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Catechin

 

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Catechin



 
 
Catechins are polyphenol
Polyphenol

Polyphenols are a group of chemical substances found in plants, characterized by the presence of more than one phenol unit or building block per molecule....
ic antioxidant
Antioxidant

An antioxidant is a molecule capable of slowing or preventing the Redox of other molecules. Oxidation is a chemical reaction that transfers electrons from a substance to an oxidizing agent....
 plant
Plant

Plants are Life organisms belonging to the Kingdom Plantae. They include familiar organisms such as trees, herbs, bushes, grasses, vines, ferns, mosses, and green algae....
 metabolites. They belong to the family of flavonoids and, to be more specific, flavan-3-ols
Flavonoid

The term flavonoid refers to a class of plant secondary metabolites. According to the IUPAC nomenclature, they can be classified into:*flavonoids, derived from 2-phenylchromone structure...
.






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Encyclopedia


Epicatechin
Epigallocatechin
Catechins are polyphenol
Polyphenol

Polyphenols are a group of chemical substances found in plants, characterized by the presence of more than one phenol unit or building block per molecule....
ic antioxidant
Antioxidant

An antioxidant is a molecule capable of slowing or preventing the Redox of other molecules. Oxidation is a chemical reaction that transfers electrons from a substance to an oxidizing agent....
 plant
Plant

Plants are Life organisms belonging to the Kingdom Plantae. They include familiar organisms such as trees, herbs, bushes, grasses, vines, ferns, mosses, and green algae....
 metabolites. They belong to the family of flavonoids and, to be more specific, flavan-3-ols
Flavonoid

The term flavonoid refers to a class of plant secondary metabolites. According to the IUPAC nomenclature, they can be classified into:*flavonoids, derived from 2-phenylchromone structure...
. These compounds are abundant in tea
Tea

Tea refers to the agricultural products of the leaves, leaf buds, and internodes of the Camellia sinensis plant, prepared and cured by various methods....
s derived from the tea-plant Camellia sinensis
Camellia sinensis

Camellia sinensis, the tea plant, is the species of plant whose leaves and leaf buds are used to produce tea. It is of the genus Camellia , a genus of flowering plants in the family Theaceae....
 as well as in some cocoa
Cocoa

Cocoa is the dried and fully fermented fatty seed of the cacao from which chocolate is made. "Cocoa" can often also refer to the drink commonly known as hot chocolate; Cocoa solids, the dry powder made by grinding cocoa seeds and removing the cocoa butter from the dark, bitter cocoa solids; or it may refer to the combination of both cocoa p...
s and chocolate
Chocolate

Chocolate comprises a number of raw and processed foods that are produced from the seed of the tropical cacao tree.Chocolate has become one of the most popular flavors in the world....
s (made from the seeds of Theobroma cacao
Cacao

Cacao , or the cocoa plant, is a small evergreen tree in the family Sterculiaceae , native to the deep tropical region of the Americas. There are two prominent competing hypotheses about the origins of the original wild Theobroma cacao tree....
).

The name of the catechin chemical family derives from catechu
Catechu

Catechu is an extract of any of several species of Acacia—but especially Acacia catechu—produced by boiling the wood in water and evaporating the resulting brew....
 which is the juice of Mimosa catechu (Acacia catechu
Acacia catechu

Acacia catechu is a deciduous, thorny tree which grows up to in height.Common names for it include Catechu, Cachou and Black Cutch....
 L.f))

Catechin, epicatechin, gallocatechin, epigallocatechin, and the gallates


Catechin and epicatechin are epimer
Epimer

In chemistry, epimers are diastereomers that differ in configuration of only one stereogenic center. Diastereomers are a class of stereoisomers that are non-superposable, non-mirror images of one another, unlike enantiomers which are non-superposable mirror images of one another....
s, with (-)-epicatechin and (+)-catechin being the most common optical isomers found in nature. Catechin was first isolated from the plant extract catechu
Catechu

Catechu is an extract of any of several species of Acacia—but especially Acacia catechu—produced by boiling the wood in water and evaporating the resulting brew....
, avove, from which it derives its name. Heating catechin past its point of decomposition releases pyrocatechol
Pyrocatechol

Catechol, formerly known as pyrocatechol, is the organic compound with the formula C6H42. It is one of three isomeric benzenediols. This colourless compound occurs naturally in trace amounts....
 (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
Pyrogallol

Pyrogallol or benzene-1,2,3-triol is a white crystalline powder and a powerful reducing agent. It was first prepared by Carl Wilhelm Scheele 1786 by heating gallic acid....
 compared to pyrocatechol.

