Metalloanthocyanin

Last updated
Blue color inflorescences of Hydrangea macrophylla Hydrangea macrophylla - Hortensia hydrangea.jpg
Blue color inflorescences of Hydrangea macrophylla

A metalloanthocyanin is a chemical complex giving color to petals of certain plants.

Contents

These complexes are self-assembled, supramolecular metal complex pigment composed of stoichiometric amounts of anthocyanins, flavones, and metal ions. The various colors, such as red, mauve, purple, violet and blue, in Hydrangea macrophylla are developed from one simple anthocyanin, delphinidin 3-glucoside forming complexes with metal ions. [1]

Anthocyanin class of chemical compounds

Anthocyanins are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue or black. 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.

<i>Hydrangea macrophylla</i> species of plant

Hydrangea macrophylla is a species of flowering plant in the family Hydrangeaceae, native to Japan. It is a deciduous shrub growing to 2 m (7 ft) tall by 2.5 m (8 ft) broad with large heads of pink or blue flowers in summer and autumn. Common names include bigleaf hydrangea, French hydrangea, lacecap hydrangea, mophead hydrangea, penny mac and hortensia. It is widely cultivated in many parts of the world in many climates. It is not to be confused with H. aspera 'Macrophylla'.

Examples

Commelinin, a blue pigment from the flowers of Commelina communis , is a complex of 4 Mg 2+ ions chelating six anthocyanin molecules. [2]

<i>Commelina communis</i> species of plant

Commelina communis, commonly known as the Asiatic dayflower, is an herbaceous annual plant in the dayflower family. It gets its name because the blooms last for only one day. It is native throughout much of East Asia and northern parts of Southeast Asia. In China, the plant is known as yazhicao, roughly translating to "duckfoot herb", while in Japan it is known as tsuyukusa, meaning "dew herb". It has also been introduced to parts of central and southeastern Europe and much of eastern North America, where it has spread to become a noxious weed. It is common in disturbed sites and in moist soil. The flowers emerge from summer through fall and are distinctive with two relatively large blue petals and one very reduced white petal.

Magnesium Chemical element with atomic number 12

Magnesium is a chemical element with the symbol Mg and atomic number 12. It is a shiny gray solid which bears a close physical resemblance to the other five elements in the second column of the periodic table: all group 2 elements have the same electron configuration in the outer electron shell and a similar crystal structure.

Cyanosalvianin, a blue pigment from the flowers of Salvia uliginosa , is a complex formed of six molecules of the anthocyanin type, six molecules of the flavone type and two magnesium ions. [3]

<i>Salvia uliginosa</i> species of plant

Salvia uliginosa, the bog sage, is a species of flowering plant in the family Lamiaceae, native to southern Brazil, Uruguay, and Argentina. It was described and named by botanist George Bentham for its typical habitat "of swamps and marshes", or uliginosa.

Related Research Articles

<i>Ipomoea tricolor</i> species of plant

Ipomoea tricolor, the Mexican morning glory or just morning glory, is a species of flowering plant in the family Convolvulaceae, native to the New World tropics, and widely cultivated and naturalised elsewhere. It is an herbaceous annual or perennial twining liana growing to 2–4 m (7–13 ft) tall. The leaves are spirally arranged, 3–7 cm long with a 1.5–6 cm long petiole. The flowers are trumpet-shaped, 4–9 cm (2–4 in) in diameter, most commonly blue with a white to golden yellow centre.

Supramolecular chemistry is the domain of chemistry concerning chemical systems composed of a discrete number of molecules. The strength of the forces responsible for spatial organization of the system range from weak intermolecular forces, electrostatic charge, or hydrogen bonding to strong covalent bonding, provided that the electronic coupling strength remains small relative to the energy parameters of the component. Whereas traditional chemistry concentrates on the covalent bond, supramolecular chemistry examines the weaker and reversible non-covalent interactions between molecules. These forces include hydrogen bonding, metal coordination, hydrophobic forces, van der Waals forces, pi–pi interactions and electrostatic effects.

Supramolecular assembly

A supramolecular assembly or "supermolecule" is a well defined complex of molecules held together by noncovalent bonds. While a supramolecular assembly can be simply composed of two molecules, it is more often used to denote larger complexes of molecules that form sphere-, rod-, or sheet-like species. Micelles, liposomes and biological membranes are examples of supramolecular assemblies. The dimensions of supramolecular assemblies can range from nanometers to micrometers. Thus they allow access to nanoscale objects using a bottom-up approach in far fewer steps than a single molecule of similar dimensions.

Delphinidin 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 that produces Cabernet Sauvignon, and can be found in cranberries and Concord grapes as well as pomegranates, and bilberries.

Protocyanin is an anthocyanin pigment that is responsible for the red colouration of roses, but in cornflowers is blue. The pigment was first isolated in 1913 from the blue cornflower, and the identical pigment was isolated from a red rose in 1915. The difference in colour had been explained as a difference in flower-petal pH, but the pigment in the blue cornflower has been shown to be a supermolecular pigment consisting of anthocyanin, flavone, one ferric ion, one magnesium and two calcium ions forming a copigmentation complex.

