Cyanidin is a natural
organic compound. It is a water-soluble pigment belongs to the group of Anthocyanins and has the typical
C6-C3-C6 structure. The color of cyanidin will depend on the pH of the
solution. Cyanidin is red when pH is below 3, blue at pH higher than 11 and
violet at neutral pH.
Cyanidin is present in most
red coloured berries such as bilberry, blackberry, blueberry, cherry,
cranberry, elderberry, hawthorn, loganberry and raspberry. In plants the
cyanidin is bound to a sugar molecule to form cyanidin 3-O-beta-Glucoside
Molecular Formula: C15H11O
Average mass 287.244 Da
IUPAC Name: 2-(3, 4-Dihydroxyphenyl)-3, 5,
1.3. Natural sources and part from plant
Bilberry (Vaccinium myrtillus L.)
It is one of the richest sources of cyanidin
which are known to have anticancer, wound healing and anti-allergic effects.
Part from plant source: Bilberry is a subshrub
with coriaceous leaves.
The cranberry (Vaccinium macrocarpon Aiton) :
It founds in the United States and Canada, is
commonly consumed as juice cocktail, juice, and other product forms (capsules,
tablets, etc.) to treat and prevent urinary tract infection.
It contains large amounts of cyanidin.
Part from plant source: fresh fruit of cranberry
is rich in cyanidin.
European elderberry (Sambucus nigra L.) :
elder is a tree native to Europe and parts of Asia and Africa, and it also
grows in the United States. The name “elder” comes from the Anglo-Saxon
word “aeld,” meaning fire. The terms “elder flower” and “elderberry” may
refer to either European elder or a different herb called American elder.
This fact sheet focuses only on European elder.
parts of the elder tree, including the bark, leaves, flowers, fruits, and
roots, have long been used in traditional medicine.
elderberry and elder flower are used as dietary supplements for flu,
colds, constipation, and other conditions.
dried flowers (elder flower) and the dried ripe or fresh berries
(elderberry) of the European elder tree are used in teas, extracts, and
Part from plant source: Ripe fruit of cranberry
is rich in cyanidin.
Red cabbage (Brassica oleracea):
It can be found in Northern Europe, throughout
the Americas, and in China (and especially in Africa). On cooking, red cabbage
will normally turn blue. To retain the red color it is necessary to add vinegar
or acidic fruit to the pot.
Part from plant source: Red cabbage
(reddish-purple in nature) is a source of novel cyanidin glycosides
Other dietary sources include chokeberries,
boysenberries, purple vegetables (such as carrots and yams), black raspberries,
and Hibiscus sabdariffa extract. Basically, dark blue to purple colored
plants. Interestingly, the darker than normal color in blood oranges relative
to normal oranges is due to cyanidin compounds.
N.B: The highest concentrations of cyanidin are
found in the skin of the fruit.
2. Pharmacological activity:
Cyanidin and its glycosides are very strong
antioxidants and are active at pharmacological concentrations. The antioxidant
activity is stronger than that of vitamin E, vitamin C and resveratrol and
similar to other commercial antioxidants. Cyanidin quickly neutralizes reactive
oxygen species such as hydrogen peroxide, reactive oxygen and hydroxyl radical.
Cyanidin may have benefits for the prevention
of obesity and diabetes. Cyanidin rich extracts significantly reduced the boy
weight gain of mice fed with a high fat diet. Cyanidin reduces blood glucose
level and improves insulin sensitivity due to the reduction of retinol binding
protein 4 expression in type 2 diabetic mice.
Cyanidin has antitoxic effect against
mycotoxins. Cyandin reduces DNA fragmentation and oxidative damage by aflatoxin
B1 and ochratoxin A.
Cyanidin from cherries alleviates arthritis in
an animal model and reduces the serum level of malonaldehyde, which is a
biomarker to measure the level of oxidative stress. It have important
implications for the prevention of nitric oxide mediated inflammatory diseases.
The anti-cancer and anti-mutagenic properties
of this anthocyanin are directly linked to its antioxidant properties. In-vivo
and in-vitro studies are linking cyanidin to a reduced risk of leukemia, lung
cancer, colon cancer, skin cancer and prostate cancer. Cyanidin induces cancer
cell apoptosis, reduces oxidative damage to DNA, inhibits cell growth and
decreases cancer cell proliferation.
2.6. Heart health
Endothelial dysfunction causes the development
of atherosclerosis, which can result in heart health problems, including stroke
and heart attacks. Cyanidin increases the levels of endothelial nitric oxide
synthase and heme oxygenase in a dose-dependent manner and inhibits the
formation of reactive oxygen species induced by platelet-derived growth factor,
a protein which has been linked to the development of atherosclerosis.
2.7. Skin protection
Cyanidin might successfully be employed for
skin protection. Ultraviolet radiation of the skin tissue causes production of
reactive oxygen species, resulting in oxidative stress, cell damage and
eventual cell death or skin cancer.
2.8. Ischemia-reperfusion protection
The strong antioxidant capacity of cyanidin can
be beneficial in conditions of increased oxidative stress, such as during a
myocardial ischemia, cerebral ischemia or liver ischemia. Myocardial ischemia
is a disease characterized by reduced blood supply to the heart muscle, usually
due to atherosclerosis of the coronary arteries.
