Profiling of oligolignols reveals monolignol coupling conditions in lignifying poplar xylem
Lignin is an aromatic heteropolymer, abundantly present in the walls of secondary thickened cells. Although much research has been devoted to the structure and composition of the polymer to obtain insight into lignin polymerization, the low-molecular weight oligolignol fraction has escaped a detaile...
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| Veröffentlicht in: | Plant physiology (Bethesda) 2004-11, Vol.136 (3), p.3537-3549 |
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| creator | Morreel, K Ralph, J Kim, H Lu, F Goeminne, G Ralph, S Messens, E Boerjan, W |
| description | Lignin is an aromatic heteropolymer, abundantly present in the walls of secondary thickened cells. Although much research has been devoted to the structure and composition of the polymer to obtain insight into lignin polymerization, the low-molecular weight oligolignol fraction has escaped a detailed characterization. This fraction, in contrast to the rather inaccessible polymer, is a simple and accessible model that reveals details about the coupling of monolignols, an issue that has raised considerable controversy over the past years. We have profiled the methanol-soluble oligolignol fraction of poplar (Populus spp.) xylem, a tissue with extensive lignification. Using liquid chromatography-mass spectrometry, chemical synthesis, and nuclear magnetic resonance, we have elucidated the structures of 38 compounds, most of which were dimers, trimers, and tetramers derived from coniferyl alcohol, sinapyl alcohol, their aldehyde analogs, or vanillin. All structures support the recently challenged random chemical coupling hypothesis for lignin polymerization. Importantly, the structures of two oligomers, each containing a gamma-p-hydroxybenzoylated syringyl unit, strongly suggest that sinapyl p-hydroxybenzoate is an authentic precursor for lignin polymerization in poplar. |
| doi_str_mv | 10.1104/pp.104.049304 |
| format | Article |
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Although much research has been devoted to the structure and composition of the polymer to obtain insight into lignin polymerization, the low-molecular weight oligolignol fraction has escaped a detailed characterization. This fraction, in contrast to the rather inaccessible polymer, is a simple and accessible model that reveals details about the coupling of monolignols, an issue that has raised considerable controversy over the past years. We have profiled the methanol-soluble oligolignol fraction of poplar (Populus spp.) xylem, a tissue with extensive lignification. Using liquid chromatography-mass spectrometry, chemical synthesis, and nuclear magnetic resonance, we have elucidated the structures of 38 compounds, most of which were dimers, trimers, and tetramers derived from coniferyl alcohol, sinapyl alcohol, their aldehyde analogs, or vanillin. All structures support the recently challenged random chemical coupling hypothesis for lignin polymerization. Importantly, the structures of two oligomers, each containing a gamma-p-hydroxybenzoylated syringyl unit, strongly suggest that sinapyl p-hydroxybenzoate is an authentic precursor for lignin polymerization in poplar.</description><identifier>ISSN: 0032-0889</identifier><identifier>EISSN: 1532-2548</identifier><identifier>DOI: 10.1104/pp.104.049304</identifier><identifier>PMID: 15516504</identifier><identifier>CODEN: PPHYA5</identifier><language>eng</language><publisher>Rockville, MD: American Society of Plant Biologists</publisher><subject>Agronomy. Soil science and plant productions ; Alcohols ; biochemical pathways ; Biochemical Processes and Macromolecular Structures ; Biological and medical sciences ; Biosynthesis ; chemical structure ; chemistry ; Dimers ; Economic plant physiology ; Ethers ; Fundamental and applied biological sciences. Psychology ; genetics ; hybrids ; lignification ; Lignin ; Lignin - biosynthesis ; Lignin - chemistry ; Lignin - genetics ; metabolism ; Molecular Structure ; monolignols ; oligolignols ; Oxidation ; phytochemicals ; plant extracts ; Plant physiology and development ; Plants ; Plants, Genetically Modified ; Plants, Genetically Modified - metabolism ; Polymerization ; Populus ; Populus - genetics ; Populus - metabolism ; Populus alba ; Populus tremula ; Water and solutes. Absorption, translocation and permeability ; Water relations, transpiration, stomata ; Xylem</subject><ispartof>Plant physiology (Bethesda), 2004-11, Vol.136 (3), p.3537-3549</ispartof><rights>Copyright 2004 American Society of Plant Biologists</rights><rights>2005 INIST-CNRS</rights><rights>Copyright © 2004, American Society of Plant Biologists 