Glycosides anthocyanidin

Toki, K. et al., Two malonylated anthocyanidin glycosides in Ranunculus asiaticus. Phytochemistry, 42, 1055, 1996. 

In contrast to flavones and flavonols, anthocyanidins are rarely, if every, found free in nature (Heller and Forkmann, 1988). 3-(9-Glycosylation is a likely prerequisite for antho-cyanin accumulation because of the instability of the flavyl-ium cation. UDP-Glucose flavonoid 3-(9-glucosyltransfer-ase is involved in formation of anthocyanidin glycosides. 

Glycosides, particularly of phenoHc compounds, are widely distributed in plant tissues (2,10). Glycosides of anthocyanidins, flavones, flavanols, flavanones, flavanonols, stilbenes and saponins, gaUic acid derivatives, and condensed tannins are all common. 

The chemical formulae for a variety of plant phenols are given in Fig. 16.2, including examples of simpler phenols, such as cinnamic acid derivative, and of tocopherols, flavonoids, flavonoid glycosides and anthocyanidins. The flavonoids include the following subclasses flavanones (taxifolin), flavones (luteolin), flavonols (quercetin) and flavanols (catechin/epicatechin). The... 

Six anthocyanidins are commonly found in plants and plant-derived foods and beverages pelargonidin, cyanidin, delphinidin, peonidin, petunidin, and malvidin. Their structures differ in the number and position of hydroxyl and methoxyl groups on the flavan nucleus. The most commonly occurring anthocyanidin is cyanidin, and all these anthocyanidins are found in plants as glycosides with or without acylation, leading to around 400 different stractures. 

The numbers and types of fragments depend on the anthocyanin structure pattern. The aglycone (anthocyanidin) ordinarily is very stable and cannot be broken easily. In most cases, cleavage of the glycosidic groups will occur to generate small amounts of anthocyanidins in addition to the intact anthocyanin molecular ions. 

Anthocyanins are the deeply colored glycosides of the aglycone anthocyanidins. Only the six aglycones shown in Figure 13.6 are common, although others occur sporadically [11,12]. 

Anthocyanins and anthocyanidins are readily separated on cellulose layers using developing solvents consisting hydrochloric acid-formic acid-water in differing proportions [24]. Glycosides and aglycones are readily separated on the same plate, provided that a sufficiently polar solvent is employed. 

Anthocyanins are colored flavonoids that attract animals when a flower is ready for pollination or a fruit is ready to eat. They are glycosides (i.e., the molecule contains a sugar) that range in color from red, pink, and purple to blue depending on the number and placement of substitutes on the B ring (see Fig. 3.7), the presence of acid residues, and the pH of the cell vacuole where they are stored. Without the sugar these molecules are called anthocyanidins. The color of some pigments results from a complex of different anthocyanin and flavone molecules with metal ions. 

Chemically, anthocyanins are glycosides of anthocyanidins and are based on a 2-phenylbenzopyrilium structure. The properties of the anthocyanins depend on the anthocyanidins from which they originate. 

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