title: The effect of structurally related metabolites on insect herbivores: A case study on pyrrolizidine alkaloids and western flower thrips.
abstract: Plant specialised metabolites (SMs) are very diverse in terms of both their number and chemical structures with more than 200,000 estimated compounds. This chemical diversity occurs not only among different groups of compounds but also within the groups themselves. In the context of plant-insect interactions, the chemical diversity within a class of structurally related metabolites is generally also related to their bioactivity. In this study, we tested firstly whether individual SMs within the group of pyrrolizidine alkaloids (PAs) differ in their effects on insect herbivores (western flower thrips, Frankliniella occidentalis). Secondly, we tested combinations of PA N-oxides to determine whether they are more active than their individual components. We also evaluated the bioactivity of six PA free bases and their corresponding N-oxides. At concentrations similar to that in plants, several PAs reduced thrip's survival but the effect also differed strongly among PAs. In general, PA free bases caused a lower survival than their corresponding N-oxides. Among the tested PA free bases, we found jacobine and retrorsine to be the most active against second instar larvae of thrips, followed by erucifoline and seneciphylline, while senecionine and monocrotaline did not exhibit significant dose-dependent effects on thrip's survival. In the case of PA N-oxides, we found that only senecionine N-oxide and jacobine N-oxide reduced thrip's survival, although the effect of senecionine N-oxide was weak. Combinations of PA N-oxides showed no synergistic effects. These findings indicate the differences observed in the effect of structurally related SMs on insect herbivores. It is of limited value to study the bioactivity of combined groups, such as PAs, without taking their composition into account.
authors.affiliation: Plant Ecology and Phytochemistry, Institute of Biology, Leiden University, PO Box 9505, 2300 RA Leiden, The Netherlands. Electronic address: x.liu.2@biology.leidenuniv.nl.
authors.forename: Xiaojie
authors.initials: X
authors.lastname: Liu
authors.affiliation: Plant Ecology and Phytochemistry, Institute of Biology, Leiden University, PO Box 9505, 2300 RA Leiden, The Netherlands.
authors.forename: Peter G L
authors.initials: PGL
authors.lastname: Klinkhamer
authors.affiliation: Plant Ecology and Phytochemistry, Institute of Biology, Leiden University, PO Box 9505, 2300 RA Leiden, The Netherlands.
authors.forename: Klaas
authors.initials: K
authors.lastname: Vrieling
mesh_terms: D000818:Animals; D060434:Herbivory; D007814:Larva; D015394:Molecular Structure; D011763:Pyrrolizidine Alkaloids / Q000737:chemistry*; D061149:Thysanoptera / Q000187:drug effects*
chemical_list: D011763:Pyrrolizidine Alkaloids; C459639:erucifoline; C013678:seneciphylline; C056840:senecionine N-oxide; C013581:jacobine; C009237:senecionine; C003300:retrorsine
keywords: Asteraceae; Chemical structure; Frankliniella occidentalis; Jacobaea vulgaris; Plant defence; Senecio spp.; Specialised metabolites