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Phycobilin

Phycobilin

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Phycobilins are chromophore
Chromophore
A chromophore is the part of a molecule responsible for its color. The color arises when a molecule absorbs certain wavelengths of visible light and transmits or reflects others. The chromophore is a region in the molecule where the energy difference between two different molecular orbitals falls...

s (light-capturing molecules) found in cyanobacteria and in the chloroplast
Chloroplast
Chloroplasts are organelles found in plant cells and other eukaryotic organisms that conduct photosynthesis. Chloroplasts capture light energy to conserve free energy in the form of ATP and reduce NADP to NADPH through a complex set of processes called photosynthesis.Chloroplasts are green...

s of red algae
Red algae
The red algae are one of the oldest groups of eukaryotic algae, and also one of the largest, with about 5,000–6,000 species  of mostly multicellular, marine algae, including many notable seaweeds...

, glaucophyte
Glaucophyte
The glaucophytes, also known as glaucocystophytes or glaucocystids, are a small group of freshwater microscopic algae. Together with the red algae and green algae plus land plants , they form the Archaeplastida...

s and some cryptomonad
Cryptomonad
The cryptomonads are a group of algae, most of which have plastids. They are common in freshwater, and also occur in marine and brackish habitats. Each cell is around 10-50 μm in size and flattened in shape, with an anterior groove or pocket...

s (though not in green algae
Green algae
The green algae are the large group of algae from which the embryophytes emerged. As such, they form a paraphyletic group, although the group including both green algae and embryophytes is monophyletic...

 and higher plant
Plant
Plants are living organisms belonging to the kingdom Plantae. Precise definitions of the kingdom vary, but as the term is used here, plants include familiar organisms such as trees, flowers, herbs, bushes, grasses, vines, ferns, mosses, and green algae. The group is also called green plants or...

s). They are unique among the photosynthetic pigments in that they are bonded to certain water-soluble protein
Protein
Proteins are biochemical compounds consisting of one or more polypeptides typically folded into a globular or fibrous form, facilitating a biological function. A polypeptide is a single linear polymer chain of amino acids bonded together by peptide bonds between the carboxyl and amino groups of...

s, known as phycobiliprotein
Phycobiliprotein
Phycobiliproteins are water-soluble proteins present in cyanobacteria and certain algae that capture light energy, which is then passed on to chlorophylls during photosynthesis. Phycobiliproteins are formed of a complex between proteins and covalently bound phycobilins that act as chromophores...

s. Phycobiliproteins then pass the light energy to chlorophyll
Chlorophyll
Chlorophyll is a green pigment found in almost all plants, algae, and cyanobacteria. Its name is derived from the Greek words χλωρος, chloros and φύλλον, phyllon . Chlorophyll is an extremely important biomolecule, critical in photosynthesis, which allows plants to obtain energy from light...

s for photosynthesis
Photosynthesis
Photosynthesis is a chemical process that converts carbon dioxide into organic compounds, especially sugars, using the energy from sunlight. Photosynthesis occurs in plants, algae, and many species of bacteria, but not in archaea. Photosynthetic organisms are called photoautotrophs, since they can...

.

The phycobilins are especially efficient at absorbing red, orange, yellow, and green light, wavelengths that are not well absorbed by chlorophyll a. Organisms growing in shallow waters tend to contain phycobilins that can capture yellow/red light, while those at greater depth often contain more of the phycobilins that can capture green light, which is relatively more abundant there.

The phycobilins fluoresce
Fluorescence
Fluorescence is the emission of light by a substance that has absorbed light or other electromagnetic radiation of a different wavelength. It is a form of luminescence. In most cases, emitted light has a longer wavelength, and therefore lower energy, than the absorbed radiation...

 at a particular wavelength, and are, therefore, often used in research as chemical tags, e.g., by binding phycobiliproteins to antibodies
Antibody
An antibody, also known as an immunoglobulin, is a large Y-shaped protein used by the immune system to identify and neutralize foreign objects such as bacteria and viruses. The antibody recognizes a unique part of the foreign target, termed an antigen...

 in a technique known as immunofluorescence
Immunofluorescence
Immunofluorescence is a technique used for light microscopy with a fluorescence microscope and is used primarily on biological samples. This technique uses the specificity of antibodies to their antigen to target fluorescent dyes to specific biomolecule targets within a cell, and therefore allows...

