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Chemical Compound Review:

CHEBI:20582 (E)-3-(3,4-dihydroxy-5- methoxy-phenyl)prop...

Synonyms: SureCN10085810, AC1L9K5E, C05619, 1782-55-4, 2041-35-2, ...

Humphreys, J.M. et al., Costa, M.A. et al., Kota, P. et al., Zubieta, C. et al., Maury, S. et al., et al.

Zhang, Wang, Goodman, Sugimoto, Okada, Sato, Ito, Takeda,

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Disease relevance of 5-Hydroxyferulic acid

Aspen lignin-specific caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase (EC 1.2.1.68) was expressed in an active form in Escherichia coli using pET-23 vector [1].

High impact information on 5-Hydroxyferulic acid

Caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase (COMT) from alfalfa is an S-adenosyl-L-Met-dependent O-methyltransferase involved in lignin biosynthesis [2].
Structural basis for the modulation of lignin monomer methylation by caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase [2].
To further test this model, recombinant F5H was incubated together with ferulic acid, coniferaldehyde, or coniferyl alcohol in the presence of native or recombinant Arabidopsis caffeic acid/5-hydroxyferulic acid O-methyltransferase and [(14)C]S-adenosylmethionine [3].
Nucleotide sequence of a Populus tremuloides gene encoding bispecific caffeic acid/5-hydroxyferulic acid O-methyltransferase [4].
cDNA cloning, sequence analysis and seasonal expression of lignin-bispecific caffeic acid/5-hydroxyferulic acid O-methyltransferase of aspen [5].

Biological context of 5-Hydroxyferulic acid

The deduced amino acid sequence showed significant identity with plant caffeic acid/5-hydroxyferulic acid OMTs [6].

Associations of 5-Hydroxyferulic acid with other chemical compounds

The biosynthesis of lignin monomers involves two methylation steps catalyzed by orthodiphenol-O-methyltransferases: caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferases (COMTs) and caffeoyl-coenzyme A (CoA)/5-hydroxyferuloyl-CoA 3/5-O-methyltransferases (CCoAOMTs) [7].
Lastly, although At4CL5 is able to convert both 5-hydroxyferulic and sinapic acids into the corresponding CoA esters, the physiological significance of the latter observation in vitro was in question, i.e. particularly since other 4CL isoforms can effectively convert 5-hydroxyferulic acid into 5-hydroxyferuloyl CoA [8].
Although S-adenosyl-l-methionine (SAM) dependent caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase (COMT) is one of the key enzymes in lignin biosynthesis, the present work demonstrates that alfalfa COMT methylates benzaldehyde derivatives more efficiently than lignin pathway intermediates [9].

Gene context of 5-Hydroxyferulic acid

Indeed, both At4CL1 and At4CL5 most effectively utilized 5-hydroxyferulic acid with kenz approximately 10-fold higher than that for At4CL2 and At4CL3 [8].
A caffeic acid/5-hydroxyferulic acid O-methyltransferase, OMT1, was identified as one of the several proteins that specifically interacts with AFT1 in yeast cells [10].

References

Characterization and site-directed mutagenesis of aspen lignin-specific O-methyltransferase expressed in Escherichia coli. Meng, H., Campbell, W.H. Arch. Biochem. Biophys. (1996) [Pubmed]
Structural basis for the modulation of lignin monomer methylation by caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase. Zubieta, C., Kota, P., Ferrer, J.L., Dixon, R.A., Noel, J.P. Plant Cell (2002) [Pubmed]
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]
Nucleotide sequence of a Populus tremuloides gene encoding bispecific caffeic acid/5-hydroxyferulic acid O-methyltransferase. Tsai, C.J., Podila, G.K., Chiang, V.L. Plant Physiol. (1995) [Pubmed]
cDNA cloning, sequence analysis and seasonal expression of lignin-bispecific caffeic acid/5-hydroxyferulic acid O-methyltransferase of aspen. Bugos, R.C., Chiang, V.L., Campbell, W.H. Plant Mol. Biol. (1991) [Pubmed]
A root-specific O-methyltransferase gene expressed in salt-tolerant barley. Sugimoto, M., Okada, Y., Sato, K., Ito, K., Takeda, K. Biosci. Biotechnol. Biochem. (2003) [Pubmed]
Tobacco O-methyltransferases involved in phenylpropanoid metabolism. The different caffeoyl-coenzyme A/5-hydroxyferuloyl-coenzyme A 3/5-O-methyltransferase and caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase classes have distinct substrate specificities and expression patterns. Maury, S., Geoffroy, P., Legrand, M. Plant Physiol. (1999) [Pubmed]
Characterization in vitro and in vivo of the putative multigene 4-coumarate:CoA ligase network in Arabidopsis: syringyl lignin and sinapate/sinapyl alcohol derivative formation. Costa, M.A., Bedgar, D.L., Moinuddin, S.G., Kim, K.W., Cardenas, C.L., Cochrane, F.C., Shockey, J.M., Helms, G.L., Amakura, Y., Takahashi, H., Milhollan, J.K., Davin, L.B., Browse, J., Lewis, N.G. Phytochemistry (2005) [Pubmed]
O-Methylation of benzaldehyde derivatives by "lignin specific" caffeic acid 3-O-methyltransferase. Kota, P., Guo, D., Zubieta, C., Noel, J., Dixon, R.A. Phytochemistry (2004) [Pubmed]
An Arabidopsis gene encoding a putative 14-3-3-interacting protein, caffeic acid/5-hydroxyferulic acid O-methyltransferase. Zhang, H., Wang, J., Goodman, H.M. Biochim. Biophys. Acta (1997) [Pubmed]

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