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.

Flavonoid biosynthesis

Enzymes

The biosynthesis of flavonoids involves several enzymes.

Flavonoid biosynthesis

Anthocyanidin reductase

Chalcone isomerase

Dihydrokaempferol 4-reductase

Flavone synthase

Flavonoid 3'-monooxygenase

Flavonol synthase

Flavanone 3-dioxygenase

Flavanone 4-reductase

Leucoanthocyanidin reductase

Leucocyanidin oxygenase

Naringenin-chalcone synthase

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

Flavonoids metabolism

Biosynthesis

Flavonoid biosynthesis