2004</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c591t-cc7b653284cd3f76d075eae0ab6acce10a89bf07bb501c4b8b61a8defe3af4e43</citedby><cites>FETCH-LOGICAL-c591t-cc7b653284cd3f76d075eae0ab6acce10a89bf07bb501c4b8b61a8defe3af4e43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.jstor.org/stable/pdf/4356707$$EPDF$$P50$$Gjstor$$H</linktopdf><linktohtml>$$Uhttps://www.jstor.org/stable/4356707$$EHTML$$P50$$Gjstor$$H</linktohtml><link.rule.ids>230,314,777,781,800,882,27905,27906,57998,58231</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16316546$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15516504$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Morreel, K</creatorcontrib><creatorcontrib>Ralph, J</creatorcontrib><creatorcontrib>Kim, H</creatorcontrib><creatorcontrib>Lu, F</creatorcontrib><creatorcontrib>Goeminne, G</creatorcontrib><creatorcontrib>Ralph, S</creatorcontrib><creatorcontrib>Messens, E</creatorcontrib><creatorcontrib>Boerjan, W</creatorcontrib><title>Profiling of oligolignols reveals monolignol coupling conditions in lignifying poplar xylem</title><title>Plant physiology (Bethesda)</title><addtitle>Plant Physiol</addtitle><description>Lignin is an aromatic heteropolymer, abundantly present in the walls of secondary thickened cells. Although much research has been devoted to the structure and composition of the polymer to obtain insight into lignin polymerization, the low-molecular weight oligolignol fraction has escaped a detailed characterization. This fraction, in contrast to the rather inaccessible polymer, is a simple and accessible model that reveals details about the coupling of monolignols, an issue that has raised considerable controversy over the past years. We have profiled the methanol-soluble oligolignol fraction of poplar (Populus spp.) xylem, a tissue with extensive lignification. Using liquid chromatography-mass spectrometry, chemical synthesis, and nuclear magnetic resonance, we have elucidated the structures of 38 compounds, most of which were dimers, trimers, and tetramers derived from coniferyl alcohol, sinapyl alcohol, their aldehyde analogs, or vanillin. All structures support the recently challenged random chemical coupling hypothesis for lignin polymerization. Importantly, the structures of two oligomers, each containing a gamma-p-hydroxybenzoylated syringyl unit, strongly suggest that sinapyl p-hydroxybenzoate is an authentic precursor for lignin polymerization in poplar.</description><subject>Agronomy. Soil science and plant productions</subject><subject>Alcohols</subject><subject>biochemical pathways</subject><subject>Biochemical Processes and Macromolecular Structures</subject><subject>Biological and medical sciences</subject><subject>Biosynthesis</subject><subject>chemical structure</subject><subject>chemistry</subject><subject>Dimers</subject><subject>Economic plant physiology</subject><subject>Ethers</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>genetics</subject><subject>hybrids</subject><subject>lignification</subject><subject>Lignin</subject><subject>Lignin - biosynthesis</subject><subject>Lignin - chemistry</subject><subject>Lignin - genetics</subject><subject>metabolism</subject><subject>Molecular Structure</subject><subject>monolignols</subject><subject>oligolignols</subject><subject>Oxidation</subject><subject>phytochemicals</subject><subject>plant extracts</subject><subject>Plant physiology and development</subject><subject>Plants</subject><subject>Plants, Genetically Modified</subject><subject>Plants, Genetically Modified - metabolism</subject><subject>Polymerization</subject><subject>Populus</subject><subject>Populus - genetics</subject><subject>Populus - metabolism</subject><subject>Populus alba</subject><subject>Populus tremula</subject><subject>Water and solutes. Absorption, translocation and permeability</subject><subject>Water relations, transpiration, stomata</subject><subject>Xylem</subject><issn>0032-0889</issn><issn>1532-2548</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkj2P1DAQhi0E4paDkg5BGuiyjOOvpKBAJ76kk0CCqygsx7EXnxLb2NkT--9xSHQHFYX1Wn6fGc94jNBTDHuMgb6OcV9kD7QjQO-hHWakqRtG2_toB1D20LbdGXqU8zUAYILpQ3SGGcOcAd2h719SsG50_lAFW4XRHZblw5irZG6MKjoFv51VOhzjH1YHP7jZBZ8r56vFdfa0GDHEUaXq12k002P0wJYE5smm5-jq_btvFx_ry88fPl28vaw16_Bcay16XqpuqR6IFXwAwYwyoHqutDYYVNv1FkTfM8Ca9m3PsWoHYw1RlhpKztGbNW889pMZtPFzUqOMyU0qnWRQTv7rePdDHsKNZI0oz1XiX23xKfw8mjzLyWVtxlF5E45ZcgG8axj_L0gFx4KIBaxXUKeQczL2thgMchmbjFEuso6t8M__7uCO3uZUgJcboLJWo03Ka5fvOE4KR5eLn63cdZ5DuvUpYaUJUewXq21VkOqQSoqrr035FQAdx20hfgNaqra5</recordid><startdate>20041101</startdate><enddate>20041101</enddate><creator>Morreel, K</creator><creator>Ralph, J</creator><creator>Kim, H</creator><creator>Lu, F</creator><creator>Goeminne, G</creator><creator>Ralph, S</creator><creator>Messens, E</creator><creator>Boerjan, W</creator><general>American Society of Plant Biologists</general><general>American Society of Plant Physiologists</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7S9</scope><scope>L.6</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20041101</creationdate><title>Profiling of oligolignols reveals monolignol coupling conditions in lignifying poplar xylem</title><author>Morreel, K ; Ralph, J ; Kim, H ; Lu, F ; Goeminne, G ; Ralph, S ; Messens, E ; Boerjan, W</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c591t-cc7b653284cd3f76d075eae0ab6acce10a89bf07bb501c4b8b61a8defe3af4e43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Agronomy. Soil