Coniferol (BioDeep_00000861609)

Main id: BioDeep_00000000453

 

PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


2-Propen-1-ol, 3-(4-hydroxy-3-methoxyphenyl), (E)-

化学式: C10H12O3 (180.0786402)
中文名称: 松柏醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: COC1=C(C=CC(=C1)C=CCO)O
InChI: InChI=1S/C10H12O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-5,7,11-12H,6H2,1H3/b3-2+

描述信息

Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of stilbenoids and coumarin[1]. Coniferyl alcohol specifically inhibits fungal growth[1].
Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of stilbenoids and coumarin[1]. Coniferyl alcohol specifically inhibits fungal growth[1].

同义名列表

22 个代谢物同义名

2-Propen-1-ol, 3-(4-hydroxy-3-methoxyphenyl), (E)-; 4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenol; 4-((1E)-3-Hydroxy-1-propenyl)-2-methoxyphenol; 2-Propen-1-ol, 3-(4-hydroxy-3-methoxyphenyl)-; 4-[(1E)-3-Hydroxy-1-propenyl]-2-methoxyphenol; 4-(3-hydroxyprop-1-enyl)-2-methoxy-phenol; 4-(3-Hydroxy-1-propenyl)-2-methoxyphenol; 4-(3-hydroxyprop-1-enyl)-2-methoxyphenol; 4-Hydroxy-3-methoxycinnamyl alcohol; Coniferyl alcohol; 223735_ALDRICH; Oprea1_201369; ZINC01532694; ZINC01532693; 27740_FLUKA; CHEBI:17745; ST5330606; Coniferol; 458-35-5; C00590; Coniferyl alcohol; Coniferyl alcohol



数据库引用编号

13 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(5)

PlantCyc(4)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

49 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • Yakun Pei, Wenhan Cao, Wenwen Yu, Chaoyang Peng, Wenhao Xu, Yayun Zuo, Wenjun Wu, Zhaonong Hu. Identification and functional characterization of the dirigent gene family in Phryma leptostachya and the contribution of PlDIR1 in lignan biosynthesis. BMC plant biology. 2023 May; 23(1):291. doi: 10.1186/s12870-023-04297-6. [PMID: 37259047]
  • Huan Liu, Dan-Dan Wang, Lin Wan, Zhao-Yang Hu, Ting-Ting He, Jun-Bo Wang, Shu-Zhen Deng, Xin-Shuai Wang. Assessment of attractancy and safeness of (E)-coniferyl alcohol for management of female adults of Oriental fruit fly, Bactrocera dorsalis (Hendel). Pest management science. 2022 Mar; 78(3):1018-1028. doi: 10.1002/ps.6713. [PMID: 34773351]
  • Bin Wang, Zhicheng Li, Zhanhong Han, Sulin Xue, Yang Bi, Dov Prusky. Effects of nitric oxide treatment on lignin biosynthesis and texture properties at wound sites of muskmelons. Food chemistry. 2021 Nov; 362(?):130193. doi: 10.1016/j.foodchem.2021.130193. [PMID: 34082290]
  • Stacie S Kim, Elizabeth S Sattely. Dirigent Proteins Guide Asymmetric Heterocoupling for the Synthesis of Complex Natural Product Analogues. Journal of the American Chemical Society. 2021 04; 143(13):5011-5021. doi: 10.1021/jacs.0c13164. [PMID: 33780244]
  • Camille Modolo, Lu Ren, Eric Besson, Viviane Robert, Stéphane Gastaldi, Pierre Rousselot-Pailley, Thierry Tron. Coniferyl Alcohol Radical Detection by the Dirigent Protein AtDIR6 Monitored by EPR. Chembiochem : a European journal of chemical biology. 2021 03; 22(6):992-995. doi: 10.1002/cbic.202000650. [PMID: 33112043]
  • Thae Thae San, Yue-Hu Wang, Dong-Bao Hu, Jun Yang, Dong-Dong Zhang, Meng-Yuan Xia, Xue-Fei Yang, Yong-Ping Yang. A new sesquineolignan and four new neolignans isolated from the leaves of Piper betle, a traditional medicinal plant in Myanmar. Bioorganic & medicinal chemistry letters. 2021 01; 31(?):127682. doi: 10.1016/j.bmcl.2020.127682. [PMID: 33207281]