Catechin gallates are gallic acid
Gallic acid

Gallic acid is an organic acid, also known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants....
 ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
s of the catechins; such as EGCG (epigallocatechin gallate
Epigallocatechin gallate

Epigallocatechin gallate , also known as Epigallocatechin 3-gallate, is the ester of epigallocatechin and gallic acid and a type of catechin.EGCG is the most abundant catechin in tea and an antioxidant that may have therapeutic properties for many disorders including cancer....
), which is commonly the most abundant catechin in tea.

Sources of catechins

Catechins constitute about 25% of the dry weight of fresh tea leaf, although total catechin content varies widely depending on clonal variation, growing location, seasonal/ light variation, and altitude. They are present in nearly all teas made from Camellia sinensis
Camellia sinensis

Camellia sinensis, the tea plant, is the species of plant whose leaves and leaf buds are used to produce tea. It is of the genus Camellia , a genus of flowering plants in the family Theaceae....
, including white tea
White tea

White tea is the uncured and unoxidized tea leaf. Like green tea, oolong tea and black tea, white tea comes from the Camellia sinensis plant....
, green tea
Green tea

'Green tea' is a type of tea made solely with the leaves of Camellia sinensis, that has undergone minimal oxidation during processing. Green tea originates from China and has become associated with many cultures in Asia from Japan to the Middle East....
, black tea
Black tea

Black tea is a variety of tea that is more oxidization than the oolong, green tea, and White tea varieties.All four varieties are made from leaves of Camellia sinensis. Black tea is generally stronger in flavor and contains more caffeine than the less Redox teas....
 and Oolong tea
Oolong

Oolong is a traditional Chinese tea somewhere between green tea and black tea in oxidation. It ranges from 10% to 70% oxidation.In Chinese tea culture, semi-oxidized oolong teas are collectively grouped as qingch? ....
.

Catechins are also present in the human diet in chocolate
Chocolate

Chocolate comprises a number of raw and processed foods that are produced from the seed of the tropical cacao tree.Chocolate has become one of the most popular flavors in the world....
, fruits, vegetables and wine and are found in many other plant species.

Epigallocatechin gallate
Epigallocatechin gallate

Epigallocatechin gallate , also known as Epigallocatechin 3-gallate, is the ester of epigallocatechin and gallic acid and a type of catechin.EGCG is the most abundant catechin in tea and an antioxidant that may have therapeutic properties for many disorders including cancer....
 is the most abundant catechin in tea.

Another stereoisomer, (-)-catechin, is released from the roots of the invasive weed, spotted knapweed. It acts as an herbicide to inhibit competition by a wide range of other plant species. . This phytotoxic compound inhibits seed germination and growth.

Health benefits of catechins


The health benefits of catechins have been studied extensively in humans and in animal models. Reduction in atherosclerotic plaques was seen in animal models. Reduction in carcinogenesis
Carcinogenesis

'Carcinogenesis' , is the process by which normal cell are transformed into cancer cells.Cell division is a physiological process that occurs in almost all tissues and under many circumstances....
 was seen in vitro
In vitro

In vitro refers to the technique of performing a given procedure in a controlled environment outside of a living organism. Some may argue that in vitro refers to a process that is created in a "test tube"; however, Robert Kail and John Cavanaugh on page 58 in the 4th edition of Human Development: A Life-Span View cite that in fact th...
.

Many studies on health benefits
Health benefits of tea

This article only deals with the effects of tea which is made from the plant Camellia sinensis . This page does not deal with the effects of other teas....
 have been linked to the catechin content. According to Norman Hollenberg, professor of medicine at Harvard Medical School
Harvard Medical School

Harvard Medical School is one of the graduate schools of Harvard University and currently the #1 medical school in America, as ranked by U.S. News and World Report....
, epicatechin can reduce the risk of four of the major health problems: stroke, heart failure, cancer and diabetes. He studied the Kuna
Kuna (people)

Kuna or Cuna is the name of an indigenous people of Panama and Colombia. The spelling Kuna is currently preferred. In the Kuna language, the name is Dule or Tule, meaning "people," and the name of the language in Kuna is Dulegaya, meaning "people-talk."...
 people in Panama
Panama

Panama, officially the Republic of Panama , is the southernmost country of Central America and, in turn, North America. Situated on an isthmus connecting North and South America, some categorize it as a transcontinental nation....
, 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.

