Anthocyanins

yvind M Andersen, University of Bergen, Bergen, Norway

The anthocyanins are a group of pigments providing many red and blue colours in the plant kingdom. These glycosides belong to the flavonoid class and are based on different anthocyanidins.

Secondary article
Article Contents
. Introduction . Chemistry of Anthocyanins . Genetics and Biosynthetic Pathway . Genetic Manipulation of Flower Colour . Colour Expression in Floral Tissues

Introduction
The anthocyanins are part of the group of compounds collectively known as avonoids. The terminology (anthos 5 ower, kyanos 5 blue) was originally used to describe the pigment in blue cornower (Centaurea cyanus). Anthocyanins are responsible for cyanic colours ranging from salmon pink through red and violet to dark blue of most owers, fruits and leaves of angiosperms. They may be visible in roots, tubers, stems, bulbils, etc., and are also found in many gymnosperms, ferns and some bryophytes. Anthocyanins occur in both epidermal and subepidermal cells (infrequently in petal mesophyll), dissolved in vacuoles or accumulated in vesicles called anthocyanoplasts. In bryophytes, anthocyanins are associated with the cell walls. Their concentration in pigmented epidermal petal cells is commonly of the order of 10 2 3 10 2 2 mol L 2 1. It is notable that for many isolated anthocyanins these concentrations exceed those achievable in aqueous solutions.

. Anthocyanins of Fruits . Anthocyanins of Vegetative Tissues . Anthocyanin Production in Cell Culture . Anthocyanins and Food Colours

Chemistry of Anthocyanins
Structures
The anthocyanins consist of an aglycone (anthocyanidin), sugar(s) and in many cases acyl group(s). While 22 monomeric anthocyanidins (Table 1) have been properly identied, nearly all reported anthocyanins (over 500) are based on just six anthocyanidins. 3-Desoxyanthocyanidins are the only anthocyanidins stable enough to occur in their nonglycosidated form in plants. Desoxyanthocyanins have a limited distribution in angiosperms and are the anthocyanins of ferns and bryophytes. The anthocyanin sugars are represented by one or more units of glucose (most common), galactose, rhamnose, arabinose, or xylose connected to the aglycone 3- and sometimes also to the 5-, 7-, 3-, 4- or 5-hydroxyl groups. Exceptionally, glucuronic acid fulls this function in Bellis perennis. The sugars increase the anthocyanin stability and water solubility. Malonic and acetic acid are the most frequent aliphatic acyl groups in anthocyanins, while malic, oxalic and succinic acid have been identied in Dianthus, Orchidaceae and Centaurea, respectively. The

most common aromatic acyl groups in anthocyanins are pcoumaric, caeic, ferulic, sinapic and p-hydroxybenzoic acid. Gallic acid is reported in Aceraceae and Nymphaeaceae, while 3,4-dimethoxy- and 3,4,5-trimethoxycinnamoyl have been identied in black carrot (Daucus carota). When determined, the acyl group in anthocyanins is mostly linked to the sugar 6-position, although 2-, 3- and 4acylations have been reported. Two anthocyanins conjugated with sulfate have been isolated from Babiana stricta, and covalent complexes including anthocyanin and avone (from Eichhornia crassipes, Pontederiaceae) or anthocyanin and avonol (from Allium schoenoprasum; Liliaceae) have recently been characterized. The largest monomeric anthocyanin recorded to date, ternatin A1 (from Clitoria ternatea), is composed of delphinidin with seven molecules of glucose, four of coumaric acid and one of malonic acid (molecular mass: 2108.87 g mol 2 1). As described below, many anthocyanins are found associated with copigments and/or metal ions.

Equilibrium forms and pH influence

Each anthocyanidin gives rise to several forms (Figure 1) with dierent colours and stability. Based on observations of some relatively simple anthocyanins in vitro, the following scheme is generally accepted. At a pH of approximately 3 or lower, the orange, red or purple avylium cation predominates. As the pH is raised, kinetic and thermodynamic competition occurs between the hydration reaction on position 2 of the avylium cation and the proton transfer reactions related to its acidic hydroxyl groups. While the rst reaction gives colourless carbinol pseudobases that can undergo ring-opening to yellow retrochalcones, the latter reactions give rise to more violet quinonoidal bases. Further deprotonation of the quinonoidal bases can take place at pH between 6 and 7 with the formation of more bluish resonance-stabilized quinonoid anions.
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Anthocyanins