  • Xiaohui Chen, Wenlong Su, Han Zhang, Yaguang Zhan, Fansuo Zeng. Fraxinus mandshurica 4-coumarate-CoA ligase 2 enhances drought and osmotic stress tolerance of tobacco by increasing coniferyl alcohol content. Plant physiology and biochemistry : PPB. 2020 Oct; 155(?):697-708. doi: 10.1016/j.plaphy.2020.08.031. [PMID: 32862019]
  • Job Tchoumtchoua, David Mathiron, Nicole Pontarin, David Gagneul, Anne-Isaline van Bohemen, Elvis Otogo N'nang, François Mesnard, Emmanuel Petit, Jean-Xavier Fontaine, Roland Molinié, Anthony Quéro. Phenolic Profiling of Flax Highlights Contrasting Patterns in Winter and Spring Varieties. Molecules (Basel, Switzerland). 2019 Nov; 24(23):. doi: 10.3390/molecules24234303. [PMID: 31779076]
  • Eric M Anderson, Michael L Stone, Rui Katahira, Michelle Reed, Wellington Muchero, Kelsey J Ramirez, Gregg T Beckham, Yuriy Román-Leshkov. Differences in S/G ratio in natural poplar variants do not predict catalytic depolymerization monomer yields. Nature communications. 2019 05; 10(1):2033. doi: 10.1038/s41467-019-09986-1. [PMID: 31048697]
  • Tengxun Zhang, Tingting Huo, Anqi Ding, Ruijie Hao, Jia Wang, Tangren Cheng, Fei Bao, Qixiang Zhang. Genome-wide identification, characterization, expression and enzyme activity analysis of coniferyl alcohol acetyltransferase genes involved in eugenol biosynthesis in Prunus mume. PloS one. 2019; 14(10):e0223974. doi: 10.1371/journal.pone.0223974. [PMID: 31618262]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Farzaneh Kordbacheh, Thomas J Carruthers, Anna Bezos, Marie Oakes, Lauren Du Fall, Charles H Hocart, Christopher R Parish, Michael A Djordjevic. Promotion of mammalian angiogenesis by neolignans derived from soybean extracellular fluids. PloS one. 2018; 13(5):e0196843. doi: 10.1371/journal.pone.0196843. [PMID: 29738532]
  • Xinlun Dai, Li Pang, Zhen Zhang, Chunfeng Yang, Yumei Li. Development of a sensitive LC-MS/MS method for quantification of coniferyl ferulate and its metabolite coniferyl alcohol in rat plasma: Application to a pharmacokinetic study. Journal of pharmaceutical and biomedical analysis. 2017 Nov; 146(?):201-205. doi: 10.1016/j.jpba.2017.08.033. [PMID: 28886520]
  • Yar-Khing Yauk, Edwige J F Souleyre, Adam J Matich, Xiuyin Chen, Mindy Y Wang, Blue Plunkett, Andrew P Dare, Richard V Espley, Sumathi Tomes, David Chagné, Ross G Atkinson. Alcohol acyl transferase 1 links two distinct volatile pathways that produce esters and phenylpropenes in apple fruit. The Plant journal : for cell and molecular biology. 2017 Jul; 91(2):292-305. doi: 10.1111/tpj.13564. [PMID: 28380280]
  • Raphael Gasper, Isabelle Effenberger, Piotr Kolesinski, Barbara Terlecka, Eckhard Hofmann, Andreas Schaller. Dirigent Protein Mode of Action Revealed by the Crystal Structure of AtDIR6. Plant physiology. 2016 12; 172(4):2165-2175. doi: 10.1104/pp.16.01281. [PMID: 27756822]
  • Amandeep K Sangha, Loukas Petridis, Xiaolin Cheng, Jeremy C Smith. Relative Binding Affinities of Monolignols to Horseradish Peroxidase. The journal of physical chemistry. B. 2016 08; 120(31):7635-40. doi: 10.1021/acs.jpcb.6b00789. [PMID: 27447548]
  • Yuanheng Cai, Mohammad-Wadud Bhuiya, John Shanklin, Chang-Jun Liu. Engineering a monolignol 4-O-methyltransferase with high selectivity for the condensed lignin precursor coniferyl alcohol. The Journal of biological chemistry. 2015 Oct; 290(44):26715-24. doi: 10.1074/jbc.m115.684217. [PMID: 26378240]
  • Enni E Väisänen, Annika I Smeds, Kurt V Fagerstedt, Teemu H Teeri, Stefan M Willför, Anna Kärkönen. Coniferyl alcohol hinders the growth of tobacco BY-2 cells and Nicotiana benthamiana seedlings. Planta. 2015 Sep; 242(3):747-60. doi: 10.1007/s00425-015-2348-7. [PMID: 26108783]
