About: Identification of new lignans in Norway spruce knotwood extracts

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Description	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, 7 S 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'R and 7R,8R,8'R,9'R configurations, 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. 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, 7 S 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'R and 7R,8R,8'R,9'R configurations, 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. (en)
Title	Identification of new lignans in Norway spruce knotwood extracts Identification of new lignans in Norway spruce knotwood extracts (en)
skos:prefLabel	Identification of new lignans in Norway spruce knotwood extracts Identification of new lignans in Norway spruce knotwood extracts (en)
skos:notation	RIV/60076658:12220/12:43884593!RIV13-MSM-12220___
http://linked.open...avai/predkladatel	Zemědělská fakulta
http://linked.open...avai/riv/aktivita	V
http://linked.open...avai/riv/aktivity	V
http://linked.open...iv/cisloPeriodika	5
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Češková, Iveta
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Jihočeská univerzita v Českých Budějovicích / Zemědělská fakulta
http://linked.open...dnocenehoVysledku	140313
http://linked.open...ai/riv/idVysledku	RIV/60076658:12220/12:43884593
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	todolactol; Norway spruce; NMR; liovil; lignans; knotwood; isoliovil; hydroxylariciresinol; GC-MS (en)
http://linked.open.../riv/klicoveSlovo	GC-MS NMR Norway spruce hydroxylariciresinol isoliovil knotwood liovil todolactol lignans
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[2898DE9118AC]
http://linked.open...i/riv/nazevZdroje	Holzforschung
http://linked.open...in/vavai/riv/obor	CB
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	4 (xsd:int)
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	66
http://linked.open...iv/tvurceVysledku	Češková, Iveta Eklund, P. C. Smeds, A. I. Willfor, S. M.
http://linked.open...ain/vavai/riv/wos	000307218900001
issn	0018-3830
number of pages	15 (xsd:int)
http://localhost/t...ganizacniJednotka	12220
is http://linked.open...avai/riv/vysledek of	Identification of new lignans in Norway spruce knotwood extracts

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