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Coniferyl aldehyde

Coniferyl aldehyde is an organic compound with the formula HO(CH3O)C6H3CH=CHCHO. It is a derivative of cinnamaldehyde, featuring 4-hydroxy and 3-methoxy substituents. It is a major precursor to lignin.[1][2]

Biosynthetic role

In sweetgum (Liquidambar styraciflua), coniferyl aldehyde is a precursor to sinapaldehyde via hydroxylation mediated by coniferyl aldehyde 5-hydroxylase.[3]

Coniferyl aldehyde is reduced to coniferyl alcohol by the action of dehydrogenase enzymes.[2]

It is found in Senra incana (Hibisceae). It is a low molecular weight phenol that is susceptible to extraction from cork stoppers into wine.[4]

See also

References

  1. ^ Boerjan, Wout; Ralph, John; Baucher, Marie (2003). "Lignin Biosynthesis". Annual Review of Plant Biology. 54: 519–546. doi:10.1146/annurev.arplant.54.031902.134938. PMID 14503002.
  2. ^ a b Li, Laigeng; Cheng, Xiao Fei; Leshkevich, Jacqueline; Umezawa, Toshiaki; Harding, Scott A.; Chiang, Vincent L. (2001). "The Last Step of Syringyl Monolignol Biosynthesis in Angiosperms is Regulated by a Novel Gene Encoding Sinapyl Alcohol Dehydrogenase". The Plant Cell. 13 (7): 1567–1586. doi:10.1105/tpc.010111. PMC 139549. PMID 11449052.
  3. ^ Osakabe, Keishi; Tsao, Cheng Chung; Li, Laigeng; Popko, Jacqueline L.; Umezawa, Toshiaki; Carraway, Daniel T.; Smeltzer, Richard H.; Joshi, Chandrashekhar P.; Chiang, Vincent L. (1999). "Coniferyl aldehyde 5-hydroxylation and methylation direct syringyl lignin biosynthesis in angiosperms". Proceedings of the National Academy of Sciences. 96 (16): 8955–8960. Bibcode:1999PNAS...96.8955O. doi:10.1073/pnas.96.16.8955. PMC 17714. PMID 10430877.
  4. ^ Conde, Elvira; Cadahía, Estrella; García-Vallejo, María Concepción; Fernández De Simón, Brígida (1998). "Polyphenolic Composition of Quercus suber Cork from Different Spanish Provenances". Journal of Agricultural and Food Chemistry. 46 (8): 3166–3171. doi:10.1021/jf970863k.