  • Wu Lan, Fachuang Lu, Matthew Regner, Yimin Zhu, Jorge Rencoret, Sally A Ralph, Uzma I Zakai, Kris Morreel, Wout Boerjan, John Ralph. Tricin, a flavonoid monomer in monocot lignification. Plant physiology. 2015 Apr; 167(4):1284-95. doi: 10.1104/pp.114.253757. [PMID: 25667313]
  • Jyotsna L Pandey, Bo Wang, Brett G Diehl, Tom L Richard, Gong Chen, Charles T Anderson. A versatile click-compatible monolignol probe to study lignin deposition in plant cell walls. PloS one. 2015; 10(4):e0121334. doi: 10.1371/journal.pone.0121334. [PMID: 25884205]
  • Jia-Ling Wu, Teng-Fei Pan, Zhi-Xiong Guo, Dong-Ming Pan. Specific lignin accumulation in granulated juice sacs of Citrus maxima. Journal of agricultural and food chemistry. 2014 Dec; 62(50):12082-9. doi: 10.1021/jf5041349. [PMID: 25419620]
  • Yuki Tobimatsu, Dorien Van de Wouwer, Eric Allen, Robert Kumpf, Bartel Vanholme, Wout Boerjan, John Ralph. A click chemistry strategy for visualization of plant cell wall lignification. Chemical communications (Cambridge, England). 2014 Oct; 50(82):12262-5. doi: 10.1039/c4cc04692g. [PMID: 25180250]
  • Stefanie König, Kirstin Feussner, Alexander Kaever, Manuel Landesfeind, Corinna Thurow, Petr Karlovsky, Christiane Gatz, Andrea Polle, Ivo Feussner. Soluble phenylpropanoids are involved in the defense response of Arabidopsis against Verticillium longisporum. The New phytologist. 2014 May; 202(3):823-837. doi: 10.1111/nph.12709. [PMID: 24483326]
  • Fang Cong, Brett G Diehl, Joseph Lee Hill, Nicole R Brown, Ming Tien. Covalent bond formation between amino acids and lignin: cross-coupling between proteins and lignin. Phytochemistry. 2013 Dec; 96(?):449-56. doi: 10.1016/j.phytochem.2013.09.012. [PMID: 24099658]
  • Hong-Ling Wang, Chang-An Geng, Yun-Bao Ma, Xue-Mei Zhang, Ji-Jun Chen. Three new secoiridoids, swermacrolactones A-C and anti-hepatitis B virus activity from Swertia macrosperma. Fitoterapia. 2013 Sep; 89(?):183-7. doi: 10.1016/j.fitote.2013.06.002. [PMID: 23756190]
  • Christian Kazenwadel, Janosch Klebensberger, Sven Richter, Jens Pfannstiel, Uwe Gerken, Benjamin Pickel, Andreas Schaller, Bernhard Hauer. Optimized expression of the dirigent protein AtDIR6 in Pichia pastoris and impact of glycosylation on protein structure and function. Applied microbiology and biotechnology. 2013 Aug; 97(16):7215-27. doi: 10.1007/s00253-012-4579-x. [PMID: 23188459]
  • Alexandre Filipe Borges, Ricardo Boavida Ferreira, Sara Monteiro. Transcriptomic changes following the compatible interaction Vitis vinifera-Erysiphe necator. Paving the way towards an enantioselective role in plant defence modulation. Plant physiology and biochemistry : PPB. 2013 Jul; 68(?):71-80. doi: 10.1016/j.plaphy.2013.03.024. [PMID: 23639450]
  • Stefan Wolters, Manuel Neeb, Anna Berim, Johannes Schulze Wischeler, Maike Petersen, Andreas Heine. Structural analysis of coniferyl alcohol 9-O-methyltransferase from Linum nodiflorum reveals a novel active-site environment. Acta crystallographica. Section D, Biological crystallography. 2013 May; 69(Pt 5):888-900. doi: 10.1107/s0907444913002874. [PMID: 23633600]
  • Toshiaki Matsutomo, Timo D Stark, Thomas Hofmann. In vitro activity-guided identification of antioxidants in aged garlic extract. Journal of agricultural and food chemistry. 2013 Mar; 61(12):3059-67. doi: 10.1021/jf305549g. [PMID: 23448127]
