Pterobilin also called biliverdin IXγ in the Fischer nomenclature, is a blue bile pigment found in Nessaea spp., Graphium agamemnon, G. antiphates, Graphium doson, and G. sarpedon. 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 phorcabilin, used by other butterflies in Graphium and Papilio (specifically Papilio phorcas and Papilio weiskei), and sarpedobilin,[Chemical structure described at Pubchem] which is used by Graphium sarpedon.
Synthetic pathways
Pterobilin is a chemical precursor to sarpedobilin in the
of the fourth
instar of
G. sarpedon through a double
cyclisation of the central
of the adjacent nitrogens.
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.
[Rüdiger, W., Klose, W., Vuillaume, M., and Barbier, M. (1969). Experimentia, 25, 487-488.]
Pterobilin can be into phorcabilin and sarpedobilin in vitro. Pterobilin can also be thermally rearranged in vitro into phorcabilin.[Bois-Choussy, Michèle; Barbier, Michel (1978). Heterocycles 9, 677-690.]
Biochemical roles
Pterobilin in
P. brassicae[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.] is thought to play a role in
photoreception for the different instars for metering
diapause.
In adult
P. brassicae butterflies the compound is thought to have a role in
heat transfer,
[Allyn, A. C., Barbier, Michel, Bois-Choussy, Michèle, and Rothschild, M. (1981). Antenna, Londres, 29-31.] as the
where pterobilin accumulates differ morphologically in a way that would facilitate photoreception.
See also
External links