Pelargonidin

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Pelargonidin
Pelargonidin.svg
Names
IUPAC name
3,4′,5,7-Tetrahydroxyflavylium
Systematic IUPAC name
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-1λ4-benzopyran-4-ylium
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-7H,(H3-,16,17,18,19)/p+1 X mark.svgN
    Key: XVFMGWDSJLBXDZ-UHFFFAOYSA-O X mark.svgN
  • InChI=1/C15H10O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-7H,(H3-,16,17,18,19)/p+1
    Key: XVFMGWDSJLBXDZ-IKLDFBCSAF
  • C1=CC(=CC=C1C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)O)O
Properties
C15H11O5+
Molar mass 271.24 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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Pelargonidin is an anthocyanidin, a type of plant pigment producing a characteristic orange color used in food and industrial dyes. [1]

Contents

Natural occurrences

Presence in flowers

Pelargonidin can be found in red geraniums (Geraniaceae). It is the predominant pigment causing the red coloration in the spathes of Philodendron (Araceae). The orange-coloured flowers of blue pimpernel ( Anagallis monelli , Myrsinaceae) have a higher concentration of pelargonidin pigment. Red and Pink Roses (Rosa) obtain their color from this phytochemical. [2]

Presence in food

Pelargonidin can be found in berries such as ripe raspberries and strawberries, as well as blueberries, blackberries, cranberries but also in saskatoon berries [3] and chokeberries. It is also found in plums and pomegranates. Pelargonidin gives red radishes their color. [4]

It is present in large amounts in kidney beans. [5]

Glycosides

In many plant systems, Pelargonidin can be added to a glucose molecule to form Pelargonidin 3-glucoside (callistephin). This is done by the 3GT, anthocyanin 3-O-glucosyltransferase gene. [6]

Pelargonidin 3-glucoside. Pelargonidin 3-O-glucoside.svg
Pelargonidin 3-glucoside.

However this glucosidation reduces its antioxidant activity, [7] and changes the wavelength of max light absorbance from 520 nm to 516 nm. [8]

Acylated pelargonidin glycosides can be found in red-purple flowers of Ipomoea purpurea . [9]

See also

Related Research Articles

<span class="mw-page-title-main">Flavonoid</span> Class of plant and fungus secondary metabolites

Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.

<span class="mw-page-title-main">Anthocyanidin</span> Class of natural compounds

Anthocyanidins are common plant pigments, the aglycones 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.

<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.

<i>Ipomoea purpurea</i> Species of plant

Ipomoea purpurea, the common morning-glory, tall morning-glory, or purple morning glory, is a species in the genus Ipomoea, native to Mexico and Central America.

<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">Antioxidant effect of polyphenols and natural phenols</span>

A polyphenol antioxidant is a hypothetized type of antioxidant, in which each instance would contain a polyphenolic substructure; such instances which have been studied in vitro. Numbering over 4,000 distinct chemical structures, such polyphenols may have antioxidant activity {{{1}}} in vitro (although they are unlikely to be antioxidants in vivo). Hypothetically, they may affect cell-to-cell signaling, receptor sensitivity, inflammatory enzyme activity or gene regulation, although high-quality clinical research has not confirmed any of these possible effects in humans as of 2020.

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

Malvin is a naturally occurring chemical of the anthocyanin family.

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

Malvidin is an O-methylated anthocyanidin, the 3',5'-methoxy derivative of delphinidin. As a primary plant pigment, its glycosides are highly abundant in nature.

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

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.

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

Betalains are a class of red and yellow tyrosine-derived pigments found in plants of the order Caryophyllales, where they replace anthocyanin pigments. Betalains also occur in some higher order fungi. They are most often noticeable in the petals of flowers, but may color the fruits, leaves, stems, and roots of plants that contain them. They include pigments such as those found in beets.

<span class="mw-page-title-main">Flavonol 3-O-glucosyltransferase</span> Class of enzymes

In enzymology, a flavonol 3-O-glucosyltransferase is an enzyme that catalyzes the chemical reaction

<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">Petunidin</span> Chemical compound

Petunidin (Pt), like Europinidin and Malvidin, is derived from Delphinidin and is an O-methylated anthocyanidin of the 3-hydroxy type. It is a natural organic compound, a dark-red or purple water-soluble pigment found in many redberries including chokeberries, Saskatoon berries or different species of grape, and also part of the pigments responsible for the petal colors in many flowers. This pigment gives the Indigo Rose tomatoes the majority of their deep purple color when the fruits are exposed to sunlight. The name of the molecule itself is derived from the word Petunia.