  • Jianfeng Ma, Zhe Ji, Xia Zhou, Zhiheng Zhang, Feng Xu. Transmission electron microscopy, fluorescence microscopy, and confocal raman microscopic analysis of ultrastructural and compositional heterogeneity of Cornus alba L. wood cell wall. Microscopy and microanalysis : the official journal of Microscopy Society of America, Microbeam Analysis Society, Microscopical Society of Canada. 2013 Feb; 19(1):243-53. doi: 10.1017/s1431927612013906. [PMID: 23380008]
  • Zhiheng Zhang, Jianfeng Ma, Zhe Ji, Feng Xu. Comparison of anatomy and composition distribution between normal and compression wood of Pinus bungeana Zucc. revealed by microscopic imaging techniques. Microscopy and microanalysis : the official journal of Microscopy Society of America, Microbeam Analysis Society, Microscopical Society of Canada. 2012 Dec; 18(6):1459-66. doi: 10.1017/s1431927612013451. [PMID: 23237521]
  • Lucia Panzella, Thomas Eidenberger, Alessandra Napolitano, Marco d'Ischia. Black sesame pigment: DPPH assay-guided purification, antioxidant/antinitrosating properties, and identification of a degradative structural marker. Journal of agricultural and food chemistry. 2012 Sep; 60(36):8895-901. doi: 10.1021/jf2053096. [PMID: 22423623]
  • Richard Sibout, Herman Höfte. Plant cell biology: the ABC of monolignol transport. Current biology : CB. 2012 Jul; 22(13):R533-5. doi: 10.1016/j.cub.2012.05.005. [PMID: 22790004]
  • Kewei Zhang, Mohammad-Wadud Bhuiya, Jorge Rencoret Pazo, Yuchen Miao, Hoon Kim, John Ralph, Chang-Jun Liu. An engineered monolignol 4-o-methyltransferase depresses lignin biosynthesis and confers novel metabolic capability in Arabidopsis. The Plant cell. 2012 Jul; 24(7):3135-52. doi: 10.1105/tpc.112.101287. [PMID: 22851762]
  • Rocío Santiago, Borja Alarcón, Roberto de Armas, Carlos Vicente, María Estrella Legaz. Changes in cinnamyl alcohol dehydrogenase activities from sugarcane cultivars inoculated with Sporisorium scitamineum sporidia. Physiologia plantarum. 2012 Jun; 145(2):245-59. doi: 10.1111/j.1399-3054.2012.01577.x. [PMID: 22248248]
  • Benjamin Pickel, Jens Pfannstiel, Alexander Steudle, Axel Lehmann, Uwe Gerken, Jürgen Pleiss, Andreas Schaller. A model of dirigent proteins derived from structural and functional similarities with allene oxide cyclase and lipocalins. The FEBS journal. 2012 Jun; 279(11):1980-93. doi: 10.1111/j.1742-4658.2012.08580.x. [PMID: 22443713]
  • Hsi-Chuan Chen, Quanzi Li, Christopher M Shuford, Jie Liu, David C Muddiman, Ronald R Sederoff, Vincent L Chiang. Membrane protein complexes catalyze both 4- and 3-hydroxylation of cinnamic acid derivatives in monolignol biosynthesis. Proceedings of the National Academy of Sciences of the United States of America. 2011 Dec; 108(52):21253-8. doi: 10.1073/pnas.1116416109. [PMID: 22160716]
  • Le Thanh Mai Pham, Su Jin Kim, Bong Keun Song, Yong Hwan Kim. Optimized refolding and characterization of S-peroxidase (CWPO_C of Populus alba) expressed in E. coli. Protein expression and purification. 2011 Dec; 80(2):268-73. doi: 10.1016/j.pep.2011.08.003. [PMID: 21856428]
  • Brijesh Pandey, Veda Prakash Pandey, Upendra Nath Dwivedi. Cloning, expression, functional validation and modeling of cinnamyl alcohol dehydrogenase isolated from xylem of Leucaena leucocephala. Protein expression and purification. 2011 Oct; 79(2):197-203. doi: 10.1016/j.pep.2011.06.003. [PMID: 21708267]
  • Ahmed M A Abd El-Mawla, Salwa F Farag, Till Beuerle. Cinnamyl alcohols and methyl esters of fatty acids from Wedelia prostrata callus cultures. Natural product research. 2011 Jan; 25(1):45-52. doi: 10.1080/14786419.2010.482937. [PMID: 21240761]
  • Kenji Kobata, Makoto Mimura, Mai Sugawara, Tatsuo Watanabe. Synthesis of stable isotope-labeled precursors for the biosyntheses of capsaicinoids, capsinoids, and capsiconinoids. Bioscience, biotechnology, and biochemistry. 2011; 75(8):1611-4. doi: 10.1271/bbb.110187. [PMID: 21821932]
