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Chemical Compound Review

SureCN15674     3-(4-hydroxy-3-methoxy- phenyl)prop-2-enoic...

Synonyms: AGN-PC-006IKU, CCRIS 3256, AG-B-93738, AG-L-23561, KBioGR_002459, ...
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Disease relevance of Coniferic acid


Psychiatry related information on Coniferic acid

  • Overall, our results predict that a treatment using nitric oxide-releasing ferulic acid may attenuate the processes that drive the pathology associated with Alzheimer's disease if the treatment is initiated before the neuroinflammatory processes can develop [6].
  • We recently reported protective effects of long-term administration of ferulic acid against learning and memory deficit induced by centrally administered beta-amyloid peptide (Abeta)1-42 in mice [7].

High impact information on Coniferic acid

  • The encoded enzyme, At4CL4, exhibits the rare property of efficiently activating sinapate, besides the usual 4CL substrates (4-coumarate, caffeate, and ferulate), indicating a distinct metabolic function [8].
  • Although the CAld5H/COMT enzyme system can mediate the biosynthesis of syringyl monolignol intermediates through either route, k(cat)/K(m) of CAld5H for coniferyl aldehyde was approximately 140 times greater than that for ferulate [9].
  • Unexpectedly, the K(m) values measured for the latter two substrates are three orders of magnitude lower than that measured for ferulic acid, suggesting that in lignifying tissues, syringyl monomers may be derived from their guaiacyl counterparts by hydroxylation and subsequent methylation [10].
  • The effects of topically applied curcumin, chlorogenic acid, caffeic acid, and ferulic acid on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced epidermal ornithine decarboxylase activity, epidermal DNA synthesis, and the promotion of skin tumors were evaluated in female CD-1 mice [11].
  • Ferulic acid (FA) is an abundantly present phenolic constituent of plant cell walls [12].

Chemical compound and disease context of Coniferic acid


Biological context of Coniferic acid


Anatomical context of Coniferic acid


Associations of Coniferic acid with other chemical compounds

  • Feruloyl-SCoA is the CoASH thioester of ferulic acid (4-hydroxy-3-methoxy-trans-cinnamic acid), an abundant constituent of plant cell walls and a degradation product of lignin [27].
  • Ferulic acid was far more toxic than caffeic acid to the wild-type strain, although the wild-type strain was more resistant to ferulic acid than was the virH mutant [20].
  • Quantum mechanics/molecular mechanics calculations were utilized to study the process of oxidation of a native substrate (ferulic acid) by the active species of horseradish peroxidase (Dunford, H. B. Heme Peroxidases; Wiley-VCH: New York, 1999), Compound I and Compound II, and the manner by which the enzyme returns to its resting state [28].
  • Xylan, which is a key component of the plant cell wall, consists of a backbone of beta-1,4-linked xylose residues that are decorated with arabinofuranose, acetyl, 4-O-methyl d-glucuronic acid and ferulate [29].
  • Despite its ability to accumulate UV-absorptive flavonoid compounds, the ferulic acid hydroxylase mutant fah1 exhibits more physiological injury (growth inhibition and foliar lesions) than either wild type or tt5 [30].

