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Chemotaxonomic investigation of Apocynaceae for retronecine-type pyrrolizidine alkaloids using HPLC-MS/MS
Journal article   Open access   Peer reviewed

Chemotaxonomic investigation of Apocynaceae for retronecine-type pyrrolizidine alkaloids using HPLC-MS/MS

Lea A. Barny, Julia A. Tasca, Hugo A. Sanchez, Chelsea R. Smith, Suzanne Koptur, Tatyana Livshultz and Kevin P.C. Minbiole
Phytochemistry (Oxford), v 185, 112662
May 2021
DOI: https://doi.org/10.1016/j.phytochem.2021.112662
PMID: 33774572
Featured in Collection :   UN Sustainable Development Goals @ Drexel
url
https://doi.org/10.1016/j.phytochem.2021.112662View
Published, Version of Record (VoR)CC BY V4.0,  Open

Abstract

Apocynaceae Chemotaxonomy Homospermidine synthase Infraspecific polymorphism Phenotypic plasticity Pyrrolizidine alkaloids Retronecine
Apocynaceae are well known for diverse specialized metabolites that are distributed in a phylogenetically informative manner. Pyrrolizidine alkaloids (PAs) have been reported sporadically in one lineage in the family, the APSA clade, but few species have been studied to date. We conducted the first systematic survey of Apocynaceae for retronecine-type PAs, sampling leaves from 231 species from 13 of 16 major lineages within the APSA clade using HPLC-MS/MS. We also followed up preliminary evidence for infra-specific variation of PA detectability in Echites umbellatus Jacq. Four precursor ion scans (PREC) were developed for a high-throughput survey for chemicals containing a structural moiety common to many PAs, the retronecine core. We identified with high confidence PAs in 7 of 8 sampled genera of tribe Echiteae, but not in samples from the closely related Odontadenieae and Mesechiteae, confirming the utility of PAs as a taxonomic character in tribal delimitation. Occurrence of PAs in Malouetieae is reported with moderate confidence in Galactophora schomburgkiana Woodson and Eucorymbia alba Stapf, but currently we have low confidence of their presence in Holarrena pubescens Wall. ex G. Don (the one Malouetieae species where they were previously reported), as well as in Holarrena curtisii King & Gamble and in Kibatalia macrophylla (Pierre ex Hua) Woodson. Candidate PAs in some species of Wrightia R. Br. (Wrightieae) and Marsdenia R. Br. (Marsdenieae) are proposed with moderate confidence, but a subset of the compounds in these taxa presenting with a PA-like fragmentation pattern are more likely to be aminobenzoyl glycosides. Candidate PAs are reported in species with predicted (VXXXD) and unexpected (IXXXN) amino acid motifs in their homospermidine synthase-like genes. Detectability of PAs varies among samples of Echites umbellatus and intra-individual plasticity contributes to this variation. Of toxicological importance, novel potential sources of human exposure to pro-toxic PAs were identified in the medicinal plant, Wrightia tinctoria R.Br., and the food plants, Marsdenia glabra Cost. and Echites panduratus A. DC., warranting immediate further research to elucidate the structures of the candidate PAs identified. Method development and limitations are discussed. [Display omitted] •HPLC- MS/MS precursor ion scans detected retronecine-core pyrrolizidine alkaloids.•Small samples of dried tissues from 231 Apocynaceae species were analyzed.•Candidate PAs are reported with high confidence for the first time in six genera.•PAs are a chemotaxonomic trait of tribe Echiteae.•Phenotypic plasticity is a cause of PA variation in Echites umbellatus.

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Collaboration types
Domestic collaboration
Web of Science research areas
Biochemistry & Molecular Biology
Plant Sciences
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