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Flavonoid biosynthesis

Flavonoids are synthesized by the phenylpropanoid metabolic pathway in which the amino acid phenylalanine is used to produce 4-coumaroyl-CoA. 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 flavanones → dihydroflavonols → anthocyanins. Along this pathway, many products can be formed, including the flavonols, flavan-3-ols, proanthocyanidins (tannins) and a host of other various polyphenolics.

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

Enzymes

The biosynthesis of flavonoids involves several enzymes.

Backbone

  • 4-oumaroyl-CoA chalcone (naringenin-chalcone)
  • Naringenin-chalcone flavanone (naringenin).

Path to cyanidin:

  • flavanone 3'-hydroxyflavonoid (eriodictyol)
  • eriodictyol dihydroflavonol (taxifolin)
  • taxifolin leucocyanidin
  • leucocyanidin cyanidin

Path to (–)-epicatechin:

  • cyanidin (–)-epicatechin

Path to (+)-catechin:

  • leucocyanidin (+)-catechin

Path to flavones:

  • Flavone synthase

Path to flavonols:

  • dihydroflavonol flavonol

Path to 3-deoxyanthocyanidins:

  • flavanone flavan-4-ol
  • (Process analogous to taxifolin → cyanidin follows)

Methylation

  • Apigenin 4'-O-methyltransferase
  • Luteolin O-methyltransferase
  • Quercetin 3-O-methyltransferase

Glycosylation

  • Anthocyanidin 3-O-glucosyltransferase
  • Flavone 7-O-beta-glucosyltransferase
  • Flavone apiosyltransferase
  • Flavonol-3-O-glucoside L-rhamnosyltransferase
  • Flavonol 3-O-glucosyltransferase

Further acetylations

  • Isoflavone-7-O-beta-glucoside 6"-O-malonyltransferase

References

References

  1. (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. (April 2007). "Methods of analysis and separation of chiral flavonoids". Journal of Chromatography B.
  3. (December 2004). "A theoretical study of the conformational behavior and electronic structure of taxifolin correlated with the free radical-scavenging activity". Food Chemistry.
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