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.