According to one researcher epigallocatechin-3-gallate is an antioxidant that helps protect the skin from UV radiation-induced damage and tumor formation.

Green tea
Green tea

'Green tea' is a type of tea made solely with the leaves of Camellia sinensis, that has undergone minimal oxidation during processing. Green tea originates from China and has become associated with many cultures in Asia from Japan to the Middle East....
 catechins have also been shown to possess antibiotic properties due to their role in disrupting a specific stage of the bacterial DNA replication process.

Catechins, when combined with habitual exercise, have been shown to delay some forms of aging. Mice fed catechins showed decreased levels of aging. Oxidative stress was lowered in cell mitochondria, as well as increase in mRNA transcription of mitochondria related proteins.

The Lancet medical journal has warned against increase one’s intake of dark chocolate in order to improve health, because the beneficial compounds are sometimes removed due to their bitter taste without an indication on the label, and because the fat, sugar, and calories of chocolate increase the risk for heart disease, unless balanced by a reduction in the intake of other foods.

Raw Cacao
Cacao

Cacao , or the cocoa plant, is a small evergreen tree in the family Sterculiaceae , native to the deep tropical region of the Americas. There are two prominent competing hypotheses about the origins of the original wild Theobroma cacao tree....
 (unprocessed except for fermenting and drying) does not contribute to these problems and is becoming an increasingly popular health food product in developed countries.

See also

  • Catechu
    Catechu

    Catechu is an extract of any of several species of Acacia—but especially Acacia catechu—produced by boiling the wood in water and evaporating the resulting brew....
  • Catechol
  • Catecholamines
  • Quercetin
    Quercetin

    Quercetin is a plant-derived flavonoid, specifically a flavonol, used as a nutritional supplement.The American Cancer Society says that quercetin "has been promoted as being effective against a wide variety of diseases, including cancer....
  • Flavonoid
    Flavonoid

    The term flavonoid refers to a class of plant secondary metabolites. According to the IUPAC nomenclature, they can be classified into:*flavonoids, derived from 2-phenylchromone structure...
  • Camellia sinensis
    Camellia sinensis

    Camellia sinensis, the tea plant, is the species of plant whose leaves and leaf buds are used to produce tea. It is of the genus Camellia , a genus of flowering plants in the family Theaceae....
  • Cocoa
    Cocoa

    Cocoa is the dried and fully fermented fatty seed of the cacao from which chocolate is made. "Cocoa" can often also refer to the drink commonly known as hot chocolate; Cocoa solids, the dry powder made by grinding cocoa seeds and removing the cocoa butter from the dark, bitter cocoa solids; or it may refer to the combination of both cocoa p...
  • Tannin
    Tannin

    Tannins are astringent, bitter plant polyphenols that either bind and Precipitation or shrink proteins. The astringency from the tannins is what causes the dry and puckery feeling in the mouth following the consumption of red wine or an unripened fruit....
  • Polyphenol
    Polyphenol

    Polyphenols are a group of chemical substances found in plants, characterized by the presence of more than one phenol unit or building block per molecule....
  • Proanthocyanidin
    Proanthocyanidin

    Proanthocyanidin is a class of flavanols. Proanthocyanidins are essentially polymer chains of flavonoids such as catechins. One was discovered in 1936 by Professor Jacques Masquelier and called Vitamin P, although this name did not gain official category status and has since fallen out of usage....
  • Polyphenon
    Polyphenon

    Polyphenon is a high grade green tea polyphenol extract. It is derived through a water based extraction method from green tea, purifying the polyphenol catechin molecules which are the bioactive molecule thought to be responsible for the health benefits of green tea....
  • Phenolic compounds in wine
    Phenolic compounds in wine

    The phenolic compounds in wine include a large group of several hundred chemical compounds, known as polyphenolics, that affect the taste , color and mouthfeel of wine....

External links

  • by Ross Chainey 12/03/07