Flavan-3-ols (sometimes referred to as flavanols) are a class of flavonoids that use the 2-phenyl-3,4-dihydro-2H-chromen-3-ol skeleton. These compounds include the catechins and the catechin gallates.
Flavanols (with an "a") are not to be confused with flavonols (with an "o"), another class of flavonoids containing a ketone group.
Flavanols are building blocks for proanthocyanidins.
Flavanols possess two chiral carbons meaning there 4 diastereoisomers for each of them.
Catechins are differentiated from the ketone-containing flavonoids such as quercitin and rutin, which are called flavonols (spelled flavonols with an o). The term bioflavonoid was first used to describe the flavonols, but as an imprecise term has been loosely applied to the larger family of flavonoids, including also the polymeric hydroxyl-only containing flavan-3-ols (catechins).
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The catechins are abundant in teas derived from the tea-plant Camellia sinensis as well as in some cocoas and chocolates[1] (made from the seeds of Theobroma cacao).
Catechins are also present in the human diet in fruits, vegetables and wine[2] and are found in many other plant species.[3]
Flavan-3-ols (sometimes referred to as flavanols) are a class of flavonoids that use the 2-phenyl-3,4-dihydro-2H-chromen-3-ol skeleton. These compounds include the catechins and the catechin gallates.
Flavanols (with an "a") are not to be confused with flavonols (with an "o"), another class of flavonoids containing a ketone group.
Flavanols are building blocks for proanthocyanidins.
Flavanols possess two chiral carbons meaning there 4 diastereoisomers for each of them.
Catechins are differentiated from the ketone-containing flavonoids such as quercitin and rutin, which are called flavonols (spelled flavonols with an o). The term bioflavonoid was first used to describe the flavonols, but as an imprecise term has been loosely applied to the larger family of flavonoids, including also the polymeric hydroxyl-only containing flavan-3-ols (catechins).
Catechin and epicatechin are epimers, with (-)-epicatechin and (+)-catechin being the most common optical isomers found in nature. Catechin was first isolated from the plant extract catechu, from which it derives its name. Heating catechin past its point of decomposition releases pyrocatechol (also called catechol), which explains the common origin of the names of these compounds.
Epigallocatechin and gallocatechin contain an additional phenolic hydroxyl group when compared to epicatechin and catechin, respectively, similar to the difference in pyrogallol compared to pyrocatechol.
Catechin gallates are gallic acid esters of the catechins; such as epigallocatechin gallate (EGCG), which is commonly the most abundant catechin in tea.
The flavonoids are products from a cinnamoyl-CoA starter unit, with chain extension using three molecules of malonyl-CoA. Reactions are catalyzed by a type III PKS enzyme. These enzyme do not utilize ACPSs, but instead employ coenzyme A esters and have a single active site to perform the necessary series of reactions e.g. chain extension, condensation, cyclization. Chain extension of 4-hydroxycinnamoyl-CoA with three molecules of malonyl-CoA gives initially a polyketide (Figure 1), which can be folded. These allow Claisen-like reactions to occur generating aromatic rings [4] [5]
Figure 1:Schematic overview of the flavan-3-ol (-)-epicatechin biosynthesis in plants. Enzymes are indicated in blue, abbreviated as follows: E1, phenylalanine ammonia lyase (PAL), E2, tyrosine ammonia lyase (TAL), E3, cinnamate 4-hydroxylase, E4, 4-coumaroyl: CoA-ligase, E5, chalcone synthase (naringerin-chalcone synthase), E6, chalcone isomerase, E7, flavonoid 3´-hydroxylase, E8, flavonone 3-hydroxylase, E9, dihydroflavanol 4-reductase, E10, anthocyanidin synthase (leucoanthocyanidin dioxygenase), E11, anthocyanidin reductase. HSCoA, Coenzyme A. L-Tyr, L-Tyrosin, L-Phe, L-Phenylalanine.
The health benefits of catechins have been studied extensively in humans and in animal models. Reduction in atherosclerotic plaques was seen in animal models.[6] Reduction in carcinogenesis was seen in vitro.[7]
Many studies on health benefits have been linked to the catechin content. According to Norman Hollenberg, professor of medicine at Harvard Medical School, epicatechin can reduce the risk of four of the major health problems: stroke, heart failure, cancer and diabetes. He studied the Kuna people in Panama, who drink up to 40 cups of cocoa a week, and found that the prevalence of the “big four” is less than 10%. He believes that epicatechin should be considered essential to the diet and thus classed as a vitamin.[8][9][10]
According to one researcher[11] epigallocatechin-3-gallate is an antioxidant that helps protect the skin from UV radiation-induced damage and tumor formation.
Catechins, when combined with habitual exercise, have been shown to delay some forms of aging. Mice fed catechins showed decreased levels of aging, lowering of oxidative stress in mitochondria, and an increase in mRNA transcription of mitochondrial-related proteins.[12]
An editorial in The Lancet medical journal warned against increasing one’s intake of dark chocolate to improve health because the beneficial compounds are sometimes removed due to their bitter taste without an indication on the label.[13] Additionally, such product may be high in lead, and also fat, sugar, and calories, which can increase the risk for heart disease.
In 2008 UCLA cancer researchers found that study participants who ate foods containing certain flavonoids seemed to be protected from developing lung cancer. Dr. Zhang, (professor of public health and epidemiology at the UCLA School of Public Health) said the flavonoids that appeared to be the most protective included catechin, found in strawberries and green and black teas; kaempferol, found in Brussels sprouts and apples; and quercetin, found in beans, onions (particularly red) and apples.[14]
| Image | Name | Formula | Oligomers |
|---|---|---|---|
| Catechin, C, (+)-Catechin | C15H14O6 | Proanthocyanidins | |
| Epicatechin, EC, (-)-Epicatechin (cis) | C15H14O6 | Proanthocyanidins | |
| Epigallocatechin, EGC | C15H14O7 | Prodelphinidins | |
| Epicatechin gallate, ECG | C22H18O10 | ||
| Epigallocatechin gallate, EGCG, (-)-Epigallocatechin gallate |
C22H18O11 | ||
| Epiafzelechin | C15H14O5 | ||
| Fisetinidol | C15H14O5 | ||
| Guibourtinidol | C15H14O4 | Proguibourtinidins | |
| Mesquitol | C15H14O6 | ||
| Robinetinidol | C15H14O6 | Prorobinetinidins |
Flavanols, usually from cocoa beans or tea, are believed to keep arteries flexible,[15] increase small vessel circulation,[16] reduce blood pressure[17] and protect against sunburns [18][19]
The Mars Corporation introduced in 2003 a line of flavanol-rich chocolate products under the brand name CocoaVia, prepared using their proprietary process called Cocoapro. In 2008, the product was rebranded as Cirku.[20]
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