.

Types


There are four types of phycobilins:
  1. Phycoerythrobilin
    Phycoerythrobilin
    Phycoerythrobilin is a red phycobilin, i.e. an open tetrapyrrole chromophore found in cyanobacteria and in the chloroplasts of red algae, glaucophytes and some cryptomonads. Phycoerythrobilin is present in the phycobiliprotein phycoerythrin, of which it is the terminal acceptor of energy. The...

    , which is red
  2. Phycourobilin
    Phycourobilin
    Phycourobilin is a tetrapyrrole orange molecule involved in photosynthesis in cyanobacteria and red algae. This chromophore is bound to the phycobiliprotein phycoerythrin, the distal component of the light-harvesting system of cyanobacteria and red algae .When bound to phycoerythrin, phycourobilin...

    , which is orange
  3. Phycoviolobilin (also known as phycobiliviolin) found in phycoerythrocyanin
    Phycoerythrocyanin
    Phycoerythrocyanin is a kind of phycobiliproteins, magenta chromoprotein involved in photosynthesis of some Cyanobacteria. This chromoprotein consists of alpha- and beta-subunits, generally aggregated as hexamer...

  4. Phycocyanobilin
    Phycocyanobilin
    Phycocyanobilin is a blue phycobilin, i.e., a tetrapyrrole chromophore found in cyanobacteria and in the chloroplasts of red algae, glaucophytes, and some cryptomonads. Phycocyanobilin is present only in the phycobiliproteins allophycocyanin and phycocyanin, of which it is the terminal acceptor of...

     (also known as phycobiliverdin), which is blue.


They can be found in different combinations attached to phycobiliproteins to confer specific spectroscopic properties.

Structural relation to other molecules


In chemical terms, phycobilins consist of an open chain of four pyrrole
Pyrrole
Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4H4NH. It is a colourless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., N-methylpyrrole, C4H4NCH3...

 rings (tetrapyrrole
Tetrapyrrole
Tetrapyrroles are compounds containing four pyrrole rings. With the exception of corrin, the four pyrrole rings are interconnected through one-carbon bridges, in either a linear or a cyclic fashion...

) and are structurally similar to the bile
Bile
Bile or gall is a bitter-tasting, dark green to yellowish brown fluid, produced by the liver of most vertebrates, that aids the process of digestion of lipids in the small intestine. In many species, bile is stored in the gallbladder and upon eating is discharged into the duodenum...

 pigment bilirubin
Bilirubin
Bilirubin is the yellow breakdown product of normal heme catabolism. Heme is found in hemoglobin, a principal component of red blood cells. Bilirubin is excreted in bile and urine, and elevated levels may indicate certain diseases...

, which explains the name. (Bilirubin's conformation is also affected by light, a fact used for the phototherapy of jaundice
Jaundice
Jaundice is a yellowish pigmentation of the skin, the conjunctival membranes over the sclerae , and other mucous membranes caused by hyperbilirubinemia . This hyperbilirubinemia subsequently causes increased levels of bilirubin in the extracellular fluid...

d newborns.)
Phycobilins are also closely related to the chromophores of the light-detecting plant pigment phytochrome
Phytochrome
Phytochrome is a photoreceptor, a pigment that plants use to detect light. It is sensitive to light in the red and far-red region of the visible spectrum. Many flowering plants use it to regulate the time of flowering based on the length of day and night and to set circadian rhythms...

, which also consist of an open chain of four pyrroles.
Chlorophyll
Chlorophyll
Chlorophyll is a green pigment found in almost all plants, algae, and cyanobacteria. Its name is derived from the Greek words χλωρος, chloros and φύλλον, phyllon . Chlorophyll is an extremely important biomolecule, critical in photosynthesis, which allows plants to obtain energy from light...

s are composed of four pyrroles as well, but there the pyrroles are arranged in a ring and contain a metal atom in the center.