The most common catechin isomer is the (+)-catechin. The other stereoisomer is (-)-catechin or ent-catechin. The most common epicatechin isomer is (-)-epicatechin (also known under the names L-epicatechin, epicatechol, (-)-epicatechol, l-acacatechin, l-epicatechol, epi-catechin, 2,3-cis-epicatechin or (2R,3R)-(-)-epicatechin).
Making reference to no particular isomer, the molecule can just be called catechin. Mixtures of the different enantiomers can be called (+/-)-catechin or DL-catechin and (+/-)-epicatechin or DL-epicatechin.
Catechin and epicatechin are the building blocks of the proanthocyanidins, a type of condensed tannin.
3D view of "pseudoequatorial" (E) conformation of(+)-catechin
Moreover, the flexibility of the C-ring allows for two conformation isomers, putting the B ring either in a pseudoequatorial position (E conformer) or in a pseudoaxial position (A conformer). 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.
As flavonoids, catechins can act as antioxidants when in high concentration in vitro, but compared with other flavonoids, their antioxidant potential is low. 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.
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 oxidation of the catechol 3',4'-dihydroxyl electron-donating groups occurs first, at very low positive potentials, and is a reversible reaction. The hydroxyl groups of the resorcinol moiety oxidised afterwards were shown to undergo an irreversible oxidation reaction.
Catechins and epicatechins are found in cocoa, which, according to one database, has the highest content (108 mg/100 g) of catechins among foods analyzed, followed by prune juice (25 mg/100 ml) and broad bean pod (16 mg/100 g).Açaí oil, obtained from the fruit of the açaí palm (Euterpe oleracea), contains (+)-catechins (67 mg/kg).
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. 4-hydroxycinnamoyl CoA is biosynthesized from L-phenylalanine through the Shikimate pathway. L-phenylalanine is first deaminated by phenylalanine ammonia lyase (PAL) forming cinnamic acid which is then oxidized to 4-hydroxycinnamic acid by cinnamate 4-hydroxylase. Chalcone synthase then catalyzes the condensation of 4-hydroxycinnamoyl CoA and three molecules of malonyl-CoA to form chalcone. Chalcone is then isomerized to naringenin by chalcone isomerase which is oxidized to eriodictyol by flavonoid 3'- hydroxylase and further oxidized to taxifolin by flavanone 3-hydroxylase. Taxifolin is then reduced by dihydroflavanol 4-reductase and leucoanthocyanidin reductase to yield catechin. The biosynthesis of catechin is shown below
Human metabolites of epicatechin (excluding colonic metabolites)
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.
The stereochemical configuration of catechins has a strong impact on their uptake and metabolism as uptake is highest for (-)-epicatechin and lowest for (-)-catechin.
Inter-species differences in (-)-epicatechin metabolism.
Nanoparticle methods are under preliminary research as potential delivery systems of catechins. Cocoa catechins are under preliminary research for their potential to affect the risk of cardiovascular diseases. 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.
(+)-Catechin and (-)-epicatechin are transformed by the endophytic filamentous fungus Diaporthe sp. into the 3,4-cis-dihydroxyflavan derivatives, (+)-(2R,3S,4S)-3,4,5,7,3',4'-hexahydroxyflavan (leucocyanidin) and (-)-(2R,3R,4R)-3,4,5,7,3',4'-hexahydroxyflavan, respectively, whereas (-)-catechin and (+)-epicatechin with a 2S-phenyl group resisted the biooxidation.
Epigeoside (Catechin-3-O-alpha-L-rhamnopyranosyl-(1-4)-beta-D-glucopyranosyl-(1–6)-beta-D-glucopyranoside) can be isolated from the rhizomes of Epigynum auritum.
Association between flavan-3-ol intake and incidence of cardiovascular disease in different cohort studies. Data compare the bottom and top quintiles of intake.
Centuries ago, catechin-containing extracts were thought to be useful for treating heart diseases, and an effect on the permeability of capillaries was shown in 1936. Limited evidence from dietary studies indicates that catechins may have an effect on endothelium-dependent vasodilation which could contribute to normal blood flow regulation in humans. Green tea catechins may improve blood pressure, especially when systolic blood pressure is above 130 mmHg. 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.
The European Food Safety Authority established that cocoa flavanols have an effect on vascular function in healthy adults by concluding: "cocoa flavanols help maintain endothelium-dependent vasodilation, which contributes to normal blood flow". Data from observational cohort studies have not shown a consistent association between flavan-3-ol intake and risk of cardiovascular diseases.
Catechins released into the ground by some plants may hinder the growth of their neighbors, a form of allelopathy.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. One hypothesis is that it causes a reactive oxygen species wave through the target plant's root to kill root cells by apoptosis. Most plants in the European ecosystem have defenses against catechin, but few plants are protected against it in the North American ecosystem where Centaurea maculosa is an invasive, uncontrolled weed.
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