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Barny, Lea [1], Tasca, Julia A. [2], Sanchez, Hugo A. [1], Smith, Chelsea R. [3], Koptur, Suzanne [4], Livshultz, Tatyana [5], Minbiole, Kevin P.C. [1].

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

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. Detectability of PAs varies among samples of Echites umbellatus and intra-individual plasticity contributes to this variation. Implications from this study for conducting broad chemotaxonomic surveys of plant specialized metabolites are discussed.

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Related Links:
Barny, L. A., J. A. Tasca, H. A. Sanchez, C. R. Smith, S. Koptur, T. Livshultz, and K. P. C. Minbiole. 2021. Chemotaxonomic investigation of Apocynaceae for retronecine-type pyrrolizidine alkaloids using HPLC-MS/MS. Phytochemistry 185: 112662.

1 - Villanova University, Chemistry, Villanova, PA, 19085, USA
2 - Perelman School of Medicine at the University of Pennsylvania, Biochemistry and Molecular Biophysics, 3400 Civic Center Blvd., Philadelphia, PA, 19104, USA
3 - Drexel University, Biodiversity Earth and Environmental Sciences, Philadelphia, PA, 19104, USA
4 - Florida International University, Department Of Biological Sciences, 11200 SW 8th St., Miami, FL, 33199, United States
5 - Academy Of Natural Sciences Of Drexel University, Department Of Botany, 1900 Benjamin Franklin Parkway, Philadelphia, PA, 19103, United States

specialized metabolites
secondary metabolites

Presentation Type: Oral Paper
Session: PHYT2, Phyochemistry II
Location: /
Date: Tuesday, July 20th, 2021
Time: 12:45 PM(EDT)
Number: PHYT2002
Abstract ID:467
Candidate for Awards:None

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