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Pterobilin

From Wikipedia, the free encyclopedia
Pterobilin
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C23H21N3O2S2/c1-15-3-5-19(16(2)11-15)20-14-30-23(26-20)29-13-18-4-6-21(28-18)22(27)25-12-17-7-9-24-10-8-17/h3-11,14H,12-13H2,1-2H3,(H,25,27)
    Key: QWUAUCVIVCXEEL-UHFFFAOYSA-N
  • CC1=C(CCC(=O)O)\C(=C\c2[nH]c(\C=C/3\N=C(\C=C\4/NC(=O)C(=C4C)CCC(=O)O)C(=C3C)C=C)c(C=C)c2C)\NC1=O
Properties
C33H34N4O6
Molar mass582.657 g·mol−1
Density1.3±0.1 g/cm3[1]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Graphium sarpedon which contains pterobilin

Pterobilin also called biliverdin IXγ in the Fischer nomenclature,[2] is a bluebile pigment found inNessaea spp.,[3]Graphium agamemnon,G. antiphates,G. doson, andG. sarpedon.[4] It is one of only a few blue pigments found in any animal species, as most animals useiridescence to create blue coloration. Other blue pigments of animal origin includephorcabilin, used by other butterflies inGraphium andPapilio (specificallyP. phorcas andP. weiskei), andsarpedobilin,[5] which is used byGraphium sarpedon.[4]

Synthetic pathways

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Pterobilin is achemical precursor to sarpedobilin in thelarvae of the fourthinstar ofG. sarpedon through a doublecyclisation of the centralvinyl groups of the adjacent nitrogens.[6] In the butterfly speciesPieris brassicae, it is produced starting withacetate and then proceeding toglycin, thenδ-aminolevulinic acid, thencoproporphyrinogen III, toprotoporphyrin IX and finally into pterobilin.[6][7]

Pterobilin can bephototransformed into phorcabilin and sarpedobilinin vitro.[6] Pterobilin can also bethermally rearrangedin vitro into phorcabilin.[6][8]

Biochemical roles

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Pterobilin inP. brassicae[9][10][11] is thought to play a role inphotoreception for the different instars for meteringdiapause.[6] In adultP. brassicae butterflies the compound is thought to have a role inheat transfer,[12] as thewing scales where pterobilin accumulates differ morphologically in a way that would facilitate photoreception.[6]

See also

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References

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  1. ^"Pterobilin (Found by synonym)".ChemSpider. Retrieved21 January 2020.
  2. ^Moss, Gerard P. (1986)."IUPAC-IUB Joint Commission on Biochemical Nomenclauture (JCBN), Nomenclature of tetrapyrroles, Recommendations 1986".European Journal of Biochemistry.178 (2). FEBSPress:277–328.doi:10.1111/j.1432-1033.1988.tb14453.x.PMID 3208761.
  3. ^Vane-Wright, Richard I. (22 February 1979)."The coloration, identification and phylogeny ofNessaea butterflies (Lepidoptera : Nymphalidae)"(PDF).Bulletin of the British Museum (Natural History). Entomology Series.38 (2):27–56.OCLC 5510989. Retrieved8 February 2018.
  4. ^abSimonis, Priscilla; Serge, Berthier (30 March 2012)."Chapter number 1 How Nature produces blue color". In Massaro, Alessandro (ed.).Photonic Crystals - Introduction, Applications and Theory. InTech.ISBN 978-953-51-0431-5. Retrieved8 February 2018.
  5. ^Chemical structure described atPubchem
  6. ^abcdefBois-Choussy, Michèle; Barbier, Michel (10 February 1983). "Biosynthesis of the bile pigment sarpedobilin from [14C]pterobilin byPapilio sarpedon (lepidoptera)".Biochemical and Biophysical Research Communications.100 (3). Elsevier:779–782.doi:10.1016/0006-291X(83)91029-X.ISSN 0006-291X.OCLC 4922987039.PMID 6838551.
  7. ^Rüdiger, W., Klose, W., Vuillaume, M., and Barbier, M. (1969). Experimentia, 25, 487-488.
  8. ^Bois-Choussy, Michèle; Barbier, Michel (1978). Heterocycles 9, 677-690.
  9. ^Barbier, Michel, Bergerard, J., Hurpin, B., and Vuillaume, M. (1970). Comptes rendus de l'Académie des Sciences Paris, 271, 342-345.
  10. ^Vuillaume, M., and Bergerard, J. (1978). Chronobiologia, 5, 286-292.
  11. ^Vuillaume, M., and Dattée, Y. (1980). Archives de zoologie expérimentale et générale, 121, 159-164.
  12. ^Allyn, A. C., Barbier, Michel, Bois-Choussy, Michèle, and Rothschild, M. (1981). Antenna, Londres, 29-31.

External links

[edit]
Bilanes
(Linear)
Phytobilins
Phycobilins
Macrocycle
Corrinoids
Porphyrins
Protoporphyrins
Phytoporphyrins
Reduced
porphyrins
Porphyrinogens
Chlorins
Bacteriochlorins
Isobacteriochlorins
Corphins
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