Biological pigment substance produced by living organisms that has a color resulting from selective color absorption

Biological pigments, also known simply as pigments or biochromes, are substances produced by living organisms that have a color resulting from selective color absorption. Biological pigments include plant pigments and flower pigments. Many biological structures, such as skin, eyes, feathers, fur and hair contain pigments such as melanin in specialized cells called chromatophores. In some species, pigments accrue over very long periods during an individual's lifespan.

Molecular sensor

A molecular sensor or chemosensor is a molecular structure that is used for sensing of an analyte to produce a detectable change or a signal. The action of a chemosensor, relies on an interaction occurring at the molecular level, usually involves the continuous monitoring of the activity of a chemical species in a given matrix such as solution, air, blood, tissue, waste effluents, drinking water, etc. The application of chemosensors is referred to as chemosensing, which is a form of molecular recognition. All chemosensors are designed to contain a signalling moiety and a recognition moiety, that is connected either directly to each other or through a some kind of connector or a spacer. The signalling is often optically based electromagnetic radiation, giving rise to changes in either the ultraviolet and visible absorption or the emission properties of the sensors. Chemosensors may also be electrochemically based. Small molecule sensors are related to chemosensors. These are traditionally, however, considered as being structurally simple molecules and reflect the need to form chelating molecules for complexing ions in analytical chemistry. Chemosensors are synthetic analogues of biosensors, but such sensors incorporate biological receptor such as antibodies, aptamers or large biopolymers.

Anthoxanthin

Anthoxanthins are a type of flavonoid pigments in plants. Anthoxanthins are water-soluble pigments which range in color from white or colorless to a creamy to yellow, often on petals of flowers. These pigments are generally whiter in an acid medium and yellowed in an alkaline medium. They are very susceptible to color changes with minerals and metal ions, similar to anthocyanins. As with all flavonoids, they exhibit antioxidant properties, and are important in nutrition, and are sometimes used as food additives. Darkening with iron is particularly prominent in food products. They are considered to have more variety than anthocyanins. Some examples are quercitin.

Croconic acid chemical compound

Croconic acid or 4,5-dihydroxycyclopentenetrione is a chemical compound with formula C
5
H
2
O
5
or (C=O)
3
(COH)
2
. It has a cyclopentene backbone with two hydroxyl groups adjacent to the double bond and three ketone groups on the remaining carbon atoms. It is sensitive to light, soluble in water and ethanol and forms yellow crystals that decompose at 212 °C.

Myrtillin chemical compound

Myrtillin is an anthocyanin. It is the 3-glucoside of delphinidin. It can be found in all green plants, most abundantly in 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.

Muriel Wheldale Onslow English biochemist

Muriel Wheldale Onslow was a British biochemist, born in Birmingham, England. She was married to biochemist Victor Alexander Herbert Huia Onslow, second son of the 4th Earl of Onslow. She studied the inheritance of flower color in the common snapdragon further contributing in the concern of biochemistry pigment molecules in plants such as anthocyanins. She attended the King Edward VI High School in Birmingham and then matriculated at Newnham College, Cambridge in 1900. At Cambridge she majored in botany. She received no degree from Cambridge, despite taking First Class Honors in both parts of the Natural Sciences Tripos, because Cambridge did not award degrees to women until 1948. Onslow later worked alongside Bateson's genetic group in Cambridge, providing expertise in biochemical genetics and investigating the inheritance of petal color in Antirrhinum (snapdragons). She was one of the first women appointed as a lecturer at Cambridge, after moving to the Biochemistry department. A play was written about her and three other female biochemists.

Copigmentation is a phenomenon where pigmentation due to anthocyanidins is reinforced by the presence of other colorless flavonoids known as cofactors or “copigments”. This occurs by the formation of a non-covalently-linked complex.

Violdelphin chemical compound

Violdelphin is an anthocyanin, a plant pigment, has been found in the purplish blue flower of Aconitum chinense, in the blue flowers in the genus Campanula and in the blue flowers of Delphinium hybridum. It is a flavenoid natural product, incorporating two p-hydroxy benzoic acid residues, one rutinoside and two glucosides associated with a delphinidin.

<i>Delphinium</i> × <i>cultorum</i> species of plant

Delphinium × cultorum is a hybrid species in the genus Delphinium derived from D. elatum.

Pelargonin chemical compound

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

Basics of blue flower colouration

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. Yoshida K, Mori M, Kondo T (2009). "Blue flower color development by anthocyanins: from chemical structure to cell physiology". Nat. Prod. Rep. 26 (7): 884–915. doi:10.1039/b800165k. PMID   19554240.
  2. Shiono M, Matsugaki N, Takeda K (2008). "Structure of commelinin, a blue complex pigment from the blue flowers of Commelina communis". Proc. Jpn. Acad., Ser. B, Phys. Biol. Sci. 84 (10): 452–6. doi:10.2183/pjab.84.452. PMC   3720548 . PMID   19075517.
  3. Mori M, Kondo T, Yoshida K (December 2008). "Cyanosalvianin, a supramolecular blue metalloanthocyanin, from petals of Salvia uliginosa". Phytochemistry. 69 (18): 3151–8. doi:10.1016/j.phytochem.2008.03.015. PMID   18466933.