Gene context of Coniferic acid


Analytical, diagnostic and therapeutic context of Coniferic acid


  1. Human endogenous retrovirus glycoprotein-mediated induction of redox reactants causes oligodendrocyte death and demyelination. Antony, J.M., van Marle, G., Opii, W., Butterfield, D.A., Mallet, F., Yong, V.W., Wallace, J.L., Deacon, R.M., Warren, K., Power, C. Nat. Neurosci. (2004) [Pubmed]
  2. A nontransformable Triticum monococcum monocotyledonous culture produces the potent Agrobacterium vir-inducing compound ethyl ferulate. Messens, E., Dekeyser, R., Stachel, S.E. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  3. Investigation of the potential of capillary electrophoresis with off-line matrix-assisted laser desorption/ionization time-of-flight mass spectrometry for clinical analysis: examination of a glycoprotein factor associated with cancer cachexia. Choudhary, G., Chakel, J., Hancock, W., Torres-Duarte, A., McMahon, G., Wainer, I. Anal. Chem. (1999) [Pubmed]
  4. Biochemical and genetic analyses of ferulic acid catabolism in Pseudomonas sp. Strain HR199. Overhage, J., Priefert, H., Steinbüchel, A. Appl. Environ. Microbiol. (1999) [Pubmed]
  5. Protection against beta-amyloid peptide toxicity in vivo with long-term administration of ferulic acid. Yan, J.J., Cho, J.Y., Kim, H.S., Kim, K.L., Jung, J.S., Huh, S.O., Suh, H.W., Kim, Y.H., Song, D.K. Br. J. Pharmacol. (2001) [Pubmed]
  6. Attenuation of chronic neuroinflammation by a nitric oxide-releasing derivative of the antioxidant ferulic acid. Wenk, G.L., McGann-Gramling, K., Hauss-Wegrzyniak, B., Ronchetti, D., Maucci, R., Rosi, S., Gasparini, L., Ongini, E. J. Neurochem. (2004) [Pubmed]
  7. Inhibitory effects of long-term administration of ferulic acid on astrocyte activation induced by intracerebroventricular injection of beta-amyloid peptide (1-42) in mice. Cho, J.Y., Kim, H.S., Kim, D.H., Yan, J.J., Suh, H.W., Song, D.K. Prog. Neuropsychopharmacol. Biol. Psychiatry (2005) [Pubmed]
  8. The 4-coumarate:CoA ligase gene family in Arabidopsis thaliana comprises one rare, sinapate-activating and three commonly occurring isoenzymes. Hamberger, B., Hahlbrock, K. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  9. Coniferyl aldehyde 5-hydroxylation and methylation direct syringyl lignin biosynthesis in angiosperms. Osakabe, K., Tsao, C.C., Li, L., Popko, J.L., Umezawa, T., Carraway, D.T., Smeltzer, R.H., Joshi, C.P., Chiang, V.L. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  10. New routes for lignin biosynthesis defined by biochemical characterization of recombinant ferulate 5-hydroxylase, a multifunctional cytochrome P450-dependent monooxygenase. Humphreys, J.M., Hemm, M.R., Chapple, C. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  11. Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate. Huang, M.T., Smart, R.C., Wong, C.Q., Conney, A.H. Cancer Res. (1988) [Pubmed]
  12. Horseradish peroxidase-catalyzed oligomerization of ferulic acid on a template of a tyrosine-containing tripeptide. Oudgenoeg, G., Dirksen, E., Ingemann, S., Hilhorst, R., Gruppen, H., Boeriu, C.G., Piersma, S.R., van Berkel, W.J., Laane, C., Voragen, A.G. J. Biol. Chem. (2002) [Pubmed]
  13. Toxicity caused by hydroxycinnamoyl-coenzyme A thioester accumulation in mutants of Acinetobacter sp. strain ADP1. Parke, D., Ornston, L.N. Appl. Environ. Microbiol. (2004) [Pubmed]
  14. Genetic analysis of a chromosomal region containing vanA and vanB, genes required for conversion of either ferulate or vanillate to protocatechuate in Acinetobacter. Segura, A., Bünz, P.V., D'Argenio, D.A., Ornston, L.N. J. Bacteriol. (1999) [Pubmed]
  15. Cloning and characterization of the ferulic acid catabolic genes of Sphingomonas paucimobilis SYK-6. Masai, E., Harada, K., Peng, X., Kitayama, H., Katayama, Y., Fukuda, M. Appl. Environ. Microbiol. (2002) [Pubmed]
  16. Biotransformation of eugenol to ferulic acid by a recombinant strain of Ralstonia eutropha H16. Overhage, J., Steinbüchel, A., Priefert, H. Appl. Environ. Microbiol. (2002) [Pubmed]
  17. An Aspergillus niger esterase (ferulic acid esterase III) and a recombinant Pseudomonas fluorescens subsp. cellulosa esterase (Xy1D) release a 5-5' ferulic dehydrodimer (diferulic acid) from barley and wheat cell walls. Bartolomé, B., Faulds, C.B., Kroon, P.A., Waldron, K., Gilbert, H.J., Hazlewood, G., Williamson, G. Appl. Environ. Microbiol. (1997) [Pubmed]
  18. Initial steps of ferulic acid polymerization by lignin peroxidase. Ward, G., Hadar, Y., Bilkis, I., Konstantinovsky, L., Dosoretz, C.G. J. Biol. Chem. (2001) [Pubmed]