  • Yu-Chen Miao, Chang-Jun Liu. ATP-binding cassette-like transporters are involved in the transport of lignin precursors across plasma and vacuolar membranes. Proceedings of the National Academy of Sciences of the United States of America. 2010 Dec; 107(52):22728-33. doi: 10.1073/pnas.1007747108. [PMID: 21149736]
  • Nathalie Demont-Caulet, Catherine Lapierre, Lise Jouanin, Stéphanie Baumberger, Valérie Méchin. Arabidopsis peroxidase-catalyzed copolymerization of coniferyl and sinapyl alcohols: kinetics of an endwise process. Phytochemistry. 2010 Oct; 71(14-15):1673-83. doi: 10.1016/j.phytochem.2010.06.011. [PMID: 20615517]
  • Fachuang Lu, Jane M Marita, Catherine Lapierre, Lise Jouanin, Kris Morreel, Wout Boerjan, John Ralph. Sequencing around 5-hydroxyconiferyl alcohol-derived units in caffeic acid O-methyltransferase-deficient poplar lignins. Plant physiology. 2010 Jun; 153(2):569-79. doi: 10.1104/pp.110.154278. [PMID: 20427467]
  • Scott E Sattler, Aaron J Saathoff, Eric J Haas, Nathan A Palmer, Deanna L Funnell-Harris, Gautam Sarath, Jeffrey F Pedersen. A nonsense mutation in a cinnamyl alcohol dehydrogenase gene is responsible for the Sorghum brown midrib6 phenotype. Plant physiology. 2009 Jun; 150(2):584-95. doi: 10.1104/pp.109.136408. [PMID: 19363091]
  • Aiping Zhang, Fachuang Lu, Runcang Sun, John Ralph. Ferulate-coniferyl alcohol cross-coupled products formed by radical coupling reactions. Planta. 2009 Apr; 229(5):1099-108. doi: 10.1007/s00425-009-0894-6. [PMID: 19234718]
  • Divya Srivastava, David E Cohen. Identification of the constituents of balsam of peru in tomatoes. Dermatitis : contact, atopic, occupational, drug. 2009 Mar; 20(2):99-105. doi: . [PMID: 19426616]
  • Hong-Chao Zhang, Hai-Ming Shi. [Studies on chemical constituents from Elaeocarpus sylvestris]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2008 Oct; 31(10):1503-5. doi: ". [PMID: 19230399]
  • Abdellatif Barakat, Brigitte Chabbert, Bernard Cathala. Effect of reaction media concentration on the solubility and the chemical structure of lignin model compounds. Phytochemistry. 2007 Aug; 68(15):2118-25. doi: 10.1016/j.phytochem.2007.05.004. [PMID: 17582447]
  • Anna Berim, Bernd Schneider, Maike Petersen. Methyl allyl ether formation in plants: novel S-adenosyl L-methionine:coniferyl alcohol 9-O-methyltransferase from suspension cultures of three Linum species. Plant molecular biology. 2007 Jun; 64(3):279-91. doi: 10.1007/s11103-007-9151-1. [PMID: 17333502]
  • Suk-Ling Wee, Keng-Hong Tan, Ritsuo Nishida. Pharmacophagy of methyl eugenol by males enhances sexual selection of Bactrocera carambolae. Journal of chemical ecology. 2007 Jun; 33(6):1272-82. doi: 10.1007/s10886-007-9295-0. [PMID: 17443401]
  • Buhyun Youn, Sung-Jin Kim, Syed G A Moinuddin, Choonseok Lee, Diana L Bedgar, Athena R Harper, Laurence B Davin, Norman G Lewis, Chulhee Kang. Mechanistic and structural studies of apoform, binary, and ternary complexes of the Arabidopsis alkenal double bond reductase At5g16970. The Journal of biological chemistry. 2006 Dec; 281(52):40076-88. doi: 10.1074/jbc.m605900200. [PMID: 17028190]
  • Yasushi Sato, Ross W Whetten. Characterization of two laccases of loblolly pine (Pinus taeda) expressed in tobacco BY-2 cells. Journal of plant research. 2006 Nov; 119(6):581-8. doi: 10.1007/s10265-006-0020-9. [PMID: 16952031]
