Anthocyanidin

Molecule in 3D of the anthocyanidin cyanidin

Anthocyanidins are common plant pigments. They are the sugar-free counterparts of anthocyanins based on the flavylium ion or 2-phenylchromenylium, which is a type of oxonium ion (chromenylium is referred also to as benzopyrylium).[1] They form a large group of polymethine dye. In particular anthocyanidins are salt derivatives of the 2-phenylchromenylium cation, also known as flavylium cation. As shown in the figure below, the phenyl group at the 2-position can carry different substituents. The counterion of the flavylium cation is mostly chloride. With this positive charge, the anthocyanidins differ from other flavonoids. 31 monomeric anthocyanidins have been properly identified, most of the anthocyanins are based on cyanidin (30%), delphinidin (22%), and pelargonidin (18%), respectively. Altogether 20% of the anthocyanins are based on the three common anthocyanidins (peonidin, malvidin, and petunidin) that are methylated. Around 3, 3, and 2% of the anthocyanins or anthocyanidins are labeled as 3-desoxyanthocyanidins, rare methylatedanthocyanidins, and 6-hydroxyanthocyanidins, respectively.

In bryophytes, anthocyanins are usually based on 3-desoxyanthocyanidins located in the cell wall. A new anthocyanidin, riccionidin A, has been isolated from the liverwort Ricciocarpos natans. It could be derived from 6,7,2′, 4′, 6′-pentahydroxyflavylium, having undergone ring closure of the 6’ -hydroxyl at the 3-position. Its visible spectrum in methanolic HCl is at 494 nm. This pigment was accompanied by riccionidin B, which most probably is based on two molecules of riccionidin A linked via the 3′- or 5′ -positions. Both pigments were also detected in the liverworts Marchantia polymorpha, Riccia duplex, and Scapania undulata.[2]

pH

The stability of anthocyanidins is dependent on pH. At a low pH (acidic conditions), colored anthocyanidins are present, whereas at a higher pH (basic conditions) the colorless chalcones forms are present.

Classification

3-Deoxyanthocyanidins such as luteolinidin are a class of anthocyanidins lacking an hydroxyl group on carbon 3.

Selected anthocyanidins and their substitutions
Anthocyanidin Basic structure (R4′ = −OH) R3′ R5′ R3 R5 R6 R7
Aurantinidin −H −H −OH −OH −OH −OH
Capensinidin −OCH3 −OCH3 −OH −OCH3 −H −OH
Cyanidin −OH −H −OH −OH −H −OH
Delphinidin −OH −OH −OH −OH −H −OH
Europinidin −OCH3 −OH −OH −OCH3 −H −OH
Hirsutidin −OCH3 −OCH3 −OH −OH −H −OCH3
Malvidin −OCH3 −OCH3 −OH −OH −H −OH
Pelargonidin −H −H −OH −OH −H −OH
Peonidin −OCH3 −H −OH −OH −H −OH
Petunidin −OH −OCH3 −OH −OH −H −OH
Pulchellidin −OH −OH −OH −OCH3 −H −OH
Rosinidin −OCH3 −H −OH −OH −H −OCH3

References

  1. ↑ IUPAC Goldbook
  2. ↑ Flavonoids : chemistry, biochemistry, and applications. Andersen, Øyvind M., Markham, Kenneth R. CRC, Taylor & Francis. 2006. ISBN 0849320216. OCLC 60454800.

Media related to Anthocyanidins at Wikimedia Commons

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.