science and plant productions</topic><topic>Alcohols</topic><topic>biochemical pathways</topic><topic>Biochemical Processes and Macromolecular Structures</topic><topic>Biological and medical sciences</topic><topic>Biosynthesis</topic><topic>chemical structure</topic><topic>chemistry</topic><topic>Dimers</topic><topic>Economic plant physiology</topic><topic>Ethers</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>genetics</topic><topic>hybrids</topic><topic>lignification</topic><topic>Lignin</topic><topic>Lignin - biosynthesis</topic><topic>Lignin - chemistry</topic><topic>Lignin - genetics</topic><topic>metabolism</topic><topic>Molecular Structure</topic><topic>monolignols</topic><topic>oligolignols</topic><topic>Oxidation</topic><topic>phytochemicals</topic><topic>plant extracts</topic><topic>Plant physiology and development</topic><topic>Plants</topic><topic>Plants, Genetically Modified</topic><topic>Plants, Genetically Modified - metabolism</topic><topic>Polymerization</topic><topic>Populus</topic><topic>Populus - genetics</topic><topic>Populus - metabolism</topic><topic>Populus alba</topic><topic>Populus tremula</topic><topic>Water and solutes. Absorption, translocation and permeability</topic><topic>Water relations, transpiration, stomata</topic><topic>Xylem</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Morreel, K</creatorcontrib><creatorcontrib>Ralph, J</creatorcontrib><creatorcontrib>Kim, H</creatorcontrib><creatorcontrib>Lu, F</creatorcontrib><creatorcontrib>Goeminne, G</creatorcontrib><creatorcontrib>Ralph, S</creatorcontrib><creatorcontrib>Messens, E</creatorcontrib><creatorcontrib>Boerjan, W</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Plant physiology (Bethesda)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Morreel, K</au><au>Ralph, J</au><au>Kim, H</au><au>Lu, F</au><au>Goeminne, G</au><au>Ralph, S</au><au>Messens, E</au><au>Boerjan, W</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Profiling of oligolignols reveals monolignol coupling conditions in lignifying poplar xylem</atitle><jtitle>Plant physiology (Bethesda)</jtitle><addtitle>Plant Physiol</addtitle><date>2004-11-01</date><risdate>2004</risdate><volume>136</volume><issue>3</issue><spage>3537</spage><epage>3549</epage><pages>3537-3549</pages><issn>0032-0889</issn><eissn>1532-2548</eissn><coden>PPHYA5</coden><abstract>Lignin is an aromatic heteropolymer, abundantly present in the walls of secondary thickened cells. Although much research has been devoted to the structure and composition of the polymer to obtain insight into lignin polymerization, the low-molecular weight oligolignol fraction has escaped a detailed characterization. This fraction, in contrast to the rather inaccessible polymer, is a simple and accessible model that reveals details about the coupling of monolignols, an issue that has raised considerable controversy over the past years. We have profiled the methanol-soluble oligolignol fraction of poplar (Populus spp.) xylem, a tissue with extensive lignification. Using liquid chromatography-mass spectrometry, chemical synthesis, and nuclear magnetic resonance, we have elucidated the structures of 38 compounds, most of which were dimers, trimers, and tetramers derived from coniferyl alcohol, sinapyl alcohol, their aldehyde analogs, or vanillin. All structures support the recently challenged random chemical coupling hypothesis for lignin polymerization. Importantly, the structures of two oligomers, each containing a gamma-p-hydroxybenzoylated syringyl unit, strongly suggest that sinapyl p-hydroxybenzoate is an authentic precursor for lignin polymerization in poplar.</abstract><cop>Rockville, MD</cop><pub>American Society of Plant Biologists</pub><pmid>15516504</pmid><doi>10.1104/pp.104.049304</doi><tpages>13</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Plant physiology (Bethesda), 2004-11, Vol.136 (3), p.3537-3549 |
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| source | MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Jstor Complete Legacy; Oxford University Press Journals All Titles (1996-Current) |
| subjects | Agronomy. Soil science and plant productions Alcohols biochemical pathways Biochemical Processes and Macromolecular Structures Biological and medical sciences Biosynthesis chemical structure chemistry Dimers Economic plant physiology Ethers Fundamental and applied biological sciences. Psychology genetics hybrids lignification Lignin Lignin - biosynthesis Lignin - chemistry Lignin - genetics metabolism Molecular Structure monolignols oligolignols Oxidation phytochemicals plant extracts Plant physiology and development Plants Plants, Genetically Modified Plants, Genetically Modified - metabolism Polymerization Populus Populus - genetics Populus - metabolism Populus alba Populus tremula Water and solutes. Absorption, translocation and permeability Water relations, transpiration, stomata Xylem |
| title | Profiling of oligolignols reveals monolignol coupling conditions in lignifying poplar xylem |
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