  • Umesh P Agarwal. Raman imaging to investigate ultrastructure and composition of plant cell walls: distribution of lignin and cellulose in black spruce wood (Picea mariana). Planta. 2006 Oct; 224(5):1141-53. doi: 10.1007/s00425-006-0295-z. [PMID: 16761135]
  • Takao Koeduka, Eyal Fridman, David R Gang, Daniel G Vassão, Brenda L Jackson, Christine M Kish, Irina Orlova, Snejina M Spassova, Norman G Lewis, Joseph P Noel, Thomas J Baiga, Natalia Dudareva, Eran Pichersky. Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester. Proceedings of the National Academy of Sciences of the United States of America. 2006 Jun; 103(26):10128-33. doi: 10.1073/pnas.0603732103. [PMID: 16782809]
  • Young Jin Kim, Dong Gwan Kim, Sun Hi Lee, Incheol Lee. Wound-induced expression of the ferulate 5-hydroxylase gene in Camptotheca acuminata. Biochimica et biophysica acta. 2006 Feb; 1760(2):182-90. doi: 10.1016/j.bbagen.2005.08.015. [PMID: 16332414]
  • Isabelle Damiani, Kris Morreel, Saïda Danoun, Geert Goeminne, Nabila Yahiaoui, Christiane Marque, Joachim Kopka, Eric Messens, Deborah Goffner, Wout Boerjan, Alain-Michel Boudet, Soizic Rochange. Metabolite profiling reveals a role for atypical cinnamyl alcohol dehydrogenase CAD1 in the synthesis of coniferyl alcohol in tobacco xylem. Plant molecular biology. 2005 Nov; 59(5):753-69. doi: 10.1007/s11103-005-0947-6. [PMID: 16270228]
  • Richard Sibout, Aymerick Eudes, Gregory Mouille, Brigitte Pollet, Catherine Lapierre, Lise Jouanin, Armand Séguin. CINNAMYL ALCOHOL DEHYDROGENASE-C and -D are the primary genes involved in lignin biosynthesis in the floral stem of Arabidopsis. The Plant cell. 2005 Jul; 17(7):2059-76. doi: 10.1105/tpc.105.030767. [PMID: 15937231]
  • Sanna Koutaniemi, Merja M Toikka, Anna Kärkönen, Maaret Mustonen, Taina Lundell, Liisa K Simola, Ilkka A Kilpeläinen, Teemu H Teeri. Characterization of basic p-coumaryl and coniferyl alcohol oxidizing peroxidases from a lignin-forming Picea abies suspension culture. Plant molecular biology. 2005 May; 58(2):141-57. doi: 10.1007/s11103-005-5345-6. [PMID: 16027971]
  • Yedidya Gafni, Yael Levy. Coniferyl alcohol, a lignin precursor, stimulates Rhizobium rhizogenes A4 virulence. Current microbiology. 2005 May; 50(5):262-5. doi: 10.1007/s00284-004-4427-z. [PMID: 15886921]
  • D Lairez, B Cathala, B Monties, F Bedos-Belval, H Duran, L Gorrichon. Aggregation during coniferyl alcohol polymerization in pectin solution: a biomimetic approach of the first steps of lignification. Biomacromolecules. 2005 Mar; 6(2):763-74. doi: 10.1021/bm049390y. [PMID: 15762640]
  • Kaori Saito, Toshiyuki Kato, Yukiko Tsuji, Kazuhiko Fukushima. Identifying the characteristic secondary ions of lignin polymer using ToF-SIMS. Biomacromolecules. 2005 Mar; 6(2):678-83. doi: 10.1021/bm049521v. [PMID: 15762629]
  • E Padu, H Kollist, I Tulva, E Oksanen, H Moldau. Components of apoplastic ascorbate use in Betula pendula leaves exposed to CO2 and O3 enrichment. The New phytologist. 2005 Jan; 165(1):131-41. doi: 10.1111/j.1469-8137.2004.01220.x. [PMID: 15720628]
  • Mirko Bunzel, John Ralph, Fachuang Lu, Ronald D Hatfield, Hans Steinhart. Lignins and ferulate-coniferyl alcohol cross-coupling products in cereal grains. Journal of agricultural and food chemistry. 2004 Oct; 52(21):6496-502. doi: 10.1021/jf040204p. [PMID: 15479013]
  • Shinya Sasaki, Tomoaki Nishida, Yuji Tsutsumi, Ryuichiro Kondo. Lignin dehydrogenative polymerization mechanism: a poplar cell wall peroxidase directly oxidizes polymer lignin and produces in vitro dehydrogenative polymer rich in beta-O-4 linkage. FEBS letters. 2004 Mar; 562(1-3):197-201. doi: 10.1016/s0014-5793(04)00224-8. [PMID: 15044025]
