Flavonoid biosynthesis

Summary

Flavonoids are synthesized by the phenylpropanoid metabolic pathway in which the amino acid phenylalanine is used to produce 4-coumaroyl-CoA.[1] This can be combined with malonyl-CoA to yield the true backbone of flavonoids, a group of compounds called chalcones, which contain two phenyl rings. Conjugate ring-closure of chalcones results in the familiar form of flavonoids, the three-ringed structure of a flavone. The metabolic pathway continues through a series of enzymatic modifications to yield flavanonesdihydroflavonolsanthocyanins. Along this pathway, many products can be formed, including the flavonols, flavan-3-ols, proanthocyanidins (tannins) and a host of other various polyphenolics.

Flavonoid Biosynthesis Diagrams
Biosynthesis of catechin
A biochemical diagram showing the class of flavonoids and their source in nature through various inter-related plant species.


Flavanoids can possess chiral carbons. Methods of analysis should take this element into account[2] especially regarding bioactivity or enzyme stereospecificity.[3]

Enzymes edit

The biosynthesis of flavonoids involves several enzymes.

Methylation edit

Glycosylation edit

Further acetylations edit

References edit

  1. ^ Ververidis Filippos, F; Trantas Emmanouil; Douglas Carl; Vollmer Guenter; Kretzschmar Georg; Panopoulos Nickolas (October 2007). "Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: Chemical diversity, impacts on plant biology and human health". Biotechnology Journal. 2 (10): 1214–34. doi:10.1002/biot.200700084. PMID 17935117.
  2. ^ Methods of analysis and separation of chiral flavonoids. Jaime A. Yáñeza, Preston K. Andrewsb and Neal M. Journal of Chromatography B, Volume 848, Issue 2, 1 April 2007, Pages 159-181
  3. ^ A theoretical study of the conformational behavior and electronic structure of taxifolin correlated with the free radical-scavenging activity. Patrick Trouillas, Catherine Fagnère, Roberto Lazzaroni, Claude Calliste, Abdelghafour Marfak and Jean-Luc Duroux, Food Chemistry, Volume 88, Issue 4, December 2004, Pages 571-582