Table Table 1 Structures of naturally occurring anthocyanidins

Substitution pattern Anthocyanidina Pelargonidin (Pg)b Cyanidin (Cy)b Peonidin (Pn)b Delphinidin (Dp)b Petunidin (Pt)b Malvidin (Mv)b Aurantinidin 6-Hydroxycyanidin 6-Hydroxydelphinidin Apigeninidin Luteolinidin Tricetinidin 5-Methylcyanidin Rosinidin Pulchellidin Europinidin Capensinidin Hirsutidin Ricciniodin Ac
a b

3 OH OH OH OH OH OH OH OH OH H H H OH OH OH OH OH OH OH

5 OH OH OH OH OH OH OH OH OH OH OH OH OMe OH OMe OMe OMe OH H

6 H H H H H H OH OH OH H H H H H H H H H OH

7 OH OH OH OH OH OH OH OH OH OH OH OH OH OMe OH OH OH OMe OH

3' H OH OMe OH OMe OMe H OH OH H OH OH OH OMe OH OMe OMe OMe H

5' H H H OH OH OMe H H OH H H OH H H OH OH OMe OMe H

In addition: sphagnorubins AC from peat moss, Sphagnum. The most common anthocyanidins. c Ring closure on the basis of ether linkage between the 3- and 6'-positions. Ricciniodin A and its dimer, ricciniodin B, have an additional OHgroup in the 2'-position
R OH HO OH O OH R OX CE OX B2 OX HO R OH AH+ HO OH OX O CZ OX B4 OX OH OX A7 OX OX A74 OX OX HO O R H2O/H+ OX O O R H+ O O R O + OX HO O R OX H2 O/H+ R OH A 4 H+ R OH R O OX HO O R OX A47 OX R OH R O H+ O O R O

R OX

R OH

2 2 Figure 1 General scheme for anthocyanin equilibrium forms. AH 1 , flavylium cation; A7 and A4, quinonoidal bases; A4 7 and A74, ionized quinonoidal bases; B2 and B4, carbinol pseudobases; CE and CZ, retrochalcones; X, glycosyl; R, H, OH or OCH3. The individual forms are supplied with their supposed colours as background.

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Analysis
Most anthocyanins show instability towards a variety of chemical and physical parameters, including oxygen, high temperatures and most pH values. The various anthocyanins have similar structures and often occur in complex mixtures (Figure 2), which makes them rather dicult to isolate. A routine analysis may consist of just one high-performance liquid chromatographic injection (5 mL) of a crude extract of 0.5 mg dried petal. However, a typical complete structure determination demands extraction of approximately 200 g plant material with acidied alcoholic solvent, followed by purication and separation using various chromatographic techniques before structure elucidation by spectroscopy and sometimes chemical degradation. Recent techniques in mass spectrometry and two-dimensional nuclear magnetic resonance spectroscopy (Strack and Wray, 1994) have become vital for the determination of many anthocyanin linkage positions and aliphatic acyl groups.

Genetics and Biosynthetic Pathway

In the nineteenth century Gregor Mendel derived his laws of inheritance from the results of experiments crossing redand white-owering peas, and today avonoid genes are the preferred genes for elucidation of structure, regulation and interaction at the molecular level. Particularly detailed gene lists have been published for Antirrhinum, Zea mays and Petunia; at least 35 genes are known to aect ower colour for the latter genus. This has led to understanding of the steps in anthocyanin biosynthesis (Figure 3), and isolation of most of the structural and regulatory genes that encode the enzymes involved (Forkman, 1994). However, the important reactions in the biosynthesis of anthocyanidins from leucoanthocyanidins (avan-2,3-trans-3,4-cis-diols) as well as in the conversion of avan-4-ols to 3-desoxyanthocyanidins are still partly unknown. Many enzymes catalysing hydroxylation, methylation, glycosylation and acylation of substrates to give the various anthocyanins have been described.

Genetic Manipulation of Flower Colour

Breeders use continuous crossing and selection to produce a variety of ower colours and patterns. However, each genus has a limited gene pool. There are no natural blue carnations, chrysanthemums or roses. Nevertheless, recent advances in genetic engineering have been used successfully in modifying the ower colour of several species, including those of Chrysanthemum, Eustoma, Gerbera, Nicotiana and Rosa. The rst case of colour manipulation by recombinant DNA techniques generated the naturally missing pelargonidin derivatives in Petunia. Through transformation of a suitable Petunia receptor line with a maize gene (A1 cDNA), orange owers were created. Another gene manipulation approach (antisense technique) involving Petunia inhibited specic steps in the biosynthesis, which produced paler colours and unexpected colour patterns. While most factors governing anthocyanin gene regulation in general are known, the inuences of copigmentation, pH, etc. on ower colours seem to be less amenable to control.