  • Hong-Jie Zhang, Kongmany Sydara, Ghee Teng Tan, Cuiying Ma, Bounhoong Southavong, D Doel Soejarto, John M Pezzuto, Harry H S Fong. Bioactive constituents from Asparagus cochinchinensis. Journal of natural products. 2004 Feb; 67(2):194-200. doi: 10.1021/np030370b. [PMID: 14987058]
  • Federico Pomar, Nuria Caballero, María Pedreño, A Ros Barceló. H(2)O(2) generation during the auto-oxidation of coniferyl alcohol drives the oxidase activity of a highly conserved class III peroxidase involved in lignin biosynthesis. FEBS letters. 2002 Oct; 529(2-3):198-202. doi: 10.1016/s0014-5793(02)03339-2. [PMID: 12372600]
  • Hans Onnerud, Liming Zhang, Göran Gellerstedt, Gunnar Henriksson. Polymerization of monolignols by redox shuttle-mediated enzymatic oxidation: a new model in lignin biosynthesis I. The Plant cell. 2002 Aug; 14(8):1953-62. doi: 10.1105/tpc.001487. [PMID: 12172033]
  • Adinpunya Mitra, Melinda J Mayer, Fred A Mellon, Anthony J Michael, Arjan Narbad, Adrian J Parr, Keith W Waldron, Nicholas J Walton. 4-Hydroxycinnamoyl-CoA hydratase/lyase, an enzyme of phenylpropanoid cleavage from Pseudomonas, causes formation of C(6)-C(1) acid and alcohol glucose conjugates when expressed in hairy roots of Datura stramonium L. Planta. 2002 May; 215(1):79-89. doi: 10.1007/s00425-001-0712-2. [PMID: 12012244]
  • T Nagasaki, S Yasuda, T Imai. Preparation of antibody against agatharesinol, a norlignan, using a hapten-carrier conjugate. Phytochemistry. 2001 Nov; 58(6):833-40. doi: 10.1016/s0031-9422(01)00323-5. [PMID: 11684179]
  • K L Nielsen, C Indiani, A Henriksen, A Feis, M Becucci, M Gajhede, G Smulevich, K G Welinder. Differential activity and structure of highly similar peroxidases. Spectroscopic, crystallographic, and enzymatic analyses of lignifying Arabidopsis thaliana peroxidase A2 and horseradish peroxidase A2. Biochemistry. 2001 Sep; 40(37):11013-21. doi: 10.1021/bi010661o. [PMID: 11551197]
  • M Hosokawa, S Suzuki, T Umezawa, Y Sato. Progress of lignification mediated by intercellular transportation of monolignols during tracheary element differentiation of isolated Zinnia mesophyll cells. Plant & cell physiology. 2001 Sep; 42(9):959-68. doi: 10.1093/pcp/pce124. [PMID: 11577190]
  • L Li, X F Cheng, J Leshkevich, T Umezawa, S A Harding, V L Chiang. The last step of syringyl monolignol biosynthesis in angiosperms is regulated by a novel gene encoding sinapyl alcohol dehydrogenase. The Plant cell. 2001 Jul; 13(7):1567-86. doi: 10.1105/tpc.010111. [PMID: 11449052]
  • G J McDougall. Cell-wall proteins from Sitka spruce xylem are selectively insolubilised during formation of dehydrogenation polymers of coniferyl alcohol. Phytochemistry. 2001 May; 57(2):157-63. doi: 10.1016/s0031-9422(01)00027-9. [PMID: 11382230]
  • M H Daurade-Le Vagueresse, C Romiti, C Grosclaude, M Bounias. Coevolutionary toxicity as suggested by differential coniferyl alcohol inhibition of ceratocystis species growth. Toxicon : official journal of the International Society on Toxinology. 2001 Feb; 39(2-3):203-8. doi: 10.1016/s0041-0101(00)00116-1. [PMID: 10978737]
  • J Ralph, C Lapierre, F Lu, J M Marita, G Pilate, J Van Doorsselaere, W Boerjan, L Jouanin. NMR evidence for benzodioxane structures resulting from incorporation of 5-hydroxyconiferyl alcohol into Lignins of O-methyltransferase-deficient poplars. Journal of agricultural and food chemistry. 2001 Jan; 49(1):86-91. doi: 10.1021/jf001042+. [PMID: 11302112]
