Anthocyanidins are common plant pigments, the sugar-free counterparts of

anthocyanin Anthocyanins (), also called anthocyans, are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue, or black. In 1835, the German pharmacist Ludwig Clamor Marquart gave the name Anthokyan to a chemical compo ...

s. They are based on the

flavylium Pyrylium is a cation (positive ion) with formula , consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively charged oxygen atom. The bonds in the ring are conjugated as in benzene, giving it an aroma ...

cation An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...

, an

oxonium ion In chemistry, an oxonium ion is any cation containing an oxygen atom that has three bonds and 1+ formal charge. The simplest oxonium ion is the hydronium ion (). Alkyloxonium Hydronium is one of a series of oxonium ions with the formula R''n''H ...

, with various groups

substituted A substitution reaction (also known as single displacement reaction or single substitution reaction) is a chemical reaction during which one functional group in a chemical compound is replaced by another functional group. Substitution reactions ar ...

for its

hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...

atoms. They generally change color from red through purple, blue, and bluish green as a function of pH. Anthocyanidins are an important subclass of the

polymethine Polymethines are compounds made up from an ''odd'' number of methine groups (CH) bound together by alternating single and double bonds.Kachovski and Dekhtyar, ''Dyes and Pigments'', 22 (1983) 83-97. Compounds made up from an ''even'' number of meth ...

dyes and

flavonoid Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans. Chemically, flavonoids ...

s. The flavylium cation is a

chromenylium Pyrylium is a cation (positive ion) with formula , consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively charged oxygen atom. The bonds in the ring are conjugated as in benzene, giving it an arom ...

cation with a

phenyl In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen ...

group substituted in position 2; and chromenylium (also called benzopyrylium) is a bicyclic version of

pyrylium Pyrylium is a cation (positive ion) with formula , consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively charged oxygen atom. The bonds in the ring are conjugated as in benzene, giving it an aroma ...

. The positive charge can move around the molecule. At least 31 monomeric anthocyanidins have been properly identified in living organisms, mostly as the core components of anthocyanins. The latter are responsible for the red, purple, blue, or black color of many fruits (like

grape A grape is a fruit, botanically a berry, of the deciduous woody vines of the flowering plant genus ''Vitis''. Grapes are a non- climacteric type of fruit, generally occurring in clusters. The cultivation of grapes began perhaps 8,000 years ago, ...

s and

blueberries Blueberries are a widely distributed and widespread group of perennial flowering plants with blue or purple berries. They are classified in the section ''Cyanococcus'' within the genus ''Vaccinium''. ''Vaccinium'' also includes cranberries, bi ...

), flowers (like

rose A rose is either a woody perennial flowering plant of the genus ''Rosa'' (), in the family Rosaceae (), or the flower it bears. There are over three hundred species and tens of thousands of cultivars. They form a group of plants that can be ...

s), leaves (like

purple cabbage The red cabbage (purple-leaved varieties of ''Brassica oleracea'' Capitata Cultivar group, Group) is a kind of cabbage, also known as Blaukraut after preparation. Its leaves are colored dark red/purple. However, the plant changes its color acco ...

), and even tubers (like

radish The radish (''Raphanus raphanistrum'' subsp. ''sativus'') is an Eating, edible root vegetable of the family Brassicaceae that was domesticated in Asia prior to Roman Empire, Roman times. Radishes are grown and consumed throughout the world, be ...

es and

purple yam ''Dioscorea alata'', also known as purple yam, ube (, ), or greater yam, among many other names, is a species of yam (a tuber). The tubers are usually a vivid violet-purple to bright lavender in color (hence the common name), but some range in ...

s). They are also found in some animals.

Classification

3-Deoxyanthocyanidins such as

luteolinidin Luteolinidin is a member of the 3-deoxyanthocyanidins. It is a cation with ill-defined anions. This orange species that can be found in '' Sorghum bicolor''. Luteolinidin was shown to inhibit CD38 with relatively high potency compared with pre ...

are a class of anthocyanidins lacking an hydroxyl group on carbon 3. :

Natural occurrence

Most plant 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 respectively labeled as 3-desoxyanthocyanidins, rare methylated anthocyanidins, 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 ''Ricciocarpos natans'' (vernacular name: fringed heartwort) is the only species in the genus ''Ricciocarpos'', a genus of Marchantiophyta, liverworts in the family Ricciaceae. It was formerly listed in 1759 as a species of ''Riccia'' by Carl Lin ...

''. 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

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...

ic 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''.

Effect of 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 Chalconoids Greek: χαλκός ''khalkós'', "copper", due to its color), also known as ''chalcones'', are natural phenols related to chalcone. They form the central core for a variety of important biological compounds. They show antibacterial, a ...

forms are present. Cyanidin - Farbstoff pH-Abhaengigkeit

References

External links

* {{Authority control PH indicators Bioindicators