Tag Archives: theaflavins

Black tea: definition, processing and polyphenols

What is black tea?

Black tea, like the other types of tea, is an infusion of processed leaves of Camellia sinensis, the tea plant, a shrub that belongs to the Theaceae family.
Black tea, a type of fully fermented tea, is the most consumed tea worldwide, accounting for about 78% of the consumed tea. It is preferred by Western populations, while the favorite tea in Asia, particularly in Japan and China, is green tea.

“Tea is drunk to forget the din of the world.”
T’ien Yiheng

Processing of black tea

The processing of the leaves of Camellia sinensins, that leads to the production of black tea, proceeds through three main steps:

  • withering or drying;
  • rolling;
  • oxidation

The last step, oxidation, gives black tea the specific organoleptic characteristics and composition in polyphenols, that are extremely different from those of green tea (green tea undergoes very slight oxidative processes during processing).

Withering or drying

Black Tea: Withering or Drying  of Tea Leaves
Fig. 1 – Withering or Drying of Tea Leaves

The withering or drying step is the first, and most basic process during processing of black tea. In this step, water in the leaves is removed (about 75% of the leaf’s weight is made up of water), thus determining the concentration of the sap of the leaf itself. The withering also makes the next step easier.
Withering can be achieved in three different ways:

  • exposing leaves to sunlight, that is, sun withering;
  • heating in an appropriate manner the rooms where the leaves are placed;
  • using machines that artificially ventilate the leaves.

Rolling

The rolling step follows the withering of the leaves. It breaks the leaf tissue, facilitating the outflow of lymph; thus, it promotes the subsequent enzymatic oxidation of polyphenols. This step is essential for the creation of the aroma, color and flavor of black tea.

Oxidation

The oxidation, also improperly called fermentation, is the last stage of black tea processing, and is crucial in determining the quality of the tea. In this step, the enzymatic oxidation of about 90–95 % of the polyphenols occurs, accompanied by other changes that make the green tea leaves into red color.
Temperature (typically 25°C), pH, relative humidity (95% or more), ventilation, and duration are crucial factors too.

Black tea polyphenols

During the oxidation step, the main compounds that undergo oxidation processes, both enzymatic, by polyphenol oxidase, and chemical, by the action of atmospheric oxygen, are:

  • monomeric catechins and gallate catechins;
  • to a lesser extent, the glycosides of catechins, especially myricetin;
  • but also not flavonoids compounds, such as teogallin (ester of gallic acid).

Therefore, throughout the process, a reduction in the concentration of monomeric catechins, characteristics of fresh leaves of Camellia sinensis and green tea, occurs, with the formation of complex polyphenols, such as:

  • thearubigins, red-brown or dark-brown in color;
  • theaflavins and theaflavic acids, red-orange in color.

Thearubigins, polymers of catechins not yet well characterized, are the major polyphenols in black tea, accounting for about 20% of extracted solids. In addition to the reddish color, thearubigins contribute the richness in taste, the so-called “body” to black tea.
Theaflavins, dimers of catechins much better characterized than thearubigins, account for about 3-5% of the solids in black tea infusion. Theaflavins contribute the astringent and brisk taste, as well as the red-orange color of the beverage.
The main theaflavins are:

  • theaflavin digallate;
  • theaflavin-3-gallate;
  • theaflavin-3′-gallate.

Black tea benefits and oxidized polyphenols

Although this type of tea is still able to improve health, oxidative processes suffered from the leaves during the processing attenuate health benefits of black tea, which are instead reported after intake of green tea (particularly, the benefits of green tea are ascribed to its content of catechins, such as EGCG, epicatechin and epicatechin gallate).

Black tea’s caffeine content does not vary significantly.

