Sinapyl alcohol (BioDeep_00000003275)

 

Secondary id: BioDeep_00000406289, BioDeep_00000861005

natural product human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenol

化学式: C11H14O4 (210.0892)
中文名称: 芥子醇
谱图信息: 最多检出来源 Viridiplantae(plant) 15.37%

分子结构信息

SMILES: COC1=CC(=CC(=C1O)OC)C=CCO
InChI: InChI=1/C11H14O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-4,6-7,12-13H,5H2,1-2H3/b4-3+

描述信息

Sinapyl alcohol is an organic compound derived from cinnamic acid. This phytochemical is one of the monolignols. It is biosynthetized via the phenylpropanoid biochemical pathway, its immediate precursor being sinapaldehyde. Sinapyl alcohol is a precursor to lignin or lignans. It is also a biosynthetic precursor to various stilbenes and coumarins.[From Wiki].

同义名列表

15 个代谢物同义名

4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenol; (e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propen-1-ol; 4-(3-Hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenol; 4-(3-Hydroxy-1-propenyl)-2,6-dimethoxy-phenol; 4-Hydroxy-3,5-dimethoxycinnamyl alcohol; trans-Sinapoyl alcohol; (e)-Sinapoyl alcohol; (e)-Sinapyl alcohol; Sinapyl alcohol(e); Sinapoyl alcohol; sinapyl alcohol; Sinapic alcohol; Sinapyl-alcohol; ACMC-20ajpw; Sinapyl alcohol



数据库引用编号

27 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(2)

PlantCyc(2)

代谢反应

159 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(4)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(155)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

