| Peonidin is an O-methylated anthocyanidin derived from Cyanidin, and a primary plant pigment. Peonidin gives purplish-red hues to flowers such as the peony, from which it takes its name, and roses. It is also present in some blue flowers, such as the morning glory.
Like most anthocyanidins, it is pH sensitive, and changes from red to blue as pH rises because anthocyanidins are highly conjugated chromophores. When the pH is changed, the extent of the conjugation (of the double bonds) is altered, which alters the wavelength of light energy absorbed by the molecule. (Natural anthocyanidins are most stable in a very low pH environment; at pH 8.0, most become colorless.) At pH 2.0, peonidin is cherry red; at 3.0 a strong yellowish pink; at 5.0 it is grape red-purple; and at 8.0 it becomes deep blue; unlike many anthocyanidins, however, it is stable at higher pH, and has been isolated as a blue colorant from the brilliant "Heavenly Blue" morning glory (Ipomoea tricolor Cav cv).
Because of its unusual color stability, a cafeyl-acylated buffered formulation of it has been patented for use as food coloring.
Peonidin, like many anthocyanidins, has shown potent inhibitory and apoptotic effects on cancer cells in vitro, notably metastatic human breast cancer cells.
A very large question, however, has been raised about anthocyanidins' penetration and retention in human cells in vivo, due to their rapid elimination from the human body.
By far the greatest dietary source of peonidin is raw cranberries, which contain 42 mg per 100 g of fruit. Blueberries, plums, grapes, and cherries also contain significant amounts, ranging from 5 to 12 mg/100 g. Only fresh fruit has been shown to contain significant peonidin; frozen blueberries have been shown to contain almost none. Peonidin has been found in concentrations of up to 40 mg per 100 g (cooked) of certain cultivars of purple fleshed sweet potatoes; the amount of peonidin varies greatly across cultivars. It has also been isolated from raw black rice and black bananas.
The higher level of peonidin in fresh fruit corresponds to the rule of thumb that more natural fruit is healthier. Specifically, the amount of phenolic compounds in cranberries has been found to be inversely correlated with fruit size and crop yield. |
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| InChI=1S/C13H10N2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H,(H2,14,15) |
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Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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mutagen
An agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
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antiinfective agent
A substance used in the prophylaxis or therapy of infectious diseases.
fluorescent dye
MALDI matrix material
A compound used to form the matrix for MALDI (matrix-assisted laser desorption/ionization) mass spectrometry. MALDI matrix materials are crystalline compounds with a fairly low molecular weight, so as to allow facile vaporization, have strong absorption at UV or IR wavelengths (to rapidly and efficiently absorb laser irradiation), generally contain polar groups (enabling them to be used in aqueous solutions) and are frequently acidic (so assisting ionisation of the compound being studied, which is contained within the matrix material).
acid-base indicator
An acid or base which exhibits a colour change on neutralization by the basic or acidic titrant at or near the equivalence point of a titration.
antiseptic drug
A substance used locally on humans and other animals to destroy harmful microorganisms or to inhibit their activity (cf. disinfectants, which destroy microorganisms found on non-living objects, and antibiotics, which can be transported through the lymphatic system to destroy bacteria within the body).
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