Fig. 1 The
mechanism of action of cyanidin
As shown in Fig. 1, cyanidin is acted by:
It had a protective effect on DNA cleavage, a
dose-dependent free radical scavenging activity and significant inhibition of
xanthine oxidase activity.
It has ability to reduce the production of ROS,
and the inhibition of protein and DNA synthesis caused by aflatoxin B1 and ochratoxin
A in a human hepatoma cell line and a human colonic adenocarcinoma cell line.
Ant edema activity.
It decreases capillary permeability and
fragility so it participates the collage of vascular walls in the control of
permeability of that wall and inhibits proteolytic collagen degradation enzymes
(elastase and collagenase).
It increases regeneration of (visual purple) or
It reduces body fat accumulation induced by fats.
This effect was probably due to suppression of lipid synthesis in the liver and
in white adipose tissue.
It has anti diabetic effects. It inhibits
elevation of blood glucose levels and improves insulin sensitivity
It delays the onset of decline of neural
functions and improves cognitive and motor performance .The effects through
inhibition of neuroinflammatory mediators. i
4. Methods of isolation and identification
Isolation of cyanidin fraction
high performance liquid chromatography (HPLC)
column 10 mm, 250 mm ´ 20 mm; mobile phase: 0–260 min, 0–10 % B in A (A= 10 %
formic acid in water, B = 10 % formic acid in MeOH, followed by 10 % B in A for
30 min; flow rate 20 mL min–1) of the methanolic extract of R. bierberstinii
resulted in the isolation of five cyanidin glycosides,
3-O-sambubiosyl-5-O-glucosyl cyanidin (1, 50.6 mg, tR = 178.0 min), cyanidin
3-O-sambubioside (2, 5.1 mg, tR = 215.0 min), cyanidin 3-O- -glucoside (3, 10.8
mg, tR = 226.3 min), cyanidin 3-O-(2G-xylosyl)-rutinoside (4, 9.3 mg, tR =
238.6 min) and cyanidin 3-O-rutinoside (5, 5.7 mg, tR = 279.1 min).
anthocyanin mixture (3 mg) was dissolved in a minimum amount of acidified
MeOH (3 mol L–1
HCl). The test tube was placed in a boiling water bath for 1 h. The
was divided into two parts and the solvent was evaporated with a
rotary-evaporator. One of the solutions was treated with acidic MeOH for
genins and the
other with water for identification of glycones by thin layer chromatography (TLC).
TLC analyses of genins and glycones were performed using the solvent system butanol/acetic
acid/water (4:1:5) (BAW) and microcrystalline cellulose as a stationary phase.
Detection of glycones was carried out using aniline-hydrogen phthalate reagent.
Ethanol (2 mL)
was added to 2 mg of purified anthocyanins. The test tube was
nitrogen and capped. The solution was saponified with 10 mL, 2 mol L–1
NaOH for 2 h in
the dark at r. t. After neutralization of the solution with 2 mL of 2 mol
L–1 HCl, it was
decanted using diethyl ether (5 mL). For identification of probable acyls
anthocyanin structure, the ether phase was examined. Aqueous phase was
identification of anthocyanins. The TLC of two phases was carried out using
is specific for sugars on the C-3 position of cyanidins. Approximately
2 mg of
anthocyanin pigment was dissolved in MeOH and treated dropwise with
3 % peroxide
solution until the pigment was bleached. After addition of conc. ammonia
mL), the mixture was concentrated, spotted on a microcrystalline cellulose
together with reference sugar solution and developed for sugars.Chromatography was
carried out using BAW (4:1:5) and microcrystalline cellulose. Mono-, di- and tri-glycosides
would be removed intact from C-3 and could be identified with appropriate reference
It formed colored complexes with salts of many
Chromatography is valuable technique for
detection of cyanidin, and paper chromatographic method s in quantities as
small as 10ug gives elution of spots from chromatogram.
Gravimetric procedure spectrophotometric analysis
of cyanidin has been also described.
Thin layer chromatography on silica gel for
detection of cyanidin by UV spectrophotometric. It measured at 273 nm.
HPLC separation or identification of cyanidin
has been developed utilizing reversed phase systems with either C-18 or C-8
columns and moving phases of combination of acetic acid, water, methanol and acetonitrile.
5. Example of cyanidin in pharmacy:
bruising, periodontal disease, bleeding gums, thin skin, loss of elasticity,
Dosage: 1 – 2 tabs, 2 – 3 times daily
Side effects: It can cause some side
effects including headache, flushing, rashes, or stomach upset.
Precautions & Warnings:
and breast-feeding: There is not enough reliable information about the safety
of taking cyanidin if you are pregnant or breast
feeding. Stay on the safe side and avoid use.
in a nutrition rich in fruits and vegetables are linked with a reduce hazard of
inflammation-related chronic diseases. However, guide that cyanidins are safe, multitargeted,
effective , and affordable desire then investigations. It remains unknown what
amount of it is necessary and for how long time and if it is greater to consume
food with cyanidin or if supplements will suffice as well.