Pterorhodin

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]

Pterorhodin
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
3D model (JSmol)
ChemSpider
MeSH pterorhodin
  • 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).
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Infobox references

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. PMC 8370806. PMID 34403644. S2CID 237154759.
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