Identification of the structure and origin of a thioacidolysis marker compound for ferulic acid incorporation into angiosperm lignins (and an indicator for cinnamoyl CoA reductase deficiency)

The Plant Journal : for Cell and Molecular Biology
John RalphCatherine Lapierre

Abstract

A molecular marker compound, derived from lignin by the thioacidolysis degradative method, for structures produced when ferulic acid is incorporated into lignin in angiosperms (poplar, Arabidopsis, tobacco), has been structurally identified as 1,2,2-trithioethyl ethylguaiacol [1-(4-hydroxy-3-methoxyphenyl)-1,2,2-tris(ethylthio)ethane]. Its truncated side chain and distinctive oxidation state suggest that it derives from ferulic acid that has undergone bis-8-O-4 (cross) coupling during lignification, as validated by model studies. A diagnostic contour for such structures is found in two-dimensional (13)C-(1)H correlated (HSQC) NMR spectra of lignins isolated from cinnamoyl CoA reductase (CCR)-deficient poplar. As low levels of the marker are also released from normal (i.e. non-transgenic) plants in which ferulic acid may be present during lignification, notably in grasses, the marker is only an indicator for CCR deficiency in general, but is a reliable marker in woody angiosperms such as poplar. Its derivation, together with evidence for 4-O-etherified ferulic acid, strongly implies that ferulic acid is incorporated into angiosperm lignins. Its endwise radical coupling reactions suggest that ferulic acid should be considered an ...Continue Reading

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Citations

Aug 7, 2012·Nature Protocols·Shawn D MansfieldJohn Ralph
Feb 7, 2012·Proceedings of the National Academy of Sciences of the United States of America·Fang ChenJohn Ralph
Aug 1, 2013·Proceedings of the National Academy of Sciences of the United States of America·Qiao ZhaoRichard A Dixon
Oct 31, 2008·Plant Physiology·Armin WagnerJohn Ralph
Apr 24, 2009·Plant Physiology·Jaclyn J StewartShawn D Mansfield
May 18, 2010·Plant Physiology·Ruben VanholmeWout Boerjan
Jan 1, 2014·Proceedings of the National Academy of Sciences of the United States of America·Rebecca Van AckerWout Boerjan
Sep 3, 2010·Annual Review of Genetics·Nicholas D Bonawitz, Clint Chapple
Jan 13, 2016·Proceedings of the National Academy of Sciences of the United States of America·Bram BeckersJaco Vangronsveld
Mar 15, 2016·Frontiers in Chemistry·Batirtze Prats MateuNotburga Gierlinger
Dec 6, 2008·Phytochemistry·Anders HolmgrenGunnar Henriksson
Oct 28, 2014·Frontiers in Plant Science·Su-Ying YehWilfried Schwab
Jan 20, 2011·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Chang-Jun LiuKe-Wei Zhang
Oct 3, 2018·The New Phytologist·Xiaojing YanVincent L Chiang
Aug 14, 2009·The New Phytologist·Katia RuelJean-Paul Joseleau
Jan 15, 2010·Plant Biotechnology Journal·Darby Harris, Seth DeBolt
Feb 13, 2010·Tropical Medicine & International Health : TM & IH·Sibylle GerstlJacob Maikere
Feb 3, 2015·Journal of the Science of Food and Agriculture·Lenka Tomková-DrábkováLadislav Kučera
Mar 11, 2020·Journal of Experimental Botany·Nerya Zexer, Rivka Elbaum
Oct 6, 2012·The New Phytologist·Ruben VanholmeWout Boerjan
Sep 11, 2019·Journal of Experimental Botany·Milan SoukupRivka Elbaum
Aug 14, 2019·Frontiers in Plant Science·Alexandra ChanocaWout Boerjan

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