The effect of structurally related metabolites on insect herbivores: A case study on pyrrolizidine alkaloids and western flower thrips. (June 2017)

• Record Type: Journal Article
• Authors: Liu, Xiaojie; Klinkhamer, Peter G.L.; Vrieling, Klaas
• Is Part Of: Phytochemistry. Volume 138(2017)
• Page Start: 93
• Page End: 103
• Publication Date: 2017-06
• Subjects: Jacobaea vulgaris -- Asteraceae -- Senecio spp. -- Specialised metabolites -- Plant defence -- Chemical structure -- Frankliniella occidentalis; IDIMIWQPUHURPV-OOFASRIMSA-N -- LHVAZUAALQTANZ-ANYXPJNNSA-N -- BCJMNZRQJAVDLD-VMOBWIEOSA-N -- HKODIGSRFALUTA-JTLQZVBZSA-N -- IJAULDQGSBFPPG-PWLBHZCXSA-N -- NKRQJWQYBNTAEV-SAJQNFQWSA-N -- IAPHXJRHXBQDQJ-WKMWQDDRSA-N -- QVCMHGGNRFRMAD-XFGHUUIASA-N -- PLGBHVNNYDZWGZ-GPUZEBNTSA-N -- NOQVBHHOUTTZGE-TZGXRXSYSA-N -- COHUFMBRBUPZPA-TUSLHEEYSA-N -- FCEVNJIUIMLVML-QPSVUOIXSA-N; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2017.02.027
• Languages: English
• ISSNs: 0031-9422

Abstract

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. Graphical abstract: Pyrrolizidine alkaloids from Jacobaea vulgaris vary in their effect on thrips survival and combinations of PA N-oxides did not show synergistic effects. Highlights: PAs at plant concentration reduced thrips survival on average with 21%. Structurally related PAs affect survival of thrips differently. PA free bases reduce thrips survival more than the corresponding PA N -oxides. No interactions were observed for mixtures of PA N -oxides on thrips survival.