Cyanidin
Encyclopedia
Cyanidin is a natural organic compound
. It is a particular type of anthocyanidin
(not to be confused with anthocyanins which are glycoside
s of anthocyanidins). It is a pigment found in many red berries including but not limited to grapes, bilberry
, blackberry
, blueberry
, cherry
, cranberry
, elderberry
, hawthorn
, loganberry
, acai berry and raspberry
. It can also be found in other fruits such as apple
s and plum
s, and in red cabbage
and red onion
. It has a characteristic reddish-orange color, though this can change with pH; solutions of the compound are red at pH < 3, violet at pH 7-8, and blue at pH > 11. The highest concentrations of cyanidin are found in the seeds and skin of a given fruit.
and radical
-scavenging effects which may protect cells from oxidative damage and reduce risk of cardiovascular disease
s and cancer
. One theory is that dietary intake of cyanidins may inhibit development of obesity
and diabetes as well as provide anti-inflammatory effects.
Other preliminary studies indicate that the glucoside
derivative of cyanidin might have a role in cancer therapy, although this remains unproven beyond laboratory testing.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
. It is a particular type of anthocyanidin
Anthocyanidin
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 . They form a large group of polymethine dye. In particular anthocyanidins are salt derivatives of the...
(not to be confused with anthocyanins which are glycoside
Glycoside
In chemistry, a glycoside is a molecule in which a sugar is bound to a non-carbohydrate moiety, usually a small organic molecule. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme...
s of anthocyanidins). It is a pigment found in many red berries including but not limited to grapes, bilberry
Bilberry
Bilberry is any of several species of low-growing shrubs in the genus Vaccinium , bearing edible berries. The species most often referred to is Vaccinium myrtillus L., but there are several other closely related species....
, blackberry
Blackberry
The blackberry is an edible fruit produced by any of several species in the Rubus genus of the Rosaceae family. The fruit is not a true berry; botanically it is termed an aggregate fruit, composed of small drupelets. The plants typically have biennial canes and perennial roots. Blackberries and...
, blueberry
Blueberry
Blueberries are flowering plants of the genus Vaccinium with dark-blue berries and are perennial...
, cherry
Cherry
The cherry is the fruit of many plants of the genus Prunus, and is a fleshy stone fruit. The cherry fruits of commerce are usually obtained from a limited number of species, including especially cultivars of the wild cherry, Prunus avium....
, cranberry
Cranberry
Cranberries are a group of evergreen dwarf shrubs or trailing vines in the subgenus Oxycoccus of the genus Vaccinium. In some methods of classification, Oxycoccus is regarded as a genus in its own right...
, elderberry
Elderberry
Sambucus is a genus of between 5 and 30 species of shrubs or small trees in the moschatel family, Adoxaceae. It was formerly placed in the honeysuckle family, Caprifoliaceae, but was reclassified due to genetic evidence...
, hawthorn
Crataegus
Crataegus , commonly called hawthorn or thornapple, is a large genus of shrubs and trees in the rose family, Rosaceae, native to temperate regions of the Northern Hemisphere in Europe, Asia and North America. The name hawthorn was originally applied to the species native to northern Europe,...
, loganberry
Loganberry
The loganberry is an hexaploid hybrid produced from crossing an octaploid blackberry and a diploid red raspberry. The plant and the fruit resemble the blackberry more than the raspberry, but the fruit colour is a dark red, rather than black...
, acai berry and raspberry
Raspberry
The raspberry or hindberry is the edible fruit of a multitude of plant species in the genus Rubus, most of which are in the subgenus Idaeobatus; the name also applies to these plants themselves...