References

Asil M.H., Rabiei B., Ansari R.H. Optimal fermentation time and temperature to improve biochemical composition and sensory characteristics of black tea. Aust J Crop Sci 2012;6(3):550-8 [PDF]

Kuhnert N. Unraveling the structure of the black tea thearubigins. Arch Biochem Biophys 2010;501(1):37-51 [Abstract]

Li S., Lo C-Y., Pan M-H., Lai C-S. and Ho C-T. Black tea: chemical analysis and stability. Food Funct 2013;4:10-18 [Abstract]

Menet M-C., Sang S., Yang C.S., Ho C-T., and Rosen R.T. Analysis of theaflavins and thearubigins from black tea extract by MALDI-TOF mass spectrometry. J Agric Food Chem 2004;52:2455-61 [Abstract]

Sharma V.K., Bhattacharya A., Kumar A. and Sharma H.K. Health benefits of tea consumption. Trop J Pharm Res 2007;6(3):785-792 [Abstract]

Tea polyphenols: bioactive compounds from leaves of tea plant

Tea polyphenols: from the leaf to the cup

Tea Polyphenols
Fig. 1 – Camellia sinensis

The leaves of the tea plant, Camellia sinensis, and tea are rich in bioactive compounds.
More than 4000 molecules have been found in the beverage.
Approximately one third of these compounds are polyphenols, the most important molecules in determining nutritional value and health benefits of the beverage.

Tea is a cup of life.” Anonymus author

Tea polyphenols are mostly flavonoids, such as catechins in green tea (e.g. EGCG), and thearubigins and theaflavins in black tea.
Other bioactive compounds present in tea are:

  • alkaloids, such as caffeine, theophylline and theobromine;
  • amino acids, and among them, theanine (r-glutamylethylamide), that is also a brain neurotransmitter and one of the most important amino acids in green tea;
  • proteins;
  • carbohydrates;
  • chlorophyll;
  • volatile organic molecules, that is, compounds that easily produce vapors and contribute to the odor of the beverage;
  • fluoride, aluminum and trace elements.

These molecules provide the nutritional value of the tea, affecting human health in many ways. Their composition is highly influenced by processing of tea leaves.

Biological activities of polyphenols

Polyphenols, both in vivo and in vitro, have a broad spectrum of biological activities such as:

  • antioxidant properties;
  • reduction of various types of tumors;
  • inhibition of inflammation;
  • protective effects against hyperlipidemia and diabetes.

Therefore, they have a protective role against the development of many diseases.
Thanks to the abundance of tea polyphenols, there has been a growing interest in recent years about the possible preventive effects of beverage against several diseases, particularly cardiovascular disease, for example in the development and progression of atherosclerosis.

Mechanisms of action of tea polyphenols

Currently, there is limited information on how tea polyphenols exert their effects at cellular level.
It seems, at least in vitro, that catechins in green tea, and theaflavins and thearubigins in black tea are the bioactive compounds responsible for the physiological effects and health benefits of tea.
And among the observed mechanisms by which tea polyphenols act at the cellular level, in addition to the antioxidant effect, it has been observed, as a consequence of polyphenol binding to specific receptors on the cell membrane, changes in the activity of various protein kinases, and growth and transcriptional factors.
Moreover, it seems that these molecules, or at least EGCG, may enter the cell and directly interact with their intracellular specific targets.

References

Dwyer J.T. and Peterson J. Tea and flavonoids: where we are, where to go next. Am J Clin Nutr 2013;98:1611S-1618S [Abstract]

Grassi D., Desideri G., Di Giosia P., De Feo M., Fellini E., Cheli P., Ferri L., and Ferri C. Tea, flavonoids, and cardiovascular health: endothelial protection. Am J Clin Nutr 2013;98:1660S-1666S [Abstract]

Lambert J.D. Does tea prevent cancer? Evidence from laboratory and human intervention studies. Am J Clin Nutr 2013;98:1667S-1675S [Abstract]

Lenore Arab L., Khan F., and Lam H. Tea consumption and cardiovascular disease risk. Am J Clin Nutr 2013;98:1651S-1659S [Abstract]

Lorenz M. Cellular targets for the beneficial actions of tea polyphenols. Am J Clin Nutr 2013;98:1642S-1650S [Abstract]

Sharma V.K., Bhattacharya A., Kumar A. and Sharma H.K. Health benefits of tea consumption. Trop J Pharm Res 2007;6(3):785-792 [Abstract]

Yuan J-M. Cancer prevention by green tea: evidence from epidemiologic studies. Am J Clin Nutr 2013;98:1676S-1681S [Abstract]

Green tea benefits for health

Benefits of green tea: science and myths

Green Tea Benefits
Fig. 1 – Green Tea Benefits

Tea drinking, particularly green tea, has always been associated, at least in East Asia cultures (mainly in China and Japan) with health benefits. Only recently, the scientific community has begun to study the health benefits of tea consumption, recognizing its preventive value in many diseases.

