Anthocyanins

The main actives, accounting for many of the biological properties of Mirtoselect®, are anthocyanins (anthocyanosides).

Nearly one thousand anthocyanins, and more than 15 anthocyanidins, exist in the vegetal kingdom, although the greater part of them occurs rarely1, 2. The term anthocyanin was initially coined to indicate the substance responsible for the color of cornflower: it derives from the Greek term anthos=flower, and kuanos=blue, and refers to a group of water-soluble pigments responsible for red, pink, mauve, purple, blue, or violet color of most flower and fruits3.

The Vaccinium myrtillus L. (common name: bilberry or European blueberry) fruits are a well-known source of anthocyanins. Prior et al.4 reported that Vaccinium myrtillus berries contain the highest amounts of anthocyanins in comparison with other berries, including those of Vaccinium angustifolium (also called “wild” (lowbush) blueberries) or V. corymbosum the most common cultivated specie in North America also called the Northern highbush blueberry.
A linear relationship between ORAC and anthocyanins or total phenolics content has been shown thus not surprisingly Vaccinium myrtillus L. showed the highest ORAC result, followed by Vaccinium angustifolium L. samples.

The amount of anthocyanins in Vaccinium myrtillus L. berries ranges from 300 to 698 mg/100 g1 and increases during the ripening process5, 6, 7.

Bilberry contains a balanced mixture (Table 1) of the five major anthocyanins aglycons (delphinidin-, petunidin-, cyanidin-, peonidin- and malvidin) bound to monosaccharides (glucose, galactose and arabinose).

Mazza G., Miniati E., “Anthocyanins in Fruits, Vegetables and Grains”, CRC Press (1993).

Andersen O.M. and M. Jordheim M., The anthocyanins. In: Anderson O.M., Markham K.R.: “Flavonoids, Chemistry, biochemistry and applications”, CRC Press, Boca Raton, FL (2006), pp. 471–530.

Kumi Yoshida, Mihoko Mori and Tadao Kondo., “Blue flower color development by anthocyanins: from chemical structure to cell physiology”, Nat. Prod. Rep., 2009, 26, 884-915, Review

Prior R.L., Cao G., Martin A., Sofic E., McEwen J., O’Brien C., Lischner N., Elhenfeldt M, Kalt W., Krewer G., Mainland C.M., “Antioxidant Capacity As Influenced by Total Phenolic and Anthocyanin Content, Maturity, and Variety of Vaccinium Species”, J. Agric. Food Chem. 46, 2686 (1998).

Mazza G., Miniati E., “Anthocyanins in Fruits, Vegetables and Grains”, CRC Press (1993).

Brenneisen R., Steinegger E., “Zur Analytik der Polyphenole der. Früchte von Vaccinium myrtillus L. (Ericaceae)”, Pharm. Acta Helv. 56, 180 (1981).

L. Jaakola, K. Määttä, A.M. Pirttilä, R. Törrönen, S. Kärenlampi and A. Hohtola, “Expression of genes involved in anthocyanin biosynthesis in relation to anthocyanin, proanthocyanidin, and flavonol levels during bilberry fruit development”, Plant Physiology 130 (2) (2002), pp. 729–739.

R R1 R2 R3
Cyanidin 3-O-glycoside OH OH H arabinose or glucose or galactose
Delphinidin 3-O-glycoside OH OH OH arabinose or glucose or galactose
Malvidin 3-O-glycoside OCH3 OH OCH3 arabinose or glucose or galactose
Peonidin 3-O-glycoside OCH3 OH H arabinose or glucose or galactose
Petunidin 3-O-glycoside OH OH OCH3 arabinose or glucose or galactose
Table 1: Main anthocyanins of V. myrtillus L.

A HPLC profile of bilberry fruits shows a typical fingerprint characterized by the 15 major constituents of this fruit (Fig 1):

Fig. 1: Bilberry (Vaccinium myrtillus L.) HPLC fingerprint.

This profile is unique and is markedly different then the one of other fruits 8, 9 including Highbush blueberry, Lowbush Blueberry, Cranberry…that are differing from the type of anthocyanins aglycones (Table 2) and/or the sugar moiety.

Kaisu R., Määttä-Riihinen KR, Kamal-Eldin A, Mattila PH, González-Paramás AM, Törrönen AR.,”Distribution and Contents of Phenolic Compounds in Eighteen Scandinavian Berry Species”, J. Agric. Food Chem. 2004, 52, 4477-4486

Internal Report: 01/08/LRA-00

Fruit Petunidin Peonidin Cyanidin Delphinidin Malvidin
Bilberry (Vaccinium myrtillus L.) X X X X X
Blackcurrant X X X
Cranberry X X
Blackberry X
Lingonberry X X
Table 2: Concentration of anthocyanins grouped by aglycones

As an exemplification an HPLC chromatogram of black currant applying Indena’s HPLC method is hereunder reported. As clearly shown the major anthocyanins of blackcurrant contain rutinose, a sugar totally absent in bilberry anthocyanins. In fact, the two major peaks in the HPLC chromatogram of blackcurrant are totally absent in bilberry profile.

Fig 2: Fingerprint of Blackcurrant (Ribes nigrum L.) fresh fruit
Anthocyanidins present in low quantity in fresh bilberry fruits and in Mirtoselect® (<1%), are anthocyanins without the sugar moiety and should be considered anthocyanin degradation products occurring when there has been incorrect extract production and/or storage. Anthocyanidins are rare in nature and the metabolism of the anthocyanins produces only trace amounts of bioavailable anthocyanidins.
  1. Mazza G., Miniati E., “Anthocyanins in Fruits, Vegetables and Grains”, CRC Press (1993).
  2. Andersen O.M. and M. Jordheim M., The anthocyanins. In: Anderson O.M., Markham K.R.: “Flavonoids, Chemistry, biochemistry and applications”, CRC Press, Boca Raton, FL (2006), pp. 471–530.
  3. Kumi Yoshida, Mihoko Mori and Tadao Kondo., “Blue flower color development by anthocyanins: from chemical structure to cell physiology”, Nat. Prod. Rep., 2009, 26, 884-915, Review
  4. Prior R.L., Cao G., Martin A., Sofic E., McEwen J., O’Brien C., Lischner N., Elhenfeldt M, Kalt W., Krewer G., Mainland C.M., “Antioxidant Capacity As Influenced by Total Phenolic and Anthocyanin Content, Maturity, and Variety of Vaccinium Species”, J. Agric. Food Chem. 46, 2686 (1998).
  5. Brenneisen R., Steinegger E., “Zur Analytik der Polyphenole der. Früchte von Vaccinium myrtillus L. (Ericaceae)”, Pharm. Acta Helv. 56, 180 (1981).
  6. Brenneisen R., Steinegger E., “Quantitativer vergleich del Polyphenole in Fruechten von Vaccinium myrtillus L. undersciedlichen Reifegrades”, Pharm. Acta Helv. 56, 341 (1981).
  7. L. Jaakola, K. Määttä, A.M. Pirttilä, R. Törrönen, S. Kärenlampi and A. Hohtola, “Expression of genes involved in anthocyanin biosynthesis in relation to anthocyanin, proanthocyanidin, and flavonol levels during bilberry fruit development”, Plant Physiology 130 (2) (2002), pp. 729–739.
  8. Kaisu R., Määttä-Riihinen KR, Kamal-Eldin A, Mattila PH, González-Paramás AM, Törrönen AR.,”Distribution and Contents of Phenolic Compounds in Eighteen Scandinavian Berry Species”, J. Agric. Food Chem. 2004, 52, 4477-4486
  9. Internal Report: 01/08/LRA-00

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