Colour Expression in Floral Tissues

The main function of ower pigmentation is to attract pollinators. Bees prefer blue, yellow and ultraviolet colours, while hummingbirds like orange, scarlet and bright red. In temperate species an evolutionary trend towards blue owers is reected in the frequency of blue-coloured species in temperate members of Labiatae, Polemoniaceae and Boraginaceae. Although the
3

Figure 2 Many plants contain a complex mixture of anthocyanins as shown by the high-performance liquid chromatogram of berries of Vaccinium uliginosum, which shows the 15 anthocyanidin-3monoglycosides typical for blueberries (Table 3).

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Figure 3 Biosynthesis of the major anthocyanin in strawberry, pelargonidin 3-O-b-glucoside. 1, chalcone synthase; 2, chalcone isomerase; 3, flavanone 3hydroxylase; 4, dihydroflavonol 4-reductase; 5, flavanone 4-reductase.

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Anthocyanins

cyanic ower colours are attributed to the individual anthocyanins present (Table 2) and their cellular concentration, the exquisite shades are highly inuenced by factors such as local pH, copigmentation, metal complexation, optical properties of the anthocyanin-containing cells, etc. Many aspects regarding the colour mechanisms have been elucidated during the last decades, but the interpretation is far from complete

display bluing of the colour, which correlates with anthocyanin transformations caused by a pH increase (Figure 1).

Metalloanthocyanins
Metals have been found important for formation of blue colours in fewer species than earlier supposed. The blue petals of Commelina communis contain the supramolecule, commelinin, which consists of six molecules of a malonylated delphinidin 3,5-diglucoside copigmented with six avone molecules complexed with two magnesium atoms (Figure 4). Similar metal complexes have also been proposed in blue owers of Centaurea cyanus, Hydrangea macrophylla, Lupinus sp. and Salvia patens.

Self-association, intra- and intermolecular copigmentation

The pH of the cell sap is usually in the region of 46. Most anthocyanins in vitro are virtually without colour in this region since they exist mainly as colourless carbinol bases before they are transformed to chalcone forms (Figure 1). The presence of one or more acyl groups in the anthocyanin molecule seems to hinder hydrolysis of the red avylium cationic form to the colourless carbinol base, allowing preferential formation of the blue quinonoidal bases and their anions. This intramolecular copigmentation thus implies more bluish colours of high intensity in mildly acidic or neutral media. A similar mechanism involving stacked complexes is proposed for intermolecular copigmentation of anthocyanins with other avonoids and similar planar compounds. Cultivars with dierent colours but the same anthocyanin have been found to contain dierent copigments, or altered molar proportions of anthocyanin to copigment. When pigment concentrations become relatively high, anthocyanins themselves may act as copigments and participate in self-association reactions. The colour intensity (absorbance) will then increase more than proportionally to anthocyanin concentration; however, the extent of anthocyanin selfassociation in vivo is far from clear. Some ageing owers

Anthocyanins of Fruits
Fruits with red to blue colours that contrast with the background green of the foliage advertise their presence to animals to ensure seed dispersal. A gardener will observe that birds prefer to eat normal red currant (Ribes rubrum) berries rather than light-yellow berries of a mutant population. Individual anthocyanins in fruits are normally without acylation; this is in contrast to many anthocyanins in owers and, curiously enough, underground plant parts that may be acylated (Table 2 and Table 3).

Anthocyanins of Vegetative Tissues

Anthocyanins in vegetative tissue are normally masked by chlorophyll pigmentation; however, their colours in

Figure 4 The supramolecule commelinin isolated from flowers of Commelina communis consists of six anthocyanin molecules (M) and six flavones (F) surrounding two magnesium ions (shown in red). Adapted from Kondo et al. (1992).