Green tea benefits in preventing cancer

Several epidemiological and laboratory studies have shown encouraging results with respect to possible preventive role of tea, particularly green tea and its catechins, a subgroup of flavonoids (the most abundant polyphenols in human diet) against the development of some cancers like:

  • oral and digestive tract cancers;
  • lung cancer among those who have never smoked, not among smokers.

Tea polyphenols, the most active of which is epigallocatechin-3-gallate (EGCG), seem to act not only as antioxidants, but also as molecules that, directly, may influence gene expression and diverse metabolic pathways.

Green tea benefits in cardiovascular disease

Cardiovascular disease is the main cause of deaths worldwide, particularly in low- and middle-income countries, with an estimate of about 17 million deaths in 2008 that will increase up to 23.3 million by 2030.
Daily tea consumption, especially green tea, seems to be associated with a reduced risk of developing cardiovascular disease, such as hypertension and stroke.
Among the proposed mechanisms, the improved bioactivity of the endothelium-derived vasodilator nitric oxide (NO), due to the action of tea polyphenols that enhance nitric oxide synthesis, and/or decrease superoxide-mediated nitric oxide breakdown seem to be important.

Drinking a daily cup of tea will surely starve the apothecary.” Chinese proverb

Green tea benefits and antioxidant properties

Tea polyphenols may act, in vitro, as free radical scavengers.
Since radical damage plays a pivotal role in the development of many diseases such as atherosclerosis, rheumatoid arthritis, cancer, or in ischemia-reoxygenation injury, tea polyphenols, particularly green tea catechins, may have a preventive role.

Green tea benefits in weight loss and weight maintenance

Green tea, but also oolong tea, that is, catechins and caffeine rich teas, has a potential thermogenic effect. This has made them a potential tool for:

  • weight loss, by increasing energy expenditure and fat oxidation;
  • weight maintenance, ensuring a high energy expenditure during the maintenance of weight loss.

Indeed, it has been shown that green tea and green tea extracts are not an aid in weight loss and weight maintenance, since:

  • they are not able to induce a significant weight loss in overweight and obese adults;
  • they are not helpful in the maintenance of weight loss.

Green tea benefits in preventing dental decay

Animal and in vitro studies have shown that tea, and in particular its polyphenols, seems to possess:

  • antibacterial properties against pathogenic action of cariogenic bacteria, as Streptococcus mutans, particularly green tea EGCG;
  • inhibitory action on salivary and bacterial amylase (it seems that black tea thearubigins and theaflavins are more effective than green tea catechins);
  • it is able to inhibit acid production in the oral cavity.

All these properties make green tea and black tea, beverages with potential anticariogenic activity.

References

Catechins: definition, structure, green tea, black tea, cocoa

What are catechins?

Catechins or flavanols, with flavonols such as quercetin, and flavones such as luteolin, are a subgroup of flavonoids among the most widespread in nature.
Flavanols and proanthocyanidins, together with anthocyanins and their oxidation products, are the most abundant flavonoids in human diet.

Chemical structure of catechins

Basic Skeleton of Catechins
Fig. 1 – Basic Flavanol Skeleton

Chemically they differ from many other flavonoids as:

  • they lack the double bond between positions 2 and 3 of the C ring;
  • they not have a keto group at position 4;
  • they have a hydroxyl group in position 3, and for this reason they are also called flavan-3-ols.

Another distinctive feature of flavan-3-ols is their ability to form oligomers (two to ten units) or polymers (eleven or more units, up to 60 units) called proanthocyanidins or condensed tannins.

