). No stilbenes could be detected in spruce (Picea abies). The resin acid contents of pine sapwood/heartwood and knots were 1-4 and 5-10 % (w/w), respectively. Minor amounts of resin acids (<0.2/<0.04 %w/w) were identified in spruce wood/knots. The lignan content in knots of Norwegian spruce was 6.5 % (w/w). Diastereomerically pure hydroxymatairesinol (HMR, 84 % of total lignans) was readily isolated from this source since only minor quantities (2.6 % of total lignans) of the allo-HMR diastereomer was detected. Insignificant amounts of lignans were present in the sapwood. Lignans could not be detected in the sapwood or knots of Norwegian sallow (Salix caprea), birch (Betula pendula) or juniper (Juniperus communis).
Stilbenes as constitutive and induced protection compounds in Scots pine ( Pinus sylvestris L.)
2012
The goals of our studies are to describe the natural variation in the concentration of constitutive heartwood extractives; estimate the genetic parameters related to heartwood characteristics; determine whether there is a genetic connection between constitutive and inducible production of stilbenes; and, together with technical experts, to develop fast and reliable techniques to quantify stilbenes from wood samples and determine whether there are rapid ways to utilize the existing variation in silviculture. We are also collaborating with molecular geneticists to find the markers for pine stilbene biosynthesis that could be used in early selection. The study material includes three generations of Scots pine (Pinus sylvestris L.): the first generation consists of grafted clones in seed orchards; their half-sib progenies growing in about 40-year-old progeny trials are the second generation; and the third generation includes seedlings in a nursery. The first and the second generations p...
Extraction and chemical characterization of Norway spruce inner and outer bark
Nordic Pulp & Paper Research Journal, 2012
Possible chemical utilization of bark requires appropriate knowledge of its composition. Extraction of valuable components before burning is an interesting option for utilization of bark. Here, Norway spruce inner and outer bark were extracted separately with a successive series of solvents of increasing polarity and the extracts, as well as the residues, were analyzed to obtain an overall picture of the bark composition. The lipophilic extractives contained the same major components as found in wood. Inner bark contained over 10% of stilbene glucosides with piceatannol (astringenin) as the main stilbene. Tannins of the proanthocyanidin type were extracted with hot water. Further extraction with pressurized hot water at 140°C or 160°C yielded 11-14% of non-cellulosic polysaccharides, on original bark basis, with pectic polysaccharides built up of arabinose, galacturonic acid and rhamnose dominating. Inner bark contained two times more cellulose than outer bark, but the opposite was ...
Forests
The aim of the study was to quantify total extractive contents and lipophilic compounds, stilbenes, and lignans in Scots pine stem wood, stem bark, branch biomass, and sawmill residues in four climatic regions of Finland to evaluate the most optimal sources of extractives for bio-based chemical biorefining and bioenergy products. Data were derived from 78 chip samples from the before-mentioned raw materials, the samples being pooled by tree height position from the sample trees of 42 experimental forest stands, and sawdust lots from 10 log stands. Accelerated solvent extraction (ASE) was employed to determine total extractive contents, followed by gas chromatography with flame ionization detection (GC–FID) to quantify extractive groups and gas chromatography-mass spectrometry (GC–MS) to analyse individual extractive compounds. Resin acids and triglycerides followed by fatty acids were the dominant extractive groups. Resin acids were most abundant in stem wood from final fellings and...
Lignans and Lipophilic Extractives in Norway Spruce Knots and Stemwood
Holzforschung, 2003
Summary The hydrophilic and lipophilic extractives in the heartwood of knots from 7 Norway spruce trees were analysed by GC, GC-MS and HPSEC. The knots contained extremely large amounts of lignans, 6–24% (w/w), with hydroxymatairesinol comprising 65–85% of the lignans. Even the knots of the young trees contained 4–8% (w/w) of lignans. The variation in the amount of lignans was large among knots, both within a single tree and between trees. In addition to the lignans, knots also contained 2–6% (w/w) of a complex mixture of lignan-like compounds with 3, 4 and even up to 6 phenyl propane units, here called oligolignans. The amounts of lignans in the knots were similar in the radial direction from the pith into the outer branch, but decreased dramatically outwards in the branch, almost disappearing after 10–20 cm. The ratio of the 2 epimers of hydroxymatairesinol differed between different knots and even within the knot. A new spruce lignan, nortrachelogenin, or its enantiomer, wikstrom...