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Table 2 Anthocyanins in selected flowers Botanical name Alstroemeria spp. Antirrhinum spp. Bellis perennis Campanula spp. Common name Parrotlily Snapdragon Daisy Bellflower Major anthocyanins presenta

Cy, Dp, 6-hydroxy Cy and 6-hydroxy Dp 3-(6-rhamnosylglucoside), C Cy, Dp and Pn 3-(6-rhamnosylglucoside), 3-glucoside, 3,5-diglucosid Cy 3-(6-malonyl-2-glucuronosylglucoside) Bisdeacylplatyconin, violdelphin, campanin, monodeacylcampanin, ru 7-glycosides)-3-(6-rhamnosylglucoside) Crocus Mv and Pt 3,7-di(6-malonylglucoside), Dp 3-glucoside-7-(6-malonylg Crocus spp. 3-(6-rhamnosylglucoside), 3,5-diglucoside Cy and Pg 3-(6-malylglucoside), Cy 3,5-diglucoside-(6,6-malyl dieste Dianthus caryophyllus Carnation Erythrina Cy and Pg 3-(2-glucosylglucoside), 3-glucoside, 3,5-diglucoside Erythrina spp. Dp, Cy and Pg 3-(6-rhamnosylgalactoside)-5-(6-acylglucosides) Eustoma grandiflorum Lisianthus Gentian Gentiodelphins, gentiocyanins, albireodelphins (acylated Dp and Cy 3 Gentiana spp. Geranium Mv 3-glucoside 5-(6-acetylglucoside), Dp 3-glucoside, Cy 3,5-digluco Geranium spp. Hibiscus Cy 3-(2-glucosylglucoside), Cy and Dp 3-(2-xylosylglucoside), Cy, M Hibiscus spp. Acylated Cy, Pg, Dp and Pt 3,5-diglucosides Hyacinthus orientalis Hyacinth Iris Dp, Mv, Pt, Pn and Cy 3-(coumaryl-6-rhamnosylglucoside)-5-glucosi Iris ensata Lobelia Acylated Cy and Dp 3-(6-rhamnosylglucosides)-5,3'-diglucosides, 3-( Lobelia erinus Malva Mv 3-(6-malonylglucoside)-5-glucoside, 3,5-diglucoside Malva sylvestris Himalayan poppy Cy 3-(malonyl-2-xylosylglucoside)-7-glucoside Meconopsis spp. Metrosideros Cy, Pn, Mv, Dp and Pt 3-glucoside, Cy and Mv 3,5-diglucoside Metrosideros spp. Water lily Dp and Cy 3-(2-galloyl-6-acetylgalactoside), Dp 3-(6-acetylgalactosid Nymphaea spp. Peony Pn, Cy, and Pg 3-glucoside, 3,5-diglucoside Paeonia spp. Pelargonium Pg, Cy, Pn, Dp, Pt and Mv 3-glucoside-5-(6-acetylglucoside), 3,5-digl Pelargonium spp. Petunia Acylated Mv, Pt and Pn 3-(6-rhamnosylglucosides)-5-glucoside, Mv, P Petunia spp. 3,5-diglucoside, 3-(6-rhamnosylglucoside)-5-glucoside, 3-(6-rhamno Norway spruce Cy and Pn 3-glucoside Picea abies Rose Cy, Pg and Pn 3,5-diglucoside, 3-glucoside Rosa spp. Pt and Mv 3-(6-rhamnosylglucoside)-5-glucoside Saintpaulia ionantha African violet Tulip Pg, Cy and Dp 3-(6-rhamnosylglucoside), Pg and Cy 3-[6-(2-acetylrha Tulipa spp. Verbena Acylated Pg, Cy and Dp 3,5-diglucosides, 3-glucosides Verbena spp.
a

Different species and cultivars may have different content. See Table 1 for Cy, Dp, Mv, Pg, Pn and Pt.

autumn leaves and trees like copper beech (Fagus sylvatica f. purpurea) are really outstanding. Their appearance in young leaves and seedlings are often transient. Anthocyanin functions in vegetative tissues are not properly established, and accumulation resulting from cold temperatures, increased sugar concentrations, metal deciency, dehydration, etc. are commonly described as stress markers. Anthocyanins are sometimes reported as protective UV lters, and their presence in leaves of some tropical plants has been related to light harvesting. Local accumulation in necrotic areas in response to pathogens and injury may represent potential defence functions. Recent evidence indicates that 3-desoxyanthocyanins in sorghum can act as phytoalexins.
6

