{{Chembox | ImageFile = Pterobilin.svg | ImageSize = 250px <!-- Names --> | IUPACName = | OtherNames = <!-- Sections --> | Section1 = {{Chembox Identifiers | CASNo = 20890-42-0 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = ZEK8SD9LJN | PubChem = 5287802 | ChemSpiderID = 4952646 | StdInChI=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) | StdInChIKey = QWUAUCVIVCXEEL-UHFFFAOYSA-N | SMILES = 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 }} | Section2 = {{Chembox Properties | C = 33 | H = 34 | N = 4 | O = 6 | Appearance = | Density = 1.3±0.1 g/cm<sup>3</sup><ref>{{cite web |title=Pterobilin (Found by synonym) |url=https://www.chemspider.com/Chemical-Structure.4952646.html?rid=7d815bcf-6cd4-461d-8880-9353450b7e0f |website=ChemSpider |access-date=21 January 2020 |language=en}}</ref> | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} thumb|right|''Graphium sarpedon'' which contains pterobilin '''Pterobilin''' also called biliverdin IXγ in the Fischer nomenclature,<ref name="nomenclature">{{cite journal |last1=Moss |first1=Gerard P. |title=IUPAC-IUB Joint Commission on Biochemical Nomenclauture (JCBN), Nomenclature of tetrapyrroles, Recommendations 1986 |journal=European Journal of Biochemistry |volume=178 | year=1986 |issue=2 | pages=277–328 |doi=10.1111/j.1432-1033.1988.tb14453.x |pmid=3208761 |publisher=FEBSPress |language=en|doi-access=free }}</ref> is a blue bile pigment found in ''Nessaea'' spp.,<ref name="Vane-Wright">{{cite journal|last1=Vane-Wright|first1=Richard I.|title=The coloration, identification and phylogeny of ''Nessaea'' butterflies (Lepidoptera : Nymphalidae)|journal=Bulletin of the British Museum (Natural History)|date=22 February 1979|volume=38|issue=2|pages=27–56|url=https://www.researchgate.net/publication/279190422|oclc=5510989|access-date=8 February 2018|language=English|format=PDF|series=Entomology Series}}</ref> ''Graphium agamemnon'', ''G. antiphates'', ''G. doson'', and ''G. sarpedon''.<ref name="Simonis">{{cite book|last1=Simonis|first1=Priscilla|last2=Serge|first2=Berthier|editor1-last=Massaro|editor1-first=Alessandro|title=Photonic Crystals - Introduction, Applications and Theory|date=30 March 2012|publisher=InTech|isbn=978-953-51-0431-5|chapter-url=https://www.researchgate.net/publication/258042644|access-date=8 February 2018|language=English|chapter=Chapter number 1 How Nature produces blue color}}</ref> It is one of only a few blue pigments found in any animal species, as most animals use structural coloration to create blue coloration. Other blue pigments of animal origin include phorcabilin, used by other butterflies in ''Graphium'' and ''Papilio'' (specifically ''P. phorcas'' and ''P. weiskei''), and sarpedobilin,<ref>Chemical structure described at [https://pubchem.ncbi.nlm.nih.gov/compound/Sarpedobilin Pubchem]</ref> which is used by ''Graphium sarpedon''.<ref name="Simonis"/>
==Synthetic pathways== Pterobilin is a chemical precursor to sarpedobilin in the larvae of the fourth instar of ''G. sarpedon'' through a double cyclisation of the central vinyl groups of the adjacent nitrogens.<ref name="Bois-ChoussyBarbier">{{cite journal |last1=Bois-Choussy |first1=Michèle |last2=Barbier |first2=Michel |title=Biosynthesis of the bile pigment sarpedobilin from [14C]pterobilin by ''Papilio sarpedon'' (lepidoptera) |journal=Biochemical and Biophysical Research Communications |date=10 February 1983 |volume=100 |issue=3 |pages=779–782 |doi=10.1016/0006-291X(83)91029-X |pmid=6838551 |publisher=Elsevier |language=en |issn=0006-291X |oclc=4922987039}}</ref> 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.<ref name="Bois-ChoussyBarbier"/><ref>Rüdiger, W., Klose, W., Vuillaume, M., and Barbier, M. (1969). Experimentia, 25, 487-488.</ref>
Pterobilin can be phototransformed into phorcabilin and sarpedobilin ''in vitro''.<ref name="Bois-ChoussyBarbier"/> Pterobilin can also be thermally rearranged ''in vitro'' into phorcabilin.<ref name="Bois-ChoussyBarbier"/><ref>Bois-Choussy, Michèle; Barbier, Michel (1978). Heterocycles 9, 677-690.</ref>
==Biochemical roles== Pterobilin in ''P. brassicae''<ref>Barbier, Michel, Bergerard, J., Hurpin, B., and Vuillaume, M. (1970). Comptes rendus de l'Académie des Sciences Paris, 271, 342-345.</ref><ref>Vuillaume, M., and Bergerard, J. (1978). Chronobiologia, 5, 286-292.</ref><ref>Vuillaume, M., and Dattée, Y. (1980). Archives de zoologie expérimentale et générale, 121, 159-164.</ref> is thought to play a role in photoreception for the different instars for metering diapause.<ref name="Bois-ChoussyBarbier"/> In adult ''P. brassicae'' butterflies the compound is thought to have a role in heat transfer,<ref>Allyn, A. C., Barbier, Michel, Bois-Choussy, Michèle, and Rothschild, M. (1981). Antenna, Londres, 29-31.</ref> as the wing scales where pterobilin accumulates differ morphologically in a way that would facilitate photoreception.<ref name="Bois-ChoussyBarbier"/>
==See also== * Basics of blue flower colouration * Biliverdin
<!-- ==Further reading== * Rüdiger, W., Klose, W., Vuillaume, M., and Barbier, M. (1969). Bulletin de la Société de Chimie Biologique, 51, 559-562. -->
==References== {{Reflist}}
==External links== *{{Wikidata-inline}}
{{Tetrapyrroles}}
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Category:Graphium (butterfly) Category:Biological pigments Category:Biblidinae Category:Tetrapyrroles Category:Dicarboxylic acids