Journal of Chemical Ecology

, Volume 38, Issue 5, pp 538–546 | Cite as

Flavonoid Metabolites in the Hemolymph of European Pine Sawfly (Neodiprion sertifer) Larvae

  • Matti Vihakas
  • Petri Tähtinen
  • Vladimir Ossipov
  • Juha-Pekka Salminen


Flavonoids in the hemolymph of European pine sawfly (Neodiprion sertifer) larvae that were feeding on Pinus sylvestris needles were identified. HPLC–ESI–MS analysis revealed that the main components in the hemolymph were flavonol di- and triglucosides and a catechin monoglucoside. These compounds were isolated from the larval hemolymph and their structures were established by HPLC–MS, GC–MS, and NMR spectroscopy. The isolated flavonoids were identified as (+)-catechin 7-O-β-glucoside, isorhamnetin 3,7,4′-tri-O-β-glucoside, kaempferol 3,7,4′-tri-O-β-glucoside, and quercetin 3,7,4′-tri-O-β-glucoside. The combined concentration of these four compounds in the hemolymph was 3.7 mg/ml. None of these compounds was present in the needles of P. sylvestris. Therefore, we propose that the flavonoid glucosides were produced by the larvae from flavonoid monoglucosides and (+)-catechin obtained from the pine needles.


European pine sawfly Scots pine Hemolymph Flavonoid glycosides Hymenoptera Diprionidae 



The authors thank Antti Pouttu for helping to find the larvae and Olli Martiskainen for advice with the analytical equipment. Maarit Karonen, Jaana Liimatainen, Johanna Moilanen, and Anu Tuominen kindly reviewed the earlier versions of the manuscript. We acknowledge the University of Turku Strategic Research Grant (Ecological Interactions) that enabled the purchase of the UHPLC–MS system used. This work was supported by grants from Kone Foundation, Niemi Foundation and Turku University Foundation.

Supplementary material

10886_2012_113_MOESM1_ESM.doc (122 kb)
ESM 1 (DOC 122 kb)


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Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • Matti Vihakas
    • 1
  • Petri Tähtinen
    • 1
  • Vladimir Ossipov
    • 1
  • Juha-Pekka Salminen
    • 1
  1. 1.Laboratory of Organic Chemistry and Chemical Biology, Department of ChemistryUniversity of TurkuTurkuFinland

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