44 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。

亚细胞结构定位 关联基因列表
Cytoplasm 11 ALB, APEH, CAT, CCR2, DHPS, HGS, LST1, MSMP, NOS2, PRX, ZNF346
Peripheral membrane protein 4 ACHE, CYP1B1, HGS, PRX
Endoplasmic reticulum membrane 2 CYP1B1, POR
Nucleus 6 ACHE, ALB, MYB, NOS2, PRX, ZNF346
cytosol 11 ALB, APEH, CAT, CBL, COMT, DHPS, HGS, LST1, MYB, NOS2, POR
dendrite 2 CCR2, COMT
centrosome 1 ALB
nucleoplasm 3 MYB, NOS2, ZNF346
RNA polymerase II transcription regulator complex 1 MYB
Cell membrane 5 ACHE, CCR2, COMT, PRX, TNF
Cytoplasmic side 3 HGS, POR, PRX
Early endosome membrane 1 HGS
Multi-pass membrane protein 2 CCR2, LST1
Synapse 2 ACHE, COMT
cell junction 1 PRX
cell surface 2 ACHE, TNF
Golgi apparatus 4 ACHE, ALB, CBL, LST1
Golgi membrane 1 LST1
growth cone 1 CBL
lysosomal membrane 1 CP
neuromuscular junction 1 ACHE
neuronal cell body 2 CCR2, TNF
Cytoplasm, cytosol 1 NOS2
Lysosome 1 HGS
endosome 1 HGS
plasma membrane 10 ACHE, BCHE, CBL, CCR2, COMT, CP, LST1, NOS2, PRX, TNF
Membrane 8 ACHE, CAT, CCR2, COMT, CYP1B1, LST1, MYB, POR
axon 1 COMT
basolateral plasma membrane 1 LST1
extracellular exosome 6 ALB, APEH, CAT, COMT, CP, HGS
endoplasmic reticulum 2 ALB, POR
extracellular space 6 ACHE, ALB, BCHE, CP, MSMP, TNF
perinuclear region of cytoplasm 4 ACHE, CBL, CCR2, NOS2
mitochondrion 2 CAT, CYP1B1
protein-containing complex 2 ALB, CAT
intracellular membrane-bounded organelle 4 CAT, COMT, CYP1B1, POR
Microsome membrane 1 CYP1B1
Secreted 5 ACHE, ALB, BCHE, CP, MSMP
extracellular region 7 ACHE, ALB, APEH, BCHE, CAT, CP, TNF
Single-pass membrane protein 1 POR
mitochondrial matrix 1 CAT
Extracellular side 2 ACHE, COMT
anchoring junction 2 ALB, PRX
Cell projection, cilium 1 CBL
nuclear membrane 1 APEH
external side of plasma membrane 2 CCR2, TNF
perikaryon 1 CCR2
nucleolus 1 ZNF346
Cytoplasm, P-body 1 NOS2
P-body 1 NOS2
Early endosome 1 HGS
recycling endosome 1 TNF
Single-pass type II membrane protein 2 COMT, TNF
Cytoplasm, perinuclear region 1 NOS2
Membrane raft 2 CBL, TNF
focal adhesion 2 CAT, CBL
flotillin complex 1 CBL
Peroxisome 2 CAT, NOS2
basement membrane 1 ACHE
Peroxisome matrix 1 CAT
peroxisomal matrix 2 CAT, NOS2
peroxisomal membrane 1 CAT
ciliary basal body 1 ALB
cilium 1 CBL
phagocytic cup 1 TNF
centriole 1 ALB
Nucleus, nucleolus 1 ZNF346
spindle pole 1 ALB
blood microparticle 3 ALB, BCHE, CP
Basolateral cell membrane 1 LST1
Lipid-anchor, GPI-anchor 1 ACHE
fibrillar center 1 CCR2
side of membrane 1 ACHE
basal plasma membrane 1 LST1
multivesicular body membrane 1 HGS
ficolin-1-rich granule lumen 2 APEH, CAT
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 3 ALB, BCHE, CP
nuclear matrix 1 MYB
platelet alpha granule lumen 1 ALB
nuclear envelope lumen 1 BCHE
[Isoform 2]: Cytoplasm 1 PRX
Endosome, multivesicular body membrane 1 HGS
ESCRT-0 complex 1 HGS
phagocytic vesicle lumen 1 HGS
synaptic cleft 1 ACHE
Basal cell membrane 1 LST1
[Isoform 1]: Cell membrane 1 PRX
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
cortical cytoskeleton 1 NOS2
catalase complex 1 CAT
[Isoform Soluble]: Cytoplasm 1 COMT
[Isoform Membrane-bound]: Cell membrane 1 COMT
[Isoform H]: Cell membrane 1 ACHE
ciliary transition fiber 1 ALB
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Fan Wang, Wanli Zhao, Wei Lv, Pirui Li, Mei Tian, Shu Xu, Linwei Li, Ruiyang Wang, Fei Liu, Yu Chen, Xu Feng. Identification and Functional Characterization of a Novel Sinapyl Alcohol Acyltransferase from Euphorbia lathyris L. Journal of agricultural and food chemistry. 2023 Dec; 71(50):20187-20197. doi: 10.1021/acs.jafc.3c07127. [PMID: 38044624]
  • Junying Ma, Xiaoyan Li, Maolin He, Yanwen Li, Wei Lu, Mengyao Li, Bo Sun, Yangxia Zheng. A Joint Transcriptomic and Metabolomic Analysis Reveals the Regulation of Shading on Lignin Biosynthesis in Asparagus. International journal of molecular sciences. 2023 Jan; 24(2):. doi: 10.3390/ijms24021539. [PMID: 36675053]
  • 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]
  • Clémence Simon, Cédric Lion, Hania Ahouari, Hervé Vezin, Simon Hawkins, Christophe Biot. EPR imaging of sinapyl alcohol and its application to the study of plant cell wall lignification. Chemical communications (Cambridge, England). 2021 Jan; 57(3):387-390. doi: 10.1039/d0cc05218c. [PMID: 33326527]
  • 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]