  • N R Guz, F R Stermitz. Synthesis and structures of regioisomeric hydnocarpin-type flavonolignans. Journal of natural products. 2000 Aug; 63(8):1140-5. doi: 10.1021/np000166d. [PMID: 10978213]
  • R R Sederoff, J J MacKay, J Ralph, R D Hatfield. Unexpected variation in lignin. Current opinion in plant biology. 1999 Apr; 2(2):145-52. doi: 10.1016/s1369-5266(99)80029-6. [PMID: 10322194]
  • P Ranocha, G McDougall, S Hawkins, R Sterjiades, G Borderies, D Stewart, M Cabanes-Macheteau, A M Boudet, D Goffner. Biochemical characterization, molecular cloning and expression of laccases - a divergent gene family - in poplar. European journal of biochemistry. 1999 Jan; 259(1-2):485-95. doi: 10.1046/j.1432-1327.1999.00061.x. [PMID: 9914531]
  • H Li, J Li, J K Prasain, Y Tezuka, T Namba, T Miyahara, S Tonami, H Seto, T Tada, S Kadota. Antiosteoporotic activity of the stems of Sambucus sieboldiana. Biological & pharmaceutical bulletin. 1998 Jun; 21(6):594-8. doi: 10.1248/bpb.21.594. [PMID: 9657044]
  • J Kaiser. New 'guiding' protein discovered. Science (New York, N.Y.). 1997 Jan; 275(5298):306. doi: 10.1126/science.275.5298.306. [PMID: 9005554]
  • R Sterjiades, P Ranocha, A M Boudet, D Goffner. Identification of specific laccase isoforms capable of polymerizing monolignols by an 'in-gel' procedure. Analytical biochemistry. 1996 Nov; 242(1):158-61. doi: 10.1006/abio.1996.0445. [PMID: 8923982]
  • V Lauvergeat, K Kennedy, C Feuillet, J H McKie, L Gorrichon, M Baltas, A M Boudet, J Grima-Pettenati, K T Douglas. Site-directed mutagenesis of a serine residue in cinnamyl alcohol dehydrogenase, a plant NADPH-dependent dehydrogenase, affects the specificity for the coenzyme. Biochemistry. 1995 Sep; 34(38):12426-34. doi: 10.1021/bi00038a041. [PMID: 7547988]
  • C B Rasmussen, H B Dunford, K G Welinder. Rate enhancement of compound I formation of barley peroxidase by ferulic acid, caffeic acid, and coniferyl alcohol. Biochemistry. 1995 Mar; 34(12):4022-9. doi: 10.1021/bi00012a021. [PMID: 7696268]
  • M A Ferrer, M A Pedreño, R Muñoz, A Ros Barceló. Hammett rho sigma correlation for the inhibition by indoles of coniferyl alcohol oxidation catalyzed by cell wall peroxidases. Biochemistry international. 1992 Dec; 28(5):949-55. doi: ". [PMID: 1288505]
  • T Katayama, L B Davin, N G Lewis. An extraordinary accumulation of (-)-pinoresinol in cell-free extracts of Forsythia intermedia: evidence for enantiospecific reduction of (+)-pinoresinol. Phytochemistry. 1992 Nov; 31(11):3875-81. doi: 10.1016/s0031-9422(00)97545-9. [PMID: 11536516]
  • L B Davin, D L Bedgar, T Katayama, N G Lewis. On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, coniferyl alcohol. Phytochemistry. 1992 Nov; 31(11):3869-74. doi: 10.1016/s0031-9422(00)97544-7. [PMID: 11536515]
  • T Hendriks, H J Wijsman, L C van Loon. Petunia peroxidase a: isolation, purification and characteristics. European journal of biochemistry. 1991 Jul; 199(1):139-46. doi: 10.1111/j.1432-1033.1991.tb16101.x. [PMID: 2065669]
  • M A Ferrer, M A Pedreño, R Muñoz, A R Barceló. Oxidation of coniferyl alcohol by cell wall peroxidases at the expense of indole-3-acetic acid and O2. A model for the lignification of plant cell walls in the absence of H2O2. FEBS letters. 1990 Dec; 276(1-2):127-30. doi: 10.1016/0014-5793(90)80524-m. [PMID: 2265691]
  • E Yamamoto, E J Inciong, L B Davin, N G Lewis. Formation of cis-coniferin in cell-free extracts of Fagus grandifolia Ehrh bark. Plant physiology. 1990; 94(?):209-13. doi: 10.1104/pp.94.1.209. [PMID: 11537477]
  • . . . . doi: . [PMID: 16443696]
  • . . . . doi: . [PMID: 14992596]
  • . . . . doi: . [PMID: 8994027]