NDLI: Recognition of pyrrolizidine alkaloid esters in the invasive aquatic plant Gymnocoronis spilanthoides (Asteraceae).

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Recognition of pyrrolizidine alkaloid esters in the invasive aquatic plant Gymnocoronis spilanthoides (Asteraceae).

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Boppré, Michael Colegate, Steven M.
Description	Country affiliation: Germany Author Affiliation: Boppré M ( Forstzoologie und Entomologie, Albert-Ludwigs-Universität, D-79085, Freiburg, Germany.)
Abstract	INTRODUCTION: The freshwater aquatic plant Gymnocoronis spilanthoides (Senegal tea plant, jazmín del bañado, Falscher Wasserfreund) is an invasive plant in many countries. Behavioural observations of pyrrolizidine alkaloid-pharmacophagous butterflies suggested the presence of pyrrolizidine alkaloids in the plant. OBJECTIVE: To determine whether the attraction of the butterflies to the plant is an accurate indicator of pyrrolizidine alkaloids in G. spilanthoides. METHODS: The alkaloid fraction of a methanolic extract of G. spilanthoides was analysed using HPLC with electrospray ionisation MS and MS/MS. Two HPLC approaches were used, that is, a C18 reversed-phase column with an acidic mobile phase, and a porous graphitic carbon column with a basic mobile phase. RESULTS: Pyrrolizidine alkaloids were confirmed, with the free base forms more prevalent than the N-oxides. The major alkaloids detected were lycopsamine and intermedine. The porous graphitic carbon HPLC column, with basic mobile phase conditions, resulted in better resolution of more pyrrolizidine alkaloids including rinderine, the heliotridine-based epimer of intermedine. Based on the MS/MS and high-resolution MS data, gymnocoronine was tentatively identified as an unusual C9 retronecine ester with 2,3-dihydroxy-2-propenylbutanoic acid. Among several minor-abundance monoester pyrrolizidines recognised, spilanthine was tentatively identified as an ester of isoretronecanol with the unusual 2-acetoxymethylbutanoic acid. CONCLUSIONS: The butterflies proved to be reliable indicators for the presence of pro-toxic 1,2-dehydropyrrolizidine alkaloids in G. spilanthoides, the first aquatic plant shown to produce these alkaloids. The presence of the anti-herbivory alkaloids may contribute to the plant's invasive capabilities and would certainly be a consideration in any risk assessment of deliberate utilisation of the plant. The prolific growth of the plant and the structural diversity of its pyrrolizidine alkaloids may make it ideal for investigating biosynthetic pathways or for large-scale production of specific alkaloids.
File Format	HTM / HTML
ISSN	09580344
Issue Number	3
Volume Number	26
e-ISSN	10991565
Journal	Phytochemical Analysis
Language	English
Publisher	Wiley
Publisher Date	2015-05-01
Publisher Place	Great Britain (UK)
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Discipline Botany Discipline Chemistry Asteraceae Chemistry Pyrrolizidine Alkaloids Analysis Chromatography, High Pressure Liquid Methods Esters Introduced Species Molecular Structure Tandem Mass Spectrometry Journal Article
Content Type	Text
Resource Type	Article
Subject	Plant Science Drug Discovery Analytical Chemistry Biochemistry Molecular Medicine Food Science Complementary and Alternative Medicine

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