Coniferyl alcohol metabolism in conifers -- II. Coniferyl alcohol and dihydroconiferyl alcohol biosynthesis.

Coniferaldehyde and NADPH when incubated with microsomes isolated from developing xylem of Pinus strobus yielded coniferyl alcohol and dihydroconiferyl alcohol in vitro. D-(+)-Pinitol was also found to be a microsomal constituent. Endogenous E-coniferyl alcohol content, quantified in dormant buds, cambium, bark and needles of Pinus resinosa and P. strobus by isotope-dilution combined gas chromatography mass spectrometry (GC/MS) using ring-(13)C(6)-coniferyl alcohol, was at a level similar to that of endogenous indol 3-ylacetic acid (IAA). Wounding (branch girdling) induced more than a 10-fold increase in content of endogenous E-coniferyl alcohol in dormant non-lignifying cambium, a clear indication that monolignol biosynthesis is not coupled to lignification.

[1]  A. Neish.  Biosynthetic Pathways of Aromatic Compounds , 1960 .

[2]  N. Smirnoff,et al.  Hydroxyl radical scavenging properties of cyclitols , 1994 .

[3]  M. Kwon,et al.  Localization of Dirigent Protein Involved in Lignan Biosynthesis: Implications for Lignification at the Tissue and Subcellular Level , 1999 .

[4]  Karl Freudenberg,et al.  Constitution and Biosynthesis of Lignin , 1968 .

[5]  R. Sederoff,et al.  Unexpected variation in lignin. , 1999, Current opinion in plant biology.

[6]  H. Hesse,et al.  Isolation of cDNAs encoding cytosolic and plastidic cysteine synthase isoforms from Solanum tuberosum , 1998 .

[7]  L. Davin,et al.  Regiochemical control of monolignol radical coupling: a new paradigm for lignin and lignan biosynthesis. , 1999, Chemistry & biology.

[8]  J. Barnett.  Xylem Cell Development , 1981 .

[9]  U. Westermark,et al.  Distribution of Coniferyl Alcohol and Coniferaldehyde Groups in the Cell Wall of Spruce Fibres , 1997 .

[10]  B. Pettersson,et al.  Poorly and Non-Lignified Regions in the Middle Lamella Cell Corners of Birch (Betula Verrucosa) and Other Wood Species , 1991 .

[11]  Fang Chen,et al.  Evidence for a novel biosynthetic pathway that regulates the ratio of syringyl to guaiacyl residues in lignin in the differentiating xylem of Magnolia kobus DC , 1999, Planta.

[12]  R. Savidge,et al.  Seasonal activity of uridine 5'-diphosphoglucose:coniferyl alcohol glucosyltransferase in relation to cambial growth and dormancy in conifers , 1998 .

[13]  M. R. Hemm,et al.  New routes for lignin biosynthesis defined by biochemical characterization of recombinant ferulate 5-hydroxylase, a multifunctional cytochrome P450-dependent monooxygenase. , 1999, Proceedings of the National Academy of Sciences of the United States of America.

[14]  R. Sederoff,et al.  Abnormal lignin in a loblolly pine mutant. , 1997, Science.

[15]  C. Rolando,et al.  A Mild Synthesis of Coumaryl, Coniferyl, Sinapyl Aldehydes and Alcohols , 1994 .

[16]  C. Lamb,et al.  Cinnamyl-alcohol dehydrogenase, a molecular marker specific for lignin synthesis: cDNA cloning and mRNA induction by fungal elicitor. , 1988, Proceedings of the National Academy of Sciences of the United States of America.

[17]  G. Wagner,et al.  Metabolic pathways as enzyme complexes: evidence for the synthesis of phenylpropanoids and flavonoids on membrane associated enzyme complexes. , 1985, Archives of biochemistry and biophysics.

[18]  G. Petersson,et al.  Phenolic compounds in kraft black liquor , 1978 .

[19]  D. Fengel,et al.  A New Process for Improving the Quality and Lignin Staining of Ultrathin Sections from Wood Tissue , 1990 .

[20]  Geoffrey D. Brown,et al.  Coniferaldehyde derivatives from tissue culture of Artemisia annua and Tanacetum parthenium , 1999 .

[21]  K. Takabe,et al.  Heterogeneity in formation of lignin. VIII. An autoradiographic study on the formation of guaiacyl and syringyl lignin in Magnolia kobus DC , 1986 .

