A new lariciresinol-type butyrolactone lignan derived from hydroxymatairesinol and its identification in spruce wood

Journal of Natural Products
Patrik C EklundBjarne R Holmbom

Abstract

When the natural lignan hydroxymatairesinol (1) was treated with an alkaline aqueous solution, it partially rearranged to isomeric forms of a lariciresinol-type butyrolactone lignan. The two major diastereomers formed (2 and 3) were isolated by column and medium-pressure chromatography, and their structures were elucidated by MS and NMR techniques. These previously unknown butyrolactone lignans were identified as naturally occurring in spruce knotwood by GC, GC-MS, and HPLC-ESI MS/MS analyses. The formation of isohydroxymatairesinol (2) and epi-isohydroxymatairesinol (3) from hydroxymatairesinol (1), and their detection in rat urine after administration of 1, is discussed.

References

Mar 28, 2002·European Journal of Cancer Prevention : the Official Journal of the European Cancer Prevention Organisation (ECP)·K BatcioğluS Celik
Sep 25, 2002·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Niina M SaarinenRisto Santti
Oct 12, 2002·The Journal of Organic Chemistry·Patrik C EklundRainer E Sjöholm
Aug 9, 2003·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Annika Smeds, Kristo Hakala

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Citations

Nov 13, 2007·Journal of Natural Products·Kee Dong YoonJinwoong Kim
Aug 31, 2007·Journal of Mass Spectrometry : JMS·Patrik C EklundRainer E Sjöholm
Apr 30, 2005·The Journal of Steroid Biochemistry and Molecular Biology·N M SaarinenS I Mäkelä
Jan 25, 2005·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Annika I SmedsSari I Mäkelä
Jul 5, 2008·Organic & Biomolecular Chemistry·Barbara RaffaelliKristiina Wähälä
Jul 8, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tuomas MansikkalaRiikka Piispanen
Jan 31, 2007·Journal of Agricultural and Food Chemistry·Annika I SmedsBjarne R Holmbom

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