Pterorhodin

Last updated
Pterorhodin
Pterorhodin.png
Names
IUPAC name
2-Amino-7-[(E)-(2-amino-4,6-dioxo-5,8-dihydro-3H-pteridin-7-ylidene)methyl]-3,5-dihydropteridine-4,6-dione
Identifiers
  • 6538-79-0 Yes check.svgY
3D model (JSmol)
ChemSpider
MeSH pterorhodin
PubChem CID
  • InChI=1S/C13H10N10O4/c14-12-20-6-4(10(26)22-12)18-8(24)2(16-6)1-3-9(25)19-5-7(17-3)21-13(15)23-11(5)27/h1H,(H,18,24)(H,19,25)(H3,14,16,20,22,26)(H4,15,17,21,23,27)/b3-1+
    Key: STEFGLSLWLJVLH-HNQUOIGGSA-N
  • C(=C/1\C(=O)NC2=C(N1)N=C(NC2=O)N)\C3=NC4=C(C(=O)NC(=N4)N)NC3=O
Properties
C13H10N10O4
Molar mass 370.289 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Pterorhodin is a pteridine pigment found in animals and plants. [1] It has been extracted in melanosomes of tree frogs, butterflies, and plants as a wine red pigment. [2] [3] In lemur tree frogs, pterorhodin allows skin to reflect the sun's heat. [4] [5] Pterorhodin gives pigment color to bristle worms [6] and is found in the iris of multiple bird species including the red-eyed vireo [7] and the common loon. [8]

Related Research Articles

Botany Science of plant life

Botany, also called plant science(s), plant biology or phytology, is the science of plant life and a branch of biology. A botanist, plant scientist or phytologist is a scientist who specialises in this field. The term "botany" comes from the Ancient Greek word βοτάνη (botanē) meaning "pasture", "herbs" "grass", or "fodder"; βοτάνη is in turn derived from βόσκειν, "to feed" or "to graze". Traditionally, botany has also included the study of fungi and algae by mycologists and phycologists respectively, with the study of these three groups of organisms remaining within the sphere of interest of the International Botanical Congress. Nowadays, botanists study approximately 410,000 species of land plants of which some 391,000 species are vascular plants, and approximately 20,000 are bryophytes.

Fluorescence Emission of light by a substance that has absorbed light

Fluorescence is the emission of light by a substance that has absorbed light or other electromagnetic radiation. It is a form of luminescence. In most cases, the emitted light has a longer wavelength, and therefore a lower photon energy, than the absorbed radiation. A perceptible example of fluorescence occurs when the absorbed radiation is in the ultraviolet region of the spectrum, while the emitted light is in the visible region; this gives the fluorescent substance a distinct color that can only be seen when exposed to UV light. Fluorescent materials cease to glow nearly immediately when the radiation source stops, unlike phosphorescent materials, which continue to emit light for some time after.

Photosynthesis Biological process to convert light into chemical energy

Photosynthesis is a process used by plants and other organisms to convert light energy into chemical energy that, through cellular respiration, can later be released to fuel the organism's activities. This chemical energy is stored in carbohydrate molecules, such as sugars and starches, which are synthesized from carbon dioxide and water – hence the name photosynthesis, from the Greek phōs, "light", and sunthesis, "putting together". In most cases, oxygen is also released as a waste product. Most plants, algae, and cyanobacteria perform photosynthesis; such organisms are called photoautotrophs. Photosynthesis is largely responsible for producing and maintaining the oxygen content of the Earth's atmosphere, and supplies most of the energy necessary for life on Earth.

Melanin Group of natural pigments found in most organisms

Melanin is a broad term for a group of natural pigments found in most organisms. Melanin is produced through a multistage chemical process known as melanogenesis, where the oxidation of the amino acid tyrosine is followed by polymerization. The melanin pigments are produced in a specialized group of cells known as melanocytes.

Melanocyte Melanin-producing cells of the skin

Melanocytes are melanin-producing neural crest-derived cells located in the bottom layer of the skin's epidermis, the middle layer of the eye, the inner ear, vaginal epithelium, meninges, bones, and heart. Melanin is a dark pigment primarily responsible for skin color. Once synthesized, melanin is contained in special organelles called melanosomes which can be transported to nearby keratinocytes to induce pigmentation. Thus darker skin tones have more melanosomes present than lighter skin tones. Functionally, melanin serves as protection against UV radiation. Melanocytes also have a role in the immune system.

