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Flavonoid Glycosides and Naphthodianthrones in the Sawfly Tenthredo zonula and its Host-Plants, Hypericum perforatum and H. hirsutum

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Abstract

Larvae of the sawfly Tenthredo zonula are specialized on Hypericum. Whether the sawfly is able to sequester plant metabolites was unknown. Aerial materials of Hypericum perforatum and H. hirsutum, as well as dissected larvae and prepupae of T. zonula, were analyzed by HPLC to determine the presence and content of flavonoid glycosides (rutin, hyperoside, isoquercitrin, and quercitrin) and naphthodianthrones (pseudohypericin and hypericin). All flavonoid glycosides were detected in both Hypericum species, with hyperoside as major compound in H. perforatum (ca. 1.7 μmol/g fresh weight, FW) and isoquercitrin in H. hirsutum (0.7 μmol/g FW). Naphthodianthrones were present at low concentrations (0.02 μmol/g FW) in the former, and almost undetected in the latter species. In the body parts (i.e., hemolymph, digestive tract, salivary glands, or miscellaneous organs) of T. zonula, the surveyed compounds were detected more frequently in prepupae than in larvae. The compounds were not present in every sample, and flavonoid glycosides especially occurred in highly variable amounts, with maximal concentrations of 41 μg rutin/prepupa in salivary glands, 8 μg hyperoside/prepupa in hemolymph (= 0.36 μmol/g FW), 32 μg isoquercitrin/prepupa in salivary glands, and 63 μg quercitrin/larva in miscellaneous organs (mainly composed of the integument). We conclude that flavonoid glycosides are sequestered since they were detected in organs other than the digestive tract of larvae, and because prepupae are a non-feeding stage. The naphthodianthrone pseudohypericin, but not hypericin, occurred generally in the digestive tract (up to 0.25 μg/larva). Both naphthodianthrones and related unidentified compounds, but not flavonoid glycosides, were found in the larval excrement. The highly variable distributions of flavonoid glycosides and naphthodianthrones in T. zonula larvae and prepupae make it difficult to determine the ecological significance of these metabolites.

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Acknowledgments

We thank three anonymous reviewers for their helpful comments. Funding for SLC was provided through a Hertha Firnberg Stipendium (T345-B05) from the Fonds zur Förderung der Wissenschaftlichen Forschung (FWF) in Austria.

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Authors and Affiliations

  1. Institute of Pharmaceutical Sciences, Department of Pharmacognosy, Karl-Franzens-University, 8010, Graz, Austria

    Sara L. Crockett

  2. Department of Entomology, IRSNB-KBIN, Royal Belgian Institute of Natural Sciences, Rue Vautier 29, 1000, Brussels, Belgium

    Jean-Luc Boevé

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  1. Sara L. Crockett
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Correspondence to Jean-Luc Boevé.

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Crockett, S.L., Boevé, JL. Flavonoid Glycosides and Naphthodianthrones in the Sawfly Tenthredo zonula and its Host-Plants, Hypericum perforatum and H. hirsutum . J Chem Ecol 37, 943–952 (2011). https://doi.org/10.1007/s10886-011-0001-x

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