Peonidin

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Peonidin
Peonidin.png
Names
IUPAC name
3,4′,5,7-Tetrahydroxy-3′-methoxyflavylium
Systematic IUPAC name
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1λ4-benzopyran-1-ylium
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C16H12O6/c1-21-15-4-8(2-3-11(15)18)16-13(20)7-10-12(19)5-9(17)6-14(10)22-16/h2-7H,1H3,(H3-,17,18,19,20)/p+1 X mark.svgN
    Key: XFDQJKDGGOEYPI-UHFFFAOYSA-O X mark.svgN
  • Oc1cc2c(O)cc(O)cc2[o+]c1c3cc(OC)c(O)cc3
Properties
C16H13O6+
Molar mass 301.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The generic garden peony Paeonia officinalis officinalis0.jpg
The generic garden peony

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. [1] 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.[ citation needed ] 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. [2] 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. [3]

List of peonidin derivatives

Related Research Articles

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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.

<span class="mw-page-title-main">Berry</span> In the culinary sense, small edible fruit

A berry is a small, pulpy, and often edible fruit. Typically, berries are juicy, rounded, brightly colored, sweet, sour or tart, and do not have a stone or pit, although many pips or seeds may be present. Common examples of berries in the culinary sense are strawberries, raspberries, blueberries, blackberries, red currants, white currants and blackcurrants. In Britain, soft fruit is a horticultural term for such fruits.

<span class="mw-page-title-main">Anthocyanidin</span>

Anthocyanidins are common plant pigments, the sugar-free counterparts of anthocyanins. They are based on the flavylium cation, an oxonium ion, with various groups substituted for its hydrogen atoms. They generally change color from red through purple, blue, and bluish green as a function of pH.

<i>Vitis vinifera</i> Species of flowering plant in the grape vine family Vitaceae

Vitis vinifera, the common grape vine, is a species of flowering plant, native to the Mediterranean region, Central Europe, and southwestern Asia, from Morocco and Portugal north to southern Germany and east to northern Iran. There are currently between 5,000 and 10,000 varieties of Vitis vinifera grapes though only a few are of commercial significance for wine and table grape production.

<i>Amelanchier alnifolia</i> Species of tree

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<span class="mw-page-title-main">Norton (grape)</span> Variety of grape

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<span class="mw-page-title-main">Delphinidin</span> Chemical compound

Delphinidin is an anthocyanidin, a primary plant pigment, and also an antioxidant. Delphinidin gives blue hues to flowers in the genera Viola and Delphinium. It also gives the blue-red color of the grape variety Cabernet Sauvignon, and can be found in cranberries and Concord grapes as well as pomegranates, and bilberries.

<span class="mw-page-title-main">Cyanidin</span> Anthocyanidin pigment in flowering plant petals and fruits

Cyanidin is a natural organic compound. It is a particular type of anthocyanidin. It is a pigment found in many red berries including grapes, bilberry, blackberry, blueberry, cherry, chokeberry, cranberry, elderberry, hawthorn, loganberry, açai berry and raspberry. It can also be found in other fruits such as apples and plums, and in red cabbage and red onion. It has a characteristic reddish-purple 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. In certain fruits, the highest concentrations of cyanidin are found in the seeds and skin. Cyanidin has been found to be a potent sirtuin 6 (SIRT6) activator.

<span class="mw-page-title-main">Berry (botany)</span> Botanical fruit with fleshy pericarp, containing one or many seeds

In botany, a berry is a fleshy fruit without a stone (pit) produced from a single flower containing one ovary. Berries so defined include grapes, currants, and tomatoes, as well as cucumbers, eggplants (aubergines) and bananas, but exclude certain fruits that meet the culinary definition of berries, such as strawberries and raspberries. The berry is the most common type of fleshy fruit in which the entire outer layer of the ovary wall ripens into a potentially edible "pericarp". Berries may be formed from one or more carpels from the same flower. The seeds are usually embedded in the fleshy interior of the ovary, but there are some non-fleshy exceptions, such as Capsicum species, with air rather than pulp around their seeds.