  • Jun Shigeto, Yukie Ueda, Shinya Sasaki, Koki Fujita, Yuji Tsutsumi. Enzymatic activities for lignin monomer intermediates highlight the biosynthetic pathway of syringyl monomers in Robinia pseudoacacia. Journal of plant research. 2017 Jan; 130(1):203-210. doi: 10.1007/s10265-016-0882-4. [PMID: 27888422]
  • 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]
  • Yuki Tobimatsu, Armin Wagner, Lloyd Donaldson, Prajakta Mitra, Claudiu Niculaes, Oana Dima, Jeong Im Kim, Nickolas Anderson, Dominique Loque, Wout Boerjan, Clint Chapple, John Ralph. Visualization of plant cell wall lignification using fluorescence-tagged monolignols. The Plant journal : for cell and molecular biology. 2013 Nov; 76(3):357-66. doi: 10.1111/tpj.12299. [PMID: 23889038]
  • Xinhui Tian, Gang Ding, Chaozhong Peng, Yanbao Hu, Li Li, Hong Chen, Zhongmei Zou. Sinapyl alcohol derivatives from the lipo-soluble part of Dichrocephala benthamii C. B. Clarke. Molecules (Basel, Switzerland). 2013 Jan; 18(2):1720-7. doi: 10.3390/molecules18021720. [PMID: 23434858]
  • Juan A Martín, Alejandro Solla, María C García-Vallejo, Luis Gil. Chemical changes in Ulmus minor xylem tissue after salicylic acid or carvacrol treatments are associated with enhanced resistance to Ophiostoma novo-ulmi. Phytochemistry. 2012 Nov; 83(?):104-9. doi: 10.1016/j.phytochem.2012.07.017. [PMID: 22910373]
  • Christian Bukh, Pia Haugaard Nord-Larsen, Søren K Rasmussen. Phylogeny and structure of the cinnamyl alcohol dehydrogenase gene family in Brachypodium distachyon. Journal of experimental botany. 2012 Oct; 63(17):6223-36. doi: 10.1093/jxb/ers275. [PMID: 23028019]
  • Lorena Palacio, Juan J Cantero, Rosa M Cusidó, Marta E Goleniowski. Phenolic compound production in relation to differentiation in cell and tissue cultures of Larrea divaricata (Cav.). Plant science : an international journal of experimental plant biology. 2012 Sep; 193-194(?):1-7. doi: 10.1016/j.plantsci.2012.05.007. [PMID: 22794913]
  • Xing Li, Dongming Ma, Jianlin Chen, Gaobin Pu, Yunpeng Ji, Caiyan Lei, Zhigao Du, Benye Liu, Hechun Ye, Hong Wang. Biochemical characterization and identification of a cinnamyl alcohol dehydrogenase from Artemisia annua. Plant science : an international journal of experimental plant biology. 2012 Sep; 193-194(?):85-95. doi: 10.1016/j.plantsci.2012.05.011. [PMID: 22794921]
  • Harleen Kaur, Kamel Shaker, Nicolas Heinzel, John Ralph, Ivan Gális, Ian T Baldwin. Environmental stresses of field growth allow cinnamyl alcohol dehydrogenase-deficient Nicotiana attenuata plants to compensate for their structural deficiencies. Plant physiology. 2012 Aug; 159(4):1545-70. doi: 10.1104/pp.112.196717. [PMID: 22645069]
  • Santiago Alejandro, Yuree Lee, Takayuki Tohge, Damien Sudre, Sonia Osorio, Jiyoung Park, Lucien Bovet, Youngsook Lee, Niko Geldner, Alisdair R Fernie, Enrico Martinoia. AtABCG29 is a monolignol transporter involved in lignin biosynthesis. Current biology : CB. 2012 Jul; 22(13):1207-12. doi: 10.1016/j.cub.2012.04.064. [PMID: 22704988]
  • 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]
  • Yan-Wen Wang, Wen-Chao Wang, Shang-Hui Jin, Jun Wang, Bo Wang, Bing-Kai Hou. Over-expression of a putative poplar glycosyltransferase gene, PtGT1, in tobacco increases lignin content and causes early flowering. Journal of experimental botany. 2012 Apr; 63(7):2799-808. doi: 10.1093/jxb/ers001. [PMID: 22268132]
  • Teresa Martínez-Cortés, Federico Pomar, José Manuel Espiñeira, Fuencisla Merino, Esther Novo-Uzal. Purification and kinetic characterization of two peroxidases of Selaginella martensii Spring. involved in lignification. Plant physiology and biochemistry : PPB. 2012 Mar; 52(?):130-9. doi: 10.1016/j.plaphy.2011.12.008. [PMID: 22305076]
  • Kyung Hye Seo, Ningning Zhuang, Cong Chen, Jae-Young Song, Hyung-Lyun Kang, Kwang-Ho Rhee, Kon Ho Lee. Unusual NADPH conformation in the crystal structure of a cinnamyl alcohol dehydrogenase from Helicobacter pylori in complex with NADP(H) and substrate docking analysis. FEBS letters. 2012 Feb; 586(4):337-43. doi: 10.1016/j.febslet.2012.01.020. [PMID: 22269576]
  • Jun Shigeto, Yoshitaka Itoh, Yuji Tsutsumi, Ryuichiro Kondo. Identification of Tyr74 and Tyr177 as substrate oxidation sites in cationic cell wall-bound peroxidase from Populus alba L. The FEBS journal. 2012 Jan; 279(2):348-57. doi: 10.1111/j.1742-4658.2011.08429.x. [PMID: 22099451]
