The creation and physiological relevance of divergent hydroxylation patterns in the flavonoid pathway

Int J Mol Sci. 2010 Feb 4;11(2):595-621. doi: 10.3390/ijms11020595.

Abstract

Flavonoids and biochemically-related chalcones are important secondary metabolites, which are ubiquitously present in plants and therefore also in human food. They fulfill a broad range of physiological functions in planta and there are numerous reports about their physiological relevance for humans. Flavonoids have in common a basic C(6)-C(3)-C(6) skeleton structure consisting of two aromatic rings (A and B) and a heterocyclic ring (C) containing one oxygen atom, whereas chalcones, as the intermediates in the formation of flavonoids, have not yet established the heterocyclic C-ring. Flavonoids are grouped into eight different classes, according to the oxidative status of the C-ring. The large number of divergent chalcones and flavonoid structures is from the extensive modification of the basic molecules. The hydroxylation pattern influences physiological properties such as light absorption and antioxidative activity, which is the base for many beneficial health effects of flavonoids. In some cases antiinfective properties are also effected.

Keywords: 2-oxoglutarate-Fe(II)-dependent dioxygenase; chalcone; cytochrome P450 dependent monooxygenase; flavonoid; hydroxylation; oxidoreductase; plant.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Anthocyanins / chemistry
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology
  • Antioxidants / chemistry
  • Antioxidants / metabolism
  • Bacteria / drug effects
  • Flavonoids / chemistry*
  • Flavonoids / metabolism
  • Flavonoids / pharmacology
  • Heterocyclic Compounds / chemistry
  • Humans
  • Hydroxylation
  • Plants / chemistry
  • Plants / metabolism
  • Reactive Oxygen Species / metabolism
  • Structure-Activity Relationship

Substances

  • Anthocyanins
  • Anti-Infective Agents
  • Antioxidants
  • Flavonoids
  • Heterocyclic Compounds
  • Reactive Oxygen Species
  • cyanidin