Catechin

Studies confirmed that (+)-catechin adopts a mixture of A- and E-conformers in aqueous solution and their conformational equilibrium has been evaluated to be 33:67.

[4] The ability to quench singlet oxygen seems to be in relation with the chemical structure of catechin, with the presence of the catechol moiety on ring B and the presence of a hydroxyl group activating the double bond on ring C.[5] Electrochemical experiments show that (+)-catechin oxidation mechanism proceeds in sequential steps, related with the catechol and resorcinol groups and the oxidation is pH-dependent.

The biosynthesis of catechin begins with ma 4-hydroxycinnamoyl CoA starter unit which undergoes chain extension by the addition of three malonyl-CoAs through a PKSIII pathway.

The biosynthesis of catechin is shown below[21][22][23] Leucocyanidin reductase (LCR) uses 2,3-trans-3,4-cis-leucocyanidin to produce (+)-catechin and is the first enzyme in the proanthocyanidin (PA) specific pathway.

[29] Catechins are metabolised upon uptake from the gastrointestinal tract, in particular the jejunum,[31] and in the liver, resulting in so-called structurally related epicatechin metabolites (SREM).

[32] The main metabolic pathways for SREMs are glucuronidation, sulfation and methylation of the catechol group by catechol-O-methyl transferase, with only small amounts detected in plasma.

[33][30] The majority of dietary catechins are however metabolised by the colonic microbiome to gamma-valerolactones and hippuric acids which undergo further biotransformation, glucuronidation, sulfation and methylation in the liver.

[37] Only limited evidence from dietary studies indicates that catechins may affect endothelium-dependent vasodilation which could contribute to normal blood flow regulation in humans.

[42][43] Due to extensive metabolism during digestion, the fate and activity of catechin metabolites responsible for this effect on blood vessels, as well as the actual mode of action, are unknown.

[33][44] Catechin and its metabolites can bind tightly to red blood cells and thereby induce the development of autoantibodies, resulting in haemolytic anaemia and renal failure.

[47] Catechins from green tea can be hepatotoxic[48] and the European Food Safety Authority has recommended not to exceed 800 mg per day.

[49] One limited meta-analysis showed that increasing consumption of green tea and its catechins to seven cups per day provided a small reduction in prostate cancer.

[52] Centaurea maculosa, the spotted knapweed often studied for this behavior, releases catechin isomers into the ground through its roots, potentially having effects as an antibiotic or herbicide.

[54] Epicatechin and catechin may prevent coffee berry disease by inhibiting appressorial melanization of Colletotrichum kahawae.

Chemical structure of (+)-Catechin
Chemical structure of (+)-Catechin
Catechin numbered
3D view of "pseudoequatorial" ( E ) conformation of (+)-catechin
UV spectrum of catechin.
Human metabolites of epicatechin (excluding colonic metabolites) [ 30 ]
Schematic representation of (−)-epicatechin metabolism in humans as a function of time post-oral intake. SREM: structurally related (−)-epicatechin metabolites. 5C-RFM: 5-carbon ring fission metabolites. 3/1C-RFM: 3- and 1-carbon-side chain ring fission metabolites. The structures of the most abundant (−)-epicatechin metabolites present in the systemic circulation and in urine are depicted. [ 30 ]
Interspecies differences in (−)-epicatechin metabolism. [ 30 ]