  • Erin D Scully, Kelli Hoover, John Carlson, Ming Tien, Scott M Geib. Proteomic analysis of Fusarium solani isolated from the Asian longhorned beetle, Anoplophora glabripennis. PloS one. 2012; 7(4):e32990. doi: 10.1371/journal.pone.0032990. [PMID: 22496740]
  • 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]
  • Ilga Porth, Björn Hamberger, Richard White, Kermit Ritland. Defense mechanisms against herbivory in Picea: sequence evolution and expression regulation of gene family members in the phenylpropanoid pathway. BMC genomics. 2011 Dec; 12(?):608. doi: 10.1186/1471-2164-12-608. [PMID: 22177423]
  • Abdellah Barakate, Jennifer Stephens, Alison Goldie, William N Hunter, David Marshall, Robert D Hancock, Catherine Lapierre, Kris Morreel, Wout Boerjan, Claire Halpin. Syringyl lignin is unaltered by severe sinapyl alcohol dehydrogenase suppression in tobacco. The Plant cell. 2011 Dec; 23(12):4492-506. doi: 10.1105/tpc.111.089037. [PMID: 22158465]
  • 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]
  • Marina Varbanova, Katie Porter, Fachuang Lu, John Ralph, Ray Hammerschmidt, A Daniel Jones, Brad Day. Molecular and biochemical basis for stress-induced accumulation of free and bound p-coumaraldehyde in cucumber. Plant physiology. 2011 Nov; 157(3):1056-66. doi: 10.1104/pp.111.184358. [PMID: 21940999]
  • Venugopal Mendu, Anne E Harman-Ware, Mark Crocker, Jungho Jae, Jozsef Stork, Samuel Morton, Andrew Placido, George Huber, Seth Debolt. Identification and thermochemical analysis of high-lignin feedstocks for biofuel and biochemical production. Biotechnology for biofuels. 2011 Oct; 4(?):43. doi: 10.1186/1754-6834-4-43. [PMID: 22018114]
  • 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]
  • Sangaalofa T Clark, Wynand S Verwoerd. A systems approach to identifying correlated gene targets for the loss of colour pigmentation in plants. BMC bioinformatics. 2011 Aug; 12(?):343. doi: 10.1186/1471-2105-12-343. [PMID: 21849042]
  • Barek Tamasloukht, Mary Sarah-Jane Wong Quai Lam, Yves Martinez, Koffi Tozo, Odile Barbier, Cyril Jourda, Alain Jauneau, Gisèle Borderies, Sandrine Balzergue, Jean-Pierre Renou, Stéphanie Huguet, Jean Pierre Martinant, Christophe Tatout, Catherine Lapierre, Yves Barrière, Deborah Goffner, Magalie Pichon. Characterization of a cinnamoyl-CoA reductase 1 (CCR1) mutant in maize: effects on lignification, fibre development, and global gene expression. Journal of experimental botany. 2011 Jul; 62(11):3837-48. doi: 10.1093/jxb/err077. [PMID: 21493812]
  • Kristen M DeAngelis, Martin Allgaier, Yaucin Chavarria, Julian L Fortney, Phillip Hugenholtz, Blake Simmons, Kerry Sublette, Whendee L Silver, Terry C Hazen. Characterization of trapped lignin-degrading microbes in tropical forest soil. PloS one. 2011 Apr; 6(4):e19306. doi: 10.1371/journal.pone.0019306. [PMID: 21559391]
  • Madana M R Ambavaram, Arjun Krishnan, Kurniawan R Trijatmiko, Andy Pereira. Coordinated activation of cellulose and repression of lignin biosynthesis pathways in rice. Plant physiology. 2011 Feb; 155(2):916-31. doi: 10.1104/pp.110.168641. [PMID: 21205614]
  • 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]
  • Sajida Abdureyim, Nurmuhammat Amat, Anwar Umar, Halmurat Upur, Benedicte Berke, Nicholas Moore. Anti-inflammatory, immunomodulatory, and heme oxygenase-1 inhibitory activities of ravan napas, a formulation of uighur traditional medicine, in a rat model of allergic asthma. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):. doi: 10.1155/2011/725926. [PMID: 20953388]
  • J M Espiñeira, E Novo Uzal, L V Gómez Ros, J S Carrión, F Merino, A Ros Barceló, F Pomar. Distribution of lignin monomers and the evolution of lignification among lower plants. Plant biology (Stuttgart, Germany). 2011 Jan; 13(1):59-68. doi: 10.1111/j.1438-8677.2010.00345.x. [PMID: 21143726]
  • Rajib Saha, Patrick F Suthers, Costas D Maranas. Zea mays iRS1563: a comprehensive genome-scale metabolic reconstruction of maize metabolism. PloS one. 2011; 6(7):e21784. doi: 10.1371/journal.pone.0021784. [PMID: 21755001]