[22]  G. G. Gross,et al.  Plant polyphenols 2 : chemistry, biology, pharmacology, ecology , 1999 .

[23]  T. Kirk,et al.  Isolation of lignin , 1988 .

[24]  T. Umezawa,et al.  Coniferyl aldehyde 5-hydroxylation and methylation direct syringyl lignin biosynthesis in angiosperms. , 1999, Proceedings of the National Academy of Sciences of the United States of America.

[25]  R. Savidge,et al.  Cell and molecular biology of wood formation , 2000 .

[26]  Leif J. Jönsson,et al.  Influence of lignocellulose-derived aromatic compounds on oxygen-limited growth and ethanolic fermentation by Saccharomyces cerevisiae , 2000, Applied biochemistry and biotechnology.

[27]  N. Kutscha,et al.  TB53: The Suitability of Certain Stains for Studying Lignification in Balsam Fir, Abies balsamea (L.) Mill , 1972 .

[28]  Hidetoshi Takahashi,et al.  Lignans and Brauns' Lignins from Softwoods , 1987 .

[29]  K. Iiyama,et al.  Structural feature of lignin in cell walls of normal and fast-growing poplar (Populus maximowiczii Henry). Linkage types of wall-bound hydroxyberizic and hydroxycinnamic acids. , 1995 .

[30]  R. Macdonald,et al.  Ethanol in the stems of trees , 1991 .

[31]  D. Goring,et al.  The Location of Guaiacyl and Syringyl Lignins in Birch Xylem Tissue , 1970 .

[32]  K. Takabe,et al.  Heterogeneity in Formation of Lignin. X. Visualization of Lignification Process in Differentiating Xylem of Pine by Microautoradiography , 2009 .

[33]  Fang Chen,et al.  Conversion of guaiacyl to syringyl moieties on the cinnamyl alcohol pathway during the biosynthesis of lignin in angiosperms , 2000, Planta.

[34]  R. Savidge,et al.  Xylogenesis, Genetic and Environmental Regulation-A Review- , 1996 .

[35]  P. Wareing,et al.  Apparent auxin production and transport during winter in the nongrowing pine tree , 1982 .

[36]  O. H. Lowry,et al.  Protein measurement with the Folin phenol reagent. , 1951, The Journal of biological chemistry.

[37]  N. Lewis.  A 20(th) century roller coaster ride: a short account of lignification. , 1999, Current opinion in plant biology.

[38]  K. Osakabe,et al.  A novel multifunctional O-methyltransferase implicated in a dual methylation pathway associated with lignin biosynthesis in loblolly pine. , 1997, Proceedings of the National Academy of Sciences of the United States of America.

[39]  T. Umezawa,et al.  5-Hydroxyconiferyl Aldehyde Modulates Enzymatic Methylation for Syringyl Monolignol Formation, a New View of Monolignol Biosynthesis in Angiosperms* , 2000, The Journal of Biological Chemistry.

[40]  K. Niemelä.  GLC-MS Studies on Pine Kraft Black Liquors Part V. Identification of Catechol Compounds , 1989 .

[41]  K. Shimoda,et al.  Asymmetric Hydrogenation of the C–C Double Bond of Enones with the Reductases from Nicotiana tabacum , 2000 .

[42]  R. Savidge.  Coniferin, a biochemical indicator of commitment to tracheid differentiation in conifers , 1989 .

[43]  E. Cadahía,et al.  Low Molecular Weight Phenolic Compounds in Spanish Oak Woods , 1996 .

[44]  R. Savidge.  Dihydroconiferyl alcohol in developing xylem of Pinus contorta , 1986 .

[45]  Michael A. Wilson,et al.  1,3,5-Hydroxybenzene structures in mosses , 1989 .

[46]  B. Kos̆iková,et al.  The Relationship between Ultrastructure and Lignin Extractability of Steamed Hardwoods , 1990 .

[47]  M. Niku‐Paavola.  Isoelectric focusing electrophoresis of lignin. , 1991, Analytical biochemistry.

[48]  R. Savidge,et al.  Metabolic Activity of Uridine 5′-Diphosphoglucose: Cinnamyl Alcohol Glucosyltransferase as an Intrinsic Indicator of Cambial Growth in Conifers , 1999 .

[49]  E. Conde,et al.  Low Molecular Weight Polyphenols in Cork of Quercus suber , 1997 .

[50]  N. Lewis,et al.  Lignin and Lignan Biosynthesis , 1998 .