  19. Identification of the substrate specificity-conferring amino acid residues of 4-coumarate:coenzyme A ligase allows the rational design of mutant enzymes with new catalytic properties. Stuible, H.P., Kombrink, E. J. Biol. Chem. (2001) [Pubmed]
  20. The phenolic vir gene inducer ferulic acid is O-demethylated by the VirH2 protein of an Agrobacterium tumefaciens Ti plasmid. Kalogeraki, V.S., Zhu, J., Eberhard, A., Madsen, E.L., Winans, S.C. Mol. Microbiol. (1999) [Pubmed]
  21. Effects of ferulic acid on fertile and asthenozoospermic infertile human sperm motility, viability, lipid peroxidation, and cyclic nucleotides. Zheng, R.L., Zhang, H. Free Radic. Biol. Med. (1997) [Pubmed]
  22. The bioavailability of ferulic acid is governed primarily by the food matrix rather than its metabolism in intestine and liver in rats. Adam, A., Crespy, V., Levrat-Verny, M.A., Leenhardt, F., Leuillet, M., Demigné, C., Rémésy, C. J. Nutr. (2002) [Pubmed]
  23. Characterization of potentially chemopreventive phenols in extracts of brown rice that inhibit the growth of human breast and colon cancer cells. Hudson, E.A., Dinh, P.A., Kokubun, T., Simmonds, M.S., Gescher, A. Cancer Epidemiol. Biomarkers Prev. (2000) [Pubmed]
  24. Interaction of ferulic acid derivatives with human erythrocytes monitored by pulse field gradient NMR diffusion and NMR relaxation studies. Anselmi, C., Bernardi, F., Centini, M., Gaggelli, E., Gaggelli, N., Valensin, D., Valensin, G. Chem. Phys. Lipids (2005) [Pubmed]
  25. Ferulic acid inhibits endothelial cell proliferation through NO down-regulating ERK1/2 pathway. Hou, Y., Yang, J., Zhao, G., Yuan, Y. J. Cell. Biochem. (2004) [Pubmed]
  26. Protective effect of ferulic acid on gamma-radiation-induced micronuclei, dicentric aberration and lipid peroxidation in human lymphocytes. Prasad, N.R., Srinivasan, M., Pugalendi, K.V., Menon, V.P. Mutat. Res. (2006) [Pubmed]
  27. Metabolism of ferulic acid to vanillin. A bacterial gene of the enoyl-SCoA hydratase/isomerase superfamily encodes an enzyme for the hydration and cleavage of a hydroxycinnamic acid SCoA thioester. Gasson, M.J., Kitamura, Y., McLauchlan, W.R., Narbad, A., Parr, A.J., Parsons, E.L., Payne, J., Rhodes, M.J., Walton, N.J. J. Biol. Chem. (1998) [Pubmed]
  28. An Efficient Proton-Coupled Electron-Transfer Process during Oxidation of Ferulic Acid by Horseradish Peroxidase: Coming Full Cycle. Derat, E., Shaik, S. J. Am. Chem. Soc. (2006) [Pubmed]
  29. A family 10 Thermoascus aurantiacus xylanase utilizes arabinose decorations of xylan as significant substrate specificity determinants. Vardakou, M., Flint, J., Christakopoulos, P., Lewis, R.J., Gilbert, H.J., Murray, J.W. J. Mol. Biol. (2005) [Pubmed]
  30. Arabidopsis mutants lacking phenolic sunscreens exhibit enhanced ultraviolet-B injury and oxidative damage. Landry, L.G., Chapple, C.C., Last, R.L. Plant Physiol. (1995) [Pubmed]
  31. A non-modular type B feruloyl esterase from Neurospora crassa exhibits concentration-dependent substrate inhibition. Crepin, V.F., Faulds, C.B., Connerton, I.F. Biochem. J. (2003) [Pubmed]
  32. Modulation of HER2 expression by ferulic acid on human breast cancer MCF7 cells. Chang, C.J., Chiu, J.H., Tseng, L.M., Chang, C.H., Chien, T.M., Wu, C.W., Lui, W.Y. Eur. J. Clin. Invest. (2006) [Pubmed]
  33. Effect of overexpression of Saccharomyces cerevisiae Pad1p on the resistance to phenylacrylic acids and lignocellulose hydrolysates under aerobic and oxygen-limited conditions. Larsson, S., Nilvebrant, N.O., Jönsson, L.J. Appl. Microbiol. Biotechnol. (2001) [Pubmed]
  34. Sodium ferulate prevents amyloid-beta-induced neurotoxicity through suppression of p38 MAPK and upregulation of ERK-1/2 and Akt/protein kinase B in rat hippocampus. Jin, Y., Yan, E.Z., Fan, Y., Zong, Z.H., Qi, Z.M., Li, Z. Acta Pharmacol. Sin. (2005) [Pubmed]
  35. Ferulic acid excretion as a marker of consumption of a French maritime pine (Pinus maritima) bark extract. Virgili, F., Pagana, G., Bourne, L., Rimbach, G., Natella, F., Rice-Evans, C., Packer, L. Free Radic. Biol. Med. (2000) [Pubmed]
  36. Purification and characterization of a ferulic acid decarboxylase from Pseudomonas fluorescens. Huang, Z., Dostal, L., Rosazza, J.P. J. Bacteriol. (1994) [Pubmed]
  37. Microbial transformations of ferulic acid by Saccharomyces cerevisiae and Pseudomonas fluorescens. Huang, Z., Dostal, L., Rosazza, J.P. Appl. Environ. Microbiol. (1993) [Pubmed]
  38. Ferulic acid inhibits vascular smooth muscle cell proliferation induced by angiotensin II. Hou, Y.Z., Yang, J., Zhao, G.R., Yuan, Y.J. Eur. J. Pharmacol. (2004) [Pubmed]
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