Anthocyanin Production in Cell Culture

Strategies for production of anthocyanins from plant cell and tissue cultures have been reported for more than 30 species including Daucus carota, Fragaria ananassa, Vaccinium spp., Vitis spp., Solanum tuberosum, Malus sylvestris, Perilla frutescens, Ipomoea batatas, Euphorbia millii and Dioscorea cirrhosa. A highly productive cell line of Aralia cordata, obtained by continuous cell aggregate cloning, has been reported to yield anthocyanins in concentrations as high as 17% on a dry weight basis. However, the myriad of variables (light, medium sugars, dissolved oxygen, etc.) that inuence the yield and quality, dictate that most current anthocyanin production systems

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Table 3 Anthocyanins in selected fruits and vegetables Botanical name Allium cepa Aronia melanocarpa Brassica oleracea Citrus sinensis Cyphomandra betacea Daucus carota Fragaria ananassa Litchi chinensis Malus pumila Mangifera indica Oryza sativa Passiflora edulis Phaseolus spp. Prunus avium Prunus cerasus Raphanus sativus Rheum rhaponticum Ribes nigrum Ribes rubrum Rubus idaeus Rubus spp. Sambucus nigra Solanum melongena Solanum tuberosum Vaccinium corumbosum Vaccinium macrocarpon Vaccinium myrtillus Vaccinium vites-idaea Vitis spp.
a b

Common name Red onion Chokeberry Red cabbage Blood orange Tamarillo Black carrot Strawberry Lychee Apple Mango Rice Passion fruit Bean Sweet cheery Sour cherry Red radish Rhubarb Blackcurrant Redcurrant Red raspberry Blackberries Elderberry Aubergine Potato Highbush blueberry American cranberry Bilberry Cowberry Grapes

Major anthocyanins presenta Cy 3-(6-malonylglucoside), 3-(6-malonyl-3-glucosylglucoside), 3-glucoside, 3-(3,6-dimalonyl glucoside) Cy 3-galactoside, 3-arabinoside, 3-glucoside Several acylated Cy 3-(2-glucosylglucosides)-5-glucoside Cy and Dp 3-glucoside, Cy 3-(4-acetylglucoside) Dp, Cy and Pg 3-(6-rhamnosylglucoside) Several acylated Cy 3-(2-xylosyl-6-glucosylgalactosides), Cy 3-(2-xylosyl-6-glucosylgalactoside) Pg and Cy 3-glucoside, Pg 3-(6-rhamnosylglucoside) Cy 3-(6-rhamnosylglucoside), 3-glucoside, Mv 3-(acetylglucoside) Cy 3-galactoside, 3-arabinoside, 3-glucoside Pn 3-galactoside Cy and Pn 3-glucoside Cy 3-glucoside Mv, Dp, Pg, Cy and Pt 3-glucoside, Mv, Dp, Pg and Cy 3,5-diglucoside Cy 3-(6-rhamnosylglucoside), 3-glucoside Cy 3-(2-glucosyl-6-rhamnosylglucoside), 3-(6-rhamnosylglucoside), 3-glucoside, 3-(2-glucosyl glucoside) Several acylated Pg 3-(2-glycosylglucosides)-5-glucoside Cy 3-glucoside, 3-(6-rhamnosylglucoside) Cy and Dp 3-glucoside, 3-(6-rhamnosylglucoside) Cy 3-(2-xylosyl-6-rhamnosylglucoside), 3-(2-xylosylglucoside), 3-(6-rhamnosylglucoside), 3-(2-glucosyl-6-rhamnosylglucoside), 3-glucoside Cy 3-(2-glucosylglucoside), 3-glucoside, 3-(6-rhamnosylglucoside), 3-(2-glucosyl-6-rhamnosylglucoside) Cy 3-glucoside, 3-(6-rhamnosylglucoside) Cy 3-(2-xylosylglucoside), 3-glucoside, 3-(2-xylosylglucoside)-5-glucoside Dp 3-[6-(4-coumarylrhamnosyl)glucoside]-5-glucoside, 3-glucoside, 3-(6-rhamnosylglucoside) Pt and Pg 3-[6-(4-coumarylrhamnosyl)glucoside]-5-glucoside Dp, Cy, Pt, Mv and Pn 3-glucoside, 3-galactoside, 3-arabinoside Cy and Pn 3-galactoside, 3-arabinoside, 3-glucoside Dp, Cy, Pt, Mv and Pn 3-glucoside, 3-galactoside, 3-arabinoside Cy 3-galactoside, 3-arabinoside Mv, Pt, Pn and Cy 3-glucoside, 3,5-diglucoside, 3-(6-coumarylglucoside), 3-(acetylglucoside), 3-(6-coumarylglucoside)-5-glucoside