  • Angela Ziebell, Kristen Gracom, Rui Katahira, Fang Chen, Yunqiao Pu, Art Ragauskas, Richard A Dixon, Mark Davis. Increase in 4-coumaryl alcohol units during lignification in alfalfa (Medicago sativa) alters the extractability and molecular weight of lignin. The Journal of biological chemistry. 2010 Dec; 285(50):38961-8. doi: 10.1074/jbc.m110.137315. [PMID: 20921228]
  • Cristiana Gomes de Oliveira Dal'Molin, Lake-Ee Quek, Robin William Palfreyman, Stevens Michael Brumbley, Lars Keld Nielsen. C4GEM, a genome-scale metabolic model to study C4 plant metabolism. Plant physiology. 2010 Dec; 154(4):1871-85. doi: 10.1104/pp.110.166488. [PMID: 20974891]
  • Gordon V Louie, Marianne E Bowman, Yi Tu, Aidyn Mouradov, German Spangenberg, Joseph P Noel. Structure-function analyses of a caffeic acid O-methyltransferase from perennial ryegrass reveal the molecular basis for substrate preference. The Plant cell. 2010 Dec; 22(12):4114-27. doi: 10.1105/tpc.110.077578. [PMID: 21177481]
  • Olga Pechanova, Chuan-Yu Hsu, Joshua P Adams, Tibor Pechan, Lindsay Vandervelde, Jenny Drnevich, Sara Jawdy, Ardeshir Adeli, Jeffrey C Suttle, Amanda M Lawrence, Timothy J Tschaplinski, Armand Séguin, Cetin Yuceer. Apoplast proteome reveals that extracellular matrix contributes to multistress response in poplar. BMC genomics. 2010 Nov; 11(?):674. doi: 10.1186/1471-2164-11-674. [PMID: 21114852]
  • Carmen Gayoso, Federico Pomar, Esther Novo-Uzal, Fuencisla Merino, Oskar Martínez de Ilárduya. The Ve-mediated resistance response of the tomato to Verticillium dahliae involves H2O2, peroxidase and lignins and drives PAL gene expression. BMC plant biology. 2010 Oct; 10(?):232. doi: 10.1186/1471-2229-10-232. [PMID: 20977727]
  • 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]
  • Dong-Mei Guo, Jin-Hua Ran, Xiao-Quan Wang. Evolution of the Cinnamyl/Sinapyl Alcohol Dehydrogenase (CAD/SAD) gene family: the emergence of real lignin is associated with the origin of Bona Fide CAD. Journal of molecular evolution. 2010 Sep; 71(3):202-18. doi: 10.1007/s00239-010-9378-3. [PMID: 20721545]
  • Peifen Zhang, Kate Dreher, A Karthikeyan, Anjo Chi, Anuradha Pujar, Ron Caspi, Peter Karp, Vanessa Kirkup, Mario Latendresse, Cynthia Lee, Lukas A Mueller, Robert Muller, Seung Yon Rhee. Creation of a genome-wide metabolic pathway database for Populus trichocarpa using a new approach for reconstruction and curation of metabolic pathways for plants. Plant physiology. 2010 Aug; 153(4):1479-91. doi: 10.1104/pp.110.157396. [PMID: 20522724]
  • Kris Morreel, Oana Dima, Hoon Kim, Fachuang Lu, Claudiu Niculaes, Ruben Vanholme, Rebecca Dauwe, Geert Goeminne, Dirk Inzé, Eric Messens, John Ralph, Wout Boerjan. Mass spectrometry-based sequencing of lignin oligomers. Plant physiology. 2010 Aug; 153(4):1464-78. doi: 10.1104/pp.110.156489. [PMID: 20554692]
  • Dennis Janz, Katja Behnke, Jörg-Peter Schnitzler, Basem Kanawati, Philippe Schmitt-Kopplin, Andrea Polle. Pathway analysis of the transcriptome and metabolome of salt sensitive and tolerant poplar species reveals evolutionary adaption of stress tolerance mechanisms. BMC plant biology. 2010 Jul; 10(?):150. doi: 10.1186/1471-2229-10-150. [PMID: 20637123]
  • Young-Hwa Kim, Jung Myung Bae, Gyung-Hye Huh. Transcriptional regulation of the cinnamyl alcohol dehydrogenase gene from sweet potato in response to plant developmental stage and environmental stress. Plant cell reports. 2010 Jul; 29(7):779-91. doi: 10.1007/s00299-010-0864-2. [PMID: 20454964]
  • Rui Ke, En-Yuan Zhu, Gui-xin Chou. A new phenylpropanoid glycoside from Cirsium setosum. Yao xue xue bao = Acta pharmaceutica Sinica. 2010 Jul; 45(7):879-82. doi: . [PMID: 20931786]
  • Frederik R D van Parijs, Kris Morreel, John Ralph, Wout Boerjan, Roeland M H Merks. Modeling lignin polymerization. I. Simulation model of dehydrogenation polymers. Plant physiology. 2010 Jul; 153(3):1332-44. doi: 10.1104/pp.110.154468. [PMID: 20472753]
  • Xinguo Li, Harry X Wu, Simon G Southerton. Comparative genomics reveals conservative evolution of the xylem transcriptome in vascular plants. BMC evolutionary biology. 2010 Jun; 10(?):190. doi: 10.1186/1471-2148-10-190. [PMID: 20565927]
  • John H Grabber, Paul F Schatz, Hoon Kim, Fachuang Lu, John Ralph. Identifying new lignin bioengineering targets: 1. Monolignol-substitute impacts on lignin formation and cell wall fermentability. BMC plant biology. 2010 Jun; 10(?):114. doi: 10.1186/1471-2229-10-114. [PMID: 20565789]