<span class="mw-page-title-main">Wine color</span> Wine characteristic

The color of wine is one of the most easily recognizable characteristics of wines. Color is also an element in wine tasting since heavy wines generally have a deeper color. The accessory traditionally used to judge the wine color was the tastevin, a shallow cup allowing one to see the color of the liquid in the dim light of a cellar. The color is an element in the classification of wines.

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

Antirrhinin is an anthocyanin. It is the 3-rutinoside of cyanidin.

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

Myrtillin is an anthocyanin. It is the 3-glucoside of delphinidin. It can be found in all green plants, most abundantly in black beans, blackcurrant, blueberry, huckleberry, bilberry leaves and in various myrtles, roselle plants, and Centella asiatica plant. It is also present in yeast and oatmeal. The sumac fruit's pericarp owes its dark red colour to anthocyanin pigments, of which chrysanthemin, myrtillin and delphinidin have yet been identified.

Sambubiose is a disaccharide. It is the β-D-xylosyl-(1→2)-β-D-glucose.

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

Pelargonin is an anthocyanin. It is the 3,5-O-diglucoside of pelargonidin.

<span class="mw-page-title-main">Basics of blue flower colouration</span>

Blue flower colour was always associated with something unusual and desired. Blue roses especially were assumed to be a dream that cannot be realised. Blue colour in flower petals is caused by anthocyanins, which are members of flavonoid class metabolites. We can diversify three main classes of anthocyanin pigments: cyaniding type responsible for red coloration, pelargonidin type responsible for orange colour and delphinidin type responsible for violet/blue flower and fruits coloration. The main difference in the structure of listed anthocyanins type is the number of hydroxyl groups in the B-ring of the anthocyanin. Nevertheless, in the monomeric state anthocyanins never show blue colour in the weak acidic and neutral pH. The mechanism of blue colour formation are very complicated in most cases, presence of delphinidin type pigments is not sufficient, great role play also the pH and the formation of complexes of anthocyanins with flavones and metal ions.

References

  1. USgranted 6,767,999,Smirnov, Vitaly; Sidorov, Viktor; Smirnova, Valentina,"Anthocyantin coloring agent and method for the production thereof from organic matter",published Nov 01, 2001,issued July 27, 2004
  2. Huihua, Wan; Chao, Yu; Yu, Han; Xuelian, Guo (2019). "Determination of Flavonoids and Carotenoids and Their Contributions to Various Colors of Rose Cultivars (Rosa spp.)". Frontiers in Plant Science. 10: 123. doi: 10.3389/fpls.2019.00123 . PMC   6379320 . PMID   30809238.
  3. Mazza, G. (2005). "Compositional and Functional Properties of Saskatoon Berry and Blueberry". International Journal of Fruit Science. 5 (3): 101–120. doi: 10.1300/J492v05n03_10 . S2CID   85691882.
  4. Takeshi Nishio (4 October 2017). Takeshi Nishio, Hiroyasu Kitashiba (ed.). The Radish Genome. Springer. p. 4. ISBN   978-3-319-59253-4.
  5. Lin, Long-Ze; Harnly, James M.; Pastor-Corrales, Marcial S.; Luthria, Devanand L. (2008). "The polyphenolic profiles of common bean (Phaseolus vulgaris L.)". Food Chemistry. 107 (1): 399–410. doi:10.1016/j.foodchem.2007.08.038. PMC   4276374 . PMID   25544796.
  6. Levisson, Mark; Patinios, Constantinios; Hein, Sascha; de Groot, Phillip A. (2018). "Engineering de novo anthocyanin production in Saccharomyces cerevisiae". Microbial Cell Factories. 17 (103): 103. doi: 10.1186/s12934-018-0951-6 . PMC   6029064 . PMID   29970082.
  7. Li, Wenfeng; Gu, Mengyuan; Gong, Pengling; Wang, Jinxia (2021). "Glycosides changed the stability and antioxidant activity of pelargonidin". Lebensmittel-Wissenschaft & Technologie. 147 (3): 111581. doi:10.1016/j.lwt.2021.111581. S2CID   235531625.
  8. Gould, Kevin S. (2009). Anthocyanidins: Biosynthesis, Functions, and Applications. New York: Springer. p. 286. ISBN   978-0-387-77334-6.
  9. Saito, N; Tatsuzawa, F; Yokoi, M; Kasahara, K; Iida, S; Shigihara, A; Honda, T (1996). "Acylated pelargonidin glycosides in red-purple flowers of Ipomoea purpurea". Phytochemistry. 43 (6): 1365–70. doi:10.1016/s0031-9422(96)00501-8. PMID   8987912.