Journal of Chemical Ecology

, Volume 16, Issue 3, pp 743–748 | Cite as

A new sarpedobilin-containing butterflyPapilio graphium stresemani stresemani and its bioecological situation within the species

  • Michel Barbier
Article
  • 56 Downloads

Abstract

The doubly cyclized bile pigment sarpedobilin (3) represents a unique case in nature. In spite of being present in trace amounts in many butterfly and moth species containing pterobilin (1) or phorcabilin (2) as the main bilin, this substance occurs as the main pigment in a restricted number of species geographically limited to Southeast Asia. We have isolated and identified sarpedobilin3 (as the dimethyl ester) as the main bile pigment fromPapilio graphium stresemani stresemani (from Ceram island, Indonesia) in the amount of ca. 0.1 mg per individual, double that found inPapilio sar-pedon orP. weiskei. We conclude thatP. sarpedon (and subspecies)P. weis-kei, andP. stresemani represent, in terms of evolution (see article), a group of closely related species. By comparison of colored wing patterns and resistance of the chromoproteins to hydrolysis by MeOH-H2SO4,P. stresemani is nearP. weiskei. The bioecological relationships of the three sarpedobilin-containing species is discussed.

Key words

Sarpedobilin bile pigment butterfly Papilio graphium stresemani stresemani P. sarpedon P. weiskei Lepidoptera Papilionidae bioecological relationships 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Barbier, M. 1981. The status of blue-green bile pigments of butterflies and their phototransformations.Experientia 37:1060–1062.Google Scholar
  2. Barbier, M. 1983. The pigments ofPapilio graphium weiskei: Sarpedobilin and ommin responsible for a unique pattern in a butterfly wing membrane.Comp. Biochem. Physiol. 76B:57–59.Google Scholar
  3. Barbier, M. 1985. Interactions between the butterfly bile pigment sarpedobilin and polycarboxylic acids in vitro.Insect Biochem. 15:651–654.Google Scholar
  4. Bois-Choussy, M. 1977. Ptérobiline, phorcabiline et sarpédobiline, pigments biliaires 1Xγ isolés de Lépidoptères. Biosynthèses, réactivités et structures. Thesis, Université de Paris-Sud, 91405 Orsay cedex, France, 122 pp.Google Scholar
  5. Bois-Choussy, M., andBarbier, M. 1977. Structure de la sarpédobiline, pigment biliaire de Lépidoptère.Experientia 33:1407–1410.Google Scholar
  6. Bois-Choussy, M., andBarbier, M. 1978. Isomerisations and cylisations in bile pigments.Het-erocycles 9:677–690.Google Scholar
  7. Bois-Choussy, M., andBarbier, M. 1983. Photooxidation and photoprotection in the 1Xγ bile pigment series. A comparison of the photoprotective roles of pterobilin, phorcabilin and sarpedobilin in vitro.Tetrahedron 39:1915–1918.Google Scholar
  8. Choussy, M., andBarbier, M. 1975. Ptérobiline et néoptérobilines, réactivités et structures.Helv. Chim. Acta 58:2651–2661.Google Scholar
  9. Choussy, M., andBarbier, M. 1976. Transformations photochimiques de pigments biliaires des séries 1Xγ et 1Xδ.C.R. Acad. Sci. Paris 282(C):619–622.Google Scholar
  10. Rudiger, W., Klose, W., Vuillaume, M., andBarbier, M. 1968. On the structure of pterobilin, the blue pigment ofPieris brassicae.Experientia 24:1000.Google Scholar
  11. Vuillaume, M., andBarbier, M. 1969. Sur les pigments tètrapyrroliques des Lépidoptères.C.R. Acad. Sci. Paris 268:2286–2289.Google Scholar
  12. Vuillaume, M., Gruest, J., andBarbier, M. 1986. Interactions biochimiques de la sarpédobiline, substance pyrrolo-azépinique présente chez les Lépidoptères.C.R. Acad. Sci. Paris 302(3): 395–400.Google Scholar

Copyright information

© Plenum Publishing Corporation 1990

Authors and Affiliations

  • Michel Barbier
    • 1
  1. 1.Institut de Chimie des Substances Naturelles CNRSGif sur Yvette CedexFrance

Personalised recommendations