  • 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]
  • Qing-Hu Ma. Functional analysis of a cinnamyl alcohol dehydrogenase involved in lignin biosynthesis in wheat. Journal of experimental botany. 2010 Jun; 61(10):2735-44. doi: 10.1093/jxb/erq107. [PMID: 20400532]
  • Abdelali Barakat, Agnieszka Bagniewska-Zadworna, Christopher J Frost, John E Carlson. Phylogeny and expression profiling of CAD and CAD-like genes in hybrid Populus (P. deltoides x P. nigra): evidence from herbivore damage for subfunctionalization and functional divergence. BMC plant biology. 2010 May; 10(?):100. doi: 10.1186/1471-2229-10-100. [PMID: 20509918]
  • Ann M Patten, Michaël Jourdes, Claudia L Cardenas, Dhrubojyoti D Laskar, Yoshihisa Nakazawa, Byung-Yeoup Chung, Vincent R Franceschi, Laurence B Davin, Norman G Lewis. Probing native lignin macromolecular configuration in Arabidopsis thaliana in specific cell wall types: further insights into limited substrate degeneracy and assembly of the lignins of ref8, fah 1-2 and C4H::F5H lines. Molecular bioSystems. 2010 Mar; 6(3):499-515. doi: 10.1039/b819206e. [PMID: 20174679]
  • Everton A Brenner, Imad Zein, Yongsheng Chen, Jeppe R Andersen, Gerhard Wenzel, Milena Ouzunova, Joachim Eder, Birte Darnhofer, Uschi Frei, Yves Barrière, Thomas Lübberstedt. Polymorphisms in O-methyltransferase genes are associated with stover cell wall digestibility in European maize (Zea mays L.). BMC plant biology. 2010 Feb; 10(?):27. doi: 10.1186/1471-2229-10-27. [PMID: 20152036]
  • Seiji Yamasaki, Eri Shimada, Tomoe Kuwano, Tae Kawano, Naoto Noguchi. Continuous UV-B irradiation induces endoreduplication and peroxidase activity in epidermal cells surrounding trichomes on cucumber cotyledons. Journal of radiation research. 2010; 51(2):187-96. doi: 10.1269/jrr.09101. [PMID: 20110622]
  • Suvi Sutela, Karoliina Niemi, Jaanika Edesi, Tapio Laakso, Pekka Saranpää, Jaana Vuosku, Riina Mäkelä, Heidi Tiimonen, Vincent L Chiang, Janne Koskimäki, Marja Suorsa, Riitta Julkunen-Tiitto, Hely Häggman. Phenolic compounds in ectomycorrhizal interaction of lignin modified silver birch. BMC plant biology. 2009 Sep; 9(?):124. doi: 10.1186/1471-2229-9-124. [PMID: 19788757]
  • Marcello Iriti, Franco Faoro. Chemical diversity and defence metabolism: how plants cope with pathogens and ozone pollution. International journal of molecular sciences. 2009 Jul; 10(8):3371-3399. doi: 10.3390/ijms10083371. [PMID: 20111684]
  • Jaclyn J Stewart, Takuya Akiyama, Clint Chapple, John Ralph, Shawn D Mansfield. The effects on lignin structure of overexpression of ferulate 5-hydroxylase in hybrid poplar. Plant physiology. 2009 Jun; 150(2):621-35. doi: 10.1104/pp.109.137059. [PMID: 19386808]
  • Abdelali Barakat, Agnieszka Bagniewska-Zadworna, Alex Choi, Urmila Plakkat, Denis S DiLoreto, Priyadarshini Yellanki, John E Carlson. The cinnamyl alcohol dehydrogenase gene family in Populus: phylogeny, organization, and expression. BMC plant biology. 2009 Mar; 9(?):26. doi: 10.1186/1471-2229-9-26. [PMID: 19267902]
  • Esther Novo Uzal, Laura V Gómez Ros, Federico Pomar, María A Bernal, Alberto Paradela, Juan P Albar, Alfonso Ros Barceló. The presence of sinapyl lignin in Ginkgo biloba cell cultures changes our views of the evolution of lignin biosynthesis. Physiologia plantarum. 2009 Feb; 135(2):196-213. doi: 10.1111/j.1399-3054.2008.01185.x. [PMID: 19055540]
  • Michaël Quentin, Valérie Allasia, Anthony Pegard, Florent Allais, Paul-Henri Ducrot, Bruno Favery, Caroline Levis, Sophie Martinet, Clarissa Masur, Michel Ponchet, Dominique Roby, Nikolaus L Schlaich, Lise Jouanin, Harald Keller. Imbalanced lignin biosynthesis promotes the sexual reproduction of homothallic oomycete pathogens. PLoS pathogens. 2009 Jan; 5(1):e1000264. doi: 10.1371/journal.ppat.1000264. [PMID: 19148278]
  • Nazmul H Bhuiyan, Gopalan Selvaraj, Yangdou Wei, John King. Gene expression profiling and silencing reveal that monolignol biosynthesis plays a critical role in penetration defence in wheat against powdery mildew invasion. Journal of experimental botany. 2009; 60(2):509-21. doi: 10.1093/jxb/ern290. [PMID: 19039100]
