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Chemical Compound Review:

Sinapaldehyde (E)-3-(4-hydroxy-3,5- dimethoxy-phenyl)prop...

Synonyms: AC1NQXM5, CHEMBL225067, CHEBI:27949, bmse000606, bmse010085, ...

Li, L. et al., Zhang, K. et al., Kim, S.J. et al., Nair, R.B. et al., Bomati, E.K. et al., et al.

Panossian, Mamikonyan, Torosyan, Gabrielyan, Mkhitaryan,

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Disease relevance of Sinapoyl aldehyde

COMT expressed in Escherichia coli methylated 5-hydroxyconiferyl aldehyde to sinapyl aldehyde [1].

High impact information on Sinapoyl aldehyde

The active site topology revealed by the crystal structure substantiates kinetic results indicating that SAD maintains highest specificity for the substrate sinapaldehyde [2].
These data indicate that REF1 encodes a sinapaldehyde dehydrogenase required for sinapic acid and sinapate ester biosynthesis [3].
Cinnamyl alcohol dehydrogenase (CAD; EC 1.1.1.195) has been thought to mediate the reduction of both coniferaldehyde and sinapaldehyde into guaiacyl and syringyl monolignols in angiosperms [4].
Liquid chromatography-mass spectrometry-based enzyme functional analysis and substrate level-controlled enzyme kinetics consistently demonstrated that PtSAD is sinapaldehyde specific and that PtCAD is coniferaldehyde specific [4].
AtCAD5 used all five substrates effectively, whereas AtCAD4 (of lower overall catalytic capacity) poorly used sinapyl aldehyde; the corresponding 270-fold decrease in k(enz) resulted from higher K(m) and lower k(cat) values, respectively [5].

Chemical compound and disease context of Sinapoyl aldehyde

When expressed in Escherichia coli, purified recombinant GH2 was found to exhibit strong catalytic ability toward coniferaldehyde and sinapaldehyde, while the mutant protein gh2 completely lost the corresponding CAD and sinapyl alcohol dehydrogenase activities [6].

Anatomical context of Sinapoyl aldehyde

Coniferaldehyde and sinapaldehyde inhibited electrically induced contractions of the guinea pig ileum in a dose-dependent way [7].

Associations of Sinapoyl aldehyde with other chemical compounds

A new method of analysis of vanillin, syringaldehyde, coniferaldehyde, and sinapaldehyde in brandy and wine by high-performance capillary electrophoresis is described [8].
Initial steps of the peroxidase-catalyzed polymerization of coniferyl alcohol and/or sinapyl aldehyde: capillary zone electrophoresis study of pH effect [9].

Gene context of Sinapoyl aldehyde

Consistent with this finding, extracts of ref1 leaves exhibit low sinapaldehyde dehydrogenase activity [3].

References

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]
Structural and kinetic basis for substrate selectivity in Populus tremuloides sinapyl alcohol dehydrogenase. Bomati, E.K., Noel, J.P. Plant Cell (2005) [Pubmed]
The Arabidopsis thaliana REDUCED EPIDERMAL FLUORESCENCE1 gene encodes an aldehyde dehydrogenase involved in ferulic acid and sinapic acid biosynthesis. Nair, R.B., Bastress, K.L., Ruegger, M.O., Denault, J.W., Chapple, C. Plant Cell (2004) [Pubmed]
The last step of syringyl monolignol biosynthesis in angiosperms is regulated by a novel gene encoding sinapyl alcohol dehydrogenase. Li, L., Cheng, X.F., Leshkevich, J., Umezawa, T., Harding, S.A., Chiang, V.L. Plant Cell (2001) [Pubmed]
Functional reclassification of the putative cinnamyl alcohol dehydrogenase multigene family in Arabidopsis. Kim, S.J., Kim, M.R., Bedgar, D.L., Moinuddin, S.G., Cardenas, C.L., Davin, L.B., Kang, C., Lewis, N.G. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
GOLD HULL AND INTERNODE2 encodes a primarily multifunctional cinnamyl-alcohol dehydrogenase in rice. Zhang, K., Qian, Q., Huang, Z., Wang, Y., Li, M., Hong, L., Zeng, D., Gu, M., Chu, C., Cheng, Z. Plant Physiol. (2006) [Pubmed]
Pharmacologically active phenylpropanoids from Senra incana. Farah, M.H., Samuelsson, G. Planta Med. (1992) [Pubmed]
Analysis of aromatic aldehydes in brandy and wine by high-performance capillary electrophoresis. Panossian, A., Mamikonyan, G., Torosyan, M., Gabrielyan, E., Mkhitaryan, S. Anal. Chem. (2001) [Pubmed]
Initial steps of the peroxidase-catalyzed polymerization of coniferyl alcohol and/or sinapyl aldehyde: capillary zone electrophoresis study of pH effect. Fournand, D., Cathala, B., Lapierre, C. Phytochemistry (2003) [Pubmed]

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