. It can also be found in other fruits such as apple
Apple
The apple is the pomaceous fruit of the apple tree, species Malus domestica in the rose family . It is one of the most widely cultivated tree fruits, and the most widely known of the many members of genus Malus that are used by humans. Apple grow on small, deciduous trees that blossom in the spring...
s and plum
Plum
A plum or gage is a stone fruit tree in the genus Prunus, subgenus Prunus. The subgenus is distinguished from other subgenera in the shoots having a terminal bud and solitary side buds , the flowers in groups of one to five together on short stems, and the fruit having a groove running down one...
s, and in red cabbage
Red Cabbage
The red cabbage is a sort of cabbage, also known as Red Kraut or Blue Kraut after preparation....
and red onion
Red onion
Red onions, sometimes called purple onions, are cultivars of the onion with purplish red skin and white flesh tinged with red.These onions tend to be medium to large in size and have a mild to sweet flavor. They are often consumed raw, grilled or lightly cooked with other foods, or added as color...
. It has a characteristic reddish-orange color, though this can change with pH; solutions of the compound are red at pH < 3, violet at pH 7-8, and blue at pH > 11. The highest concentrations of cyanidin are found in the seeds and skin of a given fruit.
Effects on the human body
Cyanidin, like other anthocyanidins, has putative antioxidantAntioxidant
An antioxidant is a molecule capable of inhibiting the oxidation of other molecules. Oxidation is a chemical reaction that transfers electrons or hydrogen from a substance to an oxidizing agent. Oxidation reactions can produce free radicals. In turn, these radicals can start chain reactions. When...
and radical
Radical (chemistry)
Radicals are atoms, molecules, or ions with unpaired electrons on an open shell configuration. Free radicals may have positive, negative, or zero charge...
-scavenging effects which may protect cells from oxidative damage and reduce risk of cardiovascular disease
Cardiovascular disease
Heart disease or cardiovascular disease are the class of diseases that involve the heart or blood vessels . While the term technically refers to any disease that affects the cardiovascular system , it is usually used to refer to those related to atherosclerosis...
s and cancer
Cancer
Cancer , known medically as a malignant neoplasm, is a large group of different diseases, all involving unregulated cell growth. In cancer, cells divide and grow uncontrollably, forming malignant tumors, and invade nearby parts of the body. The cancer may also spread to more distant parts of the...
. One theory is that dietary intake of cyanidins may inhibit development of obesity
Obesity
Obesity is a medical condition in which excess body fat has accumulated to the extent that it may have an adverse effect on health, leading to reduced life expectancy and/or increased health problems...
and diabetes as well as provide anti-inflammatory effects.
Other preliminary studies indicate that the glucoside
Glucoside
A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes....
derivative of cyanidin might have a role in cancer therapy, although this remains unproven beyond laboratory testing.
List of cyanidin derivates
- AntirrhininAntirrhininAntirrhinin is an anthocyanin. It is the 3-rutinoside of cyanidin. It can be found in blackcurrant.-Metabolism:Cyanidin 3-O-rutinoside 5-O-glucosyltransferase uses UDP-glucose and cyanidin 3-O-rutinoside to produce UDP and cyanidin 3-O-rutinoside 5-O-beta-D-glucoside....
(cyanidin-3-rutinoside or 3-C-R) - cyanidin 3-O, found in red onionRed onionRed onions, sometimes called purple onions, are cultivars of the onion with purplish red skin and white flesh tinged with red.These onions tend to be medium to large in size and have a mild to sweet flavor. They are often consumed raw, grilled or lightly cooked with other foods, or added as color...
- cyanidin 7-O, found in red onion
- cyanidin 3,4′-di-O-β-glucopyranoside, found in red onion
- cyanidin 4′-O-β-glucoside, found in red onion
- Chrysontemin (cyanidin-3-O-glucoside) found in blackcurrantBlackcurrantBlackcurrant, Ribes nigrum, is a species of Ribes berry native to central and northern Europe and northern Asia, and is a perennial....
pomace
Further reading
- Galvano, F. et al. “Bioavailability, antioxidant and biological properties of the natural free-radical scavengers cyanidin and related glycosides”, Annali dell'Istituto Superiore di Sanità (2007),43(4):382-393.