  • Ronald Hatfield, John Ralph, John H Grabber. A potential role for sinapyl p-coumarate as a radical transfer mechanism in grass lignin formation. Planta. 2008 Nov; 228(6):919-28. doi: 10.1007/s00425-008-0791-4. [PMID: 18654797]
  • Alexandra Lanot, Denise Hodge, Eng-Kiat Lim, Fabián E Vaistij, Dianna J Bowles. Redirection of flux through the phenylpropanoid pathway by increased glucosylation of soluble intermediates. Planta. 2008 Sep; 228(4):609-16. doi: 10.1007/s00425-008-0763-8. [PMID: 18563437]
  • Sabine Guillaumie, Deborah Goffner, Odile Barbier, Jean-Pierre Martinant, Magalie Pichon, Yves Barrière. Expression of cell wall related genes in basal and ear internodes of silking brown-midrib-3, caffeic acid O-methyltransferase (COMT) down-regulated, and normal maize plants. BMC plant biology. 2008 Jun; 8(?):71. doi: 10.1186/1471-2229-8-71. [PMID: 18582385]
  • Anna Aksamit-Stachurska, Alina Korobczak-Sosna, Anna Kulma, Jan Szopa. Glycosyltransferase efficiently controls phenylpropanoid pathway. BMC biotechnology. 2008 Mar; 8(?):25. doi: 10.1186/1472-6750-8-25. [PMID: 18321380]
  • Shinya Sasaki, Daisuke Nonaka, Hiroyuki Wariishi, Yuji Tsutsumi, Ryuichiro Kondo. Role of Tyr residues on the protein surface of cationic cell-wall-peroxidase (CWPO-C) from poplar: potential oxidation sites for oxidative polymerization of lignin. Phytochemistry. 2008 Jan; 69(2):348-55. doi: 10.1016/j.phytochem.2007.08.020. [PMID: 17910963]
  • Alfonso Ros Barceló, Laura V Gómez Ros, Alberto Esteban Carrasco. Looking for syringyl peroxidases. Trends in plant science. 2007 Nov; 12(11):486-491. doi: 10.1016/j.tplants.2007.09.002. [PMID: 17928259]
  • Gordon V Louie, Thomas J Baiga, Marianne E Bowman, Takao Koeduka, John H Taylor, Snejina M Spassova, Eran Pichersky, Joseph P Noel. Structure and reaction mechanism of basil eugenol synthase. PloS one. 2007 Oct; 2(10):e993. doi: 10.1371/journal.pone.0000993. [PMID: 17912370]
  • Laura V Gómez Ros, Ginés J Aznar-Asensio, Jose A Hernandez, Maria A Bernal, María J L Núñez-Flores, Juan Cuello, Alfonso Ros Barceló. Structural motifs of syringyl peroxidases are conserved during angiosperm evolution. Journal of agricultural and food chemistry. 2007 May; 55(10):4131-8. doi: 10.1021/jf063164t. [PMID: 17439232]
  • Shinya Sasaki, Kei'ichi Baba, Tomoaki Nishida, Yuji Tsutsumi, Ryuichiro Kondo. The cationic cell-wall-peroxidase having oxidation ability for polymeric substrate participates in the late stage of lignification of Populus alba L. Plant molecular biology. 2006 Dec; 62(6):797-807. doi: 10.1007/s11103-006-9057-3. [PMID: 17004015]
  • Aymerick Eudes, Brigitte Pollet, Richard Sibout, Cao-Trung Do, Armand Séguin, Catherine Lapierre, Lise Jouanin. Evidence for a role of AtCAD 1 in lignification of elongating stems of Arabidopsis thaliana. Planta. 2006 Dec; 225(1):23-39. doi: 10.1007/s00425-006-0326-9. [PMID: 16832689]
  • 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]
  • Alexandra Lanot, Denise Hodge, Rosamond G Jackson, Gilu L George, Luisa Elias, Eng-Kiat Lim, Fabián E Vaistij, Dianna J Bowles. The glucosyltransferase UGT72E2 is responsible for monolignol 4-O-glucoside production in Arabidopsis thaliana. The Plant journal : for cell and molecular biology. 2006 Oct; 48(2):286-95. doi: 10.1111/j.1365-313x.2006.02872.x. [PMID: 16995900]
  • Carlos Gabaldón, Matías López-Serrano, Federico Pomar, Fuencisla Merino, Juan Cuello, M A Pedreño, A Ros Barceló. Characterization of the last step of lignin biosynthesis in Zinnia elegans suspension cell cultures. FEBS letters. 2006 Aug; 580(18):4311-6. doi: 10.1016/j.febslet.2006.06.088. [PMID: 16842784]
  • C Hano, M Addi, L Bensaddek, D Crônier, S Baltora-Rosset, J Doussot, S Maury, F Mesnard, B Chabbert, S Hawkins, E Lainé, F Lamblin. Differential accumulation of monolignol-derived compounds in elicited flax (Linum usitatissimum) cell suspension cultures. Planta. 2006 Apr; 223(5):975-89. doi: 10.1007/s00425-005-0156-1. [PMID: 16292660]
  • Yasushi Sato, Taku Demura, Ken Yamawaki, Yukina Inoue, Seiichi Sato, Munetaka Sugiyama, Hiroo Fukuda. Isolation and characterization of a novel peroxidase gene ZPO-C whose expression and function are closely associated with lignification during tracheary element differentiation. Plant & cell physiology. 2006 Apr; 47(4):493-503. doi: 10.1093/pcp/pcj016. [PMID: 16446311]