Chromatophore Cells with a primary function of coloration found in a wide range of animals

Chromatophores are cells that produce color, of which many types are pigment-containing cells, or groups of cells, found in a wide range of animals including amphibians, fish, reptiles, crustaceans and cephalopods. Mammals and birds, in contrast, have a class of cells called melanocytes for coloration.

Sexual dimorphism The condition where males and females exhibit different characteristics

Sexual dimorphism is the condition where the sexes of the same species exhibit different characteristics, particularly characteristics not directly involved in reproduction. The condition occurs in most animals and some plants. Differences may include secondary sex characteristics, size, weight, colour, markings, or behavioural or cognitive traits. These differences may be subtle or exaggerated and may be subjected to sexual selection and natural selection. The opposite of dimorphism is monomorphism, which is when both biological sexes are phenotypically indistinguishable from each other.

Tetrachromacy Type of color vision with four types of cone cells

Tetrachromacy is the condition of possessing four independent channels for conveying color information, or possessing four types of cone cell in the eye. Organisms with tetrachromacy are called tetrachromats.

Trichromacy Possessing of three independent channels for conveying color information

Trichromacy or trichromatism is the possessing of three independent channels for conveying color information, derived from the three different types of cone cells in the eye. Organisms with trichromacy are called trichromats.

Eye color Polygenic phenotypic character

Eye color is a polygenic phenotypic character determined by two distinct factors: the pigmentation of the eye's iris and the frequency-dependence of the scattering of light by the turbid medium in the stroma of the iris.

Archaeplastida Clade of eukaryotes containing land plants and some algae

The Archaeplastida are a major group of eukaryotes, comprising the photoautotrophic red algae (Rhodophyta), green algae, land plants, and the minor group glaucophytes. It also includes the non-photosynthetic lineage Rhodelphidia, a predatorial (eukaryotrophic) flagellate that is sister to the Rhodophyta, and probably the microscopic picozoans. The Archaeplastida have chloroplasts that are surrounded by two membranes, suggesting that they were acquired directly through a single endosymbiosis event by feeding on a cyanobacterium. All other groups which have chloroplasts, besides the amoeboid genus Paulinella, have chloroplasts surrounded by three or four membranes, suggesting they were acquired secondarily from red or green algae. Unlike red and green algae, glaucophytes have never been involved in secondary endosymbiosis events.

Photoprotection is the biochemical process that helps organisms cope with molecular damage caused by sunlight. Plants and other oxygenic phototrophs have developed a suite of photoprotective mechanisms to prevent photoinhibition and oxidative stress caused by excess or fluctuating light conditions. Humans and other animals have also developed photoprotective mechanisms to avoid UV photodamage to the skin, prevent DNA damage, and minimize the downstream effects of oxidative stress.

Biological pigment Substances produced by living organisms

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.

PMEL (gene)

Melanocyte protein PMEL also known as premelanosome protein (PMEL) or silver locus protein homolog (SILV) is a protein that in humans is encoded by the PMEL gene. Its gene product may be referred to as PMEL, silver, ME20, gp100 or Pmel17.

STX12

Syntaxin-12 is a protein that in humans is encoded by the STX12 gene.

Amelanism Pigmentation abnormality

Amelanism is a pigmentation abnormality characterized by the lack of pigments called melanins, commonly associated with a genetic loss of tyrosinase function. Amelanism can affect fish, amphibians, reptiles, birds, and mammals including humans. The appearance of an amelanistic animal depends on the remaining non-melanin pigments. The opposite of amelanism is melanism, a higher percentage of melanin.

Red algae Division of archaeplastids

Red algae, or Rhodophyta, are one of the oldest groups of eukaryotic algae. The Rhodophyta also comprises one of the largest phyla of algae, containing over 7,000 currently recognized species with taxonomic revisions ongoing. The majority of species (6,793) are found in the Florideophyceae (class), and mostly consist of multicellular, marine algae, including many notable seaweeds. Red algae are abundant in marine habitats but are relatively rare in freshwaters. Approximately 5% of the red algae occur in freshwater environments with greater concentrations found in warmer areas. Except for two coastal cave dwelling species in the asexual class Cyanidiophyceae, there are no terrestrial species, which may be due to an evolutionary bottleneck where the last common ancestor lost about 25% of its core genes and much of its evolutionary plasticity.

