Nematicidal anthranilic acid derivatives from Laccaria species

Phytochemistry
Hedda SchreyPeter Spiteller

Abstract

Three undescribed natural products, the anthranilic acid derivatives laccanthrilic acids A, B, and C, as well as the known (3S)-1,2,3,4-tetrahydro-3-β-carboline-3-carboxylic acid were isolated from fruiting bodies of Laccaria laccata. The structures were established by 1D and 2D NMR spectroscopy, HR-(+)-ESIMS and chemical synthesis. The absolute configuration of laccanthrilic acids A and B was determined by GC-MS after hydrolytic cleavage and derivatisation of the resulting glutamic acid with methanol and Mosher's reagent and subsequent comparison with authentic synthetic samples of known absolute configuration. The absolute configuration of laccanthrilic acid C was determined by comparison of the CD spectra of laccanthrilic acids B and C with each other. Metabolic profiling of related species showed that the compounds are common in the genus Laccaria. Laccanthrilic acid B exhibited moderate nematicidal effects against Caenorhabditis elegans, which might explain to some degree the beneficial role of these fungi for the growth and survival of their host plants.

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Citations

Apr 30, 2019·Chemistry : a European Journal·Hedda Schrey, Peter Spiteller
Jan 24, 2020·Chembiochem : a European Journal of Chemical Biology·Rieke HimstedtPeter Spiteller
Jun 13, 2021·Drug Development Research·Parteek Prasher, Mousmee Sharma

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