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Journal of Chemical Ecology

, Volume 19, Issue 4, pp 669–679 | Cite as

Pyrrolizidine alkaloids in the arctiid mothHyalurga syma

  • José Roberto Trigo
  • Ludger Witte
  • Keith S. BrownJr.
  • Thomas Hartmann
  • Lauro E. S. Barata
Article

Abstract

The arctiid mothHyalurga syma (subfamily Pericopinae) sequesters pyrrolizidine alkaloids (PAs) from its larval food plantHeliotropium transalpinum (Boraginaceae). Colorimetric quantification of total PAs in the larvae, pupae, and adults ofHyalurga revealed mean values of about 286–445μg per individual (1.4–2.6% of dry weight). The PA mixtures found in the moth and its larval food plant were evaluated by GC-MS. Food-piant leaves were found to contain the diastereoisomeric retronecine esters indicine (IIIa), intermedine (IIIb), and lycopsamine (IIIc), and the heliotridine ester rinderine (IIId) only as minor constituents, whereas 3′-acetylrinderine (IVc) (68% of total PAs) and the respective 3′-acetyl esters of indicine (IVa) and intermedine (IVb) (both 17%) were the major alkaloids. Supinine (IIa) is detectable in traces only. The PA mixtures in eggs, larvae, pupae, and imagines ofHyalurga were identical: indicine, intermedine, and lycopsamine accompanied by considerable amounts of supinine and amabiline or coromandalinine (IIb/IIc) were the major components. Only larvae were found to store small quantities of a 3′-acetyl derivative. Rinderine and its 3′-acetyl ester were never found in the insects. Low concentrations of the arctiidspecific PA callimorphine (I) were present in larvae, pupae, and imagines. The differences in the PA patterns of the insects and their larval food plant suggest thatHyalurga is capable of modifying plant-derived PAs by inversion of the 7-OH configuration (conversion of the necine base heliotridine into retronecine), and perhaps the inversion of the 3′-OH [conversion of (+)-trachelanthic acid into (−)-viridifloric acid], although the possibility of a selective sequestration of the respective retronecine esters cannot be excluded. Some trials with the orb-weaving spiderNephila clavipes, a common neotropical predator, showed that both freshly emerged and field-caught adults ofHyalurga syma are liberated unharmed by the spider. The liberation could be related to the presence of PAs in the moths.

Key Words

Pyrrolizidine alkaloids alkaloid sequestration alkaloid transformation Boraginaceae Heliotropium transalpinum, Heliotropium peruvianum Lepidoptera Arctiidae Pericopinae Hyalurga syma chemical defense Araneidae Nephila clavipes orb-weaving spider 

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Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • José Roberto Trigo
    • 1
    • 2
    • 3
  • Ludger Witte
    • 2
  • Keith S. BrownJr.
    • 1
  • Thomas Hartmann
    • 2
  • Lauro E. S. Barata
    • 3
  1. 1.Laboratório de Ecologia Química Departamento de ZoologiaInstituto de Biologia, UNICAMPCampinas, S.P.Brazil
  2. 2.Institut für Pharmazeutische BiologieTechnische UniversitätBraunschweigGermany
  3. 3.Instituto de QuímicaUNICAMPCampinas, S.P.Brazil

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