Catechins in foods

Catechins
Fig. 2 – Flavanols

Flavanols commonly found in plant-derived food products are catechin, epicatechin, gallocatechin, epigallocatechin, and their gallic acid ester derivatives: catechin gallate, gallocatechin gallate, epicatechin gallate, and epigallocatechin gallate (EGCG).
Flavanols present with higher frequency are catechin and epicatechin, which are also among the most common known flavonoids, and almost as popular as the related flavonol quercetin.
Cocoa and green tea are by far the richest sources in flavanols. In these foods the main flavonoids are catechin and epicatechin (cocoa is also a good source of epigallocatechin), but also their gallic acid ester derivatives, the gallocatechins.
However, they are also present in many fruits, especially in the skins of apples, blueberries (Vaccinium myrtillus) and grapes, in vegetables, red wine and beer, and peanuts.
As in many cases flavanols are present in the seeds or peels of fruits and vegetables, their intake may be limited by the fact that these parts are discarded during processing or while eaten.
Furthermore, in contrast to other flavonoids, catechins are not glycosylated in foods.
Proanthocyanidins, that is polymeric flavan-3-ols, are also commonly found in plant-derived food products. Their presence has been reported in the skin of peanuts and almonds, as in the berries.

Catechins in green tea and black tea

Green tea is an excellent source of flavonoids. The main flavonoids present in the leaves of the tea (as in cocoa beans) are catechin and epicatechin, monomeric flavanols, together with their gallate derivatives such as epigallocatechin gallate (EGCG).
Epigallocatechin gallate (EGCG) is the most abundant catechin in green tea and it seems to have an important role in determining green tea benefits, as the reduction of:

  • vascular inflammation;
  • blood pressure;
  • concentration of oxidized LDL.

Black tea (fermented tea) contains fewer monomeric flavanols, as they are oxidized during fermentation of the leaves to more complex polyphenols such as theaflavins (theaflavin digallate, theaflavin-3-gallate, and theaflavin-3′-gallate, all dimers) and thearubigins (polymers).
Theaflavins and thearubigins are present only in the tea; their concentrations in brewed tea are between 50- and 100-folds lesser than in tea leaves.

It should be noted that tea epicatechins are remarkably stable to heat in acidic environment: at pH 5, only about 15% is degraded after seven hours in boiling water (therefore, adding lemon juice to brewed tea does not cause any reduction in their content).

Catechins in cocoa and cocoa products

Cocoa has the highest content of polyphenols and flavanols per serving, a concentration greater than those found in green tea and red wine. Most of the flavonoids present in cocoa beans and derived products, such as black chocolate, are catechin and epicatechin, monomeric flavanols, but also epigallocatechin, and their derivatives such as the gallocatechins; among polymers, proanthocyanidins are also important.

Catechins in fruits, vegetables, and legumes

Catechin and epicatechin are the main flavanols in fruits. They are found in many fruits in different concentrations, respectively, between 5-3 and 0.5-6 mg/100 g fresh weight.
On the contrary, gallocatechin, epicatechin gallate, epigallocatechin, and epigallocatechin gallate (EGCG) are present in various fruits such as red grapes, berries, apples, peaches and plums, but in very low concentrations, less than 1mg/100 g fresh weight.
Except for lentils and broad beans, few legumes and vegetables contain catechins, and in very low concentrations, less than 1.5 mg/100 g fresh weight.

References

de la Rosa L.A., Alvarez-Parrilla E., Gonzàlez-Aguilar G.A. Fruit and vegetable phytochemicals: chemistry, nutritional value, and stability. 1th Edition. Wiley J. & Sons, Inc., Publication, 2010

de Pascual-Teresa S., Moreno D.A. and García-Viguera C. Flavanols and anthocyanins in cardiovascular health: a review of current evidence. Int J Mol Sci 2010;11:1679-1703 [Abstract]

Han X., Shen T. and Lou H. Dietary polyphenols and their biological significance. Int J Mol Sci 2007;9:950-988 [Abstract]

Manach C., Scalbert A., Morand C., Rémésy C., and Jime´nez L. Polyphenols: food sources and bioavailability. Am J Clin Nutr 2004;79(5):727-47 [Abstract]

Tsao R. Chemistry and biochemistry of dietary polyphenols. Nutrients 2010;2:1231-1246 [Abstract]