Melatonin receptor 1C, also known as MTNR1C, is a protein that is encoded by the Mtnr1c gene. This receptor has been identified in fish, amphibia, and birds, but not in humans.

Melanocortin 1 receptor G protein–coupled receptor that binds to a class of pituitary peptide hormones known as the melanocortins,

The melanocortin 1 receptor (MC1R), also known as melanocyte-stimulating hormone receptor (MSHR), melanin-activating peptide receptor, or melanotropin receptor, is a G protein–coupled receptor that binds to a class of pituitary peptide hormones known as the melanocortins, which include adrenocorticotropic hormone (ACTH) and the different forms of melanocyte-stimulating hormone (MSH). It is coupled to Gαs and upregulates levels of cAMP by activating adenylyl cyclase in cells expressing this receptor. It is normally expressed in skin and melanocytes, and to a lesser degree in periaqueductal gray matter, astrocytes and leukocytes. In skin cancer, MC1R is highly expressed in melanomas but not carcinomas.

Albinism Congenital disorder causing skin, eyes, hair/fur, scales, etc. to lack melanin pigmentation

Albinism is the congenital absence of any pigmentation or colouration in an animal, plant, or person, resulting in white hair, feathers, scales and skin and pink eyes in mammals, birds, reptiles, amphibians and fish and invertebrates as well. Varied use and interpretation of the terms mean that written reports of albinistic animals can be difficult to verify. Albinism can reduce the survivability of an animal; for example, it has been suggested that albino alligators have an average survival span of only 24 hours due to the lack of protection from UV radiation and their lack of camouflage to avoid predators. It is a common misconception that all albino animals have characteristic pink or red eyes, however this is not the case for some forms of albinism. Familiar albino animals include in-bred strains of laboratory animals, but populations of naturally occurring albino animals exist in the wild, e.g. Mexican cave tetra. Albinism is a well-recognized phenomenon in molluscs, both in the shell and in the soft parts. It has been claimed by some, e.g. that "albinism" can occur for a number of reasons aside from inheritance, including genetic mutations, diet, living conditions, age, disease, or injury. However, this is contrary to definitions where the condition is inherited.

References

  1. Ramakrishna Rao, K.; Meenakshisundaram, S.; Shanmugasundaram, E. R. B. (February 1967). "Formation and Identification of the Pigment Pterorhodin in a Mutant of Fusarium vasinfectum Atk". Nature. 213 (5075): 503–504. Bibcode:1967Natur.213..503R. doi:10.1038/213503a0. S2CID   4200675.
  2. Bagnara, Joseph T. (October 2003). "Enigmas of Pterorhodin, a Red Melanosomal Pigment of Tree Frogs". Pigment Cell Research. 16 (5): 510–516. doi:10.1034/j.1600-0749.2003.00075.x. PMID   12950730.
  3. Russell, Peter B.; Purrmann, Robert; Schmitt, Werner; Hitchings, George H. (October 1949). "The Synthesis of Pterorhodin (Rhodopterin)". Journal of the American Chemical Society. 71 (10): 3412–3416. doi:10.1021/ja01178a042.
  4. Schwalm, Patricia Ann (1981). Ultrastructural correlates to infrared reflectance in New World treefrogs (PhD). The University of Chicago.
  5. Blount, Christopher C. (2018). Near infrared reflectance in Anura (Thesis). The University of Manchester (United Kingdom).
  6. Viscontini, M.; Hummel, W.; Fischer, A. (1970). "Pigmente von Nereiden (Annelida, Polychaeten). 1., Vorläufige Mitteilung. Isolierung von Pterindimeren aus den Augen von Platynereis dumerilii (Audouin & Milne Edwards) 1833". Helvetica Chimica Acta. 53 (5): 1207–1209. doi:10.1002/hlca.19700530538.
  7. Hudon, Jocelyn; Muir, Alister D. (April 1996). "Characterization of the Reflective Materials and Organelles in the Bright Irides of North American Blackbirds (Icterinae)". Pigment Cell Research. 9 (2): 96–104. doi:10.1111/j.1600-0749.1996.tb00096.x. PMID   8857673.
  8. Andrade, Pedro; Carneiro, Miguel (August 2021). "Pterin-based pigmentation in animals". Biology Letters. 17 (8): 20210221. doi:10.1098/rsbl.2021.0221. PMID   34403644. S2CID   237154759.