Abstract:
:Specialized metabolites in plants influence their interactions with other species, including herbivorous insects, which may adapt to tolerate defensive phytochemicals. The chemical arsenal of Alliaria petiolata (garlic mustard, Brassicaceae) includes the glucosinolate sinigrin and alliarinoside, a hydroxynitrile glucoside with defensive properties to glucosinolate-adapted specialists. To further our understanding of the chemical ecology of A. petiolata, which is spreading invasively in North America, we investigated the metabolite profile and here report a novel natural product, petiolatamide, which is structurally related to sinigrin. In an extensive study of North American populations of A. petiolata, we demonstrate that genetic population differences as well as developmental regulation contribute to variation in the leaf content of petiolatamide, alliarinoside, sinigrin, and a related glycoside. We furthermore demonstrate widely different metabolic fates of these metabolites after ingestion in the glucosinolate-adapted herbivore Pieris rapae, ranging from simple passage over metabolic conversion to sequestration. The differences in metabolic fate were influenced by plant β-glucosidases, insect-mediated degradation, and the specificity of the larval gut transport system mediating sequestration.
journal_name
J Chem Ecoljournal_title
Journal of chemical ecologyauthors
Frisch T,Agerbirk N,Davis S,Cipollini D,Olsen CE,Motawia MS,Bjarnholt N,Møller BLdoi
10.1007/s10886-014-0509-ysubject
Has Abstractpub_date
2014-10-01 00:00:00pages
1063-79issue
10eissn
0098-0331issn
1573-1561journal_volume
40pub_type
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