Proanthocyanidins are a class of polyphenols found in many plants, such as cranberry, blueberry, and grape seeds. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More complex polyphenols, having the same polymeric building block, form the group of tannins.

<i>Lonicera caerulea</i> Honeysuckle plant

Lonicera caerulea, also known by its common names blue honeysuckle, sweetberry honeysuckle, fly honeysuckle, blue-berried honeysuckle, or the honeyberry, is a non-climbing honeysuckle native throughout the cool temperate Northern Hemisphere regions of North America, Europe, and Asia.

<span class="mw-page-title-main">Toxic Waste (candy)</span>

Toxic Waste is a line of sour candies owned and marketed by American company Candy Dynamics Inc., which is headquartered in Indianapolis, Indiana. The products are sold primarily in the United States and Canada as well as several international markets such as the United Kingdom, Ireland and South Africa. The toxic waste candy is packed in novelty drum containers, each holding 16 pieces of sour candy which come in five different flavors.

<span class="mw-page-title-main">Pelargonidin</span> Red anthocyanidin pigment found in certain flowers and fruits

Pelargonidin is an anthocyanidin, a type of plant pigment producing a characteristic orange color used in food and industrial dyes.

<span class="mw-page-title-main">Blueberry</span> Section of plants

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, bilberries, huckleberries and Madeira blueberries. Commercial blueberries—both wild (lowbush) and cultivated (highbush)—are all native to North America. The highbush varieties were introduced into Europe during the 1930s.

<span class="mw-page-title-main">Anthocyanin</span> Class of chemical compounds

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 compound that gives flowers a blue color for the first time in his treatise "Die Farben der Blüthen". Food plants rich in anthocyanins include the blueberry, raspberry, black rice, and black soybean, among many others that are red, blue, purple, or black. Some of the colors of autumn leaves are derived from anthocyanins.

<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

<span class="mw-page-title-main">Blue tomato</span> Various tomato cultivars

Blue tomatoes, sometimes referred to as purple tomato, are tomatoes that have been bred to produce high levels of anthocyanins, a class of pigments responsible for the blue and purple colours of many fruits, including blueberries, blackberries and chokeberries. Anthocyanins may provide protection for the plant against insects, diseases, and ultraviolet radiation. Some of these tomatoes have been commercialized under the names "Indigo Rose" and "SunBlack".

References

  1. Jung Yeon Kwon; Ki Won Lee; Haeng Jeon Hur; Hyong Joo Lee (2007). "Peonidin Inhibits Phorbol-Ester-Induced COX-2 Expression and Transformation in JB6 P+ Cells by Blocking Phosphorylation of ERK-1 and -2". Annals of the New York Academy of Sciences. 1095 (1): 513–520. Bibcode:2007NYASA1095..513K. doi:10.1196/annals.1397.055. PMID   17404064. S2CID   34779251.
  2. Van-Den Truong; Nigel Deighton; Roger T. Thompson; Roger F. McFeeters; Lisa O. Dean; Kenneth V. Pecota & G. Craig Yencho (2009). "Characterization of Anthocyanins and Anthocyanidins in Purple-Fleshed Sweetpotatoes by HPLC-DAD/ESI-MS/MS" (PDF). Journal of Agricultural and Food Chemistry. 58 (1): 404–410. doi:10.1021/jf902799a. PMID   20017481. Archived from the original (PDF) on 2010-07-12.
  3. N. Vorsa; J. Polashock; D. Cunningham; R. Roderick; A. Howell. "Evaluation Of Fruit Chemistry In Cranberry Germplasm: Potential For Breeding Varieties With Enhanced Health Constituents". ISHS Acta Horticulturae. 574: VII International Symposium on Vaccinium Culture.