  • Hong Bin Zou, Sheng Yi Dong, Chang Xin Zhou, Li Hong Hu, Yi Hang Wu, Hai Bo Li, Jing Xu Gong, Lian Li Sun, Xiu Mei Wu, Hua Bai, Bo Tao Fan, Xiao Jiang Hao, Joachim Stöckigt, Yu Zhao. Design, synthesis, and SAR analysis of cytotoxic sinapyl alcohol derivatives. Bioorganic & medicinal chemistry. 2006 Mar; 14(6):2060-71. doi: 10.1016/j.bmc.2005.10.056. [PMID: 16303311]
  • Carlos Gabaldón, Matías López-Serrano, María A Pedreño, A Ros Barceló. Cloning and molecular characterization of the basic peroxidase isoenzyme from Zinnia elegans, an enzyme involved in lignin biosynthesis. Plant physiology. 2005 Nov; 139(3):1138-54. doi: 10.1104/pp.105.069674. [PMID: 16258008]
  • 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]
  • Erin K Bomati, Joseph P Noel. Structural and kinetic basis for substrate selectivity in Populus tremuloides sinapyl alcohol dehydrogenase. The Plant cell. 2005 May; 17(5):1598-611. doi: 10.1105/tpc.104.029983. [PMID: 15829607]
  • Jongwon Choi, Kyoung-Min Shin, Hee-Juhn Park, Hyun-Ju Jung, Hyoung Ja Kim, Yong Sup Lee, Jae-Hwan Rew, Kyung-Tae Lee. Anti-inflammatory and antinociceptive effects of sinapyl alcohol and its glucoside syringin. Planta medica. 2004 Nov; 70(11):1027-32. doi: 10.1055/s-2004-832642. [PMID: 15549657]
  • Kris Morreel, John Ralph, Hoon Kim, Fachuang Lu, Geert Goeminne, Sally Ralph, Eric Messens, Wout Boerjan. Profiling of oligolignols reveals monolignol coupling conditions in lignifying poplar xylem. Plant physiology. 2004 Nov; 136(3):3537-49. doi: 10.1104/pp.104.049304. [PMID: 15516504]
  • 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]
  • Kazuchika Yamauchi, Kazuhiko Fukushima. The regulation from guaiacyl to syringyl lignin in the differentiating xylem of Robinia pseudoacacia. Comptes rendus biologies. 2004 Sep; 327(9-10):791-7. doi: 10.1016/j.crvi.2004.07.012. [PMID: 15587070]
  • Hua-Yan Zhao, Jian-Hua Wei, Yan-Ru Song. [Advances in research on lignin biosynthesis and its genetic engineering]. Zhi wu sheng li yu fen zi sheng wu xue xue bao = Journal of plant physiology and molecular biology. 2004 Aug; 30(4):361-70. doi: ". [PMID: 15627683]
  • 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]
  • Ramesh B Nair, Kristen L Bastress, Max O Ruegger, Jeff W Denault, Clint Chapple. The Arabidopsis thaliana REDUCED EPIDERMAL FLUORESCENCE1 gene encodes an aldehyde dehydrogenase involved in ferulic acid and sinapic acid biosynthesis. The Plant cell. 2004 Feb; 16(2):544-54. doi: 10.1105/tpc.017509. [PMID: 14729911]
  • Richard Sibout, Aymerick Eudes, Brigitte Pollet, Thomas Goujon, Isabelle Mila, Fabienne Granier, Armand Séguin, Catherine Lapierre, Lise Jouanin. Expression pattern of two paralogs encoding cinnamyl alcohol dehydrogenases in Arabidopsis. Isolation and characterization of the corresponding mutants. Plant physiology. 2003 Jun; 132(2):848-60. doi: 10.1104/pp.103.021048. [PMID: 12805615]
  • Jeffrey S Amthor. Efficiency of lignin biosynthesis: a quantitative analysis. Annals of botany. 2003 May; 91(6):673-95. doi: 10.1093/aob/mcg073. [PMID: 12714366]
  • M S Kamel. Acylated phenolic glycosides from Solenostemma argel. Phytochemistry. 2003 Apr; 62(8):1247-50. doi: 10.1016/s0031-9422(03)00022-0. [PMID: 12648546]
  • Kazuchika Yamauchi, Seiichi Yasuda, Katsuyoshi Hamada, Yuji Tsutsumi, Kazuhiko Fukushima. Multiform biosynthetic pathway of syringyl lignin in angiosperms. Planta. 2003 Jan; 216(3):496-501. doi: 10.1007/s00425-002-0865-7. [PMID: 12520342]
  • Aldwin M Anterola, Norman G Lewis. Trends in lignin modification: a comprehensive analysis of the effects of genetic manipulations/mutations on lignification and vascular integrity. Phytochemistry. 2002 Oct; 61(3):221-94. doi: 10.1016/s0031-9422(02)00211-x. [PMID: 12359514]
  • F Pomar, F Merino, A Ros Barceló. O-4-Linked coniferyl and sinapyl aldehydes in lignifying cell walls are the main targets of the Wiesner (phloroglucinol-HCl) reaction. Protoplasma. 2002 Oct; 220(1-2):17-28. doi: 10.1007/s00709-002-0030-y. [PMID: 12417933]
  • Yu Zhao, Xiaojiang Hao, Wei Lu, Junchao Cai, Hong Yu, Thierry Sevénet, Françoise Guéritte. Syntheses of two cytotoxic sinapyl alcohol derivatives and isolation of four new related compounds from Ligularia nelumbifolia. Journal of natural products. 2002 Jun; 65(6):902-8. doi: 10.1021/np0200257. [PMID: 12088436]