Pterobilin

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Pterobilin
Pterobilin.svg
Identifiers
3D model (JSmol)
ChemSpider
  • 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 mass 582.6536
Density 1.3±0.1 g/cm3[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Graphium sarpedon which contains pterobilin

Pterobilin is a blue bile pigment found in Nessaea spp.,[2] Graphium agamemnon, G. antiphates, G. doson, and G. sarpedon.[3] It is one of only a few blue pigments found in any animal species, as most animals use iridescence to create blue coloration. Other blue pigments of animal origin include , used by other butterflies in Graphium and Papilio (specifically P. phorcas and P. weiskei), and , which is used by Graphium sarpedon.[3]

Synthetic pathways[]

Pterobilin 1 is a chemical precursor to sarpedobilin 3 in the larvae of the fourth instar of G. sarpedon through a double cyclisation of the central vinyl groups of the adjacent nitrogens.[4] In the butterfly species Pieris brassicae, it is produced starting with acetate and then proceeding to glycin, then δ-aminolevulinic acid, then coproporphyrinogen III, to protoporphyrin IX and finally into pterobilin.[4][5]

Pterobilin 1 can be phototransformed into Pterobilin 2 and 3 in vitro.[4] Pterobilin 1 can also be in vitro into phorcabilin 2.[4][6]

Biochemical roles[]

Pterobilin in P. brassicae[7][8][9] is thought to play a role in photoreception for the different instars for metering diapause.[4] In adult P. brassicae butterflies the compound is thought to have a role in heat transfer,[10] as the wing scales where pterobilin accumulates differ morphologically in a way that would facilitate photoreception.[4]

See also[]

Further reading[]

  • Rüdiger, W., Klose, W., Vuillaume, M., and Barbier, M. (1969). Experimentia, 25, 487-488.
  • Bois-Choussy, Michèle; Barbier, Michel (1978). Heterocycles 9, 677-690.
  • Barbier, Michel, Bergerard, J., Hurpin, B., and Vuillaume, M. (1970). Comptes rendus de l'Académie des Sciences Paris, 271, 342-345.
  • Vuillaume, M., and Bergerard, J. (1978). Chronobiologia, 5, 286-292.
  • Vuillaume, M., and Dattée, Y. (1980). Archives de zoologie expérimentale et générale, 121, 159-164.
  • Allyn, A. C., Barbier, Michel, Bois-Choussy, Michèle, and Rothschild, M. (1981). Antenna, Londres, 29-31.

References[]

  1. ^ "Pterobilin (Found by synonym)". ChemSpider. Retrieved 21 January 2020.
  2. ^ Vane-Wright, Richard I. (22 February 1979). "The coloration, identification and phylogeny of Nessaea butterflies (Lepidoptera : Nymphalidae)" (PDF). Bulletin of the British Museum (Natural History). Entomology Series. 38 (2): 27–56. OCLC 5510989. Retrieved 8 February 2018.
  3. ^ a b Simonis, 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. Retrieved 8 February 2018.
  4. ^ a b c d e f Bois-Choussy, Michèle; Barbier, Michel (10 February 1983). "Biosynthesis of the bile pigment sarpedobilin from [14C]pterobilin by Papilio sarpedon (lepidoptera)". Biochemical and Biophysical Research Communications. Elsevier. 100 (3): 779–782. doi:10.1016/0006-291X(83)91029-X. ISSN 0006-291X. OCLC 4922987039. PMID 6838551.
  5. ^ Rüdiger, W., Klose, W., Vuillaume, M., and Barbier, M. (1969). Experimentia, 25, 487-488.
  6. ^ Bois-Choussy, Michèle; Barbier, Michel (1978). Heterocycles 9, 677-690.
  7. ^ Barbier, Michel, Bergerard, J., Hurpin, B., and Vuillaume, M. (1970). Comptes rendus de l'Académie des Sciences Paris, 271, 342-345.
  8. ^ Vuillaume, M., and Bergerard, J. (1978). Chronobiologia, 5, 286-292.
  9. ^ Vuillaume, M., and Dattée, Y. (1980). Archives de zoologie expérimentale et générale, 121, 159-164.
  10. ^ Allyn, A. C., Barbier, Michel, Bois-Choussy, Michèle, and Rothschild, M. (1981). Antenna, Londres, 29-31.
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