Amountb 0.2 1.6 0.4 0.2c 0.3 1.3 0.2 1.0 2.0 <0.1 1.5 0.6 0.3 2.5 0.2 0.4 1.6 0.6 1.2 2.5 0.7 3.1 0.8 1.2d

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Anthocyanins

Different cultivars may have different content. See Table 1 for abbreviations. g per kg fresh weight. The values vary with cultivar, environmental factrors and experimental procedure. c g L1. d Wine: approximately 0.2 g L1.

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today operate on a research rather than on an industrial scale.

Instability
Anthocyanins are slowly oxidized in aqueous solutions. Although the degradation rate increases with increasing temperature and light exposure, most colour is retained during fruit canning and jam and sugar boiling. The anthocyanins react with sulfur dioxide, some cations and proteins, etc., and will undergo transformations under storage, for instance during maturation of wine. The decolorization caused by the enzymatic activity of glycosidases and polyphenoloxidases varies with the product and plant involved. The anthocyanins are furthermore dicult to purify, and most anthocyanins decolorize in weak acid and neutral solutions. It is widely cited that the stability of anthocyanins decreases with increasing pH. However, it has recently been shown that some increase in stability reappears at pH values between 7.5 and 9.0. The exploitation of acylated anthocyanins with improved colour and stability in weakly acidic solutions is the most promising area for advancing anthocyanins as natural food colours.

Anthocyanins and Food Colours

The anthocyanins form the red and blue colours of most fruits and vegetables (Table 3), and therefore are responsible for the attractive colours of many fruit juices, wines, jams and preserves. There is worldwide interest in additional use of food colourants from natural sources as a consequence of perceived consumer preferences as well as legislative action, which has continued the delisting of approved articial dyes. The motives for extended use are also inuenced by promising observations of their potential benecial health eects related to cardiovascular diseases, cancer treatment, virus inhibition and general antioxidant activity; however, further investigations of these properties are required.

References Intake
On the basis of toxicological data, although somewhat limited, anthocyanins have been approved for use in foods in Europe with label E163. Their principal applications are in soft drinks, fruit preserves and dry mixes such as drink powders and sugar confectionery. Commercial anthocyanin pigments are mainly extracted from blue grapes; however, several of the sources given in Table 3 have also been exploited (Bridle and Timberlake, 1997). In 1982, an ADI (acceptable daily intake) of 02.5 mg anthocyanins per kg bodyweight per day was calculated. Diculties in the standardization of experimental procedures used to obtain quantitative data should not be underestimated. With median consumption in some European countries of about 60 ml day 2 1 for red wines and red juices, 5 g day 2 1 for red and blue fruits, berries and vegetables, an estimated anthocyanin intake less than 20 mg day 2 1 can be anticipated. This number is 10 times less than the widely cited estimate of an average daily intake in the USA.
Bridle P and Timberlake CF (1997) Anthocyanins as natural food colours selected aspects. Food Chemistry 58: 103109. Forkman G (1994) Genetics of avonoids. In: Harborne JB (ed.) The Flavonoids Advances in Research Since 1986, pp. 537564. London: Chapman & Hall. Kondo T, Yoshida K, Nakagawa A et al. (1992) Structural basis of bluecolour development in ower petals from Commelina communis. Nature 358: 515518. Strack D and Wray V (1994) Anthocyanins. In: Harborne JB (ed.) The Flavonoids Advances in Research Since 1986, pp. 122. London: Chapman & Hall.

Further Reading
Brouillard R and Dangles O (1994) Anthocyanins and ower colour. In: Harborne JB (ed.) The Flavonoids Advances in Research Since 1986, pp. 566588. London: Chapman & Hall. Forkman G and Heller W (1999) Biosynthesis of avonoids. In: Sankawa U (ed.) Comprehensive Natural Products, vol. 1. Amsterdam: Elsevier. Harborne JB (1989) Plant phenolics. In: Dey PM and Harborne JB (series eds) Methods in Plant Biochemistry. London: Academic Press. Mazza G and Miniati E (1993) Anthocyanins in Fruits, Vegetables, and Grains. Boca Raton, FL: CRC Press.

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